A structural study of (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1,3,5-tri­phenyl­cyclo­hexan-1-ol chloro­form hemisolvate and (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1-phenyl-3,5-bis­(2-meth­oxy­phen­yl)cyclo­hexan-1-ol

(1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-1,3,5-tri­phenyl­cyclo­hexan-1-ol or (4-hy­droxy-2,4,6-tri­phenyl­cyclo­hexane-1,3-di­yl)bis­(phenyl­methanone), C₃₈H₃₂O₃, (1), is formed as a by-product in the NaOH-catalyzed synthesis of 1,3,5-tri­phenyl­pentane-1,5-dione from aceto­phenone and benzaldehyde. Single crystals of the chloro­form hemi­solvate, C₃₈H₃₂O₃·0.5CHCl₃, were grown from chloro­form. The structure has triclinic (P) symmetry. One diastereomer [as a pair of (1RS,2SR,3RS,4SR,5RS)-enanti­omers] of (1) has been found in the crystal structure and confirmed by NMR studies. The dichoro­methane hemisolvate has been reported previously [Zhang et al. (2007). Acta Cryst. E63, o4652]. (1RS,2SR,3RS,4SR,5RS)-2,4-Di­benzoyl-3,5-bis­(2-meth­oxy­phen­yl)-1-phenylcyclo­hex­an-1-ol or [4-hy­droxy-2,6-bis­(2-meth­oxy­phen­yl)-4-phenyl­cyclo­hexane-1,3-di­yl]bis­(phenyl­methanone), C₄₀H₃₆O₅, (2), is also formed as a by-product, under the same conditions, from aceto­phenone and 2-meth­oxy­benzaldehyde. Crystals of (2) have been grown from chloro­form. The structure has ortho­rhom­bic (Pca2₁) symmetry. A diastereomer of (2) possesses the same configuration as (1). In both structures, the cyclo­hexane ring adopts a chair conformation with all bulky groups (benzoyl, phenyl and 2-meth­oxy­phen­yl) in equatorial positions. The mol­ecules of (1) and (2) both display one intra­molecular O—H...O hydrogen bond.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

(mol-1) (4-Hydroxy-2,4,6-triphenylcyclohexane-1,3-diyl)bis(phenylmethanone) chloroform hemisolvate

Crystal data

C38H32O3·0.5CHCl3	F(000) = 1252
Mr = 596.32	Dx = 1.312 Mg m^−3
Triclinic, P1	Melting point = 524–525 K
a = 12.3059 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3943 (7) Å	Cell parameters from 5406 reflections
c = 20.4500 (12) Å	θ = 2.5–28.3°
α = 94.385 (1)°	µ = 0.21 mm^−1
β = 97.292 (1)°	T = 123 K
γ = 101.074 (1)°	Block, colourless
V = 3019.9 (3) Å^3	0.6 × 0.5 × 0.3 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	15042 independent reflections
Radiation source: fine-focus sealed tube	11035 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −16→16
Tmin = 0.826, Tmax = 1.000	k = −16→16
35428 measured reflections	l = −27→27

