trans-3,3′-Bis(diphenylhydroxymethyl)stilbene–benzene (3/4)

In the crystal structure of the title compound, 3C₄₀H₃₂O₂·4C₆H₆, there are one and a half host mol­ecules and two benzene mol­ecules in the asymmetric unit. The host mol­ecules form a ladder structure via O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.155
• Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The photoisomerization of cis-3,3'-bis(diphenylhydroxymethyl)stilbene to its trans isomer has been observed in inclusion-complex crystals. In the crystals of cis-host with acetone (1/1), there is an intramolecular O—H···O hydrogen bond in the host molecule, and the acetone molecule is connected to the host by an O—H···O hydrogen bond (Tanaka et al., 2002). Here, the structure of the title compound, (I), has been determined, in order to investigate the hydrogen-bonding pattern of the trans-host in the crystals.

The host molecule at the general position is asymmetric, and the two C-CPh₂OH bond axes (C17—C4 and C27—C31) are oriented on the same side of the molecule (Fig. 1). The dihedral angle between the two phenyl rings of the trans-stilbene moiety is 45.82 (12)°, and the central C21—C23═C24—C25 torsion angle is −178.5 (3)°. On the other hand, the half host molecule has a centre of symmetry at the midpoint of the C63═C63ⁱ bond [symmetry code: (i) ?].

The crystal structure of (I) along c is shown in Fig. 2. The host molecules form a ladder structure along c, and the benzene molecules are accommodated in the columns. The host molecules at general position arranged along c are connected by the O2—H2···O1ⁱⁱ hydrogen bond to form a zigzag chain (Fig. 3 and Table 2) [symmetry code: (ii) ?]. The half host molecule acts as both hydrogen donor and accepter, to connect two zigzag chains via O—H···O hydrogen bonds to complete the ladder structure (Fig. 2).

S2. Experimental

The title host compound was prepared according to the method of Tanaka et al. (2002). Crystals of (I) were grown from an acetone/benzene solution.

S3. Refinement

The hydroxyl H atoms were located from difference syntheses and refined isotropically. The other H atoms were positioned geometrically and fixed, with U_iso(H) = 1.2U_eq(parent atom). The central C23═C24 bond of the trans-stilbene moiety is 1.270 (5) Å. Such a short bond length may be the result of dynamic disorder caused by a pedal-like motion, as observed in crystals of trans-stilbene (Ogawa et al., 1992). The C—C distances of the benzene molecules are 1.30 (2)–1.37 (1) Å, and smaller than the standard value. This may be due to the large thermal motion.

Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids plotted at the 50% probability level.
	Fig. 2. The projection of the crystal structure of (I) along c.
	Fig. 3. The arrangement of the host molecules at general position along c.

trans-3,3'-Bis(diphenylhydroxymethyl)stilbene-benzene (3/4)

Crystal data

3C40H32O2·4C6H6	Z = 1
Mr = 1946.52	F(000) = 1032
Triclinic, P1	Dx = 1.176 Mg m^−3
a = 12.972 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 23.653 (4) Å	Cell parameters from 25 reflections
c = 9.304 (4) Å	θ = 10.0–11.5°
α = 100.61 (2)°	µ = 0.07 mm^−1
β = 98.53 (2)°	T = 297 K
γ = 96.030 (13)°	Plate, colourless
V = 2749.0 (14) Å^3	0.40 × 0.20 × 0.05 mm

Data collection

Rigaku AFC-7R diffractometer	θmax = 25.0°
ω scans	h = 0→15
10329 measured reflections	k = −28→28
9676 independent reflections	l = −11→11
4109 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.021	intensity decay: 0.7%

