Low-density preference of the ambient and high-pressure polymorphs of dl-menthol

Roszak, K.; Katrusiak, A.

doi:10.1107/S2052252523002452

research papers

IUCrJ

Volume 10| Part 3| May 2023| Pages 341-351

ISSN: 2052-2525

https://doi.org/10.1107/S2052252523002452

MATERIALS | COMPUTATION

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Low-density preference of the ambient and high-pressure polymorphs of DL-menthol

Kinga Roszak ^a and Andrzej Katrusiak ^a ^*

^aDeparment of Material Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, Poznań 61-614, Poland
^*Correspondence e-mail: katran@amu.edu.pl

Edited by A. Fitch, ESRF, France (Received 16 September 2022; accepted 13 March 2023; online 21 April 2023)

Lower-density polymorphs of DL-menthol were nucleated and crystallized in their high-pressure stability regions. Up to 0.30 GPa, the triclinic DL-menthol polymorph α, which is stable at atmospheric pressure, is less dense than a new β polymorph, which becomes stable above 0.40 GPa, but is less dense than the α polymorph at this pressure. The compression of polymorph α to at least 3.37 GPa is monotonic, with no signs of phase transitions. However, recrystallizations of DL-menthol above 0.40 GPa yield the β polymorph, which is less compressible and becomes less dense than α-DL-menthol. At 0.10 MPa, the melting point of the β polymorph is 14°C, much lower compared with those of α-DL-menthol (42–43°C) and L-menthol (36–38°C). The structures of both DL-menthol polymorphs α and β are very similar with respect to the lattice dimensions, the aggregation of OH⋯O molecules bonded into C_i symmetric chains, the presence of three symmetry-independent molecules (Z′ = 3), their sequence ABCC′B′A′, the disorder of the hydroxyl protons and the parallel arrangement of the chains. However, the different symmetries relating the chains constitute a high kinetic barrier for the solid–solid transition between polymorphs α and β, hence their crystallizations below or above 0.40 GPa, respectively, are required. In the structure of polymorph α, the directional OH⋯O bonds are shorter and the voids are larger compared with those in polymorph β, which leads to the reverse density relation of the polymorphs in their stability regions. This low-density preference reduces the Gibbs free-energy difference between the polymorphs: when polymorph α is compressed to above 0.40 GPa, the work component pΔV counteracts the transition to the less dense polymorph β, and on reducing the pressure of polymorph β to below 0.40 GPa, its transition to the less dense polymorph α is also hampered by the work contribution.

Keywords: polymorphism; compressibility; close-packing rule; polymorph prediction; molecular crystals; crystal engineering; intermolecular interactions.

CCDC references: 2206626; 2206627; 2206628; 2206629; 2206630; 2206631; 2206632; 2206633; 2206634; 2206635; 2206636; 2206637; 2206638; 2206639; 2206640; 2206641; 2206642; 2206643; 2206644; 2206645; 2206646; 2206647; 2206648; 2206649; 2206650; 2206651; 2206652; 2206653; 2206654; 2206655; 2206656; 2206657; 2206658

1. Introduction

The thermodynamic definition of pressure p = −∂F/∂V|_T (Feynman, 1972 ), where V is the volume of any closed system, T its absolute temperature and F is the Helmholz free energy, can be rewritten in the form p∂V = −∂F. The assumption of positive work performed on the system (∂F) and the positive p value require that ∂V be negative. This implies the positive compressibility value β = −(1/V)(∂V/∂p) for any given homogenous phase within its stability region (i.e. for monotonic pressure-induced changes of the closed system of a specified chemical composition). Although it is not strictly forbidden by thermodynamic laws, the experimental evidence shows that the pressure-induced phase transitions also lead to either discontinuous or continuous volume reduction. The volume reduction is considered a necessary condition for the formation of new forms that are stable under high pressure (e.g. Bridgman, 1949 ; Nye, 1984 ; Newnham, 2005 ; Baughman et al., 1998 ; Reichl, 1998 ), which is indeed often observed experimentally (e.g. Bridgman, 1964 ). Only very few exceptions indicate possible volume increases under high pressure: (i) when two polymorphs β and γ of 3-nitrophenyldisulfide were recrystallized at high temperature (Sobczak et al., 2021 ); (ii) when the composition of the sample was increased due to the penetration of the pressure-transmitting liquid (Lee et al., 2002 ; Li et al., 2014 ) and gases; or (iii) when the compound underwent a chemical reaction under high pressure (Zhang et al., 2020 ). Only the first of these exceptions (Sobczak et al., 2021) fulfils the condition of the same chemical composition, although the higher-volume polymorphs, nucleated under high-pressure and high-temperature conditions, are metastable under normal conditions and are built of higher-energy conformers. Thus the volume increase was attributed to the increased internal energy and the entropy contributions to the Gibbs free energy, compensating the work contribution of increased volume under high pressure and temperature when these low-density polymorphs were nucleated. This mechanism involves transformations at metastable states and in this respect, it is analogous to the concept of negative compression through destabilization of metastable equilibria of constituents (Nicolaou & Motter, 2012 ).

In the work described herein, we investigated a one-component compound, which does not change its composition, chemical formula or even the conformation of molecules, and we show that it favours the lower-density polymorphs under high-pressure conditions. To our knowledge, such a behaviour, when a low-density polymorph becomes stable under isothermally increased pressure, has not been reported to date. For this reason, as indicated above, it is often assumed that such a behaviour is not possible. Our case study on the well known fragrance compound DL-menthol demonstrates its preference to form the lower-density polymorphs, not only under atmospheric pressure, but also under high-pressure conditions. L-(−)-(1R,2S,5R)-menthol, naturally occurring in Mentha piperita and other Mentha species, is well known for its therapeutic qualities and as an ingredient in alimentary products and cosmetics (Fig. 1; Coleman et al., 1998 ). Of the four concomitant L-menthol polymorphs, three of them are monotropic at atmospheric pressure, and their transformations were described over a century ago by Wright (1917 ). The fresh, sweet, mint, cooling and refreshing smell of naturally occurring L-(−)-menthol is similar to that of D-(+)-menthol, which is somewhat less minty and less refreshing, with bitter, phenolic and herbaceous notes. Hence the D-enantiomer and DL-racemate are used as substitutes for or complements to natural menthol (Bhatia et al., 2008 ). The cooling sensation of L-(−)-menthol is about four times stronger than that of D-(+)-menthol, because the heat receptors in the skin are chiral (McKemy et al., 2002 ; Bentley, 2006 ). Unlike L-(−)-menthol, the DL-racemate is mainly obtained by chemical synthesis and applied in ointments, cough drops and nasal inhalers, but also for flavouring food, cigarettes, liqueurs, cosmetics, perfumes etc. The solubility of methanol is most relevant to its applications: it hardly dissolves in water, 0.456 mg ml⁻¹ at 25°C (298 K) (Yalkowsky et al., 2010 ), but it is very soluble in ethanol, methanol (100 mg ml⁻¹), diethyl ether, chloroform petroleum ether, hexane; and it is freely soluble in glacial acetic acid; liquid petrolatum; and in mineral, fixed and volatile oils (Hopp & Lawrence, 2006 ; Sell, 1999 ; O'Neil, 2013 ).

Figure 1
Chemical formula of L-(−)-menthol, its chiral centres (green) and atomic labels (red).

Single-crystal X-ray diffraction (SCXRD) measurements revealed that L-(−)-menthol crystallizes in the trigonal space group P3₁ (Ramsay & Rogers, 1952 ; Bombicz et al., 1999 ) and DL-menthol is triclinic, with the space group P1 (Corvis et al., 2012 ). The binary phase diagram of the L- and D-enantiomers and the formation of the DL-menthol racemate compound were studied nearly five decades ago (Kuhnert-Brandstätter et al., 1974 ) and later by Corvis et al. (2012; 2015 ), who also postulated new low-temperature metastable polymorphs of both L-(−)-menthol and DL-menthol at 233 K, but only the unit-cell dimensions and crystal symmetry (triclinic space group P1 for both), and no further structural information, were reported from the powder X-ray diffraction (PXRD) measurements. In our present study, we compressed and recrystallized DL-menthol under high-pressure in order to investigate its phase transitions and various possible forms, either polymorphs, solvates or even spontaneously separated enantiomers (Jacques et al., 1981 ; Cai et al., 2013 ; Marciniak et al., 2014 ). We have obtained and characterized a new polymorph of DL-menthol, labelled polymorph β. It can be recovered under atmospheric pressure only at low temperature, because its melting point is about 14°C (287 K). The crystallographic parameters of our polymorph β are markedly different from those of the DL-menthol polymorph reported by Corvis et al. (2012, 2015). However, we found during our study that its most intriguing aspect is the counterintuitive density relation between the DL-menthol polymorphs. Between atmospheric pressure and 0.30 GPa, i.e. with the stability range of polymorph α extending to 0.40 GPa, its density is lower than the density of the new polymorph β, which is metastable in this pressure range. Above 0.30 GPa, in the stability region of polymorph β, its density becomes lower compared with that of polymorph α over-compressed to the same high-pressure value. To our knowledge, such stability regions of low-density high-pressure polymorphs are unprecedented in the literature and they are difficult to reconcile with the close-packing rule. The structural and thermodynamic analysis of this exceptional high-pressure behaviour of DL-menthol reveals new aspects of the close (Kitaigorodsky, 1973 ) and loose aggregation of molecules (Bujak et al., 2008 , 2018 ; Kaźmierczak & Katrusiak, 2013 ).

2. Experimental

High-pressure experiments were performed in a Merrill–Bassett diamond anvil-cell (DAC, Merrill & Bassett, 1974 ), modified by mounting the anvils directly on steel backing plates with conical windows (Katrusiak, 2008 ). Crystals of DL-menthol were investigated either by gradually compressing a single crystal grown at 294 (2) K and atmospheric pressure, or by high-pressure recrystallizations and growing single crystals under isothermal and isochoric conditions from the solutions in dry methanol, ethanol, methanol:water mixture (1:2 v/v) and ethanol:water mixture (2:1 v/v), as shown in Figs. 2 and S1–S5 of the supporting information.

Figure 2
Single crystal of α-DL-menthol grown from the methanol:water mixture (1:2 v/v) under isochoric conditions in the DAC chamber at (a) 363 K, (b) 353 K, (c) 323 K, (d) 296 K and 0.10 GPa. Powder of crushed ruby chips for pressure calibration is scattered close to the gasket edge.

For the isothermal recrystallizations, the concentration of DL-menthol was adjusted to nucleate the crystal either below or above 0.40 GPa in order to check the possible role of increased temperature and entropy changes for the formation of polymorph β. Also, isochoric recrystallizations from pure molten DL-menthol were performed (Fig. S6) to eliminate the possibility of stoichiometric or stochastic cocrystallization of DL-menthol with solvent molecules. The isochoric recrystallizations of pure DL-menthol required 453 K for melting the sample at 0.90 GPa and 483 K for melting the sample at 1.28 GPa. We also performed seeded crystallizations above 0.40 GPa, when a small seed of polymorph α was left, when the temperature was lowered, but these recrystallizations also resulted in the crystals of polymorph β.

The structures of high-pressure polymorphs α and β were determined by SCXRD up to 3.37 and 2.90 GPa, respectively, although we plotted the data up to 2.5 GPa only to better represent the region around 0.40 GPa. The compression of DL-menthol crystals was determined for the sample grown under ambient conditions and then mounted in the DAC. The gaskets were made of 0.20 mm-thick Inconel foil and the initial diameter of the spark-eroded holes was 0.45 mm. Glycerine was used as the hydrostatic medium. Pressure in the DAC chamber was calibrated by the ruby-fluorescence method (Piermarini et al., 1975 ; Mao et al., 1986 ) with a Photon Control Inc. spectrometer, affording an accuracy of 0.02 GPa; the calibration was repeated before and after each diffraction measurement. Above 0.40 GPa the isochoric recrystallizations of molten DL-menthol and the solutions in methanol:water and ethanol:water mixtures (2:1 v/v) yielded a new monoclinic polymorph β (Fig. 3). Such alcohol:water mixtures start to separate under high pressure above 1 GPa, as ice VI crystallizes, which increases the methanol and ethanol concentration; eventually they become nearly pure and remain hydrostatic up to their freezing pressures at 3.50 and 1.80 GPa (Allan et al., 1998 ; Allan & Clark, 1999 ), respectively. The hydrostatic limit of glycerine was assessed as 3.00 GPa (Hazen & Finger, 1982 ). The crystallizations of DL-menthol from its melt were undertaken in order to exclude the possibility of stochastic solvation (Roszak & Katrusiak, 2021 ; Olejniczak et al., 2022a ), while the non-hydrostatic conditions due to the thermal contraction were ignored despite the markedly non-isotropic thermal contraction of the β-DL-menthol crystal (Figs. S7–S10).

Figure 3
Single crystal of β-DL-menthol grown from the ethanol:water mixture (2:1 v/v) under isochoric conditions in the DAC chamber: (a) spontaneous powder precipitation at 0.64 GPa viewed under polarized light, (b) one seed (indicated by the red arrow) at 365 K, (c) 323 K and (d) 0.64 GPa and 296 K. A large ruby chip for pressure calibration lies close to the centre of the chamber.

Low-temperature SCXRD data were measured on Oxford Diffraction diffractometers Xcalibur and SuperNova equipped with low-temperature Cryosystem attachments. High-pressure SCXRD data were recorded on diffractometers KUMA KM4-CCD and Xcalibur, equipped with EOS-CCD detectors, according to the procedure described previously (Budzianowski & Katrusiak, 2004 ). The CrysAlisPro software (CrysAlisPro Rigaku Oxford Diffraction, 2015 $[Rigaku Oxford Diffraction (2015). CrysAlisPro. Rigaku Corporation, The Woodlands, TX, USA.]$ ) was used for collecting diffraction data and their preliminary reduction. The sample reflections overlapping with diamond reflections were eliminated, and corrections for the DAC and sample absorption and for the beam shadowing by the gasket were applied. Olex2 (Dolomanov et al., 2009 ) was used, the crystal structures were solved by direct methods within SHELXT (Sheldrick, 2015b ) and refined by least-squares using SHELXL (Sheldrick, 2015a ). Anisotropic displacement parameters (ADPs) were applied for non-hydrogen atoms in all low-temperature structures, whereas for the ambient-conditions and high-pressure experiments ISOR constraints were applied for all carbon and oxygen atoms (cf. SHELXL input instructions in the supporting CIFs). The hydrogen atoms were located from the molecular geometry and their isotropic ADP values U_iso were constrained to 1.2U_eq of their carriers. In DL-menthol, the starting model with the hydroxyl proton disordered was assumed. The hydroxyl hydrogen atoms were refined with geometric constraints (OH distance 0.81 Å) and were assigned U_iso = 1.2U_eq of the oxygen atoms. We investigated the disorder of hydroxyl hydrogen atoms (labelled H1) by lowering the symmetry to space group P1 and refining the site occupation factors as free variables for two possible sites for each of the six independent hydrogen atoms. Their site occupation factors (SOFs) were refined as free variables with the constraints SOF(H1i1) + SOF(H1i2) = 1, where i = A, B, C for three independent molecules and the last digits of the labels, 1 and 2, denote the first and second of two sites of the disordered hydroxyl hydrogen atom. In all experiments performed between 296 and 100 K, the SOFs refined to values close to 0.5 and therefore we assumed that all three hydroxyl protons are 50:50 disordered. After removing the hydroxyl protons, in each OH⋯O hydrogen bond two similar electron-density peaks corresponding to the disordered hydrogen sites were found in the difference Fourier maps. Thus, no reasons were found for rejecting the symmetry of space group P1, which implies the 50:50 disorder of hydroxyl hydrogen atoms in the final refinements. Structural drawings were prepared using the program Mercury (version 4.0; Macrae et al., 2020 ).

High-pressure PXRD measurements were performed for the sample compressed in the DAC, according to the procedure described by Skumiel (2010 ). The ethanol:water mixture (1:3 v/v) was used as the solvent and hydrostatic fluid. The Xcalibur diffractometer equipped with an 0.3 mm collimator was used, and the diffraction images were recorded for the sample rotated by ±15° about the ω axis from its 0° position, for the χ axis at 0, 30, 60 and 90° positions. The diamond reflections were eliminated, the background recorded beforehand for the empty DAC was subtracted and the residue intensity was integrated at constant 2θ angles. Before each measurement the sample was almost completely dissolved by heating and then left to crystallize under isochoric conditions up to 2.23 GPa (cf. Fig. S11). The crystallographic information has been deposited in the Cambridge Structural Database (Groom et. al., 2016 ) with deposition nos. 2206626–2206658. Selected crystal data are summarized in Table 1. Experimental and crystallographic details are listed in Tables S1–S2 of the supporting information.

Table 1
Selected crystal data of DL-menthol polymorphs α and β determined at 296 K (cf. Tables S1 and S2)

Formula	α-DL-C₁₀H₂₀O	α-DL-C₁₀H₂₀O	β-DL-C₁₀H₂₀O	β-DL-C₁₀H₂₀O
Pressure (GPa)	0.0001	0.60	0.10	0.56
Crystal system	Triclinic	Triclinic	Monoclinic	Monoclinic
Space group	P1	P1	P2₁/n	P2₁/n
a (Å)	12.035 (7)	11.601 (1)	11.928 (6)	11.728 (1)
b (Å)	12.536 (6)	12.022 (3)	21.334 (2)	21.085 (1)
c (Å)	12.859 (9)	12.596 (2)	12.235 (8)	12.258 (2)
α (°)	117.56 (6)	117.58 (2)	90	90
β (°)	98.61 (5)	99.50 (3)	103.71 (3)	104.60 (5)
γ (°)	103.93 (5)	103.76 (4)	90	90
V (Å³)	1590.6 (18)	1432.9 (1)	3025 (3)	2933 (3)
Z/Z′	6/3	6/3	12/3	12/3
D_x (g cm⁻³)	0.979 (1)	1.086 (1)	1.029 (2)	1.062 (2)

Differential scanning calorimetry (DSC) measurements were performed for the samples sealed in aluminium capsules in N₂ atmospheres on a Setsys 1200 Setaram instrument between 140 and 573 K at a scan speed of 5 K min⁻¹ (cf. Fig. S12).

3. Results and discussion

Under normal conditions (273 K and 1006 hPa), DL-menthol forms triclinic crystals, hereafter referred to as polymorph α (α-DL-menthol, Table 1; Figs. 4, S13 and S14). The crystals of α-DL-menthol are built from ⋯OH⋯OH⋯ bonded chains. In the chains, three independent molecules (Z′ = 3), denoted A, B and C, are arranged in the sequence [ABCCBA]_n. The ABC intervals are of the same chirality, reversed by two non-equivalent inversion centres located between molecules AA and CC. All hydroxyl atoms (H1) are disordered 50:50 across two sites in OH⋯O hydrogen bonds (cf. Experimental) and the DSC (cf. Fig. S12) of the α-DL-menthol crystals revealed no anomalous heat flow down to 140 K. This result is consistent with our low-temperature X-ray diffraction measurements on the α-DL-menthol crystals showing the persistence of the disorder of hydroxyl hydrogen atoms down to 120 K at least, and no new phases, in particular no metastable triclinic DL-menthol postulated at 233 K by Corvis et al. (2012); its occurrence was excluded within the conditions of our experiments. Interestingly, the similar feature of the same number of three independent molecules (Z′ = 3) is also characteristic of the L-menthol enantiomorph, although the structure of helices of OH⋯O bonded L-menthol molecules is different from that of OH⋯O bonded DL-menthol chains.

Figure 4
Structures of (a) α-DL-menthol and (b) β-DL-menthol projected down the OH⋯O bonded chains. The hydrogen atoms have been omitted for clarity. The voids are represented as contact surfaces for the probing radius 0.85 and step 0.1 Å (cf. Fig. S15). The symmetry elements of space groups P1 (a) and P2₁/n (b) are marked in orange.

We found that the α-DL-menthol crystals, obtained and mounted in the DAC under ambient conditions in our laboratory, can be compressed with no signs of anomalies to 2.20 GPa at least (Fig. 5). The smooth compression of the crystal volume and unit-cell parameters are indications that the crystal remains in the same phase, whereas anomalous compression (discontinuities or changed rate of compression) would indicate phase transitions to other phases. Generally, the absence of detectable anomalies cannot be directly connected with the thermodynamic stability of crystalline or liquid phases, because of the possible effects of supercompressing (Katrusiak et al., 2011 ; Paliwoda et al., 2012 ; Anioła & Katrusiak, 2015 $[Rigaku Oxford Diffraction (2015). CrysAlisPro. Rigaku Corporation, The Woodlands, TX, USA.]$ ; Roszak et al., 2016 ; Fedorov et al., 2017 ; Andrzejewski & Katrusiak, 2017 ; Sobczak & Katrusiak, 2017 ; Safari & Katrusiak, 2021 ; Olejniczak et al., 2022b ) or supercooling (Weineerg, 1908 ) the phases.

Figure 5
Pressure (full symbols) and temperature (open squares) dependence of molecular volume (V_m = V/Z) for α-DL-menthol (squares) obtained at atmospheric pressure (green squares); and recrystallized up to 0.40 GPa from methanol:water solution (blue), ethanol:water solution (cyan) as well as from the pure melt (violet); all recrystallizations above 0.40 GPa yielded β-DL-menthol (triangles down), which also persisted after further compression (triangles right) and decompression below 0.40 GPa (triangles left). All estimated standard deviations are smaller than the plotted symbols. The least-squares functions (plotted lines) fitted to the experimental points are V_α(p) = 265.0 (4) − 52 (1)p + 18 (2)p² − 2.5 (6)p³ and V_β(p) = 255 (2) − 21 (6)p − 1(7)p² + 1(2)p³ (Å³).

In another series of experiments, when the single crystals of DL-menthol were recrystallized from the water:ethanol mixture under pressure in the DAC, the same triclinic polymorph α was obtained up to 0.40 GPa. Above 0.40 GPa, a new monoclinic form, hereafter denoted β-DL-menthol, was crystallized (Table 1). This new polymorph β-DL-menthol could not be obtained by compressing the ambient-pressure polymorph α up to 3.37 GPa. Such high-pressure polymorphs, accessible via in situ recrystallization under pressure, were found for imidazole (Paliwoda et al., 2012), 4,4′-bipiridium hydrobromide monohydrate (Anioła & Katrusiak, 2015 ), 3-hydroxy-4,5-dimethyl-1-phenylpyridazin-6-one (Roszak et al., 2016), di-p-tolyl disulfide (Sobczak & Katrusiak, 2017), resorcinol (Safari & Katrusiak, 2021) and other compounds (Fedorov et al., 2017; Andrzejewski & Katrusiak, 2017; Olejniczak et al., 2022b). However, the molecular volume of those polymorphs accessible through recrystallization is smaller compared with the compressed ambient-pressure polymorph. Our experiments show that the volume of β-DL-menthol is larger compared with α-DL-menthol and this difference increases with increasing pressure (Fig. 5). This was a surprising result because, in general, one expects the high-pressure polymorphs to be more dense compared with the low-pressure polymorphs, when both polymorphs are compared under the same pressure conditions. Moreover, the close similarity between the structures of α-DL-menthol and β-DL-menthol could imply their similar compressibility. Fig. 4 shows that both these structures are built of similar chains of OH⋯O bonded molecules. These chains are nearly identical in shape (Figs. 6, S13 and S14): each contains three independent molecules in sequence A′ABCC′′, with the inversion centres between the A′A molecules and between the CC′′ molecules (in polymorph β, the prime indicates the molecule transformed through symmetry code x, y, 1 − z and bis denotes 1 − x, y, 1 − x; in polymorph α, the prime denotes the symmetry code 1 − x, 2 − y, z and bis denotes 2 − x, 2 − y, z).

Figure 6
Projections of neighbouring OH⋯OH bonded chains along the direction perpendicular to their axes in (a) α-DL-menthol and (b) β-DL-menthol. Chain intervals ABC of L-(−)(1R,2S,5R)-menthol molecules are highlighted in blue and of D-(+)(1S,2R,5S)-menthol molecules are highlighted in yellow. The dashed ovals indicate analogous regions of the shortest contacts between chains. Hydrogen atoms have been omitted for clarity.

It appears that when viewing the structure along the chains (i.e. along a in polymorphs α and β), the arrangements of chains are nearly identical (Figs. 4 and 6) and their shortest contacts to neighbouring chains are also very similar. However, the chains are shifted differently along their axes with respect to the six close chains: in polymorph α translated along ±b_α, ±[011]_α, ±c_α; and in polymorph β translated along ±c_β, or transformed by glide plane n and screw axis 2₁, to the positions along ±[011]_β and ±[011]_β, as illustrated in Figs. 4, S7 and S8.

Furthermore, a striking similarity connects the lattices of both polymorphs: the lattice vectors of β-DL-menthol can be transformed to approximate those of α-DL-menthol through the matrix equation

$[\left(\matrix{{{a}}_{\beta }\cr {{b}}_{\beta }\cr {{c}}_{\beta }}\right) = \left(\matrix{ -1& 0& 0\cr 0& -1& -2\cr 0& -1& 0}\right)\left(\matrix{{{a}}_{\alpha }\cr {{b}}_{\alpha }\cr {{c}}_{\alpha }}\right), \eqno (1)]$

where subscript β refers to the monoclinic β-DL-menthol and subscript α denotes the triclinic α-DL-menthol. The reverse matrix transforms the lattice of polymorph β into that of polymorph α

$[\left(\matrix{{{a}}_{\alpha }\cr {{b}}_{\alpha }\cr {{c}}_{\alpha }}\right) = \left(\matrix{-1& 0& 0\cr 0& 0& -1\cr 0& -0.5& 0.5}\right)\left(\matrix{{{a}}_{\beta }\cr {{b}}_{\beta }\cr {{c}}_{\beta }}\right). \eqno (2)]$

According to Equation (1), the triclinic unit cell of α-DL-menthol at 0.1 MPa can be represented as the following pseudo-monoclinic unit cell: a^m = 12.035 Å, b^m = 22.809 Å, c^m = 12.536 Å, α^m = 88.40°, β^m = 103.93° and γ^m = 107.52° [superscript m indicates the unit-cell dimensions of polymorph α transformed according to equation (1) to the monoclinic setting of polymorph β]. The unit-cell parameters of α-DL-menthol at 0.60 GPa transformed in this way to give a^m = 11.581 Å, b^m = 22.336 Å, c^m = 12.222 Å, α^m = 88.57°, β^m = 103.76° and γ^m = 108.44°. Both these sets of pseudo-monoclinic unit cells are similar to the unit cell of β-DL-menthol (Table 1), except that angle γ significantly diverges from 90°. This departure from 90° increases with pressure, by over 1.0° GPa⁻¹, which shows that the compressed lattices of polymorphs α and β become increasingly different (Fig. S9). Equations (1) and (2) can be used for convenient comparions of the dimensions and compressions of the structures of polymorphs α and β in their corresponding directions. Fig. 7 shows that the parameters a^t and b^t of the triclinic lattice are similar in polymorphs α and β, whereas the c^t parameters differ by about 0.6 Å. These smaller differences occur along the OH⋯O bonded chains (parameter a^t) and in this direction between the chains where they are related by inversion centres (parameter b^t), whereas the largest difference along c^t is between the chains related by different symmetry elements: the inversion centres in polymorph α, and the glide planes n or screw axes 2₁ in polymorph β (Fig. 4). The strongest difference in compression occurs up to about 0.5 GPa, when polymorph α, owing to the presence of voids supported by directional OH⋯O bonds (Fig. S15), is much softer than polymorph β. Above 1.0 GPa the compressions along a^t and b^t become similar, but the compression along c^t continues to be considerably lower for polymorph β (Fig. 7). The crystal-strain analyses for compressed polymorphs α and β are presented in Tables S3, S4 and Fig. S10.

Figure 7
(a) Pressure and (b) temperature dependence of unit-cell parameters a, b, c in α-DL-menthol (squares and α subscripts) and β-DL-menthol (diamonds and β subscripts; cf. Fig. S7). For convenient comparisons of analogous lattice directions, the unit-cell parameters of the monoclinic β-DL-menthol (superscript m in the legend) are transformed to the triclinic lattice [superscript t, cf. equation (2)

]. The pressure dependence of the unit-cell parameters for the lattices in the settings of polymorphs α and β are plotted in Figs. S7–S9.

The α-DL-menthol polymorph is highly compressible, considerably more so than most crystals of organic compounds, and at 1.00 GPa its volume is reduced by about 13.2%. It is connected with an exceptionally low density of α-DL-menthol (Table 1), due to the presence of many small voids constituting nearly 25% of the structure at 0.10 MPa, according to the probing-sphere calculations (with a probing-sphere radius of 0.60 Å and a step of 0.10 Å, cf. Fig. S14). The compressibility of α-DL-menthol is strongly non-linear (Figs. 5 and S17), which is characteristic of molecular crystals with large volumes of voids. The compressibility of α-DL-menthol at 0.10 MPa is β_α(0.1 MPa) = 0.198 GPa⁻¹, compared with the nearly five times smaller compressibility at 2.00 GPa, β_α(2.0 GPa) = 0.0415 GPa⁻¹. The compressibility of β-DL-menthol at 0.10 MPa is estimated to be β_β(0.1 MPa) = 0.084 GPa⁻¹ compared with the more than four times smaller compressibility at 2.00 GPa, β_β (2.0 GPa) = 0.018 GPa⁻¹.

The very high compressibility of polymorph α-DL-menthol at 0.10 MPa (Fig. 5) is two and half times larger than that of β-DL-menthol (see the compressibility values above); at 0.40 GPa the compressibility of polymorph α is still double that of polymorph β: 0.149 compared with 0.077 GPa⁻¹, respectively. The smaller compressibility of polymorph β compared with that of polymorph α (Fig. 5) can be connected to initially significantly smaller intermolecular voids in polymorph β (Fig. S15). Consequently, starting from about 0.30 GPa, the molecular volume of the low-pressure polymorph α becomes smaller than that of the high-pressure polymorph β. We have double checked this counterintuitive result by performing the recrystallizations as a function of pressure in the DAC from different solvents, dry methanol, ethanol and finally from the molten pure DL-menthol. All these experiments confirmed that, up to 0.30 GPa, the density of polymorph α is lower than that of polymorph β and above 0.30 GPa the density of polymorph β becomes lower than that of polymorph α. Due to the molecular volume differences, the Gibbs free energy difference between the stable and unstable polymorphs is reduced by the energy value $[p\Delta V = p(V_{\rm m}^{\rm stable} - V_{\rm m}^{\rm unstable})]$ , which acts against the stability of the polymorphs obtained by recrystallization: for polymorph α up to 0.30 GPa, this work contribution $[p(V_{\rm m}^\alpha - V_{\rm m}^\beta)]$ is positive; and above 0.40 GPa in the stability region of polymorph β, the product $[p({V}_{\rm m}^{\beta }-{ V}_{\rm m}^{\alpha })]$ is also positive (cf. Figs. 5 and 8). Moreover, the recrystallizations of the pure molten DL-menthol yielded polymorph α below 0.40 GPa and polymorph β above 0.40 GPa. Because no other compounds except DL-menthol were present in the DAC chamber, this series of experiments showed that no solvent effects, such as stochastic sorption, take place (Roszak & Katrusiak, 2021; Olejniczak et al., 2022a).

Figure 8
(a) Molecular volume difference ΔV between DL-menthol polymorphs α and β and the work contribution pΔV to the Gibbs free energy G; (b) plots of Gibbs free-energy functions G_Liquid, G_α and G_β as a function of pressure, the dotted lines indicate the experimentally observed melting pressure of polymorph β at 0.1 GPa and 296 K, and the point of changed preference for the crystallization between polymorphs α and β at 0.4 GPa. Note the volume difference ΔV = 0 (and hence ΔVp = 0) at p = 0.30 GPa in (a) occurs at a lower pressure than ΔG = 0 at p = 0.40 GPa in (b).

The larger volume and hence lower density of the high-pressure polymorph is difficult to reconcile with the typical behaviour of one-component compounds, which undergo a pressure-induced phase transition. However, no phase transition has been observed in any of our high-pressure experiments on DL-menthol, even when the samples were kept at high pressure for several months. The polymorphs α and β were obtained solely by recrystallizations. Thus, their molecular volumes can be regarded as independent parameters, like the Gibbs free energy functions G_α and G_β of the polymorphs, and

$[\Delta G = U_{\alpha} - U_{\beta} + \left( V_{\alpha} - V_{\beta}\right )p - \left ( S_{\alpha} - S_{\beta}\right )T,\eqno (3)]$

where the internal energy U and entropy S of polymorphs, α and β, depend on pressure p and temperature T. The high-pressure recrystallizations and SCXRD studies on DL-menthol show that the zero value of ΔG = 0 occurs at 0.40 GPa, close to the pressure when ΔV = 0 (Fig. 8). If we assume the same pressure for ΔG = 0 and ΔV = 0, equation (3) simplifies to

$[\Delta U = \Delta ST, \eqno (4)]$

where ΔU = U_α − U_β and ΔS = S_α − S_β. Fig. 8 shows that, between 0.10 MPa and 0.40 GPa, the work contribution considered for transforming the metastable β polymorph to the stable α polymorph pΔV = p(V_α − V_β) is positive, and thus it acts against such a transition. However, the p(V_α − V_β) value is smaller than 0.5 kJ mol⁻¹, which can be overcome by the differences in the internal energy (ΔU) and entropy (ΔST) contributions, usually much higher for isomers and polymorphs of molecular hydrogen-bonded crystals (Madsen & Larsen, 2007 ; Kofoed et al., 2019 ). Above 0.40 GPa, when the β polymorph becomes stable, the work contribution pΔV = p(V_β − V_α) considered for transforming the metastable α polymorph to the stable β polymorph is positive again and hence it acts against the transition again. Despite this larger positive work contribution (Fig. 8), the β polymorph nonetheless becomes more stable than the α polymorph due to the ΔU and ΔST contributions. The comparison of the compressed structures of polymorphs α and β reveals systematic significant structural differences connected to the internal energy. The compression of all parameters is initially much stronger for polymorph α. The compression of parameters a_α and a_β along the OH⋯O bonded chains correlates with the compression of the hydrogen bonds (Figs. 6 and 9). It is plausible that the stronger compression of the OH⋯O bonds in polymorph α significantly increases the internal energy and reduces the entropy connected with the atomic displacement parameters, which counteract the work contribution and destabilize the α-DL-menthol structure above 0.40 GPa. The stronger compression of OH⋯O bonds in polymorph α contrasts with the stronger compression of van der Waals contacts H⋯H in polymorph β, plotted in Figs. S17 and S18.

Figure 9
Pressure dependence of H⋯O and O⋯O distances in four independent hydrogen bonds (see legend) in DL-menthol polymorphs α (full squares, full lines) and β (open diamonds, dashed lines). The temperature dependence of these dimensions as well as the pressure-induced changes in OH⋯O angles are plotted in Figs. S19 and S23.

The significantly larger voids in α-DL-menthol up to about 0.50 GPa are consistent with the lower density of this polymorph up to about 0.40 GPa (Fig. S15). The similar volumes of voids in α- and β-DL-menthol above 0.50 GPa can be regarded as an indication that the lengths of chains (a_β > a_α) contribute most to the lower density of β-DL-menthol above 0.40 GPa (Figs. 7, S9 and S15).

In the structure of polymorph α three of four independent OH⋯O hydrogen bonds are monotonically compressed, whereas one hydrogen bond initially increases in length, which is clearly seen for the O1B⋯O1C distance, and above about 1.0 GPa it is compressed at a slower rate compared with other hydrogen bonds (Fig. 9). The OH⋯O angle undergoes a large change, from 148 to 175° in the pressure range from 0.10 MPa to 0.10 GPa (Fig. S19). Above about 0.50 GPa, all the OH⋯O angles decrease with pressure and the smallest of the angles becomes close to 130° at about 1.50 GPa. It is also characteristic that on average all OH⋯O hydrogen bonds in polymorph α are ca 0.10 Å shorter than the corresponding four independent hydrogen bonds in polymorph β and this average difference in length does not change significantly with pressure. It was postulated that the bulky molecules cannot get close enough to form short hydrogen bonds OH⋯O owing to steric hindrances interfering with the symmetry of glide planes and 2₁ screw axis (Brock & Duncan, 1994 ), which is in agreement with the structures of DL-menthol polymorphs. The longer OH⋯O bonds in β-DL-menthol correspond with the longer chains in this polymorph and with the unit-cell dimension a_β > a_α. The compression of crystals is also reflected in conformational changes of molecules, up to about 20° in torsion angles, changing their values between the polymorphs and as a function of pressure (Figs. S20–S22).

In general, experimental evidence shows there are numerous compounds that, under ambient conditions, form stable polymorphs less dense than the more dense unstable polymorphs, which are either concomitant or can be obtained under high pressure (e.g. Boldyreva et al., 2002 ; Krawczyk & Gdaniec, 2005 ; Nelyubina et al., 2010 ; Adhikari et al., 2015 ; Zieliński & Katrusiak, 2013 ; Safari & Katrusiak, 2021). However, in all these cases, the high-density metastable polymorph continues to be more dense in its high-pressure stability region. To our knowledge, the DL-menthol polymorphs α and β document for the first time the existence of a compound, for which the high-pressure polymorph (β), obtained under isothermal conditions, becomes less dense than the low-pressure polymorph (α). These polymorphs can coexist and below 0.40 GPa the less dense polymorph α is stable, whereas at pressures above 0.40 GPa polymorph α becomes more dense and less stable than polymorph β, despite the fact that no chemical, compositional or even a significant conformational change (Fig. S24) take places. This effect of high-pressure favouring the less dense polymorph of DL-menthol is similarly as counterintuitive as the effect of increased chemical composition reducing the molecular volume. It is expected that new components added to a structure will increase its volume; however, there are rare observations that the molecular volumes of anhydrates are smaller than those of their hydrates (Zieliński & Katrusiak, 2015 ; Andrzejewski et al., 2017 ).

In order to confirm that polymorph β is stable at the same temperature as polymorph α, at 296 K, we performed isothermal crystallizations from DL-menthol dissolved in isopropanol, and nucleation occurred above 0.40 GPa. These isothermal in situ recrystallizations yielded the β polymorph, identified by PXRD, as exemplified in Fig. S25.

We also considered the possibility that polymorph β-DL-menthol is metastable in a wide range of pressures, even above 0.40 GPa. The formation of the metastable β polymorph would be consistent with Ostwald's rule of stages. In such a case, the metastable phase would have a lower melting point than the stable phase, not only below 0.40 GPa, but also above this pressure. Hence, in another series of experiments we gradually compressed the pure DL-menthol sample in the DAC and for each pressure point we recorded the temperature of the beginning and of the full melting of the sample (Fig. 10), determined by microscopic observations. The temperature required for melting the sample in the DAC chamber drastically increases above 0.40 GPa. This increase in temperature of about 80 K above 0.40 GPa, coinciding with the formation of polymorph β, indicates that it becomes more stable than polymorph α, which implies that polymorph β is not metastable above 0.40 GPa.

Figure 10
(a) Melting temperature of pure α-DL-menthol and β-DL-menthol compressed and recrystallized in the DAC chamber: the black squares mark the onset of melting of the crystal filling the volume of the chamber, and the red squares mark the melting completion, according to the microscopic observation of the sample, as exemplified for the heating run of the sample at the starting pressure 0.48 GPa in (b). The increased temperature for the full melting (red squares) compared with that at the start (black squares) results from the pressure–temperature interdependence for the isochoric process: the larger portion of the sample is molten, the higher pressure is in the DAC chamber. Due to the thermal expansion of the sample, the pressure measurements at 296 K plotted in (a) are lower than the actual values for which the melting onset, and even more so the melting completion, took place. In the DAC chamber several small irregular ruby chips are placed close to the gasket walls for the ruby-fluorescence pressure measurements.

4. Conclusions

According to the close-packing rule for molecular crystals (Kitaigorodsky, 1973), their dense structures should be favoured under specific thermodynamic conditions. We have shown that this is not the case for DL-menthol polymorphs α and β when nucleated and crystallized in their low- and high-pressure stability regions, respectively. As expected, up to 0.40 GPa, the triclinic DL-menthol polymorph α, stable at atmospheric pressure, is less dense than the high-pressure β polymorph revealed here. But the exceptional observation is that the high-pressure polymorph β-DL-menthol is less dense in its stability region above 0.40 GPa than the super-compressed ambient-pressure polymorph α. We have rationalized this counterintuitive pressure–density relation between the DL-menthol polymorphs by the shorter OH⋯O bonds enforcing larger voids in polymorph α compared with the considerably longer OH⋯O bonds allowing a more compact structure of polymorph β. Like in the structure of H₂O ice I_h, in DL-menthol polymorph α the OH⋯O bonds dominate the cohesion forces, achieved at the cost of close-packing of the molecules. This loose packing in DL-menthol polymorph α results in its high compressibility, which in turn leads above 0.30 GPa to its higher-density compared with the less-compressible polymorph β. Therefore, the densities of DL-menthol polymorphs α and β in their stability regions below and above 0.40 GPa, respectively, are lower compared with the densities of their metastable counterparts. These density relations are essential for the thermodynamic properties of the α and β polymorphs, because the work contribution pΔV to the Gibbs free energy favours the unstable polymorph. It reduces the energy difference between the Gibbs free energies of the polymorphs, |G_α − G_β|_T, while the kinetic barrier for the transition between the polymorphs, requiring considerable structural rearrangements, remains high. Consequently, the kinetics of the possible transitions between the polymorphs are very slow. Indeed, we observed no solid-state phase transitions from polymorph α to polymorph β when the pressure was increased to above 0.40 GPa, and from polymorph β to polymorph α when pressure was released to below 0.40 GPa. For obtaining the other polymorph under high pressure, the DL-menthol sample had to be either molten or dissolved. The α- and β-DL-menthol polymorphs exemplify an extremely rare system, for which the high-pressure polymorph is less dense compared with the metastable (super-compressed) one. Such a phenomenon, although counterintuitive and unprecedented in the literature, is not forbidden by any thermodynamic law, and therefore it widens our understanding of the general properties of molecular crystals. DL-Menthol exemplifies a chemical compound, which even under high pressure is not stable in its most dense polymorphs. This observation can be used for the interpretation of theoretically predicted models of crystal structures, where the density and internal energy criteria are generally applied (Bhardwaj et al., 2019 ; Tchoń et al., 2021 ; Price & Price, 2022 ).

5. Related literature

The following references are cited in the supporting information: Cliffe & Goodwin (2012 ); Langreiter & Kahlenberg (2015 ).

Supporting information

Crystal structure: contains datablocks alpha_DL_0.01MPa, alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.51GPa, alpha_DL_0.60GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_120K, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.10GPa, beta_DL_0.20GPa, beta_DL_0.45GPa, beta_DL_0.56GPa, beta_DL_0.57GPa, beta_DL_0.64GPa, beta_DL_0.67GPa, beta_DL_0.70GPa, beta_DL_0.90GPa, beta_DL_1.28GPa, beta_DL_1.34GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.39GPa, beta_DL_2.90GPa. DOI: https://doi.org/10.1107/S2052252523002452/fc5065sup1.cif

Supporting figures and tables. DOI: https://doi.org/10.1107/S2052252523002452/fc5065sup2.pdf

Computing details top

Data collection: CrysAlis (Oxford Diffraction, 2015) for alpha_DL_0.01MPa, alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.51GPa, alpha_DL_0.60GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_120K, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.70GPa, beta_DL_1.28GPa, beta_DL_2.39GPa; CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019) for beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.56GPa, beta_DL_0.57GPa, beta_DL_0.67GPa, beta_DL_0.90GPa, beta_DL_1.34GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.90GPa; CrysAlis PRO 1.171.41.93a (Rigaku OD, 2020) for beta_DL_0.20GPa; CrysAlis PRO, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) for beta_DL_0.64GPa. Cell refinement: CrysAlis (Oxford Diffraction, 2015) for alpha_DL_0.01MPa, alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.51GPa, alpha_DL_0.60GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_120K, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.70GPa, beta_DL_1.28GPa, beta_DL_2.39GPa; CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019) for beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.56GPa, beta_DL_0.57GPa, beta_DL_0.67GPa, beta_DL_0.90GPa, beta_DL_1.34GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.90GPa; CrysAlis PRO 1.171.41.93a (Rigaku OD, 2020) for beta_DL_0.20GPa; CrysAlis PRO, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) for beta_DL_0.64GPa. Data reduction: CrysAlis (Oxford Diffraction, 2015) for alpha_DL_0.01MPa, alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.51GPa, alpha_DL_0.60GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_120K, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.70GPa, beta_DL_1.28GPa, beta_DL_2.39GPa; CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019) for beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.56GPa, beta_DL_0.57GPa, beta_DL_0.67GPa, beta_DL_0.90GPa, beta_DL_1.34GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.90GPa; CrysAlis PRO 1.171.41.93a (Rigaku OD, 2020) for beta_DL_0.20GPa; CrysAlis PRO, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) for beta_DL_0.64GPa. Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for alpha_DL_0.01MPa, alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.51GPa, alpha_DL_0.60GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_120K, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.56GPa, beta_DL_0.57GPa, beta_DL_0.64GPa, beta_DL_0.67GPa, beta_DL_0.70GPa, beta_DL_0.90GPa, beta_DL_1.28GPa, beta_DL_1.34GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.39GPa, beta_DL_2.90GPa; SHELXT 2018/2 (Sheldrick, 2018) for beta_DL_0.20GPa. Program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015) for alpha_DL_0.01MPa, alpha_DL_0.51GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.20GPa, beta_DL_0.56GPa, beta_DL_0.64GPa, beta_DL_0.67GPa, beta_DL_0.70GPa, beta_DL_1.28GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.39GPa, beta_DL_2.90GPa; SHELXL 2017/1 (Sheldrick, 2015) for alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.60GPa, alpha_DL_120K, beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.57GPa, beta_DL_0.90GPa, beta_DL_1.34GPa. Molecular graphics: Olex2 1.3 (Dolomanov et al., 2009) for alpha_DL_0.01MPa, alpha_DL_0.51GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.20GPa, beta_DL_0.56GPa, beta_DL_0.64GPa, beta_DL_0.67GPa, beta_DL_0.70GPa, beta_DL_1.28GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.39GPa, beta_DL_2.90GPa; Mercury (2020) for alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.60GPa, alpha_DL_120K, beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.57GPa, beta_DL_0.90GPa, beta_DL_1.34GPa. Software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009) for alpha_DL_0.01MPa, alpha_DL_0.51GPa, alpha_DL_0.65GPa, alpha_DL_0.84GPa, alpha_DL_1.12GPa, alpha_DL_1.44GPa, alpha_DL_1.70GPa, alpha_DL_2.10GPa, alpha_DL_3.37GPa, alpha_DL_160K, alpha_DL_190K, alpha_DL_220K, alpha_DL_260K, beta_DL_0.20GPa, beta_DL_0.56GPa, beta_DL_0.64GPa, beta_DL_0.67GPa, beta_DL_0.70GPa, beta_DL_1.28GPa, beta_DL_1.67GPa, beta_DL_2.10GPa, beta_DL_2.39GPa, beta_DL_2.90GPa; SHELXL (Sheldrick, 2015) for alpha_DL_0.10GPa, alpha_DL_0.15GPa, alpha_DL_0.30GPa, alpha_DL_0.60GPa, alpha_DL_120K, beta_DL_0.10GPa, beta_DL_0.45GPa, beta_DL_0.57GPa, beta_DL_0.90GPa, beta_DL_1.34GPa.

beta-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.01MPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 0.979 Mg m⁻³
a = 12.035 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.536 (6) Å	Cell parameters from 5556 reflections
c = 12.859 (9) Å	θ = 1.8–25.0°
α = 117.56 (6)°	µ = 0.06 mm⁻¹
β = 98.61 (5)°	T = 296 K
γ = 103.93 (5)°	Plate, colourless
V = 1590.6 (18) Å³	0.23 × 0.2 × 0.08 mm

Data collection top

Xcalibur, Eos diffractometer	2997 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.032
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→13
T_min = 0.986, T_max = 0.995	k = −14→14
11264 measured reflections	l = −11→15
5556 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.059	w = 1/[σ²(F_o²) + (0.0902P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.185	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.24 e Å⁻³
5556 reflections	Δρ_min = −0.15 e Å⁻³
314 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.011 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.54705 (16)	1.07513 (13)	0.12521 (13)	0.0724 (5)
H1B	0.613457	1.069264	0.125246	0.109*	0.5
H1A	0.529 (6)	1.037 (5)	0.0499 (4)	0.109*	0.5
C1	0.5581 (2)	1.20849 (18)	0.17859 (18)	0.0629 (6)
H1	0.480130	1.212303	0.148775	0.094*
C2	0.5927 (2)	1.27390 (19)	0.31903 (18)	0.0629 (6)
H2	0.670784	1.268513	0.345713	0.094*
C3	0.6123 (2)	1.41774 (19)	0.3767 (2)	0.0725 (7)
H3A	0.536947	1.427415	0.351892	0.109*
H3B	0.637542	1.459362	0.465686	0.109*
C4	0.7065 (2)	1.4834 (2)	0.3379 (2)	0.0846 (8)
H4A	0.783259	1.478919	0.367531	0.127*
H4B	0.715434	1.573424	0.374967	0.127*
C5	0.6719 (3)	1.4203 (2)	0.1986 (2)	0.0817 (7)
H5	0.596460	1.429775	0.170649	0.123*
C6	0.6506 (2)	1.2763 (2)	0.1397 (2)	0.0709 (6)
H6A	0.623795	1.235570	0.050803	0.106*
H6B	0.726075	1.265692	0.162138	0.106*
C7	0.5050 (2)	1.2047 (2)	0.3628 (2)	0.0738 (7)
H7	0.488316	1.112344	0.310167	0.111*
C8	0.3840 (2)	1.2242 (3)	0.3504 (3)	0.0908 (8)
H8A	0.348813	1.200367	0.267199	0.109*
H8B	0.331353	1.171572	0.371206	0.109*
H8C	0.396105	1.313000	0.405164	0.109*
C9	0.5630 (3)	1.2423 (3)	0.4952 (2)	0.1112 (10)
H9A	0.638704	1.229549	0.501562	0.133*
H9B	0.575690	1.331099	0.550407	0.133*
H9C	0.510938	1.189671	0.516449	0.133*
C10	0.7677 (3)	1.4844 (3)	0.1588 (3)	0.1132 (11)
H10A	0.743164	1.442524	0.070668	0.136*
H10B	0.777198	1.573609	0.194238	0.136*
H10C	0.842666	1.477343	0.186560	0.136*
O1B	0.74691 (18)	1.0091 (2)	0.12545 (17)	0.0948 (6)
H1BA	0.8040 (19)	1.032 (4)	0.104 (2)	0.142*	0.5
H1BB	0.6986 (15)	1.046 (2)	0.1393 (17)	0.142*	0.5
C1B	0.7622 (2)	0.9521 (2)	0.1986 (2)	0.0736 (7)
H1BC	0.821848	0.911032	0.177806	0.110*
C2B	0.8068 (2)	1.0503 (2)	0.3366 (2)	0.0764 (7)
H2B	0.742683	1.084666	0.355936	0.115*
C3B	0.8185 (3)	0.9797 (3)	0.4064 (2)	0.0974 (9)
H3BA	0.879612	0.941646	0.388092	0.146*
H3BB	0.843608	1.040894	0.494257	0.146*
C4B	0.6992 (3)	0.8744 (3)	0.3700 (3)	0.1091 (10)
H4BA	0.710398	0.829343	0.412754	0.164*
H4BB	0.640646	0.913946	0.396324	0.164*
C5B	0.6503 (3)	0.7779 (3)	0.2325 (3)	0.0948 (9)
H5B	0.707742	0.734189	0.209502	0.142*
C6B	0.6433 (2)	0.8480 (2)	0.1624 (2)	0.0773 (7)
H6BA	0.619359	0.786110	0.074808	0.116*
H6BB	0.582225	0.886521	0.178527	0.116*
C7B	0.9203 (3)	1.1670 (3)	0.3777 (2)	0.0901 (8)
H7B	0.904163	1.198489	0.322136	0.135*
C8B	1.0346 (3)	1.1365 (3)	0.3661 (3)	0.1062 (10)
H8BA	1.019828	1.066554	0.284361	0.127*
H8BB	1.097366	1.210990	0.382021	0.127*
H8BC	1.058586	1.112792	0.424635	0.127*
C9B	0.9415 (3)	1.2776 (3)	0.5065 (3)	0.1518 (17)
H9BA	0.868779	1.295647	0.512381	0.182*
H9BB	0.965109	1.254376	0.565529	0.182*
H9BC	1.003889	1.352573	0.522915	0.182*
C10B	0.5294 (3)	0.6751 (3)	0.1955 (3)	0.1217 (12)
H10D	0.502716	0.616858	0.107972	0.146*
H10E	0.537864	0.628398	0.236145	0.146*
H10F	0.471521	0.715256	0.219132	0.146*
O1C	0.93830 (17)	1.08108 (16)	0.05539 (16)	0.0832 (5)
H1CA	0.8729 (18)	1.039 (2)	0.0530 (19)	0.125*	0.5
H1C	0.9743 (14)	1.0346 (14)	0.011 (6)	0.125*	0.5
C2C	1.0513 (2)	1.2516 (2)	0.0302 (2)	0.0657 (6)
H2C	1.079851	1.189773	−0.029142	0.099*
C6C	0.8352 (2)	1.1096 (2)	−0.1043 (2)	0.0692 (6)
H6CA	0.857169	1.042721	−0.164607	0.104*
H6CB	0.757523	1.069096	−0.100702	0.104*
C4C	0.9480 (3)	1.2761 (2)	−0.1421 (2)	0.0868 (8)
H4CA	0.941889	1.339254	−0.164127	0.130*
H4CB	0.976207	1.216110	−0.202077	0.130*
C1C	0.9287 (2)	1.1751 (2)	0.02237 (19)	0.0649 (6)
H1CB	0.899949	1.235151	0.083171	0.097*
C5C	0.8248 (2)	1.2041 (2)	−0.1463 (2)	0.0787 (7)
H5C	0.797558	1.267339	−0.086880	0.118*
C3C	1.0395 (2)	1.3446 (2)	−0.0133 (2)	0.0784 (7)
H3CA	1.117328	1.387284	−0.015059	0.118*
H3CB	1.014718	1.410023	0.045199	0.118*
C7C	1.1461 (2)	1.3172 (2)	0.1589 (2)	0.0808 (7)
H7C	1.146845	1.249462	0.176893	0.121*
C8C	1.1159 (3)	1.4181 (3)	0.2638 (2)	0.1093 (10)
H8CA	1.036251	1.380582	0.263675	0.131*
H8CB	1.172461	1.447711	0.340997	0.131*
H8CC	1.119990	1.489410	0.252613	0.131*
C9C	1.2725 (3)	1.3755 (3)	0.1579 (3)	0.1181 (11)
H9CA	1.290584	1.311520	0.091851	0.142*
H9CB	1.276969	1.446677	0.146464	0.142*
H9CC	1.329439	1.404979	0.234848	0.142*
C10C	0.7310 (3)	1.1368 (3)	−0.2738 (2)	0.1054 (10)
H10G	0.654837	1.092677	−0.271785	0.126*
H10H	0.723155	1.199793	−0.294120	0.126*
H10I	0.756497	1.075917	−0.334666	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0920 (13)	0.0517 (8)	0.0640 (9)	0.0241 (8)	0.0255 (9)	0.0229 (7)
C1	0.0691 (15)	0.0536 (11)	0.0611 (12)	0.0240 (10)	0.0200 (10)	0.0251 (10)
C2	0.0600 (15)	0.0600 (12)	0.0573 (11)	0.0194 (10)	0.0155 (10)	0.0233 (10)
C3	0.0718 (16)	0.0586 (12)	0.0656 (13)	0.0206 (11)	0.0203 (11)	0.0174 (10)
C4	0.0824 (19)	0.0564 (12)	0.0991 (18)	0.0212 (12)	0.0274 (14)	0.0301 (12)
C5	0.094 (2)	0.0690 (14)	0.1047 (18)	0.0391 (14)	0.0478 (15)	0.0522 (13)
C6	0.0824 (18)	0.0653 (12)	0.0744 (14)	0.0332 (12)	0.0350 (12)	0.0369 (11)
C7	0.0735 (17)	0.0755 (14)	0.0666 (13)	0.0237 (12)	0.0270 (12)	0.0321 (11)
C8	0.075 (2)	0.0858 (17)	0.1011 (19)	0.0228 (14)	0.0352 (15)	0.0409 (15)
C9	0.109 (3)	0.153 (3)	0.0824 (18)	0.043 (2)	0.0410 (17)	0.0681 (18)
C10	0.134 (3)	0.0840 (17)	0.166 (3)	0.0515 (19)	0.086 (2)	0.081 (2)
O1B	0.0926 (15)	0.1312 (15)	0.1087 (13)	0.0436 (12)	0.0389 (11)	0.0945 (12)
C1B	0.0872 (19)	0.0928 (16)	0.0756 (14)	0.0467 (14)	0.0393 (13)	0.0587 (13)
C2B	0.0767 (18)	0.0870 (16)	0.0781 (15)	0.0351 (14)	0.0371 (13)	0.0457 (13)
C3B	0.101 (2)	0.136 (2)	0.0836 (17)	0.0451 (19)	0.0370 (15)	0.0745 (17)
C4B	0.122 (3)	0.138 (2)	0.112 (2)	0.044 (2)	0.0507 (19)	0.096 (2)
C5B	0.110 (2)	0.0886 (17)	0.124 (2)	0.0509 (17)	0.0573 (19)	0.0707 (17)
C6B	0.089 (2)	0.0765 (14)	0.0779 (15)	0.0334 (14)	0.0367 (13)	0.0437 (12)
C7B	0.0746 (19)	0.0965 (18)	0.0943 (18)	0.0282 (15)	0.0311 (14)	0.0453 (15)
C8B	0.081 (2)	0.148 (3)	0.111 (2)	0.049 (2)	0.0425 (17)	0.076 (2)
C9B	0.088 (3)	0.130 (3)	0.135 (3)	0.008 (2)	0.037 (2)	0.006 (2)
C10B	0.141 (3)	0.0879 (19)	0.163 (3)	0.043 (2)	0.071 (3)	0.078 (2)
O1C	0.0937 (14)	0.0838 (11)	0.1022 (13)	0.0320 (10)	0.0361 (10)	0.0689 (10)
C2C	0.0727 (16)	0.0640 (12)	0.0720 (13)	0.0261 (11)	0.0311 (12)	0.0406 (11)
C6C	0.0802 (17)	0.0648 (12)	0.0678 (13)	0.0255 (12)	0.0275 (12)	0.0370 (11)
C4C	0.110 (2)	0.0817 (15)	0.0821 (16)	0.0267 (15)	0.0319 (15)	0.0557 (14)
C1C	0.0774 (17)	0.0646 (12)	0.0680 (13)	0.0301 (12)	0.0304 (11)	0.0414 (11)
C5C	0.089 (2)	0.0791 (15)	0.0741 (14)	0.0311 (14)	0.0241 (13)	0.0443 (12)
C3C	0.091 (2)	0.0646 (13)	0.0806 (15)	0.0171 (12)	0.0264 (13)	0.0432 (12)
C7C	0.0762 (19)	0.0799 (15)	0.0824 (16)	0.0232 (13)	0.0189 (13)	0.0427 (13)
C8C	0.103 (2)	0.118 (2)	0.0751 (17)	0.0365 (19)	0.0141 (15)	0.0318 (16)
C9C	0.082 (2)	0.134 (3)	0.131 (3)	0.0259 (19)	0.0279 (19)	0.071 (2)
C10C	0.119 (3)	0.110 (2)	0.0863 (18)	0.0379 (19)	0.0148 (17)	0.0565 (17)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.528 (4)
O1—H1A	0.8200 (13)	C5B—C10B	1.526 (4)
O1—C1	1.445 (3)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.532 (3)	C7B—H7B	0.9800
C1—C6	1.522 (3)	C7B—C8B	1.524 (4)
C2—H2	0.9800	C7B—C9B	1.519 (4)
C2—C3	1.537 (3)	C8B—H8BA	0.9600
C2—C7	1.540 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.521 (3)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.522 (4)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.534 (3)	O1C—H1CA	0.8200 (12)
C5—C10	1.532 (4)	O1C—H1C	0.86 (3)
C6—H6A	0.9700	O1C—C1C	1.448 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.514 (3)
C7—C8	1.531 (4)	C2C—C3C	1.533 (3)
C7—C9	1.534 (4)	C2C—C7C	1.563 (4)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.537 (4)
C9—H9A	0.9600	C6C—C5C	1.534 (3)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.517 (4)
C10—H10B	0.9600	C4C—C3C	1.541 (4)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (11)	C5C—H5C	0.9800
O1B—H1BB	0.8201 (11)	C5C—C10C	1.543 (4)
O1B—C1B	1.436 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.525 (4)	C7C—H7C	0.9800
C1B—C6B	1.519 (4)	C7C—C8C	1.530 (4)
C2B—H2B	0.9800	C7C—C9C	1.525 (4)
C2B—C3B	1.538 (4)	C8C—H8CA	0.9600
C2B—C7B	1.546 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.529 (4)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.517 (4)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	87.2	C10B—C5B—C6B	111.3 (3)
C1—O1—H1B	109.5	C1B—C6B—C5B	112.4 (2)
C1—O1—H1A	112 (5)	C1B—C6B—H6BA	109.1
O1—C1—H1	108.7	C1B—C6B—H6BB	109.1
O1—C1—C2	109.41 (19)	C5B—C6B—H6BA	109.1
O1—C1—C6	110.27 (17)	C5B—C6B—H6BB	109.1
C2—C1—H1	108.7	H6BA—C6B—H6BB	107.8
C6—C1—H1	108.7	C2B—C7B—H7B	106.2
C6—C1—C2	111.06 (19)	C8B—C7B—C2B	115.1 (2)
C1—C2—H2	106.6	C8B—C7B—H7B	106.2
C1—C2—C3	109.6 (2)	C9B—C7B—C2B	112.2 (2)
C1—C2—C7	112.99 (19)	C9B—C7B—H7B	106.2
C3—C2—H2	106.6	C9B—C7B—C8B	110.4 (3)
C3—C2—C7	114.00 (18)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.6	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.3	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.3	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	107.9	H8BA—C8B—H8BC	109.5
C4—C3—C2	111.79 (18)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.3	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.3	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.4	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.4	H9BA—C9B—H9BB	109.5
C3—C4—C5	111.3 (2)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	108.0	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.4	C5B—C10B—H10D	109.5
C5—C4—H4B	109.4	C5B—C10B—H10E	109.5
C4—C5—H5	108.3	C5B—C10B—H10F	109.5
C4—C5—C6	109.3 (2)	H10D—C10B—H10E	109.5
C4—C5—C10	111.6 (3)	H10D—C10B—H10F	109.5
C6—C5—H5	108.3	H10E—C10B—H10F	109.5
C10—C5—H5	108.3	H1CA—O1C—H1C	114 (3)
C10—C5—C6	111.0 (2)	C1C—O1C—H1CA	112 (3)
C1—C6—C5	113.13 (18)	C1C—O1C—H1C	110 (4)
C1—C6—H6A	109.0	C1C—C2C—H2C	106.5
C1—C6—H6B	109.0	C1C—C2C—C3C	109.9 (2)
C5—C6—H6A	109.0	C1C—C2C—C7C	113.07 (19)
C5—C6—H6B	109.0	C3C—C2C—H2C	106.5
H6A—C6—H6B	107.8	C3C—C2C—C7C	113.9 (2)
C2—C7—H7	107.0	C7C—C2C—H2C	106.5
C8—C7—C2	114.1 (2)	H6CA—C6C—H6CB	107.8
C8—C7—H7	107.0	C1C—C6C—H6CA	109.0
C8—C7—C9	110.4 (2)	C1C—C6C—H6CB	109.0
C9—C7—C2	111.1 (2)	C5C—C6C—H6CA	109.0
C9—C7—H7	107.0	C5C—C6C—H6CB	109.0
C7—C8—H8A	109.5	C5C—C6C—C1C	112.8 (2)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.3
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.3
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.6 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.3
C7—C9—H9B	109.5	O1C—C1C—C2C	110.2 (2)
C7—C9—H9C	109.5	O1C—C1C—C6C	110.47 (19)
H9A—C9—H9B	109.5	O1C—C1C—H1CB	107.5
H9A—C9—H9C	109.5	C2C—C1C—C6C	113.33 (19)
H9B—C9—H9C	109.5	C2C—C1C—H1CB	107.5
C5—C10—H10A	109.5	C6C—C1C—H1CB	107.5
C5—C10—H10B	109.5	C6C—C5C—H5C	107.5
C5—C10—H10C	109.5	C6C—C5C—C10C	112.1 (2)
H10A—C10—H10B	109.5	C4C—C5C—C6C	109.5 (2)
H10A—C10—H10C	109.5	C4C—C5C—H5C	107.5
H10B—C10—H10C	109.5	C4C—C5C—C10C	112.6 (2)
H1BA—O1B—H1BB	122 (5)	C10C—C5C—H5C	107.5
C1B—O1B—H1BA	118 (3)	C2C—C3C—C4C	112.5 (2)
C1B—O1B—H1BB	113 (3)	C2C—C3C—H3CA	109.1
O1B—C1B—H1BC	108.1	C2C—C3C—H3CB	109.1
O1B—C1B—C2B	112.9 (2)	C4C—C3C—H3CA	109.1
O1B—C1B—C6B	108.0 (2)	C4C—C3C—H3CB	109.1
C2B—C1B—H1BC	108.1	H3CA—C3C—H3CB	107.8
C6B—C1B—H1BC	108.1	C2C—C7C—H7C	107.0
C6B—C1B—C2B	111.6 (2)	C8C—C7C—C2C	113.7 (2)
C1B—C2B—H2B	106.3	C8C—C7C—H7C	107.0
C1B—C2B—C3B	108.8 (2)	C9C—C7C—C2C	111.8 (2)
C1B—C2B—C7B	114.3 (2)	C9C—C7C—H7C	107.0
C3B—C2B—H2B	106.3	C9C—C7C—C8C	110.1 (2)
C3B—C2B—C7B	114.1 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.3	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.4	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.4	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.0	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	111.1 (3)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.4	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.4	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.0	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.0	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.8 (2)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.0	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.0	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.4	C5C—C10C—H10I	109.5
C4B—C5B—C6B	110.0 (2)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	112.9 (3)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.4	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.4

O1—C1—C2—C3	176.49 (18)	C3B—C2B—C7B—C9B	−69.4 (3)
O1—C1—C2—C7	−55.2 (3)	C3B—C4B—C5B—C6B	−53.2 (4)
O1—C1—C6—C5	−177.0 (2)	C3B—C4B—C5B—C10B	−178.3 (3)
C1—C2—C3—C4	−56.5 (3)	C4B—C5B—C6B—C1B	53.4 (3)
C1—C2—C7—C8	−74.0 (2)	C6B—C1B—C2B—C3B	57.4 (3)
C1—C2—C7—C9	160.5 (2)	C6B—C1B—C2B—C7B	−173.7 (2)
C2—C1—C6—C5	−55.5 (3)	C7B—C2B—C3B—C4B	174.3 (2)
C2—C3—C4—C5	58.2 (3)	C10B—C5B—C6B—C1B	179.3 (2)
C3—C2—C7—C8	52.1 (3)	C1C—C2C—C3C—C4C	−53.6 (3)
C3—C2—C7—C9	−73.5 (3)	C1C—C2C—C7C—C8C	−63.6 (3)
C3—C4—C5—C6	−55.7 (3)	C1C—C2C—C7C—C9C	171.0 (2)
C3—C4—C5—C10	−178.9 (2)	C1C—C6C—C5C—C4C	54.1 (3)
C4—C5—C6—C1	55.2 (3)	C1C—C6C—C5C—C10C	179.8 (2)
C6—C1—C2—C3	54.5 (2)	C5C—C6C—C1C—O1C	−177.77 (18)
C6—C1—C2—C7	−177.14 (19)	C5C—C6C—C1C—C2C	−53.6 (3)
C7—C2—C3—C4	175.7 (2)	C5C—C4C—C3C—C2C	57.1 (3)
C10—C5—C6—C1	178.7 (2)	C3C—C2C—C1C—O1C	176.16 (17)
O1B—C1B—C2B—C3B	179.2 (2)	C3C—C2C—C1C—C6C	51.8 (2)
O1B—C1B—C2B—C7B	−51.9 (3)	C3C—C2C—C7C—C8C	62.8 (3)
O1B—C1B—C6B—C5B	178.39 (18)	C3C—C2C—C7C—C9C	−62.6 (3)
C1B—C2B—C3B—C4B	−56.7 (3)	C3C—C4C—C5C—C6C	−55.7 (3)
C1B—C2B—C7B—C8B	−68.1 (3)	C3C—C4C—C5C—C10C	178.9 (2)
C1B—C2B—C7B—C9B	164.5 (3)	C7C—C2C—C1C—O1C	−55.3 (2)
C2B—C1B—C6B—C5B	−57.0 (3)	C7C—C2C—C1C—C6C	−179.68 (18)
C2B—C3B—C4B—C5B	56.3 (4)	C7C—C2C—C3C—C4C	178.3 (2)
C3B—C2B—C7B—C8B	58.0 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.10GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 0.999 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.933 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.489 (3) Å	Cell parameters from 1392 reflections
c = 12.767 (3) Å	θ = 5.8–26.3°
α = 117.43 (3)°	µ = 0.06 mm⁻¹
β = 98.767 (18)°	T = 296 K
γ = 104.13 (2)°	Plate, colourless
V = 1558.3 (7) Å³	0.40 × 0.30 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	1392 independent reflections
Radiation source: fine-focus sealed tube	634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
Detector resolution: 16.4 pixels mm^-1	θ_max = 26.3°, θ_min = 5.1°
ω scans	h = −14→14
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −6→6
T_min = 0.978, T_max = 0.996	l = −12→12
7351 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.072	w = 1/[σ²(F_o²) + (0.0997P)² + 0.5955P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.220	(Δ/σ)_max = 0.005
S = 1.02	Δρ_max = 0.08 e Å⁻³
1392 reflections	Δρ_min = −0.07 e Å⁻³
314 parameters	Extinction correction: SHELXL-2015/3 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 restraints	Extinction coefficient: 0.015 (17)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.10 (2) GPa (100000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5452 (5)	1.0731 (10)	0.1261 (6)	0.097 (10)
H1B	0.611969	1.066743	0.126006	0.146*	0.5
H1A	0.527 (14)	1.000 (4)	0.067 (7)	0.146*	0.5
C1	0.5574 (8)	1.2115 (16)	0.1773 (9)	0.077 (6)
H1	0.478523	1.214204	0.145888	0.115*
C2	0.5896 (8)	1.2749 (15)	0.3176 (9)	0.075 (6)
H2	0.668820	1.270332	0.344380	0.112*
C3	0.6106 (8)	1.4162 (16)	0.3765 (9)	0.080 (6)
H3A	0.635962	1.456798	0.466069	0.119*
H3B	0.535340	1.427391	0.351687	0.119*
C4	0.7063 (8)	1.480 (2)	0.3388 (11)	0.103 (7)
H4A	0.782421	1.472796	0.367212	0.155*
H4B	0.718400	1.571650	0.377991	0.155*
C5	0.6705 (10)	1.420 (2)	0.1991 (12)	0.118 (7)
H5	0.593589	1.429006	0.172500	0.177*
C6	0.6493 (8)	1.2791 (17)	0.1395 (10)	0.087 (7)
H6A	0.622060	1.239236	0.050142	0.130*
H6B	0.725479	1.268273	0.161878	0.130*
C7	0.5036 (7)	1.2034 (16)	0.3630 (10)	0.085 (6)
H7	0.486371	1.110619	0.310614	0.128*
C8	0.3803 (7)	1.2265 (17)	0.3507 (10)	0.114 (11)
H8A	0.343884	1.200934	0.266391	0.137*
H8B	0.326675	1.176276	0.373702	0.137*
H8C	0.394855	1.316483	0.404330	0.137*
C9	0.5595 (9)	1.244 (2)	0.4946 (12)	0.141 (12)
H9A	0.503352	1.197173	0.518962	0.169*
H9B	0.632631	1.224865	0.501945	0.169*
H9C	0.578200	1.334722	0.547424	0.169*
C10	0.7661 (11)	1.489 (2)	0.1597 (13)	0.160 (12)
H10A	0.776798	1.579203	0.199956	0.192*
H10B	0.841946	1.480149	0.183299	0.192*
H10C	0.738745	1.451146	0.071414	0.192*
O1B	0.7477 (8)	1.0131 (15)	0.1308 (11)	0.126 (12)
H1BA	0.814 (2)	1.034 (11)	0.120 (3)	0.188*	0.5
H1BB	0.7047 (14)	1.057 (3)	0.137 (16)	0.188*	0.5
C1B	0.7636 (16)	0.951 (3)	0.2007 (16)	0.121 (9)
H1BC	0.824019	0.910095	0.179916	0.182*
C2B	0.8068 (13)	1.052 (3)	0.3387 (15)	0.104 (8)
H2B	0.741304	1.084260	0.358789	0.155*
C3B	0.8217 (16)	0.973 (3)	0.4034 (17)	0.129 (9)
H3BA	0.880199	0.931841	0.377876	0.193*
H3BB	0.852060	1.030452	0.492733	0.193*
C4B	0.7004 (10)	0.870 (2)	0.3682 (12)	0.144 (8)
H4BA	0.709855	0.824576	0.411604	0.216*
H4BB	0.642222	0.910982	0.393775	0.216*
C5B	0.6537 (16)	0.776 (3)	0.2331 (19)	0.132 (9)
H5B	0.713055	0.734745	0.209853	0.199*
C6B	0.6425 (12)	0.849 (3)	0.1620 (14)	0.092 (8)
H6BA	0.616757	0.788320	0.073312	0.138*
H6BB	0.582143	0.888787	0.181004	0.138*
C7B	0.9220 (8)	1.1687 (17)	0.3790 (11)	0.111 (7)
H7B	0.906304	1.198308	0.321099	0.166*
C8B	1.0370 (7)	1.1340 (18)	0.3672 (11)	0.133 (12)
H8BA	1.020460	1.062660	0.285094	0.159*
H8BB	1.102046	1.207262	0.382249	0.159*
H8BC	1.059982	1.110541	0.426770	0.159*
C9B	0.9408 (8)	1.2771 (18)	0.5022 (11)	0.125 (12)
H9BA	0.867290	1.295185	0.505178	0.150*
H9BB	0.962758	1.255309	0.563367	0.150*
H9BC	1.004822	1.352030	0.518846	0.150*
C10B	0.5325 (11)	0.671 (2)	0.1932 (14)	0.171 (13)
H10D	0.506873	0.612998	0.104938	0.206*
H10E	0.541260	0.623233	0.233577	0.206*
H10F	0.472820	0.708962	0.215899	0.206*
O1C	0.9386 (9)	1.0784 (10)	0.0526 (12)	0.122 (12)
H1CA	0.882 (3)	1.043 (4)	0.068 (3)	0.183*	0.5
H1C	0.9635 (13)	1.021 (2)	0.014 (5)	0.183*	0.5
C2C	1.0544 (12)	1.258 (3)	0.0293 (15)	0.089 (8)
H2C	1.081949	1.195788	−0.031668	0.133*
C6C	0.8359 (13)	1.113 (2)	−0.1061 (14)	0.082 (8)
H6CA	0.756537	1.072026	−0.104278	0.124*
H6CB	0.859614	1.046354	−0.164881	0.124*
C4C	0.9492 (9)	1.281 (2)	−0.1413 (12)	0.123 (7)
H4CA	0.942329	1.343028	−0.164595	0.185*
H4CB	0.979738	1.221579	−0.199930	0.185*
C1C	0.9253 (16)	1.181 (3)	0.019 (2)	0.099 (8)
H1CB	0.895213	1.240110	0.079321	0.149*
C5C	0.8294 (16)	1.208 (3)	−0.1470 (17)	0.120 (10)
H5C	0.802586	1.271646	−0.086555	0.180*
C3C	1.0355 (17)	1.348 (3)	−0.0151 (19)	0.117 (10)
H3CA	1.005803	1.409446	0.042263	0.175*
H3CB	1.113209	1.397075	−0.013844	0.175*
C7C	1.1460 (7)	1.3148 (16)	0.1605 (9)	0.095 (7)
H7C	1.142163	1.244902	0.176935	0.142*
C8C	1.1168 (8)	1.4192 (18)	0.2630 (10)	0.124 (12)
H8CA	1.036319	1.383276	0.263926	0.149*
H8CB	1.174256	1.451613	0.341559	0.149*
H8CC	1.121379	1.488533	0.247987	0.149*
C9C	1.2728 (8)	1.3712 (19)	0.1588 (11)	0.139 (12)
H9CA	1.291050	1.305371	0.094195	0.167*
H9CB	1.277450	1.440544	0.143771	0.167*
H9CC	1.330326	1.403624	0.237342	0.167*
C10C	0.7317 (8)	1.1440 (19)	−0.2780 (10)	0.116 (12)
H10G	0.654749	1.097731	−0.277625	0.139*
H10H	0.724041	1.209966	−0.294347	0.139*
H10I	0.757170	1.085158	−0.341272	0.139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.109 (4)	0.071 (12)	0.089 (6)	0.034 (6)	0.028 (4)	0.023 (7)
C1	0.083 (5)	0.070 (10)	0.070 (6)	0.023 (6)	0.020 (5)	0.033 (5)
C2	0.084 (5)	0.067 (10)	0.070 (6)	0.034 (6)	0.020 (5)	0.031 (5)
C3	0.092 (5)	0.069 (10)	0.076 (6)	0.025 (6)	0.027 (5)	0.038 (6)
C4	0.101 (5)	0.095 (10)	0.110 (7)	0.031 (6)	0.027 (5)	0.054 (6)
C5	0.123 (6)	0.113 (11)	0.120 (8)	0.036 (7)	0.057 (7)	0.058 (6)
C6	0.092 (5)	0.092 (10)	0.084 (7)	0.030 (6)	0.033 (5)	0.051 (6)
C7	0.079 (5)	0.086 (10)	0.089 (6)	0.040 (6)	0.027 (5)	0.039 (5)
C8	0.090 (5)	0.111 (16)	0.130 (9)	0.026 (7)	0.044 (6)	0.055 (9)
C9	0.128 (7)	0.163 (18)	0.137 (10)	0.046 (9)	0.043 (7)	0.084 (10)
C10	0.170 (8)	0.147 (18)	0.173 (11)	0.057 (10)	0.098 (9)	0.077 (10)
O1B	0.102 (6)	0.157 (17)	0.152 (9)	0.055 (7)	0.055 (6)	0.098 (9)
C1B	0.116 (8)	0.134 (13)	0.119 (10)	0.051 (8)	0.048 (8)	0.063 (7)
C2B	0.097 (7)	0.102 (12)	0.111 (9)	0.037 (8)	0.032 (7)	0.053 (7)
C3B	0.124 (9)	0.135 (13)	0.132 (10)	0.042 (8)	0.050 (8)	0.071 (7)
C4B	0.142 (7)	0.152 (11)	0.143 (9)	0.038 (7)	0.052 (7)	0.086 (7)
C5B	0.122 (9)	0.137 (13)	0.142 (11)	0.048 (8)	0.048 (9)	0.073 (7)
C6B	0.101 (7)	0.095 (12)	0.082 (7)	0.037 (8)	0.025 (6)	0.047 (6)
C7B	0.095 (6)	0.123 (11)	0.119 (7)	0.047 (6)	0.036 (5)	0.061 (6)
C8B	0.099 (6)	0.162 (18)	0.160 (10)	0.048 (8)	0.051 (7)	0.096 (10)
C9B	0.109 (6)	0.097 (16)	0.152 (10)	0.017 (8)	0.034 (6)	0.062 (9)
C10B	0.161 (9)	0.158 (19)	0.193 (12)	0.059 (11)	0.058 (9)	0.088 (11)
O1C	0.112 (6)	0.122 (17)	0.137 (9)	0.057 (9)	0.046 (6)	0.061 (10)
C2C	0.089 (7)	0.082 (12)	0.093 (9)	0.036 (8)	0.033 (6)	0.039 (6)
C6C	0.088 (7)	0.078 (11)	0.080 (8)	0.013 (7)	0.028 (6)	0.047 (6)
C4C	0.135 (7)	0.110 (11)	0.120 (8)	0.029 (7)	0.028 (6)	0.065 (6)
C1C	0.097 (7)	0.100 (12)	0.100 (9)	0.040 (8)	0.040 (6)	0.047 (6)
C5C	0.124 (9)	0.120 (13)	0.115 (10)	0.050 (9)	0.039 (8)	0.057 (7)
C3C	0.117 (9)	0.120 (13)	0.114 (10)	0.040 (9)	0.021 (7)	0.067 (7)
C7C	0.092 (5)	0.094 (10)	0.096 (7)	0.031 (6)	0.019 (5)	0.053 (6)
C8C	0.132 (7)	0.129 (17)	0.102 (8)	0.071 (9)	0.017 (6)	0.046 (9)
C9C	0.107 (6)	0.150 (18)	0.166 (10)	0.047 (9)	0.034 (7)	0.087 (10)
C10C	0.139 (7)	0.120 (17)	0.105 (9)	0.048 (9)	0.016 (7)	0.077 (9)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.56 (7)
O1—H1A	0.8200 (12)	C5B—C10B	1.52 (2)
O1—C1	1.50 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.523 (15)	C7B—H7B	0.9800
C1—C6	1.494 (18)	C7B—C8B	1.54 (2)
C2—H2	0.9800	C7B—C9B	1.463 (10)
C2—C3	1.50 (2)	C8B—H8BA	0.9600
C2—C7	1.55 (2)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.502 (19)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.517 (19)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.49 (3)	O1C—H1CA	0.8200 (12)
C5—C10	1.55 (2)	O1C—H1C	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.56 (5)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.55 (2)
C7—C8	1.566 (18)	C2C—C3C	1.53 (6)
C7—C9	1.50 (2)	C2C—C7C	1.57 (2)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.48 (3)
C9—H9A	0.9600	C6C—C5C	1.52 (6)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.463 (19)
C10—H10B	0.9600	C4C—C3C	1.48 (3)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (14)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.58 (3)
O1B—C1B	1.45 (5)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.523 (18)	C7C—H7C	0.9800
C1B—C6B	1.50 (2)	C7C—C8C	1.524 (14)
C2B—H2B	0.9800	C7C—C9C	1.514 (10)
C2B—C3B	1.58 (6)	C8C—H8CA	0.9600
C2B—C7B	1.55 (2)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.52 (2)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.478 (16)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	78.5	C10B—C5B—C6B	110 (2)
C1—O1—H1B	109.5	C1B—C6B—C5B	109 (2)
C1—O1—H1A	150 (8)	C1B—C6B—H6BA	109.9
O1—C1—H1	108.5	C1B—C6B—H6BB	109.9
O1—C1—C2	106.9 (16)	C5B—C6B—H6BA	109.9
C2—C1—H1	108.5	C5B—C6B—H6BB	109.9
C6—C1—O1	112.1 (9)	H6BA—C6B—H6BB	108.3
C6—C1—H1	108.5	C2B—C7B—H7B	106.2
C6—C1—C2	112.1 (8)	C8B—C7B—C2B	113.7 (17)
C1—C2—H2	105.4	C8B—C7B—H7B	106.2
C1—C2—C7	114.8 (8)	C9B—C7B—C2B	111.6 (10)
C3—C2—C1	110.1 (16)	C9B—C7B—H7B	106.2
C3—C2—H2	105.4	C9B—C7B—C8B	112.4 (9)
C3—C2—C7	114.6 (8)	C7B—C8B—H8BA	109.5
C7—C2—H2	105.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.5	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.5	H8BA—C8B—H8BB	109.5
C2—C3—C4	110.8 (10)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	108.1	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.5	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.5	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
C3—C4—C5	111.4 (8)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	108.0	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	107.9	C5B—C10B—H10F	109.5
C4—C5—C10	111.8 (9)	H10D—C10B—H10E	109.5
C6—C5—C4	109 (2)	H10D—C10B—H10F	109.5
C6—C5—H5	107.9	H10E—C10B—H10F	109.5
C6—C5—C10	112.2 (10)	H1CA—O1C—H1C	104 (4)
C10—C5—H5	107.9	C1C—O1C—H1CA	117 (5)
C1—C6—C5	112.6 (10)	C1C—O1C—H1C	125 (5)
C1—C6—H6A	109.1	C1C—C2C—H2C	106.9
C1—C6—H6B	109.1	C1C—C2C—C7C	110.8 (19)
C5—C6—H6A	109.1	C3C—C2C—H2C	106.9
C5—C6—H6B	109.1	C3C—C2C—C1C	105 (2)
H6A—C6—H6B	107.8	C3C—C2C—C7C	119.7 (17)
C2—C7—H7	108.1	C7C—C2C—H2C	106.9
C2—C7—C8	111.2 (15)	H6CA—C6C—H6CB	108.2
C8—C7—H7	108.1	C1C—C6C—H6CA	109.7
C9—C7—C2	112.2 (9)	C1C—C6C—H6CB	109.7
C9—C7—H7	108.1	C1C—C6C—C5C	110 (2)
C9—C7—C8	108.9 (8)	C5C—C6C—H6CA	109.7
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.7
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.1
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.5
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.5
H8A—C8—H8C	109.5	C5C—C4C—C3C	110.8 (17)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.5
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.5
C7—C9—H9B	109.5	O1C—C1C—H1CB	109.0
C7—C9—H9C	109.5	C2C—C1C—O1C	107 (2)
H9A—C9—H9B	109.5	C2C—C1C—H1CB	109.0
H9A—C9—H9C	109.5	C6C—C1C—O1C	109 (2)
H9B—C9—H9C	109.5	C6C—C1C—C2C	114 (2)
C5—C10—H10A	109.5	C6C—C1C—H1CB	109.0
C5—C10—H10B	109.5	C6C—C5C—H5C	106.5
C5—C10—H10C	109.5	C6C—C5C—C10C	113.0 (18)
H10A—C10—H10B	109.5	C4C—C5C—C6C	112 (3)
H10A—C10—H10C	109.5	C4C—C5C—H5C	106.5
H10B—C10—H10C	109.5	C4C—C5C—C10C	112.2 (19)
H1BA—O1B—H1BB	121 (10)	C10C—C5C—H5C	106.5
C1B—O1B—H1BA	104 (8)	C2C—C3C—H3CA	108.9
C1B—O1B—H1BB	126 (10)	C2C—C3C—H3CB	108.9
O1B—C1B—H1BC	109.7	C4C—C3C—C2C	114 (2)
O1B—C1B—C2B	109 (3)	C4C—C3C—H3CA	108.9
O1B—C1B—C6B	106 (2)	C4C—C3C—H3CB	108.9
C2B—C1B—H1BC	109.7	H3CA—C3C—H3CB	107.7
C6B—C1B—H1BC	109.7	C2C—C7C—H7C	109.0
C6B—C1B—C2B	112.3 (14)	C8C—C7C—C2C	111.8 (14)
C1B—C2B—H2B	108.1	C8C—C7C—H7C	109.0
C1B—C2B—C3B	104 (3)	C9C—C7C—C2C	108.4 (11)
C1B—C2B—C7B	113.9 (16)	C9C—C7C—H7C	109.0
C3B—C2B—H2B	108.1	C9C—C7C—C8C	109.6 (9)
C7B—C2B—H2B	108.1	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	114.5 (18)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.6	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.6	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.2	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	110 (2)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.6	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.6	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.4	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.4	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	108.0	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	111.3 (13)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.4	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.4	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.9	C5C—C10C—H10I	109.5
C4B—C5B—C6B	110 (3)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	113.3 (16)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.9	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.9

O1—C1—C2—C3	176.7 (6)	C3B—C2B—C7B—C9B	−76 (2)
O1—C1—C2—C7	−52.1 (14)	C3B—C4B—C5B—C6B	−57 (3)
O1—C1—C6—C5	−174.9 (13)	C3B—C4B—C5B—C10B	180 (3)
C1—C2—C3—C4	−55.6 (14)	C4B—C5B—C6B—C1B	56 (2)
C1—C2—C7—C8	−75.9 (14)	C6B—C1B—C2B—C3B	63 (3)
C1—C2—C7—C9	161.9 (16)	C6B—C1B—C2B—C7B	−172 (3)
C2—C1—C6—C5	−55 (2)	C7B—C2B—C3B—C4B	173.8 (7)
C2—C3—C4—C5	59 (2)	C10B—C5B—C6B—C1B	−178.8 (10)
C3—C2—C7—C8	53.1 (12)	C1C—C2C—C3C—C4C	−56.4 (18)
C3—C2—C7—C9	−69.1 (18)	C1C—C2C—C7C—C8C	−67 (2)
C3—C4—C5—C6	−57.8 (18)	C1C—C2C—C7C—C9C	172 (2)
C3—C4—C5—C10	177.7 (19)	C1C—C6C—C5C—C4C	54.6 (19)
C4—C5—C6—C1	55.6 (14)	C1C—C6C—C5C—C10C	−177.7 (9)
C6—C1—C2—C3	53.5 (15)	C5C—C6C—C1C—O1C	−174.7 (16)
C6—C1—C2—C7	−175.3 (15)	C5C—C6C—C1C—C2C	−56 (3)
C7—C2—C3—C4	173.1 (12)	C5C—C4C—C3C—C2C	60 (3)
C10—C5—C6—C1	179.9 (13)	C3C—C2C—C1C—O1C	175.2 (13)
O1B—C1B—C2B—C3B	−179.4 (15)	C3C—C2C—C1C—C6C	55 (3)
O1B—C1B—C2B—C7B	−54 (3)	C3C—C2C—C7C—C8C	55 (2)
O1B—C1B—C6B—C5B	179.2 (19)	C3C—C2C—C7C—C9C	−66 (2)
C1B—C2B—C3B—C4B	−61.3 (19)	C3C—C4C—C5C—C6C	−57 (2)
C1B—C2B—C7B—C8B	−67 (3)	C3C—C4C—C5C—C10C	175 (3)
C1B—C2B—C7B—C9B	165 (3)	C7C—C2C—C1C—O1C	−54 (2)
C2B—C1B—C6B—C5B	−62 (4)	C7C—C2C—C1C—C6C	−174 (3)
C2B—C3B—C4B—C5B	62 (3)	C7C—C2C—C3C—C4C	178.5 (6)
C3B—C2B—C7B—C8B	52.6 (19)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.15GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.005 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.923 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.429 (2) Å	Cell parameters from 1388 reflections
c = 12.770 (2) Å	θ = 4.8–26.2°
α = 117.478 (18)°	µ = 0.06 mm⁻¹
β = 99.16 (3)°	T = 296 K
γ = 103.81 (3)°	Plate, colourless
V = 1548.7 (9) Å³	0.45 × 0.45 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	1388 independent reflections
Radiation source: Enhance (Mo) X-ray Source	639 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
ω scans	θ_max = 26.2°, θ_min = 4.8°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −6→6
T_min = 0.972, T_max = 0.997	k = −15→15
7285 measured reflections	l = −15→15

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.079	w = 1/[σ²(F_o²) + (0.1609P)² + 0.1727P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.267	(Δ/σ)_max = 0.002
S = 1.04	Δρ_max = 0.12 e Å⁻³
1388 reflections	Δρ_min = −0.09 e Å⁻³
314 parameters	Extinction correction: SHELXL-2015/3 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 restraints	Extinction coefficient: 0.016 (19)
Primary atom site location: iterative

