N-(1,2-Di­phenyl-2-oxoethyl­idene)­benzen­amine N-oxide

The title compound, C₂₀H₁₅NO₂, crystallizes in a monoclinic unit cell with two independent mol­ecules in the asymmetric unit. The configurations of three phenyl rings are determined by the sp² C and N atoms of the ethyl­idene­amine group.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.125
• Data-to-parameter ratio = 18.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The nitrone compounds are important synthetic reagents for the 1,3-dipolar cycloaddition reactions. Some nitrones are also good spin traps used in electron spin resonance (ESR) experiments. The title nitrone compound was prepared in order to examine the mechanism of the formation of N,N-dibenzoylaniline product in the photoinduced reactions of nitroarene with diphenylacetylene (Tian & Xu, 2003). We report here the results of X-ray crystallographic analysis of the title compound, (I), which was undertaken to establish its configuration.

There are two crystallographic independent molecules A and B in the asymmetric unit which are related by a local pseudo-twofold rotation axis (Fig. 1). The bond lengths and angles of both molecules A and B (Fig. 1) agree with each other, and are within normal ranges (Allen et al., 1987).

In both molecules, the configurations of the three phenyl rings are determined by the joining sp² state atoms of the ethylideneamine group (C7, C8 and N1). The oxide O2 atom lies on the C7/C8/N1 plane. The phenyl rings attached at the C7, C8 and N1 atoms make dihedral angles of 75.2 (1), 35.3 (1) and 64.3 (1)°, respectively, with respect to the ethylideneamine plane in molecule A, and 78.0 (1), 35.7 (1) and 65.8 (1)° in molecule B. The phenyl rings attached at the C8 and N1 are nearly orthogonal to each other, with dihedral angles of 80.6 (1) and 78.8 (1)° in molecules A and B, respectively.

In the benzoyl moiety, the carbonyl group (C7═O1) is twisted out of the aromatic ring, so that the atom O1 deviates by 0.572 (1) Å and the C6/C7/C8/O1 plane makes an angle of 23.1 (1)° from the aromatic ring in molecule A. The same values in molecule B are 0.490 (1) Å and 27.4 (1)°. The twisted angle of the carbonyl group in this compound are comparable to that in the another benzoyl derivative [22.1 (1)°; Usman et al., 2001].

S2. Experimental

The title compound was prepared by the oxidation of the corresponding imine with m-chloroperbenzoic acid in chloroform and was isolated by column chromatography on silica gel with petroleum ether–ethyl acetate as eluants. Single crystals suitable for the X-ray diffration were obtained from slow evaporation of acetone solution.

S3. Refinement

All H atoms were geometrically fixed and treated as riding atoms on their parent C atoms, with C—H distances of 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.

N-(1,2-diphenyl-2-oxo-ethylidene)benzenamine N-oxide

Crystal data

C20H15NO2	Dx = 1.277 Mg m^−3
Mr = 301.33	Melting point: 433(1) K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2399 (5) Å	Cell parameters from 7892 reflections
b = 14.7231 (7) Å	θ = 2.3–28.3°
c = 19.6858 (9) Å	µ = 0.08 mm^−1
β = 105.754 (1)°	T = 293 K
V = 3135.4 (2) Å^3	Block, light yellow
Z = 8	0.46 × 0.42 × 0.38 mm
F(000) = 1264

