Crystal structure of dimethyl 3,4,5,6-tetra­phenyl­cyclo­hexa-3,5-diene-1,2-di­carboxyl­ate

In the title compound, C₃₄H₂₈O₄, the cyclo­hexa­diene ring has a screw-boat conformation. All four phenyl rings in the two independent mol­ecules are arranged in a propeller-like conformation. The two mol­ecules exhibit S,R- and R,S- chirality and are connected via C—H...O inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C2      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C101    (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C102    (Chiral SPGR)          S Verify
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        135 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: XT (Sheldrick, 2015); program(s) used to refine structure: XL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(I)

Crystal data

C34H28O4	Dx = 1.253 Mg m^−3
Mr = 500.56	Cu Kα radiation, λ = 1.54178 Å
Trigonal, P32	Cell parameters from 9883 reflections
a = 10.8330 (12) Å	θ = 3.4–78.4°
c = 39.169 (5) Å	µ = 0.65 mm^−1
V = 3980.8 (12) Å^3	T = 173 K
Z = 6	Plate, colourless
F(000) = 1584	0.59 × 0.34 × 0.13 mm

Data collection

Bruker Photon-100 CMOS diffractometer	10345 reflections with I > 2σ(I)
Radiation source: sealedtube	Rint = 0.043
φ and ω scans	θmax = 79.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker,2014/5)	h = −13→12
Tmin = 0.669, Tmax = 0.754	k = −13→13
53613 measured reflections	l = −48→48
10773 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.4031P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.19 e Å^−3
10773 reflections	Δρmin = −0.15 e Å^−3
702 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.38 (16)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

1. Twinned data refinement Scales: 0.62 (16) 0.38 (16) 2. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 3.a Aromatic/amide H refined with riding coordinates: C21(H21), C34(H34), C18(H18), C30(H30), C134(H134), C24(H24), C22(H22), C12(H12), C133(H133), C16(H16), C112(H112), C130(H130), C28(H28), C124(H124), C113(H113), C119(H119), C19(H19), C131(H131), C15(H15), C118(H118), C120(H120), C31(H31), C114(H114), C116(H116), C25(H25), C27(H27), C121(H121), C122(H122), C128(H128), C13(H13), C20(H20), C132(H132), C26(H26), C14(H14), C33(H33), C32(H32), C126(H126), C127(H127), C115(H115), C125(H125) 3.b Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C110(H11A,H11B,H11C), C10(H10A,H10B,H10C), C108(H10D,H10E, H10F)

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

	x	y	z	Uiso*/Ueq
O4	0.79329 (17)	0.30493 (18)	0.54107 (4)	0.0438 (4)
O101	0.96274 (18)	0.63537 (17)	0.51401 (4)	0.0443 (4)
O103	1.02631 (18)	0.4316 (2)	0.41723 (4)	0.0475 (4)
O2	0.56790 (17)	0.38169 (16)	0.51915 (4)	0.0434 (4)
O1	0.3803 (2)	0.25072 (18)	0.48545 (4)	0.0458 (4)
O3	0.64592 (18)	0.29005 (17)	0.58294 (4)	0.0452 (4)
O102	1.09927 (18)	0.5677 (2)	0.48612 (5)	0.0540 (4)
O104	1.03157 (19)	0.27494 (18)	0.45336 (5)	0.0508 (4)
C9	0.6769 (2)	0.2477 (2)	0.55396 (5)	0.0345 (4)
C123	0.7593 (2)	0.5516 (2)	0.37918 (6)	0.0363 (4)
C29	0.2698 (2)	0.2158 (2)	0.56419 (5)	0.0329 (4)
C7	0.4665 (2)	0.2687 (2)	0.51152 (5)	0.0355 (4)
C4	0.4035 (2)	−0.0443 (2)	0.58720 (5)	0.0346 (4)
C3	0.5035 (2)	−0.0149 (2)	0.56313 (5)	0.0340 (4)
C23	0.2515 (2)	0.0341 (2)	0.62110 (5)	0.0354 (4)
