2,2,7,7-Tetra­phenyl-2,7-dihydrodibenz[c,e]oxepine

The structure of the title compound, C₃₈H₂₈O, has previously been reported by Hirano, Toyota & Toda [Heterocycles (2004), 62, 749–756]. Since these authors did not publish any coordinates, we present here a redetermination of this structure using new intensity data. The mol­ecule has chemical but not crystallographic C₂ symmetry. The central seven-membered ring adopts a twist-boat conformation.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.078
• wR factor = 0.199
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

2,2,7,7-Tetraphenyl-2,7-dihydrodibenzo[c,e]oxepine

Crystal data

C38H28O	F(000) = 1056
Mr = 500.60	Dx = 1.231 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10503 reflections
a = 13.6436 (17) Å	θ = 3.6–27.6°
b = 11.5482 (9) Å	µ = 0.07 mm^−1
c = 17.1442 (19) Å	T = 173 K
β = 90.306 (10)°	Block, colourless
V = 2701.2 (5) Å^3	0.24 × 0.23 × 0.21 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	3318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.097
Graphite monochromator	θmax = 27.7°, θmin = 3.5°
ω scans	h = −17→17
31915 measured reflections	k = −14→15
6240 independent reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.199	w = 1/[σ^2(Fo^2) + (0.089P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
6240 reflections	Δρmax = 0.36 e Å^−3
353 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (19)

Special details

Experimental. ¹H NMR (250 MHz, CDCl₃): δ 8.50 (br s, 2H), 7.56 (d, J = 8 Hz, 2H), 7.60–7.06 (m, 7H), 7.05–6.92 (m, 4H), 6.90–6.63 (m, 9H), 6.51 (d, J = 8 Hz, 2H), 6.56–6.40 (m, 2H). ¹³C NMR (63 MHz, CDCl₃): δ 148.0, 146.1, 143.1, 140.9, 129.8, 129.7, 128.3, 127.9, 127.5, 126.6, 126.5, 126.2, 125.6, 86.1. MS (ESI): m/z = 500 (M⁺).

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
C1	0.7679 (2)	0.2184 (2)	0.62825 (17)	0.0262 (6)
O1	0.77184 (15)	0.30170 (16)	0.69246 (12)	0.0266 (5)
C2	0.7094 (2)	0.4046 (2)	0.69302 (17)	0.0255 (6)
C11	0.8400 (2)	0.2557 (2)	0.56300 (17)	0.0269 (6)
C12	0.8270 (3)	0.2208 (3)	0.48554 (19)	0.0364 (7)
H12	0.7713	0.1757	0.4717	0.044*
C13	0.8941 (3)	0.2511 (3)	0.4286 (2)	0.0449 (9)
H13	0.8851	0.2245	0.3766	0.054*
C14	0.9747 (3)	0.3202 (3)	0.4471 (2)	0.0428 (9)
H14	1.0188	0.3445	0.4076	0.051*
C15	0.9894 (3)	0.3530 (3)	0.5240 (2)	0.0408 (8)
