research communications
4-(4-Hydroxyphenyl)-2,2,4-trimethyl-7,8-benzothiachroman, a fused-ring counterpart of thia-Dianin's compound
aWolfson Centre for Materials Processing, Brunel University London, Kingston Lane, Uxbridge UB8 3PH, England, and bSchool of Chemistry, University of Glasgow, Glasgow G12 8QQ, Scotland
*Correspondence e-mail: chris.frampton@brunel.ac.uk
The title compound, C22H22OS [systematic name: 4-(1,3,3-trimethyl-2,3-dihydro-1H-4-thiaphenanthren-1-yl)phenol], crystallizes unsolvated from nitromethane as colourless prisms (m.p. 425–427 K) in the polar monoclinic Ia with Z′ = 2 (molecules A and B). Both independent molecules possess a very similar proximal conformation, this referring to the juxtaposition of the 4-hydroxyphenyl substituent with respect to the syn-related methyl group. In the crystal, molecule A is linked to molecule B by an O—H⋯O hydrogen bond. In turn, molecule B exhibits a weak O—H⋯π interaction with the phenolic group of molecule A related by a-glide symmetry. Together, these lead to [100] chains.
Keywords: crystal structure; thia-Dianin's compound; hydrogen bonding.
CCDC reference: 1579039
1. Chemical context
As part of a detailed study of clathrate formation by systems related to Dianin's compound (Frampton et al., 2013, 2017a,b; MacNicol, 1984), we have investigated structural modifications of thia-Dianin's compound 2, the direct thiachroman counterpart of Dianin's compound itself, 3. This led to interesting and diverse outcomes: (i) oxidation of 2 gave the colourless and beautifully crystalline sulfone 4, which crystallises in the polar Cc with Z′ = 1; (ii) crystals of 4 exhibit a significant second-harmonic generation (SHG) effect (Frampton et al., 1992); (iii) introduction of a methyl group at position carbon-7 led to with a structure in P212121, Z′ = 1; and (iv) introduction of a methyl group at either the 6- or 8-position yielded new clathrate systems isomorphous with 2 and 3, R (Hardy et al., 1979). The latter clathrate networks are comprised of columns formed from infinite stacking of hexameric hydrogen-bonded [OH]6 units along the c-axial direction, with clathrate formation being dependent upon efficient packing with adjacent threefold screw-related columns. Compound 1 was prepared to establish the effect on the resulting crystal packing of substantially extending the molecular skeleton of 2; the introduction of the bulky benzo group was expected to cause serious disruption to the intercolumn packing.
2. Structural commentary
The 1 is monoclinic, Ia, with two independent molecules in the (Z′ = 2). For clarity, each independent molecule is labelled with the suffix A or B, respectively. Figs. 1 and 2 show displacement ellipsoid plots for the two independent molecules. Both independent molecules possess a very similar proximal conformation, this referring to the juxtaposition of the 4-hydroxyphenyl substituent with respect to the syn-related methyl group. The C2—C3—C4—C11 torsion angles for molecules A and B are 79.5 (4) and 81.4 (4)°, respectively; the corresponding torsion angle for racemic Dianin's compound has magnitude 80.67° (Lee et al., 2014). The expected torsion angle value for a distal conformation is ∼160°. The torsion angle S1—C2—C3—C4, defining the heterocyclic ring has values of 62.8 (3) and 63.3 (3)° for A and B, respectively. Fig. 3 shows an overlay (Macrae et al., 2008) of molecules A and B shown in blue and brown, respectively, with an r.m.s. displacement of 0.0789 Å. In addition to showing the proximal conformation of both molecules, it can be seen that the two molecules differ only in the directional orientation of the phenolic H atom. The dihedral angles between the naphthalene C5–C10/C20–C23 ring system and the C11–C16 phenol ring are 74.25 (9) and 70.57 (9)° for molecules A and B, respectively. It is clear that the addition of the fused benzo ring to the thia-Dianin framework across positions C7 and C8 has caused significant disruption to the intercolumn packing to prevent formation of the conventional R host lattice.
of3. Supramolecular features
A view of the crystal packing down the c axis is shown in Fig. 4. In the crystal the two independent molecules in the A and B, are linked by an O—H⋯O hydrogen bond (Table 1). Molecule B exhibits a weak O—H⋯π interaction, shortest length H1B⋯C16A = 2.54 (6) Å (this being some 0.35 Å less than the Pauling sum of the van der Waals radii of 2.88 Å), with the phenolic group of molecule A related by a-glide symmetry. These two distinct hydrogen-bond interactions can be clearly detected in the IR spectrum of 1 with strong OH vibrational frequencies of 3409 and 3527 cm−1, respectively. The result is the formation of an infinite chain of molecules alternately linked by O—H⋯O and O—H⋯π interactions that propagates along the a axis of the crystal (Fig. 5).
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.38, update May 2017; Groom et al., 2016) for the thia-Dianin framework, 2, yielded 14 hits, all of which were genuine examples of analogues of the material under investigation. Although there are no entries for the empty racemic R host of thia-Dianin's compound, there are eight entries for the following host–guest ethanol (CSD refcode HPTHCR; MacNicol et al., 1969), 2,5,5-trimethylhex-3-yn-2-ol (TCHHXO; MacNicol & Wilson, 1971), cyclopentane and cyclooctane (METCCP and MSOCYO10, repectively; Hardy et al., 1979), and propan-2-ol at four different temperatures demonstrating three commensurate phase changes in the host lattice (VANFOI, 371 K, VANFOI01, 295 K, VANFOI02, 200 K, and VANFUO, 90 K; Frampton et al., 2017).