C109	0.9775 (2)	0.3424 (2)	0.44350 (6)	0.0356 (4)
C101	0.8547 (2)	0.4732 (2)	0.46876 (5)	0.0327 (4)
H101	0.772 (3)	0.452 (3)	0.4837 (7)	0.039*
C104	0.6822 (2)	0.3191 (2)	0.41216 (5)	0.0333 (4)
C105	0.7663 (2)	0.4780 (2)	0.41074 (5)	0.0328 (4)
C107	0.9869 (2)	0.5616 (2)	0.49006 (5)	0.0362 (4)
C5	0.3298 (2)	0.0406 (2)	0.58914 (5)	0.0333 (4)
C106	0.8498 (2)	0.5531 (2)	0.43712 (5)	0.0318 (4)
C102	0.8425 (2)	0.3301 (2)	0.45915 (5)	0.0327 (4)
H102	0.829 (3)	0.276 (3)	0.4797 (7)	0.039*
C2	0.5490 (2)	0.1126 (2)	0.53935 (5)	0.0335 (4)
H2	0.586 (3)	0.095 (3)	0.5182 (7)	0.040*
C6	0.3366 (2)	0.1245 (2)	0.56296 (5)	0.0322 (4)
C129	0.9408 (2)	0.7112 (2)	0.43578 (6)	0.0342 (4)
C11	0.5749 (2)	−0.1004 (2)	0.55719 (6)	0.0371 (4)
C21	0.4450 (3)	−0.2535 (3)	0.65930 (7)	0.0527 (6)
H21	0.5199	−0.2513	0.6724	0.063*
C34	0.3107 (3)	0.3209 (2)	0.58899 (6)	0.0397 (5)
H34	0.3819	0.3349	0.6052	0.048*
C18	0.2271 (3)	−0.2583 (2)	0.62137 (6)	0.0418 (5)
H18	0.1516	−0.2602	0.6086	0.050*
C103	0.7127 (2)	0.2471 (2)	0.43591 (5)	0.0337 (4)
C111	0.6241 (2)	0.0917 (2)	0.44298 (6)	0.0359 (4)
C30	0.1673 (2)	0.1994 (3)	0.54024 (6)	0.0434 (5)
H30	0.1397	0.1294	0.5228	0.052*
C134	1.0485 (2)	0.7733 (2)	0.41147 (6)	0.0401 (5)
H134	1.0651	0.7145	0.3963	0.048*
C1	0.4199 (2)	0.1303 (2)	0.53089 (5)	0.0326 (4)
H1	0.357 (3)	0.052 (3)	0.5158 (7)	0.039*
C17	0.3680 (2)	−0.1561 (2)	0.61388 (5)	0.0375 (4)
C24	0.1072 (3)	−0.0091 (2)	0.62101 (7)	0.0448 (5)
H24	0.0548	−0.0382	0.6003	0.054*
C22	0.4763 (3)	−0.1550 (3)	0.63322 (6)	0.0440 (5)
H22	0.5728	−0.0861	0.6286	0.053*
C12	0.4937 (3)	−0.2481 (2)	0.55401 (6)	0.0440 (5)
H12	0.3930	−0.2941	0.5563	0.053*
C133	1.1322 (3)	0.9209 (3)	0.40914 (7)	0.0529 (6)
H133	1.2055	0.9623	0.3925	0.063*
C117	0.5695 (2)	0.2447 (2)	0.38556 (6)	0.0371 (4)
C16	0.7221 (3)	−0.0358 (3)	0.55332 (7)	0.0479 (5)
H16	0.7794	0.0649	0.5551	0.057*
C112	0.4757 (2)	0.0265 (2)	0.44520 (6)	0.0387 (4)
H112	0.4305	0.0803	0.4403	0.046*
C130	0.9202 (3)	0.7994 (2)	0.45808 (6)	0.0429 (5)
H130	0.8489	0.7587	0.4752	0.051*
C28	0.3246 (3)	0.0744 (3)	0.65205 (6)	0.0469 (5)
H28	0.4232	0.1038	0.6526	0.056*
C124	0.7148 (3)	0.6522 (2)	0.38033 (7)	0.0473 (5)
H124	0.6850	0.6725	0.4014	0.057*
C113	0.3938 (3)	−0.1154 (3)	0.45445 (6)	0.0458 (5)
H113	0.2931	−0.1580	0.4557	0.055*
C119	0.3685 (3)	0.2182 (3)	0.35267 (7)	0.0509 (6)
H119	0.2984	0.2446	0.3485	0.061*
C19	0.1960 (3)	−0.3573 (3)	0.64730 (7)	0.0493 (6)
H19	0.0997	−0.4267	0.6520	0.059*
C131	1.0040 (3)	0.9472 (3)	0.45532 (8)	0.0554 (7)
H131	0.9885	1.0071	0.4703	0.066*
C15	0.7860 (3)	−0.1173 (3)	0.54693 (8)	0.0566 (7)
H15	0.8866	−0.0720	0.5445	0.068*
C118	0.4674 (2)	0.2838 (2)	0.37867 (6)	0.0422 (5)
H118	0.4654	0.3563	0.3919	0.051*
C120	0.3719 (3)	0.1143 (3)	0.33279 (7)	0.0559 (7)
H120	0.3049	0.0701	0.3148	0.067*
C31	0.1052 (3)	0.2850 (3)	0.54173 (8)	0.0554 (7)
H31	0.0353	0.2732	0.5254	0.066*
C114	0.4573 (3)	−0.1955 (3)	0.46184 (8)	0.0539 (6)
H114	0.4010	−0.2924	0.4685	0.065*
C116	0.6871 (3)	0.0096 (3)	0.45039 (8)	0.0498 (6)
H116	0.7878	0.0514	0.4493	0.060*
C25	0.0393 (3)	−0.0097 (3)	0.65115 (9)	0.0627 (8)
H25	−0.0591	−0.0381	0.6508	0.075*
C27	0.2558 (4)	0.0723 (3)	0.68193 (7)	0.0617 (8)
H27	0.3071	0.1000	0.7028	0.074*
C121	0.4727 (3)	0.0754 (3)	0.33914 (7)	0.0529 (6)
H121	0.4751	0.0043	0.3254	0.063*
