Weak intra- and intermolecular interactions in a binaphthol imine: an experimental charge-density study on (±)-8′-benzhydrylideneamino-1,1′-binaphthyl-2-ol

The charge density in (±)-8′-benzhydrylideneamino-1,1′-binaphthyl-2-ol (1) has been studied experimentally using Mo Kα X-ray diffraction at 100 K, and by theory using density-functional thoery (DFT) calculations at the B3LYP/6-311++G** level. The nature of the weak intramolecular peri-C...N, CH...π, H...H and C(π)...C(π) interactions has been examined by topological analysis using the Quantum Theory of Atoms in Molecules (QTAIM) approach. An analysis of the density ρ(r), the Laplacian of the density ∇²ρ(r_b) and other topological properties at the bond-critical points were used to classify these interactions. The study confirms the presence of the intramolecular CH...π interaction in (1), which was previously suspected on geometrical grounds. An analysis of the ellipticity profiles along the bond paths unambiguously shows the π-delocalization between the imine unit and one N-phenyl group. The weak intermolecular interactions in the crystal of (1) were examined experimentally and theoretically through the pairwise interactions of the seven independent dimeric pairs of (1) responsible for the set of unique intermolecular interactions, and also through examination of the Hirshfeld surface d_norm property. The theoretical dimeric-pair calculations used the BLYP-D functional which supplements the exchange-correlational functional with an empirical dispersion term to provide a more accurate determination of the energies for the weak intermolecular interactions.

Computing details

Data collection: Collect (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(xd)

Crystal data

C33H23NO	F(000) = 944
Mr = 449.52	Dx = 1.307 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1055 (1) Å	Cell parameters from 97904 reflections
b = 11.6712 (1) Å	θ = 2.9–41.2°
c = 18.0627 (1) Å	µ = 0.08 mm^−1
β = 102.6753 (3)°	T = 100 K
V = 2284.13 (3) Å^3	Prism, pale straw yellow
Z = 4	0.53 × 0.5 × 0.37 mm

Data collection

KappaCCD diffractometer	23246 independent reflections
Radiation source: Enraf Nonius FR590	19025 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
CCD rotation images, thick slices scans	θmax = 50°, θmin = 2.1°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −16→23
Tmin = 0.954, Tmax = 1.01	k = −26→26
358895 measured reflections	l = −41→38