Special details top

Experimental. Data were collected at room temperature and pressure of 0.15 (2) GPa (150000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5467 (13)	1.0762 (6)	0.1275 (4)	0.080 (8)
H1B	0.614117	1.071332	0.128010	0.120*	0.5
H1A	0.53 (4)	1.036 (19)	0.0513 (12)	0.120*	0.5
C1	0.556 (2)	1.2101 (10)	0.1805 (7)	0.065 (5)
H1	0.477287	1.213945	0.150435	0.097*
C2	0.594 (3)	1.2750 (11)	0.3190 (8)	0.071 (5)
H2	0.674040	1.271495	0.345277	0.106*
C3	0.610 (2)	1.4173 (11)	0.3778 (8)	0.076 (5)
H3A	0.531847	1.425215	0.353991	0.113*
H3B	0.637584	1.459378	0.467541	0.113*
C4	0.697 (3)	1.4810 (13)	0.3381 (10)	0.100 (6)
H4A	0.776276	1.483196	0.373011	0.151*
H4B	0.700677	1.570096	0.372947	0.151*
C5	0.671 (3)	1.4208 (13)	0.2018 (10)	0.093 (6)
H5	0.595820	1.429147	0.169349	0.140*
C6	0.649 (2)	1.2761 (11)	0.1419 (8)	0.075 (5)
H6A	0.621567	1.235244	0.052209	0.113*
H6B	0.725040	1.264697	0.164855	0.113*
C7	0.511 (3)	1.2060 (15)	0.3620 (10)	0.083 (5)
H7	0.493401	1.112927	0.307560	0.124*
C8	0.387 (4)	1.2263 (18)	0.3541 (13)	0.112 (10)
H8A	0.338674	1.179008	0.383283	0.135*
H8B	0.400467	1.316969	0.404707	0.135*
H8C	0.344483	1.195295	0.269401	0.135*
C9	0.563 (3)	1.2404 (15)	0.4994 (9)	0.142 (10)
H9A	0.502770	1.191175	0.518112	0.171*
H9B	0.634830	1.219686	0.508325	0.171*
H9C	0.581889	1.331415	0.555666	0.171*
C10	0.770 (3)	1.4843 (15)	0.1626 (12)	0.119 (9)
H10A	0.746500	1.439865	0.073575	0.142*
H10B	0.778589	1.573730	0.195659	0.142*
H10C	0.845634	1.479025	0.194092	0.142*
O1B	0.7460 (13)	1.0087 (7)	0.1243 (5)	0.131 (8)
H1BA	0.811 (3)	1.051 (5)	0.126 (3)	0.196*	0.5
H1BB	0.685 (2)	1.024 (3)	0.106 (4)	0.196*	0.5
C1B	0.761 (3)	0.9499 (15)	0.1978 (9)	0.085 (6)
H1BC	0.822066	0.909209	0.177095	0.128*
C2B	0.805 (4)	1.0443 (16)	0.3338 (11)	0.093 (6)
H2B	0.738382	1.075472	0.351973	0.140*
C3B	0.819 (4)	0.9767 (17)	0.4035 (11)	0.114 (6)
H3BA	0.882125	0.940678	0.387349	0.171*
H3BB	0.842419	1.038595	0.492016	0.171*
C4B	0.704 (4)	0.8728 (17)	0.3657 (12)	0.116 (6)
H4BA	0.644840	0.911494	0.392612	0.173*
H4BB	0.717187	0.827431	0.408606	0.173*
C5B	0.653 (4)	0.7768 (16)	0.2305 (12)	0.106 (6)
H5B	0.710419	0.731654	0.207025	0.158*
C6B	0.647 (3)	0.8484 (15)	0.1601 (10)	0.085 (6)
H6BA	0.624694	0.786468	0.071711	0.128*
H6BB	0.584687	0.885956	0.174282	0.128*
C7B	0.906 (5)	1.157 (2)	0.3729 (14)	0.110 (6)
H7B	0.886904	1.187259	0.316080	0.165*
C8B	1.033 (6)	1.136 (3)	0.3667 (17)	0.150 (11)
H8BA	1.094786	1.217414	0.394775	0.180*
H8BB	1.054226	1.103460	0.418893	0.180*
H8BC	1.024834	1.074952	0.282532	0.180*
C9B	0.944 (4)	1.2772 (18)	0.5078 (14)	0.195 (11)
H9BA	1.012959	1.345222	0.520376	0.234*
H9BB	0.877075	1.307683	0.518318	0.234*
H9BC	0.963689	1.252364	0.567140	0.234*
C10B	0.530 (4)	0.6742 (18)	0.1899 (14)	0.135 (10)
H10D	0.504020	0.616415	0.101456	0.162*
H10E	0.536335	0.625972	0.230095	0.162*
H10F	0.472038	0.715456	0.212532	0.162*
O1C	0.9353 (7)	1.0792 (6)	0.0515 (5)	0.093 (8)
H1CA	0.893 (3)	1.081 (8)	0.096 (2)	0.140*	0.5
H1C	0.9775 (16)	1.0360 (19)	0.024 (4)	0.140*	0.5
C2C	1.059 (4)	1.2553 (15)	0.0330 (11)	0.080 (6)
H2C	1.089675	1.194159	−0.024750	0.120*
C6C	0.834 (2)	1.1097 (11)	−0.1069 (8)	0.082 (5)
H6CA	0.757090	1.058269	−0.110411	0.123*
H6CB	0.865424	1.050138	−0.164653	0.123*
C4C	0.950 (4)	1.2769 (16)	−0.1402 (12)	0.087 (6)
H4CA	0.978851	1.214894	−0.197786	0.131*
H4CB	0.946738	1.339266	−0.165126	0.131*
C1C	0.917 (4)	1.1711 (15)	0.0162 (11)	0.077 (6)
H1CB	0.885940	1.229902	0.075812	0.116*
C5C	0.811 (4)	1.1994 (17)	−0.1529 (12)	0.090 (6)
H5C	0.782523	1.261801	−0.093182	0.136*
C3C	1.038 (2)	1.3456 (11)	−0.0153 (8)	0.092 (5)
H3CA	1.009411	1.408551	0.042266	0.138*
H3CB	1.114838	1.392925	−0.015972	0.138*
C7C	1.143 (4)	1.317 (2)	0.1589 (15)	0.097 (7)
H7C	1.142276	1.247674	0.175983	0.145*
C8C	1.108 (3)	1.4163 (16)	0.2622 (10)	0.142 (10)
H8CA	1.167055	1.451896	0.341069	0.171*
H8CB	1.105203	1.484774	0.247345	0.171*
H8CC	1.029335	1.374263	0.262801	0.171*
C9C	1.266 (6)	1.370 (3)	0.156 (2)	0.160 (13)
H9CA	1.323384	1.411448	0.237241	0.192*
H9CB	1.286706	1.301424	0.097578	0.192*
H9CC	1.268272	1.433002	0.131636	0.192*
C10C	0.726 (3)	1.1376 (13)	−0.2750 (9)	0.112 (9)
H10G	0.718071	1.202442	−0.293870	0.134*
H10H	0.753977	1.078895	−0.335224	0.134*
H10I	0.647750	1.090370	−0.277350	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.09 (2)	0.069 (5)	0.072 (3)	0.028 (10)	0.024 (7)	0.028 (4)
C1	0.068 (14)	0.067 (6)	0.062 (4)	0.028 (8)	0.027 (7)	0.032 (4)
C2	0.067 (14)	0.077 (6)	0.069 (5)	0.028 (8)	0.027 (7)	0.035 (4)
C3	0.070 (14)	0.072 (6)	0.068 (5)	0.023 (8)	0.028 (8)	0.022 (4)
C4	0.099 (14)	0.087 (7)	0.110 (7)	0.037 (9)	0.040 (8)	0.043 (5)
C5	0.098 (14)	0.080 (7)	0.108 (6)	0.024 (8)	0.040 (8)	0.055 (5)
C6	0.078 (14)	0.077 (6)	0.077 (5)	0.028 (8)	0.025 (7)	0.044 (5)
C7	0.081 (14)	0.080 (7)	0.076 (5)	0.015 (9)	0.029 (8)	0.037 (5)
C8	0.11 (3)	0.103 (10)	0.108 (8)	0.036 (15)	0.035 (14)	0.042 (7)
C9	0.14 (3)	0.180 (12)	0.094 (7)	0.025 (16)	0.032 (11)	0.077 (7)
C10	0.13 (3)	0.098 (9)	0.145 (8)	0.051 (13)	0.056 (13)	0.066 (7)
O1B	0.17 (2)	0.160 (7)	0.126 (5)	0.064 (12)	0.053 (8)	0.116 (5)
C1B	0.088 (14)	0.091 (7)	0.076 (6)	0.025 (9)	0.020 (8)	0.047 (5)
C2B	0.092 (14)	0.099 (8)	0.088 (6)	0.030 (9)	0.034 (9)	0.049 (6)
C3B	0.120 (14)	0.131 (8)	0.094 (6)	0.023 (9)	0.026 (8)	0.074 (6)
C4B	0.130 (15)	0.126 (8)	0.107 (7)	0.024 (9)	0.036 (8)	0.083 (7)
C5B	0.104 (14)	0.089 (7)	0.121 (7)	0.036 (9)	0.036 (8)	0.052 (6)
C6B	0.087 (14)	0.090 (7)	0.074 (5)	0.023 (9)	0.031 (8)	0.041 (5)
C7B	0.108 (15)	0.120 (9)	0.102 (7)	0.042 (10)	0.035 (9)	0.057 (6)
C8B	0.16 (3)	0.169 (14)	0.133 (9)	0.053 (18)	0.038 (16)	0.091 (10)
C9B	0.18 (3)	0.160 (13)	0.187 (11)	0.040 (17)	0.080 (15)	0.045 (9)
C10B	0.13 (3)	0.118 (11)	0.164 (10)	0.061 (15)	0.053 (15)	0.069 (9)
O1C	0.11 (2)	0.095 (5)	0.118 (4)	0.036 (10)	0.048 (8)	0.079 (4)
C2C	0.081 (14)	0.076 (7)	0.078 (6)	0.026 (9)	0.025 (8)	0.038 (5)
C6C	0.086 (14)	0.083 (6)	0.073 (5)	0.018 (8)	0.025 (7)	0.043 (4)
C4C	0.092 (14)	0.089 (7)	0.086 (7)	0.029 (9)	0.024 (8)	0.052 (5)
C1C	0.080 (14)	0.076 (7)	0.088 (6)	0.030 (9)	0.034 (8)	0.048 (5)
C5C	0.091 (14)	0.096 (8)	0.086 (7)	0.025 (9)	0.031 (8)	0.051 (5)
C3C	0.103 (14)	0.090 (6)	0.092 (5)	0.024 (8)	0.032 (7)	0.060 (5)
C7C	0.095 (15)	0.098 (8)	0.094 (7)	0.035 (10)	0.026 (9)	0.047 (6)
C8C	0.14 (3)	0.175 (12)	0.100 (7)	0.055 (16)	0.051 (12)	0.059 (8)
C9C	0.16 (3)	0.168 (16)	0.147 (12)	0.043 (18)	0.040 (16)	0.088 (11)
C10C	0.10 (3)	0.117 (9)	0.094 (7)	0.019 (14)	0.007 (11)	0.058 (7)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.534 (15)
O1—H1A	0.8200 (15)	C5B—C10B	1.52 (5)
O1—C1	1.444 (8)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.495 (11)	C7B—H7B	0.9800
C1—C6	1.50 (3)	C7B—C8B	1.60 (8)
C2—H2	0.9800	C7B—C9B	1.57 (2)
C2—C3	1.516 (11)	C8B—H8BA	0.9600
C2—C7	1.49 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.45 (3)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.484 (14)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.526 (13)	O1C—H1CA	0.8200 (12)
C5—C10	1.53 (4)	O1C—H1C	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.455 (12)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.68 (5)
C7—C8	1.56 (5)	C2C—C3C	1.558 (14)
C7—C9	1.574 (16)	C2C—C7C	1.47 (4)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.44 (3)
C9—H9A	0.9600	C6C—C5C	1.538 (15)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.64 (6)
C10—H10B	0.9600	C4C—C3C	1.47 (3)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (12)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.44 (3)
O1B—C1B	1.446 (10)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.485 (16)	C7C—H7C	0.9800
C1B—C6B	1.44 (4)	C7C—C8C	1.54 (2)
C2B—H2B	0.9800	C7C—C9C	1.47 (8)
C2B—C3B	1.494 (14)	C8C—H8CA	0.9600
C2B—C7B	1.42 (6)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.46 (5)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.481 (18)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	89.2	C10B—C5B—C6B	110 (2)
C1—O1—H1B	109.5	C1B—C6B—C5B	113 (2)
C1—O1—H1A	113 (10)	C1B—C6B—H6BA	109.1
O1—C1—H1	109.5	C1B—C6B—H6BB	109.1
O1—C1—C2	108.9 (6)	C5B—C6B—H6BA	109.1
O1—C1—C6	109.1 (12)	C5B—C6B—H6BB	109.1
C2—C1—H1	109.5	H6BA—C6B—H6BB	107.8
C2—C1—C6	110.3 (17)	C2B—C7B—H7B	106.4
C6—C1—H1	109.5	C2B—C7B—C8B	115.9 (15)
C1—C2—H2	106.9	C2B—C7B—C9B	119 (3)
C1—C2—C3	110.2 (7)	C8B—C7B—H7B	106.4
C3—C2—H2	106.9	C9B—C7B—H7B	106.4
C7—C2—C1	112.5 (17)	C9B—C7B—C8B	102 (4)
C7—C2—H2	106.9	C7B—C8B—H8BA	109.5
C7—C2—C3	113.0 (15)	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.6	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.6	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.1	H8BA—C8B—H8BC	109.5
C4—C3—C2	110.4 (15)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.6	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.6	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.3	H9BA—C9B—H9BB	109.5
C3—C4—C5	116 (2)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.4	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.3	C5B—C10B—H10D	109.5
C5—C4—H4B	108.3	C5B—C10B—H10E	109.5
C4—C5—H5	107.3	C5B—C10B—H10F	109.5
C4—C5—C6	109.6 (8)	H10D—C10B—H10E	109.5
C4—C5—C10	115 (2)	H10D—C10B—H10F	109.5
C6—C5—H5	107.3	H10E—C10B—H10F	109.5
C6—C5—C10	110.2 (16)	H1CA—O1C—H1C	134 (8)
C10—C5—H5	107.3	C1C—O1C—H1CA	104 (7)
C1—C6—C5	112.4 (15)	C1C—O1C—H1C	122 (5)
C1—C6—H6A	109.1	C1C—C2C—H2C	107.6
C1—C6—H6B	109.1	C3C—C2C—H2C	107.6
C5—C6—H6A	109.1	C3C—C2C—C1C	103 (2)
C5—C6—H6B	109.1	C7C—C2C—H2C	107.6
H6A—C6—H6B	107.9	C7C—C2C—C1C	113 (2)
C2—C7—H7	107.1	C7C—C2C—C3C	117.5 (15)
C2—C7—C8	114.4 (13)	H6CA—C6C—H6CB	107.3
C2—C7—C9	116 (2)	C1C—C6C—H6CA	108.1
C8—C7—H7	107.1	C1C—C6C—H6CB	108.1
C8—C7—C9	104.9 (19)	C1C—C6C—C5C	116.9 (13)
C9—C7—H7	107.1	C5C—C6C—H6CA	108.1
C7—C8—H8A	109.5	C5C—C6C—H6CB	108.1
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.5
C7—C8—H8C	109.5	C5C—C4C—H4CA	108.5
H8A—C8—H8B	109.5	C5C—C4C—H4CB	108.5
H8A—C8—H8C	109.5	C3C—C4C—H4CA	108.5
H8B—C8—H8C	109.5	C3C—C4C—H4CB	108.5
C7—C9—H9A	109.5	C3C—C4C—C5C	114.9 (16)
C7—C9—H9B	109.5	O1C—C1C—C2C	103 (2)
C7—C9—H9C	109.5	O1C—C1C—H1CB	108.9
H9A—C9—H9B	109.5	C2C—C1C—H1CB	108.9
H9A—C9—H9C	109.5	C6C—C1C—O1C	113.2 (13)
H9B—C9—H9C	109.5	C6C—C1C—C2C	113.3 (15)
C5—C10—H10A	109.5	C6C—C1C—H1CB	108.9
C5—C10—H10B	109.5	C6C—C5C—C4C	101 (3)
C5—C10—H10C	109.5	C6C—C5C—H5C	108.4
H10A—C10—H10B	109.5	C4C—C5C—H5C	108.4
H10A—C10—H10C	109.5	C10C—C5C—C6C	116.7 (15)
H10B—C10—H10C	109.5	C10C—C5C—C4C	113.7 (16)
H1BA—O1B—H1BB	120 (5)	C10C—C5C—H5C	108.4
C1B—O1B—H1BA	112 (5)	C2C—C3C—H3CA	108.7
C1B—O1B—H1BB	125 (5)	C2C—C3C—H3CB	108.7
O1B—C1B—H1BC	107.8	C4C—C3C—C2C	114.1 (13)
O1B—C1B—C2B	113.5 (9)	C4C—C3C—H3CA	108.7
C2B—C1B—H1BC	107.8	C4C—C3C—H3CB	108.7
C6B—C1B—O1B	108 (2)	H3CA—C3C—H3CB	107.6
C6B—C1B—H1BC	107.8	C2C—C7C—H7C	106.9
C6B—C1B—C2B	112 (2)	C2C—C7C—C8C	115 (3)
C1B—C2B—H2B	105.2	C2C—C7C—C9C	107 (2)
C1B—C2B—C3B	110.5 (10)	C8C—C7C—H7C	106.9
C3B—C2B—H2B	105.2	C9C—C7C—H7C	106.9
C7B—C2B—C1B	114 (2)	C9C—C7C—C8C	114 (2)
C7B—C2B—H2B	105.2	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	115 (3)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.6	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.6	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.1	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	110 (3)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.6	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.6	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.5	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.5	H9CA—C9C—H9CB	109.5
C3B—C4B—C5B	115 (2)	H9CA—C9C—H9CC	109.5
H4BA—C4B—H4BB	107.5	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.5	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.5	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.3	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.3 (11)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	115 (2)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.3	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.3

O1—C1—C2—C3	177.8 (19)	C3B—C2B—C7B—C9B	−64 (4)
O1—C1—C2—C7	−55 (2)	C3B—C4B—C5B—C6B	−51 (4)
O1—C1—C6—C5	−175.9 (13)	C3B—C4B—C5B—C10B	−176 (2)
C1—C2—C3—C4	−57 (3)	C4B—C5B—C6B—C1B	51 (3)
C1—C2—C7—C8	−75.4 (18)	C6B—C1B—C2B—C3B	58 (3)
C1—C2—C7—C9	162.4 (13)	C6B—C1B—C2B—C7B	−170 (3)
C2—C1—C6—C5	−56.3 (19)	C7B—C2B—C3B—C4B	173 (2)
C2—C3—C4—C5	54 (2)	C10B—C5B—C6B—C1B	178.3 (18)
C3—C2—C7—C8	50 (2)	C1C—C2C—C3C—C4C	−53 (2)
C3—C2—C7—C9	−72 (2)	C1C—C2C—C7C—C8C	−61 (2)
C3—C4—C5—C6	−51 (3)	C1C—C2C—C7C—C9C	171.7 (17)
C3—C4—C5—C10	−175.8 (15)	C1C—C6C—C5C—C4C	58 (2)
C4—C5—C6—C1	51 (3)	C1C—C6C—C5C—C10C	−178 (3)
C6—C1—C2—C3	58 (2)	C5C—C6C—C1C—O1C	−179 (2)
C6—C1—C2—C7	−174.6 (14)	C5C—C6C—C1C—C2C	−62 (3)
C7—C2—C3—C4	176.5 (17)	C5C—C4C—C3C—C2C	62 (3)
C10—C5—C6—C1	178.2 (16)	C3C—C2C—C1C—O1C	175.5 (5)
O1B—C1B—C2B—C3B	180 (3)	C3C—C2C—C1C—C6C	52.6 (14)
O1B—C1B—C2B—C7B	−48 (4)	C3C—C2C—C7C—C8C	59 (4)
O1B—C1B—C6B—C5B	179.0 (10)	C3C—C2C—C7C—C9C	−68 (3)
C1B—C2B—C3B—C4B	−56 (3)	C3C—C4C—C5C—C6C	−56.8 (14)
C1B—C2B—C7B—C8B	−71 (3)	C3C—C4C—C5C—C10C	177.5 (8)
C1B—C2B—C7B—C9B	166.8 (19)	C7C—C2C—C1C—O1C	−56.7 (15)
C2B—C1B—C6B—C5B	−56 (2)	C7C—C2C—C1C—C6C	−179.6 (10)
C2B—C3B—C4B—C5B	55 (3)	C7C—C2C—C3C—C4C	−178 (3)
C3B—C2B—C7B—C8B	58 (2)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.30GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.035 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.886 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.233 (3) Å	Cell parameters from 1378 reflections
c = 12.647 (3) Å	θ = 4.8–26.7°
α = 117.45 (3)°	µ = 0.06 mm⁻¹
β = 99.624 (18)°	T = 296 K
γ = 103.81 (2)°	Plate, colourless
V = 1500.5 (8) Å³	0.40 × 0.30 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	1378 independent reflections
Radiation source: Enhance (Mo) X-ray Source	608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ω scans	θ_max = 26.7°, θ_min = 4.8°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
T_min = 0.978, T_max = 0.996	k = −6→6
7233 measured reflections	l = −12→12

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.067	w = 1/[σ²(F_o²) + (0.1255P)² + 0.0841P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.228	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 0.08 e Å⁻³
1378 reflections	Δρ_min = −0.08 e Å⁻³
314 parameters	Extinction correction: SHELXL-2015/3 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 restraints	Extinction coefficient: 0.03 (2)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.30 (2) GPa (300000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5451 (5)	1.0736 (10)	0.1257 (6)	0.114 (10)
H1B	0.612425	1.067867	0.125960	0.171*	0.5
H1A	0.512 (16)	0.995 (4)	0.071 (9)	0.171*	0.5
C1	0.5560 (7)	1.2110 (15)	0.1764 (9)	0.080 (6)
H1	0.476403	1.213869	0.144334	0.120*
C2	0.5906 (7)	1.2746 (15)	0.3197 (8)	0.074 (6)
H2	0.669804	1.268680	0.347430	0.111*
C3	0.6127 (8)	1.4204 (17)	0.3766 (9)	0.087 (6)
H3A	0.537403	1.431415	0.348286	0.130*
H3B	0.637567	1.464320	0.467601	0.130*
C4	0.7081 (8)	1.4809 (19)	0.3394 (11)	0.106 (7)
H4A	0.783269	1.470165	0.368445	0.159*
H4B	0.723553	1.574739	0.379561	0.159*
C5	0.6723 (9)	1.4204 (19)	0.2005 (11)	0.115 (7)
H5	0.595548	1.430957	0.172943	0.173*
C6	0.6501 (7)	1.2814 (16)	0.1401 (9)	0.083 (6)
H6A	0.726217	1.269130	0.162526	0.124*
H6B	0.622193	1.242072	0.049546	0.124*
C7	0.5027 (6)	1.2045 (15)	0.3634 (9)	0.083 (6)
H7	0.485218	1.109668	0.310289	0.125*
C8	0.3820 (7)	1.2236 (16)	0.3532 (10)	0.116 (11)
H8A	0.343194	1.198769	0.268428	0.140*
H8B	0.330455	1.169623	0.375139	0.140*
H8C	0.395179	1.314763	0.409518	0.140*
C9	0.5610 (9)	1.244 (2)	0.4960 (12)	0.143 (12)
H9A	0.638396	1.232297	0.504235	0.172*
H9B	0.573358	1.334921	0.551643	0.172*
H9C	0.508634	1.189782	0.517264	0.172*
C10	0.7685 (10)	1.488 (2)	0.1612 (13)	0.162 (12)
H10A	0.781709	1.580878	0.202656	0.195*
H10B	0.843843	1.476782	0.184772	0.195*
H10C	0.739924	1.449742	0.071727	0.195*
O1B	0.7473 (8)	1.0118 (15)	0.1281 (10)	0.123 (11)
H1BA	0.802 (3)	1.025 (9)	0.099 (3)	0.185*	0.5
H1BB	0.7061 (15)	1.058 (3)	0.134 (12)	0.185*	0.5
C1B	0.7626 (15)	0.948 (3)	0.1999 (15)	0.117 (8)
H1BC	0.822721	0.905367	0.180472	0.175*
C2B	0.8035 (14)	1.050 (3)	0.3372 (15)	0.113 (8)
H2B	0.737094	1.081962	0.356128	0.170*
C3B	0.8215 (15)	0.976 (3)	0.4016 (17)	0.127 (9)
H3BA	0.854791	1.037473	0.491918	0.190*
H3BB	0.879326	0.933928	0.375041	0.190*
C4B	0.6994 (9)	0.8721 (19)	0.3693 (11)	0.142 (7)
H4BA	0.710917	0.825814	0.412802	0.213*
H4BB	0.641529	0.914221	0.396152	0.213*
C5B	0.6507 (15)	0.776 (3)	0.2301 (17)	0.126 (9)
H5B	0.709216	0.732299	0.206951	0.190*
C6B	0.6419 (12)	0.849 (3)	0.1600 (14)	0.099 (8)
H6BA	0.615286	0.786850	0.069991	0.148*
H6BB	0.582708	0.891570	0.178773	0.148*
C7B	0.9200 (7)	1.1693 (16)	0.3790 (10)	0.112 (7)
H7B	0.903242	1.199470	0.320603	0.169*
C8B	1.0358 (7)	1.1331 (17)	0.3661 (10)	0.138 (12)
H8BA	1.017497	1.059393	0.282951	0.165*
H8BB	1.100760	1.207451	0.380469	0.165*
H8BC	1.060793	1.110080	0.426909	0.165*
C9B	0.9421 (7)	1.2784 (16)	0.5010 (11)	0.125 (11)
H9BA	1.014780	1.349422	0.522480	0.150*
H9BB	0.873734	1.307244	0.501215	0.150*
H9BC	0.952564	1.251937	0.561550	0.150*
C10B	0.5296 (11)	0.671 (2)	0.1934 (14)	0.173 (12)
H10D	0.500423	0.611033	0.103870	0.208*
H10E	0.540269	0.623552	0.234763	0.208*
H10F	0.471260	0.711821	0.218137	0.208*
O1C	0.9394 (10)	1.0789 (16)	0.0530 (12)	0.123 (12)
H1CA	0.873 (3)	1.036 (5)	0.051 (2)	0.184*	0.5
H1C	0.9735 (15)	1.0348 (15)	0.009 (2)	0.184*	0.5
C2C	1.0535 (12)	1.257 (2)	0.0280 (14)	0.089 (8)
H2C	1.080451	1.193418	−0.033459	0.134*
C6C	0.8337 (13)	1.113 (2)	−0.1060 (14)	0.085 (8)
H6CA	0.753830	1.072207	−0.104452	0.128*
H6CB	0.855855	1.043788	−0.165777	0.128*
C4C	0.9482 (9)	1.279 (2)	−0.1418 (11)	0.119 (7)
H4CA	0.977992	1.217306	−0.200471	0.178*
H4CB	0.940994	1.341344	−0.166752	0.178*
C1C	0.9231 (15)	1.178 (3)	0.019 (2)	0.096 (8)
H1CB	0.894370	1.239372	0.080761	0.145*
C5C	0.8269 (16)	1.206 (3)	−0.1478 (16)	0.119 (9)
H5C	0.801203	1.271342	−0.086706	0.178*
C3C	1.0349 (17)	1.348 (3)	−0.0167 (19)	0.121 (9)
H3CA	1.006121	1.411685	0.041261	0.182*
H3CB	1.112796	1.397066	−0.015897	0.182*
C7C	1.1451 (6)	1.3148 (15)	0.1602 (9)	0.096 (7)
H7C	1.141300	1.243154	0.176293	0.144*
C8C	1.1169 (7)	1.4198 (17)	0.2629 (10)	0.123 (12)
H8CA	1.035850	1.383031	0.262719	0.148*
H8CB	1.174950	1.452241	0.342821	0.148*
H8CC	1.121830	1.491191	0.248709	0.148*
C9C	1.2736 (7)	1.3731 (18)	0.1605 (11)	0.142 (12)
H9CA	1.291577	1.306024	0.094921	0.170*
H9CB	1.278574	1.444441	0.146252	0.170*
H9CC	1.331694	1.405491	0.240364	0.170*
C10C	0.7287 (8)	1.1414 (18)	−0.2787 (9)	0.128 (12)
H10G	0.729172	1.207216	−0.300128	0.153*
H10H	0.747150	1.072184	−0.341423	0.153*
H10I	0.649305	1.105211	−0.275097	0.153*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.118 (4)	0.078 (12)	0.093 (5)	0.029 (5)	0.029 (4)	0.009 (7)
C1	0.090 (5)	0.066 (10)	0.074 (6)	0.027 (6)	0.020 (4)	0.031 (5)
C2	0.086 (4)	0.068 (9)	0.065 (6)	0.035 (5)	0.021 (4)	0.030 (5)
C3	0.104 (5)	0.072 (10)	0.077 (6)	0.031 (6)	0.022 (5)	0.035 (5)
C4	0.109 (5)	0.088 (10)	0.110 (7)	0.029 (6)	0.030 (5)	0.047 (6)
C5	0.119 (6)	0.110 (11)	0.118 (8)	0.034 (6)	0.055 (6)	0.059 (6)
C6	0.093 (5)	0.083 (10)	0.081 (6)	0.025 (6)	0.035 (5)	0.050 (5)
C7	0.081 (4)	0.086 (9)	0.081 (6)	0.036 (5)	0.029 (4)	0.038 (5)
C8	0.099 (5)	0.112 (16)	0.131 (8)	0.032 (7)	0.046 (5)	0.059 (9)
C9	0.133 (6)	0.177 (18)	0.136 (10)	0.064 (8)	0.051 (7)	0.089 (9)
C10	0.166 (8)	0.141 (18)	0.197 (11)	0.067 (9)	0.102 (8)	0.082 (10)
O1B	0.105 (5)	0.158 (17)	0.142 (9)	0.058 (7)	0.047 (6)	0.099 (9)
C1B	0.117 (8)	0.127 (12)	0.111 (10)	0.041 (8)	0.047 (8)	0.064 (7)
C2B	0.111 (8)	0.104 (12)	0.122 (9)	0.039 (8)	0.040 (7)	0.056 (7)
C3B	0.123 (8)	0.128 (13)	0.129 (9)	0.049 (8)	0.043 (7)	0.065 (7)
C4B	0.141 (7)	0.152 (11)	0.140 (8)	0.042 (7)	0.050 (6)	0.085 (6)
C5B	0.124 (8)	0.130 (13)	0.131 (10)	0.034 (8)	0.044 (8)	0.077 (7)
C6B	0.101 (7)	0.099 (12)	0.097 (7)	0.040 (7)	0.037 (6)	0.048 (6)
C7B	0.097 (5)	0.116 (10)	0.120 (7)	0.043 (6)	0.041 (5)	0.056 (6)
C8B	0.105 (5)	0.163 (17)	0.152 (9)	0.051 (8)	0.056 (6)	0.082 (9)
C9B	0.115 (6)	0.083 (15)	0.150 (9)	0.019 (7)	0.036 (6)	0.051 (9)
C10B	0.174 (9)	0.147 (18)	0.193 (11)	0.050 (10)	0.073 (8)	0.083 (10)
O1C	0.114 (6)	0.127 (18)	0.130 (9)	0.054 (9)	0.039 (6)	0.064 (10)
C2C	0.097 (7)	0.080 (11)	0.088 (8)	0.031 (7)	0.034 (6)	0.041 (6)
C6C	0.089 (6)	0.082 (11)	0.085 (8)	0.023 (7)	0.029 (6)	0.047 (6)
C4C	0.130 (6)	0.108 (11)	0.113 (7)	0.021 (7)	0.029 (6)	0.067 (6)
C1C	0.092 (7)	0.092 (12)	0.105 (9)	0.041 (8)	0.043 (6)	0.043 (6)
C5C	0.127 (9)	0.120 (13)	0.108 (10)	0.046 (9)	0.034 (7)	0.059 (7)
C3C	0.128 (9)	0.123 (13)	0.112 (10)	0.050 (9)	0.022 (7)	0.065 (7)
C7C	0.100 (5)	0.096 (10)	0.086 (6)	0.024 (6)	0.017 (5)	0.053 (6)
C8C	0.138 (6)	0.116 (16)	0.101 (8)	0.066 (9)	0.023 (6)	0.041 (9)
C9C	0.116 (6)	0.131 (17)	0.167 (10)	0.035 (8)	0.044 (6)	0.074 (10)
C10C	0.147 (7)	0.131 (17)	0.101 (8)	0.035 (9)	0.019 (6)	0.072 (9)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.53 (6)
O1—H1A	0.8200 (12)	C5B—C10B	1.51 (2)
O1—C1	1.46 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.536 (15)	C7B—H7B	0.9800
C1—C6	1.510 (16)	C7B—C8B	1.555 (18)
C2—H2	0.9800	C7B—C9B	1.425 (10)
C2—C3	1.52 (3)	C8B—H8BA	0.9600
C2—C7	1.527 (18)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.467 (18)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.489 (19)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.44 (2)	O1C—H1CA	0.8200 (12)
C5—C10	1.54 (2)	O1C—H1C	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.51 (5)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.57 (2)
C7—C8	1.503 (16)	C2C—C3C	1.51 (6)
C7—C9	1.49 (2)	C2C—C7C	1.55 (2)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.46 (3)
C9—H9A	0.9600	C6C—C5C	1.47 (6)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.473 (18)
C10—H10B	0.9600	C4C—C3C	1.44 (2)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (13)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.56 (2)
O1B—C1B	1.46 (5)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.495 (17)	C7C—H7C	0.9800
C1B—C6B	1.46 (2)	C7C—C8C	1.504 (13)
C2B—H2B	0.9800	C7C—C9C	1.522 (9)
C2B—C3B	1.49 (6)	C8C—H8CA	0.9600
C2B—C7B	1.55 (2)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.53 (2)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.497 (16)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	90.0	C10B—C5B—C6B	112 (2)
C1—O1—H1B	109.5	C1B—C6B—C5B	109 (2)
C1—O1—H1A	151 (10)	C1B—C6B—H6BA	110.0
O1—C1—H1	109.1	C1B—C6B—H6BB	110.0
O1—C1—C2	105.9 (15)	C5B—C6B—H6BA	110.0
O1—C1—C6	111.7 (8)	C5B—C6B—H6BB	110.0
C2—C1—H1	109.1	H6BA—C6B—H6BB	108.3
C6—C1—H1	109.1	C2B—C7B—H7B	105.9
C6—C1—C2	111.7 (7)	C2B—C7B—C8B	113.8 (17)
C1—C2—H2	106.4	C8B—C7B—H7B	105.9
C3—C2—C1	107.4 (15)	C9B—C7B—C2B	112.7 (9)
C3—C2—H2	106.4	C9B—C7B—H7B	105.9
C3—C2—C7	114.9 (8)	C9B—C7B—C8B	111.9 (8)
C7—C2—C1	114.7 (7)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.6	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.6	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.1	H8BA—C8B—H8BC	109.5
C4—C3—C2	110.4 (10)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.6	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.6	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
C3—C4—C5	111.8 (7)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.9	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	107.9	C5B—C10B—H10F	109.5
C4—C5—C10	112.1 (9)	H10D—C10B—H10E	109.5
C6—C5—C4	109.7 (19)	H10D—C10B—H10F	109.5
C6—C5—H5	107.9	H10E—C10B—H10F	109.5
C6—C5—C10	111.0 (10)	H1CA—O1C—H1C	115 (4)
C10—C5—H5	107.9	C1C—O1C—H1CA	109 (5)
C1—C6—H6A	109.1	C1C—O1C—H1C	110 (3)
C1—C6—H6B	109.1	C1C—C2C—H2C	107.0
C5—C6—C1	112.6 (9)	C3C—C2C—H2C	107.0
C5—C6—H6A	109.1	C3C—C2C—C1C	106 (2)
C5—C6—H6B	109.1	C3C—C2C—C7C	119.8 (17)
H6A—C6—H6B	107.8	C7C—C2C—H2C	107.0
C2—C7—H7	107.1	C7C—C2C—C1C	109.5 (18)
C8—C7—C2	115.6 (15)	H6CA—C6C—H6CB	107.9
C8—C7—H7	107.1	C1C—C6C—H6CA	109.2
C9—C7—C2	111.1 (8)	C1C—C6C—H6CB	109.2
C9—C7—H7	107.1	C1C—C6C—C5C	112 (2)
C9—C7—C8	108.3 (8)	C5C—C6C—H6CA	109.2
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.2
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.3
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.3
H8A—C8—H8C	109.5	C3C—C4C—H4CA	109.3
H8B—C8—H8C	109.5	C3C—C4C—H4CB	109.3
C7—C9—H9A	109.5	C3C—C4C—C5C	111.5 (16)
C7—C9—H9B	109.5	O1C—C1C—C2C	106 (2)
C7—C9—H9C	109.5	O1C—C1C—H1CB	109.0
H9A—C9—H9B	109.5	C2C—C1C—H1CB	108.9
H9A—C9—H9C	109.5	C6C—C1C—O1C	111 (2)
H9B—C9—H9C	109.5	C6C—C1C—C2C	113 (2)
C5—C10—H10A	109.5	C6C—C1C—H1CB	109.0
C5—C10—H10B	109.5	C6C—C5C—C4C	111 (3)
C5—C10—H10C	109.5	C6C—C5C—H5C	106.2
H10A—C10—H10B	109.5	C6C—C5C—C10C	113.9 (18)
H10A—C10—H10C	109.5	C4C—C5C—H5C	106.2
H10B—C10—H10C	109.5	C4C—C5C—C10C	112.2 (18)
H1BA—O1B—H1BB	114 (10)	C10C—C5C—H5C	106.2
C1B—O1B—H1BA	115 (7)	C2C—C3C—H3CA	109.1
C1B—O1B—H1BB	127 (10)	C2C—C3C—H3CB	109.1
O1B—C1B—H1BC	110.3	C4C—C3C—C2C	113 (2)
O1B—C1B—C2B	109 (3)	C4C—C3C—H3CA	109.1
O1B—C1B—C6B	105 (2)	C4C—C3C—H3CB	109.1
C2B—C1B—H1BC	110.3	H3CA—C3C—H3CB	107.8
C6B—C1B—H1BC	110.3	C2C—C7C—H7C	108.9
C6B—C1B—C2B	111.3 (12)	C8C—C7C—C2C	112.1 (14)
C1B—C2B—H2B	108.7	C8C—C7C—H7C	108.9
C1B—C2B—C7B	113.1 (16)	C8C—C7C—C9C	109.5 (8)
C3B—C2B—C1B	105 (3)	C9C—C7C—C2C	108.5 (11)
C3B—C2B—H2B	108.7	C9C—C7C—H7C	108.9
C3B—C2B—C7B	112.9 (19)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	108.7	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.7	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.7	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	110 (2)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.2	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.7	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.7	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	108.3	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	109.1 (13)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.7	C5C—C10C—H10I	109.5
C4B—C5B—C6B	110 (3)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	111.1 (15)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.7	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.7

O1—C1—C2—C3	175.6 (6)	C3B—C2B—C7B—C9B	−75 (2)
O1—C1—C2—C7	−55.3 (13)	C3B—C4B—C5B—C6B	−55 (3)
O1—C1—C6—C5	−173.4 (13)	C3B—C4B—C5B—C10B	−180 (3)
C1—C2—C3—C4	−57.3 (13)	C4B—C5B—C6B—C1B	56 (2)
C1—C2—C7—C8	−74.0 (13)	C6B—C1B—C2B—C3B	67 (3)
C1—C2—C7—C9	162.0 (16)	C6B—C1B—C2B—C7B	−170 (3)
C2—C1—C6—C5	−55.0 (18)	C7B—C2B—C3B—C4B	172.5 (7)
C2—C3—C4—C5	61 (2)	C10B—C5B—C6B—C1B	−179.5 (10)
C3—C2—C7—C8	51.3 (12)	C1C—C2C—C3C—C4C	−56.5 (18)
C3—C2—C7—C9	−72.7 (17)	C1C—C2C—C7C—C8C	−67 (2)
C3—C4—C5—C6	−59.4 (17)	C1C—C2C—C7C—C9C	171.7 (19)
C3—C4—C5—C10	176.8 (18)	C1C—C6C—C5C—C4C	54 (2)
C4—C5—C6—C1	55.5 (13)	C1C—C6C—C5C—C10C	−177.7 (9)
C6—C1—C2—C3	53.7 (14)	C5C—C6C—C1C—O1C	−173.2 (17)
C6—C1—C2—C7	−177.2 (14)	C5C—C6C—C1C—C2C	−54 (3)
C7—C2—C3—C4	173.8 (11)	C5C—C4C—C3C—C2C	60 (2)
C10—C5—C6—C1	179.9 (12)	C3C—C2C—C1C—O1C	175.4 (13)
O1B—C1B—C2B—C3B	−177.6 (15)	C3C—C2C—C1C—C6C	54 (3)
O1B—C1B—C2B—C7B	−54 (3)	C3C—C2C—C7C—C8C	55 (2)
O1B—C1B—C6B—C5B	179.3 (17)	C3C—C2C—C7C—C9C	−66 (2)
C1B—C2B—C3B—C4B	−64 (2)	C3C—C4C—C5C—C6C	−57 (2)
C1B—C2B—C7B—C8B	−65 (3)	C3C—C4C—C5C—C10C	174 (3)
C1B—C2B—C7B—C9B	166 (3)	C7C—C2C—C1C—O1C	−54 (2)
C2B—C1B—C6B—C5B	−63 (4)	C7C—C2C—C1C—C6C	−176 (3)
C2B—C3B—C4B—C5B	61 (3)	C7C—C2C—C3C—C4C	179.2 (6)
C3B—C2B—C7B—C8B	54 (2)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.51GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.070 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.735 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0842 (15) Å	Cell parameters from 1421 reflections
c = 12.5710 (16) Å	θ = 3.1–28.4°
α = 117.421 (13)°	µ = 0.07 mm⁻¹
β = 99.67 (10)°	T = 296 K
γ = 103.75 (9)°	Plate, colourless
V = 1455.3 (13) Å³	0.38 × 0.33 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	394 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.244
ω scans	θ_max = 29.4°, θ_min = 2.8°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
T_min = 0.975, T_max = 0.996	k = −13→12
8658 measured reflections	l = −16→16
1416 independent reflections

Refinement top

Refinement on F²	216 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.250	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.004
1416 reflections	Δρ_max = 0.07 e Å⁻³
313 parameters	Δρ_min = −0.07 e Å⁻³

Special details top

Experimental. Data were collected at room temperature and pressure of 0.51 (2) GPa (510000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5417 (11)	1.085 (2)	0.1352 (16)	0.123 (9)
H1B	0.609742	1.078324	0.135342	0.185*	0.5
H1A	0.52 (2)	1.067 (6)	0.0622 (16)	0.185*	0.5
C1	0.5550 (19)	1.221 (2)	0.1938 (18)	0.113 (9)
H1	0.475701	1.230717	0.169025	0.136*
C2	0.5917 (18)	1.261 (3)	0.325 (2)	0.110 (8)
H2	0.670090	1.249338	0.348298	0.166*
C3	0.6126 (11)	1.401 (2)	0.3778 (17)	0.077 (6)
H3A	0.632487	1.442590	0.468812	0.092*
H3B	0.534912	1.408170	0.346775	0.092*
C4	0.7147 (10)	1.485 (3)	0.352 (3)	0.105 (6)
H4A	0.718364	1.576682	0.391669	0.157*
H4B	0.795029	1.484514	0.386043	0.157*
C5	0.6805 (16)	1.422 (3)	0.210 (3)	0.100 (8)
H5	0.605421	1.435820	0.180918	0.150*
C6	0.6532 (14)	1.296 (4)	0.161 (3)	0.082 (7)
H6A	0.728827	1.281472	0.184947	0.123*
H6B	0.626680	1.254551	0.069918	0.123*
C7	0.5020 (11)	1.205 (3)	0.375 (2)	0.090 (6)
H7	0.477385	1.107934	0.321435	0.135*
C8	0.3798 (10)	1.231 (3)	0.368 (3)	0.100 (9)
H8A	0.331927	1.189396	0.403201	0.120*
H8B	0.397508	1.325879	0.415527	0.120*
H8C	0.333768	1.195206	0.281442	0.120*
C9	0.5585 (10)	1.238 (3)	0.506 (2)	0.104 (9)
H9A	0.496227	1.199010	0.531833	0.125*
H9B	0.623323	1.202279	0.507395	0.125*
H9C	0.592258	1.332971	0.562038	0.125*
C10	0.7825 (11)	1.492 (3)	0.178 (3)	0.126 (10)
H10A	0.795147	1.585101	0.219037	0.151*
H10B	0.857890	1.480549	0.206041	0.151*
H10C	0.759035	1.453603	0.087764	0.151*
O1B	0.7343 (6)	0.9932 (18)	0.1112 (15)	0.106 (8)
H1BA	0.803 (3)	1.031 (8)	0.113 (5)	0.158*	0.5
H1BB	0.704 (4)	1.050 (4)	0.144 (13)	0.158*	0.5
C1B	0.7498 (13)	0.932 (4)	0.182 (3)	0.084 (6)
H1BC	0.806283	0.883070	0.159478	0.126*
C2B	0.7993 (16)	1.041 (5)	0.332 (4)	0.110 (7)
H2B	0.730681	1.071900	0.349382	0.166*
C3B	0.8147 (12)	0.971 (3)	0.403 (3)	0.112 (6)
H3BA	0.837834	1.034306	0.493036	0.168*
H3BB	0.880084	0.935766	0.387467	0.168*
C4B	0.6912 (15)	0.856 (3)	0.358 (3)	0.123 (7)
H4BA	0.705166	0.807547	0.399691	0.185*
H4BB	0.631413	0.895594	0.388104	0.185*
C5B	0.6329 (13)	0.755 (3)	0.216 (3)	0.106 (6)
H5B	0.689544	0.708766	0.186900	0.159*
C6B	0.6281 (11)	0.841 (3)	0.157 (2)	0.091 (6)
H6BA	0.588801	0.783158	0.065981	0.136*
H6BB	0.577358	0.893278	0.189669	0.136*
C7B	0.919 (2)	1.178 (5)	0.382 (3)	0.096 (7)
H7B	0.902672	1.224028	0.337551	0.145*
C8B	1.0297 (11)	1.120 (3)	0.351 (3)	0.100 (9)
H8BA	1.011002	1.067166	0.260572	0.120*
H8BB	1.106998	1.193213	0.386392	0.120*
H8BC	1.035920	1.065697	0.386317	0.120*
C9B	0.934 (2)	1.243 (6)	0.487 (4)	0.165 (13)
H9BA	0.865275	1.272774	0.498161	0.198*
H9BB	0.938107	1.190917	0.526353	0.198*
H9BC	1.009185	1.318433	0.526428	0.198*
C10B	0.5023 (14)	0.648 (4)	0.173 (3)	0.134 (10)
H10D	0.508478	0.595821	0.210876	0.161*
H10E	0.444988	0.691607	0.198388	0.161*
H10F	0.473469	0.590297	0.082108	0.161*
O1C	0.9245 (6)	1.0690 (17)	0.0405 (13)	0.102 (8)
H1CA	0.861 (4)	1.023 (5)	0.041 (5)	0.154*	0.5
H1C	0.9653 (14)	1.0265 (17)	0.005 (3)	0.154*	0.5
C2C	1.0466 (11)	1.248 (3)	0.029 (2)	0.083 (6)
H2C	1.076100	1.184765	−0.032258	0.125*
C6C	0.8286 (9)	1.113 (3)	−0.112 (2)	0.076 (5)
H6CA	0.845622	1.039190	−0.174188	0.114*
H6CB	0.746926	1.075987	−0.108710	0.114*
C4C	0.9491 (11)	1.270 (3)	−0.153 (2)	0.099 (6)
H4CA	0.946445	1.327355	−0.186150	0.149*
H4CB	0.977509	1.201051	−0.206117	0.149*
C1C	0.9204 (11)	1.169 (3)	0.014 (2)	0.091 (6)
H1CB	0.892082	1.229942	0.077343	0.136*
C5C	0.8255 (12)	1.207 (3)	−0.155 (2)	0.103 (6)
H5C	0.799814	1.276945	−0.096681	0.154*
C3C	1.0457 (11)	1.357 (3)	−0.008 (3)	0.102 (6)
H3CA	1.127614	1.402329	−0.004288	0.153*
H3CB	1.016512	1.422878	0.048605	0.153*
C7C	1.1378 (18)	1.308 (5)	0.157 (4)	0.094 (7)
H7C	1.136276	1.236541	0.174833	0.142*
C8C	1.119 (2)	1.439 (6)	0.285 (4)	0.166 (12)
H8CA	1.181949	1.468596	0.361567	0.199*
H8CB	1.124909	1.511213	0.270994	0.199*
H8CC	1.038686	1.407439	0.291996	0.199*
C9C	1.2734 (13)	1.381 (4)	0.174 (3)	0.137 (10)
H9CA	1.325300	1.416538	0.257930	0.164*
H9CB	1.302147	1.319783	0.113751	0.164*
H9CC	1.276574	1.453266	0.159093	0.164*
C10C	0.7257 (12)	1.129 (3)	−0.295 (3)	0.117 (9)
H10G	0.645368	1.088702	−0.293704	0.140*
H10H	0.722606	1.190244	−0.322820	0.140*
H10I	0.750064	1.059986	−0.352998	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.107 (7)	0.12 (2)	0.131 (19)	0.019 (13)	0.023 (10)	0.077 (18)
C1	0.095 (9)	0.115 (15)	0.120 (14)	0.056 (10)	0.037 (8)	0.044 (11)
C2	0.126 (10)	0.110 (15)	0.108 (12)	0.044 (9)	0.031 (7)	0.068 (11)
C3	0.061 (7)	0.078 (13)	0.081 (12)	0.031 (8)	0.034 (7)	0.028 (10)
C4	0.087 (7)	0.104 (14)	0.114 (11)	0.044 (8)	0.029 (7)	0.046 (10)
C5	0.105 (9)	0.095 (14)	0.108 (12)	0.034 (9)	0.041 (7)	0.058 (11)
C6	0.078 (8)	0.080 (14)	0.085 (12)	0.024 (8)	0.032 (7)	0.041 (10)
C7	0.090 (7)	0.092 (13)	0.091 (11)	0.028 (7)	0.028 (7)	0.053 (10)
C8	0.079 (7)	0.09 (2)	0.123 (18)	0.021 (11)	0.037 (10)	0.051 (18)
C9	0.092 (8)	0.09 (2)	0.120 (18)	0.026 (11)	0.034 (10)	0.052 (18)
C10	0.118 (9)	0.12 (2)	0.131 (18)	0.024 (12)	0.040 (10)	0.068 (18)
O1B	0.111 (6)	0.11 (2)	0.106 (14)	0.025 (9)	0.030 (8)	0.073 (16)
C1B	0.079 (7)	0.084 (14)	0.086 (11)	0.036 (7)	0.026 (7)	0.040 (10)
C2B	0.105 (8)	0.111 (14)	0.114 (12)	0.037 (8)	0.037 (8)	0.058 (11)
C3B	0.108 (7)	0.115 (13)	0.110 (11)	0.041 (8)	0.043 (7)	0.054 (10)
C4B	0.133 (10)	0.118 (14)	0.126 (12)	0.042 (8)	0.031 (7)	0.074 (11)
C5B	0.099 (8)	0.107 (14)	0.114 (11)	0.045 (8)	0.040 (7)	0.052 (10)
C6B	0.090 (7)	0.092 (13)	0.094 (11)	0.039 (7)	0.036 (7)	0.047 (10)
C7B	0.086 (9)	0.097 (14)	0.102 (12)	0.042 (8)	0.040 (8)	0.040 (11)
C8B	0.083 (7)	0.11 (2)	0.089 (19)	0.056 (11)	0.050 (10)	0.023 (18)
C9B	0.116 (13)	0.16 (3)	0.19 (2)	0.049 (14)	0.074 (15)	0.06 (2)
C10B	0.143 (10)	0.13 (2)	0.147 (19)	0.038 (13)	0.057 (11)	0.081 (19)
O1C	0.113 (5)	0.09 (2)	0.126 (15)	0.035 (9)	0.033 (8)	0.079 (17)
C2C	0.089 (7)	0.082 (13)	0.083 (10)	0.025 (7)	0.028 (7)	0.049 (10)
C6C	0.079 (6)	0.077 (13)	0.079 (10)	0.032 (7)	0.041 (6)	0.038 (10)
C4C	0.116 (8)	0.102 (13)	0.095 (11)	0.039 (8)	0.034 (7)	0.063 (10)
C1C	0.100 (7)	0.094 (13)	0.084 (11)	0.033 (8)	0.019 (7)	0.055 (10)
C5C	0.109 (8)	0.097 (13)	0.110 (11)	0.050 (8)	0.021 (7)	0.059 (10)
C3C	0.105 (7)	0.104 (13)	0.100 (11)	0.034 (7)	0.032 (7)	0.058 (10)
C7C	0.100 (8)	0.091 (14)	0.098 (12)	0.040 (8)	0.025 (7)	0.053 (10)
C8C	0.168 (14)	0.18 (3)	0.14 (2)	0.069 (16)	0.022 (13)	0.08 (2)
C9C	0.116 (9)	0.15 (3)	0.14 (2)	0.057 (13)	0.046 (11)	0.063 (19)
C10C	0.135 (9)	0.13 (2)	0.113 (18)	0.066 (12)	0.041 (10)	0.071 (18)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.531 (19)
O1—H1A	0.8200 (13)	C5B—C10B	1.57 (3)
O1—C1	1.418 (19)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.444 (17)	C7B—H7B	0.9800
C1—C6	1.52 (2)	C7B—C8B	1.64 (4)
C2—H2	0.9800	C7B—C9B	1.14 (7)
C2—C3	1.44 (2)	C8B—H8BA	0.9600
C2—C7	1.489 (17)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.558 (14)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.52 (2)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.27 (5)	O1C—H1CA	0.8200 (14)
C5—C10	1.518 (16)	O1C—H1C	0.8200 (14)
C6—H6A	0.9700	O1C—C1C	1.401 (19)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.487 (15)
C7—C8	1.538 (18)	C2C—C3C	1.59 (3)
C7—C9	1.49 (2)	C2C—C7C	1.50 (3)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.48 (2)
C9—H9A	0.9600	C6C—C5C	1.48 (2)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.456 (12)
C10—H10B	0.9600	C4C—C3C	1.64 (3)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (15)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (13)	C5C—C10C	1.62 (3)
O1B—C1B	1.419 (15)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.61 (5)	C7C—H7C	0.9800
C1B—C6B	1.45 (2)	C7C—C8C	1.76 (8)
C2B—H2B	0.9800	C7C—C9C	1.55 (2)
C2B—C3B	1.50 (2)	C8C—H8CA	0.9600
C2B—C7B	1.66 (5)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.55 (2)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.53 (2)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	99.3	C10B—C5B—H5B	108.2
C1—O1—H1B	109.5	C1B—C6B—C5B	113.1 (10)
C1—O1—H1A	96 (2)	C1B—C6B—H6BA	109.0
O1—C1—H1	110.8	C1B—C6B—H6BB	109.0
O1—C1—C2	100 (2)	C5B—C6B—H6BA	109.0
O1—C1—C6	110 (2)	C5B—C6B—H6BB	109.0
C2—C1—H1	110.8	H6BA—C6B—H6BB	107.8
C2—C1—C6	113.1 (17)	C2B—C7B—H7B	111.5
C6—C1—H1	110.8	C8B—C7B—C2B	103 (3)
C1—C2—H2	109.9	C8B—C7B—H7B	111.5
C1—C2—C7	119.7 (18)	C9B—C7B—C2B	104 (3)
C3—C2—C1	97.0 (12)	C9B—C7B—H7B	111.5
C3—C2—H2	109.9	C9B—C7B—C8B	114 (2)
C3—C2—C7	110 (2)	C7B—C8B—H8BA	109.5
C7—C2—H2	109.9	C7B—C8B—H8BB	109.5
C2—C3—H3A	107.6	C7B—C8B—H8BC	109.5
C2—C3—H3B	107.6	H8BA—C8B—H8BB	109.5
C2—C3—C4	118.8 (19)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.0	H8BB—C8B—H8BC	109.5
C4—C3—H3A	107.6	C7B—C9B—H9BA	109.5
C4—C3—H3B	107.6	C7B—C9B—H9BB	109.5
C3—C4—H4A	110.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	110.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	108.5	H9BA—C9B—H9BC	109.5
C5—C4—C3	107.2 (16)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	110.3	C5B—C10B—H10D	109.5
C5—C4—H4B	110.3	C5B—C10B—H10E	109.5
C4—C5—H5	107.6	C5B—C10B—H10F	109.5
C4—C5—C10	109.8 (18)	H10D—C10B—H10E	109.5
C6—C5—C4	107 (2)	H10D—C10B—H10F	109.5
C6—C5—H5	107.6	H10E—C10B—H10F	109.5
C6—C5—C10	117 (3)	H1CA—O1C—H1C	114 (6)
C10—C5—H5	107.6	C1C—O1C—H1CA	119 (6)
C1—C6—H6A	107.6	C1C—O1C—H1C	112 (2)
C1—C6—H6B	107.6	C1C—C2C—H2C	106.5
C5—C6—C1	119 (3)	C1C—C2C—C3C	112.4 (10)
C5—C6—H6A	107.6	C1C—C2C—C7C	113.0 (11)
C5—C6—H6B	107.6	C3C—C2C—H2C	106.5
H6A—C6—H6B	107.0	C7C—C2C—H2C	106.5
C2—C7—H7	105.1	C7C—C2C—C3C	111 (2)
C2—C7—C8	119.0 (11)	H6CA—C6C—H6CB	107.4
C2—C7—C9	113.5 (13)	C1C—C6C—H6CA	108.3
C8—C7—H7	105.1	C1C—C6C—H6CB	108.3
C9—C7—H7	105.1	C5C—C6C—H6CA	108.3
C9—C7—C8	107.8 (15)	C5C—C6C—H6CB	108.3
C7—C8—H8A	109.5	C5C—C6C—C1C	115.9 (19)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.1
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.6
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.6
H8A—C8—H8C	109.5	C5C—C4C—C3C	110.2 (13)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.6
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.6
C7—C9—H9B	109.5	O1C—C1C—C2C	110.6 (10)
C7—C9—H9C	109.5	O1C—C1C—C6C	111.5 (19)
H9A—C9—H9B	109.5	O1C—C1C—H1CB	107.0
H9A—C9—H9C	109.5	C2C—C1C—C6C	113.4 (10)
H9B—C9—H9C	109.5	C2C—C1C—H1CB	107.0
C5—C10—H10A	109.5	C6C—C1C—H1CB	107.0
C5—C10—H10B	109.5	C6C—C5C—H5C	108.9
C5—C10—H10C	109.5	C6C—C5C—C10C	109 (2)
H10A—C10—H10B	109.5	C4C—C5C—C6C	109.3 (10)
H10A—C10—H10C	109.5	C4C—C5C—H5C	108.9
H10B—C10—H10C	109.5	C4C—C5C—C10C	111.4 (13)
H1BA—O1B—H1BB	108 (9)	C10C—C5C—H5C	108.9
C1B—O1B—H1BA	107 (7)	C2C—C3C—C4C	103 (2)
C1B—O1B—H1BB	110 (10)	C2C—C3C—H3CA	111.1
O1B—C1B—H1BC	110.8	C2C—C3C—H3CB	111.1
O1B—C1B—C2B	110 (3)	C4C—C3C—H3CA	111.1
O1B—C1B—C6B	107.6 (10)	C4C—C3C—H3CB	111.1
C2B—C1B—H1BC	110.8	H3CA—C3C—H3CB	109.1
C6B—C1B—H1BC	110.8	C2C—C7C—H7C	108.6
C6B—C1B—C2B	106.3 (16)	C2C—C7C—C8C	117.1 (16)
C1B—C2B—H2B	105.3	C2C—C7C—C9C	114.9 (14)
C1B—C2B—C7B	116.9 (17)	C8C—C7C—H7C	108.6
C3B—C2B—C1B	108 (3)	C9C—C7C—H7C	108.6
C3B—C2B—H2B	105.3	C9C—C7C—C8C	98 (4)
C3B—C2B—C7B	114.4 (19)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	105.3	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.8	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.8	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	109.4 (14)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.3	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.8	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.8	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.0	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.0	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.3	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	117.0 (14)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.0	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.0	C5C—C10C—H10H	109.5
C4B—C5B—H5B	108.2	C5C—C10C—H10I	109.5
C4B—C5B—C10B	115.7 (17)	H10G—C10C—H10H	109.5
C6B—C5B—C4B	104.6 (19)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	108.2	H10H—C10C—H10I	109.5
C6B—C5B—C10B	111.6 (12)

O1—C1—C2—C3	175.7 (18)	C3B—C2B—C7B—C9B	−55 (4)
O1—C1—C2—C7	−67 (3)	C3B—C4B—C5B—C6B	−51.5 (17)
O1—C1—C6—C5	−178 (2)	C3B—C4B—C5B—C10B	−174.7 (16)
C1—C2—C3—C4	−61.9 (19)	C4B—C5B—C6B—C1B	61 (2)
C1—C2—C7—C8	−61 (3)	C6B—C1B—C2B—C3B	63.8 (18)
C1—C2—C7—C9	171 (2)	C6B—C1B—C2B—C7B	−165.1 (17)
C2—C1—C6—C5	−66 (3)	C7B—C2B—C3B—C4B	173 (3)
C2—C3—C4—C5	59.3 (19)	C10B—C5B—C6B—C1B	−173 (3)
C3—C2—C7—C8	50 (3)	C1C—C2C—C3C—C4C	−56 (2)
C3—C2—C7—C9	−79 (2)	C1C—C2C—C7C—C8C	−70 (3)
C3—C4—C5—C6	−47 (2)	C1C—C2C—C7C—C9C	175 (3)
C3—C4—C5—C10	−175.1 (19)	C1C—C6C—C5C—C4C	55 (3)
C4—C5—C6—C1	54 (2)	C1C—C6C—C5C—C10C	177.1 (15)
C6—C1—C2—C3	58 (2)	C5C—C6C—C1C—O1C	−174.3 (15)
C6—C1—C2—C7	175 (2)	C5C—C6C—C1C—C2C	−49 (2)
C7—C2—C3—C4	173.0 (11)	C5C—C4C—C3C—C2C	63.3 (19)
C10—C5—C6—C1	177.8 (13)	C3C—C2C—C1C—O1C	177 (2)
O1B—C1B—C2B—C3B	−179.7 (9)	C3C—C2C—C1C—C6C	51 (3)
O1B—C1B—C2B—C7B	−49 (2)	C3C—C2C—C7C—C8C	58 (3)
O1B—C1B—C6B—C5B	173 (2)	C3C—C2C—C7C—C9C	−57 (3)
C1B—C2B—C3B—C4B	−55 (2)	C3C—C4C—C5C—C6C	−63 (3)
C1B—C2B—C7B—C8B	−64 (2)	C3C—C4C—C5C—C10C	176 (2)
C1B—C2B—C7B—C9B	177 (3)	C7C—C2C—C1C—O1C	−56 (3)
C2B—C1B—C6B—C5B	−69 (3)	C7C—C2C—C1C—C6C	178 (2)
C2B—C3B—C4B—C5B	53 (3)	C7C—C2C—C3C—C4C	176.1 (15)
C3B—C2B—C7B—C8B	65 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.60GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.086 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.601 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.022 (3) Å	Cell parameters from 1268 reflections
c = 12.596 (2) Å	θ = 5.0–26.7°
α = 117.58 (2)°	µ = 0.07 mm⁻¹
β = 99.50 (3)°	T = 296 K
γ = 103.76 (4)°	Plate, colourless
V = 1432.9 (13) Å³	0.45 × 0.45 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	1268 independent reflections
Radiation source: Enhance (Mo) X-ray Source	589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.101
Detector resolution: 16.4 pixels mm^-1	θ_max = 26.7°, θ_min = 5.0°
ω scans	h = −6→6
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −15→15
T_min = 0.975, T_max = 0.996	l = −15→15
6663 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.064	w = 1/[σ²(F_o²) + (0.1195P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.203	(Δ/σ)_max = 0.005
S = 1.01	Δρ_max = 0.08 e Å⁻³
1268 reflections	Δρ_min = −0.07 e Å⁻³
314 parameters	Extinction correction: SHELXL-2017/1 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 restraints	Extinction coefficient: 0.020 (16)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.60 (2) GPa (600000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5398 (13)	1.0727 (6)	0.1285 (4)	0.075 (8)
H1B	0.606661	1.061714	0.126588	0.113*	0.5
H1A	0.483 (6)	1.010 (8)	0.065 (5)	0.113*	0.5
C1	0.559 (2)	1.2093 (11)	0.1830 (7)	0.061 (5)
H1	0.479297	1.216483	0.153243	0.091*
C2	0.594 (2)	1.2755 (9)	0.3243 (6)	0.058 (5)
H2	0.675749	1.272321	0.354791	0.087*
C3	0.608 (2)	1.4206 (9)	0.3844 (7)	0.063 (5)
H3A	0.528081	1.428083	0.357172	0.095*
H3B	0.634356	1.463989	0.475681	0.095*
C4	0.701 (3)	1.4847 (11)	0.3458 (8)	0.080 (5)
H4A	0.780943	1.483805	0.381958	0.120*
H4B	0.708353	1.578108	0.383000	0.120*
C5	0.678 (3)	1.4252 (12)	0.2059 (9)	0.084 (5)
H5	0.602817	1.437087	0.171860	0.126*
C6	0.651 (2)	1.2761 (11)	0.1446 (7)	0.067 (5)
H6A	0.619714	1.234472	0.053610	0.101*
H6B	0.728018	1.261953	0.165172	0.101*
C7	0.500 (3)	1.2036 (13)	0.3671 (9)	0.069 (5)
H7	0.480147	1.106806	0.311549	0.104*
C8	0.377 (4)	1.2270 (15)	0.3604 (11)	0.084 (9)
H8A	0.326225	1.177954	0.388987	0.100*
H8B	0.392665	1.321248	0.413265	0.100*
H8C	0.332998	1.196587	0.274663	0.100*
C9	0.566 (3)	1.2412 (14)	0.5040 (8)	0.133 (10)
H9A	0.644249	1.226335	0.507937	0.160*
H9B	0.582015	1.334155	0.562435	0.160*
H9C	0.513192	1.186123	0.525674	0.160*
C10	0.787 (3)	1.4923 (14)	0.1718 (11)	0.105 (9)
H10A	0.765719	1.449092	0.081627	0.126*
H10B	0.799840	1.585981	0.208138	0.126*
H10C	0.862509	1.482873	0.204812	0.126*
O1B	0.7386 (15)	0.9980 (7)	0.1138 (5)	0.119 (8)
H1BA	0.805 (3)	1.053 (4)	0.127 (3)	0.179*	0.5
H1BB	0.7016 (19)	1.050 (3)	0.142 (7)	0.179*	0.5
C1B	0.753 (3)	0.9390 (14)	0.1919 (9)	0.079 (6)
H1BC	0.816561	0.897419	0.174916	0.119*
C2B	0.792 (4)	1.0365 (15)	0.3290 (10)	0.090 (6)
H2B	0.724846	1.071951	0.347730	0.136*
C3B	0.811 (3)	0.9656 (15)	0.4008 (9)	0.094 (6)
H3BA	0.876866	0.929485	0.383264	0.141*
H3BB	0.835742	1.028589	0.491112	0.141*
C4B	0.692 (3)	0.8562 (16)	0.3585 (11)	0.111 (6)
H4BA	0.703521	0.806252	0.399232	0.167*
H4BB	0.629545	0.894397	0.384158	0.167*
C5B	0.648 (3)	0.7651 (15)	0.2226 (11)	0.096 (6)
H5B	0.705487	0.717590	0.198319	0.144*
C6B	0.635 (3)	0.8352 (12)	0.1505 (8)	0.068 (5)
H6BA	0.611161	0.771251	0.060488	0.101*
H6BB	0.570772	0.874035	0.166090	0.101*
C7B	0.918 (4)	1.1598 (18)	0.3707 (11)	0.095 (6)
H7B	0.900772	1.192988	0.314288	0.143*
C8B	1.032 (5)	1.131 (3)	0.3595 (14)	0.115 (10)
H8BA	1.016038	1.059011	0.275153	0.138*
H8BB	1.096759	1.209925	0.377509	0.138*
H8BC	1.057853	1.105424	0.418547	0.138*
C9B	0.936 (3)	1.2736 (15)	0.5026 (10)	0.154 (10)
H9BA	0.858526	1.288655	0.505125	0.184*
H9BB	0.960690	1.249650	0.563308	0.184*
H9BC	0.999596	1.354151	0.522270	0.184*
C10B	0.515 (3)	0.6602 (15)	0.1831 (11)	0.110 (10)
H10D	0.485310	0.599630	0.093056	0.132*
H10E	0.520682	0.610324	0.223929	0.132*
H10F	0.458281	0.706210	0.207919	0.132*
O1C	0.9311 (13)	1.0739 (6)	0.0463 (5)	0.093 (8)
H1CA	0.884 (3)	1.060 (7)	0.085 (3)	0.140*	0.5
H1C	0.9797 (17)	1.033 (2)	0.0350 (12)	0.140*	0.5
C2C	1.054 (3)	1.2531 (14)	0.0324 (10)	0.070 (6)
H2C	1.084289	1.188193	−0.026861	0.105*
C6C	0.820 (2)	1.1056 (9)	−0.1140 (7)	0.058 (5)
H6CA	0.738814	1.058364	−0.115521	0.087*
H6CB	0.847165	1.039004	−0.173277	0.087*
C4C	0.950 (3)	1.2761 (14)	−0.1464 (10)	0.068 (6)
H4CA	0.979777	1.209237	−0.201663	0.102*
H4CB	0.951364	1.339435	−0.173910	0.102*
C1C	0.907 (3)	1.1692 (14)	0.0107 (10)	0.075 (6)
H1CB	0.876068	1.229751	0.072533	0.112*
C5C	0.805 (3)	1.2012 (15)	−0.1598 (11)	0.080 (6)
H5C	0.775227	1.267679	−0.102132	0.121*
C3C	1.034 (2)	1.3466 (9)	−0.0188 (7)	0.073 (5)
H3CA	1.001675	1.409929	0.036662	0.109*
H3CB	1.114821	1.398008	−0.014906	0.109*
C7C	1.147 (3)	1.3207 (16)	0.1601 (11)	0.072 (6)
H7C	1.147513	1.248991	0.177147	0.109*
C8C	1.105 (3)	1.4174 (13)	0.2634 (8)	0.100 (9)
H8CA	1.166554	1.459241	0.344418	0.120*
H8CB	1.094365	1.485301	0.246651	0.120*
H8CC	1.026324	1.367967	0.263389	0.120*
C9C	1.283 (5)	1.380 (2)	0.1607 (18)	0.141 (12)
H9CA	1.341123	1.422834	0.244162	0.169*
H9CB	1.305438	1.308722	0.102456	0.169*
H9CC	1.286927	1.444741	0.135752	0.169*
C10C	0.724 (2)	1.1362 (11)	−0.2869 (7)	0.089 (9)
H10G	0.719308	1.202747	−0.307873	0.106*
H10H	0.755749	1.075368	−0.343881	0.106*
H10I	0.641327	1.087128	−0.294080	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.09 (2)	0.059 (5)	0.069 (3)	0.023 (9)	0.039 (7)	0.026 (3)
C1	0.064 (14)	0.066 (6)	0.061 (4)	0.023 (8)	0.036 (7)	0.034 (4)
C2	0.051 (14)	0.060 (5)	0.057 (4)	0.024 (8)	0.013 (7)	0.025 (4)
C3	0.060 (14)	0.057 (6)	0.059 (4)	0.013 (8)	0.018 (7)	0.024 (4)
C4	0.078 (14)	0.069 (6)	0.083 (5)	0.021 (8)	0.034 (8)	0.032 (4)
C5	0.086 (14)	0.068 (6)	0.100 (6)	0.018 (8)	0.040 (8)	0.047 (5)
C6	0.066 (14)	0.072 (6)	0.066 (4)	0.032 (8)	0.024 (7)	0.034 (4)
C7	0.075 (14)	0.067 (6)	0.067 (5)	0.019 (9)	0.038 (8)	0.034 (4)
C8	0.08 (3)	0.088 (9)	0.099 (7)	0.040 (14)	0.050 (13)	0.046 (6)
C9	0.13 (3)	0.168 (10)	0.089 (6)	0.019 (15)	0.013 (11)	0.082 (7)
C10	0.12 (3)	0.090 (8)	0.132 (7)	0.041 (12)	0.065 (12)	0.072 (6)
O1B	0.15 (2)	0.123 (6)	0.113 (4)	0.039 (11)	0.034 (8)	0.091 (4)
C1B	0.085 (14)	0.082 (6)	0.079 (6)	0.026 (8)	0.024 (8)	0.051 (5)
C2B	0.094 (14)	0.084 (7)	0.090 (6)	0.020 (9)	0.028 (8)	0.050 (5)
C3B	0.096 (14)	0.111 (7)	0.075 (5)	0.014 (9)	0.032 (8)	0.057 (5)
C4B	0.127 (15)	0.115 (8)	0.114 (7)	0.026 (9)	0.037 (8)	0.085 (6)
C5B	0.093 (14)	0.087 (7)	0.107 (7)	0.037 (9)	0.031 (8)	0.050 (6)
C6B	0.068 (14)	0.063 (6)	0.060 (5)	0.010 (8)	0.017 (7)	0.031 (4)
C7B	0.098 (14)	0.102 (8)	0.084 (6)	0.039 (10)	0.020 (8)	0.049 (6)
C8B	0.12 (3)	0.140 (12)	0.131 (8)	0.081 (16)	0.055 (15)	0.084 (8)
C9B	0.14 (3)	0.138 (11)	0.132 (8)	0.033 (15)	0.076 (13)	0.032 (7)
C10B	0.10 (3)	0.081 (9)	0.121 (8)	0.034 (14)	0.009 (13)	0.037 (7)
O1C	0.11 (2)	0.079 (5)	0.106 (4)	0.018 (10)	0.030 (7)	0.069 (4)
C2C	0.076 (14)	0.065 (6)	0.079 (6)	0.023 (9)	0.033 (8)	0.043 (5)
C6C	0.053 (14)	0.055 (5)	0.062 (4)	0.014 (7)	0.016 (7)	0.031 (4)
C4C	0.072 (14)	0.072 (7)	0.065 (6)	0.021 (9)	0.026 (8)	0.041 (5)
C1C	0.082 (15)	0.073 (7)	0.079 (6)	0.017 (9)	0.024 (8)	0.053 (5)
C5C	0.080 (15)	0.085 (7)	0.079 (6)	0.028 (9)	0.029 (8)	0.045 (5)
C3C	0.076 (14)	0.075 (5)	0.075 (5)	0.026 (8)	0.016 (7)	0.048 (4)
C7C	0.076 (15)	0.083 (7)	0.064 (6)	0.029 (9)	0.016 (8)	0.045 (5)
C8C	0.08 (3)	0.129 (9)	0.086 (6)	0.045 (13)	0.032 (10)	0.050 (6)
C9C	0.14 (3)	0.157 (15)	0.130 (10)	0.029 (17)	0.060 (15)	0.086 (10)
C10C	0.08 (3)	0.103 (8)	0.073 (6)	0.026 (13)	0.019 (10)	0.045 (6)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.510 (13)
O1—H1A	0.8200 (13)	C5B—C10B	1.56 (5)
O1—C1	1.396 (8)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.505 (10)	C7B—H7B	0.9800
C1—C6	1.46 (3)	C7B—C8B	1.45 (6)
C2—H2	0.9800	C7B—C9B	1.524 (14)
C2—C3	1.499 (9)	C8B—H8BA	0.9600
C2—C7	1.55 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.46 (3)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.508 (12)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.508 (13)	O1C—H1CA	0.8200 (12)
C5—C10	1.56 (4)	O1C—H1C	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.475 (11)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.67 (5)
C7—C8	1.52 (4)	C2C—C3C	1.575 (12)
C7—C9	1.561 (15)	C2C—C7C	1.49 (3)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.44 (2)
C9—H9A	0.9600	C6C—C5C	1.536 (12)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.65 (5)
C10—H10B	0.9600	C4C—C3C	1.44 (2)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (13)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.43 (2)
O1B—C1B	1.466 (9)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.476 (14)	C7C—H7C	0.9800
C1B—C6B	1.43 (4)	C7C—C8C	1.54 (2)
C2B—H2B	0.9800	C7C—C9C	1.57 (7)
C2B—C3B	1.528 (13)	C8C—H8CA	0.9600
C2B—C7B	1.62 (6)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.47 (4)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.449 (14)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	110.3	C10B—C5B—H5B	109.0
C1—O1—H1B	109.5	C1B—C6B—C5B	108 (2)
C1—O1—H1A	126 (9)	C1B—C6B—H6BA	110.0
O1—C1—H1	107.4	C1B—C6B—H6BB	110.0
O1—C1—C2	109.5 (6)	C5B—C6B—H6BA	110.0
O1—C1—C6	112.5 (11)	C5B—C6B—H6BB	110.0
C2—C1—H1	107.4	H6BA—C6B—H6BB	108.4
C6—C1—H1	107.4	C2B—C7B—H7B	105.7
C6—C1—C2	112.4 (16)	C8B—C7B—C2B	118.2 (13)
C1—C2—H2	107.5	C8B—C7B—H7B	105.7
C1—C2—C7	113.3 (15)	C8B—C7B—C9B	113 (3)
C3—C2—C1	110.4 (6)	C9B—C7B—C2B	108 (3)
C3—C2—H2	107.5	C9B—C7B—H7B	105.7
C3—C2—C7	110.2 (14)	C7B—C8B—H8BA	109.5
C7—C2—H2	107.5	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.1	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.1	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.4	H8BA—C8B—H8BC	109.5
C4—C3—C2	107.9 (14)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.1	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.1	C7B—C9B—H9BB	109.5
C3—C4—H4A	107.9	C7B—C9B—H9BC	109.5
C3—C4—H4B	107.9	H9BA—C9B—H9BB	109.5
C3—C4—C5	117.4 (18)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.2	H9BB—C9B—H9BC	109.5
C5—C4—H4A	107.9	C5B—C10B—H10D	109.5
C5—C4—H4B	107.9	C5B—C10B—H10E	109.5
C4—C5—H5	107.6	C5B—C10B—H10F	109.5
C4—C5—C6	108.4 (8)	H10D—C10B—H10E	109.5
C4—C5—C10	114 (2)	H10D—C10B—H10F	109.5
C6—C5—H5	107.6	H10E—C10B—H10F	109.5
C6—C5—C10	111.0 (15)	H1CA—O1C—H1C	116 (5)
C10—C5—H5	107.6	C1C—O1C—H1CA	111 (6)
C1—C6—C5	114.1 (14)	C1C—O1C—H1C	133 (3)
C1—C6—H6A	108.7	C1C—C2C—H2C	107.0
C1—C6—H6B	108.7	C3C—C2C—H2C	107.0
C5—C6—H6A	108.7	C3C—C2C—C1C	101 (2)
C5—C6—H6B	108.7	C7C—C2C—H2C	107.0
H6A—C6—H6B	107.6	C7C—C2C—C1C	117.8 (17)
C2—C7—H7	106.9	C7C—C2C—C3C	116.3 (13)
C2—C7—C9	109 (2)	H6CA—C6C—H6CB	107.5
C8—C7—C2	116.5 (11)	C1C—C6C—H6CA	108.5
C8—C7—H7	106.9	C1C—C6C—H6CB	108.5
C8—C7—C9	109.7 (15)	C1C—C6C—C5C	115.1 (12)
C9—C7—H7	106.9	C5C—C6C—H6CA	108.5
C7—C8—H8A	109.5	C5C—C6C—H6CB	108.5
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.8
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.1
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.1
H8A—C8—H8C	109.5	C3C—C4C—H4CA	109.1
H8B—C8—H8C	109.5	C3C—C4C—H4CB	109.1
C7—C9—H9A	109.5	C3C—C4C—C5C	112.7 (14)
C7—C9—H9B	109.5	O1C—C1C—C2C	99 (2)
C7—C9—H9C	109.5	O1C—C1C—H1CB	109.2
H9A—C9—H9B	109.5	C2C—C1C—H1CB	109.2
H9A—C9—H9C	109.5	C6C—C1C—O1C	113.9 (10)
H9B—C9—H9C	109.5	C6C—C1C—C2C	116.1 (14)
C5—C10—H10A	109.5	C6C—C1C—H1CB	109.2
C5—C10—H10B	109.5	C6C—C5C—C4C	102 (2)
C5—C10—H10C	109.5	C6C—C5C—H5C	109.5
H10A—C10—H10B	109.5	C4C—C5C—H5C	109.5
H10A—C10—H10C	109.5	C10C—C5C—C6C	114.8 (13)
H10B—C10—H10C	109.5	C10C—C5C—C4C	111.0 (15)
H1BA—O1B—H1BB	98 (5)	C10C—C5C—H5C	109.5
C1B—O1B—H1BA	112 (5)	C2C—C3C—H3CA	108.6
C1B—O1B—H1BB	108 (7)	C2C—C3C—H3CB	108.6
O1B—C1B—H1BC	108.5	C4C—C3C—C2C	114.5 (11)
O1B—C1B—C2B	114.1 (8)	C4C—C3C—H3CA	108.6
C2B—C1B—H1BC	108.5	C4C—C3C—H3CB	108.6
C6B—C1B—O1B	106.3 (17)	H3CA—C3C—H3CB	107.6
C6B—C1B—H1BC	108.5	C2C—C7C—H7C	105.5
C6B—C1B—C2B	111 (2)	C2C—C7C—C8C	112 (2)
C1B—C2B—H2B	108.9	C2C—C7C—C9C	111.4 (17)
C1B—C2B—C3B	109.4 (8)	C8C—C7C—H7C	105.5
C1B—C2B—C7B	110 (2)	C8C—C7C—C9C	116.2 (19)
C3B—C2B—H2B	108.9	C9C—C7C—H7C	105.5
C3B—C2B—C7B	111 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	108.9	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	110.2	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	110.2	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.5	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	108 (2)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	110.2	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	110.2	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.2	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.2	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.9	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112 (2)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.2	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.2	C5C—C10C—H10H	109.5
C4B—C5B—H5B	109.0	C5C—C10C—H10I	109.5
C4B—C5B—C6B	113.2 (9)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	109 (2)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	109.0	H10H—C10C—H10I	109.5
C6B—C5B—C10B	107 (2)

O1—C1—C2—C3	−176.6 (18)	C3B—C2B—C7B—C9B	−73 (2)
O1—C1—C2—C7	−52 (2)	C3B—C4B—C5B—C6B	−55 (3)
O1—C1—C6—C5	−177.6 (13)	C3B—C4B—C5B—C10B	−174.5 (18)
C1—C2—C3—C4	−57 (2)	C4B—C5B—C6B—C1B	55 (3)
C1—C2—C7—C8	−76.5 (15)	C6B—C1B—C2B—C3B	63 (3)
C1—C2—C7—C9	158.4 (11)	C6B—C1B—C2B—C7B	−174.6 (19)
C2—C1—C6—C5	−53.4 (19)	C7B—C2B—C3B—C4B	179.6 (18)
C2—C3—C4—C5	56.5 (19)	C10B—C5B—C6B—C1B	175.9 (15)
C3—C2—C7—C8	47.8 (16)	C1C—C2C—C3C—C4C	−55 (2)
C3—C2—C7—C9	−77.3 (17)	C1C—C2C—C7C—C8C	−55.0 (17)
C3—C4—C5—C6	−51 (3)	C1C—C2C—C7C—C9C	173.2 (14)
C3—C4—C5—C10	−175.4 (13)	C1C—C6C—C5C—C4C	56.3 (18)
C4—C5—C6—C1	47 (3)	C1C—C6C—C5C—C10C	176 (2)
C6—C1—C2—C3	58 (2)	C5C—C6C—C1C—O1C	−173 (2)
C6—C1—C2—C7	−178.2 (13)	C5C—C6C—C1C—C2C	−60 (2)
C7—C2—C3—C4	177.3 (14)	C5C—C4C—C3C—C2C	66 (2)
C10—C5—C6—C1	173.8 (15)	C3C—C2C—C1C—O1C	174.0 (4)
O1B—C1B—C2B—C3B	−177 (3)	C3C—C2C—C1C—C6C	51.9 (13)
O1B—C1B—C2B—C7B	−55 (3)	C3C—C2C—C7C—C8C	65 (3)
O1B—C1B—C6B—C5B	176.5 (10)	C3C—C2C—C7C—C9C	−67 (3)
C1B—C2B—C3B—C4B	−59 (3)	C3C—C4C—C5C—C6C	−59.1 (11)
C1B—C2B—C7B—C8B	−65 (2)	C3C—C4C—C5C—C10C	178.0 (6)
C1B—C2B—C7B—C9B	165.7 (14)	C7C—C2C—C1C—O1C	−58.1 (13)
C2B—C1B—C6B—C5B	−59 (2)	C7C—C2C—C1C—C6C	179.8 (7)
C2B—C3B—C4B—C5B	56 (2)	C7C—C2C—C3C—C4C	176 (2)
C3B—C2B—C7B—C8B	55.8 (17)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.65GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.091 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.677 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9875 (14) Å	Cell parameters from 1405 reflections
c = 12.442 (9) Å	θ = 3.1–28.4°
α = 117.25 (3)°	µ = 0.07 mm⁻¹
β = 99.96 (2)°	T = 296 K
γ = 103.224 (12)°	Plate, colourless
V = 1427.5 (13) Å³	0.39 × 0.3 × 0.06 mm

Data collection top

Xcalibur, Eos diffractometer	556 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.117
ω scans	θ_max = 29.4°, θ_min = 3.1°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
T_min = 0.976, T_max = 0.996	k = −4→4
8478 measured reflections	l = −15→16
1422 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.081	w = 1/[σ²(F_o²) + (0.1609P)² + 0.047P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.294	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.10 e Å⁻³
1422 reflections	Δρ_min = −0.09 e Å⁻³
317 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
247 restraints	Extinction coefficient: 0.012 (10)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.65 (2) GPa (650000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5372 (9)	1.0644 (17)	0.1265 (9)	0.112 (10)
H1A	0.602 (3)	1.031 (7)	0.111 (9)	0.167*	0.5
H1B	0.475 (3)	0.99 (2)	0.045 (5)	0.167*	0.5
C1	0.5586 (11)	1.2037 (16)	0.1798 (8)	0.075 (7)
H1	0.480198	1.213547	0.149953	0.112*
C2	0.5946 (9)	1.2681 (15)	0.3279 (7)	0.077 (6)
H2	0.674526	1.260593	0.356673	0.116*
C3	0.6161 (10)	1.4169 (16)	0.3854 (10)	0.085 (6)
H3A	0.636061	1.458462	0.477247	0.128*
H3B	0.539008	1.426230	0.353814	0.128*
C4	0.7196 (7)	1.4945 (17)	0.3573 (7)	0.093 (6)
H4A	0.724530	1.587020	0.393706	0.140*
H4B	0.799256	1.493283	0.394372	0.140*
C5	0.6886 (10)	1.4280 (17)	0.2170 (7)	0.111 (7)
H5	0.615930	1.445207	0.184953	0.166*
C6	0.6561 (9)	1.2815 (17)	0.1539 (10)	0.078 (6)
H6A	0.731365	1.264512	0.176293	0.118*
H6B	0.631067	1.245150	0.062485	0.118*
C7	0.5040 (6)	1.1971 (16)	0.3672 (7)	0.080 (6)
H7	0.484752	1.100749	0.311283	0.119*
C8	0.3770 (7)	1.223 (2)	0.3570 (8)	0.090 (10)
H8A	0.338924	1.200503	0.271580	0.108*
H8B	0.322752	1.167865	0.377703	0.108*
H8C	0.392151	1.315467	0.415596	0.108*
C9	0.5600 (7)	1.232 (3)	0.4979 (8)	0.104 (10)
H9A	0.500744	1.185382	0.521738	0.125*
H9B	0.631740	1.205779	0.503058	0.125*
H9C	0.584254	1.326641	0.554635	0.125*
C10	0.7931 (8)	1.486 (2)	0.1812 (10)	0.127 (11)
H10A	0.813608	1.581503	0.222749	0.152*
H10B	0.864386	1.466665	0.207703	0.152*
H10C	0.767930	1.447525	0.090406	0.152*
O1B	0.7306 (5)	0.9873 (14)	0.1048 (6)	0.100 (9)
H1BA	0.7896 (18)	0.984 (4)	0.078 (3)	0.151*	0.5
H1BB	0.709 (3)	1.038 (3)	0.1618 (17)	0.151*	0.5
C1B	0.7488 (7)	0.9294 (13)	0.1853 (7)	0.081 (6)
H1BC	0.810247	0.885816	0.166656	0.122*
C2B	0.7929 (8)	1.0336 (14)	0.3212 (8)	0.082 (6)
H2B	0.728959	1.073284	0.340320	0.123*
C3B	0.8040 (8)	0.9565 (16)	0.3908 (10)	0.097 (6)
H3BA	0.828677	1.019583	0.481891	0.145*
H3BB	0.870049	0.921062	0.374846	0.145*
C4B	0.6814 (9)	0.8357 (17)	0.3521 (8)	0.116 (7)
H4BA	0.701658	0.787149	0.392654	0.174*
H4BB	0.620667	0.872508	0.384847	0.174*
C5B	0.6236 (9)	0.7387 (16)	0.2101 (8)	0.119 (7)
H5B	0.675856	0.684838	0.181224	0.179*
C6B	0.6227 (7)	0.8230 (16)	0.1421 (8)	0.086 (6)
H6BA	0.597407	0.762499	0.050494	0.129*
H6BB	0.561881	0.866243	0.160080	0.129*
C7B	0.9076 (6)	1.1386 (13)	0.3613 (8)	0.086 (6)
H7B	0.888284	1.176948	0.308786	0.129*
C8B	1.0254 (7)	1.128 (2)	0.3532 (8)	0.102 (10)
H8BA	1.085080	1.215928	0.387852	0.122*
H8BB	1.051931	1.089310	0.400857	0.122*
H8BC	1.018582	1.072625	0.265478	0.122*
C9B	0.9316 (8)	1.2499 (16)	0.4927 (8)	0.115 (11)
H9BA	0.854758	1.261199	0.503316	0.138*
H9BB	0.968332	1.229260	0.553323	0.138*
H9BC	0.987326	1.331224	0.506422	0.138*
C10B	0.4984 (9)	0.648 (2)	0.1765 (11)	0.153 (11)
H10D	0.465202	0.588200	0.085600	0.184*
H10E	0.501593	0.597071	0.217351	0.184*
H10F	0.446076	0.699357	0.204436	0.184*
O1C	0.9315 (6)	1.0682 (10)	0.0456 (7)	0.099 (10)
H1CA	0.867 (3)	1.016 (4)	0.038 (5)	0.149*	0.5
H1CB	0.986 (2)	1.035 (3)	0.0384 (11)	0.149*	0.5
C2C	1.0499 (6)	1.2532 (17)	0.0313 (7)	0.078 (6)
H2C	1.077800	1.187964	−0.030432	0.116*
C6C	0.8250 (8)	1.1291 (18)	−0.1105 (7)	0.081 (6)
H6CA	0.835885	1.050610	−0.174820	0.122*
H6CB	0.741606	1.099360	−0.107788	0.122*
C4C	0.9486 (7)	1.276 (2)	−0.1483 (7)	0.090 (6)
H4CA	0.943503	1.334866	−0.181572	0.135*
H4CB	0.979145	1.209813	−0.202523	0.135*
C1C	0.9142 (7)	1.1696 (12)	0.0186 (8)	0.072 (7)
H1C	0.888001	1.230052	0.086262	0.108*
C5C	0.8263 (8)	1.2098 (17)	−0.1550 (8)	0.086 (6)
H5C	0.802420	1.281301	−0.095494	0.130*
C3C	1.0401 (9)	1.3581 (17)	−0.0157 (8)	0.097 (6)
H3CA	1.011425	1.425356	0.040699	0.146*
H3CB	1.120431	1.402781	−0.015962	0.146*
C7C	1.1408 (5)	1.3077 (17)	0.1605 (7)	0.072 (6)
H7C	1.136948	1.234287	0.176427	0.108*
C8C	1.1102 (8)	1.4196 (19)	0.2696 (8)	0.093 (10)
H8CA	1.027091	1.383213	0.267767	0.111*
H8CB	1.167630	1.450061	0.350929	0.111*
H8CC	1.117208	1.493464	0.256523	0.111*
C9C	1.2707 (6)	1.371 (2)	0.1688 (9)	0.102 (11)
H9CA	1.325992	1.404263	0.252144	0.123*
H9CB	1.294265	1.305081	0.105505	0.123*
H9CC	1.275310	1.443331	0.154107	0.123*
C10C	0.7269 (8)	1.146 (3)	−0.2871 (9)	0.119 (11)
H10G	0.733657	1.211043	−0.313088	0.143*
H10H	0.740151	1.069577	−0.349037	0.143*
H10I	0.645600	1.119337	−0.280791	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.108 (5)	0.12 (2)	0.101 (6)	0.020 (11)	0.046 (4)	0.055 (11)
C1	0.070 (6)	0.081 (14)	0.080 (7)	0.021 (9)	0.022 (5)	0.050 (8)
C2	0.074 (5)	0.080 (14)	0.082 (6)	0.037 (9)	0.032 (4)	0.038 (8)
C3	0.084 (5)	0.085 (14)	0.084 (6)	0.019 (9)	0.035 (5)	0.044 (8)
C4	0.094 (5)	0.100 (14)	0.098 (6)	0.052 (8)	0.037 (4)	0.050 (8)
C5	0.104 (7)	0.113 (15)	0.111 (7)	0.022 (9)	0.049 (6)	0.058 (8)
C6	0.077 (5)	0.082 (14)	0.074 (5)	0.028 (9)	0.031 (4)	0.037 (8)
C7	0.079 (5)	0.087 (14)	0.078 (5)	0.031 (8)	0.029 (4)	0.045 (7)
C8	0.075 (5)	0.10 (3)	0.099 (6)	0.047 (10)	0.031 (4)	0.041 (11)
C9	0.089 (5)	0.12 (3)	0.095 (6)	0.018 (10)	0.038 (5)	0.050 (10)
C10	0.117 (7)	0.13 (3)	0.134 (8)	0.054 (12)	0.064 (6)	0.057 (12)
O1B	0.077 (4)	0.10 (2)	0.106 (5)	0.013 (7)	0.038 (3)	0.041 (8)
C1B	0.074 (5)	0.078 (14)	0.083 (6)	0.033 (8)	0.028 (4)	0.033 (8)
C2B	0.079 (5)	0.083 (14)	0.082 (5)	0.021 (8)	0.031 (4)	0.043 (8)
C3B	0.088 (6)	0.099 (14)	0.101 (6)	0.032 (8)	0.044 (5)	0.047 (8)
C4B	0.122 (6)	0.124 (14)	0.109 (6)	0.038 (8)	0.057 (5)	0.061 (8)
C5B	0.101 (6)	0.120 (15)	0.135 (7)	0.031 (8)	0.058 (6)	0.061 (8)
C6B	0.088 (6)	0.087 (14)	0.081 (5)	0.035 (8)	0.032 (4)	0.039 (7)
C7B	0.072 (5)	0.088 (14)	0.101 (6)	0.046 (8)	0.029 (4)	0.042 (8)
C8B	0.099 (6)	0.12 (3)	0.093 (6)	0.047 (11)	0.041 (5)	0.048 (11)
C9B	0.094 (6)	0.12 (3)	0.128 (8)	0.056 (11)	0.048 (5)	0.045 (12)
C10B	0.135 (8)	0.15 (3)	0.170 (10)	0.042 (13)	0.085 (7)	0.067 (13)
O1C	0.085 (4)	0.12 (3)	0.121 (5)	0.046 (10)	0.024 (3)	0.083 (10)
C2C	0.076 (5)	0.073 (14)	0.082 (6)	0.036 (8)	0.039 (4)	0.030 (8)
C6C	0.075 (5)	0.080 (14)	0.073 (5)	0.019 (8)	0.031 (4)	0.029 (7)
C4C	0.100 (5)	0.095 (14)	0.084 (5)	0.024 (8)	0.031 (4)	0.058 (7)
C1C	0.060 (5)	0.072 (14)	0.081 (6)	0.041 (8)	0.024 (4)	0.029 (8)
C5C	0.105 (6)	0.086 (14)	0.068 (5)	0.028 (8)	0.024 (5)	0.045 (7)
C3C	0.093 (6)	0.093 (14)	0.092 (6)	0.049 (8)	0.026 (5)	0.032 (8)
C7C	0.061 (4)	0.068 (14)	0.083 (5)	0.011 (7)	0.019 (4)	0.044 (7)
C8C	0.106 (6)	0.09 (3)	0.086 (6)	0.059 (11)	0.028 (5)	0.042 (11)
C9C	0.103 (6)	0.10 (3)	0.104 (6)	0.062 (11)	0.042 (5)	0.044 (11)
C10C	0.118 (7)	0.14 (3)	0.100 (7)	0.030 (12)	0.037 (5)	0.065 (11)