C8	0.4058 (4)	0.3808 (3)	0.46891 (7)	0.0588 (7)
H8A	0.3398	0.3574	0.4497	0.088*
H8B	0.5041	0.4326	0.4605	0.088*
H8C	0.3909	0.4403	0.4853	0.088*
C122	0.5707 (3)	0.1388 (2)	0.36532 (6)	0.0439 (5)
H122	0.6391	0.1101	0.3696	0.053*
C128	0.8006 (3)	0.5232 (3)	0.34810 (6)	0.0479 (5)
H128	0.8302	0.4543	0.3468	0.058*
C13	0.5581 (3)	−0.3293 (3)	0.54756 (7)	0.0509 (6)
H13	0.5012	−0.4300	0.5456	0.061*
C20	0.3049 (4)	−0.3547 (3)	0.66614 (7)	0.0543 (7)
H20	0.2837	−0.4225	0.6838	0.065*
C132	1.1094 (3)	1.0066 (3)	0.43078 (8)	0.0598 (8)
H132	1.1662	1.1073	0.4289	0.072*
C26	0.1132 (4)	0.0303 (3)	0.68154 (8)	0.0677 (9)
H26	0.0660	0.0290	0.7021	0.081*
C14	0.7037 (3)	−0.2644 (3)	0.54406 (8)	0.0543 (6)
H14	0.7477	−0.3199	0.5397	0.065*
C33	0.2479 (3)	0.4054 (3)	0.59017 (7)	0.0517 (6)
H33	0.2762	0.4768	0.6072	0.062*
C32	0.1450 (3)	0.3866 (3)	0.56682 (8)	0.0562 (7)
H32	0.1015	0.4440	0.5680	0.067*
C110	1.1609 (3)	0.4582 (4)	0.40345 (8)	0.0621 (7)
H11A	1.1830	0.5166	0.3828	0.093*
H11B	1.1551	0.3673	0.3978	0.093*
H11C	1.2362	0.5087	0.4204	0.093*
C10	0.7575 (3)	0.4261 (3)	0.59574 (8)	0.0578 (7)
H10A	0.7695	0.5023	0.5802	0.087*
H10B	0.8472	0.4248	0.5972	0.087*
H10C	0.7314	0.4433	0.6185	0.087*
C126	0.7558 (3)	0.6936 (4)	0.32010 (9)	0.0718 (10)
H126	0.7545	0.7419	0.3000	0.086*
C127	0.7991 (3)	0.5949 (4)	0.31868 (7)	0.0664 (9)
H127	0.8284	0.5750	0.2975	0.080*
C115	0.6036 (3)	−0.1331 (3)	0.45941 (9)	0.0614 (7)
H115	0.6477	−0.1882	0.4640	0.074*
C108	1.0862 (4)	0.7347 (3)	0.53338 (8)	0.0646 (8)
H10D	1.1554	0.8085	0.5181	0.097*
H10E	1.1296	0.6840	0.5441	0.097*
H10F	1.0572	0.7792	0.5511	0.097*
C125	0.7142 (3)	0.7225 (3)	0.35077 (10)	0.0658 (9)
H125	0.6846	0.7915	0.3518	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0354 (8)	0.0405 (8)	0.0537 (9)	0.0178 (7)	0.0057 (7)	0.0050 (7)
O101	0.0495 (9)	0.0365 (8)	0.0416 (8)	0.0175 (7)	−0.0063 (7)	−0.0078 (6)
O103	0.0415 (9)	0.0614 (11)	0.0440 (8)	0.0289 (8)	0.0093 (7)	0.0128 (8)
O2	0.0400 (8)	0.0322 (8)	0.0563 (9)	0.0169 (7)	0.0008 (7)	0.0066 (7)
O1	0.0583 (10)	0.0419 (8)	0.0412 (8)	0.0280 (8)	−0.0065 (7)	0.0010 (7)
O3	0.0464 (9)	0.0379 (8)	0.0429 (8)	0.0148 (7)	0.0022 (7)	−0.0064 (6)
O102	0.0349 (9)	0.0540 (10)	0.0670 (11)	0.0177 (8)	−0.0096 (8)	−0.0159 (9)
O104	0.0415 (9)	0.0425 (9)	0.0731 (11)	0.0245 (8)	0.0025 (8)	0.0080 (8)
C9	0.0395 (11)	0.0308 (10)	0.0378 (10)	0.0210 (9)	0.0015 (8)	0.0038 (8)
C123	0.0285 (9)	0.0275 (9)	0.0447 (11)	0.0079 (8)	−0.0063 (8)	0.0014 (8)
C29	0.0314 (10)	0.0299 (9)	0.0387 (11)	0.0162 (8)	0.0053 (8)	0.0043 (8)
C7	0.0397 (11)	0.0367 (11)	0.0360 (10)	0.0234 (9)	0.0049 (8)	0.0009 (8)
C4	0.0363 (10)	0.0277 (9)	0.0409 (10)	0.0169 (8)	−0.0010 (8)	−0.0003 (8)
C3	0.0368 (10)	0.0275 (9)	0.0407 (10)	0.0183 (8)	0.0017 (8)	0.0001 (8)
C23	0.0407 (11)	0.0270 (9)	0.0424 (10)	0.0199 (8)	0.0063 (9)	0.0054 (8)
C109	0.0333 (10)	0.0300 (10)	0.0405 (10)	0.0136 (8)	−0.0048 (8)	−0.0036 (8)
C101	0.0309 (10)	0.0283 (9)	0.0352 (10)	0.0120 (8)	0.0012 (8)	−0.0001 (7)
C104	0.0298 (9)	0.0275 (9)	0.0386 (10)	0.0113 (8)	−0.0011 (8)	−0.0011 (8)
C105	0.0297 (9)	0.0271 (9)	0.0391 (10)	0.0123 (8)	−0.0010 (8)	0.0006 (8)
C107	0.0366 (11)	0.0293 (10)	0.0372 (10)	0.0122 (8)	−0.0012 (8)	0.0024 (8)
C5	0.0320 (9)	0.0275 (9)	0.0403 (10)	0.0148 (8)	0.0005 (8)	−0.0008 (8)
C106	0.0285 (9)	0.0267 (9)	0.0390 (10)	0.0129 (8)	0.0015 (8)	0.0013 (7)