H15	1.0450	0.3983	0.5375	0.049*
C16	0.9236 (2)	0.3203 (3)	0.5816 (2)	0.0332 (7)
H16	0.9357	0.3420	0.6343	0.040*
C21	0.8081 (2)	0.1040 (2)	0.66433 (19)	0.0283 (6)
C22	0.8293 (2)	0.0096 (3)	0.6156 (2)	0.0375 (8)
H22	0.8217	0.0172	0.5607	0.045*
C23	0.8617 (2)	−0.0958 (3)	0.6473 (2)	0.0436 (9)
H23	0.8744	−0.1595	0.6138	0.052*
C24	0.8751 (3)	−0.1076 (3)	0.7270 (3)	0.0474 (10)
H24	0.8971	−0.1789	0.7485	0.057*
C25	0.8560 (3)	−0.0141 (3)	0.7748 (2)	0.0457 (9)
H25	0.8658	−0.0213	0.8295	0.055*
C26	0.8225 (2)	0.0908 (3)	0.7443 (2)	0.0355 (7)
H26	0.8094	0.1538	0.7783	0.043*
C31	0.7565 (2)	0.4818 (2)	0.75668 (17)	0.0257 (6)
C32	0.8552 (3)	0.4763 (3)	0.7744 (2)	0.0411 (8)
H32	0.8952	0.4214	0.7483	0.049*
C33	0.8979 (3)	0.5506 (3)	0.8305 (2)	0.0472 (9)
H33	0.9659	0.5446	0.8422	0.057*
C34	0.8413 (3)	0.6319 (3)	0.8683 (2)	0.0433 (9)
H34	0.8696	0.6817	0.9064	0.052*
C35	0.7425 (3)	0.6398 (3)	0.8500 (2)	0.0485 (10)
H35	0.7033	0.6967	0.8748	0.058*
C36	0.6999 (3)	0.5655 (3)	0.7957 (2)	0.0407 (8)
H36	0.6318	0.5713	0.7848	0.049*
C41	0.6048 (2)	0.3728 (2)	0.72066 (16)	0.0257 (6)
C42	0.5935 (2)	0.2891 (3)	0.77956 (19)	0.0343 (7)
H42	0.6490	0.2483	0.7988	0.041*
C43	0.5008 (3)	0.2660 (3)	0.8097 (2)	0.0415 (8)
H43	0.4939	0.2083	0.8487	0.050*
C44	0.4189 (3)	0.3251 (3)	0.7840 (2)	0.0400 (8)
H44	0.3562	0.3086	0.8052	0.048*
C45	0.4299 (2)	0.4099 (3)	0.7264 (2)	0.0388 (8)
H45	0.3744	0.4518	0.7082	0.047*
C46	0.5220 (2)	0.4326 (3)	0.69558 (18)	0.0308 (7)
H46	0.5285	0.4904	0.6565	0.037*
C51	0.7092 (2)	0.4661 (2)	0.61287 (17)	0.0255 (6)
C52	0.6677 (2)	0.4105 (2)	0.54721 (17)	0.0257 (6)
C53	0.6692 (2)	0.4662 (3)	0.47460 (19)	0.0329 (7)
H53	0.6418	0.4285	0.4303	0.039*
C54	0.7104 (2)	0.5763 (3)	0.4664 (2)	0.0362 (8)
H54	0.7117	0.6129	0.4168	0.043*
C55	0.7492 (2)	0.6316 (3)	0.5312 (2)	0.0352 (7)
H55	0.7762	0.7071	0.5262	0.042*
C56	0.7492 (2)	0.5775 (2)	0.60376 (18)	0.0292 (7)
H56	0.7766	0.6162	0.6476	0.035*
C61	0.6630 (2)	0.2031 (2)	0.59729 (17)	0.0259 (6)
C62	0.6187 (2)	0.2951 (2)	0.55460 (17)	0.0260 (6)
C63	0.5255 (2)	0.2796 (3)	0.52302 (18)	0.0320 (7)
H63	0.4962	0.3410	0.4944	0.038*
C64	0.4743 (2)	0.1768 (3)	0.5322 (2)	0.0368 (8)
H64	0.4118	0.1667	0.5085	0.044*
C65	0.5163 (2)	0.0882 (3)	0.5768 (2)	0.0370 (8)
H65	0.4807	0.0189	0.5861	0.044*
C66	0.6096 (2)	0.1012 (2)	0.60757 (18)	0.0292 (6)