Geometric parameters (Å, º) top

O1—H1A	0.936 (16)	C5B—C6B	1.588 (5)
O1—H1B	1.00 (12)	C5B—C10B	1.463 (9)
O1—C1	1.424 (6)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.566 (4)	C7B—H7B	0.9800
C1—C6	1.479 (8)	C7B—C8B	1.426 (5)
C2—H2	0.9800	C7B—C9B	1.4841 (16)
C2—C3	1.523 (2)	C8B—H8BA	0.9600
C2—C7	1.492 (2)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.5431 (13)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.479 (3)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.474 (2)	O1C—H1CA	0.8200 (12)
C5—C10	1.5021 (13)	O1C—H1CB	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.447 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.607 (4)
C7—C8	1.577 (8)	C2C—C3C	1.628 (6)
C7—C9	1.461 (2)	C2C—C7C	1.506 (8)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.541 (2)
C9—H9A	0.9600	C6C—C5C	1.316 (5)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.435 (8)
C10—H10B	0.9600	C4C—C3C	1.501 (8)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.8200 (12)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.555 (8)
O1B—C1B	1.471 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.468 (3)	C7C—H7C	0.9800
C1B—C6B	1.5233 (13)	C7C—C8C	1.578 (7)
C2B—H2B	0.9800	C7C—C9C	1.494 (7)
C2B—C3B	1.539 (4)	C8C—H8CA	0.9600
C2B—C7B	1.4313 (13)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.598 (2)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.5089 (16)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	92 (8)	C10B—C5B—C6B	111.1 (11)
C1—O1—H1A	121 (6)	C1B—C6B—C5B	112.9 (9)
C1—O1—H1B	129 (10)	C1B—C6B—H6BA	109.0
O1—C1—H1	108.1	C1B—C6B—H6BB	109.0
O1—C1—C2	106.6 (11)	C5B—C6B—H6BA	109.0
O1—C1—C6	117.9 (14)	C5B—C6B—H6BB	109.0
C2—C1—H1	108.1	H6BA—C6B—H6BB	107.8
C6—C1—H1	108.1	C2B—C7B—H7B	103.1
C6—C1—C2	107.6 (8)	C2B—C7B—C9B	110.1 (8)
C1—C2—H2	107.1	C8B—C7B—C2B	128.4 (12)
C3—C2—C1	106.9 (11)	C8B—C7B—H7B	103.1
C3—C2—H2	107.1	C8B—C7B—C9B	106.1 (9)
C7—C2—C1	113.0 (7)	C9B—C7B—H7B	103.1
C7—C2—H2	107.1	C7B—C8B—H8BA	109.5
C7—C2—C3	115.1 (10)	C7B—C8B—H8BB	109.5
C2—C3—H3A	108.4	C7B—C8B—H8BC	109.5
C2—C3—H3B	108.4	H8BA—C8B—H8BB	109.5
C2—C3—C4	115.5 (11)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.5	H8BB—C8B—H8BC	109.5
C4—C3—H3A	108.4	C7B—C9B—H9BA	109.5
C4—C3—H3B	108.4	C7B—C9B—H9BB	109.5
C3—C4—H4A	110.2	C7B—C9B—H9BC	109.5
C3—C4—H4B	110.2	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	108.5	H9BA—C9B—H9BC	109.5
C5—C4—C3	107.5 (8)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	110.2	C5B—C10B—H10D	109.5
C5—C4—H4B	110.2	C5B—C10B—H10E	109.5
C4—C5—H5	107.7	C5B—C10B—H10F	109.5
C4—C5—C10	110.9 (8)	H10D—C10B—H10E	109.5
C6—C5—C4	112.7 (12)	H10D—C10B—H10F	109.5
C6—C5—H5	107.7	H10E—C10B—H10F	109.5
C6—C5—C10	110.0 (13)	H1CA—O1C—H1CB	110.9 (14)
C10—C5—H5	107.7	C1C—O1C—H1CA	114 (4)
C1—C6—H6A	107.5	C1C—O1C—H1CB	130 (3)
C1—C6—H6B	107.5	C1C—C2C—H2C	105.8
C5—C6—C1	119.3 (12)	C1C—C2C—C3C	110.0 (11)
C5—C6—H6A	107.5	C3C—C2C—H2C	105.8
C5—C6—H6B	107.5	C7C—C2C—H2C	105.8
H6A—C6—H6B	107.0	C7C—C2C—C1C	110.7 (7)
C2—C7—H7	107.4	C7C—C2C—C3C	117.7 (11)
C2—C7—C8	115.5 (9)	H6CA—C6C—H6CB	106.5
C8—C7—H7	107.4	C1C—C6C—H6CA	106.4
C9—C7—C2	110.4 (8)	C1C—C6C—H6CB	106.4
C9—C7—H7	107.4	C5C—C6C—H6CA	106.4
C9—C7—C8	108.4 (7)	C5C—C6C—H6CB	106.4
C7—C8—H8A	109.5	C5C—C6C—C1C	123.8 (11)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.7
C7—C8—H8C	109.5	C5C—C4C—H4CA	108.8
H8A—C8—H8B	109.5	C5C—C4C—H4CB	108.8
H8A—C8—H8C	109.5	C5C—C4C—C3C	113.7 (7)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	108.8
C7—C9—H9A	109.5	C3C—C4C—H4CB	108.8
C7—C9—H9B	109.5	O1C—C1C—C2C	105.3 (11)
C7—C9—H9C	109.5	O1C—C1C—C6C	120.4 (11)
H9A—C9—H9B	109.5	O1C—C1C—H1C	107.7
H9A—C9—H9C	109.5	C2C—C1C—H1C	107.7
H9B—C9—H9C	109.5	C6C—C1C—C2C	107.3 (6)
C5—C10—H10A	109.5	C6C—C1C—H1C	107.7
C5—C10—H10B	109.5	C6C—C5C—C4C	112.8 (14)
C5—C10—H10C	109.5	C6C—C5C—H5C	105.0
H10A—C10—H10B	109.5	C6C—C5C—C10C	114.4 (13)
H10A—C10—H10C	109.5	C4C—C5C—H5C	105.0
H10B—C10—H10C	109.5	C4C—C5C—C10C	113.5 (8)
H1BA—O1B—H1BB	141.8 (4)	C10C—C5C—H5C	105.0
C1B—O1B—H1BA	102 (4)	C2C—C3C—H3CA	110.5
C1B—O1B—H1BB	83.6 (17)	C2C—C3C—H3CB	110.5
O1B—C1B—H1BC	109.1	C4C—C3C—C2C	106.3 (12)
O1B—C1B—C6B	104.3 (8)	C4C—C3C—H3CA	110.5
C2B—C1B—O1B	110.9 (8)	C4C—C3C—H3CB	110.5
C2B—C1B—H1BC	109.1	H3CA—C3C—H3CB	108.7
C2B—C1B—C6B	114.2 (7)	C2C—C7C—H7C	109.0
C6B—C1B—H1BC	109.1	C2C—C7C—C8C	111.3 (9)
C1B—C2B—H2B	108.7	C8C—C7C—H7C	109.0
C1B—C2B—C3B	104.2 (9)	C9C—C7C—C2C	111.7 (7)
C3B—C2B—H2B	108.7	C9C—C7C—H7C	109.0
C7B—C2B—C1B	114.7 (8)	C9C—C7C—C8C	106.6 (9)
C7B—C2B—H2B	108.7	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	111.6 (9)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	108.3	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	108.3	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	115.8 (9)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	107.4	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	108.3	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	108.3	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.8	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.8	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.7	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.9 (8)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.8	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.8	C5C—C10C—H10H	109.5
C4B—C5B—H5B	108.5	C5C—C10C—H10I	109.5
C4B—C5B—C6B	108.1 (10)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	108.5	H10G—C10C—H10I	109.5
C10B—C5B—C4B	112.2 (9)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	108.5

O1—C1—C2—C3	−179.3 (11)	C3B—C2B—C7B—C9B	−72.1 (10)
O1—C1—C2—C7	−51.7 (14)	C3B—C4B—C5B—C6B	−44.3 (12)
O1—C1—C6—C5	−174.4 (9)	C3B—C4B—C5B—C10B	−167.1 (13)
C1—C2—C3—C4	−59.9 (12)	C4B—C5B—C6B—C1B	50.3 (10)
C1—C2—C7—C8	−74.8 (12)	C6B—C1B—C2B—C3B	61.3 (11)
C1—C2—C7—C9	161.8 (15)	C6B—C1B—C2B—C7B	−176.3 (10)
C2—C1—C6—C5	−53.9 (16)	C7B—C2B—C3B—C4B	−179.4 (7)
C2—C3—C4—C5	57.1 (15)	C10B—C5B—C6B—C1B	173.8 (9)
C3—C2—C7—C8	48.4 (11)	C1C—C2C—C3C—C4C	−54.7 (11)
C3—C2—C7—C9	−75.0 (14)	C1C—C2C—C7C—C8C	−68.2 (16)
C3—C4—C5—C6	−48.8 (14)	C1C—C2C—C7C—C9C	172.7 (14)
C3—C4—C5—C10	−172.6 (13)	C1C—C6C—C5C—C4C	48.6 (14)
C4—C5—C6—C1	53.2 (14)	C1C—C6C—C5C—C10C	−179.7 (10)
C6—C1—C2—C3	53.3 (15)	C5C—C6C—C1C—O1C	−162.7 (10)
C6—C1—C2—C7	−179.1 (11)	C5C—C6C—C1C—C2C	−42.5 (16)
C7—C2—C3—C4	173.7 (6)	C5C—C4C—C3C—C2C	61.6 (17)
C10—C5—C6—C1	177.5 (9)	C3C—C2C—C1C—O1C	172.4 (7)
O1B—C1B—C2B—C3B	178.8 (7)	C3C—C2C—C1C—C6C	43.0 (13)
O1B—C1B—C2B—C7B	−58.9 (11)	C3C—C2C—C7C—C8C	59.5 (10)
O1B—C1B—C6B—C5B	175.6 (6)	C3C—C2C—C7C—C9C	−59.5 (16)
C1B—C2B—C3B—C4B	−55.0 (9)	C3C—C4C—C5C—C6C	−58.0 (18)
C1B—C2B—C7B—C8B	−58.5 (15)	C3C—C4C—C5C—C10C	169.9 (18)
C1B—C2B—C7B—C9B	169.7 (12)	C7C—C2C—C1C—O1C	−55.8 (16)
C2B—C1B—C6B—C5B	−63.3 (11)	C7C—C2C—C1C—C6C	174.8 (13)
C2B—C3B—C4B—C5B	50.9 (13)	C7C—C2C—C3C—C4C	177.2 (7)
C3B—C2B—C7B—C8B	59.7 (12)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_0.84GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.115 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.603 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8897 (10) Å	Cell parameters from 1407 reflections
c = 12.368 (9) Å	θ = 3.1–28.7°
α = 117.791 (11)°	µ = 0.07 mm⁻¹
β = 99.44 (5)°	T = 296 K
γ = 103.16 (3)°	Plate, colourless
V = 1395.7 (13) Å³	0.4 × 0.3 × 0.06 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	312 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.234
ω scans	θ_max = 30.7°, θ_min = 4.1°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
T_min = 0.415, T_max = 0.978	k = −13→13
8296 measured reflections	l = −17→17
1449 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.068	w = 1/[σ²(F_o²) + (0.1069P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.282	(Δ/σ)_max < 0.001
S = 0.89	Δρ_max = 0.05 e Å⁻³
1449 reflections	Δρ_min = −0.05 e Å⁻³
320 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
253 restraints	Extinction coefficient: 0.04 (2)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.84 (2) GPa (840000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5553 (11)	1.0701 (10)	0.1231 (6)	0.146 (10)
H1A	0.605 (3)	1.046 (7)	0.085 (3)	0.219*	0.5
H1B	0.485 (5)	0.986 (10)	0.045 (2)	0.219*	0.5
C1	0.5571 (10)	1.2120 (11)	0.1787 (8)	0.108 (7)
H1	0.477454	1.214473	0.140600	0.130*
C2	0.5869 (15)	1.2763 (12)	0.3209 (8)	0.119 (7)
H2	0.672406	1.279359	0.347535	0.143*
C3	0.6018 (13)	1.4189 (12)	0.3790 (9)	0.118 (7)
H3A	0.629951	1.463952	0.472072	0.177*
H3B	0.522716	1.428324	0.352914	0.177*
C4	0.7003 (17)	1.4847 (17)	0.3331 (8)	0.146 (7)
H4A	0.706373	1.578323	0.366449	0.175*
H4B	0.781083	1.485039	0.369742	0.175*
C5	0.6714 (11)	1.4148 (10)	0.1916 (8)	0.118 (7)
H5	0.592334	1.419353	0.154662	0.142*
C6	0.6580 (11)	1.2677 (10)	0.1384 (7)	0.101 (7)
H6A	0.636062	1.218962	0.045284	0.151*
H6B	0.735413	1.260458	0.173045	0.151*
C7	0.513 (2)	1.1801 (18)	0.3584 (10)	0.155 (9)
H7	0.496176	1.083401	0.299886	0.233*
C8	0.398 (3)	1.2262 (19)	0.3452 (16)	0.223 (14)
H8A	0.425408	1.323350	0.389456	0.334*
H8B	0.341325	1.194970	0.382326	0.334*
H8C	0.355704	1.188373	0.255866	0.334*
C9	0.576 (2)	1.232 (2)	0.4936 (11)	0.158 (12)
H9A	0.532309	1.175366	0.519683	0.189*
H9B	0.659883	1.233508	0.504122	0.189*
H9C	0.576404	1.323015	0.545683	0.189*
C10	0.7676 (16)	1.4780 (19)	0.1575 (11)	0.179 (13)
H10A	0.747013	1.431245	0.065522	0.214*
H10B	0.774713	1.571013	0.190773	0.214*
H10C	0.845362	1.474114	0.193493	0.214*
O1B	0.7511 (13)	1.0270 (12)	0.1332 (7)	0.183 (11)
H1BA	0.794 (8)	0.980 (11)	0.087 (8)	0.274*	0.5
H1BB	0.706 (9)	1.05 (2)	0.074 (18)	0.274*	0.5
C1B	0.7728 (12)	0.9528 (12)	0.1985 (9)	0.115 (7)
H1BC	0.828412	0.902576	0.168201	0.138*
C2B	0.8217 (17)	1.0523 (13)	0.3353 (10)	0.135 (7)
H2B	0.756692	1.090545	0.358098	0.162*
C3B	0.8327 (13)	0.9704 (13)	0.4035 (9)	0.117 (7)
H3BA	0.880494	0.912367	0.369514	0.176*
H3BB	0.872262	1.031117	0.495649	0.176*
C4B	0.6963 (14)	0.8852 (15)	0.3727 (10)	0.154 (8)
H4BA	0.689398	0.848255	0.427596	0.185*
H4BB	0.642081	0.938015	0.381151	0.185*
C5B	0.6670 (15)	0.7729 (13)	0.2316 (10)	0.143 (8)
H5B	0.733185	0.735150	0.213495	0.172*
C6B	0.6447 (12)	0.8614 (14)	0.1670 (10)	0.141 (7)
H6BA	0.605289	0.803114	0.074642	0.212*
H6BB	0.593129	0.913166	0.203848	0.212*
C7B	0.929 (2)	1.163 (2)	0.3698 (17)	0.158 (10)
H7B	0.913722	1.193886	0.309951	0.190*
C8B	1.036 (3)	1.1191 (19)	0.3598 (19)	0.200 (15)
H8BA	1.016047	1.031486	0.350447	0.300*
H8BB	1.105341	1.183237	0.436224	0.300*
H8BC	1.057217	1.113950	0.286234	0.300*
C9B	0.935 (2)	1.268 (2)	0.498 (2)	0.244 (15)
H9BA	1.005631	1.348065	0.529372	0.293*
H9BB	0.860092	1.289894	0.491975	0.293*
H9BC	0.942734	1.235949	0.555785	0.293*
C10B	0.541 (2)	0.670 (3)	0.1916 (18)	0.234 (14)
H10D	0.520694	0.598210	0.103697	0.281*
H10E	0.543160	0.632409	0.245804	0.281*
H10F	0.479508	0.712270	0.199733	0.281*
O1C	0.9326 (12)	1.0844 (10)	0.0545 (7)	0.169 (11)
H1CA	0.886 (11)	1.042 (16)	0.080 (19)	0.254*	0.5
H1CB	0.982 (12)	1.009 (12)	0.041 (9)	0.254*	0.5
C2C	1.0575 (11)	1.2531 (13)	0.0314 (10)	0.113 (7)
H2C	1.075658	1.178277	−0.034032	0.170*
C6C	0.8347 (14)	1.1095 (14)	−0.1032 (8)	0.131 (7)
H6CA	0.862948	1.038635	−0.157728	0.157*
H6CB	0.751319	1.068095	−0.105358	0.157*
C4C	0.9509 (13)	1.2711 (18)	−0.1435 (10)	0.146 (8)
H4CA	0.941402	1.339310	−0.162862	0.175*
H4CB	0.976603	1.208031	−0.210444	0.175*
C1C	0.9221 (11)	1.1924 (11)	0.0318 (8)	0.091 (7)
H1C	0.893265	1.258471	0.093935	0.109*
C5C	0.8365 (13)	1.2015 (14)	−0.1432 (10)	0.111 (7)
H5C	0.816058	1.272853	−0.076420	0.167*
C3C	1.0557 (12)	1.3422 (13)	−0.0085 (10)	0.147 (8)
H3CA	1.136378	1.375831	−0.016253	0.176*
H3CB	1.039630	1.418925	0.055033	0.176*
C7C	1.1554 (14)	1.311 (2)	0.1578 (15)	0.161 (9)
H7C	1.160264	1.241587	0.178433	0.193*
C8C	1.105 (2)	1.418 (2)	0.2539 (16)	0.175 (13)
H8CA	1.067761	1.457734	0.212023	0.262*
H8CB	1.173586	1.488497	0.329135	0.262*
H8CC	1.044566	1.373921	0.278549	0.262*
C9C	1.2788 (17)	1.393 (2)	0.1695 (11)	0.181 (13)
H9CA	1.336518	1.426121	0.251877	0.218*
H9CB	1.308158	1.337008	0.102598	0.218*
H9CC	1.271897	1.467461	0.161531	0.218*
C10C	0.7346 (17)	1.1515 (19)	−0.2662 (12)	0.163 (12)
H10G	0.743853	1.221843	−0.285440	0.196*
H10H	0.741126	1.073094	−0.335817	0.196*
H10I	0.654533	1.128005	−0.254855	0.196*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.126 (15)	0.160 (12)	0.125 (6)	0.011 (11)	0.027 (7)	0.075 (7)
C1	0.101 (11)	0.112 (9)	0.115 (7)	0.030 (7)	0.034 (7)	0.065 (7)
C2	0.109 (11)	0.124 (9)	0.113 (7)	0.050 (7)	0.021 (6)	0.054 (7)
C3	0.100 (11)	0.113 (9)	0.115 (7)	0.038 (7)	0.045 (7)	0.037 (7)
C4	0.147 (11)	0.143 (10)	0.142 (8)	0.048 (7)	0.058 (7)	0.067 (8)
C5	0.124 (10)	0.118 (9)	0.132 (7)	0.026 (7)	0.036 (6)	0.088 (7)
C6	0.108 (10)	0.106 (9)	0.093 (6)	0.038 (7)	0.036 (6)	0.053 (6)
C7	0.180 (13)	0.168 (11)	0.147 (10)	0.045 (7)	0.067 (8)	0.106 (9)
C8	0.25 (2)	0.263 (19)	0.214 (12)	0.070 (14)	0.071 (13)	0.181 (14)
C9	0.182 (19)	0.198 (16)	0.130 (8)	0.078 (13)	0.058 (9)	0.105 (10)
C10	0.195 (19)	0.172 (15)	0.210 (11)	0.042 (13)	0.073 (11)	0.137 (12)
O1B	0.201 (17)	0.226 (14)	0.146 (6)	0.044 (12)	0.084 (8)	0.120 (9)
C1B	0.112 (10)	0.111 (9)	0.126 (7)	0.030 (7)	0.030 (6)	0.070 (7)
C2B	0.137 (12)	0.126 (10)	0.134 (8)	0.053 (7)	0.037 (7)	0.061 (8)
C3B	0.125 (11)	0.119 (9)	0.111 (6)	0.059 (7)	0.027 (6)	0.059 (7)
C4B	0.160 (12)	0.173 (11)	0.137 (8)	0.059 (8)	0.053 (7)	0.084 (8)
C5B	0.130 (12)	0.137 (10)	0.159 (8)	0.045 (7)	0.039 (7)	0.077 (8)
C6B	0.144 (11)	0.131 (10)	0.144 (7)	0.040 (7)	0.050 (7)	0.070 (8)
C7B	0.151 (14)	0.177 (13)	0.146 (10)	0.051 (8)	0.053 (9)	0.084 (10)
C8B	0.15 (2)	0.22 (2)	0.214 (14)	0.029 (13)	0.066 (15)	0.110 (14)
C9B	0.21 (2)	0.23 (2)	0.238 (15)	0.105 (15)	0.095 (16)	0.060 (15)
C10B	0.23 (2)	0.221 (19)	0.267 (14)	0.059 (14)	0.059 (13)	0.152 (15)
O1C	0.169 (15)	0.171 (14)	0.179 (8)	0.019 (12)	0.069 (7)	0.113 (9)
C2C	0.095 (11)	0.116 (9)	0.125 (7)	0.029 (7)	0.024 (7)	0.068 (7)
C6C	0.133 (11)	0.135 (10)	0.124 (7)	0.043 (7)	0.049 (7)	0.067 (8)
C4C	0.140 (12)	0.161 (11)	0.136 (8)	0.058 (7)	0.057 (8)	0.071 (8)
C1C	0.095 (10)	0.077 (8)	0.100 (6)	0.033 (7)	0.035 (6)	0.043 (6)
C5C	0.108 (11)	0.112 (9)	0.112 (7)	0.047 (7)	0.010 (6)	0.062 (7)
C3C	0.151 (12)	0.146 (10)	0.154 (8)	0.039 (7)	0.035 (7)	0.097 (8)
C7C	0.157 (13)	0.160 (12)	0.160 (10)	0.050 (8)	0.061 (9)	0.077 (9)
C8C	0.155 (19)	0.150 (17)	0.183 (12)	0.053 (13)	0.062 (12)	0.056 (13)
C9C	0.175 (19)	0.229 (18)	0.147 (10)	0.069 (14)	0.065 (10)	0.100 (12)
C10C	0.222 (19)	0.150 (15)	0.137 (9)	0.070 (13)	0.075 (10)	0.082 (10)

Geometric parameters (Å, º) top

O1—H1A	0.8200 (13)	C5B—C6B	1.629 (9)
O1—H1B	1.04 (5)	C5B—C10B	1.504 (6)
O1—C1	1.4889 (11)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.491 (6)	C7B—H7B	0.9800
C1—C6	1.485 (5)	C7B—C8B	1.453 (9)
C2—H2	0.9800	C7B—C9B	1.470 (7)
C2—C3	1.4531 (12)	C8B—H8BA	0.9600
C2—C7	1.563 (6)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.569 (5)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.480 (6)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.5120 (12)	O1C—H1CA	0.85 (7)
C5—C10	1.434 (4)	O1C—H1CB	1.14 (4)
C6—H6A	0.9700	O1C—C1C	1.462 (7)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.575 (7)
C7—C8	1.567 (9)	C2C—C3C	1.364 (3)
C7—C9	1.462 (7)	C2C—C7C	1.5058 (18)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.497 (3)
C9—H9A	0.9600	C6C—C5C	1.392 (7)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.397 (5)
C10—H10B	0.9600	C4C—C3C	1.5907 (19)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.90 (8)	C5C—H5C	0.9800
O1B—H1BB	0.97 (10)	C5C—C10C	1.520 (9)
O1B—C1B	1.481 (5)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.448 (6)	C7C—H7C	0.9800
C1B—C6B	1.491 (5)	C7C—C8C	1.591 (10)
C2B—H2B	0.9800	C7C—C9C	1.477 (5)
C2B—C3B	1.570 (8)	C8C—H8CA	0.9600
C2B—C7B	1.418 (6)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.545 (6)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.539 (5)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	88 (3)	C10B—C5B—C6B	105.8 (11)
C1—O1—H1A	120 (6)	C1B—C6B—C5B	103.9 (8)
C1—O1—H1B	125 (6)	C1B—C6B—H6BA	111.0
O1—C1—H1	111.3	C1B—C6B—H6BB	111.0
O1—C1—C2	108.3 (10)	C5B—C6B—H6BA	111.0
C2—C1—H1	111.3	C5B—C6B—H6BB	111.0
C6—C1—O1	100.3 (7)	H6BA—C6B—H6BB	109.0
C6—C1—H1	111.3	C2B—C7B—H7B	108.6
C6—C1—C2	113.9 (7)	C2B—C7B—C8B	110 (2)
C1—C2—H2	102.7	C2B—C7B—C9B	103.5 (15)
C1—C2—C7	112.1 (7)	C8B—C7B—H7B	108.6
C3—C2—C1	109.4 (9)	C8B—C7B—C9B	117 (2)
C3—C2—H2	102.7	C9B—C7B—H7B	108.6
C3—C2—C7	124.1 (13)	C7B—C8B—H8BA	109.5
C7—C2—H2	102.7	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.1	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.1	H8BA—C8B—H8BB	109.5
C2—C3—C4	108.2 (9)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	108.4	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.1	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.1	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.7	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.7	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.6	H9BA—C9B—H9BC	109.5
C5—C4—C3	114.2 (7)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.7	C5B—C10B—H10D	109.5
C5—C4—H4B	108.7	C5B—C10B—H10E	109.5
C4—C5—H5	109.0	C5B—C10B—H10F	109.5
C4—C5—C6	109.1 (10)	H10D—C10B—H10E	109.5
C6—C5—H5	109.0	H10D—C10B—H10F	109.5
C10—C5—C4	110.8 (8)	H10E—C10B—H10F	109.5
C10—C5—H5	109.0	H1CA—O1C—H1CB	84 (5)
C10—C5—C6	110.0 (10)	C1C—O1C—H1CA	130 (7)
C1—C6—C5	105.8 (7)	C1C—O1C—H1CB	145 (3)
C1—C6—H6A	110.6	C1C—C2C—H2C	107.2
C1—C6—H6B	110.6	C3C—C2C—H2C	107.2
C5—C6—H6A	110.6	C3C—C2C—C1C	107.7 (8)
C5—C6—H6B	110.6	C3C—C2C—C7C	114.6 (9)
H6A—C6—H6B	108.7	C7C—C2C—H2C	107.2
C2—C7—H7	114.9	C7C—C2C—C1C	112.7 (8)
C2—C7—C8	91.8 (16)	H6CA—C6C—H6CB	108.9
C8—C7—H7	114.9	C1C—C6C—H6CA	110.8
C9—C7—C2	107.4 (8)	C1C—C6C—H6CB	110.8
C9—C7—H7	114.9	C5C—C6C—H6CA	110.8
C9—C7—C8	111 (2)	C5C—C6C—H6CB	110.8
C7—C8—H8A	109.5	C5C—C6C—C1C	104.8 (8)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.3
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.3
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.6 (8)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.3
C7—C9—H9B	109.5	O1C—C1C—C2C	101.7 (7)
C7—C9—H9C	109.5	O1C—C1C—C6C	100.2 (9)
H9A—C9—H9B	109.5	O1C—C1C—H1C	114.6
H9A—C9—H9C	109.5	C2C—C1C—H1C	114.6
H9B—C9—H9C	109.5	C6C—C1C—C2C	109.5 (8)
C5—C10—H10A	109.5	C6C—C1C—H1C	114.6
C5—C10—H10B	109.5	C6C—C5C—C4C	117.6 (11)
C5—C10—H10C	109.5	C6C—C5C—H5C	103.7
H10A—C10—H10B	109.5	C6C—C5C—C10C	115.9 (9)
H10A—C10—H10C	109.5	C4C—C5C—H5C	103.7
H10B—C10—H10C	109.5	C4C—C5C—C10C	110.3 (8)
H1BA—O1B—H1BB	102 (7)	C10C—C5C—H5C	103.7
C1B—O1B—H1BA	80 (3)	C2C—C3C—C4C	110.8 (9)
C1B—O1B—H1BB	157 (10)	C2C—C3C—H3CA	109.5
O1B—C1B—H1BC	112.3	C2C—C3C—H3CB	109.5
O1B—C1B—C6B	103.0 (7)	C4C—C3C—H3CA	109.5
C2B—C1B—O1B	106.8 (9)	C4C—C3C—H3CB	109.5
C2B—C1B—H1BC	112.3	H3CA—C3C—H3CB	108.1
C2B—C1B—C6B	109.7 (9)	C2C—C7C—H7C	112.2
C6B—C1B—H1BC	112.3	C2C—C7C—C8C	100.9 (13)
C1B—C2B—H2B	106.4	C8C—C7C—H7C	112.2
C1B—C2B—C3B	106.0 (9)	C9C—C7C—C2C	113.8 (10)
C3B—C2B—H2B	106.4	C9C—C7C—H7C	112.2
C7B—C2B—C1B	113.5 (11)	C9C—C7C—C8C	104.7 (17)
C7B—C2B—H2B	106.4	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	117.4 (13)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	110.9	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	110.9	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.9	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	104.2 (9)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	110.9	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	110.9	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	111.5	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	111.5	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	109.4	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	101.2 (8)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	111.5	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	111.5	C5C—C10C—H10H	109.5
C4B—C5B—H5B	114.7	C5C—C10C—H10I	109.5
C4B—C5B—C6B	97.3 (8)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	114.7	H10G—C10C—H10I	109.5
C10B—C5B—C4B	107.8 (12)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	114.7

O1—C1—C2—C3	174.2 (7)	C3B—C2B—C7B—C9B	−75 (2)
O1—C1—C2—C7	−44.0 (19)	C3B—C4B—C5B—C6B	−78.0 (10)
O1—C1—C6—C5	−179.1 (6)	C3B—C4B—C5B—C10B	172.7 (15)
C1—C2—C3—C4	−53.6 (12)	C4B—C5B—C6B—C1B	74.3 (11)
C1—C2—C7—C8	−85.7 (18)	C6B—C1B—C2B—C3B	64.1 (14)
C1—C2—C7—C9	162 (2)	C6B—C1B—C2B—C7B	−165.6 (19)
C2—C1—C6—C5	−63.6 (14)	C7B—C2B—C3B—C4B	166.0 (17)
C2—C3—C4—C5	54.4 (18)	C10B—C5B—C6B—C1B	−174.8 (14)
C3—C2—C7—C8	49.5 (13)	C1C—C2C—C3C—C4C	−54.7 (13)
C3—C2—C7—C9	−63 (2)	C1C—C2C—C7C—C8C	−56.8 (13)
C3—C4—C5—C6	−56.8 (17)	C1C—C2C—C7C—C9C	−168.3 (17)
C3—C4—C5—C10	−178.1 (15)	C1C—C6C—C5C—C4C	59.6 (14)
C4—C5—C6—C1	58.2 (12)	C1C—C6C—C5C—C10C	−167.0 (16)
C6—C1—C2—C3	63.5 (14)	C5C—C6C—C1C—O1C	−169.2 (10)
C6—C1—C2—C7	−154.7 (17)	C5C—C6C—C1C—C2C	−62.8 (13)
C7—C2—C3—C4	170.3 (13)	C5C—C4C—C3C—C2C	49.2 (16)
C10—C5—C6—C1	179.9 (8)	C3C—C2C—C1C—O1C	170.9 (8)
O1B—C1B—C2B—C3B	175.0 (11)	C3C—C2C—C1C—C6C	65.6 (12)
O1B—C1B—C2B—C7B	−55 (2)	C3C—C2C—C7C—C8C	66.9 (13)
O1B—C1B—C6B—C5B	177.1 (9)	C3C—C2C—C7C—C9C	−45 (2)
C1B—C2B—C3B—C4B	−65.9 (13)	C3C—C4C—C5C—C6C	−52.0 (16)
C1B—C2B—C7B—C8B	−73 (2)	C3C—C4C—C5C—C10C	172.1 (16)
C1B—C2B—C7B—C9B	161 (2)	C7C—C2C—C1C—O1C	−61.7 (13)
C2B—C1B—C6B—C5B	−69.5 (13)	C7C—C2C—C1C—C6C	−167.1 (15)
C2B—C3B—C4B—C5B	76.2 (11)	C7C—C2C—C3C—C4C	179.1 (15)
C3B—C2B—C7B—C8B	51 (2)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_1.12GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.152 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.441 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.726 (4) Å	Cell parameters from 1404 reflections
c = 12.238 (4) Å	θ = 3.1–29.1°
α = 117.51 (3)°	µ = 0.07 mm⁻¹
β = 99.78 (2)°	T = 296 K
γ = 102.45 (3)°	Plate, colourless
V = 1351.3 (8) Å³	0.4 × 0.3 × 0.06 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	299 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.215
ω scans	θ_max = 27.7°, θ_min = 4.3°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
T_min = 0.975, T_max = 0.996	k = −15→14
6494 measured reflections	l = −11→11
1172 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.1008P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.248	(Δ/σ)_max < 0.001
S = 0.94	Δρ_max = 0.08 e Å⁻³
1172 reflections	Δρ_min = −0.08 e Å⁻³
318 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
223 restraints	Extinction coefficient: 0.006 (5)

Special details top

Experimental. Data were collected at room temperature and pressure of 1.12 (2) GPa (1120000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5395 (10)	1.0723 (19)	0.131 (3)	0.097 (9)
H1A	0.6006 (17)	1.048 (3)	0.138 (5)	0.146*	0.5
H1B	0.504 (12)	1.01 (2)	0.0432 (12)	0.146*	0.5
C1	0.561 (3)	1.219 (5)	0.195 (7)	0.081 (7)
H1	0.483166	1.232579	0.163404	0.121*
C2	0.592 (3)	1.278 (5)	0.332 (6)	0.084 (8)
H2	0.671488	1.264394	0.356073	0.126*
C3	0.627 (2)	1.451 (3)	0.422 (5)	0.119 (7)
H3A	0.552570	1.476390	0.411305	0.179*
H3B	0.664907	1.485580	0.513711	0.179*
C4	0.724 (2)	1.504 (4)	0.364 (5)	0.085 (7)
H4A	0.804447	1.496581	0.395486	0.128*
H4B	0.736899	1.599560	0.396023	0.128*
C5	0.679 (2)	1.419 (4)	0.203 (5)	0.076 (7)
H5	0.601002	1.429000	0.167904	0.114*
C6	0.6642 (16)	1.289 (3)	0.166 (4)	0.080 (6)
H6A	0.742306	1.285074	0.206912	0.120*
H6B	0.649543	1.238331	0.072895	0.120*
C7	0.500 (2)	1.197 (4)	0.368 (5)	0.085 (7)
H7	0.484427	1.098655	0.313266	0.127*
C8	0.3779 (14)	1.228 (2)	0.361 (3)	0.084 (9)
H8A	0.322425	1.174913	0.383717	0.101*
H8B	0.395353	1.323267	0.419727	0.101*
H8C	0.338691	1.205088	0.274013	0.101*
C9	0.568 (2)	1.252 (4)	0.518 (6)	0.124 (11)
H9A	0.646495	1.233885	0.526778	0.149*
H9B	0.584712	1.348243	0.569175	0.149*
H9C	0.514504	1.205762	0.548203	0.149*
C10	0.7946 (14)	1.508 (2)	0.195 (3)	0.082 (9)
H10A	0.790396	1.598623	0.225388	0.099*
H10B	0.870653	1.513719	0.246886	0.099*
H10C	0.794277	1.468383	0.106075	0.099*
O1B	0.7318 (8)	0.9893 (13)	0.1089 (18)	0.100 (8)
H1BA	0.7980 (13)	0.985 (3)	0.093 (2)	0.150*	0.5
H1BB	0.7025 (12)	1.040 (2)	0.160 (2)	0.150*	0.5
C1B	0.741 (2)	0.927 (3)	0.181 (4)	0.084 (8)
H1BC	0.796908	0.874156	0.151828	0.100*
C2B	0.806 (2)	1.029 (3)	0.325 (4)	0.084 (8)
H2B	0.738236	1.064723	0.347097	0.101*
C3B	0.8200 (13)	0.971 (2)	0.413 (3)	0.083 (6)
H3BA	0.835572	1.040375	0.502307	0.124*
H3BB	0.889446	0.935312	0.408064	0.124*
C4B	0.6959 (18)	0.856 (3)	0.364 (3)	0.104 (9)
H4BA	0.710952	0.806397	0.407397	0.124*
H4BB	0.637255	0.900124	0.398608	0.124*
C5B	0.624 (2)	0.748 (3)	0.223 (3)	0.075 (7)
H5B	0.678487	0.693520	0.191578	0.090*
C6B	0.6281 (15)	0.833 (2)	0.161 (3)	0.086 (6)
H6BA	0.592275	0.769377	0.067667	0.129*
H6BB	0.570944	0.882825	0.186678	0.129*
C7B	0.9201 (19)	1.172 (3)	0.392 (4)	0.095 (8)
H7B	0.898926	1.210610	0.338667	0.114*
C8B	1.0281 (17)	1.118 (3)	0.350 (4)	0.110 (10)
H8BA	0.996635	1.046579	0.260618	0.132*
H8BB	1.095489	1.191862	0.361525	0.132*
H8BC	1.058841	1.083983	0.402550	0.132*
C9B	0.945 (2)	1.285 (3)	0.529 (4)	0.152 (14)
H9BA	0.866886	1.294985	0.542745	0.228*
H9BB	0.998283	1.369243	0.542506	0.228*
H9BC	0.986378	1.264106	0.588769	0.228*
C10B	0.503 (2)	0.651 (3)	0.190 (4)	0.121 (10)
H10D	0.510861	0.602265	0.234252	0.146*
H10E	0.444466	0.698287	0.214727	0.146*
H10F	0.472002	0.586951	0.097724	0.146*
O1C	0.9283 (8)	1.0704 (10)	0.0426 (15)	0.086 (8)
H1CA	0.873 (3)	1.014 (3)	0.044 (3)	0.130*	0.5
H1CB	0.9893 (10)	1.045 (2)	0.033 (4)	0.130*	0.5
C2C	1.048 (2)	1.249 (3)	0.026 (5)	0.080 (7)
H2C	1.075089	1.179536	−0.036459	0.120*
C6C	0.8222 (19)	1.099 (3)	−0.128 (4)	0.083 (6)
H6CA	0.849552	1.030095	−0.189277	0.125*
H6CB	0.737848	1.056431	−0.131913	0.125*
C4C	0.958 (2)	1.296 (3)	−0.119 (5)	0.085 (7)
H4CA	0.990666	1.241437	−0.185459	0.128*
H4CB	0.952757	1.371122	−0.131207	0.128*
C1C	0.9210 (18)	1.179 (3)	0.020 (4)	0.072 (6)
H1C	0.889594	1.242725	0.083377	0.107*
C5C	0.827 (2)	1.212 (3)	−0.157 (4)	0.103 (7)
H5C	0.792222	1.271361	−0.093854	0.155*
C3C	1.047 (2)	1.352 (3)	−0.014 (5)	0.088 (7)
H3CA	1.035615	1.430813	0.052944	0.132*
H3CB	1.127168	1.381418	−0.026936	0.132*
C7C	1.1436 (18)	1.313 (3)	0.156 (4)	0.085 (7)
H7C	1.144161	1.237818	0.170855	0.127*
C8C	1.1138 (16)	1.415 (3)	0.269 (4)	0.114 (10)
H8CA	1.180056	1.450189	0.347821	0.137*
H8CB	1.106729	1.489034	0.257164	0.137*
H8CC	1.035688	1.371531	0.274821	0.137*
C9C	1.2796 (16)	1.382 (3)	0.173 (4)	0.092 (9)
H9CA	1.330649	1.418088	0.259880	0.110*
H9CB	1.309611	1.316149	0.113144	0.110*
H9CC	1.284548	1.454548	0.155736	0.110*
C10C	0.7220 (19)	1.139 (3)	−0.285 (4)	0.099 (10)
H10G	0.646683	1.091762	−0.277101	0.118*
H10H	0.706468	1.204123	−0.306177	0.118*
H10I	0.746588	1.073866	−0.351404	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.106 (10)	0.112 (14)	0.09 (3)	0.035 (10)	0.049 (15)	0.058 (17)
C1	0.081 (9)	0.083 (11)	0.078 (15)	0.011 (7)	0.022 (10)	0.050 (11)
C2	0.083 (9)	0.090 (12)	0.081 (15)	0.030 (8)	0.034 (10)	0.043 (10)
C3	0.129 (10)	0.113 (11)	0.120 (15)	0.020 (7)	0.039 (9)	0.072 (10)
C4	0.097 (10)	0.090 (11)	0.081 (15)	0.025 (7)	0.021 (9)	0.059 (11)
C5	0.070 (8)	0.075 (11)	0.080 (15)	0.030 (7)	0.017 (9)	0.037 (10)
C6	0.082 (8)	0.083 (10)	0.078 (14)	0.027 (7)	0.027 (9)	0.043 (10)
C7	0.083 (9)	0.094 (11)	0.083 (15)	0.029 (7)	0.033 (9)	0.049 (10)
C8	0.081 (10)	0.073 (15)	0.09 (3)	0.028 (10)	0.035 (14)	0.034 (17)
C9	0.091 (13)	0.15 (2)	0.12 (3)	0.025 (11)	0.041 (16)	0.061 (19)
C10	0.091 (10)	0.059 (15)	0.09 (3)	0.016 (10)	0.038 (14)	0.035 (17)
O1B	0.137 (9)	0.120 (13)	0.10 (2)	0.070 (9)	0.061 (12)	0.076 (16)
C1B	0.078 (9)	0.088 (12)	0.087 (15)	0.045 (9)	0.024 (9)	0.039 (10)
C2B	0.090 (10)	0.083 (12)	0.085 (15)	0.021 (8)	0.011 (9)	0.056 (11)
C3B	0.079 (8)	0.091 (10)	0.081 (14)	0.028 (7)	0.022 (9)	0.047 (10)
C4B	0.115 (12)	0.091 (12)	0.108 (16)	0.017 (8)	0.029 (9)	0.065 (11)
C5B	0.069 (8)	0.075 (11)	0.079 (15)	0.039 (8)	0.023 (9)	0.032 (10)
C6B	0.087 (8)	0.079 (10)	0.089 (14)	0.027 (7)	0.033 (9)	0.039 (10)
C7B	0.097 (10)	0.094 (12)	0.096 (15)	0.027 (8)	0.041 (10)	0.050 (11)
C8B	0.098 (12)	0.122 (17)	0.10 (3)	0.031 (11)	0.023 (15)	0.054 (18)
C9B	0.131 (16)	0.15 (2)	0.16 (3)	0.065 (15)	0.043 (18)	0.064 (19)
C10B	0.138 (12)	0.112 (17)	0.12 (3)	0.033 (11)	0.093 (15)	0.056 (18)
O1C	0.109 (8)	0.072 (12)	0.10 (2)	0.031 (8)	0.037 (11)	0.061 (15)
C2C	0.094 (9)	0.080 (11)	0.079 (15)	0.026 (7)	0.030 (9)	0.051 (10)
C6C	0.088 (8)	0.079 (11)	0.084 (14)	0.027 (7)	0.041 (9)	0.039 (10)
C4C	0.091 (10)	0.094 (11)	0.082 (15)	0.028 (8)	0.024 (9)	0.056 (11)
C1C	0.078 (8)	0.062 (10)	0.076 (14)	0.021 (7)	0.018 (9)	0.039 (10)
C5C	0.096 (9)	0.113 (11)	0.100 (15)	0.040 (8)	0.032 (9)	0.053 (10)
C3C	0.087 (9)	0.085 (11)	0.090 (15)	0.020 (7)	0.029 (9)	0.047 (10)
C7C	0.077 (9)	0.087 (11)	0.084 (15)	0.018 (7)	0.027 (9)	0.043 (10)
C8C	0.077 (12)	0.112 (19)	0.12 (3)	0.005 (12)	−0.002 (17)	0.059 (19)
C9C	0.081 (11)	0.079 (16)	0.09 (3)	0.017 (10)	0.023 (14)	0.035 (18)
C10C	0.110 (12)	0.082 (17)	0.11 (3)	0.060 (11)	0.062 (15)	0.031 (18)

Geometric parameters (Å, º) top

O1—H1A	0.8200 (12)	C5B—C6B	1.504 (19)
O1—H1B	0.92 (2)	C5B—C10B	1.45 (2)
O1—C1	1.46 (6)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.43 (10)	C7B—H7B	0.9800
C1—C6	1.482 (18)	C7B—C8B	1.56 (3)
C2—H2	0.9800	C7B—C9B	1.51 (2)
C2—C3	1.70 (6)	C8B—H8BA	0.9600
C2—C7	1.52 (2)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.59 (2)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.66 (8)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.34 (3)	O1C—H1CA	0.8200 (12)
C5—C10	1.550 (17)	O1C—H1CB	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.439 (11)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.482 (18)
C7—C8	1.520 (17)	C2C—C3C	1.493 (18)
C7—C9	1.62 (7)	C2C—C7C	1.49 (5)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.65 (6)
C9—H9A	0.9700	C6C—C5C	1.502 (18)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9700	C4C—C5C	1.47 (2)
C10—H10B	0.9600	C4C—C3C	1.27 (6)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.8200 (12)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.52 (2)
O1B—C1B	1.38 (2)	C3C—H3CA	0.9600
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.52 (2)	C7C—H7C	0.9800
C1B—C6B	1.41 (2)	C7C—C8C	1.51 (2)
C2B—H2B	0.9800	C7C—C9C	1.521 (19)
C2B—C3B	1.523 (18)	C8C—H8CA	0.9600
C2B—C7B	1.61 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.525 (17)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.52 (2)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	97 (2)	C10B—C5B—C6B	116.4 (19)
C1—O1—H1A	118 (3)	C1B—C6B—C5B	122 (2)
C1—O1—H1B	123 (10)	C1B—C6B—H6BA	106.8
O1—C1—H1	108.9	C1B—C6B—H6BB	106.8
O1—C1—C6	111 (3)	C5B—C6B—H6BA	106.8
C2—C1—O1	110 (2)	C5B—C6B—H6BB	106.8
C2—C1—H1	108.9	H6BA—C6B—H6BB	106.7
C2—C1—C6	109 (4)	C2B—C7B—H7B	104.1
C6—C1—H1	108.9	C8B—C7B—C2B	100 (2)
C1—C2—H2	104.1	C8B—C7B—H7B	104.1
C1—C2—C3	117 (3)	C9B—C7B—C2B	122 (2)
C1—C2—C7	111 (5)	C9B—C7B—H7B	104.1
C3—C2—H2	104.1	C9B—C7B—C8B	120 (3)
C7—C2—H2	104.1	C7B—C8B—H8BA	109.5
C7—C2—C3	115 (4)	C7B—C8B—H8BB	109.5
C2—C3—H3A	111.4	C7B—C8B—H8BC	109.5
C2—C3—H3B	111.4	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	109.3	H8BA—C8B—H8BC	109.5
C4—C3—C2	102 (3)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	111.4	C7B—C9B—H9BA	109.5
C4—C3—H3B	111.4	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.7	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.7	H9BA—C9B—H9BB	109.5
C3—C4—C5	114 (3)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.6	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.7	C5B—C10B—H10D	109.5
C5—C4—H4B	108.7	C5B—C10B—H10E	109.5
C4—C5—H5	111.3	C5B—C10B—H10F	109.5
C6—C5—C4	106 (2)	H10D—C10B—H10E	109.5
C6—C5—H5	111.3	H10D—C10B—H10F	109.5
C6—C5—C10	120.7 (19)	H10E—C10B—H10F	109.5
C10—C5—C4	95 (3)	H1CA—O1C—H1CB	110.9 (14)
C10—C5—H5	111.3	C1C—O1C—H1CA	130 (4)
C1—C6—H6A	108.3	C1C—O1C—H1CB	117 (4)
C1—C6—H6B	108.3	C1C—C2C—H2C	106.9
C5—C6—C1	116 (2)	C1C—C2C—C3C	112.1 (14)
C5—C6—H6A	108.3	C1C—C2C—C7C	113 (3)
C5—C6—H6B	108.3	C3C—C2C—H2C	106.9
H6A—C6—H6B	107.4	C3C—C2C—C7C	111 (3)
C2—C7—H7	110.0	C7C—C2C—H2C	106.9
C2—C7—C9	105 (3)	H6CA—C6C—H6CB	109.1
C8—C7—C2	111.6 (12)	C1C—C6C—H6CA	111.1
C8—C7—H7	111.1	C1C—C6C—H6CB	111.1
C8—C7—C9	107 (3)	C5C—C6C—H6CA	111.1
C9—C7—H7	111.1	C5C—C6C—H6CB	111.1
C7—C8—H8A	109.5	C5C—C6C—C1C	103 (3)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	105.7
C7—C8—H8C	109.5	C5C—C4C—H4CA	104.6
H8A—C8—H8B	109.5	C5C—C4C—H4CB	104.6
H8A—C8—H8C	109.5	C3C—C4C—H4CA	104.6
H8B—C8—H8C	109.5	C3C—C4C—H4CB	104.6
C7—C9—H9A	109.5	C3C—C4C—C5C	131 (3)
C7—C9—H9B	109.5	O1C—C1C—C2C	107.9 (10)
C7—C9—H9C	109.5	O1C—C1C—C6C	104 (2)
H9A—C9—H9B	109.5	O1C—C1C—H1C	111.4
H9A—C9—H9C	109.5	C2C—C1C—C6C	111 (3)
H9B—C9—H9C	109.5	C2C—C1C—H1C	111.4
C5—C10—H10A	109.5	C6C—C1C—H1C	111.4
C5—C10—H10B	109.5	C6C—C5C—H5C	104.1
C5—C10—H10C	109.5	C6C—C5C—C10C	102 (2)
H10A—C10—H10B	109.5	C4C—C5C—C6C	109.8 (17)
H10A—C10—H10C	109.5	C4C—C5C—H5C	104.1
H10B—C10—H10C	109.5	C4C—C5C—C10C	131 (2)
H1BA—O1B—H1BB	141.9 (4)	C10C—C5C—H5C	104.1
C1B—O1B—H1BA	95 (3)	C2C—C3C—H3CA	110.0
C1B—O1B—H1BB	89 (2)	C2C—C3C—H3CB	110.0
O1B—C1B—H1BC	105.7	C4C—C3C—C2C	108 (3)
O1B—C1B—C2B	112.8 (18)	C4C—C3C—H3CA	110.0
O1B—C1B—C6B	115 (2)	C4C—C3C—H3CB	110.0
C2B—C1B—H1BC	105.7	H3CA—C3C—H3CB	108.4
C6B—C1B—H1BC	105.7	C2C—C7C—H7C	105.6
C6B—C1B—C2B	111 (2)	C2C—C7C—C8C	115.6 (16)
C1B—C2B—H2B	99.2	C2C—C7C—C9C	118 (2)
C1B—C2B—C7B	127.6 (19)	C8C—C7C—H7C	105.6
C3B—C2B—C1B	117 (2)	C8C—C7C—C9C	105 (2)
C3B—C2B—H2B	99.2	C9C—C7C—H7C	105.6
C3B—C2B—C7B	108 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	99.2	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	110.5	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	110.5	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	106.2 (16)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.7	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	110.5	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	110.5	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	105.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	105.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	106.2	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	125.6 (19)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	105.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	105.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	106.0	C5C—C10C—H10I	109.5
C6B—C5B—C4B	102 (2)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	106.0	H10G—C10C—H10I	109.5
C10B—C5B—C4B	120 (2)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	106.0

O1—C1—C2—C3	177.1 (8)	C3B—C2B—C7B—C9B	−55 (3)
O1—C1—C2—C7	−49 (2)	C3B—C4B—C5B—C6B	−46 (2)
O1—C1—C6—C5	171 (3)	C3B—C4B—C5B—C10B	−175.5 (10)
C1—C2—C3—C4	−48 (3)	C4B—C5B—C6B—C1B	51 (3)
C1—C2—C7—C8	−79 (4)	C6B—C1B—C2B—C3B	48 (2)
C1—C2—C7—C9	165 (3)	C6B—C1B—C2B—C7B	−165.9 (14)
C2—C1—C6—C5	−68 (4)	C7B—C2B—C3B—C4B	166.9 (19)
C2—C3—C4—C5	46 (2)	C10B—C5B—C6B—C1B	−178 (3)
C3—C2—C7—C8	56 (5)	C1C—C2C—C3C—C4C	−48 (5)
C3—C2—C7—C9	−59 (3)	C1C—C2C—C7C—C8C	−57 (2)
C3—C4—C5—C6	−58.8 (18)	C1C—C2C—C7C—C9C	176.8 (16)
C3—C4—C5—C10	177.3 (10)	C1C—C6C—C5C—C4C	46 (3)
C4—C5—C6—C1	66 (3)	C1C—C6C—C5C—C10C	−172.3 (16)
C6—C1—C2—C3	55 (2)	C5C—C6C—C1C—O1C	−173.7 (10)
C6—C1—C2—C7	−170.8 (10)	C5C—C6C—C1C—C2C	−58 (2)
C7—C2—C3—C4	179 (3)	C5C—C4C—C3C—C2C	45 (5)
C10—C5—C6—C1	172 (3)	C3C—C2C—C1C—O1C	172 (3)
O1B—C1B—C2B—C3B	179.3 (8)	C3C—C2C—C1C—C6C	59 (4)
O1B—C1B—C2B—C7B	−35 (3)	C3C—C2C—C7C—C8C	69 (2)
O1B—C1B—C6B—C5B	175 (2)	C3C—C2C—C7C—C9C	−57 (3)
C1B—C2B—C3B—C4B	−41 (2)	C3C—C4C—C5C—C6C	−50 (5)
C1B—C2B—C7B—C8B	−67 (2)	C3C—C4C—C5C—C10C	−176 (3)
C1B—C2B—C7B—C9B	157 (2)	C7C—C2C—C1C—O1C	−62 (3)
C2B—C1B—C6B—C5B	−56 (3)	C7C—C2C—C1C—C6C	−175 (2)
C2B—C3B—C4B—C5B	44 (2)	C7C—C2C—C3C—C4C	−174 (3)
C3B—C2B—C7B—C8B	81 (2)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_1.44GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.185 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.3399 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6116 (11) Å	Cell parameters from 1409 reflections
c = 12.094 (3) Å	θ = 3.2–29.5°
α = 117.748 (13)°	µ = 0.07 mm⁻¹
β = 99.55 (2)°	T = 296 K
γ = 101.95 (3)°	Plate, colourless
V = 1314.0 (5) Å³	0.39 × 0.3 × 0.06 mm

Data collection top

Xcalibur, Eos diffractometer	373 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.220
ω scans	θ_max = 31.0°, θ_min = 2.8°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
T_min = 0.974, T_max = 0.996	k = −11→11
9339 measured reflections	l = −17→17
1521 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.075	w = 1/[σ²(F_o²) + (0.1193P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.291	(Δ/σ)_max < 0.001
S = 0.94	Δρ_max = 0.09 e Å⁻³
1521 reflections	Δρ_min = −0.09 e Å⁻³
317 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
214 restraints	Extinction coefficient: 0.083 (18)

Special details top

Experimental. Data were collected at room temperature and pressure of 1.44 (2) GPa (1440000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5441 (12)	1.0728 (14)	0.1248 (7)	0.119 (11)
H1A	0.615 (2)	1.102 (3)	0.177 (3)	0.179*	0.5
H1B	0.499 (10)	1.011 (10)	0.0511 (6)	0.179*	0.5
C1	0.5489 (14)	1.2122 (15)	0.1800 (10)	0.101 (7)
H1	0.465197	1.217448	0.151238	0.151*
C2	0.5897 (18)	1.273 (2)	0.3231 (9)	0.086 (7)
H2	0.671972	1.262515	0.347770	0.129*
C3	0.609 (2)	1.419 (2)	0.3767 (11)	0.105 (7)
H3A	0.633348	1.465355	0.471623	0.158*
H3B	0.529254	1.430051	0.347311	0.158*
C4	0.7060 (19)	1.483 (2)	0.3371 (11)	0.116 (7)
H4A	0.717574	1.580568	0.378157	0.174*
H4B	0.785833	1.472927	0.367504	0.174*
C5	0.672 (2)	1.423 (2)	0.2001 (12)	0.118 (8)
H5	0.594919	1.440769	0.173666	0.176*
C6	0.645 (2)	1.288 (2)	0.1430 (10)	0.112 (7)
H6A	0.722546	1.268887	0.161026	0.168*
H6B	0.614009	1.248741	0.049069	0.168*
C7	0.507 (3)	1.208 (3)	0.3635 (14)	0.097 (8)
H7	0.495240	1.109790	0.310758	0.145*
C8	0.393 (3)	1.219 (3)	0.3500 (15)	0.123 (12)
H8A	0.345464	1.169712	0.381928	0.148*
H8B	0.399776	1.314753	0.399311	0.148*
H8C	0.350988	1.182103	0.259095	0.148*
C9	0.556 (2)	1.247 (2)	0.4957 (11)	0.140 (12)
H9A	0.639925	1.240997	0.510625	0.168*
H9B	0.559909	1.340586	0.552057	0.168*
H9C	0.502724	1.187510	0.514359	0.168*
C10	0.765 (3)	1.488 (3)	0.1661 (13)	0.180 (14)
H10A	0.779067	1.584842	0.212060	0.215*
H10B	0.842683	1.471273	0.189384	0.215*
H10C	0.738192	1.451206	0.073319	0.215*
O1B	0.7342 (16)	1.0251 (15)	0.1287 (8)	0.160 (12)
H1BA	0.81 (2)	1.08 (3)	0.14 (2)	0.241*	0.5
H1BB	0.695 (3)	1.051 (5)	0.182 (2)	0.241*	0.5
C1B	0.7709 (18)	0.945 (2)	0.1969 (11)	0.118 (8)
H1BC	0.828793	0.893728	0.165286	0.177*
C2B	0.8117 (19)	1.048 (2)	0.3370 (11)	0.108 (7)
H2B	0.739236	1.081363	0.348733	0.162*
C3B	0.813 (2)	0.986 (2)	0.4005 (11)	0.125 (8)
H3BA	0.837089	1.055436	0.492956	0.187*
H3BB	0.879232	0.944902	0.387526	0.187*
C4B	0.692 (2)	0.875 (2)	0.3692 (12)	0.132 (7)
H4BA	0.709352	0.828907	0.416455	0.198*
H4BB	0.628150	0.916032	0.396160	0.198*
C5B	0.647 (2)	0.775 (3)	0.2269 (14)	0.152 (8)
H5B	0.711614	0.731926	0.201773	0.228*
C6B	0.6351 (19)	0.858 (2)	0.1655 (11)	0.113 (7)
H6BA	0.585242	0.917007	0.202399	0.169*
H6BB	0.595393	0.799732	0.071533	0.169*
C7B	0.917 (4)	1.175 (4)	0.379 (2)	0.146 (9)
H7B	0.896607	1.208317	0.319775	0.219*
C8B	1.031 (4)	1.137 (4)	0.3668 (17)	0.178 (14)
H8BA	1.015170	1.064494	0.278522	0.213*
H8BB	1.098670	1.215724	0.387306	0.213*
H8BC	1.052885	1.106670	0.426194	0.213*
C9B	0.937 (2)	1.280 (2)	0.5053 (13)	0.156 (12)
H9BA	0.860712	1.303351	0.511878	0.188*
H9BB	0.958410	1.249689	0.565375	0.188*
H9BC	1.004195	1.358744	0.526486	0.188*
C10B	0.529 (3)	0.668 (3)	0.1933 (16)	0.192 (14)
H10D	0.500320	0.603129	0.100507	0.230*
H10E	0.544118	0.620722	0.239017	0.230*
H10F	0.465735	0.709420	0.218407	0.230*
O1C	0.9369 (9)	1.0799 (9)	0.0514 (8)	0.136 (11)
H1C	0.868 (19)	1.05 (4)	0.07 (2)	0.204*	0.5
H1CA	0.976 (3)	1.025 (3)	0.037 (3)	0.204*	0.5
C2C	1.0516 (18)	1.252 (2)	0.0292 (10)	0.097 (7)
H2C	1.077819	1.181644	−0.036177	0.146*
C6C	0.8326 (17)	1.1115 (19)	−0.1068 (9)	0.095 (7)
H6CA	0.855827	1.036709	−0.169035	0.143*
H6CB	0.750344	1.072637	−0.102498	0.143*
C4C	0.9498 (17)	1.2794 (19)	−0.1439 (9)	0.096 (7)
H4CA	0.941929	1.345717	−0.169675	0.144*
H4CB	0.981206	1.213921	−0.206283	0.144*
C1C	0.928 (2)	1.183 (2)	0.0255 (11)	0.091 (7)
H1CB	0.898563	1.248679	0.091293	0.136*
C5C	0.8257 (19)	1.207 (2)	−0.1511 (12)	0.121 (8)
H5C	0.800335	1.277628	−0.084936	0.182*
C3C	1.042 (2)	1.351 (2)	−0.0145 (11)	0.114 (7)
H3CA	1.015504	1.423102	0.047240	0.170*
H3CB	1.123438	1.393165	−0.017323	0.170*
C7C	1.146 (2)	1.309 (2)	0.1578 (14)	0.115 (8)
H7C	1.145820	1.235977	0.176762	0.173*
C8C	1.111 (2)	1.422 (2)	0.2643 (12)	0.136 (12)
H8CA	1.027800	1.383290	0.265579	0.164*
H8CB	1.170944	1.458858	0.348084	0.164*
H8CC	1.111170	1.493955	0.245914	0.164*
C9C	1.273 (3)	1.369 (3)	0.1561 (12)	0.167 (13)
H9CA	1.332850	1.405211	0.239802	0.200*
H9CB	1.294821	1.298359	0.089148	0.200*
H9CC	1.273120	1.440980	0.138169	0.200*
C10C	0.724 (2)	1.148 (2)	−0.2765 (10)	0.122 (12)
H10G	0.725326	1.216986	−0.299401	0.146*
H10H	0.737999	1.070954	−0.344796	0.146*
H10I	0.643300	1.118167	−0.266063	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.136 (16)	0.121 (15)	0.092 (5)	0.042 (13)	0.023 (7)	0.052 (7)
C1	0.115 (11)	0.105 (11)	0.088 (7)	0.045 (8)	0.013 (7)	0.055 (8)
C2	0.086 (10)	0.091 (10)	0.076 (6)	0.039 (8)	0.001 (6)	0.043 (7)
C3	0.120 (11)	0.096 (11)	0.111 (7)	0.035 (7)	0.016 (7)	0.068 (7)
C4	0.115 (11)	0.100 (10)	0.121 (7)	0.032 (8)	0.034 (7)	0.050 (7)
C5	0.123 (11)	0.108 (11)	0.128 (8)	0.023 (7)	0.055 (7)	0.067 (8)
C6	0.105 (11)	0.112 (11)	0.118 (7)	0.029 (7)	0.046 (7)	0.058 (8)
C7	0.092 (11)	0.085 (11)	0.110 (8)	0.029 (8)	0.020 (8)	0.051 (7)
C8	0.115 (18)	0.130 (18)	0.132 (9)	0.035 (14)	0.027 (12)	0.078 (11)
C9	0.128 (18)	0.171 (18)	0.113 (8)	0.069 (14)	0.023 (9)	0.063 (10)
C10	0.190 (19)	0.18 (2)	0.185 (11)	0.040 (14)	0.079 (12)	0.108 (13)
O1B	0.182 (17)	0.188 (17)	0.135 (6)	0.038 (13)	0.035 (8)	0.114 (9)
C1B	0.135 (11)	0.130 (11)	0.113 (7)	0.037 (7)	0.036 (7)	0.085 (8)
C2B	0.099 (11)	0.110 (11)	0.114 (7)	0.036 (8)	0.031 (7)	0.057 (8)
C3B	0.124 (12)	0.128 (11)	0.115 (7)	0.043 (8)	0.046 (7)	0.055 (8)
C4B	0.143 (11)	0.145 (11)	0.122 (7)	0.048 (8)	0.040 (7)	0.080 (8)
C5B	0.145 (12)	0.142 (12)	0.161 (9)	0.039 (8)	0.057 (8)	0.072 (9)
C6B	0.127 (11)	0.114 (10)	0.105 (6)	0.040 (7)	0.032 (7)	0.064 (7)
C7B	0.139 (13)	0.155 (13)	0.141 (9)	0.049 (8)	0.046 (9)	0.073 (9)
C8B	0.18 (2)	0.21 (2)	0.138 (11)	0.070 (15)	0.073 (14)	0.081 (13)
C9B	0.103 (17)	0.156 (18)	0.161 (10)	0.037 (14)	0.059 (11)	0.041 (12)
C10B	0.21 (2)	0.15 (2)	0.224 (12)	0.036 (14)	0.065 (13)	0.113 (13)
O1C	0.160 (16)	0.125 (16)	0.142 (7)	0.041 (12)	0.051 (7)	0.085 (9)
C2C	0.106 (11)	0.093 (10)	0.088 (6)	0.038 (7)	0.030 (7)	0.041 (7)
C6C	0.100 (11)	0.091 (10)	0.077 (6)	0.042 (7)	0.034 (6)	0.023 (7)
C4C	0.109 (11)	0.109 (10)	0.079 (5)	0.047 (7)	0.021 (6)	0.054 (7)
C1C	0.081 (11)	0.095 (11)	0.086 (6)	0.046 (8)	0.012 (7)	0.036 (8)
C5C	0.132 (12)	0.121 (11)	0.121 (8)	0.039 (8)	0.041 (8)	0.071 (8)
C3C	0.096 (11)	0.108 (11)	0.124 (7)	0.030 (7)	0.029 (7)	0.053 (8)
C7C	0.120 (11)	0.107 (11)	0.121 (8)	0.036 (8)	0.038 (8)	0.061 (8)
C8C	0.149 (18)	0.139 (18)	0.102 (8)	0.060 (14)	0.037 (10)	0.043 (10)
C9C	0.17 (2)	0.179 (19)	0.139 (9)	0.076 (15)	0.053 (11)	0.061 (12)
C10C	0.148 (17)	0.134 (17)	0.096 (7)	0.064 (14)	0.009 (8)	0.072 (9)

Geometric parameters (Å, º) top

O1—H1A	0.8200 (12)	C5B—C6B	1.48 (3)
O1—H1B	0.8200 (12)	C5B—C10B	1.473 (19)
O1—C1	1.420 (6)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.473 (13)	C7B—H7B	0.9800
C1—C6	1.510 (16)	C7B—C8B	1.46 (9)
C2—H2	0.9800	C7B—C9B	1.38 (3)
C2—C3	1.45 (3)	C8B—H8BA	0.9600
C2—C7	1.371 (16)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.476 (16)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.407 (13)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.32 (3)	O1C—H1C	0.87 (10)
C5—C10	1.395 (19)	O1C—H1CA	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.39 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.45 (2)
C7—C8	1.32 (5)	C2C—C3C	1.48 (3)
C7—C9	1.413 (17)	C2C—C7C	1.483 (18)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.497 (15)
C9—H9A	0.9600	C6C—C5C	1.45 (2)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.448 (18)
C10—H10B	0.9600	C4C—C3C	1.454 (14)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.90 (11)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (11)	C5C—C10C	1.492 (19)
O1B—C1B	1.58 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.464 (18)	C7C—H7C	0.9800
C1B—C6B	1.527 (18)	C7C—C8C	1.53 (4)
C2B—H2B	0.9800	C7C—C9C	1.47 (2)
C2B—C3B	1.27 (2)	C8C—H8CA	0.9600
C2B—C7B	1.49 (2)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.525 (15)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.47 (2)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	143 (10)	C10B—C5B—C6B	115 (2)
C1—O1—H1A	86.9 (17)	C1B—C6B—H6BA	110.8
C1—O1—H1B	124 (10)	C1B—C6B—H6BB	110.8
O1—C1—H1	110.3	C5B—C6B—C1B	104.6 (17)
O1—C1—C2	105.7 (13)	C5B—C6B—H6BA	110.8
O1—C1—C6	110.7 (15)	C5B—C6B—H6BB	110.8
C2—C1—H1	110.3	H6BA—C6B—H6BB	108.9
C2—C1—C6	109.3 (9)	C2B—C7B—H7B	108.4
C6—C1—H1	110.3	C8B—C7B—C2B	108 (5)
C1—C2—H2	108.0	C8B—C7B—H7B	108.4
C3—C2—C1	104.3 (14)	C9B—C7B—C2B	113.3 (19)
C3—C2—H2	108.0	C9B—C7B—H7B	108.4
C7—C2—C1	112.4 (10)	C9B—C7B—C8B	111 (2)
C7—C2—H2	108.0	C7B—C8B—H8BA	109.5
C7—C2—C3	116 (2)	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.1	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.1	H8BA—C8B—H8BB	109.5
C2—C3—C4	113 (2)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.8	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.1	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.1	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	108.0	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.6 (9)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	107.1	C5B—C10B—H10F	109.5
C6—C5—C4	109.5 (16)	H10D—C10B—H10E	109.5
C6—C5—H5	107.1	H10D—C10B—H10F	109.5
C6—C5—C10	115 (2)	H10E—C10B—H10F	109.5
C10—C5—C4	110.2 (11)	H1C—O1C—H1CA	109.00
C10—C5—H5	107.1	C1C—O1C—H1C	110.00
C1—C6—H6A	107.7	C1C—O1C—H1CA	138 (2)
C1—C6—H6B	107.7	C1C—C2C—H2C	106.5
C5—C6—C1	118 (2)	C1C—C2C—C3C	110 (2)
C5—C6—H6A	107.7	C1C—C2C—C7C	110.9 (9)
C5—C6—H6B	107.7	C3C—C2C—H2C	106.5
H6A—C6—H6B	107.1	C7C—C2C—H2C	106.5
C2—C7—H7	106.3	C7C—C2C—C3C	116.0 (12)
C2—C7—C9	112.7 (12)	H6CA—C6C—H6CB	108.1
C8—C7—C2	118 (3)	C1C—C6C—H6CA	109.5
C8—C7—H7	106.3	C1C—C6C—H6CB	109.5
C8—C7—C9	106 (2)	C5C—C6C—H6CA	109.5
C9—C7—H7	106.3	C5C—C6C—H6CB	109.5
C7—C8—H8A	109.5	C5C—C6C—C1C	110.6 (13)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.7
C7—C8—H8C	109.5	C5C—C4C—H4CA	108.8
H8A—C8—H8B	109.5	C5C—C4C—H4CB	108.8
H8A—C8—H8C	109.5	C5C—C4C—C3C	113.8 (8)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	108.8
C7—C9—H9A	109.5	C3C—C4C—H4CB	108.8
C7—C9—H9B	109.5	O1C—C1C—C2C	109 (2)
C7—C9—H9C	109.5	O1C—C1C—C6C	105.6 (13)
H9A—C9—H9B	109.5	O1C—C1C—H1CB	109.8
H9A—C9—H9C	109.5	C2C—C1C—C6C	112.8 (10)
H9B—C9—H9C	109.5	C2C—C1C—H1CB	109.8
C5—C10—H10A	109.5	C6C—C1C—H1CB	109.8
C5—C10—H10B	109.5	C6C—C5C—C4C	111 (2)
C5—C10—H10C	109.5	C6C—C5C—H5C	104.8
H10A—C10—H10B	109.5	C6C—C5C—C10C	114.3 (12)
H10A—C10—H10C	109.5	C4C—C5C—H5C	104.8
H10B—C10—H10C	109.5	C4C—C5C—C10C	115.7 (9)
H1BA—O1B—H1BB	121 (10)	C10C—C5C—H5C	104.8
C1B—O1B—H1BA	103 (10)	C2C—C3C—H3CA	109.7
C1B—O1B—H1BB	84 (2)	C2C—C3C—H3CB	109.7
O1B—C1B—H1BC	116.4	C4C—C3C—C2C	109.8 (13)
C2B—C1B—O1B	103.6 (18)	C4C—C3C—H3CA	109.7
C2B—C1B—H1BC	116.4	C4C—C3C—H3CB	109.7
C2B—C1B—C6B	106.0 (13)	H3CA—C3C—H3CB	108.2
C6B—C1B—O1B	95.4 (15)	C2C—C7C—H7C	109.4
C6B—C1B—H1BC	116.4	C2C—C7C—C8C	109 (3)
C1B—C2B—H2B	103.2	C8C—C7C—H7C	109.4
C1B—C2B—C7B	115.3 (13)	C9C—C7C—C2C	110.3 (11)
C3B—C2B—C1B	108.1 (18)	C9C—C7C—H7C	109.4
C3B—C2B—H2B	103.2	C9C—C7C—C8C	109.3 (14)
C3B—C2B—C7B	121 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	103.2	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	107.6	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	107.6	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	118.7 (17)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	107.1	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	107.6	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	107.6	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	108.3	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	108.7 (12)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	109.0	C5C—C10C—H10I	109.5
C4B—C5B—C6B	105.0 (19)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	109.0	H10G—C10C—H10I	109.5
C10B—C5B—C4B	110.0 (14)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	109.0

O1—C1—C2—C3	173.3 (16)	C3B—C2B—C7B—C9B	−58 (6)
O1—C1—C2—C7	−61 (3)	C3B—C4B—C5B—C6B	−55 (3)
O1—C1—C6—C5	−171.5 (17)	C3B—C4B—C5B—C10B	−179 (3)
C1—C2—C3—C4	−61 (2)	C4B—C5B—C6B—C1B	68 (2)
C1—C2—C7—C8	−67 (3)	C6B—C1B—C2B—C3B	64 (3)
C1—C2—C7—C9	169 (3)	C6B—C1B—C2B—C7B	−157 (3)
C2—C1—C6—C5	−55 (3)	C7B—C2B—C3B—C4B	168 (3)
C2—C3—C4—C5	61 (3)	C10B—C5B—C6B—C1B	−171 (2)
C3—C2—C7—C8	53 (2)	C1C—C2C—C3C—C4C	−56 (2)
C3—C2—C7—C9	−71 (3)	C1C—C2C—C7C—C8C	−65 (2)
C3—C4—C5—C6	−53 (3)	C1C—C2C—C7C—C9C	175 (2)
C3—C4—C5—C10	179 (3)	C1C—C6C—C5C—C4C	52 (2)
C4—C5—C6—C1	52 (3)	C1C—C6C—C5C—C10C	−174 (2)
C6—C1—C2—C3	54 (3)	C5C—C6C—C1C—O1C	−173.7 (17)
C6—C1—C2—C7	−180 (3)	C5C—C6C—C1C—C2C	−55 (3)
C7—C2—C3—C4	175.5 (15)	C5C—C4C—C3C—C2C	56 (3)
C10—C5—C6—C1	177.3 (17)	C3C—C2C—C1C—O1C	173.0 (12)
O1B—C1B—C2B—C3B	163.9 (19)	C3C—C2C—C1C—C6C	56 (2)
O1B—C1B—C2B—C7B	−57 (4)	C3C—C2C—C7C—C8C	61 (2)
O1B—C1B—C6B—C5B	−178.1 (16)	C3C—C2C—C7C—C9C	−59 (3)
C1B—C2B—C3B—C4B	−56 (3)	C3C—C4C—C5C—C6C	−55 (2)
C1B—C2B—C7B—C8B	−69 (3)	C3C—C4C—C5C—C10C	172 (2)
C1B—C2B—C7B—C9B	169 (3)	C7C—C2C—C1C—O1C	−57 (2)
C2B—C1B—C6B—C5B	−72 (2)	C7C—C2C—C1C—C6C	−174 (2)
C2B—C3B—C4B—C5B	53 (3)	C7C—C2C—C3C—C4C	177.5 (19)
C3B—C2B—C7B—C8B	65 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_1.70GPa) top

Crystal data top

C₁₀H₂₀O	Z = 6
M_r = 156.26	F(000) = 528
Triclinic, P1	D_x = 1.209 Mg m⁻³
Hall symbol: -P 1	Melting point: 308 K
a = 11.262 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.533 (4) Å	Cell parameters from 1408 reflections
c = 11.991 (4) Å	θ = 3.2–29.8°
α = 117.74 (3)°	µ = 0.08 mm⁻¹
β = 99.47 (2)°	T = 296 K
γ = 101.75 (3)°	Plate, colourless
V = 1287.7 (8) Å³	0.39 × 0.3 × 0.06 mm

Data collection top

Xcalibur, Eos diffractometer	318 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.259
ω scans	θ_max = 28.4°, θ_min = 4.4°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
T_min = 0.397, T_max = 0.929	k = −15→15
6757 measured reflections	l = −11→11
1201 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.079	w = 1/[σ²(F_o²) + (0.1287P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.295	(Δ/σ)_max < 0.001
S = 0.94	Δρ_max = 0.10 e Å⁻³
1201 reflections	Δρ_min = −0.09 e Å⁻³
321 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
243 restraints	Extinction coefficient: 0.005 (6)

Special details top

Experimental. Data were collected at room temperature and pressure of 1.70 (2) GPa (1700000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5366 (10)	1.0673 (15)	0.1224 (16)	0.094 (9)
H1A	0.610 (2)	1.066 (6)	0.135 (16)	0.141*	0.5
H1B	0.539 (7)	1.008 (7)	0.0510 (7)	0.141*	0.5
C1	0.5593 (12)	1.2122 (15)	0.1916 (17)	0.064 (6)
H1	0.480074	1.225823	0.160557	0.077*
C2	0.5950 (14)	1.2920 (16)	0.3459 (17)	0.093 (7)
H2	0.677068	1.280478	0.371348	0.111*
C3	0.6272 (13)	1.4487 (17)	0.418 (2)	0.096 (6)
H3A	0.666811	1.489552	0.511836	0.144*
H3B	0.551129	1.474092	0.406121	0.144*
C4	0.7201 (12)	1.4978 (17)	0.3559 (18)	0.073 (6)
H4A	0.735643	1.596125	0.391952	0.088*
H4B	0.800415	1.485749	0.383269	0.088*
C5	0.6790 (11)	1.4278 (14)	0.2102 (18)	0.076 (6)
H5	0.600833	1.444054	0.180949	0.091*
C6	0.6556 (12)	1.2781 (16)	0.151 (2)	0.071 (6)
H6A	0.628175	1.233878	0.055872	0.106*
H6B	0.734724	1.262736	0.176238	0.106*
C7	0.5133 (11)	1.2204 (18)	0.396 (2)	0.067 (6)
H7	0.502553	1.122052	0.340338	0.100*
C8	0.3784 (12)	1.233 (2)	0.362 (3)	0.079 (9)
H8A	0.351275	1.206239	0.270981	0.095*
H8B	0.319495	1.173651	0.377889	0.095*
H8C	0.381552	1.327073	0.416794	0.095*
C9	0.5734 (16)	1.2563 (19)	0.530 (2)	0.122 (10)
H9A	0.659840	1.256891	0.540139	0.184*
H9B	0.527968	1.189316	0.547567	0.184*
H9C	0.571749	1.346323	0.592017	0.184*
C10	0.7861 (13)	1.501 (2)	0.183 (3)	0.080 (9)
H10A	0.794414	1.597986	0.224834	0.096*
H10B	0.863774	1.490738	0.216903	0.096*
H10C	0.768394	1.462750	0.089289	0.096*
O1B	0.7362 (8)	0.9923 (13)	0.1074 (16)	0.084 (8)
H1BA	0.801 (4)	1.051 (5)	0.121 (9)	0.126*	0.5
H1BB	0.714 (5)	1.054 (4)	0.160 (3)	0.126*	0.5
C1B	0.7527 (12)	0.9372 (15)	0.1956 (15)	0.064 (6)
H1BC	0.816423	0.890344	0.174720	0.077*
C2B	0.8060 (13)	1.0473 (14)	0.3349 (16)	0.065 (6)
H2B	0.739531	1.089333	0.357607	0.078*
C3B	0.8223 (11)	0.9764 (19)	0.416 (2)	0.094 (6)
H3BA	0.838712	1.041144	0.508949	0.141*
H3BB	0.891715	0.938433	0.403888	0.141*
C4B	0.6895 (14)	0.8562 (17)	0.357 (2)	0.088 (7)
H4BA	0.697216	0.807016	0.403874	0.106*
H4BB	0.626774	0.901490	0.383227	0.106*
C5B	0.6321 (16)	0.747 (2)	0.213 (2)	0.095 (8)
H5B	0.690994	0.694800	0.186879	0.114*
C6B	0.6247 (10)	0.8233 (16)	0.132 (2)	0.079 (6)
H6BA	0.613008	0.760270	0.038887	0.119*
H6BB	0.555438	0.861900	0.139202	0.119*
C7B	0.9193 (11)	1.1595 (17)	0.379 (2)	0.100 (8)
H7B	0.901532	1.192807	0.318849	0.149*
C8B	1.0312 (16)	1.124 (3)	0.361 (4)	0.094 (9)
H8BA	1.101111	1.206198	0.393750	0.113*
H8BB	1.049998	1.077711	0.407140	0.113*
H8BC	1.018010	1.063335	0.268105	0.113*
C9B	0.9420 (14)	1.283 (2)	0.511 (2)	0.121 (11)
H9BA	0.863685	1.301916	0.518068	0.146*
H9BB	0.973975	1.265101	0.578765	0.146*
H9BC	1.003094	1.360904	0.520679	0.146*
C10B	0.5092 (17)	0.649 (3)	0.181 (4)	0.112 (10)
H10D	0.522189	0.577363	0.195827	0.167*
H10E	0.463335	0.609190	0.089460	0.167*
H10F	0.461342	0.696209	0.235404	0.167*
O1C	0.9304 (8)	1.0742 (10)	0.0493 (13)	0.080 (8)
H1C	0.902 (4)	1.097 (12)	0.113 (3)	0.120*	0.5
H1CA	0.9914 (17)	1.049 (3)	0.032 (12)	0.120*	0.5
C2C	1.0537 (11)	1.2579 (18)	0.043 (2)	0.069 (6)
H2C	1.093987	1.195204	−0.012430	0.082*
C6C	0.8119 (12)	1.0892 (14)	−0.1436 (18)	0.075 (6)
H6CA	0.835697	1.018695	−0.211497	0.090*
H6CB	0.727347	1.049026	−0.143710	0.090*
C4C	0.9388 (19)	1.260 (2)	−0.161 (3)	0.124 (8)
H4CA	0.929464	1.317578	−0.197798	0.149*
H4CB	0.970628	1.189055	−0.217323	0.149*
C1C	0.9098 (11)	1.1583 (15)	−0.0067 (19)	0.062 (6)
H1CB	0.869837	1.218903	0.051922	0.074*
C5C	0.819 (2)	1.197 (2)	−0.158 (4)	0.104 (8)
H5C	0.792160	1.265042	−0.090756	0.124*
C3C	1.0315 (19)	1.345 (3)	−0.028 (3)	0.086 (7)
H3CA	1.002197	1.419708	0.026579	0.103*
H3CB	1.112070	1.386240	−0.035039	0.103*
C7C	1.1483 (13)	1.329 (2)	0.176 (2)	0.097 (7)
H7C	1.151487	1.255538	0.195695	0.116*
C8C	1.1234 (18)	1.443 (2)	0.299 (3)	0.147 (11)
H8CA	1.132480	1.524729	0.293078	0.220*
H8CB	1.183699	1.465961	0.378673	0.220*
H8CC	1.038825	1.409770	0.300887	0.220*
C9C	1.2790 (19)	1.383 (3)	0.171 (5)	0.132 (10)
H9CA	1.338521	1.428061	0.257922	0.159*
H9CB	1.302362	1.307325	0.111015	0.159*
H9CC	1.279718	1.447626	0.142422	0.159*
C10C	0.723 (2)	1.131 (3)	−0.296 (4)	0.097 (10)
H10G	0.753060	1.068305	−0.362405	0.145*
H10H	0.712797	1.201996	−0.313604	0.145*
H10I	0.642161	1.080693	−0.298296	0.145*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.088 (10)	0.097 (13)	0.10 (3)	0.019 (9)	0.015 (15)	0.064 (17)
C1	0.065 (8)	0.066 (10)	0.064 (14)	0.024 (7)	0.016 (9)	0.036 (10)
C2	0.092 (9)	0.094 (11)	0.093 (15)	0.032 (8)	0.024 (10)	0.050 (10)
C3	0.094 (8)	0.097 (10)	0.097 (14)	0.032 (7)	0.030 (9)	0.050 (10)
C4	0.080 (9)	0.078 (10)	0.068 (14)	0.022 (7)	0.021 (9)	0.044 (10)
C5	0.065 (8)	0.073 (11)	0.078 (15)	0.027 (7)	0.019 (9)	0.030 (10)
C6	0.068 (7)	0.078 (10)	0.070 (14)	0.028 (7)	0.013 (8)	0.041 (10)
C7	0.067 (8)	0.064 (10)	0.067 (14)	0.018 (7)	0.028 (9)	0.031 (10)
C8	0.077 (10)	0.064 (15)	0.10 (3)	0.037 (10)	0.041 (13)	0.033 (17)
C9	0.117 (13)	0.137 (19)	0.12 (3)	0.039 (12)	0.040 (16)	0.065 (19)
C10	0.096 (10)	0.058 (15)	0.09 (3)	0.031 (10)	0.033 (14)	0.039 (17)
O1B	0.093 (8)	0.096 (13)	0.09 (2)	0.032 (8)	0.040 (11)	0.059 (16)
C1B	0.063 (8)	0.058 (10)	0.070 (14)	0.017 (7)	0.018 (9)	0.033 (10)
C2B	0.056 (8)	0.069 (11)	0.064 (14)	0.015 (7)	0.012 (9)	0.035 (10)
C3B	0.081 (8)	0.097 (10)	0.094 (14)	0.020 (7)	0.033 (9)	0.044 (10)
C4B	0.090 (9)	0.083 (11)	0.089 (15)	0.021 (7)	0.032 (9)	0.044 (10)
C5B	0.091 (9)	0.094 (11)	0.095 (15)	0.031 (8)	0.034 (9)	0.041 (10)
C6B	0.065 (7)	0.082 (10)	0.080 (14)	0.023 (7)	0.021 (9)	0.035 (10)
C7B	0.093 (10)	0.097 (12)	0.101 (15)	0.032 (8)	0.042 (10)	0.040 (10)
C8B	0.083 (11)	0.093 (16)	0.09 (3)	0.041 (10)	0.037 (14)	0.031 (18)
C9B	0.089 (13)	0.130 (19)	0.13 (3)	0.045 (12)	0.031 (16)	0.047 (19)
C10B	0.112 (12)	0.097 (17)	0.13 (3)	0.038 (11)	0.044 (15)	0.052 (18)
O1C	0.088 (7)	0.083 (12)	0.09 (2)	0.034 (8)	0.030 (11)	0.051 (16)
C2C	0.067 (8)	0.065 (10)	0.070 (14)	0.014 (7)	0.024 (9)	0.033 (10)
C6C	0.084 (8)	0.075 (10)	0.071 (14)	0.021 (7)	0.026 (9)	0.043 (10)
C4C	0.120 (11)	0.123 (12)	0.124 (15)	0.018 (8)	0.046 (10)	0.067 (11)
C1C	0.075 (8)	0.056 (10)	0.063 (14)	0.029 (7)	0.021 (8)	0.034 (10)
C5C	0.105 (10)	0.111 (11)	0.102 (15)	0.039 (8)	0.019 (9)	0.063 (10)
C3C	0.103 (9)	0.085 (10)	0.083 (15)	0.013 (7)	0.029 (9)	0.061 (10)
C7C	0.107 (10)	0.092 (11)	0.099 (15)	0.027 (8)	0.036 (10)	0.056 (10)
C8C	0.135 (14)	0.149 (19)	0.16 (3)	0.064 (13)	0.038 (17)	0.073 (19)
C9C	0.106 (12)	0.157 (19)	0.13 (3)	0.025 (12)	0.054 (16)	0.069 (19)
C10C	0.119 (12)	0.095 (17)	0.09 (3)	0.045 (11)	0.036 (15)	0.055 (18)

Geometric parameters (Å, º) top

O1—H1A	0.8200 (18)	C5B—C6B	1.585 (5)
O1—H1B	0.8200 (12)	C5B—C10B	1.459 (10)
O1—C1	1.419 (6)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.566 (4)	C7B—H7B	0.9800
C1—C6	1.472 (8)	C7B—C8B	1.424 (6)
C2—H2	0.9800	C7B—C9B	1.4840 (15)
C2—C3	1.523 (2)	C8B—H8BA	0.9600
C2—C7	1.492 (2)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.5429 (12)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.479 (2)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.473 (2)	O1C—H1C	0.8200 (12)
C5—C10	1.5020 (13)	O1C—H1CA	0.8200 (13)
C6—H6A	0.9700	O1C—C1C	1.447 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.607 (5)
C7—C8	1.560 (8)	C2C—C3C	1.628 (6)
C7—C9	1.460 (2)	C2C—C7C	1.488 (10)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.541 (2)
C9—H9A	0.9600	C6C—C5C	1.320 (5)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.404 (9)
C10—H10B	0.9600	C4C—C3C	1.471 (10)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (13)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.548 (9)
O1B—C1B	1.471 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.466 (4)	C7C—H7C	0.9800
C1B—C6B	1.5231 (14)	C7C—C8C	1.573 (7)
C2B—H2B	0.9800	C7C—C9C	1.498 (7)
C2B—C3B	1.543 (5)	C8C—H8CA	0.9600
C2B—C7B	1.4312 (14)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.599 (2)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.5089 (15)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	75 (9)	C10B—C5B—C6B	111.8 (11)
C1—O1—H1A	100 (4)	C1B—C6B—C5B	103.6 (10)
C1—O1—H1B	138 (7)	C1B—C6B—H6BA	111.0
O1—C1—H1	106.2	C1B—C6B—H6BB	111.0
O1—C1—C2	118.6 (13)	C5B—C6B—H6BA	111.0
O1—C1—C6	109.3 (10)	C5B—C6B—H6BB	111.0
C2—C1—H1	106.2	H6BA—C6B—H6BB	109.0
C6—C1—H1	106.2	C2B—C7B—H7B	103.1
C6—C1—C2	109.5 (12)	C2B—C7B—C9B	115.5 (16)
C1—C2—H2	102.6	C8B—C7B—C2B	116.4 (14)
C3—C2—C1	117.5 (14)	C8B—C7B—H7B	103.1
C3—C2—H2	102.6	C8B—C7B—C9B	113 (2)
C7—C2—C1	113.1 (14)	C9B—C7B—H7B	103.1
C7—C2—H2	102.6	C7B—C8B—H8BA	109.5
C7—C2—C3	115.7 (11)	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.7	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.7	H8BA—C8B—H8BB	109.5
C2—C3—C4	105.4 (10)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	108.8	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.7	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.7	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.2	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.2	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.4	H9BA—C9B—H9BC	109.5
C5—C4—C3	116.3 (12)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.2	C5B—C10B—H10D	109.5
C5—C4—H4B	108.2	C5B—C10B—H10E	109.5
C4—C5—H5	109.5	C5B—C10B—H10F	109.5
C4—C5—C10	102.9 (14)	H10D—C10B—H10E	109.5
C6—C5—C4	110.0 (15)	H10D—C10B—H10F	109.5
C6—C5—H5	109.5	H10E—C10B—H10F	109.5
C6—C5—C10	115.2 (10)	H1C—O1C—H1CA	135 (10)
C10—C5—H5	109.5	C1C—O1C—H1C	108 (10)
C1—C6—C5	113.6 (10)	C1C—O1C—H1CA	109 (10)
C1—C6—H6A	108.8	C1C—C2C—H2C	102.0
C1—C6—H6B	108.8	C1C—C2C—C3C	98.6 (8)
C5—C6—H6A	108.8	C3C—C2C—H2C	102.0
C5—C6—H6B	108.8	C7C—C2C—H2C	102.0
H6A—C6—H6B	107.7	C7C—C2C—C1C	128.7 (12)
C2—C7—H7	105.2	C7C—C2C—C3C	119.5 (16)
C2—C7—C8	107.4 (11)	H6CA—C6C—H6CB	109.4
C8—C7—H7	105.2	C1C—C6C—H6CA	111.6
C9—C7—C2	113.7 (14)	C1C—C6C—H6CB	111.6
C9—C7—H7	105.2	C5C—C6C—H6CA	111.6
C9—C7—C8	118.8 (17)	C5C—C6C—H6CB	111.6
C7—C8—H8A	109.5	C5C—C6C—C1C	100.6 (17)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.9
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.2
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.2
H8A—C8—H8C	109.5	C5C—C4C—C3C	112 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.2
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.2
C7—C9—H9B	109.5	O1C—C1C—C2C	98.8 (7)
C7—C9—H9C	109.5	O1C—C1C—C6C	118.8 (10)
H9A—C9—H9B	109.5	O1C—C1C—H1CB	102.6
H9A—C9—H9C	109.5	C2C—C1C—H1CB	102.6
H9B—C9—H9C	109.5	C6C—C1C—C2C	127.9 (12)
C5—C10—H10A	109.5	C6C—C1C—H1CB	102.6
C5—C10—H10B	109.5	C6C—C5C—C4C	115.1 (13)
C5—C10—H10C	109.5	C6C—C5C—H5C	110.2
H10A—C10—H10B	109.5	C6C—C5C—C10C	102.1 (17)
H10A—C10—H10C	109.5	C4C—C5C—H5C	110.2
H10B—C10—H10C	109.5	C4C—C5C—C10C	109 (2)
H1BA—O1B—H1BB	89 (7)	C10C—C5C—H5C	110.2
C1B—O1B—H1BA	113 (7)	C2C—C3C—H3CA	109.0
C1B—O1B—H1BB	91.6 (19)	C2C—C3C—H3CB	109.0
O1B—C1B—H1BC	106.1	C4C—C3C—C2C	113.1 (18)
O1B—C1B—C6B	97.9 (7)	C4C—C3C—H3CA	109.0
C2B—C1B—O1B	112.2 (12)	C4C—C3C—H3CB	109.0
C2B—C1B—H1BC	106.1	H3CA—C3C—H3CB	107.8
C2B—C1B—C6B	126.7 (14)	C2C—C7C—H7C	105.2
C6B—C1B—H1BC	106.1	C2C—C7C—C8C	119.8 (13)
C1B—C2B—H2B	106.0	C2C—C7C—C9C	111 (2)
C1B—C2B—C3B	107.0 (12)	C8C—C7C—H7C	105.2
C3B—C2B—H2B	106.0	C9C—C7C—H7C	105.2
C7B—C2B—C1B	121.2 (15)	C9C—C7C—C8C	109.5 (19)
C7B—C2B—H2B	106.0	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	109.6 (12)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	110.9	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	110.9	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	104.1 (10)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	109.0	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	110.9	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	110.9	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	106.5	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	106.5	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	106.5	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	123.4 (17)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	106.5	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	106.5	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.4	C5C—C10C—H10I	109.5
C4B—C5B—C6B	108.3 (16)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	107.4	H10G—C10C—H10I	109.5
C10B—C5B—C4B	114 (2)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.4

O1—C1—C2—C3	176.1 (9)	C3B—C2B—C7B—C9B	−72.0 (18)
O1—C1—C2—C7	−45 (2)	C3B—C4B—C5B—C6B	−54 (2)
O1—C1—C6—C5	175.7 (12)	C3B—C4B—C5B—C10B	−178.9 (10)
C1—C2—C3—C4	−46.8 (18)	C4B—C5B—C6B—C1B	43.5 (18)
C1—C2—C7—C8	−71 (2)	C6B—C1B—C2B—C3B	62.4 (17)
C1—C2—C7—C9	155.6 (15)	C6B—C1B—C2B—C7B	−171.1 (9)
C2—C1—C6—C5	−52.8 (19)	C7B—C2B—C3B—C4B	179.3 (12)
C2—C3—C4—C5	51.6 (18)	C10B—C5B—C6B—C1B	170.2 (17)
C3—C2—C7—C8	69 (2)	C1C—C2C—C3C—C4C	−38.0 (19)
C3—C2—C7—C9	−64.8 (18)	C1C—C2C—C7C—C8C	−65 (2)
C3—C4—C5—C6	−58.6 (16)	C1C—C2C—C7C—C9C	166.3 (13)
C3—C4—C5—C10	178.1 (9)	C1C—C6C—C5C—C4C	62 (3)
C4—C5—C6—C1	58.2 (17)	C1C—C6C—C5C—C10C	179.5 (11)
C6—C1—C2—C3	49.7 (19)	C5C—C6C—C1C—O1C	179.2 (12)
C6—C1—C2—C7	−171.5 (9)	C5C—C6C—C1C—C2C	−50.3 (17)
C7—C2—C3—C4	175.4 (13)	C5C—C4C—C3C—C2C	59 (2)
C10—C5—C6—C1	173.9 (15)	C3C—C2C—C1C—O1C	176.4 (14)
O1B—C1B—C2B—C3B	−178.2 (7)	C3C—C2C—C1C—C6C	38.7 (19)
O1B—C1B—C2B—C7B	−51.7 (19)	C3C—C2C—C7C—C8C	67.3 (18)
O1B—C1B—C6B—C5B	176.7 (12)	C3C—C2C—C7C—C9C	−61.5 (19)
C1B—C2B—C3B—C4B	−47.6 (17)	C3C—C4C—C5C—C6C	−76 (3)
C1B—C2B—C7B—C8B	−61 (2)	C3C—C4C—C5C—C10C	170.3 (14)
C1B—C2B—C7B—C9B	162.7 (16)	C7C—C2C—C1C—O1C	−44.4 (18)
C2B—C1B—C6B—C5B	−57.9 (18)	C7C—C2C—C1C—C6C	178.0 (13)
C2B—C3B—C4B—C5B	55 (2)	C7C—C2C—C3C—C4C	177.8 (14)
C3B—C2B—C7B—C8B	64 (2)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_2.10GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.232 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.198 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.459 (4) Å	Cell parameters from 1420 reflections
c = 11.898 (4) Å	θ = 3.2–30.0°
α = 117.74 (3)°	µ = 0.08 mm⁻¹
β = 99.72 (2)°	T = 296 K
γ = 101.39 (3)°	Plate, colourless
V = 1263.5 (8) Å³	0.39 × 0.3 × 0.05 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	334 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.197
ω scans	θ_max = 27.5°, θ_min = 4.3°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
T_min = 0.973, T_max = 0.996	k = −14→14
5978 measured reflections	l = −11→11
1063 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.084	w = 1/[σ²(F_o²) + (0.148P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.291	(Δ/σ)_max = 0.001
S = 0.95	Δρ_max = 0.12 e Å⁻³
1063 reflections	Δρ_min = −0.11 e Å⁻³
319 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
246 restraints	Extinction coefficient: 0.012 (9)

