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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 81| Part 12| December 2025| Pages 1131-1135
https://doi.org/10.1107/S2056989025009533

Crystal structures of two isomers of 1-(naphthalen-1-yl)ethanol

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Christopher Golza*

aGeorg-August-Universität Göttingen, Institut für Organische und Biomolekulare Chemie, Tammannstrasse 2, D-37077 Göttingen, Germany
*Correspondence e-mail: [email protected]

Edited by A. S. Batsanov, University of Durham, United Kingdom (Received 26 June 2025; accepted 29 October 2025; online 11 November 2025)

Crystal structures, Hirshfeld surfaces and energy lattices of (S)-1-(naphthalen-1-yl)ethanol (1) and (R)-1-(naphthalen-2-yl)ethanol (2), both C12H12O, were studied to understand much the lower crystallization propensity of the latter. In both structures, mol­ecules are linked by strong hydrogen bonds into helical chains where Coulombic inter­actions expectedly dominate, but dispersive inter­actions of 1 and 2 differ significantly, resulting in large gaps in the total energy lattice of 2. The poor crystallization and and higher Z′ (4 vs 2 in structure 1) of 2 can be explained by frustration between supra­molecular synthons (⋯O—H⋯O—H⋯ hydrogen-bonding chain vs π–π- inter­actions between naphthalene moieties). The study provides new insights into the supra­molecular inter­actions and crystal packing of regioisomeric naphthalenyl-ethanol compounds, which may have implications for the design of new materials with tailored properties.

CCDC references: 2498864; 2498863

Similar articles

1. Chemical context

1 and 2 are chiral aromatic alcohols, mutually regioisomeric and differing by the attachment position of the ethanol moiety to the naphthalene group. Such rather simple monoalcohols are inter­esting objects to explore certain packing principles and are often discussed in this connection; monoalcohols specifically appear to behave in a rather systematic way governed by (i) the propensity to form strongly directional hydrogen bonds that link OH groups in chains or rings and (ii) the sterical bulkiness of the organic residue (Brock & Duncan, 1994View full citation). This also leads to frequent occurrence of Z′>1 and extensive polymorphism (Steed & Steed, 2015View full citation; Taylor et al., 2016View full citation). One common approach is to group certain inter­actions into supra­molecular synthons, which prefer definite relative orientations (Anderson et al., 2008View full citation). It is further suggested that, in cases where the synthons are not acting synergistically, structural frustration is building up leading to the formation of high-Z′ structures. For the alcohols studied here, the synthons are the hydrogen bonding between hy­droxy groups and the π–π-inter­actions between naphthalene groups. To explain the contrasting crystallization behavior, with 1 forming very readily sizable single crystals while 2 only reluctantly crystallizing at all, the single crystal structures of both were determined and compared.

[Scheme 1]

2. Structural commentary

Alcohol 1 crystallizes in the ortho­rhom­bic space group P212121 with two independent mol­ecules in the asymmetric unit, while 2 crystallizes in monoclinic P21 with four independent mol­ecules (see Fig. 1[link]). The independent mol­ecules differ mainly in the conformation of the ethanol group (see the mol­ecular overlay in Fig. 2[link]). For 1 the difference is limited to a ca. 20° rotation around the C2—C3 bond. In structure 2, mol­ecules B and D have their hy­droxy group O—H bond oriented roughly in the plane of the naphthalene moiety, while in mol­ecules A and C it is oriented almost perpendicularly to this plane, with consequences for the packing (see Section 3).

[Figure 1]
Figure 1
Mol­ecular structures and atom-numbering schemes of alcohols 1 (top) and 2 (bottom), showing a full asymmetric unit for either. Independent mol­ecules label carry the suffix A to D, respectively. Atomic displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
Overlay of the independent mol­ecules of 1 (top) and 2 (bottom) in which the naphthalene moieties were aligned. Mol­ecules A are shown in red, B in blue, C in orange and D in magenta.

3. Supra­molecular features

At first glance, both alcohols form apparently similar columns of mol­ecules with a central hydrogen-bonding chain following a helical motif that can be described by a pseudo-41 screw (see Fig. 3[link]). Two differences become notable at closer inspection. Firstly, the naphthalene groups are arranged differently. In 1, their orientations approximately follow the same pseudo-41 motif, while in 2 they do not. Instead, the naphthalene and methyl groups each are arranged on opposite faces of the formed column. Secondly, the hydrogen bonds vary in length (defined as the donor-acceptor O⋯O distance) differently in both structures. In 1, it is alternating between one short and one long hydrogen bond (Table 1[link]) while in 2, there are three longer hydrogen bonds, followed by one particularly short one of 2.665 (2) Å (Table 2[link]).

Table 1
Hydrogen-bond geometry (Å, °) for 1[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1A⋯O1Bi 0.85 (2) 1.84 (2) 2.6849 (15) 172 (2)
O1B—H1B⋯O1A 0.85 (2) 1.89 (2) 2.7119 (14) 165 (2)
Symmetry code: (i) Mathematical equation.

Table 2
Hydrogen-bond geometry (Å, °) for 2[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1A⋯O1Di 0.86 (3) 1.94 (3) 2.7890 (18) 171 (2)
O1B—H1B⋯O1A 0.84 (3) 1.95 (3) 2.761 (2) 162 (3)
O1C—H1C⋯O1B 0.91 (3) 1.76 (3) 2.6648 (18) 177 (2)
O1D—H1D⋯O1C 0.87 (3) 1.93 (3) 2.7747 (18) 163 (2)
Symmetry code: (i) Mathematical equation.
[Figure 3]
Figure 3
Packing diagrams for 1 and 2, showing the hydrogen-bond chain motif.

3.1. Hirshfeld surface and energy lattice analysis

To better understand how the mol­ecules inter­act within the columns, the corresponding Hirshfeld surfaces were computed with CrystalExplorer21 and analyzed (Spackman et al., 2021View full citation). The most prominent red spot on the Hirshfeld surface is clearly indicating the hydrogen bond between the adjacent hy­droxy groups, and the fingerprint plot shows the corresponding sharp spike (marked ‘a’ in Fig. 4[link]). An inter­esting feature in 1 is the peripheral spike of H⋯C contacts (marked ‘b’ in Fig. 4[link]), which indicates C—H⋯π inter­actions. This feature is not symmetrically present for both independent mol­ecules of 1, indicating that some of the close C—H⋯π inter­actions occur between two A mol­ecules when they are symmetric contacts, and between A and B when they are not symmetric, whereas mol­ecule B acts mostly as an acceptor. Upon further inspection of these contacts, they appear as inter-column edge-to-face inter­actions (Martinez & Iverson, 2012View full citation).

[Figure 4]
Figure 4
Hirshfeld surface and fingerprint plots for 1 and 2. Red letters indicate close inter­actions H⋯O (a), H⋯C (b) and H⋯H (c).

Further insight into the relative strength of these inter­actions can be obtained from comparison of the energy lattices (Mackenzie et al., 2017View full citation), see Fig. 5[link]. In both structures, the Coulombic inter­actions are clearly dominating along the hydrogen-bonding direction (Table 3[link]), replicating the helical column structure discussed above. In terms of absolute energy, these are also the strongest inter­actions. A noticeable difference becomes visible when the dispersive inter­actions are scrutinized. Although weaker in absolute strength than the electrostatics, they are more numerous because they connect the columns. The dispersive intra-column inter­actions, following the hydrogen bonding, are on a similar scale as the inter-column ones. Inter­estingly, the inter­actions add up differently: noticeable gaps are present in the energy framework of 2, which is not the case in 1. This might indicate the aforementioned frustration between supra­molecular synthons in 2 (Anderson et al., 2008View full citation) and serve to explain the higher Z′ and lower observed crystallization propensity.

