Diethyl trans-2,3-di­benzoyl-2-butenedioate

The title compound, C₂₂H₂₀O₆, has a central double bond of length 1.3694 (12) Å. Two benzene rings, lying on different sides of the diethyl 2-butenedioate main chain, are almost parallel to each other and nearly perpendicular to the main chain. In the unit cell, two symmetry-equivalent mol­ecules are in general positions and two mol­ecules lie on inversion centres.

S1. Comment

The title compound, (I), is a member of the lignans, which are natural products. Because of its broad range of biological activities (Macrae et al., 1984), limited deposition in nature and complicated stereochemistry, much interest has been focused on it (Knorr, 1896; Pelter et al., 1982; Wu et al., 1997). Many consider it to be formed by dimerization of an ArC₃ fragment at the β,β-C atoms through a single bond and the β-C atoms are chiral (Wu et al. 1997). In order to deepen the understanding of the structure of the title compound at a molecular level and to provide some information on the synthesis of this class of organic compounds, we determined the crystal structure. We found that the title compound does not have chiral C atoms; the two β-C atoms (C12 and C13) are joined by a double bond of length 1.3694 (12) Å and the sums of the bond angles at C12 and C13 are 359.92 (7) and 359.89 (7)°, respectively. Two benzene rings, lying on different sides of the diethyl 2-butenedioate main chain, are almost parallel to each other and nearly perpendicular to the main chain. In the unit cell, one molecule lies in a general position, with its inversion-related partner, and two molecules lie on inversion centres.

S2. Experimental

The title compound was synthesized according to the literature method of Wu et al. (1997) and recrystallized from dry ethanol. Crystals suitable for X-ray determination were obtained by slow evaporation from a solution in formyl acetoacetate over a period of three weeks.

S3. Refinement

All H atoms were refined as riding (C—H 0.93–0.97 Å).

Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1989); cell refinement: CAD-4-PC (Enraf-Nonius, 1989); data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

trans-2,3-Dibenzoyl-2-butenedioic acide diethyl ester

Crystal data

C22H20O6	Z = 4
Mr = 380.38	F(000) = 800
Triclinic, P1	Dx = 1.271 Mg m^−3
a = 8.828 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.174 (5) Å	Cell parameters from 25 reflections
c = 16.420 (7) Å	θ = 10.9–12.8°
α = 113.52 (3)°	µ = 0.09 mm^−1
β = 99.27 (4)°	T = 293 K
γ = 83.53 (4)°	Block, colourless
V = 1987.6 (17) Å^3	0.45 × 0.37 × 0.35 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	6310 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.4°
Graphite monochromator	h = −10→10
θ/2θ scans	k = −18→16
Absorption correction: ψ scan (North et al., 1968)	l = 0→19
Tmin = 0.941, Tmax = 0.966	3 standard reflections every 400 reflections
6828 measured reflections	intensity decay: 0.1%
6828 independent reflections

