Two crystallographic forms and the absolute structure of 5α,14α-androstane

Crittenden, C.M.; DiPasquale, A.G.

doi:10.1107/S2053229621008408

Two crystallographic forms and the absolute structure of 5α,14α-androstane

5α,14α-Androstane (C₁₉H₃₂) crystallizes in two different polymorphic forms in the same vapor diffusion experiment. The major form (Form I) crystallizes as thin plates in the space group P2₁, with Z = 4. These plates are twinned along a long c axis of length 43 Å and readily suffer from radiation damage when diffracted. The minor form (Form II) crystallizes as fine needles in the space group P2₁2₁2₁, Z = 3. In the minor form, 5α,14α-androstane cocrystallizes with 5α,14α-androstan-17-one, an oxidation product of 5α,14α-androstane. The presence of 5α,14α-androstan-17-one in the minor form of the crystals was confirmed by HR-MS. Form II can be crystallized as a pure form without the ketone impurity using a different solvent system. High level density functional theory (DFT) lattice free energy calculations were performed and show that both pure forms are isoergic within the estimated error of the calculations.

Keywords: androstane; crystal structure; absolute structure; chiral hydrocarbon; polymorphic forms; free energy; light-atom structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621008408/yp3218sup1.cif Contains datablocks Form_I, Form_II_impure, Form_II, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621008408/yp3218Form_Isup2.hkl Contains datablock Form_I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621008408/yp3218Form_II_impuresup3.hkl Contains datablock Form_II_impure
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621008408/yp3218Form_IIsup4.hkl Contains datablock Form_II
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621008408/yp3218sup5.pdf Supplementary material

CCDC references: 2102883; 2102884; 2102885

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: WinGX (Farrugia, 2012) and SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: WinGX (Farrugia, 2012) and SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-32 (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).

5α,14α-Androstane, Form I (Form_I) top

Crystal data top

C₁₉H₃₂	F(000) = 1168
M_r = 260.44	D_x = 1.095 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 7.4417 (1) Å	Cell parameters from 31493 reflections
b = 9.8831 (1) Å	θ = 2.1–75.2°
c = 43.0002 (6) Å	µ = 0.44 mm⁻¹
β = 92.742 (1)°	T = 90 K
V = 3158.92 (7) Å³	Plate, colorless
Z = 8	0.20 × 0.13 × 0.06 mm

Data collection top

ROD, Synergy Custom system, HyPix diffractometer	15656 independent reflections
Radiation source: Rotating-anode X-ray tube	15312 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.025
ω scans	θ_max = 75.5°, θ_min = 2.1°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021)	h = −9→9
T_min = 0.776, T_max = 1.000	k = −12→12
64068 measured reflections	l = −53→52

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0523P)² + 2.5739P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.133	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.31 e Å⁻³
15656 reflections	Δρ_min = −0.21 e Å⁻³
695 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0006 (2)
Primary atom site location: iterative	Absolute structure: Flack x determined using 5698 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (5)

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. Refined as a 2-component twin

Data were integrated and scaled using CrysAlis PRO (Rigaku OD, 2021). WinGX (Farrugia, 2012) was used for the solution and refinement of the crystal structures. Solution by intrinsic phasing (SHELXT2014; Sheldrick, 2015a) produced a complete heavy-atom phasing model. All non-H atoms were refined anisotropically by full-matrix least-squares (SHELXL2018; Sheldrick, 2015b).

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

	x	y	z	U_iso*/U_eq
C1	1.1169 (6)	0.7345 (5)	0.81549 (9)	0.0201 (9)
H1A	1.214915	0.679497	0.807196	0.024*
H1B	1.151996	0.830878	0.814033	0.024*
C2	1.0973 (7)	0.6982 (5)	0.84980 (9)	0.0238 (10)
H2A	1.078475	0.599437	0.851672	0.029*
H2B	1.209828	0.721660	0.861800	0.029*
C3	0.9395 (7)	0.7729 (5)	0.86366 (9)	0.0242 (10)
H3A	0.922241	0.738711	0.884956	0.029*
H3B	0.967826	0.870625	0.865189	0.029*
C4	0.7657 (6)	0.7537 (5)	0.84382 (9)	0.0201 (9)
H4A	0.669682	0.810288	0.852253	0.024*
H4B	0.727358	0.657914	0.844882	0.024*
C5	0.7907 (6)	0.7925 (4)	0.80970 (9)	0.0187 (9)
H5	0.829102	0.889465	0.809821	0.022*
C6	0.6148 (6)	0.7860 (5)	0.79032 (10)	0.0221 (9)
H6A	0.523145	0.841779	0.800279	0.027*
H6B	0.571054	0.691387	0.789497	0.027*
C7	0.6392 (6)	0.8372 (5)	0.75724 (9)	0.0220 (9)
H7A	0.668026	0.934993	0.757960	0.026*
H7B	0.524942	0.825778	0.744758	0.026*
C8	0.7892 (6)	0.7616 (4)	0.74145 (9)	0.0187 (9)
H8	0.752512	0.664734	0.738811	0.022*
C9	0.9663 (6)	0.7669 (4)	0.76164 (9)	0.0153 (8)
H9	0.997063	0.864951	0.764078	0.018*
C10	0.9444 (6)	0.7113 (4)	0.79523 (9)	0.0174 (8)
C11	1.1224 (6)	0.7024 (5)	0.74492 (9)	0.0217 (9)
H11A	1.102650	0.603481	0.743565	0.026*
H11B	1.235601	0.717873	0.757465	0.026*
C12	1.1436 (7)	0.7589 (5)	0.71185 (10)	0.0237 (10)
H12A	1.180945	0.854943	0.713268	0.028*
H12B	1.239178	0.708044	0.701671	0.028*
C13	0.9694 (7)	0.7482 (4)	0.69218 (9)	0.0208 (9)
C14	0.8203 (6)	0.8208 (4)	0.70944 (9)	0.0187 (9)
H14	0.862475	0.915810	0.713002	0.022*
C15	0.6621 (7)	0.8284 (5)	0.68530 (9)	0.0246 (10)
H15A	0.580708	0.904360	0.689843	0.030*
H15B	0.592476	0.743036	0.684646	0.030*
C16	0.7565 (7)	0.8521 (6)	0.65422 (10)	0.0299 (11)
H16A	0.735304	0.945704	0.646713	0.036*
H16B	0.709466	0.788384	0.638035	0.036*
C17	0.9618 (7)	0.8274 (5)	0.66145 (10)	0.0265 (10)
H17A	1.014709	0.774077	0.644673	0.032*
H17B	1.027391	0.914233	0.663793	0.032*
C18	0.9012 (6)	0.5583 (4)	0.79400 (9)	0.0187 (8)
H18A	1.002852	0.509220	0.785723	0.028*
H18B	0.793310	0.543117	0.780474	0.028*
H18C	0.879925	0.525624	0.815026	0.028*
C19	0.9256 (7)	0.5987 (5)	0.68504 (10)	0.0255 (10)
H19A	1.024054	0.558133	0.673912	0.038*
H19B	0.813841	0.593109	0.672080	0.038*
H19C	0.910893	0.549794	0.704578	0.038*
C20	−0.4513 (7)	0.1102 (5)	0.44527 (9)	0.0215 (9)
H20A	−0.556822	0.089018	0.457569	0.026*
H20B	−0.422194	0.207135	0.448402	0.026*
C21	−0.5006 (7)	0.0855 (5)	0.41054 (10)	0.0241 (10)
H21A	−0.544590	−0.008501	0.407735	0.029*
H21B	−0.599329	0.147386	0.403695	0.029*
C22	−0.3414 (8)	0.1077 (5)	0.39039 (9)	0.0282 (11)
H22A	−0.308996	0.204889	0.390644	0.034*
H22B	−0.375504	0.082245	0.368634	0.034*
C23	−0.1775 (6)	0.0237 (5)	0.40193 (10)	0.0226 (10)
H23A	−0.203092	−0.073638	0.398589	0.027*
H23B	−0.072385	0.047980	0.389813	0.027*
C24	−0.1336 (6)	0.0495 (4)	0.43646 (9)	0.0178 (9)
H24	−0.105272	0.148108	0.438400	0.021*
C25	0.0415 (6)	−0.0272 (5)	0.44742 (9)	0.0205 (9)
H25A	0.021412	−0.125985	0.445763	0.025*
H25B	0.140215	−0.002754	0.433839	0.025*
C26	0.0941 (6)	0.0099 (5)	0.48101 (9)	0.0197 (9)
H26A	0.197261	−0.047030	0.488251	0.024*
H26B	0.134259	0.105378	0.481719	0.024*
C27	−0.0562 (6)	−0.0078 (4)	0.50315 (9)	0.0160 (8)
H27	−0.084281	−0.106458	0.504619	0.019*
C28	−0.2312 (6)	0.0683 (4)	0.49122 (9)	0.0157 (8)
H28	−0.196929	0.165866	0.489691	0.019*
C29	−0.2888 (6)	0.0234 (4)	0.45754 (9)	0.0156 (8)
C30	−0.3775 (6)	0.0624 (5)	0.51479 (9)	0.0179 (9)
H30A	−0.421792	−0.031818	0.516116	0.022*
H30B	−0.479719	0.119816	0.507344	0.022*
C31	−0.3120 (6)	0.1099 (5)	0.54762 (9)	0.0200 (9)
H31A	−0.280468	0.207172	0.546903	0.024*
H31B	−0.410335	0.098976	0.562125	0.024*
C32	−0.1497 (6)	0.0298 (4)	0.55949 (9)	0.0179 (9)
C33	−0.0019 (6)	0.0438 (4)	0.53568 (9)	0.0182 (9)
H33	0.020066	0.143071	0.533438	0.022*
C34	0.1657 (6)	−0.0134 (5)	0.55255 (10)	0.0210 (9)
H34A	0.276031	0.024297	0.543925	0.025*
H34B	0.168808	−0.113268	0.550858	0.025*
C35	0.1483 (7)	0.0313 (5)	0.58687 (10)	0.0255 (10)
H35A	0.236460	0.103397	0.592469	0.031*
H35B	0.169653	−0.046174	0.601166	0.031*
C36	−0.0472 (6)	0.0850 (5)	0.58888 (9)	0.0205 (9)
H36A	−0.101748	0.051406	0.607960	0.025*
H36B	−0.048884	0.185124	0.589061	0.025*
C37	−0.3478 (6)	−0.1268 (4)	0.45731 (9)	0.0197 (9)
H37A	−0.368464	−0.157338	0.435752	0.030*
H37B	−0.459117	−0.136103	0.468404	0.030*
H37C	−0.253134	−0.181951	0.467620	0.030*
C38	−0.2011 (7)	−0.1177 (5)	0.56571 (10)	0.0235 (10)
H38A	−0.300969	−0.120135	0.579743	0.035*
H38B	−0.097274	−0.165434	0.575360	0.035*
H38C	−0.237743	−0.161816	0.546005	0.035*
C39	0.6365 (7)	0.2470 (5)	0.69536 (10)	0.0233 (10)
H39A	0.731389	0.299791	0.706825	0.028*
H39B	0.664819	0.149889	0.698326	0.028*
C40	0.6407 (7)	0.2810 (5)	0.66050 (10)	0.0272 (10)
H40A	0.630497	0.380187	0.657699	0.033*
H40B	0.757415	0.252034	0.652613	0.033*
C41	0.4873 (7)	0.2112 (5)	0.64152 (9)	0.0260 (10)
H41A	0.485956	0.243588	0.619727	0.031*
H41B	0.508598	0.112295	0.641404	0.031*
C42	0.3050 (7)	0.2402 (5)	0.65512 (9)	0.0243 (10)
H42A	0.210060	0.188004	0.643523	0.029*
H42B	0.276303	0.337599	0.652780	0.029*
C43	0.3076 (6)	0.2015 (4)	0.68963 (9)	0.0185 (9)
H43	0.339828	0.103372	0.690830	0.022*
C44	0.1207 (6)	0.2148 (5)	0.70262 (9)	0.0221 (9)
H44A	0.082251	0.310674	0.701630	0.027*
H44B	0.033382	0.161037	0.689657	0.027*
C45	0.1205 (6)	0.1657 (4)	0.73621 (9)	0.0185 (8)
H45A	0.141402	0.066741	0.736696	0.022*
H45B	0.000775	0.182978	0.744492	0.022*
C46	0.2643 (6)	0.2353 (4)	0.75715 (9)	0.0149 (8)
H46	0.234116	0.333635	0.758478	0.018*
C47	0.4521 (6)	0.2211 (5)	0.74321 (9)	0.0181 (9)
H47	0.475188	0.121789	0.741543	0.022*
C48	0.4528 (6)	0.2775 (4)	0.70952 (9)	0.0175 (8)
C49	0.6021 (6)	0.2773 (5)	0.76537 (10)	0.0250 (10)
H49A	0.591348	0.377073	0.766124	0.030*
H49B	0.719950	0.255387	0.756896	0.030*
C50	0.5977 (6)	0.2212 (5)	0.79871 (10)	0.0252 (10)
H50A	0.626072	0.123390	0.798592	0.030*
H50B	0.690515	0.267346	0.812146	0.030*
C51	0.4145 (7)	0.2424 (4)	0.81191 (9)	0.0209 (9)
C52	0.2699 (6)	0.1756 (4)	0.78997 (9)	0.0177 (8)
H52	0.306190	0.078751	0.787866	0.021*
C53	0.1014 (7)	0.1757 (5)	0.80849 (10)	0.0232 (10)
H53A	0.020117	0.100762	0.801832	0.028*
H53B	0.035833	0.262460	0.805895	0.028*
C54	0.1721 (8)	0.1563 (5)	0.84273 (10)	0.0300 (11)
H54A	0.123537	0.227434	0.856203	0.036*
H54B	0.135994	0.066780	0.850636	0.036*
C55	0.3794 (7)	0.1669 (5)	0.84232 (10)	0.0259 (10)
H55A	0.428477	0.218031	0.860605	0.031*
H55B	0.434957	0.075834	0.842387	0.031*
C56	0.4224 (7)	0.4317 (4)	0.70900 (10)	0.0228 (9)
H56A	0.522944	0.476686	0.720363	0.034*
H56B	0.309970	0.453007	0.718913	0.034*
H56C	0.415108	0.463644	0.687398	0.034*
C57	0.3797 (7)	0.3943 (5)	0.81721 (9)	0.0239 (10)
H57A	0.377414	0.441879	0.797196	0.036*
H57B	0.475817	0.431649	0.831029	0.036*
H57C	0.263762	0.405883	0.826762	0.036*
C58	0.0786 (6)	0.8877 (5)	1.05343 (9)	0.0183 (8)
H58A	−0.034470	0.906386	1.041108	0.022*
H58B	0.109236	0.791197	1.050439	0.022*
C59	0.0479 (7)	0.9126 (5)	1.08796 (9)	0.0225 (10)
H59A	0.005323	1.006500	1.090728	0.027*
H59B	−0.046793	0.850521	1.094826	0.027*
C60	0.2197 (7)	0.8904 (5)	1.10815 (9)	0.0239 (9)
H60A	0.197345	0.914331	1.129992	0.029*
H60B	0.253520	0.793617	1.107578	0.029*
C61	0.3743 (7)	0.9760 (5)	1.09693 (9)	0.0239 (10)
H61A	0.486011	0.953485	1.109267	0.029*
H61B	0.347704	1.072965	1.100219	0.029*
C62	0.4028 (6)	0.9511 (4)	1.06234 (9)	0.0177 (9)
H62	0.431783	0.852745	1.060319	0.021*
C63	0.5643 (6)	1.0279 (5)	1.05121 (9)	0.0186 (9)
H63A	0.670434	1.007890	1.065210	0.022*
H63B	0.540318	1.126249	1.052291	0.022*
C64	0.6062 (7)	0.9901 (5)	1.01788 (9)	0.0211 (9)
H64A	0.705044	1.048120	1.010937	0.025*
H64B	0.647399	0.894960	1.017384	0.025*
C65	0.4423 (6)	1.0070 (4)	0.99550 (9)	0.0154 (8)
H65	0.412822	1.105601	0.993912	0.018*
C66	0.2773 (6)	0.9320 (4)	1.00757 (9)	0.0171 (9)
H66	0.312722	0.834564	1.009233	0.020*
C67	0.2305 (6)	0.9766 (4)	1.04105 (9)	0.0149 (8)
C68	0.1146 (6)	0.9374 (5)	0.98373 (9)	0.0175 (9)
H68A	0.017050	0.879613	0.991256	0.021*
H68B	0.068922	1.031415	0.982397	0.021*
C69	0.1616 (6)	0.8900 (5)	0.95102 (9)	0.0189 (9)
H69A	0.192217	0.792484	0.951709	0.023*
H69B	0.055488	0.901719	0.936496	0.023*
C70	0.3187 (6)	0.9688 (4)	0.93907 (9)	0.0162 (8)
C71	0.4774 (6)	0.9547 (4)	0.96312 (9)	0.0161 (8)
H71	0.498854	0.855260	0.965538	0.019*
C72	0.6400 (6)	1.0101 (5)	0.94636 (9)	0.0182 (9)
H72A	0.753917	0.971203	0.955216	0.022*
H72B	0.646169	1.109970	0.947840	0.022*
C73	0.6032 (7)	0.9640 (5)	0.91226 (9)	0.0245 (10)
H73A	0.686896	0.890655	0.906921	0.029*
H73B	0.618746	1.040571	0.897781	0.029*
C74	0.4042 (7)	0.9122 (4)	0.91003 (9)	0.0208 (9)
H74A	0.340555	0.946124	0.890843	0.025*
H74B	0.400410	0.812109	0.909952	0.025*
C75	0.1725 (6)	1.1254 (4)	1.04120 (9)	0.0191 (9)
H75A	0.261536	1.180403	1.030860	0.029*
H75B	0.163748	1.156237	1.062739	0.029*
H75C	0.055029	1.134793	1.030096	0.029*
C76	0.2670 (7)	1.1172 (4)	0.93268 (9)	0.0220 (9)
H76A	0.159642	1.120717	0.918600	0.033*
H76B	0.366675	1.163536	0.923039	0.033*
H76C	0.241919	1.162038	0.952336	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.014 (2)	0.022 (2)	0.0242 (19)	−0.0018 (18)	0.0021 (17)	−0.0019 (16)
C2	0.021 (2)	0.028 (2)	0.0227 (19)	0.001 (2)	−0.0026 (18)	−0.0012 (17)
C3	0.029 (3)	0.024 (2)	0.0195 (19)	−0.001 (2)	0.0017 (18)	−0.0015 (16)
C4	0.016 (2)	0.020 (2)	0.0243 (19)	0.0008 (19)	0.0050 (17)	−0.0017 (16)
C5	0.016 (2)	0.016 (2)	0.0238 (19)	−0.0006 (18)	0.0026 (18)	−0.0008 (15)
C6	0.016 (2)	0.024 (2)	0.027 (2)	0.001 (2)	0.0044 (18)	0.0016 (17)
C7	0.016 (2)	0.027 (2)	0.0233 (19)	0.004 (2)	0.0015 (17)	0.0016 (17)
C8	0.020 (2)	0.015 (2)	0.0205 (18)	0.0003 (18)	0.0009 (18)	0.0001 (15)
C9	0.008 (2)	0.0150 (19)	0.0234 (18)	−0.0033 (17)	0.0026 (15)	−0.0031 (15)
C10	0.017 (2)	0.015 (2)	0.0211 (18)	0.0020 (18)	0.0007 (17)	0.0001 (15)
C11	0.017 (2)	0.024 (2)	0.0241 (19)	0.0046 (19)	0.0016 (18)	0.0004 (17)
C12	0.022 (2)	0.021 (2)	0.029 (2)	0.002 (2)	0.0106 (19)	−0.0013 (18)
C13	0.025 (2)	0.017 (2)	0.0210 (19)	−0.001 (2)	0.0048 (18)	−0.0007 (16)
C14	0.020 (2)	0.016 (2)	0.0210 (18)	−0.0026 (18)	0.0023 (18)	−0.0012 (15)
C15	0.026 (3)	0.025 (2)	0.0227 (19)	0.001 (2)	0.0002 (19)	0.0019 (17)
C16	0.024 (3)	0.039 (3)	0.027 (2)	0.004 (2)	0.002 (2)	0.0053 (19)
C17	0.030 (3)	0.025 (2)	0.025 (2)	0.001 (2)	0.005 (2)	0.0017 (17)
C18	0.015 (2)	0.016 (2)	0.0244 (19)	0.0016 (17)	0.0002 (16)	−0.0014 (15)
C19	0.029 (3)	0.019 (2)	0.028 (2)	0.000 (2)	0.0044 (19)	−0.0046 (17)
C20	0.022 (2)	0.018 (2)	0.025 (2)	0.0012 (19)	0.0019 (18)	−0.0018 (17)
C21	0.017 (2)	0.025 (2)	0.029 (2)	0.003 (2)	−0.0013 (19)	0.0001 (17)
C22	0.034 (3)	0.030 (2)	0.0202 (19)	0.003 (2)	−0.0012 (19)	0.0016 (18)
C23	0.018 (2)	0.026 (2)	0.024 (2)	0.002 (2)	0.0046 (18)	−0.0012 (17)
C24	0.013 (2)	0.016 (2)	0.0245 (19)	−0.0026 (18)	0.0035 (17)	−0.0005 (16)
C25	0.015 (2)	0.022 (2)	0.025 (2)	0.0014 (19)	0.0046 (18)	−0.0035 (17)
C26	0.009 (2)	0.023 (2)	0.028 (2)	−0.0014 (18)	0.0041 (17)	−0.0007 (16)
C27	0.010 (2)	0.018 (2)	0.0206 (18)	0.0009 (17)	0.0025 (16)	−0.0008 (15)
C28	0.011 (2)	0.015 (2)	0.0211 (18)	0.0021 (17)	0.0021 (16)	−0.0002 (15)
C29	0.009 (2)	0.013 (2)	0.0242 (19)	−0.0019 (17)	0.0014 (16)	−0.0004 (15)
C30	0.0070 (19)	0.022 (2)	0.0248 (19)	−0.0012 (18)	0.0042 (16)	−0.0016 (16)
C31	0.018 (2)	0.020 (2)	0.0215 (19)	−0.0011 (19)	0.0047 (17)	−0.0021 (16)
C32	0.016 (2)	0.015 (2)	0.0233 (18)	−0.0051 (18)	0.0049 (17)	0.0002 (16)
C33	0.018 (2)	0.014 (2)	0.0236 (19)	−0.0037 (18)	0.0056 (18)	−0.0005 (15)
C34	0.012 (2)	0.025 (2)	0.026 (2)	−0.0003 (19)	−0.0001 (17)	0.0016 (17)
C35	0.018 (2)	0.036 (3)	0.022 (2)	0.000 (2)	0.0000 (18)	0.0010 (18)
C36	0.017 (2)	0.023 (2)	0.0212 (18)	−0.0028 (19)	0.0010 (17)	−0.0014 (16)
C37	0.019 (2)	0.017 (2)	0.0234 (18)	−0.0036 (19)	0.0002 (17)	−0.0011 (15)
C38	0.024 (3)	0.021 (2)	0.027 (2)	−0.004 (2)	0.0067 (18)	0.0014 (17)
C39	0.021 (2)	0.023 (2)	0.025 (2)	−0.001 (2)	−0.0005 (18)	−0.0005 (17)
C40	0.021 (2)	0.035 (3)	0.025 (2)	−0.003 (2)	0.0055 (19)	0.0012 (19)
C41	0.027 (3)	0.032 (3)	0.0196 (18)	0.002 (2)	0.0044 (18)	−0.0030 (18)
C42	0.022 (2)	0.031 (3)	0.0198 (19)	0.001 (2)	0.0012 (18)	−0.0023 (17)
C43	0.018 (2)	0.016 (2)	0.0214 (19)	0.0039 (18)	0.0001 (17)	−0.0020 (15)
C44	0.020 (2)	0.022 (2)	0.025 (2)	0.0005 (19)	−0.0010 (19)	−0.0020 (17)
C45	0.0054 (19)	0.023 (2)	0.027 (2)	0.0013 (18)	0.0014 (16)	−0.0028 (17)
C46	0.0090 (19)	0.016 (2)	0.0203 (17)	0.0027 (16)	0.0028 (15)	−0.0009 (15)
C47	0.015 (2)	0.020 (2)	0.0200 (18)	0.0009 (18)	0.0014 (16)	−0.0028 (16)
C48	0.013 (2)	0.019 (2)	0.0214 (18)	0.0006 (18)	0.0023 (16)	0.0000 (16)
C49	0.012 (2)	0.037 (3)	0.025 (2)	−0.006 (2)	−0.0010 (18)	−0.0064 (19)
C50	0.016 (2)	0.035 (3)	0.023 (2)	0.002 (2)	−0.0046 (18)	−0.0025 (19)
C51	0.027 (3)	0.018 (2)	0.0176 (18)	0.004 (2)	−0.0012 (17)	−0.0001 (16)
C52	0.015 (2)	0.014 (2)	0.0237 (18)	0.0007 (17)	0.0013 (17)	0.0013 (15)
C53	0.022 (2)	0.020 (2)	0.027 (2)	0.000 (2)	0.0037 (19)	0.0014 (17)
C54	0.037 (3)	0.029 (3)	0.024 (2)	−0.006 (2)	0.004 (2)	0.0028 (18)
C55	0.027 (3)	0.027 (3)	0.023 (2)	0.004 (2)	0.0006 (19)	0.0040 (18)
C56	0.022 (2)	0.019 (2)	0.027 (2)	−0.0013 (19)	0.0029 (18)	−0.0017 (16)
C57	0.026 (2)	0.022 (2)	0.0241 (19)	−0.001 (2)	0.0012 (18)	−0.0039 (17)
C58	0.016 (2)	0.017 (2)	0.0219 (18)	−0.0008 (18)	−0.0001 (17)	0.0003 (16)
C59	0.023 (3)	0.021 (2)	0.0231 (19)	−0.001 (2)	−0.0007 (19)	0.0022 (16)
C60	0.022 (2)	0.030 (2)	0.0202 (18)	0.000 (2)	0.0016 (18)	0.0031 (17)
C61	0.030 (3)	0.025 (2)	0.0167 (18)	−0.003 (2)	−0.0028 (18)	0.0012 (16)
C62	0.018 (2)	0.014 (2)	0.0215 (19)	0.0036 (18)	−0.0002 (17)	−0.0014 (15)
C63	0.011 (2)	0.024 (2)	0.0208 (19)	0.0011 (18)	−0.0049 (16)	−0.0009 (16)
C64	0.023 (2)	0.018 (2)	0.0211 (19)	0.000 (2)	−0.0033 (18)	0.0000 (15)
C65	0.013 (2)	0.014 (2)	0.0183 (17)	−0.0004 (17)	−0.0001 (16)	−0.0019 (15)
C66	0.023 (2)	0.012 (2)	0.0156 (17)	−0.0002 (18)	−0.0014 (17)	0.0003 (14)
C67	0.011 (2)	0.014 (2)	0.0196 (17)	−0.0011 (17)	−0.0007 (16)	0.0005 (15)
C68	0.0078 (19)	0.022 (2)	0.0230 (19)	−0.0021 (18)	0.0008 (16)	−0.0008 (16)
C69	0.018 (2)	0.020 (2)	0.0187 (17)	−0.0041 (19)	−0.0014 (16)	−0.0027 (16)
C70	0.014 (2)	0.017 (2)	0.0181 (17)	0.0002 (17)	0.0012 (16)	0.0002 (15)
C71	0.012 (2)	0.016 (2)	0.0196 (18)	0.0016 (17)	0.0014 (16)	−0.0008 (15)
C72	0.008 (2)	0.023 (2)	0.0234 (19)	−0.0002 (18)	0.0028 (16)	0.0000 (16)
C73	0.022 (2)	0.031 (3)	0.0207 (19)	0.003 (2)	0.0044 (18)	0.0028 (18)
C74	0.027 (3)	0.017 (2)	0.0185 (18)	0.0041 (19)	−0.0004 (18)	0.0001 (15)
C75	0.022 (2)	0.015 (2)	0.0204 (18)	0.0056 (18)	0.0019 (17)	−0.0008 (15)
C76	0.027 (3)	0.017 (2)	0.0219 (18)	0.0009 (19)	0.0015 (19)	0.0027 (16)