Table 3
Calculated inter­action energies (kJ mol−1) between hydrogen-bonded mol­ecules

Comp Path Eele Epol Edis Erep Etot
1 A⋯Bi −50.8 −10.9 −24.8 72.3 −38.7
1 B⋯A −45.3 −10.6 −33.9 69.9 −42.0
2 A⋯Dii −47.3 −10.4 −41.2 69.5 −50.6
2 B⋯A −43.1 −9.5 −19.8 55.4 −35.6
2 C⋯B −61.0 −13.5 −37.7 88.2 −52.8
2 D⋯C −40.6 −8.8 −21.2 54.5 −34.2
Symmetry codes: (i) x + Mathematical equation, −y + Mathematical equation, −z + 1, (ii) x, y − 1, z.
[Figure 5]
Figure 5
Calculated energy lattices (CE-B3LYP) for 1 and 2, viewed perpendicular to (leftmost figures) and down the propagation axes of the pseudo 41-screw. Coulombic inter­actions are represented by red tubes, dispersive inter­actions by green and total energy by blue ones. The tube scale is set to 150 and the cut-off for weak inter­actions is set to 10 kJ mol−1.

4. Database survey

Several related arenyl methanols can be found in the Cambridge Crystallographic Database (CSD ver. 5.43; Groom et al., 2016View full citation), all featuring the hydrogen-bond chain motif. In phenanthren-4-yl-methanol (FUGZAI; Gerkin, 2000View full citation), a very similar packing arrangement is found as in 1 and 2, but in a more ideal realization with Z′ = 1 in space group I41/a. Herein, the hydrogen bond column is following a perfect 41 screw symmetry. On the other hand, the organization of the hydrogen bond column appears to be more distorted when the π-system is enlarged: in anthracen-9-yl-methanol (VAFMUK; Sweeting & Rheingold, 1988View full citation; Islor et al., 2013View full citation) the packing features columns that are not following any screw but a glide operation. In pyren-1-yl-methanol (DUPBAS; Gruber et al., 2010View full citation; Morales-Espinoza et al., 2011View full citation) the mol­ecules appear to favor the formation of discrete π-stacked dimers, that further stretches the pseudo-41 screw motif along the propagation direction. This is notable when comparing the period lengths, involving four mol­ecules per 360° rotation of the helix, viz. 6.03 Å in 2, 7.75 Å in 1, 8.30 Å in FUGZAI and 8.86 Å DUPBAS.

Furthermore, the racemic structure of 2 is known (TAZTAQ; Staples & George, 2005View full citation); it contains discrete centrosymmetric tetra­mers rather than helical columns. The mol­ecular volumes of racemic and enanti­opure structures of 2 are 230.6 Å3 (193 K) versus 233.6 Å3 (100 K), respectively. The former is more dense and thus in accordance with Wallach's rule (Brock et al., 1991View full citation).

5. Synthesis and crystallization

Compounds 1 and 2 were both purchased from BLD Pharmatech GmbH. 1 was received as crystalline material from which suitable single crystals could be taken without further recrystallization. 2 was received as semi-amorphous solid and its recrystallization from various organic solvents yielded finely fibrous material. Single crystals of 2 suitable for diffraction experiments were grown from a solution in ethanol/water over the course of one week.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4[link]. C-bound H atoms were placed geometrically and treated as riding atoms, with C—H = 0.95 Å (aromatic), 0.98 Å (meth­yl), and 1.00 Å (tert-C). Uiso(H) was set to 1.5Ueq(C) for methyl hydrogen atoms and 1.2Ueq(C) otherwise. The positions of hydroxyl H atoms were refined freely, while Uiso(H) were set to 1.5Ueq(O).

Table 4
Experimental details

  1 2
Crystal data
Chemical formula C12H12O C12H12O
Mr 172.22 172.22
Crystal system, space group Orthorhombic, P212121 Monoclinic, P21
Temperature (K) 100 100
a, b, c (Å) 7.7519 (7), 12.9750 (12), 18.794 (3) 17.3408 (5), 6.0327 (2), 19.1125 (5)
α, β, γ (°) 90, 90, 90 90, 110.821 (1), 90
V (Å3) 1890.3 (4) 1868.82 (10)
Z 8 8
Radiation type Cu Kα Cu Kα
μ (mm−1) 0.59 0.60
Crystal size (mm) 0.41 × 0.39 × 0.23 0.56 × 0.05 × 0.04
 
Data collection
Diffractometer Bruker D8 VENTURE dual wavelength Mo/Cu Bruker D8 VENTURE dual wavelength Mo/Cu
Absorption correction Numerical (SADABS; Krause et al., 2015View full citation) Numerical (SADABS; Krause et al., 2015View full citation)
Tmin, Tmax 0.771, 0.982 0.355, 0.473
No. of measured, independent and observed [I > 2σ(I)] reflections 63841, 4063, 4058 70639, 7878, 7515
Rint 0.040 0.051
(sin θ/λ)max (Å−1) 0.637 0.637
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.068, 1.04 0.035, 0.096, 1.03
No. of reflections 4063 7878
No. of parameters 244 486
No. of restraints 0 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.19, −0.12 0.19, −0.16
Absolute structure Flack x determined using 1715 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013View full citation) Flack x determined using 3213 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013View full citation)
Absolute structure parameter 0.04 (4) 0.00 (15)
Computer programs: APEX6 (Bruker, 2024View full citation), SAINT (Bruker, 2016View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation) and OLEX2 (Dolomanov et al., 2009View full citation).

Supporting information

CCDC references: 2498864; 2498863

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989025009533/zv2039sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989025009533/zv20391sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989025009533/zv20392sup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025009533/zv20391sup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989025009533/zv20392sup5.cml

