Stigmasterol hemihydrate

The title compound, stigmasta-5,22-dien-3β-ol hemihydrate, C₂₉H₄₈O·0.5H₂O, previously thought to be the monohydrate, has two sterol mol­ecules and one water mol­ecule in the asymmetric unit. In both sterol mol­ecules, the methyl group of the ethyl substituent at the end of the hydro­carbon chain is disordered over two sites. The OH group of mol­ecule A donates a hydrogen bond to a water mol­ecule and accepts a hydrogen bond from the OH group of mol­ecule B. The OH group of mol­ecule B accepts two hydrogen bonds from water mol­ecules.

S1. Comment

Stigmasterol is a ubiquitous phytosterol, occurring naturally in a wide variety of plants. In each of the past 25 years, it was mentioned in 100–200 publications in the chemical literature. It is thus somewhat surprising that, despite the fact that cell dimensions of a material said to be stigmasterol monohydrate were reported over 60 years ago (Bernal et al., 1940), no crystal structure of stigmasterol or of any solvate has yet been reported. We have encountered crystals of stigmasterol hemihydrate on a number of occasions during our phytochemical studies over the last two decades. Such crystals are frequently of poor quality. Room-temperature diffraction data from the better ones has led to models in which the hydrocarbon chain at C17 is particularly poorly defined. We have now obtained fairly high-quality crystals of the title compound, (I), from Parthenium hysterophorus, and diffraction data at 120 K have yielded a model for which the hydrocarbon chain is reasonably well defined, except for a slight disorder of the ethyl group.

The asymmetric unit consists of two sterol molecules, one of which is illustrated in Fig. 1, and one water molecule. In the A molecule, the terminal methyl group of the disordered ethyl substituent occupies two sites with occupancy about 70:30. In the B molecule, the occupancies are about 60:40. The water molecule forms hydrogen bonds with the OH groups of both A and B molecules, but in different fashions. Both water H atoms donate to OH groups on B molecules, and the water molecule also accepts a hydrogen bond from the OH group of the A molecule (Table 2). Additionally, the OH group of the B molecule donates a hydrogen bond to the OH group of the A molecule. Molecules are arranged in the cell (Fig. 2) in a bilayer structure, with all the hydrogen bonding occurring near z = 1/2, and the hydrocarbon ends of the molecules near z = 0.

Neither the A nor B molecules exhibit significant out-of-plane bending of the sterol skeleton. For the A molecule, the 21-atom group O1/C1—C17/C20–C22 exhibits a maximum deviation of 0.472 (5) Å from coplanarity. The planarity of the B molecule is similar, with a maximum deviation of 0.490 (5) Å.

The close match of the room-temperature cell dimensions of stigmasterol hemihydrate [a = 9.523 (2), b = 7.5789 (7), c = 36.980 (3) Å, β = 94.213 (10)°, V = 2661.8 (8) ų at 299 K] to those of the `monohydrate' reported by Bernal et al. (1940) make it nearly certain that the previously studied compound was also the hemihydrate. One of the aims of that study was molecular-weight determination of steroids by measurement of densities and unit-cell volumes, a process complicated by the uncertainty in the degree of hydration. They report a derived molecular weight of 406±7 amu (atomic mass units), which differs from the calculated value (412.67) by about half the mass of a water molecule, but within experimental error. Although the hemihydrate fit their data better, Bernal et al. (1940) considered the monohydrate to be the best interpretation, by analogy to ergosterol, which was well known at the time to crystallize as the monohydrate. Hull & Woolfson (1976) later confirmed the structure of ergosterol monohydrate, which also suffers from a poorly defined hydrocarbon chain at room temperature.

The structure of stigmasta-5en-3β-ol, differing from the title sterol only in having the C22—C23 bond saturated (Argay et al., 1996), has also been reported as the monohydrate, and has cell dimensions a = 10.399 (2), b = 7.5888 (10), c = 35.369 (4) Å, β = 94.51 (2)° at 295 K, also quite similar to the cell dimensions of stigmasterol hemihydrate. While that structure is not isostructural with the title compound, it also has Z' = 2, with a similar bilayer packing. Its water molecules are reported to be disordered, as is the C1—C5/C10 ring and the OH groups.

S2. Experimental

The crude dichloromethane extract from the arial parts of Parthenium hysterophorus was chromatographed by standard vacuum liquid chromatography procedures (Cantrell et al., 1996) using silica gel with solvent mixtures of increasing polarity. Stigmasterol hemihydrate was isolated from non-polar fractions. Crystals were obtained from dichloromethane.

S3. Refinement

The ethyl CH₃ group (C29) is disordered over two positions in both the A and B molecules. Population parameters were initially refined, then fixed at 70:30 in the A molecule and at 60:40 in the B molecule for the final structure refinement. The absolute structure was not determined, but was chosen to agree with the accepted configuration of steroids (Fieser & Fieser, 1959). The water H-atom positions were refined isotropically, with U_iso = 1.5U_eq(O). Other H atoms were placed in calculated positions with C—H bond distances of 0.98 (CH), 0.97 (CH₂) and 0.96 Å (CH₃), and U_iso = 1.2U_eq of the attached C atom (1.5 for methyl), and thereafter treated as riding. A torsional parameter was refined for each OH group and for methyl groups C18, C19, and C21. The remaining methyl groups were modelled as staggered.

Computing details

Data collection: COLLECT (Nonius 1999); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The atom-numbering scheme and ellipsoids at the 40% probability level for molecule A of the title compound. Partially occupied methyl sites have been shown with boundary ellipses only.
	Fig. 2. Stereoview of the unit cell. The origin is in the lower left foreground, the a axis is horizontal, and the c axis is vertical. Only H atoms on O atoms are shown.

stigmasta-5,22-dien-3β-ol hemihydrate

Crystal data

C29H48O·0.5H2O	Cell dimensions at 299K were measured with CuKα radiation on an Enraf-Nonius CAD4 diffractometer, 25 reflections, theta limits 18.8-42.2°.
Mr = 421.68	Dx = 1.082 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.367 (2) Å	Cell parameters from 3373 reflections
b = 7.5127 (15) Å	θ = 2.5–27.4°
c = 36.857 (7) Å	µ = 0.06 mm^−1
β = 93.184 (9)°	T = 120 K
V = 2589.7 (10) Å^3	Prism, colorless
Z = 4	0.47 × 0.18 × 0.10 mm
F(000) = 940

Data collection

KappaCCD (with Oxford Cryostream) diffractometer	4631 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 27.4°, θmin = 2.6°
ω scans with κ offsets	h = −12→12
10659 measured reflections	k = −9→5
6072 independent reflections	l = −47→47