Geometric parameters (Å, º) top

C1—C2	1.532 (6)	C39—C40	1.538 (6)
C1—C10	1.534 (6)	C39—C48	1.552 (6)
C1—H1A	0.9900	C39—H39A	0.9900
C1—H1B	0.9900	C39—H39B	0.9900
C2—C3	1.532 (6)	C40—C41	1.535 (7)
C2—H2A	0.9900	C40—H40A	0.9900
C2—H2B	0.9900	C40—H40B	0.9900
C3—C4	1.527 (6)	C41—C42	1.531 (6)
C3—H3A	0.9900	C41—H41A	0.9900
C3—H3B	0.9900	C41—H41B	0.9900
C4—C5	1.536 (5)	C42—C43	1.531 (5)
C4—H4A	0.9900	C42—H42A	0.9900
C4—H4B	0.9900	C42—H42B	0.9900
C5—C6	1.519 (6)	C43—C44	1.530 (6)
C5—C10	1.551 (6)	C43—C48	1.540 (6)
C5—H5	1.0000	C43—H43	1.0000
C6—C7	1.529 (5)	C44—C45	1.524 (5)
C6—H6A	0.9900	C44—H44A	0.9900
C6—H6B	0.9900	C44—H44B	0.9900
C7—C8	1.529 (6)	C45—C46	1.529 (6)
C7—H7A	0.9900	C45—H45A	0.9900
C7—H7B	0.9900	C45—H45B	0.9900
C8—C14	1.523 (5)	C46—C52	1.528 (5)
C8—C9	1.544 (5)	C46—C47	1.553 (6)
C8—H8	1.0000	C46—H46	1.0000
C9—C11	1.534 (6)	C47—C49	1.536 (6)
C9—C10	1.561 (5)	C47—C48	1.552 (5)
C9—H9	1.0000	C47—H47	1.0000
C10—C18	1.547 (6)	C48—C56	1.541 (6)
C11—C12	1.543 (6)	C49—C50	1.539 (6)
C11—H11A	0.9900	C49—H49A	0.9900
C11—H11B	0.9900	C49—H49B	0.9900
C12—C13	1.517 (6)	C50—C51	1.516 (7)
C12—H12A	0.9900	C50—H50A	0.9900
C12—H12B	0.9900	C50—H50B	0.9900
C13—C17	1.534 (6)	C51—C55	1.539 (6)
C13—C14	1.541 (6)	C51—C57	1.542 (6)
C13—C19	1.541 (6)	C51—C52	1.545 (6)
C14—C15	1.533 (6)	C52—C53	1.517 (6)
C14—H14	1.0000	C52—H52	1.0000
C15—C16	1.556 (6)	C53—C54	1.551 (6)
C15—H15A	0.9900	C53—H53A	0.9900
C15—H15B	0.9900	C53—H53B	0.9900
C16—C17	1.564 (7)	C54—C55	1.547 (7)
C16—H16A	0.9900	C54—H54A	0.9900
C16—H16B	0.9900	C54—H54B	0.9900
C17—H17A	0.9900	C55—H55A	0.9900
C17—H17B	0.9900	C55—H55B	0.9900
C18—H18A	0.9800	C56—H56A	0.9800
C18—H18B	0.9800	C56—H56B	0.9800
C18—H18C	0.9800	C56—H56C	0.9800
C19—H19A	0.9800	C57—H57A	0.9800
C19—H19B	0.9800	C57—H57B	0.9800
C19—H19C	0.9800	C57—H57C	0.9800
C20—C21	1.540 (6)	C58—C59	1.533 (5)
C20—C29	1.554 (6)	C58—C67	1.546 (6)
C20—H20A	0.9900	C58—H58A	0.9900
C20—H20B	0.9900	C58—H58B	0.9900
C21—C22	1.517 (7)	C59—C60	1.526 (6)
C21—H21A	0.9900	C59—H59A	0.9900
C21—H21B	0.9900	C59—H59B	0.9900
C22—C23	1.538 (7)	C60—C61	1.525 (7)
C22—H22A	0.9900	C60—H60A	0.9900
C22—H22B	0.9900	C60—H60B	0.9900
C23—C24	1.526 (5)	C61—C62	1.532 (5)
C23—H23A	0.9900	C61—H61A	0.9900
C23—H23B	0.9900	C61—H61B	0.9900
C24—C29	1.523 (6)	C62—C63	1.518 (6)
C24—C25	1.560 (6)	C62—C67	1.560 (6)
C24—H24	1.0000	C62—H62	1.0000
C25—C26	1.523 (6)	C63—C64	1.527 (5)
C25—H25A	0.9900	C63—H63A	0.9900
C25—H25B	0.9900	C63—H63B	0.9900
C26—C27	1.513 (6)	C64—C65	1.526 (6)
C26—H26A	0.9900	C64—H64A	0.9900
C26—H26B	0.9900	C64—H64B	0.9900
C27—C33	1.525 (5)	C65—C71	1.520 (5)
C27—C28	1.569 (6)	C65—C66	1.545 (6)
C27—H27	1.0000	C65—H65	1.0000
C28—C30	1.524 (5)	C66—C68	1.550 (6)
C28—C29	1.555 (5)	C66—C67	1.561 (5)
C28—H28	1.0000	C66—H66	1.0000
C29—C37	1.548 (6)	C67—C75	1.533 (6)
C30—C31	1.544 (5)	C68—C69	1.539 (5)
C30—H30A	0.9900	C68—H68A	0.9900
C30—H30B	0.9900	C68—H68B	0.9900
C31—C32	1.513 (6)	C69—C70	1.515 (6)
C31—H31A	0.9900	C69—H69A	0.9900
C31—H31B	0.9900	C69—H69B	0.9900
C32—C38	1.534 (6)	C70—C74	1.534 (6)
C32—C36	1.544 (6)	C70—C76	1.538 (6)
C32—C33	1.544 (6)	C70—C71	1.538 (6)
C33—C34	1.521 (6)	C71—C72	1.539 (6)
C33—H33	1.0000	C71—H71	1.0000
C34—C35	1.552 (6)	C72—C73	1.548 (5)
C34—H34A	0.9900	C72—H72A	0.9900
C34—H34B	0.9900	C72—H72B	0.9900
C35—C36	1.555 (6)	C73—C74	1.565 (7)
C35—H35A	0.9900	C73—H73A	0.9900
C35—H35B	0.9900	C73—H73B	0.9900
C36—H36A	0.9900	C74—H74A	0.9900
C36—H36B	0.9900	C74—H74B	0.9900
C37—H37A	0.9800	C75—H75A	0.9800
C37—H37B	0.9800	C75—H75B	0.9800
C37—H37C	0.9800	C75—H75C	0.9800
C38—H38A	0.9800	C76—H76A	0.9800
C38—H38B	0.9800	C76—H76B	0.9800
C38—H38C	0.9800	C76—H76C	0.9800