checkCIF report


Computing details top

(S)-1-(Naphthalen-1-yl)ethanol (1) top
Crystal data top
C12H12ODx = 1.210 Mg m−3
Mr = 172.22Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 9660 reflections
a = 7.7519 (7) Åθ = 5.8–78.9°
b = 12.9750 (12) ŵ = 0.59 mm−1
c = 18.794 (3) ÅT = 100 K
V = 1890.3 (4) Å3Block, colourless
Z = 80.41 × 0.39 × 0.23 mm
F(000) = 736
Data collection top
Bruker D8 VENTURE dual wavelength Mo/Cu
diffractometer		4063 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs4058 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.040
Detector resolution: 7.41 pixels mm-1θmax = 79.1°, θmin = 4.1°
ω and φ scansh = −9→9
Absorption correction: numerical
(SADABS; Krause et al., 2015)		k = −16→16
Tmin = 0.771, Tmax = 0.982l = −23→23
63841 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.027 w = 1/[σ2(Fo2) + (0.0307P)2 + 0.3995P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.068(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.19 e Å−3
4063 reflectionsΔρmin = −0.12 e Å−3
244 parametersExtinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0034 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack x determined using 1715 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.04 (4)
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.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C2A(H2A), C2B(H2B) 2.b Aromatic/amide H refined with riding coordinates: C4A(H4A), C5A(H5A), C6A(H6A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C4B(H4B), C5B(H5B), C6B(H6B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B) 2.c Idealised Me refined as rotating group: C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.74231 (13)0.62472 (8)0.49349 (6)0.0251 (2)
H1A0.811 (3)0.6732 (16)0.5051 (11)0.038*
C1A0.63141 (19)0.46242 (12)0.52883 (9)0.0269 (3)
H1AA0.5328080.4975910.5506350.040*
H1AB0.6562380.3989430.5551730.040*
H1AC0.6040830.4454310.4792940.040*
C2A0.78844 (17)0.53276 (10)0.53101 (8)0.0213 (3)
H2A0.8153880.5503980.5816020.026*
C3A0.94438 (17)0.48044 (10)0.49746 (8)0.0205 (3)
C4A0.97819 (19)0.49383 (12)0.42632 (8)0.0244 (3)
H4A0.9081020.5394540.3993470.029*
C5A1.1150 (2)0.44119 (12)0.39235 (8)0.0285 (3)
H5A1.1359260.4518660.3430930.034*
C6A1.21719 (19)0.37518 (12)0.42994 (8)0.0265 (3)
H6A1.3086230.3399840.4066580.032*
C7A1.18786 (18)0.35871 (10)0.50358 (8)0.0224 (3)
C8A1.04973 (17)0.41166 (10)0.53840 (8)0.0200 (3)
C9A1.02091 (19)0.39056 (11)0.61172 (8)0.0238 (3)
H9A0.9311170.4256560.6361410.029*
C10A1.1204 (2)0.32046 (12)0.64783 (8)0.0287 (3)
H10A1.0976260.3068070.6965900.034*
C11A1.2563 (2)0.26847 (12)0.61307 (9)0.0297 (3)
H11A1.3247120.2199710.6383400.036*
C12A1.28916 (18)0.28809 (11)0.54313 (9)0.0267 (3)
H12A1.3821150.2536170.5203550.032*
O1B0.43141 (14)0.71203 (8)0.46621 (6)0.0265 (2)
H1B0.525 (3)0.6885 (16)0.4823 (11)0.040*
C1B0.23951 (19)0.70286 (12)0.36738 (8)0.0281 (3)
H1BA0.1466480.6857130.4007200.042*
H1BB0.2181660.6687090.3217110.042*
H1BC0.2431980.7776520.3602740.042*
C2B0.41076 (18)0.66646 (11)0.39748 (8)0.0240 (3)
H2B0.4082040.5897510.4025540.029*
C3B0.56084 (18)0.69671 (11)0.34933 (8)0.0230 (3)
C4B0.6156 (2)0.79748 (12)0.34891 (9)0.0284 (3)
H4B0.5587200.8462050.3784440.034*
C5B0.7542 (2)0.83057 (12)0.30581 (9)0.0307 (3)
H5B0.7862870.9012230.3053300.037*
C6B0.8418 (2)0.76161 (12)0.26494 (9)0.0288 (3)
H6B0.9363830.7841650.2367990.035*
C7B0.79270 (18)0.65571 (11)0.26410 (8)0.0234 (3)
C8B0.64765 (18)0.62333 (11)0.30537 (7)0.0219 (3)
C9B0.59869 (19)0.51755 (11)0.30078 (8)0.0252 (3)
H9B0.5008390.4940470.3265280.030*
C10B0.6898 (2)0.44943 (11)0.26010 (8)0.0268 (3)
H10B0.6543460.3794190.2578800.032*
C11B0.8359 (2)0.48176 (12)0.22131 (8)0.0278 (3)
H11B0.8998900.4333250.1940890.033*
C12B0.88542 (19)0.58302 (12)0.22294 (8)0.0268 (3)
H12B0.9828830.6047100.1962090.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0203 (5)0.0208 (5)0.0343 (5)0.0024 (4)−0.0059 (4)0.0016 (4)
C1A0.0173 (6)0.0267 (7)0.0367 (8)−0.0001 (6)0.0008 (6)−0.0006 (6)
C2A0.0166 (6)0.0211 (6)0.0263 (6)0.0027 (5)−0.0026 (5)0.0003 (5)
C3A0.0148 (6)0.0192 (6)0.0274 (6)−0.0023 (5)−0.0023 (5)−0.0022 (5)
C4A0.0200 (7)0.0258 (7)0.0276 (7)−0.0031 (6)−0.0028 (6)−0.0004 (6)
C5A0.0261 (8)0.0340 (8)0.0255 (7)−0.0060 (6)0.0031 (6)−0.0040 (6)
C6A0.0184 (7)0.0276 (7)0.0336 (7)−0.0018 (6)0.0054 (6)−0.0083 (6)
C7A0.0158 (6)0.0186 (6)0.0327 (7)−0.0029 (5)0.0004 (5)−0.0060 (5)
C8A0.0141 (6)0.0188 (6)0.0271 (7)−0.0020 (5)−0.0016 (5)−0.0032 (5)
C9A0.0201 (7)0.0233 (7)0.0280 (7)0.0039 (5)−0.0002 (6)−0.0022 (6)
C10A0.0276 (7)0.0288 (7)0.0297 (7)0.0060 (6)−0.0022 (6)0.0014 (6)
C11A0.0245 (8)0.0243 (7)0.0403 (8)0.0063 (6)−0.0067 (7)0.0007 (6)