H66	0.6380	0.0393	0.6364	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0368 (16)	0.0150 (13)	0.0269 (15)	0.0021 (11)	0.0013 (12)	−0.0056 (11)
O1	0.0368 (11)	0.0158 (9)	0.0271 (11)	0.0053 (8)	−0.0018 (9)	−0.0035 (8)
C2	0.0334 (15)	0.0171 (13)	0.0260 (15)	0.0039 (11)	−0.0005 (12)	−0.0022 (11)
C11	0.0350 (16)	0.0162 (13)	0.0294 (16)	0.0066 (11)	0.0015 (12)	0.0014 (11)
C12	0.0425 (18)	0.0317 (17)	0.0351 (18)	0.0059 (14)	0.0023 (14)	−0.0034 (14)
C13	0.059 (2)	0.047 (2)	0.0290 (18)	0.0156 (18)	0.0076 (16)	−0.0024 (15)
C14	0.048 (2)	0.0344 (18)	0.046 (2)	0.0110 (16)	0.0178 (17)	0.0092 (15)
C15	0.0406 (19)	0.0285 (17)	0.054 (2)	0.0011 (14)	0.0092 (16)	0.0023 (15)
C16	0.0403 (17)	0.0236 (15)	0.0357 (18)	0.0020 (13)	0.0033 (14)	−0.0020 (13)
C21	0.0292 (15)	0.0174 (13)	0.0384 (17)	0.0004 (11)	−0.0021 (12)	−0.0004 (12)
C22	0.0434 (19)	0.0198 (15)	0.049 (2)	0.0022 (13)	−0.0051 (15)	−0.0059 (14)
C23	0.0419 (19)	0.0176 (15)	0.071 (3)	0.0041 (13)	−0.0050 (17)	−0.0069 (16)
C24	0.0406 (19)	0.0222 (17)	0.079 (3)	0.0028 (14)	−0.0064 (18)	0.0173 (17)
C25	0.048 (2)	0.037 (2)	0.052 (2)	0.0012 (16)	−0.0027 (17)	0.0153 (17)
C26	0.0442 (19)	0.0264 (16)	0.0360 (18)	0.0059 (14)	0.0010 (14)	0.0040 (13)
C31	0.0380 (16)	0.0161 (13)	0.0231 (15)	0.0003 (11)	0.0012 (12)	−0.0012 (11)
C32	0.045 (2)	0.0339 (18)	0.044 (2)	0.0070 (15)	−0.0050 (16)	−0.0153 (15)
C33	0.042 (2)	0.041 (2)	0.059 (2)	0.0035 (16)	−0.0151 (17)	−0.0183 (17)
C34	0.057 (2)	0.0330 (18)	0.040 (2)	−0.0097 (16)	0.0004 (16)	−0.0151 (15)
C35	0.054 (2)	0.0375 (19)	0.054 (2)	−0.0056 (17)	0.0111 (18)	−0.0260 (17)
C36	0.0349 (17)	0.0296 (17)	0.058 (2)	−0.0024 (13)	0.0036 (15)	−0.0152 (16)
C41	0.0362 (16)	0.0182 (13)	0.0228 (15)	−0.0004 (12)	−0.0010 (12)	−0.0059 (11)
C42	0.0436 (18)	0.0233 (15)	0.0361 (18)	0.0050 (13)	0.0043 (14)	0.0027 (13)
C43	0.060 (2)	0.0245 (16)	0.041 (2)	−0.0028 (15)	0.0162 (16)	0.0006 (14)
C44	0.0382 (18)	0.0390 (19)	0.043 (2)	−0.0120 (15)	0.0139 (15)	−0.0106 (15)
C45	0.0338 (17)	0.045 (2)	0.0377 (19)	0.0034 (15)	−0.0007 (14)	−0.0079 (15)
C46	0.0341 (16)	0.0280 (16)	0.0302 (17)	0.0030 (13)	0.0030 (13)	−0.0036 (12)
C51	0.0287 (15)	0.0179 (13)	0.0300 (16)	0.0058 (11)	0.0045 (12)	0.0005 (11)
C52	0.0305 (15)	0.0198 (14)	0.0269 (15)	0.0071 (11)	0.0013 (12)	0.0013 (11)