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0579P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.155	(Δ/σ)max = 0.005
S = 0.97	Δρmax = 0.25 e Å^−3
9676 reflections	Δρmin = −0.17 e Å^−3
688 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.7767 (2)	0.1623 (1)	0.8478 (3)	0.0602 (6)
O2	0.9854 (2)	0.1929 (1)	−0.0157 (3)	0.0576 (6)
O3	0.8244 (2)	0.2487 (1)	0.1006 (3)	0.0617 (7)
C4	0.6740 (2)	0.1323 (1)	0.7762 (3)	0.0458 (7)
C5	0.6134 (2)	0.1747 (1)	0.7011 (3)	0.0496 (8)
C6	0.5619 (3)	0.1605 (2)	0.5555 (4)	0.0665 (9)
C7	0.5107 (3)	0.2010 (2)	0.4917 (5)	0.091 (1)
C8	0.5113 (3)	0.2553 (2)	0.5709 (6)	0.094 (1)
C9	0.5595 (3)	0.2696 (2)	0.7164 (6)	0.086 (1)
C10	0.6098 (3)	0.2296 (2)	0.7817 (4)	0.0656 (9)
C11	0.6153 (2)	0.1113 (1)	0.8920 (3)	0.0474 (7)
C12	0.5072 (3)	0.1038 (2)	0.8736 (4)	0.071 (1)
C13	0.4555 (3)	0.0847 (2)	0.9796 (6)	0.096 (1)
C14	0.5110 (5)	0.0739 (2)	1.1048 (5)	0.101 (1)
C15	0.6177 (5)	0.0803 (2)	1.1238 (4)	0.095 (1)
C16	0.6700 (3)	0.0989 (2)	1.0186 (4)	0.0688 (10)
C17	0.6970 (2)	0.0826 (1)	0.6604 (3)	0.0463 (7)
C18	0.6439 (2)	0.0269 (1)	0.6339 (4)	0.0597 (9)
C19	0.6673 (3)	−0.0152 (1)	0.5224 (4)	0.074 (1)
C20	0.7423 (3)	−0.0017 (2)	0.4393 (4)	0.0690 (10)
C21	0.7953 (3)	0.0533 (2)	0.4636 (3)	0.0598 (9)
C22	0.7718 (2)	0.0946 (1)	0.5734 (3)	0.0543 (8)
C23	0.8764 (3)	0.0705 (2)	0.3728 (4)	0.0706 (10)
C24	0.9297 (3)	0.0378 (2)	0.2983 (4)	0.074 (1)
C25	1.0104 (3)	0.0546 (2)	0.2127 (3)	0.0588 (9)
C26	1.0111 (2)	0.1060 (1)	0.1564 (3)	0.0564 (8)
C27	1.0871 (2)	0.1214 (1)	0.0747 (3)	0.0477 (7)
C28	1.1614 (3)	0.0841 (2)	0.0502 (4)	0.0634 (9)
C29	1.1609 (3)	0.0341 (2)	0.1066 (4)	0.075 (1)
C30	1.0865 (3)	0.0196 (2)	0.1856 (4)	0.0708 (10)
C31	1.0907 (2)	0.1787 (1)	0.0183 (3)	0.0454 (7)
C32	1.1424 (2)	0.1734 (1)	−0.1204 (3)	0.0447 (7)
C33	1.2451 (2)	0.1969 (1)	−0.1152 (4)	0.0599 (9)
C34	1.2919 (3)	0.1895 (2)	−0.2409 (5)	0.0710 (10)
C35	1.2372 (3)	0.1586 (2)	−0.3723 (4)	0.073 (1)
C36	1.1352 (3)	0.1346 (2)	−0.3811 (4)	0.075 (1)
C37	1.0874 (2)	0.1419 (1)	−0.2557 (4)	0.0579 (8)
C38	1.1463 (2)	0.2299 (1)	0.1397 (3)	0.0473 (7)
C39	1.2012 (2)	0.2237 (2)	0.2733 (4)	0.0620 (9)
C40	1.2468 (3)	0.2717 (2)	0.3801 (4)	0.078 (1)
C41	1.2381 (3)	0.3264 (2)	0.3570 (4)	0.081 (1)
C42	1.1838 (3)	0.3338 (2)	0.2232 (5)	0.075 (1)
C43	1.1390 (2)	0.2856 (2)	0.1153 (4)	0.0584 (8)
C44	0.8157 (2)	0.2968 (1)	0.2176 (3)	0.0458 (7)
C45	0.6985 (2)	0.3036 (1)	0.1922 (3)	0.0505 (8)
C46	0.6628 (3)	0.3559 (2)	0.1808 (4)	0.074 (1)
C47	0.5554 (3)	0.3601 (2)	0.1577 (5)	0.097 (1)
C48	0.4841 (3)	0.3120 (2)	0.1462 (4)	0.087 (1)
C49	0.5180 (3)	0.2599 (2)	0.1558 (4)	0.075 (1)
C50	0.6241 (2)	0.2556 (1)	0.1789 (4)	0.0608 (9)
C51	0.8535 (2)	0.2816 (1)	0.3677 (3)	0.0453 (7)
C52	0.7946 (2)	0.2839 (1)	0.4787 (4)	0.0599 (9)
C53	0.8349 (3)	0.2714 (2)	0.6146 (4)	0.072 (1)
C54	0.9324 (3)	0.2560 (2)	0.6401 (4)	0.0708 (10)
C55	0.9921 (3)	0.2533 (2)	0.5300 (4)	0.073 (1)
C56	0.9534 (2)	0.2662 (1)	0.3964 (4)	0.0615 (9)
C57	0.8834 (2)	0.3514 (1)	0.1995 (3)	0.0482 (7)
C58	0.9079 (3)	0.3574 (2)	0.0625 (4)	0.0641 (9)
C59	0.9680 (3)	0.4079 (2)	0.0485 (4)	0.076 (1)
C60	1.0038 (3)	0.4520 (2)	0.1703 (4)	0.072 (1)
C61	0.9785 (2)	0.4475 (1)	0.3077 (4)	0.0565 (8)
C62	0.9195 (2)	0.3966 (1)	0.3195 (3)	0.0519 (8)
C63	1.0153 (3)	0.4960 (1)	0.4350 (4)	0.0641 (9)
C64	0.7810 (7)	0.6394 (3)	1.2224 (6)	0.130 (2)
C65	0.6765 (7)	0.6384 (3)	1.1916 (6)	0.126 (2)
C66	0.6114 (4)	0.5938 (4)	1.2085 (7)	0.127 (2)
C67	0.6512 (6)	0.5493 (3)	1.2573 (7)	0.130 (2)
C68	0.7545 (7)	0.5489 (3)	1.2880 (7)	0.138 (2)
C69	0.8210 (5)	0.5938 (4)	1.2716 (7)	0.140 (2)
C70	0.3250 (7)	0.5779 (4)	0.375 (1)	0.169 (3)