C12A0.0169 (6)0.0214 (6)0.0417 (8)0.0020 (5)−0.0007 (6)−0.0063 (6)
O1B0.0205 (5)0.0295 (5)0.0295 (5)0.0065 (4)−0.0024 (4)0.0007 (4)
C1B0.0186 (7)0.0312 (7)0.0346 (8)−0.0014 (6)−0.0021 (6)0.0035 (6)
C2B0.0201 (7)0.0243 (7)0.0275 (7)0.0015 (6)0.0010 (5)0.0015 (6)
C3B0.0186 (6)0.0236 (7)0.0268 (7)0.0005 (5)−0.0011 (5)0.0027 (6)
C4B0.0236 (7)0.0232 (7)0.0384 (8)0.0005 (6)0.0009 (6)0.0001 (6)
C5B0.0261 (7)0.0210 (6)0.0450 (9)−0.0040 (6)0.0023 (7)0.0018 (6)
C6B0.0220 (7)0.0287 (7)0.0356 (8)−0.0024 (6)0.0019 (6)0.0039 (6)
C7B0.0177 (6)0.0283 (7)0.0241 (6)0.0015 (5)−0.0028 (5)0.0025 (5)
C8B0.0177 (6)0.0252 (7)0.0228 (6)0.0016 (5)−0.0032 (5)0.0023 (5)
C9B0.0235 (7)0.0253 (7)0.0270 (7)0.0000 (6)−0.0033 (6)0.0017 (6)
C10B0.0298 (8)0.0215 (7)0.0293 (7)0.0015 (6)−0.0074 (6)−0.0016 (5)
C11B0.0256 (7)0.0298 (7)0.0280 (7)0.0062 (6)−0.0052 (6)−0.0037 (6)
C12B0.0190 (7)0.0344 (8)0.0270 (7)0.0023 (6)−0.0012 (6)−0.0003 (6)
Geometric parameters (Å, º) top
O1A—H1A0.85 (2)O1B—H1B0.85 (2)
O1A—C2A1.4315 (16)O1B—C2B1.4295 (18)
C1A—H1AA0.9800C1B—H1BA0.9800
C1A—H1AB0.9800C1B—H1BB0.9800
C1A—H1AC0.9800C1B—H1BC0.9800
C1A—C2A1.522 (2)C1B—C2B1.518 (2)
C2A—H2A1.0000C2B—H2B1.0000
C2A—C3A1.5230 (19)C2B—C3B1.525 (2)
C3A—C4A1.374 (2)C3B—C4B1.375 (2)
C3A—C8A1.4336 (19)C3B—C8B1.429 (2)
C4A—H4A0.9500C4B—H4B0.9500
C4A—C5A1.414 (2)C4B—C5B1.412 (2)
C5A—H5A0.9500C5B—H5B0.9500
C5A—C6A1.364 (2)C5B—C6B1.361 (2)
C6A—H6A0.9500C6B—H6B0.9500
C6A—C7A1.419 (2)C6B—C7B1.426 (2)
C7A—C8A1.4306 (19)C7B—C8B1.429 (2)
C7A—C12A1.417 (2)C7B—C12B1.416 (2)
C8A—C9A1.423 (2)C8B—C9B1.427 (2)
C9A—H9A0.9500C9B—H9B0.9500
C9A—C10A1.372 (2)C9B—C10B1.365 (2)
C10A—H10A0.9500C10B—H10B0.9500
C10A—C11A1.411 (2)C10B—C11B1.411 (2)
C11A—H11A0.9500C11B—H11B0.9500
C11A—C12A1.363 (2)C11B—C12B1.369 (2)
C12A—H12A0.9500C12B—H12B0.9500
C2A—O1A—H1A109.4 (14)C2B—O1B—H1B105.6 (15)
H1AA—C1A—H1AB109.5H1BA—C1B—H1BB109.5
H1AA—C1A—H1AC109.5H1BA—C1B—H1BC109.5
H1AB—C1A—H1AC109.5H1BB—C1B—H1BC109.5
C2A—C1A—H1AA109.5C2B—C1B—H1BA109.5
C2A—C1A—H1AB109.5C2B—C1B—H1BB109.5
C2A—C1A—H1AC109.5C2B—C1B—H1BC109.5
O1A—C2A—C1A106.67 (11)O1B—C2B—C1B107.81 (12)
O1A—C2A—H2A109.3O1B—C2B—H2B109.1
O1A—C2A—C3A111.46 (12)O1B—C2B—C3B110.13 (12)
C1A—C2A—H2A109.3C1B—C2B—H2B109.1
C1A—C2A—C3A110.88 (11)C1B—C2B—C3B111.45 (12)
C3A—C2A—H2A109.3C3B—C2B—H2B109.1
C4A—C3A—C2A119.87 (13)C4B—C3B—C2B118.94 (13)
C4A—C3A—C8A119.50 (13)C4B—C3B—C8B119.00 (14)
C8A—C3A—C2A120.49 (12)C8B—C3B—C2B122.06 (13)
C3A—C4A—H4A119.3C3B—C4B—H4B119.1
C3A—C4A—C5A121.43 (14)C3B—C4B—C5B121.84 (14)
C5A—C4A—H4A119.3C5B—C4B—H4B119.1
C4A—C5A—H5A119.8C4B—C5B—H5B119.9
C6A—C5A—C4A120.34 (14)C6B—C5B—C4B120.24 (14)
C6A—C5A—H5A119.8C6B—C5B—H5B119.9
C5A—C6A—H6A119.8C5B—C6B—H6B119.8
C5A—C6A—C7A120.46 (14)C5B—C6B—C7B120.42 (14)
C7A—C6A—H6A119.8C7B—C6B—H6B119.8
C6A—C7A—C8A119.59 (13)C6B—C7B—C8B119.18 (13)
C12A—C7A—C6A121.35 (14)C12B—C7B—C6B120.82 (14)
C12A—C7A—C8A119.02 (13)C12B—C7B—C8B120.01 (13)
C7A—C8A—C3A118.67 (13)C3B—C8B—C7B119.24 (13)
C9A—C8A—C3A123.38 (12)C9B—C8B—C3B123.41 (13)
C9A—C8A—C7A117.92 (13)C9B—C8B—C7B117.34 (13)
C8A—C9A—H9A119.4C8B—C9B—H9B119.4
C10A—C9A—C8A121.22 (14)C10B—C9B—C8B121.26 (14)
C10A—C9A—H9A119.4C10B—C9B—H9B119.4
C9A—C10A—H10A119.7C9B—C10B—H10B119.6
C9A—C10A—C11A120.51 (15)C9B—C10B—C11B120.81 (14)
C11A—C10A—H10A119.7C11B—C10B—H10B119.6
C10A—C11A—H11A120.1C10B—C11B—H11B120.0
C12A—C11A—C10A119.77 (14)C12B—C11B—C10B119.91 (14)
C12A—C11A—H11A120.1C12B—C11B—H11B120.0
C7A—C12A—H12A119.2C7B—C12B—H12B119.7
C11A—C12A—C7A121.55 (14)C11B—C12B—C7B120.62 (14)
C11A—C12A—H12A119.2C11B—C12B—H12B119.7
O1A—C2A—C3A—C4A−26.91 (17)O1B—C2B—C3B—C4B−44.17 (18)
O1A—C2A—C3A—C8A157.32 (11)O1B—C2B—C3B—C8B134.99 (13)
C1A—C2A—C3A—C4A91.76 (16)C1B—C2B—C3B—C4B75.44 (18)
C1A—C2A—C3A—C8A−84.01 (16)C1B—C2B—C3B—C8B−105.40 (15)
C2A—C3A—C4A—C5A−175.82 (13)C2B—C3B—C4B—C5B179.76 (14)
C2A—C3A—C8A—C7A175.77 (12)C2B—C3B—C8B—C7B−176.97 (13)
C2A—C3A—C8A—C9A−2.2 (2)C2B—C3B—C8B—C9B2.2 (2)
C3A—C4A—C5A—C6A0.1 (2)C3B—C4B—C5B—C6B−2.4 (2)
C3A—C8A—C9A—C10A176.93 (14)C3B—C8B—C9B—C10B−177.44 (13)
C4A—C3A—C8A—C7A−0.01 (19)C4B—C3B—C8B—C7B2.2 (2)
C4A—C3A—C8A—C9A−177.95 (13)C4B—C3B—C8B—C9B−178.63 (14)
C4A—C5A—C6A—C7A−0.2 (2)C4B—C5B—C6B—C7B1.3 (2)
C5A—C6A—C7A—C8A0.2 (2)C5B—C6B—C7B—C8B1.5 (2)
C5A—C6A—C7A—C12A178.05 (14)C5B—C6B—C7B—C12B−178.64 (15)
C6A—C7A—C8A—C3A−0.06 (19)C6B—C7B—C8B—C3B−3.2 (2)
C6A—C7A—C8A—C9A177.99 (13)C6B—C7B—C8B—C9B177.55 (13)
C6A—C7A—C12A—C11A−176.91 (14)C6B—C7B—C12B—C11B−178.84 (14)
C7A—C8A—C9A—C10A−1.0 (2)C7B—C8B—C9B—C10B1.8 (2)
C8A—C3A—C4A—C5A0.0 (2)C8B—C3B—C4B—C5B0.6 (2)
C8A—C7A—C12A—C11A1.0 (2)C8B—C7B—C12B—C11B1.0 (2)
C8A—C9A—C10A—C11A1.0 (2)C8B—C9B—C10B—C11B0.1 (2)