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)] = 0.046	Hydrogen site location: mixed
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.9957P] where P = (Fo^2 + 2Fc^2)/3
15042 reflections	(Δ/σ)max = 0.001
783 parameters	Δρmax = 0.79 e Å^−3
2 restraints	Δρmin = −0.35 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
Cl1	0.16036 (4)	0.28466 (4)	0.36573 (2)	0.02701 (10)
Cl2	0.11889 (4)	0.44456 (4)	0.46621 (2)	0.03033 (11)
Cl3	0.21120 (4)	0.25728 (4)	0.50478 (2)	0.02812 (11)
O1	0.86315 (10)	−0.09124 (10)	0.35920 (6)	0.0208 (3)
H1	0.8121 (16)	−0.1332 (16)	0.3782 (10)	0.034 (6)*
O2	0.65566 (10)	−0.15878 (10)	0.39113 (6)	0.0219 (3)
O3	0.75886 (10)	−0.25280 (10)	0.16312 (6)	0.0220 (3)
C1	0.82050 (13)	0.00492 (13)	0.34348 (8)	0.0156 (3)
C2	0.69368 (13)	−0.02700 (13)	0.31476 (8)	0.0142 (3)
H2	0.6667	0.0410	0.3027	0.017*
C3	0.67357 (13)	−0.11134 (13)	0.25232 (8)	0.0146 (3)
H3	0.6953	−0.1806	0.2665	0.017*
C4	0.74760 (13)	−0.06989 (13)	0.19990 (8)	0.0148 (3)
H4	0.7205	−0.0071	0.1798	0.018*
C5	0.87304 (13)	−0.03252 (13)	0.22937 (8)	0.0146 (3)
H5	0.8995	−0.0989	0.2450	0.018*
C6	0.88679 (14)	0.05262 (13)	0.28993 (8)	0.0166 (3)
H6A	0.8603	0.1191	0.2761	0.020*
H6B	0.9670	0.0753	0.3085	0.020*
C7	0.83923 (13)	0.08945 (13)	0.40485 (8)	0.0165 (3)
C8	0.88948 (14)	0.06657 (14)	0.46583 (8)	0.0184 (3)
H8	0.9108	−0.0027	0.4697	0.022*
C9	0.90884 (14)	0.14440 (15)	0.52132 (8)	0.0213 (4)
H9	0.9436	0.1280	0.5625	0.026*
C10	0.87759 (14)	0.24535 (15)	0.51663 (8)	0.0214 (4)
H10	0.8902	0.2980	0.5545	0.026*
C11	0.82747 (15)	0.26892 (15)	0.45580 (9)	0.0226 (4)
H11	0.8060	0.3381	0.4522	0.027*
C12	0.80868 (15)	0.19170 (14)	0.40037 (8)	0.0212 (4)
H12	0.7748	0.2087	0.3591	0.025*
C13	0.62662 (13)	−0.07956 (13)	0.36620 (8)	0.0156 (3)
C14	0.52752 (13)	−0.04018 (13)	0.38601 (8)	0.0166 (3)
C15	0.46618 (14)	−0.10081 (14)	0.42928 (8)	0.0193 (3)
H15	0.4890	−0.1644	0.4448	0.023*
C16	0.37325 (14)	−0.06928 (15)	0.44944 (8)	0.0223 (4)
H16	0.3320	−0.1114	0.4784	0.027*
C17	0.33994 (15)	0.02420 (16)	0.42736 (9)	0.0255 (4)
H17	0.2759	0.0460	0.4412	0.031*
C18	0.40005 (15)	0.08568 (16)	0.38511 (9)	0.0253 (4)
H18	0.3773	0.1498	0.3703	0.030*
C19	0.49362 (15)	0.05376 (14)	0.36427 (9)	0.0212 (4)
H19	0.5344	0.0960	0.3352	0.025*
C20	0.55081 (13)	−0.14096 (13)	0.22153 (7)	0.0154 (3)
C21	0.49356 (15)	−0.25064 (14)	0.21275 (8)	0.0211 (4)
H21	0.5309	−0.3068	0.2271	0.025*
C22	0.38218 (16)	−0.27898 (15)	0.18316 (9)	0.0265 (4)
H22	0.3443	−0.3542	0.1772	0.032*
C23	0.32670 (15)	−0.19822 (16)	0.16240 (9)	0.0247 (4)
H23	0.2505	−0.2176	0.1426	0.030*
C24	0.38253 (15)	−0.08865 (15)	0.17061 (9)	0.0234 (4)
H24	0.3445	−0.0328	0.1564	0.028*
C25	0.49412 (14)	−0.06033 (14)	0.19960 (8)	0.0196 (3)
H25	0.5321	0.0148	0.2045	0.023*
C26	0.73613 (13)	−0.16608 (13)	0.14622 (8)	0.0166 (3)
C27	0.69905 (14)	−0.15658 (14)	0.07465 (8)	0.0188 (3)
C28	0.70456 (15)	−0.24413 (15)	0.02846 (9)	0.0242 (4)
H28	0.7337	−0.3053	0.0430	0.029*
C29	0.66770 (17)	−0.24208 (17)	−0.03847 (9)	0.0300 (4)
H29	0.6715	−0.3018	−0.0695	0.036*
C30	0.62570 (17)	−0.15360 (17)	−0.05976 (9)	0.0315 (4)
H30	0.6003	−0.1526	−0.1055	0.038*
C31	0.62028 (19)	−0.06607 (17)	−0.01479 (10)	0.0353 (5)
H31	0.5912	−0.0052	−0.0297	0.042*
C32	0.65752 (17)	−0.06729 (16)	0.05245 (9)	0.0289 (4)
H32	0.6544	−0.0068	0.0832	0.035*
C33	0.94237 (14)	0.00899 (14)	0.17643 (8)	0.0174 (3)
C34	1.01253 (14)	−0.05437 (14)	0.15097 (8)	0.0202 (3)
H34	1.0190	−0.1223	0.1682	0.024*
C35	1.07322 (15)	−0.01955 (15)	0.10067 (9)	0.0247 (4)
H35	1.1208	−0.0636	0.0840	0.030*
C36	1.06425 (15)	0.07927 (15)	0.07493 (9)	0.0249 (4)
H36	1.1046	0.1025	0.0401	0.030*
C37	0.99622 (16)	0.14366 (15)	0.10031 (9)	0.0247 (4)
H37	0.9908	0.2120	0.0833	0.030*
C38	0.93565 (15)	0.10898 (14)	0.15061 (9)	0.0210 (3)
H38	0.8891	0.1539	0.1676	0.025*
O4	0.93260 (11)	0.41154 (11)	0.31559 (7)	0.0258 (3)
H39	0.961 (3)	0.376 (2)	0.2832 (13)	0.085 (11)*
O5	0.97595 (10)	0.37361 (10)	0.18672 (6)	0.0235 (3)
O6	0.60445 (10)	0.22212 (10)	0.24810 (6)	0.0230 (3)
C39	0.90657 (14)	0.51145 (14)	0.29188 (8)	0.0177 (3)
C40	0.85630 (13)	0.49095 (13)	0.21687 (8)	0.0155 (3)
H40	0.8350	0.5601	0.2021	0.019*
C41	0.75245 (13)	0.39591 (13)	0.20405 (8)	0.0156 (3)
H41	0.7771	0.3266	0.2157	0.019*
C42	0.66379 (13)	0.41618 (13)	0.24807 (8)	0.0155 (3)
H42	0.6285	0.4774	0.2321	0.019*
C43	0.71338 (13)	0.44550 (14)	0.32269 (8)	0.0171 (3)
H43	0.7383	0.3790	0.3392	0.021*
C44	0.81605 (14)	0.54033 (14)	0.33148 (8)	0.0190 (3)
H44A	0.8473	0.5562	0.3791	0.023*
H44B	0.7931	0.6077	0.3164	0.023*
C45	1.01111 (14)	0.60416 (14)	0.30101 (8)	0.0187 (3)
C46	1.11758 (14)	0.57953 (16)	0.31002 (9)	0.0229 (4)
H46	1.1254	0.5053	0.3136	0.027*
C47	1.21230 (15)	0.66270 (17)	0.31387 (9)	0.0267 (4)
H47	1.2843	0.6447	0.3200	0.032*
C48	1.20316 (15)	0.77174 (16)	0.30887 (9)	0.0254 (4)
H48	1.2682	0.8282	0.3111	0.030*
C49	1.09754 (16)	0.79709 (15)	0.30058 (9)	0.0248 (4)
H49	1.0901	0.8716	0.2979	0.030*
C50	1.00253 (15)	0.71406 (15)	0.29622 (9)	0.0224 (4)
H50	0.9307	0.7324	0.2899	0.027*
C51	0.94415 (13)	0.45989 (13)	0.17693 (8)	0.0167 (3)
C52	0.99308 (13)	0.53065 (14)	0.12776 (8)	0.0173 (3)
C53	1.08083 (14)	0.49903 (15)	0.09831 (9)	0.0220 (4)
H53	1.1076	0.4353	0.1105	0.026*
C54	1.12841 (15)	0.56051 (16)	0.05164 (9)	0.0254 (4)
H54	1.1884	0.5394	0.0323	0.031*
C55	1.08894 (15)	0.65275 (16)	0.03305 (9)	0.0262 (4)
H55	1.1218	0.6947	0.0010	0.031*
C56	1.00138 (16)	0.68395 (15)	0.06134 (9)	0.0245 (4)
H56	0.9736	0.7465	0.0480	0.029*
C57	0.95440 (15)	0.62383 (14)	0.10906 (8)	0.0208 (4)
H57	0.8956	0.6464	0.1290	0.025*
C58	0.70126 (13)	0.37846 (14)	0.13135 (8)	0.0177 (3)
C59	0.69034 (15)	0.27660 (15)	0.09453 (9)	0.0243 (4)
H59	0.7152	0.2176	0.1150	0.029*
C60	0.64317 (16)	0.26056 (17)	0.02783 (10)	0.0319 (5)
H60A	0.6364	0.1908	0.0032	0.038*
C61	0.60640 (15)	0.34503 (18)	−0.00263 (9)	0.0321 (5)
H61	0.5732	0.3334	−0.0478	0.039*
C62	0.61833 (15)	0.44717 (17)	0.03335 (9)	0.0275 (4)
H62	0.5944	0.5062	0.0125	0.033*
C63	0.66529 (14)	0.46361 (15)	0.09990 (9)	0.0209 (4)
H63	0.6728	0.5338	0.1241	0.025*
C64	0.57390 (14)	0.30980 (13)	0.24223 (8)	0.0167 (3)
C65	0.45204 (13)	0.31176 (14)	0.23228 (8)	0.0167 (3)
C66	0.37637 (14)	0.21202 (14)	0.23251 (8)	0.0183 (3)
H66	0.4038	0.1464	0.2390	0.022*
C67	0.26196 (15)	0.20741 (15)	0.22346 (8)	0.0224 (4)
H67	0.2114	0.1389	0.2230	0.027*
C68	0.22144 (14)	0.30341 (15)	0.21500 (8)	0.0231 (4)
H68	0.1431	0.3006	0.2085	0.028*
C69	0.29533 (15)	0.40294 (15)	0.21599 (9)	0.0242 (4)
H69	0.2675	0.4687	0.2113	0.029*
C70	0.41020 (14)	0.40754 (14)	0.22382 (9)	0.0209 (3)
H70	0.4603	0.4761	0.2234	0.025*
C71	0.62127 (13)	0.46964 (14)	0.36107 (8)	0.0186 (3)
C72	0.56217 (15)	0.38604 (16)	0.39288 (9)	0.0241 (4)
