(E)-3,5,4'-Tri­methoxy­stilbene

The title compound, C₁₇H₁₈O₃, was prepared from the Wittig-Horner reaction of 3,5-di­methoxy­benzyl­dehyde and di­methyl(4-methoxy­benzyl)­phosphite. There are two mol­ecules in the asymmetric unit, with different conformations.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.152
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Recently, (E)-stilbene derivatives have attracted considerable interest because of their non-linear optical properties (Bustmante et al., 1995; Papper & Likhtenshtein, 2001) and biological activities. The title compound, (I), is a key intermediate in the synthesis of trans-resveratrol, which has been shown to prevent cancer, lower blood pressure, and reduce osteoporosis (Frémont, 2000; Savouret & Quesne, 2002).

There are two molecules, A and B, in the asymmetric unit (Fig. 1); the 3,5-dimethoxy groups adopt s-syn and s-anti conformations in moleules A and B, respectively. The torsion angles of the 4-methoxy groups relative to the benzene rings in A and B are −171.1 (3) and 170.3 (2)°, respectively, and those of the 3,5-dimethoxy groups are in the range 174.9 (3)–177.8 (3)°. The fact that these methoxy groups are almost coplanar with the benzene rings indicates that all these O atoms are sp² hybridized (Zhang et al., 2001; Zheng et al., 2001). The angles between the benzene ring planes in A and B are 26.1 (3) and 25.0 (3)°, respectively; however, that in 2,4'-dihydroxy-3,3'-dimethoxy-5-methylstilbene is 8.90 (9)° (Li et al., 1999). From Fig. 1, it can be seen that the alkene moieties are slightly twisted; the torsion angles C1—C6—C7—C8 and C7—C8—C9—C10 in molecule A are 165.3 (3) and 170.8 (3)°, respectively, while C21—C22—C24—C25 and C24—C25—C26—C31 in molecule B are −159.6 (3) and −178.1 (3)°, respectively.

S2. Experimental

4-Methoxybenzyl chloride (0.06 mol) was heated in a 100 ml round-bottomed flask with trimethylphosphite (20 ml) until the evolution of methyl chloride had ceased. The excess trimethylphosphite was removed by distillation in vacuo. The residue was charged with 3,5-dimethoxybenzaldehyde (DMBA, 0.06 mol), KOH (7.5 g) and DMSO (50 ml). The reaction mixture was stirred at 303 K until there was no DMBA detected by thin-layer chromatography. Then water (50 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na₂SO₄. The solvent was removed by distillation in vacuo. The resulting (E)-3,5,4'-trimethoxystilbene was pure, according to HPLC; yield 15.4 g (95%), m.p. 329.5–330.5 K (literature m.p. 330 K; Ali et al., 1992). Crystals were obtained by slow evaporation of a solution in ethyl acetate. ¹H NMR spectrum (400 MHz, CDCl₃): δ 3.83 (9H, s), 6.38 (1H, t; J = 2 Hz, H-4), 6.65 (2H, d; J = 2 Hz, H-2, 6), 6.87–6.93 (3H, m), 7.04 (1H, d; J = 16 Hz, –CH═CH–), 7.45 (2 H, d; J = 8.8 Hz, H-2', 6').

S3. Refinement

H atoms were placed geometrically and refined with a riding model.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. View of the molecular structure of (I), shown with 50% probability ellipsoids.
	Fig. 2. A packing diagram of (I), viewed along the a axis.

(E)-3,4',5-trimethoxystilbene

Crystal data

C17H18O3	Z = 4
Mr = 270.31	F(000) = 576
Triclinic, P1	Dx = 1.248 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.958 (4) Å	Cell parameters from 664 reflections
b = 10.048 (4) Å	θ = 2.3–22.9°
c = 16.205 (6) Å	µ = 0.09 mm^−1
α = 90.695 (8)°	T = 273 K
β = 105.545 (7)°	Prism, colorless
γ = 111.835 (7)°	0.30 × 0.25 × 0.20 mm
V = 1438.7 (10) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5058 independent reflections
Radiation source: fine-focus sealed tube	2459 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ϕ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.975, Tmax = 0.983	k = −6→11
5991 measured reflections	l = −19→18

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.07P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.053	(Δ/σ)max = 0.001
wR(F^2) = 0.152	Δρmax = 0.18 e Å^−3
S = 0.96	Δρmin = −0.14 e Å^−3
5058 reflections	Extinction correction: SHELXL
368 parameters	Extinction coefficient: 0.026 (3)
0 restraints