C9A—C10A—C11A—C12A0.1 (2)C9B—C10B—C11B—C12B−1.5 (2)
C10A—C11A—C12A—C7A−1.0 (2)C10B—C11B—C12B—C7B0.9 (2)
C12A—C7A—C8A—C3A−178.00 (12)C12B—C7B—C8B—C3B176.92 (13)
C12A—C7A—C8A—C9A0.05 (19)C12B—C7B—C8B—C9B−2.31 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Bi0.85 (2)1.84 (2)2.6849 (15)172 (2)
O1B—H1B···O1A0.85 (2)1.89 (2)2.7119 (14)165 (2)
Symmetry code: (i) x+1/2, −y+3/2, −z+1.
(R)-1-(Naphthalen-2-yl)ethanol (2) top
Crystal data top
C12H12OF(000) = 736
Mr = 172.22Dx = 1.224 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 17.3408 (5) ÅCell parameters from 9778 reflections
b = 6.0327 (2) Åθ = 2.5–78.8°
c = 19.1125 (5) ŵ = 0.60 mm−1
β = 110.821 (1)°T = 100 K
V = 1868.82 (10) Å3Needle, colourless
Z = 80.56 × 0.05 × 0.04 mm
Data collection top
Bruker D8 VENTURE dual wavelength Mo/Cu
diffractometer		7878 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs7515 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.051
Detector resolution: 7.41 pixels mm-1θmax = 79.1°, θmin = 2.5°
ω and φ scansh = −21→21
Absorption correction: numerical
(SADABS; Krause et al., 2015)		k = −7→7
Tmin = 0.355, Tmax = 0.473l = −24→24
70639 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0657P)2 + 0.2081P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.19 e Å−3
7878 reflectionsΔρmin = −0.16 e Å−3
486 parametersExtinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0019 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack x determined using 3213 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (15)
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.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C2A(H2A), C2B(H2B), C2C(H2C), C2D(H2D) 2.b Aromatic/amide H refined with riding coordinates: C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C11B(H11B), C12B(H12B), C4C(H4C), C6C(H6C), C7C(H7C), C8C(H8C), C9C(H9C), C11C(H11C), C12C(H12C), C4D(H4D), C6D(H6D), C7D(H7D), C8D(H8D), C9D(H9D), C11D(H11D), C12D(H12D) 2.c Idealised Me refined as rotating group: C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB, H1DC)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.39030 (8)−0.0225 (2)0.72219 (7)0.0247 (3)
H1A0.3483 (17)−0.082 (5)0.6890 (15)0.037*
C1A0.53036 (12)0.0875 (4)0.75148 (11)0.0309 (4)
H1AA0.5174830.2436710.7563300.046*
H1AB0.5782690.0777080.7358140.046*
H1AC0.5428260.0129810.7998180.046*
C2A0.45672 (10)−0.0237 (3)0.69335 (10)0.0236 (3)
H2A0.471455−0.1809180.6871880.028*
C3A0.43001 (10)0.0900 (3)0.61778 (10)0.0210 (3)
C4A0.43768 (10)−0.0146 (3)0.55675 (10)0.0204 (3)
H4A0.462998−0.1564840.5627970.024*
C5A0.40842 (10)0.0855 (3)0.48470 (10)0.0195 (3)
C6A0.41427 (10)−0.0224 (3)0.42066 (10)0.0230 (3)
H6A0.440380−0.1629580.4257400.028*
C7A0.38245 (11)0.0755 (3)0.35172 (10)0.0257 (4)
H7A0.3871140.0028420.3093100.031*
C8A0.34270 (11)0.2838 (3)0.34297 (10)0.0259 (4)
H8A0.3195630.3480680.2945960.031*
C9A0.33738 (11)0.3933 (3)0.40387 (10)0.0238 (4)
H9A0.3114000.5342700.3975480.029*
C10A0.37034 (10)0.2978 (3)0.47634 (10)0.0203 (3)
C11A0.36459 (10)0.4047 (3)0.54063 (10)0.0224 (3)
H11A0.3403400.5477410.5358780.027*
C12A0.39349 (11)0.3042 (3)0.60911 (10)0.0226 (4)
H12A0.3891630.3782500.6514310.027*
O1B0.31560 (9)0.3220 (3)0.76906 (7)0.0328 (3)
H1B0.3481 (19)0.231 (6)0.7609 (16)0.049*
C1B0.43974 (13)0.5252 (4)0.84375 (12)0.0332 (4)
H1BA0.4747440.3930230.8523260.050*
H1BB0.4614170.6258070.8865580.050*
H1BC0.4394380.6005400.7982290.050*
C2B0.35249 (11)0.4574 (3)0.83469 (10)0.0273 (4)
H2B0.3188700.5958600.8278380.033*
C3B0.34888 (11)0.3404 (3)0.90343 (10)0.0243 (4)
C4B0.31125 (11)0.4384 (3)0.94742 (10)0.0250 (4)
H4B0.2867390.5804090.9339810.030*
C5B0.30800 (11)0.3326 (3)1.01283 (10)0.0252 (4)
C6B0.26646 (12)0.4295 (4)1.05733 (11)0.0323 (4)
H6B0.2422530.5722321.0449570.039*
C7B0.26112 (13)0.3187 (4)1.11786 (12)0.0388 (5)
H7B0.2329910.3845511.1471190.047*
C8B0.29710 (13)0.1070 (5)1.13716 (11)0.0383 (5)
H8B0.2927680.0311021.1791600.046*
C9B0.33829 (12)0.0101 (4)1.09572 (11)0.0329 (4)
H9B0.362970−0.1315041.1096980.039*
C10B0.34433 (11)0.1194 (3)1.03221 (10)0.0269 (4)
C11B0.38353 (11)0.0206 (3)0.98591 (11)0.0277 (4)
H11B0.408560−0.1210730.9985290.033*
C12B0.38551 (12)0.1275 (3)0.92345 (11)0.0269 (4)
H12B0.4116770.0587960.8930520.032*
O1C0.18245 (7)0.4837 (2)0.66222 (6)0.0207 (2)
H1C0.2289 (16)0.430 (4)0.6976 (14)0.031*
C1C0.03587 (10)0.4844 (3)0.62168 (10)0.0245 (4)
H1CA0.0339330.6400100.6064150.037*
H1CB−0.0115220.4520940.6365550.037*
H1CC0.0340090.3886320.5796920.037*
C2C0.11532 (10)0.4417 (3)0.68743 (9)0.0196 (3)
H2C0.1168680.2823290.7022380.024*
C3C0.12073 (10)0.5853 (3)0.75442 (9)0.0191 (3)