H72	0.5862	0.3178	0.3951	0.029*
C73	0.46892 (16)	0.40155 (18)	0.42122 (9)	0.0314 (4)
H73	0.4294	0.3441	0.4425	0.038*
C74	0.43352 (16)	0.50089 (18)	0.41840 (10)	0.0348 (5)
H74	0.3686	0.5110	0.4368	0.042*
C75	0.49268 (16)	0.58506 (17)	0.38882 (10)	0.0309 (4)
H75	0.4696	0.6539	0.3879	0.037*
C76	0.58624 (15)	0.56964 (15)	0.36023 (9)	0.0236 (4)
H76	0.6265	0.6281	0.3400	0.028*
C77	0.11978 (15)	0.30446 (14)	0.44493 (8)	0.0205 (3)
H77	0.0424	0.2602	0.4439	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0291 (2)	0.0325 (2)	0.0200 (2)	0.00686 (19)	0.00626 (17)	0.00007 (17)
Cl2	0.0420 (3)	0.0233 (2)	0.0278 (2)	0.0111 (2)	0.0067 (2)	0.00162 (18)
Cl3	0.0294 (2)	0.0326 (2)	0.0252 (2)	0.01055 (19)	0.00426 (18)	0.00915 (18)
O1	0.0212 (6)	0.0208 (6)	0.0213 (6)	0.0069 (5)	0.0021 (5)	0.0029 (5)
O2	0.0218 (6)	0.0208 (6)	0.0250 (6)	0.0058 (5)	0.0046 (5)	0.0082 (5)
O3	0.0241 (6)	0.0186 (6)	0.0236 (6)	0.0060 (5)	0.0038 (5)	−0.0009 (5)
C1	0.0160 (8)	0.0143 (8)	0.0158 (7)	0.0035 (6)	0.0008 (6)	−0.0004 (6)
C2	0.0137 (7)	0.0133 (7)	0.0154 (7)	0.0032 (6)	0.0018 (6)	0.0012 (6)
C3	0.0159 (8)	0.0133 (7)	0.0140 (7)	0.0023 (6)	0.0015 (6)	0.0008 (6)
C4	0.0156 (8)	0.0135 (7)	0.0151 (7)	0.0035 (6)	0.0015 (6)	0.0004 (6)
C5	0.0137 (7)	0.0141 (7)	0.0156 (7)	0.0022 (6)	0.0020 (6)	0.0012 (6)
C6	0.0153 (8)	0.0160 (8)	0.0171 (8)	0.0007 (6)	0.0018 (6)	−0.0003 (6)
C7	0.0130 (7)	0.0190 (8)	0.0163 (8)	0.0011 (6)	0.0023 (6)	−0.0013 (6)
C8	0.0165 (8)	0.0207 (8)	0.0180 (8)	0.0026 (7)	0.0040 (6)	0.0018 (6)
C9	0.0172 (8)	0.0316 (10)	0.0132 (8)	0.0009 (7)	0.0020 (6)	0.0014 (7)
C10	0.0173 (8)	0.0239 (9)	0.0194 (8)	−0.0017 (7)	0.0037 (7)	−0.0070 (7)
C11	0.0229 (9)	0.0184 (8)	0.0253 (9)	0.0034 (7)	0.0035 (7)	−0.0028 (7)
C12	0.0220 (9)	0.0212 (9)	0.0184 (8)	0.0038 (7)	−0.0011 (7)	−0.0017 (7)
C13	0.0161 (8)	0.0156 (8)	0.0128 (7)	0.0006 (6)	−0.0006 (6)	−0.0009 (6)
C14	0.0154 (8)	0.0179 (8)	0.0146 (7)	0.0008 (6)	0.0008 (6)	−0.0016 (6)
C15	0.0217 (8)	0.0177 (8)	0.0160 (8)	−0.0008 (7)	0.0014 (6)	0.0000 (6)
C16	0.0189 (8)	0.0250 (9)	0.0193 (8)	−0.0045 (7)	0.0046 (7)	−0.0003 (7)
C17	0.0200 (9)	0.0310 (10)	0.0250 (9)	0.0042 (8)	0.0069 (7)	−0.0041 (8)
C18	0.0251 (9)	0.0256 (9)	0.0290 (10)	0.0111 (8)	0.0076 (8)	0.0045 (8)
C19	0.0229 (9)	0.0209 (9)	0.0214 (8)	0.0053 (7)	0.0069 (7)	0.0038 (7)
C20	0.0155 (8)	0.0188 (8)	0.0112 (7)	0.0015 (6)	0.0032 (6)	0.0000 (6)
C21	0.0232 (9)	0.0182 (8)	0.0204 (8)	0.0016 (7)	0.0010 (7)	0.0029 (7)
C22	0.0251 (9)	0.0222 (9)	0.0266 (9)	−0.0066 (7)	0.0004 (7)	0.0012 (7)
C23	0.0169 (8)	0.0329 (10)	0.0195 (8)	−0.0023 (7)	−0.0018 (7)	−0.0013 (7)
C24	0.0204 (9)	0.0278 (10)	0.0217 (9)	0.0073 (7)	−0.0008 (7)	0.0014 (7)
C25	0.0196 (8)	0.0161 (8)	0.0212 (8)	0.0015 (7)	0.0005 (7)	0.0000 (6)
C26	0.0130 (7)	0.0166 (8)	0.0191 (8)	0.0003 (6)	0.0041 (6)	−0.0012 (6)
C27	0.0168 (8)	0.0199 (8)	0.0176 (8)	−0.0012 (7)	0.0040 (6)	−0.0018 (6)
C28	0.0246 (9)	0.0233 (9)	0.0226 (9)	−0.0003 (7)	0.0076 (7)	−0.0040 (7)
C29	0.0317 (10)	0.0329 (11)	0.0215 (9)	−0.0017 (9)	0.0090 (8)	−0.0082 (8)
C30	0.0351 (11)	0.0394 (11)	0.0154 (8)	−0.0035 (9)	0.0042 (8)	0.0014 (8)
C31	0.0517 (13)	0.0317 (11)	0.0207 (9)	0.0082 (10)	−0.0017 (9)	0.0041 (8)
C32	0.0412 (11)	0.0246 (9)	0.0188 (9)	0.0058 (8)	0.0008 (8)	−0.0020 (7)
C33	0.0155 (8)	0.0200 (8)	0.0145 (7)	0.0000 (6)	0.0007 (6)	−0.0006 (6)
C34	0.0205 (8)	0.0192 (8)	0.0206 (8)	0.0030 (7)	0.0034 (7)	0.0013 (7)
C35	0.0212 (9)	0.0288 (10)	0.0231 (9)	0.0025 (8)	0.0064 (7)	−0.0025 (7)
C36	0.0226 (9)	0.0289 (10)	0.0195 (8)	−0.0053 (8)	0.0052 (7)	0.0014 (7)
C37	0.0284 (10)	0.0210 (9)	0.0225 (9)	−0.0009 (7)	0.0019 (7)	0.0058 (7)
C38	0.0222 (9)	0.0187 (8)	0.0218 (8)	0.0034 (7)	0.0034 (7)	0.0014 (7)
O4	0.0236 (7)	0.0270 (7)	0.0284 (7)	0.0075 (6)	0.0031 (5)	0.0085 (6)
O5	0.0199 (6)	0.0205 (6)	0.0314 (7)	0.0063 (5)	0.0059 (5)	0.0015 (5)
O6	0.0196 (6)	0.0171 (6)	0.0333 (7)	0.0040 (5)	0.0059 (5)	0.0045 (5)
C39	0.0159 (8)	0.0190 (8)	0.0183 (8)	0.0043 (7)	0.0017 (6)	0.0023 (6)
C40	0.0127 (7)	0.0166 (8)	0.0174 (8)	0.0033 (6)	0.0029 (6)	0.0016 (6)
C41	0.0139 (7)	0.0147 (8)	0.0187 (8)	0.0037 (6)	0.0031 (6)	0.0012 (6)
C42	0.0138 (7)	0.0153 (8)	0.0178 (8)	0.0033 (6)	0.0028 (6)	0.0025 (6)
C43	0.0152 (8)	0.0195 (8)	0.0168 (8)	0.0031 (6)	0.0022 (6)	0.0031 (6)
C44	0.0171 (8)	0.0228 (9)	0.0159 (8)	0.0026 (7)	0.0021 (6)	−0.0004 (6)
C45	0.0163 (8)	0.0248 (9)	0.0136 (7)	0.0017 (7)	0.0018 (6)	0.0000 (6)
C46	0.0194 (9)	0.0277 (9)	0.0214 (9)	0.0049 (7)	0.0031 (7)	0.0011 (7)
C47	0.0142 (8)	0.0407 (11)	0.0232 (9)	0.0027 (8)	0.0013 (7)	0.0009 (8)
C48	0.0213 (9)	0.0321 (10)	0.0173 (8)	−0.0057 (8)	0.0021 (7)	−0.0014 (7)
C49	0.0270 (9)	0.0237 (9)	0.0218 (9)	0.0001 (8)	0.0044 (7)	0.0015 (7)
C50	0.0205 (9)	0.0250 (9)	0.0210 (8)	0.0039 (7)	0.0023 (7)	0.0009 (7)
C51	0.0133 (8)	0.0163 (8)	0.0189 (8)	0.0023 (6)	0.0001 (6)	−0.0023 (6)
C52	0.0147 (8)	0.0190 (8)	0.0157 (8)	0.0000 (6)	0.0013 (6)	−0.0031 (6)
C53	0.0158 (8)	0.0268 (9)	0.0223 (9)	0.0034 (7)	0.0027 (7)	−0.0023 (7)
C54	0.0164 (8)	0.0354 (10)	0.0227 (9)	0.0015 (8)	0.0061 (7)	−0.0042 (8)
C55	0.0229 (9)	0.0306 (10)	0.0209 (9)	−0.0053 (8)	0.0046 (7)	0.0007 (7)
C56	0.0277 (10)	0.0219 (9)	0.0233 (9)	0.0029 (8)	0.0047 (7)	0.0020 (7)
C57	0.0209 (8)	0.0197 (8)	0.0214 (8)	0.0035 (7)	0.0050 (7)	−0.0019 (7)
C58	0.0108 (7)	0.0207 (8)	0.0197 (8)	−0.0008 (6)	0.0034 (6)	−0.0010 (6)
C59	0.0205 (9)	0.0231 (9)	0.0274 (9)	0.0017 (7)	0.0045 (7)	−0.0041 (7)
C60	0.0256 (10)	0.0356 (11)	0.0280 (10)	−0.0060 (8)	0.0065 (8)	−0.0115 (8)
C61	0.0180 (9)	0.0533 (13)	0.0182 (9)	−0.0068 (9)	0.0028 (7)	−0.0029 (8)
C62	0.0170 (8)	0.0388 (11)	0.0251 (9)	0.0015 (8)	0.0009 (7)	0.0082 (8)
C63	0.0165 (8)	0.0234 (9)	0.0218 (8)	0.0018 (7)	0.0026 (7)	0.0015 (7)
C64	0.0170 (8)	0.0170 (8)	0.0157 (8)	0.0023 (6)	0.0035 (6)	0.0009 (6)
C65	0.0159 (8)	0.0194 (8)	0.0138 (7)	0.0026 (6)	0.0022 (6)	−0.0020 (6)
C66	0.0198 (8)	0.0174 (8)	0.0172 (8)	0.0031 (7)	0.0027 (6)	0.0005 (6)
C67	0.0195 (8)	0.0245 (9)	0.0207 (8)	−0.0010 (7)	0.0032 (7)	0.0009 (7)
C68	0.0151 (8)	0.0331 (10)	0.0196 (8)	0.0038 (7)	0.0009 (7)	−0.0006 (7)
C69	0.0199 (9)	0.0243 (9)	0.0284 (9)	0.0072 (7)	0.0000 (7)	0.0006 (7)
C70	0.0188 (8)	0.0173 (8)	0.0248 (9)	0.0010 (7)	0.0012 (7)	0.0002 (7)
C71	0.0132 (8)	0.0250 (9)	0.0156 (8)	0.0015 (7)	0.0000 (6)	−0.0004 (6)
C72	0.0215 (9)	0.0280 (10)	0.0212 (9)	0.0011 (7)	0.0036 (7)	0.0022 (7)
C73	0.0238 (9)	0.0416 (12)	0.0248 (10)	−0.0053 (9)	0.0096 (8)	−0.0014 (8)
C74	0.0192 (9)	0.0480 (13)	0.0333 (11)	0.0020 (9)	0.0082 (8)	−0.0152 (9)
C75	0.0203 (9)	0.0330 (11)	0.0366 (11)	0.0069 (8)	0.0015 (8)	−0.0129 (9)
C76	0.0189 (8)	0.0255 (9)	0.0237 (9)	0.0016 (7)	0.0005 (7)	−0.0025 (7)
C77	0.0221 (9)	0.0207 (8)	0.0187 (8)	0.0037 (7)	0.0039 (7)	0.0019 (7)