C2—C1—C10	113.3 (4)	C40—C39—C48	113.5 (4)
C2—C1—H1A	108.9	C40—C39—H39A	108.9
C10—C1—H1A	108.9	C48—C39—H39A	108.9
C2—C1—H1B	108.9	C40—C39—H39B	108.9
C10—C1—H1B	108.9	C48—C39—H39B	108.9
H1A—C1—H1B	107.7	H39A—C39—H39B	107.7
C3—C2—C1	111.8 (4)	C41—C40—C39	111.8 (4)
C3—C2—H2A	109.2	C41—C40—H40A	109.3
C1—C2—H2A	109.2	C39—C40—H40A	109.3
C3—C2—H2B	109.2	C41—C40—H40B	109.3
C1—C2—H2B	109.2	C39—C40—H40B	109.3
H2A—C2—H2B	107.9	H40A—C40—H40B	107.9
C4—C3—C2	111.5 (3)	C42—C41—C40	111.3 (4)
C4—C3—H3A	109.3	C42—C41—H41A	109.4
C2—C3—H3A	109.3	C40—C41—H41A	109.4
C4—C3—H3B	109.3	C42—C41—H41B	109.4
C2—C3—H3B	109.3	C40—C41—H41B	109.4
H3A—C3—H3B	108.0	H41A—C41—H41B	108.0
C3—C4—C5	111.4 (4)	C41—C42—C43	110.7 (4)
C3—C4—H4A	109.4	C41—C42—H42A	109.5
C5—C4—H4A	109.4	C43—C42—H42A	109.5
C3—C4—H4B	109.4	C41—C42—H42B	109.5
C5—C4—H4B	109.4	C43—C42—H42B	109.5
H4A—C4—H4B	108.0	H42A—C42—H42B	108.1
C6—C5—C4	111.9 (4)	C44—C43—C42	111.2 (4)
C6—C5—C10	113.0 (3)	C44—C43—C48	112.4 (3)
C4—C5—C10	112.3 (3)	C42—C43—C48	113.1 (4)
C6—C5—H5	106.4	C44—C43—H43	106.5
C4—C5—H5	106.4	C42—C43—H43	106.5
C10—C5—H5	106.4	C48—C43—H43	106.5
C5—C6—C7	111.0 (4)	C45—C44—C43	111.1 (4)
C5—C6—H6A	109.4	C45—C44—H44A	109.4
C7—C6—H6A	109.4	C43—C44—H44A	109.4
C5—C6—H6B	109.4	C45—C44—H44B	109.4
C7—C6—H6B	109.4	C43—C44—H44B	109.4
H6A—C6—H6B	108.0	H44A—C44—H44B	108.0
C6—C7—C8	111.9 (4)	C44—C45—C46	112.5 (4)
C6—C7—H7A	109.2	C44—C45—H45A	109.1
C8—C7—H7A	109.2	C46—C45—H45A	109.1
C6—C7—H7B	109.2	C44—C45—H45B	109.1
C8—C7—H7B	109.2	C46—C45—H45B	109.1
H7A—C7—H7B	107.9	H45A—C45—H45B	107.8
C14—C8—C7	111.0 (4)	C52—C46—C45	111.0 (4)
C14—C8—C9	109.4 (4)	C52—C46—C47	109.6 (3)
C7—C8—C9	110.8 (3)	C45—C46—C47	110.5 (3)
C14—C8—H8	108.5	C52—C46—H46	108.6
C7—C8—H8	108.5	C45—C46—H46	108.6
C9—C8—H8	108.5	C47—C46—H46	108.6
C11—C9—C8	111.6 (3)	C49—C47—C48	114.5 (4)
C11—C9—C10	113.7 (3)	C49—C47—C46	111.6 (3)
C8—C9—C10	112.6 (3)	C48—C47—C46	111.8 (3)
C11—C9—H9	106.1	C49—C47—H47	106.1
C8—C9—H9	106.1	C48—C47—H47	106.1
C10—C9—H9	106.1	C46—C47—H47	106.1
C1—C10—C18	109.4 (3)	C43—C48—C56	112.1 (4)
C1—C10—C5	107.9 (3)	C43—C48—C47	108.1 (3)
C18—C10—C5	111.3 (4)	C56—C48—C47	111.2 (3)
C1—C10—C9	110.6 (4)	C43—C48—C39	107.2 (3)
C18—C10—C9	110.1 (3)	C56—C48—C39	108.5 (4)
C5—C10—C9	107.5 (3)	C47—C48—C39	109.8 (4)
C9—C11—C12	113.2 (4)	C47—C49—C50	113.6 (4)
C9—C11—H11A	108.9	C47—C49—H49A	108.8
C12—C11—H11A	108.9	C50—C49—H49A	108.8
C9—C11—H11B	108.9	C47—C49—H49B	108.8
C12—C11—H11B	108.9	C50—C49—H49B	108.8
H11A—C11—H11B	107.7	H49A—C49—H49B	107.7
C13—C12—C11	111.5 (4)	C51—C50—C49	111.0 (4)
C13—C12—H12A	109.3	C51—C50—H50A	109.4
C11—C12—H12A	109.3	C49—C50—H50A	109.4
C13—C12—H12B	109.3	C51—C50—H50B	109.4
C11—C12—H12B	109.3	C49—C50—H50B	109.4
H12A—C12—H12B	108.0	H50A—C50—H50B	108.0
C12—C13—C17	116.1 (4)	C50—C51—C55	116.3 (4)
C12—C13—C14	108.4 (3)	C50—C51—C57	110.5 (4)
C17—C13—C14	100.4 (4)	C55—C51—C57	108.1 (4)
C12—C13—C19	110.2 (4)	C50—C51—C52	109.0 (3)
C17—C13—C19	108.6 (4)	C55—C51—C52	99.8 (4)
C14—C13—C19	113.0 (4)	C57—C51—C52	112.9 (4)
C8—C14—C15	119.1 (4)	C53—C52—C46	119.8 (4)
C8—C14—C13	113.6 (4)	C53—C52—C51	104.4 (3)
C15—C14—C13	104.1 (3)	C46—C52—C51	112.7 (4)
C8—C14—H14	106.4	C53—C52—H52	106.3
C15—C14—H14	106.4	C46—C52—H52	106.3
C13—C14—H14	106.4	C51—C52—H52	106.3
C14—C15—C16	103.0 (4)	C52—C53—C54	104.3 (4)
C14—C15—H15A	111.2	C52—C53—H53A	110.9
C16—C15—H15A	111.2	C54—C53—H53A	110.9
C14—C15—H15B	111.2	C52—C53—H53B	110.9
C16—C15—H15B	111.2	C54—C53—H53B	110.9
H15A—C15—H15B	109.1	H53A—C53—H53B	108.9
C15—C16—C17	106.4 (4)	C55—C54—C53	105.9 (4)
C15—C16—H16A	110.4	C55—C54—H54A	110.6
C17—C16—H16A	110.4	C53—C54—H54A	110.6
C15—C16—H16B	110.4	C55—C54—H54B	110.6
C17—C16—H16B	110.4	C53—C54—H54B	110.6
H16A—C16—H16B	108.6	H54A—C54—H54B	108.7
C13—C17—C16	104.3 (4)	C51—C55—C54	104.6 (4)
C13—C17—H17A	110.9	C51—C55—H55A	110.8
C16—C17—H17A	110.9	C54—C55—H55A	110.8
C13—C17—H17B	110.9	C51—C55—H55B	110.8
C16—C17—H17B	110.9	C54—C55—H55B	110.8
H17A—C17—H17B	108.9	H55A—C55—H55B	108.9
C10—C18—H18A	109.5	C48—C56—H56A	109.5
C10—C18—H18B	109.5	C48—C56—H56B	109.5
H18A—C18—H18B	109.5	H56A—C56—H56B	109.5
C10—C18—H18C	109.5	C48—C56—H56C	109.5
H18A—C18—H18C	109.5	H56A—C56—H56C	109.5
H18B—C18—H18C	109.5	H56B—C56—H56C	109.5
C13—C19—H19A	109.5	C51—C57—H57A	109.5
C13—C19—H19B	109.5	C51—C57—H57B	109.5
H19A—C19—H19B	109.5	H57A—C57—H57B	109.5
C13—C19—H19C	109.5	C51—C57—H57C	109.5
H19A—C19—H19C	109.5	H57A—C57—H57C	109.5
H19B—C19—H19C	109.5	H57B—C57—H57C	109.5
C21—C20—C29	112.8 (4)	C59—C58—C67	112.8 (4)
C21—C20—H20A	109.0	C59—C58—H58A	109.0
C29—C20—H20A	109.0	C67—C58—H58A	109.0
C21—C20—H20B	109.0	C59—C58—H58B	109.0
C29—C20—H20B	109.0	C67—C58—H58B	109.0
H20A—C20—H20B	107.8	H58A—C58—H58B	107.8
C22—C21—C20	112.0 (4)	C60—C59—C58	111.6 (4)
C22—C21—H21A	109.2	C60—C59—H59A	109.3
C20—C21—H21A	109.2	C58—C59—H59A	109.3
C22—C21—H21B	109.2	C60—C59—H59B	109.3
C20—C21—H21B	109.2	C58—C59—H59B	109.3
H21A—C21—H21B	107.9	H59A—C59—H59B	108.0
C21—C22—C23	111.5 (4)	C61—C60—C59	111.4 (4)
C21—C22—H22A	109.3	C61—C60—H60A	109.4
C23—C22—H22A	109.3	C59—C60—H60A	109.4
C21—C22—H22B	109.3	C61—C60—H60B	109.4
C23—C22—H22B	109.3	C59—C60—H60B	109.4
H22A—C22—H22B	108.0	H60A—C60—H60B	108.0
C24—C23—C22	110.7 (4)	C60—C61—C62	111.1 (4)
C24—C23—H23A	109.5	C60—C61—H61A	109.4
C22—C23—H23A	109.5	C62—C61—H61A	109.4
C24—C23—H23B	109.5	C60—C61—H61B	109.4
C22—C23—H23B	109.5	C62—C61—H61B	109.4
H23A—C23—H23B	108.1	H61A—C61—H61B	108.0
C29—C24—C23	114.7 (4)	C63—C62—C61	112.0 (4)
C29—C24—C25	112.6 (3)	C63—C62—C67	112.0 (3)
C23—C24—C25	110.5 (4)	C61—C62—C67	113.3 (4)
C29—C24—H24	106.1	C63—C62—H62	106.3
C23—C24—H24	106.1	C61—C62—H62	106.3
C25—C24—H24	106.1	C67—C62—H62	106.3
C26—C25—C24	110.0 (3)	C62—C63—C64	112.0 (4)
C26—C25—H25A	109.7	C62—C63—H63A	109.2
C24—C25—H25A	109.7	C64—C63—H63A	109.2
C26—C25—H25B	109.7	C62—C63—H63B	109.2
C24—C25—H25B	109.7	C64—C63—H63B	109.2
H25A—C25—H25B	108.2	H63A—C63—H63B	107.9
C27—C26—C25	113.9 (4)	C65—C64—C63	111.8 (4)
C27—C26—H26A	108.8	C65—C64—H64A	109.2
C25—C26—H26A	108.8	C63—C64—H64A	109.2
C27—C26—H26B	108.8	C65—C64—H64B	109.2
C25—C26—H26B	108.8	C63—C64—H64B	109.2
H26A—C26—H26B	107.7	H64A—C64—H64B	107.9
C26—C27—C33	111.5 (4)	C71—C65—C64	111.9 (4)
C26—C27—C28	111.4 (3)	C71—C65—C66	108.6 (3)
C33—C27—C28	108.6 (3)	C64—C65—C66	111.1 (3)
C26—C27—H27	108.4	C71—C65—H65	108.4
C33—C27—H27	108.4	C64—C65—H65	108.4
C28—C27—H27	108.4	C66—C65—H65	108.4
C30—C28—C29	115.7 (4)	C65—C66—C68	111.7 (3)
C30—C28—C27	111.9 (3)	C65—C66—C67	113.0 (3)
C29—C28—C27	110.8 (3)	C68—C66—C67	113.5 (4)
C30—C28—H28	105.9	C65—C66—H66	106.0
C29—C28—H28	105.9	C68—C66—H66	106.0
C27—C28—H28	105.9	C67—C66—H66	106.0
C24—C29—C37	112.4 (3)	C75—C67—C58	109.5 (4)
C24—C29—C20	107.7 (3)	C75—C67—C62	112.1 (3)
C37—C29—C20	108.1 (4)	C58—C67—C62	107.5 (3)
C24—C29—C28	108.8 (3)	C75—C67—C66	110.5 (3)
C37—C29—C28	110.2 (3)	C58—C67—C66	110.8 (3)
C20—C29—C28	109.5 (3)	C62—C67—C66	106.4 (3)
C28—C30—C31	113.1 (3)	C69—C68—C66	112.9 (4)
C28—C30—H30A	109.0	C69—C68—H68A	109.0
C31—C30—H30A	109.0	C66—C68—H68A	109.0
C28—C30—H30B	109.0	C69—C68—H68B	109.0
C31—C30—H30B	109.0	C66—C68—H68B	109.0
H30A—C30—H30B	107.8	H68A—C68—H68B	107.8
C32—C31—C30	111.2 (4)	C70—C69—C68	111.5 (3)
C32—C31—H31A	109.4	C70—C69—H69A	109.3
C30—C31—H31A	109.4	C68—C69—H69A	109.3
C32—C31—H31B	109.4	C70—C69—H69B	109.3
C30—C31—H31B	109.4	C68—C69—H69B	109.3
H31A—C31—H31B	108.0	H69A—C69—H69B	108.0
C31—C32—C38	110.8 (4)	C69—C70—C74	116.4 (4)
C31—C32—C36	116.5 (4)	C69—C70—C76	111.2 (4)
C38—C32—C36	108.1 (3)	C74—C70—C76	108.2 (3)
C31—C32—C33	108.2 (3)	C69—C70—C71	107.8 (3)
C38—C32—C33	113.1 (4)	C74—C70—C71	100.3 (3)
C36—C32—C33	99.8 (3)	C76—C70—C71	112.6 (3)
C34—C33—C27	119.2 (4)	C65—C71—C70	115.1 (4)
C34—C33—C32	104.1 (3)	C65—C71—C72	118.8 (4)
C27—C33—C32	114.3 (4)	C70—C71—C72	104.4 (3)
C34—C33—H33	106.1	C65—C71—H71	105.8
C27—C33—H33	106.1	C70—C71—H71	105.8
C32—C33—H33	106.1	C72—C71—H71	105.8
C33—C34—C35	104.1 (4)	C71—C72—C73	103.4 (3)
C33—C34—H34A	110.9	C71—C72—H72A	111.1
C35—C34—H34A	110.9	C73—C72—H72A	111.1
C33—C34—H34B	110.9	C71—C72—H72B	111.1
C35—C34—H34B	110.9	C73—C72—H72B	111.1
H34A—C34—H34B	108.9	H72A—C72—H72B	109.1
C34—C35—C36	105.7 (3)	C72—C73—C74	106.2 (3)
C34—C35—H35A	110.6	C72—C73—H73A	110.5
C36—C35—H35A	110.6	C74—C73—H73A	110.5
C34—C35—H35B	110.6	C72—C73—H73B	110.5
C36—C35—H35B	110.6	C74—C73—H73B	110.5
H35A—C35—H35B	108.7	H73A—C73—H73B	108.7
C32—C36—C35	105.1 (3)	C70—C74—C73	105.0 (3)
C32—C36—H36A	110.7	C70—C74—H74A	110.7
C35—C36—H36A	110.7	C73—C74—H74A	110.7
C32—C36—H36B	110.7	C70—C74—H74B	110.7
C35—C36—H36B	110.7	C73—C74—H74B	110.7
H36A—C36—H36B	108.8	H74A—C74—H74B	108.8
C29—C37—H37A	109.5	C67—C75—H75A	109.5
C29—C37—H37B	109.5	C67—C75—H75B	109.5
H37A—C37—H37B	109.5	H75A—C75—H75B	109.5
C29—C37—H37C	109.5	C67—C75—H75C	109.5
H37A—C37—H37C	109.5	H75A—C75—H75C	109.5
H37B—C37—H37C	109.5	H75B—C75—H75C	109.5
C32—C38—H38A	109.5	C70—C76—H76A	109.5
C32—C38—H38B	109.5	C70—C76—H76B	109.5
H38A—C38—H38B	109.5	H76A—C76—H76B	109.5
C32—C38—H38C	109.5	C70—C76—H76C	109.5
H38A—C38—H38C	109.5	H76A—C76—H76C	109.5
H38B—C38—H38C	109.5	H76B—C76—H76C	109.5

C10—C1—C2—C3	−54.9 (5)	C48—C39—C40—C41	−54.1 (5)
C1—C2—C3—C4	52.3 (5)	C39—C40—C41—C42	52.6 (6)
C2—C3—C4—C5	−53.5 (5)	C40—C41—C42—C43	−54.5 (5)
C3—C4—C5—C6	−174.8 (4)	C41—C42—C43—C44	−173.6 (4)
C3—C4—C5—C10	56.9 (5)	C41—C42—C43—C48	58.8 (5)
C4—C5—C6—C7	174.8 (4)	C42—C43—C44—C45	175.5 (4)
C10—C5—C6—C7	−57.3 (5)	C48—C43—C44—C45	−56.5 (5)
C5—C6—C7—C8	54.9 (5)	C43—C44—C45—C46	53.9 (5)
C6—C7—C8—C14	−176.0 (4)	C44—C45—C46—C52	−175.5 (4)
C6—C7—C8—C9	−54.2 (5)	C44—C45—C46—C47	−53.7 (5)
C14—C8—C9—C11	−52.2 (5)	C52—C46—C47—C49	−51.5 (5)
C7—C8—C9—C11	−175.0 (4)	C45—C46—C47—C49	−174.1 (4)
C14—C8—C9—C10	178.5 (3)	C52—C46—C47—C48	178.8 (3)
C7—C8—C9—C10	55.7 (5)	C45—C46—C47—C48	56.2 (5)
C2—C1—C10—C18	−65.6 (5)	C44—C43—C48—C56	−65.3 (5)
C2—C1—C10—C5	55.6 (5)	C42—C43—C48—C56	61.7 (5)
C2—C1—C10—C9	173.0 (4)	C44—C43—C48—C47	57.5 (5)
C6—C5—C10—C1	175.8 (4)	C42—C43—C48—C47	−175.4 (4)
C4—C5—C10—C1	−56.5 (5)	C44—C43—C48—C39	175.8 (3)
C6—C5—C10—C18	−64.1 (5)	C42—C43—C48—C39	−57.1 (5)
C4—C5—C10—C18	63.6 (5)	C49—C47—C48—C43	174.5 (4)
C6—C5—C10—C9	56.5 (5)	C46—C47—C48—C43	−57.3 (5)
C4—C5—C10—C9	−175.8 (3)	C49—C47—C48—C56	−62.1 (5)
C11—C9—C10—C1	58.7 (5)	C46—C47—C48—C56	66.1 (5)
C8—C9—C10—C1	−173.1 (3)	C49—C47—C48—C39	57.9 (5)
C11—C9—C10—C18	−62.3 (5)	C46—C47—C48—C39	−173.9 (3)
C8—C9—C10—C18	65.8 (5)	C40—C39—C48—C43	54.7 (5)
C11—C9—C10—C5	176.3 (4)	C40—C39—C48—C56	−66.5 (5)
C8—C9—C10—C5	−55.5 (4)	C40—C39—C48—C47	171.8 (4)
C8—C9—C11—C12	51.8 (5)	C48—C47—C49—C50	179.4 (4)
C10—C9—C11—C12	−179.6 (4)	C46—C47—C49—C50	51.1 (5)
C9—C11—C12—C13	−54.2 (5)	C47—C49—C50—C51	−54.1 (5)
C11—C12—C13—C17	167.6 (4)	C49—C50—C51—C55	168.3 (4)
C11—C12—C13—C14	55.6 (5)	C49—C50—C51—C57	−68.0 (5)
C11—C12—C13—C19	−68.5 (5)	C49—C50—C51—C52	56.6 (5)
C7—C8—C14—C15	−56.5 (5)	C45—C46—C52—C53	−57.0 (5)
C9—C8—C14—C15	−179.1 (4)	C47—C46—C52—C53	−179.3 (4)
C7—C8—C14—C13	−179.7 (4)	C45—C46—C52—C51	179.6 (3)
C9—C8—C14—C13	57.7 (5)	C47—C46—C52—C51	57.3 (5)
C12—C13—C14—C8	−59.6 (5)	C50—C51—C52—C53	168.1 (4)
C17—C13—C14—C8	178.3 (4)	C55—C51—C52—C53	45.8 (4)
C19—C13—C14—C8	62.9 (5)	C57—C51—C52—C53	−68.7 (4)
C12—C13—C14—C15	169.4 (4)	C50—C51—C52—C46	−60.3 (5)
C17—C13—C14—C15	47.2 (4)	C55—C51—C52—C46	177.4 (4)
C19—C13—C14—C15	−68.2 (4)	C57—C51—C52—C46	62.9 (5)
C8—C14—C15—C16	−163.9 (4)	C46—C52—C53—C54	−160.9 (4)
C13—C14—C15—C16	−36.1 (4)	C51—C52—C53—C54	−33.5 (5)
C14—C15—C16—C17	11.2 (5)	C52—C53—C54—C55	7.9 (5)
C12—C13—C17—C16	−155.5 (4)	C50—C51—C55—C54	−156.9 (4)
C14—C13—C17—C16	−39.0 (4)	C57—C51—C55—C54	78.1 (5)
C19—C13—C17—C16	79.7 (5)	C52—C51—C55—C54	−40.0 (5)
C15—C16—C17—C13	17.7 (5)	C53—C54—C55—C51	20.5 (5)
C29—C20—C21—C22	−55.3 (5)	C67—C58—C59—C60	−56.6 (5)
C20—C21—C22—C23	53.5 (5)	C58—C59—C60—C61	54.6 (5)
C21—C22—C23—C24	−53.0 (5)	C59—C60—C61—C62	−54.1 (5)
C22—C23—C24—C29	55.9 (5)	C60—C61—C62—C63	−176.0 (4)
C22—C23—C24—C25	−175.6 (4)	C60—C61—C62—C67	56.1 (5)
C29—C24—C25—C26	−55.8 (5)	C61—C62—C63—C64	173.2 (4)
C23—C24—C25—C26	174.6 (4)	C67—C62—C63—C64	−58.3 (5)
C24—C25—C26—C27	52.4 (5)	C62—C63—C64—C65	54.0 (5)
C25—C26—C27—C33	−174.4 (4)	C63—C64—C65—C71	−173.6 (4)
C25—C26—C27—C28	−52.8 (5)	C63—C64—C65—C66	−52.0 (5)
C26—C27—C28—C30	−174.6 (4)	C71—C65—C66—C68	−51.5 (4)
C33—C27—C28—C30	−51.3 (5)	C64—C65—C66—C68	−174.9 (3)
C26—C27—C28—C29	54.6 (5)	C71—C65—C66—C67	179.2 (3)
C33—C27—C28—C29	177.9 (3)	C64—C65—C66—C67	55.7 (5)
C23—C24—C29—C37	63.7 (5)	C59—C58—C67—C75	−66.8 (5)
C25—C24—C29—C37	−63.8 (4)	C59—C58—C67—C62	55.2 (5)
C23—C24—C29—C20	−55.3 (5)	C59—C58—C67—C66	171.0 (4)
C25—C24—C29—C20	177.2 (3)	C63—C62—C67—C75	−62.8 (4)
C23—C24—C29—C28	−174.0 (3)	C61—C62—C67—C75	65.0 (5)
C25—C24—C29—C28	58.6 (5)	C63—C62—C67—C58	176.8 (3)
C21—C20—C29—C24	54.1 (5)	C61—C62—C67—C58	−55.3 (5)
C21—C20—C29—C37	−67.6 (5)	C63—C62—C67—C66	58.1 (4)
C21—C20—C29—C28	172.3 (4)	C61—C62—C67—C66	−174.1 (4)
C30—C28—C29—C24	174.1 (3)	C65—C66—C67—C75	64.8 (5)
C27—C28—C29—C24	−57.1 (4)	C68—C66—C67—C75	−63.7 (5)
C30—C28—C29—C37	−62.2 (5)	C65—C66—C67—C58	−173.7 (3)
C27—C28—C29—C37	66.5 (4)	C68—C66—C67—C58	57.9 (5)
C30—C28—C29—C20	56.6 (5)	C65—C66—C67—C62	−57.1 (4)
C27—C28—C29—C20	−174.7 (3)	C68—C66—C67—C62	174.4 (3)
C29—C28—C30—C31	−179.3 (4)	C65—C66—C68—C69	52.3 (5)
C27—C28—C30—C31	52.5 (5)	C67—C66—C68—C69	−178.6 (4)
C28—C30—C31—C32	−55.9 (5)	C66—C68—C69—C70	−55.0 (5)
C30—C31—C32—C38	−67.9 (4)	C68—C69—C70—C74	167.5 (4)
C30—C31—C32—C36	168.0 (4)	C68—C69—C70—C76	−68.0 (4)
C30—C31—C32—C33	56.6 (5)	C68—C69—C70—C71	55.9 (4)
C26—C27—C33—C34	−56.3 (5)	C64—C65—C71—C70	−179.7 (3)
C28—C27—C33—C34	−179.6 (4)	C66—C65—C71—C70	57.4 (5)
C26—C27—C33—C32	179.6 (4)	C64—C65—C71—C72	−54.8 (5)
C28—C27—C33—C32	56.4 (5)	C66—C65—C71—C72	−177.8 (4)
C31—C32—C33—C34	168.4 (4)	C69—C70—C71—C65	−59.8 (5)
C38—C32—C33—C34	−68.5 (4)	C74—C70—C71—C65	178.0 (4)
C36—C32—C33—C34	46.1 (4)	C76—C70—C71—C65	63.2 (5)
C31—C32—C33—C27	−59.8 (5)	C69—C70—C71—C72	168.2 (3)
C38—C32—C33—C27	63.3 (5)	C74—C70—C71—C72	46.0 (4)
C36—C32—C33—C27	177.9 (4)	C76—C70—C71—C72	−68.8 (4)
C27—C33—C34—C35	−165.1 (4)	C65—C71—C72—C73	−165.8 (4)
C32—C33—C34—C35	−36.2 (4)	C70—C71—C72—C73	−35.9 (4)
C33—C34—C35—C36	11.7 (5)	C71—C72—C73—C74	11.6 (5)
C31—C32—C36—C35	−154.2 (4)	C69—C70—C74—C73	−153.7 (4)
C38—C32—C36—C35	80.3 (4)	C76—C70—C74—C73	80.3 (4)
C33—C32—C36—C35	−38.1 (4)	C71—C70—C74—C73	−37.8 (4)
C34—C35—C36—C32	16.9 (5)	C72—C73—C74—C70	16.6 (4)