C4C0.08734 (10)0.5134 (3)0.80584 (9)0.0199 (3)
H4C0.0617450.3718940.7996620.024*
C5C0.09049 (10)0.6471 (3)0.86803 (9)0.0191 (3)
C6C0.05706 (11)0.5760 (3)0.92223 (10)0.0223 (3)
H6C0.0303320.4362050.9166730.027*
C7C0.06309 (12)0.7078 (3)0.98266 (10)0.0251 (4)
H7C0.0409900.6578111.0187780.030*
C8C0.10188 (11)0.9169 (3)0.99138 (10)0.0243 (4)
H8C0.1057561.0068991.0332930.029*
C9C0.13396 (10)0.9906 (3)0.93964 (10)0.0229 (3)
H9C0.1594551.1322500.9457790.027*
C10C0.12965 (10)0.8585 (3)0.87711 (9)0.0197 (3)
C11C0.16374 (10)0.9291 (3)0.82350 (10)0.0215 (3)
H11C0.1899781.0696360.8289900.026*
C12C0.15923 (11)0.7969 (3)0.76385 (10)0.0213 (3)
H12C0.1821360.8473210.7283390.026*
O1D0.26221 (8)0.7902 (2)0.60343 (7)0.0219 (3)
H1D0.2286 (16)0.710 (5)0.6173 (14)0.033*
C1D0.14051 (12)1.0235 (3)0.55515 (10)0.0246 (4)
H1DA0.1039420.9042950.5592620.037*
H1DB0.1102611.1216870.5136140.037*
H1DC0.1599321.1084720.6018780.037*
C2D0.21417 (10)0.9238 (3)0.54066 (9)0.0199 (3)
H2D0.2498131.0485750.5356400.024*
C3D0.18596 (10)0.7947 (3)0.46782 (9)0.0183 (3)
C4D0.19249 (10)0.8838 (3)0.40404 (9)0.0185 (3)
H4D0.2196601.0221070.4068670.022*
C5D0.15950 (10)0.7738 (3)0.33394 (9)0.0189 (3)
C6D0.16599 (11)0.8622 (3)0.26731 (10)0.0235 (4)
H6D0.1930101.0000650.2688620.028*
C7D0.13354 (12)0.7499 (3)0.20069 (10)0.0275 (4)
H7D0.1384610.8106950.1566100.033*
C8D0.09286 (12)0.5448 (3)0.19713 (10)0.0276 (4)
H8D0.0704360.4687500.1507370.033*
C9D0.08573 (11)0.4556 (3)0.26030 (10)0.0248 (4)
H9D0.0579110.3183000.2573870.030*
C10D0.11944 (10)0.5659 (3)0.33018 (9)0.0201 (3)
C11D0.11518 (11)0.4746 (3)0.39733 (10)0.0231 (3)
H11D0.0895410.3346460.3959230.028*
C12D0.14744 (11)0.5853 (3)0.46390 (10)0.0222 (3)
H12D0.1440060.5210350.5080760.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0227 (6)0.0283 (7)0.0217 (6)−0.0025 (5)0.0064 (5)−0.0004 (5)
C1A0.0237 (9)0.0373 (10)0.0277 (9)0.0007 (8)0.0043 (7)−0.0029 (8)
C2A0.0223 (8)0.0245 (8)0.0231 (8)0.0017 (7)0.0070 (7)0.0000 (7)
C3A0.0152 (7)0.0219 (8)0.0242 (8)−0.0020 (6)0.0050 (6)0.0001 (7)
C4A0.0162 (7)0.0183 (8)0.0254 (8)0.0002 (6)0.0060 (6)0.0005 (6)
C5A0.0133 (7)0.0192 (8)0.0249 (8)−0.0030 (6)0.0053 (6)−0.0011 (6)
C6A0.0184 (7)0.0222 (8)0.0274 (8)−0.0008 (6)0.0071 (6)−0.0012 (7)
C7A0.0217 (8)0.0305 (9)0.0242 (9)−0.0035 (7)0.0074 (7)−0.0038 (7)
C8A0.0209 (8)0.0297 (10)0.0243 (8)−0.0036 (7)0.0046 (7)0.0056 (7)
C9A0.0175 (8)0.0214 (8)0.0303 (9)−0.0008 (6)0.0058 (7)0.0040 (7)
C10A0.0142 (7)0.0198 (8)0.0267 (8)−0.0032 (6)0.0068 (6)0.0010 (7)
C11A0.0183 (8)0.0175 (8)0.0318 (9)0.0002 (6)0.0093 (7)−0.0007 (7)
C12A0.0208 (8)0.0213 (8)0.0273 (9)−0.0020 (6)0.0103 (7)−0.0046 (7)
O1B0.0269 (7)0.0413 (8)0.0232 (6)0.0112 (6)0.0001 (5)−0.0036 (6)
C1B0.0309 (10)0.0367 (11)0.0307 (10)0.0014 (8)0.0093 (8)0.0062 (8)
C2B0.0261 (9)0.0276 (9)0.0236 (8)0.0069 (7)0.0032 (7)0.0014 (7)
C3B0.0190 (8)0.0255 (9)0.0238 (8)0.0006 (7)0.0019 (7)−0.0010 (7)
C4B0.0198 (8)0.0209 (8)0.0293 (9)0.0006 (6)0.0024 (7)−0.0034 (7)
C5B0.0171 (8)0.0294 (9)0.0255 (9)−0.0025 (7)0.0032 (7)−0.0058 (7)
C6B0.0231 (9)0.0389 (11)0.0318 (10)−0.0011 (8)0.0060 (7)−0.0103 (8)
C7B0.0256 (10)0.0601 (14)0.0289 (10)−0.0060 (10)0.0076 (8)−0.0109 (10)
C8B0.0276 (10)0.0597 (15)0.0238 (9)−0.0109 (10)0.0046 (8)0.0019 (9)
C9B0.0240 (9)0.0386 (11)0.0293 (9)−0.0049 (8)0.0014 (7)0.0050 (8)
C10B0.0189 (8)0.0312 (10)0.0254 (9)−0.0036 (7)0.0014 (7)−0.0015 (7)
C11B0.0233 (9)0.0238 (9)0.0303 (9)0.0019 (7)0.0024 (7)−0.0004 (7)
C12B0.0240 (9)0.0253 (9)0.0280 (9)0.0045 (7)0.0052 (7)−0.0035 (7)
O1C0.0177 (5)0.0266 (6)0.0184 (5)0.0022 (5)0.0071 (4)0.0013 (5)
C1C0.0196 (8)0.0290 (9)0.0243 (8)−0.0003 (7)0.0071 (7)−0.0035 (7)
C2C0.0207 (8)0.0190 (8)0.0207 (8)0.0003 (6)0.0092 (6)0.0001 (6)
C3C0.0173 (7)0.0194 (8)0.0197 (8)0.0018 (6)0.0057 (6)0.0007 (6)
C4C0.0188 (8)0.0177 (8)0.0223 (8)0.0007 (6)0.0062 (6)0.0010 (6)
C5C0.0165 (8)0.0197 (8)0.0193 (8)0.0018 (6)0.0043 (6)0.0014 (6)
C6C0.0206 (8)0.0234 (8)0.0229 (8)−0.0002 (6)0.0078 (7)0.0006 (7)
C7C0.0238 (9)0.0315 (9)0.0206 (8)0.0022 (7)0.0088 (7)0.0012 (7)
C8C0.0215 (8)0.0296 (9)0.0195 (8)0.0024 (7)0.0046 (6)−0.0049 (7)
C9C0.0187 (8)0.0219 (8)0.0249 (8)0.0010 (7)0.0037 (6)−0.0032 (7)
C10C0.0163 (7)0.0202 (8)0.0208 (8)0.0023 (6)0.0043 (6)0.0009 (6)
C11C0.0203 (8)0.0177 (8)0.0256 (8)−0.0008 (6)0.0072 (7)0.0001 (6)
C12C0.0204 (8)0.0217 (8)0.0230 (8)0.0004 (6)0.0090 (7)0.0026 (6)
O1D0.0209 (6)0.0242 (6)0.0191 (6)−0.0022 (5)0.0050 (5)0.0009 (5)
C1D0.0294 (9)0.0223 (9)0.0226 (8)0.0031 (7)0.0098 (7)−0.0020 (7)
C2D0.0223 (8)0.0188 (8)0.0177 (7)−0.0029 (6)0.0060 (6)−0.0012 (6)
C3D0.0159 (7)0.0191 (8)0.0193 (7)0.0009 (6)0.0056 (6)−0.0019 (6)