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.140P] where P = (Fo^2 + 2Fc^2)/3
6828 reflections	(Δ/σ)max = 0.002
505 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.32 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
O11	0.00662 (8)	0.50155 (5)	0.12518 (4)	0.07635 (19)
O12	0.20153 (8)	0.39634 (5)	0.08928 (4)	0.0799 (2)
O13	−0.15387 (7)	0.49208 (5)	0.28150 (5)	0.07019 (16)
O14	0.29288 (6)	0.51417 (4)	0.42116 (4)	0.05981 (14)
O15	0.07138 (6)	0.59348 (4)	0.45891 (3)	0.05397 (13)
O16	0.44367 (7)	0.51032 (5)	0.25929 (5)	0.07042 (16)
C11	0.12183 (9)	0.46319 (5)	0.14712 (5)	0.05022 (17)
C12	0.18923 (8)	0.48043 (5)	0.23955 (5)	0.04256 (15)
C13	0.10007 (8)	0.52521 (5)	0.30725 (4)	0.04064 (14)
C14	0.16661 (8)	0.54263 (5)	0.39989 (5)	0.04497 (16)
C15	0.15276 (12)	0.36875 (9)	−0.00669 (7)	0.0805 (3)
H151	0.0607	0.4061	−0.0172	0.080*
H152	0.1327	0.3009	−0.0355	0.080*
C16	0.28599 (15)	0.39035 (9)	−0.04097 (8)	0.0929 (3)
H161	0.2630	0.3736	−0.1044	0.080*
H162	0.3761	0.3535	−0.0290	0.080*
H163	0.3041	0.4577	−0.0115	0.080*
C17	0.12746 (10)	0.61271 (7)	0.55240 (5)	0.0627 (2)
H171	0.2190	0.6493	0.5710	0.080*
H172	0.1527	0.5528	0.5608	0.080*
C18	0.00133 (11)	0.66939 (6)	0.60635 (6)	0.0654 (2)
H181	0.0344	0.6834	0.6687	0.080*
H182	−0.0886	0.6325	0.5873	0.080*
H183	−0.0225	0.7285	0.5975	0.080*
C111	0.40709 (7)	0.35697 (5)	0.25058 (4)	0.04054 (14)
C112	0.56257 (9)	0.32814 (6)	0.25347 (5)	0.05188 (17)
H11A	0.6344	0.3707	0.2578	0.080*
C113	0.61092 (10)	0.23801 (6)	0.25006 (6)	0.0655 (2)
H11B	0.7148	0.2189	0.2506	0.080*
C114	0.50469 (11)	0.17523 (6)	0.24574 (6)	0.0661 (2)
H11C	0.5376	0.1147	0.2455	0.080*
C115	0.35100 (10)	0.20222 (6)	0.24180 (6)	0.0603 (2)
H11D	0.2798	0.1594	0.2376	0.080*
C116	0.30173 (8)	0.29194 (5)	0.24396 (5)	0.04793 (16)
H11E	0.1972	0.3095	0.2410	0.080*
C117	0.35294 (8)	0.45200 (5)	0.25282 (5)	0.04772 (16)
C121	−0.11949 (8)	0.64702 (5)	0.29435 (4)	0.04367 (15)
C122	−0.27624 (9)	0.67151 (6)	0.28460 (5)	0.05212 (17)
H12B	−0.3474	0.6274	0.2774	0.080*
C123	−0.32579 (10)	0.76161 (6)	0.28559 (6)	0.0611 (2)
H12C	−0.4305	0.7782	0.2803	0.080*
C124	−0.22442 (11)	0.82591 (6)	0.29404 (6)	0.0620 (2)