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	−0.0032 (2)	0.6268 (3)	0.56782 (14)	0.0751 (7)
O2	0.4243 (2)	1.0334 (2)	0.57601 (13)	0.0689 (7)
O3	0.9097 (2)	0.6888 (2)	1.17518 (13)	0.0614 (6)
O4	−0.3335 (3)	0.6819 (2)	0.63850 (15)	0.0817 (8)
O5	0.0308 (3)	1.1228 (3)	0.60074 (14)	0.0829 (8)
O6	0.4803 (2)	0.7043 (2)	1.21916 (12)	0.0579 (6)
C1	0.2212 (3)	0.6783 (3)	0.69072 (19)	0.0549 (8)
H1	0.1727	0.5975	0.7149	0.066*
C2	0.1446 (4)	0.7089 (4)	0.61339 (19)	0.0545 (8)
C3	0.2152 (4)	0.8281 (3)	0.57634 (19)	0.0558 (8)
H3	0.1632	0.8481	0.5244	0.067*
C4	0.3631 (4)	0.9168 (3)	0.61701 (18)	0.0508 (8)
C5	0.4414 (3)	0.8888 (3)	0.69429 (18)	0.0516 (8)
H5	0.5414	0.9502	0.7212	0.062*
C6	0.3706 (3)	0.7685 (3)	0.73213 (18)	0.0475 (8)
C7	0.4491 (4)	0.7377 (3)	0.81533 (18)	0.0527 (8)
H7	0.3888	0.6724	0.8437	0.063*
C8	0.5960 (3)	0.7927 (3)	0.85426 (18)	0.0491 (8)
H8	0.6555	0.8554	0.8244	0.059*
C9	0.6776 (3)	0.7681 (3)	0.93831 (18)	0.0429 (7)
C10	0.8341 (3)	0.8191 (3)	0.96368 (19)	0.0492 (8)
H10	0.8859	0.8709	0.9269	0.059*
C11	0.9161 (3)	0.7961 (3)	1.04152 (19)	0.0507 (8)
H11	1.0211	0.8311	1.0562	0.061*
C12	0.8413 (3)	0.7208 (3)	1.09727 (18)	0.0444 (7)
C13	0.6861 (3)	0.6709 (3)	1.07416 (18)	0.0502 (8)
H13	0.6352	0.6208	1.1117	0.060*
C14	0.6050 (3)	0.6937 (3)	0.99671 (18)	0.0473 (8)
H14	0.5001	0.6591	0.9828	0.057*
C15	−0.0813 (4)	0.5002 (4)	0.6001 (2)	0.0847 (11)
H15A	−0.0280	0.4370	0.6050	0.127*
H15B	−0.1815	0.4522	0.5613	0.127*
H15C	−0.0876	0.5255	0.6558	0.127*
C16	0.5796 (4)	1.1235 (3)	0.6126 (2)	0.0705 (10)
H16A	0.5944	1.1695	0.6684	0.106*
H16B	0.6101	1.1959	0.5757	0.106*
H16C	0.6393	1.0661	0.6183	0.106*
C17	1.0694 (4)	0.7555 (4)	1.2070 (2)	0.0813 (11)
H17A	1.1134	0.7191	1.1708	0.122*
H17B	1.1021	0.7346	1.2649	0.122*
H17C	1.1009	0.8582	1.2069	0.122*
C18	−0.1941 (4)	0.7934 (4)	0.6645 (2)	0.0567 (8)
C19	−0.1477 (4)	0.9063 (3)	0.61767 (19)	0.0584 (9)
H19	−0.2115	0.9110	0.5651	0.070*
C20	−0.0040 (4)	1.0125 (3)	0.6508 (2)	0.0562 (9)
C21	0.0929 (3)	1.0073 (3)	0.72851 (19)	0.0534 (8)
H21	0.1892	1.0798	0.7495	0.064*