C4D0.0170 (7)0.0167 (7)0.0213 (8)−0.0011 (6)0.0061 (6)−0.0002 (6)
C5D0.0159 (8)0.0210 (8)0.0198 (8)0.0016 (6)0.0062 (6)0.0007 (6)
C6D0.0222 (8)0.0266 (9)0.0219 (8)−0.0020 (7)0.0083 (7)0.0021 (7)
C7D0.0282 (10)0.0348 (10)0.0190 (8)−0.0011 (8)0.0078 (7)0.0018 (7)
C8D0.0265 (9)0.0342 (10)0.0190 (8)−0.0013 (7)0.0044 (7)−0.0063 (7)
C9D0.0239 (8)0.0242 (9)0.0236 (8)−0.0030 (7)0.0050 (7)−0.0033 (7)
C10D0.0184 (8)0.0213 (8)0.0196 (8)0.0001 (6)0.0053 (6)−0.0011 (6)
C11D0.0251 (8)0.0191 (8)0.0245 (8)−0.0046 (7)0.0080 (7)−0.0013 (7)
C12D0.0251 (8)0.0212 (8)0.0209 (8)−0.0021 (7)0.0088 (7)0.0011 (6)
Geometric parameters (Å, º) top
O1A—H1A0.86 (3)O1C—H1C0.91 (3)
O1A—C2A1.443 (2)O1C—C2C1.4318 (19)
C1A—H1AA0.9800C1C—H1CA0.9800
C1A—H1AB0.9800C1C—H1CB0.9800
C1A—H1AC0.9800C1C—H1CC0.9800
C1A—C2A1.519 (3)C1C—C2C1.521 (2)
C2A—H2A1.0000C2C—H2C1.0000
C2A—C3A1.515 (2)C2C—C3C1.521 (2)
C3A—C4A1.374 (2)C3C—C4C1.376 (2)
C3A—C12A1.423 (2)C3C—C12C1.422 (2)
C4A—H4A0.9500C4C—H4C0.9500
C4A—C5A1.422 (2)C4C—C5C1.422 (2)
C5A—C6A1.421 (2)C5C—C6C1.421 (2)
C5A—C10A1.424 (2)C5C—C10C1.426 (2)
C6A—H6A0.9500C6C—H6C0.9500
C6A—C7A1.368 (3)C6C—C7C1.375 (3)
C7A—H7A0.9500C7C—H7C0.9500
C7A—C8A1.414 (3)C7C—C8C1.411 (3)
C8A—H8A0.9500C8C—H8C0.9500
C8A—C9A1.370 (3)C8C—C9C1.370 (3)
C9A—H9A0.9500C9C—H9C0.9500
C9A—C10A1.419 (2)C9C—C10C1.416 (2)
C10A—C11A1.422 (2)C10C—C11C1.418 (2)
C11A—H11A0.9500C11C—H11C0.9500
C11A—C12A1.366 (3)C11C—C12C1.371 (2)
C12A—H12A0.9500C12C—H12C0.9500
O1B—H1B0.84 (3)O1D—H1D0.87 (3)
O1B—C2B1.442 (2)O1D—C2D1.440 (2)
C1B—H1BA0.9800C1D—H1DA0.9800
C1B—H1BB0.9800C1D—H1DB0.9800
C1B—H1BC0.9800C1D—H1DC0.9800
C1B—C2B1.517 (3)C1D—C2D1.524 (2)
C2B—H2B1.0000C2D—H2D1.0000
C2B—C3B1.512 (3)C2D—C3D1.517 (2)
C3B—C4B1.369 (3)C3D—C4D1.373 (2)
C3B—C12B1.424 (3)C3D—C12D1.419 (2)
C4B—H4B0.9500C4D—H4D0.9500
C4B—C5B1.423 (3)C4D—C5D1.421 (2)
C5B—C6B1.421 (3)C5D—C6D1.421 (2)
C5B—C10B1.422 (3)C5D—C10D1.423 (2)
C6B—H6B0.9500C6D—H6D0.9500
C6B—C7B1.368 (3)C6D—C7D1.374 (3)
C7B—H7B0.9500C7D—H7D0.9500
C7B—C8B1.412 (4)C7D—C8D1.414 (3)
C8B—H8B0.9500C8D—H8D0.9500
C8B—C9B1.372 (3)C8D—C9D1.367 (3)
C9B—H9B0.9500C9D—H9D0.9500
C9B—C10B1.418 (3)C9D—C10D1.419 (2)
C10B—C11B1.424 (3)C10D—C11D1.422 (2)
C11B—H11B0.9500C11D—H11D0.9500
C11B—C12B1.368 (3)C11D—C12D1.368 (2)
C12B—H12B0.9500C12D—H12D0.9500
C2A—O1A—H1A107.4 (17)C2C—O1C—H1C107.4 (15)
H1AA—C1A—H1AB109.5H1CA—C1C—H1CB109.5
H1AA—C1A—H1AC109.5H1CA—C1C—H1CC109.5
H1AB—C1A—H1AC109.5H1CB—C1C—H1CC109.5
C2A—C1A—H1AA109.5C2C—C1C—H1CA109.5
C2A—C1A—H1AB109.5C2C—C1C—H1CB109.5
C2A—C1A—H1AC109.5C2C—C1C—H1CC109.5
O1A—C2A—C1A107.21 (14)O1C—C2C—C1C107.34 (13)
O1A—C2A—H2A108.8O1C—C2C—H2C108.8
O1A—C2A—C3A110.30 (14)O1C—C2C—C3C111.61 (13)
C1A—C2A—H2A108.8C1C—C2C—H2C108.8
C3A—C2A—C1A112.95 (16)C1C—C2C—C3C111.47 (14)
C3A—C2A—H2A108.8C3C—C2C—H2C108.8
C4A—C3A—C2A120.81 (16)C4C—C3C—C2C120.39 (15)
C4A—C3A—C12A119.47 (16)C4C—C3C—C12C119.36 (15)
C12A—C3A—C2A119.67 (16)C12C—C3C—C2C120.25 (15)
C3A—C4A—H4A119.4C3C—C4C—H4C119.4
C3A—C4A—C5A121.21 (16)C3C—C4C—C5C121.16 (16)
C5A—C4A—H4A119.4C5C—C4C—H4C119.4
C4A—C5A—C10A118.85 (16)C4C—C5C—C10C118.97 (15)
C6A—C5A—C4A121.96 (16)C6C—C5C—C4C122.26 (16)
C6A—C5A—C10A119.18 (16)C6C—C5C—C10C118.77 (15)
C5A—C6A—H6A119.9C5C—C6C—H6C119.7
C7A—C6A—C5A120.25 (17)C7C—C6C—C5C120.57 (17)
C7A—C6A—H6A119.9C7C—C6C—H6C119.7
C6A—C7A—H7A119.7C6C—C7C—H7C119.8
C6A—C7A—C8A120.67 (17)C6C—C7C—C8C120.45 (17)
C8A—C7A—H7A119.7C8C—C7C—H7C119.8
C7A—C8A—H8A119.8C7C—C8C—H8C119.9
C9A—C8A—C7A120.34 (17)C9C—C8C—C7C120.24 (17)
C9A—C8A—H8A119.8C9C—C8C—H8C119.9
C8A—C9A—H9A119.7C8C—C9C—H9C119.6
C8A—C9A—C10A120.55 (17)C8C—C9C—C10C120.90 (17)
C10A—C9A—H9A119.7C10C—C9C—H9C119.6
C9A—C10A—C5A118.98 (16)C9C—C10C—C5C119.07 (15)
C9A—C10A—C11A122.11 (16)C9C—C10C—C11C122.00 (16)
C11A—C10A—C5A118.89 (16)C11C—C10C—C5C118.92 (15)
C10A—C11A—H11A119.6C10C—C11C—H11C119.6
C12A—C11A—C10A120.81 (16)C12C—C11C—C10C120.72 (16)
C12A—C11A—H11A119.6C12C—C11C—H11C119.6
C3A—C12A—H12A119.6C3C—C12C—H12C119.6
C11A—C12A—C3A120.75 (16)C11C—C12C—C3C120.88 (16)
C11A—C12A—H12A119.6C11C—C12C—H12C119.6
C2B—O1B—H1B114 (2)C2D—O1D—H1D108.3 (17)
H1BA—C1B—H1BB109.5H1DA—C1D—H1DB109.5
H1BA—C1B—H1BC109.5H1DA—C1D—H1DC109.5
H1BB—C1B—H1BC109.5H1DB—C1D—H1DC109.5
C2B—C1B—H1BA109.5C2D—C1D—H1DA109.5
C2B—C1B—H1BB109.5C2D—C1D—H1DB109.5
C2B—C1B—H1BC109.5C2D—C1D—H1DC109.5
O1B—C2B—C1B111.60 (16)O1D—C2D—C1D110.11 (13)
O1B—C2B—H2B107.5O1D—C2D—H2D107.9
O1B—C2B—C3B110.39 (16)O1D—C2D—C3D112.32 (13)
C1B—C2B—H2B107.5C1D—C2D—H2D107.9
C3B—C2B—C1B111.99 (15)C3D—C2D—C1D110.59 (14)
C3B—C2B—H2B107.5C3D—C2D—H2D107.9
C4B—C3B—C2B120.52 (17)C4D—C3D—C2D120.81 (15)
C4B—C3B—C12B119.31 (17)C4D—C3D—C12D119.19 (15)