Special details top

Experimental. Data were collected at room temperature and pressure of 2.10 (2) GPa (2100000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5274 (8)	1.0647 (16)	0.1266 (13)	0.099 (9)
H1A	0.5984 (16)	1.057 (4)	0.126 (7)	0.149*	0.5
H1B	0.486 (8)	1.03 (2)	0.0480 (9)	0.149*	0.5
C1	0.5543 (12)	1.2113 (16)	0.1962 (19)	0.075 (6)
H1	0.476726	1.232070	0.171303	0.112*
C2	0.5974 (12)	1.2765 (15)	0.3508 (19)	0.082 (7)
H2	0.679418	1.263227	0.376007	0.098*
C3	0.6203 (11)	1.4314 (17)	0.408 (2)	0.079 (6)
H3A	0.633230	1.475141	0.502664	0.094*
H3B	0.543178	1.443117	0.369329	0.094*
C4	0.7334 (11)	1.5108 (18)	0.385 (2)	0.084 (7)
H4A	0.741534	1.608747	0.426198	0.101*
H4B	0.813097	1.501120	0.420780	0.101*
C5	0.6967 (12)	1.4411 (16)	0.2387 (19)	0.080 (7)
H5	0.620650	1.463105	0.211629	0.096*
C6	0.6590 (12)	1.2886 (16)	0.173 (2)	0.072 (6)
H6A	0.637150	1.251760	0.077757	0.108*
H6B	0.734305	1.265496	0.197015	0.108*
C7	0.4997 (10)	1.192 (2)	0.378 (3)	0.081 (6)
H7	0.486264	1.096046	0.307852	0.121*
C8	0.3646 (12)	1.210 (3)	0.351 (3)	0.074 (9)
H8A	0.340674	1.202639	0.266674	0.089*
H8B	0.303263	1.137961	0.351433	0.089*
H8C	0.366871	1.298900	0.420276	0.089*
C9	0.5593 (14)	1.198 (2)	0.500 (3)	0.104 (10)
H9A	0.627030	1.157604	0.488087	0.157*
H9B	0.496714	1.147088	0.520558	0.157*
H9C	0.593480	1.293046	0.571542	0.157*
C10	0.7996 (12)	1.506 (2)	0.200 (3)	0.072 (9)
H10A	0.817563	1.605178	0.247503	0.086*
H10B	0.875504	1.484304	0.221268	0.086*
H10C	0.771307	1.470595	0.105853	0.086*
O1B	0.7203 (8)	0.9746 (13)	0.0940 (16)	0.088 (8)
H1BA	0.773 (3)	0.946 (2)	0.058 (4)	0.131*	0.5
H1BB	0.7038 (11)	1.0465 (15)	0.136 (3)	0.131*	0.5
C1B	0.7418 (11)	0.9268 (14)	0.1886 (16)	0.056 (6)
H1BC	0.800953	0.873635	0.162070	0.084*
C2B	0.8028 (15)	1.0286 (14)	0.3307 (16)	0.090 (8)
H2B	0.738564	1.074401	0.356475	0.135*
C3B	0.8211 (11)	0.968 (2)	0.422 (2)	0.072 (6)
H3BA	0.832520	1.036876	0.513883	0.108*
H3BB	0.893005	0.932907	0.417237	0.108*
C4B	0.6884 (16)	0.8460 (19)	0.359 (2)	0.120 (9)
H4BA	0.696436	0.799552	0.408632	0.180*
H4BB	0.625918	0.892887	0.384490	0.180*
C5B	0.6226 (13)	0.7300 (18)	0.2162 (19)	0.061 (6)
H5B	0.676964	0.672012	0.184017	0.091*
C6B	0.6144 (10)	0.8177 (18)	0.146 (2)	0.083 (6)
H6BA	0.587766	0.755563	0.050341	0.124*
H6BB	0.550307	0.863291	0.168312	0.124*
C7B	0.9074 (12)	1.1385 (18)	0.352 (2)	0.090 (8)
H7B	0.878583	1.168322	0.289805	0.134*
C8B	1.0219 (18)	1.108 (3)	0.333 (4)	0.112 (10)
H8BA	1.084735	1.188946	0.349959	0.135*
H8BB	1.053389	1.079702	0.393770	0.135*
H8BC	1.005008	1.033841	0.243346	0.135*
C9B	0.9245 (14)	1.253 (2)	0.488 (2)	0.108 (10)
H9BA	0.844301	1.268728	0.494544	0.130*
H9BB	0.954793	1.227522	0.551451	0.130*
H9BC	0.985627	1.335963	0.506618	0.130*
C10B	0.4934 (15)	0.643 (3)	0.186 (4)	0.125 (10)
H10D	0.461978	0.573439	0.092732	0.150*
H10E	0.494971	0.598715	0.237275	0.150*
H10F	0.438515	0.699642	0.207472	0.150*
O1C	0.9139 (9)	1.0586 (13)	0.0289 (17)	0.072 (8)
H1CA	0.858 (4)	1.008 (4)	0.038 (5)	0.108*	0.5
H1CB	0.979 (2)	1.037 (4)	0.0340 (17)	0.108*	0.5
C2C	1.0527 (10)	1.2408 (19)	0.031 (3)	0.058 (6)
H2C	1.084351	1.172828	−0.033314	0.088*
C6C	0.8170 (14)	1.1113 (17)	−0.144 (2)	0.106 (7)
H6CA	0.840627	1.039878	−0.212608	0.160*
H6CB	0.727816	1.075280	−0.152851	0.160*
C4C	0.9633 (16)	1.296 (2)	−0.138 (3)	0.098 (8)
H4CA	0.957922	1.367739	−0.158793	0.118*
H4CB	0.994041	1.230963	−0.204174	0.118*
C1C	0.9037 (10)	1.1636 (17)	−0.004 (2)	0.070 (6)
H1C	0.870341	1.228389	0.060920	0.106*
C5C	0.8401 (16)	1.226 (2)	−0.149 (3)	0.080 (6)
H5C	0.813309	1.292181	−0.078507	0.119*
C3C	1.0576 (17)	1.361 (2)	−0.007 (3)	0.063 (6)
H3CA	1.036591	1.437402	0.059374	0.076*
H3CB	1.142344	1.396909	−0.009600	0.076*
C7C	1.1493 (15)	1.306 (2)	0.163 (2)	0.116 (8)
H7C	1.153081	1.231279	0.180460	0.139*
C8C	1.1061 (17)	1.412 (2)	0.277 (3)	0.112 (10)
H8CA	1.115426	1.495014	0.273259	0.167*
H8CB	1.158175	1.434618	0.361819	0.167*
H8CC	1.018279	1.370851	0.265979	0.167*
C9C	1.2845 (15)	1.380 (3)	0.182 (4)	0.096 (9)
H9CA	1.335654	1.416994	0.271138	0.115*
H9CB	1.318431	1.316180	0.120313	0.115*
H9CC	1.285566	1.455008	0.165331	0.115*
C10C	0.7320 (18)	1.162 (2)	−0.281 (3)	0.111 (10)
H10G	0.730757	1.230607	−0.305271	0.133*
H10H	0.746753	1.083987	−0.349844	0.133*
H10I	0.651514	1.131679	−0.268571	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.115 (9)	0.103 (15)	0.09 (3)	0.034 (10)	0.053 (14)	0.053 (18)
C1	0.078 (8)	0.077 (11)	0.074 (15)	0.021 (7)	0.018 (9)	0.046 (10)
C2	0.070 (8)	0.089 (12)	0.081 (15)	0.024 (7)	0.032 (9)	0.036 (10)
C3	0.077 (8)	0.079 (11)	0.079 (14)	0.031 (7)	0.022 (9)	0.038 (10)
C4	0.082 (9)	0.087 (12)	0.085 (15)	0.036 (7)	0.027 (9)	0.041 (11)
C5	0.081 (9)	0.080 (11)	0.080 (15)	0.030 (7)	0.020 (9)	0.042 (11)
C6	0.075 (7)	0.066 (10)	0.076 (14)	0.018 (7)	0.023 (9)	0.039 (10)
C7	0.075 (8)	0.085 (11)	0.081 (14)	0.031 (7)	0.027 (9)	0.039 (10)
C8	0.078 (10)	0.085 (16)	0.07 (3)	0.034 (10)	0.027 (13)	0.046 (18)
C9	0.099 (11)	0.124 (19)	0.09 (3)	0.052 (12)	0.037 (15)	0.048 (19)
C10	0.085 (10)	0.059 (16)	0.08 (3)	0.023 (10)	0.037 (14)	0.034 (18)
O1B	0.091 (9)	0.079 (14)	0.09 (2)	0.014 (9)	0.018 (12)	0.049 (17)
C1B	0.054 (8)	0.046 (10)	0.066 (14)	0.019 (7)	0.015 (9)	0.028 (10)
C2B	0.087 (9)	0.086 (12)	0.096 (15)	0.039 (8)	0.017 (9)	0.045 (11)
C3B	0.053 (7)	0.081 (11)	0.070 (14)	0.023 (7)	0.023 (8)	0.029 (10)
C4B	0.132 (12)	0.112 (13)	0.122 (16)	0.025 (8)	0.041 (10)	0.069 (12)
C5B	0.059 (8)	0.052 (11)	0.066 (14)	0.007 (7)	0.015 (9)	0.032 (10)
C6B	0.079 (8)	0.092 (11)	0.081 (14)	0.039 (7)	0.016 (8)	0.046 (10)
C7B	0.082 (10)	0.097 (12)	0.085 (15)	0.025 (8)	0.044 (10)	0.040 (11)
C8B	0.107 (13)	0.116 (19)	0.11 (3)	0.019 (11)	0.050 (15)	0.060 (19)
C9B	0.085 (12)	0.10 (2)	0.12 (3)	0.030 (12)	0.044 (16)	0.037 (19)
C10B	0.105 (12)	0.110 (19)	0.13 (3)	0.023 (12)	0.041 (15)	0.045 (19)
O1C	0.101 (7)	0.057 (13)	0.08 (2)	0.031 (8)	0.033 (11)	0.044 (16)
C2C	0.057 (8)	0.058 (11)	0.058 (14)	0.014 (7)	0.034 (9)	0.024 (10)
C6C	0.107 (9)	0.111 (12)	0.105 (15)	0.043 (8)	0.022 (9)	0.058 (11)
C4C	0.109 (11)	0.091 (11)	0.102 (15)	0.030 (8)	0.010 (9)	0.064 (11)
C1C	0.082 (8)	0.067 (11)	0.070 (14)	0.000 (6)	0.027 (9)	0.050 (10)
C5C	0.082 (8)	0.086 (11)	0.076 (14)	0.025 (7)	0.018 (9)	0.048 (10)
C3C	0.066 (8)	0.059 (10)	0.065 (14)	0.015 (6)	0.020 (9)	0.034 (10)
C7C	0.123 (11)	0.117 (12)	0.114 (15)	0.033 (8)	0.036 (10)	0.067 (11)
C8C	0.112 (12)	0.099 (19)	0.12 (3)	0.045 (12)	0.030 (16)	0.054 (19)
C9C	0.094 (12)	0.095 (17)	0.10 (3)	0.035 (11)	0.036 (14)	0.046 (19)
C10C	0.118 (12)	0.119 (19)	0.11 (3)	0.072 (12)	0.047 (15)	0.052 (19)

Geometric parameters (Å, º) top

O1—H1A	0.8200 (13)	C5B—C6B	1.582 (5)
O1—H1B	0.8200 (13)	C5B—C10B	1.461 (10)
O1—C1	1.420 (6)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.566 (4)	C7B—H7B	0.9800
C1—C6	1.470 (8)	C7B—C8B	1.421 (6)
C2—H2	0.9800	C7B—C9B	1.4840 (15)
C2—C3	1.523 (2)	C8B—H8BA	0.9600
C2—C7	1.492 (2)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.5429 (13)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.479 (2)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.473 (3)	O1C—H1CA	0.8200 (12)
C5—C10	1.5021 (13)	O1C—H1CB	0.8200 (12)
C6—H6A	0.9700	O1C—C1C	1.447 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.607 (5)
C7—C8	1.565 (8)	C2C—C3C	1.628 (6)
C7—C9	1.460 (2)	C2C—C7C	1.488 (10)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9700	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.541 (2)
C9—H9A	0.9600	C6C—C5C	1.318 (5)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.404 (9)
C10—H10B	0.9600	C4C—C3C	1.471 (11)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.8200 (12)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.545 (9)
O1B—C1B	1.470 (4)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.465 (4)	C7C—H7C	0.9800
C1B—C6B	1.5230 (14)	C7C—C8C	1.572 (7)
C2B—H2B	0.9800	C7C—C9C	1.505 (8)
C2B—C3B	1.541 (5)	C8C—H8CA	0.9600
C2B—C7B	1.4310 (13)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.599 (3)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9700
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.5090 (15)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	104.9 (14)	C10B—C5B—C6B	108.3 (10)
C1—O1—H1A	102 (3)	C1B—C6B—C5B	112.0 (8)
C1—O1—H1B	113 (10)	C1B—C6B—H6BA	109.2
O1—C1—H1	108.5	C1B—C6B—H6BB	109.2
O1—C1—C2	112.0 (11)	C5B—C6B—H6BA	109.2
O1—C1—C6	115.4 (12)	C5B—C6B—H6BB	109.2
C2—C1—H1	108.5	H6BA—C6B—H6BB	107.9
C6—C1—H1	108.5	C2B—C7B—H7B	107.5
C6—C1—C2	103.6 (12)	C2B—C7B—C9B	103.5 (15)
C1—C2—H2	108.1	C8B—C7B—C2B	117.1 (14)
C3—C2—C1	104.5 (14)	C8B—C7B—H7B	107.5
C3—C2—H2	108.1	C8B—C7B—C9B	113 (2)
C7—C2—C1	105.4 (14)	C9B—C7B—H7B	107.5
C7—C2—H2	108.1	C7B—C8B—H8BA	109.5
C7—C2—C3	121.9 (12)	C7B—C8B—H8BB	109.5
C2—C3—H3A	108.0	C7B—C8B—H8BC	109.5
C2—C3—H3B	108.0	H8BA—C8B—H8BB	109.5
C2—C3—C4	117.1 (10)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.3	H8BB—C8B—H8BC	109.5
C4—C3—H3A	108.0	C7B—C9B—H9BA	109.5
C4—C3—H3B	108.0	C7B—C9B—H9BB	109.5
C3—C4—H4A	111.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	111.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	109.2	H9BA—C9B—H9BC	109.5
C5—C4—C3	102.2 (12)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	111.3	C5B—C10B—H10D	109.5
C5—C4—H4B	111.3	C5B—C10B—H10E	109.5
C4—C5—H5	106.4	C5B—C10B—H10F	109.5
C4—C5—C10	109.0 (14)	H10D—C10B—H10E	109.5
C6—C5—C4	112.6 (14)	H10D—C10B—H10F	109.5
C6—C5—H5	106.4	H10E—C10B—H10F	109.5
C6—C5—C10	115.5 (10)	H1CA—O1C—H1CB	110.8 (15)
C10—C5—H5	106.4	C1C—O1C—H1CA	128 (4)
C1—C6—C5	121.0 (10)	C1C—O1C—H1CB	121 (4)
C1—C6—H6A	107.1	C1C—C2C—H2C	106.1
C1—C6—H6B	107.1	C1C—C2C—C3C	105.6 (8)
C5—C6—H6A	107.1	C3C—C2C—H2C	106.1
C5—C6—H6B	107.1	C7C—C2C—H2C	106.1
H6A—C6—H6B	106.8	C7C—C2C—C1C	125.0 (13)
C2—C7—H7	103.6	C7C—C2C—C3C	106.7 (15)
C2—C7—C8	114.5 (10)	H6CA—C6C—H6CB	109.3
C8—C7—H7	103.6	C1C—C6C—H6CA	111.4
C9—C7—C2	108.4 (13)	C1C—C6C—H6CB	111.4
C9—C7—H7	103.6	C5C—C6C—H6CA	111.4
C9—C7—C8	120.9 (15)	C5C—C6C—H6CB	111.4
C7—C8—H8A	109.5	C5C—C6C—C1C	101.7 (14)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.5
C7—C8—H8C	109.5	C5C—C4C—H4CA	108.5
H8A—C8—H8B	109.5	C5C—C4C—H4CB	108.5
H8A—C8—H8C	109.5	C5C—C4C—C3C	115 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	108.5
C7—C9—H9A	109.5	C3C—C4C—H4CB	108.5
C7—C9—H9B	109.5	O1C—C1C—C2C	99.5 (6)
C7—C9—H9C	109.5	O1C—C1C—C6C	116.3 (13)
H9A—C9—H9B	109.5	O1C—C1C—H1C	107.7
H9A—C9—H9C	109.5	C2C—C1C—H1C	107.7
H9B—C9—H9C	109.5	C6C—C1C—C2C	117.2 (13)
C5—C10—H10A	109.5	C6C—C1C—H1C	107.7
C5—C10—H10B	109.5	C6C—C5C—C4C	121.2 (12)
C5—C10—H10C	109.5	C6C—C5C—H5C	106.8
H10A—C10—H10B	109.5	C6C—C5C—C10C	94.7 (15)
H10A—C10—H10C	109.5	C4C—C5C—H5C	106.8
H10B—C10—H10C	109.5	C4C—C5C—C10C	119 (2)
H1BA—O1B—H1BB	141.9 (4)	C10C—C5C—H5C	106.8
C1B—O1B—H1BA	95 (3)	C2C—C3C—H3CA	110.4
C1B—O1B—H1BB	103 (3)	C2C—C3C—H3CB	110.4
O1B—C1B—H1BC	104.7	C4C—C3C—C2C	106.8 (15)
O1B—C1B—C6B	102.8 (6)	C4C—C3C—H3CA	110.4
C2B—C1B—O1B	119.8 (13)	C4C—C3C—H3CB	110.4
C2B—C1B—H1BC	104.7	H3CA—C3C—H3CB	108.6
C2B—C1B—C6B	118.5 (14)	C2C—C7C—H7C	106.5
C6B—C1B—H1BC	104.7	C2C—C7C—C8C	111.4 (15)
C1B—C2B—H2B	103.1	C2C—C7C—C9C	118.8 (17)
C1B—C2B—C3B	116.0 (14)	C8C—C7C—H7C	106.5
C3B—C2B—H2B	103.1	C9C—C7C—H7C	106.5
C7B—C2B—C1B	111.3 (14)	C9C—C7C—C8C	106.6 (15)
C7B—C2B—H2B	103.1	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	117.8 (13)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	111.6	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	111.6	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	100.8 (11)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	109.4	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	111.6	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	111.6	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	104.8	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	104.8	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	105.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	130.1 (16)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	104.8	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	104.8	C5C—C10C—H10H	109.5
C4B—C5B—H5B	110.2	C5C—C10C—H10I	109.5
C4B—C5B—C6B	100.0 (15)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	110.2	H10G—C10C—H10I	109.5
C10B—C5B—C4B	117.3 (19)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	110.2

O1—C1—C2—C3	−179.4 (8)	C3B—C2B—C7B—C9B	−63.1 (19)
O1—C1—C2—C7	−49.8 (16)	C3B—C4B—C5B—C6B	−56 (2)
O1—C1—C6—C5	179.9 (14)	C3B—C4B—C5B—C10B	−172.6 (14)
C1—C2—C3—C4	−67.4 (19)	C4B—C5B—C6B—C1B	48.4 (18)
C1—C2—C7—C8	−69 (2)	C6B—C1B—C2B—C3B	53 (2)
C1—C2—C7—C9	153.0 (12)	C6B—C1B—C2B—C7B	−168.7 (9)
C2—C1—C6—C5	−57.3 (19)	C7B—C2B—C3B—C4B	−176.5 (14)
C2—C3—C4—C5	62.0 (19)	C10B—C5B—C6B—C1B	171.7 (16)
C3—C2—C7—C8	50 (3)	C1C—C2C—C3C—C4C	−45.8 (18)
C3—C2—C7—C9	−88.5 (18)	C1C—C2C—C7C—C8C	−52.9 (17)
C3—C4—C5—C6	−49.7 (16)	C1C—C2C—C7C—C9C	−177.3 (14)
C3—C4—C5—C10	−179.3 (9)	C1C—C6C—C5C—C4C	61 (3)
C4—C5—C6—C1	57 (2)	C1C—C6C—C5C—C10C	−170.9 (12)
C6—C1—C2—C3	55.6 (13)	C5C—C6C—C1C—O1C	−172.5 (12)
C6—C1—C2—C7	−174.8 (9)	C5C—C6C—C1C—C2C	−55.0 (15)
C7—C2—C3—C4	173.7 (16)	C5C—C4C—C3C—C2C	52.5 (16)
C10—C5—C6—C1	−176.4 (16)	C3C—C2C—C1C—O1C	178.1 (17)
O1B—C1B—C2B—C3B	179.9 (8)	C3C—C2C—C1C—C6C	52 (2)
O1B—C1B—C2B—C7B	−42 (2)	C3C—C2C—C7C—C8C	70.6 (14)
O1B—C1B—C6B—C5B	168.9 (12)	C3C—C2C—C7C—C9C	−53.7 (19)
C1B—C2B—C3B—C4B	−40.9 (18)	C3C—C4C—C5C—C6C	−67 (3)
C1B—C2B—C7B—C8B	−75 (3)	C3C—C4C—C5C—C10C	176.1 (11)
C1B—C2B—C7B—C9B	159.4 (15)	C7C—C2C—C1C—O1C	−57.9 (19)
C2B—C1B—C6B—C5B	−56 (2)	C7C—C2C—C1C—C6C	175.9 (13)
C2B—C3B—C4B—C5B	52 (2)	C7C—C2C—C3C—C4C	179.3 (11)
C3B—C2B—C7B—C8B	62 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_3.37GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.263 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.166 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.346 (4) Å	Cell parameters from 8331 reflections
c = 11.760 (6) Å	θ = 3.2–30.4°
α = 118.10 (4)°	µ = 0.08 mm⁻¹
β = 99.90 (5)°	T = 296 K
γ = 100.68 (4)°	Plate, colourless
V = 1232.3 (9) Å³	0.3 × 0.3 × 0.05 mm
Z = 6

Data collection top

Multiwire proportional diffractometer	1391 independent reflections
Graphite monochromator	313 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.389
phi and ω scans	θ_max = 30.4°, θ_min = 3.2°
Absorption correction: integration CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −13→13
T_min = 0.415, T_max = 0.978	k = −6→6
8331 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.094	w = 1/[σ²(F_o²) + (0.1466P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.357	(Δ/σ)_max = 0.001
S = 0.96	Δρ_max = 0.10 e Å⁻³
1391 reflections	Δρ_min = −0.11 e Å⁻³
317 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
245 restraints	Extinction coefficient: 0.011 (10)

Special details top

Experimental. Data were collected at room temperature and pressure of 3.37 (2) GPa (33700000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5452 (11)	1.0673 (18)	0.1291 (10)	0.111 (12)
H1A	0.6231 (19)	1.092 (5)	0.161 (9)	0.166*	0.5
H1B	0.533 (10)	1.045 (8)	0.0498 (12)	0.166*	0.5
C1	0.5477 (14)	1.2153 (19)	0.1783 (12)	0.081 (9)
H1	0.465470	1.226320	0.147538	0.121*
C2	0.5962 (13)	1.2776 (16)	0.3268 (11)	0.064 (8)
H2	0.681085	1.266953	0.346524	0.096*
C3	0.6126 (14)	1.4269 (16)	0.3882 (13)	0.066 (8)
H3A	0.636791	1.470649	0.485687	0.099*
H3B	0.531883	1.440051	0.359524	0.099*
C4	0.7172 (18)	1.501 (3)	0.3488 (13)	0.095 (9)
H4A	0.728370	1.600711	0.393292	0.143*
H4B	0.798437	1.487327	0.375148	0.143*
C5	0.6708 (15)	1.435 (2)	0.2014 (14)	0.106 (10)
H5	0.595682	1.455842	0.168322	0.159*
C6	0.6541 (15)	1.281 (2)	0.1470 (14)	0.082 (9)
H6A	0.637868	1.232408	0.049801	0.123*
H6B	0.732467	1.270250	0.185760	0.123*
C7	0.5072 (17)	1.189 (2)	0.3659 (14)	0.070 (8)
H7	0.489441	1.088038	0.303391	0.105*
C8	0.3807 (17)	1.232 (2)	0.3584 (14)	0.082 (13)
H8A	0.341921	1.207772	0.267515	0.098*
H8B	0.322421	1.184165	0.384974	0.098*
H8C	0.401185	1.331944	0.418024	0.098*
C9	0.5634 (15)	1.228 (3)	0.5051 (13)	0.115 (14)
H9A	0.507768	1.172428	0.527732	0.138*
H9B	0.644772	1.211184	0.514317	0.138*
H9C	0.574657	1.325467	0.564745	0.138*
C10	0.783 (2)	1.480 (3)	0.1710 (19)	0.135 (14)
H10A	0.763307	1.442879	0.075481	0.162*
H10B	0.811521	1.581154	0.217914	0.162*
H10C	0.848857	1.447998	0.199308	0.162*
O1B	0.7387 (14)	1.000 (2)	0.1187 (15)	0.130 (13)
H1BA	0.80 (2)	1.00 (3)	0.08 (3)	0.195*	0.5
H1BB	0.709 (4)	1.057 (6)	0.170 (4)	0.195*	0.5
C1B	0.7589 (15)	0.923 (2)	0.1903 (19)	0.111 (11)
H1BC	0.816824	0.866204	0.167437	0.166*
C2B	0.7966 (19)	1.044 (2)	0.325 (2)	0.102 (10)
H2B	0.727577	1.085286	0.345147	0.152*
C3B	0.8214 (17)	0.961 (3)	0.3993 (19)	0.090 (9)
H3BA	0.882044	0.912242	0.367264	0.135*
H3BB	0.858485	1.027531	0.495639	0.135*
C4B	0.696 (2)	0.855 (3)	0.3734 (18)	0.127 (10)
H4BA	0.712271	0.805889	0.420769	0.190*
H4BB	0.633690	0.901376	0.403048	0.190*
C5B	0.650 (2)	0.752 (3)	0.2199 (19)	0.126 (12)
H5B	0.708988	0.699930	0.185350	0.189*
C6B	0.6221 (18)	0.849 (3)	0.156 (2)	0.090 (10)
H6BA	0.579829	0.793879	0.059124	0.135*
H6BB	0.575165	0.911483	0.201353	0.135*
C7B	0.9150 (19)	1.146 (3)	0.3710 (19)	0.122 (10)
H7B	0.900050	1.179122	0.307975	0.183*
C8B	1.0392 (19)	1.128 (3)	0.3662 (16)	0.114 (14)
H8BA	1.101726	1.217320	0.405449	0.136*
H8BB	1.061556	1.083782	0.416052	0.136*
H8BC	1.036586	1.069104	0.273970	0.136*
C9B	0.9385 (18)	1.276 (3)	0.4995 (17)	0.120 (14)
H9BA	1.020989	1.338622	0.522562	0.144*
H9BB	0.874010	1.318913	0.491274	0.144*
H9BC	0.935795	1.254079	0.569012	0.144*
C10B	0.517 (2)	0.659 (4)	0.1839 (19)	0.129 (14)
H10D	0.486011	0.593941	0.088160	0.155*
H10E	0.519211	0.608630	0.230213	0.155*
H10F	0.461684	0.716034	0.210433	0.155*
O1C	0.9350 (9)	1.0837 (11)	0.0450 (11)	0.100 (12)
H1CA	0.872 (4)	1.028 (5)	0.038 (7)	0.150*	0.5
H1CB	0.9945 (19)	1.050 (3)	0.037 (5)	0.150*	0.5
C2C	1.0528 (16)	1.243 (2)	0.0259 (16)	0.101 (11)
H2C	1.073223	1.166604	−0.045140	0.151*
C6C	0.8204 (16)	1.112 (3)	−0.1201 (15)	0.075 (9)
H6CA	0.850369	1.038593	−0.180505	0.112*
H6CB	0.735014	1.070789	−0.122764	0.112*
C4C	0.9420 (15)	1.279 (3)	−0.1541 (14)	0.103 (9)
H4CA	0.937788	1.354295	−0.170680	0.155*
H4CB	0.969588	1.211424	−0.224178	0.155*
C1C	0.9095 (16)	1.1919 (19)	0.0210 (18)	0.154 (14)
H1C	0.880806	1.261633	0.089505	0.231*
C5C	0.8225 (14)	1.214 (3)	−0.1545 (17)	0.092 (10)
H5C	0.795585	1.287694	−0.087551	0.138*
C3C	1.0394 (18)	1.339 (2)	−0.0095 (17)	0.098 (11)
H3CA	1.122578	1.386552	−0.007083	0.147*
H3CB	1.011659	1.409668	0.057978	0.147*
C7C	1.1500 (12)	1.302 (2)	0.1602 (14)	0.090 (9)
H7C	1.148346	1.231352	0.186603	0.135*
C8C	1.1074 (17)	1.429 (3)	0.2601 (18)	0.121 (14)
H8CA	1.022795	1.393316	0.261153	0.145*
H8CB	1.165639	1.475177	0.349485	0.145*
H8CC	1.108121	1.493792	0.229796	0.145*
C9C	1.2803 (17)	1.367 (3)	0.1664 (17)	0.096 (13)
H9CA	1.338039	1.402462	0.253783	0.115*
H9CB	1.307288	1.298717	0.098144	0.115*
H9CC	1.280168	1.443322	0.151201	0.115*
C10C	0.7190 (19)	1.144 (3)	−0.2900 (14)	0.112 (14)
H10G	0.716338	1.209989	−0.318654	0.134*
H10H	0.738119	1.065104	−0.356217	0.134*
H10I	0.637698	1.112068	−0.280223	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.136 (12)	0.101 (19)	0.090 (8)	0.026 (12)	0.051 (8)	0.043 (10)
C1	0.086 (10)	0.082 (13)	0.079 (9)	0.027 (9)	0.041 (8)	0.039 (8)
C2	0.060 (9)	0.066 (12)	0.068 (8)	0.025 (8)	0.026 (8)	0.032 (7)
C3	0.071 (10)	0.063 (12)	0.061 (8)	0.025 (8)	0.012 (7)	0.031 (7)
C4	0.097 (10)	0.088 (13)	0.096 (9)	0.025 (9)	0.027 (8)	0.047 (8)
C5	0.108 (11)	0.115 (14)	0.105 (10)	0.028 (9)	0.046 (10)	0.062 (8)
C6	0.092 (10)	0.079 (13)	0.077 (9)	0.021 (8)	0.031 (8)	0.042 (8)
C7	0.083 (10)	0.079 (13)	0.061 (8)	0.018 (8)	0.032 (8)	0.045 (7)
C8	0.100 (14)	0.08 (2)	0.069 (10)	0.017 (14)	0.011 (11)	0.052 (11)
C9	0.101 (15)	0.11 (2)	0.121 (13)	0.054 (14)	0.056 (12)	0.039 (12)
C10	0.117 (15)	0.16 (2)	0.138 (13)	0.028 (13)	0.067 (12)	0.079 (12)
O1B	0.122 (13)	0.15 (2)	0.133 (11)	0.033 (12)	0.058 (9)	0.084 (11)
C1B	0.112 (13)	0.116 (15)	0.109 (12)	0.034 (9)	0.035 (10)	0.062 (9)
C2B	0.103 (12)	0.101 (15)	0.105 (10)	0.026 (9)	0.044 (10)	0.054 (9)
C3B	0.097 (12)	0.092 (14)	0.084 (9)	0.032 (9)	0.017 (9)	0.050 (8)
C4B	0.134 (12)	0.130 (14)	0.121 (10)	0.036 (9)	0.044 (9)	0.068 (8)
C5B	0.127 (14)	0.120 (16)	0.123 (13)	0.044 (10)	0.021 (10)	0.061 (10)
C6B	0.097 (12)	0.081 (14)	0.092 (9)	0.017 (9)	0.020 (9)	0.052 (9)
C7B	0.132 (12)	0.131 (15)	0.110 (10)	0.041 (9)	0.053 (10)	0.063 (8)
C8B	0.116 (15)	0.14 (2)	0.097 (12)	0.046 (14)	0.050 (11)	0.063 (12)
C9B	0.127 (17)	0.11 (2)	0.110 (13)	0.035 (14)	0.022 (12)	0.051 (13)
C10B	0.144 (16)	0.12 (2)	0.117 (13)	0.049 (14)	0.066 (12)	0.046 (12)
O1C	0.094 (12)	0.105 (19)	0.107 (9)	0.040 (12)	0.043 (8)	0.052 (10)
C2C	0.096 (13)	0.096 (15)	0.104 (11)	0.036 (9)	0.032 (10)	0.044 (9)
C6C	0.093 (11)	0.070 (13)	0.062 (8)	0.024 (9)	0.020 (8)	0.037 (8)
C4C	0.105 (11)	0.109 (13)	0.104 (10)	0.022 (9)	0.041 (9)	0.062 (8)
C1C	0.154 (16)	0.154 (18)	0.156 (15)	0.042 (10)	0.045 (11)	0.084 (11)
C5C	0.092 (12)	0.091 (14)	0.092 (10)	0.025 (9)	0.038 (9)	0.045 (9)
C3C	0.097 (12)	0.093 (15)	0.106 (11)	0.016 (9)	0.026 (9)	0.059 (9)
C7C	0.101 (10)	0.096 (13)	0.081 (9)	0.020 (8)	0.041 (9)	0.051 (7)
C8C	0.128 (15)	0.12 (2)	0.104 (12)	0.026 (15)	0.024 (12)	0.060 (12)
C9C	0.072 (13)	0.10 (2)	0.114 (12)	0.039 (13)	0.027 (10)	0.045 (12)
C10C	0.130 (15)	0.12 (2)	0.091 (12)	0.031 (14)	0.003 (12)	0.073 (12)

Geometric parameters (Å, º) top

O1—H1A	0.8200 (15)	C5B—C6B	1.646 (10)
O1—H1B	0.8200 (13)	C5B—C10B	1.505 (6)
O1—C1	1.4890 (13)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.488 (7)	C7B—H7B	0.9800
C1—C6	1.476 (5)	C7B—C8B	1.447 (9)
C2—H2	0.9800	C7B—C9B	1.463 (7)
C2—C3	1.4529 (14)	C8B—H8BA	0.9600
C2—C7	1.561 (7)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.573 (6)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.469 (7)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.5120 (14)	O1C—H1CA	0.8200 (12)
C5—C10	1.432 (4)	O1C—H1CB	0.8199 (12)
C6—H6A	0.9700	O1C—C1C	1.449 (8)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.579 (8)
C7—C8	1.583 (10)	C2C—C3C	1.363 (3)
C7—C9	1.459 (7)	C2C—C7C	1.5060 (17)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.498 (3)
C9—H9A	0.9600	C6C—C5C	1.393 (8)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.397 (5)
C10—H10B	0.9600	C4C—C3C	1.5908 (17)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.86 (10)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (12)	C5C—C10C	1.528 (10)
O1B—C1B	1.488 (6)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.442 (7)	C7C—H7C	0.9800
C1B—C6B	1.481 (6)	C7C—C8C	1.592 (10)
C2B—H2B	0.9800	C7C—C9C	1.480 (4)
C2B—C3B	1.579 (9)	C8C—H8CA	0.9600
C2B—C7B	1.407 (6)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.545 (7)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9600	C10C—H10G	0.9600
C4B—C5B	1.535 (6)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	105.0 (13)	C10B—C5B—C6B	102 (3)
C1—O1—H1A	91 (5)	C1B—C6B—C5B	95 (2)
C1—O1—H1B	95 (7)	C1B—C6B—H6BA	112.8
O1—C1—H1	114.6	C1B—C6B—H6BB	112.8
C2—C1—O1	100.5 (11)	C5B—C6B—H6BA	112.8
C2—C1—H1	114.6	C5B—C6B—H6BB	112.8
C6—C1—O1	107.6 (15)	H6BA—C6B—H6BB	110.3
C6—C1—H1	114.6	C2B—C7B—H7B	100.6
C6—C1—C2	103.6 (10)	C2B—C7B—C8B	129.0 (19)
C1—C2—H2	107.4	C2B—C7B—C9B	115.3 (14)
C1—C2—C7	108.0 (10)	C8B—C7B—H7B	100.6
C3—C2—C1	106.3 (12)	C8B—C7B—C9B	105.5 (16)
C3—C2—H2	107.4	C9B—C7B—H7B	100.6
C3—C2—C7	119.8 (13)	C7B—C8B—H8BA	109.5
C7—C2—H2	107.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.2	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.2	H8BA—C8B—H8BB	109.5
C2—C3—C4	112.1 (15)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.9	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.2	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.2	C7B—C9B—H9BB	109.5
C3—C4—H4A	110.5	C7B—C9B—H9BC	109.5
C3—C4—H4B	110.5	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	108.7	H9BA—C9B—H9BC	109.5
C5—C4—C3	106.1 (11)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	110.5	C5B—C10B—H10D	109.5
C5—C4—H4B	110.5	C5B—C10B—H10E	109.5
C4—C5—H5	115.1	C5B—C10B—H10F	109.5
C4—C5—C6	104.5 (15)	H10D—C10B—H10E	109.5
C6—C5—H5	115.1	H10D—C10B—H10F	109.5
C10—C5—C4	102.2 (13)	H10E—C10B—H10F	109.5
C10—C5—H5	115.1	H1CA—O1C—H1CB	110.8 (14)
C10—C5—C6	103.3 (19)	C1C—O1C—H1CA	115 (5)
C1—C6—C5	111.9 (14)	C1C—O1C—H1CB	130 (5)
C1—C6—H6A	109.2	C1C—C2C—H2C	109.8
C1—C6—H6B	109.2	C3C—C2C—H2C	109.8
C5—C6—H6A	109.2	C3C—C2C—C1C	97.1 (16)
C5—C6—H6B	109.2	C3C—C2C—C7C	115 (2)
H6A—C6—H6B	107.9	C7C—C2C—H2C	109.8
C2—C7—H7	111.1	C7C—C2C—C1C	114.9 (13)
C2—C7—C8	104.9 (12)	H6CA—C6C—H6CB	109.0
C8—C7—H7	111.1	C1C—C6C—H6CA	111.1
C9—C7—C2	110.4 (13)	C1C—C6C—H6CB	111.1
C9—C7—H7	111.1	C5C—C6C—H6CA	111.1
C9—C7—C8	107.9 (14)	C5C—C6C—H6CB	111.1
C7—C8—H8A	109.5	C5C—C6C—C1C	103.5 (17)
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.5
C7—C8—H8C	109.5	C5C—C4C—H4CA	110.2
H8A—C8—H8B	109.5	C5C—C4C—H4CB	110.2
H8A—C8—H8C	109.5	C5C—C4C—C3C	107.5 (14)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	110.2
C7—C9—H9A	109.5	C3C—C4C—H4CB	110.2
C7—C9—H9B	109.5	O1C—C1C—C2C	90.9 (16)
C7—C9—H9C	109.5	O1C—C1C—C6C	104 (2)
H9A—C9—H9B	109.5	O1C—C1C—H1C	115.5
H9A—C9—H9C	109.5	C2C—C1C—H1C	115.5
H9B—C9—H9C	109.5	C6C—C1C—C2C	112.2 (15)
C5—C10—H10A	109.5	C6C—C1C—H1C	115.5
C5—C10—H10B	109.5	C6C—C5C—C4C	115 (2)
C5—C10—H10C	109.5	C6C—C5C—H5C	107.2
H10A—C10—H10B	109.5	C6C—C5C—C10C	106.0 (19)
H10A—C10—H10C	109.5	C4C—C5C—H5C	107.2
H10B—C10—H10C	109.5	C4C—C5C—C10C	113.8 (15)
H1BA—O1B—H1BB	139 (10)	C10C—C5C—H5C	107.2
C1B—O1B—H1BA	106 (10)	C2C—C3C—C4C	115.7 (19)
C1B—O1B—H1BB	99 (5)	C2C—C3C—H3CA	108.4
O1B—C1B—H1BC	117.6	C2C—C3C—H3CB	108.4
C2B—C1B—O1B	96.3 (19)	C4C—C3C—H3CA	108.4
C2B—C1B—H1BC	117.6	C4C—C3C—H3CB	108.4
C2B—C1B—C6B	107.7 (13)	H3CA—C3C—H3CB	107.4
C6B—C1B—O1B	96 (2)	C2C—C7C—H7C	111.9
C6B—C1B—H1BC	117.6	C2C—C7C—C8C	102.8 (13)
C1B—C2B—H2B	112.5	C8C—C7C—H7C	111.9
C1B—C2B—C3B	95 (2)	C9C—C7C—C2C	113.0 (15)
C3B—C2B—H2B	112.5	C9C—C7C—H7C	111.9
C7B—C2B—C1B	118.2 (14)	C9C—C7C—C8C	104.9 (16)
C7B—C2B—H2B	112.5	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	104 (2)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.4	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.4	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.0	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	111 (2)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.4	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.4	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	110.8	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	110.8	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	108.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	105.0 (12)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	110.8	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	110.8	C5C—C10C—H10H	109.5
C4B—C5B—H5B	113.8	C5C—C10C—H10I	109.5
C4B—C5B—C6B	105 (3)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	113.8	H10G—C10C—H10I	109.5
C10B—C5B—C4B	108.0 (14)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	113.8

O1—C1—C2—C3	175.8 (10)	C3B—C2B—C7B—C9B	−85 (2)
O1—C1—C2—C7	−54.5 (16)	C3B—C4B—C5B—C6B	−63 (3)
O1—C1—C6—C5	−176.1 (10)	C3B—C4B—C5B—C10B	−171 (3)
C1—C2—C3—C4	−64.0 (16)	C4B—C5B—C6B—C1B	71.5 (16)
C1—C2—C7—C8	−74.8 (16)	C6B—C1B—C2B—C3B	83 (3)
C1—C2—C7—C9	169.2 (17)	C6B—C1B—C2B—C7B	−168 (3)
C2—C1—C6—C5	−70.2 (17)	C7B—C2B—C3B—C4B	173.5 (15)
C2—C3—C4—C5	62 (2)	C10B—C5B—C6B—C1B	−176.1 (13)
C3—C2—C7—C8	46.9 (16)	C1C—C2C—C3C—C4C	−61 (2)
C3—C2—C7—C9	−69.1 (19)	C1C—C2C—C7C—C8C	−59 (2)
C3—C4—C5—C6	−58 (2)	C1C—C2C—C7C—C9C	−171 (2)
C3—C4—C5—C10	−166 (3)	C1C—C6C—C5C—C4C	61 (2)
C4—C5—C6—C1	68.8 (15)	C1C—C6C—C5C—C10C	−172.2 (15)
C6—C1—C2—C3	64.6 (18)	C5C—C6C—C1C—O1C	−165.3 (15)
C6—C1—C2—C7	−165.7 (16)	C5C—C6C—C1C—C2C	−68 (2)
C7—C2—C3—C4	173.5 (13)	C5C—C4C—C3C—C2C	59 (3)
C10—C5—C6—C1	175.4 (17)	C3C—C2C—C1C—O1C	174.2 (15)
O1B—C1B—C2B—C3B	−178.4 (12)	C3C—C2C—C1C—C6C	69 (2)
O1B—C1B—C2B—C7B	−69 (3)	C3C—C2C—C7C—C8C	52 (2)
O1B—C1B—C6B—C5B	173.4 (13)	C3C—C2C—C7C—C9C	−60 (3)
C1B—C2B—C3B—C4B	−65.6 (17)	C3C—C4C—C5C—C6C	−55 (2)
C1B—C2B—C7B—C8B	−49 (4)	C3C—C4C—C5C—C10C	−177 (2)
C1B—C2B—C7B—C9B	171 (3)	C7C—C2C—C1C—O1C	−64 (2)
C2B—C1B—C6B—C5B	−88 (2)	C7C—C2C—C1C—C6C	−169.7 (19)
C2B—C3B—C4B—C5B	62 (3)	C7C—C2C—C3C—C4C	177.3 (11)
C3B—C2B—C7B—C8B	55 (2)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_120K) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.022 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 12.0054 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2439 (10) Å	Cell parameters from 5915 reflections
c = 12.6778 (9) Å	θ = 1.9–26.2°
α = 117.176 (7)°	µ = 0.06 mm⁻¹
β = 100.286 (7)°	T = 120 K
γ = 103.377 (7)°	Plate, colourless
V = 1523.4 (2) Å³	0.25 × 0.10 × 0.05 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	5915 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3346 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 26.2°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→13
T_min = 0.992, T_max = 0.997	k = −15→15
11319 measured reflections	l = −11→15

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.061	w = 1/[σ²(F_o²) + (0.1068P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.220	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.30 e Å⁻³
5915 reflections	Δρ_min = −0.27 e Å⁻³
335 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.013 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.54999 (19)	1.07582 (16)	0.12517 (15)	0.0521 (5)
H1BC	0.616202	1.068739	0.124739	0.078*	0.5
H1A	0.539 (6)	1.053 (6)	0.051 (2)	0.078*	0.5
C1	0.5630 (2)	1.2121 (2)	0.1790 (2)	0.0450 (6)
H1	0.485141	1.216947	0.146030	0.068*
C2	0.5961 (2)	1.2772 (2)	0.3204 (2)	0.0446 (6)
H2	0.674655	1.271882	0.350351	0.067*
C3	0.6164 (3)	1.4245 (2)	0.3785 (2)	0.0493 (6)
H3A	0.541011	1.434371	0.349520	0.074*
H3B	0.640273	1.466909	0.469180	0.074*
C4	0.7137 (3)	1.4912 (3)	0.3432 (3)	0.0572 (7)
H4A	0.723006	1.583171	0.379994	0.086*
H4B	0.790344	1.486977	0.377796	0.086*
C5	0.6831 (3)	1.4278 (3)	0.2026 (3)	0.0558 (7)
H5	0.608734	1.438973	0.170421	0.084*
C6	0.6578 (3)	1.2802 (2)	0.1425 (2)	0.0486 (6)
H6A	0.630712	1.239283	0.051898	0.073*
H6B	0.732725	1.267338	0.166923	0.073*
C7	0.5074 (3)	1.2073 (3)	0.3630 (2)	0.0498 (6)
H7	0.489152	1.112812	0.309115	0.075*
C8	0.3871 (3)	1.2287 (3)	0.3478 (3)	0.0569 (7)
H8A	0.351837	1.205543	0.262863	0.068*
H8B	0.333153	1.174682	0.366981	0.068*
H8C	0.400408	1.319467	0.403966	0.068*
C9	0.5646 (3)	1.2436 (4)	0.4972 (3)	0.0710 (9)
H9A	0.640417	1.229764	0.505733	0.085*
H9B	0.578394	1.334410	0.553770	0.085*
H9C	0.511139	1.189624	0.516784	0.085*
C10	0.7820 (3)	1.4918 (3)	0.1674 (3)	0.0720 (9)
H10G	0.759311	1.448866	0.077661	0.086*
H10H	0.792905	1.583057	0.202523	0.086*
H10I	0.856505	1.483897	0.199727	0.086*
O1B	0.73921 (19)	0.99140 (19)	0.11098 (16)	0.0578 (5)
H1B	0.805901	1.025134	0.109395	0.087*	0.5
H1BA	0.704 (4)	1.044 (5)	0.138 (5)	0.087*	0.5
C1B	0.7526 (3)	0.9361 (3)	0.1883 (2)	0.0488 (6)
H1BB	0.811691	0.892540	0.170640	0.073*
C2B	0.7983 (3)	1.0401 (3)	0.3282 (2)	0.0513 (7)
H2B	0.733979	1.075657	0.344802	0.077*
C3B	0.8102 (3)	0.9716 (3)	0.4022 (3)	0.0639 (8)
H3BA	0.838095	1.036275	0.491328	0.096*
H3BB	0.870014	0.930475	0.384877	0.096*
C4B	0.6891 (3)	0.8674 (3)	0.3675 (3)	0.0692 (9)
H4BA	0.700243	0.823901	0.413959	0.104*
H4BB	0.631520	0.909983	0.391869	0.104*
C5B	0.6378 (3)	0.7655 (3)	0.2280 (3)	0.0623 (8)
H5B	0.693699	0.718130	0.207220	0.093*
C6B	0.6325 (3)	0.8336 (3)	0.1533 (2)	0.0504 (6)
H6BA	0.606460	0.768069	0.064606	0.076*
H6BB	0.572475	0.875056	0.167281	0.076*
C7B	0.9124 (3)	1.1572 (3)	0.3684 (2)	0.0571 (7)
H7B	0.895367	1.188501	0.310824	0.086*
C8B	1.0261 (3)	1.1236 (4)	0.3583 (3)	0.0679 (9)
H8BA	1.009462	1.051546	0.275334	0.081*
H8BB	1.090149	1.198780	0.374811	0.081*
H8BC	1.050213	1.099463	0.418564	0.081*
C9B	0.9376 (3)	1.2717 (4)	0.5000 (3)	0.0846 (11)
H9BA	0.865578	1.292193	0.505518	0.102*
H9BB	0.961570	1.247820	0.560483	0.102*
H9BC	1.001506	1.347136	0.516730	0.102*
C10B	0.5156 (3)	0.6659 (3)	0.1930 (3)	0.0751 (10)
H10A	0.486408	0.603476	0.104347	0.090*
H10B	0.523183	0.621003	0.237706	0.090*
H10C	0.459401	0.710095	0.214766	0.090*
O1C	0.93620 (19)	1.07788 (18)	0.05626 (18)	0.0546 (5)
H1CA	0.878 (2)	1.039 (4)	0.065 (3)	0.082*	0.5
H1C	0.978 (6)	1.041 (6)	0.023 (6)	0.082*	0.5
C2C	1.0475 (3)	1.2496 (3)	0.0295 (2)	0.0471 (6)
H2C	1.074844	1.185834	−0.030376	0.057*
C6C	0.8305 (3)	1.1055 (2)	−0.1063 (2)	0.0467 (6)
H6CA	0.752704	1.064414	−0.103243	0.070*
H6CB	0.851934	1.036774	−0.166544	0.070*
C4C	0.9415 (3)	1.2732 (3)	−0.1458 (2)	0.0558 (7)
H4CA	0.934619	1.336840	−0.169701	0.084*
H4CB	0.969250	1.211424	−0.205630	0.084*
C1C	0.9253 (3)	1.1730 (2)	0.0223 (2)	0.0463 (6)
H1CB	0.897496	1.234897	0.083525	0.056*
C5C	0.8189 (3)	1.2006 (3)	−0.1508 (2)	0.0524 (7)
H5C	0.791604	1.265471	−0.092008	0.079*
C3C	1.0340 (3)	1.3438 (3)	−0.0152 (3)	0.0542 (8)
H3CA	1.009183	1.410261	0.043361	0.081*
H3CB	1.111932	1.387952	−0.015891	0.073 (10)
C7C	1.1443 (3)	1.3171 (3)	0.1605 (2)	0.0520 (7)
H7C	1.147387	1.247953	0.178688	0.078*
C8C	1.1144 (3)	1.4180 (3)	0.2665 (3)	0.0656 (8)
H8CA	1.035140	1.378032	0.265640	0.079*
H8CB	1.173190	1.449041	0.345489	0.085 (11)
H8CC	1.116053	1.490630	0.255078	0.101*
C9C	1.2686 (3)	1.3774 (4)	0.1597 (3)	0.0692 (8)
H9CA	1.285932	1.312601	0.092460	0.083*
H9CB	1.270890	1.449853	0.147809	0.098 (13)
H9CC	1.328027	1.408265	0.238220	0.117*
C10C	0.7245 (3)	1.1300 (3)	−0.2807 (3)	0.0632 (8)
H10D	0.648115	1.085254	−0.279450	0.076*
H10E	0.715857	1.192897	−0.303745	0.091 (12)
H10F	0.750058	1.067243	−0.340714	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0695 (14)	0.0449 (9)	0.0463 (9)	0.0247 (10)	0.0257 (10)	0.0228 (8)
C1	0.0503 (17)	0.0443 (13)	0.0432 (12)	0.0205 (12)	0.0175 (12)	0.0224 (11)
C2	0.0460 (16)	0.0482 (13)	0.0439 (12)	0.0205 (12)	0.0180 (11)	0.0244 (11)
C3	0.0516 (17)	0.0469 (13)	0.0462 (13)	0.0207 (13)	0.0187 (12)	0.0194 (11)
C4	0.060 (2)	0.0477 (14)	0.0662 (17)	0.0237 (14)	0.0247 (15)	0.0280 (13)
C5	0.065 (2)	0.0529 (15)	0.0699 (17)	0.0307 (15)	0.0356 (15)	0.0380 (14)
C6	0.0594 (18)	0.0510 (14)	0.0495 (13)	0.0284 (13)	0.0276 (13)	0.0295 (12)
C7	0.0560 (18)	0.0549 (14)	0.0433 (13)	0.0228 (14)	0.0212 (12)	0.0262 (12)
C8	0.0517 (18)	0.0590 (16)	0.0597 (16)	0.0226 (14)	0.0230 (14)	0.0276 (14)
C9	0.068 (2)	0.101 (2)	0.0570 (17)	0.0273 (19)	0.0279 (16)	0.0499 (17)
C10	0.087 (3)	0.0643 (18)	0.102 (2)	0.0418 (19)	0.057 (2)	0.0560 (18)
O1B	0.0631 (14)	0.0761 (13)	0.0573 (11)	0.0264 (11)	0.0233 (10)	0.0503 (10)
C1B	0.0583 (18)	0.0613 (15)	0.0488 (13)	0.0313 (14)	0.0269 (13)	0.0376 (12)
C2B	0.0538 (18)	0.0648 (16)	0.0489 (14)	0.0291 (15)	0.0240 (13)	0.0339 (13)
C3B	0.070 (2)	0.092 (2)	0.0545 (15)	0.0369 (18)	0.0287 (15)	0.0499 (16)
C4B	0.082 (2)	0.088 (2)	0.0754 (19)	0.0395 (19)	0.0418 (18)	0.0616 (18)
C5B	0.074 (2)	0.0700 (18)	0.0790 (19)	0.0410 (17)	0.0446 (17)	0.0522 (16)
C6B	0.0565 (18)	0.0547 (14)	0.0510 (14)	0.0248 (14)	0.0258 (13)	0.0308 (12)
C7B	0.0562 (19)	0.0699 (17)	0.0515 (14)	0.0272 (15)	0.0216 (14)	0.0329 (14)
C8B	0.061 (2)	0.102 (2)	0.0610 (17)	0.0397 (19)	0.0275 (15)	0.0507 (17)
C9B	0.061 (2)	0.091 (2)	0.067 (2)	0.020 (2)	0.0229 (17)	0.0169 (18)
C10B	0.093 (3)	0.0639 (18)	0.100 (2)	0.0370 (19)	0.057 (2)	0.0538 (18)
O1C	0.0610 (14)	0.0588 (11)	0.0660 (12)	0.0228 (10)	0.0221 (10)	0.0480 (10)
C2C	0.0548 (18)	0.0552 (14)	0.0472 (13)	0.0267 (13)	0.0238 (12)	0.0330 (12)
C6C	0.0552 (17)	0.0503 (13)	0.0466 (13)	0.0227 (13)	0.0217 (12)	0.0308 (11)
C4C	0.073 (2)	0.0585 (15)	0.0515 (14)	0.0236 (15)	0.0229 (14)	0.0400 (13)
C1C	0.0577 (18)	0.0562 (14)	0.0470 (13)	0.0298 (13)	0.0254 (12)	0.0363 (12)
C5C	0.0633 (19)	0.0584 (15)	0.0485 (14)	0.0280 (15)	0.0209 (13)	0.0340 (13)
C3C	0.068 (2)	0.0542 (16)	0.0516 (15)	0.0219 (16)	0.0224 (15)	0.0352 (13)
H3CB	0.10 (3)	0.05 (2)	0.020 (15)	0.02 (2)	−0.009 (17)	0.001 (14)
C7C	0.0530 (18)	0.0575 (15)	0.0540 (15)	0.0221 (14)	0.0168 (13)	0.0348 (13)
C8C	0.059 (2)	0.079 (2)	0.0476 (16)	0.0242 (18)	0.0111 (15)	0.0274 (16)
H8CB	0.03 (2)	0.09 (2)	0.08 (2)	0.016 (19)	−0.012 (17)	0.02 (2)
C9C	0.056 (2)	0.080 (2)	0.0720 (19)	0.0218 (18)	0.0212 (16)	0.0415 (18)
H9CB	0.08 (3)	0.10 (3)	0.13 (3)	−0.02 (2)	0.01 (2)	0.10 (3)
C10C	0.071 (2)	0.0737 (19)	0.0533 (16)	0.0260 (17)	0.0144 (15)	0.0413 (15)
H10E	0.17 (4)	0.08 (2)	0.06 (2)	0.05 (2)	0.03 (2)	0.06 (2)

Geometric parameters (Å, º) top

O1—H1BC	0.8200	C5B—C6B	1.523 (3)
O1—H1A	0.825 (19)	C5B—C10B	1.510 (4)
O1—C1	1.441 (3)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.516 (3)	C7B—H7B	0.9800
C1—C6	1.519 (3)	C7B—C8B	1.523 (4)
C2—H2	0.9800	C7B—C9B	1.526 (4)
C2—C3	1.541 (3)	C8B—H8BA	0.9600
C2—C7	1.537 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.520 (4)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10A	0.9600
C4—C5	1.512 (4)	C10B—H10B	0.9600
C5—H5	0.9800	C10B—H10C	0.9600
C5—C6	1.531 (3)	O1C—H1CA	0.800 (14)
C5—C10	1.517 (4)	O1C—H1C	0.802 (19)
C6—H6A	0.9700	O1C—C1C	1.438 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.508 (4)
C7—C8	1.521 (4)	C2C—C3C	1.526 (3)
C7—C9	1.522 (4)	C2C—C7C	1.551 (4)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.519 (4)
C9—H9A	0.9600	C6C—C5C	1.531 (3)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10G	0.9600	C4C—C5C	1.507 (4)
C10—H10H	0.9600	C4C—C3C	1.521 (4)
C10—H10I	0.9600	C1C—H1CB	0.9800
O1B—H1B	0.8200	C5C—H5C	0.9800
O1B—H1BA	0.827 (18)	C5C—C10C	1.524 (4)
O1B—C1B	1.430 (3)	C3C—H3CA	0.9700
C1B—H1BB	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.528 (3)	C7C—H7C	0.9800
C1B—C6B	1.510 (4)	C7C—C8C	1.524 (4)
C2B—H2B	0.9800	C7C—C9C	1.508 (4)
C2B—C3B	1.526 (4)	C8C—H8CA	0.9600
C2B—C7B	1.539 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.528 (4)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10D	0.9600
C4B—C5B	1.518 (4)	C10C—H10E	0.9600
C5B—H5B	0.9800	C10C—H10F	0.9600

H1BC—O1—H1A	84.5	C10B—C5B—C6B	111.7 (3)
C1—O1—H1BC	109.5	C1B—C6B—C5B	113.0 (2)
C1—O1—H1A	101 (4)	C1B—C6B—H6BA	109.0
O1—C1—H1	108.7	C1B—C6B—H6BB	109.0
O1—C1—C2	109.23 (19)	C5B—C6B—H6BA	109.0
O1—C1—C6	110.04 (18)	C5B—C6B—H6BB	109.0
C2—C1—H1	108.7	H6BA—C6B—H6BB	107.8
C2—C1—C6	111.6 (2)	C2B—C7B—H7B	106.6
C6—C1—H1	108.7	C8B—C7B—C2B	114.7 (2)
C1—C2—H2	106.5	C8B—C7B—H7B	106.6
C1—C2—C3	109.2 (2)	C8B—C7B—C9B	110.0 (3)
C1—C2—C7	113.9 (2)	C9B—C7B—C2B	111.9 (2)
C3—C2—H2	106.5	C9B—C7B—H7B	106.6
C7—C2—H2	106.5	C7B—C8B—H8BA	109.5
C7—C2—C3	113.70 (19)	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.3	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.4	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.0	H8BA—C8B—H8BC	109.5
C4—C3—C2	111.39 (19)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.4	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.4	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.2	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.2	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	112.0 (2)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.2	C5B—C10B—H10A	109.5
C5—C4—H4B	109.2	C5B—C10B—H10B	109.5
C4—C5—H5	107.9	C5B—C10B—H10C	109.5
C4—C5—C6	109.6 (2)	H10A—C10B—H10B	109.5
C4—C5—C10	112.0 (3)	H10A—C10B—H10C	109.5
C6—C5—H5	107.9	H10B—C10B—H10C	109.5
C10—C5—H5	107.9	H1CA—O1C—H1C	121 (6)
C10—C5—C6	111.3 (2)	C1C—O1C—H1CA	118 (4)
C1—C6—C5	113.48 (19)	C1C—O1C—H1C	110 (5)
C1—C6—H6A	108.9	C1C—C2C—H2C	106.7
C1—C6—H6B	108.9	C1C—C2C—C3C	109.9 (2)
C5—C6—H6A	108.9	C1C—C2C—C7C	112.63 (19)
C5—C6—H6B	108.9	C3C—C2C—H2C	106.7
H6A—C6—H6B	107.7	C3C—C2C—C7C	113.7 (2)
C2—C7—H7	106.8	C7C—C2C—H2C	106.7
C8—C7—C2	114.0 (2)	H6CA—C6C—H6CB	107.8
C8—C7—H7	106.8	C1C—C6C—H6CA	109.1
C8—C7—C9	110.2 (2)	C1C—C6C—H6CB	109.1
C9—C7—C2	111.7 (2)	C1C—C6C—C5C	112.7 (2)
C9—C7—H7	106.8	C5C—C6C—H6CA	109.1
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.1
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.3
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.3
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.5 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.3
C7—C9—H9B	109.5	O1C—C1C—C2C	110.1 (2)
C7—C9—H9C	109.5	O1C—C1C—C6C	110.0 (2)
H9A—C9—H9B	109.5	O1C—C1C—H1CB	107.9
H9A—C9—H9C	109.5	C2C—C1C—C6C	112.78 (19)
H9B—C9—H9C	109.5	C2C—C1C—H1CB	107.9
C5—C10—H10G	109.5	C6C—C1C—H1CB	107.9
C5—C10—H10H	109.5	C6C—C5C—H5C	107.7
C5—C10—H10I	109.5	C4C—C5C—C6C	109.5 (2)
H10G—C10—H10H	109.5	C4C—C5C—H5C	107.7
H10G—C10—H10I	109.5	C4C—C5C—C10C	112.4 (2)
H10H—C10—H10I	109.5	C10C—C5C—C6C	111.5 (2)
H1B—O1B—H1BA	113.5	C10C—C5C—H5C	107.7
C1B—O1B—H1B	109.5	C2C—C3C—H3CA	109.2
C1B—O1B—H1BA	108 (5)	C2C—C3C—H3CB	109.2
O1B—C1B—H1BB	108.3	C4C—C3C—C2C	112.1 (2)
O1B—C1B—C2B	112.5 (2)	C4C—C3C—H3CA	109.2
O1B—C1B—C6B	108.8 (2)	C4C—C3C—H3CB	109.2
C2B—C1B—H1BB	108.3	H3CA—C3C—H3CB	107.9
C6B—C1B—H1BB	108.3	C2C—C7C—H7C	106.9
C6B—C1B—C2B	110.7 (2)	C8C—C7C—C2C	113.8 (2)
C1B—C2B—H2B	106.5	C8C—C7C—H7C	106.9
C1B—C2B—C7B	113.9 (2)	C9C—C7C—C2C	111.2 (2)
C3B—C2B—C1B	108.4 (2)	C9C—C7C—H7C	106.9
C3B—C2B—H2B	106.5	C9C—C7C—C8C	110.6 (3)
C3B—C2B—C7B	114.5 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.5	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.4	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.4	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	111.2 (3)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.0	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.4	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.4	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.2	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.2	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.9	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.2 (2)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.2	C5C—C10C—H10D	109.5
C5B—C4B—H4BB	109.2	C5C—C10C—H10E	109.5
C4B—C5B—H5B	107.7	C5C—C10C—H10F	109.5
C4B—C5B—C6B	109.8 (2)	H10D—C10C—H10E	109.5
C6B—C5B—H5B	107.7	H10D—C10C—H10F	109.5
C10B—C5B—C4B	112.2 (2)	H10E—C10C—H10F	109.5
C10B—C5B—H5B	107.7

O1—C1—C2—C3	177.1 (2)	C3B—C2B—C7B—C9B	−67.6 (3)
O1—C1—C2—C7	−54.6 (3)	C3B—C4B—C5B—C6B	−52.8 (3)
O1—C1—C6—C5	−176.4 (2)	C3B—C4B—C5B—C10B	−177.5 (3)
C1—C2—C3—C4	−57.1 (3)	C4B—C5B—C6B—C1B	53.6 (3)
C1—C2—C7—C8	−74.4 (3)	C6B—C1B—C2B—C3B	58.4 (3)
C1—C2—C7—C9	159.9 (2)	C6B—C1B—C2B—C7B	−172.9 (2)
C2—C1—C6—C5	−55.0 (3)	C7B—C2B—C3B—C4B	173.3 (2)
C2—C3—C4—C5	57.8 (3)	C10B—C5B—C6B—C1B	178.6 (2)
C3—C2—C7—C8	51.5 (3)	C1C—C2C—C3C—C4C	−54.8 (3)
C3—C2—C7—C9	−74.2 (3)	C1C—C2C—C7C—C8C	−61.8 (3)
C3—C4—C5—C6	−54.2 (3)	C1C—C2C—C7C—C9C	172.5 (2)
C3—C4—C5—C10	−178.3 (2)	C1C—C6C—C5C—C4C	54.2 (3)
C4—C5—C6—C1	53.1 (3)	C1C—C6C—C5C—C10C	179.2 (2)
C6—C1—C2—C3	55.3 (3)	C5C—C6C—C1C—O1C	−177.2 (2)
C6—C1—C2—C7	−176.4 (2)	C5C—C6C—C1C—C2C	−53.9 (3)
C7—C2—C3—C4	174.5 (2)	C5C—C4C—C3C—C2C	57.8 (3)
C10—C5—C6—C1	177.6 (2)	C3C—C2C—C1C—O1C	176.14 (19)
O1B—C1B—C2B—C3B	−179.7 (2)	C3C—C2C—C1C—C6C	52.8 (3)
O1B—C1B—C2B—C7B	−51.0 (3)	C3C—C2C—C7C—C8C	63.9 (3)
O1B—C1B—C6B—C5B	178.35 (19)	C3C—C2C—C7C—C9C	−61.8 (3)
C1B—C2B—C3B—C4B	−58.3 (3)	C3C—C4C—C5C—C6C	−55.9 (3)
C1B—C2B—C7B—C8B	−66.9 (3)	C3C—C4C—C5C—C10C	179.6 (2)
C1B—C2B—C7B—C9B	166.9 (2)	C7C—C2C—C1C—O1C	−56.0 (3)
C2B—C1B—C6B—C5B	−57.6 (3)	C7C—C2C—C1C—C6C	−179.4 (2)
C2B—C3B—C4B—C5B	57.0 (3)	C7C—C2C—C3C—C4C	177.9 (2)
C3B—C2B—C7B—C8B	58.6 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_160K) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.013 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.9503 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3527 (10) Å	Cell parameters from 5994 reflections
c = 12.7242 (9) Å	θ = 1.9–26.3°
α = 117.256 (7)°	µ = 0.06 mm⁻¹
β = 99.818 (7)°	T = 160 K
γ = 103.584 (8)°	Plate, colourless
V = 1536.7 (2) Å³	0.25 × 0.1 × 0.05 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	R_int = 0.045
ω scans	θ_max = 26.3°, θ_min = 1.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→13
T_min = 0.993, T_max = 0.997	k = −15→15
11620 measured reflections	l = −11→15
5994 independent reflections	3 standard reflections every 120 min
3295 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.0948P)² + 0.0212P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.212	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.23 e Å⁻³
5994 reflections	Δρ_min = −0.18 e Å⁻³
317 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
16 restraints	Extinction coefficient: 0.013 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.54777 (16)	1.07505 (15)	0.12528 (13)	0.0592 (5)
H1A	0.6132 (6)	1.0643 (11)	0.1289 (16)	0.089*	0.5
H1B	0.511 (3)	1.040 (3)	0.0508 (4)	0.089*	0.5
C1	0.5599 (2)	1.2100 (2)	0.1786 (2)	0.0516 (6)
H1	0.481214	1.213959	0.146663	0.077*
C2	0.5941 (2)	1.2754 (2)	0.32005 (19)	0.0510 (6)
H2	0.673114	1.270383	0.348967	0.076*
C3	0.6140 (2)	1.4207 (2)	0.3772 (2)	0.0574 (6)
H3A	0.537987	1.430152	0.349637	0.086*
H3B	0.639025	1.463242	0.467427	0.086*
C4	0.7101 (3)	1.4872 (2)	0.3401 (2)	0.0666 (7)
H4A	0.718944	1.578229	0.376757	0.100*
H4B	0.787539	1.483324	0.372933	0.100*
C5	0.6771 (3)	1.4234 (2)	0.1997 (3)	0.0655 (7)
H5	0.601517	1.433630	0.169271	0.098*
C6	0.6529 (3)	1.2772 (2)	0.1402 (2)	0.0581 (7)
H6A	0.624751	1.236113	0.050109	0.087*
H6B	0.728603	1.265201	0.163446	0.087*
C7	0.5057 (3)	1.2058 (3)	0.3631 (2)	0.0589 (7)
H7	0.487867	1.112105	0.309962	0.088*
C8	0.3853 (3)	1.2268 (3)	0.3494 (3)	0.0679 (7)
H8A	0.349096	1.202650	0.264764	0.081*
H8B	0.331833	1.174026	0.370086	0.081*
H8C	0.398698	1.317003	0.404603	0.081*
C9	0.5642 (3)	1.2438 (4)	0.4971 (3)	0.0854 (10)
H9A	0.640369	1.230225	0.504922	0.103*
H9B	0.578046	1.334041	0.552634	0.103*
H9C	0.511181	1.191064	0.518117	0.103*
C10	0.7737 (3)	1.4871 (3)	0.1619 (3)	0.0896 (11)
H10A	0.749425	1.443987	0.072552	0.108*
H10B	0.783512	1.577326	0.196759	0.108*
H10C	0.849289	1.480234	0.192556	0.108*
O1B	0.74222 (18)	1.0001 (2)	0.11826 (17)	0.0724 (6)
H1BA	0.8086 (9)	1.017 (3)	0.108 (2)	0.109*	0.5
H1BB	0.7003 (11)	1.0433 (19)	0.1457 (12)	0.109*	0.5
C1B	0.7580 (3)	0.9447 (3)	0.1941 (2)	0.0586 (7)
H1BC	0.818180	0.902922	0.175509	0.088*
C2B	0.8022 (3)	1.0457 (3)	0.3327 (2)	0.0602 (7)
H2B	0.737097	1.079908	0.350114	0.090*
C3B	0.8158 (3)	0.9767 (3)	0.4049 (3)	0.0769 (9)
H3BA	0.876325	0.936827	0.386328	0.115*
H3BB	0.843655	1.039994	0.493759	0.115*
C4B	0.6953 (3)	0.8724 (3)	0.3701 (3)	0.0846 (10)
H4BA	0.706704	0.828899	0.415843	0.127*
H4BB	0.636722	0.913576	0.394540	0.127*
C5B	0.6453 (3)	0.7723 (3)	0.2314 (3)	0.0759 (9)
H5B	0.702672	0.727086	0.210001	0.114*
C6B	0.6381 (3)	0.8411 (2)	0.1588 (2)	0.0606 (7)
H6BA	0.612227	0.777142	0.070239	0.091*
H6BB	0.577128	0.881073	0.174036	0.091*
C7B	0.9166 (3)	1.1633 (3)	0.3731 (3)	0.0711 (8)
H7B	0.899350	1.194667	0.316258	0.107*
C8B	1.0307 (3)	1.1314 (4)	0.3625 (3)	0.0840 (9)
H8BA	1.014663	1.060548	0.279627	0.101*
H8BB	1.094664	1.206582	0.379319	0.101*
H8BC	1.054948	1.106868	0.421808	0.101*
C9B	0.9399 (3)	1.2755 (4)	0.5039 (3)	0.1101 (14)
H9BA	0.866934	1.294536	0.509216	0.132*
H9BB	0.963808	1.251486	0.563744	0.132*
H9BC	1.003524	1.351201	0.521255	0.132*
C10B	0.5228 (4)	0.6707 (3)	0.1955 (3)	0.0938 (11)
H10D	0.494586	0.609378	0.107179	0.113*
H10E	0.531202	0.625644	0.239329	0.113*
H10F	0.465304	0.712841	0.217361	0.113*
O1C	0.93720 (18)	1.07976 (17)	0.05544 (16)	0.0660 (5)
H1CA	0.8939 (9)	1.0451 (19)	0.0832 (19)	0.099*	0.5
H1CB	0.9750 (14)	1.0347 (12)	0.0204 (16)	0.099*	0.5
C2C	1.0489 (2)	1.2501 (2)	0.0294 (2)	0.0531 (6)
H2C	1.076946	1.187128	−0.030179	0.080*
C6C	0.8322 (2)	1.1072 (2)	−0.1058 (2)	0.0544 (6)
H6CA	0.753908	1.066208	−0.102786	0.082*
H6CB	0.853974	1.039304	−0.166015	0.082*
C4C	0.9438 (3)	1.2740 (3)	−0.1447 (2)	0.0683 (8)
H4CA	0.936969	1.337138	−0.168296	0.102*
H4CB	0.971879	1.212852	−0.204484	0.102*
C1C	0.9268 (2)	1.1738 (2)	0.0221 (2)	0.0522 (6)
H1C	0.898412	1.234885	0.083148	0.078*
C5C	0.8210 (3)	1.2019 (2)	−0.1494 (2)	0.0617 (7)
H5C	0.793639	1.266086	−0.090327	0.093*
C3C	1.0366 (3)	1.3442 (2)	−0.0147 (2)	0.0618 (7)
H3CA	1.011951	1.410408	0.043816	0.093*
H3CB	1.115068	1.387482	−0.015850	0.093*
C7C	1.1455 (3)	1.3173 (3)	0.1593 (2)	0.0615 (7)
H7C	1.147831	1.249110	0.178048	0.092*
C8C	1.1152 (3)	1.4184 (3)	0.2644 (2)	0.0828 (9)
H8CA	1.035280	1.379263	0.263673	0.099*
H8CB	1.173520	1.449228	0.343128	0.099*
H8CC	1.117723	1.490156	0.252578	0.099*
C9C	1.2710 (3)	1.3767 (3)	0.1587 (3)	0.0892 (10)
H9CA	1.288769	1.312075	0.092140	0.107*
H9CB	1.274057	1.448364	0.146466	0.107*
H9CC	1.329854	1.407437	0.237016	0.107*
C10C	0.7263 (3)	1.1324 (3)	−0.2780 (2)	0.0791 (9)
H10G	0.649682	1.087929	−0.276417	0.095*
H10H	0.717712	1.195180	−0.300377	0.095*
H10I	0.751903	1.070384	−0.338399	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0756 (13)	0.0450 (8)	0.0485 (8)	0.0227 (9)	0.0196 (8)	0.0175 (7)
C1	0.0557 (16)	0.0476 (12)	0.0470 (12)	0.0216 (12)	0.0146 (11)	0.0202 (10)
C2	0.0512 (16)	0.0529 (12)	0.0424 (11)	0.0197 (12)	0.0119 (10)	0.0203 (10)
C3	0.0560 (17)	0.0500 (12)	0.0485 (12)	0.0181 (12)	0.0143 (11)	0.0134 (10)
C4	0.064 (2)	0.0499 (13)	0.0746 (17)	0.0203 (13)	0.0200 (14)	0.0248 (12)
C5	0.073 (2)	0.0587 (14)	0.0802 (17)	0.0325 (15)	0.0369 (15)	0.0398 (13)
C6	0.0701 (19)	0.0582 (13)	0.0569 (13)	0.0325 (14)	0.0293 (13)	0.0308 (11)
C7	0.0640 (18)	0.0631 (14)	0.0490 (12)	0.0243 (14)	0.0207 (12)	0.0271 (11)
C8	0.0582 (19)	0.0653 (15)	0.0709 (16)	0.0224 (14)	0.0235 (14)	0.0273 (13)
C9	0.081 (2)	0.121 (3)	0.0651 (17)	0.033 (2)	0.0296 (16)	0.0556 (18)
C10	0.110 (3)	0.0699 (17)	0.127 (3)	0.046 (2)	0.068 (2)	0.0630 (19)
O1B	0.0732 (15)	0.0987 (14)	0.0717 (11)	0.0327 (12)	0.0252 (10)	0.0627 (11)
C1B	0.0674 (19)	0.0793 (16)	0.0548 (13)	0.0400 (15)	0.0303 (13)	0.0444 (13)
C2B	0.0614 (18)	0.0732 (16)	0.0537 (13)	0.0307 (15)	0.0239 (12)	0.0339 (12)
C3B	0.080 (2)	0.111 (2)	0.0636 (16)	0.040 (2)	0.0303 (15)	0.0585 (17)
C4B	0.100 (3)	0.109 (2)	0.084 (2)	0.043 (2)	0.0416 (19)	0.0731 (19)
C5B	0.092 (3)	0.0780 (18)	0.093 (2)	0.0477 (19)	0.0476 (19)	0.0572 (17)
C6B	0.0686 (19)	0.0639 (14)	0.0576 (14)	0.0280 (14)	0.0278 (13)	0.0334 (12)
C7B	0.065 (2)	0.0820 (18)	0.0647 (16)	0.0291 (16)	0.0237 (14)	0.0349 (14)
C8B	0.074 (2)	0.123 (3)	0.0769 (18)	0.047 (2)	0.0328 (16)	0.0598 (19)
C9B	0.070 (3)	0.100 (3)	0.088 (2)	0.011 (2)	0.0212 (18)	0.004 (2)
C10B	0.116 (3)	0.0695 (18)	0.116 (3)	0.037 (2)	0.057 (2)	0.0551 (19)
O1C	0.0754 (14)	0.0683 (11)	0.0765 (11)	0.0270 (10)	0.0247 (10)	0.0538 (10)
C2C	0.0600 (17)	0.0555 (12)	0.0518 (12)	0.0239 (12)	0.0227 (12)	0.0309 (11)
C6C	0.0635 (18)	0.0525 (12)	0.0505 (12)	0.0217 (12)	0.0198 (12)	0.0285 (10)
C4C	0.091 (2)	0.0642 (15)	0.0566 (14)	0.0223 (15)	0.0214 (14)	0.0400 (13)
C1C	0.0614 (17)	0.0571 (12)	0.0516 (12)	0.0263 (12)	0.0235 (12)	0.0344 (11)
C5C	0.073 (2)	0.0620 (14)	0.0543 (13)	0.0272 (14)	0.0180 (13)	0.0331 (12)
C3C	0.076 (2)	0.0536 (13)	0.0568 (14)	0.0163 (13)	0.0184 (13)	0.0333 (12)
C7C	0.0586 (18)	0.0656 (15)	0.0602 (14)	0.0215 (14)	0.0128 (12)	0.0352 (12)
C8C	0.075 (2)	0.095 (2)	0.0540 (15)	0.0294 (19)	0.0080 (14)	0.0249 (15)
C9C	0.064 (2)	0.102 (2)	0.096 (2)	0.0242 (19)	0.0198 (17)	0.050 (2)
C10C	0.091 (3)	0.0840 (19)	0.0611 (16)	0.0297 (18)	0.0095 (15)	0.0425 (15)

Geometric parameters (Å, º) top

O1—H1A	0.8202 (10)	C5B—C6B	1.520 (4)
O1—H1B	0.8201 (10)	C5B—C10B	1.520 (5)
O1—C1	1.442 (3)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.524 (3)	C7B—H7B	0.9800
C1—C6	1.511 (3)	C7B—C8B	1.515 (4)
C2—H2	0.9800	C7B—C9B	1.522 (4)
C2—C3	1.534 (3)	C8B—H8BA	0.9600
C2—C7	1.535 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.519 (4)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.514 (4)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.531 (3)	O1C—H1CA	0.8200 (10)
C5—C10	1.513 (4)	O1C—H1CB	0.8201 (10)
C6—H6A	0.9700	O1C—C1C	1.431 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.502 (3)
C7—C8	1.517 (4)	C2C—C3C	1.529 (3)
C7—C9	1.524 (4)	C2C—C7C	1.548 (3)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.520 (3)
C9—H9A	0.9600	C6C—C5C	1.528 (3)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.503 (4)
C10—H10B	0.9600	C4C—C3C	1.526 (4)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.8205 (10)	C5C—H5C	0.9800
O1B—H1BB	0.8201 (10)	C5C—C10C	1.524 (4)
O1B—C1B	1.427 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.518 (3)	C7C—H7C	0.9800
C1B—C6B	1.512 (4)	C7C—C8C	1.525 (3)
C2B—H2B	0.9800	C7C—C9C	1.510 (4)
C2B—C3B	1.525 (4)	C8C—H8CA	0.9600
C2B—C7B	1.545 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.523 (5)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.515 (4)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	106.1 (18)	C10B—C5B—C6B	111.4 (3)
C1—O1—H1A	113.1 (8)	C1B—C6B—C5B	112.8 (2)
C1—O1—H1B	105.2 (19)	C1B—C6B—H6BA	109.0
O1—C1—H1	108.6	C1B—C6B—H6BB	109.0
O1—C1—C2	109.19 (18)	C5B—C6B—H6BA	109.0
O1—C1—C6	110.11 (18)	C5B—C6B—H6BB	109.0
C2—C1—H1	108.6	H6BA—C6B—H6BB	107.8
C6—C1—H1	108.6	C2B—C7B—H7B	106.6
C6—C1—C2	111.8 (2)	C8B—C7B—C2B	114.7 (3)
C1—C2—H2	106.5	C8B—C7B—H7B	106.6
C1—C2—C3	109.12 (19)	C8B—C7B—C9B	110.4 (3)
C1—C2—C7	113.5 (2)	C9B—C7B—C2B	111.5 (2)
C3—C2—H2	106.5	C9B—C7B—H7B	106.6
C3—C2—C7	114.03 (19)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.5	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.3	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.3	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	107.9	H8BA—C8B—H8BC	109.5
C4—C3—C2	111.79 (19)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.3	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.3	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.7 (2)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	107.9	C5B—C10B—H10F	109.5
C4—C5—C6	109.6 (2)	H10D—C10B—H10E	109.5
C6—C5—H5	107.9	H10D—C10B—H10F	109.5
C10—C5—C4	112.0 (3)	H10E—C10B—H10F	109.5
C10—C5—H5	107.9	H1CA—O1C—H1CB	110.9 (13)
C10—C5—C6	111.4 (2)	C1C—O1C—H1CA	130.1 (5)
C1—C6—C5	113.44 (19)	C1C—O1C—H1CB	115.2 (9)
C1—C6—H6A	108.9	C1C—C2C—H2C	106.7
C1—C6—H6B	108.9	C1C—C2C—C3C	110.3 (2)
C5—C6—H6A	108.9	C1C—C2C—C7C	112.83 (19)
C5—C6—H6B	108.9	C3C—C2C—H2C	106.7
H6A—C6—H6B	107.7	C3C—C2C—C7C	113.2 (2)
C2—C7—H7	107.1	C7C—C2C—H2C	106.7
C8—C7—C2	113.9 (2)	H6CA—C6C—H6CB	107.8
C8—C7—H7	107.1	C1C—C6C—H6CA	109.1
C8—C7—C9	110.0 (2)	C1C—C6C—H6CB	109.1
C9—C7—C2	111.2 (2)	C1C—C6C—C5C	112.7 (2)
C9—C7—H7	107.1	C5C—C6C—H6CA	109.1
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.1
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.3
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.3
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.6 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.3
C7—C9—H9B	109.5	O1C—C1C—C2C	110.3 (2)
C7—C9—H9C	109.5	O1C—C1C—C6C	110.2 (2)
H9A—C9—H9B	109.5	O1C—C1C—H1C	107.8
H9A—C9—H9C	109.5	C2C—C1C—C6C	112.75 (18)
H9B—C9—H9C	109.5	C2C—C1C—H1C	107.8
C5—C10—H10A	109.5	C6C—C1C—H1C	107.8
C5—C10—H10B	109.5	C6C—C5C—H5C	107.6
C5—C10—H10C	109.5	C4C—C5C—C6C	109.6 (2)
H10A—C10—H10B	109.5	C4C—C5C—H5C	107.6
H10A—C10—H10C	109.5	C4C—C5C—C10C	112.5 (2)
H10B—C10—H10C	109.5	C10C—C5C—C6C	111.5 (2)
H1BA—O1B—H1BB	134 (3)	C10C—C5C—H5C	107.6
C1B—O1B—H1BA	102.8 (5)	C2C—C3C—H3CA	109.3
C1B—O1B—H1BB	104 (2)	C2C—C3C—H3CB	109.3
O1B—C1B—H1BC	108.4	C4C—C3C—C2C	111.8 (2)
O1B—C1B—C2B	112.7 (2)	C4C—C3C—H3CA	109.3
O1B—C1B—C6B	108.2 (2)	C4C—C3C—H3CB	109.3
C2B—C1B—H1BC	108.4	H3CA—C3C—H3CB	107.9
C6B—C1B—H1BC	108.4	C2C—C7C—H7C	106.9
C6B—C1B—C2B	110.51 (19)	C8C—C7C—C2C	113.7 (2)
C1B—C2B—H2B	106.8	C8C—C7C—H7C	106.9
C1B—C2B—C3B	108.5 (2)	C9C—C7C—C2C	111.6 (2)
C1B—C2B—C7B	113.5 (2)	C9C—C7C—H7C	106.9
C3B—C2B—H2B	106.8	C9C—C7C—C8C	110.4 (2)
C3B—C2B—C7B	114.1 (3)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.8	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.5	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.5	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.1	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	110.8 (3)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.5	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.5	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.2	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.2	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.9	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.0 (2)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.2	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.2	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.9	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.5 (2)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	112.2 (2)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.9	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.9