C22	0.0445 (3)	0.8917 (3)	0.77516 (18)	0.0477 (8)
C23	−0.1001 (4)	0.7873 (3)	0.74229 (19)	0.0569 (8)
H23	−0.1344	0.7113	0.7736	0.068*
C24	0.1467 (3)	0.8851 (3)	0.85742 (18)	0.0504 (8)
H24	0.2262	0.9708	0.8854	0.060*
C25	0.1347 (3)	0.7664 (3)	0.89528 (18)	0.0494 (8)
H25	0.0571	0.6815	0.8647	0.059*
C26	0.2275 (3)	0.7514 (3)	0.97881 (18)	0.0424 (7)
C27	0.3433 (3)	0.8674 (3)	1.03543 (18)	0.0460 (7)
H27	0.3657	0.9601	1.0197	0.055*
C28	0.4249 (3)	0.8485 (3)	1.11361 (18)	0.0461 (7)
H28	0.5027	0.9278	1.1498	0.055*
C29	0.3923 (3)	0.7114 (3)	1.13931 (18)	0.0436 (7)
C30	0.2787 (3)	0.5942 (3)	1.08430 (19)	0.0488 (8)
H30	0.2564	0.5016	1.1002	0.059*
C31	0.1985 (3)	0.6158 (3)	1.00548 (18)	0.0478 (8)
H31	0.1220	0.5362	0.9689	0.057*
C32	−0.4395 (4)	0.6868 (4)	0.5622 (2)	0.0791 (11)
H32A	−0.4540	0.7756	0.5664	0.119*
H32B	−0.5341	0.6067	0.5545	0.119*
H32C	−0.4026	0.6814	0.5138	0.119*
C33	0.1790 (4)	1.2307 (4)	0.6251 (2)	0.0822 (11)
H33A	0.1994	1.2810	0.6806	0.123*
H33B	0.1879	1.2977	0.5832	0.123*
H33C	0.2504	1.1865	0.6280	0.123*
C34	0.4351 (4)	0.5702 (3)	1.2535 (2)	0.0749 (11)
H34A	0.3315	0.5401	1.2531	0.112*
H34B	0.4980	0.5817	1.3117	0.112*
H34C	0.4455	0.4985	1.2188	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0578 (16)	0.0748 (16)	0.0669 (15)	0.0081 (13)	0.0029 (13)	0.0073 (13)
O2	0.0617 (16)	0.0732 (15)	0.0553 (14)	0.0136 (13)	0.0088 (12)	0.0202 (13)
O3	0.0536 (14)	0.0746 (15)	0.0559 (14)	0.0279 (12)	0.0112 (11)	0.0171 (12)
O4	0.0566 (16)	0.0727 (16)	0.0805 (17)	0.0050 (13)	−0.0071 (13)	0.0208 (14)
O5	0.0706 (17)	0.0782 (16)	0.0759 (16)	0.0119 (14)	0.0070 (13)	0.0365 (14)
O6	0.0649 (14)	0.0517 (13)	0.0520 (13)	0.0191 (11)	0.0140 (11)	0.0163 (11)
C1	0.060 (2)	0.051 (2)	0.053 (2)	0.0194 (18)	0.0179 (18)	0.0031 (17)
C2	0.053 (2)	0.062 (2)	0.0442 (19)	0.0224 (18)	0.0063 (17)	−0.0018 (17)
C3	0.057 (2)	0.061 (2)	0.0445 (19)	0.0228 (18)	0.0062 (17)	0.0056 (17)
C4	0.058 (2)	0.056 (2)	0.0407 (18)	0.0261 (18)	0.0126 (17)	0.0056 (16)
C5	0.053 (2)	0.052 (2)	0.0463 (19)	0.0181 (16)	0.0130 (16)	0.0025 (16)