5α,14α-Androstane, Form II w/ impurity (Form_II_impure) top

Crystal data top

2C₁₉H₃₁O_0.50·C₁₉H₃₂	D_x = 1.114 Mg m⁻³
M_r = 795.32	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 31747 reflections
a = 7.1699 (1) Å	θ = 2.0–74.8°
b = 22.1480 (3) Å	µ = 0.46 mm⁻¹
c = 29.8734 (5) Å	T = 90 K
V = 4743.86 (12) Å³	Needle, colorless
Z = 4	0.19 × 0.06 × 0.03 mm
F(000) = 1776

Data collection top

ROD, Synergy Custom system, HyPix diffractometer	9113 independent reflections
Radiation source: Rotating-anode X-ray tube	8487 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.059
ω scans	θ_max = 75.1°, θ_min = 2.5°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021)	h = −8→7
T_min = 0.757, T_max = 1.000	k = −26→27
59898 measured reflections	l = −36→34

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0541P)² + 1.8106P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.24 e Å⁻³
9113 reflections	Δρ_min = −0.34 e Å⁻³
539 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00062 (10)
Primary atom site location: iterative	Absolute structure: Flack x determined using 3326 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (2)

Special details top

Refinement. Data were integrated and scaled using CrysAlis PRO (Rigaku OD, 2021). WinGX (Farrugia, 2012) was used for the solution and refinement of the crystal structures. Solution by intrinsic phasing (SHELXT2014; Sheldrick, 2015a) produced a complete heavy-atom phasing model. All non-H atoms were refined anisotropically by full-matrix least-squares (SHELXL2018; Sheldrick, 2015b).

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3096 (3)	0.69774 (11)	0.46259 (9)	0.0256 (5)
H1A	0.429224	0.716861	0.454056	0.031*
H1B	0.264300	0.717920	0.490091	0.031*
C2	0.3441 (4)	0.63099 (12)	0.47277 (9)	0.0303 (6)
H2A	0.401442	0.611506	0.446307	0.036*
H2B	0.432906	0.627557	0.498019	0.036*
C3	0.1641 (4)	0.59809 (12)	0.48469 (10)	0.0327 (6)
H3A	0.115443	0.613690	0.513466	0.039*
H3B	0.189902	0.554452	0.488358	0.039*
C4	0.0181 (4)	0.60706 (12)	0.44811 (9)	0.0303 (6)
H4A	−0.100861	0.588437	0.457729	0.036*
H4B	0.059683	0.586276	0.420522	0.036*
C5	−0.0148 (3)	0.67409 (12)	0.43780 (8)	0.0246 (5)
H5	−0.059826	0.692943	0.466233	0.030*
C6	−0.1690 (3)	0.68352 (12)	0.40326 (9)	0.0267 (5)
H6A	−0.282637	0.661773	0.412981	0.032*
H6B	−0.129108	0.666382	0.374186	0.032*
C7	−0.2144 (4)	0.75054 (12)	0.39730 (9)	0.0263 (5)
H7A	−0.304438	0.755148	0.372413	0.032*
H7B	−0.274598	0.765758	0.424899	0.032*
C8	−0.0416 (3)	0.78878 (11)	0.38739 (8)	0.0222 (5)
H8	0.004952	0.778308	0.356802	0.027*
C9	0.1160 (3)	0.77643 (11)	0.42159 (8)	0.0223 (5)
H9	0.064183	0.787692	0.451519	0.027*
C10	0.1666 (3)	0.70791 (12)	0.42473 (8)	0.0236 (5)
C11	0.2840 (3)	0.81831 (12)	0.41387 (9)	0.0263 (5)
H11A	0.343411	0.807794	0.384991	0.032*
H11B	0.376854	0.811457	0.437866	0.032*
C12	0.2300 (3)	0.88577 (11)	0.41327 (9)	0.0263 (5)
H12A	0.185016	0.897870	0.443295	0.032*
H12B	0.341247	0.910384	0.406080	0.032*
C13	0.0777 (3)	0.89781 (11)	0.37867 (8)	0.0249 (5)
C14	−0.0884 (3)	0.85607 (11)	0.38845 (8)	0.0237 (5)
H14	−0.127463	0.865077	0.419882	0.028*
C15	−0.2436 (4)	0.88051 (12)	0.35853 (9)	0.0280 (6)
H15A	−0.367894	0.870314	0.370796	0.034*
H15B	−0.233363	0.864062	0.327811	0.034*
C16	−0.2110 (4)	0.94973 (13)	0.35886 (10)	0.0338 (6)
H16A	−0.210189	0.965804	0.327941	0.041*
H16B	−0.310653	0.970332	0.375977	0.041*
C17	−0.0189 (4)	0.95970 (12)	0.38149 (9)	0.0297 (6)
H17A	0.054016	0.990819	0.365373	0.036*
H17B	−0.034348	0.972421	0.413044	0.036*
C18	0.2495 (4)	0.68511 (12)	0.38036 (9)	0.0274 (5)
H18A	0.264547	0.641175	0.381702	0.041*
H18B	0.371231	0.704074	0.375411	0.041*
H18C	0.165392	0.695568	0.355679	0.041*
C19	0.1557 (4)	0.89004 (13)	0.33101 (9)	0.0318 (6)
H19A	0.195832	0.848141	0.326730	0.048*
H19B	0.262342	0.917115	0.326819	0.048*
H19C	0.058448	0.899913	0.309144	0.048*
C20	0.4793 (3)	0.82137 (11)	0.24893 (8)	0.0230 (5)
H20A	0.360295	0.798781	0.250223	0.028*
H20B	0.521855	0.828052	0.280065	0.028*
C21	0.4442 (4)	0.88292 (11)	0.22671 (9)	0.0267 (5)
H21A	0.386836	0.876610	0.196923	0.032*
H21B	0.355488	0.906431	0.245182	0.032*
C22	0.6247 (4)	0.91862 (11)	0.22134 (9)	0.0287 (6)
H22A	0.599183	0.956319	0.204618	0.034*
H22B	0.673331	0.929774	0.251234	0.034*
C23	0.7706 (4)	0.88177 (11)	0.19644 (9)	0.0266 (5)
H23A	0.888696	0.904848	0.195083	0.032*
H23B	0.727838	0.874649	0.165372	0.032*
C24	0.8057 (3)	0.82099 (11)	0.21944 (8)	0.0224 (5)
H24	0.847208	0.830638	0.250586	0.027*
C25	0.9643 (3)	0.78534 (12)	0.19809 (8)	0.0250 (5)
H25A	1.076921	0.811078	0.196261	0.030*
H25B	0.928754	0.773583	0.167278	0.030*
C26	1.0082 (3)	0.72878 (11)	0.22538 (9)	0.0259 (5)
H26A	1.057084	0.740862	0.255051	0.031*
H26B	1.106435	0.705277	0.209934	0.031*
C27	0.8361 (3)	0.68892 (11)	0.23182 (8)	0.0210 (5)
H27	0.795289	0.673894	0.201808	0.025*
C28	0.6737 (3)	0.72582 (11)	0.25266 (8)	0.0201 (5)
H28	0.720740	0.741176	0.282052	0.024*
C29	0.6253 (3)	0.78271 (11)	0.22425 (8)	0.0203 (5)
C30	0.5042 (3)	0.68561 (11)	0.26348 (8)	0.0230 (5)
H30A	0.410944	0.709839	0.280057	0.028*
H30B	0.445974	0.672352	0.235084	0.028*
C31	0.5544 (3)	0.62957 (11)	0.29141 (8)	0.0244 (5)
H31A	0.596563	0.642376	0.321503	0.029*
H31B	0.442251	0.603984	0.295142	0.029*
C32	0.7077 (3)	0.59312 (11)	0.26888 (9)	0.0240 (5)
C33	0.8774 (3)	0.63460 (11)	0.26148 (9)	0.0242 (5)
H33	0.910985	0.651153	0.291564	0.029*
C34	1.0338 (4)	0.59056 (13)	0.24873 (11)	0.0351 (6)
H34A	1.158057	0.608208	0.254900	0.042*
H34B	1.026471	0.579338	0.216703	0.042*
C35	0.9958 (4)	0.53525 (14)	0.27926 (13)	0.0454 (8)
H35A	1.005634	0.497250	0.261971	0.054*
H35B	1.086292	0.533907	0.304268	0.054*
C36	0.7968 (4)	0.54379 (12)	0.29705 (9)	0.0261 (5)	0.5
H36A	0.725233	0.505747	0.294302	0.031*	0.5
H36B	0.799535	0.555813	0.328962	0.031*	0.5
C36A	0.7968 (4)	0.54379 (12)	0.29705 (9)	0.0261 (5)	0.5
C37	0.5469 (3)	0.76430 (11)	0.17819 (8)	0.0236 (5)
H37A	0.422338	0.746845	0.181987	0.035*
H37B	0.629631	0.734365	0.164411	0.035*
H37C	0.539014	0.799975	0.158878	0.035*
C38	0.6357 (4)	0.56397 (12)	0.22526 (9)	0.0292 (6)
H38A	0.735771	0.540175	0.211536	0.044*
H38B	0.595868	0.595661	0.204461	0.044*
H38C	0.529795	0.537561	0.232081	0.044*
C39	1.3496 (4)	0.33732 (13)	0.53750 (10)	0.0322 (6)
H39A	1.354491	0.305355	0.514364	0.039*
H39B	1.419921	0.372544	0.526052	0.039*
C40	1.4440 (4)	0.31436 (13)	0.57959 (10)	0.0342 (6)
H40A	1.575956	0.304757	0.572880	0.041*
H40B	1.382107	0.276720	0.589533	0.041*
C41	1.4359 (4)	0.36074 (13)	0.61707 (10)	0.0326 (6)
H41A	1.508589	0.396918	0.608444	0.039*
H41B	1.492303	0.343594	0.644518	0.039*
C42	1.2337 (4)	0.37879 (13)	0.62647 (9)	0.0295 (6)
H42A	1.164734	0.343472	0.638261	0.035*
H42B	1.231230	0.410816	0.649581	0.035*
C43	1.1377 (3)	0.40169 (11)	0.58407 (8)	0.0232 (5)
H43	1.211205	0.437565	0.573979	0.028*
C44	0.9406 (4)	0.42460 (12)	0.59292 (8)	0.0256 (5)
H44A	0.942864	0.453809	0.618004	0.031*
H44B	0.859726	0.390357	0.601676	0.031*
C45	0.8606 (4)	0.45509 (12)	0.55128 (8)	0.0252 (5)
H45A	0.930991	0.492699	0.545348	0.030*
H45B	0.729117	0.466316	0.557086	0.030*
C46	0.8689 (4)	0.41484 (11)	0.50980 (8)	0.0230 (5)
H46	0.780431	0.380378	0.513921	0.028*
C47	1.0676 (3)	0.38923 (11)	0.50277 (8)	0.0247 (5)
H47	1.150666	0.424978	0.498202	0.030*
C48	1.1434 (3)	0.35606 (11)	0.54478 (9)	0.0246 (5)
C49	1.0793 (4)	0.35205 (15)	0.45941 (10)	0.0381 (7)
H49A	1.001705	0.315340	0.462667	0.046*
H49B	1.209939	0.339008	0.454747	0.046*
C50	1.0134 (4)	0.38759 (16)	0.41800 (9)	0.0418 (7)
H50A	1.099747	0.421646	0.412395	0.050*
H50B	1.015593	0.360872	0.391436	0.050*
C51	0.8163 (4)	0.41186 (13)	0.42490 (9)	0.0316 (6)
C52	0.8128 (4)	0.44977 (11)	0.46790 (8)	0.0248 (5)
H52	0.909730	0.481792	0.463866	0.030*
C53	0.6238 (4)	0.48232 (12)	0.46601 (9)	0.0309 (6)
H53A	0.625754	0.519753	0.484115	0.037*
H53B	0.522073	0.455880	0.476851	0.037*
C54	0.6004 (4)	0.49676 (14)	0.41545 (10)	0.0374 (7)
H54A	0.473588	0.485916	0.405120	0.045*
H54B	0.621387	0.540259	0.409713	0.045*
C55	0.7472 (4)	0.45863 (13)	0.39143 (9)	0.0363 (7)	0.5
H55A	0.691789	0.438468	0.365012	0.044*	0.5
H55B	0.851740	0.484382	0.381241	0.044*	0.5
C55A	0.7472 (4)	0.45863 (13)	0.39143 (9)	0.0363 (7)	0.5
C56	1.0282 (4)	0.29894 (12)	0.55494 (10)	0.0310 (6)
H56A	1.048451	0.269021	0.531264	0.047*
H56B	0.895506	0.309431	0.556259	0.047*
H56C	1.067317	0.282028	0.583765	0.047*
C57	0.6750 (5)	0.35999 (13)	0.42512 (11)	0.0407 (7)
H57A	0.549272	0.376264	0.429547	0.061*
H57B	0.704870	0.331989	0.449488	0.061*
H57C	0.680537	0.338536	0.396458	0.061*
O1	0.6982 (6)	0.5160 (2)	0.32882 (14)	0.0440 (10)	0.5
O2	0.7997 (6)	0.4697 (2)	0.35179 (15)	0.0447 (11)	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0206 (12)	0.0274 (13)	0.0287 (13)	−0.0001 (10)	−0.0014 (10)	−0.0025 (10)
C2	0.0270 (14)	0.0313 (14)	0.0326 (14)	0.0024 (11)	−0.0036 (11)	−0.0007 (11)
C3	0.0343 (15)	0.0279 (13)	0.0360 (15)	0.0000 (12)	−0.0023 (12)	0.0066 (11)
C4	0.0259 (13)	0.0266 (13)	0.0385 (15)	−0.0043 (11)	−0.0001 (11)	0.0011 (11)
C5	0.0200 (12)	0.0266 (13)	0.0272 (12)	−0.0040 (10)	0.0005 (10)	−0.0007 (10)
C6	0.0191 (12)	0.0290 (13)	0.0320 (13)	−0.0048 (10)	−0.0012 (10)	−0.0013 (11)
C7	0.0189 (12)	0.0301 (14)	0.0299 (14)	−0.0012 (10)	−0.0011 (10)	−0.0004 (11)
C8	0.0175 (11)	0.0251 (12)	0.0241 (12)	−0.0016 (9)	0.0006 (9)	−0.0006 (10)
C9	0.0184 (11)	0.0254 (12)	0.0232 (12)	−0.0008 (10)	0.0006 (9)	−0.0027 (10)
C10	0.0180 (11)	0.0279 (13)	0.0249 (12)	−0.0037 (10)	−0.0006 (10)	−0.0016 (10)
C11	0.0159 (12)	0.0264 (13)	0.0366 (14)	−0.0013 (10)	−0.0004 (10)	0.0000 (11)
C12	0.0203 (12)	0.0250 (13)	0.0337 (14)	−0.0012 (10)	0.0003 (10)	−0.0013 (11)
C13	0.0226 (12)	0.0226 (12)	0.0294 (13)	−0.0021 (10)	0.0015 (10)	−0.0021 (10)
C14	0.0201 (12)	0.0287 (13)	0.0224 (12)	−0.0009 (10)	0.0008 (9)	−0.0031 (10)
C15	0.0229 (13)	0.0310 (14)	0.0300 (14)	0.0023 (11)	−0.0029 (10)	−0.0001 (11)
C16	0.0299 (15)	0.0308 (15)	0.0406 (16)	0.0030 (12)	−0.0070 (12)	−0.0030 (12)
C17	0.0291 (14)	0.0242 (13)	0.0357 (14)	0.0014 (11)	−0.0014 (11)	−0.0033 (11)
C18	0.0234 (12)	0.0291 (13)	0.0298 (13)	0.0022 (11)	0.0003 (10)	−0.0020 (11)
C19	0.0307 (14)	0.0318 (14)	0.0329 (14)	−0.0013 (12)	0.0051 (11)	0.0022 (12)
C20	0.0188 (12)	0.0244 (12)	0.0259 (12)	0.0004 (10)	0.0018 (9)	−0.0005 (10)
C21	0.0259 (13)	0.0245 (13)	0.0298 (13)	0.0028 (10)	0.0026 (10)	0.0002 (10)
C22	0.0292 (14)	0.0209 (12)	0.0361 (14)	0.0003 (11)	0.0021 (11)	0.0008 (11)
C23	0.0250 (13)	0.0226 (12)	0.0321 (14)	−0.0033 (10)	0.0028 (10)	0.0001 (11)
C24	0.0193 (12)	0.0229 (12)	0.0249 (12)	−0.0031 (10)	0.0009 (9)	−0.0021 (10)
C25	0.0197 (12)	0.0258 (13)	0.0296 (13)	−0.0043 (10)	0.0045 (10)	0.0019 (10)
C26	0.0174 (12)	0.0273 (13)	0.0330 (13)	−0.0004 (10)	0.0011 (10)	0.0006 (11)
C27	0.0151 (11)	0.0232 (12)	0.0247 (12)	−0.0007 (9)	0.0009 (9)	0.0003 (10)
C28	0.0174 (11)	0.0218 (12)	0.0212 (11)	−0.0015 (9)	−0.0008 (9)	−0.0003 (9)
C29	0.0165 (11)	0.0221 (11)	0.0222 (12)	0.0000 (9)	0.0004 (9)	−0.0009 (10)
C30	0.0160 (11)	0.0251 (12)	0.0280 (12)	−0.0010 (10)	0.0012 (9)	0.0047 (10)
C31	0.0201 (12)	0.0262 (13)	0.0268 (13)	−0.0011 (10)	0.0008 (10)	0.0046 (10)
C32	0.0217 (12)	0.0229 (12)	0.0274 (13)	−0.0001 (10)	−0.0004 (10)	0.0035 (10)
C33	0.0180 (12)	0.0258 (13)	0.0289 (13)	0.0001 (10)	−0.0017 (10)	0.0010 (10)
C34	0.0210 (13)	0.0319 (15)	0.0523 (17)	0.0031 (11)	0.0030 (12)	0.0039 (13)
C35	0.0277 (15)	0.0312 (16)	0.077 (2)	0.0058 (13)	0.0025 (15)	0.0134 (15)
C36	0.0282 (14)	0.0227 (12)	0.0275 (13)	0.0000 (11)	−0.0025 (11)	0.0023 (10)
C36A	0.0282 (14)	0.0227 (12)	0.0275 (13)	0.0000 (11)	−0.0025 (11)	0.0023 (10)
C37	0.0219 (12)	0.0241 (12)	0.0249 (12)	−0.0029 (10)	−0.0025 (10)	0.0010 (10)
C38	0.0299 (14)	0.0248 (13)	0.0330 (14)	−0.0006 (11)	−0.0012 (11)	0.0008 (11)
C39	0.0216 (13)	0.0359 (15)	0.0392 (15)	0.0047 (11)	0.0043 (12)	−0.0033 (12)
C40	0.0195 (13)	0.0337 (15)	0.0493 (17)	0.0044 (11)	−0.0019 (12)	0.0042 (13)
C41	0.0232 (13)	0.0349 (15)	0.0398 (15)	−0.0029 (11)	−0.0064 (12)	0.0086 (12)
C42	0.0259 (13)	0.0323 (14)	0.0304 (14)	−0.0027 (11)	−0.0029 (11)	0.0061 (11)
C43	0.0189 (12)	0.0239 (12)	0.0270 (13)	−0.0014 (10)	0.0022 (10)	0.0031 (10)
C44	0.0248 (13)	0.0305 (13)	0.0216 (12)	0.0029 (10)	0.0023 (10)	0.0016 (10)
C45	0.0240 (12)	0.0277 (13)	0.0239 (12)	0.0062 (11)	0.0015 (10)	0.0012 (10)
C46	0.0212 (12)	0.0227 (12)	0.0249 (12)	−0.0015 (10)	0.0015 (10)	0.0010 (10)
C47	0.0225 (12)	0.0254 (12)	0.0264 (13)	−0.0015 (10)	0.0031 (10)	−0.0022 (10)
C48	0.0189 (12)	0.0225 (12)	0.0325 (13)	−0.0013 (10)	0.0018 (10)	−0.0012 (10)
C49	0.0344 (15)	0.0457 (17)	0.0341 (15)	0.0107 (13)	−0.0007 (12)	−0.0129 (13)
C50	0.0414 (17)	0.058 (2)	0.0256 (14)	0.0078 (15)	0.0003 (12)	−0.0127 (14)
C51	0.0338 (15)	0.0344 (14)	0.0266 (13)	−0.0026 (12)	−0.0036 (11)	−0.0016 (11)
C52	0.0266 (13)	0.0231 (12)	0.0247 (12)	−0.0040 (10)	0.0006 (10)	0.0012 (10)
C53	0.0329 (14)	0.0270 (13)	0.0326 (14)	0.0014 (11)	−0.0049 (12)	0.0023 (11)
C54	0.0362 (16)	0.0412 (16)	0.0346 (16)	−0.0032 (13)	−0.0098 (12)	0.0098 (13)
C55	0.0448 (17)	0.0390 (16)	0.0252 (14)	−0.0120 (14)	−0.0073 (12)	0.0045 (12)
C55A	0.0448 (17)	0.0390 (16)	0.0252 (14)	−0.0120 (14)	−0.0073 (12)	0.0045 (12)
C56	0.0239 (13)	0.0227 (13)	0.0464 (16)	−0.0026 (11)	−0.0055 (12)	0.0030 (11)
C57	0.0468 (18)	0.0307 (15)	0.0445 (17)	−0.0054 (13)	−0.0164 (14)	−0.0064 (13)
O1	0.048 (3)	0.041 (2)	0.042 (2)	0.000 (2)	−0.006 (2)	0.0053 (19)
O2	0.048 (3)	0.043 (2)	0.043 (2)	0.004 (2)	−0.002 (2)	0.003 (2)