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 0.6772P] where P = (Fo^2 + 2Fc^2)/3
6072 reflections	(Δ/σ)max = 0.007
582 parameters	Δρmax = 0.30 e Å^−3
1 restraint	Δρmin = −0.27 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.7206 (3)	−0.0056 (3)	0.51414 (7)	0.0376 (6)
H1A	0.7530	0.0940	0.5209	0.056*
C1A	0.6838 (3)	−0.2135 (4)	0.42149 (9)	0.0277 (7)
H1A1	0.6704	−0.3392	0.4140	0.033*
H1A2	0.7769	−0.1734	0.4130	0.033*
C2A	0.6899 (4)	−0.2044 (5)	0.46296 (9)	0.0315 (8)
H2A1	0.6001	−0.2521	0.4721	0.038*
H2A2	0.7703	−0.2779	0.4731	0.038*
C3A	0.7102 (4)	−0.0125 (5)	0.47519 (9)	0.0302 (8)
H3A	0.8011	0.0340	0.4658	0.036*
C4A	0.5855 (4)	0.0999 (5)	0.45962 (9)	0.0329 (8)
H4A1	0.4957	0.0583	0.4697	0.040*
H4A2	0.6004	0.2256	0.4669	0.040*
C5A	0.5723 (3)	0.0875 (4)	0.41853 (9)	0.0255 (7)
C6A	0.5700 (3)	0.2333 (4)	0.39819 (9)	0.0270 (7)
H6A	0.5772	0.3446	0.4104	0.032*
C7A	0.5568 (3)	0.2365 (4)	0.35759 (9)	0.0254 (7)
H7A1	0.6510	0.2657	0.3482	0.030*
H7A2	0.4888	0.3313	0.3495	0.030*
C8A	0.5051 (3)	0.0589 (4)	0.34158 (9)	0.0223 (7)
H8A	0.4009	0.0455	0.3455	0.027*
C9A	0.5874 (3)	−0.0944 (4)	0.36108 (9)	0.0219 (6)
H9A	0.6912	−0.0677	0.3590	0.026*
C10A	0.5632 (3)	−0.0998 (4)	0.40238 (9)	0.0245 (7)
C11A	0.5601 (4)	−0.2739 (4)	0.34183 (9)	0.0265 (7)
H11A	0.6286	−0.3624	0.3525	0.032*
H11B	0.4627	−0.3150	0.3468	0.032*
C12A	0.5737 (3)	−0.2697 (4)	0.30060 (9)	0.0248 (7)
H12A	0.5453	−0.3869	0.2902	0.030*
H12B	0.6748	−0.2485	0.2954	0.030*
C13A	0.4799 (3)	−0.1240 (4)	0.28228 (8)	0.0232 (7)
C14A	0.5274 (3)	0.0511 (4)	0.30106 (9)	0.0226 (7)
H14A	0.6330	0.0593	0.2987	0.027*
C15A	0.4608 (4)	0.1967 (4)	0.27635 (9)	0.0287 (7)
H15A	0.3619	0.2233	0.2828	0.034*
H15B	0.5181	0.3074	0.2782	0.034*
C16A	0.4621 (4)	0.1180 (4)	0.23800 (10)	0.0307 (8)
H16A	0.5314	0.1827	0.2235	0.037*
H16B	0.3661	0.1278	0.2255	0.037*
C17A	0.5060 (3)	−0.0799 (4)	0.24211 (9)	0.0250 (7)
H17A	0.6112	−0.0880	0.2390	0.030*
C18A	0.3205 (3)	−0.1627 (4)	0.28655 (9)	0.0277 (7)
H18A	0.2972	−0.2814	0.2769	0.042*
H18B	0.2625	−0.0734	0.2731	0.042*
H18C	0.3003	−0.1578	0.3123	0.042*
C19A	0.4163 (3)	−0.1806 (5)	0.41003 (9)	0.0317 (8)
H19A	0.3933	−0.1532	0.4350	0.048*
H19B	0.4195	−0.3099	0.4068	0.048*
H19C	0.3427	−0.1299	0.3931	0.048*
C20A	0.4294 (4)	−0.1958 (5)	0.21226 (9)	0.0295 (7)
H20A	0.3245	−0.1907	0.2160	0.035*
C21A	0.4742 (4)	−0.3920 (5)	0.21377 (10)	0.0366 (9)
H21A	0.4282	−0.4556	0.1931	0.055*
H21B	0.4449	−0.4451	0.2365	0.055*
H21C	0.5783	−0.4006	0.2127	0.055*
C22A	0.4526 (4)	−0.1200 (5)	0.17495 (10)	0.0354 (8)
H22A	0.5477	−0.0951	0.1688	0.043*
C23A	0.3459 (5)	−0.0866 (6)	0.15033 (11)	0.0507 (11)
H23A	0.2511	−0.1062	0.1574	0.061*
C24A	0.3641 (5)	−0.0201 (7)	0.11214 (12)	0.0556 (12)
H24A	0.4674	0.0107	0.1107	0.067*
C25A	0.2787 (5)	0.1552 (7)	0.10539 (13)	0.0609 (12)
H25A	0.1760	0.1276	0.1090	0.073*
C26A	0.2871 (7)	0.2231 (9)	0.06674 (15)	0.0901 (19)
H26A	0.2555	0.1294	0.0496	0.135*
H26B	0.3860	0.2561	0.0625	0.135*
H26C	0.2252	0.3275	0.0632	0.135*
C27A	0.3232 (6)	0.2966 (7)	0.13234 (14)	0.0675 (14)
H27A	0.2653	0.4036	0.1276	0.101*
H27B	0.4244	0.3251	0.1301	0.101*
H27C	0.3089	0.2535	0.1570	0.101*
C28A	0.3320 (8)	−0.1629 (8)	0.08459 (15)	0.0868 (19)
H28A	0.3950	−0.2648	0.0901	0.104*	0.70
H28B	0.3532	−0.1160	0.0604	0.104*	0.70
C291	0.1692 (10)	−0.2310 (14)	0.0827 (2)	0.095 (3)	0.70
H29A	0.1566	−0.3232	0.0640	0.143*	0.70
H29B	0.1052	−0.1309	0.0766	0.143*	0.70
H29C	0.1465	−0.2803	0.1063	0.143*	0.70
H28C	0.3139	−0.1071	0.0604	0.114*	0.30
H28D	0.2429	−0.2257	0.0907	0.114*	0.30
C292	0.455 (3)	−0.300 (2)	0.0841 (5)	0.090 (7)	0.30
H29D	0.4313	−0.3907	0.0655	0.136*	0.30
H29E	0.4673	−0.3573	0.1080	0.136*	0.30
H29F	0.5435	−0.2397	0.0784	0.136*	0.30
O1B	1.0659 (3)	0.2486 (3)	0.46645 (7)	0.0369 (6)
H1B	1.1349	0.3185	0.4706	0.055*
C1B	0.9505 (3)	0.4654 (4)	0.37678 (9)	0.0261 (7)
H1B1	0.9485	0.5914	0.3689	0.031*
H1B2	0.8508	0.4211	0.3754	0.031*
C2B	1.0094 (4)	0.4566 (4)	0.41643 (9)	0.0295 (7)
H2B1	1.1066	0.5084	0.4185	0.035*
H2B2	0.9475	0.5271	0.4319	0.035*