C53	0.0403 (18)	0.0303 (17)	0.0281 (16)	0.0049 (13)	−0.0031 (13)	0.0008 (13)
C54	0.0465 (19)	0.0272 (17)	0.0349 (18)	0.0044 (14)	0.0030 (14)	0.0095 (13)
C55	0.0420 (18)	0.0210 (15)	0.0427 (19)	−0.0033 (13)	0.0017 (15)	0.0047 (13)
C56	0.0332 (16)	0.0219 (15)	0.0326 (17)	−0.0007 (12)	0.0020 (13)	−0.0010 (12)
C61	0.0379 (16)	0.0169 (13)	0.0228 (14)	0.0013 (12)	0.0033 (12)	−0.0037 (11)
C62	0.0349 (16)	0.0182 (13)	0.0248 (15)	0.0024 (12)	0.0027 (12)	−0.0025 (11)
C63	0.0416 (18)	0.0272 (16)	0.0273 (16)	0.0047 (13)	0.0009 (13)	−0.0037 (12)
C64	0.0354 (17)	0.0343 (18)	0.040 (2)	−0.0019 (14)	−0.0039 (14)	−0.0068 (14)
C65	0.0433 (19)	0.0253 (16)	0.042 (2)	−0.0073 (14)	0.0044 (15)	−0.0061 (13)
C66	0.0366 (16)	0.0201 (14)	0.0309 (16)	0.0019 (12)	0.0028 (13)	−0.0007 (12)

Geometric parameters (Å, º)

C1—O1	1.463 (3)	C34—H34	0.9500
C1—C61	1.535 (4)	C35—C36	1.390 (5)
C1—C11	1.554 (4)	C35—H35	0.9500
C1—C21	1.557 (4)	C36—H36	0.9500
O1—C2	1.463 (3)	C41—C46	1.391 (4)
C2—C51	1.546 (4)	C41—C42	1.407 (4)
C2—C31	1.547 (4)	C42—C43	1.394 (5)
C2—C41	1.550 (4)	C42—H42	0.9500
C11—C12	1.398 (4)	C43—C44	1.379 (5)
C11—C16	1.399 (4)	C43—H43	0.9500
C12—C13	1.387 (5)	C44—C45	1.400 (5)
C12—H12	0.9500	C44—H44	0.9500
C13—C14	1.394 (5)	C45—C46	1.390 (5)
C13—H13	0.9500	C45—H45	0.9500
C14—C15	1.385 (5)	C46—H46	0.9500
C14—H14	0.9500	C51—C56	1.407 (4)
C15—C16	1.390 (5)	C51—C52	1.412 (4)
C15—H15	0.9500	C52—C53	1.401 (4)
C16—H16	0.9500	C52—C62	1.496 (4)
C21—C26	1.392 (5)	C53—C54	1.398 (5)
C21—C22	1.405 (4)	C53—H53	0.9500
C22—C23	1.403 (5)	C54—C55	1.384 (5)
C22—H22	0.9500	C54—H54	0.9500
C23—C24	1.385 (6)	C55—C56	1.391 (4)
C23—H23	0.9500	C55—H55	0.9500
C24—C25	1.382 (6)	C56—H56	0.9500
C24—H24	0.9500	C61—C66	1.395 (4)
C25—C26	1.396 (5)	C61—C62	1.423 (4)
C25—H25	0.9500	C62—C63	1.391 (4)
C26—H26	0.9500	C63—C64	1.387 (5)
C31—C32	1.380 (5)	C63—H63	0.9500
C31—C36	1.408 (4)	C64—C65	1.398 (5)
C32—C33	1.412 (5)	C64—H64	0.9500
C32—H32	0.9500	C65—C66	1.383 (4)
C33—C34	1.380 (5)	C65—H65	0.9500
C33—H33	0.9500	C66—H66	0.9500
C34—C35	1.385 (5)
O1—C1—C61	111.5 (2)	C34—C35—C36	120.9 (3)
O1—C1—C11	109.8 (2)	C34—C35—H35	119.5
C61—C1—C11	112.0 (2)	C36—C35—H35	119.5
O1—C1—C21	104.4 (2)	C35—C36—C31	120.9 (3)
C61—C1—C21	111.4 (2)	C35—C36—H36	119.6
C11—C1—C21	107.4 (2)	C31—C36—H36	119.6
C2—O1—C1	121.4 (2)	C46—C41—C42	118.1 (3)