Refinement

Refinement on F	1066 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.024	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.015	(Δ/σ)max = 0.00001
S = 1.77	Δρmax = 0.25 e Å^−3
19692 reflections	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq
O(1)	0.55996 (2)	0.11811 (2)	0.174392 (14)	0.02
N(1)	0.290160 (16)	0.147690 (14)	0.213561 (9)	0.013
C(1)	0.336483 (12)	0.131168 (13)	0.057112 (9)	0.012
C(2)	0.365365 (14)	0.138882 (14)	−0.013624 (9)	0.015
C(3)	0.324964 (15)	0.231376 (15)	−0.063320 (10)	0.016
C(4)	0.253475 (15)	0.315536 (15)	−0.041702 (10)	0.016
C(5)	0.151440 (15)	0.403266 (14)	0.051222 (11)	0.018
C(6)	0.125577 (15)	0.405623 (15)	0.122144 (12)	0.019
C(7)	0.169115 (14)	0.317084 (15)	0.174414 (11)	0.017
C(8)	0.236300 (12)	0.225332 (13)	0.156011 (9)	0.013
C(9)	0.265874 (12)	0.220649 (12)	0.082194 (9)	0.012
C(10)	0.222646 (13)	0.312533 (13)	0.030487 (9)	0.013
C(11)	0.376893 (16)	0.025569 (14)	0.102265 (8)	0.013
C(12)	0.485175 (16)	0.024117 (16)	0.157289 (9)	0.016
C(13)	0.52410 (2)	−0.07543 (2)	0.200740 (10)	0.02
C(14)	0.45304 (2)	−0.17289 (2)	0.189237 (12)	0.022
C(15)	0.26567 (3)	−0.275525 (18)	0.120344 (15)	0.025
C(16)	0.15754 (3)	−0.27652 (2)	0.065585 (16)	0.027
C(17)	0.12156 (2)	−0.178551 (19)	0.019794 (13)	0.024
C(18)	0.193018 (19)	−0.080873 (16)	0.030866 (10)	0.018
C(19)	0.304199 (18)	−0.076416 (15)	0.087807 (9)	0.015
C(20)	0.34165 (2)	−0.176217 (17)	0.132638 (11)	0.019
C(21)	0.226765 (15)	0.078707 (12)	0.245682 (8)	0.012
C(22)	0.293940 (16)	0.005906 (13)	0.309035 (8)	0.013
C(23)	0.419297 (18)	0.026350 (15)	0.340462 (9)	0.016
C(24)	0.48275 (2)	−0.039313 (19)	0.400607 (11)	0.022
C(25)	0.42215 (3)	−0.127395 (19)	0.430242 (11)	0.024
C(26)	0.29802 (2)	−0.149484 (17)	0.399011 (11)	0.022
C(27)	0.233906 (19)	−0.082757 (14)	0.338942 (9)	0.017
C(28)	0.090252 (16)	0.061384 (13)	0.220842 (8)	0.013
C(29)	0.048384 (17)	−0.032501 (15)	0.174141 (8)	0.015
C(30)	−0.077460 (19)	−0.052271 (18)	0.148596 (9)	0.019
C(31)	−0.16291 (2)	0.02098 (2)	0.169862 (11)	0.02
C(32)	−0.12199 (2)	0.113142 (19)	0.218071 (11)	0.02
C(33)	0.004527 (19)	0.133056 (15)	0.244084 (10)	0.017
H(2)	0.420541	0.072019	−0.031339	0.032
H(3)	0.350179	0.235829	−0.117866	0.033
H(4)	0.220064	0.38521	−0.080364	0.034
H(5)	0.117424	0.470901	0.011015	0.036
H(6)	0.071944	0.475319	0.137971	0.037
H(7)	0.149458	0.321014	0.230494	0.031
H(13)	0.609769	−0.074921	0.243184	0.038
H(14)	0.482358	−0.248012	0.223677	0.039
H(15)	0.292904	−0.351425	0.154397	0.041
H(16)	0.100047	−0.352426	0.057597	0.043
H(17)	0.037678	−0.180586	−0.024103	0.038
H(18)	0.16394	−0.006312	−0.004195	0.03
H(23)	0.467225	0.093947	0.31759	0.031
H(24)	0.579251	−0.022375	0.424766	0.041
H(25)	0.47156	−0.178369	0.477302	0.043
H(26)	0.251439	−0.2186	0.421358	0.037
H(27)	0.137224	−0.099713	0.315338	0.031
H(29)	0.114335	−0.090266	0.157804	0.029
H(30)	−0.109287	−0.124709	0.112058	0.037
H(31)	−0.260872	0.006634	0.149177	0.042
H(32)	−0.188174	0.169513	0.235451	0.039
H(33)	0.036033	0.203981	0.282062	0.031
H(1)	0.528556	0.17986	0.139545	0.028