Geometric parameters (Å, º) top

C1—C2	1.530 (4)	C30—H30A	0.9900
C1—C10	1.543 (3)	C30—H30B	0.9900
C1—H1A	0.9900	C31—C32	1.521 (4)
C1—H1B	0.9900	C31—H31A	0.9900
C2—C3	1.524 (4)	C31—H31B	0.9900
C2—H2A	0.9900	C32—C36A	1.520 (3)
C2—H2B	0.9900	C32—C36	1.520 (3)
C3—C4	1.526 (4)	C32—C33	1.540 (3)
C3—H3A	0.9900	C32—C38	1.543 (4)
C3—H3B	0.9900	C33—C34	1.534 (4)
C4—C5	1.535 (4)	C33—H33	1.0000
C4—H4A	0.9900	C34—C35	1.551 (4)
C4—H4B	0.9900	C34—H34A	0.9900
C5—C6	1.527 (3)	C34—H34B	0.9900
C5—C10	1.551 (3)	C35—C36A	1.534 (4)
C5—H5	1.0000	C35—C36	1.534 (4)
C6—C7	1.530 (4)	C35—H35A	0.9900
C6—H6A	0.9900	C35—H35B	0.9900
C6—H6B	0.9900	C36—H36A	0.9900
C7—C8	1.530 (3)	C36—H36B	0.9900
C7—H7A	0.9900	C36A—O1	1.335 (5)
C7—H7B	0.9900	C37—H37A	0.9800
C8—C14	1.528 (3)	C37—H37B	0.9800
C8—C9	1.548 (3)	C37—H37C	0.9800
C8—H8	1.0000	C38—H38A	0.9800
C9—C11	1.538 (3)	C38—H38B	0.9800
C9—C10	1.563 (3)	C38—H38C	0.9800
C9—H9	1.0000	C39—C40	1.516 (4)
C10—C18	1.538 (4)	C39—C48	1.551 (3)
C11—C12	1.544 (4)	C39—H39A	0.9900
C11—H11A	0.9900	C39—H39B	0.9900
C11—H11B	0.9900	C40—C41	1.520 (4)
C12—C13	1.527 (4)	C40—H40A	0.9900
C12—H12A	0.9900	C40—H40B	0.9900
C12—H12B	0.9900	C41—C42	1.530 (4)
C13—C14	1.536 (3)	C41—H41A	0.9900
C13—C17	1.538 (3)	C41—H41B	0.9900
C13—C19	1.539 (4)	C42—C43	1.528 (3)
C14—C15	1.526 (3)	C42—H42A	0.9900
C14—H14	1.0000	C42—H42B	0.9900
C15—C16	1.551 (4)	C43—C44	1.525 (3)
C15—H15A	0.9900	C43—C48	1.549 (3)
C15—H15B	0.9900	C43—H43	1.0000
C16—C17	1.550 (4)	C44—C45	1.527 (3)
C16—H16A	0.9900	C44—H44A	0.9900
C16—H16B	0.9900	C44—H44B	0.9900
C17—H17A	0.9900	C45—C46	1.528 (3)
C17—H17B	0.9900	C45—H45A	0.9900
C18—H18A	0.9800	C45—H45B	0.9900
C18—H18B	0.9800	C46—C52	1.525 (3)
C18—H18C	0.9800	C46—C47	1.548 (3)
C19—H19A	0.9800	C46—H46	1.0000
C19—H19B	0.9800	C47—C49	1.537 (4)
C19—H19C	0.9800	C47—C48	1.552 (4)
C20—C21	1.537 (3)	C47—H47	1.0000
C20—C29	1.540 (3)	C48—C56	1.541 (3)
C20—H20A	0.9900	C49—C50	1.540 (4)
C20—H20B	0.9900	C49—H49A	0.9900
C21—C22	1.525 (4)	C49—H49B	0.9900
C21—H21A	0.9900	C50—C51	1.526 (4)
C21—H21B	0.9900	C50—H50A	0.9900
C22—C23	1.521 (4)	C50—H50B	0.9900
C22—H22A	0.9900	C51—C55A	1.523 (4)
C22—H22B	0.9900	C51—C55	1.523 (4)
C23—C24	1.532 (3)	C51—C57	1.532 (4)
C23—H23A	0.9900	C51—C52	1.535 (4)
C23—H23B	0.9900	C52—C53	1.536 (4)
C24—C25	1.524 (3)	C52—H52	1.0000
C24—C29	1.553 (3)	C53—C54	1.553 (4)
C24—H24	1.0000	C53—H53A	0.9900
C25—C26	1.527 (4)	C53—H53B	0.9900
C25—H25A	0.9900	C54—C55A	1.528 (4)
C25—H25B	0.9900	C54—C55	1.528 (4)
C26—C27	1.529 (3)	C54—H54A	0.9900
C26—H26A	0.9900	C54—H54B	0.9900
C26—H26B	0.9900	C55—H55A	0.9900
C27—C33	1.523 (3)	C55—H55B	0.9900
C27—C28	1.553 (3)	C55A—O2	1.267 (5)
C27—H27	1.0000	C56—H56A	0.9800
C28—C30	1.541 (3)	C56—H56B	0.9800
C28—C29	1.558 (3)	C56—H56C	0.9800
C28—H28	1.0000	C57—H57A	0.9800
C29—C37	1.541 (3)	C57—H57B	0.9800
C30—C31	1.538 (3)	C57—H57C	0.9800

C2—C1—C10	113.2 (2)	C28—C30—H30B	108.9
C2—C1—H1A	108.9	H30A—C30—H30B	107.7
C10—C1—H1A	108.9	C32—C31—C30	111.0 (2)
C2—C1—H1B	108.9	C32—C31—H31A	109.4
C10—C1—H1B	108.9	C30—C31—H31A	109.4
H1A—C1—H1B	107.7	C32—C31—H31B	109.4
C3—C2—C1	111.8 (2)	C30—C31—H31B	109.4
C3—C2—H2A	109.3	H31A—C31—H31B	108.0
C1—C2—H2A	109.3	C36A—C32—C31	116.1 (2)
C3—C2—H2B	109.3	C36—C32—C31	116.1 (2)
C1—C2—H2B	109.3	C36A—C32—C33	100.2 (2)
H2A—C2—H2B	107.9	C36—C32—C33	100.2 (2)
C2—C3—C4	110.6 (2)	C31—C32—C33	108.5 (2)
C2—C3—H3A	109.5	C36A—C32—C38	107.9 (2)
C4—C3—H3A	109.5	C36—C32—C38	107.9 (2)
C2—C3—H3B	109.5	C31—C32—C38	110.7 (2)
C4—C3—H3B	109.5	C33—C32—C38	113.1 (2)
H3A—C3—H3B	108.1	C27—C33—C34	120.0 (2)
C3—C4—C5	112.0 (2)	C27—C33—C32	113.6 (2)
C3—C4—H4A	109.2	C34—C33—C32	103.5 (2)
C5—C4—H4A	109.2	C27—C33—H33	106.3
C3—C4—H4B	109.2	C34—C33—H33	106.3
C5—C4—H4B	109.2	C32—C33—H33	106.3
H4A—C4—H4B	107.9	C33—C34—C35	103.1 (2)
C6—C5—C4	112.3 (2)	C33—C34—H34A	111.1
C6—C5—C10	111.8 (2)	C35—C34—H34A	111.1
C4—C5—C10	112.9 (2)	C33—C34—H34B	111.1
C6—C5—H5	106.4	C35—C34—H34B	111.1
C4—C5—H5	106.4	H34A—C34—H34B	109.1
C10—C5—H5	106.4	C36A—C35—C34	105.6 (2)
C5—C6—C7	111.4 (2)	C36—C35—C34	105.6 (2)
C5—C6—H6A	109.3	C36—C35—H35A	110.6
C7—C6—H6A	109.3	C34—C35—H35A	110.6
C5—C6—H6B	109.3	C36—C35—H35B	110.6
C7—C6—H6B	109.3	C34—C35—H35B	110.6
H6A—C6—H6B	108.0	H35A—C35—H35B	108.7
C8—C7—C6	112.8 (2)	C32—C36—C35	106.7 (2)
C8—C7—H7A	109.0	C32—C36—H36A	110.4
C6—C7—H7A	109.0	C35—C36—H36A	110.4
C8—C7—H7B	109.0	C32—C36—H36B	110.4
C6—C7—H7B	109.0	C35—C36—H36B	110.4
H7A—C7—H7B	107.8	H36A—C36—H36B	108.6
C14—C8—C7	111.0 (2)	O1—C36A—C32	120.2 (3)
C14—C8—C9	108.62 (19)	O1—C36A—C35	133.0 (3)
C7—C8—C9	111.5 (2)	C32—C36A—C35	106.7 (2)
C14—C8—H8	108.6	C29—C37—H37A	109.5
C7—C8—H8	108.6	C29—C37—H37B	109.5
C9—C8—H8	108.6	H37A—C37—H37B	109.5
C11—C9—C8	111.5 (2)	C29—C37—H37C	109.5
C11—C9—C10	114.4 (2)	H37A—C37—H37C	109.5
C8—C9—C10	112.38 (19)	H37B—C37—H37C	109.5
C11—C9—H9	105.9	C32—C38—H38A	109.5
C8—C9—H9	105.9	C32—C38—H38B	109.5
C10—C9—H9	105.9	H38A—C38—H38B	109.5
C18—C10—C1	109.1 (2)	C32—C38—H38C	109.5
C18—C10—C5	112.5 (2)	H38A—C38—H38C	109.5
C1—C10—C5	107.6 (2)	H38B—C38—H38C	109.5
C18—C10—C9	110.9 (2)	C40—C39—C48	113.5 (2)
C1—C10—C9	109.9 (2)	C40—C39—H39A	108.9
C5—C10—C9	106.8 (2)	C48—C39—H39A	108.9
C9—C11—C12	112.9 (2)	C40—C39—H39B	108.9
C9—C11—H11A	109.0	C48—C39—H39B	108.9
C12—C11—H11A	109.0	H39A—C39—H39B	107.7
C9—C11—H11B	109.0	C39—C40—C41	111.5 (2)
C12—C11—H11B	109.0	C39—C40—H40A	109.3
H11A—C11—H11B	107.8	C41—C40—H40A	109.3
C13—C12—C11	110.9 (2)	C39—C40—H40B	109.3
C13—C12—H12A	109.5	C41—C40—H40B	109.3
C11—C12—H12A	109.5	H40A—C40—H40B	108.0
C13—C12—H12B	109.5	C40—C41—C42	110.4 (2)
C11—C12—H12B	109.5	C40—C41—H41A	109.6
H12A—C12—H12B	108.1	C42—C41—H41A	109.6
C12—C13—C14	108.7 (2)	C40—C41—H41B	109.6
C12—C13—C17	116.1 (2)	C42—C41—H41B	109.6
C14—C13—C17	100.2 (2)	H41A—C41—H41B	108.1
C12—C13—C19	110.3 (2)	C43—C42—C41	111.2 (2)
C14—C13—C19	113.0 (2)	C43—C42—H42A	109.4
C17—C13—C19	108.3 (2)	C41—C42—H42A	109.4
C15—C14—C8	119.6 (2)	C43—C42—H42B	109.4
C15—C14—C13	103.9 (2)	C41—C42—H42B	109.4
C8—C14—C13	114.4 (2)	H42A—C42—H42B	108.0
C15—C14—H14	106.0	C44—C43—C42	112.6 (2)
C8—C14—H14	106.0	C44—C43—C48	111.9 (2)
C13—C14—H14	106.0	C42—C43—C48	113.6 (2)
C14—C15—C16	103.7 (2)	C44—C43—H43	106.0
C14—C15—H15A	111.0	C42—C43—H43	106.0
C16—C15—H15A	111.0	C48—C43—H43	106.0
C14—C15—H15B	111.0	C43—C44—C45	110.7 (2)
C16—C15—H15B	111.0	C43—C44—H44A	109.5
H15A—C15—H15B	109.0	C45—C44—H44A	109.5
C17—C16—C15	106.1 (2)	C43—C44—H44B	109.5
C17—C16—H16A	110.5	C45—C44—H44B	109.5
C15—C16—H16A	110.5	H44A—C44—H44B	108.1
C17—C16—H16B	110.5	C44—C45—C46	112.8 (2)
C15—C16—H16B	110.5	C44—C45—H45A	109.0
H16A—C16—H16B	108.7	C46—C45—H45A	109.0
C13—C17—C16	104.4 (2)	C44—C45—H45B	109.0
C13—C17—H17A	110.9	C46—C45—H45B	109.0
C16—C17—H17A	110.9	H45A—C45—H45B	107.8
C13—C17—H17B	110.9	C52—C46—C45	111.1 (2)
C16—C17—H17B	110.9	C52—C46—C47	108.5 (2)
H17A—C17—H17B	108.9	C45—C46—C47	111.1 (2)
C10—C18—H18A	109.5	C52—C46—H46	108.7
C10—C18—H18B	109.5	C45—C46—H46	108.7
H18A—C18—H18B	109.5	C47—C46—H46	108.7
C10—C18—H18C	109.5	C49—C47—C46	111.2 (2)
H18A—C18—H18C	109.5	C49—C47—C48	114.1 (2)
H18B—C18—H18C	109.5	C46—C47—C48	112.7 (2)
C13—C19—H19A	109.5	C49—C47—H47	106.1
C13—C19—H19B	109.5	C46—C47—H47	106.1
H19A—C19—H19B	109.5	C48—C47—H47	106.1
C13—C19—H19C	109.5	C56—C48—C43	111.9 (2)
H19A—C19—H19C	109.5	C56—C48—C39	108.6 (2)
H19B—C19—H19C	109.5	C43—C48—C39	107.8 (2)
C21—C20—C29	113.4 (2)	C56—C48—C47	111.1 (2)
C21—C20—H20A	108.9	C43—C48—C47	107.13 (19)
C29—C20—H20A	108.9	C39—C48—C47	110.3 (2)
C21—C20—H20B	108.9	C47—C49—C50	112.7 (2)
C29—C20—H20B	108.9	C47—C49—H49A	109.0
H20A—C20—H20B	107.7	C50—C49—H49A	109.0
C22—C21—C20	111.5 (2)	C47—C49—H49B	109.0
C22—C21—H21A	109.3	C50—C49—H49B	109.0
C20—C21—H21A	109.3	H49A—C49—H49B	107.8
C22—C21—H21B	109.3	C51—C50—C49	110.8 (2)
C20—C21—H21B	109.3	C51—C50—H50A	109.5
H21A—C21—H21B	108.0	C49—C50—H50A	109.5
C23—C22—C21	110.9 (2)	C51—C50—H50B	109.5
C23—C22—H22A	109.5	C49—C50—H50B	109.5
C21—C22—H22A	109.5	H50A—C50—H50B	108.1
C23—C22—H22B	109.5	C55A—C51—C50	116.9 (3)
C21—C22—H22B	109.5	C55—C51—C50	116.9 (3)
H22A—C22—H22B	108.0	C55A—C51—C57	107.3 (2)
C22—C23—C24	111.4 (2)	C55—C51—C57	107.3 (2)
C22—C23—H23A	109.3	C50—C51—C57	110.4 (3)
C24—C23—H23A	109.3	C55A—C51—C52	99.9 (2)
C22—C23—H23B	109.3	C55—C51—C52	99.9 (2)
C24—C23—H23B	109.3	C50—C51—C52	108.7 (2)
H23A—C23—H23B	108.0	C57—C51—C52	113.3 (2)
C25—C24—C23	113.0 (2)	C46—C52—C51	113.9 (2)
C25—C24—C29	112.2 (2)	C46—C52—C53	120.1 (2)
C23—C24—C29	112.6 (2)	C51—C52—C53	103.9 (2)
C25—C24—H24	106.2	C46—C52—H52	106.0
C23—C24—H24	106.2	C51—C52—H52	106.0
C29—C24—H24	106.2	C53—C52—H52	106.0
C24—C25—C26	110.8 (2)	C52—C53—C54	103.2 (2)
C24—C25—H25A	109.5	C52—C53—H53A	111.1
C26—C25—H25A	109.5	C54—C53—H53A	111.1
C24—C25—H25B	109.5	C52—C53—H53B	111.1
C26—C25—H25B	109.5	C54—C53—H53B	111.1
H25A—C25—H25B	108.1	H53A—C53—H53B	109.1
C25—C26—C27	112.0 (2)	C55A—C54—C53	105.6 (2)
C25—C26—H26A	109.2	C55—C54—C53	105.6 (2)
C27—C26—H26A	109.2	C55—C54—H54A	110.6
C25—C26—H26B	109.2	C53—C54—H54A	110.6
C27—C26—H26B	109.2	C55—C54—H54B	110.6
H26A—C26—H26B	107.9	C53—C54—H54B	110.6
C33—C27—C26	111.9 (2)	H54A—C54—H54B	108.8
C33—C27—C28	109.15 (19)	C51—C55—C54	107.0 (2)
C26—C27—C28	110.58 (19)	C51—C55—H55A	110.3
C33—C27—H27	108.4	C54—C55—H55A	110.3
C26—C27—H27	108.4	C51—C55—H55B	110.3
C28—C27—H27	108.4	C54—C55—H55B	110.3
C30—C28—C27	111.80 (19)	H55A—C55—H55B	108.6
C30—C28—C29	113.94 (19)	O2—C55A—C51	130.5 (3)
C27—C28—C29	111.96 (19)	O2—C55A—C54	122.4 (3)
C30—C28—H28	106.2	C51—C55A—C54	107.0 (2)
C27—C28—H28	106.2	C48—C56—H56A	109.5
C29—C28—H28	106.2	C48—C56—H56B	109.5
C20—C29—C37	109.07 (19)	H56A—C56—H56B	109.5
C20—C29—C24	107.87 (19)	C48—C56—H56C	109.5
C37—C29—C24	111.4 (2)	H56A—C56—H56C	109.5
C20—C29—C28	109.88 (19)	H56B—C56—H56C	109.5
C37—C29—C28	110.71 (19)	C51—C57—H57A	109.5
C24—C29—C28	107.83 (19)	C51—C57—H57B	109.5
C31—C30—C28	113.3 (2)	H57A—C57—H57B	109.5
C31—C30—H30A	108.9	C51—C57—H57C	109.5
C28—C30—H30A	108.9	H57A—C57—H57C	109.5
C31—C30—H30B	108.9	H57B—C57—H57C	109.5