Data collection

Siemens SMART CCD area-detector diffractometer	7725 independent reflections
Radiation source: fine-focus sealed tube	5330 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.3°
ω scans	h = −14→13
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −19→13
Tmin = 0.963, Tmax = 0.969	l = −24→26
19495 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 0.567P] where P = (Fo^2 + 2Fc^2)/3
7725 reflections	(Δ/σ)max < 0.001
415 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1A	0.76781 (9)	0.37685 (7)	0.01733 (5)	0.0549 (3)
O2A	0.74656 (10)	0.24279 (9)	0.22056 (6)	0.0703 (3)
N1A	0.79208 (10)	0.28566 (8)	0.17658 (6)	0.0435 (3)
C1A	0.88860 (14)	0.49785 (9)	0.17816 (7)	0.0489 (3)
H1AA	0.8266	0.4837	0.1995	0.059*
C2A	0.97732 (16)	0.56198 (10)	0.20804 (9)	0.0609 (4)
H2AA	0.9741	0.5915	0.2493	0.073*
C3A	1.07013 (16)	0.58236 (11)	0.17729 (9)	0.0632 (4)
H3AA	1.1292	0.6257	0.1977	0.076*
C4A	1.07589 (15)	0.53872 (11)	0.11634 (9)	0.0600 (4)
H4AA	1.1395	0.5520	0.0960	0.072*
C5A	0.98737 (13)	0.47547 (10)	0.08555 (7)	0.0486 (3)
H5AA	0.9909	0.4465	0.0442	0.058*
C6A	0.89269 (12)	0.45471 (8)	0.11613 (6)	0.0388 (3)
C7A	0.79640 (11)	0.38819 (8)	0.08063 (7)	0.0384 (3)
C8A	0.72776 (11)	0.33692 (8)	0.12477 (6)	0.0385 (3)
C9A	0.59321 (12)	0.34638 (9)	0.10966 (7)	0.0406 (3)
C10A	0.53839 (14)	0.42901 (11)	0.08456 (8)	0.0526 (4)
H10A	0.5872	0.4770	0.0771	0.063*
C11A	0.41162 (16)	0.44022 (14)	0.07058 (9)	0.0692 (5)
H11A	0.3760	0.4962	0.0552	0.083*
C12A	0.33881 (15)	0.36910 (16)	0.07928 (9)	0.0739 (5)
H12A	0.2537	0.3766	0.0695	0.089*
C13A	0.39146 (15)	0.28656 (14)	0.10248 (10)	0.0688 (5)
H13A	0.3414	0.2381	0.1073	0.083*
C14A	0.51741 (14)	0.27496 (11)	0.11863 (8)	0.0525 (4)
H14A	0.5522	0.2193	0.1356	0.063*
C15A	0.92376 (12)	0.27184 (9)	0.18659 (7)	0.0404 (3)
C16A	1.00428 (14)	0.30024 (10)	0.24903 (8)	0.0509 (3)
H16A	0.9750	0.3276	0.2839	0.061*
C17A	1.12902 (15)	0.28710 (12)	0.25849 (8)	0.0618 (4)
H17A	1.1849	0.3063	0.3000	0.074*
C18A	1.17131 (14)	0.24594 (13)	0.20716 (9)	0.0640 (4)
H18A	1.2558	0.2381	0.2139	0.077*
C19A	1.08969 (14)	0.21600 (11)	0.14563 (8)	0.0569 (4)
H19A	1.1191	0.1870	0.1114	0.068*
C20A	0.96425 (13)	0.22902 (10)	0.13474 (7)	0.0463 (3)
H20A	0.9083	0.2093	0.0933	0.056*
O1B	0.71417 (10)	0.14793 (8)	0.00341 (5)	0.0588 (3)
O2B	0.75680 (12)	0.00250 (10)	−0.18977 (7)	0.0827 (4)
N1B	0.70687 (11)	0.04904 (8)	−0.14929 (6)	0.0518 (3)
C1B	0.60575 (15)	0.26218 (10)	−0.16201 (8)	0.0524 (4)
H1BA	0.6687	0.2441	−0.1815	0.063*
C2B	0.52032 (18)	0.32621 (11)	−0.19632 (9)	0.0652 (4)
H2BA	0.5267	0.3517	−0.2384	0.078*
C3B	0.42665 (17)	0.35217 (12)	−0.16858 (10)	0.0710 (5)
H3BA	0.3693	0.3950	−0.1919	0.085*
C4B	0.41694 (16)	0.31501 (12)	−0.10610 (11)	0.0699 (5)
H4BA	0.3523	0.3323	−0.0878	0.084*
C5B	0.50264 (14)	0.25212 (11)	−0.07052 (8)	0.0551 (4)
H5BA	0.4967	0.2281	−0.0279	0.066*
C6B	0.59771 (12)	0.22495 (9)	−0.09866 (7)	0.0421 (3)