Geometric parameters (Å, º)

Cl1—C77	1.7676 (17)	C38—H38	0.9500
Cl2—C77	1.7600 (18)	O4—C39	1.441 (2)
Cl3—C77	1.7659 (18)	O4—H39	0.911 (18)
O1—C1	1.4336 (19)	O5—C51	1.229 (2)
O1—H1	0.886 (15)	O6—C64	1.226 (2)
O2—C13	1.2315 (19)	C39—C45	1.532 (2)
O3—C26	1.225 (2)	C39—C44	1.537 (2)
C1—C6	1.534 (2)	C39—C40	1.562 (2)
C1—C7	1.536 (2)	C40—C51	1.523 (2)
C1—C2	1.559 (2)	C40—C41	1.542 (2)
C2—C13	1.527 (2)	C40—H40	1.0000
C2—C3	1.549 (2)	C41—C58	1.521 (2)
C2—H2	1.0000	C41—C42	1.544 (2)
C3—C20	1.524 (2)	C41—H41	1.0000
C3—C4	1.548 (2)	C42—C64	1.536 (2)
C3—H3	1.0000	C42—C43	1.558 (2)
C4—C26	1.530 (2)	C42—H42	1.0000
C4—C5	1.551 (2)	C43—C71	1.520 (2)
C4—H4	1.0000	C43—C44	1.533 (2)
C5—C33	1.522 (2)	C43—H43	1.0000
C5—C6	1.534 (2)	C44—H44A	0.9900
C5—H5	1.0000	C44—H44B	0.9900
C6—H6A	0.9900	C45—C46	1.394 (2)
C6—H6B	0.9900	C45—C50	1.396 (2)
C7—C8	1.394 (2)	C46—C47	1.389 (3)
C7—C12	1.396 (2)	C46—H46	0.9500
C8—C9	1.397 (2)	C47—C48	1.388 (3)
C8—H8	0.9500	C47—H47	0.9500
C9—C10	1.384 (3)	C48—C49	1.388 (3)
C9—H9	0.9500	C48—H48	0.9500
C10—C11	1.394 (2)	C49—C50	1.390 (2)
C10—H10	0.9500	C49—H49	0.9500
C11—C12	1.392 (2)	C50—H50	0.9500
C11—H11	0.9500	C51—C52	1.493 (2)
C12—H12	0.9500	C52—C57	1.393 (2)
C13—C14	1.488 (2)	C52—C53	1.405 (2)
C14—C19	1.395 (2)	C53—C54	1.384 (3)
C14—C15	1.404 (2)	C53—H53	0.9500
C15—C16	1.377 (2)	C54—C55	1.386 (3)
C15—H15	0.9500	C54—H54	0.9500
C16—C17	1.389 (3)	C55—C56	1.389 (3)
C16—H16	0.9500	C55—H55	0.9500
C17—C18	1.386 (3)	C56—C57	1.390 (2)
C17—H17	0.9500	C56—H56	0.9500
C18—C19	1.392 (2)	C57—H57	0.9500
C18—H18	0.9500	C58—C63	1.391 (2)
C19—H19	0.9500	C58—C59	1.394 (2)
C20—C21	1.393 (2)	C59—C60	1.396 (3)
C20—C25	1.394 (2)	C59—H59	0.9500
C21—C22	1.393 (2)	C60—C61	1.378 (3)
C21—H21	0.9500	C60—H60A	0.9500
C22—C23	1.379 (3)	C61—C62	1.387 (3)
C22—H22	0.9500	C61—H61	0.9500
C23—C24	1.386 (3)	C62—C63	1.393 (2)
C23—H23	0.9500	C62—H62	0.9500
C24—C25	1.392 (2)	C63—H63	0.9500
C24—H24	0.9500	C64—C65	1.493 (2)
C25—H25	0.9500	C65—C70	1.396 (2)
C26—C27	1.497 (2)	C65—C66	1.398 (2)
C27—C32	1.388 (3)	C66—C67	1.386 (2)
C27—C28	1.401 (2)	C66—H66	0.9500
C28—C29	1.390 (3)	C67—C68	1.390 (3)
C28—H28	0.9500	C67—H67	0.9500
C29—C30	1.376 (3)	C68—C69	1.382 (3)
C29—H29	0.9500	C68—H68	0.9500
C30—C31	1.385 (3)	C69—C70	1.392 (2)
C30—H30	0.9500	C69—H69	0.9500
C31—C32	1.395 (3)	C70—H70	0.9500
C31—H31	0.9500	C71—C76	1.389 (3)
C32—H32	0.9500	C71—C72	1.400 (2)
C33—C34	1.395 (2)	C72—C73	1.388 (3)
C33—C38	1.396 (2)	C72—H72	0.9500
C34—C35	1.393 (2)	C73—C74	1.386 (3)
C34—H34	0.9500	C73—H73	0.9500
C35—C36	1.388 (3)	C74—C75	1.379 (3)
C35—H35	0.9500	C74—H74	0.9500
C36—C37	1.382 (3)	C75—C76	1.394 (3)
C36—H36	0.9500	C75—H75	0.9500
C37—C38	1.392 (2)	C76—H76	0.9500
C37—H37	0.9500	C77—H77	1.0000
C1—O1—H1	107.0 (14)	C45—C39—C44	112.34 (14)
O1—C1—C6	105.18 (13)	O4—C39—C40	110.67 (13)
O1—C1—C7	110.79 (13)	C45—C39—C40	108.81 (13)
C6—C1—C7	110.47 (13)	C44—C39—C40	108.24 (13)
O1—C1—C2	110.82 (13)	C51—C40—C41	108.41 (13)
C6—C1—C2	109.22 (13)	C51—C40—C39	108.99 (13)
C7—C1—C2	110.25 (13)	C41—C40—C39	111.36 (13)
C13—C2—C3	108.10 (12)	C51—C40—H40	109.4
C13—C2—C1	110.13 (13)	C41—C40—H40	109.4
C3—C2—C1	110.87 (13)	C39—C40—H40	109.4
C13—C2—H2	109.2	C58—C41—C40	111.34 (13)
C3—C2—H2	109.2	C58—C41—C42	110.19 (13)
C1—C2—H2	109.2	C40—C41—C42	111.51 (13)
C20—C3—C4	110.20 (12)	C58—C41—H41	107.9
C20—C3—C2	112.14 (13)	C40—C41—H41	107.9
C4—C3—C2	111.84 (12)	C42—C41—H41	107.9
C20—C3—H3	107.5	C64—C42—C41	108.40 (13)
C4—C3—H3	107.5	C64—C42—C43	107.61 (13)
C2—C3—H3	107.5	C41—C42—C43	112.83 (13)
C26—C4—C3	107.48 (12)	C64—C42—H42	109.3
C26—C4—C5	108.31 (13)	C41—C42—H42	109.3
C3—C4—C5	112.52 (13)	C43—C42—H42	109.3
C26—C4—H4	109.5	C71—C43—C44	113.54 (14)
C3—C4—H4	109.5	C71—C43—C42	108.74 (13)
C5—C4—H4	109.5	C44—C43—C42	110.74 (13)
C33—C5—C6	113.08 (13)	C71—C43—H43	107.9
C33—C5—C4	110.73 (13)	C44—C43—H43	107.9
C6—C5—C4	110.16 (13)	C42—C43—H43	107.9
C33—C5—H5	107.5	C43—C44—C39	111.37 (14)
C6—C5—H5	107.5	C43—C44—H44A	109.4
C4—C5—H5	107.5	C39—C44—H44A	109.4
C5—C6—C1	111.19 (13)	C43—C44—H44B	109.4
C5—C6—H6A	109.4	C39—C44—H44B	109.4
C1—C6—H6A	109.4	H44A—C44—H44B	108.0
C5—C6—H6B	109.4	C46—C45—C50	118.33 (16)
C1—C6—H6B	109.4	C46—C45—C39	120.43 (16)
H6A—C6—H6B	108.0	C50—C45—C39	121.11 (15)
C8—C7—C12	118.66 (15)	C47—C46—C45	120.49 (17)
C8—C7—C1	120.63 (15)	C47—C46—H46	119.8
C12—C7—C1	120.69 (14)	C45—C46—H46	119.8
C7—C8—C9	120.66 (16)	C48—C47—C46	120.88 (17)
C7—C8—H8	119.7	C48—C47—H47	119.6
C9—C8—H8	119.7	C46—C47—H47	119.6