C71	0.3606 (7)	0.5325 (5)	0.4138 (8)	0.170 (3)
C72	0.3585 (6)	0.4842 (4)	0.309 (2)	0.155 (3)
C73	0.3176 (7)	0.4835 (4)	0.167 (1)	0.156 (3)
C74	0.2815 (6)	0.5314 (6)	0.1322 (9)	0.162 (3)
C75	0.2838 (6)	0.5777 (4)	0.238 (2)	0.162 (3)
H1	0.771 (3)	0.188 (1)	0.913 (4)	0.0748 (2)*
H2	0.946 (3)	0.167 (2)	−0.071 (4)	0.0991 (2)*
H3	0.879 (3)	0.241 (1)	0.110 (4)	0.0684 (2)*
H6	0.5616	0.1228	0.4983	0.0789*
H7	0.4749	0.1905	0.3924	0.1084*
H8	0.4783	0.2831	0.5255	0.1118*
H9	0.5587	0.3074	0.7729	0.1016*
H10	0.6421	0.2399	0.8832	0.0773*
H12	0.4671	0.1116	0.7869	0.0845*
H13	0.3808	0.0791	0.9650	0.1132*
H14	0.4758	0.0621	1.1793	0.1190*
H15	0.6571	0.0719	1.2101	0.1128*
H16	0.7447	0.1031	1.0330	0.0804*
H18	0.5922	0.0176	0.6916	0.0699*
H19	0.6311	−0.0536	0.5036	0.0873*
H20	0.7574	−0.0311	0.3635	0.0816*
H22	0.8081	0.1329	0.5907	0.0639*
H23	0.8889	0.1106	0.3710	0.0837*
H24	0.9156	−0.0023	0.2979	0.0873*
H26	0.9588	0.1303	0.1740	0.0668*
H28	1.2135	0.0932	−0.0071	0.0746*
H29	1.2133	0.0097	0.0899	0.0890*
H30	1.0867	−0.0154	0.2222	0.0835*
H33	1.2843	0.2187	−0.0236	0.0706*
H34	1.3628	0.2061	−0.2344	0.0841*
H35	1.2697	0.1538	−0.4579	0.0864*
H36	1.0969	0.1129	−0.4737	0.0885*
H37	1.0165	0.1252	−0.2626	0.0682*
H39	1.2077	0.1859	0.2920	0.0723*
H40	1.2849	0.2667	0.4711	0.0926*
H41	1.2688	0.3593	0.4320	0.0969*
H42	1.1777	0.3717	0.2049	0.0884*
H43	1.1021	0.2907	0.0235	0.0677*
H46	0.7121	0.3896	0.1886	0.0859*
H47	0.5318	0.3964	0.1507	0.1152*
H48	0.4109	0.3149	0.1317	0.1034*
H49	0.4681	0.2264	0.1468	0.0892*
H50	0.6468	0.2190	0.1854	0.0724*
H52	0.7257	0.2941	0.4631	0.0711*
H53	0.7936	0.2739	0.6912	0.0854*
H54	0.9592	0.2470	0.7327	0.0836*
H55	1.0606	0.2425	0.5458	0.0850*
H56	0.9964	0.2645	0.3215	0.0718*
H58	0.8834	0.3271	−0.0220	0.0751*
H59	0.9843	0.4118	−0.0455	0.0901*
H60	1.0463	0.4857	0.1598	0.0844*
H62	0.9035	0.3929	0.4136	0.0614*
H63	1.0765	0.5253	0.4197	0.0997*
H64	0.8268	0.6718	1.2106	0.1540*
H65	0.6482	0.6698	1.1567	0.1503*
H66	0.5375	0.5931	1.1865	0.1506*
H67	0.6050	0.5173	1.2698	0.1551*
H68	0.7820	0.5172	1.3228	0.1652*
H69	0.8947	0.5940	1.2930	0.1654*
H70	0.3283	0.6121	0.4484	0.2023*
H71	0.3878	0.5334	0.5146	0.2031*
H72	0.3862	0.4511	0.3350	0.1867*
H73	0.3151	0.4502	0.0918	0.1889*
H74	0.2522	0.5318	0.0325	0.1937*
H75	0.2566	0.6110	0.2134	0.1950*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.041 (1)	0.071 (2)	0.057 (1)	−0.002 (1)	0.003 (1)	−0.009 (1)
O2	0.033 (1)	0.068 (2)	0.069 (2)	0.012 (1)	0.004 (1)	0.008 (1)
O3	0.050 (2)	0.060 (2)	0.067 (2)	0.011 (1)	0.010 (1)	−0.013 (1)
C4	0.035 (2)	0.052 (2)	0.047 (2)	0.001 (1)	0.003 (1)	0.007 (1)
C5	0.040 (2)	0.058 (2)	0.056 (2)	0.004 (1)	0.017 (2)	0.019 (2)
C6	0.057 (2)	0.084 (3)	0.061 (2)	0.007 (2)	0.006 (2)	0.027 (2)
C7	0.078 (3)	0.127 (4)	0.083 (3)	0.024 (3)	0.009 (2)	0.056 (3)
C8	0.071 (3)	0.108 (4)	0.130 (4)	0.031 (3)	0.032 (3)	0.072 (3)
C9	0.068 (3)	0.075 (3)	0.131 (4)	0.023 (2)	0.042 (3)	0.037 (3)
C10	0.057 (2)	0.065 (2)	0.080 (2)	0.014 (2)	0.021 (2)	0.018 (2)
C11	0.052 (2)	0.049 (2)	0.042 (2)	0.008 (1)	0.011 (1)	0.010 (1)
C12	0.057 (2)	0.092 (3)	0.080 (3)	0.018 (2)	0.026 (2)	0.041 (2)
C13	0.083 (3)	0.111 (4)	0.122 (4)	0.029 (3)	0.058 (3)	0.058 (3)
C14	0.142 (5)	0.093 (3)	0.095 (4)	0.027 (3)	0.067 (3)	0.042 (3)
C15	0.139 (4)	0.089 (3)	0.064 (3)	0.016 (3)	0.013 (3)	0.034 (2)
C16	0.075 (2)	0.071 (2)	0.062 (2)	0.012 (2)	0.005 (2)	0.020 (2)
C17	0.044 (2)	0.053 (2)	0.039 (2)	0.003 (1)	0.004 (1)	0.005 (1)
C18	0.062 (2)	0.058 (2)	0.058 (2)	−0.003 (2)	0.017 (2)	0.009 (2)
C19	0.092 (3)	0.047 (2)	0.076 (3)	−0.004 (2)	0.018 (2)	0.000 (2)