H12D	−0.2603	0.8856	0.2933	0.080*
C125	−0.06708 (10)	0.80406 (6)	0.30380 (6)	0.0605 (2)
H12E	0.0023	0.8488	0.3099	0.080*
C126	−0.01497 (9)	0.71435 (5)	0.30438 (5)	0.05078 (17)
H12F	0.0900	0.6991	0.3115	0.080*
C127	−0.06356 (9)	0.55232 (5)	0.29246 (5)	0.04917 (17)
O21	0.28058 (7)	−0.02632 (5)	−0.02297 (5)	0.07907 (19)
O22	0.23038 (5)	0.13180 (4)	0.01489 (3)	0.04960 (12)
O23	−0.02822 (7)	0.16621 (4)	0.14567 (4)	0.06527 (15)
C21	0.19269 (8)	0.04491 (5)	0.00059 (5)	0.05027 (17)
C22	0.03379 (8)	0.04454 (5)	0.01468 (5)	0.04837 (16)
C23	0.38731 (9)	0.14387 (6)	0.00614 (6)	0.05532 (18)
H231	0.4574	0.1040	0.0306	0.080*
H232	0.4122	0.2104	0.0404	0.080*
C24	0.40877 (12)	0.11695 (8)	−0.08979 (7)	0.0748 (2)
H241	0.5142	0.1233	−0.0935	0.080*
H242	0.3437	0.1588	−0.1132	0.080*
H243	0.3822	0.0515	−0.1241	0.080*
C211	−0.12743 (8)	0.19704 (5)	0.01826 (5)	0.04716 (16)
C212	−0.19498 (10)	0.28516 (6)	0.06529 (6)	0.0611 (2)
H21A	−0.1871	0.3079	0.1274	0.080*
C213	−0.27430 (12)	0.34027 (7)	0.02128 (7)	0.0766 (3)
H21B	−0.3196	0.3998	0.0540	0.080*
C214	−0.28707 (12)	0.30865 (7)	−0.06912 (8)	0.0788 (3)
H21C	−0.3416	0.3465	−0.0979	0.080*
C215	−0.21962 (11)	0.22045 (7)	−0.11912 (7)	0.0727 (2)
H21D	−0.2276	0.1987	−0.1811	0.080*
C216	−0.13982 (10)	0.16535 (6)	−0.07437 (6)	0.0590 (2)
H21E	−0.0938	0.1061	−0.1070	0.080*
C217	−0.04359 (8)	0.13709 (5)	0.06365 (5)	0.04819 (16)
O31	0.34255 (7)	0.85144 (4)	0.40777 (4)	0.06878 (16)
O32	0.51699 (7)	0.80945 (4)	0.50126 (4)	0.06315 (15)
O33	0.53995 (7)	1.00782 (4)	0.67139 (4)	0.06577 (15)
C31	0.44906 (9)	0.87216 (6)	0.47036 (5)	0.05367 (18)
C32	0.51740 (9)	0.96528 (6)	0.51851 (5)	0.05484 (18)
C33	0.46692 (11)	0.71254 (6)	0.46203 (6)	0.0653 (2)
H331	0.4504	0.6903	0.3973	0.080*
H332	0.3714	0.7096	0.4827	0.080*
C34	0.59145 (13)	0.65127 (7)	0.49072 (7)	0.0809 (3)
H341	0.5465	0.6007	0.4982	0.080*
H342	0.6479	0.6901	0.5464	0.080*
H343	0.6598	0.6237	0.4459	0.080*
C311	0.77690 (8)	0.95936 (5)	0.61405 (5)	0.04459 (15)
C312	0.85644 (9)	0.92821 (6)	0.53976 (5)	0.05626 (19)
H31A	0.8035	0.9212	0.4839	0.080*
C313	1.01386 (10)	0.90758 (7)	0.54853 (6)	0.0655 (2)
H31B	1.0660	0.8863	0.4986	0.080*
C314	1.09319 (10)	0.91872 (6)	0.63161 (6)	0.0658 (2)