Thia-Dianin's compound, 2, was also found in the 1:1 quasi-racemic R3 host with Dianin's compound, 3, in the following three entries: apohost (BIBNAD and BIBNAD01) and CCl4/H2O (HIDQAO) (Frampton et al., 2013).
The structure and absolute stereochemistry determination of the resolved S-enantiomer of thia-Dianin's compound was used in the formation of the quasi-racemates above (BIBNEH; Frampton et al., 2013).
Two further examples demonstrating a slightly modified framework include the 7-methyl analogue (HPMTCM; Hardy et al., 1977) and the oxidized sulfone, 4 (KUTDUY; Frampton et al., 1992).
5. Synthesis and crystallization
Compound 1 was produced, as described in the literature, by the action of gaseous hydrogen chloride on a mixture of phenol and 4-methyl-4-(1-naphthylsulfanyl)pentan-2-one (Hardy et al., 1979). Unsolvated colourless prisms suitable for X-ray diffraction were obtained by recrystallisation from nitromethane solution, m.p. 425–427 K.
6. Refinement
The positional coordinates of the O-bound H atom were located from a difference Fourier map and freely refined along with an isotropic displacement parameter. All the remaining H atoms were placed geometrically in idealized positions and refined using a riding model (including Uiso(H) = 1.5Ueq(C) for methyl groups, or 1.2Ueq(C) for other H atoms. Initial refinements demonstrated that the crystal was a near-perfect twin rotated 179° about the [001] direction. The for the twinned data set (Rint = 0.0747) converged with R[F2 > 2σ(F2)], wR(F2), S = 0.0611, 0.2328, 1.115, Flack x = 0.01 (4) (Flack, 1983) by classical fit to all intensities. Deconvolution of the twin yielded a data set that was 91.7% complete to 0.80 Å after the reflections where the overlap was greater than 0.8 were removed. Crystal data, data collection, and structure details for the full data set with individual twin components are summarized in Table 2.
about the methyl C—C bond), with C–H = 0.95–0.99 Å andSupporting information
CCDC reference: 1579039
https://doi.org/10.1107/S2056989017014608/hb7711sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017014608/hb7711Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017014608/hb7711Isup3.cml
Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell
CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXD2014/6 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).C22H22OS | F(000) = 1424 |
Mr = 334.45 | Dx = 1.317 Mg m−3 |
Monoclinic, Ia | Cu Kα radiation, λ = 1.54184 Å |
a = 10.3190 (3) Å | Cell parameters from 5117 reflections |
b = 20.6009 (7) Å | θ = 3.5–76.6° |
c = 15.8756 (5) Å | µ = 1.72 mm−1 |
β = 91.640 (3)° | T = 100 K |
V = 3373.5 (2) Å3 | Plate, colourless |
Z = 8 | 0.36 × 0.14 × 0.05 mm |
Rigaku Oxford Diffraction SuperNova, Dualflex, AtlasS2 diffractometer | 7560 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray source | 7158 reflections with I > 2σ(I) |
Detector resolution: 5.2921 pixels mm-1 | θmax = 74.5°, θmin = 3.5° |
ω scans | h = −12→12 |
Absorption correction: analytical [CrysAlis PRO (Rigaku Oxford Diffraction, 2015), based on expressions derived by Clark & Reid (1995)] | k = −25→25 |
Tmin = 0.740, Tmax = 0.914 | l = −19→19 |
7560 measured reflections |
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)] = 0.037 | w = 1/[σ2(Fo2) + (0.0825P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.103 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.29 e Å−3 |