C10—C1—C2—C3	−56.7 (3)	C26—C27—C33—C32	−180.0 (2)
C1—C2—C3—C4	54.1 (3)	C28—C27—C33—C32	57.3 (3)
C2—C3—C4—C5	−53.9 (3)	C36A—C32—C33—C27	177.5 (2)
C3—C4—C5—C6	−176.6 (2)	C36—C32—C33—C27	177.5 (2)
C3—C4—C5—C10	56.0 (3)	C31—C32—C33—C27	−60.3 (3)
C4—C5—C6—C7	173.7 (2)	C38—C32—C33—C27	62.9 (3)
C10—C5—C6—C7	−58.2 (3)	C36A—C32—C33—C34	45.7 (2)
C5—C6—C7—C8	52.6 (3)	C36—C32—C33—C34	45.7 (2)
C6—C7—C8—C14	−171.7 (2)	C31—C32—C33—C34	167.9 (2)
C6—C7—C8—C9	−50.5 (3)	C38—C32—C33—C34	−68.8 (3)
C14—C8—C9—C11	−53.0 (3)	C27—C33—C34—C35	−165.8 (2)
C7—C8—C9—C11	−175.6 (2)	C32—C33—C34—C35	−37.9 (3)
C14—C8—C9—C10	177.0 (2)	C33—C34—C35—C36A	15.0 (3)
C7—C8—C9—C10	54.4 (3)	C33—C34—C35—C36	15.0 (3)
C2—C1—C10—C18	−67.1 (3)	C31—C32—C36—C35	−152.7 (2)
C2—C1—C10—C5	55.2 (3)	C33—C32—C36—C35	−36.1 (3)
C2—C1—C10—C9	171.1 (2)	C38—C32—C36—C35	82.3 (3)
C6—C5—C10—C18	−62.2 (3)	C34—C35—C36—C32	13.5 (3)
C4—C5—C10—C18	65.5 (3)	C31—C32—C36A—O1	29.7 (4)
C6—C5—C10—C1	177.6 (2)	C33—C32—C36A—O1	146.3 (3)
C4—C5—C10—C1	−54.7 (3)	C38—C32—C36A—O1	−95.3 (3)
C6—C5—C10—C9	59.7 (3)	C31—C32—C36A—C35	−152.7 (2)
C4—C5—C10—C9	−172.6 (2)	C33—C32—C36A—C35	−36.1 (3)
C11—C9—C10—C18	−63.4 (3)	C38—C32—C36A—C35	82.3 (3)
C8—C9—C10—C18	65.0 (3)	C34—C35—C36A—O1	−169.4 (4)
C11—C9—C10—C1	57.3 (3)	C34—C35—C36A—C32	13.5 (3)
C8—C9—C10—C1	−174.3 (2)	C48—C39—C40—C41	−56.8 (3)
C11—C9—C10—C5	173.7 (2)	C39—C40—C41—C42	56.1 (3)
C8—C9—C10—C5	−57.8 (3)	C40—C41—C42—C43	−55.5 (3)
C8—C9—C11—C12	53.9 (3)	C41—C42—C43—C44	−175.6 (2)
C10—C9—C11—C12	−177.2 (2)	C41—C42—C43—C48	55.9 (3)
C9—C11—C12—C13	−55.1 (3)	C42—C43—C44—C45	172.0 (2)
C11—C12—C13—C14	55.2 (3)	C48—C43—C44—C45	−58.7 (3)
C11—C12—C13—C17	167.2 (2)	C43—C44—C45—C46	53.8 (3)
C11—C12—C13—C19	−69.1 (3)	C44—C45—C46—C52	−172.2 (2)
C7—C8—C14—C15	−55.7 (3)	C44—C45—C46—C47	−51.4 (3)
C9—C8—C14—C15	−178.6 (2)	C52—C46—C47—C49	−54.0 (3)
C7—C8—C14—C13	−179.8 (2)	C45—C46—C47—C49	−176.3 (2)
C9—C8—C14—C13	57.3 (3)	C52—C46—C47—C48	176.4 (2)
C12—C13—C14—C15	169.0 (2)	C45—C46—C47—C48	54.1 (3)
C17—C13—C14—C15	46.7 (2)	C44—C43—C48—C56	−62.6 (3)
C19—C13—C14—C15	−68.2 (3)	C42—C43—C48—C56	66.2 (3)
C12—C13—C14—C8	−58.9 (3)	C44—C43—C48—C39	178.1 (2)
C17—C13—C14—C8	178.9 (2)	C42—C43—C48—C39	−53.1 (3)
C19—C13—C14—C8	63.9 (3)	C44—C43—C48—C47	59.4 (3)
C8—C14—C15—C16	−164.5 (2)	C42—C43—C48—C47	−171.8 (2)
C13—C14—C15—C16	−35.5 (3)	C40—C39—C48—C56	−67.9 (3)
C14—C15—C16—C17	10.3 (3)	C40—C39—C48—C43	53.4 (3)
C12—C13—C17—C16	−156.3 (2)	C40—C39—C48—C47	170.1 (2)
C14—C13—C17—C16	−39.4 (3)	C49—C47—C48—C56	−62.6 (3)
C19—C13—C17—C16	79.0 (3)	C46—C47—C48—C56	65.4 (3)
C15—C16—C17—C13	18.4 (3)	C49—C47—C48—C43	174.9 (2)
C29—C20—C21—C22	−55.4 (3)	C46—C47—C48—C43	−57.0 (3)
C20—C21—C22—C23	54.2 (3)	C49—C47—C48—C39	57.9 (3)
C21—C22—C23—C24	−55.4 (3)	C46—C47—C48—C39	−174.1 (2)
C22—C23—C24—C25	−174.5 (2)	C46—C47—C49—C50	54.5 (3)
C22—C23—C24—C29	57.2 (3)	C48—C47—C49—C50	−176.7 (2)
C23—C24—C25—C26	173.5 (2)	C47—C49—C50—C51	−55.3 (3)
C29—C24—C25—C26	−58.0 (3)	C49—C50—C51—C55A	167.6 (3)
C24—C25—C26—C27	55.7 (3)	C49—C50—C51—C55	167.6 (3)
C25—C26—C27—C33	−176.4 (2)	C49—C50—C51—C57	−69.4 (3)
C25—C26—C27—C28	−54.5 (3)	C49—C50—C51—C52	55.5 (3)
C33—C27—C28—C30	−51.4 (3)	C45—C46—C52—C51	−179.5 (2)
C26—C27—C28—C30	−174.88 (19)	C47—C46—C52—C51	58.2 (3)
C33—C27—C28—C29	179.34 (19)	C45—C46—C52—C53	−55.4 (3)
C26—C27—C28—C29	55.9 (3)	C47—C46—C52—C53	−177.8 (2)
C21—C20—C29—C37	−66.9 (3)	C55A—C51—C52—C46	177.7 (2)
C21—C20—C29—C24	54.3 (3)	C55—C51—C52—C46	177.7 (2)
C21—C20—C29—C28	171.6 (2)	C50—C51—C52—C46	−59.3 (3)
C25—C24—C29—C20	176.21 (19)	C57—C51—C52—C46	63.9 (3)
C23—C24—C29—C20	−55.1 (3)	C55A—C51—C52—C53	45.3 (3)
C25—C24—C29—C37	−64.1 (3)	C55—C51—C52—C53	45.3 (3)
C23—C24—C29—C37	64.6 (3)	C50—C51—C52—C53	168.3 (2)
C25—C24—C29—C28	57.6 (3)	C57—C51—C52—C53	−68.5 (3)
C23—C24—C29—C28	−173.67 (19)	C46—C52—C53—C54	−165.8 (2)
C30—C28—C29—C20	58.2 (3)	C51—C52—C53—C54	−37.1 (3)
C27—C28—C29—C20	−173.71 (19)	C52—C53—C54—C55A	13.9 (3)
C30—C28—C29—C37	−62.3 (3)	C52—C53—C54—C55	13.9 (3)
C27—C28—C29—C37	65.8 (2)	C50—C51—C55—C54	−153.6 (2)
C30—C28—C29—C24	175.51 (19)	C57—C51—C55—C54	81.8 (3)
C27—C28—C29—C24	−56.4 (2)	C52—C51—C55—C54	−36.6 (3)
C27—C28—C30—C31	51.6 (3)	C53—C54—C55—C51	14.4 (3)
C29—C28—C30—C31	179.8 (2)	C50—C51—C55A—O2	22.5 (5)
C28—C30—C31—C32	−54.6 (3)	C57—C51—C55A—O2	−102.1 (4)
C30—C31—C32—C36A	168.4 (2)	C52—C51—C55A—O2	139.5 (4)
C30—C31—C32—C36	168.4 (2)	C50—C51—C55A—C54	−153.6 (2)
C30—C31—C32—C33	56.6 (3)	C57—C51—C55A—C54	81.8 (3)
C30—C31—C32—C38	−68.1 (3)	C52—C51—C55A—C54	−36.6 (3)
C26—C27—C33—C34	−56.8 (3)	C53—C54—C55A—O2	−162.0 (3)
C28—C27—C33—C34	−179.5 (2)	C53—C54—C55A—C51	14.4 (3)

5α,14α-Androstane (Form_II) top

Crystal data top

C₁₉H₃₂	D_x = 1.088 Mg m⁻³
M_r = 260.44	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 86352 reflections
a = 7.1465 (1) Å	θ = 2.5–74.7°
b = 22.2064 (1) Å	µ = 0.44 mm⁻¹
c = 30.0679 (1) Å	T = 90 K
V = 4771.72 (7) Å³	Rod, colorless
Z = 12	0.16 × 0.14 × 0.07 mm
F(000) = 1752

Data collection top

ROD, Synergy Custom system, HyPix diffractometer	9535 independent reflections
Radiation source: Rotating-anode X-ray tube	9414 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.030
ω scans	θ_max = 75.3°, θ_min = 2.5°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021)	h = −8→8
T_min = 0.798, T_max = 1.000	k = −27→27
116227 measured reflections	l = −36→37

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0474P)² + 0.9086P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.29 e Å⁻³
9535 reflections	Δρ_min = −0.14 e Å⁻³
521 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00036 (8)
Primary atom site location: iterative	Absolute structure: Flack x determined using 4010 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.16 (12)