C3B	1.0146 (4)	0.2655 (4)	0.42934 (9)	0.0294 (7)
H3B	0.9149	0.2175	0.4273	0.035*
C4B	1.1051 (4)	0.1530 (5)	0.40524 (9)	0.0323 (8)
H4B1	1.1011	0.0270	0.4130	0.039*
H4B2	1.2059	0.1926	0.4081	0.039*
C5B	1.0538 (3)	0.1669 (4)	0.36542 (9)	0.0262 (7)
C6B	1.0244 (3)	0.0212 (4)	0.34599 (9)	0.0271 (7)
H6B	1.0342	−0.0905	0.3579	0.033*
C7B	0.9770 (3)	0.0212 (4)	0.30667 (9)	0.0244 (7)
H7B1	0.8732	−0.0043	0.3042	0.029*
H7B2	1.0273	−0.0752	0.2942	0.029*
C8B	1.0063 (3)	0.1984 (4)	0.28805 (8)	0.0216 (6)
H8B	1.1116	0.2095	0.2855	0.026*
C9B	0.9571 (3)	0.3531 (4)	0.31218 (8)	0.0221 (6)
H9B	0.8544	0.3297	0.3166	0.027*
C10B	1.0382 (3)	0.3563 (4)	0.35013 (8)	0.0217 (6)
C11B	0.9611 (4)	0.5328 (4)	0.29247 (9)	0.0255 (7)
H11C	1.0620	0.5698	0.2910	0.031*
H11D	0.9129	0.6231	0.3071	0.031*
C12B	0.8893 (3)	0.5300 (4)	0.25388 (9)	0.0286 (7)
H12C	0.7856	0.5081	0.2554	0.034*
H12D	0.9014	0.6476	0.2423	0.034*
C13B	0.9528 (3)	0.3864 (4)	0.23037 (9)	0.0251 (7)
C14B	0.9317 (3)	0.2084 (4)	0.25055 (9)	0.0252 (7)
H14B	0.8270	0.1998	0.2543	0.030*
C15B	0.9630 (4)	0.0652 (5)	0.22293 (10)	0.0349 (8)
H15C	0.9129	−0.0470	0.2283	0.042*
H15D	1.0670	0.0414	0.2228	0.042*
C16B	0.9061 (4)	0.1445 (5)	0.18628 (10)	0.0381 (9)
H16C	0.8194	0.0800	0.1771	0.046*
H16D	0.9794	0.1350	0.1680	0.046*
C17B	0.8704 (4)	0.3433 (5)	0.19344 (9)	0.0305 (8)
H17B	0.7660	0.3499	0.1976	0.037*
C18B	1.1104 (3)	0.4220 (5)	0.22427 (10)	0.0307 (7)
H18D	1.1201	0.5387	0.2128	0.046*
H18E	1.1467	0.3295	0.2085	0.046*
H18F	1.1654	0.4207	0.2477	0.046*
C19B	1.1881 (3)	0.4399 (5)	0.34841 (9)	0.0288 (7)
H19D	1.1789	0.5689	0.3451	0.043*
H19E	1.2365	0.3888	0.3279	0.043*
H19F	1.2442	0.4151	0.3711	0.043*
C20B	0.8962 (4)	0.4584 (5)	0.15973 (10)	0.0346 (8)
H20B	0.9983	0.4426	0.1538	0.041*
C21B	0.8708 (5)	0.6576 (5)	0.16553 (11)	0.0480 (10)
H21D	0.8790	0.7209	0.1425	0.072*
H21E	0.9424	0.7035	0.1836	0.072*
H21F	0.7750	0.6757	0.1743	0.072*
C22B	0.8045 (5)	0.3943 (6)	0.12777 (11)	0.0463 (10)
H22B	0.7067	0.3689	0.1311	0.056*
C23B	0.8537 (7)	0.3713 (11)	0.09482 (13)	0.088 (2)
H23B	0.9517	0.3949	0.0915	0.106*
C24B	0.7585 (8)	0.3081 (12)	0.06200 (16)	0.102 (2)
H24B	0.6604	0.2894	0.0707	0.123*
C25B	0.8129 (11)	0.1215 (13)	0.04849 (19)	0.130 (3)
H25B	0.9111	0.1363	0.0396	0.156*
C26B	0.8176 (12)	−0.0270 (14)	0.0796 (3)	0.164 (4)
H26D	0.8871	0.0077	0.0992	0.246*
H26E	0.8459	−0.1413	0.0694	0.246*
H26F	0.7227	−0.0385	0.0893	0.246*
C27B	0.7169 (14)	0.0507 (17)	0.0183 (2)	0.201 (6)
H27D	0.7145	0.1342	−0.0022	0.301*
H27E	0.6202	0.0360	0.0267	0.301*
H27F	0.7529	−0.0648	0.0104	0.301*
C28B	0.7470 (16)	0.4484 (18)	0.0337 (3)	0.164 (5)
H28E	0.7179	0.5593	0.0435	0.197*	0.60
H28F	0.6854	0.4095	0.0132	0.197*	0.60
C293	0.9014 (16)	0.466 (3)	0.0196 (4)	0.147 (6)	0.60
H29G	0.9013	0.5565	0.0004	0.220*	0.60
H29H	0.9312	0.3515	0.0098	0.220*	0.60
H29I	0.9682	0.5016	0.0397	0.220*	0.60
H28G	0.7353	0.3907	0.0093	0.176*	0.40
H28H	0.8443	0.5115	0.0337	0.176*	0.40
C294	0.622 (3)	0.589 (3)	0.0422 (6)	0.154 (10)	0.40
H29J	0.6149	0.6802	0.0230	0.232*	0.40
H29K	0.6441	0.6466	0.0657	0.232*	0.40
H29L	0.5301	0.5266	0.0429	0.232*	0.40
O1W	1.1397 (4)	−0.1620 (5)	0.48299 (9)	0.0528 (8)
H1W	1.127 (6)	−0.051 (8)	0.4807 (15)	0.079*
H2W	1.070 (5)	−0.178 (8)	0.4963 (15)	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0525 (16)	0.0374 (14)	0.0222 (13)	−0.0016 (12)	−0.0025 (11)	−0.0035 (11)
C1A	0.0343 (18)	0.0225 (16)	0.0260 (18)	0.0030 (13)	−0.0023 (14)	0.0023 (13)
C2A	0.0427 (19)	0.0310 (18)	0.0206 (18)	0.0016 (15)	−0.0012 (14)	0.0015 (14)
C3A	0.0363 (18)	0.0295 (18)	0.0246 (19)	−0.0027 (15)	0.0002 (14)	0.0014 (14)
C4A	0.0408 (19)	0.0295 (18)	0.029 (2)	0.0022 (15)	0.0039 (15)	−0.0052 (15)
C5A	0.0250 (16)	0.0246 (16)	0.0269 (18)	0.0008 (13)	0.0019 (13)	−0.0033 (13)
C6A	0.0298 (16)	0.0186 (15)	0.032 (2)	0.0023 (13)	−0.0032 (13)	−0.0037 (14)
C7A	0.0264 (16)	0.0201 (15)	0.0294 (19)	−0.0009 (13)	−0.0008 (13)	0.0005 (13)
C8A	0.0199 (14)	0.0181 (15)	0.0287 (18)	0.0005 (12)	−0.0003 (12)	−0.0008 (13)
C9A	0.0198 (15)	0.0199 (15)	0.0256 (17)	0.0020 (12)	−0.0031 (12)	−0.0003 (13)