7560 reflections | Δρmin = −0.26 e Å−3 |
447 parameters | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. Value quoted is from the twinned data set |
2 restraints | Absolute structure parameter: 0.01 (4) |
Primary atom site location: structure-invariant direct methods |
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. Refined as a 2-component perfect twin |
x | y | z | Uiso*/Ueq | ||
S1A | 0.51009 (7) | 0.35123 (4) | 0.09817 (5) | 0.01486 (18) | |
O1A | 0.0378 (2) | 0.43051 (14) | 0.46900 (15) | 0.0178 (5) | |
H1A | 0.052 (6) | 0.470 (3) | 0.477 (4) | 0.049 (18)* | |
C2A | 0.3492 (3) | 0.32341 (17) | 0.1298 (2) | 0.0147 (6) | |
C3A | 0.3674 (3) | 0.27563 (16) | 0.20243 (19) | 0.0135 (6) | |
H3AA | 0.4203 | 0.2390 | 0.1822 | 0.016* | |
H3AB | 0.2811 | 0.2579 | 0.2154 | 0.016* | |
C4A | 0.4307 (3) | 0.30021 (16) | 0.28593 (19) | 0.0121 (6) | |
C5A | 0.6335 (3) | 0.35373 (16) | 0.3449 (2) | 0.0148 (6) | |
H5AA | 0.6058 | 0.3391 | 0.3982 | 0.018* | |
C6A | 0.7480 (3) | 0.38594 (17) | 0.3417 (2) | 0.0153 (7) | |
H6AA | 0.7983 | 0.3931 | 0.3919 | 0.018* | |
C7A | 0.7925 (3) | 0.40907 (16) | 0.2631 (2) | 0.0142 (6) | |
C8A | 0.7129 (3) | 0.39895 (16) | 0.1893 (2) | 0.0135 (6) | |
C9A | 0.5928 (3) | 0.36405 (16) | 0.1954 (2) | 0.0124 (6) | |
C10A | 0.5526 (3) | 0.34068 (16) | 0.2725 (2) | 0.0124 (6) | |
C11A | 0.3310 (3) | 0.33736 (16) | 0.33830 (19) | 0.0123 (6) | |
C12A | 0.2219 (3) | 0.30484 (16) | 0.36687 (19) | 0.0148 (6) | |
H12A | 0.2126 | 0.2598 | 0.3555 | 0.018* | |
C13A | 0.1268 (3) | 0.33628 (17) | 0.4112 (2) | 0.0149 (6) | |
H13A | 0.0541 | 0.3127 | 0.4302 | 0.018* | |
C14A | 0.1377 (3) | 0.40280 (17) | 0.42807 (18) | 0.0133 (6) | |
C15A | 0.2463 (3) | 0.43601 (17) | 0.40170 (19) | 0.0141 (6) | |
H15A | 0.2561 | 0.4809 | 0.4140 | 0.017* | |
C16A | 0.3413 (3) | 0.40343 (16) | 0.35715 (19) | 0.0126 (6) | |
H16A | 0.4149 | 0.4268 | 0.3392 | 0.015* | |
C17A | 0.4708 (3) | 0.23763 (17) | 0.3346 (2) | 0.0158 (6) | |
H17A | 0.5427 | 0.2166 | 0.3062 | 0.024* | |
H17B | 0.3968 | 0.2079 | 0.3359 | 0.024* | |
H17C | 0.4982 | 0.2490 | 0.3924 | 0.024* | |
C18A | 0.2637 (3) | 0.38209 (17) | 0.1493 (2) | 0.0171 (7) | |
H18A | 0.1811 | 0.3670 | 0.1712 | 0.026* | |
H18B | 0.2474 | 0.4072 | 0.0977 | 0.026* | |
H18C | 0.3079 | 0.4095 | 0.1916 | 0.026* | |
C19A | 0.2932 (4) | 0.28720 (18) | 0.0526 (2) | 0.0176 (7) | |
H19A | 0.2037 | 0.2742 | 0.0631 | 0.026* | |
H19B | 0.3456 | 0.2485 | 0.0422 | 0.026* | |
H19C | 0.2943 | 0.3158 | 0.0033 | 0.026* | |
C20A | 0.9137 (4) | 0.44096 (18) | 0.2562 (2) | 0.0190 (7) | |
H20A | 0.9663 | 0.4478 | 0.3055 | 0.023* | |
C21A | 0.9561 (4) | 0.46198 (18) | 0.1802 (2) | 0.0206 (7) | |
H21A | 1.0380 | 0.4827 | 0.1765 | 0.025* | |
C22A | 0.8771 (4) | 0.45259 (19) | 0.1076 (2) | 0.0208 (7) | |
H22A | 0.9064 | 0.4672 | 0.0546 | 0.025* | |
C23A | 0.7588 (3) | 0.42281 (18) | 0.1118 (2) | 0.0167 (7) | |
H23A | 0.7065 | 0.4180 | 0.0619 | 0.020* | |
S1B | 0.52638 (7) | 0.64688 (4) | 0.89907 (5) | 0.01474 (18) | |
O1B | 0.0356 (3) | 0.56057 (13) | 0.51496 (15) | 0.0181 (5) | |
H1B | −0.014 (6) | 0.585 (3) | 0.488 (4) | 0.047 (16)* | |
C2B | 0.3602 (3) | 0.67165 (16) | 0.8687 (2) | 0.0138 (6) | |
C3B | 0.3668 (3) | 0.72023 (16) | 0.79605 (19) | 0.0135 (6) | |
H3BA | 0.4195 | 0.7577 | 0.8160 | 0.016* | |
H3BB | 0.2779 | 0.7365 | 0.7842 | 0.016* | |