C102	0.0317 (10)	0.0280 (9)	0.0352 (10)	0.0127 (8)	−0.0014 (8)	0.0018 (8)
C2	0.0366 (10)	0.0293 (10)	0.0371 (10)	0.0185 (9)	0.0029 (8)	0.0003 (8)
C6	0.0297 (9)	0.0285 (9)	0.0379 (10)	0.0141 (8)	−0.0003 (8)	−0.0017 (7)
C129	0.0310 (9)	0.0279 (9)	0.0407 (11)	0.0124 (8)	−0.0076 (8)	−0.0002 (8)
C11	0.0409 (11)	0.0331 (10)	0.0435 (11)	0.0231 (9)	0.0053 (9)	0.0023 (8)
C21	0.0789 (19)	0.0489 (14)	0.0456 (13)	0.0434 (14)	−0.0060 (12)	−0.0020 (11)
C34	0.0435 (11)	0.0334 (10)	0.0439 (11)	0.0206 (9)	0.0057 (9)	0.0020 (8)
C18	0.0512 (13)	0.0328 (10)	0.0444 (11)	0.0232 (10)	0.0078 (10)	0.0023 (9)
C103	0.0296 (9)	0.0273 (9)	0.0407 (10)	0.0117 (8)	−0.0004 (8)	−0.0021 (8)
C111	0.0333 (10)	0.0287 (10)	0.0399 (10)	0.0111 (8)	−0.0013 (8)	−0.0005 (8)
C30	0.0386 (11)	0.0473 (12)	0.0462 (12)	0.0230 (10)	−0.0007 (9)	0.0023 (10)
C134	0.0330 (10)	0.0325 (11)	0.0479 (12)	0.0111 (9)	−0.0018 (9)	0.0046 (9)
C1	0.0341 (10)	0.0282 (9)	0.0362 (10)	0.0162 (8)	0.0013 (8)	0.0001 (8)
C17	0.0475 (12)	0.0311 (10)	0.0413 (11)	0.0253 (9)	0.0055 (9)	0.0008 (8)
C24	0.0429 (12)	0.0338 (11)	0.0601 (14)	0.0211 (10)	0.0096 (10)	0.0063 (10)
C22	0.0540 (13)	0.0405 (12)	0.0479 (12)	0.0314 (11)	−0.0010 (10)	−0.0019 (9)
C12	0.0470 (13)	0.0328 (11)	0.0551 (13)	0.0221 (10)	0.0115 (10)	0.0026 (9)
C133	0.0401 (13)	0.0383 (12)	0.0644 (16)	0.0076 (10)	−0.0075 (11)	0.0143 (11)
C117	0.0306 (10)	0.0291 (9)	0.0405 (10)	0.0065 (8)	−0.0004 (8)	0.0038 (8)
C16	0.0426 (12)	0.0359 (11)	0.0693 (16)	0.0228 (10)	0.0041 (11)	0.0035 (11)
C112	0.0350 (10)	0.0323 (11)	0.0439 (11)	0.0132 (9)	−0.0009 (9)	0.0015 (9)
C130	0.0483 (13)	0.0372 (11)	0.0466 (12)	0.0240 (10)	−0.0086 (10)	−0.0053 (9)
C28	0.0597 (15)	0.0412 (12)	0.0442 (12)	0.0284 (11)	0.0031 (11)	0.0043 (10)
C124	0.0358 (11)	0.0352 (11)	0.0671 (15)	0.0149 (10)	−0.0128 (10)	0.0014 (10)
C113	0.0353 (11)	0.0368 (12)	0.0510 (13)	0.0072 (9)	−0.0015 (10)	0.0045 (10)
C119	0.0336 (11)	0.0499 (14)	0.0525 (13)	0.0083 (10)	−0.0045 (10)	0.0143 (11)
C19	0.0654 (16)	0.0325 (11)	0.0494 (13)	0.0240 (11)	0.0166 (11)	0.0035 (9)
C131	0.0707 (18)	0.0381 (12)	0.0644 (16)	0.0325 (13)	−0.0281 (14)	−0.0136 (11)
C15	0.0479 (14)	0.0536 (15)	0.0787 (18)	0.0331 (13)	0.0109 (13)	0.0082 (13)
C118	0.0325 (10)	0.0364 (11)	0.0482 (12)	0.0100 (9)	−0.0028 (9)	0.0057 (9)
C120	0.0425 (13)	0.0533 (15)	0.0414 (12)	0.0010 (11)	−0.0077 (10)	0.0037 (11)
C31	0.0486 (14)	0.0681 (17)	0.0632 (16)	0.0395 (13)	0.0062 (12)	0.0192 (14)
C114	0.0485 (14)	0.0295 (11)	0.0682 (16)	0.0079 (10)	−0.0093 (12)	0.0084 (10)
C116	0.0372 (12)	0.0345 (12)	0.0738 (17)	0.0150 (10)	−0.0039 (11)	0.0053 (11)
C25	0.0582 (16)	0.0410 (13)	0.093 (2)	0.0279 (12)	0.0374 (16)	0.0202 (14)
C27	0.099 (2)	0.0475 (14)	0.0420 (13)	0.0394 (16)	0.0096 (14)	0.0059 (11)
C121	0.0499 (14)	0.0384 (12)	0.0451 (12)	0.0032 (11)	0.0017 (11)	−0.0038 (10)
C8	0.079 (2)	0.0536 (15)	0.0515 (14)	0.0394 (15)	−0.0100 (13)	0.0079 (11)
C122	0.0402 (12)	0.0330 (11)	0.0464 (12)	0.0093 (9)	−0.0002 (9)	−0.0011 (9)
C128	0.0423 (12)	0.0469 (13)	0.0429 (12)	0.0136 (11)	−0.0050 (9)	−0.0004 (10)
C13	0.0634 (16)	0.0358 (12)	0.0622 (15)	0.0314 (12)	0.0172 (12)	0.0056 (11)
C20	0.090 (2)	0.0389 (12)	0.0417 (12)	0.0383 (14)	0.0087 (12)	0.0054 (10)
C132	0.0591 (16)	0.0268 (11)	0.0795 (19)	0.0111 (11)	−0.0274 (14)	0.0048 (12)