C10A	0.0278 (16)	0.0173 (15)	0.0284 (18)	0.0008 (12)	0.0012 (13)	0.0011 (13)
C11A	0.0328 (17)	0.0189 (15)	0.0273 (18)	0.0032 (13)	−0.0036 (13)	0.0012 (13)
C12A	0.0303 (16)	0.0166 (14)	0.0269 (18)	0.0036 (13)	−0.0029 (13)	−0.0013 (13)
C13A	0.0233 (15)	0.0226 (16)	0.0234 (17)	0.0006 (12)	−0.0023 (12)	0.0027 (13)
C14A	0.0202 (14)	0.0190 (15)	0.0284 (18)	0.0001 (12)	0.0009 (12)	0.0021 (13)
C15A	0.0334 (17)	0.0228 (17)	0.0294 (19)	0.0034 (14)	−0.0021 (13)	0.0027 (14)
C16A	0.0338 (18)	0.0254 (18)	0.033 (2)	0.0008 (14)	−0.0015 (14)	0.0055 (14)
C17A	0.0238 (16)	0.0259 (17)	0.0253 (18)	0.0017 (13)	0.0013 (12)	0.0025 (13)
C18A	0.0262 (16)	0.0247 (16)	0.0320 (19)	−0.0016 (13)	−0.0002 (13)	0.0008 (14)
C19A	0.0308 (17)	0.0334 (18)	0.0310 (19)	−0.0050 (15)	0.0030 (14)	0.0008 (15)
C20A	0.0328 (17)	0.0329 (18)	0.0224 (18)	0.0027 (14)	−0.0025 (13)	0.0012 (14)
C21A	0.048 (2)	0.0294 (18)	0.031 (2)	0.0027 (16)	−0.0058 (16)	−0.0040 (15)
C22A	0.0391 (19)	0.037 (2)	0.031 (2)	0.0084 (16)	0.0019 (15)	0.0009 (16)
C23A	0.060 (3)	0.056 (3)	0.036 (2)	0.013 (2)	−0.0033 (19)	0.003 (2)
C24A	0.068 (3)	0.068 (3)	0.030 (2)	0.010 (2)	−0.0034 (19)	0.004 (2)
C25A	0.068 (3)	0.063 (3)	0.051 (3)	0.004 (3)	−0.005 (2)	0.011 (2)
C26A	0.137 (6)	0.081 (4)	0.051 (4)	0.013 (4)	−0.008 (3)	0.020 (3)
C27A	0.077 (3)	0.067 (3)	0.059 (3)	0.013 (3)	0.005 (3)	0.001 (3)
C28A	0.150 (6)	0.063 (3)	0.046 (3)	0.017 (4)	−0.009 (3)	0.005 (3)
C291	0.129 (8)	0.097 (7)	0.055 (5)	−0.021 (6)	−0.028 (5)	−0.001 (5)
C292	0.17 (2)	0.038 (9)	0.065 (12)	0.026 (11)	−0.004 (12)	−0.010 (8)
O1B	0.0449 (15)	0.0388 (14)	0.0264 (14)	−0.0043 (11)	−0.0019 (10)	0.0029 (11)
C1B	0.0269 (16)	0.0243 (16)	0.0270 (18)	0.0005 (13)	−0.0004 (13)	−0.0006 (13)
C2B	0.0331 (17)	0.0275 (17)	0.0277 (19)	0.0045 (14)	0.0010 (14)	−0.0017 (14)
C3B	0.0315 (17)	0.0327 (18)	0.0239 (18)	−0.0037 (14)	0.0001 (13)	0.0061 (14)
C4B	0.0374 (19)	0.0268 (17)	0.032 (2)	0.0042 (15)	−0.0021 (15)	0.0032 (15)
C5B	0.0275 (16)	0.0250 (17)	0.0263 (18)	0.0025 (13)	0.0016 (13)	0.0040 (14)
C6B	0.0302 (17)	0.0196 (16)	0.032 (2)	0.0030 (13)	0.0042 (14)	0.0042 (14)
C7B	0.0227 (15)	0.0193 (15)	0.0314 (19)	0.0004 (12)	0.0042 (13)	−0.0002 (13)
C8B	0.0225 (15)	0.0180 (15)	0.0242 (17)	0.0010 (12)	0.0005 (12)	−0.0004 (12)
C9B	0.0187 (14)	0.0214 (15)	0.0261 (17)	−0.0026 (12)	0.0012 (12)	0.0021 (13)
C10B	0.0219 (15)	0.0194 (15)	0.0239 (17)	−0.0004 (12)	0.0013 (12)	0.0001 (13)
C11B	0.0346 (17)	0.0186 (15)	0.0236 (18)	0.0029 (13)	0.0046 (13)	−0.0014 (13)
C12B	0.0340 (17)	0.0264 (17)	0.0253 (19)	0.0028 (14)	0.0001 (14)	0.0028 (14)
C13B	0.0275 (16)	0.0237 (16)	0.0240 (17)	0.0022 (13)	0.0002 (13)	0.0003 (13)
C14B	0.0255 (15)	0.0224 (16)	0.0273 (18)	−0.0006 (13)	−0.0005 (12)	−0.0017 (13)
C15B	0.048 (2)	0.0270 (18)	0.029 (2)	0.0033 (16)	−0.0015 (15)	−0.0031 (15)
C16B	0.049 (2)	0.0319 (19)	0.033 (2)	0.0012 (17)	−0.0029 (16)	−0.0077 (16)
C17B	0.0315 (17)	0.0370 (19)	0.0228 (18)	0.0058 (15)	−0.0007 (13)	−0.0006 (15)
C18B	0.0319 (17)	0.0293 (18)	0.0311 (19)	−0.0010 (14)	0.0025 (14)	0.0032 (14)
C19B	0.0249 (16)	0.0317 (18)	0.0296 (19)	−0.0040 (14)	−0.0015 (13)	−0.0021 (15)
C20B	0.0401 (19)	0.0336 (19)	0.030 (2)	0.0049 (16)	0.0004 (15)	0.0029 (16)
C21B	0.072 (3)	0.036 (2)	0.036 (2)	0.007 (2)	0.0068 (19)	0.0082 (18)
C22B	0.054 (2)	0.051 (2)	0.033 (2)	0.009 (2)	−0.0078 (17)	0.0052 (19)
C23B	0.093 (4)	0.140 (6)	0.033 (3)	−0.018 (4)	0.006 (2)	−0.019 (3)
C24B	0.126 (6)	0.143 (7)	0.037 (3)	−0.014 (5)	−0.011 (3)	−0.015 (4)
C25B	0.203 (9)	0.136 (7)	0.051 (4)	−0.030 (7)	−0.007 (5)	−0.023 (5)
C26B	0.252 (12)	0.133 (8)	0.103 (7)	−0.031 (9)	−0.023 (7)	−0.006 (6)
C27B	0.358 (17)	0.166 (10)	0.072 (6)	−0.072 (11)	−0.039 (8)	−0.021 (6)
C28B	0.245 (13)	0.177 (11)	0.068 (6)	−0.056 (10)	−0.021 (7)	−0.014 (6)
C293	0.162 (14)	0.211 (19)	0.066 (9)	−0.027 (14)	−0.015 (8)	0.030 (10)
C294	0.26 (3)	0.087 (14)	0.117 (19)	−0.039 (18)	0.041 (19)	−0.015 (13)
O1W	0.0627 (19)	0.0472 (18)	0.0503 (19)	0.0103 (16)	0.0197 (14)	0.0125 (15)