H31C	1.1992	0.9068	0.6378	0.080*
C315	1.01562 (11)	0.94735 (6)	0.70486 (6)	0.0646 (2)
H31D	1.0686	0.9530	0.7603	0.080*
C316	0.85847 (9)	0.96784 (6)	0.69610 (5)	0.05354 (18)
H31E	0.8068	0.9876	0.7461	0.080*
C317	0.61051 (9)	0.98141 (5)	0.60530 (5)	0.04932 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0772 (4)	0.0808 (4)	0.0586 (3)	0.0187 (3)	0.0033 (3)	0.0221 (3)
O12	0.0768 (4)	0.1017 (5)	0.0562 (3)	0.0255 (4)	0.0128 (3)	0.0318 (3)
O13	0.0588 (3)	0.0666 (4)	0.0882 (4)	−0.0031 (3)	0.0075 (3)	0.0340 (3)
O14	0.0560 (3)	0.0662 (3)	0.0536 (3)	0.0002 (3)	0.0032 (2)	0.0218 (3)
O15	0.0526 (3)	0.0600 (3)	0.0478 (3)	−0.0009 (2)	0.0079 (2)	0.0193 (2)
O16	0.0628 (4)	0.0685 (4)	0.0863 (4)	−0.0048 (3)	0.0135 (3)	0.0348 (3)
C11	0.0517 (4)	0.0495 (4)	0.0498 (4)	0.0042 (3)	0.0056 (3)	0.0218 (3)
C12	0.0437 (4)	0.0402 (3)	0.0443 (4)	−0.0026 (3)	0.0051 (3)	0.0170 (3)
C13	0.0424 (3)	0.0376 (3)	0.0433 (4)	−0.0019 (3)	0.0060 (3)	0.0170 (3)
C14	0.0460 (4)	0.0429 (4)	0.0466 (4)	−0.0045 (3)	0.0053 (3)	0.0176 (3)
C15	0.0760 (6)	0.0952 (7)	0.0690 (6)	0.0172 (5)	0.0139 (5)	0.0347 (5)
C16	0.1136 (9)	0.0933 (8)	0.0735 (6)	0.0051 (7)	0.0103 (6)	0.0375 (6)
C17	0.0639 (5)	0.0713 (5)	0.0518 (4)	−0.0101 (4)	0.0057 (4)	0.0216 (4)
C18	0.0728 (5)	0.0653 (5)	0.0575 (5)	−0.0098 (4)	0.0138 (4)	0.0195 (4)
C111	0.0373 (3)	0.0452 (4)	0.0381 (3)	−0.0022 (3)	0.0043 (3)	0.0153 (3)
C112	0.0445 (4)	0.0544 (4)	0.0543 (4)	−0.0029 (3)	0.0038 (3)	0.0195 (3)
C113	0.0517 (5)	0.0647 (5)	0.0723 (5)	0.0070 (4)	0.0037 (4)	0.0228 (4)
C114	0.0724 (6)	0.0554 (5)	0.0683 (5)	0.0062 (4)	0.0051 (4)	0.0257 (4)
C115	0.0647 (5)	0.0558 (5)	0.0640 (5)	−0.0079 (4)	0.0081 (4)	0.0258 (4)
C116	0.0448 (4)	0.0499 (4)	0.0484 (4)	−0.0007 (3)	0.0072 (3)	0.0184 (3)
C117	0.0477 (4)	0.0497 (4)	0.0460 (4)	−0.0012 (3)	0.0068 (3)	0.0189 (3)
C121	0.0433 (4)	0.0472 (4)	0.0408 (3)	−0.0009 (3)	0.0072 (3)	0.0172 (3)
C122	0.0471 (4)	0.0577 (4)	0.0514 (4)	−0.0020 (3)	0.0057 (3)	0.0214 (3)
C123	0.0526 (4)	0.0665 (5)	0.0597 (5)	0.0113 (4)	0.0098 (4)	0.0227 (4)
C124	0.0711 (5)	0.0531 (4)	0.0609 (5)	0.0088 (4)	0.0126 (4)	0.0227 (4)
C125	0.0673 (5)	0.0527 (4)	0.0651 (5)	−0.0076 (4)	0.0119 (4)	0.0241 (4)