C6	0.053 (2)	0.0505 (19)	0.0416 (18)	0.0239 (17)	0.0125 (16)	0.0013 (16)
C7	0.060 (2)	0.0471 (18)	0.051 (2)	0.0201 (17)	0.0179 (17)	0.0073 (16)
C8	0.056 (2)	0.0470 (18)	0.0497 (19)	0.0221 (17)	0.0214 (17)	0.0102 (15)
C9	0.0442 (19)	0.0390 (17)	0.0486 (18)	0.0165 (15)	0.0180 (15)	0.0044 (14)
C10	0.052 (2)	0.0447 (18)	0.055 (2)	0.0173 (16)	0.0243 (17)	0.0133 (16)
C11	0.0356 (18)	0.054 (2)	0.063 (2)	0.0154 (15)	0.0176 (16)	0.0055 (17)
C12	0.047 (2)	0.0454 (18)	0.0468 (18)	0.0239 (16)	0.0152 (16)	0.0066 (15)
C13	0.046 (2)	0.056 (2)	0.052 (2)	0.0169 (16)	0.0235 (16)	0.0139 (16)
C14	0.0396 (17)	0.0525 (19)	0.0497 (19)	0.0178 (15)	0.0130 (15)	0.0056 (15)
C15	0.068 (3)	0.075 (3)	0.091 (3)	0.008 (2)	0.022 (2)	0.007 (2)
C16	0.070 (3)	0.067 (2)	0.063 (2)	0.017 (2)	0.0143 (19)	0.0138 (19)
C17	0.060 (3)	0.115 (3)	0.070 (2)	0.042 (2)	0.0067 (19)	0.013 (2)
C18	0.054 (2)	0.058 (2)	0.053 (2)	0.0216 (18)	0.0076 (17)	0.0096 (18)
C19	0.060 (2)	0.061 (2)	0.049 (2)	0.0242 (18)	0.0063 (17)	0.0088 (18)
C20	0.062 (2)	0.055 (2)	0.055 (2)	0.0253 (19)	0.0180 (18)	0.0166 (18)
C21	0.0497 (19)	0.055 (2)	0.056 (2)	0.0200 (16)	0.0164 (17)	0.0100 (17)
C22	0.049 (2)	0.0527 (19)	0.0462 (18)	0.0233 (17)	0.0162 (16)	0.0097 (16)
C23	0.053 (2)	0.060 (2)	0.055 (2)	0.0194 (18)	0.0154 (17)	0.0145 (17)
C24	0.0460 (19)	0.058 (2)	0.0498 (19)	0.0212 (16)	0.0166 (16)	0.0073 (16)
C25	0.0485 (19)	0.0496 (19)	0.0500 (19)	0.0210 (16)	0.0116 (16)	0.0027 (16)
C26	0.0418 (18)	0.0407 (17)	0.0486 (18)	0.0180 (15)	0.0167 (15)	0.0059 (15)
C27	0.0510 (19)	0.0389 (17)	0.0542 (19)	0.0190 (16)	0.0225 (16)	0.0122 (15)
C28	0.0465 (18)	0.0376 (17)	0.0501 (19)	0.0120 (14)	0.0141 (15)	0.0031 (15)
C29	0.0477 (19)	0.0457 (18)	0.0441 (18)	0.0219 (16)	0.0184 (16)	0.0083 (15)
C30	0.055 (2)	0.0383 (17)	0.057 (2)	0.0191 (16)	0.0214 (17)	0.0114 (16)
C31	0.0433 (18)	0.0379 (18)	0.056 (2)	0.0112 (15)	0.0117 (16)	−0.0012 (15)
C32	0.070 (3)	0.079 (3)	0.066 (2)	0.023 (2)	−0.007 (2)	−0.001 (2)
C33	0.076 (3)	0.080 (3)	0.084 (3)	0.020 (2)	0.027 (2)	0.032 (2)
C34	0.089 (3)	0.060 (2)	0.067 (2)	0.025 (2)	0.014 (2)	0.0260 (19)