C20	0.082 (3)	0.071 (3)	0.058 (2)	0.023 (2)	0.026 (2)	0.004 (2)
C21	0.060 (2)	0.064 (2)	0.053 (2)	0.007 (2)	0.014 (2)	0.005 (2)
C22	0.050 (2)	0.057 (2)	0.051 (2)	0.000 (2)	0.010 (2)	0.003 (2)
C23	0.067 (2)	0.080 (3)	0.062 (2)	0.015 (2)	0.018 (2)	−0.002 (2)
C24	0.077 (3)	0.073 (3)	0.072 (2)	0.005 (2)	0.017 (2)	0.014 (2)
C25	0.061 (2)	0.069 (2)	0.046 (2)	−0.011 (2)	0.016 (2)	0.016 (2)
C26	0.047 (2)	0.067 (2)	0.053 (2)	0.002 (2)	0.010 (2)	0.010 (2)
C27	0.037 (2)	0.058 (2)	0.048 (2)	0.002 (1)	0.009 (1)	0.011 (2)
C28	0.057 (2)	0.070 (2)	0.075 (2)	0.016 (2)	0.026 (2)	0.030 (2)
C29	0.077 (3)	0.072 (3)	0.090 (3)	0.027 (2)	0.029 (2)	0.031 (2)
C30	0.078 (3)	0.064 (2)	0.076 (3)	0.015 (2)	0.020 (2)	0.021 (2)
C31	0.029 (2)	0.056 (2)	0.053 (2)	0.010 (1)	0.009 (1)	0.011 (2)
C32	0.041 (2)	0.047 (2)	0.048 (2)	0.011 (1)	0.008 (1)	0.012 (1)
C33	0.047 (2)	0.073 (2)	0.060 (2)	0.000 (2)	0.018 (2)	0.011 (2)
C34	0.061 (2)	0.071 (2)	0.091 (3)	0.011 (2)	0.034 (2)	0.025 (2)
C35	0.083 (3)	0.080 (3)	0.071 (3)	0.032 (2)	0.034 (2)	0.027 (2)
C36	0.086 (3)	0.091 (3)	0.047 (2)	0.031 (2)	0.006 (2)	0.007 (2)
C37	0.050 (2)	0.065 (2)	0.058 (2)	0.011 (2)	0.007 (2)	0.010 (2)
C38	0.035 (2)	0.055 (2)	0.052 (2)	0.006 (1)	0.011 (1)	0.009 (2)
C39	0.051 (2)	0.071 (2)	0.059 (2)	0.004 (2)	−0.001 (2)	0.012 (2)
C40	0.067 (2)	0.093 (3)	0.060 (2)	0.002 (2)	−0.008 (2)	0.005 (2)
C41	0.070 (3)	0.083 (3)	0.074 (3)	−0.007 (2)	0.008 (2)	−0.012 (2)
C42	0.074 (3)	0.056 (2)	0.089 (3)	0.004 (2)	0.016 (2)	0.001 (2)
C43	0.055 (2)	0.060 (2)	0.059 (2)	0.004 (2)	0.010 (2)	0.011 (2)
C44	0.039 (2)	0.042 (2)	0.052 (2)	0.006 (1)	0.012 (1)	−0.003 (1)
C45	0.046 (2)	0.055 (2)	0.045 (2)	0.008 (2)	0.003 (1)	0.000 (2)
C46	0.054 (2)	0.063 (2)	0.099 (3)	0.015 (2)	0.001 (2)	0.008 (2)
C47	0.063 (3)	0.088 (3)	0.135 (4)	0.029 (2)	0.001 (2)	0.008 (3)
C48	0.049 (2)	0.115 (4)	0.091 (3)	0.021 (3)	0.006 (2)	0.010 (3)
C49	0.048 (2)	0.099 (3)	0.074 (3)	−0.002 (2)	0.005 (2)	0.016 (2)
C50	0.045 (2)	0.070 (2)	0.066 (2)	0.006 (2)	0.009 (2)	0.012 (2)
C51	0.041 (2)	0.038 (2)	0.055 (2)	0.002 (1)	0.008 (1)	0.007 (1)
C52	0.046 (2)	0.072 (2)	0.061 (2)	0.011 (2)	0.010 (2)	0.010 (2)
C53	0.064 (2)	0.096 (3)	0.063 (2)	0.008 (2)	0.018 (2)	0.025 (2)
C54	0.067 (2)	0.078 (3)	0.072 (2)	0.006 (2)	0.007 (2)	0.034 (2)
C55	0.062 (2)	0.088 (3)	0.080 (3)	0.029 (2)	0.013 (2)	0.034 (2)
C56	0.051 (2)	0.077 (2)	0.063 (2)	0.020 (2)	0.016 (2)	0.018 (2)
C57	0.045 (2)	0.053 (2)	0.045 (2)	0.009 (1)	0.005 (1)	0.009 (2)
C58	0.073 (2)	0.065 (2)	0.053 (2)	0.010 (2)	0.010 (2)	0.010 (2)
C59	0.094 (3)	0.078 (3)	0.067 (3)	0.013 (2)	0.030 (2)	0.027 (2)
C60	0.079 (3)	0.060 (2)	0.084 (3)	0.003 (2)	0.020 (2)	0.030 (2)
C61	0.054 (2)	0.049 (2)	0.066 (2)	0.000 (2)	0.009 (2)	0.015 (2)
C62	0.048 (2)	0.055 (2)	0.053 (2)	0.005 (2)	0.008 (2)	0.011 (2)
C63	0.060 (2)	0.049 (2)	0.080 (3)	−0.003 (2)	0.009 (2)	0.015 (2)
C64	0.144 (6)	0.139 (6)	0.097 (4)	−0.025 (5)	0.014 (4)	0.029 (4)
C65	0.166 (6)	0.098 (4)	0.112 (4)	0.038 (4)	0.003 (4)	0.024 (3)
C66	0.096 (4)	0.145 (6)	0.142 (5)	0.039 (4)	0.013 (3)	0.027 (4)
C67	0.134 (5)	0.118 (5)	0.144 (5)	0.006 (4)	0.025 (4)	0.044 (4)
C68	0.152 (6)	0.130 (6)	0.145 (5)	0.064 (5)	0.021 (5)	0.038 (4)
C69	0.093 (4)	0.202 (8)	0.125 (5)	0.036 (5)	0.016 (3)	0.029 (5)
C70	0.217 (8)	0.123 (6)	0.161 (8)	0.059 (5)	0.035 (6)	−0.008 (5)
C71	0.237 (9)	0.167 (7)	0.122 (6)	0.044 (7)	0.048 (5)	0.048 (6)
C72	0.148 (6)	0.103 (6)	0.223 (9)	0.023 (4)	0.033 (7)	0.056 (6)
C73	0.145 (6)	0.110 (6)	0.189 (9)	−0.008 (5)	0.049 (6)	−0.034 (6)
C74	0.154 (6)	0.185 (8)	0.127 (6)	−0.027 (7)	0.010 (5)	0.022 (6)
C75	0.141 (6)	0.134 (7)	0.220 (9)	0.023 (5)	−0.001 (6)	0.078 (7)