C4B | 0.4223 (3) | 0.69694 (16) | 0.71187 (19) | 0.0124 (6) | |
C5B | 0.6165 (4) | 0.64319 (16) | 0.6496 (2) | 0.0152 (6) | |
H5BA | 0.5798 | 0.6559 | 0.5966 | 0.018* | |
C6B | 0.7329 (4) | 0.61284 (18) | 0.6515 (2) | 0.0163 (7) | |
H6BA | 0.7765 | 0.6058 | 0.6004 | 0.020* | |
C7B | 0.7904 (3) | 0.59146 (16) | 0.7290 (2) | 0.0148 (6) | |
C8B | 0.7207 (3) | 0.60154 (16) | 0.8042 (2) | 0.0129 (6) | |
C9B | 0.5974 (3) | 0.63472 (16) | 0.8002 (2) | 0.0124 (6) | |
C10B | 0.5467 (3) | 0.65688 (16) | 0.7238 (2) | 0.0131 (6) | |
C11B | 0.3193 (3) | 0.66021 (17) | 0.65836 (19) | 0.0136 (6) | |
C12B | 0.2095 (3) | 0.69261 (16) | 0.62686 (19) | 0.0148 (6) | |
H12B | 0.1993 | 0.7375 | 0.6388 | 0.018* | |
C13B | 0.1148 (3) | 0.66103 (18) | 0.5785 (2) | 0.0162 (7) | |
H13B | 0.0409 | 0.6841 | 0.5577 | 0.019* | |
C14B | 0.1287 (3) | 0.59546 (17) | 0.56087 (19) | 0.0151 (6) | |
C15B | 0.2358 (3) | 0.56191 (17) | 0.5911 (2) | 0.0158 (6) | |
H15B | 0.2451 | 0.5170 | 0.5792 | 0.019* | |
C16B | 0.3308 (3) | 0.59444 (17) | 0.6394 (2) | 0.0162 (7) | |
H16B | 0.4048 | 0.5712 | 0.6598 | 0.019* | |
C17B | 0.4583 (3) | 0.76053 (18) | 0.6652 (2) | 0.0164 (6) | |
H17D | 0.4825 | 0.7502 | 0.6075 | 0.025* | |
H17E | 0.5315 | 0.7815 | 0.6950 | 0.025* | |
H17F | 0.3836 | 0.7899 | 0.6638 | 0.025* | |
C18B | 0.2769 (3) | 0.61185 (17) | 0.8491 (2) | 0.0171 (7) | |
H18D | 0.1910 | 0.6256 | 0.8282 | 0.026* | |
H18E | 0.2679 | 0.5861 | 0.9006 | 0.026* | |
H18F | 0.3184 | 0.5855 | 0.8062 | 0.026* | |
C19B | 0.3099 (4) | 0.70637 (18) | 0.9469 (2) | 0.0173 (6) | |
H19D | 0.2174 | 0.7159 | 0.9385 | 0.026* | |
H19E | 0.3577 | 0.7470 | 0.9559 | 0.026* | |
H19F | 0.3223 | 0.6783 | 0.9964 | 0.026* | |
C20B | 0.9126 (4) | 0.56092 (18) | 0.7331 (2) | 0.0179 (7) | |
H20B | 0.9581 | 0.5542 | 0.6826 | 0.021* | |
C21B | 0.9672 (4) | 0.54077 (17) | 0.8083 (2) | 0.0187 (7) | |
H21B | 1.0499 | 0.5204 | 0.8100 | 0.022* | |
C22B | 0.8995 (4) | 0.55050 (17) | 0.8832 (2) | 0.0186 (7) | |
H22B | 0.9374 | 0.5371 | 0.9356 | 0.022* | |
C23B | 0.7789 (3) | 0.57927 (17) | 0.8812 (2) | 0.0158 (6) | |
H23B | 0.7338 | 0.5843 | 0.9321 | 0.019* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0142 (4) | 0.0190 (4) | 0.0113 (4) | −0.0012 (3) | −0.0001 (3) | 0.0011 (3) |
O1A | 0.0157 (12) | 0.0184 (13) | 0.0196 (11) | −0.0003 (10) | 0.0041 (9) | −0.0050 (9) |
C2A | 0.0134 (15) | 0.0158 (17) | 0.0149 (15) | −0.0004 (13) | 0.0000 (11) | 0.0002 (12) |
C3A | 0.0138 (16) | 0.0114 (16) | 0.0152 (14) | 0.0009 (12) | 0.0008 (11) | −0.0025 (11) |
C4A | 0.0130 (15) | 0.0099 (15) | 0.0134 (14) | −0.0002 (12) | 0.0010 (11) | 0.0003 (10) |
C5A | 0.0170 (17) | 0.0138 (16) | 0.0137 (15) | 0.0024 (12) | 0.0018 (12) | −0.0003 (11) |
C6A | 0.0170 (17) | 0.0131 (17) | 0.0157 (16) | 0.0009 (13) | −0.0021 (12) | −0.0030 (12) |
C7A | 0.0131 (16) | 0.0099 (16) | 0.0194 (16) | 0.0026 (13) | 0.0009 (12) | −0.0009 (11) |
C8A | 0.0139 (16) | 0.0099 (16) | 0.0167 (16) | 0.0020 (13) | 0.0024 (11) | −0.0008 (11) |
C9A | 0.0115 (16) | 0.0116 (15) | 0.0140 (14) | 0.0030 (12) | −0.0008 (11) | −0.0005 (11) |
C10A | 0.0143 (17) | 0.0105 (15) | 0.0126 (15) | 0.0016 (13) | 0.0011 (11) | −0.0016 (11) |
C11A | 0.0149 (16) | 0.0124 (15) | 0.0095 (13) | −0.0006 (13) | −0.0011 (11) | 0.0009 (11) |
C12A | 0.0180 (16) | 0.0137 (16) | 0.0127 (14) | −0.0023 (13) | 0.0009 (11) | −0.0015 (11) |