Geometric parameters (Å, º)

O1—C2	1.376 (3)	C16—H16A	0.960
O1—C15	1.412 (3)	C16—H16B	0.960
O2—C4	1.375 (3)	C16—H16C	0.960
O2—C16	1.421 (3)	C17—H17A	0.960
O3—C12	1.369 (3)	C17—H17B	0.960
O3—C17	1.415 (4)	C17—H17C	0.960
O4—C18	1.370 (4)	C18—C23	1.371 (4)
O4—C32	1.409 (3)	C18—C19	1.377 (4)
O5—C20	1.376 (3)	C19—C20	1.384 (4)
O5—C33	1.413 (4)	C19—H19	0.930
O6—C29	1.374 (3)	C20—C21	1.381 (4)
O6—C34	1.424 (3)	C21—C22	1.398 (4)
C1—C2	1.385 (4)	C21—H21	0.930
C1—C6	1.390 (4)	C22—C23	1.382 (4)
C1—H1	0.930	C22—C24	1.463 (4)
C2—C3	1.380 (4)	C23—H23	0.930
C3—C4	1.374 (4)	C24—C25	1.328 (4)
C3—H3	0.930	C24—H24	0.930
C4—C5	1.380 (4)	C25—C26	1.465 (4)
C5—C6	1.397 (4)	C25—H25	0.930
C5—H5	0.930	C26—C31	1.384 (4)
C6—C7	1.466 (4)	C26—C27	1.391 (4)
C7—C8	1.319 (4)	C27—C28	1.368 (3)
C7—H7	0.930	C27—H27	0.930
C8—C9	1.463 (4)	C28—C29	1.389 (4)
C8—H8	0.930	C28—H28	0.930
C9—C10	1.384 (4)	C29—C30	1.380 (4)
C9—C14	1.400 (4)	C30—C31	1.380 (4)
C10—C11	1.381 (4)	C30—H30	0.930
C10—H10	0.930	C31—H31	0.930
C11—C12	1.379 (4)	C32—H32A	0.960
C11—H11	0.930	C32—H32B	0.960
C12—C13	1.374 (4)	C32—H32C	0.960
C13—C14	1.371 (4)	C33—H33A	0.960
C13—H13	0.930	C33—H33B	0.960
C14—H14	0.930	C33—H33C	0.960
C15—H15A	0.960	C34—H34A	0.960
C15—H15B	0.960	C34—H34B	0.960
C15—H15C	0.960	C34—H34C	0.960
C2—O1—C15	118.3 (3)	O3—C17—H17C	109.5
C4—O2—C16	117.7 (2)	H17A—C17—H17C	109.5
C12—O3—C17	117.6 (2)	H17B—C17—H17C	109.5
C18—O4—C32	118.5 (3)	C23—C18—O4	115.6 (3)
C20—O5—C33	118.7 (2)	C23—C18—C19	120.6 (3)
C29—O6—C34	117.3 (2)	O4—C18—C19	123.7 (3)
C2—C1—C6	120.0 (3)	C18—C19—C20	118.3 (3)
C2—C1—H1	120.0	C18—C19—H19	120.8
C6—C1—H1	120.0	C20—C19—H19	120.8
O1—C2—C3	115.0 (3)	O5—C20—C21	123.9 (3)
O1—C2—C1	124.3 (3)	O5—C20—C19	114.2 (3)
C3—C2—C1	120.7 (3)	C21—C20—C19	121.9 (3)
C4—C3—C2	119.3 (3)	C20—C21—C22	119.2 (3)
C4—C3—H3	120.4	C20—C21—H21	120.4
C2—C3—H3	120.4	C22—C21—H21	120.4
C3—C4—O2	115.5 (3)	C23—C22—C21	118.6 (3)
C3—C4—C5	121.0 (3)	C23—C22—C24	121.9 (3)
O2—C4—C5	123.5 (3)	C21—C22—C24	119.5 (3)
C4—C5—C6	120.0 (3)	C18—C23—C22	121.4 (3)
C4—C5—H5	120.0	C18—C23—H23	119.3
C6—C5—H5	120.0	C22—C23—H23	119.3
C1—C6—C5	119.0 (3)	C25—C24—C22	125.2 (3)
C1—C6—C7	119.5 (3)	C25—C24—H24	117.4
C5—C6—C7	121.5 (3)	C22—C24—H24	117.4
C8—C7—C6	127.0 (3)	C24—C25—C26	128.7 (3)
C8—C7—H7	116.5	C24—C25—H25	115.7
C6—C7—H7	116.5	C26—C25—H25	115.7
C7—C8—C9	128.4 (3)	C31—C26—C27	116.8 (3)
C7—C8—H8	115.8	C31—C26—C25	119.4 (3)
C9—C8—H8	115.8	C27—C26—C25	123.8 (3)
C10—C9—C14	116.6 (3)	C28—C27—C26	121.7 (3)
C10—C9—C8	120.3 (3)	C28—C27—H27	119.1
C14—C9—C8	123.1 (3)	C26—C27—H27	119.1
C11—C10—C9	122.5 (3)	C27—C28—C29	120.4 (3)
C11—C10—H10	118.7	C27—C28—H28	119.8
C9—C10—H10	118.7	C29—C28—H28	119.8