Geometric parameters (Å, º)

O1A—C3A	1.435 (4)	O1B—H1B	0.8400
O1A—H1A	0.8400	C1B—C2B	1.534 (4)
C1A—C2A	1.528 (4)	C1B—C10B	1.549 (4)
C1A—C10A	1.554 (4)	C1B—H1B1	0.9900
C1A—H1A1	0.9900	C1B—H1B2	0.9900
C1A—H1A2	0.9900	C2B—C3B	1.512 (5)
C2A—C3A	1.519 (5)	C2B—H2B1	0.9900
C2A—H2A1	0.9900	C2B—H2B2	0.9900
C2A—H2A2	0.9900	C3B—C4B	1.519 (5)
C3A—C4A	1.527 (5)	C3B—H3B	1.0000
C3A—H3A	1.0000	C4B—C5B	1.523 (5)
C4A—C5A	1.516 (5)	C4B—H4B1	0.9900
C4A—H4A1	0.9900	C4B—H4B2	0.9900
C4A—H4A2	0.9900	C5B—C6B	1.329 (5)
C5A—C6A	1.327 (5)	C5B—C10B	1.534 (4)
C5A—C10A	1.528 (4)	C6B—C7B	1.492 (5)
C6A—C7A	1.495 (5)	C6B—H6B	0.9500
C6A—H6A	0.9500	C7B—C8B	1.529 (4)
C7A—C8A	1.526 (4)	C7B—H7B1	0.9900
C7A—H7A1	0.9900	C7B—H7B2	0.9900
C7A—H7A2	0.9900	C8B—C14B	1.515 (4)
C8A—C14A	1.520 (5)	C8B—C9B	1.549 (4)
C8A—C9A	1.541 (4)	C8B—H8B	1.0000
C8A—H8A	1.0000	C9B—C11B	1.534 (4)
C9A—C11A	1.539 (4)	C9B—C10B	1.554 (4)
C9A—C10A	1.552 (4)	C9B—H9B	1.0000
C9A—H9A	1.0000	C10B—C19B	1.543 (4)
C10A—C19A	1.544 (4)	C11B—C12B	1.539 (5)
C11A—C12A	1.532 (5)	C11B—H11C	0.9900
C11A—H11A	0.9900	C11B—H11D	0.9900
C11A—H11B	0.9900	C12B—C13B	1.524 (5)
C12A—C13A	1.536 (4)	C12B—H12C	0.9900
C12A—H12A	0.9900	C12B—H12D	0.9900
C12A—H12B	0.9900	C13B—C18B	1.529 (4)
C13A—C18A	1.537 (4)	C13B—C14B	1.548 (5)
C13A—C14A	1.541 (4)	C13B—C17B	1.561 (5)
C13A—C17A	1.549 (4)	C14B—C15B	1.521 (5)
C14A—C15A	1.534 (4)	C14B—H14B	1.0000
C14A—H14A	1.0000	C15B—C16B	1.544 (5)
C15A—C16A	1.533 (5)	C15B—H15C	0.9900
C15A—H15A	0.9900	C15B—H15D	0.9900
C15A—H15B	0.9900	C16B—C17B	1.556 (5)
C16A—C17A	1.548 (4)	C16B—H16C	0.9900
C16A—H16A	0.9900	C16B—H16D	0.9900
C16A—H16B	0.9900	C17B—C20B	1.543 (5)
C17A—C20A	1.548 (5)	C17B—H17B	1.0000
C17A—H17A	1.0000	C18B—H18D	0.9800
C18A—H18A	0.9800	C18B—H18E	0.9800
C18A—H18B	0.9800	C18B—H18F	0.9800
C18A—H18C	0.9800	C19B—H19D	0.9800
C19A—H19A	0.9800	C19B—H19E	0.9800
C19A—H19B	0.9800	C19B—H19F	0.9800
C19A—H19C	0.9800	C20B—C22B	1.498 (5)
C20A—C22A	1.515 (5)	C20B—C21B	1.532 (6)
C20A—C21A	1.532 (5)	C20B—H20B	1.0000
C20A—H20A	1.0000	C21B—H21D	0.9800
C21A—H21A	0.9800	C21B—H21E	0.9800
C21A—H21B	0.9800	C21B—H21F	0.9800
C21A—H21C	0.9800	C22B—C23B	1.334 (6)
C22A—C23A	1.336 (5)	C22B—H22B	0.9500
C22A—H22A	0.9500	C23B—C24B	1.537 (8)
C23A—C24A	1.512 (6)	C23B—H23B	0.9500
C23A—H23A	0.9500	C24B—C28B	1.483 (13)
C24A—C28A	1.496 (8)	C24B—C25B	1.582 (12)
C24A—C25A	1.553 (7)	C24B—H24B	1.0000
C24A—H24A	1.0000	C25B—C27B	1.490 (11)
C25A—C27A	1.498 (7)	C25B—C26B	1.598 (13)
C25A—C26A	1.519 (7)	C25B—H25B	1.0000
C25A—H25A	1.0000	C26B—H26D	0.9800
C26A—H26A	0.9800	C26B—H26E	0.9800
C26A—H26B	0.9800	C26B—H26F	0.9800
C26A—H26C	0.9800	C27B—H27D	0.9800
C27A—H27A	0.9800	C27B—H27E	0.9800
C27A—H27B	0.9800	C27B—H27F	0.9800
C27A—H27C	0.9800	C28B—C293	1.570 (16)
C28A—C292	1.55 (2)	C28B—C294	1.63 (3)
C28A—C291	1.606 (11)	C28B—H28E	0.955
C28A—H28A	0.980	C28B—H28F	0.971
C28A—H28B	0.988	C28B—H28G	1.000
C28A—H28C	0.992	C28B—H28H	1.028
C28A—H28D	0.995	C293—H29G	0.9800
C291—H29A	0.9800	C293—H29H	0.9800
C291—H29B	0.9800	C293—H29I	0.9800
C291—H29C	0.9800	C294—H29J	0.9800
C292—H29D	0.9800	C294—H29K	0.9800
C292—H29E	0.9800	C294—H29L	0.9800
C292—H29F	0.9800	O1W—H1W	0.85 (6)
O1B—C3B	1.430 (4)	O1W—H2W	0.85 (5)
C3A—O1A—H1A	109.5	C3B—O1B—H1B	109.5
C2A—C1A—C10A	114.5 (3)	C2B—C1B—C10B	113.9 (3)
C2A—C1A—H1A1	108.6	C2B—C1B—H1B1	108.8
C10A—C1A—H1A1	108.6	C10B—C1B—H1B1	108.8
C2A—C1A—H1A2	108.6	C2B—C1B—H1B2	108.8
C10A—C1A—H1A2	108.6	C10B—C1B—H1B2	108.8
H1A1—C1A—H1A2	107.6	H1B1—C1B—H1B2	107.7
C3A—C2A—C1A	109.7 (3)	C3B—C2B—C1B	110.2 (3)
C3A—C2A—H2A1	109.7	C3B—C2B—H2B1	109.6
C1A—C2A—H2A1	109.7	C1B—C2B—H2B1	109.6
C3A—C2A—H2A2	109.7	C3B—C2B—H2B2	109.6
C1A—C2A—H2A2	109.7	C1B—C2B—H2B2	109.6
H2A1—C2A—H2A2	108.2	H2B1—C2B—H2B2	108.1
O1A—C3A—C2A	109.4 (3)	O1B—C3B—C2B	112.9 (3)
O1A—C3A—C4A	111.3 (3)	O1B—C3B—C4B	110.0 (3)
C2A—C3A—C4A	109.4 (3)	C2B—C3B—C4B	110.7 (3)