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.3130 (2)	0.69729 (7)	0.46329 (5)	0.0210 (3)
H1A	0.433221	0.716740	0.455461	0.025*
H1B	0.264658	0.717135	0.490441	0.025*
C2	0.3486 (2)	0.63075 (7)	0.47338 (5)	0.0252 (3)
H2A	0.409089	0.611630	0.447348	0.030*
H2B	0.435303	0.627429	0.498935	0.030*
C3	0.1679 (2)	0.59747 (7)	0.48413 (6)	0.0278 (3)
H3A	0.115985	0.612818	0.512474	0.033*
H3B	0.194644	0.554026	0.487873	0.033*
C4	0.0237 (2)	0.60598 (7)	0.44700 (6)	0.0259 (3)
H4A	0.068292	0.585514	0.419733	0.031*
H4B	−0.095931	0.587027	0.455950	0.031*
C5	−0.0098 (2)	0.67267 (7)	0.43691 (5)	0.0198 (3)
H5	−0.057370	0.691020	0.465098	0.024*
C6	−0.1628 (2)	0.68212 (7)	0.40223 (5)	0.0224 (3)
H6A	−0.277149	0.660367	0.411560	0.027*
H6B	−0.121351	0.665130	0.373432	0.027*
C7	−0.2082 (2)	0.74884 (7)	0.39630 (5)	0.0207 (3)
H7A	−0.270397	0.763828	0.423556	0.025*
H7B	−0.297322	0.753404	0.371314	0.025*
C8	−0.0350 (2)	0.78750 (6)	0.38705 (5)	0.0170 (3)
H8	0.013737	0.777186	0.356816	0.020*
C9	0.1214 (2)	0.77534 (6)	0.42159 (5)	0.0174 (3)
H9	0.067340	0.786519	0.451139	0.021*
C10	0.1724 (2)	0.70732 (6)	0.42494 (5)	0.0176 (3)
C11	0.2896 (2)	0.81756 (7)	0.41450 (5)	0.0208 (3)
H11A	0.381202	0.811024	0.438735	0.025*
H11B	0.351551	0.807051	0.386088	0.025*
C12	0.2347 (2)	0.88440 (7)	0.41350 (5)	0.0210 (3)
H12A	0.187663	0.896517	0.443152	0.025*
H12B	0.346531	0.909048	0.406729	0.025*
C13	0.0839 (2)	0.89643 (6)	0.37861 (5)	0.0197 (3)
C14	−0.0832 (2)	0.85457 (6)	0.38797 (5)	0.0180 (3)
H14	−0.124535	0.863605	0.419033	0.022*
C15	−0.2369 (2)	0.87856 (7)	0.35744 (5)	0.0231 (3)
H15A	−0.362445	0.868250	0.369071	0.028*
H15B	−0.223884	0.862053	0.327010	0.028*
C16	−0.2051 (3)	0.94772 (7)	0.35780 (6)	0.0292 (4)
H16A	−0.306188	0.968161	0.374495	0.035*
H16B	−0.203004	0.963699	0.327060	0.035*
C17	−0.0132 (2)	0.95806 (7)	0.38084 (5)	0.0246 (3)
H17A	0.060552	0.988998	0.364887	0.030*
H17B	−0.030440	0.971016	0.412079	0.030*
C18	0.2589 (2)	0.68474 (7)	0.38108 (5)	0.0215 (3)
H18A	0.276597	0.641035	0.382643	0.032*
H18B	0.380082	0.704380	0.376387	0.032*
H18C	0.174985	0.694454	0.356318	0.032*
C19	0.1650 (2)	0.88863 (7)	0.33150 (5)	0.0262 (3)
H19A	0.204687	0.846773	0.327324	0.039*
H19B	0.272822	0.915420	0.327749	0.039*
H19C	0.069028	0.898749	0.309446	0.039*
C20	0.4800 (2)	0.82160 (6)	0.24857 (5)	0.0162 (3)
H20A	0.360901	0.798972	0.250375	0.019*
H20B	0.524297	0.828724	0.279322	0.019*
C21	0.4433 (2)	0.88242 (7)	0.22618 (5)	0.0203 (3)
H21A	0.384695	0.875593	0.196774	0.024*
H21B	0.354576	0.905952	0.244543	0.024*
C22	0.6235 (2)	0.91851 (6)	0.22009 (5)	0.0225 (3)
H22A	0.596176	0.955641	0.203059	0.027*
H22B	0.672668	0.930478	0.249571	0.027*
C23	0.7712 (2)	0.88161 (6)	0.19548 (5)	0.0198 (3)
H23A	0.889479	0.904746	0.194137	0.024*
H23B	0.728810	0.874251	0.164605	0.024*
C24	0.80678 (19)	0.82109 (6)	0.21863 (5)	0.0156 (3)
H24	0.849291	0.830925	0.249468	0.019*
C25	0.9655 (2)	0.78552 (7)	0.19715 (5)	0.0188 (3)
H25A	1.078461	0.811199	0.195174	0.023*
H25B	0.929100	0.773794	0.166591	0.023*
C26	1.0103 (2)	0.72907 (6)	0.22422 (5)	0.0188 (3)
H26A	1.108354	0.705590	0.208699	0.023*
H26B	1.060370	0.741112	0.253606	0.023*
C27	0.83791 (19)	0.68941 (6)	0.23092 (4)	0.0147 (3)
H27	0.795759	0.674617	0.201149	0.018*
C28	0.67619 (19)	0.72620 (6)	0.25199 (4)	0.0138 (3)
H28	0.724676	0.741616	0.281034	0.017*
C29	0.62593 (19)	0.78284 (6)	0.22377 (4)	0.0133 (3)
C30	0.5066 (2)	0.68603 (6)	0.26323 (5)	0.0169 (3)
H30A	0.414007	0.710141	0.280028	0.020*
H30B	0.446680	0.672852	0.235192	0.020*
C31	0.5588 (2)	0.63008 (6)	0.29076 (5)	0.0176 (3)
H31A	0.603190	0.642837	0.320489	0.021*
H31B	0.446399	0.604633	0.294915	0.021*
C32	0.7117 (2)	0.59336 (6)	0.26774 (5)	0.0168 (3)
C33	0.8808 (2)	0.63499 (6)	0.26001 (5)	0.0168 (3)
H33	0.916568	0.651190	0.289854	0.020*
C34	1.0371 (2)	0.59147 (7)	0.24633 (6)	0.0248 (3)
H34A	1.161797	0.608529	0.253195	0.030*
H34B	1.030575	0.582208	0.214162	0.030*
C35	0.9982 (2)	0.53429 (7)	0.27474 (6)	0.0280 (3)
H35A	0.997943	0.497858	0.255767	0.034*
H35B	1.095142	0.529492	0.298004	0.034*
C36	0.8028 (2)	0.54404 (7)	0.29616 (5)	0.0216 (3)
H36A	0.728125	0.506520	0.295235	0.026*
H36B	0.815122	0.557247	0.327475	0.026*
C37	0.5454 (2)	0.76431 (6)	0.17816 (4)	0.0166 (3)
H37A	0.420595	0.746892	0.182247	0.025*
H37B	0.627883	0.734430	0.164338	0.025*
H37C	0.536642	0.799836	0.158942	0.025*
C38	0.6365 (2)	0.56492 (7)	0.22461 (5)	0.0222 (3)
H38A	0.734724	0.540339	0.210893	0.033*
H38B	0.598734	0.596820	0.203959	0.033*
H38C	0.528298	0.539481	0.231513	0.033*
C39	1.3354 (2)	0.33356 (7)	0.53877 (5)	0.0220 (3)
H39A	1.333065	0.300154	0.516978	0.026*
H39B	1.409367	0.366802	0.525655	0.026*
C40	1.4330 (2)	0.31189 (7)	0.58108 (5)	0.0246 (3)
H40A	1.367606	0.275855	0.592684	0.030*
H40B	1.563354	0.300291	0.574008	0.030*
C41	1.4338 (2)	0.36102 (7)	0.61665 (6)	0.0246 (3)
H41A	1.491366	0.345214	0.644231	0.030*
H41B	1.509749	0.395558	0.606276	0.030*
C42	1.2345 (2)	0.38205 (7)	0.62642 (5)	0.0202 (3)
H42A	1.237921	0.415133	0.648474	0.024*
H42B	1.162001	0.348370	0.639384	0.024*
C43	1.1379 (2)	0.40402 (6)	0.58402 (4)	0.0152 (3)
H43	1.215549	0.438032	0.572430	0.018*
C44	0.9436 (2)	0.43000 (6)	0.59295 (4)	0.0174 (3)
H44A	0.951505	0.460420	0.616954	0.021*
H44B	0.858844	0.397470	0.603002	0.021*
C45	0.8642 (2)	0.45918 (6)	0.55097 (4)	0.0176 (3)
H45A	0.939885	0.495090	0.543451	0.021*
H45B	0.734660	0.472799	0.556942	0.021*
C46	0.8629 (2)	0.41622 (6)	0.51122 (4)	0.0151 (3)
H46	0.769754	0.383570	0.517058	0.018*
C47	1.0576 (2)	0.38699 (6)	0.50394 (4)	0.0162 (3)
H47	1.145624	0.420900	0.497553	0.019*
C48	1.1331 (2)	0.35570 (6)	0.54652 (5)	0.0156 (3)
C49	1.0594 (2)	0.34663 (7)	0.46228 (5)	0.0228 (3)
H49A	1.188109	0.331617	0.457278	0.027*
H49B	0.977521	0.311360	0.467459	0.027*
C50	0.9925 (3)	0.38011 (7)	0.42040 (5)	0.0266 (3)
H50A	1.082954	0.412316	0.412939	0.032*
H50B	0.987751	0.351655	0.395083	0.032*
C51	0.7995 (2)	0.40773 (7)	0.42735 (5)	0.0237 (3)
C52	0.8074 (2)	0.44885 (6)	0.46850 (5)	0.0183 (3)
H52	0.908952	0.478769	0.462555	0.022*
C53	0.6228 (2)	0.48422 (7)	0.46669 (5)	0.0245 (3)
H53A	0.634517	0.523406	0.482138	0.029*
H53B	0.519383	0.460999	0.480314	0.029*
C54	0.5900 (3)	0.49321 (8)	0.41579 (6)	0.0328 (4)
H54A	0.461831	0.480609	0.407462	0.039*
H54B	0.606839	0.536028	0.407524	0.039*
C55	0.7370 (3)	0.45342 (7)	0.39211 (5)	0.0319 (4)
H55A	0.681152	0.432698	0.366154	0.038*
H55B	0.844274	0.477988	0.381852	0.038*
C56	1.0103 (2)	0.30139 (6)	0.55920 (5)	0.0193 (3)
H56A	1.020154	0.270413	0.536101	0.029*
H56B	0.879678	0.314351	0.561888	0.029*
H56C	1.052787	0.284832	0.587668	0.029*
C57	0.6499 (3)	0.35826 (7)	0.43114 (6)	0.0297 (4)
H57A	0.526197	0.376847	0.434189	0.045*
H57B	0.675743	0.333272	0.457292	0.045*
H57C	0.652443	0.333128	0.404357	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0202 (7)	0.0206 (7)	0.0222 (7)	−0.0001 (6)	−0.0025 (6)	−0.0011 (6)
C2	0.0255 (8)	0.0230 (7)	0.0270 (8)	0.0026 (6)	−0.0044 (6)	0.0007 (6)
C3	0.0326 (9)	0.0203 (7)	0.0307 (8)	0.0012 (7)	0.0001 (7)	0.0067 (6)
C4	0.0234 (8)	0.0186 (7)	0.0357 (8)	−0.0037 (6)	−0.0003 (7)	0.0021 (6)
C5	0.0179 (7)	0.0196 (7)	0.0218 (7)	−0.0029 (6)	0.0013 (6)	−0.0002 (5)
C6	0.0166 (7)	0.0202 (7)	0.0305 (8)	−0.0049 (6)	−0.0014 (6)	−0.0025 (6)
C7	0.0156 (7)	0.0219 (7)	0.0246 (7)	−0.0037 (6)	−0.0015 (6)	−0.0001 (6)
C8	0.0140 (6)	0.0174 (6)	0.0194 (6)	−0.0013 (5)	0.0011 (5)	−0.0026 (5)
C9	0.0156 (6)	0.0185 (7)	0.0181 (6)	−0.0017 (5)	0.0008 (5)	−0.0024 (5)
C10	0.0154 (6)	0.0184 (7)	0.0190 (6)	−0.0016 (5)	0.0006 (6)	−0.0014 (5)
C11	0.0140 (7)	0.0188 (7)	0.0297 (8)	−0.0009 (6)	−0.0013 (6)	−0.0006 (6)
C12	0.0179 (7)	0.0174 (7)	0.0276 (7)	−0.0033 (6)	−0.0005 (6)	−0.0006 (6)
C13	0.0195 (7)	0.0172 (7)	0.0224 (7)	−0.0013 (6)	0.0014 (6)	−0.0019 (5)
C14	0.0166 (7)	0.0189 (7)	0.0185 (6)	−0.0005 (6)	0.0002 (5)	−0.0017 (5)
C15	0.0204 (7)	0.0228 (7)	0.0260 (7)	0.0002 (6)	−0.0026 (6)	−0.0010 (6)
C16	0.0294 (9)	0.0222 (8)	0.0359 (9)	0.0035 (7)	−0.0085 (7)	0.0001 (6)
C17	0.0254 (8)	0.0171 (7)	0.0314 (8)	0.0010 (6)	−0.0015 (6)	−0.0022 (6)
C18	0.0200 (7)	0.0209 (7)	0.0236 (7)	0.0012 (6)	0.0020 (6)	−0.0032 (6)
C19	0.0267 (8)	0.0266 (8)	0.0253 (8)	−0.0029 (7)	0.0058 (6)	0.0012 (6)
C20	0.0147 (6)	0.0161 (6)	0.0176 (6)	0.0005 (5)	0.0017 (5)	0.0005 (5)
C21	0.0190 (7)	0.0169 (7)	0.0249 (7)	0.0035 (6)	0.0032 (6)	0.0012 (6)
C22	0.0228 (7)	0.0148 (7)	0.0300 (8)	0.0009 (6)	0.0016 (6)	0.0007 (6)
C23	0.0191 (7)	0.0145 (6)	0.0256 (7)	−0.0024 (6)	0.0032 (6)	0.0024 (5)
C24	0.0135 (6)	0.0152 (6)	0.0181 (6)	−0.0021 (5)	0.0006 (5)	0.0006 (5)
C25	0.0143 (7)	0.0178 (7)	0.0244 (7)	−0.0015 (5)	0.0040 (6)	0.0042 (5)
C26	0.0124 (6)	0.0176 (7)	0.0265 (7)	0.0000 (5)	0.0019 (6)	0.0042 (5)
C27	0.0120 (6)	0.0155 (6)	0.0167 (6)	−0.0007 (5)	0.0007 (5)	0.0025 (5)
C28	0.0135 (6)	0.0150 (6)	0.0128 (6)	−0.0008 (5)	−0.0005 (5)	0.0014 (5)
C29	0.0122 (6)	0.0136 (6)	0.0141 (6)	−0.0003 (5)	0.0010 (5)	0.0009 (5)
C30	0.0129 (6)	0.0178 (7)	0.0201 (6)	−0.0002 (5)	0.0017 (5)	0.0043 (5)
C31	0.0165 (7)	0.0185 (7)	0.0179 (6)	−0.0015 (5)	0.0027 (5)	0.0048 (5)
C32	0.0172 (7)	0.0157 (6)	0.0176 (6)	−0.0015 (6)	−0.0006 (5)	0.0034 (5)
C33	0.0133 (6)	0.0172 (7)	0.0198 (7)	−0.0004 (5)	−0.0008 (5)	0.0032 (5)
C34	0.0173 (7)	0.0203 (7)	0.0368 (8)	0.0034 (6)	0.0043 (6)	0.0080 (6)
C35	0.0249 (8)	0.0210 (7)	0.0382 (9)	0.0045 (6)	0.0021 (7)	0.0092 (7)
C36	0.0236 (8)	0.0175 (7)	0.0236 (7)	−0.0007 (6)	−0.0015 (6)	0.0061 (6)
C37	0.0171 (7)	0.0167 (6)	0.0159 (6)	−0.0020 (5)	−0.0023 (5)	0.0011 (5)
C38	0.0267 (8)	0.0185 (7)	0.0212 (7)	−0.0038 (6)	−0.0023 (6)	0.0002 (5)
C39	0.0182 (7)	0.0209 (7)	0.0269 (7)	0.0035 (6)	0.0037 (6)	0.0002 (6)
C40	0.0156 (7)	0.0226 (7)	0.0356 (8)	0.0045 (6)	−0.0005 (6)	0.0036 (6)
C41	0.0177 (7)	0.0241 (7)	0.0320 (8)	−0.0010 (6)	−0.0070 (6)	0.0043 (6)
C42	0.0192 (7)	0.0213 (7)	0.0201 (7)	−0.0006 (6)	−0.0039 (6)	0.0021 (6)
C43	0.0148 (6)	0.0145 (6)	0.0165 (6)	−0.0013 (5)	−0.0003 (5)	0.0013 (5)
C44	0.0181 (7)	0.0203 (7)	0.0139 (6)	0.0022 (6)	0.0010 (5)	−0.0017 (5)
C45	0.0181 (7)	0.0170 (6)	0.0176 (6)	0.0042 (6)	−0.0002 (5)	−0.0009 (5)
C46	0.0166 (6)	0.0136 (6)	0.0152 (6)	−0.0009 (5)	0.0000 (5)	0.0006 (5)
C47	0.0197 (7)	0.0136 (6)	0.0152 (6)	−0.0007 (5)	0.0025 (5)	0.0003 (5)
C48	0.0150 (6)	0.0137 (6)	0.0181 (6)	−0.0009 (5)	0.0011 (5)	0.0004 (5)
C49	0.0314 (8)	0.0186 (7)	0.0183 (7)	0.0039 (6)	0.0026 (6)	−0.0028 (5)
C50	0.0444 (10)	0.0217 (7)	0.0137 (6)	0.0003 (7)	0.0028 (7)	−0.0023 (6)
C51	0.0379 (9)	0.0169 (7)	0.0162 (6)	−0.0044 (7)	−0.0050 (6)	0.0016 (5)
C52	0.0244 (7)	0.0133 (6)	0.0172 (6)	−0.0017 (5)	−0.0024 (6)	0.0012 (5)
C53	0.0270 (8)	0.0209 (7)	0.0256 (7)	0.0012 (6)	−0.0083 (6)	0.0041 (6)
C54	0.0456 (10)	0.0246 (8)	0.0283 (8)	0.0000 (7)	−0.0170 (8)	0.0060 (6)
C55	0.0539 (11)	0.0225 (7)	0.0192 (7)	−0.0033 (8)	−0.0112 (7)	0.0045 (6)
C56	0.0206 (7)	0.0149 (6)	0.0225 (7)	−0.0030 (6)	−0.0019 (6)	0.0035 (5)
C57	0.0435 (10)	0.0188 (7)	0.0268 (8)	−0.0073 (7)	−0.0134 (7)	0.0006 (6)

Geometric parameters (Å, º) top

C1—C2	1.530 (2)	C28—H28	1.0000
C1—C10	1.546 (2)	C29—C37	1.5430 (18)
C1—H1A	0.9900	C30—C31	1.5385 (18)
C1—H1B	0.9900	C30—H30A	0.9900
C2—C3	1.523 (2)	C30—H30B	0.9900
C2—H2A	0.9900	C31—C32	1.529 (2)
C2—H2B	0.9900	C31—H31A	0.9900
C3—C4	1.531 (2)	C31—H31B	0.9900
C3—H3A	0.9900	C32—C36	1.5344 (19)
C3—H3B	0.9900	C32—C38	1.539 (2)
C4—C5	1.531 (2)	C32—C33	1.5394 (19)
C4—H4A	0.9900	C33—C34	1.533 (2)
C4—H4B	0.9900	C33—H33	1.0000
C5—C6	1.525 (2)	C34—C35	1.555 (2)
C5—C10	1.554 (2)	C34—H34A	0.9900
C5—H5	1.0000	C34—H34B	0.9900
C6—C7	1.527 (2)	C35—C36	1.553 (2)
C6—H6A	0.9900	C35—H35A	0.9900
C6—H6B	0.9900	C35—H35B	0.9900
C7—C8	1.532 (2)	C36—H36A	0.9900
C7—H7A	0.9900	C36—H36B	0.9900
C7—H7B	0.9900	C37—H37A	0.9800
C8—C14	1.5289 (19)	C37—H37B	0.9800
C8—C9	1.550 (2)	C37—H37C	0.9800
C8—H8	1.0000	C38—H38A	0.9800
C9—C11	1.539 (2)	C38—H38B	0.9800
C9—C10	1.557 (2)	C38—H38C	0.9800
C9—H9	1.0000	C39—C40	1.528 (2)
C10—C18	1.540 (2)	C39—C48	1.5446 (19)
C11—C12	1.536 (2)	C39—H39A	0.9900
C11—H11A	0.9900	C39—H39B	0.9900
C11—H11B	0.9900	C40—C41	1.528 (2)
C12—C13	1.527 (2)	C40—H40A	0.9900
C12—H12A	0.9900	C40—H40B	0.9900
C12—H12B	0.9900	C41—C42	1.527 (2)
C13—C17	1.536 (2)	C41—H41A	0.9900
C13—C14	1.539 (2)	C41—H41B	0.9900
C13—C19	1.540 (2)	C42—C43	1.5298 (19)
C14—C15	1.527 (2)	C42—H42A	0.9900
C14—H14	1.0000	C42—H42B	0.9900
C15—C16	1.553 (2)	C43—C44	1.5274 (19)
C15—H15A	0.9900	C43—C48	1.5568 (19)
C15—H15B	0.9900	C43—H43	1.0000
C16—C17	1.553 (2)	C44—C45	1.5282 (19)
C16—H16A	0.9900	C44—H44A	0.9900
C16—H16B	0.9900	C44—H44B	0.9900
C17—H17A	0.9900	C45—C46	1.5294 (18)
C17—H17B	0.9900	C45—H45A	0.9900
C18—H18A	0.9800	C45—H45B	0.9900
C18—H18B	0.9800	C46—C52	1.5270 (18)
C18—H18C	0.9800	C46—C47	1.5503 (19)
C19—H19A	0.9800	C46—H46	1.0000
C19—H19B	0.9800	C47—C49	1.5404 (19)
C19—H19C	0.9800	C47—C48	1.5535 (18)
C20—C21	1.5319 (19)	C47—H47	1.0000
C20—C29	1.5440 (19)	C48—C56	1.5395 (19)
C20—H20A	0.9900	C49—C50	1.538 (2)
C20—H20B	0.9900	C49—H49A	0.9900
C21—C22	1.528 (2)	C49—H49B	0.9900
C21—H21A	0.9900	C50—C51	1.524 (2)
C21—H21B	0.9900	C50—H50A	0.9900
C22—C23	1.527 (2)	C50—H50B	0.9900
C22—H22A	0.9900	C51—C55	1.533 (2)
C22—H22B	0.9900	C51—C57	1.537 (2)
C23—C24	1.5348 (19)	C51—C52	1.539 (2)
C23—H23A	0.9900	C52—C53	1.536 (2)
C23—H23B	0.9900	C52—H52	1.0000
C24—C25	1.526 (2)	C53—C54	1.561 (2)
C24—C29	1.5543 (18)	C53—H53A	0.9900
C24—H24	1.0000	C53—H53B	0.9900
C25—C26	1.5286 (19)	C54—C55	1.547 (3)
C25—H25A	0.9900	C54—H54A	0.9900
C25—H25B	0.9900	C54—H54B	0.9900
C26—C27	1.5280 (19)	C55—H55A	0.9900
C26—H26A	0.9900	C55—H55B	0.9900
C26—H26B	0.9900	C56—H56A	0.9800
C27—C33	1.5229 (18)	C56—H56B	0.9800
C27—C28	1.5507 (18)	C56—H56C	0.9800
C27—H27	1.0000	C57—H57A	0.9800
C28—C30	1.5421 (19)	C57—H57B	0.9800
C28—C29	1.5591 (18)	C57—H57C	0.9800