C10—C9—C8	120.36 (16)	C49—C48—C47	118.98 (17)
C10—C9—H9	119.8	C49—C48—H48	120.5
C8—C9—H9	119.8	C47—C48—H48	120.5
C9—C10—C11	119.31 (16)	C48—C49—C50	120.33 (18)
C9—C10—H10	120.3	C48—C49—H49	119.8
C11—C10—H10	120.3	C50—C49—H49	119.8
C12—C11—C10	120.40 (17)	C49—C50—C45	120.98 (17)
C12—C11—H11	119.8	C49—C50—H50	119.5
C10—C11—H11	119.8	C45—C50—H50	119.5
C11—C12—C7	120.60 (16)	O5—C51—C52	119.61 (15)
C11—C12—H12	119.7	O5—C51—C40	117.85 (14)
C7—C12—H12	119.7	C52—C51—C40	122.53 (14)
O2—C13—C14	119.43 (14)	C57—C52—C53	119.19 (16)
O2—C13—C2	117.91 (14)	C57—C52—C51	123.26 (15)
C14—C13—C2	122.66 (14)	C53—C52—C51	117.54 (15)
C19—C14—C15	118.85 (15)	C54—C53—C52	120.14 (17)
C19—C14—C13	123.38 (15)	C54—C53—H53	119.9
C15—C14—C13	117.77 (15)	C52—C53—H53	119.9
C16—C15—C14	120.84 (16)	C53—C54—C55	120.28 (17)
C16—C15—H15	119.6	C53—C54—H54	119.9
C14—C15—H15	119.6	C55—C54—H54	119.9
C15—C16—C17	119.89 (16)	C54—C55—C56	120.00 (17)
C15—C16—H16	120.1	C54—C55—H55	120.0
C17—C16—H16	120.1	C56—C55—H55	120.0
C18—C17—C16	120.09 (17)	C55—C56—C57	120.11 (17)
C18—C17—H17	120.0	C55—C56—H56	119.9
C16—C17—H17	120.0	C57—C56—H56	119.9
C17—C18—C19	120.23 (17)	C56—C57—C52	120.27 (16)
C17—C18—H18	119.9	C56—C57—H57	119.9
C19—C18—H18	119.9	C52—C57—H57	119.9
C18—C19—C14	120.10 (16)	C63—C58—C59	118.44 (16)
C18—C19—H19	120.0	C63—C58—C41	121.02 (15)
C14—C19—H19	120.0	C59—C58—C41	120.54 (16)
C21—C20—C25	118.37 (15)	C58—C59—C60	120.51 (18)
C21—C20—C3	120.30 (15)	C58—C59—H59	119.7
C25—C20—C3	121.30 (14)	C60—C59—H59	119.7
C20—C21—C22	120.80 (16)	C61—C60—C59	120.58 (18)
C20—C21—H21	119.6	C61—C60—H60A	119.7
C22—C21—H21	119.6	C59—C60—H60A	119.7
C23—C22—C21	120.23 (16)	C60—C61—C62	119.33 (18)
C23—C22—H22	119.9	C60—C61—H61	120.3
C21—C22—H22	119.9	C62—C61—H61	120.3
C22—C23—C24	119.72 (16)	C61—C62—C63	120.32 (18)
C22—C23—H23	120.1	C61—C62—H62	119.8
C24—C23—H23	120.1	C63—C62—H62	119.8
C23—C24—C25	120.11 (17)	C58—C63—C62	120.80 (17)
C23—C24—H24	119.9	C58—C63—H63	119.6
C25—C24—H24	119.9	C62—C63—H63	119.6
C24—C25—C20	120.76 (16)	O6—C64—C65	119.97 (15)
C24—C25—H25	119.6	O6—C64—C42	118.27 (14)
C20—C25—H25	119.6	C65—C64—C42	121.71 (14)
O3—C26—C27	119.81 (15)	C70—C65—C66	118.65 (15)
O3—C26—C4	118.13 (14)	C70—C65—C64	123.61 (15)
C27—C26—C4	122.06 (14)	C66—C65—C64	117.73 (15)
C32—C27—C28	119.01 (16)	C67—C66—C65	120.99 (16)
C32—C27—C26	123.36 (15)	C67—C66—H66	119.5
C28—C27—C26	117.62 (16)	C65—C66—H66	119.5
C29—C28—C27	120.41 (18)	C66—C67—C68	119.75 (16)
C29—C28—H28	119.8	C66—C67—H67	120.1
C27—C28—H28	119.8	C68—C67—H67	120.1
C30—C29—C28	120.02 (18)	C69—C68—C67	119.88 (16)
C30—C29—H29	120.0	C69—C68—H68	120.1
C28—C29—H29	120.0	C67—C68—H68	120.1
C29—C30—C31	120.30 (18)	C68—C69—C70	120.52 (17)
C29—C30—H30	119.8	C68—C69—H69	119.7
C31—C30—H30	119.8	C70—C69—H69	119.7
C30—C31—C32	120.02 (19)	C69—C70—C65	120.19 (16)
C30—C31—H31	120.0	C69—C70—H70	119.9
C32—C31—H31	120.0	C65—C70—H70	119.9
C27—C32—C31	120.23 (18)	C76—C71—C72	118.36 (16)
C27—C32—H32	119.9	C76—C71—C43	121.63 (15)
C31—C32—H32	119.9	C72—C71—C43	119.71 (16)
C34—C33—C38	118.12 (15)	C73—C72—C71	120.83 (18)
C34—C33—C5	120.27 (15)	C73—C72—H72	119.6
C38—C33—C5	121.58 (15)	C71—C72—H72	119.6
C35—C34—C33	120.97 (16)	C74—C73—C72	119.97 (18)
C35—C34—H34	119.5	C74—C73—H73	120.0
C33—C34—H34	119.5	C72—C73—H73	120.0
C36—C35—C34	120.13 (17)	C75—C74—C73	119.85 (18)
C36—C35—H35	119.9	C75—C74—H74	120.1
C34—C35—H35	119.9	C73—C74—H74	120.1
C37—C36—C35	119.53 (16)	C74—C75—C76	120.27 (19)
C37—C36—H36	120.2	C74—C75—H75	119.9
C35—C36—H36	120.2	C76—C75—H75	119.9
C36—C37—C38	120.36 (17)	C71—C76—C75	120.67 (18)
C36—C37—H37	119.8	C71—C76—H76	119.7
C38—C37—H37	119.8	C75—C76—H76	119.7
C37—C38—C33	120.87 (17)	Cl2—C77—Cl3	110.24 (9)
C37—C38—H38	119.6	Cl2—C77—Cl1	110.91 (9)
C33—C38—H38	119.6	Cl3—C77—Cl1	109.92 (9)
C39—O4—H39	108 (2)	Cl2—C77—H77	108.6
O4—C39—C45	111.15 (13)	Cl3—C77—H77	108.6
O4—C39—C44	105.59 (13)	Cl1—C77—H77	108.6
O1—C1—C2—C13	62.01 (16)	O4—C39—C40—C51	−63.60 (16)
C6—C1—C2—C13	177.42 (13)	C45—C39—C40—C51	58.80 (17)
C7—C1—C2—C13	−61.02 (17)	C44—C39—C40—C51	−178.86 (13)
O1—C1—C2—C3	−57.59 (16)	O4—C39—C40—C41	55.94 (17)
C6—C1—C2—C3	57.83 (16)	C45—C39—C40—C41	178.34 (13)
C7—C1—C2—C3	179.38 (12)	C44—C39—C40—C41	−59.32 (17)
C13—C2—C3—C20	61.34 (16)	C51—C40—C41—C58	−61.97 (17)
C1—C2—C3—C20	−177.85 (13)	C39—C40—C41—C58	178.14 (13)
C13—C2—C3—C4	−174.28 (13)	C51—C40—C41—C42	174.51 (13)
C1—C2—C3—C4	−53.47 (17)	C39—C40—C41—C42	54.62 (17)