C126	0.0470 (4)	0.0507 (4)	0.0553 (4)	−0.0012 (3)	0.0084 (3)	0.0209 (3)
C127	0.0475 (4)	0.0516 (4)	0.0477 (4)	−0.0008 (3)	0.0061 (3)	0.0191 (3)
O21	0.0561 (4)	0.0656 (4)	0.1194 (6)	0.0039 (3)	0.0224 (4)	0.0376 (4)
O22	0.0417 (3)	0.0498 (3)	0.0579 (3)	−0.0036 (2)	0.0076 (2)	0.0207 (2)
O23	0.0633 (3)	0.0675 (4)	0.0635 (4)	0.0021 (3)	0.0117 (3)	0.0241 (3)
C21	0.0425 (4)	0.0497 (4)	0.0603 (4)	−0.0003 (3)	0.0071 (3)	0.0235 (3)
C22	0.0420 (4)	0.0503 (4)	0.0549 (4)	0.0013 (3)	0.0083 (3)	0.0228 (3)
C23	0.0447 (4)	0.0553 (4)	0.0671 (5)	−0.0060 (3)	0.0065 (3)	0.0244 (4)
C24	0.0701 (6)	0.0793 (6)	0.0790 (6)	−0.0064 (5)	0.0176 (5)	0.0311 (5)
C211	0.0397 (3)	0.0464 (4)	0.0547 (4)	−0.0029 (3)	0.0066 (3)	0.0186 (3)
C212	0.0631 (5)	0.0526 (4)	0.0642 (5)	0.0010 (4)	0.0125 (4)	0.0187 (4)
C213	0.0783 (6)	0.0607 (5)	0.0892 (7)	0.0105 (5)	0.0191 (5)	0.0279 (5)
C214	0.0738 (6)	0.0716 (6)	0.0955 (7)	0.0012 (5)	−0.0007 (5)	0.0427 (6)
C215	0.0730 (6)	0.0790 (6)	0.0691 (6)	−0.0008 (5)	0.0059 (5)	0.0339 (5)
C216	0.0582 (5)	0.0545 (4)	0.0598 (5)	0.0024 (4)	0.0061 (4)	0.0193 (4)
C217	0.0424 (4)	0.0508 (4)	0.0510 (4)	−0.0033 (3)	0.0083 (3)	0.0183 (3)
O31	0.0687 (4)	0.0588 (3)	0.0780 (4)	−0.0026 (3)	0.0029 (3)	0.0284 (3)
O32	0.0638 (3)	0.0553 (3)	0.0681 (4)	−0.0095 (3)	−0.0022 (3)	0.0241 (3)
O33	0.0646 (4)	0.0728 (4)	0.0608 (3)	0.0007 (3)	0.0130 (3)	0.0261 (3)
C31	0.0492 (4)	0.0524 (4)	0.0595 (5)	−0.0062 (3)	0.0075 (4)	0.0206 (4)
C32	0.0518 (4)	0.0544 (4)	0.0570 (4)	0.0000 (3)	0.0096 (3)	0.0201 (4)
C33	0.0683 (5)	0.0570 (5)	0.0709 (5)	−0.0117 (4)	0.0013 (4)	0.0256 (4)
C34	0.0870 (7)	0.0735 (6)	0.0794 (6)	−0.0071 (5)	−0.0028 (5)	0.0309 (5)
C311	0.0485 (4)	0.0392 (3)	0.0454 (4)	−0.0042 (3)	0.0029 (3)	0.0164 (3)
C312	0.0529 (4)	0.0653 (5)	0.0502 (4)	−0.0042 (4)	0.0020 (3)	0.0235 (4)
C313	0.0608 (5)	0.0735 (6)	0.0650 (5)	−0.0006 (4)	0.0130 (4)	0.0288 (4)
C314	0.0542 (5)	0.0669 (5)	0.0764 (6)	−0.0008 (4)	0.0001 (4)	0.0316 (5)
C315	0.0673 (5)	0.0658 (5)	0.0592 (5)	−0.0075 (4)	−0.0057 (4)	0.0269 (4)
C316	0.0614 (5)	0.0518 (4)	0.0481 (4)	−0.0069 (3)	0.0037 (3)	0.0203 (3)
C317	0.0539 (4)	0.0454 (4)	0.0491 (4)	−0.0043 (3)	0.0083 (3)	0.0178 (3)