Geometric parameters (Å, º)

O1—C4	1.444 (3)	C39—C40	1.377 (5)
O1—H1	0.79 (3)	C39—H39	0.950
O2—C31	1.446 (4)	C40—C41	1.363 (7)
O2—H2	0.80 (3)	C40—H40	0.949
O3—C44	1.450 (4)	C41—C42	1.387 (6)
O3—H3	0.75 (3)	C41—H41	0.950
C4—C5	1.539 (4)	C42—C43	1.382 (4)
C4—C11	1.531 (4)	C42—H42	0.952
C4—C17	1.529 (4)	C43—H43	0.950
C5—C6	1.382 (4)	C44—C45	1.534 (4)
C5—C10	1.384 (4)	C44—C51	1.530 (4)
C6—C7	1.391 (7)	C44—C57	1.534 (4)
C6—H6	0.950	C45—C46	1.380 (5)
C7—C8	1.357 (7)	C45—C50	1.385 (4)
C7—H7	0.946	C46—C47	1.396 (6)
C8—C9	1.369 (7)	C46—H46	0.952
C8—H8	0.950	C47—C48	1.365 (6)
C9—C10	1.383 (6)	C47—H47	0.952
C9—H9	0.954	C48—C49	1.366 (7)
C10—H10	0.951	C48—H48	0.950
C11—C12	1.376 (5)	C49—C50	1.378 (5)
C11—C16	1.378 (5)	C49—H49	0.950
C12—C13	1.387 (7)	C50—H50	0.952
C12—H12	0.951	C51—C52	1.369 (5)
C13—C14	1.356 (7)	C51—C56	1.385 (4)
C13—H13	0.950	C52—C53	1.391 (5)
C14—C15	1.357 (8)	C52—H52	0.948
C14—H14	0.951	C53—C54	1.352 (6)
C15—C16	1.380 (6)	C53—H53	0.950
C15—H15	0.951	C54—C55	1.369 (6)
C16—H16	0.951	C54—H54	0.951
C17—C18	1.383 (4)	C55—C56	1.370 (5)
C17—C22	1.391 (4)	C55—H55	0.948
C18—C19	1.392 (5)	C56—H56	0.952
C18—H18	0.951	C57—C58	1.387 (5)
C19—C20	1.377 (6)	C57—C62	1.382 (4)
C19—H19	0.949	C58—C59	1.394 (5)
C20—C21	1.368 (5)	C58—H58	0.950
C20—H20	0.953	C59—C60	1.378 (5)
C21—C22	1.372 (4)	C59—H59	0.948
C21—C23	1.512 (5)	C60—C61	1.386 (6)
C22—H22	0.950	C60—H60	0.950
C23—C24	1.270 (5)	C61—C62	1.389 (4)
C23—H23	0.950	C61—C63	1.471 (4)
C24—C25	1.472 (5)	C62—H62	0.947
C24—H24	0.948	C63—C63^i	1.314 (7)
C25—C26	1.408 (5)	C63—H63	1.043
C25—C30	1.375 (5)	C64—C65	1.34 (1)
C26—C27	1.390 (4)	C64—C69	1.37 (1)
C26—H26	0.948	C64—H64	0.952
C27—C28	1.389 (5)	C65—C66	1.33 (1)
C27—C31	1.539 (5)	C65—H65	0.950
C28—C29	1.379 (6)	C66—C67	1.34 (1)
C28—H28	0.952	C66—H66	0.948
C29—C30	1.350 (6)	C67—C68	1.33 (1)
C29—H29	0.948	C67—H67	0.951
C30—H30	0.951	C68—C69	1.34 (1)
C31—C32	1.531 (4)	C68—H68	0.952
C31—C38	1.527 (4)	C69—H69	0.947
C32—C33	1.379 (4)	C70—C71	1.30 (2)
C32—C37	1.388 (4)	C70—C75	1.31 (2)
C33—C34	1.387 (6)	C70—H70	0.949
C33—H33	0.952	C71—C72	1.36 (1)
C34—C35	1.355 (5)	C71—H71	0.947
C34—H34	0.951	C72—C73	1.34 (2)
C35—C36	1.369 (6)	C72—H72	0.952
C35—H35	0.949	C73—C74	1.34 (2)
C36—C37	1.393 (5)	C73—H73	0.947
C36—H36	0.953	C74—C75	1.33 (2)
C37—H37	0.950	C74—H74	0.951
C38—C39	1.378 (4)	C75—H75	0.947
C38—C43	1.390 (5)
C4—O1—H1	110 (3)	C38—C39—C40	120.6 (3)
C31—O2—H2	113 (3)	C38—C39—H39	119.7
C44—O3—H3	111 (3)	C40—C39—H39	119.6
O1—C4—C5	108.3 (2)	C39—C40—C41	121.0 (3)
O1—C4—C11	109.5 (2)	C39—C40—H40	119.6
O1—C4—C17	104.2 (2)	C41—C40—H40	119.4
C5—C4—C11	110.6 (2)	C40—C41—C42	119.5 (3)
C5—C4—C17	110.8 (2)	C40—C41—H41	120.4
C11—C4—C17	113.1 (2)	C42—C41—H41	120.0
C4—C5—C6	123.0 (3)	C41—C42—C43	119.5 (4)