O1A—C3A—H3A	108.9	O1B—C3B—H3B	107.7
C2A—C3A—H3A	108.9	C2B—C3B—H3B	107.7
C4A—C3A—H3A	108.9	C4B—C3B—H3B	107.7
C5A—C4A—C3A	111.1 (3)	C3B—C4B—C5B	111.6 (3)
C5A—C4A—H4A1	109.4	C3B—C4B—H4B1	109.3
C3A—C4A—H4A1	109.4	C5B—C4B—H4B1	109.3
C5A—C4A—H4A2	109.4	C3B—C4B—H4B2	109.3
C3A—C4A—H4A2	109.4	C5B—C4B—H4B2	109.3
H4A1—C4A—H4A2	108.0	H4B1—C4B—H4B2	108.0
C6A—C5A—C4A	120.8 (3)	C6B—C5B—C4B	120.5 (3)
C6A—C5A—C10A	122.8 (3)	C6B—C5B—C10B	123.6 (3)
C4A—C5A—C10A	116.5 (3)	C4B—C5B—C10B	115.9 (3)
C5A—C6A—C7A	125.2 (3)	C5B—C6B—C7B	124.4 (3)
C5A—C6A—H6A	117.4	C5B—C6B—H6B	117.8
C7A—C6A—H6A	117.4	C7B—C6B—H6B	117.8
C6A—C7A—C8A	112.3 (3)	C6B—C7B—C8B	112.6 (3)
C6A—C7A—H7A1	109.1	C6B—C7B—H7B1	109.1
C8A—C7A—H7A1	109.1	C8B—C7B—H7B1	109.1
C6A—C7A—H7A2	109.1	C6B—C7B—H7B2	109.1
C8A—C7A—H7A2	109.1	C8B—C7B—H7B2	109.1
H7A1—C7A—H7A2	107.9	H7B1—C7B—H7B2	107.8
C14A—C8A—C7A	110.9 (3)	C14B—C8B—C7B	111.6 (3)
C14A—C8A—C9A	109.7 (2)	C14B—C8B—C9B	110.5 (2)
C7A—C8A—C9A	109.5 (2)	C7B—C8B—C9B	109.2 (2)
C14A—C8A—H8A	108.9	C14B—C8B—H8B	108.5
C7A—C8A—H8A	108.9	C7B—C8B—H8B	108.5
C9A—C8A—H8A	108.9	C9B—C8B—H8B	108.5
C11A—C9A—C8A	112.0 (2)	C11B—C9B—C8B	111.9 (2)
C11A—C9A—C10A	113.6 (3)	C11B—C9B—C10B	112.9 (2)
C8A—C9A—C10A	112.4 (2)	C8B—C9B—C10B	112.4 (2)
C11A—C9A—H9A	106.1	C11B—C9B—H9B	106.4
C8A—C9A—H9A	106.1	C8B—C9B—H9B	106.4
C10A—C9A—H9A	106.1	C10B—C9B—H9B	106.4
C5A—C10A—C19A	108.8 (3)	C5B—C10B—C19B	108.9 (2)
C5A—C10A—C9A	110.5 (3)	C5B—C10B—C1B	107.5 (3)
C19A—C10A—C9A	111.7 (3)	C19B—C10B—C1B	109.0 (3)
C5A—C10A—C1A	107.8 (3)	C5B—C10B—C9B	110.4 (2)
C19A—C10A—C1A	109.5 (3)	C19B—C10B—C9B	111.7 (2)
C9A—C10A—C1A	108.5 (3)	C1B—C10B—C9B	109.2 (2)
C12A—C11A—C9A	114.7 (3)	C9B—C11B—C12B	113.9 (3)
C12A—C11A—H11A	108.6	C9B—C11B—H11C	108.8
C9A—C11A—H11A	108.6	C12B—C11B—H11C	108.8
C12A—C11A—H11B	108.6	C9B—C11B—H11D	108.8
C9A—C11A—H11B	108.6	C12B—C11B—H11D	108.8
H11A—C11A—H11B	107.6	H11C—C11B—H11D	107.7
C11A—C12A—C13A	111.9 (3)	C13B—C12B—C11B	111.8 (3)
C11A—C12A—H12A	109.2	C13B—C12B—H12C	109.3
C13A—C12A—H12A	109.2	C11B—C12B—H12C	109.3
C11A—C12A—H12B	109.2	C13B—C12B—H12D	109.3
C13A—C12A—H12B	109.2	C11B—C12B—H12D	109.3
H12A—C12A—H12B	107.9	H12C—C12B—H12D	107.9
C12A—C13A—C18A	110.8 (3)	C12B—C13B—C18B	111.7 (3)
C12A—C13A—C14A	105.5 (2)	C12B—C13B—C14B	105.9 (3)
C18A—C13A—C14A	111.9 (3)	C18B—C13B—C14B	111.8 (3)
C12A—C13A—C17A	117.1 (3)	C12B—C13B—C17B	116.9 (3)
C18A—C13A—C17A	110.1 (2)	C18B—C13B—C17B	110.0 (3)
C14A—C13A—C17A	100.9 (2)	C14B—C13B—C17B	99.8 (3)
C8A—C14A—C15A	118.8 (3)	C8B—C14B—C15B	118.6 (3)
C8A—C14A—C13A	115.0 (3)	C8B—C14B—C13B	114.6 (3)
C15A—C14A—C13A	104.1 (2)	C15B—C14B—C13B	104.8 (3)
C8A—C14A—H14A	106.0	C8B—C14B—H14B	106.0
C15A—C14A—H14A	106.0	C15B—C14B—H14B	106.0
C13A—C14A—H14A	106.0	C13B—C14B—H14B	106.0
C16A—C15A—C14A	104.4 (3)	C14B—C15B—C16B	104.0 (3)
C16A—C15A—H15A	110.9	C14B—C15B—H15C	111.0
C14A—C15A—H15A	110.9	C16B—C15B—H15C	111.0
C16A—C15A—H15B	110.9	C14B—C15B—H15D	111.0
C14A—C15A—H15B	110.9	C16B—C15B—H15D	111.0
H15A—C15A—H15B	108.9	H15C—C15B—H15D	109.0
C15A—C16A—C17A	107.2 (3)	C15B—C16B—C17B	106.8 (3)
C15A—C16A—H16A	110.3	C15B—C16B—H16C	110.4
C17A—C16A—H16A	110.3	C17B—C16B—H16C	110.4
C15A—C16A—H16B	110.3	C15B—C16B—H16D	110.4
C17A—C16A—H16B	110.3	C17B—C16B—H16D	110.4
H16A—C16A—H16B	108.5	H16C—C16B—H16D	108.6
C16A—C17A—C13A	104.1 (3)	C20B—C17B—C16B	110.9 (3)
C16A—C17A—C20A	111.2 (3)	C20B—C17B—C13B	119.6 (3)
C13A—C17A—C20A	117.9 (3)	C16B—C17B—C13B	104.3 (3)
C16A—C17A—H17A	107.8	C20B—C17B—H17B	107.2
C13A—C17A—H17A	107.8	C16B—C17B—H17B	107.2
C20A—C17A—H17A	107.8	C13B—C17B—H17B	107.2
C13A—C18A—H18A	109.5	C13B—C18B—H18D	109.5
C13A—C18A—H18B	109.5	C13B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C13A—C18A—H18C	109.5	C13B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C10A—C19A—H19A	109.5	C10B—C19B—H19D	109.5