C2—C1—C10	113.28 (12)	C37—C29—C28	110.75 (11)
C2—C1—H1A	108.9	C20—C29—C28	110.03 (11)
C10—C1—H1A	108.9	C24—C29—C28	107.67 (11)
C2—C1—H1B	108.9	C31—C30—C28	113.25 (12)
C10—C1—H1B	108.9	C31—C30—H30A	108.9
H1A—C1—H1B	107.7	C28—C30—H30A	108.9
C3—C2—C1	111.72 (13)	C31—C30—H30B	108.9
C3—C2—H2A	109.3	C28—C30—H30B	108.9
C1—C2—H2A	109.3	H30A—C30—H30B	107.7
C3—C2—H2B	109.3	C32—C31—C30	111.11 (11)
C1—C2—H2B	109.3	C32—C31—H31A	109.4
H2A—C2—H2B	107.9	C30—C31—H31A	109.4
C2—C3—C4	110.87 (13)	C32—C31—H31B	109.4
C2—C3—H3A	109.5	C30—C31—H31B	109.4
C4—C3—H3A	109.5	H31A—C31—H31B	108.0
C2—C3—H3B	109.5	C31—C32—C36	115.59 (12)
C4—C3—H3B	109.5	C31—C32—C38	110.55 (12)
H3A—C3—H3B	108.1	C36—C32—C38	108.94 (12)
C5—C4—C3	111.65 (13)	C31—C32—C33	108.01 (11)
C5—C4—H4A	109.3	C36—C32—C33	100.32 (11)
C3—C4—H4A	109.3	C38—C32—C33	113.15 (12)
C5—C4—H4B	109.3	C27—C33—C34	119.52 (12)
C3—C4—H4B	109.3	C27—C33—C32	113.90 (11)
H4A—C4—H4B	108.0	C34—C33—C32	103.54 (11)
C6—C5—C4	112.36 (12)	C27—C33—H33	106.3
C6—C5—C10	111.96 (12)	C34—C33—H33	106.3
C4—C5—C10	113.21 (13)	C32—C33—H33	106.3
C6—C5—H5	106.2	C33—C34—C35	103.71 (12)
C4—C5—H5	106.2	C33—C34—H34A	111.0
C10—C5—H5	106.2	C35—C34—H34A	111.0
C5—C6—C7	111.45 (12)	C33—C34—H34B	111.0
C5—C6—H6A	109.3	C35—C34—H34B	111.0
C7—C6—H6A	109.3	H34A—C34—H34B	109.0
C5—C6—H6B	109.3	C36—C35—C34	105.94 (12)
C7—C6—H6B	109.3	C36—C35—H35A	110.5
H6A—C6—H6B	108.0	C34—C35—H35A	110.5
C6—C7—C8	113.15 (12)	C36—C35—H35B	110.5
C6—C7—H7A	108.9	C34—C35—H35B	110.5
C8—C7—H7A	108.9	H35A—C35—H35B	108.7
C6—C7—H7B	108.9	C32—C36—C35	104.50 (12)
C8—C7—H7B	108.9	C32—C36—H36A	110.9
H7A—C7—H7B	107.8	C35—C36—H36A	110.9
C14—C8—C7	111.15 (12)	C32—C36—H36B	110.9
C14—C8—C9	108.66 (11)	C35—C36—H36B	110.9
C7—C8—C9	111.31 (12)	H36A—C36—H36B	108.9
C14—C8—H8	108.5	C29—C37—H37A	109.5
C7—C8—H8	108.5	C29—C37—H37B	109.5
C9—C8—H8	108.5	H37A—C37—H37B	109.5
C11—C9—C8	111.37 (12)	C29—C37—H37C	109.5
C11—C9—C10	114.64 (12)	H37A—C37—H37C	109.5
C8—C9—C10	112.40 (11)	H37B—C37—H37C	109.5
C11—C9—H9	105.9	C32—C38—H38A	109.5
C8—C9—H9	105.9	C32—C38—H38B	109.5
C10—C9—H9	105.9	H38A—C38—H38B	109.5
C18—C10—C1	109.31 (12)	C32—C38—H38C	109.5
C18—C10—C5	111.92 (12)	H38A—C38—H38C	109.5
C1—C10—C5	107.49 (12)	H38B—C38—H38C	109.5
C18—C10—C9	110.75 (12)	C40—C39—C48	113.68 (12)
C1—C10—C9	109.88 (11)	C40—C39—H39A	108.8
C5—C10—C9	107.42 (11)	C48—C39—H39A	108.8
C12—C11—C9	113.04 (12)	C40—C39—H39B	108.8
C12—C11—H11A	109.0	C48—C39—H39B	108.8
C9—C11—H11A	109.0	H39A—C39—H39B	107.7
C12—C11—H11B	109.0	C41—C40—C39	111.08 (12)
C9—C11—H11B	109.0	C41—C40—H40A	109.4
H11A—C11—H11B	107.8	C39—C40—H40A	109.4
C13—C12—C11	111.28 (12)	C41—C40—H40B	109.4
C13—C12—H12A	109.4	C39—C40—H40B	109.4
C11—C12—H12A	109.4	H40A—C40—H40B	108.0
C13—C12—H12B	109.4	C42—C41—C40	110.44 (12)
C11—C12—H12B	109.4	C42—C41—H41A	109.6
H12A—C12—H12B	108.0	C40—C41—H41A	109.6
C12—C13—C17	116.41 (12)	C42—C41—H41B	109.6
C12—C13—C14	108.43 (12)	C40—C41—H41B	109.6
C17—C13—C14	100.34 (12)	H41A—C41—H41B	108.1
C12—C13—C19	110.29 (13)	C41—C42—C43	111.00 (12)
C17—C13—C19	108.07 (12)	C41—C42—H42A	109.4
C14—C13—C19	113.08 (12)	C43—C42—H42A	109.4
C15—C14—C8	119.39 (12)	C41—C42—H42B	109.4
C15—C14—C13	103.74 (12)	C43—C42—H42B	109.4
C8—C14—C13	114.22 (12)	H42A—C42—H42B	108.0
C15—C14—H14	106.2	C44—C43—C42	112.60 (11)
C8—C14—H14	106.2	C44—C43—C48	111.59 (11)
C13—C14—H14	106.2	C42—C43—C48	113.18 (11)
C14—C15—C16	103.63 (12)	C44—C43—H43	106.3
C14—C15—H15A	111.0	C42—C43—H43	106.3
C16—C15—H15A	111.0	C48—C43—H43	106.3
C14—C15—H15B	111.0	C43—C44—C45	110.64 (11)
C16—C15—H15B	111.0	C43—C44—H44A	109.5
H15A—C15—H15B	109.0	C45—C44—H44A	109.5
C15—C16—C17	106.16 (13)	C43—C44—H44B	109.5
C15—C16—H16A	110.5	C45—C44—H44B	109.5
C17—C16—H16A	110.5	H44A—C44—H44B	108.1
C15—C16—H16B	110.5	C44—C45—C46	112.54 (11)
C17—C16—H16B	110.5	C44—C45—H45A	109.1
H16A—C16—H16B	108.7	C46—C45—H45A	109.1
C13—C17—C16	104.35 (12)	C44—C45—H45B	109.1
C13—C17—H17A	110.9	C46—C45—H45B	109.1
C16—C17—H17A	110.9	H45A—C45—H45B	107.8
C13—C17—H17B	110.9	C52—C46—C45	111.27 (11)
C16—C17—H17B	110.9	C52—C46—C47	108.25 (11)
H17A—C17—H17B	108.9	C45—C46—C47	111.49 (11)
C10—C18—H18A	109.5	C52—C46—H46	108.6
C10—C18—H18B	109.5	C45—C46—H46	108.6
H18A—C18—H18B	109.5	C47—C46—H46	108.6
C10—C18—H18C	109.5	C49—C47—C46	111.46 (12)
H18A—C18—H18C	109.5	C49—C47—C48	114.02 (11)
H18B—C18—H18C	109.5	C46—C47—C48	112.51 (11)
C13—C19—H19A	109.5	C49—C47—H47	106.1
C13—C19—H19B	109.5	C46—C47—H47	106.1
H19A—C19—H19B	109.5	C48—C47—H47	106.1
C13—C19—H19C	109.5	C56—C48—C39	108.76 (11)
H19A—C19—H19C	109.5	C56—C48—C47	110.87 (12)
H19B—C19—H19C	109.5	C39—C48—C47	110.08 (12)
C21—C20—C29	113.26 (11)	C56—C48—C43	111.91 (11)
C21—C20—H20A	108.9	C39—C48—C43	107.94 (11)
C29—C20—H20A	108.9	C47—C48—C43	107.22 (10)
C21—C20—H20B	108.9	C50—C49—C47	112.45 (12)
C29—C20—H20B	108.9	C50—C49—H49A	109.1
H20A—C20—H20B	107.7	C47—C49—H49A	109.1
C22—C21—C20	111.77 (12)	C50—C49—H49B	109.1
C22—C21—H21A	109.3	C47—C49—H49B	109.1
C20—C21—H21A	109.3	H49A—C49—H49B	107.8
C22—C21—H21B	109.3	C51—C50—C49	111.33 (13)
C20—C21—H21B	109.3	C51—C50—H50A	109.4
H21A—C21—H21B	107.9	C49—C50—H50A	109.4
C23—C22—C21	111.05 (12)	C51—C50—H50B	109.4
C23—C22—H22A	109.4	C49—C50—H50B	109.4
C21—C22—H22A	109.4	H50A—C50—H50B	108.0
C23—C22—H22B	109.4	C50—C51—C55	115.79 (14)
C21—C22—H22B	109.4	C50—C51—C57	110.60 (13)
H22A—C22—H22B	108.0	C55—C51—C57	108.77 (14)
C22—C23—C24	111.38 (12)	C50—C51—C52	108.40 (13)
C22—C23—H23A	109.4	C55—C51—C52	100.01 (12)
C24—C23—H23A	109.4	C57—C51—C52	112.96 (13)
C22—C23—H23B	109.4	C46—C52—C53	119.71 (13)
C24—C23—H23B	109.4	C46—C52—C51	113.85 (11)
H23A—C23—H23B	108.0	C53—C52—C51	104.07 (12)
C25—C24—C23	112.62 (11)	C46—C52—H52	106.1
C25—C24—C29	112.18 (11)	C53—C52—H52	106.1
C23—C24—C29	112.70 (11)	C51—C52—H52	106.1
C25—C24—H24	106.2	C52—C53—C54	103.25 (13)
C23—C24—H24	106.2	C52—C53—H53A	111.1
C29—C24—H24	106.2	C54—C53—H53A	111.1
C24—C25—C26	110.80 (11)	C52—C53—H53B	111.1
C24—C25—H25A	109.5	C54—C53—H53B	111.1
C26—C25—H25A	109.5	H53A—C53—H53B	109.1
C24—C25—H25B	109.5	C55—C54—C53	106.03 (13)
C26—C25—H25B	109.5	C55—C54—H54A	110.5
H25A—C25—H25B	108.1	C53—C54—H54A	110.5
C27—C26—C25	111.96 (12)	C55—C54—H54B	110.5
C27—C26—H26A	109.2	C53—C54—H54B	110.5
C25—C26—H26A	109.2	H54A—C54—H54B	108.7
C27—C26—H26B	109.2	C51—C55—C54	104.93 (13)
C25—C26—H26B	109.2	C51—C55—H55A	110.8
H26A—C26—H26B	107.9	C54—C55—H55A	110.8
C33—C27—C26	111.76 (11)	C51—C55—H55B	110.8
C33—C27—C28	109.48 (11)	C54—C55—H55B	110.8
C26—C27—C28	110.57 (11)	H55A—C55—H55B	108.8
C33—C27—H27	108.3	C48—C56—H56A	109.5
C26—C27—H27	108.3	C48—C56—H56B	109.5
C28—C27—H27	108.3	H56A—C56—H56B	109.5
C30—C28—C27	111.74 (11)	C48—C56—H56C	109.5
C30—C28—C29	113.89 (11)	H56A—C56—H56C	109.5
C27—C28—C29	111.99 (11)	H56B—C56—H56C	109.5
C30—C28—H28	106.2	C51—C57—H57A	109.5
C27—C28—H28	106.2	C51—C57—H57B	109.5
C29—C28—H28	106.2	H57A—C57—H57B	109.5
C37—C29—C20	109.03 (11)	C51—C57—H57C	109.5
C37—C29—C24	111.55 (11)	H57A—C57—H57C	109.5
C20—C29—C24	107.76 (11)	H57B—C57—H57C	109.5

C10—C1—C2—C3	−56.62 (18)	C27—C28—C29—C20	−173.80 (11)
C1—C2—C3—C4	54.22 (18)	C30—C28—C29—C24	175.38 (11)
C2—C3—C4—C5	−53.98 (18)	C27—C28—C29—C24	−56.61 (14)
C3—C4—C5—C6	−176.07 (13)	C27—C28—C30—C31	51.40 (15)
C3—C4—C5—C10	55.88 (17)	C29—C28—C30—C31	179.54 (11)
C4—C5—C6—C7	173.97 (13)	C28—C30—C31—C32	−54.78 (16)
C10—C5—C6—C7	−57.32 (17)	C30—C31—C32—C36	168.07 (12)
C5—C6—C7—C8	52.42 (17)	C30—C31—C32—C38	−67.60 (15)
C6—C7—C8—C14	−171.88 (12)	C30—C31—C32—C33	56.69 (15)
C6—C7—C8—C9	−50.60 (16)	C26—C27—C33—C34	−56.81 (17)
C14—C8—C9—C11	−52.96 (15)	C28—C27—C33—C34	−179.67 (12)
C7—C8—C9—C11	−175.68 (12)	C26—C27—C33—C32	−179.85 (11)
C14—C8—C9—C10	176.82 (11)	C28—C27—C33—C32	57.30 (15)
C7—C8—C9—C10	54.11 (15)	C31—C32—C33—C27	−60.18 (15)
C2—C1—C10—C18	−66.77 (16)	C36—C32—C33—C27	178.42 (12)
C2—C1—C10—C5	54.90 (16)	C38—C32—C33—C27	62.53 (16)
C2—C1—C10—C9	171.50 (12)	C31—C32—C33—C34	168.44 (11)
C6—C5—C10—C18	−62.88 (16)	C36—C32—C33—C34	47.04 (14)
C4—C5—C10—C18	65.38 (16)	C38—C32—C33—C34	−68.85 (15)
C6—C5—C10—C1	177.09 (12)	C27—C33—C34—C35	−163.47 (13)
C4—C5—C10—C1	−54.65 (15)	C32—C33—C34—C35	−35.51 (16)
C6—C5—C10—C9	58.89 (15)	C33—C34—C35—C36	10.22 (17)
C4—C5—C10—C9	−172.85 (12)	C31—C32—C36—C35	−155.81 (13)
C11—C9—C10—C18	−63.32 (16)	C38—C32—C36—C35	79.03 (15)
C8—C9—C10—C18	65.20 (15)	C33—C32—C36—C35	−39.98 (14)
C11—C9—C10—C1	57.55 (16)	C34—C35—C36—C32	18.76 (16)
C8—C9—C10—C1	−173.93 (12)	C48—C39—C40—C41	−56.35 (17)
C11—C9—C10—C5	174.19 (12)	C39—C40—C41—C42	56.13 (17)
C8—C9—C10—C5	−57.29 (15)	C40—C41—C42—C43	−56.52 (16)
C8—C9—C11—C12	53.58 (16)	C41—C42—C43—C44	−175.54 (12)
C10—C9—C11—C12	−177.39 (12)	C41—C42—C43—C48	56.75 (16)
C9—C11—C12—C13	−55.03 (17)	C42—C43—C44—C45	172.12 (12)
C11—C12—C13—C17	167.40 (13)	C48—C43—C44—C45	−59.33 (15)
C11—C12—C13—C14	55.27 (16)	C43—C44—C45—C46	54.40 (16)
C11—C12—C13—C19	−69.04 (16)	C44—C45—C46—C52	−172.49 (12)
C7—C8—C14—C15	−56.08 (17)	C44—C45—C46—C47	−51.53 (15)
C9—C8—C14—C15	−178.89 (13)	C52—C46—C47—C49	−53.94 (14)
C7—C8—C14—C13	−179.60 (12)	C45—C46—C47—C49	−176.65 (11)
C9—C8—C14—C13	57.58 (15)	C52—C46—C47—C48	176.55 (11)
C12—C13—C14—C15	169.46 (12)	C45—C46—C47—C48	53.84 (14)
C17—C13—C14—C15	46.96 (14)	C40—C39—C48—C56	−68.22 (15)
C19—C13—C14—C15	−67.90 (15)	C40—C39—C48—C47	170.12 (12)
C12—C13—C14—C8	−58.93 (15)	C40—C39—C48—C43	53.40 (15)
C17—C13—C14—C8	178.57 (12)	C49—C47—C48—C56	−62.46 (16)
C19—C13—C14—C8	63.70 (16)	C46—C47—C48—C56	65.73 (14)
C8—C14—C15—C16	−164.31 (13)	C49—C47—C48—C39	57.93 (16)
C13—C14—C15—C16	−35.81 (15)	C46—C47—C48—C39	−173.88 (11)
C14—C15—C16—C17	10.78 (17)	C49—C47—C48—C43	175.10 (12)
C12—C13—C17—C16	−156.05 (14)	C46—C47—C48—C43	−56.71 (14)
C14—C13—C17—C16	−39.35 (15)	C44—C43—C48—C56	−62.14 (15)
C19—C13—C17—C16	79.25 (15)	C42—C43—C48—C56	66.10 (15)
C15—C16—C17—C13	18.08 (17)	C44—C43—C48—C39	178.21 (11)
C29—C20—C21—C22	−55.67 (16)	C42—C43—C48—C39	−53.55 (15)
C20—C21—C22—C23	53.82 (17)	C44—C43—C48—C47	59.65 (14)
C21—C22—C23—C24	−54.47 (17)	C42—C43—C48—C47	−172.11 (12)
C22—C23—C24—C25	−175.05 (12)	C46—C47—C49—C50	54.01 (17)
C22—C23—C24—C29	56.80 (16)	C48—C47—C49—C50	−177.28 (13)
C23—C24—C25—C26	173.76 (12)	C47—C49—C50—C51	−55.13 (18)
C29—C24—C25—C26	−57.82 (15)	C49—C50—C51—C55	167.09 (13)
C24—C25—C26—C27	55.59 (16)	C49—C50—C51—C57	−68.62 (16)
C25—C26—C27—C33	−176.90 (12)	C49—C50—C51—C52	55.73 (16)
C25—C26—C27—C28	−54.66 (15)	C45—C46—C52—C53	−54.84 (17)
C33—C27—C28—C30	−51.06 (15)	C47—C46—C52—C53	−177.68 (12)
C26—C27—C28—C30	−174.63 (11)	C45—C46—C52—C51	−178.77 (13)
C33—C27—C28—C29	179.79 (11)	C47—C46—C52—C51	58.39 (16)
C26—C27—C28—C29	56.23 (15)	C50—C51—C52—C46	−59.64 (16)
C21—C20—C29—C37	−66.37 (15)	C55—C51—C52—C46	178.74 (14)
C21—C20—C29—C24	54.86 (15)	C57—C51—C52—C46	63.29 (18)
C21—C20—C29—C28	171.98 (11)	C50—C51—C52—C53	168.33 (12)
C25—C24—C29—C37	−64.15 (15)	C55—C51—C52—C53	46.71 (16)
C23—C24—C29—C37	64.23 (15)	C57—C51—C52—C53	−68.74 (16)
C25—C24—C29—C20	176.21 (11)	C46—C52—C53—C54	−163.51 (13)
C23—C24—C29—C20	−55.41 (14)	C51—C52—C53—C54	−34.98 (15)
C25—C24—C29—C28	57.56 (14)	C52—C53—C54—C55	9.59 (17)
C23—C24—C29—C28	−174.06 (11)	C50—C51—C55—C54	−156.18 (14)
C30—C28—C29—C37	−62.42 (14)	C57—C51—C55—C54	78.58 (16)
C27—C28—C29—C37	65.59 (14)	C52—C51—C55—C54	−40.00 (17)
C30—C28—C29—C20	58.20 (14)	C53—C54—C55—C51	19.21 (18)

Maximum deviation (and RMSD, Å) between crystallograpically independent molecule overlays of Form I top

Ring definitions: (#1) C1–C19, (#2) C20–C38, (#3) C39–C57, and (#4) C58–C76.

	#2	#3	#4
#1	0.0651 (0.0336)	0.0597 (0.0220)	0.0635 (0.0318)
#2	-	0.0764 (0.0359)	0.0321 (0.0196)
#3	-	-	0.0943 (0.0407)

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