O1—C1—C2—C3	176.8 (2)	C3B—C2B—C7B—C9B	−68.6 (3)
O1—C1—C2—C7	−54.8 (3)	C3B—C4B—C5B—C6B	−53.7 (4)
O1—C1—C6—C5	−176.4 (2)	C3B—C4B—C5B—C10B	−178.0 (3)
C1—C2—C3—C4	−56.7 (3)	C4B—C5B—C6B—C1B	54.2 (3)
C1—C2—C7—C8	−74.6 (3)	C6B—C1B—C2B—C3B	58.7 (3)
C1—C2—C7—C9	160.4 (2)	C6B—C1B—C2B—C7B	−173.3 (2)
C2—C1—C6—C5	−54.8 (3)	C7B—C2B—C3B—C4B	173.5 (2)
C2—C3—C4—C5	58.0 (3)	C10B—C5B—C6B—C1B	178.9 (2)
C3—C2—C7—C8	51.3 (3)	C1C—C2C—C3C—C4C	−54.4 (3)
C3—C2—C7—C9	−73.8 (3)	C1C—C2C—C7C—C8C	−62.6 (3)
C3—C4—C5—C6	−54.4 (3)	C1C—C2C—C7C—C9C	171.7 (2)
C3—C4—C5—C10	−178.7 (2)	C1C—C6C—C5C—C4C	54.3 (3)
C4—C5—C6—C1	53.5 (3)	C1C—C6C—C5C—C10C	179.6 (2)
C6—C1—C2—C3	54.7 (3)	C5C—C6C—C1C—O1C	−177.4 (2)
C6—C1—C2—C7	−176.8 (2)	C5C—C6C—C1C—C2C	−53.7 (3)
C7—C2—C3—C4	175.2 (2)	C5C—C4C—C3C—C2C	57.4 (3)
C10—C5—C6—C1	178.1 (3)	C3C—C2C—C1C—O1C	176.16 (17)
O1B—C1B—C2B—C3B	179.9 (2)	C3C—C2C—C1C—C6C	52.6 (2)
O1B—C1B—C2B—C7B	−52.1 (3)	C3C—C2C—C7C—C8C	63.6 (3)
O1B—C1B—C6B—C5B	178.22 (19)	C3C—C2C—C7C—C9C	−62.0 (3)
C1B—C2B—C3B—C4B	−58.9 (3)	C3C—C4C—C5C—C6C	−56.0 (3)
C1B—C2B—C7B—C8B	−67.1 (3)	C3C—C4C—C5C—C10C	179.2 (2)
C1B—C2B—C7B—C9B	166.4 (3)	C7C—C2C—C1C—O1C	−56.1 (3)
C2B—C1B—C6B—C5B	−57.9 (3)	C7C—C2C—C1C—C6C	−179.69 (19)
C2B—C3B—C4B—C5B	57.7 (3)	C7C—C2C—C3C—C4C	178.1 (2)
C3B—C2B—C7B—C8B	57.9 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_190K) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.006 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.9443 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4081 (9) Å	Cell parameters from 6036 reflections
c = 12.7491 (10) Å	θ = 1.9–26.2°
α = 117.321 (8)°	µ = 0.06 mm⁻¹
β = 99.504 (7)°	T = 190 K
γ = 103.673 (7)°	Plate, colourless
V = 1547.0 (2) Å³	0.25 × 0.1 × 0.05 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	R_int = 0.035
Radiation source: Enhance (Mo) X-ray Source	θ_max = 26.3°, θ_min = 1.9°
ω scans	h = −14→13
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −15→15
T_min = 0.993, T_max = 0.997	l = −11→15
11808 measured reflections	3 standard reflections every 120 min
6036 independent reflections	intensity decay: none
3297 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.0879P)² + 0.091P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.204	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.24 e Å⁻³
6036 reflections	Δρ_min = −0.17 e Å⁻³
314 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
14 restraints	Extinction coefficient: 0.016 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.54768 (14)	1.07496 (14)	0.12565 (13)	0.0641 (5)
H1B	0.614463	1.069173	0.124219	0.096*	0.5
H1A	0.525 (5)	1.0436 (15)	0.0501 (3)	0.096*	0.5
C1	0.5583 (2)	1.20891 (19)	0.17845 (19)	0.0553 (6)
H1	0.479357	1.212220	0.146969	0.083*
C2	0.5930 (2)	1.2742 (2)	0.31931 (19)	0.0554 (6)
H2	0.671978	1.268966	0.347393	0.083*
C3	0.6130 (2)	1.4188 (2)	0.3769 (2)	0.0637 (6)
H3A	0.536799	1.428473	0.350973	0.096*
H3B	0.638987	1.460950	0.466896	0.096*
C4	0.7078 (3)	1.4847 (2)	0.3383 (2)	0.0738 (8)
H4A	0.716526	1.575393	0.375052	0.111*
H4B	0.785531	1.480938	0.369929	0.111*
C5	0.6736 (3)	1.4211 (2)	0.1984 (3)	0.0717 (7)
H5	0.597498	1.430596	0.168757	0.108*
C6	0.6515 (2)	1.2766 (2)	0.1396 (2)	0.0626 (6)
H6A	0.623861	1.235454	0.049756	0.094*
H6B	0.727685	1.265734	0.163083	0.094*
C7	0.5053 (2)	1.2055 (2)	0.3632 (2)	0.0648 (7)
H7	0.487690	1.112246	0.310256	0.097*
C8	0.3843 (3)	1.2256 (3)	0.3502 (3)	0.0776 (8)
H8A	0.348177	1.201855	0.265999	0.093*
H8B	0.331174	1.172401	0.370668	0.093*
H8C	0.397103	1.315189	0.405614	0.093*
C9	0.5637 (3)	1.2428 (4)	0.4963 (3)	0.0969 (10)
H9A	0.640086	1.229797	0.503635	0.116*
H9B	0.576940	1.332419	0.552056	0.116*
H9C	0.511011	1.189631	0.517110	0.116*
C10	0.7698 (3)	1.4853 (3)	0.1600 (3)	0.1004 (11)
H10A	0.745340	1.442748	0.070909	0.121*
H10B	0.779365	1.575207	0.195165	0.121*
H10C	0.845673	1.478659	0.189717	0.121*
O1B	0.74404 (15)	1.00584 (19)	0.12238 (17)	0.0824 (6)
H1BA	0.8006 (14)	1.0105 (8)	0.094 (2)	0.124*	0.5
H1BB	0.7056 (2)	1.0549 (3)	0.1364 (14)	0.124*	0.5
C1B	0.7604 (3)	0.9491 (3)	0.1968 (2)	0.0648 (7)
H1BC	0.820786	0.907970	0.177162	0.097*
C2B	0.8049 (3)	1.0485 (2)	0.3351 (2)	0.0683 (7)
H2B	0.739825	1.082615	0.353139	0.102*
C3B	0.8175 (3)	0.9787 (3)	0.4058 (3)	0.0860 (9)
H3BA	0.878524	0.939537	0.387357	0.129*
H3BB	0.844594	1.041058	0.494569	0.129*
C4B	0.6977 (3)	0.8740 (3)	0.3707 (3)	0.0934 (10)
H4BA	0.709489	0.829850	0.415377	0.140*
H4BB	0.638798	0.914234	0.395771	0.140*
C5B	0.6483 (3)	0.7755 (3)	0.2322 (3)	0.0831 (9)
H5B	0.706211	0.731226	0.210319	0.125*
C6B	0.6412 (3)	0.8450 (2)	0.1613 (2)	0.0660 (7)
H6BA	0.615881	0.781987	0.072854	0.099*
H6BB	0.579805	0.884166	0.176913	0.099*
C7B	0.9187 (3)	1.1659 (3)	0.3757 (3)	0.0799 (8)
H7B	0.901252	1.197448	0.319357	0.120*
C8B	1.0333 (3)	1.1348 (4)	0.3643 (3)	0.0929 (10)
H8BA	1.017514	1.064388	0.281624	0.112*
H8BB	1.096863	1.209911	0.380906	0.112*
H8BC	1.057990	1.110395	0.423322	0.112*
C9B	0.9413 (3)	1.2768 (4)	0.5056 (3)	0.1312 (16)
H9BA	0.868104	1.295249	0.511248	0.157*
H9BB	0.965579	1.252968	0.565103	0.157*
H9BC	1.004452	1.352484	0.522687	0.157*
C10B	0.5269 (3)	0.6733 (3)	0.1958 (3)	0.1058 (11)
H10D	0.534573	0.631220	0.242257	0.127*
H10E	0.467566	0.713736	0.213543	0.127*
H10F	0.501535	0.610207	0.108373	0.127*
O1C	0.93803 (17)	1.08066 (16)	0.05543 (16)	0.0731 (5)
H1CA	0.8811 (15)	1.0334 (5)	0.061 (2)	0.110*	0.5
H1CB	0.9750 (14)	1.0347 (13)	0.0200 (15)	0.110*	0.5
C2C	1.0500 (2)	1.2511 (2)	0.0299 (2)	0.0586 (6)
H2C	1.078518	1.188595	−0.029418	0.088*
C6C	0.8336 (2)	1.1084 (2)	−0.1052 (2)	0.0607 (6)
H6CA	0.755290	1.067637	−0.101995	0.091*
H6CB	0.855399	1.040738	−0.165574	0.091*
C4C	0.9458 (3)	1.2750 (3)	−0.1432 (2)	0.0752 (8)
H4CA	0.939072	1.338222	−0.166263	0.113*
H4CB	0.973903	1.214312	−0.203167	0.113*
C1C	0.9278 (2)	1.1744 (2)	0.0219 (2)	0.0574 (6)
H1C	0.899046	1.234949	0.082733	0.086*
C5C	0.8231 (3)	1.2032 (2)	−0.1479 (2)	0.0694 (7)
H5C	0.795585	1.266967	−0.088678	0.104*
C3C	1.0381 (3)	1.3442 (2)	−0.0144 (2)	0.0692 (7)
H3CA	1.013654	1.410509	0.044177	0.104*
H3CB	1.116537	1.386854	−0.015991	0.104*
C7C	1.1459 (2)	1.3174 (2)	0.1588 (2)	0.0700 (7)
H7C	1.147419	1.249109	0.177067	0.105*
C8C	1.1153 (3)	1.4176 (3)	0.2638 (2)	0.0941 (10)
H8CA	1.034968	1.378887	0.262579	0.113*
H8CB	1.172800	1.447459	0.342182	0.113*
H8CC	1.118745	1.489762	0.252789	0.113*
C9C	1.2720 (3)	1.3757 (4)	0.1583 (3)	0.1025 (10)
H9CA	1.289620	1.311266	0.091652	0.123*
H9CB	1.276199	1.447666	0.146842	0.123*
H9CC	1.330254	1.405363	0.236235	0.123*
C10C	0.7285 (3)	1.1343 (3)	−0.2760 (3)	0.0898 (9)
H10G	0.651909	1.089966	−0.274262	0.108*
H10H	0.720040	1.197071	−0.297940	0.108*
H10I	0.754212	1.072689	−0.336545	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0807 (13)	0.0469 (8)	0.0535 (8)	0.0212 (8)	0.0211 (9)	0.0184 (7)
C1	0.0618 (16)	0.0450 (11)	0.0502 (12)	0.0206 (10)	0.0161 (10)	0.0179 (9)
C2	0.0533 (15)	0.0553 (12)	0.0475 (11)	0.0189 (11)	0.0128 (10)	0.0203 (10)
C3	0.0633 (16)	0.0510 (12)	0.0543 (13)	0.0166 (11)	0.0152 (11)	0.0131 (10)
C4	0.0692 (19)	0.0499 (12)	0.0844 (18)	0.0164 (12)	0.0224 (14)	0.0241 (12)
C5	0.081 (2)	0.0594 (13)	0.0887 (18)	0.0312 (13)	0.0395 (15)	0.0417 (13)
C6	0.0724 (18)	0.0605 (13)	0.0628 (14)	0.0305 (12)	0.0295 (12)	0.0323 (11)
C7	0.0690 (18)	0.0648 (14)	0.0545 (13)	0.0220 (13)	0.0228 (12)	0.0263 (11)
C8	0.0628 (19)	0.0749 (16)	0.0830 (18)	0.0200 (14)	0.0262 (14)	0.0330 (14)
C9	0.093 (3)	0.134 (3)	0.0729 (18)	0.035 (2)	0.0336 (17)	0.0606 (19)
C10	0.123 (3)	0.0758 (18)	0.143 (3)	0.049 (2)	0.077 (2)	0.070 (2)
O1B	0.0823 (15)	0.1124 (15)	0.0871 (12)	0.0365 (12)	0.0308 (10)	0.0761 (12)
C1B	0.0733 (18)	0.0836 (16)	0.0635 (14)	0.0397 (14)	0.0325 (13)	0.0488 (13)
C2B	0.0714 (19)	0.0781 (16)	0.0652 (15)	0.0328 (14)	0.0309 (13)	0.0388 (13)
C3B	0.086 (2)	0.121 (2)	0.0720 (17)	0.0381 (19)	0.0314 (15)	0.0641 (17)
C4B	0.104 (3)	0.119 (2)	0.093 (2)	0.040 (2)	0.0421 (19)	0.079 (2)
C5B	0.097 (2)	0.0797 (18)	0.109 (2)	0.0479 (17)	0.0523 (19)	0.0629 (17)
C6B	0.0750 (19)	0.0677 (14)	0.0640 (14)	0.0303 (13)	0.0307 (13)	0.0356 (12)
C7B	0.070 (2)	0.0848 (18)	0.0777 (17)	0.0247 (15)	0.0251 (14)	0.0371 (15)
C8B	0.072 (2)	0.135 (3)	0.090 (2)	0.044 (2)	0.0338 (16)	0.066 (2)
C9B	0.082 (3)	0.113 (3)	0.109 (3)	0.009 (2)	0.028 (2)	0.002 (2)
C10B	0.126 (3)	0.0741 (18)	0.136 (3)	0.038 (2)	0.061 (2)	0.062 (2)
O1C	0.0808 (14)	0.0715 (10)	0.0889 (12)	0.0256 (9)	0.0277 (10)	0.0589 (10)
C2C	0.0645 (16)	0.0581 (12)	0.0601 (13)	0.0225 (11)	0.0249 (11)	0.0339 (11)
C6C	0.0687 (17)	0.0561 (12)	0.0582 (13)	0.0209 (11)	0.0233 (12)	0.0300 (10)
C4C	0.095 (2)	0.0717 (15)	0.0659 (15)	0.0212 (15)	0.0240 (14)	0.0454 (13)
C1C	0.0672 (17)	0.0593 (12)	0.0589 (13)	0.0265 (12)	0.0253 (11)	0.0372 (11)
C5C	0.081 (2)	0.0685 (15)	0.0607 (14)	0.0271 (14)	0.0194 (13)	0.0359 (12)
C3C	0.080 (2)	0.0591 (13)	0.0678 (15)	0.0165 (13)	0.0203 (13)	0.0377 (12)
C7C	0.0629 (18)	0.0715 (15)	0.0711 (15)	0.0214 (13)	0.0141 (13)	0.0372 (13)
C8C	0.088 (2)	0.104 (2)	0.0606 (16)	0.0306 (19)	0.0083 (15)	0.0273 (15)
C9C	0.069 (2)	0.118 (3)	0.111 (3)	0.0255 (19)	0.0213 (18)	0.058 (2)
C10C	0.101 (3)	0.093 (2)	0.0703 (17)	0.0298 (18)	0.0095 (16)	0.0460 (16)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.514 (4)
O1—H1A	0.8200 (10)	C5B—C10B	1.515 (4)
O1—C1	1.441 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.521 (3)	C7B—H7B	0.9800
C1—C6	1.520 (3)	C7B—C8B	1.520 (4)
C2—H2	0.9800	C7B—C9B	1.514 (4)
C2—C3	1.531 (3)	C8B—H8BA	0.9600
C2—C7	1.532 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.519 (3)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.512 (4)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.524 (3)	O1C—H1CA	0.8201 (10)
C5—C10	1.519 (4)	O1C—H1CB	0.8201 (10)
C6—H6A	0.9700	O1C—C1C	1.434 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.500 (3)
C7—C8	1.519 (4)	C2C—C3C	1.525 (3)
C7—C9	1.521 (4)	C2C—C7C	1.542 (3)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.518 (3)
C9—H9A	0.9600	C6C—C5C	1.527 (3)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.501 (4)
C10—H10B	0.9600	C4C—C3C	1.520 (3)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.8204 (10)	C5C—H5C	0.9800
O1B—H1BB	0.8201 (10)	C5C—C10C	1.525 (4)
O1B—C1B	1.432 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.515 (3)	C7C—H7C	0.9800
C1B—C6B	1.510 (4)	C7C—C8C	1.524 (4)
C2B—H2B	0.9800	C7C—C9C	1.511 (4)
C2B—C3B	1.524 (4)	C8C—H8CA	0.9600
C2B—C7B	1.541 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.520 (4)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.515 (4)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	90.9	C10B—C5B—H5B	107.7
C1—O1—H1B	109.5	C1B—C6B—C5B	113.0 (2)
C1—O1—H1A	105 (2)	C1B—C6B—H6BA	109.0
O1—C1—H1	108.8	C1B—C6B—H6BB	109.0
O1—C1—C2	109.09 (18)	C5B—C6B—H6BA	109.0
O1—C1—C6	109.92 (17)	C5B—C6B—H6BB	109.0
C2—C1—H1	108.8	H6BA—C6B—H6BB	107.8
C6—C1—H1	108.8	C2B—C7B—H7B	106.4
C6—C1—C2	111.48 (19)	C8B—C7B—C2B	114.7 (3)
C1—C2—H2	106.5	C8B—C7B—H7B	106.4
C1—C2—C3	109.48 (19)	C9B—C7B—C2B	111.8 (2)
C1—C2—C7	113.57 (19)	C9B—C7B—H7B	106.4
C3—C2—H2	106.5	C9B—C7B—C8B	110.5 (3)
C3—C2—C7	113.73 (18)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.5	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.3	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.3	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	107.9	H8BA—C8B—H8BC	109.5
C4—C3—C2	111.73 (19)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.3	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.3	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.7 (2)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	108.1	C5B—C10B—H10F	109.5
C4—C5—C6	109.5 (2)	H10D—C10B—H10E	109.5
C4—C5—C10	111.6 (2)	H10D—C10B—H10F	109.5
C6—C5—H5	108.1	H10E—C10B—H10F	109.5
C10—C5—H5	108.1	H1CA—O1C—H1CB	106.1 (12)
C10—C5—C6	111.1 (2)	C1C—O1C—H1CA	123.8 (16)
C1—C6—C5	113.03 (19)	C1C—O1C—H1CB	115.7 (9)
C1—C6—H6A	109.0	C1C—C2C—H2C	106.4
C1—C6—H6B	109.0	C1C—C2C—C3C	110.4 (2)
C5—C6—H6A	109.0	C1C—C2C—C7C	113.15 (19)
C5—C6—H6B	109.0	C3C—C2C—H2C	106.4
H6A—C6—H6B	107.8	C3C—C2C—C7C	113.5 (2)
C2—C7—H7	106.9	C7C—C2C—H2C	106.4
C8—C7—C2	114.2 (2)	H6CA—C6C—H6CB	107.8
C8—C7—H7	106.9	C1C—C6C—H6CA	109.1
C8—C7—C9	110.1 (2)	C1C—C6C—H6CB	109.1
C9—C7—C2	111.5 (2)	C1C—C6C—C5C	112.43 (19)
C9—C7—H7	106.9	C5C—C6C—H6CA	109.1
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.1
C7—C8—H8B	109.5	H4CA—C4C—H4CB	107.9
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.3
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.3
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.8 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.3
C7—C9—H9B	109.5	O1C—C1C—C2C	110.4 (2)
C7—C9—H9C	109.5	O1C—C1C—C6C	110.30 (19)
H9A—C9—H9B	109.5	O1C—C1C—H1C	107.6
H9A—C9—H9C	109.5	C2C—C1C—C6C	113.19 (19)
H9B—C9—H9C	109.5	C2C—C1C—H1C	107.6
C5—C10—H10A	109.5	C6C—C1C—H1C	107.6
C5—C10—H10B	109.5	C6C—C5C—H5C	107.6
C5—C10—H10C	109.5	C4C—C5C—C6C	109.7 (2)
H10A—C10—H10B	109.5	C4C—C5C—H5C	107.6
H10A—C10—H10C	109.5	C4C—C5C—C10C	112.7 (2)
H10B—C10—H10C	109.5	C10C—C5C—C6C	111.4 (2)
H1BA—O1B—H1BB	124.6 (14)	C10C—C5C—H5C	107.6
C1B—O1B—H1BA	108.8 (15)	C2C—C3C—H3CA	109.2
C1B—O1B—H1BB	120.4 (12)	C2C—C3C—H3CB	109.2
O1B—C1B—H1BC	108.3	C4C—C3C—C2C	112.1 (2)
O1B—C1B—C2B	112.5 (2)	C4C—C3C—H3CA	109.2
O1B—C1B—C6B	108.3 (2)	C4C—C3C—H3CB	109.2
C2B—C1B—H1BC	108.3	H3CA—C3C—H3CB	107.9
C6B—C1B—H1BC	108.3	C2C—C7C—H7C	106.7
C6B—C1B—C2B	110.88 (19)	C8C—C7C—C2C	113.6 (2)
C1B—C2B—H2B	106.5	C8C—C7C—H7C	106.7
C1B—C2B—C3B	108.5 (2)	C9C—C7C—C2C	111.9 (2)
C1B—C2B—C7B	113.8 (2)	C9C—C7C—H7C	106.7
C3B—C2B—H2B	106.5	C9C—C7C—C8C	110.7 (2)
C3B—C2B—C7B	114.5 (3)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.5	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.4	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.4	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.0	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	111.3 (3)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.4	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.4	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.2	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.2	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.9	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.0 (2)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.2	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.2	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.7	C5C—C10C—H10I	109.5
C4B—C5B—C10B	112.4 (3)	H10G—C10C—H10H	109.5
C6B—C5B—C4B	109.5 (2)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.7	H10H—C10C—H10I	109.5
C6B—C5B—C10B	111.6 (3)

O1—C1—C2—C3	176.18 (19)	C3B—C2B—C7B—C9B	−68.6 (4)
O1—C1—C2—C7	−55.5 (3)	C3B—C4B—C5B—C6B	−53.4 (4)
O1—C1—C6—C5	−176.5 (2)	C3B—C4B—C5B—C10B	−178.1 (3)
C1—C2—C3—C4	−56.2 (3)	C4B—C5B—C6B—C1B	54.0 (3)
C1—C2—C7—C8	−74.2 (2)	C6B—C1B—C2B—C3B	57.7 (3)
C1—C2—C7—C9	160.3 (2)	C6B—C1B—C2B—C7B	−173.5 (2)
C2—C1—C6—C5	−55.4 (3)	C7B—C2B—C3B—C4B	173.7 (2)
C2—C3—C4—C5	57.7 (3)	C10B—C5B—C6B—C1B	179.1 (2)
C3—C2—C7—C8	51.9 (3)	C1C—C2C—C3C—C4C	−53.5 (3)
C3—C2—C7—C9	−73.6 (3)	C1C—C2C—C7C—C8C	−62.8 (3)
C3—C4—C5—C6	−55.2 (3)	C1C—C2C—C7C—C9C	170.9 (2)
C3—C4—C5—C10	−178.7 (2)	C1C—C6C—C5C—C4C	54.2 (3)
C4—C5—C6—C1	54.5 (3)	C1C—C6C—C5C—C10C	179.6 (2)
C6—C1—C2—C3	54.6 (3)	C5C—C6C—C1C—O1C	−177.56 (19)
C6—C1—C2—C7	−177.1 (2)	C5C—C6C—C1C—C2C	−53.4 (3)
C7—C2—C3—C4	175.6 (2)	C5C—C4C—C3C—C2C	56.9 (3)
C10—C5—C6—C1	178.3 (2)	C3C—C2C—C1C—O1C	176.06 (18)
O1B—C1B—C2B—C3B	179.2 (2)	C3C—C2C—C1C—C6C	51.9 (3)
O1B—C1B—C2B—C7B	−52.1 (3)	C3C—C2C—C7C—C8C	64.0 (3)
O1B—C1B—C6B—C5B	178.56 (19)	C3C—C2C—C7C—C9C	−62.3 (3)
C1B—C2B—C3B—C4B	−58.0 (3)	C3C—C4C—C5C—C6C	−56.0 (3)
C1B—C2B—C7B—C8B	−67.4 (3)	C3C—C4C—C5C—C10C	179.3 (2)
C1B—C2B—C7B—C9B	165.8 (3)	C7C—C2C—C1C—O1C	−55.5 (3)
C2B—C1B—C6B—C5B	−57.5 (3)	C7C—C2C—C1C—C6C	−179.66 (19)
C2B—C3B—C4B—C5B	57.2 (4)	C7C—C2C—C3C—C4C	178.2 (2)
C3B—C2B—C7B—C8B	58.2 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_220K) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 1.001 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.9423 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4458 (11) Å	Cell parameters from 6062 reflections
c = 12.7755 (11) Å	θ = 1.9–26.3°
α = 117.352 (9)°	µ = 0.06 mm⁻¹
β = 99.261 (7)°	T = 220 K
γ = 103.787 (8)°	Plate, colourless
V = 1555.4 (3) Å³	0.25 × 0.1 × 0.05 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	3146 reflections with I > 2σ(I)
ω scans	R_int = 0.028
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θ_max = 26.3°, θ_min = 1.9°
T_min = 0.993, T_max = 0.997	h = −14→13
11917 measured reflections	k = −15→15
6069 independent reflections	l = −11→15

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²) + (0.0906P)² + 0.078P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.203	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.25 e Å⁻³
6069 reflections	Δρ_min = −0.14 e Å⁻³
317 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
14 restraints	Extinction coefficient: 0.014 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.54740 (15)	1.07544 (14)	0.12533 (14)	0.0707 (5)
H1A	0.6127 (8)	1.0649 (14)	0.1271 (18)	0.106*	0.5
H1B	0.508 (3)	1.022 (4)	0.05237 (18)	0.106*	0.5
C1	0.5581 (2)	1.20849 (19)	0.17873 (19)	0.0613 (6)
H1	0.479066	1.211676	0.147804	0.092*
C2	0.5927 (2)	1.2740 (2)	0.31892 (19)	0.0612 (6)
H2	0.671679	1.268829	0.346587	0.092*
C3	0.6126 (2)	1.4177 (2)	0.3770 (2)	0.0710 (7)
H3A	0.536359	1.427541	0.352156	0.107*
H3B	0.639182	1.459387	0.466660	0.107*
C4	0.7066 (3)	1.4835 (2)	0.3377 (3)	0.0831 (8)
H4A	0.715221	1.573867	0.374567	0.125*
H4B	0.784477	1.479759	0.368536	0.125*
C5	0.6719 (3)	1.4203 (2)	0.1984 (3)	0.0797 (8)
H5	0.595560	1.429460	0.169462	0.120*
C6	0.6505 (2)	1.2764 (2)	0.1395 (2)	0.0692 (6)
H6A	0.622562	1.235498	0.049916	0.104*
H6B	0.726896	1.265903	0.162267	0.104*
C7	0.5051 (2)	1.2046 (2)	0.3627 (2)	0.0721 (7)
H7	0.487951	1.111683	0.309900	0.108*
C8	0.3839 (3)	1.2241 (3)	0.3503 (3)	0.0886 (8)
H8A	0.347623	1.200356	0.266432	0.106*
H8B	0.331120	1.170952	0.371015	0.106*
H8C	0.396476	1.313416	0.405609	0.106*
C9	0.5631 (3)	1.2422 (4)	0.4955 (3)	0.1078 (11)
H9A	0.639669	1.229699	0.502963	0.129*
H9B	0.575841	1.331452	0.550919	0.129*
H9C	0.510485	1.188988	0.516325	0.129*
C10	0.7676 (3)	1.4845 (3)	0.1589 (4)	0.1104 (12)
H10A	0.742552	1.441948	0.070019	0.132*
H10B	0.777021	1.574097	0.194036	0.132*
H10C	0.843623	1.477916	0.187702	0.132*
O1B	0.74687 (17)	1.0092 (2)	0.12566 (18)	0.0926 (6)
H1BA	0.7954 (16)	1.016 (2)	0.0883 (11)	0.139*	0.5
H1BB	0.7041 (9)	1.0529 (16)	0.147 (2)	0.139*	0.5
C1B	0.7622 (3)	0.9522 (3)	0.1987 (2)	0.0715 (7)
H1BC	0.822519	0.911120	0.178628	0.107*
C2B	0.8067 (2)	1.0502 (2)	0.3367 (2)	0.0733 (7)
H2B	0.741813	1.084262	0.355223	0.110*
C3B	0.8187 (3)	0.9799 (3)	0.4062 (3)	0.0959 (9)
H3BA	0.844777	1.041514	0.494734	0.144*
H3BB	0.880278	0.941619	0.388082	0.144*
C4B	0.6990 (3)	0.8742 (4)	0.3699 (3)	0.1064 (11)
H4BA	0.710903	0.829308	0.413482	0.160*
H4BB	0.639791	0.913641	0.395497	0.160*
C5B	0.6504 (3)	0.7780 (3)	0.2326 (3)	0.0926 (9)
H5B	0.708585	0.734309	0.210312	0.139*
C6B	0.6430 (3)	0.8480 (2)	0.1623 (2)	0.0756 (7)
H6BA	0.618241	0.785631	0.074016	0.113*
H6BB	0.581424	0.886660	0.178106	0.113*
C7B	0.9201 (3)	1.1671 (3)	0.3776 (3)	0.0890 (8)
H7B	0.902976	1.198640	0.321428	0.134*
C8B	1.0344 (3)	1.1365 (4)	0.3660 (3)	0.1046 (10)
H8BA	1.018768	1.066330	0.283471	0.126*
H8BB	1.097840	1.211513	0.382332	0.126*
H8BC	1.059128	1.112240	0.424751	0.126*
C9B	0.9415 (3)	1.2772 (4)	0.5064 (4)	0.1510 (19)
H9BA	0.867987	1.294961	0.511644	0.181*
H9BB	0.965689	1.253747	0.565952	0.181*
H9BC	1.004401	1.353019	0.523533	0.181*
C10B	0.5294 (4)	0.6751 (3)	0.1953 (4)	0.1191 (12)
H10D	0.502167	0.616152	0.107147	0.143*
H10E	0.538351	0.628606	0.236838	0.143*
H10F	0.470969	0.715361	0.218274	0.143*
O1C	0.93850 (17)	1.08136 (16)	0.05529 (16)	0.0813 (5)
H1CA	0.8716 (15)	1.038 (2)	0.0496 (10)	0.122*	0.5
H1CB	0.9741 (14)	1.0336 (14)	0.0201 (15)	0.122*	0.5
C2C	1.0514 (2)	1.2517 (2)	0.0302 (2)	0.0649 (6)
H2C	1.080063	1.189551	−0.029062	0.097*
C6C	0.8354 (2)	1.1098 (2)	−0.1042 (2)	0.0679 (6)
H6CA	0.756856	1.068576	−0.101519	0.102*
H6CB	0.857657	1.042699	−0.164431	0.102*
C4C	0.9481 (3)	1.2760 (3)	−0.1422 (2)	0.0853 (8)
H4CA	0.941666	1.339230	−0.164947	0.128*
H4CB	0.976460	1.215611	−0.201910	0.128*
C1C	0.9284 (2)	1.1749 (2)	0.0223 (2)	0.0631 (6)
H1C	0.899472	1.235155	0.083047	0.095*
C5C	0.8247 (3)	1.2040 (3)	−0.1467 (2)	0.0770 (7)
H5C	0.797346	1.267623	−0.087322	0.115*
C3C	1.0395 (3)	1.3446 (2)	−0.0133 (2)	0.0763 (7)
H3CA	1.118073	1.387944	−0.014307	0.114*
H3CB	1.014322	1.410157	0.045028	0.114*
C7C	1.1462 (2)	1.3172 (3)	0.1589 (2)	0.0788 (7)
H7C	1.147257	1.249094	0.177253	0.118*
C8C	1.1158 (3)	1.4183 (3)	0.2636 (3)	0.1074 (11)
H8CA	1.035537	1.380159	0.262959	0.129*
H8CB	1.173322	1.448529	0.341783	0.129*
H8CC	1.119482	1.489782	0.251884	0.129*
C9C	1.2727 (3)	1.3755 (4)	0.1582 (3)	0.1156 (11)
H9CA	1.290657	1.310975	0.092040	0.139*
H9CB	1.276902	1.446801	0.146155	0.139*
H9CC	1.330742	1.405548	0.236054	0.139*
C10C	0.7309 (3)	1.1368 (3)	−0.2739 (3)	0.1032 (10)
H10G	0.654078	1.092312	−0.272383	0.124*
H10H	0.722864	1.199958	−0.294880	0.124*
H10I	0.756570	1.075547	−0.334672	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0867 (13)	0.0488 (8)	0.0643 (9)	0.0213 (8)	0.0232 (9)	0.0216 (7)
C1	0.0644 (15)	0.0524 (12)	0.0600 (13)	0.0213 (11)	0.0190 (11)	0.0236 (10)
C2	0.0559 (14)	0.0587 (12)	0.0561 (12)	0.0166 (11)	0.0148 (10)	0.0226 (10)
C3	0.0688 (17)	0.0575 (13)	0.0649 (14)	0.0190 (12)	0.0197 (12)	0.0172 (11)
C4	0.0780 (19)	0.0552 (13)	0.099 (2)	0.0187 (13)	0.0280 (15)	0.0290 (13)
C5	0.089 (2)	0.0675 (15)	0.102 (2)	0.0363 (14)	0.0461 (16)	0.0496 (15)
C6	0.0790 (18)	0.0645 (13)	0.0726 (15)	0.0320 (13)	0.0337 (13)	0.0361 (12)
C7	0.0700 (17)	0.0740 (15)	0.0651 (14)	0.0216 (13)	0.0258 (12)	0.0311 (12)
C8	0.0695 (19)	0.0824 (17)	0.100 (2)	0.0201 (14)	0.0328 (15)	0.0380 (15)
C9	0.102 (3)	0.150 (3)	0.0804 (19)	0.040 (2)	0.0385 (17)	0.066 (2)
C10	0.127 (3)	0.0841 (19)	0.165 (3)	0.050 (2)	0.086 (3)	0.080 (2)
O1B	0.0895 (15)	0.1286 (16)	0.1048 (14)	0.0424 (12)	0.0380 (11)	0.0909 (13)
C1B	0.0833 (19)	0.0903 (17)	0.0753 (15)	0.0456 (15)	0.0390 (14)	0.0579 (14)
C2B	0.0719 (18)	0.0836 (16)	0.0756 (16)	0.0329 (14)	0.0350 (13)	0.0436 (14)
C3B	0.094 (2)	0.138 (3)	0.0814 (18)	0.042 (2)	0.0349 (16)	0.0734 (19)
C4B	0.116 (3)	0.138 (3)	0.109 (2)	0.045 (2)	0.049 (2)	0.093 (2)
C5B	0.106 (2)	0.0866 (19)	0.123 (3)	0.0492 (18)	0.057 (2)	0.0694 (19)
C6B	0.086 (2)	0.0743 (15)	0.0759 (15)	0.0323 (14)	0.0353 (14)	0.0414 (13)
C7B	0.0693 (19)	0.0956 (19)	0.094 (2)	0.0255 (16)	0.0305 (15)	0.0433 (16)
C8B	0.077 (2)	0.146 (3)	0.110 (2)	0.046 (2)	0.0407 (18)	0.074 (2)
C9B	0.082 (3)	0.127 (3)	0.134 (3)	0.002 (2)	0.035 (2)	0.000 (2)
C10B	0.137 (3)	0.086 (2)	0.161 (3)	0.042 (2)	0.068 (3)	0.076 (2)
O1C	0.0882 (14)	0.0817 (11)	0.1010 (13)	0.0297 (10)	0.0342 (10)	0.0668 (10)
C2C	0.0695 (16)	0.0625 (13)	0.0706 (14)	0.0239 (12)	0.0296 (12)	0.0380 (11)
C6C	0.0747 (17)	0.0645 (13)	0.0669 (14)	0.0235 (12)	0.0258 (12)	0.0354 (11)
C4C	0.106 (2)	0.0797 (17)	0.0788 (17)	0.0236 (16)	0.0288 (16)	0.0526 (15)
C1C	0.0739 (17)	0.0635 (13)	0.0661 (13)	0.0281 (12)	0.0288 (12)	0.0405 (11)
C5C	0.086 (2)	0.0774 (16)	0.0708 (15)	0.0295 (15)	0.0223 (13)	0.0413 (13)
C3C	0.086 (2)	0.0621 (14)	0.0802 (16)	0.0160 (13)	0.0258 (14)	0.0417 (13)
C7C	0.0697 (18)	0.0788 (16)	0.0824 (17)	0.0207 (14)	0.0179 (14)	0.0423 (14)
C8C	0.099 (3)	0.115 (2)	0.0736 (18)	0.033 (2)	0.0124 (16)	0.0305 (17)
C9C	0.077 (2)	0.133 (3)	0.127 (3)	0.025 (2)	0.0262 (19)	0.067 (2)
C10C	0.114 (3)	0.108 (2)	0.0850 (19)	0.036 (2)	0.0135 (18)	0.0550 (18)

Geometric parameters (Å, º) top

O1—H1A	0.8201 (11)	C5B—C6B	1.517 (4)
O1—H1B	0.8199 (10)	C5B—C10B	1.513 (4)
O1—C1	1.434 (3)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.517 (3)	C7B—H7B	0.9800
C1—C6	1.519 (3)	C7B—C8B	1.514 (4)
C2—H2	0.9800	C7B—C9B	1.509 (4)
C2—C3	1.525 (3)	C8B—H8BA	0.9600
C2—C7	1.534 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.517 (3)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.510 (4)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.523 (3)	O1C—H1CA	0.8201 (10)
C5—C10	1.524 (4)	O1C—H1CB	0.8201 (10)
C6—H6A	0.9700	O1C—C1C	1.431 (3)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.508 (3)
C7—C8	1.519 (4)	C2C—C3C	1.521 (3)
C7—C9	1.521 (4)	C2C—C7C	1.542 (3)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.514 (3)
C9—H9A	0.9600	C6C—C5C	1.523 (3)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.508 (4)
C10—H10B	0.9600	C4C—C3C	1.522 (4)
C10—H10C	0.9600	C1C—H1C	0.9800
O1B—H1BA	0.8203 (9)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (10)	C5C—C10C	1.521 (4)
O1B—C1B	1.423 (3)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.513 (3)	C7C—H7C	0.9800
C1B—C6B	1.509 (4)	C7C—C8C	1.527 (4)
C2B—H2B	0.9800	C7C—C9C	1.515 (4)
C2B—C3B	1.520 (4)	C8C—H8CA	0.9600
C2B—C7B	1.536 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.522 (4)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.503 (4)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	101 (4)	C10B—C5B—C6B	111.5 (3)
C1—O1—H1A	113.5 (10)	C1B—C6B—C5B	112.6 (2)
C1—O1—H1B	120 (5)	C1B—C6B—H6BA	109.1
O1—C1—H1	108.5	C1B—C6B—H6BB	109.1
O1—C1—C2	109.77 (19)	C5B—C6B—H6BA	109.1
O1—C1—C6	109.95 (17)	C5B—C6B—H6BB	109.1
C2—C1—H1	108.5	H6BA—C6B—H6BB	107.8
C2—C1—C6	111.44 (19)	C2B—C7B—H7B	106.2
C6—C1—H1	108.5	C8B—C7B—C2B	114.8 (3)
C1—C2—H2	106.4	C8B—C7B—H7B	106.2
C1—C2—C3	110.1 (2)	C9B—C7B—C2B	111.8 (2)
C1—C2—C7	113.25 (19)	C9B—C7B—H7B	106.2
C3—C2—H2	106.4	C9B—C7B—C8B	110.9 (3)
C3—C2—C7	113.80 (19)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.3	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.3	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.0	H8BA—C8B—H8BC	109.5
C4—C3—C2	111.61 (19)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.3	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.3	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.8 (2)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	108.2	C5B—C10B—H10F	109.5
C4—C5—C6	109.5 (2)	H10D—C10B—H10E	109.5
C4—C5—C10	111.8 (3)	H10D—C10B—H10F	109.5
C6—C5—H5	108.2	H10E—C10B—H10F	109.5
C6—C5—C10	110.9 (2)	H1CA—O1C—H1CB	110 (2)
C10—C5—H5	108.2	C1C—O1C—H1CA	111 (3)
C1—C6—C5	112.98 (19)	C1C—O1C—H1CB	117.5 (14)
C1—C6—H6A	109.0	C1C—C2C—H2C	106.5
C1—C6—H6B	109.0	C1C—C2C—C3C	110.2 (2)
C5—C6—H6A	109.0	C1C—C2C—C7C	112.75 (19)
C5—C6—H6B	109.0	C3C—C2C—H2C	106.5
H6A—C6—H6B	107.8	C3C—C2C—C7C	113.7 (2)
C2—C7—H7	107.0	C7C—C2C—H2C	106.5
C8—C7—C2	114.2 (2)	H6CA—C6C—H6CB	107.8
C8—C7—H7	107.0	C1C—C6C—H6CA	109.0
C8—C7—C9	109.7 (2)	C1C—C6C—H6CB	109.0
C9—C7—C2	111.5 (2)	C1C—C6C—C5C	112.8 (2)
C9—C7—H7	107.0	C5C—C6C—H6CA	109.0
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.0
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.4
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.4
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.3 (2)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.4
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.4
C7—C9—H9B	109.5	O1C—C1C—C2C	110.2 (2)
C7—C9—H9C	109.5	O1C—C1C—C6C	110.47 (19)
H9A—C9—H9B	109.5	O1C—C1C—H1C	107.7
H9A—C9—H9C	109.5	C2C—C1C—C6C	112.84 (18)
H9B—C9—H9C	109.5	C2C—C1C—H1C	107.7
C5—C10—H10A	109.5	C6C—C1C—H1C	107.7
C5—C10—H10B	109.5	C6C—C5C—H5C	107.5
C5—C10—H10C	109.5	C4C—C5C—C6C	109.6 (2)
H10A—C10—H10B	109.5	C4C—C5C—H5C	107.5
H10A—C10—H10C	109.5	C4C—C5C—C10C	112.4 (2)
H10B—C10—H10C	109.5	C10C—C5C—C6C	112.0 (2)
H1BA—O1B—H1BB	127 (4)	C10C—C5C—H5C	107.5
C1B—O1B—H1BA	119 (3)	C2C—C3C—C4C	112.3 (2)
C1B—O1B—H1BB	111 (3)	C2C—C3C—H3CA	109.2
O1B—C1B—H1BC	108.1	C2C—C3C—H3CB	109.2
O1B—C1B—C2B	112.8 (2)	C4C—C3C—H3CA	109.2
O1B—C1B—C6B	108.3 (2)	C4C—C3C—H3CB	109.2
C2B—C1B—H1BC	108.1	H3CA—C3C—H3CB	107.9
C6B—C1B—H1BC	108.1	C2C—C7C—H7C	107.0
C6B—C1B—C2B	111.21 (19)	C8C—C7C—C2C	113.7 (2)
C1B—C2B—H2B	106.4	C8C—C7C—H7C	107.0
C1B—C2B—C3B	108.7 (2)	C9C—C7C—C2C	111.5 (2)
C1B—C2B—C7B	113.8 (2)	C9C—C7C—H7C	107.0
C3B—C2B—H2B	106.4	C9C—C7C—C8C	110.3 (2)
C3B—C2B—C7B	114.6 (3)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.4	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.3	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.3	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	111.5 (3)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.0	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.3	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.3	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.2	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.2	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.9	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.3 (2)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.2	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.2	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.6	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.9 (2)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	112.6 (3)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.6	H10H—C10C—H10I	109.5
C10B—C5B—H5B	107.6

O1—C1—C2—C3	176.20 (19)	C3B—C2B—C7B—C9B	−69.2 (4)
O1—C1—C2—C7	−55.1 (3)	C3B—C4B—C5B—C6B	−53.3 (4)
O1—C1—C6—C5	−176.9 (2)	C3B—C4B—C5B—C10B	−178.1 (3)
C1—C2—C3—C4	−55.7 (3)	C4B—C5B—C6B—C1B	53.9 (3)
C1—C2—C7—C8	−74.6 (3)	C6B—C1B—C2B—C3B	57.5 (3)
C1—C2—C7—C9	160.3 (2)	C6B—C1B—C2B—C7B	−173.5 (2)
C2—C1—C6—C5	−54.9 (3)	C7B—C2B—C3B—C4B	174.2 (2)
C2—C3—C4—C5	57.4 (3)	C10B—C5B—C6B—C1B	179.4 (2)
C3—C2—C7—C8	52.2 (3)	C1C—C2C—C3C—C4C	−54.1 (3)
C3—C2—C7—C9	−72.9 (3)	C1C—C2C—C7C—C8C	−63.6 (3)
C3—C4—C5—C6	−55.4 (3)	C1C—C2C—C7C—C9C	171.0 (2)
C3—C4—C5—C10	−178.8 (2)	C1C—C6C—C5C—C4C	54.5 (3)
C4—C5—C6—C1	54.6 (3)	C1C—C6C—C5C—C10C	180.0 (2)
C6—C1—C2—C3	54.2 (3)	C5C—C6C—C1C—O1C	−177.55 (19)
C6—C1—C2—C7	−177.2 (2)	C5C—C6C—C1C—C2C	−53.7 (3)
C7—C2—C3—C4	175.9 (2)	C5C—C4C—C3C—C2C	57.3 (3)
C10—C5—C6—C1	178.5 (3)	C3C—C2C—C1C—O1C	176.13 (18)
O1B—C1B—C2B—C3B	179.3 (2)	C3C—C2C—C1C—C6C	52.1 (3)
O1B—C1B—C2B—C7B	−51.6 (3)	C3C—C2C—C7C—C8C	62.8 (3)
O1B—C1B—C6B—C5B	178.4 (2)	C3C—C2C—C7C—C9C	−62.7 (3)
C1B—C2B—C3B—C4B	−57.2 (3)	C3C—C4C—C5C—C6C	−56.0 (3)
C1B—C2B—C7B—C8B	−67.8 (3)	C3C—C4C—C5C—C10C	178.8 (2)
C1B—C2B—C7B—C9B	164.8 (3)	C7C—C2C—C1C—O1C	−55.6 (3)
C2B—C1B—C6B—C5B	−57.2 (3)	C7C—C2C—C1C—C6C	−179.6 (2)
C2B—C3B—C4B—C5B	56.6 (4)	C7C—C2C—C3C—C4C	178.2 (2)
C3B—C2B—C7B—C8B	58.2 (3)

alpha-DL-2-Isopropyl-5-methylcyclohexanol (alpha_DL_260K) top

Crystal data top

C₁₀H₂₀O	F(000) = 528
M_r = 156.26	D_x = 0.989 Mg m⁻³
Triclinic, P1	Melting point: 308 K
a = 11.9801 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5078 (12) Å	Cell parameters from 6121 reflections
c = 12.8269 (16) Å	θ = 1.8–26.3°
α = 117.531 (11)°	µ = 0.06 mm⁻¹
β = 98.822 (10)°	T = 260 K
γ = 103.945 (9)°	Plate, colourless
V = 1573.9 (3) Å³	0.25 × 0.1 × 0.05 mm
Z = 6

Data collection top

Xcalibur, Eos diffractometer	R_int = 0.062
ω scans	θ_max = 26.3°, θ_min = 1.8°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→13
T_min = 0.993, T_max = 0.997	k = −15→15
11914 measured reflections	l = −11→15
6121 independent reflections	3 standard reflections every 120 min
1638 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.083	w = 1/[σ²(F_o²) + (0.1423P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.346	(Δ/σ)_max = 0.039
S = 0.93	Δρ_max = 0.19 e Å⁻³
6121 reflections	Δρ_min = −0.21 e Å⁻³
314 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
13 restraints	Extinction coefficient: 0.052 (7)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5481 (2)	1.0748 (3)	0.1252 (2)	0.1019 (10)
H1B	0.615051	1.069778	0.124579	0.153*	0.5
H1A	0.513 (7)	1.038 (6)	0.0510 (10)	0.153*	0.5
C1	0.5577 (4)	1.2082 (4)	0.1780 (4)	0.0913 (13)
H1	0.478754	1.210845	0.147795	0.137*
C2	0.5928 (4)	1.2731 (4)	0.3183 (4)	0.0903 (13)
H2	0.671515	1.268171	0.345539	0.135*
C3	0.6110 (4)	1.4167 (4)	0.3765 (4)	0.1045 (15)
H3A	0.534855	1.425650	0.351447	0.157*
H3B	0.636810	1.458497	0.465830	0.157*
C4	0.7052 (4)	1.4823 (4)	0.3371 (5)	0.1163 (17)
H4A	0.714055	1.572540	0.374228	0.174*
H4B	0.782513	1.478250	0.367088	0.174*
C5	0.6704 (5)	1.4193 (5)	0.1976 (5)	0.1125 (16)
H5	0.594136	1.428037	0.169528	0.169*
C6	0.6496 (4)	1.2765 (4)	0.1390 (4)	0.1001 (14)
H6A	0.622118	1.235665	0.049821	0.150*
H6B	0.725817	1.266325	0.161368	0.150*
C7	0.5043 (4)	1.2038 (5)	0.3618 (4)	0.1040 (15)
H7	0.486904	1.111090	0.309101	0.156*
C8	0.3840 (4)	1.2239 (5)	0.3505 (5)	0.1273 (19)
H8A	0.347888	1.200022	0.267035	0.153*
H8B	0.331276	1.171430	0.371604	0.153*
H8C	0.396930	1.313077	0.405524	0.153*
C9	0.5628 (5)	1.2419 (6)	0.4953 (5)	0.149 (2)
H9A	0.638770	1.228956	0.501987	0.178*
H9B	0.575904	1.331041	0.550517	0.178*
H9C	0.510250	1.189395	0.516597	0.178*
C10	0.7650 (5)	1.4849 (5)	0.1587 (6)	0.150 (2)
H10A	0.740445	1.442853	0.070310	0.181*
H10B	0.773305	1.573891	0.194285	0.181*
H10C	0.841152	1.479207	0.187085	0.181*
O1B	0.7480 (2)	1.0142 (3)	0.1293 (3)	0.1271 (13)
H1BA	0.8136 (19)	1.046 (5)	0.1241 (11)	0.191*	0.5
H1BB	0.6985 (8)	1.0431 (14)	0.1114 (12)	0.191*	0.5
C1B	0.7637 (5)	0.9552 (5)	0.2003 (4)	0.1039 (15)
H1BC	0.823941	0.914742	0.178707	0.156*
C2B	0.8078 (5)	1.0501 (5)	0.3373 (5)	0.1056 (15)
H2B	0.743059	1.083729	0.356974	0.158*
C3B	0.8198 (5)	0.9784 (6)	0.4053 (5)	0.134 (2)
H3BA	0.880625	0.939733	0.385871	0.201*
H3BB	0.845758	1.038839	0.493717	0.201*
C4B	0.6998 (6)	0.8739 (7)	0.3680 (6)	0.142 (2)
H4BA	0.710284	0.828101	0.410400	0.213*
H4BB	0.641374	0.913939	0.394288	0.213*
C5B	0.6510 (5)	0.7788 (6)	0.2312 (6)	0.1251 (18)
H5B	0.708773	0.735153	0.208008	0.188*
C6B	0.6449 (5)	0.8499 (5)	0.1631 (4)	0.1050 (15)
H6BA	0.583145	0.887916	0.179134	0.157*
H6BB	0.620969	0.788533	0.075052	0.157*
C7B	0.9212 (5)	1.1683 (6)	0.3796 (5)	0.1250 (18)
H7B	0.904605	1.199482	0.323545	0.188*
C8B	1.0352 (5)	1.1371 (6)	0.3671 (5)	0.143 (2)
H8BA	1.019404	1.066750	0.284975	0.171*
H8BB	1.098437	1.211529	0.382628	0.171*
H8BC	1.059824	1.113461	0.425778	0.171*
C9B	0.9420 (5)	1.2777 (6)	0.5064 (6)	0.201 (4)
H9BA	0.868757	1.295349	0.511739	0.242*
H9BB	0.966007	1.254951	0.566020	0.242*
H9BC	1.004620	1.353020	0.522870	0.242*
C10B	0.5307 (6)	0.6761 (6)	0.1943 (6)	0.163 (2)
H10D	0.503317	0.617918	0.106440	0.196*
H10E	0.539756	0.629155	0.234810	0.196*
H10F	0.472543	0.716127	0.218422	0.196*
O1C	0.9384 (3)	1.0814 (3)	0.0546 (3)	0.1153 (11)
H1CA	0.876 (2)	1.0370 (15)	0.055 (2)	0.173*	0.5
H1C	0.9751 (15)	1.0338 (17)	0.022 (4)	0.173*	0.5
C2C	1.0524 (4)	1.2518 (5)	0.0307 (4)	0.0968 (14)
H2C	1.080591	1.189436	−0.028726	0.145*
C6C	0.8371 (4)	1.1103 (4)	−0.1037 (4)	0.1002 (14)
H6CA	0.758801	1.069267	−0.100847	0.150*
H6CB	0.859432	1.043649	−0.164078	0.150*
C4C	0.9507 (5)	1.2772 (5)	−0.1406 (5)	0.1224 (18)
H4CA	0.944932	1.340621	−0.162572	0.184*
H4CB	0.978713	1.216812	−0.200803	0.184*
C1C	0.9302 (4)	1.1760 (5)	0.0228 (4)	0.0977 (14)
H1CB	0.901260	1.236178	0.083539	0.147*
C5C	0.8273 (5)	1.2056 (5)	−0.1448 (5)	0.1122 (16)
H5C	0.800340	1.269109	−0.084941	0.168*
C3C	1.0414 (5)	1.3445 (5)	−0.0128 (5)	0.1117 (16)
H3CA	1.016968	1.410368	0.045695	0.168*
H3CB	1.119982	1.386886	−0.014249	0.168*
C7C	1.1467 (5)	1.3163 (5)	0.1576 (5)	0.1123 (16)
H7C	1.147173	1.248555	0.175979	0.168*
C8C	1.1170 (5)	1.4181 (6)	0.2623 (5)	0.151 (2)
H8CA	1.036951	1.380854	0.262221	0.181*
H8CB	1.174119	1.448134	0.339915	0.181*
H8CC	1.121405	1.489221	0.250497	0.181*
C9C	1.2720 (5)	1.3737 (6)	0.1569 (5)	0.158 (2)
H9CA	1.290090	1.309283	0.090987	0.189*
H9CB	1.276623	1.444742	0.144963	0.189*
H9CC	1.329338	1.403655	0.234382	0.189*
C10C	0.7338 (5)	1.1393 (6)	−0.2712 (5)	0.143 (2)
H10G	0.657086	1.095300	−0.269441	0.171*
H10H	0.726269	1.202708	−0.291466	0.171*
H10I	0.759012	1.078169	−0.332395	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.115 (3)	0.085 (2)	0.099 (2)	0.0316 (18)	0.0276 (19)	0.0462 (18)
C1	0.085 (3)	0.087 (3)	0.091 (3)	0.020 (2)	0.019 (2)	0.046 (3)
C2	0.082 (3)	0.087 (3)	0.094 (3)	0.018 (2)	0.017 (2)	0.050 (3)
C3	0.097 (4)	0.081 (3)	0.107 (3)	0.019 (3)	0.026 (3)	0.035 (3)
C4	0.102 (4)	0.086 (3)	0.138 (4)	0.019 (3)	0.031 (3)	0.049 (3)
C5	0.120 (4)	0.096 (4)	0.141 (4)	0.042 (3)	0.054 (3)	0.071 (3)
C6	0.108 (4)	0.090 (3)	0.116 (3)	0.042 (3)	0.044 (3)	0.058 (3)
C7	0.094 (4)	0.108 (4)	0.105 (3)	0.030 (3)	0.032 (3)	0.054 (3)
C8	0.098 (4)	0.130 (4)	0.155 (5)	0.035 (3)	0.050 (3)	0.074 (4)
C9	0.137 (5)	0.201 (6)	0.124 (4)	0.052 (4)	0.048 (4)	0.099 (4)
C10	0.163 (6)	0.113 (4)	0.221 (6)	0.060 (4)	0.105 (5)	0.102 (5)
O1B	0.115 (3)	0.173 (3)	0.153 (3)	0.056 (2)	0.047 (2)	0.126 (3)
C1B	0.109 (4)	0.130 (4)	0.112 (4)	0.054 (3)	0.042 (3)	0.084 (3)
C2B	0.103 (4)	0.120 (4)	0.112 (4)	0.048 (3)	0.043 (3)	0.067 (3)
C3B	0.126 (5)	0.181 (6)	0.122 (4)	0.052 (4)	0.037 (4)	0.101 (4)
C4B	0.152 (6)	0.173 (6)	0.144 (5)	0.049 (5)	0.052 (4)	0.119 (5)
C5B	0.135 (5)	0.124 (5)	0.157 (5)	0.053 (4)	0.058 (4)	0.097 (4)
C6B	0.116 (4)	0.104 (4)	0.113 (3)	0.039 (3)	0.042 (3)	0.068 (3)
C7B	0.090 (4)	0.134 (5)	0.143 (5)	0.034 (4)	0.039 (3)	0.068 (4)
C8B	0.106 (5)	0.192 (6)	0.151 (5)	0.058 (4)	0.051 (4)	0.099 (4)
C9B	0.123 (5)	0.171 (6)	0.166 (6)	0.012 (4)	0.040 (4)	−0.001 (5)
C10B	0.167 (7)	0.131 (5)	0.220 (7)	0.048 (5)	0.079 (5)	0.110 (5)
O1C	0.121 (3)	0.116 (3)	0.144 (3)	0.041 (2)	0.047 (2)	0.093 (2)
C2C	0.098 (4)	0.105 (3)	0.105 (3)	0.031 (3)	0.035 (3)	0.070 (3)
C6C	0.098 (4)	0.103 (3)	0.107 (3)	0.026 (3)	0.033 (3)	0.065 (3)
C4C	0.152 (5)	0.122 (4)	0.109 (4)	0.037 (4)	0.039 (4)	0.078 (3)
C1C	0.098 (4)	0.105 (3)	0.110 (4)	0.038 (3)	0.033 (3)	0.071 (3)
C5C	0.118 (4)	0.123 (4)	0.109 (4)	0.039 (3)	0.028 (3)	0.075 (3)
C3C	0.118 (4)	0.106 (4)	0.122 (4)	0.025 (3)	0.032 (3)	0.076 (3)
C7C	0.098 (4)	0.121 (4)	0.116 (4)	0.035 (3)	0.028 (3)	0.064 (3)
C8C	0.131 (5)	0.170 (6)	0.114 (4)	0.051 (4)	0.014 (4)	0.054 (4)
C9C	0.105 (5)	0.181 (6)	0.181 (6)	0.039 (4)	0.033 (4)	0.098 (5)
C10C	0.150 (5)	0.155 (5)	0.133 (5)	0.046 (4)	0.021 (4)	0.092 (4)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.512 (6)
O1—H1A	0.8201 (10)	C5B—C10B	1.513 (7)
O1—C1	1.447 (5)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.526 (5)	C7B—H7B	0.9800
C1—C6	1.518 (6)	C7B—C8B	1.519 (7)
C2—H2	0.9800	C7B—C9B	1.495 (7)
C2—C3	1.534 (5)	C8B—H8BA	0.9600
C2—C7	1.541 (6)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.521 (6)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.518 (7)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.519 (6)	O1C—H1CA	0.8200 (10)
C5—C10	1.519 (6)	O1C—H1C	0.8203 (10)
C6—H6A	0.9700	O1C—C1C	1.437 (5)
C6—H6B	0.9700	C2C—H2C	0.9800
C7—H7	0.9800	C2C—C1C	1.499 (6)
C7—C8	1.518 (6)	C2C—C3C	1.525 (6)
C7—C9	1.538 (6)	C2C—C7C	1.536 (6)
C8—H8A	0.9600	C6C—H6CA	0.9700
C8—H8B	0.9600	C6C—H6CB	0.9700
C8—H8C	0.9600	C6C—C1C	1.524 (6)
C9—H9A	0.9600	C6C—C5C	1.530 (6)
C9—H9B	0.9600	C4C—H4CA	0.9700
C9—H9C	0.9600	C4C—H4CB	0.9700
C10—H10A	0.9600	C4C—C5C	1.511 (6)
C10—H10B	0.9600	C4C—C3C	1.521 (6)
C10—H10C	0.9600	C1C—H1CB	0.9800
O1B—H1BA	0.8200 (11)	C5C—H5C	0.9800
O1B—H1BB	0.8200 (10)	C5C—C10C	1.524 (6)
O1B—C1B	1.430 (5)	C3C—H3CA	0.9700
C1B—H1BC	0.9800	C3C—H3CB	0.9700
C1B—C2B	1.504 (6)	C7C—H7C	0.9800
C1B—C6B	1.516 (6)	C7C—C8C	1.528 (6)
C2B—H2B	0.9800	C7C—C9C	1.503 (6)
C2B—C3B	1.528 (6)	C8C—H8CA	0.9600
C2B—C7B	1.547 (7)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.519 (7)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.502 (7)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	101.2	C10B—C5B—H5B	107.4
C1—O1—H1B	109.5	C1B—C6B—H6BA	108.9
C1—O1—H1A	107 (4)	C1B—C6B—H6BB	108.9
O1—C1—H1	108.8	C5B—C6B—C1B	113.1 (5)
O1—C1—C2	108.8 (4)	C5B—C6B—H6BA	108.9
O1—C1—C6	110.2 (3)	C5B—C6B—H6BB	108.9
C2—C1—H1	108.8	H6BA—C6B—H6BB	107.8
C6—C1—H1	108.8	C2B—C7B—H7B	106.0
C6—C1—C2	111.3 (3)	C8B—C7B—C2B	114.1 (5)
C1—C2—H2	106.9	C8B—C7B—H7B	106.0
C1—C2—C3	109.6 (4)	C9B—C7B—C2B	112.7 (5)
C1—C2—C7	113.0 (3)	C9B—C7B—H7B	106.0
C3—C2—H2	106.9	C9B—C7B—C8B	111.2 (5)
C3—C2—C7	113.1 (4)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.9	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.4	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.4	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.0	H8BA—C8B—H8BC	109.5
C4—C3—C2	111.0 (4)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.4	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.4	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.3	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.3	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.8 (4)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.3	C5B—C10B—H10D	109.5
C5—C4—H4B	109.3	C5B—C10B—H10E	109.5
C4—C5—H5	108.1	C5B—C10B—H10F	109.5
C4—C5—C6	109.3 (4)	H10D—C10B—H10E	109.5
C4—C5—C10	111.6 (5)	H10D—C10B—H10F	109.5
C6—C5—H5	108.1	H10E—C10B—H10F	109.5
C6—C5—C10	111.6 (4)	H1CA—O1C—H1C	107 (3)
C10—C5—H5	108.1	C1C—O1C—H1CA	117 (3)
C1—C6—C5	113.2 (4)	C1C—O1C—H1C	120 (4)
C1—C6—H6A	108.9	C1C—C2C—H2C	106.3
C1—C6—H6B	108.9	C1C—C2C—C3C	110.2 (4)
C5—C6—H6A	108.9	C1C—C2C—C7C	113.3 (4)
C5—C6—H6B	108.9	C3C—C2C—H2C	106.3
H6A—C6—H6B	107.8	C3C—C2C—C7C	113.8 (4)
C2—C7—H7	107.1	C7C—C2C—H2C	106.3
C8—C7—C2	114.5 (4)	H6CA—C6C—H6CB	107.9
C8—C7—H7	107.1	C1C—C6C—H6CA	109.2
C8—C7—C9	109.8 (4)	C1C—C6C—H6CB	109.2
C9—C7—C2	111.0 (4)	C1C—C6C—C5C	112.1 (4)
C9—C7—H7	107.1	C5C—C6C—H6CA	109.2
C7—C8—H8A	109.5	C5C—C6C—H6CB	109.2
C7—C8—H8B	109.5	H4CA—C4C—H4CB	108.0
C7—C8—H8C	109.5	C5C—C4C—H4CA	109.4
H8A—C8—H8B	109.5	C5C—C4C—H4CB	109.4
H8A—C8—H8C	109.5	C5C—C4C—C3C	111.3 (4)
H8B—C8—H8C	109.5	C3C—C4C—H4CA	109.4
C7—C9—H9A	109.5	C3C—C4C—H4CB	109.4
C7—C9—H9B	109.5	O1C—C1C—C2C	110.5 (4)
C7—C9—H9C	109.5	O1C—C1C—C6C	109.7 (4)
H9A—C9—H9B	109.5	O1C—C1C—H1CB	107.7
H9A—C9—H9C	109.5	C2C—C1C—C6C	113.2 (4)
H9B—C9—H9C	109.5	C2C—C1C—H1CB	107.7
C5—C10—H10A	109.5	C6C—C1C—H1CB	107.7
C5—C10—H10B	109.5	C6C—C5C—H5C	107.6
C5—C10—H10C	109.5	C4C—C5C—C6C	109.6 (4)
H10A—C10—H10B	109.5	C4C—C5C—H5C	107.6
H10A—C10—H10C	109.5	C4C—C5C—C10C	112.5 (4)
H10B—C10—H10C	109.5	C10C—C5C—C6C	111.8 (4)
H1BA—O1B—H1BB	111 (5)	C10C—C5C—H5C	107.6
C1B—O1B—H1BA	109 (4)	C2C—C3C—H3CA	109.1
C1B—O1B—H1BB	136.4 (4)	C2C—C3C—H3CB	109.1
O1B—C1B—H1BC	108.1	C4C—C3C—C2C	112.7 (4)
O1B—C1B—C2B	113.0 (4)	C4C—C3C—H3CA	109.1
O1B—C1B—C6B	108.3 (4)	C4C—C3C—H3CB	109.1
C2B—C1B—H1BC	108.1	H3CA—C3C—H3CB	107.8
C2B—C1B—C6B	111.2 (4)	C2C—C7C—H7C	107.1
C6B—C1B—H1BC	108.1	C8C—C7C—C2C	113.4 (4)
C1B—C2B—H2B	106.2	C8C—C7C—H7C	107.1
C1B—C2B—C3B	109.3 (4)	C9C—C7C—C2C	112.0 (4)
C1B—C2B—C7B	113.8 (4)	C9C—C7C—H7C	107.1
C3B—C2B—H2B	106.2	C9C—C7C—C8C	109.9 (5)
C3B—C2B—C7B	114.5 (5)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.2	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.5	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.5	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.1	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	110.5 (5)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.5	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.5	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.0	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.0	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.8 (5)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.0	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.0	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.4	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.7 (5)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	112.6 (5)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.4	H10H—C10C—H10I	109.5
C6B—C5B—C10B	112.1 (5)

O1—C1—C2—C3	176.6 (3)	C3B—C2B—C7B—C9B	−70.1 (7)
O1—C1—C2—C7	−56.3 (5)	C3B—C4B—C5B—C6B	−53.6 (7)
O1—C1—C6—C5	−176.3 (4)	C3B—C4B—C5B—C10B	−179.1 (5)
C1—C2—C3—C4	−56.6 (5)	C4B—C5B—C6B—C1B	53.0 (6)
C1—C2—C7—C8	−74.1 (5)	C6B—C1B—C2B—C3B	57.0 (6)
C1—C2—C7—C9	161.0 (4)	C6B—C1B—C2B—C7B	−173.6 (4)
C2—C1—C6—C5	−55.5 (6)	C7B—C2B—C3B—C4B	173.6 (4)
C2—C3—C4—C5	58.2 (6)	C10B—C5B—C6B—C1B	178.8 (4)
C3—C2—C7—C8	51.2 (5)	C1C—C2C—C3C—C4C	−53.6 (6)
C3—C2—C7—C9	−73.8 (5)	C1C—C2C—C7C—C8C	−64.0 (6)
C3—C4—C5—C6	−55.8 (6)	C1C—C2C—C7C—C9C	171.0 (4)
C3—C4—C5—C10	−179.7 (4)	C1C—C6C—C5C—C4C	54.8 (5)
C4—C5—C6—C1	54.8 (6)	C1C—C6C—C5C—C10C	−179.8 (4)
C6—C1—C2—C3	54.9 (5)	C5C—C6C—C1C—O1C	−178.1 (3)
C6—C1—C2—C7	−177.9 (4)	C5C—C6C—C1C—C2C	−54.1 (6)
C7—C2—C3—C4	176.3 (4)	C5C—C4C—C3C—C2C	56.9 (6)
C10—C5—C6—C1	178.7 (4)	C3C—C2C—C1C—O1C	175.6 (4)
O1B—C1B—C2B—C3B	179.0 (4)	C3C—C2C—C1C—C6C	52.1 (6)
O1B—C1B—C2B—C7B	−51.6 (6)	C3C—C2C—C7C—C8C	62.9 (6)
O1B—C1B—C6B—C5B	179.1 (4)	C3C—C2C—C7C—C9C	−62.1 (6)
C1B—C2B—C3B—C4B	−57.4 (6)	C3C—C4C—C5C—C6C	−56.1 (6)
C1B—C2B—C7B—C8B	−68.7 (6)	C3C—C4C—C5C—C10C	178.9 (4)
C1B—C2B—C7B—C9B	163.2 (5)	C7C—C2C—C1C—O1C	−55.7 (5)
C2B—C1B—C6B—C5B	−56.2 (6)	C7C—C2C—C1C—C6C	−179.1 (4)
C2B—C3B—C4B—C5B	57.1 (7)	C7C—C2C—C3C—C4C	177.9 (4)
C3B—C2B—C7B—C8B	58.0 (6)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.10GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.029 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.928 (6) Å	Cell parameters from 1506 reflections
b = 21.3338 (19) Å	θ = 4.6–26.8°
c = 12.235 (8) Å	µ = 0.06 mm⁻¹
β = 103.71 (7)°	T = 296 K
V = 3025 (3) Å³	Plate, colourless
Z = 12	0.45 × 0.25 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	1506 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	600 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.168
Detector resolution: 16.4 pixels mm^-1	θ_max = 26.8°, θ_min = 4.6°
ω and φ scans	h = −10→10
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −26→26
T_min = 0.970, T_max = 0.999	l = −9→9
14374 measured reflections

Refinement top

Refinement on F²	189 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.220	w = 1/[σ²(F_o²) + (0.1015P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1506 reflections	Δρ_max = 0.07 e Å⁻³
296 parameters	Δρ_min = −0.07 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0014 (8)	0.06447 (19)	0.5071 (8)	0.076 (9)
H1B	0.064306	0.063941	0.497356	0.113*	0.5
H1A	−0.015 (14)	0.0264 (13)	0.50 (2)	0.113*	0.5
C1	−0.0002 (11)	0.0928 (3)	0.6121 (13)	0.058 (6)
H1	−0.068586	0.078628	0.636478	0.070*
C2	−0.0075 (11)	0.1629 (3)	0.5974 (12)	0.064 (6)
H2	0.064111	0.175136	0.577003	0.096*
C3	−0.0013 (11)	0.1930 (3)	0.7107 (12)	0.068 (6)
H3A	−0.069371	0.181292	0.736446	0.082*
H3B	−0.001802	0.238191	0.702288	0.082*
C4	0.1052 (11)	0.1738 (3)	0.7985 (12)	0.086 (6)
H4A	0.172758	0.191196	0.778439	0.103*
H4B	0.101084	0.191513	0.870511	0.103*
C5	0.1187 (13)	0.1048 (3)	0.8103 (15)	0.087 (6)
H5	0.053816	0.090207	0.839860	0.105*
C6	0.1063 (11)	0.0735 (3)	0.7007 (12)	0.061 (6)
H6A	0.103712	0.028559	0.711880	0.074*
H6B	0.174062	0.082509	0.672623	0.074*
C7	−0.1055 (14)	0.1850 (4)	0.4990 (17)	0.071 (6)
H7	−0.107224	0.158335	0.433392	0.085*
C8	−0.0915 (12)	0.2522 (3)	0.4676 (13)	0.104 (11)
H8A	−0.019408	0.257176	0.446643	0.156*
H8B	−0.153734	0.263689	0.405440	0.156*
H8C	−0.092517	0.278747	0.530784	0.156*
C9	−0.2219 (16)	0.1800 (4)	0.532 (2)	0.106 (11)
H9A	−0.233764	0.137604	0.552494	0.158*
H9B	−0.282951	0.192029	0.468736	0.158*
H9C	−0.221812	0.207346	0.593992	0.158*
C10	0.2289 (15)	0.0851 (4)	0.8979 (16)	0.128 (11)
H10A	0.232401	0.106878	0.967266	0.192*
H10B	0.227211	0.040722	0.910512	0.192*
H10C	0.295586	0.095407	0.870350	0.192*
O1B	0.2004 (8)	0.0540 (2)	0.4253 (8)	0.085 (9)
H1BB	0.141904	0.057988	0.448806	0.128*	0.5
H1CA	0.353 (13)	0.041 (6)	0.52 (3)	0.128*	0.5
C1B	0.1920 (12)	0.0920 (3)	0.3297 (12)	0.068 (6)
H1BC	0.256413	0.081585	0.295901	0.082*
C2B	0.1954 (12)	0.1606 (3)	0.3525 (13)	0.074 (6)
H2B	0.125165	0.169803	0.377790	0.088*
C3B	0.1843 (12)	0.1962 (3)	0.2464 (13)	0.091 (6)
H3BA	0.251128	0.187981	0.216219	0.109*
H3BB	0.182670	0.240672	0.262025	0.109*
C4B	0.0760 (13)	0.1784 (4)	0.1596 (14)	0.113 (7)
H4BA	0.009335	0.193057	0.184785	0.136*
H4BB	0.076111	0.199544	0.089449	0.136*
C5B	0.0642 (13)	0.1091 (4)	0.1382 (14)	0.101 (6)
H5B	0.126389	0.096357	0.102963	0.121*
C6B	0.0806 (12)	0.0740 (3)	0.2470 (13)	0.081 (6)
H6BA	0.081111	0.029388	0.232134	0.097*
H6BB	0.016034	0.082716	0.280252	0.097*
C7B	0.2968 (16)	0.1804 (4)	0.4507 (19)	0.095 (7)
H7B	0.298602	0.150461	0.511875	0.114*
C8B	0.2822 (13)	0.2436 (3)	0.4965 (14)	0.111 (11)
H8BA	0.347570	0.253003	0.556917	0.167*
H8BB	0.276167	0.274312	0.438132	0.167*
H8BC	0.213260	0.244243	0.524187	0.167*
C9B	0.4147 (15)	0.1741 (4)	0.4171 (19)	0.101 (11)
H9BA	0.421159	0.132771	0.387949	0.152*
H9BB	0.418809	0.204611	0.360558	0.152*
H9BC	0.476741	0.180882	0.482082	0.152*
C10B	−0.0518 (18)	0.0928 (4)	0.055 (2)	0.136 (11)
H10D	−0.114216	0.111764	0.080193	0.204*
H10E	−0.061920	0.048156	0.051496	0.204*
H10F	−0.051241	0.108476	−0.018511	0.204*
O1C	0.4130 (10)	0.0230 (2)	0.5483 (12)	0.087 (9)
H1C	0.469507	0.007666	0.531056	0.131*	0.5
H1BA	0.267 (4)	0.057 (5)	0.462 (9)	0.131*	0.5
C1C	0.4153 (13)	0.0072 (4)	0.6645 (16)	0.075 (7)
H1CB	0.366628	0.037446	0.692250	0.090*
C2C	0.5366 (11)	0.0139 (3)	0.7340 (12)	0.062 (6)
H2C	0.582631	−0.015939	0.702031	0.074*
C3C	0.5433 (13)	−0.0084 (3)	0.8513 (13)	0.084 (6)
H3CA	0.501674	0.020680	0.888134	0.100*
H3CB	0.623398	−0.008459	0.892895	0.100*
C4C	0.4941 (11)	−0.0730 (3)	0.8546 (11)	0.076 (6)
H4CA	0.540892	−0.102903	0.825506	0.091*
H4CB	0.496594	−0.084176	0.931990	0.091*
C5C	0.3730 (12)	−0.0765 (3)	0.7871 (14)	0.081 (6)
H5C	0.328315	−0.046390	0.820110	0.097*
C6C	0.3647 (11)	−0.0557 (3)	0.6671 (13)	0.064 (6)
H6CA	0.405085	−0.085415	0.630283	0.096*
H6CB	0.284326	−0.054983	0.626323	0.096*
C7C	0.5922 (12)	0.0787 (4)	0.7265 (15)	0.087 (6)
H7C	0.587324	0.086964	0.646680	0.104*
C8C	0.7180 (14)	0.0808 (4)	0.7861 (18)	0.109 (11)
H8CA	0.760342	0.052008	0.750903	0.163*
H8CB	0.726683	0.069274	0.863517	0.163*
H8CC	0.747058	0.122468	0.781960	0.163*
C9C	0.5279 (13)	0.1317 (4)	0.7698 (15)	0.116 (11)
H9CA	0.526157	0.123517	0.846514	0.173*
H9CB	0.450437	0.134158	0.724477	0.173*
H9CC	0.566854	0.170696	0.765565	0.173*
C10C	0.3175 (12)	−0.1409 (3)	0.7915 (14)	0.101 (11)
H10G	0.239699	−0.140162	0.746531	0.151*
H10H	0.360952	−0.172054	0.762841	0.151*
H10I	0.316918	−0.150707	0.867956	0.151*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.099 (12)	0.062 (3)	0.072 (14)	−0.008 (4)	0.032 (12)	−0.008 (5)
C1	0.065 (9)	0.048 (4)	0.064 (10)	−0.008 (5)	0.022 (8)	−0.006 (5)
C2	0.059 (9)	0.061 (4)	0.074 (10)	0.002 (5)	0.020 (8)	−0.005 (5)
C3	0.067 (9)	0.060 (4)	0.080 (10)	−0.002 (5)	0.024 (8)	−0.019 (5)
C4	0.082 (9)	0.094 (5)	0.079 (10)	−0.011 (5)	0.015 (8)	−0.029 (6)
C5	0.084 (9)	0.097 (5)	0.078 (10)	0.004 (6)	0.014 (8)	−0.010 (6)
C6	0.070 (9)	0.057 (4)	0.063 (10)	0.010 (5)	0.027 (8)	0.011 (5)
C7	0.078 (9)	0.068 (4)	0.068 (10)	0.016 (6)	0.021 (8)	−0.009 (6)
C8	0.090 (14)	0.103 (6)	0.126 (17)	0.003 (7)	0.037 (14)	0.038 (8)
C9	0.082 (15)	0.109 (6)	0.128 (18)	0.014 (9)	0.028 (15)	−0.020 (8)
C10	0.112 (15)	0.160 (7)	0.102 (17)	0.030 (9)	0.006 (14)	0.013 (9)
O1B	0.079 (11)	0.094 (3)	0.083 (14)	0.006 (4)	0.019 (12)	0.019 (5)
C1B	0.081 (9)	0.062 (4)	0.065 (10)	0.016 (5)	0.024 (8)	0.015 (5)
C2B	0.073 (9)	0.071 (4)	0.077 (10)	0.013 (5)	0.016 (8)	−0.003 (6)
C3B	0.098 (9)	0.080 (4)	0.096 (10)	0.012 (5)	0.026 (8)	0.020 (6)
C4B	0.107 (10)	0.121 (6)	0.108 (10)	0.021 (6)	0.018 (8)	0.034 (6)
C5B	0.090 (9)	0.114 (6)	0.095 (10)	0.008 (6)	0.014 (8)	0.012 (7)
C6B	0.081 (9)	0.087 (4)	0.071 (10)	0.002 (5)	0.015 (8)	0.010 (6)
C7B	0.100 (10)	0.079 (5)	0.108 (11)	0.002 (7)	0.027 (8)	−0.013 (6)
C8B	0.086 (14)	0.108 (6)	0.155 (17)	−0.029 (7)	0.059 (14)	−0.040 (8)
C9B	0.082 (14)	0.099 (6)	0.120 (18)	0.001 (8)	0.020 (14)	0.009 (8)
C10B	0.099 (15)	0.192 (8)	0.099 (18)	0.008 (9)	−0.013 (14)	−0.004 (9)
O1C	0.091 (12)	0.095 (4)	0.072 (14)	0.006 (4)	0.012 (12)	0.006 (6)
C1C	0.076 (10)	0.074 (5)	0.074 (10)	0.004 (5)	0.014 (8)	0.006 (6)
C2C	0.053 (9)	0.062 (4)	0.071 (10)	−0.003 (5)	0.015 (8)	0.008 (5)
C3C	0.086 (9)	0.090 (5)	0.071 (10)	−0.003 (5)	0.011 (8)	0.011 (6)
C4C	0.088 (9)	0.072 (4)	0.063 (10)	0.002 (5)	0.009 (8)	−0.005 (5)
C5C	0.096 (10)	0.071 (4)	0.078 (10)	0.004 (5)	0.024 (8)	0.002 (6)
C6C	0.063 (9)	0.063 (4)	0.068 (10)	−0.003 (5)	0.016 (8)	−0.004 (5)
C7C	0.092 (9)	0.084 (5)	0.084 (10)	−0.003 (6)	0.018 (8)	−0.003 (6)
C8C	0.063 (14)	0.133 (6)	0.128 (18)	−0.027 (7)	0.018 (14)	−0.001 (8)
C9C	0.137 (16)	0.086 (6)	0.129 (17)	−0.010 (7)	0.043 (14)	0.006 (8)
C10C	0.131 (15)	0.087 (5)	0.096 (17)	−0.011 (7)	0.049 (14)	0.016 (7)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.50 (2)
O1—H1A	0.83 (2)	C5B—C10B	1.551 (10)
O1—C1	1.417 (18)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.507 (8)	C7B—H7B	0.9800
C1—C6	1.519 (9)	C7B—C8B	1.486 (17)
C2—H2	0.9800	C7B—C9B	1.56 (4)
C2—C3	1.51 (2)	C8B—H8BA	0.9600
C2—C7	1.540 (11)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.513 (8)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.485 (9)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.47 (2)	O1C—H1CA	0.82 (2)
C5—C10	1.545 (9)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.45 (3)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.502 (12)
C7—C8	1.504 (13)	C1C—C6C	1.476 (12)
C7—C9	1.54 (4)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.50 (2)
C8—H8B	0.9600	C2C—C7C	1.545 (14)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.502 (11)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.486 (11)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.51 (2)
O1B—C1B	1.407 (15)	C5C—C10C	1.532 (13)
O1B—H1BA	0.81 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.489 (9)	C7C—H7C	0.9800
C1B—C6B	1.517 (10)	C7C—C8C	1.505 (13)
C2B—H2B	0.9800	C7C—C9C	1.53 (2)
C2B—C3B	1.482 (19)	C8C—H8CA	0.9600
C2B—C7B	1.548 (11)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.514 (9)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.502 (10)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	97.8	C10B—C5B—H5B	107.5
C1—O1—H1B	109.5	C1B—C6B—H6BA	109.2
C1—O1—H1A	118 (10)	C1B—C6B—H6BB	109.2
O1—C1—H1	108.3	C5B—C6B—C1B	112.1 (12)
O1—C1—C2	109.1 (12)	C5B—C6B—H6BA	109.2
O1—C1—C6	111.0 (11)	C5B—C6B—H6BB	109.2
C2—C1—H1	108.3	H6BA—C6B—H6BB	107.9
C2—C1—C6	111.7 (5)	C2B—C7B—H7B	106.7
C6—C1—H1	108.3	C2B—C7B—C9B	111 (2)
C1—C2—H2	105.4	C8B—C7B—C2B	113.6 (9)
C1—C2—C3	108.8 (11)	C8B—C7B—H7B	106.7
C1—C2—C7	114.1 (6)	C8B—C7B—C9B	111.8 (12)
C3—C2—H2	105.4	C9B—C7B—H7B	106.7
C3—C2—C7	116.7 (12)	C7B—C8B—H8BA	109.5
C7—C2—H2	105.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.0	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.0	H8BA—C8B—H8BB	109.5
C2—C3—C4	112.7 (11)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.8	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.0	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.0	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.0	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.0	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.8	H9BA—C9B—H9BC	109.5
C5—C4—C3	113.0 (5)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.0	C5B—C10B—H10D	109.5
C5—C4—H4B	109.0	C5B—C10B—H10E	109.5
C4—C5—H5	105.9	C5B—C10B—H10F	109.5
C4—C5—C10	113.1 (6)	H10D—C10B—H10E	109.5
C6—C5—C4	112.1 (12)	H10D—C10B—H10F	109.5
C6—C5—H5	105.9	H10E—C10B—H10F	109.5
C6—C5—C10	113.2 (14)	H1CA—O1C—H1C	136.7
C10—C5—H5	105.9	C1C—O1C—H1CA	111.00
C1—C6—H6A	108.7	C1C—O1C—H1C	109.5
C1—C6—H6B	108.7	O1C—C1C—H1CB	108.2
C5—C6—C1	114.4 (11)	O1C—C1C—C2C	108.9 (17)
C5—C6—H6A	108.7	O1C—C1C—C6C	108.6 (9)
C5—C6—H6B	108.7	C2C—C1C—H1CB	108.2
H6A—C6—H6B	107.6	C6C—C1C—H1CB	108.2
C2—C7—H7	109.1	C6C—C1C—C2C	114.7 (6)
C8—C7—C2	112.4 (7)	C1C—C2C—H2C	105.6
C8—C7—H7	109.1	C1C—C2C—C7C	114.9 (6)
C8—C7—C9	107.1 (12)	C3C—C2C—C1C	109.8 (14)
C9—C7—C2	109.9 (19)	C3C—C2C—H2C	105.6
C9—C7—H7	109.1	C3C—C2C—C7C	114.5 (9)
C7—C8—H8A	109.5	C7C—C2C—H2C	105.6
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.1
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.1
H8A—C8—H8B	109.5	C2C—C3C—C4C	112.7 (8)
H8A—C8—H8C	109.5	H3CA—C3C—H3CB	107.8
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.1
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.1
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.3
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	108.0
H9A—C9—H9C	109.5	C5C—C4C—C3C	111.4 (6)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.3
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.3
C5—C10—H10B	109.5	C4C—C5C—H5C	106.9
C5—C10—H10C	109.5	C4C—C5C—C6C	110.9 (15)
H10A—C10—H10B	109.5	C4C—C5C—C10C	113.4 (6)
H10A—C10—H10C	109.5	C6C—C5C—H5C	106.9
H10B—C10—H10C	109.5	C6C—C5C—C10C	111.5 (9)
H1BB—O1B—H1BA	126.8	C10C—C5C—H5C	106.9
C1B—O1B—H1BB	109.5	C1C—C6C—C5C	110.7 (10)
C1B—O1B—H1BA	106 (6)	C1C—C6C—H6CA	109.5
O1B—C1B—H1BC	108.2	C1C—C6C—H6CB	109.5
O1B—C1B—C2B	114.7 (12)	C5C—C6C—H6CA	109.5
O1B—C1B—C6B	106.7 (10)	C5C—C6C—H6CB	109.5
C2B—C1B—H1BC	108.2	H6CA—C6C—H6CB	108.1
C2B—C1B—C6B	110.7 (6)	C2C—C7C—H7C	107.2
C6B—C1B—H1BC	108.2	C8C—C7C—C2C	113.0 (6)
C1B—C2B—H2B	105.6	C8C—C7C—H7C	107.2
C1B—C2B—C7B	113.3 (6)	C8C—C7C—C9C	109.5 (9)
C3B—C2B—C1B	110.3 (12)	C9C—C7C—C2C	112.5 (15)
C3B—C2B—H2B	105.6	C9C—C7C—H7C	107.2
C3B—C2B—C7B	115.6 (12)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	105.6	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.3	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.3	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	111.7 (11)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	107.9	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.3	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.3	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.7	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.4 (6)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.5	C5C—C10C—H10I	109.5
C4B—C5B—C10B	111.5 (7)	H10G—C10C—H10H	109.5
C6B—C5B—C4B	110.4 (11)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.5	H10H—C10C—H10I	109.5
C6B—C5B—C10B	112.3 (15)

O1—C1—C2—C3	−177.7 (11)	C3B—C2B—C7B—C9B	−58.4 (14)
O1—C1—C2—C7	50 (2)	C3B—C4B—C5B—C6B	51 (2)
O1—C1—C6—C5	175.5 (12)	C3B—C4B—C5B—C10B	176.1 (19)
C1—C2—C3—C4	55.7 (15)	C4B—C5B—C6B—C1B	−52.7 (18)
C1—C2—C7—C8	−164.9 (18)	C6B—C1B—C2B—C3B	−58.4 (19)
C1—C2—C7—C9	75.9 (18)	C6B—C1B—C2B—C7B	170.3 (18)
C2—C1—C6—C5	53 (2)	C7B—C2B—C3B—C4B	−173.9 (13)
C2—C3—C4—C5	−53.8 (19)	C10B—C5B—C6B—C1B	−177.8 (13)
C3—C2—C7—C8	67 (2)	O1C—C1C—C2C—C3C	−174.2 (8)
C3—C2—C7—C9	−52.5 (13)	O1C—C1C—C2C—C7C	55.0 (17)
C3—C4—C5—C6	49 (2)	O1C—C1C—C6C—C5C	175.7 (14)
C3—C4—C5—C10	178.7 (19)	C1C—C2C—C3C—C4C	52.2 (14)
C4—C5—C6—C1	−49.6 (18)	C1C—C2C—C7C—C8C	−173.1 (17)
C6—C1—C2—C3	−54.7 (18)	C1C—C2C—C7C—C9C	62.2 (17)
C6—C1—C2—C7	173.0 (18)	C2C—C1C—C6C—C5C	54 (2)
C7—C2—C3—C4	−173.4 (10)	C2C—C3C—C4C—C5C	−55.9 (18)
C10—C5—C6—C1	−179.0 (12)	C3C—C2C—C7C—C8C	58 (2)
O1B—C1B—C2B—C3B	−179.2 (11)	C3C—C2C—C7C—C9C	−66.2 (12)
O1B—C1B—C2B—C7B	49 (2)	C3C—C4C—C5C—C6C	55.8 (16)
O1B—C1B—C6B—C5B	−177.0 (13)	C3C—C4C—C5C—C10C	−177.9 (15)
C1B—C2B—C3B—C4B	56.0 (17)	C4C—C5C—C6C—C1C	−54.4 (14)
C1B—C2B—C7B—C8B	−162.7 (19)	C6C—C1C—C2C—C3C	−52.3 (19)
C1B—C2B—C7B—C9B	70.3 (19)	C6C—C1C—C2C—C7C	176.9 (17)
C2B—C1B—C6B—C5B	58 (2)	C7C—C2C—C3C—C4C	−176.9 (12)
C2B—C3B—C4B—C5B	−53 (2)	C10C—C5C—C6C—C1C	178.2 (12)
C3B—C2B—C7B—C8B	69 (2)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.20GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.024 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.031 (4) Å	Cell parameters from 1533 reflections
b = 21.3330 (14) Å	θ = 4.6–26.7°
c = 12.212 (5) Å	µ = 0.06 mm⁻¹
β = 104.03 (5)°	T = 296 K
V = 3040.9 (18) Å³	Plate, colourless
Z = 12	0.45 × 0.35 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	574 reflections with I > 2σ(I)
Detector resolution: 16.2413 pixels mm^-1	R_int = 0.157
ω and φ scans	θ_max = 26.6°, θ_min = 4.6°
Absorption correction: multi-scan CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
T_min = 0.865, T_max = 1.000	k = −26→26
14702 measured reflections	l = −9→9
1533 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.073	w = 1/[σ²(F_o²) + (0.139P)² + 0.4033P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.283	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.07 e Å⁻³
1533 reflections	Δρ_min = −0.08 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.005 (9)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.0005 (9)	0.0646 (2)	0.5040 (11)	0.085 (10)
H1B	0.065829	0.064349	0.494995	0.128*	0.5
H1A	−0.008 (18)	0.0261 (13)	0.50 (2)	0.128*	0.5
C1	0.0007 (13)	0.0930 (3)	0.6105 (15)	0.068 (6)
H1	−0.066829	0.078571	0.634899	0.081*
C2	−0.0061 (13)	0.1637 (3)	0.5957 (15)	0.077 (6)
H2	0.064723	0.177392	0.576781	0.115*
C3	−0.0069 (13)	0.1929 (3)	0.7158 (15)	0.081 (6)
H3A	−0.011972	0.238247	0.710572	0.098*
H3B	−0.072459	0.177494	0.740799	0.098*
C4	0.1044 (13)	0.1736 (3)	0.7999 (15)	0.093 (6)
H4A	0.168876	0.192397	0.777408	0.112*
H4B	0.103806	0.189702	0.874087	0.112*
C5	0.1201 (15)	0.1047 (4)	0.8069 (17)	0.095 (7)
H5	0.054958	0.089370	0.834378	0.113*
C6	0.1088 (13)	0.0732 (3)	0.6990 (14)	0.077 (6)
H6A	0.106807	0.028277	0.710393	0.093*
H6B	0.175619	0.082547	0.670589	0.093*
C7	−0.1064 (16)	0.1855 (4)	0.500 (2)	0.080 (7)
H7	−0.108451	0.159139	0.433787	0.096*
C8	−0.0905 (13)	0.2532 (4)	0.4682 (15)	0.109 (11)
H8A	−0.017954	0.257656	0.449213	0.164*
H8B	−0.150928	0.264754	0.404372	0.164*
H8C	−0.092487	0.280036	0.530788	0.164*
C9	−0.2215 (18)	0.1806 (5)	0.529 (2)	0.107 (11)
H9A	−0.234404	0.137960	0.548237	0.160*
H9B	−0.280904	0.193378	0.465492	0.160*
H9C	−0.222059	0.207232	0.592376	0.160*
C10	0.2257 (17)	0.0854 (5)	0.8987 (19)	0.136 (12)
H10A	0.226812	0.108085	0.966848	0.203*
H10B	0.222547	0.041205	0.912792	0.203*
H10C	0.293749	0.094711	0.874023	0.203*
O1B	0.2002 (9)	0.0541 (3)	0.4263 (10)	0.104 (10)
H1BB	0.141183	0.058909	0.447740	0.155*	0.5
H1CA	0.349 (11)	0.034 (10)	0.51 (3)	0.155*	0.5
C1B	0.1946 (14)	0.0916 (3)	0.3260 (15)	0.079 (6)
H1BC	0.259075	0.081657	0.293008	0.095*
C2B	0.1946 (15)	0.1602 (4)	0.3546 (16)	0.089 (6)
H2B	0.124424	0.168529	0.379434	0.107*
C3B	0.1851 (14)	0.1954 (4)	0.2464 (15)	0.094 (6)
H3BA	0.250222	0.185369	0.215793	0.113*
H3BB	0.186441	0.240091	0.261194	0.113*
C4B	0.0752 (15)	0.1785 (4)	0.1610 (17)	0.121 (7)
H4BA	0.010599	0.192943	0.188676	0.145*
H4BB	0.073244	0.200312	0.090875	0.145*
C5B	0.0628 (15)	0.1095 (5)	0.1380 (17)	0.115 (7)
H5B	0.124315	0.097475	0.102281	0.138*
C6B	0.0817 (14)	0.0743 (4)	0.2447 (16)	0.088 (6)
H6BA	0.081363	0.029710	0.228670	0.106*
H6BB	0.019292	0.082741	0.280131	0.106*
C7B	0.2968 (18)	0.1808 (4)	0.451 (2)	0.097 (7)
H7B	0.299378	0.151452	0.513757	0.117*
C8B	0.2821 (15)	0.2439 (4)	0.4959 (17)	0.126 (11)
H8BA	0.347801	0.254038	0.555419	0.189*
H8BB	0.274378	0.274190	0.436318	0.189*
H8BC	0.214634	0.244516	0.524671	0.189*
C9B	0.4156 (18)	0.1740 (5)	0.418 (2)	0.116 (11)
H9BA	0.421988	0.132558	0.389295	0.173*
H9BB	0.419442	0.204222	0.360383	0.173*
H9BC	0.477299	0.181223	0.482863	0.173*
C10B	−0.051 (2)	0.0927 (5)	0.054 (2)	0.146 (12)
H10D	−0.114356	0.108015	0.081600	0.219*
H10E	−0.057387	0.048044	0.044817	0.219*
H10F	−0.053615	0.111739	−0.018201	0.219*
O1C	0.4142 (11)	0.0235 (3)	0.5457 (14)	0.097 (10)
H1C	0.470563	0.007983	0.529464	0.146*	0.5
H1BA	0.267 (4)	0.056 (6)	0.459 (9)	0.146*	0.5
C1C	0.4153 (16)	0.0083 (4)	0.6613 (18)	0.086 (7)
H1CB	0.367636	0.038959	0.688546	0.103*
C2C	0.5374 (13)	0.0141 (4)	0.7327 (15)	0.072 (6)
H2C	0.583517	−0.015649	0.701248	0.086*
C3C	0.5425 (16)	−0.0076 (4)	0.8512 (17)	0.101 (7)
H3CA	0.500976	0.021920	0.886778	0.121*
H3CB	0.621738	−0.007726	0.894088	0.121*
C4C	0.4921 (13)	−0.0730 (3)	0.8558 (14)	0.087 (6)
H4CA	0.538223	−0.103318	0.827262	0.105*
H4CB	0.495165	−0.083657	0.933705	0.105*
C5C	0.3727 (15)	−0.0769 (4)	0.7890 (17)	0.095 (7)
H5C	0.328373	−0.046849	0.821882	0.114*
C6C	0.3646 (13)	−0.0556 (4)	0.6668 (15)	0.082 (6)
H6CA	0.404443	−0.085658	0.630360	0.122*
H6CB	0.284809	−0.055118	0.625600	0.122*
C7C	0.5905 (14)	0.0789 (4)	0.7268 (17)	0.090 (6)
H7C	0.585074	0.087391	0.646815	0.108*
C8C	0.7174 (16)	0.0804 (5)	0.786 (2)	0.123 (12)
H8CA	0.757565	0.050199	0.751477	0.184*
H8CB	0.727137	0.070375	0.864174	0.184*
H8CC	0.747479	0.121468	0.778839	0.184*
C9C	0.5283 (15)	0.1313 (4)	0.7689 (18)	0.124 (11)
H9CA	0.537317	0.126950	0.848787	0.185*
H9CB	0.448344	0.129481	0.731474	0.185*
H9CC	0.559349	0.170755	0.753152	0.185*
C10C	0.3179 (13)	−0.1411 (4)	0.7933 (16)	0.107 (11)
H10G	0.240493	−0.140397	0.748233	0.161*
H10H	0.360792	−0.172267	0.764393	0.161*
H10I	0.317871	−0.151026	0.869985	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.108 (13)	0.068 (3)	0.085 (15)	−0.005 (5)	0.033 (12)	−0.008 (5)
C1	0.066 (9)	0.068 (5)	0.073 (10)	−0.002 (5)	0.024 (8)	−0.005 (6)
C2	0.082 (9)	0.069 (4)	0.082 (10)	0.007 (5)	0.026 (8)	−0.002 (6)
C3	0.086 (9)	0.072 (4)	0.090 (10)	0.004 (5)	0.030 (8)	−0.027 (6)
C4	0.100 (9)	0.096 (5)	0.084 (10)	−0.009 (6)	0.022 (8)	−0.027 (6)
C5	0.087 (10)	0.105 (6)	0.089 (10)	0.001 (6)	0.016 (8)	−0.002 (7)
C6	0.087 (10)	0.066 (4)	0.083 (10)	−0.001 (5)	0.030 (8)	0.004 (6)
C7	0.081 (10)	0.076 (5)	0.085 (11)	0.012 (7)	0.025 (8)	−0.004 (6)
C8	0.103 (15)	0.103 (6)	0.123 (18)	−0.006 (7)	0.031 (14)	0.035 (8)
C9	0.081 (15)	0.116 (7)	0.126 (19)	0.013 (9)	0.030 (15)	−0.014 (9)
C10	0.109 (16)	0.159 (8)	0.129 (19)	0.014 (9)	0.011 (15)	0.005 (10)
O1B	0.096 (12)	0.107 (4)	0.101 (15)	0.008 (5)	0.011 (13)	0.012 (6)
C1B	0.090 (10)	0.071 (5)	0.082 (11)	0.008 (6)	0.031 (8)	0.021 (6)
C2B	0.086 (9)	0.095 (5)	0.085 (10)	0.000 (6)	0.019 (8)	0.005 (7)
C3B	0.102 (10)	0.091 (5)	0.093 (10)	0.011 (6)	0.030 (8)	0.014 (7)
C4B	0.117 (10)	0.124 (6)	0.121 (11)	0.026 (7)	0.028 (8)	0.038 (7)
C5B	0.111 (10)	0.120 (6)	0.110 (11)	0.015 (7)	0.019 (8)	0.011 (7)
C6B	0.083 (9)	0.092 (5)	0.091 (10)	0.002 (6)	0.023 (8)	0.007 (6)
C7B	0.101 (10)	0.085 (5)	0.106 (11)	0.000 (7)	0.026 (8)	−0.008 (6)
C8B	0.121 (15)	0.106 (6)	0.161 (18)	−0.029 (8)	0.053 (15)	−0.047 (9)
C9B	0.090 (15)	0.117 (7)	0.137 (19)	0.009 (9)	0.024 (15)	0.012 (9)
C10B	0.100 (15)	0.197 (9)	0.121 (19)	0.008 (10)	−0.013 (15)	−0.008 (10)
O1C	0.095 (13)	0.115 (5)	0.079 (15)	0.007 (5)	0.016 (13)	0.009 (7)
C1C	0.092 (10)	0.078 (5)	0.089 (11)	0.009 (6)	0.024 (8)	0.001 (7)
C2C	0.069 (9)	0.074 (4)	0.073 (10)	0.000 (5)	0.018 (8)	0.000 (6)
C3C	0.104 (10)	0.104 (6)	0.092 (11)	−0.002 (6)	0.017 (8)	0.013 (6)
C4C	0.103 (9)	0.082 (5)	0.075 (10)	0.004 (5)	0.017 (8)	0.010 (6)
C5C	0.106 (10)	0.089 (5)	0.091 (10)	0.009 (6)	0.025 (8)	0.003 (6)
C6C	0.082 (10)	0.078 (5)	0.085 (10)	−0.003 (5)	0.021 (8)	0.004 (6)
C7C	0.094 (9)	0.093 (5)	0.081 (10)	0.000 (6)	0.019 (8)	0.004 (6)
C8C	0.080 (15)	0.140 (7)	0.145 (19)	−0.002 (8)	0.023 (15)	−0.007 (9)
C9C	0.158 (17)	0.084 (6)	0.139 (19)	−0.013 (8)	0.054 (15)	0.004 (8)
C10C	0.131 (15)	0.089 (6)	0.108 (18)	−0.010 (7)	0.043 (14)	0.002 (7)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.47 (2)
O1—H1A	0.83 (2)	C5B—C10B	1.547 (12)
O1—C1	1.43 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.519 (10)	C7B—H7B	0.9800
C1—C6	1.535 (11)	C7B—C8B	1.477 (19)
C2—H2	0.9800	C7B—C9B	1.59 (4)
C2—C3	1.60 (3)	C8B—H8BA	0.9600
C2—C7	1.534 (12)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.534 (11)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.482 (10)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.46 (2)	O1C—H1CA	0.82 (2)
C5—C10	1.533 (11)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.45 (3)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.521 (14)
C7—C8	1.521 (16)	C1C—C6C	1.502 (15)
C7—C9	1.51 (4)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.51 (3)
C8—H8B	0.9600	C2C—C7C	1.533 (16)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.527 (14)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.473 (14)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.54 (3)
O1B—C1B	1.45 (2)	C5C—C10C	1.526 (15)
O1B—H1BA	0.81 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.506 (12)	C7C—H7C	0.9800
C1B—C6B	1.521 (12)	C7C—C8C	1.522 (16)
C2B—H2B	0.9800	C7C—C9C	1.50 (2)
C2B—C3B	1.50 (2)	C8C—H8CA	0.9600
C2B—C7B	1.549 (13)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.515 (11)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.500 (11)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	95.9	C10B—C5B—H5B	106.8
C1—O1—H1B	109.5	C1B—C6B—H6BA	109.2
C1—O1—H1A	115 (10)	C1B—C6B—H6BB	109.2
O1—C1—H1	108.9	C5B—C6B—C1B	112.1 (14)
O1—C1—C2	108.8 (14)	C5B—C6B—H6BA	109.2
O1—C1—C6	109.7 (13)	C5B—C6B—H6BB	109.2
C2—C1—H1	108.9	H6BA—C6B—H6BB	107.9
C2—C1—C6	111.7 (6)	C2B—C7B—H7B	106.4
C6—C1—H1	108.9	C2B—C7B—C9B	112 (2)
C1—C2—H2	107.4	C8B—C7B—C2B	113.3 (10)
C1—C2—C3	106.9 (14)	C8B—C7B—H7B	106.4
C1—C2—C7	113.7 (7)	C8B—C7B—C9B	111.9 (13)
C3—C2—H2	107.4	C9B—C7B—H7B	106.4
C7—C2—H2	107.4	C7B—C8B—H8BA	109.5
C7—C2—C3	113.8 (15)	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.1	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.1	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.4	H8BA—C8B—H8BC	109.5
C4—C3—C2	108.2 (14)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.1	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.1	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.1	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.1	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.8	H9BA—C9B—H9BC	109.5
C5—C4—C3	112.5 (6)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.1	C5B—C10B—H10D	109.5
C5—C4—H4B	109.1	C5B—C10B—H10E	109.5
C4—C5—H5	104.5	C5B—C10B—H10F	109.5
C4—C5—C10	112.3 (7)	H10D—C10B—H10E	109.5
C6—C5—C4	115.0 (14)	H10D—C10B—H10F	109.5
C6—C5—H5	104.5	H10E—C10B—H10F	109.5
C6—C5—C10	114.6 (16)	H1CA—O1C—H1C	138.2
C10—C5—H5	104.5	C1C—O1C—H1CA	111
C1—C6—H6A	109.0	C1C—O1C—H1C	109.5
C1—C6—H6B	109.0	O1C—C1C—H1CB	108.3
C5—C6—C1	112.8 (13)	O1C—C1C—C2C	109 (2)
C5—C6—H6A	109.0	O1C—C1C—C6C	109.8 (11)
C5—C6—H6B	109.0	C2C—C1C—H1CB	108.3
H6A—C6—H6B	107.8	C6C—C1C—H1CB	108.3
C2—C7—H7	108.2	C6C—C1C—C2C	113.2 (8)
C8—C7—C2	111.0 (8)	C1C—C2C—H2C	106.4
C8—C7—H7	108.2	C1C—C2C—C7C	113.7 (7)
C9—C7—C2	113 (2)	C3C—C2C—C1C	109.5 (18)
C9—C7—H7	108.2	C3C—C2C—H2C	106.4
C9—C7—C8	107.7 (13)	C3C—C2C—C7C	113.7 (10)
C7—C8—H8A	109.5	C7C—C2C—H2C	106.4
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.0
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.0
H8A—C8—H8B	109.5	C2C—C3C—C4C	113.1 (10)
H8A—C8—H8C	109.5	H3CA—C3C—H3CB	107.8
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.0
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.0
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.2
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.2
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.9
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.0 (7)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.2
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.2
C5—C10—H10B	109.5	C4C—C5C—H5C	106.9
C5—C10—H10C	109.5	C4C—C5C—C6C	110.1 (18)
H10A—C10—H10B	109.5	C4C—C5C—C10C	113.8 (7)
H10A—C10—H10C	109.5	C6C—C5C—H5C	106.9
H10B—C10—H10C	109.5	C10C—C5C—H5C	106.9
H1BB—O1B—H1BA	132.0	C10C—C5C—C6C	111.8 (10)
C1B—O1B—H1BB	109.5	C1C—C6C—C5C	112.3 (11)
C1B—O1B—H1BA	103 (5)	C1C—C6C—H6CA	109.1
O1B—C1B—H1BC	110.5	C1C—C6C—H6CB	109.1
O1B—C1B—C2B	110.1 (15)	C5C—C6C—H6CA	109.1
O1B—C1B—C6B	105.6 (12)	C5C—C6C—H6CB	109.1
C2B—C1B—H1BC	110.5	H6CA—C6C—H6CB	107.9
C2B—C1B—C6B	109.7 (8)	C2C—C7C—H7C	106.6
C6B—C1B—H1BC	110.5	C8C—C7C—C2C	112.2 (7)
C1B—C2B—H2B	107.2	C8C—C7C—H7C	106.6
C1B—C2B—C7B	114.1 (7)	C9C—C7C—C2C	114.0 (18)
C3B—C2B—C1B	106.7 (15)	C9C—C7C—H7C	106.6
C3B—C2B—H2B	107.2	C9C—C7C—C8C	110.4 (11)
C3B—C2B—C7B	114.1 (14)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	107.2	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.5	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.5	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	110.8 (14)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.1	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.5	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.5	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.2 (7)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	106.8	C5C—C10C—H10I	109.5
C4B—C5B—C10B	112.6 (8)	H10G—C10C—H10H	109.5
C6B—C5B—C4B	110.3 (14)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	106.8	H10H—C10C—H10I	109.5
C6B—C5B—C10B	113.2 (17)