C20—C3—C4—C26	−63.92 (16)	C58—C41—C42—C64	66.24 (16)
C2—C3—C4—C26	170.63 (13)	C40—C41—C42—C64	−169.59 (13)
C20—C3—C4—C5	176.94 (13)	C58—C41—C42—C43	−174.68 (13)
C2—C3—C4—C5	51.48 (17)	C40—C41—C42—C43	−50.52 (18)
C26—C4—C5—C33	62.12 (17)	C64—C42—C43—C71	−63.38 (17)
C3—C4—C5—C33	−179.22 (13)	C41—C42—C43—C71	177.09 (13)
C26—C4—C5—C6	−172.05 (13)	C64—C42—C43—C44	171.20 (13)
C3—C4—C5—C6	−53.39 (17)	C41—C42—C43—C44	51.67 (18)
C33—C5—C6—C1	−176.90 (13)	C71—C43—C44—C39	179.81 (13)
C4—C5—C6—C1	58.60 (17)	C42—C43—C44—C39	−57.52 (18)
O1—C1—C6—C5	58.00 (16)	O4—C39—C44—C43	−57.54 (17)
C7—C1—C6—C5	177.59 (13)	C45—C39—C44—C43	−178.84 (13)
C2—C1—C6—C5	−60.99 (17)	C40—C39—C44—C43	61.00 (17)
O1—C1—C7—C8	−1.4 (2)	O4—C39—C45—C46	19.3 (2)
C6—C1—C7—C8	−117.51 (16)	C44—C39—C45—C46	137.33 (16)
C2—C1—C7—C8	121.68 (16)	C40—C39—C45—C46	−102.85 (17)
O1—C1—C7—C12	177.14 (14)	O4—C39—C45—C50	−164.96 (15)
C6—C1—C7—C12	61.00 (19)	C44—C39—C45—C50	−46.9 (2)
C2—C1—C7—C12	−59.81 (19)	C40—C39—C45—C50	72.93 (19)
C12—C7—C8—C9	0.0 (2)	C50—C45—C46—C47	−0.2 (3)
C1—C7—C8—C9	178.55 (15)	C39—C45—C46—C47	175.67 (16)
C7—C8—C9—C10	0.4 (2)	C45—C46—C47—C48	0.0 (3)
C8—C9—C10—C11	−0.5 (2)	C46—C47—C48—C49	0.6 (3)
C9—C10—C11—C12	0.2 (3)	C47—C48—C49—C50	−1.1 (3)
C10—C11—C12—C7	0.3 (3)	C48—C49—C50—C45	0.9 (3)
C8—C7—C12—C11	−0.4 (2)	C46—C45—C50—C49	−0.2 (3)
C1—C7—C12—C11	−178.90 (15)	C39—C45—C50—C49	−176.11 (15)
C3—C2—C13—O2	67.69 (18)	C41—C40—C51—O5	−57.49 (19)
C1—C2—C13—O2	−53.57 (19)	C39—C40—C51—O5	63.87 (18)
C3—C2—C13—C14	−111.15 (16)	C41—C40—C51—C52	123.34 (16)
C1—C2—C13—C14	127.58 (15)	C39—C40—C51—C52	−115.30 (16)
O2—C13—C14—C19	174.99 (16)	O5—C51—C52—C57	173.65 (16)
C2—C13—C14—C19	−6.2 (2)	C40—C51—C52—C57	−7.2 (2)
O2—C13—C14—C15	−4.4 (2)	O5—C51—C52—C53	−4.9 (2)
C2—C13—C14—C15	174.38 (14)	C40—C51—C52—C53	174.24 (15)
C19—C14—C15—C16	0.8 (2)	C57—C52—C53—C54	0.4 (2)
C13—C14—C15—C16	−179.75 (15)	C51—C52—C53—C54	179.05 (15)
C14—C15—C16—C17	−0.6 (3)	C52—C53—C54—C55	−0.8 (3)
C15—C16—C17—C18	0.0 (3)	C53—C54—C55—C56	0.1 (3)
C16—C17—C18—C19	0.4 (3)	C54—C55—C56—C57	1.0 (3)
C17—C18—C19—C14	−0.2 (3)	C55—C56—C57—C52	−1.4 (3)
C15—C14—C19—C18	−0.4 (3)	C53—C52—C57—C56	0.7 (2)
C13—C14—C19—C18	−179.82 (16)	C51—C52—C57—C56	−177.87 (16)
C4—C3—C20—C21	111.65 (16)	C40—C41—C58—C63	−57.98 (19)
C2—C3—C20—C21	−123.06 (16)	C42—C41—C58—C63	66.28 (19)
C4—C3—C20—C25	−66.28 (19)	C40—C41—C58—C59	121.41 (16)
C2—C3—C20—C25	59.00 (19)	C42—C41—C58—C59	−114.33 (17)
C25—C20—C21—C22	−0.4 (2)	C63—C58—C59—C60	−0.7 (3)
C3—C20—C21—C22	−178.38 (16)	C41—C58—C59—C60	179.89 (16)
C20—C21—C22—C23	−0.4 (3)	C58—C59—C60—C61	−0.2 (3)
C21—C22—C23—C24	0.5 (3)	C59—C60—C61—C62	1.1 (3)
C22—C23—C24—C25	0.1 (3)	C60—C61—C62—C63	−1.1 (3)
C23—C24—C25—C20	−0.8 (3)	C59—C58—C63—C62	0.7 (2)
C21—C20—C25—C24	1.0 (2)	C41—C58—C63—C62	−179.91 (15)
C3—C20—C25—C24	178.97 (15)	C61—C62—C63—C58	0.2 (3)
C3—C4—C26—O3	−56.54 (18)	C41—C42—C64—O6	48.02 (19)
C5—C4—C26—O3	65.27 (18)	C43—C42—C64—O6	−74.30 (18)
C3—C4—C26—C27	123.84 (15)	C41—C42—C64—C65	−134.31 (15)
C5—C4—C26—C27	−114.35 (16)	C43—C42—C64—C65	103.37 (16)
O3—C26—C27—C32	171.04 (17)	O6—C64—C65—C70	−178.63 (16)
C4—C26—C27—C32	−9.4 (2)	C42—C64—C65—C70	3.7 (2)
O3—C26—C27—C28	−7.4 (2)	O6—C64—C65—C66	2.3 (2)
C4—C26—C27—C28	172.22 (15)	C42—C64—C65—C66	−175.29 (14)
C32—C27—C28—C29	−0.8 (3)	C70—C65—C66—C67	1.0 (2)
C26—C27—C28—C29	177.74 (16)	C64—C65—C66—C67	−179.89 (15)
C27—C28—C29—C30	0.1 (3)	C65—C66—C67—C68	−1.0 (3)
C28—C29—C30—C31	0.2 (3)	C66—C67—C68—C69	−0.3 (3)
C29—C30—C31—C32	0.0 (3)	C67—C68—C69—C70	1.6 (3)
C28—C27—C32—C31	1.0 (3)	C68—C69—C70—C65	−1.5 (3)
C26—C27—C32—C31	−177.40 (18)	C66—C65—C70—C69	0.2 (2)
C30—C31—C32—C27	−0.7 (3)	C64—C65—C70—C69	−178.84 (16)
C6—C5—C33—C34	128.65 (16)	C44—C43—C71—C76	46.3 (2)
C4—C5—C33—C34	−107.16 (17)	C42—C43—C71—C76	−77.49 (19)
C6—C5—C33—C38	−53.2 (2)	C44—C43—C71—C72	−140.13 (16)
C4—C5—C33—C38	70.99 (19)	C42—C43—C71—C72	96.10 (18)
C38—C33—C34—C35	−0.7 (2)	C76—C71—C72—C73	1.8 (3)
C5—C33—C34—C35	177.48 (16)	C43—C71—C72—C73	−171.96 (16)
C33—C34—C35—C36	−0.2 (3)	C71—C72—C73—C74	−0.2 (3)
C34—C35—C36—C37	1.1 (3)	C72—C73—C74—C75	−1.5 (3)
C35—C36—C37—C38	−1.0 (3)	C73—C74—C75—C76	1.7 (3)
C36—C37—C38—C33	0.1 (3)	C72—C71—C76—C75	−1.7 (3)
C34—C33—C38—C37	0.8 (3)	C43—C71—C76—C75	171.95 (16)
C5—C33—C38—C37	−177.39 (16)	C74—C75—C76—C71	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.89 (2)	1.95 (2)	2.7078 (17)	143 (2)
O4—H39···O5	0.91 (2)	2.00 (2)	2.7776 (18)	142 (3)