C13A | 0.0148 (16) | 0.0153 (16) | 0.0145 (15) | −0.0022 (13) | 0.0004 (11) | −0.0009 (12) |
C14A | 0.0138 (15) | 0.0166 (16) | 0.0095 (14) | 0.0013 (12) | −0.0007 (10) | −0.0010 (11) |
C15A | 0.0192 (17) | 0.0108 (15) | 0.0122 (14) | −0.0007 (12) | −0.0005 (12) | −0.0012 (11) |
C16A | 0.0122 (15) | 0.0125 (16) | 0.0129 (15) | −0.0028 (12) | −0.0012 (11) | 0.0022 (11) |
C17A | 0.0177 (16) | 0.0120 (16) | 0.0175 (15) | −0.0006 (12) | −0.0023 (12) | 0.0014 (11) |
C18A | 0.0178 (17) | 0.0154 (17) | 0.0180 (16) | 0.0034 (13) | −0.0005 (12) | 0.0014 (12) |
C19A | 0.0200 (17) | 0.0190 (18) | 0.0135 (15) | −0.0002 (13) | −0.0013 (12) | −0.0008 (12) |
C20A | 0.0170 (17) | 0.0149 (18) | 0.0251 (17) | −0.0011 (14) | −0.0003 (12) | −0.0020 (12) |
C21A | 0.0165 (17) | 0.0136 (17) | 0.032 (2) | −0.0022 (13) | 0.0031 (13) | 0.0003 (13) |
C22A | 0.0212 (18) | 0.0188 (18) | 0.0227 (17) | −0.0032 (14) | 0.0071 (13) | 0.0024 (13) |
C23A | 0.0172 (16) | 0.0142 (17) | 0.0188 (16) | −0.0004 (13) | 0.0023 (12) | −0.0001 (12) |
S1B | 0.0136 (4) | 0.0194 (4) | 0.0112 (4) | 0.0009 (3) | −0.0001 (3) | 0.0008 (3) |
O1B | 0.0176 (13) | 0.0176 (13) | 0.0187 (12) | 0.0001 (10) | −0.0071 (9) | −0.0017 (9) |
C2B | 0.0143 (15) | 0.0122 (16) | 0.0148 (14) | 0.0010 (12) | 0.0000 (11) | −0.0007 (11) |
C3B | 0.0147 (16) | 0.0108 (16) | 0.0150 (15) | 0.0002 (12) | −0.0015 (11) | −0.0026 (11) |
C4B | 0.0134 (15) | 0.0111 (16) | 0.0125 (14) | 0.0012 (12) | −0.0007 (11) | −0.0008 (11) |
C5B | 0.0192 (18) | 0.0140 (16) | 0.0122 (15) | −0.0001 (13) | −0.0002 (12) | −0.0012 (11) |
C6B | 0.0179 (17) | 0.0166 (17) | 0.0145 (15) | −0.0006 (13) | 0.0031 (12) | −0.0013 (12) |
C7B | 0.0154 (17) | 0.0098 (16) | 0.0191 (16) | −0.0006 (13) | −0.0014 (12) | −0.0017 (11) |
C8B | 0.0129 (16) | 0.0087 (15) | 0.0170 (16) | −0.0027 (12) | −0.0001 (11) | 0.0005 (11) |
C9B | 0.0131 (16) | 0.0104 (15) | 0.0136 (14) | −0.0011 (12) | 0.0011 (11) | −0.0009 (11) |
C10B | 0.0144 (17) | 0.0122 (16) | 0.0127 (15) | −0.0001 (13) | −0.0006 (12) | −0.0029 (11) |
C11B | 0.0178 (17) | 0.0127 (15) | 0.0101 (14) | −0.0006 (13) | −0.0006 (11) | 0.0002 (11) |
C12B | 0.0190 (17) | 0.0137 (16) | 0.0117 (14) | 0.0022 (13) | 0.0004 (11) | −0.0020 (11) |
C13B | 0.0171 (17) | 0.0176 (17) | 0.0138 (15) | 0.0032 (13) | −0.0001 (12) | 0.0000 (12) |
C14B | 0.0185 (16) | 0.0180 (17) | 0.0087 (14) | −0.0039 (13) | 0.0002 (11) | −0.0012 (11) |
C15B | 0.0201 (17) | 0.0115 (16) | 0.0156 (15) | −0.0005 (13) | −0.0021 (12) | −0.0007 (11) |
C16B | 0.0186 (17) | 0.0145 (17) | 0.0152 (15) | 0.0019 (13) | −0.0026 (12) | 0.0011 (12) |
C17B | 0.0171 (16) | 0.0158 (17) | 0.0164 (15) | 0.0009 (13) | 0.0004 (11) | 0.0005 (12) |
C18B | 0.0175 (17) | 0.0158 (18) | 0.0178 (16) | −0.0026 (13) | −0.0007 (12) | 0.0010 (12) |
C19B | 0.0184 (16) | 0.0175 (17) | 0.0159 (15) | 0.0005 (13) | 0.0008 (11) | −0.0013 (12) |
C20B | 0.0189 (18) | 0.0123 (17) | 0.0226 (17) | −0.0023 (13) | 0.0025 (13) | −0.0017 (12) |
C21B | 0.0143 (17) | 0.0122 (17) | 0.0296 (18) | −0.0001 (12) | −0.0006 (13) | 0.0004 (13) |
C22B | 0.0192 (18) | 0.0136 (17) | 0.0226 (17) | −0.0014 (13) | −0.0056 (13) | 0.0039 (13) |
C23B | 0.0164 (17) | 0.0141 (16) | 0.0166 (16) | −0.0020 (13) | −0.0012 (12) | 0.0002 (11) |
S1A—C9A | 1.762 (3) | S1B—C9B | 1.768 (3) |
S1A—C2A | 1.839 (4) | S1B—C2B | 1.840 (3) |
O1A—C14A | 1.360 (4) | O1B—C14B | 1.389 (4) |
O1A—H1A | 0.84 (6) | O1B—H1B | 0.83 (6) |