Geometric parameters (Å, º)

O11—C11	1.1912 (11)	O22—C21	1.3156 (10)
O12—C11	1.3082 (12)	O22—C23	1.4546 (13)
O12—C15	1.4625 (13)	O23—C217	1.2277 (11)
O13—C127	1.2207 (11)	C21—C22	1.4590 (14)
O14—C14	1.1990 (11)	C22—C22^i	1.4086 (16)
O15—C14	1.3270 (12)	C22—C217	1.4646 (13)
O15—C17	1.4551 (12)	C23—C24	1.4996 (14)
O16—C117	1.2219 (11)	C23—H231	0.9700
C11—C12	1.4674 (12)	C23—H232	0.9700
C12—C13	1.3694 (12)	C24—H241	0.9600
C12—C117	1.4681 (14)	C24—H242	0.9600
C13—C127	1.4654 (14)	C24—H243	0.9600
C13—C14	1.4680 (12)	C211—C212	1.3727 (13)
C15—C16	1.5017 (18)	C211—C216	1.3896 (13)
C15—H151	0.9700	C211—C217	1.4637 (12)
C15—H152	0.9700	C212—C213	1.3781 (14)
C16—H161	0.9600	C212—H21A	0.9300
C16—H162	0.9600	C213—C214	1.3549 (16)
C16—H163	0.9600	C213—H21B	0.9300
C17—C18	1.5026 (15)	C214—C215	1.3858 (16)
C17—H171	0.9700	C214—H21C	0.9300
C17—H172	0.9700	C215—C216	1.3879 (14)
C18—H181	0.9600	C215—H21D	0.9300
C18—H182	0.9600	C216—H21E	0.9300
C18—H183	0.9600	O31—C31	1.2397 (12)
C111—C112	1.3921 (13)	O32—C31	1.2965 (11)
C111—C116	1.3926 (12)	O32—C33	1.4393 (12)
C111—C117	1.4551 (11)	O33—C317	1.2411 (11)
C112—C113	1.3678 (13)	C31—C32	1.4603 (13)
C112—H11A	0.9300	C32—C32^ii	1.3970 (17)
C113—C114	1.3848 (15)	C32—C317	1.4684 (13)
C113—H11B	0.9300	C33—C34	1.4991 (15)
C114—C115	1.3712 (15)	C33—H331	0.9700
C114—H11C	0.9300	C33—H332	0.9700
C115—C116	1.3700 (12)	C34—H341	0.9600
C115—H11D	0.9300	C34—H342	0.9600
C116—H11E	0.9300	C34—H343	0.9600
C121—C122	1.3924 (14)	C311—C316	1.3857 (12)
C121—C126	1.3970 (12)	C311—C312	1.3948 (13)
C121—C127	1.4557 (12)	C311—C317	1.4662 (14)
C122—C123	1.3821 (13)	C312—C313	1.3868 (15)
C122—H12B	0.9300	C312—H31A	0.9300
C123—C124	1.3494 (14)	C313—C314	1.3838 (15)
C123—H12C	0.9300	C313—H31B	0.9300
C124—C125	1.3899 (16)	C314—C315	1.3732 (15)
C124—H12D	0.9300	C314—H31C	0.9300
C125—C126	1.3902 (12)	C315—C316	1.3842 (15)
C125—H12E	0.9300	C315—H31D	0.9300
C126—H12F	0.9300	C316—H31E	0.9300
O21—C21	1.2223 (11)
C11—O12—C15	119.79 (8)	C21—O22—C23	117.89 (7)
C14—O15—C17	116.35 (7)	O21—C21—O22	123.47 (8)
O11—C11—O12	122.68 (8)	O21—C21—C22	124.85 (8)
O11—C11—C12	125.80 (8)	O22—C21—C22	111.68 (7)
O12—C11—C12	111.48 (7)	C22^i—C22—C21	118.61 (9)
C13—C12—C11	119.09 (7)	C22^i—C22—C217	123.56 (9)
C13—C12—C117	124.49 (8)	C21—C22—C217	117.72 (8)
C11—C12—C117	116.34 (7)	O22—C23—C24	111.57 (8)
C12—C13—C127	123.61 (8)	O22—C23—H231	109.3
C12—C13—C14	119.42 (7)	C24—C23—H231	109.3
C127—C13—C14	116.86 (7)	O22—C23—H232	109.3
O14—C14—O15	122.78 (8)	C24—C23—H232	109.3
O14—C14—C13	124.45 (8)	H231—C23—H232	108.0
O15—C14—C13	112.77 (7)	C23—C24—H241	109.5
O12—C15—C16	104.34 (10)	C23—C24—H242	109.5
O12—C15—H151	110.9	H241—C24—H242	109.5
C16—C15—H151	110.9	C23—C24—H243	109.5
O12—C15—H152	110.9	H241—C24—H243	109.5
C16—C15—H152	110.9	H242—C24—H243	109.5
H151—C15—H152	108.9	C212—C211—C216	118.46 (8)