C12—C11—C10	119.6 (3)	O6—C29—C30	125.0 (3)
C12—C11—H11	120.2	O6—C29—C28	115.8 (3)
C10—C11—H11	120.2	C30—C29—C28	119.2 (3)
O3—C12—C13	116.0 (3)	C29—C30—C31	119.4 (3)
O3—C12—C11	124.9 (3)	C29—C30—H30	120.3
C13—C12—C11	119.0 (3)	C31—C30—H30	120.3
C14—C13—C12	121.2 (3)	C30—C31—C26	122.5 (3)
C14—C13—H13	119.4	C30—C31—H31	118.7
C12—C13—H13	119.4	C26—C31—H31	118.7
C13—C14—C9	121.0 (3)	O4—C32—H32A	109.5
C13—C14—H14	119.5	O4—C32—H32B	109.5
C9—C14—H14	119.5	H32A—C32—H32B	109.5
O1—C15—H15A	109.5	O4—C32—H32C	109.5
O1—C15—H15B	109.5	H32A—C32—H32C	109.5
H15A—C15—H15B	109.5	H32B—C32—H32C	109.5
O1—C15—H15C	109.5	O5—C33—H33A	109.5
H15A—C15—H15C	109.5	O5—C33—H33B	109.5
H15B—C15—H15C	109.5	H33A—C33—H33B	109.5
O2—C16—H16A	109.5	O5—C33—H33C	109.5
O2—C16—H16B	109.5	H33A—C33—H33C	109.5
H16A—C16—H16B	109.5	H33B—C33—H33C	109.5
O2—C16—H16C	109.5	O6—C34—H34A	109.5
H16A—C16—H16C	109.5	O6—C34—H34B	109.5
H16B—C16—H16C	109.5	H34A—C34—H34B	109.5
O3—C17—H17A	109.5	O6—C34—H34C	109.5
O3—C17—H17B	109.5	H34A—C34—H34C	109.5
H17A—C17—H17B	109.5	H34B—C34—H34C	109.5
C15—O1—C2—C3	177.8 (3)	C32—O4—C18—C23	175.6 (3)
C15—O1—C2—C1	−2.1 (4)	C32—O4—C18—C19	−4.1 (5)
C6—C1—C2—O1	−179.7 (3)	C23—C18—C19—C20	0.4 (4)
C6—C1—C2—C3	0.3 (4)	O4—C18—C19—C20	−179.9 (3)
O1—C2—C3—C4	−179.9 (3)	C33—O5—C20—C21	6.4 (4)
C1—C2—C3—C4	0.0 (4)	C33—O5—C20—C19	−174.9 (3)
C2—C3—C4—O2	−179.6 (3)	C18—C19—C20—O5	−178.3 (3)
C2—C3—C4—C5	−0.3 (4)	C18—C19—C20—C21	0.4 (4)
C16—O2—C4—C3	−176.2 (3)	O5—C20—C21—C22	178.4 (3)
C16—O2—C4—C5	4.6 (4)	C19—C20—C21—C22	−0.1 (4)
C3—C4—C5—C6	0.3 (4)	C20—C21—C22—C23	−0.9 (4)
O2—C4—C5—C6	179.5 (2)	C20—C21—C22—C24	179.8 (3)
C2—C1—C6—C5	−0.3 (4)	O4—C18—C23—C22	178.9 (3)
C2—C1—C6—C7	178.0 (3)	C19—C18—C23—C22	−1.4 (5)
C4—C5—C6—C1	0.0 (4)	C21—C22—C23—C18	1.7 (4)
C4—C5—C6—C7	−178.3 (3)	C24—C22—C23—C18	−179.0 (3)
C1—C6—C7—C8	165.3 (3)	C23—C22—C24—C25	21.2 (4)
C5—C6—C7—C8	−16.4 (5)	C21—C22—C24—C25	−159.6 (3)
C6—C7—C8—C9	177.9 (3)	C22—C24—C25—C26	−177.1 (3)
C7—C8—C9—C10	170.8 (3)	C24—C25—C26—C31	−178.1 (3)
C7—C8—C9—C14	−9.2 (5)	C24—C25—C26—C27	3.5 (5)
C14—C9—C10—C11	1.4 (4)	C31—C26—C27—C28	0.2 (4)
C8—C9—C10—C11	−178.6 (3)	C25—C26—C27—C28	178.6 (2)
C9—C10—C11—C12	−0.7 (4)	C26—C27—C28—C29	−1.0 (4)
C17—O3—C12—C13	−171.1 (3)	C34—O6—C29—C30	−10.7 (4)
C17—O3—C12—C11	9.9 (4)	C34—O6—C29—C28	170.3 (2)
C10—C11—C12—O3	178.6 (3)	C27—C28—C29—O6	−179.6 (2)
C10—C11—C12—C13	−0.3 (4)	C27—C28—C29—C30	1.3 (4)
O3—C12—C13—C14	−178.5 (3)	O6—C29—C30—C31	−179.9 (2)
C11—C12—C13—C14	0.5 (4)	C28—C29—C30—C31	−0.9 (4)
C12—C13—C14—C9	0.3 (4)	C29—C30—C31—C26	0.1 (4)
C10—C9—C14—C13	−1.2 (4)	C27—C26—C31—C30	0.3 (4)
C8—C9—C14—C13	178.8 (3)	C25—C26—C31—C30	−178.3 (2)