C4—C5—C10	119.1 (3)	C41—C42—H42	120.6
C6—C5—C10	117.9 (3)	C43—C42—H42	119.9
C5—C6—C7	120.7 (3)	C38—C43—C42	121.0 (3)
C5—C6—H6	119.7	C38—C43—H43	119.4
C7—C6—H6	119.6	C42—C43—H43	119.6
C6—C7—C8	120.5 (4)	O3—C44—C45	104.1 (2)
C6—C7—H7	119.9	O3—C44—C51	108.8 (2)
C8—C7—H7	119.6	O3—C44—C57	109.2 (2)
C7—C8—C9	119.6 (5)	C45—C44—C51	113.2 (3)
C7—C8—H8	120.1	C45—C44—C57	111.0 (2)
C9—C8—H8	120.3	C51—C44—C57	110.3 (2)
C8—C9—C10	120.5 (4)	C44—C45—C46	122.8 (3)
C8—C9—H9	119.7	C44—C45—C50	119.3 (3)
C10—C9—H9	119.8	C46—C45—C50	117.8 (3)
C5—C10—C9	120.8 (3)	C45—C46—C47	120.9 (3)
C5—C10—H10	119.6	C45—C46—H46	119.7
C9—C10—H10	119.6	C47—C46—H46	119.4
C4—C11—C12	121.7 (3)	C46—C47—C48	119.8 (4)
C4—C11—C16	120.6 (3)	C46—C47—H47	120.1
C12—C11—C16	117.7 (3)	C48—C47—H47	120.1
C11—C12—C13	120.9 (3)	C47—C48—C49	120.0 (4)
C11—C12—H12	119.8	C47—C48—H48	119.9
C13—C12—H12	119.3	C49—C48—H48	120.1
C12—C13—C14	120.3 (4)	C48—C49—C50	120.3 (3)
C12—C13—H13	120.1	C48—C49—H49	119.8
C14—C13—H13	119.6	C50—C49—H49	119.9
C13—C14—C15	119.6 (5)	C45—C50—C49	121.1 (3)
C13—C14—H14	120.5	C45—C50—H50	119.3
C15—C14—H14	119.9	C49—C50—H50	119.6
C14—C15—C16	120.6 (4)	C44—C51—C52	123.4 (3)
C14—C15—H15	120.1	C44—C51—C56	119.1 (3)
C16—C15—H15	119.4	C52—C51—C56	117.4 (3)
C11—C16—C15	120.9 (4)	C51—C52—C53	120.7 (3)
C11—C16—H16	119.2	C51—C52—H52	119.9
C15—C16—H16	119.8	C53—C52—H52	119.4
C4—C17—C18	123.0 (3)	C52—C53—C54	121.0 (4)
C4—C17—C22	118.4 (3)	C52—C53—H53	119.7
C18—C17—C22	118.6 (3)	C54—C53—H53	119.3
C17—C18—C19	119.1 (3)	C53—C54—C55	119.0 (4)
C17—C18—H18	120.2	C53—C54—H54	120.7
C19—C18—H18	120.6	C55—C54—H54	120.2
C18—C19—C20	120.5 (3)	C54—C55—C56	120.3 (3)
C18—C19—H19	119.6	C54—C55—H55	120.2
C20—C19—H19	119.9	C56—C55—H55	119.6
C19—C20—C21	121.1 (3)	C51—C56—C55	121.6 (3)
C19—C20—H20	119.4	C51—C56—H56	119.3
C21—C20—H20	119.5	C55—C56—H56	119.1
C20—C21—C22	118.1 (3)	C44—C57—C58	121.2 (2)
C20—C21—C23	123.0 (3)	C44—C57—C62	120.5 (3)
C22—C21—C23	118.9 (3)	C58—C57—C62	118.3 (3)
C17—C22—C21	122.5 (3)	C57—C58—C59	120.1 (3)
C17—C22—H22	118.9	C57—C58—H58	119.9
C21—C22—H22	118.6	C59—C58—H58	120.0
C21—C23—C24	127.9 (4)	C58—C59—C60	120.4 (4)
C21—C23—H23	116.1	C58—C59—H59	119.8
C24—C23—H23	116.1	C60—C59—H59	119.8
C23—C24—C25	128.0 (4)	C59—C60—C61	120.6 (3)
C23—C24—H24	115.8	C59—C60—H60	119.5
C25—C24—H24	116.2	C61—C60—H60	119.9
C24—C25—C26	121.2 (3)	C60—C61—C62	118.0 (3)
C24—C25—C30	119.8 (3)	C60—C61—C63	119.5 (3)
C26—C25—C30	119.0 (3)	C62—C61—C63	122.5 (3)
C25—C26—C27	120.9 (3)	C57—C62—C61	122.6 (3)
C25—C26—H26	119.6	C57—C62—H62	118.9
C27—C26—H26	119.5	C61—C62—H62	118.5
C26—C27—C28	117.5 (3)	C61—C63—C63^i	127.8 (4)
C26—C27—C31	121.1 (3)	C61—C63—H63	114.0
C28—C27—C31	121.4 (3)	C63^i—C63—H63	118.0
C27—C28—C29	121.3 (3)	C65—C64—C69	119.4 (7)