O1—C1—C2—C3	179.4 (12)	C3B—C2B—C7B—C9B	−57.5 (16)
O1—C1—C2—C7	53 (2)	C3B—C4B—C5B—C6B	51 (2)
O1—C1—C6—C5	174.8 (13)	C3B—C4B—C5B—C10B	178 (2)
C1—C2—C3—C4	60.3 (15)	C4B—C5B—C6B—C1B	−53 (2)
C1—C2—C7—C8	−164 (2)	C6B—C1B—C2B—C3B	−63 (2)
C1—C2—C7—C9	74 (2)	C6B—C1B—C2B—C7B	171 (2)
C2—C1—C6—C5	54 (2)	C7B—C2B—C3B—C4B	−172.7 (14)
C2—C3—C4—C5	−57 (2)	C10B—C5B—C6B—C1B	179.9 (16)
C3—C2—C7—C8	73 (3)	O1C—C1C—C2C—C3C	−174.5 (10)
C3—C2—C7—C9	−48.4 (14)	O1C—C1C—C2C—C7C	57.0 (19)
C3—C4—C5—C6	52 (2)	O1C—C1C—C6C—C5C	175.1 (16)
C3—C4—C5—C10	−175 (2)	C1C—C2C—C3C—C4C	53.1 (17)
C4—C5—C6—C1	−49 (2)	C1C—C2C—C7C—C8C	−172 (2)
C6—C1—C2—C3	−59 (2)	C1C—C2C—C7C—C9C	61 (2)
C6—C1—C2—C7	174 (2)	C2C—C1C—C6C—C5C	53 (2)
C7—C2—C3—C4	−173.4 (11)	C2C—C3C—C4C—C5C	−57 (2)
C10—C5—C6—C1	178.8 (15)	C3C—C2C—C7C—C8C	62 (2)
O1B—C1B—C2B—C3B	−178.3 (13)	C3C—C2C—C7C—C9C	−64.8 (14)
O1B—C1B—C2B—C7B	55 (2)	C3C—C4C—C5C—C6C	54.9 (19)
O1B—C1B—C6B—C5B	179.3 (15)	C3C—C4C—C5C—C10C	−178.7 (18)
C1B—C2B—C3B—C4B	60.4 (19)	C4C—C5C—C6C—C1C	−54.1 (17)
C1B—C2B—C7B—C8B	−167 (2)	C6C—C1C—C2C—C3C	−52 (2)
C1B—C2B—C7B—C9B	65 (2)	C6C—C1C—C2C—C7C	179 (2)
C2B—C1B—C6B—C5B	61 (2)	C7C—C2C—C3C—C4C	−178.5 (13)
C2B—C3B—C4B—C5B	−56 (2)	C10C—C5C—C6C—C1C	178.4 (14)
C3B—C2B—C7B—C8B	70 (3)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.45GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.050 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.855 (4) Å	Cell parameters from 1684 reflections
b = 21.1144 (11) Å	θ = 4.2–27.1°
c = 12.228 (4) Å	µ = 0.07 mm⁻¹
β = 104.37 (4)°	T = 296 K
V = 2964.9 (15) Å³	Plate, colourless
Z = 12	0.48 × 0.48 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	1684 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
Detector resolution: 16.4 pixels mm^-1	θ_max = 27.1°, θ_min = 4.2°
ω and φ scans	h = −10→10
Absorption correction: integration CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −26→27
T_min = 0.969, T_max = 0.997	l = −10→10
14984 measured reflections

Refinement top

Refinement on F²	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.199	w = 1/[σ²(F_o²) + (0.1046P)² + 0.4325P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1684 reflections	Δρ_max = 0.12 e Å⁻³
311 parameters	Δρ_min = −0.08 e Å⁻³

Special details top

Experimental. Data were collected at room temperature and pressure of 0.45 (2) GPa (450000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0044 (7)	0.06487 (14)	0.5041 (7)	0.087 (10)
H1B	0.061956	0.065739	0.495289	0.130*	0.5
H1A	−0.042 (9)	0.035 (5)	0.519 (13)	0.130*	0.5
C1	−0.0052 (9)	0.0934 (2)	0.6131 (8)	0.094 (13)
H1	−0.074347	0.079395	0.636829	0.113*
C2	−0.0089 (8)	0.16442 (18)	0.5962 (8)	0.075 (12)
H2	0.062286	0.176948	0.574652	0.112*
C3	−0.0050 (8)	0.1942 (2)	0.7132 (8)	0.065 (11)
H3A	−0.007308	0.239995	0.706743	0.079*
H3B	−0.072515	0.180629	0.738393	0.079*
C4	0.1038 (9)	0.1745 (2)	0.7979 (9)	0.084 (13)
H4A	0.170745	0.190431	0.774143	0.101*
H4B	0.104520	0.193766	0.870094	0.101*
C5	0.1153 (9)	0.1046 (2)	0.8129 (8)	0.084 (14)
H5	0.050871	0.089810	0.843294	0.100*
C6	0.1031 (8)	0.0738 (2)	0.6993 (8)	0.087 (12)
H6A	0.170487	0.084578	0.671445	0.105*
H6B	0.102462	0.028189	0.708507	0.105*
C7	−0.1134 (12)	0.1869 (3)	0.5029 (13)	0.093 (15)
H7	−0.116656	0.159395	0.437636	0.111*
C8	−0.0894 (9)	0.2548 (2)	0.4660 (10)	0.153 (15)
H8A	−0.014235	0.256074	0.449730	0.229*
H8B	−0.148096	0.266312	0.399651	0.229*
H8C	−0.090919	0.284024	0.525735	0.229*
C9	−0.2282 (12)	0.1820 (3)	0.5291 (14)	0.103 (19)
H9A	−0.240225	0.139284	0.550700	0.154*
H9B	−0.288158	0.193336	0.463679	0.154*
H9C	−0.230703	0.210161	0.590111	0.154*
C10	0.2287 (11)	0.0847 (3)	0.8947 (10)	0.105 (17)
H10A	0.231289	0.039357	0.900970	0.157*
H10B	0.293359	0.099171	0.867208	0.157*
H10C	0.233004	0.102962	0.967500	0.157*
O1B	0.1957 (7)	0.05172 (15)	0.4277 (7)	0.107 (11)
H1BB	0.136556	0.055919	0.450355	0.160*	0.5
H1BA	0.268 (5)	0.067 (3)	0.458 (4)	0.160*	0.5
C1B	0.1880 (10)	0.0910 (2)	0.3305 (9)	0.108 (15)
H1BC	0.252465	0.079947	0.297055	0.129*
C2B	0.1956 (10)	0.1590 (2)	0.3567 (9)	0.105 (13)
H2B	0.125575	0.169206	0.382074	0.126*
C3B	0.1846 (9)	0.1953 (2)	0.2469 (9)	0.116 (13)
H3BA	0.185660	0.240395	0.262290	0.139*
H3BB	0.250901	0.185628	0.216677	0.139*
C4B	0.0735 (10)	0.1788 (3)	0.1598 (10)	0.129 (16)
H4BA	0.007375	0.193219	0.186562	0.154*
H4BB	0.072280	0.201316	0.090313	0.154*
C5B	0.0610 (10)	0.1108 (3)	0.1357 (9)	0.130 (15)
H5B	0.123295	0.097776	0.100814	0.156*
C6B	0.0748 (9)	0.0737 (2)	0.2468 (8)	0.114 (13)
H6BA	0.009878	0.083238	0.279227	0.137*
H6BB	0.073787	0.028655	0.231342	0.137*
C7B	0.3003 (14)	0.1782 (3)	0.4552 (16)	0.114 (19)
H7B	0.304443	0.147569	0.516228	0.137*
C8B	0.2807 (10)	0.2420 (3)	0.5003 (10)	0.110 (16)
H8BA	0.346173	0.253034	0.560972	0.165*
H8BB	0.271765	0.272950	0.441236	0.165*
H8BC	0.211466	0.241015	0.527672	0.165*
C9B	0.4233 (15)	0.1745 (3)	0.4188 (19)	0.12 (2)
H9BA	0.432525	0.132986	0.390404	0.187*
H9BB	0.423457	0.205399	0.361217	0.187*
H9BC	0.486290	0.183057	0.483412	0.187*
C10B	−0.0563 (13)	0.0935 (3)	0.0550 (13)	0.12 (2)
H10D	−0.118524	0.105153	0.088491	0.179*
H10E	−0.058994	0.048753	0.040953	0.179*
H10F	−0.064805	0.115871	−0.014988	0.179*
O1C	0.4128 (7)	0.02179 (15)	0.5459 (7)	0.094 (9)
H1CA	0.469039	0.004521	0.530905	0.142*	0.5
H1C	0.345 (5)	0.031 (5)	0.489 (17)	0.142*	0.5
C1C	0.4116 (9)	0.0075 (2)	0.6641 (9)	0.095 (15)
H1CB	0.362624	0.038829	0.689407	0.115*
C2C	0.5340 (8)	0.0140 (2)	0.7347 (8)	0.069 (11)
H2C	0.580486	−0.016165	0.703415	0.083*
C3C	0.5416 (9)	−0.0079 (2)	0.8541 (8)	0.102 (13)
H3CA	0.499485	0.021646	0.890099	0.122*
H3CB	0.622508	−0.007599	0.896421	0.122*
C4C	0.4921 (9)	−0.0739 (2)	0.8585 (8)	0.100 (13)
H4CA	0.538902	−0.104114	0.829277	0.120*
H4CB	0.496414	−0.084982	0.936400	0.120*
C5C	0.3687 (9)	−0.0785 (2)	0.7917 (9)	0.072 (13)
H5C	0.323695	−0.048180	0.824303	0.086*
C6C	0.3607 (8)	−0.0572 (2)	0.6701 (8)	0.069 (12)
H6CA	0.401490	−0.087471	0.634208	0.104*
H6CB	0.279651	−0.056871	0.628378	0.104*
C7C	0.5895 (8)	0.0797 (2)	0.7277 (8)	0.093 (13)
H7C	0.581932	0.088584	0.647530	0.112*
C8C	0.7179 (11)	0.0810 (3)	0.7850 (13)	0.133 (17)
H8CA	0.759336	0.054902	0.743868	0.200*
H8CB	0.730006	0.065299	0.860732	0.200*
H8CC	0.746060	0.123755	0.786999	0.200*
C9C	0.5249 (9)	0.1325 (2)	0.7731 (9)	0.133 (15)
H9CA	0.531373	0.125709	0.852042	0.199*
H9CB	0.444207	0.132089	0.733024	0.199*
H9CC	0.558483	0.172685	0.762601	0.199*
C10C	0.3146 (9)	−0.1439 (2)	0.7973 (9)	0.110 (14)
H10G	0.235502	−0.143719	0.752742	0.164*
H10H	0.358272	−0.175166	0.768358	0.164*
H10I	0.315915	−0.153664	0.874255	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.107 (12)	0.068 (2)	0.082 (12)	−0.004 (3)	0.018 (12)	−0.007 (3)
C1	0.120 (17)	0.061 (3)	0.079 (15)	0.012 (4)	−0.016 (16)	−0.016 (4)
C2	0.086 (16)	0.059 (3)	0.073 (15)	0.008 (4)	0.009 (16)	−0.004 (4)
C3	0.072 (14)	0.062 (3)	0.071 (14)	0.000 (4)	0.034 (13)	−0.016 (4)
C4	0.084 (17)	0.086 (4)	0.084 (16)	0.002 (4)	0.022 (17)	−0.029 (4)
C5	0.080 (18)	0.095 (4)	0.072 (16)	0.008 (4)	0.012 (17)	−0.003 (4)
C6	0.097 (15)	0.064 (3)	0.089 (15)	0.005 (4)	0.001 (15)	0.001 (4)
C7	0.08 (2)	0.060 (3)	0.120 (18)	0.001 (5)	0.00 (2)	−0.006 (4)
C8	0.132 (19)	0.095 (4)	0.19 (2)	0.002 (5)	−0.028 (19)	0.050 (5)
C9	0.09 (2)	0.097 (4)	0.11 (2)	−0.013 (6)	0.01 (2)	−0.012 (5)
C10	0.12 (2)	0.137 (5)	0.05 (2)	0.027 (6)	0.01 (2)	−0.009 (5)
O1B	0.115 (14)	0.092 (3)	0.098 (12)	−0.012 (3)	−0.004 (13)	0.034 (3)
C1B	0.139 (19)	0.078 (3)	0.083 (18)	−0.010 (5)	−0.017 (19)	0.033 (5)
C2B	0.132 (16)	0.066 (3)	0.098 (16)	−0.005 (4)	−0.007 (16)	0.003 (4)
C3B	0.137 (18)	0.071 (3)	0.126 (16)	−0.001 (5)	0.006 (17)	0.034 (5)
C4B	0.15 (2)	0.114 (5)	0.109 (19)	0.015 (5)	0.00 (2)	0.040 (5)
C5B	0.13 (2)	0.134 (6)	0.101 (19)	−0.004 (6)	−0.02 (2)	0.031 (6)
C6B	0.127 (16)	0.074 (3)	0.111 (15)	0.005 (4)	−0.028 (16)	0.002 (4)
C7B	0.11 (2)	0.067 (4)	0.15 (2)	−0.006 (6)	0.00 (2)	−0.008 (5)
C8B	0.09 (2)	0.117 (5)	0.14 (2)	−0.010 (6)	0.06 (2)	−0.054 (6)
C9B	0.10 (3)	0.105 (5)	0.16 (3)	0.009 (7)	0.02 (3)	−0.005 (6)
C10B	0.11 (2)	0.188 (7)	0.06 (2)	0.011 (7)	0.02 (3)	0.002 (7)
O1C	0.114 (13)	0.095 (3)	0.060 (11)	0.004 (3)	−0.005 (12)	0.009 (3)
C1C	0.112 (19)	0.075 (3)	0.078 (17)	−0.004 (4)	−0.017 (18)	−0.001 (4)
C2C	0.094 (15)	0.068 (3)	0.041 (14)	−0.004 (4)	0.010 (14)	0.005 (3)
C3C	0.133 (17)	0.081 (3)	0.068 (15)	−0.008 (4)	−0.021 (16)	0.005 (4)
C4C	0.140 (17)	0.072 (3)	0.070 (15)	−0.012 (4)	−0.007 (16)	0.014 (4)
C5C	0.097 (17)	0.070 (3)	0.060 (16)	−0.002 (4)	0.041 (16)	0.004 (4)
C6C	0.074 (16)	0.066 (3)	0.066 (14)	−0.004 (4)	0.015 (15)	0.006 (4)
C7C	0.111 (17)	0.071 (3)	0.084 (16)	−0.002 (4)	−0.004 (16)	−0.002 (4)
C8C	0.08 (2)	0.126 (5)	0.18 (2)	−0.012 (5)	0.00 (2)	0.004 (6)
C9C	0.166 (19)	0.061 (3)	0.17 (2)	−0.008 (5)	0.039 (19)	−0.006 (5)
C10C	0.123 (17)	0.073 (3)	0.133 (18)	−0.010 (4)	0.032 (17)	0.018 (4)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.542 (14)
O1—H1A	0.822 (16)	C5B—C10B	1.536 (9)
O1—C1	1.465 (13)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.514 (6)	C7B—H7B	0.9800
C1—C6	1.503 (7)	C7B—C8B	1.495 (14)
C2—H2	0.9800	C7B—C9B	1.63 (4)
C2—C3	1.553 (14)	C8B—H8BA	0.9600
C2—C7	1.536 (8)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.499 (7)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.489 (6)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.507 (13)	O1C—H1CA	0.8200
C5—C10	1.523 (8)	O1C—H1C	0.95 (8)
C6—H6A	0.9700	O1C—C1C	1.479 (17)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.499 (9)
C7—C8	1.551 (12)	C1C—C6C	1.502 (9)
C7—C9	1.48 (3)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.513 (15)
C8—H8B	0.9600	C2C—C7C	1.546 (9)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.519 (8)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.490 (9)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.534 (15)
O1B—H1BA	0.90 (5)	C5C—C10C	1.531 (9)
O1B—C1B	1.434 (12)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.468 (7)	C7C—H7C	0.9800
C1B—C6B	1.517 (8)	C7C—C8C	1.510 (11)
C2B—H2B	0.9800	C7C—C9C	1.533 (15)
C2B—C3B	1.523 (14)	C8C—H8CA	0.9600
C2B—C7B	1.553 (9)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.515 (8)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.466 (7)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	129.8	C10B—C5B—C6B	109.1 (10)
C1—O1—H1B	109.5	C1B—C6B—C5B	110.8 (8)
C1—O1—H1A	89 (10)	C1B—C6B—H6BA	109.5
O1—C1—H1	109.9	C1B—C6B—H6BB	109.5
O1—C1—C2	106.8 (8)	C5B—C6B—H6BA	109.5
O1—C1—C6	109.2 (8)	C5B—C6B—H6BB	109.5
C2—C1—H1	109.9	H6BA—C6B—H6BB	108.1
C6—C1—H1	109.9	C2B—C7B—H7B	107.3
C6—C1—C2	111.0 (4)	C2B—C7B—C9B	111.9 (19)
C1—C2—H2	107.9	C8B—C7B—C2B	110.8 (7)
C1—C2—C3	106.4 (8)	C8B—C7B—H7B	107.3
C1—C2—C7	113.4 (4)	C8B—C7B—C9B	112.1 (9)
C3—C2—H2	107.9	C9B—C7B—H7B	107.3
C7—C2—H2	107.9	C7B—C8B—H8BA	109.5
C7—C2—C3	113.1 (10)	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.6	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.6	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.1	H8BA—C8B—H8BC	109.5
C4—C3—C2	110.4 (8)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.6	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.6	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.9	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.9	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.7	H9BA—C9B—H9BC	109.5
C5—C4—C3	113.3 (4)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.9	C5B—C10B—H10D	109.5
C5—C4—H4B	108.9	C5B—C10B—H10E	109.5
C4—C5—H5	107.9	C5B—C10B—H10F	109.5
C4—C5—C6	109.2 (7)	H10D—C10B—H10E	109.5
C4—C5—C10	113.2 (5)	H10D—C10B—H10F	109.5
C6—C5—H5	107.9	H10E—C10B—H10F	109.5
C6—C5—C10	110.7 (9)	H1CA—O1C—H1C	121.4
C10—C5—H5	107.9	C1C—O1C—H1CA	109.5
C1—C6—C5	113.4 (8)	C1C—O1C—H1C	123 (10)
C1—C6—H6A	108.9	O1C—C1C—H1CB	108.7
C1—C6—H6B	108.9	O1C—C1C—C2C	107.6 (11)
C5—C6—H6A	108.9	O1C—C1C—C6C	109.5 (6)
C5—C6—H6B	108.9	C2C—C1C—H1CB	108.7
H6A—C6—H6B	107.7	C2C—C1C—C6C	113.5 (4)
C2—C7—H7	106.5	C6C—C1C—H1CB	108.7
C2—C7—C8	109.2 (6)	C1C—C2C—H2C	105.9
C8—C7—H7	106.5	C1C—C2C—C3C	110.2 (10)
C9—C7—C2	115.7 (16)	C1C—C2C—C7C	114.5 (4)
C9—C7—H7	106.5	C3C—C2C—H2C	105.9
C9—C7—C8	111.9 (9)	C3C—C2C—C7C	113.8 (5)
C7—C8—H8A	109.5	C7C—C2C—H2C	105.9
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.1
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.1
H8A—C8—H8B	109.5	C2C—C3C—C4C	112.5 (5)
H8A—C8—H8C	109.5	H3CA—C3C—H3CB	107.8
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.1
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.1
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.2
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.2
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.9
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.1 (4)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.2
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.2
C5—C10—H10B	109.5	C4C—C5C—H5C	107.1
C5—C10—H10C	109.5	C4C—C5C—C6C	109.2 (10)
H10A—C10—H10B	109.5	C4C—C5C—C10C	113.6 (4)
H10A—C10—H10C	109.5	C6C—C5C—H5C	107.1
H10B—C10—H10C	109.5	C10C—C5C—H5C	107.1
H1BB—O1B—H1BA	128.9	C10C—C5C—C6C	112.5 (6)
C1B—O1B—H1BB	109.5	C1C—C6C—C5C	112.7 (6)
C1B—O1B—H1BA	90 (3)	C1C—C6C—H6CA	109.1
O1B—C1B—H1BC	108.2	C1C—C6C—H6CB	109.1
O1B—C1B—C2B	113.4 (9)	C5C—C6C—H6CA	109.1
O1B—C1B—C6B	106.5 (8)	C5C—C6C—H6CB	109.1
C2B—C1B—H1BC	108.2	H6CA—C6C—H6CB	107.8
C2B—C1B—C6B	112.2 (5)	C2C—C7C—H7C	107.0
C6B—C1B—H1BC	108.2	C8C—C7C—C2C	112.7 (4)
C1B—C2B—H2B	105.9	C8C—C7C—H7C	107.0
C1B—C2B—C3B	108.2 (8)	C8C—C7C—C9C	110.8 (7)
C1B—C2B—C7B	114.8 (4)	C9C—C7C—C2C	112.0 (10)
C3B—C2B—H2B	105.9	C9C—C7C—H7C	107.0
C3B—C2B—C7B	115.4 (10)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	105.9	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.2	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.2	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	107.9	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	112.0 (8)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.2	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.2	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.2 (5)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	108.3	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.7 (8)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	113.1 (6)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	108.3	H10H—C10C—H10I	109.5
C10B—C5B—H5B	108.3

O1—C1—C2—C3	−177.9 (7)	C3B—C2B—C7B—C9B	−54.3 (11)
O1—C1—C2—C7	57.1 (15)	C3B—C4B—C5B—C6B	53.1 (15)
O1—C1—C6—C5	175.7 (7)	C3B—C4B—C5B—C10B	175.1 (14)
C1—C2—C3—C4	59.4 (10)	C4B—C5B—C6B—C1B	−53.8 (12)
C1—C2—C7—C8	−162.1 (12)	C6B—C1B—C2B—C3B	−58.5 (15)
C1—C2—C7—C9	70.5 (15)	C6B—C1B—C2B—C7B	171.1 (15)
C2—C1—C6—C5	58.2 (14)	C7B—C2B—C3B—C4B	−173.7 (11)
C2—C3—C4—C5	−58.8 (14)	C10B—C5B—C6B—C1B	−178.2 (9)
C3—C2—C7—C8	76.6 (16)	O1C—C1C—C2C—C3C	−173.0 (5)
C3—C2—C7—C9	−50.8 (9)	O1C—C1C—C2C—C7C	57.3 (10)
C3—C4—C5—C6	53.4 (14)	O1C—C1C—C6C—C5C	173.7 (9)
C3—C4—C5—C10	177.2 (12)	C1C—C2C—C3C—C4C	52.8 (10)
C4—C5—C6—C1	−52.7 (12)	C1C—C2C—C7C—C8C	−171.0 (12)
C6—C1—C2—C3	−59.0 (13)	C1C—C2C—C7C—C9C	63.3 (11)
C6—C1—C2—C7	176.0 (13)	C2C—C1C—C6C—C5C	53.5 (14)
C7—C2—C3—C4	−175.4 (8)	C2C—C3C—C4C—C5C	−56.8 (14)
C10—C5—C6—C1	−177.9 (8)	C3C—C2C—C7C—C8C	61.0 (15)
O1B—C1B—C2B—C3B	−179.2 (9)	C3C—C2C—C7C—C9C	−64.7 (9)
O1B—C1B—C2B—C7B	50.4 (18)	C3C—C4C—C5C—C6C	55.5 (11)
O1B—C1B—C6B—C5B	−176.8 (9)	C3C—C4C—C5C—C10C	−178.1 (11)
C1B—C2B—C3B—C4B	56.2 (13)	C4C—C5C—C6C—C1C	−54.1 (10)
C1B—C2B—C7B—C8B	−161.6 (15)	C6C—C1C—C2C—C3C	−51.6 (12)
C1B—C2B—C7B—C9B	72.6 (16)	C6C—C1C—C2C—C7C	178.6 (11)
C2B—C1B—C6B—C5B	58.6 (15)	C7C—C2C—C3C—C4C	−177.0 (8)
C2B—C3B—C4B—C5B	−55.7 (16)	C10C—C5C—C6C—C1C	178.8 (9)
C3B—C2B—C7B—C8B	72 (2)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.56GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.062 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.728 (11) Å	Cell parameters from 1645 reflections
b = 21.0850 (12) Å	θ = 2.9–28.4°
c = 12.258 (2) Å	µ = 0.07 mm⁻¹
β = 104.60 (5)°	T = 296 K
V = 2933 (3) Å³	Plate, colourless
Z = 12	0.4 × 0.4 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	713 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.082
ω and π scans	θ_max = 28.4°, θ_min = 2.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
T_min = 0.974, T_max = 0.997	k = −28→27
16901 measured reflections	l = −16→16
1645 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.066	w = 1/[σ²(F_o²) + (0.1321P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.232	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.08 e Å⁻³
1645 reflections	Δρ_min = −0.09 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
205 restraints	Extinction coefficient: 0.002 (4)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.56 (2) GPa (560000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0061 (10)	0.06487 (15)	0.5018 (4)	0.076 (7)
H1B	0.060577	0.064437	0.492033	0.115*	0.5
H1A	−0.020 (17)	0.0280 (15)	0.518 (12)	0.115*	0.5
C1	−0.0028 (17)	0.0927 (2)	0.6092 (7)	0.067 (4)
H1	−0.072176	0.078002	0.632782	0.081*
C2	−0.011 (2)	0.1645 (3)	0.5967 (8)	0.073 (5)
H2	0.061364	0.177903	0.576941	0.110*
C3	−0.0057 (18)	0.1939 (3)	0.7125 (7)	0.078 (5)
H3A	−0.005767	0.239787	0.706046	0.093*
H3B	−0.075389	0.181615	0.736230	0.093*
C4	0.1018 (19)	0.1734 (3)	0.7998 (8)	0.092 (5)
H4A	0.171315	0.189854	0.780221	0.111*
H4B	0.099428	0.191327	0.872118	0.111*
C5	0.111 (2)	0.1037 (3)	0.8100 (8)	0.083 (5)
H5	0.044056	0.088262	0.836888	0.100*
C6	0.1049 (18)	0.0736 (3)	0.6983 (7)	0.070 (4)
H6A	0.105392	0.027866	0.706824	0.084*
H6B	0.174538	0.085381	0.673860	0.084*
C7	−0.111 (2)	0.1872 (3)	0.5025 (10)	0.079 (5)
H7	−0.113723	0.159371	0.437846	0.095*
C8	−0.089 (2)	0.2551 (3)	0.4653 (8)	0.144 (8)
H8A	−0.154727	0.268190	0.405236	0.216*
H8B	−0.081282	0.283547	0.527995	0.216*
H8C	−0.018506	0.255885	0.439631	0.216*
C9	−0.233 (3)	0.1852 (4)	0.5250 (12)	0.107 (9)
H9A	−0.248875	0.143148	0.547825	0.161*
H9B	−0.291575	0.196430	0.457570	0.161*
H9C	−0.236507	0.214662	0.583869	0.161*
C10	0.226 (2)	0.0829 (4)	0.8960 (9)	0.107 (8)
H10A	0.229108	0.037407	0.900395	0.160*
H10B	0.292907	0.098223	0.871921	0.160*
H10C	0.227619	0.100079	0.968830	0.160*
O1B	0.1959 (13)	0.05220 (19)	0.4292 (5)	0.107 (7)
H1BB	0.136048	0.057318	0.451234	0.161*	0.5
H1CA	0.337 (14)	0.015 (12)	0.519 (19)	0.161*	0.5
C1B	0.189 (2)	0.0903 (3)	0.3306 (8)	0.084 (5)
H1BC	0.254883	0.078534	0.298687	0.101*
C2B	0.198 (2)	0.1590 (3)	0.3554 (8)	0.085 (5)
H2B	0.126679	0.169519	0.379988	0.102*
C3B	0.187 (2)	0.1955 (3)	0.2476 (9)	0.093 (5)
H3BA	0.183243	0.240428	0.262930	0.111*
H3BB	0.256981	0.188120	0.220755	0.111*
C4B	0.084 (2)	0.1778 (4)	0.1603 (9)	0.109 (5)
H4BA	0.089074	0.198924	0.091310	0.131*
H4BB	0.015526	0.194247	0.180950	0.131*
C5B	0.065 (3)	0.1104 (4)	0.1359 (10)	0.113 (5)
H5B	0.128310	0.095595	0.102495	0.135*
C6B	0.077 (2)	0.0737 (3)	0.2465 (8)	0.079 (5)
H6BA	0.010277	0.083899	0.277321	0.095*
H6BB	0.074714	0.028489	0.231485	0.095*
C7B	0.301 (3)	0.1782 (4)	0.4531 (11)	0.097 (5)
H7B	0.302383	0.146984	0.512816	0.117*
C8B	0.2810 (19)	0.2427 (3)	0.5034 (8)	0.145 (8)
H8BA	0.204183	0.243596	0.517524	0.218*
H8BB	0.339771	0.249089	0.572785	0.218*
H8BC	0.286803	0.275745	0.451159	0.218*
C9B	0.422 (4)	0.1755 (5)	0.4299 (16)	0.137 (9)
H9BA	0.480348	0.188312	0.496136	0.206*
H9BB	0.437881	0.132954	0.410111	0.206*
H9BC	0.424020	0.203551	0.368757	0.206*
C10B	−0.054 (3)	0.0938 (5)	0.0524 (11)	0.131 (9)
H10D	−0.117656	0.104042	0.086111	0.197*
H10E	−0.056673	0.049303	0.035226	0.197*
H10F	−0.063058	0.117777	−0.015793	0.197*
O1C	0.4098 (11)	0.0210 (3)	0.5460 (5)	0.087 (7)
H1C	0.466713	0.005521	0.528212	0.130*	0.5
H1BA	0.258 (5)	0.064 (4)	0.472 (6)	0.130*	0.5
C1C	0.417 (2)	0.0061 (4)	0.6638 (9)	0.078 (5)
H1CB	0.367644	0.037696	0.689368	0.094*
C2C	0.538 (2)	0.0145 (4)	0.7357 (9)	0.080 (5)
H2C	0.586842	−0.015233	0.705868	0.096*
C3C	0.5452 (15)	−0.0079 (2)	0.8553 (6)	0.077 (4)
H3CA	0.626975	−0.008050	0.897910	0.092*
H3CB	0.502962	0.021811	0.891208	0.092*
C4C	0.494 (2)	−0.0734 (4)	0.8585 (9)	0.080 (5)
H4CA	0.499771	−0.084704	0.936416	0.096*
H4CB	0.541179	−0.103502	0.828894	0.096*
C5C	0.363 (2)	−0.0795 (4)	0.7902 (9)	0.088 (5)
H5C	0.316753	−0.049260	0.822112	0.105*
C6C	0.3576 (15)	−0.0581 (2)	0.6689 (6)	0.073 (4)
H6CA	0.395846	−0.089737	0.632949	0.109*
H6CB	0.275765	−0.055483	0.626739	0.109*
C7C	0.595 (3)	0.0812 (5)	0.7303 (11)	0.080 (5)
H7C	0.587510	0.090240	0.650443	0.096*
C8C	0.714 (4)	0.0805 (7)	0.7828 (14)	0.142 (11)
H8CA	0.752772	0.050192	0.746217	0.213*
H8CB	0.725011	0.069039	0.860532	0.213*
H8CC	0.746360	0.121899	0.777945	0.213*
C9C	0.5235 (19)	0.1326 (3)	0.7734 (9)	0.108 (8)
H9CA	0.533665	0.127599	0.853155	0.162*
H9CB	0.441504	0.128400	0.735671	0.162*
H9CC	0.550895	0.173750	0.758320	0.162*
C10C	0.3116 (17)	−0.1438 (3)	0.7954 (7)	0.096 (8)
H10G	0.317241	−0.154777	0.872620	0.144*
H10H	0.230355	−0.143692	0.754086	0.144*
H10I	0.354173	−0.174315	0.762967	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.08 (2)	0.066 (2)	0.079 (4)	0.000 (4)	0.006 (8)	−0.016 (2)
C1	0.065 (13)	0.063 (3)	0.073 (5)	0.002 (6)	0.016 (7)	−0.010 (3)
C2	0.074 (13)	0.067 (4)	0.076 (5)	−0.003 (7)	0.012 (8)	−0.005 (3)
C3	0.077 (13)	0.058 (3)	0.092 (5)	−0.003 (6)	0.011 (7)	−0.015 (4)
C4	0.096 (13)	0.088 (5)	0.090 (5)	0.006 (7)	0.018 (8)	−0.017 (4)
C5	0.082 (13)	0.090 (4)	0.081 (5)	0.009 (7)	0.027 (7)	−0.001 (4)
C6	0.073 (13)	0.064 (3)	0.071 (5)	−0.005 (6)	0.012 (7)	−0.002 (3)
C7	0.080 (13)	0.071 (4)	0.085 (6)	−0.005 (7)	0.018 (8)	−0.007 (4)
C8	0.15 (2)	0.098 (5)	0.171 (9)	−0.002 (9)	0.027 (12)	0.046 (5)
C9	0.11 (3)	0.107 (5)	0.110 (9)	−0.015 (13)	0.032 (13)	−0.019 (5)
C10	0.11 (2)	0.130 (5)	0.074 (6)	0.019 (10)	0.008 (11)	0.002 (5)
O1B	0.12 (2)	0.106 (3)	0.088 (4)	−0.006 (6)	0.007 (9)	0.037 (3)
C1B	0.084 (13)	0.086 (5)	0.081 (5)	0.002 (7)	0.019 (7)	0.012 (4)
C2B	0.088 (13)	0.085 (4)	0.077 (5)	−0.003 (7)	0.008 (8)	−0.008 (4)
C3B	0.096 (13)	0.069 (4)	0.110 (6)	0.000 (6)	0.021 (8)	0.016 (4)
C4B	0.114 (13)	0.111 (6)	0.095 (6)	0.003 (8)	0.011 (8)	0.030 (4)
C5B	0.113 (13)	0.128 (6)	0.102 (6)	0.000 (8)	0.036 (8)	0.005 (5)
C6B	0.078 (13)	0.069 (4)	0.085 (6)	0.008 (6)	0.008 (8)	0.008 (4)
C7B	0.100 (13)	0.073 (4)	0.109 (7)	0.000 (7)	0.008 (9)	0.006 (4)
C8B	0.14 (2)	0.104 (5)	0.188 (9)	0.002 (9)	0.040 (12)	−0.067 (5)
C9B	0.13 (3)	0.133 (7)	0.154 (11)	−0.009 (15)	0.054 (16)	0.003 (6)
C10B	0.13 (3)	0.156 (8)	0.120 (8)	−0.003 (11)	0.045 (13)	−0.015 (6)
O1C	0.10 (2)	0.094 (3)	0.066 (4)	−0.007 (6)	0.019 (8)	0.012 (2)
C1C	0.076 (13)	0.084 (5)	0.077 (6)	−0.002 (8)	0.024 (8)	0.007 (4)
C2C	0.079 (13)	0.074 (4)	0.086 (6)	−0.008 (8)	0.021 (8)	0.001 (4)
C3C	0.083 (13)	0.081 (4)	0.063 (4)	−0.006 (6)	0.009 (7)	0.004 (3)
C4C	0.083 (13)	0.078 (4)	0.077 (6)	−0.008 (8)	0.014 (8)	0.010 (4)
C5C	0.090 (13)	0.083 (5)	0.086 (7)	−0.011 (8)	0.015 (8)	0.012 (4)
C6C	0.070 (13)	0.068 (3)	0.077 (5)	−0.005 (6)	0.012 (7)	0.002 (3)
C7C	0.078 (14)	0.083 (5)	0.080 (6)	−0.023 (8)	0.024 (9)	0.002 (4)
C8C	0.14 (3)	0.145 (9)	0.141 (12)	0.010 (16)	0.029 (16)	0.011 (8)
C9C	0.09 (2)	0.077 (4)	0.152 (8)	−0.014 (8)	0.027 (12)	−0.019 (5)
C10C	0.10 (2)	0.082 (4)	0.106 (6)	−0.033 (8)	0.022 (10)	0.009 (4)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.537 (11)
O1—H1A	0.83 (2)	C5B—C10B	1.56 (4)
O1—C1	1.433 (7)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.522 (8)	C7B—H7B	0.9800
C1—C6	1.50 (2)	C7B—C8B	1.535 (11)
C2—H2	0.9800	C7B—C9B	1.52 (4)
C2—C3	1.536 (9)	C8B—H8BA	0.9600
C2—C7	1.50 (3)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.50 (2)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.478 (10)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.494 (9)	O1C—H1CA	0.84 (18)
C5—C10	1.55 (3)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.460 (12)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.48 (4)
C7—C8	1.544 (10)	C1C—C6C	1.529 (15)
C7—C9	1.53 (4)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.522 (10)
C8—H8B	0.9600	C2C—C7C	1.56 (2)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.510 (13)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.56 (4)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.540 (10)
O1B—C1B	1.438 (8)	C5C—C10C	1.493 (14)
O1B—H1BA	0.82 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.478 (10)	C7C—H7C	0.9800
C1B—C6B	1.50 (3)	C7C—C8C	1.38 (5)
C2B—H2B	0.9800	C7C—C9C	1.54 (2)
C2B—C3B	1.506 (10)	C8C—H8CA	0.9600
C2B—C7B	1.53 (4)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.44 (3)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.458 (12)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	106.3	C10B—C5B—H5B	107.7
C1—O1—H1B	109.5	C1B—C6B—C5B	110.7 (14)
C1—O1—H1A	97 (7)	C1B—C6B—H6BA	109.5
O1—C1—H1	108.0	C1B—C6B—H6BB	109.5
O1—C1—C2	109.2 (5)	C5B—C6B—H6BA	109.5
O1—C1—C6	112.4 (11)	C5B—C6B—H6BB	109.5
C2—C1—H1	108.0	H6BA—C6B—H6BB	108.1
C6—C1—H1	108.0	C2B—C7B—H7B	105.8
C6—C1—C2	111.1 (12)	C2B—C7B—C8B	112.3 (19)
C1—C2—H2	106.0	C8B—C7B—H7B	105.8
C1—C2—C3	108.8 (6)	C9B—C7B—C2B	115.9 (11)
C3—C2—H2	106.0	C9B—C7B—H7B	105.8
C7—C2—C1	114.3 (13)	C9B—C7B—C8B	110.5 (17)
C7—C2—H2	106.0	C7B—C8B—H8BA	109.5
C7—C2—C3	115.0 (14)	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.2	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.2	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	107.9	H8BA—C8B—H8BC	109.5
C4—C3—C2	112.0 (13)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.2	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.2	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.2	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.2	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	112.2 (13)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.2	C5B—C10B—H10D	109.5
C5—C4—H4B	109.2	C5B—C10B—H10E	109.5
C4—C5—H5	108.1	C5B—C10B—H10F	109.5
C4—C5—C6	111.1 (6)	H10D—C10B—H10E	109.5
C4—C5—C10	111.8 (14)	H10D—C10B—H10F	109.5
C6—C5—H5	108.1	H10E—C10B—H10F	109.5
C6—C5—C10	109.5 (13)	H1CA—O1C—H1C	130.5
C10—C5—H5	108.1	C1C—O1C—H1CA	98 (10)
C1—C6—H6A	109.0	C1C—O1C—H1C	109.5
C1—C6—H6B	109.0	O1C—C1C—H1CB	106.3
C5—C6—C1	112.9 (12)	O1C—C1C—C2C	111.5 (17)
C5—C6—H6A	109.0	O1C—C1C—C6C	108.5 (9)
C5—C6—H6B	109.0	C2C—C1C—H1CB	106.3
H6A—C6—H6B	107.8	C2C—C1C—C6C	117.2 (11)
C2—C7—H7	106.9	C6C—C1C—H1CB	106.3
C2—C7—C8	111.5 (18)	C1C—C2C—H2C	105.4
C2—C7—C9	116.1 (10)	C1C—C2C—C3C	110.3 (18)
C8—C7—H7	106.9	C1C—C2C—C7C	115.8 (15)
C9—C7—H7	106.9	C3C—C2C—H2C	105.4
C9—C7—C8	108.1 (15)	C3C—C2C—C7C	113.5 (11)
C7—C8—H8A	109.5	C7C—C2C—H2C	105.4
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.1
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.1
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.8
H8A—C8—H8C	109.5	C4C—C3C—C2C	112.6 (9)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.1
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.1
C7—C9—H9B	109.5	C3C—C4C—H4CA	108.8
C7—C9—H9C	109.5	C3C—C4C—H4CB	108.8
H9A—C9—H9B	109.5	C3C—C4C—C5C	113.9 (12)
H9A—C9—H9C	109.5	H4CA—C4C—H4CB	107.7
H9B—C9—H9C	109.5	C5C—C4C—H4CA	108.8
C5—C10—H10A	109.5	C5C—C4C—H4CB	108.8
C5—C10—H10B	109.5	C4C—C5C—H5C	107.6
C5—C10—H10C	109.5	C6C—C5C—C4C	106.9 (16)
H10A—C10—H10B	109.5	C6C—C5C—H5C	107.6
H10A—C10—H10C	109.5	C10C—C5C—C4C	113.9 (12)
H10B—C10—H10C	109.5	C10C—C5C—H5C	107.6
H1BB—O1B—H1BA	116.5	C10C—C5C—C6C	112.9 (9)
C1B—O1B—H1BB	109.5	C1C—C6C—C5C	112.9 (8)
C1B—O1B—H1BA	103 (5)	C1C—C6C—H6CA	109.0
O1B—C1B—H1BC	108.2	C1C—C6C—H6CB	109.0
O1B—C1B—C2B	112.9 (6)	C5C—C6C—H6CA	109.0
O1B—C1B—C6B	107.4 (12)	C5C—C6C—H6CB	109.0
C2B—C1B—H1BC	108.2	H6CA—C6C—H6CB	107.8
C2B—C1B—C6B	111.9 (16)	C2C—C7C—H7C	106.7
C6B—C1B—H1BC	108.2	C8C—C7C—C2C	111.2 (17)
C1B—C2B—H2B	105.4	C8C—C7C—H7C	106.7
C1B—C2B—C3B	109.4 (6)	C8C—C7C—C9C	114.7 (15)
C1B—C2B—C7B	114.8 (15)	C9C—C7C—C2C	110.2 (17)
C3B—C2B—H2B	105.4	C9C—C7C—H7C	106.7
C3B—C2B—C7B	115.4 (15)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	105.4	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.0	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.0	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	107.8	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	112.8 (14)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.0	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.0	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.0	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.0	H9CA—C9C—H9CB	109.5
C3B—C4B—C5B	117.4 (15)	H9CA—C9C—H9CC	109.5
H4BA—C4B—H4BB	107.2	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.0	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.0	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.7	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.6 (8)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	114.8 (17)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	107.7	H10H—C10C—H10I	109.5
C6B—C5B—C10B	109.2 (16)

O1—C1—C2—C3	−179.2 (15)	C3B—C2B—C7B—C9B	−55.7 (16)
O1—C1—C2—C7	51 (2)	C3B—C4B—C5B—C6B	49 (2)
O1—C1—C6—C5	178.5 (8)	C3B—C4B—C5B—C10B	172.5 (14)
C1—C2—C3—C4	55 (2)	C4B—C5B—C6B—C1B	−51 (2)
C1—C2—C7—C8	−158.9 (10)	C6B—C1B—C2B—C3B	−57 (2)
C1—C2—C7—C9	76.7 (13)	C6B—C1B—C2B—C7B	171.1 (14)
C2—C1—C6—C5	55.9 (14)	C7B—C2B—C3B—C4B	−176.7 (16)
C2—C3—C4—C5	−55.9 (16)	C10B—C5B—C6B—C1B	−177.9 (14)
C3—C2—C7—C8	74.3 (18)	O1C—C1C—C2C—C3C	−174.0 (5)
C3—C2—C7—C9	−50.2 (15)	O1C—C1C—C2C—C7C	55.3 (17)
C3—C4—C5—C6	54.2 (19)	O1C—C1C—C6C—C5C	178.2 (16)
C3—C4—C5—C10	176.8 (11)	C1C—C2C—C3C—C4C	50.3 (18)
C4—C5—C6—C1	−54.6 (19)	C1C—C2C—C7C—C8C	−168.7 (15)
C6—C1—C2—C3	−55 (2)	C1C—C2C—C7C—C9C	62.9 (16)
C6—C1—C2—C7	175.2 (13)	C2C—C1C—C6C—C5C	51 (2)
C7—C2—C3—C4	−175.1 (13)	C2C—C3C—C4C—C5C	−57.5 (19)
C10—C5—C6—C1	−178.5 (11)	C3C—C2C—C7C—C8C	62 (2)
O1B—C1B—C2B—C3B	−178.6 (18)	C3C—C2C—C7C—C9C	−66 (2)
O1B—C1B—C2B—C7B	50 (2)	C3C—C4C—C5C—C6C	55.9 (13)
O1B—C1B—C6B—C5B	−177.3 (9)	C3C—C4C—C5C—C10C	−178.7 (5)
C1B—C2B—C3B—C4B	52 (2)	C4C—C5C—C6C—C1C	−50.7 (16)
C1B—C2B—C7B—C8B	−158.8 (11)	C6C—C1C—C2C—C3C	−48.1 (16)
C1B—C2B—C7B—C9B	72.9 (15)	C6C—C1C—C2C—C7C	−178.8 (7)
C2B—C1B—C6B—C5B	58.3 (16)	C7C—C2C—C3C—C4C	−177.8 (18)
C2B—C3B—C4B—C5B	−50 (2)	C10C—C5C—C6C—C1C	−176.7 (16)
C3B—C2B—C7B—C8B	73 (2)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.57GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.088 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.707 (10) Å	Cell parameters from 1419 reflections
b = 20.974 (3) Å	θ = 26.6–3.4°
c = 11.987 (10) Å	µ = 0.07 mm⁻¹
β = 103.48 (10)°	T = 296 K
V = 2862 (4) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	1419 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	564 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.189
ω and φ scans	θ_max = 28.4°, θ_min = 3.4°
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
T_min = 0.970, T_max = 0.999	k = −27→27
16614 measured reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.095	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.348	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.12 e Å⁻³
1419 reflections	Δρ_min = −0.12 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.007 (8)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0119 (14)	0.0653 (3)	0.5043 (12)	0.086 (11)
H1B	0.052894	0.063292	0.489231	0.130*	0.5
H1A	−0.01 (2)	0.0259 (11)	0.51 (2)	0.130*	0.5
C1	−0.0017 (17)	0.0932 (4)	0.6059 (17)	0.061 (7)
H1	−0.070842	0.078804	0.631876	0.073*
C2	−0.0142 (17)	0.1653 (4)	0.5983 (16)	0.072 (7)
H2	0.057788	0.178190	0.575863	0.108*
C3	−0.0011 (18)	0.1953 (4)	0.7071 (16)	0.068 (7)
H3A	−0.071914	0.187343	0.733749	0.082*
H3B	0.003719	0.240951	0.696045	0.082*
C4	0.1019 (18)	0.1758 (4)	0.8004 (17)	0.083 (7)
H4A	0.172728	0.194367	0.785237	0.099*
H4B	0.092104	0.192799	0.872838	0.099*
C5	0.117 (2)	0.1054 (5)	0.811 (2)	0.087 (7)
H5	0.050759	0.090739	0.841592	0.105*
C6	0.1007 (18)	0.0735 (4)	0.6999 (16)	0.076 (7)
H6A	0.093894	0.028120	0.712427	0.091*
H6B	0.171654	0.079856	0.672577	0.091*
C7	−0.110 (3)	0.1881 (5)	0.496 (3)	0.082 (7)
H7	−0.111899	0.160376	0.430007	0.098*
C8	−0.092 (2)	0.2569 (5)	0.4635 (18)	0.108 (12)
H8A	−0.153819	0.269177	0.399485	0.162*
H8B	−0.092517	0.284261	0.527532	0.162*
H8C	−0.017678	0.260531	0.442944	0.162*
C9	−0.237 (3)	0.1838 (5)	0.532 (2)	0.082 (12)
H9A	−0.251854	0.140507	0.550641	0.124*
H9B	−0.298761	0.197658	0.468417	0.124*
H9C	−0.235983	0.210645	0.596866	0.124*
C10	0.226 (2)	0.0848 (5)	0.899 (2)	0.109 (12)
H10A	0.230514	0.107684	0.969160	0.163*
H10B	0.222145	0.039866	0.912852	0.163*
H10C	0.294448	0.093851	0.870441	0.163*
O1B	0.1917 (14)	0.0486 (3)	0.4252 (13)	0.101 (11)
H1BB	0.132700	0.051982	0.450624	0.152*	0.5
H1CA	0.339 (5)	0.029 (13)	0.530 (11)	0.152*	0.5
C1B	0.182 (2)	0.0893 (4)	0.3296 (18)	0.075 (7)
H1BC	0.247668	0.077470	0.296037	0.089*
C2B	0.196 (2)	0.1587 (4)	0.3515 (19)	0.088 (7)
H2B	0.125864	0.168356	0.380122	0.106*
C3B	0.174 (2)	0.1948 (4)	0.2498 (19)	0.088 (7)
H3BA	0.243761	0.191812	0.218795	0.106*
H3BB	0.166901	0.239035	0.270424	0.106*
C4B	0.072 (2)	0.1789 (5)	0.157 (2)	0.115 (7)
H4BA	0.081503	0.199353	0.087094	0.138*
H4BB	0.002530	0.196978	0.175753	0.138*
C5B	0.051 (2)	0.1096 (6)	0.133 (2)	0.108 (7)
H5B	0.113707	0.096861	0.096538	0.129*
C6B	0.0733 (18)	0.0730 (5)	0.2387 (17)	0.086 (7)
H6BA	0.078117	0.028371	0.219084	0.103*
H6BB	0.005989	0.077618	0.272310	0.103*
C7B	0.294 (3)	0.1771 (6)	0.454 (3)	0.084 (7)
H7B	0.293921	0.145757	0.514954	0.101*
C8B	0.278 (2)	0.2414 (5)	0.5020 (19)	0.116 (12)
H8BA	0.341792	0.250119	0.566179	0.174*
H8BB	0.275228	0.273129	0.443856	0.174*
H8BC	0.205180	0.242116	0.526566	0.174*
C9B	0.418 (3)	0.1716 (6)	0.420 (3)	0.107 (13)
H9BA	0.425318	0.129808	0.389401	0.160*
H9BB	0.421748	0.203023	0.362503	0.160*
H9BC	0.480192	0.178561	0.486215	0.160*
C10B	−0.058 (3)	0.0929 (6)	0.047 (3)	0.140 (13)
H10D	−0.124494	0.109742	0.071187	0.209*
H10E	−0.064372	0.047392	0.040817	0.209*
H10F	−0.054639	0.110797	−0.025598	0.209*
O1C	0.4103 (13)	0.0219 (3)	0.5455 (15)	0.094 (11)
H1C	0.467043	0.006732	0.525633	0.141*	0.5
H1BA	0.258 (5)	0.053 (5)	0.463 (9)	0.141*	0.5
C1C	0.416 (2)	0.0060 (5)	0.660 (2)	0.084 (7)
H1CB	0.365313	0.037250	0.684716	0.100*
C2C	0.5290 (18)	0.0144 (4)	0.7383 (18)	0.066 (7)
H2C	0.579381	−0.014546	0.706947	0.080*
C3C	0.5429 (19)	−0.0091 (4)	0.8540 (19)	0.081 (7)
H3CA	0.502225	0.019142	0.895890	0.098*
H3CB	0.625585	−0.008858	0.892344	0.098*
C4C	0.4956 (17)	−0.0752 (4)	0.8560 (16)	0.077 (7)
H4CA	0.503554	−0.088449	0.934960	0.092*
H4CB	0.541463	−0.104171	0.820817	0.092*
C5C	0.3676 (19)	−0.0794 (4)	0.7928 (18)	0.084 (7)
H5C	0.321156	−0.050769	0.829507	0.100*
C6C	0.3575 (18)	−0.0576 (4)	0.6689 (17)	0.070 (7)
H6CA	0.392676	−0.089762	0.629209	0.105*
H6CB	0.275051	−0.054485	0.630514	0.105*
C7C	0.5852 (18)	0.0796 (5)	0.7284 (18)	0.079 (7)
H7C	0.580169	0.087676	0.646896	0.095*
C8C	0.713 (2)	0.0840 (5)	0.791 (3)	0.117 (12)
H8CA	0.760724	0.067569	0.742505	0.175*
H8CB	0.725391	0.059610	0.860095	0.175*
H8CC	0.732554	0.127824	0.808703	0.175*
C9C	0.518 (2)	0.1338 (5)	0.774 (2)	0.126 (12)
H9CA	0.534439	0.131791	0.855960	0.189*
H9CB	0.435414	0.128891	0.742688	0.189*
H9CC	0.543472	0.174240	0.750717	0.189*
C10C	0.321 (2)	−0.1462 (5)	0.794 (2)	0.110 (12)
H10G	0.240244	−0.147374	0.753741	0.165*
H10H	0.365954	−0.174461	0.757821	0.165*
H10I	0.328069	−0.159529	0.872187	0.165*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.119 (17)	0.073 (4)	0.066 (15)	0.004 (7)	0.019 (14)	−0.017 (6)
C1	0.064 (11)	0.062 (5)	0.057 (10)	−0.008 (6)	0.016 (8)	0.002 (6)
C2	0.062 (11)	0.073 (5)	0.078 (10)	0.008 (6)	0.014 (8)	−0.011 (6)
C3	0.067 (11)	0.072 (5)	0.067 (10)	−0.002 (6)	0.018 (8)	−0.011 (6)
C4	0.075 (11)	0.090 (6)	0.080 (10)	−0.001 (7)	0.013 (8)	−0.019 (7)
C5	0.082 (11)	0.094 (6)	0.086 (11)	0.008 (7)	0.021 (8)	−0.001 (7)
C6	0.079 (11)	0.069 (5)	0.081 (10)	0.003 (6)	0.019 (8)	0.001 (6)
C7	0.086 (11)	0.078 (6)	0.084 (11)	−0.007 (8)	0.023 (9)	−0.002 (7)
C8	0.090 (19)	0.105 (7)	0.128 (17)	0.001 (9)	0.026 (15)	0.043 (10)
C9	0.090 (19)	0.083 (6)	0.081 (18)	0.013 (11)	0.033 (16)	−0.017 (9)
C10	0.097 (19)	0.129 (8)	0.096 (18)	0.010 (10)	0.016 (15)	0.009 (10)
O1B	0.110 (16)	0.095 (4)	0.085 (15)	0.014 (7)	−0.003 (14)	0.001 (7)
C1B	0.071 (11)	0.075 (5)	0.078 (10)	0.008 (7)	0.018 (8)	0.011 (7)
C2B	0.090 (11)	0.081 (6)	0.098 (11)	0.010 (7)	0.030 (8)	−0.004 (7)
C3B	0.087 (11)	0.088 (6)	0.091 (10)	0.008 (7)	0.022 (8)	0.009 (7)
C4B	0.110 (11)	0.127 (7)	0.106 (11)	0.017 (8)	0.017 (9)	0.023 (8)
C5B	0.097 (11)	0.126 (7)	0.094 (11)	0.000 (8)	0.009 (8)	0.009 (8)
C6B	0.080 (11)	0.094 (6)	0.080 (10)	−0.001 (7)	0.011 (8)	0.007 (7)
C7B	0.082 (11)	0.084 (6)	0.086 (11)	−0.006 (8)	0.021 (9)	−0.012 (7)
C8B	0.11 (2)	0.120 (8)	0.124 (18)	−0.009 (10)	0.033 (15)	−0.046 (11)
C9B	0.10 (2)	0.108 (8)	0.110 (19)	0.008 (13)	0.025 (16)	−0.016 (10)
C10B	0.12 (2)	0.177 (11)	0.103 (18)	0.015 (12)	−0.002 (16)	−0.003 (12)
O1C	0.091 (16)	0.102 (5)	0.077 (14)	0.000 (6)	−0.005 (14)	0.007 (6)
C1C	0.082 (11)	0.086 (6)	0.081 (11)	0.000 (7)	0.015 (8)	−0.001 (7)
C2C	0.068 (11)	0.074 (5)	0.056 (10)	−0.012 (6)	0.011 (8)	0.002 (6)
C3C	0.071 (11)	0.088 (6)	0.079 (10)	−0.014 (7)	0.008 (8)	0.002 (7)
C4C	0.087 (11)	0.079 (5)	0.062 (10)	0.008 (6)	0.014 (8)	0.006 (6)
C5C	0.088 (11)	0.076 (5)	0.090 (11)	−0.001 (7)	0.026 (8)	0.011 (7)
C6C	0.073 (11)	0.068 (5)	0.069 (10)	−0.003 (6)	0.015 (8)	0.004 (6)
C7C	0.081 (11)	0.089 (6)	0.067 (10)	−0.003 (7)	0.015 (8)	−0.006 (7)
C8C	0.084 (19)	0.132 (9)	0.129 (18)	−0.036 (10)	0.015 (16)	0.024 (10)
C9C	0.15 (2)	0.095 (7)	0.133 (19)	−0.008 (10)	0.044 (16)	−0.023 (10)
C10C	0.126 (19)	0.092 (7)	0.115 (18)	−0.009 (10)	0.035 (16)	0.007 (9)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.45 (3)
O1—H1A	0.83 (2)	C5B—C10B	1.474 (16)
O1—C1	1.33 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.520 (11)	C7B—H7B	0.9800
C1—C6	1.500 (12)	C7B—C8B	1.49 (2)
C2—H2	0.9800	C7B—C9B	1.60 (7)
C2—C3	1.42 (3)	C8B—H8BA	0.9600
C2—C7	1.535 (16)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.498 (12)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.489 (12)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.46 (3)	O1C—H1CA	0.82 (2)
C5—C10	1.522 (14)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.39 (3)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.443 (15)
C7—C8	1.52 (2)	C1C—C6C	1.52 (2)
C7—C9	1.64 (6)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.44 (3)
C8—H8B	0.9600	C2C—C7C	1.53 (2)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9700	C3C—C4C	1.495 (16)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.516 (19)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.53 (3)
O1B—C1B	1.41 (2)	C5C—C10C	1.504 (19)
O1B—H1BA	0.81 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.482 (12)	C7C—H7C	0.9800
C1B—C6B	1.508 (14)	C7C—C8C	1.51 (2)
C2B—H2B	0.9800	C7C—C9C	1.55 (3)
C2B—C3B	1.41 (3)	C8C—H8CA	0.9600
C2B—C7B	1.525 (16)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.473 (14)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.491 (14)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	88.00	C10B—C5B—H5B	103.9
C1—O1—H1B	109.5	C1B—C6B—H6BA	107.9
C1—O1—H1A	113 (10)	C1B—C6B—H6BB	107.9
O1—C1—H1	104.5	C5B—C6B—C1B	117.6 (17)
O1—C1—C2	113.4 (14)	C5B—C6B—H6BA	107.9
O1—C1—C6	116.8 (17)	C5B—C6B—H6BB	107.9
C2—C1—H1	104.5	H6BA—C6B—H6BB	107.2
C6—C1—H1	104.5	C2B—C7B—H7B	107.4
C6—C1—C2	111.6 (7)	C2B—C7B—C9B	109 (3)
C1—C2—H2	102.4	C8B—C7B—C2B	113.5 (13)
C1—C2—C7	113.6 (8)	C8B—C7B—H7B	107.4
C3—C2—C1	113.3 (14)	C8B—C7B—C9B	111.6 (17)
C3—C2—H2	102.4	C9B—C7B—H7B	107.4
C3—C2—C7	119.7 (18)	C7B—C8B—H8BA	109.5
C7—C2—H2	102.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	108.0	C7B—C8B—H8BC	109.5
C2—C3—H3B	108.0	H8BA—C8B—H8BB	109.5
C2—C3—C4	117.4 (16)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.2	H8BB—C8B—H8BC	109.5
C4—C3—H3A	108.0	C7B—C9B—H9BA	109.5
C4—C3—H3B	108.0	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.0	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.0	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.8	H9BA—C9B—H9BC	109.5
C5—C4—C3	112.9 (7)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.0	C5B—C10B—H10D	109.5
C5—C4—H4B	109.0	C5B—C10B—H10E	109.5
C4—C5—H5	104.9	C5B—C10B—H10F	109.5
C4—C5—C10	113.6 (9)	H10D—C10B—H10E	109.5
C6—C5—C4	113.1 (15)	H10D—C10B—H10F	109.5
C6—C5—H5	104.9	H10E—C10B—H10F	109.5
C6—C5—C10	114 (2)	H1CA—O1C—H1C	147.7
C10—C5—H5	104.9	C1C—O1C—H1CA	95 (9)
C1—C6—H6A	107.8	C1C—O1C—H1C	109.5
C1—C6—H6B	107.8	O1C—C1C—H1CB	104.3
C5—C6—C1	117.9 (16)	O1C—C1C—C2C	116 (2)
C5—C6—H6A	107.8	O1C—C1C—C6C	111.2 (11)
C5—C6—H6B	107.8	C2C—C1C—H1CB	104.3
H6A—C6—H6B	107.2	C2C—C1C—C6C	114.8 (10)
C2—C7—H7	109.3	C6C—C1C—H1CB	104.3
C2—C7—C9	108 (3)	C1C—C2C—H2C	102.4
C8—C7—C2	112.2 (11)	C1C—C2C—C3C	118 (2)
C8—C7—H7	109.3	C1C—C2C—C7C	113.7 (10)
C8—C7—C9	108.1 (18)	C3C—C2C—H2C	102.4
C9—C7—H7	109.3	C3C—C2C—C7C	115.1 (10)
C7—C8—H8A	109.5	C7C—C2C—H2C	102.4
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.3
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.3
H8A—C8—H8B	109.5	C2C—C3C—C4C	111.8 (11)
H8A—C8—H8C	109.5	H3CA—C3C—H3CB	107.9
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.3
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.3
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.2
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.2
H9A—C9—H9B	109.5	C3C—C4C—C5C	111.9 (8)
H9A—C9—H9C	109.5	H4CA—C4C—H4CB	107.9
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.2
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.2
C5—C10—H10B	109.5	C4C—C5C—H5C	109.1
C5—C10—H10C	109.5	C4C—C5C—C6C	108 (2)
H10A—C10—H10B	109.5	C6C—C5C—H5C	109.1
H10A—C10—H10C	109.5	C10C—C5C—C4C	111.4 (9)
H10B—C10—H10C	109.5	C10C—C5C—H5C	109.1
H1BB—O1B—H1BA	124.3	C10C—C5C—C6C	110.0 (13)
C1B—O1B—H1BB	109.5	C1C—C6C—C5C	113.6 (12)
C1B—O1B—H1BA	106 (6)	C1C—C6C—H6CA	108.9
O1B—C1B—H1BC	104.9	C1C—C6C—H6CB	108.9
O1B—C1B—C2B	117.7 (17)	C5C—C6C—H6CA	108.9
O1B—C1B—C6B	110.1 (16)	C5C—C6C—H6CB	108.9
C2B—C1B—H1BC	104.9	H6CA—C6C—H6CB	107.7
C2B—C1B—C6B	113.0 (8)	C2C—C7C—H7C	107.7
C6B—C1B—H1BC	104.9	C2C—C7C—C9C	111 (2)
C1B—C2B—H2B	101.4	C8C—C7C—C2C	114.2 (9)
C1B—C2B—C7B	115.0 (9)	C8C—C7C—H7C	107.7
C3B—C2B—C1B	112.6 (16)	C8C—C7C—C9C	107.7 (13)
C3B—C2B—H2B	101.4	C9C—C7C—H7C	107.7
C3B—C2B—C7B	120.8 (18)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	101.4	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	107.6	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	107.6	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	118.9 (17)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	107.0	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	107.6	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	107.6	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.3	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.3	H9CA—C9C—H9CB	109.5
C3B—C4B—C5B	115.9 (8)	H9CA—C9C—H9CC	109.5
H4BA—C4B—H4BB	107.4	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.3	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.3	C5C—C10C—H10H	109.5
C4B—C5B—H5B	103.9	C5C—C10C—H10I	109.5
C6B—C5B—C4B	111.0 (15)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	103.9	H10G—C10C—H10I	109.5
C6B—C5B—C10B	116 (2)	H10H—C10C—H10I	109.5
C10B—C5B—C4B	116.3 (10)

O1—C1—C2—C3	−178.9 (19)	C3B—C2B—C7B—C9B	−63 (2)
O1—C1—C2—C7	40 (3)	C3B—C4B—C5B—C6B	39 (3)
O1—C1—C6—C5	177.4 (18)	C3B—C4B—C5B—C10B	175 (3)
C1—C2—C3—C4	48 (3)	C4B—C5B—C6B—C1B	−43 (3)
C1—C2—C7—C8	−158 (2)	C6B—C1B—C2B—C3B	−45 (4)
C1—C2—C7—C9	82 (3)	C6B—C1B—C2B—C7B	171 (3)
C2—C1—C6—C5	45 (3)	C7B—C2B—C3B—C4B	−174 (2)
C2—C3—C4—C5	−47 (3)	C10B—C5B—C6B—C1B	−179 (2)
C3—C2—C7—C8	63 (4)	O1C—C1C—C2C—C3C	−172.2 (14)
C3—C2—C7—C9	−56 (2)	O1C—C1C—C2C—C7C	49 (3)
C3—C4—C5—C6	43 (3)	O1C—C1C—C6C—C5C	176.7 (19)
C3—C4—C5—C10	176 (3)	C1C—C2C—C3C—C4C	47 (2)
C4—C5—C6—C1	−45 (3)	C1C—C2C—C7C—C8C	−167 (2)
C6—C1—C2—C3	−45 (3)	C1C—C2C—C7C—C9C	70 (2)
C6—C1—C2—C7	174 (3)	C2C—C1C—C6C—C5C	42 (3)
C7—C2—C3—C4	−173.7 (19)	C2C—C3C—C4C—C5C	−57 (3)
C10—C5—C6—C1	−177.1 (18)	C3C—C2C—C7C—C8C	52 (3)
O1B—C1B—C2B—C3B	−175 (2)	C3C—C2C—C7C—C9C	−70.0 (19)
O1B—C1B—C2B—C7B	41 (4)	C3C—C4C—C5C—C6C	58 (2)
O1B—C1B—C6B—C5B	−179 (2)	C3C—C4C—C5C—C10C	179 (2)
C1B—C2B—C3B—C4B	44 (3)	C4C—C5C—C6C—C1C	−51 (2)
C1B—C2B—C7B—C8B	−157 (3)	C6C—C1C—C2C—C3C	−40 (3)
C1B—C2B—C7B—C9B	77 (3)	C6C—C1C—C2C—C7C	−179 (2)
C2B—C1B—C6B—C5B	47 (3)	C7C—C2C—C3C—C4C	−174.8 (19)
C2B—C3B—C4B—C5B	−43 (4)	C10C—C5C—C6C—C1C	−172.7 (19)
C3B—C2B—C7B—C8B	62 (4)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.64GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.064 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.638 (5) Å	Cell parameters from 2311 reflections
b = 21.198 (6) Å	θ = 5.0–26.4°
c = 12.2482 (19) Å	µ = 0.07 mm⁻¹
β = 104.36 (2)°	T = 296 K
V = 2927.4 (16) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	740 reflections with I > 2σ(I)
Detector resolution: 16.2413 pixels mm^-1	R_int = 0.134
ω and π scans	θ_max = 26.3°, θ_min = 5.0°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
T_min = 0.971, T_max = 0.997	k = −21→21
13201 measured reflections	l = −15→14
2311 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.083	w = 1/[σ²(F_o²) + (0.1662P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.301	(Δ/σ)_max < 0.001
S = 0.90	Δρ_max = 0.16 e Å⁻³
2311 reflections	Δρ_min = −0.11 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 restraints	Extinction coefficient: 0.010 (7)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.64 (2) GPa (640000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0081 (6)	0.0644 (3)	0.5036 (4)	0.113 (2)
H1B	0.058871	0.063789	0.493269	0.170*	0.5
H1A	−0.04 (2)	0.033 (4)	0.524 (8)	0.170*	0.5
C1	−0.0048 (8)	0.0943 (4)	0.6095 (5)	0.101 (3)
H1	−0.075722	0.081135	0.633077	0.121*
C2	−0.0097 (8)	0.1663 (4)	0.5952 (6)	0.101 (3)
H2	0.062087	0.179497	0.573156	0.152*
C3	−0.0044 (8)	0.1947 (4)	0.7118 (5)	0.103 (3)
H3A	−0.003151	0.240306	0.706738	0.124*
H3B	−0.075128	0.182634	0.735026	0.124*
C4	0.1046 (8)	0.1726 (5)	0.8000 (6)	0.108 (3)
H4A	0.174987	0.188604	0.780525	0.130*
H4B	0.102363	0.190403	0.872416	0.130*
C5	0.1138 (8)	0.1028 (5)	0.8108 (5)	0.110 (3)
H5	0.046904	0.088353	0.839616	0.132*
C6	0.1021 (7)	0.0724 (3)	0.6980 (5)	0.092 (2)
H6A	0.097329	0.027003	0.706406	0.110*
H6B	0.172883	0.081314	0.672383	0.110*
C7	−0.1165 (11)	0.1864 (5)	0.5016 (6)	0.106 (3)
H7	−0.120394	0.158364	0.437244	0.127*
C8	−0.0915 (10)	0.2536 (5)	0.4651 (7)	0.154 (4)
H8A	−0.015479	0.254498	0.447799	0.231*
H8B	−0.151863	0.265444	0.399472	0.231*
H8C	−0.091717	0.282647	0.525139	0.231*
C9	−0.2357 (10)	0.1844 (4)	0.5290 (7)	0.123 (3)
H9A	−0.253078	0.141848	0.546499	0.184*
H9B	−0.295634	0.198957	0.465209	0.184*
H9C	−0.234366	0.211051	0.592623	0.184*
C10	0.2280 (9)	0.0842 (4)	0.8978 (5)	0.128 (3)
H10A	0.232736	0.039059	0.903879	0.191*
H10B	0.295409	0.099878	0.874221	0.191*
H10C	0.227386	0.101955	0.969762	0.191*
O1B	0.1956 (6)	0.0541 (3)	0.4318 (4)	0.123 (2)
H1BB	0.135305	0.059063	0.454019	0.185*	0.5
H1CA	0.355 (7)	0.034 (11)	0.498 (10)	0.185*	0.5
C1B	0.1879 (8)	0.0914 (5)	0.3319 (6)	0.104 (3)
H1BC	0.255941	0.080181	0.302031	0.124*
C2B	0.1968 (8)	0.1593 (5)	0.3579 (6)	0.101 (3)
H2B	0.124542	0.169950	0.381345	0.121*
C3B	0.1883 (9)	0.1952 (4)	0.2483 (6)	0.120 (3)
H3BA	0.186806	0.240163	0.262819	0.144*
H3BB	0.258086	0.186375	0.221042	0.144*
C4B	0.0778 (9)	0.1772 (5)	0.1579 (6)	0.133 (3)
H4BA	0.008995	0.193960	0.179392	0.160*
H4BB	0.081628	0.197451	0.087885	0.160*
C5B	0.0596 (9)	0.1085 (5)	0.1367 (6)	0.116 (3)
H5B	0.123677	0.095052	0.102980	0.139*
C6B	0.0799 (8)	0.0740 (4)	0.2459 (5)	0.103 (3)
H6BA	0.012015	0.080946	0.277029	0.124*
H6BB	0.083218	0.029158	0.230809	0.124*
C7B	0.2973 (11)	0.1788 (5)	0.4534 (7)	0.117 (3)
H7B	0.298851	0.147890	0.513218	0.141*
C8B	0.2773 (10)	0.2416 (5)	0.5030 (7)	0.154 (4)
H8BA	0.344398	0.251705	0.563709	0.230*
H8BB	0.267449	0.273542	0.445892	0.230*
H8BC	0.207273	0.239464	0.530882	0.230*
C9B	0.4197 (10)	0.1760 (4)	0.4310 (7)	0.123 (3)
H9BA	0.477825	0.189394	0.497116	0.184*
H9BB	0.436423	0.133544	0.412617	0.184*
H9BC	0.422257	0.203375	0.369216	0.184*
C10B	−0.0534 (9)	0.0913 (4)	0.0523 (6)	0.147 (4)
H10D	−0.119964	0.103633	0.080609	0.220*
H10E	−0.055640	0.046602	0.039794	0.220*
H10F	−0.056786	0.112836	−0.017400	0.220*
O1C	0.4107 (5)	0.0204 (2)	0.5470 (3)	0.108 (2)
H1C	0.467841	0.004884	0.528952	0.162*	0.5
H1BA	0.262 (5)	0.042 (7)	0.450 (8)	0.162*	0.5
C1C	0.4175 (9)	0.0063 (4)	0.6616 (5)	0.104 (3)
H1CB	0.365952	0.037115	0.685641	0.125*
C2C	0.5322 (8)	0.0144 (4)	0.7371 (5)	0.103 (3)
H2C	0.582577	−0.015057	0.708238	0.124*
C3C	0.5408 (8)	−0.0086 (4)	0.8553 (5)	0.105 (3)
H3CA	0.623526	−0.008904	0.896513	0.127*
H3CB	0.499389	0.020831	0.892673	0.127*
C4C	0.4901 (10)	−0.0733 (4)	0.8606 (6)	0.121 (3)
H4CA	0.541061	−0.104108	0.837371	0.145*
H4CB	0.489134	−0.082608	0.937900	0.145*
C5C	0.3731 (9)	−0.0793 (4)	0.7908 (6)	0.111 (3)
H5C	0.325297	−0.049311	0.821506	0.133*
C6C	0.3609 (8)	−0.0588 (4)	0.6714 (5)	0.100 (3)
H6CA	0.277393	−0.057074	0.633027	0.150*
H6CB	0.397990	−0.090030	0.633375	0.150*
C7C	0.5910 (12)	0.0811 (5)	0.7285 (6)	0.105 (3)
H7C	0.583345	0.090077	0.648556	0.126*
C8C	0.7191 (11)	0.0812 (4)	0.7861 (9)	0.153 (4)
H8CA	0.758695	0.048868	0.754285	0.229*
H8CB	0.728927	0.073153	0.865017	0.229*
H8CC	0.752597	0.121503	0.776231	0.229*
C9C	0.5245 (10)	0.1317 (5)	0.7746 (7)	0.145 (4)
H9CA	0.527240	0.122717	0.851993	0.218*
H9CB	0.443476	0.132604	0.731535	0.218*
H9CC	0.560699	0.171931	0.769443	0.218*
C10C	0.3145 (9)	−0.1444 (5)	0.7969 (6)	0.138 (4)
H10G	0.236232	−0.144586	0.747682	0.207*
H10H	0.361380	−0.176764	0.774093	0.207*
H10I	0.309671	−0.152222	0.872867	0.207*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.143 (7)	0.097 (6)	0.094 (3)	−0.001 (3)	0.019 (3)	−0.012 (3)
C1	0.109 (8)	0.105 (7)	0.081 (4)	−0.002 (4)	0.010 (4)	−0.012 (4)
C2	0.098 (8)	0.103 (7)	0.105 (5)	−0.005 (4)	0.030 (4)	0.002 (4)
C3	0.110 (8)	0.092 (6)	0.103 (4)	0.006 (4)	0.016 (4)	−0.015 (4)
C4	0.109 (8)	0.115 (7)	0.096 (4)	0.005 (4)	0.015 (4)	−0.006 (5)
C5	0.121 (8)	0.122 (7)	0.085 (4)	0.011 (5)	0.020 (4)	0.017 (5)
C6	0.091 (7)	0.096 (6)	0.088 (4)	−0.005 (4)	0.021 (4)	−0.006 (4)
C7	0.115 (8)	0.103 (7)	0.100 (5)	−0.003 (5)	0.025 (5)	0.003 (4)
C8	0.141 (12)	0.132 (11)	0.177 (7)	0.006 (6)	0.016 (6)	0.028 (7)
C9	0.103 (12)	0.138 (10)	0.125 (6)	−0.006 (5)	0.024 (6)	−0.012 (5)
C10	0.144 (11)	0.148 (9)	0.089 (4)	0.014 (5)	0.026 (5)	0.005 (4)
O1B	0.118 (8)	0.137 (7)	0.112 (3)	0.014 (4)	0.023 (4)	0.039 (3)
C1B	0.106 (8)	0.103 (7)	0.093 (5)	0.006 (4)	0.007 (4)	0.018 (5)
C2B	0.104 (8)	0.096 (7)	0.095 (4)	0.004 (4)	0.012 (4)	−0.009 (5)
C3B	0.121 (8)	0.109 (7)	0.131 (5)	0.009 (4)	0.030 (5)	0.014 (5)
C4B	0.142 (9)	0.137 (8)	0.111 (5)	0.009 (5)	0.015 (5)	0.033 (5)
C5B	0.117 (8)	0.129 (7)	0.102 (5)	0.002 (5)	0.027 (5)	0.010 (5)
C6B	0.110 (8)	0.093 (7)	0.096 (4)	0.000 (4)	0.006 (4)	0.011 (4)
C7B	0.125 (9)	0.110 (7)	0.119 (5)	0.013 (5)	0.033 (6)	−0.012 (5)
C8B	0.139 (12)	0.146 (11)	0.180 (7)	−0.004 (6)	0.049 (6)	−0.062 (6)
C9B	0.103 (11)	0.126 (10)	0.139 (6)	0.017 (5)	0.032 (6)	0.006 (5)
C10B	0.139 (12)	0.187 (11)	0.099 (5)	0.005 (6)	0.001 (6)	−0.018 (5)
O1C	0.120 (7)	0.124 (6)	0.074 (3)	0.007 (3)	0.012 (3)	0.015 (3)
C1C	0.122 (8)	0.112 (7)	0.072 (4)	−0.005 (4)	0.011 (4)	0.013 (4)
C2C	0.113 (8)	0.105 (7)	0.078 (4)	−0.001 (4)	−0.003 (4)	0.006 (4)
C3C	0.128 (8)	0.109 (7)	0.074 (4)	−0.009 (5)	0.012 (4)	0.009 (4)
C4C	0.135 (8)	0.120 (8)	0.095 (4)	−0.002 (5)	0.006 (5)	0.021 (4)
C5C	0.113 (8)	0.123 (8)	0.091 (4)	−0.006 (5)	0.018 (5)	0.025 (4)
C6C	0.112 (7)	0.099 (7)	0.086 (4)	−0.004 (4)	0.019 (4)	0.005 (4)
C7C	0.118 (8)	0.106 (8)	0.088 (4)	−0.003 (5)	0.023 (5)	0.001 (4)
C8C	0.116 (12)	0.155 (12)	0.174 (7)	−0.010 (6)	0.009 (7)	0.010 (6)
C9C	0.152 (12)	0.133 (11)	0.165 (7)	−0.008 (6)	0.069 (7)	−0.005 (6)
C10C	0.169 (12)	0.124 (10)	0.124 (5)	−0.018 (6)	0.043 (6)	0.022 (5)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.491 (9)
O1—H1A	0.81 (2)	C5B—C10B	1.502 (11)
O1—C1	1.435 (7)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.537 (9)	C7B—H7B	0.9800
C1—C6	1.507 (9)	C7B—C8B	1.504 (10)
C2—H2	0.9800	C7B—C9B	1.516 (11)
C2—C3	1.535 (9)	C8B—H8BA	0.9600
C2—C7	1.528 (12)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.521 (9)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.486 (9)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.501 (9)	O1C—H1CA	0.82 (2)
C5—C10	1.535 (10)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.418 (7)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.433 (10)
C7—C8	1.542 (10)	C1C—C6C	1.545 (10)
C7—C9	1.506 (10)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.508 (9)
C8—H8B	0.9600	C2C—C7C	1.585 (12)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.500 (10)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.423 (11)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.498 (8)
O1B—C1B	1.441 (8)	C5C—C10C	1.549 (10)
O1B—H1BA	0.80 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.472 (9)	C7C—H7C	0.9800
C1B—C6B	1.473 (10)	C7C—C8C	1.483 (12)
C2B—H2B	0.9800	C7C—C9C	1.512 (12)
C2B—C3B	1.525 (9)	C8C—H8CA	0.9600
C2B—C7B	1.493 (11)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.523 (11)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.486 (10)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	123.00	C10B—C5B—H5B	105.5
C1—O1—H1B	109.5	C1B—C6B—C5B	115.8 (7)
C1—O1—H1A	90.1 (16)	C1B—C6B—H6BA	108.3
O1—C1—H1	107.8	C1B—C6B—H6BB	108.3
O1—C1—C2	110.1 (6)	C5B—C6B—H6BA	108.3
O1—C1—C6	110.3 (7)	C5B—C6B—H6BB	108.3
C2—C1—H1	107.8	H6BA—C6B—H6BB	107.4
C6—C1—H1	107.8	C2B—C7B—H7B	105.4
C6—C1—C2	112.9 (6)	C2B—C7B—C8B	113.0 (8)
C1—C2—H2	107.7	C2B—C7B—C9B	115.9 (8)
C3—C2—C1	106.9 (6)	C8B—C7B—H7B	105.4
C3—C2—H2	107.7	C8B—C7B—C9B	110.7 (8)
C7—C2—C1	111.2 (7)	C9B—C7B—H7B	105.4
C7—C2—H2	107.7	C7B—C8B—H8BA	109.5
C7—C2—C3	115.2 (7)	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.2	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.2	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	107.9	H8BA—C8B—H8BC	109.5
C4—C3—C2	112.0 (6)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.2	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.2	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.9	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.9	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.7	H9BA—C9B—H9BC	109.5
C5—C4—C3	113.5 (6)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.9	C5B—C10B—H10D	109.5
C5—C4—H4B	108.9	C5B—C10B—H10E	109.5
C4—C5—H5	107.3	C5B—C10B—H10F	109.5
C4—C5—C6	111.0 (6)	H10D—C10B—H10E	109.5
C4—C5—C10	110.4 (7)	H10D—C10B—H10F	109.5
C6—C5—H5	107.3	H10E—C10B—H10F	109.5
C6—C5—C10	113.1 (7)	H1CA—O1C—H1C	119.6
C10—C5—H5	107.3	C1C—O1C—H1CA	129 (9)
C1—C6—H6A	108.9	C1C—O1C—H1C	109.5
C1—C6—H6B	108.9	O1C—C1C—H1CB	105.6
C5—C6—C1	113.6 (7)	O1C—C1C—C2C	115.3 (7)
C5—C6—H6A	108.9	O1C—C1C—C6C	110.1 (6)
C5—C6—H6B	108.9	C2C—C1C—H1CB	105.6
H6A—C6—H6B	107.7	C2C—C1C—C6C	113.8 (6)
C2—C7—H7	107.5	C6C—C1C—H1CB	105.6
C2—C7—C8	107.3 (8)	C1C—C2C—H2C	103.7
C8—C7—H7	107.5	C1C—C2C—C3C	114.2 (7)
C9—C7—C2	116.6 (7)	C1C—C2C—C7C	114.4 (7)
C9—C7—H7	107.5	C3C—C2C—H2C	103.7
C9—C7—C8	110.0 (8)	C3C—C2C—C7C	115.1 (6)
C7—C8—H8A	109.5	C7C—C2C—H2C	103.7
C7—C8—H8B	109.5	C2C—C3C—H3CA	108.8
C7—C8—H8C	109.5	C2C—C3C—H3CB	108.8
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.7
H8A—C8—H8C	109.5	C4C—C3C—C2C	113.8 (6)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	108.8
C7—C9—H9A	109.5	C4C—C3C—H3CB	108.8
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.1
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.1
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.8
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.5 (7)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.1
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.1
C5—C10—H10B	109.5	C4C—C5C—H5C	105.1
C5—C10—H10C	109.5	C4C—C5C—C6C	113.9 (8)
H10A—C10—H10B	109.5	C4C—C5C—C10C	114.7 (8)
H10A—C10—H10C	109.5	C6C—C5C—H5C	105.1
H10B—C10—H10C	109.5	C6C—C5C—C10C	111.7 (7)
H1BB—O1B—H1BA	143.4	C10C—C5C—H5C	105.1
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.9
C1B—O1B—H1BA	106 (5)	C1C—C6C—H6CB	108.9
O1B—C1B—H1BC	107.3	C5C—C6C—C1C	113.3 (6)
O1B—C1B—C2B	111.4 (6)	C5C—C6C—H6CA	108.9
O1B—C1B—C6B	109.4 (7)	C5C—C6C—H6CB	108.9
C2B—C1B—H1BC	107.3	H6CA—C6C—H6CB	107.7
C2B—C1B—C6B	113.7 (6)	C2C—C7C—H7C	107.8
C6B—C1B—H1BC	107.3	C8C—C7C—C2C	111.7 (7)
C1B—C2B—H2B	105.6	C8C—C7C—H7C	107.8
C1B—C2B—C3B	108.2 (6)	C8C—C7C—C9C	111.6 (8)
C1B—C2B—C7B	116.1 (7)	C9C—C7C—C2C	109.8 (11)
C3B—C2B—H2B	105.6	C9C—C7C—H7C	107.8
C7B—C2B—H2B	105.6	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	114.7 (8)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.2	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.2	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	107.9	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	111.9 (7)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.2	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.2	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.4	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.4	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.5	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	115.5 (7)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.4	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.4	C5C—C10C—H10H	109.5
C4B—C5B—H5B	105.5	C5C—C10C—H10I	109.5
C4B—C5B—C6B	109.9 (7)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	114.8 (7)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	105.5	H10H—C10C—H10I	109.5
C6B—C5B—C10B	114.6 (8)