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.01438 (8)	0.02289 (9)	0.02155 (8)	0.00186 (7)	0.00147 (7)	0.00012 (8)
N(1)	0.01334 (6)	0.01265 (5)	0.01222 (5)	−0.00018 (5)	0.00338 (5)	0.00116 (4)
C(1)	0.01365 (5)	0.01104 (5)	0.01225 (5)	0.00123 (4)	0.00369 (4)	0.00082 (4)
C(2)	0.01717 (6)	0.01468 (5)	0.01322 (5)	0.00161 (5)	0.00554 (4)	0.00072 (5)
C(3)	0.01970 (6)	0.01625 (6)	0.01292 (5)	0.00021 (5)	0.00547 (5)	0.00215 (5)
C(4)	0.01942 (6)	0.01395 (5)	0.01388 (5)	0.00077 (5)	0.00426 (5)	0.00333 (5)
C(5)	0.02185 (7)	0.01216 (5)	0.01934 (6)	0.00462 (5)	0.00619 (5)	0.00303 (5)
C(6)	0.02482 (7)	0.01328 (6)	0.02178 (7)	0.00597 (6)	0.00938 (6)	0.00176 (5)
C(7)	0.02159 (6)	0.01340 (5)	0.01718 (6)	0.00347 (5)	0.00829 (5)	0.00034 (5)
C(8)	0.01456 (5)	0.01103 (5)	0.01267 (5)	0.00097 (4)	0.00427 (4)	0.00066 (4)
C(9)	0.01333 (5)	0.00997 (5)	0.01200 (5)	0.00071 (4)	0.00349 (4)	0.00094 (4)
C(10)	0.01582 (5)	0.01069 (5)	0.01396 (5)	0.00109 (4)	0.00369 (4)	0.00203 (4)
C(11)	0.01529 (6)	0.01174 (5)	0.01338 (5)	0.00279 (5)	0.00384 (5)	0.00108 (4)
C(12)	0.01495 (6)	0.01720 (6)	0.01520 (5)	0.00528 (5)	0.00381 (5)	0.00145 (5)
C(13)	0.02079 (7)	0.02236 (8)	0.01760 (6)	0.01070 (6)	0.00525 (6)	0.00462 (6)
C(14)	0.02924 (8)	0.01775 (7)	0.02018 (6)	0.01126 (7)	0.01004 (7)	0.00633 (6)
C(15)	0.03998 (10)	0.01131 (7)	0.02861 (8)	0.00152 (7)	0.01642 (9)	0.00224 (6)
C(16)	0.04170 (11)	0.01345 (7)	0.03030 (8)	−0.00676 (8)	0.01500 (10)	−0.00355 (7)
C(17)	0.03274 (9)	0.01702 (7)	0.02202 (7)	−0.00819 (7)	0.00801 (8)	−0.00498 (6)
C(18)	0.02419 (7)	0.01406 (6)	0.01598 (5)	−0.00338 (6)	0.00441 (6)	−0.00116 (5)
C(19)	0.02093 (6)	0.01074 (5)	0.01461 (5)	0.00169 (5)	0.00636 (5)	0.00055 (4)
C(20)	0.02850 (8)	0.01165 (6)	0.01947 (6)	0.00500 (6)	0.01104 (7)	0.00289 (5)
C(21)	0.01205 (6)	0.01215 (5)	0.01098 (4)	0.00043 (4)	0.00286 (4)	0.00038 (4)
C(22)	0.01399 (6)	0.01280 (5)	0.01094 (4)	0.00099 (4)	0.00237 (4)	0.00048 (4)
C(23)	0.01432 (7)	0.01770 (6)	0.01564 (5)	0.00158 (5)	0.00049 (5)	0.00071 (5)
C(24)	0.02009 (8)	0.02229 (7)	0.01880 (6)	0.00479 (6)	−0.00301 (6)	0.00127 (6)
C(25)	0.03012 (10)	0.02058 (7)	0.01736 (6)	0.00557 (7)	−0.00250 (7)	0.00408 (6)
C(26)	0.03022 (9)	0.01812 (6)	0.01715 (6)	0.00026 (6)	0.00216 (7)	0.00596 (6)
C(27)	0.02008 (7)	0.01562 (5)	0.01433 (5)	−0.00100 (5)	0.00286 (5)	0.00321 (5)
C(28)	0.01168 (6)	0.01397 (5)	0.01297 (5)	0.00085 (4)	0.00335 (4)	0.00039 (4)
C(29)	0.01273 (7)	0.01742 (6)	0.01569 (5)	−0.00068 (5)	0.00277 (4)	−0.00216 (5)
C(30)	0.01345 (7)	0.02338 (7)	0.01803 (6)	−0.00273 (6)	0.00179 (5)	−0.00054 (6)
C(31)	0.01240 (7)	0.02720 (8)	0.02123 (6)	0.00004 (6)	0.00309 (5)	0.00350 (7)
C(32)	0.01408 (8)	0.02355 (7)	0.02493 (7)	0.00422 (6)	0.00743 (6)	0.00275 (7)
C(33)	0.01542 (7)	0.01727 (6)	0.02046 (6)	0.00253 (5)	0.00687 (5)	−0.00072 (5)
H(2)	0.038754	0.028071	0.032059	0.009434	0.016335	−0.000923
H(3)	0.045369	0.035353	0.023092	0.002111	0.015823	0.003195
H(4)	0.045386	0.028341	0.028492	0.00845	0.009055	0.011506
H(5)	0.048363	0.027432	0.033853	0.014511	0.011496	0.013287
H(6)	0.049061	0.025666	0.041028	0.017932	0.019686	0.004139
H(7)	0.041738	0.028561	0.025019	0.00723	0.015376	0.001011
H(13)	0.026745	0.044383	0.039166	0.009797	−0.001284	0.009688
H(14)	0.0476	0.027505	0.042442	0.01486	0.009276	0.013549
H(15)	0.062304	0.019609	0.041885	0.005255	0.014456	0.007353
H(16)	0.064226	0.023873	0.041677	−0.016798	0.013408	−0.00474
H(17)	0.044302	0.036751	0.029921	−0.013533	−0.000417	−0.003244
H(18)	0.036172	0.023883	0.028155	−0.001506	0.001827	0.0049
H(23)	0.028001	0.033841	0.031101	−0.004709	0.003388	0.00827
H(24)	0.027531	0.053815	0.035513	0.000241	−0.005108	0.0113
H(25)	0.045941	0.046236	0.032135	0.008375	−0.001163	0.019308
H(26)	0.047117	0.030376	0.034786	−0.003169	0.010149	0.012225
H(27)	0.027339	0.031427	0.031903	−0.004234	0.003666	0.004145
H(29)	0.028684	0.026008	0.03411	0.001873	0.008855	−0.006114
H(30)	0.034606	0.038273	0.036335	−0.013223	0.004535	−0.009371
H(31)	0.019102	0.059386	0.047266	−0.006669	0.004512	−0.00013
H(32)	0.026967	0.046387	0.048623	0.009883	0.01628	−0.000698
H(33)	0.03257	0.027993	0.035061	0.001187	0.01018	−0.008144
H(1)	0.024478	0.028497	0.028228	0.000254	0.002753	0.004593