C15—C16—H161	109.5	C212—C211—C217	121.42 (8)
C15—C16—H162	109.5	C216—C211—C217	120.12 (7)
H161—C16—H162	109.5	C211—C212—C213	120.55 (9)
C15—C16—H163	109.5	C211—C212—H21A	119.7
H161—C16—H163	109.5	C213—C212—H21A	119.7
H162—C16—H163	109.5	C214—C213—C212	120.72 (10)
O15—C17—C18	107.17 (8)	C214—C213—H21B	119.6
O15—C17—H171	110.3	C212—C213—H21B	119.6
C18—C17—H171	110.3	C213—C214—C215	120.60 (10)
O15—C17—H172	110.3	C213—C214—H21C	119.7
C18—C17—H172	110.3	C215—C214—H21C	119.7
H171—C17—H172	108.5	C214—C215—C216	118.38 (10)
C17—C18—H181	109.5	C214—C215—H21D	120.8
C17—C18—H182	109.5	C216—C215—H21D	120.8
H181—C18—H182	109.5	C215—C216—C211	121.28 (9)
C17—C18—H183	109.5	C215—C216—H21E	119.4
H181—C18—H183	109.5	C211—C216—H21E	119.4
H182—C18—H183	109.5	O23—C217—C211	120.27 (8)
C112—C111—C116	118.54 (8)	O23—C217—C22	117.57 (7)
C112—C111—C117	121.68 (7)	C211—C217—C22	122.01 (7)
C116—C111—C117	119.77 (7)	C31—O32—C33	119.08 (7)
C113—C112—C111	120.77 (8)	O31—C31—O32	122.23 (8)
C113—C112—H11A	119.6	O31—C31—C32	127.29 (8)
C111—C112—H11A	119.6	O32—C31—C32	110.48 (8)
C112—C113—C114	119.81 (9)	C32^ii—C32—C31	117.88 (10)
C112—C113—H11B	120.1	C32^ii—C32—C317	124.46 (10)
C114—C113—H11B	120.1	C31—C32—C317	117.55 (8)
C115—C114—C113	120.05 (9)	O32—C33—C34	106.90 (8)
C115—C114—H11C	120.0	O32—C33—H331	110.3
C113—C114—H11C	120.0	C34—C33—H331	110.3
C116—C115—C114	120.37 (9)	O32—C33—H332	110.3
C116—C115—H11D	119.8	C34—C33—H332	110.3
C114—C115—H11D	119.8	H331—C33—H332	108.6
C115—C116—C111	120.43 (8)	C33—C34—H341	109.5
C115—C116—H11E	119.8	C33—C34—H342	109.5
C111—C116—H11E	119.8	H341—C34—H342	109.5
O16—C117—C111	120.74 (8)	C33—C34—H343	109.5
O16—C117—C12	116.22 (8)	H341—C34—H343	109.5
C111—C117—C12	122.82 (7)	H342—C34—H343	109.5
C122—C121—C126	118.99 (8)	C316—C311—C312	118.45 (8)
C122—C121—C127	121.17 (8)	C316—C311—C317	120.77 (8)
C126—C121—C127	119.83 (7)	C312—C311—C317	120.77 (8)
C123—C122—C121	119.81 (8)	C313—C312—C311	120.47 (8)
C123—C122—H12B	120.1	C313—C312—H31A	119.8
C121—C122—H12B	120.1	C311—C312—H31A	119.8
C124—C123—C122	120.97 (9)	C314—C313—C312	119.93 (9)
C124—C123—H12C	119.5	C314—C313—H31B	120.0
C122—C123—H12C	119.5	C312—C313—H31B	120.0
C123—C124—C125	120.89 (9)	C315—C314—C313	120.10 (9)
C123—C124—H12D	119.6	C315—C314—H31C	119.9
C125—C124—H12D	119.6	C313—C314—H31C	119.9
C126—C125—C124	118.97 (9)	C314—C315—C316	119.94 (9)
C126—C125—H12E	120.5	C314—C315—H31D	120.0
C124—C125—H12E	120.5	C316—C315—H31D	120.0
C125—C126—C121	120.36 (8)	C315—C316—C311	121.07 (9)
C125—C126—H12F	119.8	C315—C316—H31E	119.5
C121—C126—H12F	119.8	C311—C316—H31E	119.5
O13—C127—C121	120.40 (8)	O33—C317—C311	120.51 (8)
O13—C127—C13	116.54 (8)	O33—C317—C32	116.67 (8)
C121—C127—C13	123.00 (8)	C311—C317—C32	122.59 (8)
C15—O12—C11—O11	2.31 (14)	C12—C13—C127—C121	−93.28 (10)