(mol-2) (4-Hydroxy-2,6-bis(2-methoxyphenyl)-4-phenylcyclohexane-1,3-diyl)bis(phenylmethanone)

Crystal data

C40H36O5	Dx = 1.260 Mg m^−3
Mr = 596.69	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pca21	Cell parameters from 9945 reflections
a = 13.6530 (3) Å	θ = 4.6–67.8°
b = 12.0003 (2) Å	µ = 0.65 mm^−1
c = 19.1982 (4) Å	T = 120 K
V = 3145.44 (11) Å^3	Block, colourless
Z = 4	0.5 × 0.3 × 0.2 mm
F(000) = 1264

Data collection

Bruker APEXII CCD area-detector diffractometer	5520 independent reflections
Radiation source: fine-focus sealed tube	5281 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 67.8°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −16→16
Tmin = 0.255, Tmax = 0.467	k = −14→14
41259 measured reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.8854P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5520 reflections	Δρmax = 0.28 e Å^−3
412 parameters	Δρmin = −0.17 e Å^−3
2 restraints	Absolute structure: Flack x determined using 2368 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.12 (7)

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
O1	0.49073 (12)	0.46442 (14)	0.12075 (10)	0.0266 (4)
H1	0.462 (3)	0.501 (3)	0.1550 (17)	0.061 (12)*
O2	0.48300 (13)	0.54302 (14)	0.25537 (10)	0.0310 (4)
O3	0.46167 (13)	0.10206 (15)	0.18168 (11)	0.0329 (4)
O4	0.73762 (13)	0.27105 (14)	0.30053 (10)	0.0290 (4)
O5	0.77952 (15)	0.16606 (16)	0.09204 (12)	0.0433 (5)
C1	0.59342 (17)	0.45737 (19)	0.13628 (13)	0.0226 (5)
C2	0.60861 (17)	0.42196 (18)	0.21314 (13)	0.0215 (5)
H2	0.6805	0.4153	0.2221	0.026*
C3	0.56002 (17)	0.30784 (19)	0.22856 (13)	0.0227 (5)
H3	0.4890	0.3154	0.2167	0.027*
C4	0.60273 (17)	0.21777 (18)	0.17987 (13)	0.0223 (5)
H4	0.6743	0.2082	0.1893	0.027*
C5	0.58698 (19)	0.25192 (18)	0.10291 (13)	0.0254 (5)
H5	0.5148	0.2620	0.0965	0.030*
C6	0.63460 (19)	0.36608 (19)	0.08848 (13)	0.0249 (5)
H6A	0.7062	0.3603	0.0956	0.030*
H6B	0.6230	0.3871	0.0393	0.030*
C7	0.64372 (17)	0.56949 (19)	0.12480 (13)	0.0221 (5)
C8	0.59099 (19)	0.6623 (2)	0.10273 (15)	0.0288 (5)
H8	0.5232	0.6551	0.0925	0.035*
C9	0.6362 (2)	0.7652 (2)	0.09549 (16)	0.0336 (6)
H9	0.5994	0.8276	0.0802	0.040*
C10	0.7345 (2)	0.7772 (2)	0.11044 (14)	0.0302 (6)
H10	0.7650	0.8480	0.1063	0.036*
C11	0.78810 (18)	0.6858 (2)	0.13142 (13)	0.0283 (5)
H11	0.8560	0.6936	0.1412	0.034*
C12	0.74328 (18)	0.58237 (19)	0.13836 (14)	0.0248 (5)
H12	0.7810	0.5198	0.1525	0.030*
C13	0.56609 (17)	0.50631 (18)	0.26432 (13)	0.0230 (5)
C14	0.62248 (18)	0.53663 (19)	0.32777 (13)	0.0239 (5)
C15	0.5708 (2)	0.5673 (2)	0.38768 (15)	0.0313 (6)
H15	0.5013	0.5716	0.3862	0.038*
C16	0.6193 (2)	0.5915 (2)	0.44909 (15)	0.0380 (7)
H16	0.5834	0.6110	0.4897	0.046*
C17	0.7208 (2)	0.5869 (2)	0.45098 (15)	0.0367 (7)
H17	0.7545	0.6040	0.4929	0.044*
C18	0.7734 (2)	0.5575 (2)	0.39195 (15)	0.0308 (6)
H18	0.8429	0.5550	0.3935	0.037*
C19	0.72458 (18)	0.5319 (2)	0.33060 (13)	0.0258 (5)
H19	0.7608	0.5110	0.2904	0.031*
C20	0.56580 (18)	0.27982 (18)	0.30559 (13)	0.0233 (5)
C21	0.4797 (2)	0.2755 (2)	0.34438 (15)	0.0313 (6)
H21	0.4185	0.2803	0.3211	0.038*
C22	0.4814 (3)	0.2642 (2)	0.41623 (16)	0.0427 (8)
H22	0.4219	0.2617	0.4419	0.051*
C23	0.5701 (3)	0.2568 (3)	0.45005 (17)	0.0491 (9)
H23	0.5716	0.2515	0.4994	0.059*
C24	0.6572 (2)	0.2568 (2)	0.41282 (15)	0.0384 (7)
H24	0.7181	0.2498	0.4364	0.046*
C25	0.65455 (19)	0.26721 (19)	0.34112 (14)	0.0274 (6)
C26	0.54845 (18)	0.11005 (19)	0.19641 (13)	0.0245 (5)
C27	0.59920 (19)	0.0179 (2)	0.23457 (14)	0.0271 (5)
C28	0.5420 (2)	−0.0633 (2)	0.2669 (2)	0.0483 (8)
H28	0.4726	−0.0591	0.2642	0.058*
C29	0.5856 (3)	−0.1496 (3)	0.3030 (3)	0.0624 (11)
H29	0.5460	−0.2033	0.3260	0.075*
C30	0.6860 (2)	−0.1587 (2)	0.30592 (19)	0.0443 (8)
H30	0.7156	−0.2198	0.3293	0.053*
C31	0.7432 (2)	−0.0787 (2)	0.27476 (15)	0.0335 (6)
H31	0.8125	−0.0841	0.2771	0.040*
C32	0.70012 (19)	0.0099 (2)	0.23981 (14)	0.0296 (6)
H32	0.7403	0.0656	0.2193	0.036*
C33	0.6182 (2)	0.1617 (2)	0.05224 (15)	0.0351 (6)
C34	0.5463 (3)	0.1174 (2)	0.00662 (16)	0.0445 (8)
H34	0.4818	0.1472	0.0070	0.053*
C35	0.5693 (4)	0.0310 (3)	−0.03861 (18)	0.0584 (10)
H35	0.5208	0.0007	−0.0686	0.070*
C36	0.6620 (4)	−0.0098 (3)	−0.03948 (18)	0.0578 (11)
H36	0.6774	−0.0685	−0.0709	0.069*
C37	0.7343 (3)	0.0303 (3)	0.0030 (2)	0.0582 (11)
H37	0.7983	−0.0005	0.0012	0.070*
C38	0.7123 (2)	0.1183 (2)	0.04975 (16)	0.0397 (7)
C39	0.8295 (2)	0.2552 (3)	0.33398 (19)	0.0420 (7)
H39A	0.8821	0.2601	0.2994	0.063*
H39B	0.8308	0.1817	0.3561	0.063*
H39C	0.8387	0.3130	0.3694	0.063*
C40	0.8695 (2)	0.1069 (3)	0.1046 (2)	0.0593 (10)
H40A	0.9094	0.1485	0.1381	0.089*
H40B	0.9056	0.0990	0.0608	0.089*
H40C	0.8547	0.0329	0.1235	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0242 (9)	0.0260 (8)	0.0295 (10)	−0.0018 (7)	−0.0047 (7)	0.0017 (8)
O2	0.0283 (9)	0.0304 (9)	0.0344 (11)	0.0065 (7)	−0.0011 (8)	−0.0018 (8)
O3	0.0292 (10)	0.0271 (9)	0.0425 (11)	−0.0063 (7)	−0.0047 (8)	0.0037 (8)
O4	0.0252 (9)	0.0293 (8)	0.0326 (10)	0.0014 (7)	−0.0043 (8)	0.0038 (8)
O5	0.0376 (11)	0.0387 (10)	0.0536 (14)	0.0126 (9)	0.0121 (10)	0.0115 (10)
C1	0.0227 (12)	0.0214 (11)	0.0236 (13)	−0.0008 (9)	−0.0033 (10)	0.0012 (10)
C2	0.0221 (11)	0.0198 (11)	0.0227 (13)	−0.0001 (9)	−0.0006 (9)	0.0001 (10)
C3	0.0237 (11)	0.0199 (11)	0.0244 (13)	−0.0025 (9)	0.0006 (10)	0.0003 (9)
C4	0.0257 (12)	0.0175 (11)	0.0238 (13)	−0.0010 (9)	0.0014 (10)	0.0001 (10)
C5	0.0327 (13)	0.0209 (11)	0.0227 (13)	−0.0038 (10)	0.0008 (10)	0.0002 (10)
C6	0.0339 (13)	0.0203 (11)	0.0205 (13)	−0.0021 (9)	0.0007 (10)	0.0005 (10)
C7	0.0270 (12)	0.0201 (11)	0.0191 (12)	−0.0003 (9)	0.0006 (9)	−0.0013 (9)
C8	0.0272 (12)	0.0250 (12)	0.0342 (15)	0.0018 (10)	−0.0032 (11)	0.0054 (11)
C9	0.0374 (15)	0.0218 (11)	0.0417 (17)	0.0042 (10)	−0.0019 (12)	0.0057 (11)
C10	0.0403 (15)	0.0198 (11)	0.0304 (15)	−0.0056 (10)	0.0005 (12)	0.0017 (10)
C11	0.0289 (13)	0.0296 (13)	0.0264 (14)	−0.0067 (10)	−0.0017 (11)	0.0019 (10)
C12	0.0267 (12)	0.0218 (11)	0.0259 (13)	−0.0010 (10)	−0.0006 (10)	0.0050 (10)
C13	0.0263 (12)	0.0184 (10)	0.0241 (12)	−0.0013 (9)	0.0016 (10)	0.0031 (10)
C14	0.0305 (13)	0.0167 (10)	0.0245 (13)	−0.0016 (10)	0.0005 (10)	0.0025 (9)
C15	0.0352 (14)	0.0289 (12)	0.0299 (14)	0.0024 (11)	0.0041 (12)	−0.0027 (11)
C16	0.0485 (17)	0.0407 (15)	0.0247 (14)	0.0012 (13)	0.0049 (12)	−0.0046 (12)
C17	0.0489 (17)	0.0364 (14)	0.0249 (15)	−0.0014 (13)	−0.0077 (12)	−0.0028 (12)
C18	0.0350 (14)	0.0259 (12)	0.0316 (14)	−0.0029 (10)	−0.0056 (12)	0.0014 (11)
C19	0.0311 (13)	0.0212 (11)	0.0249 (13)	−0.0016 (10)	0.0005 (10)	−0.0002 (10)
C20	0.0309 (13)	0.0156 (10)	0.0235 (13)	0.0006 (9)	0.0013 (10)	0.0004 (9)
C21	0.0365 (14)	0.0221 (11)	0.0354 (15)	0.0019 (11)	0.0089 (12)	0.0050 (11)
C22	0.0562 (19)	0.0371 (15)	0.0350 (16)	0.0126 (14)	0.0206 (15)	0.0128 (13)
C23	0.073 (2)	0.0493 (18)	0.0250 (15)	0.0237 (17)	0.0077 (15)	0.0124 (14)
C24	0.0514 (17)	0.0351 (14)	0.0286 (15)	0.0122 (13)	−0.0061 (13)	0.0075 (12)
C25	0.0346 (14)	0.0182 (11)	0.0294 (14)	0.0025 (10)	0.0004 (11)	0.0044 (10)
C26	0.0274 (13)	0.0227 (11)	0.0234 (13)	−0.0040 (10)	0.0030 (10)	−0.0012 (10)
C27	0.0331 (13)	0.0200 (11)	0.0283 (14)	−0.0021 (10)	0.0015 (11)	−0.0004 (10)
C28	0.0316 (15)	0.0362 (15)	0.077 (2)	−0.0060 (12)	−0.0049 (15)	0.0232 (16)
C29	0.0422 (18)	0.0429 (17)	0.102 (3)	−0.0102 (14)	−0.0059 (19)	0.041 (2)
C30	0.0477 (18)	0.0253 (13)	0.060 (2)	−0.0002 (12)	−0.0086 (15)	0.0137 (14)
C31	0.0330 (14)	0.0282 (12)	0.0392 (16)	0.0039 (11)	0.0000 (12)	0.0002 (11)
C32	0.0302 (14)	0.0267 (12)	0.0319 (15)	−0.0011 (10)	0.0033 (11)	0.0023 (10)
C33	0.0593 (18)	0.0198 (11)	0.0262 (14)	−0.0021 (12)	0.0097 (13)	0.0022 (10)
C34	0.079 (2)	0.0279 (13)	0.0263 (15)	−0.0172 (14)	0.0037 (14)	−0.0045 (12)
C35	0.106 (3)	0.0343 (16)	0.0351 (19)	−0.0162 (19)	0.002 (2)	−0.0050 (14)
C36	0.109 (3)	0.0318 (15)	0.0332 (18)	−0.0064 (19)	0.0212 (19)	−0.0017 (14)
C37	0.086 (3)	0.0321 (15)	0.056 (2)	0.0087 (17)	0.035 (2)	0.0141 (16)
C38	0.0595 (19)	0.0240 (12)	0.0356 (16)	−0.0025 (12)	0.0168 (15)	0.0063 (12)
C39	0.0295 (14)	0.0417 (15)	0.055 (2)	0.0015 (12)	−0.0135 (13)	0.0094 (14)
C40	0.0454 (19)	0.0515 (19)	0.081 (3)	0.0196 (15)	0.0162 (18)	0.0282 (19)