C27—C28—H28	119.2	C65—C64—H64	120.1
C29—C28—H28	119.5	C69—C64—H64	120.5
C28—C29—C30	120.6 (4)	C64—C65—C66	120.9 (7)
C28—C29—H29	119.7	C64—C65—H65	119.9
C30—C29—H29	119.8	C66—C65—H65	119.3
C25—C30—C29	120.7 (4)	C65—C66—C67	119.3 (6)
C25—C30—H30	119.9	C65—C66—H66	120.6
C29—C30—H30	119.3	C67—C66—H66	120.0
O2—C31—C27	110.0 (2)	C66—C67—C68	121.2 (7)
O2—C31—C32	109.8 (2)	C66—C67—H67	119.7
O2—C31—C38	103.7 (2)	C68—C67—H67	119.1
C27—C31—C32	110.2 (2)	C67—C68—C69	120.0 (7)
C27—C31—C38	111.4 (2)	C67—C68—H68	120.6
C32—C31—C38	111.7 (2)	C69—C68—H68	119.4
C31—C32—C33	122.1 (2)	C64—C69—C68	119.2 (7)
C31—C32—C37	120.1 (3)	C64—C69—H69	120.0
C33—C32—C37	117.7 (3)	C68—C69—H69	120.9
C32—C33—C34	121.3 (3)	C71—C70—C75	121.7 (9)
C32—C33—H33	119.2	C71—C70—H70	119.7
C34—C33—H33	119.6	C75—C70—H70	118.6
C33—C34—C35	120.4 (3)	C70—C71—C72	119.5 (9)
C33—C34—H34	119.6	C70—C71—H71	120.0
C35—C34—H34	120.0	C72—C71—H71	120.5
C34—C35—C36	119.8 (4)	C71—C72—C73	119.5 (9)
C34—C35—H35	120.0	C71—C72—H72	120.3
C36—C35—H35	120.2	C73—C72—H72	120.3
C35—C36—C37	120.3 (3)	C72—C73—C74	119.0 (9)
C35—C36—H36	119.7	C72—C73—H73	120.9
C37—C36—H36	120.0	C74—C73—H73	120.0
C32—C37—C36	120.6 (3)	C73—C74—C75	120.0 (10)
C32—C37—H37	119.6	C73—C74—H74	120.4
C36—C37—H37	119.9	C75—C74—H74	119.6
C31—C38—C39	123.5 (3)	C70—C75—C74	120 (1)
C31—C38—C43	118.1 (3)	C70—C75—H75	120.0
C39—C38—C43	118.3 (3)	C74—C75—H75	119.8
O1—C4—C5—C6	130.9 (3)	C28—C27—C31—C38	−96.4 (3)
O1—C4—C5—C10	−49.2 (4)	C29—C28—C27—C31	177.0 (3)
O1—C4—C11—C12	152.6 (3)	C31—C32—C33—C34	177.3 (3)
O1—C4—C11—C16	−27.9 (4)	C31—C32—C37—C36	−177.1 (3)
O1—C4—C17—C18	137.8 (3)	C31—C38—C39—C40	−177.9 (3)
O1—C4—C17—C22	−45.0 (3)	C31—C38—C43—C42	177.3 (3)
O2—C31—C27—C26	−32.8 (3)	C32—C31—C38—C39	−113.5 (3)
O2—C31—C27—C28	149.3 (2)	C32—C31—C38—C43	68.1 (3)
O2—C31—C32—C33	136.7 (3)	C32—C33—C34—C35	−0.3 (6)
O2—C31—C32—C37	−46.3 (4)	C32—C37—C36—C35	−0.2 (6)
O2—C31—C38—C39	128.4 (3)	C33—C32—C31—C38	22.2 (4)
O2—C31—C38—C43	−50.1 (4)	C33—C32—C37—C36	0.0 (5)
O3—C44—C45—C46	−127.7 (3)	C33—C34—C35—C36	0.1 (6)
O3—C44—C45—C50	51.8 (4)	C34—C33—C32—C37	0.2 (5)
O3—C44—C51—C52	−126.1 (3)	C34—C35—C36—C37	0.1 (6)
O3—C44—C51—C56	55.7 (3)	C37—C32—C31—C38	−160.8 (3)
O3—C44—C57—C58	24.8 (4)	C38—C39—C40—C41	0.5 (6)
O3—C44—C57—C62	−156.7 (3)	C38—C43—C42—C41	0.8 (6)
C4—C5—C6—C7	−178.2 (3)	C39—C38—C43—C42	−1.2 (5)
C4—C5—C10—C9	177.6 (3)	C39—C40—C41—C42	−0.9 (6)
C4—C11—C12—C13	−180.0 (3)	C40—C39—C38—C43	0.5 (5)
C4—C11—C16—C15	179.6 (3)	C40—C41—C42—C43	0.2 (6)
C4—C17—C18—C19	177.6 (3)	C44—C45—C46—C47	180.0 (3)
C4—C17—C22—C21	−177.9 (3)	C44—C45—C50—C49	−179.9 (3)
C5—C4—C11—C12	33.2 (4)	C44—C51—C52—C53	−177.8 (3)
C5—C4—C11—C16	−147.3 (3)	C44—C51—C56—C55	178.7 (3)