C26	0.102 (3)	0.0474 (15)	0.0592 (17)	0.0412 (16)	0.0416 (18)	0.0158 (13)
C14	0.0666 (17)	0.0505 (14)	0.0664 (16)	0.0446 (14)	0.0177 (13)	0.0105 (12)
C33	0.0654 (16)	0.0380 (12)	0.0602 (15)	0.0322 (12)	0.0197 (13)	0.0059 (11)
C32	0.0607 (16)	0.0552 (15)	0.0737 (17)	0.0447 (14)	0.0236 (14)	0.0229 (13)
C110	0.0464 (14)	0.082 (2)	0.0612 (16)	0.0350 (14)	0.0173 (12)	0.0150 (14)
C10	0.0629 (17)	0.0386 (12)	0.0589 (15)	0.0156 (12)	−0.0056 (12)	−0.0118 (11)
C126	0.0500 (16)	0.0654 (19)	0.0699 (19)	0.0064 (14)	−0.0224 (14)	0.0262 (15)
C127	0.0517 (15)	0.074 (2)	0.0434 (13)	0.0089 (15)	−0.0114 (11)	0.0078 (13)
C115	0.0510 (15)	0.0342 (12)	0.096 (2)	0.0194 (11)	−0.0111 (14)	0.0103 (13)
C108	0.0704 (19)	0.0515 (15)	0.0595 (16)	0.0213 (15)	−0.0239 (14)	−0.0203 (13)
C125	0.0434 (14)	0.0411 (14)	0.103 (3)	0.0135 (12)	−0.0251 (15)	0.0133 (14)

Geometric parameters (Å, º)

O4—C9	1.203 (3)	C133—H133	0.9500
O101—C107	1.340 (3)	C133—C132	1.368 (5)
O101—C108	1.443 (3)	C117—C118	1.395 (3)
O103—C109	1.327 (3)	C117—C122	1.400 (3)
O103—C110	1.442 (3)	C16—H16	0.9500
O2—C7	1.204 (3)	C16—C15	1.389 (4)
O1—C7	1.331 (3)	C112—H112	0.9500
O1—C8	1.446 (3)	C112—C113	1.385 (3)
O3—C9	1.329 (3)	C130—H130	0.9500
O3—C10	1.451 (3)	C130—C131	1.396 (4)
O102—C107	1.196 (3)	C28—H28	0.9500
O104—C109	1.206 (3)	C28—C27	1.382 (4)
C9—C2	1.537 (3)	C124—H124	0.9500
C123—C105	1.493 (3)	C124—C125	1.388 (4)
C123—C124	1.395 (3)	C113—H113	0.9500
C123—C128	1.383 (3)	C113—C114	1.380 (4)
C29—C6	1.489 (3)	C119—H119	0.9500
C29—C34	1.390 (3)	C119—C118	1.389 (3)
C29—C30	1.396 (3)	C119—C120	1.384 (5)
C7—C1	1.524 (3)	C19—H19	0.9500
C4—C3	1.349 (3)	C19—C20	1.381 (4)
C4—C5	1.491 (3)	C131—H131	0.9500
C4—C17	1.496 (3)	C131—C132	1.381 (5)
C3—C2	1.529 (3)	C15—H15	0.9500
C3—C11	1.492 (3)	C15—C14	1.388 (4)
C23—C5	1.494 (3)	C118—H118	0.9500
C23—C24	1.390 (3)	C120—H120	0.9500
C23—C28	1.393 (3)	C120—C121	1.376 (4)
C109—C102	1.529 (3)	C31—H31	0.9500
C101—H101	0.99 (3)	C31—C32	1.375 (5)
C101—C107	1.514 (3)	C114—H114	0.9500
C101—C106	1.527 (3)	C114—C115	1.381 (4)
C101—C102	1.536 (3)	C116—H116	0.9500
C104—C105	1.493 (3)	C116—C115	1.390 (4)
C104—C103	1.356 (3)	C25—H25	0.9500
C104—C117	1.497 (3)	C25—C26	1.378 (5)
C105—C106	1.346 (3)	C27—H27	0.9500
C5—C6	1.348 (3)	C27—C26	1.374 (5)
C106—C129	1.490 (3)	C121—H121	0.9500
C102—H102	0.96 (3)	C121—C122	1.386 (4)
C102—C103	1.533 (3)	C8—H8A	0.9800
C2—H2	0.98 (3)	C8—H8B	0.9800
C2—C1	1.539 (3)	C8—H8C	0.9800
C6—C1	1.530 (3)	C122—H122	0.9500
C129—C134	1.391 (3)	C128—H128	0.9500
C129—C130	1.392 (3)	C128—C127	1.394 (4)
C11—C12	1.394 (3)	C13—H13	0.9500
C11—C16	1.393 (3)	C13—C14	1.376 (4)
C21—H21	0.9500	C20—H20	0.9500
C21—C22	1.391 (4)	C132—H132	0.9500
C21—C20	1.383 (4)	C26—H26	0.9500
C34—H34	0.9500	C14—H14	0.9500
C34—C33	1.388 (3)	C33—H33	0.9500
C18—H18	0.9500	C33—C32	1.376 (4)
C18—C17	1.397 (3)	C32—H32	0.9500
C18—C19	1.391 (3)	C110—H11A	0.9800
C103—C111	1.489 (3)	C110—H11B	0.9800
C111—C112	1.398 (3)	C110—H11C	0.9800
C111—C116	1.396 (3)	C10—H10A	0.9800
C30—H30	0.9500	C10—H10B	0.9800
C30—C31	1.393 (4)	C10—H10C	0.9800
C134—H134	0.9500	C126—H126	0.9500
C134—C133	1.392 (3)	C126—C127	1.368 (6)
C1—H1	0.98 (3)	C126—C125	1.373 (6)
C17—C22	1.392 (3)	C127—H127	0.9500
C24—H24	0.9500	C115—H115	0.9500
C24—C25	1.389 (4)	C108—H10D	0.9800
C22—H22	0.9500	C108—H10E	0.9800