Geometric parameters (Å, º)

O1—C1	1.436 (3)	C17—C18	1.387 (4)
O1—H1	0.88 (2)	C17—H17	0.9500
O2—C13	1.229 (3)	C18—C19	1.388 (4)
O3—C26	1.222 (3)	C18—H18	0.9500
O4—C25	1.377 (3)	C19—H19	0.9500
O4—C39	1.421 (3)	C20—C21	1.392 (4)
O5—C38	1.353 (4)	C20—C25	1.399 (4)
O5—C40	1.439 (4)	C21—C22	1.386 (4)
C1—C7	1.527 (3)	C21—H21	0.9500
C1—C6	1.536 (3)	C22—C23	1.377 (5)
C1—C2	1.549 (3)	C22—H22	0.9500
C2—C13	1.525 (3)	C23—C24	1.388 (5)
C2—C3	1.550 (3)	C23—H23	0.9500
C2—H2	1.0000	C24—C25	1.383 (4)
C3—C20	1.519 (4)	C24—H24	0.9500
C3—C4	1.543 (3)	C26—C27	1.497 (4)
C3—H3	1.0000	C27—C32	1.385 (4)
C4—C26	1.523 (3)	C27—C28	1.395 (4)
C4—C5	1.548 (3)	C28—C29	1.382 (4)
C4—H4	1.0000	C28—H28	0.9500
C5—C33	1.517 (4)	C29—C30	1.376 (5)
C5—C6	1.541 (3)	C29—H29	0.9500
C5—H5	1.0000	C30—C31	1.374 (4)
C6—H6A	0.9900	C30—H30	0.9500
C6—H6B	0.9900	C31—C32	1.388 (4)
C7—C8	1.392 (3)	C31—H31	0.9500
C7—C12	1.393 (3)	C32—H32	0.9500
C8—C9	1.387 (4)	C33—C38	1.386 (4)
C8—H8	0.9500	C33—C34	1.419 (5)
C9—C10	1.379 (4)	C34—C35	1.389 (5)
C9—H9	0.9500	C34—H34	0.9500
C10—C11	1.379 (4)	C35—C36	1.357 (6)
C10—H10	0.9500	C35—H35	0.9500
C11—C12	1.391 (3)	C36—C37	1.367 (6)
C11—H11	0.9500	C36—H36	0.9500
C12—H12	0.9500	C37—C38	1.419 (5)
C13—C14	1.486 (4)	C37—H37	0.9500
C14—C19	1.396 (4)	C39—H39A	0.9800
C14—C15	1.399 (4)	C39—H39B	0.9800
C15—C16	1.383 (4)	C39—H39C	0.9800
C15—H15	0.9500	C40—H40A	0.9800
C16—C17	1.387 (4)	C40—H40B	0.9800
C16—H16	0.9500	C40—H40C	0.9800
C1—O1—H1	108 (3)	C19—C18—H18	120.0
C25—O4—C39	117.8 (2)	C18—C19—C14	120.2 (2)
C38—O5—C40	118.1 (3)	C18—C19—H19	119.9
O1—C1—C7	110.94 (18)	C14—C19—H19	119.9
O1—C1—C6	105.99 (19)	C21—C20—C25	117.8 (2)
C7—C1—C6	112.2 (2)	C21—C20—C3	119.0 (2)
O1—C1—C2	110.2 (2)	C25—C20—C3	122.9 (2)
C7—C1—C2	108.59 (19)	C22—C21—C20	121.5 (3)
C6—C1—C2	108.93 (19)	C22—C21—H21	119.3
C13—C2—C1	112.37 (19)	C20—C21—H21	119.3
C13—C2—C3	107.48 (19)	C23—C22—C21	119.3 (3)
C1—C2—C3	111.52 (19)	C23—C22—H22	120.3
C13—C2—H2	108.5	C21—C22—H22	120.3
C1—C2—H2	108.5	C22—C23—C24	120.7 (3)
C3—C2—H2	108.5	C22—C23—H23	119.6
C20—C3—C4	114.5 (2)	C24—C23—H23	119.6
C20—C3—C2	111.06 (19)	C25—C24—C23	119.4 (3)
C4—C3—C2	109.96 (19)	C25—C24—H24	120.3
C20—C3—H3	107.0	C23—C24—H24	120.3
C4—C3—H3	107.0	O4—C25—C24	123.0 (3)
C2—C3—H3	107.0	O4—C25—C20	115.7 (2)
C26—C4—C3	106.51 (19)	C24—C25—C20	121.2 (3)
C26—C4—C5	110.85 (19)	O3—C26—C27	120.3 (2)
C3—C4—C5	109.88 (19)	O3—C26—C4	119.3 (2)
C26—C4—H4	109.8	C27—C26—C4	120.3 (2)
C3—C4—H4	109.8	C32—C27—C28	118.5 (2)
C5—C4—H4	109.8	C32—C27—C26	123.2 (2)
C33—C5—C6	113.6 (2)	C28—C27—C26	118.3 (2)
C33—C5—C4	112.6 (2)	C29—C28—C27	120.4 (3)
C6—C5—C4	110.37 (19)	C29—C28—H28	119.8
C33—C5—H5	106.6	C27—C28—H28	119.8
C6—C5—H5	106.6	C30—C29—C28	120.6 (3)
C4—C5—H5	106.6	C30—C29—H29	119.7
C1—C6—C5	111.8 (2)	C28—C29—H29	119.7
C1—C6—H6A	109.2	C31—C30—C29	119.5 (3)
C5—C6—H6A	109.2	C31—C30—H30	120.2
C1—C6—H6B	109.2	C29—C30—H30	120.2
C5—C6—H6B	109.2	C30—C31—C32	120.3 (3)
H6A—C6—H6B	107.9	C30—C31—H31	119.8
C8—C7—C12	118.2 (2)	C32—C31—H31	119.8
C8—C7—C1	121.1 (2)	C27—C32—C31	120.7 (2)
C12—C7—C1	120.7 (2)	C27—C32—H32	119.7
C9—C8—C7	120.8 (2)	C31—C32—H32	119.7
C9—C8—H8	119.6	C38—C33—C34	118.7 (3)
C7—C8—H8	119.6	C38—C33—C5	123.4 (3)
C10—C9—C8	120.4 (2)	C34—C33—C5	117.9 (3)
C10—C9—H9	119.8	C35—C34—C33	120.5 (4)
C8—C9—H9	119.8	C35—C34—H34	119.7
C11—C10—C9	119.6 (2)	C33—C34—H34	119.7
C11—C10—H10	120.2	C36—C35—C34	119.2 (4)
C9—C10—H10	120.2	C36—C35—H35	120.4
C10—C11—C12	120.3 (2)	C34—C35—H35	120.4
C10—C11—H11	119.9	C35—C36—C37	122.6 (3)
C12—C11—H11	119.9	C35—C36—H36	118.7
C11—C12—C7	120.7 (2)	C37—C36—H36	118.7
C11—C12—H12	119.6	C36—C37—C38	119.1 (4)
C7—C12—H12	119.6	C36—C37—H37	120.4
O2—C13—C14	120.3 (2)	C38—C37—H37	120.4
O2—C13—C2	119.9 (2)	O5—C38—C33	116.7 (3)
C14—C13—C2	119.6 (2)	O5—C38—C37	123.4 (3)
C19—C14—C15	118.9 (2)	C33—C38—C37	119.8 (3)
C19—C14—C13	122.6 (2)	O4—C39—H39A	109.5
C15—C14—C13	118.5 (2)	O4—C39—H39B	109.5
C16—C15—C14	120.9 (2)	H39A—C39—H39B	109.5
C16—C15—H15	119.5	O4—C39—H39C	109.5
C14—C15—H15	119.5	H39A—C39—H39C	109.5
C15—C16—C17	119.5 (3)	H39B—C39—H39C	109.5
C15—C16—H16	120.2	O5—C40—H40A	109.5
C17—C16—H16	120.2	O5—C40—H40B	109.5
C16—C17—C18	120.4 (3)	H40A—C40—H40B	109.5
C16—C17—H17	119.8	O5—C40—H40C	109.5
C18—C17—H17	119.8	H40A—C40—H40C	109.5
C17—C18—C19	120.1 (2)	H40B—C40—H40C	109.5
C17—C18—H18	120.0
O1—C1—C2—C13	−62.0 (2)	C13—C14—C19—C18	−177.8 (2)
C7—C1—C2—C13	59.7 (2)	C4—C3—C20—C21	−121.5 (2)
C6—C1—C2—C13	−177.82 (19)	C2—C3—C20—C21	113.3 (2)
O1—C1—C2—C3	58.8 (2)	C4—C3—C20—C25	64.1 (3)
C7—C1—C2—C3	−179.53 (19)	C2—C3—C20—C25	−61.2 (3)
C6—C1—C2—C3	−57.1 (2)	C25—C20—C21—C22	3.0 (4)
C13—C2—C3—C20	−50.3 (3)	C3—C20—C21—C22	−171.8 (2)
C1—C2—C3—C20	−173.9 (2)	C20—C21—C22—C23	−0.3 (4)
C13—C2—C3—C4	−178.12 (19)	C21—C22—C23—C24	−2.0 (5)
C1—C2—C3—C4	58.3 (3)	C22—C23—C24—C25	1.5 (5)
C20—C3—C4—C26	56.3 (3)	C39—O4—C25—C24	4.8 (4)
C2—C3—C4—C26	−177.80 (19)	C39—O4—C25—C20	−178.1 (2)
C20—C3—C4—C5	176.5 (2)	C23—C24—C25—O4	178.2 (2)
C2—C3—C4—C5	−57.7 (2)	C23—C24—C25—C20	1.3 (4)
C26—C4—C5—C33	−56.9 (3)	C21—C20—C25—O4	179.4 (2)
C3—C4—C5—C33	−174.3 (2)	C3—C20—C25—O4	−6.1 (3)
C26—C4—C5—C6	175.0 (2)	C21—C20—C25—C24	−3.5 (4)
C3—C4—C5—C6	57.6 (3)	C3—C20—C25—C24	171.0 (2)
O1—C1—C6—C5	−61.6 (3)	C3—C4—C26—O3	68.2 (3)
C7—C1—C6—C5	177.2 (2)	C5—C4—C26—O3	−51.3 (3)
C2—C1—C6—C5	56.9 (3)	C3—C4—C26—C27	−107.8 (2)
C33—C5—C6—C1	174.4 (2)	C5—C4—C26—C27	132.7 (2)
C4—C5—C6—C1	−58.1 (3)	O3—C26—C27—C32	165.6 (3)
O1—C1—C7—C8	0.5 (3)	C4—C26—C27—C32	−18.4 (4)
C6—C1—C7—C8	118.9 (3)	O3—C26—C27—C28	−15.0 (4)
C2—C1—C7—C8	−120.7 (3)	C4—C26—C27—C28	161.0 (3)
O1—C1—C7—C12	178.5 (2)	C32—C27—C28—C29	−0.3 (5)
C6—C1—C7—C12	−63.2 (3)	C26—C27—C28—C29	−179.8 (3)
C2—C1—C7—C12	57.3 (3)	C27—C28—C29—C30	−1.8 (7)
C12—C7—C8—C9	−1.0 (4)	C28—C29—C30—C31	2.3 (6)
C1—C7—C8—C9	177.0 (2)	C29—C30—C31—C32	−0.8 (5)
C7—C8—C9—C10	−0.3 (5)	C28—C27—C32—C31	1.9 (4)
C8—C9—C10—C11	1.2 (4)	C26—C27—C32—C31	−178.7 (3)
C9—C10—C11—C12	−0.8 (4)	C30—C31—C32—C27	−1.3 (4)
C10—C11—C12—C7	−0.5 (4)	C6—C5—C33—C38	68.2 (3)
C8—C7—C12—C11	1.4 (4)	C4—C5—C33—C38	−58.2 (3)
C1—C7—C12—C11	−176.6 (2)	C6—C5—C33—C34	−113.8 (3)
C1—C2—C13—O2	47.2 (3)	C4—C5—C33—C34	119.9 (3)
C3—C2—C13—O2	−75.9 (3)	C38—C33—C34—C35	1.2 (4)
C1—C2—C13—C14	−137.7 (2)	C5—C33—C34—C35	−176.9 (3)
C3—C2—C13—C14	99.2 (2)	C33—C34—C35—C36	−1.0 (5)
O2—C13—C14—C19	−157.0 (2)	C34—C35—C36—C37	0.6 (5)
C2—C13—C14—C19	27.8 (3)	C35—C36—C37—C38	−0.4 (5)
O2—C13—C14—C15	25.3 (3)	C40—O5—C38—C33	164.2 (3)
C2—C13—C14—C15	−149.8 (2)	C40—O5—C38—C37	−17.5 (4)
C19—C14—C15—C16	−0.7 (4)	C34—C33—C38—O5	177.3 (2)
C13—C14—C15—C16	177.1 (2)	C5—C33—C38—O5	−4.6 (4)
C14—C15—C16—C17	1.0 (4)	C34—C33—C38—C37	−1.0 (4)
C15—C16—C17—C18	−0.5 (4)	C5—C33—C38—C37	177.0 (2)
C16—C17—C18—C19	−0.4 (4)	C36—C37—C38—O5	−177.6 (3)
C17—C18—C19—C14	0.7 (4)	C36—C37—C38—C33	0.6 (4)
C15—C14—C19—C18	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.88 (2)	2.01 (3)	2.753 (3)	141 (3)
C2—H2···O4	1.00	2.42	3.033 (3)	119
C4—H4···O4	1.00	2.42	3.028 (3)	118
C4—H4···O5	1.00	2.41	3.009 (3)	118
C6—H6A···O5	0.99	2.54	3.111 (3)	117
C40—H40C···O3^i	0.98	2.45	3.172 (4)	130

Symmetry code: (i) x+1/2, −y, z.