C10A—C19A—H19B	109.5	C10B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C10A—C19A—H19C	109.5	C10B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C22A—C20A—C21A	110.0 (3)	C22B—C20B—C21B	109.7 (3)
C22A—C20A—C17A	110.5 (3)	C22B—C20B—C17B	110.2 (3)
C21A—C20A—C17A	113.6 (3)	C21B—C20B—C17B	113.7 (3)
C22A—C20A—H20A	107.5	C22B—C20B—H20B	107.7
C21A—C20A—H20A	107.5	C21B—C20B—H20B	107.7
C17A—C20A—H20A	107.5	C17B—C20B—H20B	107.7
C20A—C21A—H21A	109.5	C20B—C21B—H21D	109.5
C20A—C21A—H21B	109.5	C20B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
C20A—C21A—H21C	109.5	C20B—C21B—H21F	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21F	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21F	109.5
C23A—C22A—C20A	123.2 (4)	C23B—C22B—C20B	123.1 (4)
C23A—C22A—H22A	118.4	C23B—C22B—H22B	118.5
C20A—C22A—H22A	118.4	C20B—C22B—H22B	118.5
C22A—C23A—C24A	125.2 (4)	C22B—C23B—C24B	122.8 (6)
C22A—C23A—H23A	117.4	C22B—C23B—H23B	118.6
C24A—C23A—H23A	117.4	C24B—C23B—H23B	118.6
C28A—C24A—C23A	111.5 (5)	C28B—C24B—C23B	110.5 (7)
C28A—C24A—C25A	114.6 (4)	C28B—C24B—C25B	114.9 (7)
C23A—C24A—C25A	110.2 (4)	C23B—C24B—C25B	109.8 (7)
C28A—C24A—H24A	106.7	C28B—C24B—H24B	107.1
C23A—C24A—H24A	106.7	C23B—C24B—H24B	107.1
C25A—C24A—H24A	106.7	C25B—C24B—H24B	107.1
C27A—C25A—C26A	110.9 (5)	C27B—C25B—C24B	111.1 (9)
C27A—C25A—C24A	111.9 (4)	C27B—C25B—C26B	106.2 (8)
C26A—C25A—C24A	112.5 (4)	C24B—C25B—C26B	112.9 (7)
C27A—C25A—H25A	107.1	C27B—C25B—H25B	108.8
C26A—C25A—H25A	107.1	C24B—C25B—H25B	108.8
C24A—C25A—H25A	107.1	C26B—C25B—H25B	108.8
C25A—C26A—H26A	109.5	C25B—C26B—H26D	109.5
C25A—C26A—H26B	109.5	C25B—C26B—H26E	109.5
H26A—C26A—H26B	109.5	H26D—C26B—H26E	109.5
C25A—C26A—H26C	109.5	C25B—C26B—H26F	109.5
H26A—C26A—H26C	109.5	H26D—C26B—H26F	109.5
H26B—C26A—H26C	109.5	H26E—C26B—H26F	109.5
C25A—C27A—H27A	109.5	C25B—C27B—H27D	109.5
C25A—C27A—H27B	109.5	C25B—C27B—H27E	109.5
H27A—C27A—H27B	109.5	H27D—C27B—H27E	109.5
C25A—C27A—H27C	109.5	C25B—C27B—H27F	109.5
H27A—C27A—H27C	109.5	H27D—C27B—H27F	109.5
H27B—C27A—H27C	109.5	H27E—C27B—H27F	109.5
C24A—C28A—C292	111.4 (8)	C24B—C28B—C293	105.1 (12)
C24A—C28A—C291	114.4 (6)	C24B—C28B—C294	110.7 (11)
C292—C28A—C291	119.5 (10)	C293—C28B—C294	134.2 (14)
C24A—C28A—H28A	108.9	C24B—C28B—H28E	111.3
C291—C28A—H28A	108.6	C293—C28B—H28E	109.9
C24A—C28A—H28B	108.2	C24B—C28B—H28F	110.5
C291—C28A—H28B	108.2	H28E—C28B—H28F	112.9
H28A—C28A—H28B	108.5	C24B—C28B—H28G	109.0
C24A—C28A—H28C	109.0	C294—C28B—H28G	114.3
C292—C28A—H28C	111.2	C24B—C28B—H28H	107.3
C24A—C28A—H28D	109.0	C294—C28B—H28H	110.5
C292—C28A—H28D	108.7	H28G—C28B—H28H	104.8
H28C—C28A—H28D	107.5	C28B—C293—H29G	109.5
C28A—C291—H29A	109.5	C28B—C293—H29H	109.5
C28A—C291—H29B	109.5	H29G—C293—H29H	109.5
H29A—C291—H29B	109.5	C28B—C293—H29I	109.5
C28A—C291—H29C	109.5	H29G—C293—H29I	109.5
H29A—C291—H29C	109.5	H29H—C293—H29I	109.5
H29B—C291—H29C	109.5	C28B—C294—H29J	109.5
C28A—C292—H29D	109.5	C28B—C294—H29K	109.5
C28A—C292—H29E	109.5	H29J—C294—H29K	109.5
H29D—C292—H29E	109.5	C28B—C294—H29L	109.5
C28A—C292—H29F	109.5	H29J—C294—H29L	109.5
H29D—C292—H29F	109.5	H29K—C294—H29L	109.5
H29E—C292—H29F	109.5	H1W—O1W—H2W	95 (5)
C10A—C1A—C2A—C3A	−58.3 (4)	C10B—C1B—C2B—C3B	−58.2 (4)
C1A—C2A—C3A—O1A	−178.1 (3)	C1B—C2B—C3B—O1B	−178.8 (3)
C1A—C2A—C3A—C4A	59.7 (4)	C1B—C2B—C3B—C4B	57.5 (4)
O1A—C3A—C4A—C5A	−178.2 (3)	O1B—C3B—C4B—C5B	179.9 (3)
C2A—C3A—C4A—C5A	−57.2 (4)	C2B—C3B—C4B—C5B	−54.7 (4)
C3A—C4A—C5A—C6A	−126.2 (3)	C3B—C4B—C5B—C6B	−126.9 (3)
C3A—C4A—C5A—C10A	53.4 (4)	C3B—C4B—C5B—C10B	52.7 (4)
C4A—C5A—C6A—C7A	−179.8 (3)	C4B—C5B—C6B—C7B	−178.5 (3)
C10A—C5A—C6A—C7A	0.7 (5)	C10B—C5B—C6B—C7B	2.0 (5)
C5A—C6A—C7A—C8A	15.9 (4)	C5B—C6B—C7B—C8B	16.6 (4)
C6A—C7A—C8A—C14A	−166.1 (2)	C6B—C7B—C8B—C14B	−168.7 (3)
C6A—C7A—C8A—C9A	−45.0 (3)	C6B—C7B—C8B—C9B	−46.3 (3)
C14A—C8A—C9A—C11A	−48.0 (3)	C14B—C8B—C9B—C11B	−47.9 (3)
C7A—C8A—C9A—C11A	−169.8 (3)	C7B—C8B—C9B—C11B	−170.9 (3)
C14A—C8A—C9A—C10A	−177.2 (2)	C14B—C8B—C9B—C10B	−176.1 (2)