C2A—C3A | 1.524 (4) | C2B—C18B | 1.529 (5) |
C2A—C19A | 1.533 (4) | C2B—C3B | 1.530 (4) |
C2A—C18A | 1.534 (5) | C2B—C19B | 1.537 (4) |
C3A—C4A | 1.546 (4) | C3B—C4B | 1.545 (4) |
C3A—H3AA | 0.9900 | C3B—H3BA | 0.9900 |
C3A—H3AB | 0.9900 | C3B—H3BB | 0.9900 |
C4A—C10A | 1.529 (5) | C4B—C10B | 1.533 (5) |
C4A—C11A | 1.544 (4) | C4B—C11B | 1.540 (4) |
C4A—C17A | 1.553 (4) | C4B—C17B | 1.555 (5) |
C5A—C6A | 1.357 (5) | C5B—C6B | 1.353 (5) |
C5A—C10A | 1.427 (5) | C5B—C10B | 1.427 (4) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.424 (5) | C6B—C7B | 1.421 (5) |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—C20A | 1.419 (5) | C7B—C20B | 1.409 (5) |
C7A—C8A | 1.427 (4) | C7B—C8B | 1.426 (5) |
C8A—C23A | 1.419 (5) | C8B—C23B | 1.423 (5) |
C8A—C9A | 1.439 (5) | C8B—C9B | 1.444 (5) |
C9A—C10A | 1.390 (5) | C9B—C10B | 1.385 (5) |
C11A—C16A | 1.397 (5) | C11B—C16B | 1.394 (5) |
C11A—C12A | 1.397 (5) | C11B—C12B | 1.396 (5) |
C12A—C13A | 1.384 (5) | C12B—C13B | 1.387 (5) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.400 (5) | C13B—C14B | 1.388 (5) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—C15A | 1.388 (5) | C14B—C15B | 1.379 (5) |
C15A—C16A | 1.397 (5) | C15B—C16B | 1.398 (5) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—H17A | 0.9800 | C17B—H17D | 0.9800 |
C17A—H17B | 0.9800 | C17B—H17E | 0.9800 |
C17A—H17C | 0.9800 | C17B—H17F | 0.9800 |
C18A—H18A | 0.9800 | C18B—H18D | 0.9800 |
C18A—H18B | 0.9800 | C18B—H18E | 0.9800 |
C18A—H18C | 0.9800 | C18B—H18F | 0.9800 |
C19A—H19A | 0.9800 | C19B—H19D | 0.9800 |
C19A—H19B | 0.9800 | C19B—H19E | 0.9800 |
C19A—H19C | 0.9800 | C19B—H19F | 0.9800 |
C20A—C21A | 1.365 (5) | C20B—C21B | 1.370 (5) |
C20A—H20A | 0.9500 | C20B—H20B | 0.9500 |
C21A—C22A | 1.407 (5) | C21B—C22B | 1.411 (5) |
C21A—H21A | 0.9500 | C21B—H21B | 0.9500 |
C22A—C23A | 1.370 (5) | C22B—C23B | 1.378 (5) |
C22A—H22A | 0.9500 | C22B—H22B | 0.9500 |
C23A—H23A | 0.9500 | C23B—H23B | 0.9500 |
C9A—S1A—C2A | 103.04 (15) | C9B—S1B—C2B | 102.31 (15) |
C14A—O1A—H1A | 111 (4) | C14B—O1B—H1B | 111 (4) |
C3A—C2A—C19A | 109.0 (3) | C18B—C2B—C3B | 114.3 (3) |
C3A—C2A—C18A | 114.5 (3) | C18B—C2B—C19B | 109.7 (3) |
C19A—C2A—C18A | 109.8 (3) | C3B—C2B—C19B | 109.2 (3) |
C3A—C2A—S1A | 108.4 (2) | C18B—C2B—S1B | 110.1 (2) |
C19A—C2A—S1A | 104.8 (2) | C3B—C2B—S1B | 108.5 (2) |
C18A—C2A—S1A | 109.8 (2) | C19B—C2B—S1B | 104.6 (2) |
C2A—C3A—C4A | 118.5 (3) | C2B—C3B—C4B | 118.3 (3) |
C2A—C3A—H3AA | 107.7 | C2B—C3B—H3BA | 107.7 |
C4A—C3A—H3AA | 107.7 | C4B—C3B—H3BA | 107.7 |
C2A—C3A—H3AB | 107.7 | C2B—C3B—H3BB | 107.7 |
C4A—C3A—H3AB | 107.7 | C4B—C3B—H3BB | 107.7 |
H3AA—C3A—H3AB | 107.1 | H3BA—C3B—H3BB | 107.1 |
C10A—C4A—C11A | 111.6 (3) | C10B—C4B—C11B | 111.5 (3) |
C10A—C4A—C3A | 112.8 (3) | C10B—C4B—C3B | 112.9 (3) |
C11A—C4A—C3A | 110.6 (3) | C11B—C4B—C3B | 111.3 (3) |
C10A—C4A—C17A | 108.3 (3) | C10B—C4B—C17B | 107.6 (3) |
C11A—C4A—C17A | 108.4 (3) | C11B—C4B—C17B | 108.8 (3) |
C3A—C4A—C17A | 104.8 (3) | C3B—C4B—C17B | 104.5 (3) |
C6A—C5A—C10A | 123.5 (3) | C6B—C5B—C10B | 122.8 (3) |
C6A—C5A—H5AA | 118.2 | C6B—C5B—H5BA | 118.6 |
C10A—C5A—H5AA | 118.2 | C10B—C5B—H5BA | 118.6 |
C5A—C6A—C7A | 120.0 (3) | C5B—C6B—C7B | 120.7 (3) |
C5A—C6A—H6AA | 120.0 | C5B—C6B—H6BA | 119.7 |
C7A—C6A—H6AA | 120.0 | C7B—C6B—H6BA | 119.7 |
C20A—C7A—C6A | 122.0 (3) | C20B—C7B—C6B | 122.0 (3) |