C15—O12—C11—C12	−179.96 (8)	C14—C13—C127—C121	90.52 (9)
O11—C11—C12—C13	16.95 (12)	C23—O22—C21—O21	−2.98 (11)
O12—C11—C12—C13	−160.70 (7)	C23—O22—C21—C22	178.10 (6)
O11—C11—C12—C117	−159.99 (8)	O21—C21—C22—C22^i	−11.31 (14)
O12—C11—C12—C117	22.36 (10)	O22—C21—C22—C22^i	167.60 (8)
C11—C12—C13—C127	3.82 (10)	O21—C21—C22—C217	165.08 (8)
C117—C12—C13—C127	−179.50 (7)	O22—C21—C22—C217	−16.01 (10)
C11—C12—C13—C14	179.93 (6)	C21—O22—C23—C24	81.94 (9)
C117—C12—C13—C14	−3.39 (10)	C216—C211—C212—C213	0.58 (13)
C17—O15—C14—O14	−0.64 (10)	C217—C211—C212—C213	−179.57 (8)
C17—O15—C14—C13	179.04 (6)	C211—C212—C213—C214	−0.06 (15)
C12—C13—C14—O14	−5.58 (11)	C212—C213—C214—C215	−0.45 (16)
C127—C13—C14—O14	170.79 (7)	C213—C214—C215—C216	0.40 (16)
C12—C13—C14—O15	174.74 (6)	C214—C215—C216—C211	0.14 (14)
C127—C13—C14—O15	−8.89 (9)	C212—C211—C216—C215	−0.62 (12)
C11—O12—C15—C16	119.76 (10)	C217—C211—C216—C215	179.53 (8)
C14—O15—C17—C18	−179.22 (7)	C212—C211—C217—O23	−2.18 (11)
C116—C111—C112—C113	−0.13 (11)	C216—C211—C217—O23	177.66 (7)
C117—C111—C112—C113	−179.10 (7)	C212—C211—C217—C22	−177.73 (7)
C111—C112—C113—C114	−1.49 (13)	C216—C211—C217—C22	2.12 (11)
C112—C113—C114—C115	2.23 (14)	C22^i—C22—C217—O23	89.27 (12)
C113—C114—C115—C116	−1.35 (13)	C21—C22—C217—O23	−86.93 (10)
C114—C115—C116—C111	−0.29 (12)	C22^i—C22—C217—C211	−95.08 (12)
C112—C111—C116—C115	1.02 (11)	C21—C22—C217—C211	88.73 (10)
C117—C111—C116—C115	−179.98 (7)	C33—O32—C31—O31	−0.30 (12)
C112—C111—C117—O16	−1.60 (11)	C33—O32—C31—C32	−179.56 (7)
C116—C111—C117—O16	179.44 (7)	O31—C31—C32—C32^ii	−13.29 (15)
C112—C111—C117—C12	172.80 (7)	O32—C31—C32—C32^ii	165.92 (9)
C116—C111—C117—C12	−6.17 (10)	O31—C31—C32—C317	163.08 (8)
C13—C12—C117—O16	−92.82 (10)	O32—C31—C32—C317	−17.71 (10)
C11—C12—C117—O16	83.94 (9)	C31—O32—C33—C34	163.63 (8)
C13—C12—C117—C111	92.56 (10)	C316—C311—C312—C313	−0.85 (12)
C11—C12—C117—C111	−90.68 (9)	C317—C311—C312—C313	179.93 (8)
C126—C121—C122—C123	−0.44 (11)	C311—C312—C313—C314	−0.59 (13)
C127—C121—C122—C123	−179.21 (7)	C312—C313—C314—C315	1.98 (14)
C121—C122—C123—C124	1.38 (12)	C313—C314—C315—C316	−1.91 (14)
C122—C123—C124—C125	−1.30 (13)	C314—C315—C316—C311	0.44 (13)
C123—C124—C125—C126	0.27 (13)	C312—C311—C316—C315	0.93 (11)
C124—C125—C126—C121	0.66 (12)	C317—C311—C316—C315	−179.85 (7)
C122—C121—C126—C125	−0.57 (11)	C316—C311—C317—O33	−0.19 (11)
C127—C121—C126—C125	178.22 (7)	C312—C311—C317—O33	179.01 (7)
C122—C121—C127—O13	0.59 (11)	C316—C311—C317—C32	−174.44 (7)
C126—C121—C127—O13	−178.17 (7)	C312—C311—C317—C32	4.76 (11)
C122—C121—C127—C13	−176.62 (7)	C32^ii—C32—C317—O33	92.67 (13)
C126—C121—C127—C13	4.62 (11)	C31—C32—C317—O33	−83.44 (10)
C12—C13—C127—O13	89.41 (10)	C32^ii—C32—C317—C311	−92.88 (12)
C14—C13—C127—O13	−86.79 (9)	C31—C32—C317—C311	91.01 (10)

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