O1—C1—C2—C3	−179.4 (7)	C3B—C2B—C7B—C9B	−55.5 (11)
O1—C1—C2—C7	54.1 (9)	C3B—C4B—C5B—C6B	45.7 (10)
O1—C1—C6—C5	178.4 (6)	C3B—C4B—C5B—C10B	176.5 (8)
C1—C2—C3—C4	56.0 (9)	C4B—C5B—C6B—C1B	−46.9 (10)
C1—C2—C7—C8	−160.5 (7)	C6B—C1B—C2B—C3B	−56.0 (9)
C1—C2—C7—C9	75.7 (9)	C6B—C1B—C2B—C7B	173.4 (8)
C2—C1—C6—C5	54.8 (10)	C7B—C2B—C3B—C4B	−174.8 (9)
C2—C3—C4—C5	−56.5 (9)	C10B—C5B—C6B—C1B	−177.9 (8)
C3—C2—C7—C8	77.6 (10)	O1C—C1C—C2C—C3C	−172.7 (7)
C3—C2—C7—C9	−46.2 (11)	O1C—C1C—C2C—C7C	51.7 (11)
C3—C4—C5—C6	51.5 (8)	O1C—C1C—C6C—C5C	175.5 (7)
C3—C4—C5—C10	177.8 (7)	C1C—C2C—C3C—C4C	47.8 (11)
C4—C5—C6—C1	−50.7 (10)	C1C—C2C—C7C—C8C	−165.8 (8)
C6—C1—C2—C3	−55.7 (8)	C1C—C2C—C7C—C9C	69.8 (9)
C6—C1—C2—C7	177.7 (8)	C2C—C1C—C6C—C5C	44.3 (12)
C7—C2—C3—C4	−179.8 (8)	C2C—C3C—C4C—C5C	−51.3 (11)
C10—C5—C6—C1	−175.5 (8)	C3C—C2C—C7C—C8C	59.0 (12)
O1B—C1B—C2B—C3B	179.8 (7)	C3C—C2C—C7C—C9C	−65.4 (11)
O1B—C1B—C2B—C7B	49.2 (9)	C3C—C4C—C5C—C6C	52.0 (11)
O1B—C1B—C6B—C5B	−179.7 (7)	C3C—C4C—C5C—C10C	−177.5 (8)
C1B—C2B—C3B—C4B	53.8 (9)	C4C—C5C—C6C—C1C	−48.5 (11)
C1B—C2B—C7B—C8B	−158.7 (8)	C6C—C1C—C2C—C3C	−44.1 (11)
C1B—C2B—C7B—C9B	71.9 (9)	C6C—C1C—C2C—C7C	−179.7 (7)
C2B—C1B—C6B—C5B	55.0 (10)	C7C—C2C—C3C—C4C	−176.9 (9)
C2B—C3B—C4B—C5B	−51.5 (10)	C10C—C5C—C6C—C1C	179.5 (9)
C3B—C2B—C7B—C8B	73.8 (11)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.67GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.072 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.745 (5) Å	Cell parameters from 1202 reflections
b = 21.172 (3) Å	θ = 3.4–22.0°
c = 12.054 (8) Å	µ = 0.07 mm⁻¹
β = 104.29 (7)°	T = 296 K
V = 2905 (3) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	584 reflections with I > 2σ(I)
Detector resolution: 16.2413 pixels mm^-1	R_int = 0.276
ω and π scans	θ_max = 22.0°, θ_min = 3.4°
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
T_min = 0.971, T_max = 0.999	k = −21→22
20654 measured reflections	l = −9→9
1202 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.100	w = 1/[σ²(F_o²) + (0.1098P)² + 11.5695P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.307	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.11 e Å⁻³
1202 reflections	Δρ_min = −0.11 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
205 restraints	Extinction coefficient: 0.005 (3)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.67 (2) GPa (670000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0052 (14)	0.0648 (4)	0.5045 (16)	0.070 (6)
H1B	0.061364	0.064448	0.494570	0.105*	0.5
H1A	−0.056 (18)	0.037 (11)	0.50 (4)	0.105*	0.5
C1	−0.0028 (19)	0.0932 (6)	0.614 (2)	0.066 (5)
H1	−0.072149	0.079323	0.638444	0.079*
C2	−0.0092 (19)	0.1644 (5)	0.596 (2)	0.061 (5)
H2	0.063661	0.176787	0.575938	0.092*
C3	−0.0049 (18)	0.1940 (6)	0.712 (2)	0.067 (5)
H3A	−0.006292	0.239708	0.705599	0.080*
H3B	−0.073067	0.180961	0.738293	0.080*
C4	0.1037 (18)	0.1739 (6)	0.796 (2)	0.074 (5)
H4A	0.170935	0.190645	0.772395	0.089*
H4B	0.104219	0.191962	0.869951	0.089*
C5	0.117 (2)	0.1051 (6)	0.808 (2)	0.080 (6)
H5	0.051248	0.090541	0.838817	0.096*
C6	0.1052 (18)	0.0724 (5)	0.700 (2)	0.055 (5)
H6A	0.101321	0.027248	0.712392	0.066*
H6B	0.173844	0.080827	0.671434	0.066*
C7	−0.110 (2)	0.1871 (6)	0.497 (3)	0.065 (5)
H7	−0.111962	0.160345	0.430713	0.078*
C8	−0.093 (2)	0.2540 (6)	0.465 (2)	0.092 (6)
H8A	−0.018640	0.257763	0.445475	0.138*
H8B	−0.154940	0.265757	0.400306	0.138*
H8C	−0.093739	0.281297	0.528293	0.138*
C9	−0.228 (2)	0.1804 (7)	0.529 (3)	0.092 (7)
H9A	−0.237698	0.137390	0.549632	0.139*
H9B	−0.290012	0.191814	0.464003	0.139*
H9C	−0.228917	0.207660	0.591886	0.139*
C10	0.229 (2)	0.0857 (7)	0.896 (3)	0.108 (8)
H10A	0.234470	0.108044	0.966382	0.162*
H10B	0.227850	0.041079	0.909650	0.162*
H10C	0.296191	0.095845	0.866955	0.162*
O1B	0.1936 (14)	0.0513 (4)	0.4279 (16)	0.080 (6)
H1BA	0.133714	0.056109	0.450417	0.120*	0.5
H1BB	0.25 (2)	0.066 (12)	0.474 (11)	0.120*	0.5
C1B	0.188 (2)	0.0899 (6)	0.329 (2)	0.073 (5)
H1BC	0.253063	0.078553	0.296016	0.087*
C2B	0.194 (2)	0.1597 (7)	0.354 (3)	0.092 (6)
H2B	0.122058	0.170114	0.377925	0.110*
C3B	0.185 (2)	0.1945 (6)	0.241 (2)	0.086 (6)
H3BA	0.187355	0.239674	0.254199	0.104*
H3BB	0.251013	0.183159	0.210345	0.104*
C4B	0.072 (2)	0.1776 (7)	0.155 (3)	0.113 (7)
H4BA	0.005429	0.191941	0.182864	0.135*
H4BB	0.068893	0.198871	0.083108	0.135*
C5B	0.063 (2)	0.1085 (7)	0.136 (3)	0.091 (6)
H5B	0.126296	0.095017	0.100999	0.109*
C6B	0.072 (2)	0.0717 (6)	0.243 (2)	0.077 (5)
H6BA	0.070858	0.026781	0.227191	0.093*
H6BB	0.005505	0.081379	0.275021	0.093*
C7B	0.294 (2)	0.1787 (7)	0.453 (3)	0.082 (6)
H7B	0.295443	0.148510	0.514427	0.099*
C8B	0.280 (2)	0.2430 (6)	0.499 (2)	0.098 (7)
H8BA	0.346769	0.252154	0.561589	0.148*
H8BB	0.274608	0.273960	0.440289	0.148*
H8BC	0.209908	0.243910	0.526687	0.148*
C9B	0.413 (2)	0.1728 (7)	0.423 (3)	0.093 (7)
H9BA	0.420315	0.131422	0.392731	0.139*
H9BB	0.418211	0.203948	0.366105	0.139*
H9BC	0.475056	0.179517	0.490194	0.139*
C10B	−0.057 (3)	0.0935 (11)	0.052 (3)	0.138 (9)
H10D	−0.118604	0.098370	0.091664	0.207*
H10E	−0.057038	0.050857	0.025418	0.207*
H10F	−0.070614	0.122021	−0.011400	0.207*
O1C	0.4132 (16)	0.0224 (5)	0.5438 (19)	0.081 (6)
H1CA	0.471133	0.006323	0.528719	0.122*	0.5
H1C	0.343 (6)	0.031 (15)	0.53 (4)	0.122*	0.5
C1C	0.412 (2)	0.0072 (6)	0.666 (3)	0.072 (6)
H1CB	0.362237	0.037329	0.693336	0.087*
C2C	0.5359 (18)	0.0138 (5)	0.734 (2)	0.059 (5)
H2C	0.581204	−0.016542	0.700781	0.071*
C3C	0.542 (2)	−0.0092 (6)	0.850 (2)	0.072 (5)
H3CA	0.498194	0.019343	0.886678	0.086*
H3CB	0.623467	−0.008253	0.893615	0.086*
C4C	0.4957 (17)	−0.0743 (5)	0.854 (2)	0.068 (5)
H4CA	0.542329	−0.103650	0.821756	0.082*
H4CB	0.501923	−0.086249	0.932781	0.082*
C5C	0.371 (2)	−0.0780 (6)	0.788 (3)	0.081 (6)
H5C	0.327272	−0.047177	0.822034	0.098*
C6C	0.3635 (19)	−0.0571 (5)	0.665 (2)	0.062 (5)
H6CA	0.407315	−0.086174	0.628964	0.093*
H6CB	0.282163	−0.057440	0.621291	0.093*
C7C	0.590 (2)	0.0782 (6)	0.722 (2)	0.075 (5)
H7C	0.585521	0.086394	0.640637	0.090*
C8C	0.715 (2)	0.0821 (8)	0.789 (3)	0.103 (8)
H8CA	0.761651	0.053482	0.757442	0.155*
H8CB	0.719423	0.070844	0.867261	0.155*
H8CC	0.742995	0.124401	0.785929	0.155*
C9C	0.524 (2)	0.1321 (7)	0.770 (3)	0.103 (8)
H9CA	0.525975	0.123194	0.848507	0.154*
H9CB	0.444407	0.134370	0.725949	0.154*
H9CC	0.562834	0.171656	0.765411	0.154*
C10C	0.3163 (19)	−0.1439 (6)	0.797 (2)	0.095 (7)
H10G	0.235968	−0.143980	0.753699	0.143*
H10H	0.359470	−0.175503	0.767625	0.143*
H10I	0.319417	−0.153042	0.876004	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.072 (8)	0.066 (5)	0.076 (9)	0.004 (5)	0.025 (7)	−0.006 (6)
C1	0.066 (6)	0.066 (6)	0.066 (7)	0.000 (4)	0.017 (4)	−0.004 (4)
C2	0.062 (6)	0.060 (5)	0.062 (6)	0.000 (4)	0.017 (4)	0.000 (4)
C3	0.068 (6)	0.066 (5)	0.068 (6)	−0.001 (4)	0.018 (4)	−0.002 (4)
C4	0.073 (6)	0.075 (6)	0.073 (7)	−0.005 (4)	0.017 (4)	−0.006 (4)
C5	0.080 (7)	0.080 (6)	0.081 (7)	0.000 (4)	0.020 (4)	−0.001 (4)
C6	0.056 (6)	0.054 (5)	0.057 (6)	0.001 (4)	0.016 (4)	0.000 (4)
C7	0.066 (6)	0.064 (5)	0.066 (7)	−0.001 (4)	0.018 (4)	−0.002 (4)
C8	0.092 (6)	0.091 (6)	0.092 (6)	0.001 (2)	0.023 (2)	0.001 (2)
C9	0.088 (10)	0.096 (8)	0.092 (11)	−0.002 (7)	0.020 (8)	−0.003 (7)
C10	0.106 (10)	0.114 (8)	0.103 (11)	0.004 (7)	0.023 (8)	0.003 (8)
O1B	0.075 (8)	0.085 (5)	0.078 (9)	0.003 (5)	0.015 (7)	0.014 (6)
C1B	0.076 (6)	0.070 (6)	0.074 (7)	0.001 (4)	0.021 (4)	0.004 (4)
C2B	0.092 (7)	0.091 (6)	0.092 (7)	0.002 (4)	0.023 (4)	−0.001 (4)
C3B	0.088 (7)	0.085 (6)	0.087 (7)	0.001 (4)	0.022 (4)	0.003 (4)
C4B	0.112 (8)	0.113 (7)	0.112 (8)	0.004 (4)	0.027 (4)	0.004 (4)
C5B	0.089 (7)	0.093 (6)	0.089 (7)	−0.001 (4)	0.021 (4)	0.002 (4)
C6B	0.077 (6)	0.077 (6)	0.077 (7)	0.003 (4)	0.019 (4)	0.005 (4)
C7B	0.083 (7)	0.081 (6)	0.083 (7)	0.000 (4)	0.021 (4)	0.000 (4)
C8B	0.098 (10)	0.097 (8)	0.102 (11)	−0.010 (7)	0.028 (8)	−0.010 (8)
C9B	0.091 (10)	0.094 (8)	0.095 (11)	0.003 (7)	0.023 (8)	−0.001 (7)
C10B	0.130 (11)	0.148 (10)	0.132 (12)	0.002 (8)	0.026 (8)	0.000 (8)
O1C	0.078 (8)	0.089 (6)	0.075 (10)	−0.008 (6)	0.016 (7)	0.007 (7)
C1C	0.072 (7)	0.071 (6)	0.074 (7)	0.003 (4)	0.018 (4)	0.001 (4)
C2C	0.059 (6)	0.059 (5)	0.059 (6)	0.002 (4)	0.015 (4)	0.001 (4)
C3C	0.071 (6)	0.073 (6)	0.070 (7)	0.000 (4)	0.017 (4)	0.001 (4)
C4C	0.071 (6)	0.068 (5)	0.066 (6)	0.002 (4)	0.017 (4)	0.002 (4)
C5C	0.082 (7)	0.079 (6)	0.083 (7)	−0.001 (4)	0.022 (4)	−0.001 (4)
C6C	0.064 (6)	0.061 (5)	0.063 (6)	0.000 (4)	0.017 (4)	0.000 (4)
C7C	0.075 (6)	0.076 (6)	0.073 (7)	−0.002 (4)	0.018 (4)	0.000 (4)
C8C	0.098 (10)	0.109 (8)	0.102 (11)	−0.003 (7)	0.024 (8)	0.001 (8)
C9C	0.109 (10)	0.096 (8)	0.107 (11)	−0.005 (7)	0.032 (8)	−0.002 (8)
C10C	0.100 (10)	0.089 (7)	0.099 (11)	−0.006 (7)	0.030 (8)	−0.002 (7)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.49 (4)
O1—H1A	0.82 (2)	C5B—C10B	1.55 (2)
O1—C1	1.44 (3)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.523 (17)	C7B—H7B	0.9800
C1—C6	1.496 (16)	C7B—C8B	1.50 (3)
C2—H2	0.9800	C7B—C9B	1.53 (5)
C2—C3	1.53 (4)	C8B—H8BA	0.9600
C2—C7	1.532 (19)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.481 (15)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9700
C4—C5	1.467 (16)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.45 (3)	O1C—H1CA	0.8200
C5—C10	1.532 (18)	O1C—H1C	0.82 (2)
C6—H6A	0.9700	O1C—C1C	1.51 (5)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.49 (2)
C7—C8	1.50 (2)	C1C—C6C	1.48 (2)
C7—C9	1.52 (5)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.47 (4)
C8—H8B	0.9600	C2C—C7C	1.53 (2)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.49 (2)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.48 (2)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BA	0.8200	C5C—C6C	1.53 (4)
O1B—H1BB	0.82 (2)	C5C—C10C	1.55 (2)
O1B—C1B	1.43 (3)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.508 (19)	C7C—H7C	0.9800
C1B—C6B	1.541 (17)	C7C—C8C	1.49 (2)
C2B—H2B	0.9800	C7C—C9C	1.57 (4)
C2B—C3B	1.53 (4)	C8C—H8CA	0.9600
C2B—C7B	1.51 (2)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.510 (17)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.481 (18)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	132.3	C10B—C5B—H5B	109.0
C1—O1—H1B	109.5	C1B—C6B—H6BA	110.1
C1—O1—H1A	102.00	C1B—C6B—H6BB	110.1
O1—C1—H1	108.9	C5B—C6B—C1B	108 (2)
O1—C1—C2	107 (2)	C5B—C6B—H6BA	110.1
O1—C1—C6	110 (2)	C5B—C6B—H6BB	110.1
C2—C1—H1	108.9	H6BA—C6B—H6BB	108.4
C6—C1—H1	108.9	C2B—C7B—H7B	106.6
C6—C1—C2	113.2 (10)	C2B—C7B—C9B	112 (3)
C1—C2—H2	106.4	C8B—C7B—C2B	113.6 (15)
C1—C2—C3	107 (2)	C8B—C7B—H7B	106.6
C1—C2—C7	114.9 (10)	C8B—C7B—C9B	110.8 (18)
C3—C2—H2	106.4	C9B—C7B—H7B	106.6
C3—C2—C7	115 (2)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.4	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.7	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.7	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.2	H8BA—C8B—H8BC	109.5
C4—C3—C2	110 (2)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.7	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.7	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.8	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.8	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.7	H9BA—C9B—H9BC	109.5
C5—C4—C3	113.9 (11)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.8	C5B—C10B—H10D	109.5
C5—C4—H4B	108.8	C5B—C10B—H10E	109.5
C4—C5—H5	106.2	C5B—C10B—H10F	109.5
C4—C5—C10	112.7 (11)	H10D—C10B—H10E	109.5
C6—C5—C4	113 (2)	H10D—C10B—H10F	109.5
C6—C5—H5	106.2	H10E—C10B—H10F	109.5
C6—C5—C10	111 (2)	H1CA—O1C—H1C	153.00
C10—C5—H5	106.2	C1C—O1C—H1CA	109.5
C1—C6—H6A	109.4	C1C—O1C—H1C	90.00
C1—C6—H6B	109.4	O1C—C1C—H1CB	109.8
C5—C6—C1	111.1 (19)	C2C—C1C—O1C	106 (3)
C5—C6—H6A	109.4	C2C—C1C—H1CB	109.8
C5—C6—H6B	109.4	C6C—C1C—O1C	106.5 (18)
H6A—C6—H6B	108.0	C6C—C1C—H1CB	109.8
C2—C7—H7	108.1	C6C—C1C—C2C	114.6 (12)
C8—C7—C2	111.7 (12)	C1C—C2C—H2C	105.5
C8—C7—H7	108.1	C1C—C2C—C7C	113.7 (11)
C8—C7—C9	110.1 (18)	C3C—C2C—C1C	108 (3)
C9—C7—C2	111 (3)	C3C—C2C—H2C	105.5
C9—C7—H7	108.1	C3C—C2C—C7C	117.8 (15)
C7—C8—H8A	109.5	C7C—C2C—H2C	105.5
C7—C8—H8B	109.5	C2C—C3C—H3CA	108.8
C7—C8—H8C	109.5	C2C—C3C—H3CB	108.8
H8A—C8—H8B	109.5	C2C—C3C—C4C	113.9 (15)
H8A—C8—H8C	109.5	H3CA—C3C—H3CB	107.7
H8B—C8—H8C	109.5	C4C—C3C—H3CA	108.8
C7—C9—H9A	109.5	C4C—C3C—H3CB	108.8
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.5
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.5
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	108.1
H9A—C9—H9C	109.5	C5C—C4C—C3C	110.7 (11)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.5
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.5
C5—C10—H10B	109.5	C4C—C5C—H5C	107.3
C5—C10—H10C	109.5	C4C—C5C—C6C	108 (3)
H10A—C10—H10B	109.5	C4C—C5C—C10C	112.6 (12)
H10A—C10—H10C	109.5	C6C—C5C—H5C	107.3
H10B—C10—H10C	109.5	C6C—C5C—C10C	113.5 (16)
H1BA—O1B—H1BB	110.00	C10C—C5C—H5C	107.3
C1B—O1B—H1BA	109.5	C1C—C6C—C5C	109.1 (18)
C1B—O1B—H1BB	103 (4)	C1C—C6C—H6CA	109.9
O1B—C1B—H1BC	108.5	C1C—C6C—H6CB	109.9
O1B—C1B—C2B	114 (2)	C5C—C6C—H6CA	109.9
O1B—C1B—C6B	105.7 (18)	C5C—C6C—H6CB	109.9
C2B—C1B—H1BC	108.5	H6CA—C6C—H6CB	108.3
C2B—C1B—C6B	111.8 (12)	C2C—C7C—H7C	109.5
C6B—C1B—H1BC	108.5	C2C—C7C—C9C	111 (3)
C1B—C2B—H2B	106.0	C8C—C7C—C2C	111.7 (12)
C1B—C2B—C3B	108 (2)	C8C—C7C—H7C	109.5
C3B—C2B—H2B	106.0	C8C—C7C—C9C	105.2 (18)
C7B—C2B—C1B	114.2 (12)	C9C—C7C—H7C	109.5
C7B—C2B—H2B	106.0	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	116 (2)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.5	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.5	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.1	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	111 (2)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.5	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.5	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.5	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.5	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	108.1	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	110.7 (13)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.5	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.5	C5C—C10C—H10H	109.5
C4B—C5B—H5B	109.0	C5C—C10C—H10I	109.5
C4B—C5B—C6B	113 (2)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	108.5 (15)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	109.0	H10H—C10C—H10I	109.5
C6B—C5B—C10B	108 (2)

O1—C1—C2—C3	−179.2 (19)	C3B—C2B—C7B—C9B	−55 (3)
O1—C1—C2—C7	52 (3)	C3B—C4B—C5B—C6B	57 (4)
O1—C1—C6—C5	174 (2)	C3B—C4B—C5B—C10B	177 (3)
C1—C2—C3—C4	58 (2)	C4B—C5B—C6B—C1B	−56 (3)
C1—C2—C7—C8	−165 (3)	C6B—C1B—C2B—C3B	−60 (3)
C1—C2—C7—C9	72 (3)	C6B—C1B—C2B—C7B	170 (3)
C2—C1—C6—C5	54 (3)	C7B—C2B—C3B—C4B	−172 (2)
C2—C3—C4—C5	−57 (3)	C10B—C5B—C6B—C1B	−176 (2)
C3—C2—C7—C8	70 (4)	O1C—C1C—C2C—C3C	−172.1 (15)
C3—C2—C7—C9	−53 (2)	O1C—C1C—C2C—C7C	55 (3)
C3—C4—C5—C6	53 (4)	O1C—C1C—C6C—C5C	175 (2)
C3—C4—C5—C10	−180 (3)	C1C—C2C—C3C—C4C	54 (3)
C4—C5—C6—C1	−50 (3)	C1C—C2C—C7C—C8C	−179 (3)
C6—C1—C2—C3	−58 (3)	C1C—C2C—C7C—C9C	64 (3)
C6—C1—C2—C7	173 (3)	C2C—C1C—C6C—C5C	58 (4)
C7—C2—C3—C4	−173.4 (18)	C2C—C3C—C4C—C5C	−59 (3)
C10—C5—C6—C1	−178 (2)	C3C—C2C—C7C—C8C	54 (4)
O1B—C1B—C2B—C3B	−179 (2)	C3C—C2C—C7C—C9C	−63 (2)
O1B—C1B—C2B—C7B	50 (4)	C3C—C4C—C5C—C6C	58 (3)
O1B—C1B—C6B—C5B	−177 (2)	C3C—C4C—C5C—C10C	−176 (3)
C1B—C2B—C3B—C4B	58 (3)	C4C—C5C—C6C—C1C	−57 (3)
C1B—C2B—C7B—C8B	−163 (3)	C6C—C1C—C2C—C3C	−55 (3)
C1B—C2B—C7B—C9B	71 (3)	C6C—C1C—C2C—C7C	173 (3)
C2B—C1B—C6B—C5B	58 (4)	C7C—C2C—C3C—C4C	−175.6 (19)
C2B—C3B—C4B—C5B	−57 (4)	C10C—C5C—C6C—C1C	177 (2)
C3B—C2B—C7B—C8B	71 (4)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.70GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.073 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.7042 (12) Å	Cell parameters from 2354 reflections
b = 21.036 (3) Å	θ = 4.8–26.4°
c = 12.178 (3) Å	µ = 0.07 mm⁻¹
β = 104.505 (14)°	T = 296 K
V = 2902.8 (8) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	R_int = 0.090
ω and π scans	θ_max = 26.4°, θ_min = 4.8°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
T_min = 0.971, T_max = 0.997	k = −21→21
13598 measured reflections	l = −10→10
2354 independent reflections	3 standard reflections every 120 min
1080 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.079	w = 1/[σ²(F_o²) + (0.142P)² + 0.2464P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.273	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.15 e Å⁻³
2354 reflections	Δρ_min = −0.15 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.006 (5)

Special details top

Experimental. Data were collected at room temperature and pressure of 0.70 (2) GPa (700000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0078 (4)	0.0648 (2)	0.5018 (4)	0.0913 (17)
H1A	0.059012	0.064478	0.492015	0.137*	0.5
H1B	0.002 (8)	0.0309 (12)	0.536 (3)	0.137*	0.5
C1	−0.0057 (5)	0.0945 (3)	0.6075 (6)	0.077 (2)
H1	−0.075229	0.079900	0.631449	0.092*
C2	−0.0137 (5)	0.1656 (3)	0.5963 (6)	0.073 (2)
H2	0.058331	0.179002	0.575550	0.110*
C3	−0.0073 (5)	0.1953 (3)	0.7111 (6)	0.074 (2)
H3A	−0.076516	0.182946	0.736253	0.089*
H3B	−0.007952	0.241208	0.703846	0.089*
C4	0.1029 (5)	0.1750 (3)	0.7994 (6)	0.093 (2)
H4A	0.171814	0.191679	0.778557	0.111*
H4B	0.101115	0.193224	0.872195	0.111*
C5	0.1136 (6)	0.1040 (4)	0.8109 (6)	0.083 (2)
H5	0.046893	0.089037	0.839078	0.100*
C6	0.1028 (5)	0.0736 (3)	0.6971 (6)	0.073 (2)
H6A	0.100377	0.027777	0.705488	0.088*
H6B	0.172565	0.083781	0.671141	0.088*
C7	−0.1158 (5)	0.1882 (3)	0.5005 (6)	0.077 (2)
H7	−0.118901	0.160217	0.435436	0.092*
C8	−0.0933 (5)	0.2551 (4)	0.4642 (8)	0.120 (3)
H8A	−0.017454	0.256787	0.447452	0.179*
H8B	−0.153405	0.266493	0.397729	0.179*
H8C	−0.094874	0.284303	0.524330	0.179*
C9	−0.2355 (5)	0.1847 (3)	0.5272 (7)	0.095 (2)
H9A	−0.250029	0.141847	0.547472	0.142*
H9B	−0.295710	0.197336	0.461795	0.142*
H9C	−0.236479	0.212557	0.589379	0.142*
C10	0.2258 (5)	0.0835 (3)	0.8966 (6)	0.102 (2)
H10A	0.229746	0.103747	0.968048	0.153*
H10B	0.225310	0.038181	0.905935	0.153*
H10C	0.293152	0.095579	0.869769	0.153*
O1B	0.1942 (3)	0.0515 (2)	0.4277 (5)	0.102 (2)
H1BB	0.134898	0.055957	0.451170	0.153*	0.5
H1BA	0.263 (4)	0.043 (8)	0.452 (17)	0.153*	0.5
C1B	0.1842 (5)	0.0890 (3)	0.3293 (6)	0.077 (2)
H1BC	0.249872	0.077389	0.296825	0.092*
C2B	0.1954 (6)	0.1581 (3)	0.3561 (7)	0.086 (2)
H2B	0.123781	0.168956	0.379912	0.104*
C3B	0.1857 (5)	0.1958 (3)	0.2458 (7)	0.088 (2)
H3BA	0.186189	0.241048	0.261669	0.106*
H3BB	0.252904	0.186378	0.215501	0.106*
C4B	0.0739 (6)	0.1786 (4)	0.1603 (7)	0.113 (3)
H4BA	0.072388	0.200619	0.089957	0.135*
H4BB	0.007586	0.193911	0.187245	0.135*
C5B	0.0575 (6)	0.1085 (4)	0.1358 (7)	0.099 (3)
H5B	0.121481	0.095431	0.101974	0.118*
C6B	0.0753 (5)	0.0733 (3)	0.2453 (6)	0.078 (2)
H6BA	0.009090	0.082073	0.277485	0.094*
H6BB	0.075011	0.028052	0.229716	0.094*
C7B	0.2984 (5)	0.1778 (3)	0.4570 (6)	0.084 (2)
H7B	0.299931	0.147553	0.518607	0.100*
C8B	0.2811 (5)	0.2419 (4)	0.5003 (8)	0.115 (3)
H8BA	0.205455	0.243938	0.517462	0.173*
H8BB	0.342017	0.250306	0.567798	0.173*
H8BC	0.284550	0.273141	0.443709	0.173*
C9B	0.4195 (5)	0.1744 (3)	0.4294 (7)	0.109 (3)
H9BA	0.430512	0.132769	0.401382	0.164*
H9BB	0.423021	0.205547	0.372786	0.164*
H9BC	0.480487	0.182712	0.496876	0.164*
C10B	−0.0556 (6)	0.0931 (4)	0.0509 (8)	0.118 (3)
H10D	−0.121036	0.104861	0.080862	0.176*
H10E	−0.058760	0.048316	0.035247	0.176*
H10F	−0.059455	0.116233	−0.017903	0.176*
O1C	0.4103 (3)	0.0201 (2)	0.5464 (4)	0.0872 (18)
H1C	0.467857	0.004593	0.529486	0.131*	0.5
H1CA	0.347 (13)	0.023 (8)	0.532 (6)	0.131*	0.5
C1C	0.4146 (5)	0.0057 (3)	0.6605 (7)	0.078 (2)
H1CB	0.364350	0.037203	0.684793	0.094*
C2C	0.5330 (5)	0.0146 (3)	0.7340 (6)	0.071 (2)
H2C	0.582988	−0.014495	0.703902	0.085*
C3C	0.5430 (5)	−0.0083 (3)	0.8546 (6)	0.083 (2)
H3CA	0.625577	−0.008460	0.895539	0.100*
H3CB	0.502242	0.021488	0.892283	0.100*
C4C	0.4924 (6)	−0.0743 (3)	0.8609 (7)	0.099 (2)
H4CA	0.540786	−0.105189	0.834262	0.119*
H4CB	0.495228	−0.084164	0.939332	0.119*
C5C	0.3703 (5)	−0.0797 (3)	0.7930 (7)	0.084 (2)
H5C	0.324021	−0.049436	0.825249	0.101*
C6C	0.3597 (5)	−0.0587 (3)	0.6718 (6)	0.074 (2)
H6CA	0.276690	−0.057137	0.632456	0.111*
H6CB	0.396866	−0.090349	0.634434	0.111*
C7C	0.5865 (5)	0.0795 (3)	0.7282 (6)	0.078 (2)
H7C	0.577180	0.088530	0.647437	0.094*
C8C	0.7178 (5)	0.0813 (4)	0.7822 (7)	0.116 (3)
H8CA	0.755970	0.047759	0.751371	0.175*
H8CB	0.731526	0.075598	0.862711	0.175*
H8CC	0.749223	0.121524	0.766938	0.175*
C9C	0.5237 (6)	0.1335 (3)	0.7739 (7)	0.117 (3)
H9CA	0.541509	0.130964	0.855085	0.176*
H9CB	0.440003	0.129679	0.743208	0.176*
H9CC	0.550085	0.173627	0.751905	0.176*
C10C	0.3153 (5)	−0.1447 (3)	0.7988 (7)	0.098 (2)
H10G	0.235793	−0.144789	0.752503	0.147*
H10H	0.360487	−0.176457	0.771658	0.147*
H10I	0.315009	−0.153968	0.875914	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.110 (3)	0.077 (5)	0.081 (6)	0.001 (2)	0.013 (3)	−0.023 (2)
C1	0.086 (4)	0.066 (6)	0.074 (7)	0.009 (3)	0.013 (4)	−0.007 (3)
C2	0.075 (3)	0.056 (5)	0.084 (6)	0.003 (3)	0.013 (3)	−0.003 (3)
C3	0.079 (4)	0.059 (5)	0.078 (6)	0.003 (3)	0.007 (3)	−0.012 (3)
C4	0.095 (4)	0.095 (6)	0.084 (7)	−0.008 (4)	0.015 (4)	−0.027 (3)
C5	0.087 (4)	0.097 (6)	0.067 (7)	0.007 (3)	0.021 (4)	−0.004 (3)
C6	0.078 (4)	0.068 (5)	0.075 (6)	0.004 (3)	0.023 (4)	−0.001 (3)
C7	0.072 (4)	0.069 (5)	0.085 (6)	0.008 (3)	0.012 (4)	0.005 (3)
C8	0.086 (4)	0.107 (8)	0.156 (10)	0.006 (4)	0.012 (5)	0.048 (5)
C9	0.076 (4)	0.103 (7)	0.101 (8)	−0.002 (3)	0.015 (4)	−0.020 (3)
C10	0.101 (4)	0.128 (7)	0.071 (7)	0.014 (4)	0.011 (4)	−0.003 (3)
O1B	0.091 (3)	0.115 (5)	0.089 (6)	0.000 (3)	0.003 (3)	0.045 (3)
C1B	0.087 (4)	0.071 (6)	0.071 (6)	0.005 (3)	0.017 (4)	0.009 (3)
C2B	0.094 (4)	0.082 (6)	0.081 (7)	0.005 (4)	0.019 (4)	−0.014 (3)
C3B	0.093 (4)	0.073 (5)	0.100 (7)	0.008 (3)	0.024 (4)	0.022 (3)
C4B	0.125 (5)	0.115 (7)	0.092 (7)	0.015 (4)	0.016 (5)	0.036 (4)
C5B	0.094 (4)	0.104 (6)	0.097 (7)	0.008 (4)	0.021 (4)	0.013 (4)
C6B	0.072 (4)	0.080 (5)	0.075 (6)	0.001 (3)	0.005 (4)	0.008 (3)
C7B	0.076 (4)	0.081 (6)	0.096 (6)	−0.005 (3)	0.025 (4)	−0.009 (3)
C8B	0.087 (4)	0.112 (8)	0.145 (9)	−0.011 (4)	0.028 (5)	−0.055 (5)
C9B	0.082 (4)	0.113 (7)	0.134 (9)	0.010 (4)	0.029 (4)	−0.003 (4)
C10B	0.101 (5)	0.161 (9)	0.079 (9)	0.009 (4)	0.000 (5)	−0.005 (4)
O1C	0.093 (3)	0.109 (5)	0.055 (6)	0.001 (3)	0.009 (3)	0.017 (2)
C1C	0.081 (4)	0.076 (6)	0.075 (7)	0.001 (3)	0.014 (4)	0.009 (3)
C2C	0.082 (4)	0.072 (5)	0.053 (6)	0.001 (3)	0.008 (3)	0.009 (3)
C3C	0.096 (4)	0.074 (6)	0.070 (7)	−0.004 (3)	0.002 (4)	0.004 (3)
C4C	0.125 (5)	0.079 (6)	0.082 (6)	0.003 (4)	0.006 (4)	0.023 (3)
C5C	0.092 (4)	0.087 (6)	0.078 (7)	−0.001 (3)	0.028 (4)	0.019 (3)
C6C	0.074 (3)	0.062 (5)	0.079 (6)	−0.004 (3)	0.007 (3)	0.006 (3)
C7C	0.086 (4)	0.073 (6)	0.069 (6)	−0.008 (3)	0.009 (4)	0.003 (3)
C8C	0.087 (5)	0.135 (8)	0.121 (9)	−0.012 (4)	0.016 (5)	0.016 (4)
C9C	0.135 (5)	0.071 (7)	0.154 (10)	−0.009 (4)	0.051 (5)	−0.004 (4)
C10C	0.115 (5)	0.083 (7)	0.101 (8)	−0.008 (4)	0.039 (4)	0.019 (3)

Geometric parameters (Å, º) top

O1—H1A	0.8200	C5B—C6B	1.494 (10)
O1—H1B	0.82 (2)	C5B—C10B	1.497 (9)
O1—C1	1.426 (8)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.501 (8)	C7B—H7B	0.9800
C1—C6	1.518 (8)	C7B—C8B	1.482 (8)
C2—H2	0.9800	C7B—C9B	1.538 (9)
C2—C3	1.516 (9)	C8B—H8BA	0.9600
C2—C7	1.523 (8)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.519 (8)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.504 (8)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.503 (9)	O1C—H1C	0.8200
C5—C10	1.520 (8)	O1C—H1CA	0.72 (15)
C6—H6A	0.9700	O1C—C1C	1.410 (7)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.462 (6)
C7—C8	1.518 (8)	C1C—C6C	1.519 (7)
C7—C9	1.518 (8)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.523 (9)
C8—H8B	0.9600	C2C—C7C	1.511 (6)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.518 (7)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.465 (8)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.515 (9)
O1B—H1BA	0.81 (2)	C5C—C10C	1.521 (7)
O1B—C1B	1.414 (8)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.489 (9)	C7C—H7C	0.9800
C1B—C6B	1.458 (8)	C7C—C8C	1.513 (7)
C2B—H2B	0.9800	C7C—C9C	1.531 (9)
C2B—C3B	1.539 (11)	C8C—H8CA	0.9600
C2B—C7B	1.547 (8)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.498 (8)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.508 (9)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1A—O1—H1B	92.4	C10B—C5B—H5B	106.6
C1—O1—H1A	109.5	C1B—C6B—C5B	114.6 (6)
C1—O1—H1B	88 (2)	C1B—C6B—H6BA	108.6
O1—C1—H1	107.6	C1B—C6B—H6BB	108.6
O1—C1—C2	111.6 (6)	C5B—C6B—H6BA	108.6
O1—C1—C6	110.1 (5)	C5B—C6B—H6BB	108.6
C2—C1—H1	107.6	H6BA—C6B—H6BB	107.6
C2—C1—C6	112.1 (5)	C2B—C7B—H7B	107.2
C6—C1—H1	107.6	C8B—C7B—C2B	112.2 (5)
C1—C2—H2	105.8	C8B—C7B—H7B	107.2
C1—C2—C3	109.8 (6)	C8B—C7B—C9B	109.6 (5)
C1—C2—C7	113.5 (5)	C9B—C7B—C2B	113.1 (6)
C3—C2—H2	105.8	C9B—C7B—H7B	107.2
C3—C2—C7	115.2 (5)	C7B—C8B—H8BA	109.5
C7—C2—H2	105.8	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.2	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.2	H8BA—C8B—H8BB	109.5
C2—C3—C4	112.0 (5)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.9	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.2	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.2	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.1	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.1	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	112.4 (5)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.1	C5B—C10B—H10D	109.5
C5—C4—H4B	109.1	C5B—C10B—H10E	109.5
C4—C5—H5	107.2	C5B—C10B—H10F	109.5
C4—C5—C10	112.5 (5)	H10D—C10B—H10E	109.5
C6—C5—C4	110.6 (6)	H10D—C10B—H10F	109.5
C6—C5—H5	107.2	H10E—C10B—H10F	109.5
C6—C5—C10	111.8 (6)	H1C—O1C—H1CA	146.7
C10—C5—H5	107.2	C1C—O1C—H1C	109.5
C1—C6—H6A	108.8	C1C—O1C—H1CA	92 (7)
C1—C6—H6B	108.8	O1C—C1C—H1CB	106.0
C5—C6—C1	113.6 (5)	O1C—C1C—C2C	111.7 (5)
C5—C6—H6A	108.8	O1C—C1C—C6C	111.7 (5)
C5—C6—H6B	108.8	C2C—C1C—H1CB	106.0
H6A—C6—H6B	107.7	C2C—C1C—C6C	114.6 (5)
C2—C7—H7	107.2	C6C—C1C—H1CB	106.0
C8—C7—C2	110.7 (5)	C1C—C2C—H2C	104.7
C8—C7—H7	107.2	C1C—C2C—C3C	112.5 (5)
C9—C7—C2	114.2 (6)	C1C—C2C—C7C	115.4 (4)
C9—C7—H7	107.2	C3C—C2C—H2C	104.7
C9—C7—C8	110.2 (5)	C7C—C2C—H2C	104.7
C7—C8—H8A	109.5	C7C—C2C—C3C	113.5 (5)
C7—C8—H8B	109.5	C2C—C3C—H3CA	108.8
C7—C8—H8C	109.5	C2C—C3C—H3CB	108.8
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.7
H8A—C8—H8C	109.5	C4C—C3C—C2C	113.7 (5)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	108.8
C7—C9—H9A	109.5	C4C—C3C—H3CB	108.8
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.1
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.1
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.9
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.4 (5)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.1
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.1
C5—C10—H10B	109.5	C4C—C5C—H5C	106.4
C5—C10—H10C	109.5	C4C—C5C—C6C	111.0 (5)
H10A—C10—H10B	109.5	C4C—C5C—C10C	114.1 (5)
H10A—C10—H10C	109.5	C6C—C5C—H5C	106.4
H10B—C10—H10C	109.5	C6C—C5C—C10C	112.1 (5)
H1BB—O1B—H1BA	138.8	C10C—C5C—H5C	106.4
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.6
C1B—O1B—H1BA	107 (10)	C1C—C6C—H6CB	108.6
O1B—C1B—H1BC	107.2	C5C—C6C—C1C	114.5 (5)
O1B—C1B—C2B	112.1 (7)	C5C—C6C—H6CA	108.6
O1B—C1B—C6B	109.9 (5)	C5C—C6C—H6CB	108.6
C2B—C1B—H1BC	107.2	H6CA—C6C—H6CB	107.6
C6B—C1B—H1BC	107.2	C2C—C7C—H7C	106.2
C6B—C1B—C2B	112.9 (5)	C2C—C7C—C8C	112.9 (5)
C1B—C2B—H2B	104.9	C2C—C7C—C9C	114.2 (6)
C1B—C2B—C3B	109.3 (7)	C8C—C7C—H7C	106.2
C1B—C2B—C7B	116.3 (5)	C8C—C7C—C9C	110.6 (6)
C3B—C2B—H2B	104.9	C9C—C7C—H7C	106.2
C3B—C2B—C7B	115.3 (6)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	104.9	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.7	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.7	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.2	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	110.0 (6)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.7	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.7	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.6	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.6	H9CA—C9C—H9CB	109.5
C3B—C4B—C5B	114.8 (5)	H9CA—C9C—H9CC	109.5
H4BA—C4B—H4BB	107.5	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.6	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.6	C5C—C10C—H10H	109.5
C4B—C5B—H5B	106.6	C5C—C10C—H10I	109.5
C6B—C5B—C4B	109.0 (7)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	106.6	H10G—C10C—H10I	109.5
C6B—C5B—C10B	114.2 (6)	H10H—C10C—H10I	109.5
C10B—C5B—C4B	113.3 (6)

O1—C1—C2—C3	−178.3 (5)	C3B—C2B—C7B—C9B	−56.1 (9)
O1—C1—C2—C7	51.2 (7)	C3B—C4B—C5B—C6B	51.0 (8)
O1—C1—C6—C5	178.6 (7)	C3B—C4B—C5B—C10B	179.4 (8)
C1—C2—C3—C4	55.6 (7)	C4B—C5B—C6B—C1B	−50.9 (9)
C1—C2—C7—C8	−158.3 (6)	C6B—C1B—C2B—C3B	−56.2 (8)
C1—C2—C7—C9	76.7 (7)	C6B—C1B—C2B—C7B	171.1 (7)
C2—C1—C6—C5	53.8 (9)	C7B—C2B—C3B—C4B	−172.3 (5)
C2—C3—C4—C5	−55.7 (8)	C10B—C5B—C6B—C1B	−178.8 (6)
C3—C2—C7—C8	73.8 (8)	O1C—C1C—C2C—C3C	−173.0 (5)
C3—C2—C7—C9	−51.1 (8)	O1C—C1C—C2C—C7C	54.5 (8)
C3—C4—C5—C6	52.4 (7)	O1C—C1C—C6C—C5C	175.1 (5)
C3—C4—C5—C10	178.2 (7)	C1C—C2C—C3C—C4C	48.3 (8)
C4—C5—C6—C1	−51.7 (8)	C1C—C2C—C7C—C8C	−165.7 (7)
C6—C1—C2—C3	−54.3 (7)	C1C—C2C—C7C—C9C	66.7 (8)
C6—C1—C2—C7	175.1 (6)	C2C—C1C—C6C—C5C	46.8 (9)
C7—C2—C3—C4	−174.7 (5)	C2C—C3C—C4C—C5C	−53.7 (8)
C10—C5—C6—C1	−177.9 (6)	C3C—C2C—C7C—C8C	62.3 (8)
O1B—C1B—C2B—C3B	179.1 (6)	C3C—C2C—C7C—C9C	−65.2 (7)
O1B—C1B—C2B—C7B	46.4 (8)	C3C—C4C—C5C—C6C	53.5 (8)
O1B—C1B—C6B—C5B	−177.9 (8)	C3C—C4C—C5C—C10C	−178.8 (6)
C1B—C2B—C3B—C4B	54.5 (9)	C4C—C5C—C6C—C1C	−50.4 (8)
C1B—C2B—C7B—C8B	−161.7 (7)	C6C—C1C—C2C—C3C	−44.6 (9)
C1B—C2B—C7B—C9B	73.7 (8)	C6C—C1C—C2C—C7C	−177.1 (6)
C2B—C1B—C6B—C5B	56.2 (10)	C7C—C2C—C3C—C4C	−178.4 (5)
C2B—C3B—C4B—C5B	−54.3 (10)	C10C—C5C—C6C—C1C	−179.2 (5)
C3B—C2B—C7B—C8B	68.4 (10)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_0.90GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.096 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.665 (4) Å	Cell parameters from 1440 reflections
b = 20.8990 (9) Å	θ = 27.1–4.3°
c = 12.025 (4) Å	µ = 0.07 mm⁻¹
β = 104.25 (4)°	T = 296 K
V = 2841.2 (14) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	1440 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	709 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.110
Detector resolution: 16.2413 pixels mm^-1	θ_max = 27.1°, θ_min = 4.3°
ω and φ scans	h = −9→9
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −26→26
T_min = 0.970, T_max = 0.999	l = −10→10
14619 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.085	w = 1/[σ²(F_o²) + (0.1337P)² + 3.4124P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.288	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.10 e Å⁻³
1440 reflections	Δρ_min = −0.13 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.005 (7)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0128 (12)	0.0649 (2)	0.5021 (11)	0.074 (10)
H1B	0.053228	0.063674	0.489727	0.112*	0.5
H1A	−0.02 (2)	0.0300 (17)	0.532 (6)	0.112*	0.5
C1	−0.0060 (15)	0.0941 (3)	0.6068 (15)	0.058 (6)
H1	−0.075698	0.080425	0.632526	0.069*
C2	−0.0122 (15)	0.1656 (3)	0.5958 (14)	0.061 (6)
H2	0.060108	0.178831	0.574446	0.091*
C3	−0.0067 (15)	0.1958 (4)	0.7106 (14)	0.062 (6)
H3A	−0.075078	0.182664	0.737374	0.074*
H3B	−0.009091	0.242024	0.702638	0.074*
C4	0.1048 (16)	0.1766 (4)	0.7977 (15)	0.071 (7)
H4A	0.105254	0.196030	0.871021	0.085*
H4B	0.172881	0.192503	0.773430	0.085*
C5	0.1149 (17)	0.1045 (4)	0.8122 (16)	0.070 (6)
H5	0.049049	0.090071	0.843161	0.084*
C6	0.1011 (15)	0.0739 (4)	0.6981 (14)	0.063 (6)
H6A	0.097875	0.027944	0.707708	0.076*
H6B	0.170999	0.083284	0.671018	0.076*
C7	−0.116 (2)	0.1896 (4)	0.499 (2)	0.067 (7)
H7	−0.119412	0.161878	0.432400	0.081*
C8	−0.0938 (18)	0.2571 (4)	0.4622 (16)	0.101 (12)
H8A	−0.018168	0.258785	0.444040	0.151*
H8B	−0.154560	0.268859	0.395826	0.151*
H8C	−0.094386	0.286338	0.523655	0.151*
C9	−0.234 (2)	0.1832 (5)	0.529 (2)	0.084 (12)
H9A	−0.247005	0.139126	0.544300	0.126*
H9B	−0.295512	0.197858	0.465658	0.126*
H9C	−0.233196	0.208482	0.595530	0.126*
C10	0.2295 (18)	0.0841 (5)	0.8965 (17)	0.092 (12)
H10A	0.235410	0.104656	0.969003	0.137*
H10B	0.229480	0.038478	0.906462	0.137*
H10C	0.295695	0.096178	0.866923	0.137*
O1B	0.1908 (11)	0.0479 (3)	0.4235 (10)	0.085 (10)
H1BB	0.130924	0.052271	0.446913	0.128*	0.5
H1CA	0.352 (8)	0.030 (10)	0.491 (9)	0.128*	0.5
C1B	0.1833 (17)	0.0876 (4)	0.3264 (15)	0.065 (7)
H1BC	0.248414	0.076111	0.292004	0.078*
C2B	0.1923 (17)	0.1576 (4)	0.3526 (15)	0.074 (7)
H2B	0.121269	0.167358	0.379097	0.088*
C3B	0.1781 (17)	0.1947 (4)	0.2457 (16)	0.080 (7)
H3BA	0.245463	0.186578	0.213909	0.097*
H3BB	0.177929	0.239914	0.263748	0.097*
C4B	0.0667 (18)	0.1789 (5)	0.1569 (16)	0.093 (7)
H4BA	0.065633	0.203009	0.087663	0.112*
H4BB	−0.000699	0.192449	0.184726	0.112*
C5B	0.0540 (18)	0.1087 (5)	0.1274 (17)	0.093 (7)
H5B	0.117632	0.096171	0.091746	0.111*
C6B	0.0675 (15)	0.0706 (4)	0.2407 (14)	0.072 (7)
H6BA	0.001564	0.080360	0.273765	0.086*
H6BB	0.065868	0.025144	0.224437	0.086*
C7B	0.295 (2)	0.1760 (5)	0.454 (2)	0.074 (7)
H7B	0.296965	0.144973	0.515270	0.089*
C8B	0.2779 (18)	0.2410 (4)	0.4999 (16)	0.101 (12)
H8BA	0.202690	0.242497	0.519037	0.152*
H8BB	0.339767	0.249314	0.567436	0.152*
H8BC	0.279888	0.272846	0.442889	0.152*
C9B	0.415 (2)	0.1715 (6)	0.422 (2)	0.096 (12)
H9BA	0.424420	0.129523	0.392684	0.143*
H9BB	0.418409	0.202846	0.364326	0.143*
H9BC	0.478287	0.179314	0.488872	0.143*
C10B	−0.064 (2)	0.0931 (6)	0.046 (2)	0.116 (12)
H10D	−0.126329	0.111698	0.073791	0.174*
H10E	−0.073590	0.047500	0.040685	0.174*
H10F	−0.065380	0.110116	−0.028723	0.174*
O1C	0.4083 (11)	0.0207 (3)	0.5440 (11)	0.077 (10)
H1C	0.465774	0.005096	0.526238	0.115*	0.5
H1BA	0.257 (5)	0.052 (5)	0.464 (8)	0.115*	0.5
C1C	0.4127 (16)	0.0054 (4)	0.6606 (16)	0.065 (7)
H1CB	0.362545	0.037045	0.686134	0.078*
C2C	0.5322 (14)	0.0139 (3)	0.7353 (14)	0.056 (6)
H2C	0.582781	−0.014977	0.704181	0.067*
C3C	0.5420 (16)	−0.0089 (4)	0.8559 (15)	0.064 (6)
H3CA	0.624470	−0.008694	0.897775	0.077*
H3CB	0.499565	0.020334	0.893992	0.077*
C4C	0.4928 (15)	−0.0751 (4)	0.8585 (14)	0.070 (6)
H4CA	0.541698	−0.105178	0.829396	0.084*
H4CB	0.496033	−0.086685	0.937362	0.084*
C5C	0.3710 (16)	−0.0802 (4)	0.7905 (15)	0.069 (6)
H5C	0.325152	−0.049913	0.824360	0.083*
C6C	0.3575 (15)	−0.0594 (4)	0.6712 (14)	0.057 (6)
H6CA	0.273919	−0.057505	0.633353	0.085*
H6CB	0.393562	−0.090999	0.631445	0.085*
C7C	0.5823 (15)	0.0798 (4)	0.7279 (15)	0.068 (7)
H7C	0.574946	0.088459	0.646301	0.082*
C8C	0.715 (2)	0.0828 (5)	0.787 (2)	0.093 (12)
H8CA	0.759486	0.064312	0.737961	0.139*
H8CB	0.729864	0.059321	0.857953	0.139*
H8CC	0.738215	0.126581	0.802768	0.139*
C9C	0.5183 (18)	0.1342 (4)	0.7730 (17)	0.103 (12)
H9CA	0.530600	0.130144	0.854647	0.155*
H9CB	0.435192	0.132071	0.737320	0.155*
H9CC	0.549022	0.174587	0.755459	0.155*
C10C	0.3154 (18)	−0.1463 (4)	0.7976 (18)	0.097 (12)
H10G	0.235679	−0.146512	0.751144	0.145*
H10H	0.360676	−0.178382	0.770214	0.145*
H10I	0.315231	−0.155310	0.875822	0.145*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.104 (15)	0.063 (3)	0.056 (14)	0.000 (6)	0.019 (13)	−0.019 (5)
C1	0.062 (10)	0.056 (4)	0.052 (9)	−0.004 (6)	0.011 (8)	−0.005 (6)
C2	0.057 (10)	0.063 (4)	0.062 (10)	0.007 (6)	0.014 (8)	−0.008 (6)
C3	0.060 (10)	0.065 (4)	0.061 (10)	−0.001 (6)	0.016 (8)	−0.013 (6)
C4	0.067 (10)	0.078 (5)	0.066 (10)	0.003 (6)	0.014 (8)	−0.021 (6)
C5	0.072 (10)	0.071 (5)	0.067 (10)	0.000 (6)	0.015 (8)	0.000 (6)
C6	0.062 (10)	0.063 (4)	0.064 (10)	−0.002 (6)	0.014 (8)	−0.002 (6)
C7	0.069 (11)	0.063 (5)	0.072 (10)	−0.014 (7)	0.021 (8)	0.005 (6)
C8	0.084 (17)	0.090 (6)	0.122 (16)	0.001 (8)	0.015 (14)	0.044 (8)
C9	0.091 (18)	0.090 (6)	0.070 (17)	−0.007 (10)	0.017 (15)	−0.026 (8)
C10	0.079 (17)	0.124 (7)	0.063 (16)	0.020 (9)	0.003 (14)	0.002 (9)
O1B	0.090 (14)	0.084 (4)	0.069 (13)	−0.002 (6)	−0.004 (13)	0.026 (5)
C1B	0.065 (10)	0.076 (5)	0.052 (10)	0.008 (6)	0.011 (8)	0.009 (6)
C2B	0.068 (10)	0.077 (5)	0.076 (10)	0.007 (6)	0.018 (8)	−0.004 (6)
C3B	0.083 (10)	0.079 (5)	0.080 (10)	0.009 (6)	0.022 (8)	0.019 (6)
C4B	0.090 (10)	0.108 (6)	0.076 (10)	0.012 (7)	0.010 (8)	0.022 (7)
C5B	0.076 (10)	0.115 (6)	0.079 (10)	−0.002 (7)	0.002 (8)	0.011 (7)
C6B	0.066 (10)	0.077 (5)	0.066 (10)	0.007 (6)	0.004 (8)	−0.001 (6)
C7B	0.073 (11)	0.068 (5)	0.083 (10)	−0.005 (7)	0.021 (8)	−0.012 (6)
C8B	0.091 (18)	0.102 (7)	0.111 (17)	−0.021 (9)	0.024 (15)	−0.030 (9)
C9B	0.086 (18)	0.090 (6)	0.108 (18)	0.007 (10)	0.020 (15)	−0.008 (9)
C10B	0.080 (17)	0.163 (9)	0.086 (17)	0.023 (10)	−0.016 (15)	0.000 (10)
O1C	0.081 (14)	0.090 (4)	0.048 (12)	−0.009 (5)	−0.006 (12)	0.018 (5)
C1C	0.062 (10)	0.074 (5)	0.054 (10)	0.000 (6)	0.007 (8)	0.004 (6)
C2C	0.055 (10)	0.063 (4)	0.046 (9)	−0.005 (5)	0.006 (8)	0.005 (5)
C3C	0.065 (10)	0.070 (5)	0.055 (10)	−0.001 (6)	0.008 (8)	−0.006 (6)
C4C	0.076 (10)	0.072 (5)	0.058 (10)	−0.001 (6)	0.010 (8)	0.011 (6)
C5C	0.073 (10)	0.065 (4)	0.071 (10)	−0.005 (6)	0.022 (8)	0.000 (6)
C6C	0.049 (10)	0.067 (4)	0.051 (9)	0.005 (5)	0.005 (8)	0.002 (5)
C7C	0.060 (10)	0.082 (5)	0.058 (10)	−0.004 (6)	0.007 (8)	0.000 (6)
C8C	0.070 (17)	0.115 (7)	0.095 (17)	−0.014 (9)	0.022 (15)	−0.001 (9)
C9C	0.128 (18)	0.067 (5)	0.121 (17)	0.002 (8)	0.042 (15)	−0.021 (8)
C10C	0.098 (18)	0.074 (5)	0.123 (18)	0.003 (8)	0.036 (15)	−0.003 (8)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.55 (2)
O1—H1A	0.82 (2)	C5B—C10B	1.512 (14)
O1—C1	1.38 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.502 (10)	C7B—H7B	0.9800
C1—C6	1.506 (10)	C7B—C8B	1.50 (2)
C2—H2	0.9800	C7B—C9B	1.54 (5)
C2—C3	1.50 (2)	C8B—H8BA	0.9600
C2—C7	1.545 (13)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.510 (11)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.518 (10)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.48 (2)	O1C—H1CA	0.82 (2)
C5—C10	1.526 (12)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.43 (3)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.471 (14)
C7—C8	1.519 (19)	C1C—C6C	1.518 (17)
C7—C9	1.51 (5)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.50 (3)
C8—H8B	0.9600	C2C—C7C	1.507 (16)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.500 (14)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.458 (16)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.47 (2)
O1B—C1B	1.42 (2)	C5C—C10C	1.538 (18)
O1B—H1BA	0.81 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.494 (12)	C7C—H7C	0.9800
C1B—C6B	1.526 (12)	C7C—C8C	1.54 (2)
C2B—H2B	0.9800	C7C—C9C	1.53 (3)
C2B—C3B	1.47 (2)	C8C—H8CA	0.9600
C2B—C7B	1.534 (13)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.501 (12)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.508 (13)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	104.9	C10B—C5B—C6B	109.7 (18)
C1—O1—H1B	109.5	C1B—C6B—C5B	110.8 (14)
C1—O1—H1A	89.1 (19)	C1B—C6B—H6BA	109.5
O1—C1—H1	107.0	C1B—C6B—H6BB	109.5
O1—C1—C2	111.6 (13)	C5B—C6B—H6BA	109.5
O1—C1—C6	113.0 (14)	C5B—C6B—H6BB	109.5
C2—C1—H1	107.0	H6BA—C6B—H6BB	108.1
C2—C1—C6	110.8 (6)	C2B—C7B—H7B	107.3
C6—C1—H1	107.0	C8B—C7B—C2B	111.6 (12)
C1—C2—H2	106.1	C8B—C7B—H7B	107.3
C1—C2—C3	110.2 (14)	C8B—C7B—C9B	111.2 (14)
C1—C2—C7	113.7 (7)	C9B—C7B—C2B	112 (3)
C3—C2—H2	106.1	C9B—C7B—H7B	107.3
C3—C2—C7	113.9 (16)	C7B—C8B—H8BA	109.5
C7—C2—H2	106.1	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.4	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.4	H8BA—C8B—H8BB	109.5
C2—C3—C4	111.0 (14)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	108.0	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.4	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.4	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.2	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.2	H9BA—C9B—H9BB	109.5
C3—C4—C5	111.9 (7)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.9	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.2	C5B—C10B—H10D	109.5
C5—C4—H4B	109.2	C5B—C10B—H10E	109.5
C4—C5—H5	107.6	C5B—C10B—H10F	109.5
C4—C5—C10	112.6 (8)	H10D—C10B—H10E	109.5
C6—C5—C4	109.4 (13)	H10D—C10B—H10F	109.5
C6—C5—H5	107.6	H10E—C10B—H10F	109.5
C6—C5—C10	111.8 (16)	H1CA—O1C—H1C	116.5
C10—C5—H5	107.6	C1C—O1C—H1CA	130 (10)
C1—C6—H6A	108.3	C1C—O1C—H1C	109.5
C1—C6—H6B	108.3	O1C—C1C—H1CB	106.1
C5—C6—C1	115.8 (14)	O1C—C1C—C2C	112 (2)
C5—C6—H6A	108.3	O1C—C1C—C6C	111.6 (10)
C5—C6—H6B	108.3	C2C—C1C—H1CB	106.1
H6A—C6—H6B	107.4	C2C—C1C—C6C	114.5 (7)
C2—C7—H7	106.7	C6C—C1C—H1CB	106.1
C8—C7—C2	111.1 (11)	C1C—C2C—H2C	105.2
C8—C7—H7	106.7	C1C—C2C—C3C	112.7 (18)
C9—C7—C2	112 (2)	C1C—C2C—C7C	113.4 (7)
C9—C7—H7	106.7	C3C—C2C—H2C	105.2
C9—C7—C8	112.6 (15)	C3C—C2C—C7C	114.1 (9)
C7—C8—H8A	109.5	C7C—C2C—H2C	105.2
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.2
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.2
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.9
H8A—C8—H8C	109.5	C4C—C3C—C2C	112.0 (9)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.2
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.2
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.1
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.1
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.9
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.3 (7)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.1
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.1
C5—C10—H10B	109.5	C4C—C5C—H5C	106.0
C5—C10—H10C	109.5	C4C—C5C—C6C	112.4 (18)
H10A—C10—H10B	109.5	C4C—C5C—C10C	113.6 (8)
H10A—C10—H10C	109.5	C6C—C5C—H5C	106.0
H10B—C10—H10C	109.5	C6C—C5C—C10C	112.0 (10)
H1BB—O1B—H1BA	123.1	C10C—C5C—H5C	106.0
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.9
C1B—O1B—H1BA	107 (6)	C1C—C6C—H6CB	108.9
O1B—C1B—H1BC	107.9	C5C—C6C—C1C	113.6 (10)
O1B—C1B—C2B	114.4 (15)	C5C—C6C—H6CA	108.9
O1B—C1B—C6B	106.6 (14)	C5C—C6C—H6CB	108.9
C2B—C1B—H1BC	107.9	H6CA—C6C—H6CB	107.7
C2B—C1B—C6B	112.0 (8)	C2C—C7C—H7C	106.7
C6B—C1B—H1BC	107.9	C2C—C7C—C8C	111.7 (8)
C1B—C2B—H2B	104.5	C2C—C7C—C9C	115.3 (19)
C1B—C2B—C7B	114.4 (7)	C8C—C7C—H7C	106.7
C3B—C2B—C1B	110.1 (14)	C9C—C7C—H7C	106.7
C3B—C2B—H2B	104.5	C9C—C7C—C8C	109.2 (11)
C3B—C2B—C7B	117.2 (16)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	104.5	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	108.9	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	108.9	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	113.4 (15)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	107.7	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	108.9	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	108.9	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.9	H9CA—C9C—H9CB	109.5
C3B—C4B—C5B	113.5 (8)	H9CA—C9C—H9CC	109.5
H4BA—C4B—H4BB	107.7	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	108.8	C5C—C10C—H10I	109.5
C4B—C5B—C6B	108.0 (14)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	112.6 (10)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	108.8	H10H—C10C—H10I	109.5
C10B—C5B—H5B	108.8

O1—C1—C2—C3	179.0 (14)	C3B—C2B—C7B—C9B	−57.9 (19)
O1—C1—C2—C7	50 (3)	C3B—C4B—C5B—C6B	53 (3)
O1—C1—C6—C5	178.9 (14)	C3B—C4B—C5B—C10B	175 (2)
C1—C2—C3—C4	57.9 (19)	C4B—C5B—C6B—C1B	−55 (2)
C1—C2—C7—C8	−159 (2)	C6B—C1B—C2B—C3B	−56 (3)
C1—C2—C7—C9	74 (2)	C6B—C1B—C2B—C7B	169 (2)
C2—C1—C6—C5	53 (3)	C7B—C2B—C3B—C4B	−172.8 (18)
C2—C3—C4—C5	−58 (2)	C10B—C5B—C6B—C1B	−177.7 (17)
C3—C2—C7—C8	74 (3)	O1C—C1C—C2C—C3C	−173.5 (10)
C3—C2—C7—C9	−53.6 (16)	O1C—C1C—C2C—C7C	55 (2)
C3—C4—C5—C6	53 (2)	O1C—C1C—C6C—C5C	174.0 (16)
C3—C4—C5—C10	178 (2)	C1C—C2C—C3C—C4C	49.8 (19)
C4—C5—C6—C1	−51 (2)	C1C—C2C—C7C—C8C	−168 (2)
C6—C1—C2—C3	−54 (2)	C1C—C2C—C7C—C9C	66 (2)
C6—C1—C2—C7	177 (2)	C2C—C1C—C6C—C5C	46 (3)
C7—C2—C3—C4	−173.0 (14)	C2C—C3C—C4C—C5C	−55 (2)
C10—C5—C6—C1	−176.6 (15)	C3C—C2C—C7C—C8C	61 (3)
O1B—C1B—C2B—C3B	−177.4 (16)	C3C—C2C—C7C—C9C	−64.7 (15)
O1B—C1B—C2B—C7B	48 (3)	C3C—C4C—C5C—C6C	55 (2)
O1B—C1B—C6B—C5B	−176.6 (15)	C3C—C4C—C5C—C10C	−176 (2)
C1B—C2B—C3B—C4B	54 (2)	C4C—C5C—C6C—C1C	−50.0 (19)
C1B—C2B—C7B—C8B	−162 (2)	C6C—C1C—C2C—C3C	−45 (2)
C1B—C2B—C7B—C9B	73 (2)	C6C—C1C—C2C—C7C	−176.9 (19)
C2B—C1B—C6B—C5B	58 (3)	C7C—C2C—C3C—C4C	−179.0 (15)
C2B—C3B—C4B—C5B	−55 (3)	C10C—C5C—C6C—C1C	−179.3 (16)
C3B—C2B—C7B—C8B	67 (3)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_1.28GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.122 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.528 (2) Å	Cell parameters from 2237 reflections
b = 20.785 (6) Å	θ = 4.8–26.4°
c = 11.959 (5) Å	µ = 0.07 mm⁻¹
β = 104.36 (3)°	T = 296 K
V = 2775.9 (15) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	873 reflections with I > 2σ(I)
Detector resolution: 16.4 pixels mm^-1	R_int = 0.135
ω and π scans	θ_max = 26.4°, θ_min = 4.8°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −13→14
T_min = 0.969, T_max = 0.997	k = −20→21
12745 measured reflections	l = −10→10
2237 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.092	w = 1/[σ²(F_o²) + (0.1731P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.322	(Δ/σ)_max < 0.001
S = 0.99	Δρ_max = 0.16 e Å⁻³
2237 reflections	Δρ_min = −0.16 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 restraints	Extinction coefficient: 0.010 (6)

Special details top

Experimental. Data were collected at room temperature and pressure of 1.28 (2) GPa (1280000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0164 (5)	0.0641 (3)	0.4991 (6)	0.105 (2)
H1B	0.050142	0.062159	0.486160	0.157*	0.5
H1A	−0.004 (10)	0.0299 (13)	0.533 (3)	0.157*	0.5
C1	−0.0079 (7)	0.0951 (5)	0.6039 (9)	0.089 (3)
H1	−0.078196	0.081452	0.630100	0.107*
C2	−0.0168 (7)	0.1674 (4)	0.5922 (8)	0.084 (3)
H2	0.056492	0.180393	0.570744	0.126*
C3	−0.0082 (6)	0.1986 (4)	0.7081 (8)	0.085 (3)
H3A	−0.078605	0.187758	0.734777	0.102*
H3B	−0.006144	0.245023	0.699763	0.102*
C4	0.1038 (7)	0.1766 (4)	0.7972 (8)	0.095 (3)
H4A	0.173968	0.192733	0.775235	0.113*
H4B	0.103375	0.195233	0.871505	0.113*
C5	0.1133 (7)	0.1053 (5)	0.8094 (8)	0.091 (3)
H5	0.046589	0.090967	0.840477	0.109*
C6	0.1007 (6)	0.0723 (4)	0.6962 (7)	0.075 (2)
H6A	0.094094	0.026299	0.706990	0.090*
H6B	0.172404	0.079840	0.669424	0.090*
C7	−0.1187 (7)	0.1907 (4)	0.4932 (8)	0.085 (3)
H7	−0.122480	0.162573	0.426577	0.102*
C8	−0.0959 (7)	0.2574 (4)	0.4598 (9)	0.121 (4)
H8A	−0.160824	0.271233	0.397476	0.181*
H8B	−0.089620	0.285476	0.524723	0.181*
H8C	−0.022544	0.258564	0.435532	0.181*
C9	−0.2420 (7)	0.1885 (4)	0.5233 (9)	0.108 (3)
H9A	−0.258375	0.145260	0.543227	0.163*
H9B	−0.303269	0.202340	0.457766	0.163*
H9C	−0.240608	0.216454	0.587453	0.163*
C10	0.2276 (7)	0.0846 (4)	0.8942 (8)	0.103 (3)
H10A	0.229963	0.038536	0.899338	0.155*
H10B	0.295229	0.099684	0.868303	0.155*
H10C	0.230116	0.102527	0.968763	0.155*
O1B	0.1901 (4)	0.0460 (3)	0.4231 (6)	0.102 (2)
H1BB	0.130403	0.049450	0.448311	0.154*	0.5
H1CA	0.338 (6)	0.031 (9)	0.526 (10)	0.154*	0.5
C1B	0.1795 (7)	0.0882 (5)	0.3261 (9)	0.091 (3)
H1BC	0.246209	0.077526	0.292094	0.109*
C2B	0.1913 (7)	0.1559 (4)	0.3542 (8)	0.090 (3)
H2B	0.118754	0.166633	0.379127	0.108*
C3B	0.1821 (7)	0.1962 (4)	0.2443 (9)	0.098 (3)
H3BA	0.181961	0.241713	0.262453	0.118*
H3BB	0.250282	0.187574	0.212586	0.118*
C4B	0.0682 (8)	0.1786 (5)	0.1582 (9)	0.122 (4)
H4BA	0.065507	0.201686	0.087159	0.146*
H4BB	0.001532	0.193547	0.187243	0.146*
C5B	0.0496 (8)	0.1080 (5)	0.1297 (9)	0.102 (3)
H5B	0.114229	0.095480	0.094191	0.123*
C6B	0.0694 (6)	0.0707 (4)	0.2391 (8)	0.089 (3)
H6BA	0.001374	0.077182	0.272062	0.106*
H6BB	0.072649	0.025275	0.221459	0.106*
C7B	0.2946 (6)	0.1752 (4)	0.4558 (8)	0.084 (3)
H7B	0.296291	0.144700	0.518661	0.101*
C8B	0.2797 (7)	0.2414 (4)	0.5003 (9)	0.120 (4)
H8BA	0.346630	0.251123	0.563789	0.179*
H8BB	0.275839	0.272279	0.439807	0.179*
H8BC	0.207118	0.243174	0.525883	0.179*
C9B	0.4182 (7)	0.1720 (4)	0.4257 (9)	0.115 (3)
H9BA	0.429262	0.129865	0.397044	0.172*
H9BB	0.420913	0.203507	0.367812	0.172*
H9BC	0.480609	0.180514	0.493791	0.172*
C10B	−0.0640 (8)	0.0932 (4)	0.0431 (10)	0.122 (4)
H10D	−0.130690	0.105629	0.072961	0.184*
H10E	−0.068100	0.047937	0.026978	0.184*
H10F	−0.066542	0.116641	−0.026722	0.184*
O1C	0.4073 (4)	0.0177 (3)	0.5438 (5)	0.094 (2)
H1C	0.466235	0.001289	0.528513	0.140*	0.5
H1BA	0.259 (3)	0.037 (7)	0.444 (9)	0.140*	0.5
C1C	0.4099 (7)	0.0058 (4)	0.6618 (9)	0.088 (3)
H1CB	0.358702	0.038157	0.685208	0.106*
C2C	0.5303 (6)	0.0147 (4)	0.7336 (8)	0.086 (3)
H2C	0.578869	−0.015205	0.701023	0.104*
C3C	0.5448 (7)	−0.0088 (4)	0.8556 (8)	0.091 (3)
H3CA	0.629358	−0.009238	0.894527	0.110*
H3CB	0.505442	0.021120	0.896372	0.110*
C4C	0.4941 (7)	−0.0751 (4)	0.8623 (8)	0.100 (3)
H4CA	0.543200	−0.106158	0.834542	0.120*
H4CB	0.498532	−0.085121	0.942514	0.120*
C5C	0.3722 (7)	−0.0820 (4)	0.7969 (9)	0.099 (3)
H5C	0.325794	−0.051731	0.831320	0.119*
C6C	0.3554 (6)	−0.0606 (4)	0.6742 (9)	0.094 (3)
H6CA	0.270379	−0.059303	0.637445	0.141*
H6CB	0.391587	−0.092168	0.633564	0.141*
C7C	0.5861 (7)	0.0802 (4)	0.7231 (9)	0.089 (3)
H7C	0.575724	0.088376	0.640470	0.107*
C8C	0.7174 (7)	0.0849 (4)	0.7780 (9)	0.119 (3)
H8CA	0.758938	0.051744	0.747723	0.179*
H8CB	0.731050	0.079692	0.859993	0.179*
H8CC	0.746329	0.126240	0.761493	0.179*
C9C	0.5213 (8)	0.1345 (4)	0.7693 (10)	0.118 (3)
H9CA	0.436844	0.131529	0.735261	0.177*
H9CB	0.550418	0.175288	0.750088	0.177*
H9CC	0.536090	0.130811	0.851683	0.177*
C10C	0.3153 (7)	−0.1481 (4)	0.8030 (8)	0.109 (3)
H10G	0.234369	−0.147785	0.756692	0.163*
H10H	0.360350	−0.180300	0.774534	0.163*
H10I	0.315639	−0.157551	0.881647	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.125 (4)	0.084 (6)	0.088 (7)	0.017 (3)	−0.008 (4)	−0.020 (3)
C1	0.088 (5)	0.094 (7)	0.082 (8)	−0.011 (4)	0.014 (5)	−0.019 (5)
C2	0.085 (5)	0.082 (6)	0.081 (8)	−0.002 (4)	0.013 (4)	−0.001 (4)
C3	0.088 (5)	0.076 (6)	0.082 (8)	−0.003 (4)	0.003 (4)	−0.013 (4)
C4	0.098 (5)	0.097 (7)	0.077 (7)	−0.002 (4)	0.002 (5)	−0.021 (4)
C5	0.092 (5)	0.091 (7)	0.087 (8)	−0.002 (4)	0.019 (5)	−0.001 (4)
C6	0.076 (4)	0.069 (6)	0.074 (7)	0.002 (3)	0.011 (4)	0.001 (3)
C7	0.083 (5)	0.079 (6)	0.090 (7)	0.009 (4)	0.016 (5)	0.015 (4)
C8	0.096 (6)	0.105 (9)	0.150 (11)	0.004 (5)	0.009 (6)	0.040 (6)
C9	0.088 (6)	0.112 (9)	0.117 (11)	−0.005 (5)	0.010 (5)	−0.005 (4)
C10	0.104 (6)	0.136 (9)	0.069 (9)	0.012 (5)	0.021 (5)	0.013 (4)
O1B	0.095 (3)	0.108 (6)	0.093 (7)	−0.001 (3)	0.003 (4)	0.028 (3)
C1B	0.092 (5)	0.084 (7)	0.089 (8)	−0.008 (4)	0.008 (5)	0.007 (4)
C2B	0.097 (5)	0.091 (7)	0.080 (8)	−0.001 (4)	0.018 (5)	−0.010 (4)
C3B	0.106 (5)	0.086 (7)	0.099 (8)	0.010 (4)	0.019 (5)	0.020 (4)
C4B	0.125 (6)	0.127 (8)	0.104 (8)	0.016 (5)	0.010 (6)	0.030 (5)
C5B	0.102 (5)	0.108 (7)	0.096 (8)	−0.003 (5)	0.023 (5)	−0.001 (5)
C6B	0.079 (5)	0.085 (6)	0.089 (7)	0.008 (4)	−0.003 (5)	0.007 (4)
C7B	0.080 (5)	0.083 (6)	0.089 (7)	−0.008 (4)	0.020 (4)	−0.018 (4)
C8B	0.091 (5)	0.128 (9)	0.140 (11)	−0.007 (5)	0.027 (6)	−0.048 (6)
C9B	0.085 (5)	0.118 (9)	0.137 (11)	0.005 (5)	0.018 (6)	−0.003 (5)
C10B	0.105 (6)	0.144 (10)	0.105 (10)	0.012 (5)	0.001 (6)	−0.021 (5)
O1C	0.101 (4)	0.102 (6)	0.065 (7)	0.008 (3)	−0.002 (4)	0.009 (3)
C1C	0.088 (5)	0.081 (7)	0.084 (8)	−0.010 (4)	−0.002 (5)	0.008 (4)
C2C	0.085 (5)	0.082 (6)	0.078 (7)	0.002 (4)	−0.006 (4)	0.007 (4)
C3C	0.103 (5)	0.082 (7)	0.074 (7)	−0.001 (4)	−0.007 (5)	0.002 (4)
C4C	0.114 (5)	0.085 (7)	0.087 (7)	0.000 (4)	−0.001 (5)	0.023 (4)
C5C	0.105 (5)	0.089 (7)	0.101 (8)	0.001 (4)	0.020 (5)	0.021 (4)
C6C	0.090 (5)	0.082 (7)	0.099 (8)	−0.005 (4)	0.003 (5)	0.012 (4)
C7C	0.094 (5)	0.077 (7)	0.086 (7)	−0.003 (4)	0.005 (5)	−0.001 (4)
C8C	0.101 (6)	0.132 (9)	0.112 (10)	−0.002 (5)	0.003 (6)	0.011 (5)
C9C	0.128 (6)	0.096 (9)	0.140 (11)	−0.017 (5)	0.051 (6)	0.004 (5)
C10C	0.123 (6)	0.093 (9)	0.117 (10)	−0.007 (5)	0.043 (6)	0.022 (4)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.489 (12)
O1—H1A	0.81 (2)	C5B—C10B	1.487 (10)
O1—C1	1.391 (11)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.510 (10)	C7B—H7B	0.9800
C1—C6	1.524 (10)	C7B—C8B	1.500 (9)
C2—H2	0.9800	C7B—C9B	1.555 (11)
C2—C3	1.511 (12)	C8B—H8BA	0.9600
C2—C7	1.526 (10)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.527 (9)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.490 (10)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.494 (12)	O1C—H1CA	0.82 (2)
C5—C10	1.512 (9)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.426 (10)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.452 (9)
C7—C8	1.485 (9)	C1C—C6C	1.539 (9)
C7—C9	1.551 (11)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.509 (11)
C8—H8B	0.9600	C2C—C7C	1.524 (10)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.507 (8)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.435 (9)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.499 (12)
O1B—C1B	1.435 (10)	C5C—C10C	1.532 (9)
O1B—H1BA	0.80 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.446 (11)	C7C—H7C	0.9800
C1B—C6B	1.473 (10)	C7C—C8C	1.496 (9)
C2B—H2B	0.9800	C7C—C9C	1.530 (12)
C2B—C3B	1.540 (13)	C8C—H8CA	0.9600
C2B—C7B	1.529 (10)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.500 (11)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.508 (11)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	89.9	C10B—C5B—C6B	114.9 (8)
C1—O1—H1B	109.5	C1B—C6B—C5B	114.1 (7)
C1—O1—H1A	89 (2)	C1B—C6B—H6BA	108.7
O1—C1—H1	106.0	C1B—C6B—H6BB	108.7
O1—C1—C2	112.9 (9)	C5B—C6B—H6BA	108.7
O1—C1—C6	111.7 (7)	C5B—C6B—H6BB	108.7
C2—C1—H1	106.0	H6BA—C6B—H6BB	107.6
C2—C1—C6	113.6 (6)	C2B—C7B—H7B	107.7
C6—C1—H1	106.0	C2B—C7B—C9B	112.5 (7)
C1—C2—H2	104.9	C8B—C7B—C2B	112.8 (6)
C1—C2—C7	114.2 (6)	C8B—C7B—H7B	107.7
C3—C2—C1	110.8 (8)	C8B—C7B—C9B	108.3 (6)
C3—C2—H2	104.9	C9B—C7B—H7B	107.7
C3—C2—C7	116.0 (7)	C7B—C8B—H8BA	109.5
C7—C2—H2	104.9	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.4	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.4	H8BA—C8B—H8BB	109.5
C2—C3—C4	111.3 (7)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	108.0	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.4	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.4	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.9	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.9	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.7	H9BA—C9B—H9BC	109.5
C5—C4—C3	113.3 (6)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.9	C5B—C10B—H10D	109.5
C5—C4—H4B	108.9	C5B—C10B—H10E	109.5
C4—C5—H5	107.1	C5B—C10B—H10F	109.5
C4—C5—C6	112.4 (7)	H10D—C10B—H10E	109.5
C4—C5—C10	112.3 (6)	H10D—C10B—H10F	109.5
C6—C5—H5	107.1	H10E—C10B—H10F	109.5
C6—C5—C10	110.5 (7)	H1CA—O1C—H1C	152.5
C10—C5—H5	107.1	C1C—O1C—H1CA	95 (10)
C1—C6—H6A	109.0	C1C—O1C—H1C	109.5
C1—C6—H6B	109.0	O1C—C1C—H1CB	107.4
C5—C6—C1	113.0 (7)	O1C—C1C—C2C	110.2 (8)
C5—C6—H6A	109.0	O1C—C1C—C6C	110.0 (7)
C5—C6—H6B	109.0	C2C—C1C—H1CB	107.4
H6A—C6—H6B	107.8	C2C—C1C—C6C	114.3 (6)
C2—C7—H7	108.2	C6C—C1C—H1CB	107.4
C2—C7—C9	112.6 (7)	C1C—C2C—H2C	103.9
C8—C7—C2	110.6 (6)	C1C—C2C—C3C	113.0 (8)
C8—C7—H7	108.2	C1C—C2C—C7C	115.3 (6)
C8—C7—C9	108.9 (7)	C3C—C2C—H2C	103.9
C9—C7—H7	108.2	C3C—C2C—C7C	114.9 (6)
C7—C8—H8A	109.5	C7C—C2C—H2C	103.9
C7—C8—H8B	109.5	C2C—C3C—H3CA	108.9
C7—C8—H8C	109.5	C2C—C3C—H3CB	108.9
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.7
H8A—C8—H8C	109.5	C4C—C3C—C2C	113.4 (6)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	108.9
C7—C9—H9A	109.5	C4C—C3C—H3CB	108.9
C7—C9—H9B	109.5	C3C—C4C—H4CA	108.8
C7—C9—H9C	109.5	C3C—C4C—H4CB	108.8
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.7
H9A—C9—H9C	109.5	C5C—C4C—C3C	113.7 (6)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	108.8
C5—C10—H10A	109.5	C5C—C4C—H4CB	108.8
C5—C10—H10B	109.5	C4C—C5C—H5C	105.7
C5—C10—H10C	109.5	C4C—C5C—C6C	112.1 (7)
H10A—C10—H10B	109.5	C4C—C5C—C10C	115.8 (7)
H10A—C10—H10C	109.5	C6C—C5C—H5C	105.7
H10B—C10—H10C	109.5	C6C—C5C—C10C	111.1 (7)
H1BB—O1B—H1BA	140.3	C10C—C5C—H5C	105.7
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.8
C1B—O1B—H1BA	106 (5)	C1C—C6C—H6CB	108.8
O1B—C1B—H1BC	106.2	C5C—C6C—C1C	113.8 (7)
O1B—C1B—C2B	115.0 (10)	C5C—C6C—H6CA	108.8
O1B—C1B—C6B	107.8 (7)	C5C—C6C—H6CB	108.8
C2B—C1B—H1BC	106.2	H6CA—C6C—H6CB	107.7
C2B—C1B—C6B	114.8 (7)	C2C—C7C—H7C	106.8
C6B—C1B—H1BC	106.2	C2C—C7C—C9C	112.0 (8)
C1B—C2B—H2B	104.7	C8C—C7C—C2C	115.0 (7)
C1B—C2B—C3B	110.4 (9)	C8C—C7C—H7C	106.8
C1B—C2B—C7B	116.7 (7)	C8C—C7C—C9C	108.9 (7)
C3B—C2B—H2B	104.7	C9C—C7C—H7C	106.8
C7B—C2B—H2B	104.7	C7C—C8C—H8CA	109.5
C7B—C2B—C3B	114.3 (8)	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	110.0	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	110.0	H8CA—C8C—H8CB	109.5
H3BA—C3B—H3BB	108.4	H8CA—C8C—H8CC	109.5
C4B—C3B—C2B	108.4 (7)	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	110.0	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	110.0	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.2	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.2	H9CA—C9C—H9CB	109.5
C3B—C4B—C5B	116.4 (7)	H9CA—C9C—H9CC	109.5
H4BA—C4B—H4BB	107.3	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.2	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.2	C5C—C10C—H10H	109.5
C4B—C5B—H5B	106.0	C5C—C10C—H10I	109.5
C6B—C5B—C4B	109.0 (9)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	106.0	H10G—C10C—H10I	109.5
C10B—C5B—C4B	114.2 (7)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	106.0

O1—C1—C2—C3	179.5 (7)	C3B—C2B—C7B—C9B	−57.0 (11)
O1—C1—C2—C7	46.4 (10)	C3B—C4B—C5B—C6B	50.6 (11)
O1—C1—C6—C5	179.2 (9)	C3B—C4B—C5B—C10B	−179.4 (10)
C1—C2—C3—C4	53.5 (10)	C4B—C5B—C6B—C1B	−47.6 (12)
C1—C2—C7—C8	−159.1 (8)	C6B—C1B—C2B—C3B	−55.8 (11)
C1—C2—C7—C9	78.8 (10)	C6B—C1B—C2B—C7B	171.6 (9)
C2—C1—C6—C5	50.1 (11)	C7B—C2B—C3B—C4B	−172.2 (7)
C2—C3—C4—C5	−54.6 (10)	C10B—C5B—C6B—C1B	−177.2 (8)
C3—C2—C7—C8	70.2 (11)	O1C—C1C—C2C—C3C	−169.2 (7)
C3—C2—C7—C9	−51.8 (10)	O1C—C1C—C2C—C7C	55.8 (10)
C3—C4—C5—C6	52.2 (9)	O1C—C1C—C6C—C5C	170.6 (7)
C3—C4—C5—C10	177.4 (9)	C1C—C2C—C3C—C4C	47.8 (11)
C4—C5—C6—C1	−49.2 (10)	C1C—C2C—C7C—C8C	−168.2 (9)
C6—C1—C2—C3	−52.0 (10)	C1C—C2C—C7C—C9C	66.6 (11)
C6—C1—C2—C7	174.9 (8)	C2C—C1C—C6C—C5C	46.0 (12)
C7—C2—C3—C4	−174.3 (6)	C2C—C3C—C4C—C5C	−52.3 (11)
C10—C5—C6—C1	−175.5 (7)	C3C—C2C—C7C—C8C	57.6 (11)
O1B—C1B—C2B—C3B	178.3 (7)	C3C—C2C—C7C—C9C	−67.5 (10)
O1B—C1B—C2B—C7B	45.7 (11)	C3C—C4C—C5C—C6C	52.5 (11)
O1B—C1B—C6B—C5B	−176.7 (10)	C3C—C4C—C5C—C10C	−178.6 (8)
C1B—C2B—C3B—C4B	53.9 (11)	C4C—C5C—C6C—C1C	−49.1 (11)
C1B—C2B—C7B—C8B	−163.3 (9)	C6C—C1C—C2C—C3C	−44.8 (12)
C1B—C2B—C7B—C9B	73.8 (10)	C6C—C1C—C2C—C7C	−179.8 (8)
C2B—C1B—C6B—C5B	53.8 (13)	C7C—C2C—C3C—C4C	−177.1 (7)
C2B—C3B—C4B—C5B	−53.9 (13)	C10C—C5C—C6C—C1C	179.6 (7)
C3B—C2B—C7B—C8B	65.8 (12)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_1.34GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.132 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.529 (6) Å	Cell parameters from 1401 reflections
b = 20.7315 (15) Å	θ = 27.3–4.3°
c = 11.880 (6) Å	µ = 0.07 mm⁻¹
β = 104.42 (6)°	T = 296 K
V = 2750 (2) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	1401 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	707 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
Detector resolution: 16.2413 pixels mm^-1	θ_max = 27.3°, θ_min = 4.3°
ω and φ scans	h = −9→9
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −26→26
T_min = 0.970, T_max = 0.999	l = −10→10
14113 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.098	w = 1/[σ²(F_o²) + (0.155P)² + 4.5958P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.330	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.12 e Å⁻³
1401 reflections	Δρ_min = −0.13 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.006 (9)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0165 (13)	0.0649 (3)	0.4995 (12)	0.072 (11)
H1B	0.049967	0.063577	0.486248	0.109*	0.5
H1A	−0.020 (19)	0.0257 (16)	0.51 (2)	0.109*	0.5
C1	−0.0081 (18)	0.0941 (4)	0.6051 (17)	0.059 (7)
H1	−0.078429	0.080040	0.630874	0.071*
C2	−0.0170 (17)	0.1665 (4)	0.5939 (17)	0.061 (7)
H2	0.056586	0.179578	0.572861	0.091*
C3	−0.0084 (18)	0.1973 (4)	0.7093 (17)	0.064 (7)
H3A	−0.078347	0.185636	0.736340	0.077*
H3B	−0.008153	0.243779	0.700601	0.077*
C4	0.1015 (19)	0.1772 (4)	0.7977 (17)	0.070 (7)
H4A	0.100169	0.196368	0.871842	0.085*
H4B	0.171071	0.193914	0.775285	0.085*
C5	0.1144 (19)	0.1053 (4)	0.8127 (18)	0.068 (7)
H5	0.048308	0.090650	0.844518	0.081*
C6	0.0984 (18)	0.0742 (4)	0.6982 (16)	0.064 (7)
H6A	0.094037	0.028003	0.708884	0.077*
H6B	0.169470	0.082620	0.670722	0.077*
C7	−0.119 (2)	0.1917 (5)	0.494 (2)	0.067 (7)
H7	−0.122665	0.163812	0.426485	0.080*
C8	−0.0965 (19)	0.2587 (5)	0.4599 (18)	0.088 (12)
H8A	−0.161859	0.272527	0.397487	0.132*
H8B	−0.089691	0.286921	0.525294	0.132*
H8C	−0.023483	0.259961	0.434860	0.132*
C9	−0.242 (2)	0.1850 (5)	0.529 (2)	0.076 (12)
H9A	−0.253577	0.140970	0.548716	0.115*
H9B	−0.306385	0.198076	0.465115	0.115*
H9C	−0.240889	0.212074	0.595077	0.115*
C10	0.228 (2)	0.0841 (5)	0.8959 (19)	0.079 (12)
H10A	0.235602	0.105153	0.969372	0.119*
H10B	0.226171	0.038196	0.906410	0.119*
H10C	0.295026	0.095229	0.865433	0.119*
O1B	0.1895 (12)	0.0456 (3)	0.4188 (12)	0.080 (11)
H1BB	0.129475	0.049499	0.443482	0.120*	0.5
H1CA	0.349 (11)	0.018 (11)	0.486 (12)	0.120*	0.5
C1B	0.1802 (19)	0.0858 (4)	0.3231 (18)	0.062 (7)
H1BC	0.246212	0.075310	0.287872	0.075*
C2B	0.1871 (19)	0.1560 (4)	0.3506 (17)	0.071 (7)
H2B	0.115690	0.166582	0.377670	0.085*
C3B	0.179 (2)	0.1941 (5)	0.2418 (19)	0.079 (7)
H3BA	0.245660	0.183331	0.209314	0.095*
H3BB	0.182763	0.239780	0.259663	0.095*
C4B	0.062 (2)	0.1790 (5)	0.1542 (18)	0.086 (7)
H4BA	−0.003941	0.193913	0.184380	0.103*
H4BB	0.059558	0.202456	0.082997	0.103*
C5B	0.046 (2)	0.1085 (5)	0.1272 (18)	0.084 (7)
H5B	0.111354	0.096362	0.091479	0.100*
C6B	0.0647 (17)	0.0695 (4)	0.2361 (16)	0.070 (7)
H6BA	0.064858	0.024088	0.216752	0.084*
H6BB	−0.001635	0.077099	0.271070	0.084*
C7B	0.297 (2)	0.1756 (5)	0.449 (2)	0.067 (7)
H7B	0.299160	0.144361	0.511852	0.080*
C8B	0.276 (2)	0.2401 (5)	0.4994 (19)	0.099 (12)
H8BA	0.198149	0.240409	0.515476	0.148*
H8BB	0.336063	0.247520	0.570133	0.148*
H8BC	0.279578	0.273561	0.444550	0.148*
C9B	0.418 (3)	0.1695 (6)	0.420 (2)	0.083 (12)
H9BA	0.425070	0.127370	0.389044	0.124*
H9BB	0.424383	0.201633	0.364015	0.124*
H9BC	0.480868	0.175591	0.489598	0.124*
C10B	−0.067 (2)	0.0915 (6)	0.041 (2)	0.098 (12)
H10D	−0.133853	0.103691	0.071098	0.147*
H10E	−0.069255	0.045861	0.027188	0.147*
H10F	−0.070995	0.114030	−0.030323	0.147*
O1C	0.4057 (13)	0.0199 (3)	0.5426 (13)	0.071 (10)
H1C	0.463643	0.004209	0.524184	0.107*	0.5
H1BA	0.256 (4)	0.031 (5)	0.436 (8)	0.107*	0.5
C1C	0.4119 (19)	0.0052 (5)	0.6597 (19)	0.064 (7)
H1CB	0.361172	0.037199	0.684927	0.077*
C2C	0.5307 (16)	0.0138 (4)	0.7357 (17)	0.058 (6)
H2C	0.581173	−0.015531	0.703834	0.069*
C3C	0.5449 (18)	−0.0088 (4)	0.8554 (17)	0.063 (7)
H3CA	0.504012	0.020607	0.896061	0.075*
H3CB	0.629242	−0.008803	0.895423	0.075*
C4C	0.4947 (17)	−0.0762 (4)	0.8587 (17)	0.068 (7)
H4CA	0.540848	−0.106163	0.824655	0.081*
H4CB	0.503261	−0.088742	0.939048	0.081*
C5C	0.3666 (19)	−0.0807 (5)	0.7953 (18)	0.071 (7)
H5C	0.322118	−0.049576	0.830431	0.085*
C6C	0.3554 (18)	−0.0604 (4)	0.6730 (17)	0.057 (7)
H6CA	0.271106	−0.058802	0.633177	0.085*
H6CB	0.392638	−0.092910	0.634839	0.085*
C7C	0.5835 (18)	0.0810 (5)	0.7243 (17)	0.066 (7)
H7C	0.575177	0.089181	0.641392	0.079*
C8C	0.715 (2)	0.0846 (6)	0.784 (2)	0.085 (12)
H8CA	0.759012	0.057166	0.745201	0.127*
H8CB	0.726681	0.070737	0.863602	0.127*
H8CC	0.741896	0.128291	0.782889	0.127*
C9C	0.512 (2)	0.1356 (5)	0.772 (2)	0.095 (12)
H9CA	0.521961	0.130141	0.853910	0.142*
H9CB	0.428058	0.132495	0.733209	0.142*
H9CC	0.541258	0.177171	0.756843	0.142*
C10C	0.312 (2)	−0.1491 (5)	0.805 (2)	0.095 (12)
H10G	0.229655	−0.149550	0.762804	0.142*
H10H	0.355678	−0.180821	0.773150	0.142*
H10I	0.318177	−0.158830	0.885327	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.095 (16)	0.070 (4)	0.050 (14)	0.006 (6)	0.015 (13)	−0.026 (6)
C1	0.057 (10)	0.059 (5)	0.058 (10)	−0.004 (6)	0.010 (8)	−0.004 (6)
C2	0.061 (10)	0.061 (5)	0.059 (10)	0.000 (6)	0.014 (8)	−0.004 (6)
C3	0.061 (10)	0.068 (5)	0.063 (10)	0.003 (6)	0.013 (8)	−0.007 (6)
C4	0.072 (10)	0.078 (5)	0.060 (10)	0.000 (6)	0.014 (8)	−0.017 (6)
C5	0.068 (10)	0.068 (5)	0.066 (10)	−0.001 (6)	0.014 (8)	−0.004 (6)
C6	0.059 (10)	0.065 (5)	0.064 (10)	−0.005 (6)	0.010 (8)	0.000 (6)
C7	0.067 (11)	0.067 (5)	0.065 (10)	−0.011 (7)	0.014 (8)	0.002 (6)
C8	0.081 (18)	0.085 (7)	0.095 (17)	−0.003 (9)	0.016 (15)	0.042 (9)
C9	0.066 (18)	0.089 (7)	0.072 (17)	−0.018 (10)	0.012 (15)	−0.018 (9)
C10	0.072 (17)	0.116 (7)	0.044 (16)	0.007 (10)	0.005 (14)	0.003 (9)
O1B	0.074 (15)	0.083 (4)	0.072 (14)	−0.005 (6)	−0.002 (13)	0.034 (6)
C1B	0.058 (10)	0.075 (5)	0.051 (10)	0.006 (7)	0.007 (8)	−0.005 (7)
C2B	0.069 (10)	0.075 (5)	0.066 (10)	0.004 (6)	0.013 (8)	0.002 (7)
C3B	0.077 (11)	0.083 (6)	0.077 (10)	0.004 (7)	0.018 (8)	0.028 (7)
C4B	0.081 (11)	0.101 (6)	0.069 (10)	0.018 (7)	0.007 (8)	0.016 (7)
C5B	0.070 (11)	0.102 (6)	0.071 (10)	0.010 (7)	0.003 (8)	0.002 (7)
C6B	0.060 (10)	0.080 (5)	0.063 (10)	0.001 (6)	0.000 (8)	0.006 (6)
C7B	0.061 (11)	0.067 (5)	0.073 (11)	0.005 (7)	0.016 (8)	−0.015 (7)
C8B	0.090 (18)	0.090 (7)	0.113 (17)	−0.011 (9)	0.019 (15)	−0.016 (9)
C9B	0.083 (18)	0.089 (7)	0.076 (18)	0.025 (11)	0.018 (15)	−0.006 (9)
C10B	0.072 (18)	0.139 (9)	0.067 (17)	0.024 (10)	−0.014 (15)	−0.008 (10)
O1C	0.070 (15)	0.089 (5)	0.046 (13)	−0.005 (5)	−0.002 (13)	0.016 (6)
C1C	0.057 (10)	0.077 (5)	0.052 (10)	−0.011 (7)	0.004 (8)	0.010 (7)
C2C	0.051 (10)	0.067 (5)	0.050 (10)	0.001 (6)	0.002 (8)	0.006 (6)
C3C	0.061 (10)	0.069 (5)	0.053 (10)	−0.003 (6)	0.003 (8)	−0.001 (6)
C4C	0.072 (10)	0.071 (5)	0.055 (10)	0.001 (6)	0.009 (8)	0.004 (6)
C5C	0.076 (11)	0.069 (5)	0.067 (10)	−0.003 (6)	0.018 (8)	−0.003 (6)
C6C	0.052 (10)	0.067 (5)	0.047 (10)	0.002 (6)	0.006 (8)	0.003 (6)
C7C	0.057 (10)	0.083 (6)	0.054 (10)	−0.001 (7)	0.007 (8)	−0.002 (7)
C8C	0.057 (18)	0.111 (8)	0.087 (17)	−0.013 (9)	0.020 (15)	−0.003 (10)
C9C	0.103 (18)	0.078 (6)	0.104 (18)	0.010 (9)	0.028 (15)	−0.022 (9)
C10C	0.109 (19)	0.077 (6)	0.102 (18)	−0.005 (9)	0.034 (15)	0.003 (9)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.50 (2)
O1—H1A	0.82 (2)	C5B—C10B	1.487 (14)
O1—C1	1.37 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.510 (12)	C7B—H7B	0.9800
C1—C6	1.491 (12)	C7B—C8B	1.51 (2)
C2—H2	0.9800	C7B—C9B	1.53 (6)
C2—C3	1.49 (3)	C8B—H8BA	0.9600
C2—C7	1.537 (14)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.490 (13)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.503 (12)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.47 (3)	O1C—H1CA	0.82 (2)
C5—C10	1.498 (14)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.41 (3)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.452 (15)
C7—C8	1.49 (2)	C1C—C6C	1.53 (2)
C7—C9	1.58 (6)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.47 (3)
C8—H8B	0.9600	C2C—C7C	1.539 (19)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.516 (17)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.48 (2)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.49 (3)
O1B—C1B	1.39 (2)	C5C—C10C	1.57 (2)
O1B—H1BA	0.80 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.490 (14)	C7C—H7C	0.9800
C1B—C6B	1.506 (14)	C7C—C8C	1.51 (2)
C2B—H2B	0.9800	C7C—C9C	1.59 (3)
C2B—C3B	1.50 (3)	C8C—H8CA	0.9600
C2B—C7B	1.551 (14)	C8C—H8CB	0.9700
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.514 (15)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.499 (14)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	94.4	C10B—C5B—C6B	112.2 (18)
C1—O1—H1B	109.5	C1B—C6B—H6BA	109.1
C1—O1—H1A	108 (10)	C1B—C6B—H6BB	109.1
O1—C1—H1	106.2	C5B—C6B—C1B	112.5 (16)
O1—C1—C2	111.7 (15)	C5B—C6B—H6BA	109.1
O1—C1—C6	114.5 (16)	C5B—C6B—H6BB	109.1
C2—C1—H1	106.2	H6BA—C6B—H6BB	107.8
C6—C1—H1	106.2	C2B—C7B—H7B	105.3
C6—C1—C2	111.4 (7)	C8B—C7B—C2B	110.4 (14)
C1—C2—H2	104.6	C8B—C7B—H7B	105.3
C1—C2—C7	115.3 (7)	C8B—C7B—C9B	114.2 (15)
C3—C2—C1	110.9 (16)	C9B—C7B—C2B	115 (3)
C3—C2—H2	104.6	C9B—C7B—H7B	105.3
C3—C2—C7	115.3 (18)	C7B—C8B—H8BA	109.5
C7—C2—H2	104.6	C7B—C8B—H8BB	109.5
C2—C3—H3A	109.2	C7B—C8B—H8BC	109.5
C2—C3—H3B	109.2	H8BA—C8B—H8BB	109.5
C2—C3—C4	112.3 (17)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	107.9	H8BB—C8B—H8BC	109.5
C4—C3—H3A	109.2	C7B—C9B—H9BA	109.5
C4—C3—H3B	109.2	C7B—C9B—H9BB	109.5
C3—C4—H4A	108.8	C7B—C9B—H9BC	109.5
C3—C4—H4B	108.8	H9BA—C9B—H9BB	109.5
C3—C4—C5	113.7 (8)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.7	H9BB—C9B—H9BC	109.5
C5—C4—H4A	108.8	C5B—C10B—H10D	109.5
C5—C4—H4B	108.8	C5B—C10B—H10E	109.5
C4—C5—H5	106.8	C5B—C10B—H10F	109.5
C6—C5—C4	109.8 (15)	H10D—C10B—H10E	109.5
C6—C5—H5	106.8	H10D—C10B—H10F	109.5
C6—C5—C10	111.6 (18)	H10E—C10B—H10F	109.5
C10—C5—C4	114.5 (9)	H1CA—O1C—H1C	107.5
C10—C5—H5	106.8	C1C—O1C—H1CA	130 (10)
C1—C6—H6A	108.0	C1C—O1C—H1C	109.5
C1—C6—H6B	108.0	O1C—C1C—H1CB	105.6
C5—C6—C1	117.0 (16)	O1C—C1C—C2C	113 (2)
C5—C6—H6A	108.0	O1C—C1C—C6C	112.1 (11)
C5—C6—H6B	108.0	C2C—C1C—H1CB	105.6
H6A—C6—H6B	107.3	C2C—C1C—C6C	113.9 (9)
C2—C7—H7	107.7	C6C—C1C—H1CB	105.6
C2—C7—C9	109 (3)	C1C—C2C—H2C	104.0
C8—C7—C2	112.1 (12)	C1C—C2C—C3C	115 (2)
C8—C7—H7	107.7	C1C—C2C—C7C	112.9 (8)
C8—C7—C9	112.3 (17)	C3C—C2C—H2C	104.0
C9—C7—H7	107.7	C3C—C2C—C7C	115.1 (10)
C7—C8—H8A	109.5	C7C—C2C—H2C	104.0
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.3
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.3
H8A—C8—H8B	109.5	C2C—C3C—C4C	111.6 (10)
H8A—C8—H8C	109.5	H3CA—C3C—H3CB	108.0
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.3
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.3
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.1
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.1
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.8
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.5 (8)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.1
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.1
C5—C10—H10B	109.5	C4C—C5C—H5C	107.6
C5—C10—H10C	109.5	C4C—C5C—C6C	108 (2)
H10A—C10—H10B	109.5	C4C—C5C—C10C	112.7 (9)
H10A—C10—H10C	109.5	C6C—C5C—H5C	107.6
H10B—C10—H10C	109.5	C6C—C5C—C10C	112.9 (11)
H1BB—O1B—H1BA	141.3	C10C—C5C—H5C	107.6
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.6
C1B—O1B—H1BA	108 (6)	C1C—C6C—H6CB	108.6
O1B—C1B—H1BC	107.8	C5C—C6C—C1C	114.6 (11)
O1B—C1B—C2B	114.6 (17)	C5C—C6C—H6CA	108.6
O1B—C1B—C6B	107.6 (15)	C5C—C6C—H6CB	108.6
C2B—C1B—H1BC	107.8	H6CA—C6C—H6CB	107.6
C2B—C1B—C6B	111.0 (9)	C2C—C7C—H7C	107.7
C6B—C1B—H1BC	107.8	C2C—C7C—C9C	111 (2)
C1B—C2B—H2B	106.7	C8C—C7C—C2C	112.1 (9)
C1B—C2B—C3B	109.7 (17)	C8C—C7C—H7C	107.7
C1B—C2B—C7B	114.2 (8)	C8C—C7C—C9C	110.3 (13)
C3B—C2B—H2B	106.7	C9C—C7C—H7C	107.7
C3B—C2B—C7B	112.3 (17)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	106.7	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.7	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.7	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	109.9 (17)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.2	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.7	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.7	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	109.0	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	109.0	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.8	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	112.8 (9)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	109.0	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	109.0	C5C—C10C—H10H	109.5
C4B—C5B—H5B	106.1	C5C—C10C—H10I	109.5
C6B—C5B—C4B	110.9 (15)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	106.1	H10G—C10C—H10I	109.5
C10B—C5B—C4B	114.6 (10)	H10H—C10C—H10I	109.5
C10B—C5B—H5B	106.1