Geometric parameters (Å, º)

O(1)—C(12)	1.3697 (3)	C(16)—C(17)	1.4164 (4)
O(1)—H(1)	0.97	C(16)—H(16)	1.083
N(1)—C(8)	1.4095 (2)	C(17)—C(18)	1.3783 (3)
N(1)—C(21)	1.2883 (2)	C(17)—H(17)	1.083
C(1)—C(2)	1.3868 (2)	C(18)—C(19)	1.4240 (3)
C(1)—C(9)	1.4376 (2)	C(18)—H(18)	1.083
C(1)—C(11)	1.4916 (2)	C(19)—C(20)	1.4275 (2)
C(2)—C(3)	1.4127 (2)	C(21)—C(22)	1.4877 (2)
C(2)—H(2)	1.083	C(21)—C(28)	1.4974 (2)
C(3)—C(4)	1.3725 (2)	C(22)—C(23)	1.4037 (2)
C(3)—H(3)	1.083	C(22)—C(27)	1.4019 (2)
C(4)—C(10)	1.4194 (2)	C(23)—C(24)	1.3886 (3)
C(4)—H(4)	1.083	C(23)—H(23)	1.083
C(5)—C(6)	1.3732 (3)	C(24)—C(25)	1.3979 (3)
C(5)—C(10)	1.4202 (2)	C(24)—H(24)	1.083
C(5)—H(5)	1.0823	C(25)—C(26)	1.3942 (3)
C(6)—C(7)	1.4116 (3)	C(25)—H(25)	1.083
C(6)—H(6)	1.083	C(26)—C(27)	1.3970 (3)
C(7)—C(8)	1.3866 (2)	C(26)—H(26)	1.083
C(7)—H(7)	1.083	C(27)—H(27)	1.083
C(8)—C(9)	1.4425 (2)	C(28)—C(29)	1.3987 (2)
C(9)—C(10)	1.4339 (2)	C(28)—C(33)	1.3992 (2)
C(11)—C(12)	1.3819 (2)	C(29)—C(30)	1.3915 (2)
C(11)—C(19)	1.4298 (2)	C(29)—H(29)	1.083
C(12)—C(13)	1.4156 (3)	C(30)—C(31)	1.3924 (3)
C(13)—C(14)	1.3739 (3)	C(30)—H(30)	1.083
C(13)—H(13)	1.083	C(31)—C(32)	1.3958 (3)
C(14)—C(20)	1.4219 (3)	C(31)—H(31)	1.083
C(14)—H(14)	1.083	C(32)—C(33)	1.3997 (3)
C(15)—C(16)	1.3781 (4)	C(32)—H(32)	1.083
C(15)—C(20)	1.4221 (3)	C(33)—H(33)	1.083
C(15)—H(15)	1.083
C(8)—N(1)—C(21)	123.265 (16)	C(15)—C(16)—C(17)	120.14 (2)
C(2)—C(1)—C(9)	119.709 (15)	C(16)—C(17)—C(18)	120.22 (3)
C(2)—C(1)—C(11)	117.047 (14)	C(17)—C(18)—C(19)	121.02 (2)
C(9)—C(1)—C(11)	123.189 (14)	C(11)—C(19)—C(18)	121.850 (17)
C(1)—C(2)—C(3)	121.979 (17)	C(11)—C(19)—C(20)	119.55 (2)
C(2)—C(3)—C(4)	119.276 (17)	C(18)—C(19)—C(20)	118.586 (19)
C(3)—C(4)—C(10)	120.991 (17)	C(14)—C(20)—C(15)	121.82 (2)
C(6)—C(5)—C(10)	120.231 (18)	C(14)—C(20)—C(19)	119.00 (2)
C(5)—C(6)—C(7)	119.881 (18)	C(15)—C(20)—C(19)	119.17 (2)
C(6)—C(7)—C(8)	121.894 (18)	N(1)—C(21)—C(22)	118.162 (16)