C7A—C8A—C9A—C10A	61.0 (3)	C7B—C8B—C9B—C10B	60.8 (3)
C6A—C5A—C10A—C19A	−109.5 (3)	C6B—C5B—C10B—C19B	−112.1 (3)
C4A—C5A—C10A—C19A	70.9 (3)	C4B—C5B—C10B—C19B	68.4 (3)
C6A—C5A—C10A—C9A	13.4 (4)	C6B—C5B—C10B—C1B	129.9 (3)
C4A—C5A—C10A—C9A	−166.2 (3)	C4B—C5B—C10B—C1B	−49.6 (3)
C6A—C5A—C10A—C1A	131.8 (3)	C6B—C5B—C10B—C9B	10.9 (4)
C4A—C5A—C10A—C1A	−47.8 (4)	C4B—C5B—C10B—C9B	−168.6 (3)
C11A—C9A—C10A—C5A	−172.3 (2)	C2B—C1B—C10B—C5B	52.2 (3)
C8A—C9A—C10A—C5A	−43.9 (3)	C2B—C1B—C10B—C19B	−65.7 (3)
C11A—C9A—C10A—C19A	−51.1 (3)	C2B—C1B—C10B—C9B	172.0 (3)
C8A—C9A—C10A—C19A	77.3 (3)	C11B—C9B—C10B—C5B	−169.8 (3)
C11A—C9A—C10A—C1A	69.7 (3)	C8B—C9B—C10B—C5B	−42.0 (3)
C8A—C9A—C10A—C1A	−161.9 (2)	C11B—C9B—C10B—C19B	−48.4 (3)
C2A—C1A—C10A—C5A	50.1 (4)	C8B—C9B—C10B—C19B	79.3 (3)
C2A—C1A—C10A—C19A	−68.1 (4)	C11B—C9B—C10B—C1B	72.2 (3)
C2A—C1A—C10A—C9A	169.7 (3)	C8B—C9B—C10B—C1B	−160.0 (2)
C8A—C9A—C11A—C12A	47.6 (4)	C8B—C9B—C11B—C12B	48.5 (3)
C10A—C9A—C11A—C12A	176.2 (2)	C10B—C9B—C11B—C12B	176.5 (3)
C9A—C11A—C12A—C13A	−53.4 (4)	C9B—C11B—C12B—C13B	−55.4 (4)
C11A—C12A—C13A—C18A	−64.5 (3)	C11B—C12B—C13B—C18B	−63.9 (3)
C11A—C12A—C13A—C14A	56.7 (3)	C11B—C12B—C13B—C14B	58.1 (3)
C11A—C12A—C13A—C17A	168.0 (3)	C11B—C12B—C13B—C17B	168.1 (3)
C7A—C8A—C14A—C15A	−56.2 (4)	C7B—C8B—C14B—C15B	−57.0 (4)
C9A—C8A—C14A—C15A	−177.2 (3)	C9B—C8B—C14B—C15B	−178.6 (3)
C7A—C8A—C14A—C13A	179.4 (2)	C7B—C8B—C14B—C13B	178.4 (3)
C9A—C8A—C14A—C13A	58.4 (3)	C9B—C8B—C14B—C13B	56.7 (3)
C12A—C13A—C14A—C8A	−61.9 (3)	C12B—C13B—C14B—C8B	−61.1 (3)
C18A—C13A—C14A—C8A	58.6 (3)	C18B—C13B—C14B—C8B	60.8 (4)
C17A—C13A—C14A—C8A	175.7 (2)	C17B—C13B—C14B—C8B	177.1 (3)
C12A—C13A—C14A—C15A	166.3 (3)	C12B—C13B—C14B—C15B	167.2 (3)
C18A—C13A—C14A—C15A	−73.1 (3)	C18B—C13B—C14B—C15B	−70.9 (3)
C17A—C13A—C14A—C15A	43.9 (3)	C17B—C13B—C14B—C15B	45.4 (3)
C8A—C14A—C15A—C16A	−162.5 (3)	C8B—C14B—C15B—C16B	−164.4 (3)
C13A—C14A—C15A—C16A	−33.0 (3)	C13B—C14B—C15B—C16B	−35.0 (3)
C14A—C15A—C16A—C17A	9.0 (3)	C14B—C15B—C16B—C17B	10.3 (4)
C15A—C16A—C17A—C13A	18.1 (3)	C15B—C16B—C17B—C20B	147.6 (3)
C15A—C16A—C17A—C20A	146.0 (3)	C15B—C16B—C17B—C13B	17.7 (4)
C12A—C13A—C17A—C16A	−151.5 (3)	C12B—C13B—C17B—C20B	84.2 (4)
C18A—C13A—C17A—C16A	80.7 (3)	C18B—C13B—C17B—C20B	−44.7 (4)
C14A—C13A—C17A—C16A	−37.6 (3)	C14B—C13B—C17B—C20B	−162.3 (3)
C12A—C13A—C17A—C20A	84.9 (3)	C12B—C13B—C17B—C16B	−151.3 (3)
C18A—C13A—C17A—C20A	−42.9 (4)	C18B—C13B—C17B—C16B	79.9 (3)
C14A—C13A—C17A—C20A	−161.3 (3)	C14B—C13B—C17B—C16B	−37.8 (3)
C16A—C17A—C20A—C22A	53.0 (4)	C16B—C17B—C20B—C22B	59.5 (4)
C13A—C17A—C20A—C22A	173.1 (3)	C13B—C17B—C20B—C22B	−179.2 (3)
C16A—C17A—C20A—C21A	177.1 (3)	C16B—C17B—C20B—C21B	−176.9 (3)
C13A—C17A—C20A—C21A	−62.8 (4)	C13B—C17B—C20B—C21B	−55.5 (4)
C21A—C20A—C22A—C23A	105.6 (4)	C21B—C20B—C22B—C23B	99.8 (6)
C17A—C20A—C22A—C23A	−128.2 (4)	C17B—C20B—C22B—C23B	−134.3 (5)
C20A—C22A—C23A—C24A	−176.7 (4)	C20B—C22B—C23B—C24B	−179.1 (6)
C22A—C23A—C24A—C28A	107.6 (6)	C22B—C23B—C24B—C28B	115.9 (10)
C22A—C23A—C24A—C25A	−123.9 (5)	C22B—C23B—C24B—C25B	−116.4 (8)
C28A—C24A—C25A—C27A	−176.0 (5)	C28B—C24B—C25B—C27B	−58.6 (11)
C23A—C24A—C25A—C27A	57.3 (6)	C23B—C24B—C25B—C27B	176.2 (8)
C28A—C24A—C25A—C26A	−50.4 (7)	C28B—C24B—C25B—C26B	−177.8 (8)
C23A—C24A—C25A—C26A	−177.1 (4)	C23B—C24B—C25B—C26B	57.0 (10)
C23A—C24A—C28A—C292	−75.2 (10)	C23B—C24B—C28B—C293	66.4 (11)
C25A—C24A—C28A—C292	158.7 (9)	C25B—C24B—C28B—C293	−58.5 (11)
C23A—C24A—C28A—C291	64.1 (6)	C23B—C24B—C28B—C294	−84.6 (13)
C25A—C24A—C28A—C291	−62.0 (7)	C25B—C24B—C28B—C294	150.5 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1W^i	0.84	2.10	2.894 (4)	158
O1B—H1B···O1A^i	0.84	1.95	2.787 (4)	172
O1W—H1W···O1B	0.85 (6)	2.37 (6)	3.212 (4)	171 (5)
O1W—H2W···O1B^ii	0.85 (5)	2.00 (5)	2.834 (4)	168 (5)

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+2, y−1/2, −z+1.