C12—H12	0.9500	C108—H10F	0.9800
C12—C13	1.392 (3)	C125—H125	0.9500
C107—O101—C108	115.4 (2)	C15—C16—C11	120.6 (2)
C109—O103—C110	115.50 (19)	C15—C16—H16	119.7
C7—O1—C8	115.0 (2)	C111—C112—H112	119.5
C9—O3—C10	114.9 (2)	C113—C112—C111	120.9 (2)
O4—C9—O3	124.1 (2)	C113—C112—H112	119.5
O4—C9—C2	123.3 (2)	C129—C130—H130	119.9
O3—C9—C2	112.58 (18)	C129—C130—C131	120.2 (2)
C124—C123—C105	121.3 (2)	C131—C130—H130	119.9
C128—C123—C105	120.1 (2)	C23—C28—H28	119.5
C128—C123—C124	118.6 (2)	C27—C28—C23	120.9 (3)
C34—C29—C6	120.32 (19)	C27—C28—H28	119.5
C34—C29—C30	118.8 (2)	C123—C124—H124	120.0
C30—C29—C6	120.9 (2)	C125—C124—C123	120.0 (3)
O2—C7—O1	123.8 (2)	C125—C124—H124	120.0
O2—C7—C1	124.2 (2)	C112—C113—H113	119.7
O1—C7—C1	112.05 (18)	C114—C113—C112	120.6 (2)
C3—C4—C5	120.32 (19)	C114—C113—H113	119.7
C3—C4—C17	122.02 (19)	C118—C119—H119	119.9
C5—C4—C17	117.58 (18)	C120—C119—H119	119.9
C4—C3—C2	119.78 (18)	C120—C119—C118	120.1 (3)
C4—C3—C11	124.55 (19)	C18—C19—H19	120.0
C11—C3—C2	115.66 (18)	C20—C19—C18	120.0 (3)
C24—C23—C5	122.0 (2)	C20—C19—H19	120.0
C24—C23—C28	118.4 (2)	C130—C131—H131	120.0
C28—C23—C5	119.6 (2)	C132—C131—C130	120.0 (3)
O103—C109—C102	112.96 (17)	C132—C131—H131	120.0
O104—C109—O103	123.5 (2)	C16—C15—H15	119.8
O104—C109—C102	123.5 (2)	C14—C15—C16	120.4 (3)
C107—C101—H101	106.2 (15)	C14—C15—H15	119.8
C107—C101—C106	112.23 (17)	C117—C118—H118	119.6
C107—C101—C102	110.49 (17)	C119—C118—C117	120.8 (2)
C106—C101—H101	109.1 (15)	C119—C118—H118	119.6
C106—C101—C102	111.29 (17)	C119—C120—H120	120.2
C102—C101—H101	107.2 (16)	C121—C120—C119	119.7 (2)
C105—C104—C117	117.26 (18)	C121—C120—H120	120.2
C103—C104—C105	120.32 (18)	C30—C31—H31	120.0
C103—C104—C117	122.36 (19)	C32—C31—C30	120.0 (3)
C104—C105—C123	118.82 (18)	C32—C31—H31	120.0
C106—C105—C123	120.74 (18)	C113—C114—H114	120.4
C106—C105—C104	120.42 (18)	C113—C114—C115	119.2 (2)
O101—C107—C101	110.97 (18)	C115—C114—H114	120.4
O102—C107—O101	123.7 (2)	C111—C116—H116	119.8
O102—C107—C101	125.4 (2)	C115—C116—C111	120.5 (2)
C4—C5—C23	118.71 (18)	C115—C116—H116	119.8
C6—C5—C4	120.79 (19)	C24—C25—H25	119.7
C6—C5—C23	120.48 (18)	C26—C25—C24	120.6 (3)
C105—C106—C101	118.93 (18)	C26—C25—H25	119.7
C105—C106—C129	121.73 (18)	C28—C27—H27	119.9
C129—C106—C101	119.31 (17)	C26—C27—C28	120.3 (3)
C109—C102—C101	114.49 (17)	C26—C27—H27	119.9
C109—C102—H102	103.6 (16)	C120—C121—H121	119.6
C109—C102—C103	111.72 (17)	C120—C121—C122	120.7 (3)
C101—C102—H102	108.5 (16)	C122—C121—H121	119.6
C103—C102—C101	109.15 (17)	O1—C8—H8A	109.5
C103—C102—H102	109.1 (16)	O1—C8—H8B	109.5
C9—C2—H2	103.9 (16)	O1—C8—H8C	109.5
C9—C2—C1	113.86 (16)	H8A—C8—H8B	109.5
C3—C2—C9	111.29 (17)	H8A—C8—H8C	109.5
C3—C2—H2	108.7 (16)	H8B—C8—H8C	109.5
C3—C2—C1	109.97 (17)	C117—C122—H122	119.8
C1—C2—H2	108.8 (16)	C121—C122—C117	120.4 (2)
C29—C6—C1	118.19 (17)	C121—C122—H122	119.8
C5—C6—C29	122.85 (18)	C123—C128—H128	119.7
C5—C6—C1	118.93 (18)	C123—C128—C127	120.6 (3)
C134—C129—C106	119.5 (2)	C127—C128—H128	119.7
C134—C129—C130	118.7 (2)	C12—C13—H13	119.9
C130—C129—C106	121.7 (2)	C14—C13—C12	120.3 (2)
C12—C11—C3	120.1 (2)	C14—C13—H13	119.9
C16—C11—C3	121.59 (19)	C21—C20—H20	120.0
C16—C11—C12	118.3 (2)	C19—C20—C21	120.0 (2)
C22—C21—H21	120.0	C19—C20—H20	120.0
C20—C21—H21	120.0	C133—C132—C131	120.2 (2)
C20—C21—C22	120.0 (3)	C133—C132—H132	119.9