O1—C2—C51	111.4 (2)	C46—C41—C2	122.4 (3)
O1—C2—C31	103.5 (2)	C42—C41—C2	119.2 (3)
C51—C2—C31	111.2 (2)	C43—C42—C41	120.0 (3)
O1—C2—C41	110.3 (2)	C43—C42—H42	120.0
C51—C2—C41	112.5 (2)	C41—C42—H42	120.0
C31—C2—C41	107.5 (2)	C44—C43—C42	121.5 (3)
C12—C11—C16	118.0 (3)	C44—C43—H43	119.3
C12—C11—C1	121.8 (3)	C42—C43—H43	119.3
C16—C11—C1	120.1 (3)	C43—C44—C45	118.8 (3)
C13—C12—C11	121.0 (3)	C43—C44—H44	120.6
C13—C12—H12	119.5	C45—C44—H44	120.6
C11—C12—H12	119.5	C46—C45—C44	120.0 (3)
C12—C13—C14	120.5 (3)	C46—C45—H45	120.0
C12—C13—H13	119.7	C44—C45—H45	120.0
C14—C13—H13	119.7	C45—C46—C41	121.5 (3)
C15—C14—C13	118.8 (3)	C45—C46—H46	119.2
C15—C14—H14	120.6	C41—C46—H46	119.2
C13—C14—H14	120.6	C56—C51—C52	118.8 (3)
C14—C15—C16	120.8 (3)	C56—C51—C2	121.3 (3)
C14—C15—H15	119.6	C52—C51—C2	119.9 (2)
C16—C15—H15	119.6	C53—C52—C51	119.5 (3)
C15—C16—C11	120.8 (3)	C53—C52—C62	119.5 (3)
C15—C16—H16	119.6	C51—C52—C62	121.0 (3)
C11—C16—H16	119.6	C54—C53—C52	120.9 (3)
C26—C21—C22	118.2 (3)	C54—C53—H53	119.5
C26—C21—C1	122.1 (3)	C52—C53—H53	119.5
C22—C21—C1	119.7 (3)	C55—C54—C53	119.5 (3)
C23—C22—C21	120.5 (3)	C55—C54—H54	120.3
C23—C22—H22	119.8	C53—C54—H54	120.3
C21—C22—H22	119.8	C54—C55—C56	120.5 (3)
C24—C23—C22	120.5 (3)	C54—C55—H55	119.7
C24—C23—H23	119.7	C56—C55—H55	119.7
C22—C23—H23	119.7	C55—C56—C51	120.8 (3)
C25—C24—C23	119.0 (3)	C55—C56—H56	119.6
C25—C24—H24	120.5	C51—C56—H56	119.6
C23—C24—H24	120.5	C66—C61—C62	118.3 (3)
C24—C25—C26	121.2 (4)	C66—C61—C1	122.7 (3)
C24—C25—H25	119.4	C62—C61—C1	119.0 (2)
C26—C25—H25	119.4	C63—C62—C61	119.2 (3)
C21—C26—C25	120.6 (3)	C63—C62—C52	119.3 (3)
C21—C26—H26	119.7	C61—C62—C52	121.4 (3)
C25—C26—H26	119.7	C64—C63—C62	121.8 (3)
C32—C31—C36	117.6 (3)	C64—C63—H63	119.1
C32—C31—C2	122.0 (3)	C62—C63—H63	119.1
C36—C31—C2	120.3 (3)	C63—C64—C65	118.9 (3)
C31—C32—C33	121.4 (3)	C63—C64—H64	120.6
C31—C32—H32	119.3	C65—C64—H64	120.6
C33—C32—H32	119.3	C66—C65—C64	120.2 (3)
C34—C33—C32	120.2 (3)	C66—C65—H65	119.9
C34—C33—H33	119.9	C64—C65—H65	119.9
C32—C33—H33	119.9	C65—C66—C61	121.6 (3)
C33—C34—C35	119.0 (3)	C65—C66—H66	119.2
C33—C34—H34	120.5	C61—C66—H66	119.2
C35—C34—H34	120.5
C61—C1—O1—C2	−36.7 (3)	C31—C2—C41—C46	97.5 (3)
C11—C1—O1—C2	88.1 (3)	O1—C2—C41—C42	36.8 (3)
C21—C1—O1—C2	−157.1 (2)	C51—C2—C41—C42	161.9 (3)
C1—O1—C2—C51	−45.5 (3)	C31—C2—C41—C42	−75.4 (3)