C12B—C3B—C2B120.16 (17)C12D—C3D—C2D119.87 (15)
C3B—C4B—H4B119.3C3D—C4D—H4D119.3
C3B—C4B—C5B121.49 (17)C3D—C4D—C5D121.43 (15)
C5B—C4B—H4B119.3C5D—C4D—H4D119.3
C6B—C5B—C4B121.86 (18)C4D—C5D—C6D122.42 (16)
C6B—C5B—C10B119.23 (18)C4D—C5D—C10D119.02 (15)
C10B—C5B—C4B118.85 (17)C6D—C5D—C10D118.55 (15)
C5B—C6B—H6B119.8C5D—C6D—H6D119.7
C7B—C6B—C5B120.4 (2)C7D—C6D—C5D120.58 (17)
C7B—C6B—H6B119.8C7D—C6D—H6D119.7
C6B—C7B—H7B119.8C6D—C7D—H7D119.7
C6B—C7B—C8B120.5 (2)C6D—C7D—C8D120.60 (17)
C8B—C7B—H7B119.8C8D—C7D—H7D119.7
C7B—C8B—H8B119.8C7D—C8D—H8D119.9
C9B—C8B—C7B120.5 (2)C9D—C8D—C7D120.14 (16)
C9B—C8B—H8B119.8C9D—C8D—H8D119.9
C8B—C9B—H9B119.7C8D—C9D—H9D119.7
C8B—C9B—C10B120.5 (2)C8D—C9D—C10D120.69 (17)
C10B—C9B—H9B119.7C10D—C9D—H9D119.7
C5B—C10B—C11B118.81 (17)C9D—C10D—C5D119.43 (16)
C9B—C10B—C5B118.88 (18)C9D—C10D—C11D122.10 (16)
C9B—C10B—C11B122.29 (19)C11D—C10D—C5D118.47 (15)
C10B—C11B—H11B119.6C10D—C11D—H11D119.5
C12B—C11B—C10B120.70 (18)C12D—C11D—C10D120.98 (16)
C12B—C11B—H11B119.6C12D—C11D—H11D119.5
C3B—C12B—H12B119.6C3D—C12D—H12D119.6
C11B—C12B—C3B120.84 (17)C11D—C12D—C3D120.87 (16)
C11B—C12B—H12B119.6C11D—C12D—H12D119.6
O1A—C2A—C3A—C4A−126.61 (17)O1C—C2C—C3C—C4C−152.07 (15)
O1A—C2A—C3A—C12A50.9 (2)O1C—C2C—C3C—C12C28.9 (2)
C1A—C2A—C3A—C4A113.44 (19)C1C—C2C—C3C—C4C87.92 (19)
C1A—C2A—C3A—C12A−69.1 (2)C1C—C2C—C3C—C12C−91.07 (19)
C2A—C3A—C4A—C5A176.32 (14)C2C—C3C—C4C—C5C−178.83 (14)
C2A—C3A—C12A—C11A−176.19 (15)C2C—C3C—C12C—C11C179.27 (15)
C3A—C4A—C5A—C6A−178.65 (15)C3C—C4C—C5C—C6C−179.49 (16)
C3A—C4A—C5A—C10A−0.2 (2)C3C—C4C—C5C—C10C−0.5 (2)
C4A—C3A—C12A—C11A1.3 (3)C4C—C3C—C12C—C11C0.3 (2)
C4A—C5A—C6A—C7A177.39 (16)C4C—C5C—C6C—C7C178.39 (16)
C4A—C5A—C10A—C9A−176.88 (15)C4C—C5C—C10C—C9C−179.05 (15)
C4A—C5A—C10A—C11A1.4 (2)C4C—C5C—C10C—C11C0.4 (2)
C5A—C6A—C7A—C8A−0.6 (3)C5C—C6C—C7C—C8C0.6 (3)
C5A—C10A—C11A—C12A−1.3 (2)C5C—C10C—C11C—C12C0.0 (2)
C6A—C5A—C10A—C9A1.6 (2)C6C—C5C—C10C—C9C0.0 (2)
C6A—C5A—C10A—C11A179.92 (15)C6C—C5C—C10C—C11C179.43 (15)
C6A—C7A—C8A—C9A1.7 (3)C6C—C7C—C8C—C9C0.0 (3)
C7A—C8A—C9A—C10A−1.1 (3)C7C—C8C—C9C—C10C−0.6 (3)
C8A—C9A—C10A—C5A−0.5 (2)C8C—C9C—C10C—C5C0.7 (2)
C8A—C9A—C10A—C11A−178.80 (16)C8C—C9C—C10C—C11C−178.81 (16)
C9A—C10A—C11A—C12A176.95 (16)C9C—C10C—C11C—C12C179.46 (16)
C10A—C5A—C6A—C7A−1.0 (2)C10C—C5C—C6C—C7C−0.6 (3)
C10A—C11A—C12A—C3A−0.1 (3)C10C—C11C—C12C—C3C−0.3 (3)
C12A—C3A—C4A—C5A−1.2 (3)C12C—C3C—C4C—C5C0.2 (2)
O1B—C2B—C3B—C4B−123.14 (18)O1D—C2D—C3D—C4D−134.67 (16)
O1B—C2B—C3B—C12B57.6 (2)O1D—C2D—C3D—C12D49.4 (2)
C1B—C2B—C3B—C4B111.9 (2)C1D—C2D—C3D—C4D101.89 (18)
C1B—C2B—C3B—C12B−67.4 (2)C1D—C2D—C3D—C12D−74.01 (19)
C2B—C3B—C4B—C5B−179.22 (15)C2D—C3D—C4D—C5D−174.15 (15)
C2B—C3B—C12B—C11B179.29 (17)C2D—C3D—C12D—C11D174.36 (16)
C3B—C4B—C5B—C6B−177.67 (17)C3D—C4D—C5D—C6D−179.58 (16)
C3B—C4B—C5B—C10B−0.5 (3)C3D—C4D—C5D—C10D−0.5 (2)
C4B—C3B—C12B—C11B0.0 (3)C4D—C3D—C12D—C11D−1.6 (3)
C4B—C5B—C6B—C7B176.88 (17)C4D—C5D—C6D—C7D179.71 (17)
C4B—C5B—C10B—C9B−177.55 (16)C4D—C5D—C10D—C9D179.51 (16)
C4B—C5B—C10B—C11B0.7 (2)C4D—C5D—C10D—C11D−1.0 (2)
C5B—C6B—C7B—C8B0.3 (3)C5D—C6D—C7D—C8D0.2 (3)
C5B—C10B—C11B—C12B−0.7 (3)C5D—C10D—C11D—C12D1.2 (3)
C6B—C5B—C10B—C9B−0.3 (3)C6D—C5D—C10D—C9D−1.4 (2)
C6B—C5B—C10B—C11B178.02 (17)C6D—C5D—C10D—C11D178.15 (16)
C6B—C7B—C8B—C9B0.3 (3)C6D—C7D—C8D—C9D−0.2 (3)
C7B—C8B—C9B—C10B−0.9 (3)C7D—C8D—C9D—C10D−0.5 (3)
C8B—C9B—C10B—C5B0.9 (3)C8D—C9D—C10D—C5D1.3 (3)
C8B—C9B—C10B—C11B−177.32 (19)C8D—C9D—C10D—C11D−178.16 (17)
C9B—C10B—C11B—C12B177.54 (17)C9D—C10D—C11D—C12D−179.34 (16)
C10B—C5B—C6B—C7B−0.3 (3)C10D—C5D—C6D—C7D0.6 (3)
C10B—C11B—C12B—C3B0.3 (3)C10D—C11D—C12D—C3D0.1 (3)
C12B—C3B—C4B—C5B0.1 (3)C12D—C3D—C4D—C5D1.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Di0.86 (3)1.94 (3)2.7890 (18)171 (2)
O1B—H1B···O1A0.84 (3)1.95 (3)2.761 (2)162 (3)
O1C—H1C···O1B0.91 (3)1.76 (3)2.6648 (18)177 (2)
O1D—H1D···O1C0.87 (3)1.93 (3)2.7747 (18)163 (2)
Symmetry code: (i) x, y−1, z.
Calculated interaction energies (kJ mol-1) between hydrogen-bonded molecules top
CompPathEeleEpolEdisErepEtot
1A···Bi-50.8-10.9-24.872.3-38.7
1B···A-45.3-10.6-33.969.9-42.0
2A···Dii-47.3-10.4-41.269.5-50.6
2B···A-43.1-9.5-19.855.4-35.6
2C···B-61.0-13.5-37.788.2-52.8
2D···C-40.6-8.8-21.254.5-34.2
Symmetry codes: (i) x + 1/2, -y + 3/2, -z + 1, (ii) x, y - 1, z.
 

Funding information

Funding for this research was provided by: Deutsche Forschungsgemeinschaft (grant No. 334853423).

References

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ISSN: 2056-9890
Volume 81| Part 12| December 2025| Pages 1131-1135
https://doi.org/10.1107/S2056989025009533
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