C5—C4—C17—C18	−105.9 (3)	C44—C57—C58—C59	178.9 (3)
C5—C4—C17—C22	71.3 (3)	C44—C57—C62—C61	−178.2 (3)
C5—C6—C7—C8	0.5 (6)	C45—C44—C51—C52	−10.9 (4)
C5—C10—C9—C8	0.8 (6)	C45—C44—C51—C56	170.9 (2)
C6—C5—C4—C11	−109.0 (3)	C45—C44—C57—C58	−89.4 (3)
C6—C5—C4—C17	17.2 (4)	C45—C44—C57—C62	89.2 (3)
C6—C5—C10—C9	−2.5 (5)	C45—C46—C47—C48	0.1 (6)
C6—C7—C8—C9	−2.2 (7)	C45—C50—C49—C48	−0.3 (5)
C7—C6—C5—C10	1.9 (5)	C46—C45—C44—C51	114.3 (3)
C7—C8—C9—C10	1.6 (7)	C46—C45—C44—C57	−10.4 (4)
C10—C5—C4—C11	70.9 (3)	C46—C45—C50—C49	−0.3 (5)
C10—C5—C4—C17	−162.9 (3)	C46—C47—C48—C49	−0.7 (6)
C11—C4—C17—C18	19.0 (4)	C47—C46—C45—C50	0.4 (5)
C11—C4—C17—C22	−163.9 (3)	C47—C48—C49—C50	0.8 (6)
C11—C12—C13—C14	0.9 (6)	C50—C45—C44—C51	−66.2 (3)
C11—C16—C15—C14	0.0 (6)	C50—C45—C44—C57	169.1 (3)
C12—C11—C4—C17	−91.7 (3)	C51—C44—C57—C58	144.3 (3)
C12—C11—C16—C15	−0.9 (5)	C51—C44—C57—C62	−37.1 (4)
C12—C13—C14—C15	−1.8 (6)	C51—C52—C53—C54	−0.9 (5)
C13—C12—C11—C16	0.5 (5)	C51—C56—C55—C54	−0.8 (5)
C13—C14—C15—C16	1.4 (6)	C52—C51—C44—C57	114.1 (3)
C16—C11—C4—C17	87.8 (3)	C52—C51—C56—C55	0.5 (4)
C17—C18—C19—C20	−0.1 (5)	C52—C53—C54—C55	0.5 (5)
C17—C22—C21—C20	0.4 (5)	C53—C52—C51—C56	0.3 (4)
C17—C22—C21—C23	179.0 (3)	C53—C54—C55—C56	0.3 (5)
C18—C17—C22—C21	−0.6 (5)	C56—C51—C44—C57	−64.0 (3)
C18—C19—C20—C21	−0.2 (6)	C57—C58—C59—C60	0.3 (6)
C19—C18—C17—C22	0.4 (5)	C57—C62—C61—C60	−1.7 (5)
C19—C20—C21—C22	0.0 (5)	C57—C62—C61—C63	178.8 (3)
C19—C20—C21—C23	−178.6 (3)	C58—C57—C62—C61	0.4 (5)
C20—C21—C23—C24	−22.9 (6)	C58—C59—C60—C61	−1.6 (6)
C21—C23—C24—C25	−178.5 (3)	C59—C58—C57—C62	0.3 (5)
C22—C21—C23—C24	158.5 (4)	C59—C60—C61—C62	2.2 (5)
C23—C24—C25—C26	−24.8 (5)	C59—C60—C61—C63	−178.2 (3)
C23—C24—C25—C30	155.7 (4)	C60—C61—C63—C63^i	167.2 (5)
C24—C25—C26—C27	−179.6 (3)	C61—C63—C63^i—C61^i	−180.0
C24—C25—C30—C29	179.6 (3)	C62—C61—C63—C63^i	−13.3 (7)
C25—C26—C27—C28	0.5 (4)	C64—C65—C66—C67	0.0 (9)
C25—C26—C27—C31	−177.6 (2)	C64—C69—C68—C67	−0.4 (10)
C25—C30—C29—C28	−0.7 (5)	C65—C64—C69—C68	0.0 (9)
C26—C25—C30—C29	0.1 (4)	C65—C66—C67—C68	−0.5 (9)
C26—C27—C28—C29	−1.0 (4)	C66—C65—C64—C69	0.2 (9)
C26—C27—C31—C32	−153.9 (2)	C66—C67—C68—C69	0.7 (10)
C26—C27—C31—C38	81.6 (3)	C70—C71—C72—C73	−1 (1)
C27—C26—C25—C30	0.0 (4)	C70—C75—C74—C73	2 (1)
C27—C28—C29—C30	1.1 (5)	C71—C70—C75—C74	−2 (1)
C27—C31—C32—C33	−102.1 (3)	C71—C72—C73—C74	1 (1)
C27—C31—C32—C37	74.9 (3)	C72—C71—C70—C75	2 (1)
C27—C31—C38—C39	10.2 (4)	C72—C73—C74—C75	−1 (1)
C27—C31—C38—C43	−168.3 (3)	C72—C73—C74—C75	−1 (1)
C28—C27—C31—C32	28.1 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.75 (3)	2.20 (3)	2.827 (3)	141 (3)
O1—H1···O3^ii	0.79 (3)	2.03 (2)	2.761 (3)	154 (3)
O2—H2···O1^iii	0.80 (3)	2.19 (3)	2.774 (2)	129 (3)

Symmetry codes: (ii) x, y, z+1; (iii) x, y, z−1.