C20A—C7A—C8A | 119.5 (3) | C20B—C7B—C8B | 119.9 (3) |
C6A—C7A—C8A | 118.5 (3) | C6B—C7B—C8B | 118.1 (3) |
C23A—C8A—C7A | 117.6 (3) | C23B—C8B—C7B | 117.5 (3) |
C23A—C8A—C9A | 122.8 (3) | C23B—C8B—C9B | 122.6 (3) |
C7A—C8A—C9A | 119.6 (3) | C7B—C8B—C9B | 119.9 (3) |
C10A—C9A—C8A | 120.8 (3) | C10B—C9B—C8B | 120.3 (3) |
C10A—C9A—S1A | 124.8 (3) | C10B—C9B—S1B | 125.1 (3) |
C8A—C9A—S1A | 114.4 (2) | C8B—C9B—S1B | 114.6 (2) |
C9A—C10A—C5A | 117.5 (3) | C9B—C10B—C5B | 118.1 (3) |
C9A—C10A—C4A | 125.4 (3) | C9B—C10B—C4B | 125.5 (3) |
C5A—C10A—C4A | 117.1 (3) | C5B—C10B—C4B | 116.4 (3) |
C16A—C11A—C12A | 117.0 (3) | C16B—C11B—C12B | 117.4 (3) |
C16A—C11A—C4A | 123.4 (3) | C16B—C11B—C4B | 122.3 (3) |
C12A—C11A—C4A | 119.5 (3) | C12B—C11B—C4B | 120.2 (3) |
C13A—C12A—C11A | 122.0 (3) | C13B—C12B—C11B | 121.7 (3) |
C13A—C12A—H12A | 119.0 | C13B—C12B—H12B | 119.1 |
C11A—C12A—H12A | 119.0 | C11B—C12B—H12B | 119.1 |
C12A—C13A—C14A | 120.1 (3) | C12B—C13B—C14B | 119.5 (3) |
C12A—C13A—H13A | 120.0 | C12B—C13B—H13B | 120.2 |
C14A—C13A—H13A | 120.0 | C14B—C13B—H13B | 120.2 |
O1A—C14A—C15A | 124.5 (3) | C15B—C14B—C13B | 120.3 (3) |
O1A—C14A—C13A | 116.4 (3) | C15B—C14B—O1B | 117.3 (3) |
C15A—C14A—C13A | 119.1 (3) | C13B—C14B—O1B | 122.4 (3) |
C14A—C15A—C16A | 120.0 (3) | C14B—C15B—C16B | 119.6 (3) |
C14A—C15A—H15A | 120.0 | C14B—C15B—H15B | 120.2 |
C16A—C15A—H15A | 120.0 | C16B—C15B—H15B | 120.2 |
C15A—C16A—C11A | 121.8 (3) | C11B—C16B—C15B | 121.4 (3) |
C15A—C16A—H16A | 119.1 | C11B—C16B—H16B | 119.3 |
C11A—C16A—H16A | 119.1 | C15B—C16B—H16B | 119.3 |
C4A—C17A—H17A | 109.5 | C4B—C17B—H17D | 109.5 |
C4A—C17A—H17B | 109.5 | C4B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
C4A—C17A—H17C | 109.5 | C4B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
C2A—C18A—H18A | 109.5 | C2B—C18B—H18D | 109.5 |
C2A—C18A—H18B | 109.5 | C2B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C2A—C18A—H18C | 109.5 | C2B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C2A—C19A—H19A | 109.5 | C2B—C19B—H19D | 109.5 |
C2A—C19A—H19B | 109.5 | C2B—C19B—H19E | 109.5 |
H19A—C19A—H19B | 109.5 | H19D—C19B—H19E | 109.5 |
C2A—C19A—H19C | 109.5 | C2B—C19B—H19F | 109.5 |
H19A—C19A—H19C | 109.5 | H19D—C19B—H19F | 109.5 |
H19B—C19A—H19C | 109.5 | H19E—C19B—H19F | 109.5 |
C21A—C20A—C7A | 121.4 (3) | C21B—C20B—C7B | 121.4 (3) |
C21A—C20A—H20A | 119.3 | C21B—C20B—H20B | 119.3 |
C7A—C20A—H20A | 119.3 | C7B—C20B—H20B | 119.3 |
C20A—C21A—C22A | 119.2 (4) | C20B—C21B—C22B | 119.4 (4) |
C20A—C21A—H21A | 120.4 | C20B—C21B—H21B | 120.3 |
C22A—C21A—H21A | 120.4 | C22B—C21B—H21B | 120.3 |
C23A—C22A—C21A | 121.2 (3) | C23B—C22B—C21B | 120.7 (3) |
C23A—C22A—H22A | 119.4 | C23B—C22B—H22B | 119.7 |
C21A—C22A—H22A | 119.4 | C21B—C22B—H22B | 119.7 |
C22A—C23A—C8A | 121.2 (3) | C22B—C23B—C8B | 121.1 (3) |
C22A—C23A—H23A | 119.4 | C22B—C23B—H23B | 119.4 |
C8A—C23A—H23A | 119.4 | C8B—C23B—H23B | 119.4 |
C9A—S1A—C2A—C3A | −42.3 (2) | C9B—S1B—C2B—C18B | 82.3 (2) |
C9A—S1A—C2A—C19A | −158.7 (2) | C9B—S1B—C2B—C3B | −43.5 (2) |
C9A—S1A—C2A—C18A | 83.4 (2) | C9B—S1B—C2B—C19B | −159.9 (2) |
C19A—C2A—C3A—C4A | 176.4 (3) | C18B—C2B—C3B—C4B | −60.1 (4) |
C18A—C2A—C3A—C4A | −60.1 (4) | C19B—C2B—C3B—C4B | 176.7 (3) |
S1A—C2A—C3A—C4A | 62.8 (3) | S1B—C2B—C3B—C4B | 63.3 (3) |
C2A—C3A—C4A—C10A | −46.3 (4) | C2B—C3B—C4B—C10B | −44.8 (4) |
C2A—C3A—C4A—C11A | 79.5 (4) | C2B—C3B—C4B—C11B | 81.4 (4) |