N(1)—C(8)—C(7)	118.901 (16)	N(1)—C(21)—C(28)	124.531 (15)
N(1)—C(8)—C(9)	120.763 (15)	C(22)—C(21)—C(28)	117.208 (14)
C(7)—C(8)—C(9)	119.634 (16)	C(21)—C(22)—C(23)	119.960 (16)
C(1)—C(9)—C(8)	124.707 (15)	C(21)—C(22)—C(27)	121.156 (17)
C(1)—C(9)—C(10)	117.766 (15)	C(23)—C(22)—C(27)	118.879 (17)
C(8)—C(9)—C(10)	117.525 (15)	C(22)—C(23)—C(24)	120.70 (2)
C(4)—C(10)—C(5)	118.971 (17)	C(23)—C(24)—C(25)	120.08 (2)
C(4)—C(10)—C(9)	120.204 (16)	C(24)—C(25)—C(26)	119.82 (2)
C(5)—C(10)—C(9)	120.804 (16)	C(25)—C(26)—C(27)	120.09 (2)
C(1)—C(11)—C(12)	120.885 (16)	C(22)—C(27)—C(26)	120.42 (2)
C(1)—C(11)—C(19)	119.863 (15)	C(21)—C(28)—C(29)	117.855 (15)
C(12)—C(11)—C(19)	119.244 (17)	C(21)—C(28)—C(33)	122.697 (16)
O(1)—C(12)—C(11)	122.771 (19)	C(29)—C(28)—C(33)	119.425 (18)
O(1)—C(12)—C(13)	115.85 (2)	C(28)—C(29)—C(30)	120.442 (19)
C(11)—C(12)—C(13)	121.36 (2)	C(29)—C(30)—C(31)	120.16 (2)
C(12)—C(13)—C(14)	120.02 (2)	C(30)—C(31)—C(32)	119.80 (2)
C(13)—C(14)—C(20)	120.77 (2)	C(31)—C(32)—C(33)	120.18 (2)
C(16)—C(15)—C(20)	120.84 (2)	C(28)—C(33)—C(32)	119.93 (2)
C(21)—N(1)—C(8)—C(7)	68.659 (19)	O(1)—C(12)—C(13)—C(14)	178.00 (3)
C(21)—N(1)—C(8)—C(9)	−120.98 (2)	C(11)—C(12)—C(13)—C(14)	−0.764 (19)
C(8)—N(1)—C(21)—C(22)	−176.28 (2)	C(12)—C(13)—C(14)—C(20)	1.57 (2)
C(8)—N(1)—C(21)—C(28)	7.444 (15)	C(13)—C(14)—C(20)—C(15)	−179.13 (3)
C(9)—C(1)—C(2)—C(3)	−1.518 (15)	C(13)—C(14)—C(20)—C(19)	−0.16 (2)
C(2)—C(1)—C(9)—C(8)	−176.30 (2)	C(16)—C(15)—C(20)—C(14)	179.45 (4)
C(2)—C(1)—C(9)—C(10)	3.064 (14)	C(20)—C(15)—C(16)—C(17)	0.99 (2)
C(11)—C(1)—C(2)—C(3)	175.86 (2)	C(16)—C(15)—C(20)—C(19)	0.48 (2)
C(2)—C(1)—C(11)—C(12)	96.71 (2)	C(15)—C(16)—C(17)—C(18)	−1.45 (2)
C(2)—C(1)—C(11)—C(19)	−82.173 (18)	C(16)—C(17)—C(18)—C(19)	0.40 (2)
C(11)—C(1)—C(9)—C(8)	6.492 (14)	C(17)—C(18)—C(19)—C(11)	−177.37 (3)
C(11)—C(1)—C(9)—C(10)	−174.15 (2)	C(17)—C(18)—C(19)—C(20)	1.062 (19)