C29—C34—H34	119.9	C131—C132—H132	119.9
C33—C34—C29	120.2 (2)	C25—C26—H26	120.2
C33—C34—H34	119.9	C27—C26—C25	119.6 (2)
C17—C18—H18	119.6	C27—C26—H26	120.2
C19—C18—H18	119.6	C15—C14—H14	120.3
C19—C18—C17	120.8 (2)	C13—C14—C15	119.5 (2)
C104—C103—C102	119.08 (18)	C13—C14—H14	120.3
C104—C103—C111	124.94 (19)	C34—C33—H33	119.7
C111—C103—C102	115.87 (18)	C32—C33—C34	120.6 (2)
C112—C111—C103	120.8 (2)	C32—C33—H33	119.7
C116—C111—C103	120.99 (19)	C31—C32—C33	120.0 (2)
C116—C111—C112	118.0 (2)	C31—C32—H32	120.0
C29—C30—H30	119.8	C33—C32—H32	120.0
C31—C30—C29	120.4 (2)	O103—C110—H11A	109.5
C31—C30—H30	119.8	O103—C110—H11B	109.5
C129—C134—H134	119.8	O103—C110—H11C	109.5
C129—C134—C133	120.5 (2)	H11A—C110—H11B	109.5
C133—C134—H134	119.8	H11A—C110—H11C	109.5
C7—C1—C2	110.82 (17)	H11B—C110—H11C	109.5
C7—C1—C6	110.29 (16)	O3—C10—H10A	109.5
C7—C1—H1	107.3 (16)	O3—C10—H10B	109.5
C2—C1—H1	107.5 (16)	O3—C10—H10C	109.5
C6—C1—C2	111.88 (17)	H10A—C10—H10B	109.5
C6—C1—H1	108.9 (16)	H10A—C10—H10C	109.5
C18—C17—C4	121.7 (2)	H10B—C10—H10C	109.5
C22—C17—C4	119.9 (2)	C127—C126—H126	120.2
C22—C17—C18	118.3 (2)	C127—C126—C125	119.6 (3)
C23—C24—H24	119.9	C125—C126—H126	120.2
C25—C24—C23	120.2 (3)	C128—C127—H127	119.8
C25—C24—H24	119.9	C126—C127—C128	120.4 (3)
C21—C22—C17	120.8 (3)	C126—C127—H127	119.8
C21—C22—H22	119.6	C114—C115—C116	120.8 (2)
C17—C22—H22	119.6	C114—C115—H115	119.6
C11—C12—H12	119.6	C116—C115—H115	119.6
C13—C12—C11	120.9 (2)	O101—C108—H10D	109.5
C13—C12—H12	119.6	O101—C108—H10E	109.5
C134—C133—H133	119.9	O101—C108—H10F	109.5
C132—C133—C134	120.3 (3)	H10D—C108—H10E	109.5
C132—C133—H133	119.9	H10D—C108—H10F	109.5
C118—C117—C104	121.9 (2)	H10E—C108—H10F	109.5
C118—C117—C122	118.2 (2)	C124—C125—H125	119.6
C122—C117—C104	119.8 (2)	C126—C125—C124	120.8 (3)
C11—C16—H16	119.7	C126—C125—H125	119.6
O4—C9—C2—C3	112.9 (2)	C102—C103—C111—C116	−42.2 (3)
O4—C9—C2—C1	−122.1 (2)	C2—C3—C11—C12	−129.8 (2)
O103—C109—C102—C101	−52.7 (2)	C2—C3—C11—C16	47.6 (3)
O103—C109—C102—C103	72.0 (2)	C6—C29—C34—C33	−179.7 (2)
O2—C7—C1—C2	−44.6 (3)	C6—C29—C30—C31	179.8 (2)
O2—C7—C1—C6	79.8 (3)	C129—C134—C133—C132	0.0 (4)
O1—C7—C1—C2	136.50 (18)	C129—C130—C131—C132	−1.1 (4)
O1—C7—C1—C6	−99.1 (2)	C11—C3—C2—C9	−89.4 (2)
O3—C9—C2—C3	−64.5 (2)	C11—C3—C2—C1	143.46 (19)
O3—C9—C2—C1	60.5 (2)	C11—C12—C13—C14	−0.3 (4)
O104—C109—C102—C101	129.4 (2)	C11—C16—C15—C14	0.5 (4)
O104—C109—C102—C103	−105.9 (2)	C34—C29—C6—C5	59.7 (3)
C9—C2—C1—C7	46.1 (2)	C34—C29—C6—C1	−118.4 (2)
C9—C2—C1—C6	−77.4 (2)	C34—C29—C30—C31	−1.3 (3)
C123—C105—C106—C101	−179.44 (18)	C34—C33—C32—C31	−1.0 (4)
C123—C105—C106—C129	−1.4 (3)	C18—C17—C22—C21	0.2 (3)
C123—C124—C125—C126	0.6 (4)	C18—C19—C20—C21	0.1 (4)
C123—C128—C127—C126	−0.5 (4)	C103—C104—C105—C123	163.0 (2)
C29—C6—C1—C7	21.4 (3)	C103—C104—C105—C106	−15.3 (3)
C29—C6—C1—C2	145.28 (18)	C103—C104—C117—C118	132.3 (2)
C29—C34—C33—C32	−0.2 (4)	C103—C104—C117—C122	−51.8 (3)
C29—C30—C31—C32	0.2 (4)	C103—C111—C112—C113	−174.8 (2)
C4—C3—C2—C9	91.4 (2)	C103—C111—C116—C115	175.3 (3)
C4—C3—C2—C1	−35.7 (3)	C111—C112—C113—C114	0.3 (4)
C4—C3—C11—C12	49.4 (3)	C111—C116—C115—C114	−1.2 (5)
C4—C3—C11—C16	−133.2 (3)	C30—C29—C6—C5	−121.4 (2)
C4—C5—C6—C29	−177.45 (19)	C30—C29—C6—C1	60.5 (3)
C4—C5—C6—C1	0.7 (3)	C30—C29—C34—C33	1.4 (3)