C2A—C3A—C4A—C17A | −163.9 (3) | C2B—C3B—C4B—C17B | −161.4 (3) |
C10A—C5A—C6A—C7A | 0.4 (5) | C10B—C5B—C6B—C7B | 1.5 (6) |
C5A—C6A—C7A—C20A | −177.7 (3) | C5B—C6B—C7B—C20B | −178.7 (3) |
C5A—C6A—C7A—C8A | 1.6 (5) | C5B—C6B—C7B—C8B | 1.4 (5) |
C20A—C7A—C8A—C23A | −1.1 (5) | C20B—C7B—C8B—C23B | −0.5 (5) |
C6A—C7A—C8A—C23A | 179.6 (3) | C6B—C7B—C8B—C23B | 179.4 (3) |
C20A—C7A—C8A—C9A | 177.2 (3) | C20B—C7B—C8B—C9B | 178.0 (3) |
C6A—C7A—C8A—C9A | −2.1 (5) | C6B—C7B—C8B—C9B | −2.1 (5) |
C23A—C8A—C9A—C10A | 179.0 (3) | C23B—C8B—C9B—C10B | 178.3 (3) |
C7A—C8A—C9A—C10A | 0.7 (5) | C7B—C8B—C9B—C10B | −0.1 (5) |
C23A—C8A—C9A—S1A | 1.9 (4) | C23B—C8B—C9B—S1B | 1.3 (4) |
C7A—C8A—C9A—S1A | −176.4 (2) | C7B—C8B—C9B—S1B | −177.2 (2) |
C2A—S1A—C9A—C10A | 15.4 (3) | C2B—S1B—C9B—C10B | 15.7 (3) |
C2A—S1A—C9A—C8A | −167.7 (2) | C2B—S1B—C9B—C8B | −167.4 (2) |
C8A—C9A—C10A—C5A | 1.1 (5) | C8B—C9B—C10B—C5B | 3.0 (5) |
S1A—C9A—C10A—C5A | 177.9 (2) | S1B—C9B—C10B—C5B | 179.7 (3) |
C8A—C9A—C10A—C4A | −176.8 (3) | C8B—C9B—C10B—C4B | −175.3 (3) |
S1A—C9A—C10A—C4A | 0.0 (5) | S1B—C9B—C10B—C4B | 1.4 (5) |
C6A—C5A—C10A—C9A | −1.8 (5) | C6B—C5B—C10B—C9B | −3.8 (5) |
C6A—C5A—C10A—C4A | 176.3 (3) | C6B—C5B—C10B—C4B | 174.7 (3) |
C11A—C4A—C10A—C9A | −114.1 (4) | C11B—C4B—C10B—C9B | −117.2 (4) |
C3A—C4A—C10A—C9A | 11.2 (5) | C3B—C4B—C10B—C9B | 8.9 (5) |
C17A—C4A—C10A—C9A | 126.6 (3) | C17B—C4B—C10B—C9B | 123.7 (3) |
C11A—C4A—C10A—C5A | 67.9 (4) | C11B—C4B—C10B—C5B | 64.5 (4) |
C3A—C4A—C10A—C5A | −166.8 (3) | C3B—C4B—C10B—C5B | −169.4 (3) |
C17A—C4A—C10A—C5A | −51.3 (4) | C17B—C4B—C10B—C5B | −54.6 (4) |
C10A—C4A—C11A—C16A | 11.0 (4) | C10B—C4B—C11B—C16B | 12.2 (4) |
C3A—C4A—C11A—C16A | −115.5 (3) | C3B—C4B—C11B—C16B | −114.8 (3) |
C17A—C4A—C11A—C16A | 130.2 (3) | C17B—C4B—C11B—C16B | 130.7 (3) |
C10A—C4A—C11A—C12A | −171.1 (3) | C10B—C4B—C11B—C12B | −167.8 (3) |
C3A—C4A—C11A—C12A | 62.4 (4) | C3B—C4B—C11B—C12B | 65.2 (4) |
C17A—C4A—C11A—C12A | −51.9 (4) | C17B—C4B—C11B—C12B | −49.4 (4) |
C16A—C11A—C12A—C13A | 0.6 (5) | C16B—C11B—C12B—C13B | 0.0 (5) |
C4A—C11A—C12A—C13A | −177.4 (3) | C4B—C11B—C12B—C13B | −179.9 (3) |
C11A—C12A—C13A—C14A | 0.5 (5) | C11B—C12B—C13B—C14B | 0.1 (5) |
C12A—C13A—C14A—O1A | 177.5 (3) | C12B—C13B—C14B—C15B | 0.0 (5) |
C12A—C13A—C14A—C15A | −1.7 (5) | C12B—C13B—C14B—O1B | 178.1 (3) |
O1A—C14A—C15A—C16A | −177.5 (3) | C13B—C14B—C15B—C16B | −0.3 (5) |
C13A—C14A—C15A—C16A | 1.6 (5) | O1B—C14B—C15B—C16B | −178.4 (3) |
C14A—C15A—C16A—C11A | −0.4 (5) | C12B—C11B—C16B—C15B | −0.3 (5) |
C12A—C11A—C16A—C15A | −0.7 (5) | C4B—C11B—C16B—C15B | 179.6 (3) |
C4A—C11A—C16A—C15A | 177.2 (3) | C14B—C15B—C16B—C11B | 0.4 (5) |
C6A—C7A—C20A—C21A | 179.0 (3) | C6B—C7B—C20B—C21B | 179.7 (3) |
C8A—C7A—C20A—C21A | −0.3 (5) | C8B—C7B—C20B—C21B | −0.4 (5) |
C7A—C20A—C21A—C22A | 0.9 (5) | C7B—C20B—C21B—C22B | 0.3 (5) |
C20A—C21A—C22A—C23A | 0.0 (6) | C20B—C21B—C22B—C23B | 0.8 (5) |
C21A—C22A—C23A—C8A | −1.5 (6) | C21B—C22B—C23B—C8B | −1.7 (5) |
C7A—C8A—C23A—C22A | 2.1 (5) | C7B—C8B—C23B—C22B | 1.6 (5) |
C9A—C8A—C23A—C22A | −176.2 (3) | C9B—C8B—C23B—C22B | −176.9 (3) |
Cg1 is the centroid of the C11A–C16A ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1B | 0.84 (6) | 1.96 (6) | 2.777 (4) | 162 (6) |
O1B—H1B···Cg1i | 0.83 (6) | 3.18 (6) | 3.959 (4) | 158 (6) |
Symmetry code: (i) x−1/2, −y+1, z. |
References
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