O1—C1—C2—C3	179.7 (17)	C3B—C2B—C7B—C9B	−57 (2)
O1—C1—C2—C7	46 (3)	C3B—C4B—C5B—C6B	52 (3)
O1—C1—C6—C5	178.2 (17)	C3B—C4B—C5B—C10B	−180 (3)
C1—C2—C3—C4	54 (2)	C4B—C5B—C6B—C1B	−51 (3)
C1—C2—C7—C8	−159 (3)	C6B—C1B—C2B—C3B	−59 (3)
C1—C2—C7—C9	76 (3)	C6B—C1B—C2B—C7B	174 (3)
C2—C1—C6—C5	50 (3)	C7B—C2B—C3B—C4B	−172.8 (18)
C2—C3—C4—C5	−55 (3)	C10B—C5B—C6B—C1B	179 (2)
C3—C2—C7—C8	70 (3)	O1C—C1C—C2C—C3C	−172.5 (12)
C3—C2—C7—C9	−55.1 (18)	O1C—C1C—C2C—C7C	53 (2)
C3—C4—C5—C6	50 (3)	O1C—C1C—C6C—C5C	176.0 (19)
C3—C4—C5—C10	176 (2)	C1C—C2C—C3C—C4C	48 (2)
C4—C5—C6—C1	−49 (3)	C1C—C2C—C7C—C8C	−168 (2)
C6—C1—C2—C3	−51 (3)	C1C—C2C—C7C—C9C	68 (2)
C6—C1—C2—C7	176 (3)	C2C—C1C—C6C—C5C	46 (3)
C7—C2—C3—C4	−172.2 (17)	C2C—C3C—C4C—C5C	−57 (3)
C10—C5—C6—C1	−176.7 (17)	C3C—C2C—C7C—C8C	57 (3)
O1B—C1B—C2B—C3B	178.7 (18)	C3C—C2C—C7C—C9C	−67.2 (18)
O1B—C1B—C2B—C7B	52 (3)	C3C—C4C—C5C—C6C	58 (2)
O1B—C1B—C6B—C5B	−178.2 (17)	C3C—C4C—C5C—C10C	−176 (2)
C1B—C2B—C3B—C4B	59 (2)	C4C—C5C—C6C—C1C	−52 (2)
C1B—C2B—C7B—C8B	−160 (3)	C6C—C1C—C2C—C3C	−43 (3)
C1B—C2B—C7B—C9B	68 (3)	C6C—C1C—C2C—C7C	−178 (2)
C2B—C1B—C6B—C5B	56 (3)	C7C—C2C—C3C—C4C	−177.9 (17)
C2B—C3B—C4B—C5B	−56 (3)	C10C—C5C—C6C—C1C	−177.7 (19)
C3B—C2B—C7B—C8B	74 (3)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_1.67GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.149 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.48 (2) Å	Cell parameters from 1267 reflections
b = 20.557 (6) Å	θ = 4.4–26.8°
c = 11.79 (2) Å	µ = 0.07 mm⁻¹
β = 103.2 (2)°	T = 296 K
V = 2709 (8) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	460 reflections with I > 2σ(I)
Detector resolution: 16.2413 pixels mm^-1	R_int = 0.189
ω and φ scans	θ_max = 26.8°, θ_min = 4.4°
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
T_min = 0.969, T_max = 0.999	k = −26→26
12550 measured reflections	l = −10→10
1267 independent reflections

Refinement top

Refinement on F²	206 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.081	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.294	w = 1/[σ²(F_o²) + (0.1646P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
1267 reflections	Δρ_max = 0.11 e Å⁻³
311 parameters	Δρ_min = −0.10 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0204 (14)	0.0663 (3)	0.4980 (13)	0.098 (3)
H1B	0.045203	0.063986	0.481770	0.147*	0.5
H1A	−0.02 (3)	0.024 (7)	0.52 (3)	0.147*	0.5
C1	−0.0082 (18)	0.0941 (5)	0.6045 (17)	0.085 (7)
H1	−0.078172	0.081802	0.634138	0.102*
C2	−0.0118 (18)	0.1682 (4)	0.5875 (17)	0.087 (7)
H2	0.062992	0.181847	0.567970	0.130*
C3	−0.0147 (16)	0.1973 (4)	0.7126 (15)	0.074 (7)
H3A	−0.023011	0.244293	0.708685	0.089*
H3B	−0.081157	0.179272	0.740279	0.089*
C4	0.1054 (17)	0.1780 (4)	0.7944 (16)	0.083 (7)
H4A	0.170819	0.194204	0.762919	0.100*
H4B	0.111476	0.197854	0.870163	0.100*
C5	0.1160 (19)	0.1067 (4)	0.8080 (18)	0.079 (7)
H5	0.049130	0.092406	0.840774	0.095*
C6	0.1019 (17)	0.0738 (4)	0.6946 (16)	0.082 (7)
H6A	0.098592	0.027188	0.706584	0.098*
H6B	0.172003	0.082629	0.664263	0.098*
C7	−0.116 (2)	0.1940 (5)	0.493 (2)	0.084 (7)
H7	−0.120748	0.166270	0.424649	0.101*
C8	−0.0940 (18)	0.2611 (5)	0.4568 (17)	0.112 (12)
H8A	−0.161117	0.275564	0.397770	0.169*
H8B	−0.082861	0.289635	0.522822	0.169*
H8C	−0.023332	0.261438	0.426196	0.169*
C9	−0.244 (2)	0.1872 (5)	0.528 (2)	0.086 (12)
H9A	−0.253051	0.143594	0.553623	0.130*
H9B	−0.306952	0.196717	0.461029	0.130*
H9C	−0.247367	0.217195	0.589289	0.130*
C10	0.2290 (19)	0.0850 (5)	0.8920 (18)	0.100 (12)
H10A	0.236136	0.107060	0.965079	0.149*
H10B	0.226023	0.038897	0.903964	0.149*
H10C	0.296820	0.095278	0.860507	0.149*
O1B	0.1893 (13)	0.0447 (3)	0.4179 (13)	0.101 (11)
H1BB	0.131649	0.045720	0.447966	0.151*	0.5
H1CA	0.336 (6)	0.015 (9)	0.51 (3)	0.151*	0.5
C1B	0.1716 (19)	0.0860 (5)	0.3284 (17)	0.094 (7)
H1BC	0.236613	0.075480	0.290214	0.112*
C2B	0.1855 (19)	0.1544 (5)	0.3487 (17)	0.091 (7)
H2B	0.116963	0.167454	0.379975	0.109*
C3B	0.1765 (19)	0.1939 (5)	0.2415 (17)	0.093 (7)
H3BA	0.244100	0.184319	0.207746	0.111*
H3BB	0.179468	0.239705	0.261513	0.111*
C4B	0.0602 (19)	0.1793 (5)	0.1522 (17)	0.103 (7)
H4BA	−0.006510	0.195907	0.181402	0.123*
H4BB	0.060979	0.202271	0.080510	0.123*
C5B	0.0413 (19)	0.1098 (5)	0.1265 (18)	0.094 (7)
H5B	0.105742	0.097249	0.089032	0.113*
C6B	0.0617 (16)	0.0689 (4)	0.2379 (15)	0.084 (7)
H6BA	−0.007297	0.073600	0.271692	0.100*
H6BB	0.066663	0.023475	0.217038	0.100*
C7B	0.302 (2)	0.1751 (6)	0.447 (2)	0.091 (7)
H7B	0.306400	0.143151	0.509392	0.109*
C8B	0.2686 (19)	0.2410 (5)	0.5004 (16)	0.122 (12)
H8BA	0.190330	0.237224	0.515838	0.183*
H8BB	0.325907	0.250025	0.571728	0.183*
H8BC	0.268913	0.275747	0.446086	0.183*
C9B	0.422 (3)	0.1702 (6)	0.416 (3)	0.106 (12)
H9BA	0.430293	0.127779	0.384668	0.159*
H9BB	0.427328	0.202653	0.358909	0.159*
H9BC	0.484322	0.176931	0.484551	0.159*
C10B	−0.072 (2)	0.0915 (5)	0.041 (2)	0.108 (12)
H10D	−0.139527	0.109747	0.065055	0.162*
H10E	−0.079664	0.045029	0.036869	0.162*
H10F	−0.070122	0.108188	−0.034979	0.162*
O1C	0.4082 (12)	0.0187 (3)	0.5403 (13)	0.095 (11)
H1C	0.467383	0.002451	0.523713	0.143*	0.5
H1BA	0.251 (6)	0.052 (4)	0.465 (8)	0.143*	0.5
C1C	0.4096 (15)	0.0055 (5)	0.6583 (15)	0.092 (7)
H1CB	0.358825	0.038667	0.682470	0.110*
C2C	0.5331 (16)	0.0155 (4)	0.7330 (16)	0.079 (7)
H2C	0.584095	−0.013704	0.699908	0.095*
C3C	0.5411 (17)	−0.0110 (4)	0.8589 (16)	0.082 (7)
H3CA	0.623855	−0.009766	0.901892	0.098*
H3CB	0.495546	0.017376	0.898309	0.098*
C4C	0.4959 (16)	−0.0776 (4)	0.8603 (15)	0.079 (7)
H4CA	0.508853	−0.092433	0.940335	0.095*
H4CB	0.540366	−0.106013	0.819865	0.095*
C5C	0.3636 (19)	−0.0820 (5)	0.8028 (18)	0.100 (7)
H5C	0.319166	−0.051386	0.840702	0.120*
C6C	0.3539 (17)	−0.0609 (4)	0.6772 (16)	0.075 (7)
H6CA	0.269858	−0.059806	0.638246	0.112*
H6CB	0.391538	−0.094010	0.639049	0.112*
C7C	0.5832 (16)	0.0824 (5)	0.7228 (16)	0.082 (7)
H7C	0.574713	0.091711	0.639758	0.098*
C8C	0.7144 (19)	0.0868 (5)	0.781 (2)	0.094 (12)
H8CA	0.758917	0.057634	0.743743	0.140*
H8CB	0.725829	0.075134	0.861933	0.140*
H8CC	0.741853	0.130544	0.775411	0.140*
C9C	0.504 (2)	0.1369 (5)	0.7752 (19)	0.115 (12)
H9CA	0.540313	0.144580	0.855947	0.172*
H9CB	0.424154	0.121122	0.767755	0.172*
H9CC	0.502173	0.176826	0.732480	0.172*
C10C	0.3136 (18)	−0.1496 (5)	0.8077 (18)	0.114 (12)
H10G	0.230027	−0.149742	0.770290	0.171*
H10H	0.355266	−0.179466	0.768351	0.171*
H10I	0.323694	−0.162717	0.887540	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.098 (4)	0.100 (3)	0.096 (4)	−0.001 (2)	0.021 (2)	−0.002 (2)
C1	0.073 (11)	0.096 (6)	0.085 (10)	−0.012 (7)	0.012 (8)	−0.010 (7)
C2	0.084 (11)	0.100 (6)	0.072 (10)	0.004 (7)	0.008 (8)	0.001 (7)
C3	0.066 (11)	0.078 (5)	0.074 (10)	−0.004 (6)	0.010 (8)	−0.006 (6)
C4	0.080 (11)	0.097 (6)	0.071 (10)	−0.013 (7)	0.013 (8)	−0.009 (6)
C5	0.084 (11)	0.083 (5)	0.068 (10)	0.003 (7)	0.014 (8)	0.006 (6)
C6	0.067 (11)	0.091 (5)	0.082 (10)	−0.014 (6)	0.008 (8)	0.010 (7)
C7	0.082 (11)	0.084 (6)	0.086 (11)	0.004 (8)	0.018 (9)	0.008 (7)
C8	0.082 (18)	0.110 (7)	0.137 (17)	0.011 (9)	0.007 (15)	0.005 (10)
C9	0.066 (18)	0.104 (7)	0.088 (17)	−0.001 (10)	0.015 (15)	−0.008 (9)
C10	0.077 (18)	0.136 (8)	0.078 (17)	0.023 (10)	0.003 (15)	−0.021 (10)
O1B	0.086 (15)	0.120 (5)	0.088 (14)	−0.004 (7)	0.002 (14)	0.037 (7)
C1B	0.087 (11)	0.109 (6)	0.077 (10)	−0.001 (8)	0.002 (8)	0.004 (7)
C2B	0.082 (11)	0.100 (6)	0.089 (10)	0.010 (7)	0.015 (8)	−0.002 (7)
C3B	0.094 (11)	0.092 (6)	0.092 (11)	0.008 (7)	0.022 (9)	0.008 (7)
C4B	0.095 (11)	0.125 (7)	0.081 (10)	0.009 (7)	0.005 (8)	−0.001 (7)
C5B	0.085 (11)	0.107 (6)	0.084 (10)	−0.005 (7)	0.008 (8)	−0.003 (7)
C6B	0.074 (11)	0.092 (5)	0.079 (10)	−0.006 (6)	0.006 (8)	0.010 (7)
C7B	0.085 (12)	0.090 (7)	0.097 (11)	0.004 (8)	0.020 (9)	−0.014 (7)
C8B	0.129 (19)	0.136 (9)	0.093 (17)	−0.022 (11)	0.008 (16)	0.005 (10)
C9B	0.100 (19)	0.108 (8)	0.104 (18)	0.014 (12)	0.011 (16)	0.020 (10)
C10B	0.089 (19)	0.139 (8)	0.087 (18)	0.007 (10)	0.004 (16)	−0.008 (9)
O1C	0.085 (15)	0.115 (5)	0.074 (14)	0.000 (6)	−0.006 (14)	0.011 (6)
C1C	0.082 (11)	0.108 (7)	0.081 (11)	−0.005 (7)	0.008 (9)	0.018 (8)
C2C	0.076 (10)	0.093 (6)	0.062 (10)	0.000 (6)	0.003 (8)	−0.004 (6)
C3C	0.077 (11)	0.089 (6)	0.077 (11)	0.009 (7)	0.012 (8)	0.003 (6)
C4C	0.089 (11)	0.088 (6)	0.059 (10)	0.002 (7)	0.014 (8)	0.012 (6)
C5C	0.104 (11)	0.101 (6)	0.092 (11)	0.007 (7)	0.016 (9)	0.011 (7)
C6C	0.060 (11)	0.083 (5)	0.078 (10)	−0.009 (6)	0.007 (8)	0.008 (6)
C7C	0.061 (10)	0.094 (6)	0.086 (10)	−0.019 (7)	0.008 (8)	0.014 (7)
C8C	0.047 (18)	0.124 (7)	0.110 (17)	−0.020 (9)	0.017 (15)	0.001 (9)
C9C	0.104 (18)	0.100 (7)	0.139 (18)	0.022 (10)	0.024 (16)	−0.022 (10)
C10C	0.106 (18)	0.097 (7)	0.135 (18)	0.007 (9)	0.019 (16)	0.009 (9)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.53 (2)
O1—H1A	0.9 (3)	C5B—C10B	1.504 (13)
O1—C1	1.36 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.537 (12)	C7B—H7B	0.9800
C1—C6	1.511 (13)	C7B—C8B	1.58 (3)
C2—H2	0.9800	C7B—C9B	1.50 (6)
C2—C3	1.60 (3)	C8B—H8BA	0.9600
C2—C7	1.532 (15)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.543 (14)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.477 (11)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.47 (3)	O1C—H1CA	0.82 (2)
C5—C10	1.508 (13)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.41 (2)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.502 (15)
C7—C8	1.49 (2)	C1C—C6C	1.545 (19)
C7—C9	1.61 (5)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.56 (3)
C8—H8B	0.9600	C2C—C7C	1.507 (17)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.465 (15)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.52 (2)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.52 (3)
O1B—C1B	1.33 (2)	C5C—C10C	1.511 (19)
O1B—H1BA	0.81 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.428 (12)	C7C—H7C	0.9800
C1B—C6B	1.496 (14)	C7C—C8C	1.509 (19)
C2B—H2B	0.9800	C7C—C9C	1.65 (3)
C2B—C3B	1.49 (3)	C8C—H8CA	0.9600
C2B—C7B	1.617 (16)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.529 (14)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.467 (11)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	93.9	C10B—C5B—C6B	112.3 (17)
C1—O1—H1B	109.5	C1B—C6B—C5B	114.8 (15)
C1—O1—H1A	98 (10)	C1B—C6B—H6BA	108.6
O1—C1—H1	107.5	C1B—C6B—H6BB	108.6
O1—C1—C2	107.6 (15)	C5B—C6B—H6BA	108.6
O1—C1—C6	115.2 (16)	C5B—C6B—H6BB	108.6
C2—C1—H1	107.5	H6BA—C6B—H6BB	107.5
C6—C1—H1	107.5	C2B—C7B—H7B	104.4
C6—C1—C2	111.0 (8)	C8B—C7B—C2B	105.8 (15)
C1—C2—H2	108.3	C8B—C7B—H7B	104.4
C1—C2—C3	104.9 (16)	C9B—C7B—C2B	118 (3)
C3—C2—H2	108.3	C9B—C7B—H7B	104.4
C7—C2—C1	115.5 (8)	C9B—C7B—C8B	118.5 (15)
C7—C2—H2	108.3	C7B—C8B—H8BA	109.5
C7—C2—C3	111.2 (19)	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.5	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.5	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.7	H8BA—C8B—H8BC	109.5
C4—C3—C2	106.0 (16)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.5	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.5	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.4	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.4	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	108.0	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.3 (8)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.4	C5B—C10B—H10D	109.5
C5—C4—H4B	109.4	C5B—C10B—H10E	109.5
C4—C5—H5	106.7	C5B—C10B—H10F	109.5
C4—C5—C10	113.7 (9)	H10D—C10B—H10E	109.5
C6—C5—C4	111.6 (14)	H10D—C10B—H10F	109.5
C6—C5—H5	106.7	H10E—C10B—H10F	109.5
C6—C5—C10	111.1 (17)	H1CA—O1C—H1C	131.00
C10—C5—H5	106.7	C1C—O1C—H1CA	101.00
C1—C6—H6A	108.7	C1C—O1C—H1C	109.5
C1—C6—H6B	108.7	O1C—C1C—H1CB	106.2
C5—C6—C1	114.3 (16)	O1C—C1C—C2C	110.3 (17)
C5—C6—H6A	108.7	O1C—C1C—C6C	113.5 (11)
C5—C6—H6B	108.7	C2C—C1C—H1CB	106.2
H6A—C6—H6B	107.6	C2C—C1C—C6C	113.7 (9)
C2—C7—H7	106.3	C6C—C1C—H1CB	106.2
C2—C7—C9	113 (3)	C1C—C2C—H2C	104.7
C8—C7—C2	111.8 (13)	C1C—C2C—C3C	110.5 (18)
C8—C7—H7	106.3	C1C—C2C—C7C	113.9 (8)
C8—C7—C9	112.4 (16)	C3C—C2C—H2C	104.7
C9—C7—H7	106.3	C7C—C2C—H2C	104.7
C7—C8—H8A	109.5	C7C—C2C—C3C	116.9 (10)
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.0
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.0
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.8
H8A—C8—H8C	109.5	C4C—C3C—C2C	113.1 (11)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.0
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.0
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.3
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.3
H9A—C9—H9B	109.5	C3C—C4C—C5C	111.8 (9)
H9A—C9—H9C	109.5	H4CA—C4C—H4CB	107.9
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.3
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.3
C5—C10—H10B	109.5	C4C—C5C—H5C	109.3
C5—C10—H10C	109.5	C4C—C5C—C6C	105.1 (19)
H10A—C10—H10B	109.5	C6C—C5C—H5C	109.3
H10A—C10—H10C	109.5	C10C—C5C—C4C	112.9 (9)
H10B—C10—H10C	109.5	C10C—C5C—H5C	109.3
H1BB—O1B—H1BA	111.7	C10C—C5C—C6C	110.8 (12)
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.1
C1B—O1B—H1BA	112 (6)	C1C—C6C—H6CB	108.1
O1B—C1B—H1BC	103.2	C5C—C6C—C1C	116.8 (10)
O1B—C1B—C2B	120.2 (15)	C5C—C6C—H6CA	108.1
O1B—C1B—C6B	111.4 (14)	C5C—C6C—H6CB	108.1
C2B—C1B—H1BC	103.2	H6CA—C6C—H6CB	107.3
C2B—C1B—C6B	113.3 (9)	C2C—C7C—H7C	107.8
C6B—C1B—H1BC	103.2	C2C—C7C—C8C	112.2 (8)
C1B—C2B—H2B	105.4	C2C—C7C—C9C	109.7 (19)
C1B—C2B—C3B	114.3 (16)	C8C—C7C—H7C	107.8
C1B—C2B—C7B	115.0 (9)	C8C—C7C—C9C	111.4 (12)
C3B—C2B—H2B	105.4	C9C—C7C—H7C	107.8
C3B—C2B—C7B	110.4 (17)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	105.4	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.4	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.4	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	111.0 (16)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.0	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.4	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.4	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.9	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.9	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.7	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.4 (9)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.9	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.9	C5C—C10C—H10H	109.5
C4B—C5B—H5B	105.0	C5C—C10C—H10I	109.5
C4B—C5B—C6B	111.8 (13)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	116.5 (10)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	105.0	H10H—C10C—H10I	109.5
C10B—C5B—H5B	105.0

O1—C1—C2—C3	172.6 (15)	C3B—C2B—C7B—C9B	−58 (2)
O1—C1—C2—C7	50 (3)	C3B—C4B—C5B—C6B	48 (3)
O1—C1—C6—C5	177.5 (16)	C3B—C4B—C5B—C10B	179 (2)
C1—C2—C3—C4	64.4 (18)	C4B—C5B—C6B—C1B	−45 (3)
C1—C2—C7—C8	−162 (2)	C6B—C1B—C2B—C3B	−51 (3)
C1—C2—C7—C9	70 (3)	C6B—C1B—C2B—C7B	179 (3)
C2—C1—C6—C5	55 (3)	C7B—C2B—C3B—C4B	−174.6 (17)
C2—C3—C4—C5	−64 (2)	C10B—C5B—C6B—C1B	−178 (2)
C3—C2—C7—C8	78 (3)	O1C—C1C—C2C—C3C	−169.6 (11)
C3—C2—C7—C9	−49.7 (16)	O1C—C1C—C2C—C7C	56 (2)
C3—C4—C5—C6	56 (3)	O1C—C1C—C6C—C5C	173.8 (16)
C3—C4—C5—C10	−177 (2)	C1C—C2C—C3C—C4C	51 (2)
C4—C5—C6—C1	−51 (3)	C1C—C2C—C7C—C8C	−170 (2)
C6—C1—C2—C3	−60 (3)	C1C—C2C—C7C—C9C	66 (2)
C6—C1—C2—C7	177 (3)	C2C—C1C—C6C—C5C	47 (3)
C7—C2—C3—C4	−170.1 (14)	C2C—C3C—C4C—C5C	−63 (2)
C10—C5—C6—C1	−178.7 (16)	C3C—C2C—C7C—C8C	59 (3)
O1B—C1B—C2B—C3B	173 (2)	C3C—C2C—C7C—C9C	−65.0 (17)
O1B—C1B—C2B—C7B	44 (4)	C3C—C4C—C5C—C6C	61.6 (19)
O1B—C1B—C6B—C5B	−174.3 (18)	C3C—C4C—C5C—C10C	−178 (2)
C1B—C2B—C3B—C4B	54 (3)	C4C—C5C—C6C—C1C	−53.7 (19)
C1B—C2B—C7B—C8B	−152 (2)	C6C—C1C—C2C—C3C	−41 (2)
C1B—C2B—C7B—C9B	73 (3)	C6C—C1C—C2C—C7C	−175 (2)
C2B—C1B—C6B—C5B	47 (3)	C7C—C2C—C3C—C4C	−177.0 (16)
C2B—C3B—C4B—C5B	−53 (3)	C10C—C5C—C6C—C1C	−175.9 (17)
C3B—C2B—C7B—C8B	77 (3)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_2.10GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.194 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.24 (2) Å	Cell parameters from 1252 reflections
b = 20.451 (5) Å	θ = 4.4–27.1°
c = 11.661 (18) Å	µ = 0.07 mm⁻¹
β = 103.31 (7)°	T = 296 K
V = 2609 (6) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	477 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.241
ω and φ scans	θ_max = 27.1°, θ_min = 4.4°
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
T_min = 0.968, T_max = 0.999	k = −26→25
12410 measured reflections	l = −10→10
1252 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.095	w = 1/[σ²(F_o²) + (0.1917P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.341	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.11 e Å⁻³
1252 reflections	Δρ_min = −0.12 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.021 (15)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0251 (16)	0.0656 (4)	0.4991 (14)	0.091 (3)
H1B	0.039999	0.062392	0.479213	0.137*	0.5
H1A	−0.02 (2)	0.026 (2)	0.51 (2)	0.137*	0.5
C1	−0.007 (2)	0.0947 (5)	0.601 (2)	0.078 (7)
H1	−0.075428	0.082627	0.635884	0.093*
C2	−0.013 (2)	0.1716 (5)	0.583 (2)	0.088 (7)
H2	0.064080	0.185831	0.564959	0.132*
C3	−0.016 (2)	0.1983 (5)	0.712 (2)	0.082 (7)
H3A	−0.024148	0.245579	0.710360	0.098*
H3B	−0.085642	0.179949	0.736983	0.098*
C4	0.102 (2)	0.1786 (5)	0.797 (2)	0.090 (7)
H4A	0.170933	0.193341	0.767861	0.109*
H4B	0.105939	0.199200	0.873146	0.109*
C5	0.106 (3)	0.1064 (5)	0.812 (2)	0.088 (7)
H5	0.037194	0.090301	0.841579	0.106*
C6	0.1072 (19)	0.0747 (5)	0.6864 (18)	0.067 (7)
H6A	0.178040	0.089790	0.659628	0.081*
H6B	0.111224	0.027419	0.692878	0.081*
C7	−0.115 (3)	0.1948 (6)	0.487 (3)	0.079 (7)
H7	−0.119550	0.166559	0.418442	0.095*
C8	−0.099 (2)	0.2599 (6)	0.453 (2)	0.104 (13)
H8A	−0.167635	0.272534	0.391321	0.156*
H8B	−0.093987	0.288336	0.519611	0.156*
H8C	−0.025458	0.262951	0.425460	0.156*
C9	−0.247 (3)	0.1876 (6)	0.529 (3)	0.090 (13)
H9A	−0.256801	0.143241	0.551688	0.135*
H9B	−0.313241	0.199379	0.464486	0.135*
H9C	−0.245938	0.216136	0.594413	0.135*
C10	0.227 (2)	0.0868 (5)	0.892 (2)	0.095 (12)
H10A	0.230310	0.040088	0.901539	0.143*
H10B	0.293478	0.100830	0.858865	0.143*
H10C	0.234953	0.106965	0.968121	0.143*
O1B	0.1892 (16)	0.0431 (4)	0.4130 (15)	0.097 (11)
H1BB	0.130118	0.044433	0.443107	0.146*	0.5
H1CA	0.34 (2)	0.010 (10)	0.49 (3)	0.146*	0.5
C1B	0.174 (2)	0.0865 (6)	0.325 (2)	0.082 (7)
H1BC	0.239704	0.075798	0.285634	0.099*
C2B	0.188 (2)	0.1551 (5)	0.346 (2)	0.086 (7)
H2B	0.114484	0.167521	0.372740	0.103*
C3B	0.178 (2)	0.1929 (6)	0.236 (2)	0.096 (8)
H3BA	0.247014	0.182527	0.202119	0.116*
H3BB	0.181425	0.239320	0.254127	0.116*
C4B	0.061 (2)	0.1774 (6)	0.1489 (19)	0.095 (7)
H4BA	−0.006768	0.194189	0.179229	0.114*
H4BB	0.060207	0.200328	0.076016	0.114*
C5B	0.040 (3)	0.1084 (7)	0.123 (2)	0.112 (8)
H5B	0.104824	0.094901	0.084586	0.135*
C6B	0.059 (2)	0.0691 (5)	0.234 (2)	0.086 (7)
H6BA	0.062639	0.023138	0.214422	0.104*
H6BB	−0.010634	0.075159	0.268705	0.104*
C7B	0.295 (3)	0.1723 (6)	0.452 (3)	0.077 (7)
H7B	0.297883	0.140135	0.514540	0.092*
C8B	0.272 (2)	0.2412 (6)	0.498 (2)	0.114 (13)
H8BA	0.337349	0.252448	0.563481	0.171*
H8BB	0.267118	0.272761	0.436256	0.171*
H8BC	0.195996	0.240894	0.522940	0.171*
C9B	0.432 (3)	0.1677 (7)	0.403 (3)	0.111 (13)
H9BA	0.441373	0.124268	0.375441	0.167*
H9BB	0.428512	0.198302	0.339896	0.167*
H9BC	0.499418	0.178128	0.466972	0.167*
C10B	−0.076 (3)	0.0901 (9)	0.039 (2)	0.118 (13)
H10D	−0.141037	0.089056	0.080241	0.177*
H10E	−0.067395	0.047743	0.006849	0.177*
H10F	−0.094704	0.121757	−0.023031	0.177*
O1C	0.4022 (17)	0.0193 (4)	0.5456 (19)	0.102 (12)
H1C	0.461388	0.003296	0.526042	0.153*	0.5
H1BA	0.246 (7)	0.052 (4)	0.466 (7)	0.153*	0.5
C1C	0.408 (3)	0.0054 (6)	0.661 (2)	0.084 (7)
H1CB	0.357070	0.038060	0.687989	0.100*
C2C	0.535 (2)	0.0160 (5)	0.730 (2)	0.075 (7)
H2C	0.584433	−0.015575	0.698344	0.090*
C3C	0.539 (2)	−0.0098 (5)	0.861 (2)	0.080 (7)
H3CA	0.622020	−0.007127	0.908792	0.096*
H3CB	0.487271	0.017351	0.897527	0.096*
C4C	0.497 (2)	−0.0765 (5)	0.8562 (19)	0.079 (7)
H4CA	0.545262	−0.102481	0.813652	0.095*
H4CB	0.511041	−0.093685	0.935697	0.095*
C5C	0.370 (2)	−0.0828 (6)	0.800 (2)	0.100 (8)
H5C	0.328978	−0.049757	0.837549	0.120*
C6C	0.353 (2)	−0.0610 (5)	0.6775 (19)	0.069 (7)
H6CA	0.266386	−0.059578	0.642221	0.103*
H6CB	0.389195	−0.093408	0.634840	0.103*
C7C	0.590 (2)	0.0818 (6)	0.713 (2)	0.087 (7)
H7C	0.582816	0.089812	0.628985	0.105*
C8C	0.722 (3)	0.0877 (7)	0.778 (2)	0.104 (13)
H8CA	0.761061	0.120897	0.741912	0.156*
H8CB	0.762383	0.046650	0.775609	0.156*
H8CC	0.725775	0.099391	0.858799	0.156*
C9C	0.507 (3)	0.1370 (6)	0.767 (3)	0.115 (13)
H9CA	0.512743	0.128300	0.849432	0.173*
H9CB	0.422978	0.134233	0.725231	0.173*
H9CC	0.537424	0.180152	0.758643	0.173*
C10C	0.303 (3)	−0.1500 (6)	0.815 (2)	0.118 (13)
H10G	0.219374	−0.147579	0.773115	0.177*
H10H	0.342987	−0.185215	0.784014	0.177*
H10I	0.307696	−0.157576	0.897126	0.177*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.091 (4)	0.092 (3)	0.090 (4)	−0.001 (2)	0.020 (2)	−0.002 (2)
C1	0.076 (11)	0.080 (6)	0.076 (11)	−0.012 (7)	0.015 (9)	−0.004 (7)
C2	0.079 (11)	0.104 (7)	0.074 (11)	0.005 (8)	0.006 (8)	0.003 (8)
C3	0.074 (11)	0.084 (6)	0.087 (11)	0.009 (7)	0.018 (9)	0.002 (7)
C4	0.087 (11)	0.104 (7)	0.075 (10)	0.000 (8)	0.008 (8)	−0.007 (7)
C5	0.083 (11)	0.095 (7)	0.083 (11)	0.006 (7)	0.015 (9)	−0.001 (7)
C6	0.056 (11)	0.077 (5)	0.064 (10)	−0.008 (6)	0.004 (8)	−0.004 (7)
C7	0.076 (12)	0.076 (6)	0.084 (11)	0.004 (8)	0.019 (9)	0.012 (7)
C8	0.092 (19)	0.122 (9)	0.094 (18)	0.026 (11)	0.012 (16)	0.029 (11)
C9	0.09 (2)	0.089 (7)	0.093 (18)	−0.030 (11)	0.015 (16)	−0.016 (9)
C10	0.065 (18)	0.119 (8)	0.088 (18)	0.006 (10)	−0.012 (15)	−0.002 (10)
O1B	0.077 (16)	0.114 (6)	0.095 (15)	−0.015 (7)	0.007 (14)	0.024 (8)
C1B	0.073 (11)	0.102 (7)	0.064 (11)	0.001 (8)	0.000 (8)	−0.003 (8)
C2B	0.085 (11)	0.092 (6)	0.080 (11)	0.003 (7)	0.017 (9)	0.011 (7)
C3B	0.095 (12)	0.100 (7)	0.093 (11)	0.006 (8)	0.019 (9)	0.011 (8)
C4B	0.078 (11)	0.119 (7)	0.080 (10)	0.005 (8)	0.000 (8)	0.005 (7)
C5B	0.095 (12)	0.132 (8)	0.102 (11)	0.014 (8)	0.007 (9)	0.005 (8)
C6B	0.077 (11)	0.093 (6)	0.087 (11)	0.000 (7)	0.014 (8)	0.010 (7)
C7B	0.085 (12)	0.064 (6)	0.085 (11)	−0.009 (8)	0.026 (9)	−0.012 (7)
C8B	0.10 (2)	0.134 (9)	0.100 (18)	−0.003 (12)	0.014 (16)	−0.003 (11)
C9B	0.11 (2)	0.120 (9)	0.097 (19)	0.000 (14)	0.016 (16)	0.011 (12)
C10B	0.10 (2)	0.164 (10)	0.077 (19)	0.006 (13)	−0.009 (16)	−0.003 (11)
O1C	0.087 (17)	0.117 (6)	0.087 (15)	−0.004 (7)	−0.012 (14)	0.012 (8)
C1C	0.071 (11)	0.104 (7)	0.070 (11)	−0.009 (8)	0.002 (9)	0.011 (8)
C2C	0.073 (11)	0.084 (6)	0.063 (10)	0.003 (7)	0.007 (8)	−0.003 (7)
C3C	0.078 (11)	0.085 (6)	0.072 (11)	0.006 (7)	0.009 (8)	−0.003 (7)
C4C	0.081 (11)	0.091 (6)	0.061 (11)	−0.004 (7)	0.010 (8)	0.008 (7)
C5C	0.102 (12)	0.106 (7)	0.089 (11)	0.001 (8)	0.016 (9)	0.003 (8)
C6C	0.059 (11)	0.077 (6)	0.067 (11)	0.007 (7)	0.007 (8)	−0.003 (7)
C7C	0.077 (11)	0.091 (7)	0.092 (11)	−0.017 (8)	0.017 (9)	0.005 (7)
C8C	0.084 (19)	0.141 (9)	0.079 (18)	−0.024 (11)	0.001 (15)	0.023 (10)
C9C	0.09 (2)	0.114 (9)	0.139 (19)	0.002 (11)	0.025 (16)	−0.014 (11)
C10C	0.13 (2)	0.098 (8)	0.125 (19)	−0.002 (11)	0.027 (16)	0.027 (10)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.50 (3)
O1—H1A	0.82 (2)	C5B—C10B	1.481 (17)
O1—C1	1.30 (2)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.586 (14)	C7B—H7B	0.9800
C1—C6	1.490 (14)	C7B—C8B	1.55 (3)
C2—H2	0.9800	C7B—C9B	1.76 (6)
C2—C3	1.61 (4)	C8B—H8BA	0.9600
C2—C7	1.488 (16)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.515 (17)	C9B—H9BB	0.9600
C4—H4A	0.9600	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.487 (14)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.60 (4)	O1C—H1CA	0.82 (2)
C5—C10	1.519 (17)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.36 (4)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.49 (2)
C7—C8	1.41 (2)	C1C—C6C	1.52 (3)
C7—C9	1.66 (6)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.61 (3)
C8—H8B	0.9600	C2C—C7C	1.51 (3)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.438 (16)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.43 (2)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.46 (3)
O1B—C1B	1.34 (2)	C5C—C10C	1.60 (3)
O1B—H1BA	0.80 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.427 (14)	C7C—H7C	0.9800
C1B—C6B	1.510 (16)	C7C—C8C	1.50 (2)
C2B—H2B	0.9800	C7C—C9C	1.68 (4)
C2B—C3B	1.48 (3)	C8C—H8CA	0.9600
C2B—C7B	1.555 (17)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9700
C3B—C4B	1.505 (16)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.452 (15)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	85.4	C10B—C5B—C6B	111 (2)
C1—O1—H1B	109.5	C1B—C6B—H6BA	108.7
C1—O1—H1A	108 (10)	C1B—C6B—H6BB	108.7
O1—C1—H1	107.0	C5B—C6B—C1B	114.4 (19)
O1—C1—C2	109.8 (17)	C5B—C6B—H6BA	108.7
O1—C1—C6	114.5 (19)	C5B—C6B—H6BB	108.7
C2—C1—H1	107.0	H6BA—C6B—H6BB	107.6
C6—C1—H1	107.0	C2B—C7B—H7B	109.1
C6—C1—C2	111.3 (9)	C2B—C7B—C9B	108 (3)
C1—C2—H2	108.2	C8B—C7B—C2B	108.6 (15)
C1—C2—C3	102.9 (19)	C8B—C7B—H7B	109.1
C3—C2—H2	108.2	C8B—C7B—C9B	113.1 (19)
C7—C2—C1	114.6 (10)	C9B—C7B—H7B	109.1
C7—C2—H2	108.2	C7B—C8B—H8BA	109.5
C7—C2—C3	114 (3)	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.0	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.0	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.4	H8BA—C8B—H8BC	109.5
C4—C3—C2	109 (2)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.0	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.0	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.7	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.7	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	108.2	H9BA—C9B—H9BC	109.5
C5—C4—C3	110.0 (11)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.7	C5B—C10B—H10D	109.5
C5—C4—H4B	109.7	C5B—C10B—H10E	109.5
C4—C5—H5	111.2	C5B—C10B—H10F	109.5
C4—C5—C6	108 (2)	H10D—C10B—H10E	109.5
C4—C5—C10	109.7 (12)	H10D—C10B—H10F	109.5
C6—C5—H5	111.2	H10E—C10B—H10F	109.5
C10—C5—H5	111.2	H1CA—O1C—H1C	106.3
C10—C5—C6	106 (2)	C1C—O1C—H1CA	122 (10)
C1—C6—C5	108.3 (19)	C1C—O1C—H1C	109.5
C1—C6—H6A	110.0	O1C—C1C—H1CB	106.3
C1—C6—H6B	110.0	O1C—C1C—C2C	109 (3)
C5—C6—H6A	110.0	O1C—C1C—C6C	112.7 (13)
C5—C6—H6B	110.0	C2C—C1C—H1CB	106.3
H6A—C6—H6B	108.4	C2C—C1C—C6C	115.1 (10)
C2—C7—H7	108.0	C6C—C1C—H1CB	106.3
C2—C7—C9	110 (3)	C1C—C2C—H2C	104.5
C8—C7—C2	112.6 (15)	C1C—C2C—C3C	107 (2)
C8—C7—H7	108.0	C1C—C2C—C7C	115.3 (11)
C8—C7—C9	110 (2)	C3C—C2C—H2C	104.5
C9—C7—H7	108.0	C7C—C2C—H2C	104.5
C7—C8—H8A	109.5	C7C—C2C—C3C	119.7 (13)
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.7
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.7
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	108.2
H8A—C8—H8C	109.5	C4C—C3C—C2C	109.6 (14)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.7
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.7
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.1
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.1
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.8
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.6 (11)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.1
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.1
C5—C10—H10B	109.5	C4C—C5C—H5C	105.0
C5—C10—H10C	109.5	C4C—C5C—C6C	108 (2)
H10A—C10—H10B	109.5	C4C—C5C—C10C	118.1 (11)
H10A—C10—H10C	109.5	C6C—C5C—H5C	105.0
H10B—C10—H10C	109.5	C6C—C5C—C10C	114.2 (12)
H1BB—O1B—H1BA	104.1	C10C—C5C—H5C	105.0
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.4
C1B—O1B—H1BA	113 (7)	C1C—C6C—H6CB	108.4
O1B—C1B—H1BC	103.5	C5C—C6C—C1C	115.6 (13)
O1B—C1B—C2B	122.1 (18)	C5C—C6C—H6CA	108.4
O1B—C1B—C6B	108.7 (16)	C5C—C6C—H6CB	108.4
C2B—C1B—H1BC	103.5	H6CA—C6C—H6CB	107.4
C2B—C1B—C6B	113.2 (10)	C2C—C7C—H7C	109.8
C6B—C1B—H1BC	103.5	C2C—C7C—C9C	105 (2)
C1B—C2B—H2B	104.1	C8C—C7C—C2C	112.9 (11)
C1B—C2B—C3B	113 (2)	C8C—C7C—H7C	109.8
C1B—C2B—C7B	113.1 (9)	C8C—C7C—C9C	108.9 (14)
C3B—C2B—H2B	104.1	C9C—C7C—H7C	109.8
C3B—C2B—C7B	117 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	104.1	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.5	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.5	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	111 (2)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.1	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.5	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.5	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.5	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.5	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.5	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	115.0 (11)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.5	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.5	C5C—C10C—H10H	109.5
C4B—C5B—H5B	105.4	C5C—C10C—H10I	109.5
C4B—C5B—C6B	110.8 (18)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	117.3 (13)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	105.4	H10H—C10C—H10I	109.5
C10B—C5B—H5B	105.4

O1—C1—C2—C3	169 (2)	C3B—C2B—C7B—C9B	−54 (2)
O1—C1—C2—C7	44 (4)	C3B—C4B—C5B—C6B	49 (4)
O1—C1—C6—C5	−172 (2)	C3B—C4B—C5B—C10B	179 (3)
C1—C2—C3—C4	63 (2)	C4B—C5B—C6B—C1B	−46 (3)
C1—C2—C7—C8	−164 (3)	C6B—C1B—C2B—C3B	−53 (4)
C1—C2—C7—C9	73 (3)	C6B—C1B—C2B—C7B	172 (3)
C2—C1—C6—C5	63 (3)	C7B—C2B—C3B—C4B	−172 (2)
C2—C3—C4—C5	−67 (3)	C10B—C5B—C6B—C1B	−178 (2)
C3—C2—C7—C8	77 (4)	O1C—C1C—C2C—C3C	−173.0 (14)
C3—C2—C7—C9	−46 (2)	O1C—C1C—C2C—C7C	51 (3)
C3—C4—C5—C6	63 (3)	O1C—C1C—C6C—C5C	173 (2)
C3—C4—C5—C10	177 (3)	C1C—C2C—C3C—C4C	55 (2)
C4—C5—C6—C1	−60 (3)	C1C—C2C—C7C—C8C	−175 (3)
C6—C1—C2—C3	−63 (3)	C1C—C2C—C7C—C9C	66 (3)
C6—C1—C2—C7	172 (3)	C2C—C1C—C6C—C5C	46 (4)
C7—C2—C3—C4	−172.4 (17)	C2C—C3C—C4C—C5C	−67 (3)
C10—C5—C6—C1	−177.4 (16)	C3C—C2C—C7C—C8C	55 (3)
O1B—C1B—C2B—C3B	174 (2)	C3C—C2C—C7C—C9C	−63.6 (19)
O1B—C1B—C2B—C7B	39 (4)	C3C—C4C—C5C—C6C	63 (3)
O1B—C1B—C6B—C5B	−172 (2)	C3C—C4C—C5C—C10C	−165 (3)
C1B—C2B—C3B—C4B	54 (3)	C4C—C5C—C6C—C1C	−51 (3)
C1B—C2B—C7B—C8B	−158 (3)	C6C—C1C—C2C—C3C	−45 (3)
C1B—C2B—C7B—C9B	80 (3)	C6C—C1C—C2C—C7C	180 (3)
C2B—C1B—C6B—C5B	49 (4)	C7C—C2C—C3C—C4C	−172 (2)
C2B—C3B—C4B—C5B	−54 (4)	C10C—C5C—C6C—C1C	176 (2)
C3B—C2B—C7B—C8B	69 (4)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_2.39GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.183 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3823 (16) Å	Cell parameters from 1917 reflections
b = 20.381 (5) Å	θ = 5.8–18.3°
c = 11.656 (3) Å	µ = 0.07 mm⁻¹
β = 103.206 (18)°	T = 296 K
V = 2632.4 (10) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.05 mm

Data collection top

Xcalibur, Eos diffractometer	681 reflections with I > 2σ(I)
Detector resolution: 16.2413 pixels mm^-1	R_int = 0.164
ω and π scans	θ_max = 25.7°, θ_min = 5.6°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −13→13
T_min = 0.968, T_max = 0.997	k = −20→20
10113 measured reflections	l = −10→10
1917 independent reflections

Refinement top

Refinement on F²	208 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.092	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.317	w = 1/[σ²(F_o²) + (0.166P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
1917 reflections	Δρ_max = 0.12 e Å⁻³
311 parameters	Δρ_min = −0.10 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0227 (6)	0.0643 (3)	0.4943 (7)	0.125 (3)
H1B	0.043494	0.062048	0.477864	0.188*	0.5
H1A	−0.01 (2)	0.0273 (13)	0.538 (4)	0.188*	0.5
C1	−0.0111 (8)	0.0970 (6)	0.6027 (12)	0.114 (3)
H1	−0.080284	0.084241	0.634665	0.137*
C2	−0.0153 (8)	0.1713 (5)	0.5887 (10)	0.103 (3)
H2	0.059549	0.184649	0.567064	0.155*
C3	−0.0128 (7)	0.2001 (4)	0.7075 (10)	0.107 (3)
H3A	−0.081513	0.184560	0.736010	0.128*
H3B	−0.017038	0.247591	0.702300	0.128*
C4	0.1042 (7)	0.1793 (5)	0.7919 (9)	0.110 (3)
H4A	0.172135	0.195061	0.762435	0.132*
H4B	0.108542	0.199233	0.868270	0.132*
C5	0.1128 (8)	0.1063 (5)	0.8057 (10)	0.104 (3)
H5	0.046247	0.091235	0.839525	0.125*
C6	0.1004 (7)	0.0754 (4)	0.6893 (9)	0.096 (3)
H6A	0.098516	0.028145	0.698049	0.115*
H6B	0.170461	0.086319	0.658709	0.115*
C7	−0.1206 (7)	0.1926 (5)	0.4875 (9)	0.100 (3)
H7	−0.121523	0.164657	0.418768	0.120*
C8	−0.0993 (8)	0.2606 (6)	0.4573 (12)	0.151 (5)
H8A	−0.164020	0.274943	0.394135	0.227*
H8B	−0.095666	0.288043	0.524892	0.227*
H8C	−0.024397	0.263348	0.432929	0.227*
C9	−0.2468 (7)	0.1885 (4)	0.5196 (10)	0.123 (4)
H9A	−0.259445	0.144763	0.545059	0.184*
H9B	−0.308985	0.199249	0.451576	0.184*
H9C	−0.249288	0.218893	0.581893	0.184*
C10	0.2288 (8)	0.0872 (4)	0.8868 (8)	0.108 (3)
H10A	0.234913	0.107873	0.961968	0.162*
H10B	0.231412	0.040433	0.896591	0.162*
H10C	0.294964	0.101053	0.854171	0.162*
O1B	0.1870 (5)	0.0443 (4)	0.4189 (7)	0.122 (3)
H1BB	0.126226	0.047849	0.445004	0.184*	0.5
H1CA	0.341 (5)	0.038 (5)	0.529 (4)	0.184*	0.5
C1B	0.1769 (8)	0.0849 (5)	0.3209 (10)	0.104 (3)
H1BC	0.243918	0.073352	0.284862	0.125*
C2B	0.1899 (8)	0.1559 (5)	0.3496 (10)	0.102 (3)
H2B	0.117298	0.166229	0.377803	0.123*
C3B	0.1782 (8)	0.1962 (5)	0.2451 (11)	0.110 (3)
H3BA	0.246408	0.188590	0.209864	0.132*
H3BB	0.178362	0.242207	0.266694	0.132*
C4B	0.0599 (8)	0.1798 (5)	0.1550 (9)	0.120 (4)
H4BA	−0.007772	0.193731	0.186716	0.144*
H4BB	0.057277	0.204683	0.083450	0.144*
C5B	0.0457 (8)	0.1071 (6)	0.1241 (11)	0.116 (4)
H5B	0.110680	0.095408	0.085291	0.139*
C6B	0.0639 (7)	0.0690 (5)	0.2321 (9)	0.101 (3)
H6BA	0.065186	0.022783	0.212254	0.121*
H6BB	−0.004295	0.076021	0.267511	0.121*
C7B	0.2939 (7)	0.1725 (5)	0.4555 (9)	0.104 (3)
H7B	0.292647	0.141123	0.518864	0.125*
C8B	0.2779 (7)	0.2401 (5)	0.4996 (10)	0.137 (5)
H8BA	0.343141	0.249902	0.565493	0.206*
H8BB	0.277317	0.271337	0.437809	0.206*
H8BC	0.202769	0.242438	0.523711	0.206*
C9B	0.4190 (7)	0.1692 (4)	0.4249 (10)	0.124 (4)
H9BA	0.431204	0.126178	0.396333	0.186*
H9BB	0.422693	0.201105	0.365124	0.186*
H9BC	0.480772	0.178422	0.494132	0.186*
C10B	−0.0725 (7)	0.0912 (5)	0.0387 (9)	0.126 (4)
H10D	−0.138069	0.098525	0.076360	0.188*
H10E	−0.072259	0.046067	0.015137	0.188*
H10F	−0.082083	0.118873	−0.029432	0.188*
O1C	0.4044 (5)	0.0168 (3)	0.5442 (7)	0.110 (2)
H1C	0.463966	0.000473	0.527089	0.165*	0.5
H1BA	0.255 (4)	0.031 (6)	0.433 (7)	0.165*	0.5
C1C	0.4063 (8)	0.0036 (5)	0.6612 (11)	0.104 (3)
H1CB	0.355281	0.036895	0.686256	0.124*
C2C	0.5301 (7)	0.0155 (5)	0.7302 (10)	0.107 (3)
H2C	0.578574	−0.015504	0.696227	0.128*
C3C	0.5465 (8)	−0.0091 (5)	0.8601 (10)	0.105 (3)
H3CA	0.631798	−0.009118	0.898030	0.126*
H3CB	0.506404	0.021190	0.902866	0.126*
C4C	0.4967 (8)	−0.0763 (5)	0.8669 (9)	0.120 (4)
H4CA	0.544888	−0.107491	0.834549	0.144*
H4CB	0.503050	−0.087589	0.948895	0.144*
C5C	0.3751 (9)	−0.0817 (6)	0.8052 (12)	0.122 (4)
H5C	0.329859	−0.050877	0.843175	0.147*
C6C	0.3527 (7)	−0.0614 (5)	0.6798 (10)	0.108 (3)
H6CA	0.266234	−0.059575	0.647696	0.162*
H6CB	0.385526	−0.094533	0.636171	0.162*
C7C	0.5875 (7)	0.0818 (5)	0.7155 (9)	0.103 (3)
H7C	0.578544	0.089908	0.631020	0.124*
C8C	0.7181 (7)	0.0857 (5)	0.7736 (11)	0.140 (4)
H8CA	0.750527	0.126375	0.753125	0.210*
H8CB	0.760024	0.049756	0.747543	0.210*
H8CC	0.727959	0.083342	0.857486	0.210*
C9C	0.5148 (9)	0.1354 (5)	0.7649 (12)	0.145 (4)
H9CA	0.531793	0.132263	0.849313	0.218*
H9CB	0.430029	0.128824	0.733372	0.218*
H9CC	0.537708	0.177993	0.742631	0.218*
C10C	0.3162 (8)	−0.1496 (5)	0.8111 (10)	0.131 (4)
H10G	0.234062	−0.148406	0.766820	0.197*
H10H	0.359955	−0.182213	0.778472	0.197*
H10I	0.318140	−0.160233	0.891750	0.197*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.141 (5)	0.123 (7)	0.097 (8)	0.008 (4)	−0.002 (4)	−0.009 (4)
C1	0.115 (6)	0.114 (7)	0.105 (9)	−0.003 (5)	0.008 (6)	−0.004 (5)
C2	0.115 (5)	0.095 (7)	0.098 (9)	0.006 (5)	0.021 (5)	0.021 (5)
C3	0.105 (5)	0.107 (7)	0.097 (8)	0.000 (4)	0.001 (5)	−0.004 (5)
C4	0.111 (5)	0.111 (7)	0.097 (8)	0.000 (5)	0.000 (5)	−0.012 (4)
C5	0.105 (5)	0.105 (7)	0.095 (8)	0.005 (5)	0.005 (5)	−0.002 (5)
C6	0.093 (5)	0.090 (7)	0.095 (8)	0.008 (4)	0.005 (5)	0.001 (4)
C7	0.087 (5)	0.099 (7)	0.108 (8)	0.022 (4)	0.009 (5)	0.024 (4)
C8	0.121 (6)	0.145 (11)	0.174 (13)	0.012 (6)	0.006 (7)	0.055 (7)
C9	0.115 (6)	0.103 (9)	0.140 (11)	−0.005 (5)	0.004 (6)	−0.007 (5)
C10	0.140 (6)	0.109 (8)	0.062 (8)	0.021 (5)	−0.005 (5)	0.007 (4)
O1B	0.114 (4)	0.133 (7)	0.103 (8)	0.004 (4)	−0.009 (4)	0.027 (4)
C1B	0.107 (5)	0.101 (7)	0.096 (8)	−0.011 (5)	0.007 (5)	0.006 (5)
C2B	0.115 (5)	0.108 (7)	0.082 (8)	−0.005 (5)	0.020 (5)	−0.006 (5)
C3B	0.113 (5)	0.100 (7)	0.113 (8)	0.027 (5)	0.017 (6)	0.015 (5)
C4B	0.132 (6)	0.127 (8)	0.092 (8)	0.006 (5)	0.007 (6)	0.009 (5)
C5B	0.110 (6)	0.124 (8)	0.112 (9)	0.009 (5)	0.023 (6)	0.016 (5)
C6B	0.098 (5)	0.108 (7)	0.081 (8)	−0.005 (4)	−0.010 (5)	0.006 (4)
C7B	0.103 (5)	0.104 (7)	0.104 (8)	−0.011 (4)	0.021 (5)	−0.019 (4)
C8B	0.115 (6)	0.124 (10)	0.159 (12)	−0.001 (6)	0.002 (6)	−0.055 (7)
C9B	0.103 (6)	0.125 (9)	0.141 (11)	0.005 (5)	0.022 (6)	−0.005 (5)
C10B	0.112 (6)	0.142 (10)	0.110 (11)	0.013 (5)	0.000 (6)	−0.017 (5)
O1C	0.124 (4)	0.119 (7)	0.080 (8)	0.006 (3)	0.010 (4)	0.011 (3)
C1C	0.109 (6)	0.099 (7)	0.096 (8)	−0.006 (5)	0.008 (6)	0.009 (5)
C2C	0.099 (5)	0.103 (7)	0.103 (8)	−0.001 (5)	−0.010 (5)	0.002 (5)
C3C	0.113 (5)	0.100 (7)	0.095 (8)	0.005 (5)	0.008 (5)	0.000 (4)
C4C	0.132 (6)	0.109 (7)	0.104 (8)	−0.006 (5)	−0.003 (6)	0.015 (4)
C5C	0.126 (6)	0.121 (8)	0.119 (9)	0.005 (5)	0.028 (6)	0.023 (6)
C6C	0.094 (5)	0.100 (7)	0.116 (9)	0.004 (4)	−0.005 (5)	0.008 (5)
C7C	0.107 (5)	0.095 (7)	0.096 (8)	−0.009 (5)	−0.003 (5)	−0.001 (4)
C8C	0.096 (6)	0.150 (10)	0.162 (12)	−0.006 (5)	0.005 (6)	0.020 (6)
C9C	0.138 (7)	0.111 (10)	0.186 (13)	−0.037 (6)	0.036 (8)	−0.016 (6)
C10C	0.126 (6)	0.114 (10)	0.147 (12)	0.008 (6)	0.018 (7)	0.027 (6)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.454 (13)
O1—H1A	0.90 (2)	C5B—C10B	1.515 (11)
O1—C1	1.408 (13)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.523 (12)	C7B—H7B	0.9800
C1—C6	1.496 (11)	C7B—C8B	1.495 (11)
C2—H2	0.9800	C7B—C9B	1.546 (11)
C2—C3	1.499 (14)	C8B—H8BA	0.9600
C2—C7	1.539 (11)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.524 (11)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.497 (11)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.473 (13)	O1C—H1CA	0.82 (2)
C5—C10	1.490 (10)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.385 (11)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.474 (10)
C7—C8	1.464 (10)	C1C—C6C	1.495 (10)
C7—C9	1.568 (12)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.565 (13)
C8—H8B	0.9600	C2C—C7C	1.528 (11)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.492 (10)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.411 (11)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.484 (14)
O1B—C1B	1.393 (11)	C5C—C10C	1.545 (12)
O1B—H1BA	0.81 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.485 (13)	C7C—H7C	0.9800
C1B—C6B	1.490 (11)	C7C—C8C	1.488 (10)
C2B—H2B	0.9800	C7C—C9C	1.558 (13)
C2B—C3B	1.451 (14)	C8C—H8CA	0.9600
C2B—C7B	1.540 (11)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.543 (11)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.525 (12)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	94.5	C10B—C5B—H5B	107.2
C1—O1—H1B	109.5	C1B—C6B—H6BA	108.6
C1—O1—H1A	85.1 (19)	C1B—C6B—H6BB	108.6
O1—C1—H1	107.3	C5B—C6B—C1B	114.5 (8)
O1—C1—C2	112.4 (11)	C5B—C6B—H6BA	108.6
O1—C1—C6	110.9 (8)	C5B—C6B—H6BB	108.6
C2—C1—H1	107.3	H6BA—C6B—H6BB	107.6
C6—C1—H1	107.3	C2B—C7B—H7B	108.6
C6—C1—C2	111.4 (7)	C2B—C7B—C9B	112.6 (8)
C1—C2—H2	107.2	C8B—C7B—C2B	110.3 (7)
C1—C2—C7	111.2 (8)	C8B—C7B—H7B	108.6
C3—C2—C1	107.3 (8)	C8B—C7B—C9B	108.1 (8)
C3—C2—H2	107.2	C9B—C7B—H7B	108.6
C3—C2—C7	116.5 (8)	C7B—C8B—H8BA	109.5
C7—C2—H2	107.2	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.0	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.0	H8BA—C8B—H8BB	109.5
C2—C3—C4	108.4 (8)	H8BA—C8B—H8BC	109.5
H3A—C3—H3B	108.4	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.0	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.0	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.2	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.2	H9BA—C9B—H9BB	109.5
H4A—C4—H4B	107.9	H9BA—C9B—H9BC	109.5
C5—C4—C3	111.9 (7)	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.2	C5B—C10B—H10D	109.5
C5—C4—H4B	109.2	C5B—C10B—H10E	109.5
C4—C5—H5	108.5	C5B—C10B—H10F	109.5
C6—C5—C4	109.6 (9)	H10D—C10B—H10E	109.5
C6—C5—H5	108.5	H10D—C10B—H10F	109.5
C6—C5—C10	110.9 (8)	H10E—C10B—H10F	109.5
C10—C5—C4	110.8 (7)	H1CA—O1C—H1C	152.8
C10—C5—H5	108.5	C1C—O1C—H1CA	98 (2)
C1—C6—H6A	109.1	C1C—O1C—H1C	109.5
C1—C6—H6B	109.1	O1C—C1C—H1CB	106.3
C5—C6—C1	112.5 (8)	O1C—C1C—C2C	107.6 (9)
C5—C6—H6A	109.1	O1C—C1C—C6C	113.5 (8)
C5—C6—H6B	109.1	C2C—C1C—H1CB	106.3
H6A—C6—H6B	107.8	C2C—C1C—C6C	116.0 (7)
C2—C7—H7	108.9	C6C—C1C—H1CB	106.3
C2—C7—C9	113.4 (8)	C1C—C2C—H2C	103.3
C8—C7—C2	107.9 (7)	C1C—C2C—C3C	111.3 (9)
C8—C7—H7	108.9	C1C—C2C—C7C	117.7 (7)
C8—C7—C9	108.6 (7)	C3C—C2C—H2C	103.3
C9—C7—H7	108.9	C7C—C2C—H2C	103.3
C7—C8—H8A	109.5	C7C—C2C—C3C	115.6 (7)
C7—C8—H8B	109.5	C2C—C3C—H3CA	109.1
C7—C8—H8C	109.5	C2C—C3C—H3CB	109.1
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.8
H8A—C8—H8C	109.5	C4C—C3C—C2C	112.4 (7)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	109.1
C7—C9—H9A	109.5	C4C—C3C—H3CB	109.1
C7—C9—H9B	109.5	C3C—C4C—H4CA	109.1
C7—C9—H9C	109.5	C3C—C4C—H4CB	109.1
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.8
H9A—C9—H9C	109.5	C5C—C4C—C3C	112.7 (8)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	109.1
C5—C10—H10A	109.5	C5C—C4C—H4CB	109.1
C5—C10—H10B	109.5	C4C—C5C—H5C	106.0
C5—C10—H10C	109.5	C4C—C5C—C6C	114.1 (9)
H10A—C10—H10B	109.5	C4C—C5C—C10C	115.6 (8)
H10A—C10—H10C	109.5	C6C—C5C—H5C	106.0
H10B—C10—H10C	109.5	C6C—C5C—C10C	108.3 (9)
H1BB—O1B—H1BA	144.3	C10C—C5C—H5C	106.0
C1B—O1B—H1BB	109.5	C1C—C6C—H6CA	108.8
C1B—O1B—H1BA	105 (5)	C1C—C6C—H6CB	108.8
O1B—C1B—H1BC	106.4	C5C—C6C—C1C	113.9 (8)
O1B—C1B—C2B	114.1 (11)	C5C—C6C—H6CA	108.8
O1B—C1B—C6B	109.7 (8)	C5C—C6C—H6CB	108.8
C2B—C1B—H1BC	106.4	H6CA—C6C—H6CB	107.7
C2B—C1B—C6B	113.2 (7)	C2C—C7C—H7C	108.2
C6B—C1B—H1BC	106.4	C2C—C7C—C9C	107.5 (9)
C1B—C2B—H2B	103.7	C8C—C7C—C2C	113.8 (8)
C1B—C2B—C7B	114.5 (7)	C8C—C7C—H7C	108.2
C3B—C2B—C1B	112.2 (10)	C8C—C7C—C9C	110.8 (8)
C3B—C2B—H2B	103.7	C9C—C7C—H7C	108.2
C3B—C2B—C7B	117.0 (9)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	103.7	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	109.6	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	109.6	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	110.3 (8)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	108.1	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	109.6	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	109.6	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.8	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.8	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.7	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.6 (7)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.8	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.8	C5C—C10C—H10H	109.5
C4B—C5B—H5B	107.2	C5C—C10C—H10I	109.5
C6B—C5B—C4B	109.2 (11)	H10G—C10C—H10H	109.5
C6B—C5B—H5B	107.2	H10G—C10C—H10I	109.5
C6B—C5B—C10B	112.5 (8)	H10H—C10C—H10I	109.5
C10B—C5B—C4B	113.2 (7)

O1—C1—C2—C3	175.3 (8)	C3B—C2B—C7B—C9B	−58.4 (13)
O1—C1—C2—C7	46.9 (11)	C3B—C4B—C5B—C6B	51.8 (11)
O1—C1—C6—C5	−177.3 (10)	C3B—C4B—C5B—C10B	178.1 (9)
C1—C2—C3—C4	60.9 (10)	C4B—C5B—C6B—C1B	−51.1 (13)
C1—C2—C7—C8	−164.2 (9)	C6B—C1B—C2B—C3B	−53.3 (12)
C1—C2—C7—C9	75.5 (11)	C6B—C1B—C2B—C7B	170.2 (9)
C2—C1—C6—C5	56.7 (13)	C7B—C2B—C3B—C4B	−171.7 (7)
C2—C3—C4—C5	−61.5 (11)	C10B—C5B—C6B—C1B	−177.7 (8)
C3—C2—C7—C8	72.6 (12)	O1C—C1C—C2C—C3C	−170.7 (8)
C3—C2—C7—C9	−47.7 (12)	O1C—C1C—C2C—C7C	52.7 (12)
C3—C4—C5—C6	56.3 (10)	O1C—C1C—C6C—C5C	168.9 (9)
C3—C4—C5—C10	179.0 (10)	C1C—C2C—C3C—C4C	46.9 (11)
C4—C5—C6—C1	−53.5 (11)	C1C—C2C—C7C—C8C	−171.0 (10)
C6—C1—C2—C3	−59.5 (11)	C1C—C2C—C7C—C9C	65.9 (12)
C6—C1—C2—C7	172.1 (10)	C2C—C1C—C6C—C5C	43.4 (14)
C7—C2—C3—C4	−173.9 (7)	C2C—C3C—C4C—C5C	−54.0 (12)
C10—C5—C6—C1	−176.1 (8)	C3C—C2C—C7C—C8C	54.1 (12)
O1B—C1B—C2B—C3B	−179.7 (8)	C3C—C2C—C7C—C9C	−69.0 (10)
O1B—C1B—C2B—C7B	43.8 (11)	C3C—C4C—C5C—C6C	55.0 (13)
O1B—C1B—C6B—C5B	−178.2 (11)	C3C—C4C—C5C—C10C	−178.4 (9)
C1B—C2B—C3B—C4B	53.0 (12)	C4C—C5C—C6C—C1C	−49.1 (13)
C1B—C2B—C7B—C8B	−163.2 (10)	C6C—C1C—C2C—C3C	−42.3 (14)
C1B—C2B—C7B—C9B	76.0 (11)	C6C—C1C—C2C—C7C	−178.9 (10)
C2B—C1B—C6B—C5B	53.0 (14)	C7C—C2C—C3C—C4C	−175.4 (7)
C2B—C3B—C4B—C5B	−53.8 (13)	C10C—C5C—C6C—C1C	−179.4 (8)
C3B—C2B—C7B—C8B	62.5 (14)

beta-DL-2-Isopropyl-5-methylcyclohexanol (beta_DL_2.90GPa) top

Crystal data top

C₁₀H₂₀O	F(000) = 1056
M_r = 156.26	D_x = 1.204 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.171 (3) Å	Cell parameters from 1145 reflections
b = 20.436 (8) Å	θ = 4.8–26.7°
c = 11.620 (4) Å	µ = 0.07 mm⁻¹
β = 102.80 (3)°	T = 296 K
V = 2586.7 (15) Å³	Plate, colourless
Z = 12	0.45 × 0.45 × 0.02 mm

Data collection top

Xcalibur, Eos diffractometer	402 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.227
ω and φ scans	θ_max = 26.7°, θ_min = 4.8°
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
T_min = 0.967, T_max = 0.999	k = −25→25
8700 measured reflections	l = −10→10
1145 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.099	w = 1/[σ²(F_o²) + (0.0593P)² + 6.7529P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.285	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.10 e Å⁻³
1145 reflections	Δρ_min = −0.12 e Å⁻³
312 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
208 restraints	Extinction coefficient: 0.012 (8)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.032 (2)	0.0645 (5)	0.4973 (19)	0.097 (12)
H1B	0.036132	0.062525	0.482849	0.146*	0.5
H1A	−0.01 (5)	0.027 (6)	0.518 (5)	0.146*	0.5
C1	−0.023 (3)	0.0947 (7)	0.614 (3)	0.082 (8)
H1	−0.093819	0.084800	0.648766	0.099*
C2	−0.014 (3)	0.1710 (6)	0.581 (3)	0.075 (8)
H2	0.065365	0.180430	0.562388	0.112*
C3	−0.020 (3)	0.2007 (6)	0.709 (3)	0.071 (8)
H3A	−0.026801	0.247984	0.704999	0.086*
H3B	−0.091128	0.183510	0.734417	0.086*
C4	0.097 (3)	0.1808 (6)	0.796 (2)	0.078 (8)
H4A	0.095954	0.198451	0.872764	0.094*
H4B	0.166722	0.199509	0.770366	0.094*
C5	0.113 (3)	0.1055 (6)	0.805 (3)	0.075 (8)
H5	0.046203	0.089146	0.839850	0.090*
C6	0.097 (3)	0.0758 (6)	0.691 (3)	0.072 (8)
H6A	0.100260	0.028582	0.700050	0.086*
H6B	0.162564	0.089297	0.654735	0.086*
C7	−0.117 (4)	0.1938 (8)	0.483 (4)	0.079 (9)
H7	−0.116681	0.166223	0.414214	0.095*
C8	−0.096 (3)	0.2620 (8)	0.450 (3)	0.116 (14)
H8A	−0.162610	0.275686	0.387542	0.175*
H8B	−0.091942	0.289968	0.517402	0.175*
H8C	−0.020355	0.264704	0.424386	0.175*
C9	−0.241 (4)	0.1877 (9)	0.513 (4)	0.106 (14)
H9A	−0.251576	0.144161	0.540074	0.159*
H9B	−0.304266	0.196531	0.443540	0.159*
H9C	−0.247748	0.218579	0.573432	0.159*
C10	0.231 (3)	0.0894 (7)	0.892 (3)	0.095 (13)
H10A	0.232776	0.111655	0.965298	0.143*
H10B	0.235813	0.043047	0.905663	0.143*
H10C	0.299407	0.103321	0.860822	0.143*
O1B	0.1874 (19)	0.0405 (5)	0.4095 (17)	0.098 (12)
H1BB	0.127176	0.042308	0.438982	0.147*	0.5
H1CA	0.324 (5)	0.009 (7)	0.525 (7)	0.147*	0.5
C1B	0.175 (4)	0.0844 (8)	0.321 (3)	0.089 (8)
H1BC	0.239591	0.071868	0.280047	0.107*
C2B	0.193 (3)	0.1518 (6)	0.338 (2)	0.075 (8)
H2B	0.118401	0.162394	0.366134	0.090*
C3B	0.174 (3)	0.1929 (7)	0.236 (3)	0.094 (8)
H3BA	0.242272	0.187542	0.198255	0.113*
H3BB	0.172736	0.238174	0.260910	0.113*
C4B	0.057 (3)	0.1785 (7)	0.148 (2)	0.084 (8)
H4BA	−0.011229	0.195892	0.177717	0.101*
H4BB	0.058684	0.200971	0.075167	0.101*
C5B	0.036 (3)	0.1089 (8)	0.124 (3)	0.099 (9)
H5B	0.102214	0.096188	0.084909	0.119*
C6B	0.055 (3)	0.0663 (6)	0.231 (3)	0.081 (8)
H6BA	0.059397	0.020935	0.207322	0.098*
H6BB	−0.013880	0.070966	0.267711	0.098*
C7B	0.294 (4)	0.1713 (8)	0.453 (4)	0.085 (9)
H7B	0.294524	0.141086	0.518980	0.102*
C8B	0.273 (3)	0.2425 (7)	0.487 (3)	0.103 (13)
H8BA	0.333756	0.254469	0.555845	0.155*
H8BB	0.279712	0.270874	0.422674	0.155*
H8BC	0.192733	0.246588	0.502769	0.155*
C9B	0.430 (4)	0.1663 (9)	0.402 (4)	0.103 (14)
H9BA	0.442730	0.121812	0.381349	0.155*
H9BB	0.423107	0.193752	0.334097	0.155*
H9BC	0.497445	0.180518	0.463078	0.155*
C10B	−0.080 (4)	0.0889 (8)	0.037 (3)	0.096 (14)
H10D	−0.149830	0.106434	0.062231	0.144*
H10E	−0.085619	0.042032	0.034095	0.144*
H10F	−0.078516	0.105549	−0.039741	0.144*
O1C	0.396 (2)	0.0195 (5)	0.550 (2)	0.093 (12)
H1C	0.455680	0.003439	0.529928	0.140*	0.5
H1BA	0.253 (5)	0.022 (5)	0.423 (7)	0.140*	0.5
C1C	0.402 (3)	0.0055 (7)	0.669 (3)	0.077 (8)
H1CB	0.350328	0.037614	0.698052	0.092*
C2C	0.530 (3)	0.0163 (6)	0.733 (3)	0.077 (8)
H2C	0.578323	−0.013943	0.695926	0.093*
C3C	0.546 (3)	−0.0095 (6)	0.858 (3)	0.074 (8)
H3CA	0.632712	−0.010637	0.894289	0.089*
H3CB	0.506908	0.020677	0.902280	0.089*
C4C	0.493 (3)	−0.0769 (6)	0.865 (3)	0.075 (8)
H4CA	0.543555	−0.108339	0.835404	0.090*
H4CB	0.497855	−0.087036	0.947628	0.090*
C5C	0.367 (4)	−0.0856 (9)	0.802 (3)	0.106 (9)
H5C	0.322638	−0.053669	0.839418	0.127*
C6C	0.349 (3)	−0.0599 (7)	0.679 (3)	0.079 (8)
H6CA	0.385017	−0.090483	0.632569	0.119*
H6CB	0.261451	−0.058065	0.644487	0.119*
C7C	0.584 (3)	0.0817 (6)	0.720 (3)	0.074 (8)
H7C	0.585208	0.084889	0.636069	0.089*
C8C	0.717 (4)	0.0902 (9)	0.784 (3)	0.114 (14)
H8CA	0.767369	0.061050	0.750219	0.171*
H8CB	0.725240	0.080267	0.865732	0.171*
H8CC	0.741678	0.134526	0.775123	0.171*
C9C	0.508 (3)	0.1397 (8)	0.743 (3)	0.112 (14)
H9CA	0.433284	0.141262	0.684243	0.168*
H9CB	0.553767	0.179363	0.740783	0.168*
H9CC	0.489996	0.135167	0.819849	0.168*
C10C	0.303 (4)	−0.1513 (7)	0.820 (3)	0.115 (14)
H10G	0.220532	−0.151270	0.773855	0.173*
H10H	0.347694	−0.187092	0.796445	0.173*
H10I	0.301735	−0.156010	0.902219	0.173*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.10 (2)	0.093 (7)	0.101 (18)	0.007 (11)	0.025 (16)	−0.014 (10)
C1	0.082 (13)	0.087 (8)	0.077 (12)	−0.012 (9)	0.014 (9)	−0.008 (9)
C2	0.065 (12)	0.078 (7)	0.080 (12)	0.003 (8)	0.014 (9)	−0.001 (8)
C3	0.067 (12)	0.068 (7)	0.080 (12)	−0.006 (8)	0.019 (9)	0.007 (8)
C4	0.079 (12)	0.081 (7)	0.075 (12)	−0.010 (9)	0.016 (9)	−0.001 (8)
C5	0.077 (12)	0.081 (7)	0.067 (11)	0.001 (9)	0.013 (9)	−0.003 (8)
C6	0.074 (12)	0.074 (7)	0.066 (12)	−0.012 (8)	0.013 (9)	0.003 (8)
C7	0.079 (13)	0.078 (8)	0.082 (13)	0.001 (9)	0.020 (10)	0.003 (9)
C8	0.13 (2)	0.115 (11)	0.11 (2)	0.003 (14)	0.020 (17)	0.043 (13)
C9	0.11 (2)	0.110 (11)	0.09 (2)	−0.010 (15)	0.018 (17)	−0.034 (13)
C10	0.08 (2)	0.093 (9)	0.11 (2)	0.028 (13)	0.013 (17)	−0.016 (12)
O1B	0.094 (19)	0.094 (7)	0.102 (18)	−0.008 (9)	0.012 (16)	0.020 (10)
C1B	0.088 (13)	0.092 (8)	0.086 (12)	0.006 (9)	0.018 (9)	0.000 (9)
C2B	0.079 (12)	0.068 (7)	0.080 (12)	−0.005 (8)	0.022 (9)	0.016 (8)
C3B	0.090 (13)	0.101 (8)	0.090 (12)	−0.002 (9)	0.015 (9)	0.016 (9)
C4B	0.077 (12)	0.096 (8)	0.076 (12)	0.004 (9)	0.007 (9)	0.000 (8)
C5B	0.093 (13)	0.112 (9)	0.090 (12)	0.000 (9)	0.014 (9)	0.011 (9)
C6B	0.081 (13)	0.083 (7)	0.080 (12)	0.006 (8)	0.018 (9)	0.001 (8)
C7B	0.091 (13)	0.072 (8)	0.097 (13)	−0.004 (10)	0.029 (10)	−0.010 (9)
C8B	0.11 (2)	0.098 (10)	0.11 (2)	−0.010 (13)	0.031 (17)	−0.015 (12)
C9B	0.09 (2)	0.102 (11)	0.11 (2)	−0.002 (15)	0.011 (17)	0.005 (14)
C10B	0.07 (2)	0.142 (11)	0.07 (2)	−0.001 (14)	−0.008 (17)	−0.014 (13)
O1C	0.094 (19)	0.097 (7)	0.084 (16)	−0.001 (9)	0.010 (16)	−0.003 (9)
C1C	0.074 (13)	0.081 (8)	0.074 (12)	−0.007 (9)	0.014 (9)	0.002 (9)
C2C	0.077 (12)	0.079 (7)	0.071 (12)	0.007 (8)	0.008 (9)	0.001 (8)
C3C	0.072 (12)	0.074 (7)	0.077 (12)	0.007 (8)	0.016 (9)	−0.003 (8)
C4C	0.081 (12)	0.070 (7)	0.075 (12)	0.006 (8)	0.021 (9)	0.007 (8)
C5C	0.106 (13)	0.108 (9)	0.102 (13)	0.005 (9)	0.020 (10)	0.003 (9)
C6C	0.078 (12)	0.076 (7)	0.082 (12)	−0.001 (8)	0.018 (9)	0.012 (8)
C7C	0.074 (12)	0.070 (7)	0.082 (12)	−0.003 (8)	0.024 (9)	0.004 (8)
C8C	0.10 (2)	0.130 (12)	0.11 (2)	−0.011 (14)	0.017 (17)	−0.028 (13)
C9C	0.11 (2)	0.100 (10)	0.12 (2)	0.018 (13)	0.016 (17)	−0.027 (13)
C10C	0.13 (2)	0.087 (9)	0.14 (2)	−0.014 (14)	0.044 (17)	0.029 (13)

Geometric parameters (Å, º) top

O1—H1B	0.8200	C5B—C6B	1.49 (4)
O1—H1A	0.82 (2)	C5B—C10B	1.51 (2)
O1—C1	1.47 (4)	C6B—H6BA	0.9700
C1—H1	0.9800	C6B—H6BB	0.9700
C1—C2	1.62 (2)	C7B—H7B	0.9800
C1—C6	1.49 (2)	C7B—C8B	1.54 (3)
C2—H2	0.9800	C7B—C9B	1.75 (9)
C2—C3	1.62 (4)	C8B—H8BA	0.9600
C2—C7	1.49 (2)	C8B—H8BB	0.9600
C3—H3A	0.9700	C8B—H8BC	0.9600
C3—H3B	0.9700	C9B—H9BA	0.9600
C3—C4	1.518 (19)	C9B—H9BB	0.9600
C4—H4A	0.9700	C9B—H9BC	0.9600
C4—H4B	0.9700	C10B—H10D	0.9600
C4—C5	1.550 (17)	C10B—H10E	0.9600
C5—H5	0.9800	C10B—H10F	0.9600
C5—C6	1.43 (4)	O1C—H1CA	0.82 (2)
C5—C10	1.51 (2)	O1C—H1C	0.8200
C6—H6A	0.9700	O1C—C1C	1.40 (5)
C6—H6B	0.9700	C1C—H1CB	0.9800
C7—H7	0.9800	C1C—C2C	1.48 (3)
C7—C8	1.48 (3)	C1C—C6C	1.48 (3)
C7—C9	1.51 (9)	C2C—H2C	0.9800
C8—H8A	0.9600	C2C—C3C	1.51 (4)
C8—H8B	0.9600	C2C—C7C	1.49 (3)
C8—H8C	0.9600	C3C—H3CA	0.9700
C9—H9A	0.9600	C3C—H3CB	0.9700
C9—H9B	0.9600	C3C—C4C	1.51 (3)
C9—H9C	0.9600	C4C—H4CA	0.9700
C10—H10A	0.9600	C4C—H4CB	0.9700
C10—H10B	0.9600	C4C—C5C	1.45 (3)
C10—H10C	0.9600	C5C—H5C	0.9800
O1B—H1BB	0.8200	C5C—C6C	1.49 (4)
O1B—C1B	1.35 (3)	C5C—C10C	1.56 (4)
O1B—H1BA	0.80 (2)	C6C—H6CA	0.9700
C1B—H1BC	0.9800	C6C—H6CB	0.9700
C1B—C2B	1.400 (17)	C7C—H7C	0.9800
C1B—C6B	1.55 (2)	C7C—C8C	1.51 (3)
C2B—H2B	0.9800	C7C—C9C	1.52 (4)
C2B—C3B	1.43 (3)	C8C—H8CA	0.9600
C2B—C7B	1.60 (2)	C8C—H8CB	0.9600
C3B—H3BA	0.9700	C8C—H8CC	0.9600
C3B—H3BB	0.9700	C9C—H9CA	0.9600
C3B—C4B	1.50 (2)	C9C—H9CB	0.9600
C4B—H4BA	0.9700	C9C—H9CC	0.9600
C4B—H4BB	0.9700	C10C—H10G	0.9600
C4B—C5B	1.459 (18)	C10C—H10H	0.9600
C5B—H5B	0.9800	C10C—H10I	0.9600

H1B—O1—H1A	80.4	C10B—C5B—H5B	104.2
C1—O1—H1B	109.5	C1B—C6B—H6BA	109.3
C1—O1—H1A	99 (4)	C1B—C6B—H6BB	109.3
O1—C1—H1	113.3	C5B—C6B—C1B	111 (2)
O1—C1—C2	100 (2)	C5B—C6B—H6BA	109.3
O1—C1—C6	108 (3)	C5B—C6B—H6BB	109.3
C2—C1—H1	113.3	H6BA—C6B—H6BB	108.0
C6—C1—H1	113.3	C2B—C7B—H7B	111.9
C6—C1—C2	107.3 (17)	C2B—C7B—C9B	102 (4)
C1—C2—H2	110.5	C8B—C7B—C2B	109.1 (16)
C1—C2—C3	97 (2)	C8B—C7B—H7B	111.9
C3—C2—H2	110.5	C8B—C7B—C9B	109 (3)
C7—C2—C1	113.9 (15)	C9B—C7B—H7B	111.9
C7—C2—H2	110.5	C7B—C8B—H8BA	109.5
C7—C2—C3	114 (3)	C7B—C8B—H8BB	109.5
C2—C3—H3A	110.2	C7B—C8B—H8BC	109.5
C2—C3—H3B	110.2	H8BA—C8B—H8BB	109.5
H3A—C3—H3B	108.5	H8BA—C8B—H8BC	109.5
C4—C3—C2	108 (2)	H8BB—C8B—H8BC	109.5
C4—C3—H3A	110.2	C7B—C9B—H9BA	109.5
C4—C3—H3B	110.2	C7B—C9B—H9BB	109.5
C3—C4—H4A	109.1	C7B—C9B—H9BC	109.5
C3—C4—H4B	109.1	H9BA—C9B—H9BB	109.5
C3—C4—C5	112.5 (12)	H9BA—C9B—H9BC	109.5
H4A—C4—H4B	107.8	H9BB—C9B—H9BC	109.5
C5—C4—H4A	109.1	C5B—C10B—H10D	109.5
C5—C4—H4B	109.1	C5B—C10B—H10E	109.5
C4—C5—H5	106.4	C5B—C10B—H10F	109.5
C6—C5—C4	111 (2)	H10D—C10B—H10E	109.5
C6—C5—H5	106.4	H10D—C10B—H10F	109.5
C6—C5—C10	116 (3)	H10E—C10B—H10F	109.5
C10—C5—C4	109.5 (12)	H1CA—O1C—H1C	126.3
C10—C5—H5	106.4	C1C—O1C—H1CA	97 (6)
C1—C6—H6A	109.4	C1C—O1C—H1C	109.5
C1—C6—H6B	109.4	O1C—C1C—H1CB	107.7
C5—C6—C1	111 (3)	O1C—C1C—C2C	107 (4)
C5—C6—H6A	109.4	O1C—C1C—C6C	109.3 (18)
C5—C6—H6B	109.4	C2C—C1C—H1CB	107.7
H6A—C6—H6B	108.0	C6C—C1C—H1CB	107.7
C2—C7—H7	107.7	C6C—C1C—C2C	117.1 (14)
C2—C7—C9	113 (5)	C1C—C2C—H2C	104.3
C8—C7—C2	110.8 (18)	C1C—C2C—C3C	109 (3)
C8—C7—H7	107.7	C1C—C2C—C7C	116.8 (13)
C8—C7—C9	110 (3)	C3C—C2C—H2C	104.3
C9—C7—H7	107.7	C7C—C2C—H2C	104.3
C7—C8—H8A	109.5	C7C—C2C—C3C	116.7 (16)
C7—C8—H8B	109.5	C2C—C3C—H3CA	108.7
C7—C8—H8C	109.5	C2C—C3C—H3CB	108.7
H8A—C8—H8B	109.5	H3CA—C3C—H3CB	107.6
H8A—C8—H8C	109.5	C4C—C3C—C2C	114.3 (16)
H8B—C8—H8C	109.5	C4C—C3C—H3CA	108.7
C7—C9—H9A	109.5	C4C—C3C—H3CB	108.7
C7—C9—H9B	109.5	C3C—C4C—H4CA	108.4
C7—C9—H9C	109.5	C3C—C4C—H4CB	108.4
H9A—C9—H9B	109.5	H4CA—C4C—H4CB	107.4
H9A—C9—H9C	109.5	C5C—C4C—C3C	115.6 (13)
H9B—C9—H9C	109.5	C5C—C4C—H4CA	108.4
C5—C10—H10A	109.5	C5C—C4C—H4CB	108.4
C5—C10—H10B	109.5	C4C—C5C—H5C	102.7
C5—C10—H10C	109.5	C4C—C5C—C6C	111 (3)
H10A—C10—H10B	109.5	C4C—C5C—C10C	117.2 (15)
H10A—C10—H10C	109.5	C6C—C5C—H5C	102.7
H10B—C10—H10C	109.5	C6C—C5C—C10C	117.9 (17)
H1BB—O1B—H1BA	136.9	C10C—C5C—H5C	102.7
C1B—O1B—H1BB	109.5	C1C—C6C—C5C	115.0 (18)
C1B—O1B—H1BA	113 (7)	C1C—C6C—H6CA	108.5
O1B—C1B—H1BC	103.4	C1C—C6C—H6CB	108.5
O1B—C1B—C2B	124 (2)	C5C—C6C—H6CA	108.5
O1B—C1B—C6B	107 (2)	C5C—C6C—H6CB	108.5
C2B—C1B—H1BC	103.4	H6CA—C6C—H6CB	107.5
C2B—C1B—C6B	114.1 (14)	C2C—C7C—H7C	104.8
C6B—C1B—H1BC	103.4	C2C—C7C—C8C	115.3 (14)
C1B—C2B—H2B	99.4	C2C—C7C—C9C	115 (3)
C1B—C2B—C3B	118 (2)	C8C—C7C—H7C	104.8
C1B—C2B—C7B	114.8 (12)	C8C—C7C—C9C	110.5 (17)
C3B—C2B—H2B	99.4	C9C—C7C—H7C	104.8
C3B—C2B—C7B	120 (2)	C7C—C8C—H8CA	109.5
C7B—C2B—H2B	99.4	C7C—C8C—H8CB	109.5
C2B—C3B—H3BA	108.9	C7C—C8C—H8CC	109.5
C2B—C3B—H3BB	108.9	H8CA—C8C—H8CB	109.5
C2B—C3B—C4B	113 (2)	H8CA—C8C—H8CC	109.5
H3BA—C3B—H3BB	107.7	H8CB—C8C—H8CC	109.5
C4B—C3B—H3BA	108.9	C7C—C9C—H9CA	109.5
C4B—C3B—H3BB	108.9	C7C—C9C—H9CB	109.5
C3B—C4B—H4BA	108.8	C7C—C9C—H9CC	109.5
C3B—C4B—H4BB	108.8	H9CA—C9C—H9CB	109.5
H4BA—C4B—H4BB	107.7	H9CA—C9C—H9CC	109.5
C5B—C4B—C3B	113.7 (14)	H9CB—C9C—H9CC	109.5
C5B—C4B—H4BA	108.8	C5C—C10C—H10G	109.5
C5B—C4B—H4BB	108.8	C5C—C10C—H10H	109.5
C4B—C5B—H5B	104.2	C5C—C10C—H10I	109.5
C4B—C5B—C6B	115 (2)	H10G—C10C—H10H	109.5
C4B—C5B—C10B	118.0 (16)	H10G—C10C—H10I	109.5
C6B—C5B—H5B	104.2	H10H—C10C—H10I	109.5
C6B—C5B—C10B	110 (3)

O1—C1—C2—C3	174 (2)	C3B—C2B—C7B—C9B	−64 (3)
O1—C1—C2—C7	54 (4)	C3B—C4B—C5B—C6B	47 (5)
O1—C1—C6—C5	178 (2)	C3B—C4B—C5B—C10B	179 (4)
C1—C2—C3—C4	67 (2)	C4B—C5B—C6B—C1B	−45 (4)
C1—C2—C7—C8	−175 (4)	C6B—C1B—C2B—C3B	−46 (6)
C1—C2—C7—C9	62 (4)	C6B—C1B—C2B—C7B	164 (4)
C2—C1—C6—C5	70 (4)	C7B—C2B—C3B—C4B	−165 (3)
C2—C3—C4—C5	−59 (4)	C10B—C5B—C6B—C1B	179 (4)
C3—C2—C7—C8	75 (5)	O1C—C1C—C2C—C3C	−170.1 (18)
C3—C2—C7—C9	−48 (3)	O1C—C1C—C2C—C7C	55 (4)
C3—C4—C5—C6	50 (4)	O1C—C1C—C6C—C5C	171 (3)
C3—C4—C5—C10	180 (4)	C1C—C2C—C3C—C4C	47 (3)
C4—C5—C6—C1	−54 (4)	C1C—C2C—C7C—C8C	−178 (4)
C6—C1—C2—C3	−73 (3)	C1C—C2C—C7C—C9C	51 (4)
C6—C1—C2—C7	167 (4)	C2C—C1C—C6C—C5C	49 (5)
C7—C2—C3—C4	−173 (2)	C2C—C3C—C4C—C5C	−51 (5)
C10—C5—C6—C1	179 (3)	C3C—C2C—C7C—C8C	51 (5)
O1B—C1B—C2B—C3B	−179 (4)	C3C—C2C—C7C—C9C	−80 (3)
O1B—C1B—C2B—C7B	32 (6)	C3C—C4C—C5C—C6C	48 (4)
O1B—C1B—C6B—C5B	−176 (3)	C3C—C4C—C5C—C10C	−172 (4)
C1B—C2B—C3B—C4B	47 (5)	C4C—C5C—C6C—C1C	−47 (4)
C1B—C2B—C7B—C8B	−160 (4)	C6C—C1C—C2C—C3C	−47 (4)
C1B—C2B—C7B—C9B	84 (4)	C6C—C1C—C2C—C7C	178 (4)
C2B—C1B—C6B—C5B	44 (5)	C7C—C2C—C3C—C4C	−178 (3)
C2B—C3B—C4B—C5B	−46 (5)	C10C—C5C—C6C—C1C	174 (4)
C3B—C2B—C7B—C8B	52 (5)

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Volume 10| Part 3| May 2023| Pages 341-351

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