C1—O1—C2—C31	−165.0 (2)	C46—C41—C42—C43	1.7 (4)
C1—O1—C2—C41	80.2 (3)	C2—C41—C42—C43	174.8 (3)
O1—C1—C11—C12	−155.9 (3)	C41—C42—C43—C44	−1.2 (5)
C61—C1—C11—C12	−31.4 (4)	C42—C43—C44—C45	0.1 (5)
C21—C1—C11—C12	91.2 (3)	C43—C44—C45—C46	0.4 (5)
O1—C1—C11—C16	28.0 (4)	C44—C45—C46—C41	0.1 (5)
C61—C1—C11—C16	152.4 (3)	C42—C41—C46—C45	−1.1 (4)
C21—C1—C11—C16	−84.9 (3)	C2—C41—C46—C45	−174.0 (3)
C16—C11—C12—C13	−1.2 (5)	O1—C2—C51—C56	−114.2 (3)
C1—C11—C12—C13	−177.4 (3)	C31—C2—C51—C56	0.6 (4)
C11—C12—C13—C14	−2.0 (5)	C41—C2—C51—C56	121.3 (3)
C12—C13—C14—C15	3.4 (5)	O1—C2—C51—C52	66.2 (3)
C13—C14—C15—C16	−1.7 (5)	C31—C2—C51—C52	−178.9 (2)
C14—C15—C16—C11	−1.4 (5)	C41—C2—C51—C52	−58.2 (3)
C12—C11—C16—C15	2.9 (4)	C56—C51—C52—C53	1.4 (4)
C1—C11—C16—C15	179.1 (3)	C2—C51—C52—C53	−179.0 (3)
O1—C1—C21—C26	11.1 (4)	C56—C51—C52—C62	−176.3 (3)
C61—C1—C21—C26	−109.3 (3)	C2—C51—C52—C62	3.3 (4)
C11—C1—C21—C26	127.6 (3)	C51—C52—C53—C54	−0.6 (4)
O1—C1—C21—C22	−169.9 (3)	C62—C52—C53—C54	177.1 (3)
C61—C1—C21—C22	69.7 (3)	C52—C53—C54—C55	−0.7 (5)
C11—C1—C21—C22	−53.4 (4)	C53—C54—C55—C56	1.2 (5)
C26—C21—C22—C23	1.7 (5)	C54—C55—C56—C51	−0.4 (5)
C1—C21—C22—C23	−177.3 (3)	C52—C51—C56—C55	−0.9 (4)
C21—C22—C23—C24	−1.3 (5)	C2—C51—C56—C55	179.6 (3)
C22—C23—C24—C25	0.1 (5)	O1—C1—C61—C66	−110.8 (3)
C23—C24—C25—C26	0.8 (6)	C11—C1—C61—C66	125.7 (3)
C22—C21—C26—C25	−0.8 (5)	C21—C1—C61—C66	5.3 (4)
C1—C21—C26—C25	178.2 (3)	O1—C1—C61—C62	70.8 (3)
C24—C25—C26—C21	−0.4 (5)	C11—C1—C61—C62	−52.7 (3)
O1—C2—C31—C32	28.1 (4)	C21—C1—C61—C62	−173.1 (3)
C51—C2—C31—C32	−91.6 (3)	C66—C61—C62—C63	−1.6 (4)
C41—C2—C31—C32	144.8 (3)	C1—C61—C62—C63	176.8 (3)
O1—C2—C31—C36	−155.5 (3)	C66—C61—C62—C52	174.5 (3)
C51—C2—C31—C36	84.8 (3)	C1—C61—C62—C52	−7.1 (4)
C41—C2—C31—C36	−38.8 (4)	C53—C52—C62—C63	−47.8 (4)
C36—C31—C32—C33	0.9 (5)	C51—C52—C62—C63	129.9 (3)
C2—C31—C32—C33	177.4 (3)	C53—C52—C62—C61	136.1 (3)
C31—C32—C33—C34	−0.8 (6)	C51—C52—C62—C61	−46.2 (4)
C32—C33—C34—C35	−0.4 (6)	C61—C62—C63—C64	0.1 (5)
C33—C34—C35—C36	1.5 (6)	C52—C62—C63—C64	−176.1 (3)
C34—C35—C36—C31	−1.3 (6)	C62—C63—C64—C65	2.4 (5)
C32—C31—C36—C35	0.1 (5)	C63—C64—C65—C66	−3.5 (5)
C2—C31—C36—C35	−176.5 (3)	C64—C65—C66—C61	2.0 (5)
O1—C2—C41—C46	−150.4 (3)	C62—C61—C66—C65	0.6 (4)
C51—C2—C41—C46	−25.3 (4)	C1—C61—C66—C65	−177.8 (3)