C4—C17—C22—C21	176.8 (2)	C30—C31—C32—C33	1.0 (4)
C3—C4—C5—C23	−163.1 (2)	C134—C129—C130—C131	1.7 (3)
C3—C4—C5—C6	15.2 (3)	C134—C133—C132—C131	0.6 (4)
C3—C4—C17—C18	−132.3 (2)	C17—C4—C3—C2	−172.26 (19)
C3—C4—C17—C22	51.2 (3)	C17—C4—C3—C11	8.6 (3)
C3—C2—C1—C7	171.79 (17)	C17—C4—C5—C23	13.6 (3)
C3—C2—C1—C6	48.2 (2)	C17—C4—C5—C6	−168.1 (2)
C3—C11—C12—C13	178.3 (2)	C17—C18—C19—C20	0.4 (3)
C3—C11—C16—C15	−178.3 (2)	C24—C23—C5—C4	−122.2 (2)
C23—C5—C6—C29	0.8 (3)	C24—C23—C5—C6	59.5 (3)
C23—C5—C6—C1	178.93 (18)	C24—C23—C28—C27	−0.3 (3)
C23—C24—C25—C26	−0.9 (4)	C24—C25—C26—C27	0.5 (4)
C23—C28—C27—C26	−0.1 (4)	C22—C21—C20—C19	−0.5 (4)
C109—C102—C103—C104	−89.5 (2)	C12—C11—C16—C15	−0.9 (4)
C109—C102—C103—C111	94.1 (2)	C12—C13—C14—C15	−0.1 (4)
C101—C106—C129—C134	115.8 (2)	C117—C104—C105—C123	−14.3 (3)
C101—C106—C129—C130	−64.9 (3)	C117—C104—C105—C106	167.5 (2)
C101—C102—C103—C104	38.2 (3)	C117—C104—C103—C102	171.84 (19)
C101—C102—C103—C111	−138.24 (19)	C117—C104—C103—C111	−12.1 (3)
C104—C105—C106—C101	−1.3 (3)	C16—C11—C12—C13	0.8 (4)
C104—C105—C106—C129	176.77 (18)	C16—C15—C14—C13	0.1 (4)
C104—C103—C111—C112	−43.7 (3)	C112—C111—C116—C115	0.5 (4)
C104—C103—C111—C116	141.7 (2)	C112—C113—C114—C115	−1.0 (4)
C104—C117—C118—C119	176.6 (2)	C130—C129—C134—C133	−1.2 (3)
C104—C117—C122—C121	−175.8 (2)	C130—C131—C132—C133	−0.1 (4)
C105—C123—C124—C125	177.7 (2)	C28—C23—C5—C4	58.8 (3)
C105—C123—C128—C127	−177.8 (2)	C28—C23—C5—C6	−119.5 (2)
C105—C104—C103—C102	−5.2 (3)	C28—C23—C24—C25	0.8 (3)
C105—C104—C103—C111	170.81 (19)	C28—C27—C26—C25	0.0 (4)
C105—C104—C117—C118	−50.5 (3)	C124—C123—C105—C104	122.2 (2)
C105—C104—C117—C122	125.3 (2)	C124—C123—C105—C106	−59.6 (3)
C105—C106—C129—C134	−62.2 (3)	C124—C123—C128—C127	0.7 (3)
C105—C106—C129—C130	117.1 (2)	C113—C114—C115—C116	1.4 (5)
C107—C101—C106—C105	159.64 (19)	C119—C120—C121—C122	0.2 (4)
C107—C101—C106—C129	−18.4 (3)	C19—C18—C17—C4	−177.1 (2)
C107—C101—C102—C109	−50.6 (2)	C19—C18—C17—C22	−0.6 (3)
C107—C101—C102—C103	−176.70 (17)	C118—C117—C122—C121	0.2 (3)
C5—C4—C3—C2	4.3 (3)	C118—C119—C120—C121	0.7 (4)
C5—C4—C3—C11	−174.8 (2)	C120—C119—C118—C117	−1.2 (4)
C5—C4—C17—C18	51.0 (3)	C120—C121—C122—C117	−0.6 (4)
C5—C4—C17—C22	−125.4 (2)	C116—C111—C112—C113	−0.1 (3)
C5—C23—C24—C25	−178.2 (2)	C8—O1—C7—O2	−7.3 (3)
C5—C23—C28—C27	178.7 (2)	C8—O1—C7—C1	171.6 (2)
C5—C6—C1—C7	−156.78 (19)	C122—C117—C118—C119	0.7 (3)
C5—C6—C1—C2	−32.9 (3)	C128—C123—C105—C104	−59.4 (3)
C106—C101—C107—O101	91.5 (2)	C128—C123—C105—C106	118.9 (2)
C106—C101—C107—O102	−87.5 (3)	C128—C123—C124—C125	−0.7 (3)
C106—C101—C102—C109	74.7 (2)	C20—C21—C22—C17	0.4 (4)
C106—C101—C102—C103	−51.3 (2)	C110—O103—C109—O104	−7.8 (3)
C106—C129—C134—C133	178.2 (2)	C110—O103—C109—C102	174.3 (2)
C106—C129—C130—C131	−177.7 (2)	C10—O3—C9—O4	9.6 (3)
C102—C101—C107—O101	−143.65 (18)	C10—O3—C9—C2	−173.1 (2)
C102—C101—C107—O102	37.3 (3)	C127—C126—C125—C124	−0.4 (4)
C102—C101—C106—C105	35.2 (3)	C108—O101—C107—O102	5.3 (3)
C102—C101—C106—C129	−142.85 (18)	C108—O101—C107—C101	−173.7 (2)
C102—C103—C111—C112	132.4 (2)	C125—C126—C127—C128	0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C101—H101···O2	0.99 (3)	2.39 (3)	3.384 (3)	176 (2)
C102—H102···O4	0.96 (3)	2.48 (3)	3.242 (3)	136 (2)
C16—H16···O4	0.95	2.59	3.407 (3)	145
C116—H116···O104	0.95	2.54	3.388 (3)	148