C(9)—C(1)—C(11)—C(12)	−86.009 (19)	C(11)—C(19)—C(20)—C(14)	−2.023 (18)
C(9)—C(1)—C(11)—C(19)	95.11 (2)	C(11)—C(19)—C(20)—C(15)	176.97 (3)
C(1)—C(2)—C(3)—C(4)	−0.956 (16)	C(18)—C(19)—C(20)—C(14)	179.51 (3)
C(2)—C(3)—C(4)—C(10)	1.781 (15)	C(18)—C(19)—C(20)—C(15)	−1.49 (2)
C(3)—C(4)—C(10)—C(5)	178.18 (2)	N(1)—C(21)—C(22)—C(23)	10.386 (16)
C(3)—C(4)—C(10)—C(9)	−0.143 (15)	N(1)—C(21)—C(22)—C(27)	−170.35 (2)
C(6)—C(5)—C(10)—C(4)	−176.67 (2)	N(1)—C(21)—C(28)—C(29)	97.52 (2)
C(10)—C(5)—C(6)—C(7)	−0.490 (16)	N(1)—C(21)—C(28)—C(33)	−84.23 (2)
C(6)—C(5)—C(10)—C(9)	1.642 (16)	C(28)—C(21)—C(22)—C(23)	−173.07 (2)
C(5)—C(6)—C(7)—C(8)	−1.154 (17)	C(28)—C(21)—C(22)—C(27)	6.200 (15)
C(6)—C(7)—C(8)—N(1)	172.08 (2)	C(22)—C(21)—C(28)—C(29)	−78.785 (17)
C(6)—C(7)—C(8)—C(9)	1.608 (15)	C(22)—C(21)—C(28)—C(33)	99.46 (2)
N(1)—C(8)—C(9)—C(1)	8.628 (14)	C(21)—C(22)—C(23)—C(24)	178.71 (3)
N(1)—C(8)—C(9)—C(10)	−170.73 (2)	C(21)—C(22)—C(27)—C(26)	−179.27 (3)
C(7)—C(8)—C(9)—C(1)	178.92 (2)	C(27)—C(22)—C(23)—C(24)	−0.574 (17)
C(7)—C(8)—C(9)—C(10)	−0.439 (14)	C(22)—C(23)—C(24)—C(25)	0.423 (19)
C(1)—C(9)—C(10)—C(4)	−2.270 (14)	C(23)—C(24)—C(25)—C(26)	0.31 (2)
C(1)—C(9)—C(10)—C(5)	179.44 (2)	C(24)—C(25)—C(26)—C(27)	−0.88 (2)
C(8)—C(9)—C(10)—C(4)	177.14 (2)	C(25)—C(26)—C(27)—C(22)	0.723 (19)
C(8)—C(9)—C(10)—C(5)	−1.157 (14)	C(21)—C(28)—C(29)—C(30)	−179.31 (2)
C(1)—C(11)—C(12)—O(1)	0.995 (18)	C(21)—C(28)—C(33)—C(32)	179.19 (3)
C(1)—C(11)—C(12)—C(13)	179.68 (3)	C(33)—C(28)—C(29)—C(30)	2.384 (17)
C(1)—C(11)—C(19)—C(18)	0.121 (16)	C(29)—C(28)—C(33)—C(32)	−2.591 (17)
C(1)—C(11)—C(19)—C(20)	−178.29 (2)	C(28)—C(29)—C(30)—C(31)	−0.488 (18)
C(19)—C(11)—C(12)—O(1)	179.88 (3)	C(29)—C(30)—C(31)—C(32)	−1.203 (19)
C(19)—C(11)—C(12)—C(13)	−1.435 (17)	C(30)—C(31)—C(32)—C(33)	0.984 (19)
C(12)—C(11)—C(19)—C(18)	−178.78 (3)	C(31)—C(32)—C(33)—C(28)	0.922 (18)
C(12)—C(11)—C(19)—C(20)	2.806 (17)