C7B	0.69124 (12)	0.15926 (9)	−0.05988 (7)	0.0433 (3)
C8B	0.76583 (13)	0.10645 (9)	−0.10053 (7)	0.0454 (3)
C9B	0.89980 (13)	0.12045 (11)	−0.08339 (7)	0.0501 (3)
C10B	0.94724 (15)	0.20622 (12)	−0.06274 (9)	0.0619 (4)
H10B	0.8940	0.2534	−0.0596	0.074*
C11B	1.07304 (18)	0.22213 (16)	−0.04683 (10)	0.0809 (6)
H11B	1.1036	0.2803	−0.0347	0.097*
C12B	1.15268 (18)	0.1525 (2)	−0.04882 (11)	0.0870 (7)
H12B	1.2373	0.1634	−0.0377	0.104*
C13B	1.10779 (18)	0.06696 (18)	−0.06724 (11)	0.0850 (6)
H13B	1.1624	0.0195	−0.0673	0.102*
C14B	0.98214 (16)	0.05046 (13)	−0.08577 (10)	0.0687 (5)
H14B	0.9524	−0.0074	−0.0999	0.082*
C15B	0.57584 (13)	0.03141 (9)	−0.15930 (8)	0.0475 (3)
C16B	0.49383 (15)	0.05400 (11)	−0.22297 (8)	0.0573 (4)
H16B	0.5216	0.0802	−0.2589	0.069*
C17B	0.37011 (16)	0.03692 (13)	−0.23214 (10)	0.0690 (5)
H17B	0.3134	0.0524	−0.2745	0.083*
C18B	0.32980 (17)	−0.00271 (13)	−0.17947 (11)	0.0719 (5)
H18B	0.2459	−0.0139	−0.1863	0.086*
C19B	0.41230 (17)	−0.02596 (12)	−0.11674 (10)	0.0672 (5)
H19B	0.3843	−0.0531	−0.0813	0.081*
C20B	0.53713 (15)	−0.00918 (10)	−0.10610 (8)	0.0571 (4)
H20B	0.5937	−0.0250	−0.0638	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0599 (6)	0.0671 (7)	0.0360 (5)	−0.0134 (5)	0.0101 (4)	0.0008 (4)
O2A	0.0584 (7)	0.0925 (9)	0.0677 (7)	0.0096 (6)	0.0304 (6)	0.0412 (6)
N1A	0.0423 (6)	0.0489 (6)	0.0425 (6)	0.0027 (5)	0.0167 (5)	0.0102 (5)
C1A	0.0589 (9)	0.0437 (7)	0.0484 (8)	0.0010 (6)	0.0217 (7)	−0.0024 (6)
C2A	0.0813 (12)	0.0466 (8)	0.0535 (9)	−0.0039 (8)	0.0161 (8)	−0.0134 (7)
C3A	0.0670 (11)	0.0479 (8)	0.0679 (10)	−0.0165 (7)	0.0065 (8)	−0.0042 (8)
C4A	0.0555 (9)	0.0600 (9)	0.0672 (10)	−0.0165 (7)	0.0211 (8)	0.0016 (8)
C5A	0.0547 (8)	0.0514 (8)	0.0434 (7)	−0.0096 (6)	0.0196 (6)	−0.0012 (6)
C6A	0.0440 (7)	0.0357 (6)	0.0371 (6)	−0.0005 (5)	0.0116 (5)	0.0045 (5)
C7A	0.0393 (7)	0.0384 (7)	0.0387 (6)	0.0019 (5)	0.0123 (5)	0.0048 (5)
C8A	0.0392 (7)	0.0388 (6)	0.0383 (6)	−0.0005 (5)	0.0117 (5)	0.0023 (5)
C9A	0.0393 (7)	0.0465 (7)	0.0372 (6)	−0.0001 (5)	0.0124 (5)	−0.0024 (5)
C10A	0.0511 (8)	0.0542 (9)	0.0515 (8)	0.0067 (7)	0.0125 (6)	0.0036 (7)
C11A	0.0565 (10)	0.0858 (13)	0.0619 (10)	0.0269 (9)	0.0103 (8)	0.0020 (9)
C12A	0.0369 (8)	0.1181 (17)	0.0660 (11)	0.0058 (10)	0.0127 (7)	−0.0131 (11)
C13A	0.0469 (9)	0.0922 (13)	0.0720 (11)	−0.0184 (9)	0.0242 (8)	−0.0127 (10)
C14A	0.0477 (8)	0.0571 (9)	0.0569 (9)	−0.0073 (7)	0.0212 (7)	−0.0028 (7)
C15A	0.0389 (7)	0.0428 (7)	0.0396 (7)	0.0029 (5)	0.0110 (5)	0.0100 (5)
C16A	0.0548 (9)	0.0549 (8)	0.0422 (7)	0.0010 (7)	0.0119 (6)	0.0024 (6)
C17A	0.0491 (9)	0.0801 (11)	0.0494 (8)	−0.0078 (8)	0.0019 (7)	0.0056 (8)
C18A	0.0391 (8)	0.0879 (12)	0.0640 (10)	0.0044 (8)	0.0125 (7)	0.0172 (9)
C19A	0.0521 (9)	0.0673 (10)	0.0564 (9)	0.0099 (7)	0.0233 (7)	0.0077 (7)
C20A	0.0459 (8)	0.0509 (8)	0.0414 (7)	0.0020 (6)	0.0105 (6)	0.0026 (6)
O1B	0.0674 (7)	0.0691 (7)	0.0403 (5)	−0.0006 (5)	0.0151 (5)	0.0037 (5)
O2B	0.0700 (8)	0.1013 (10)	0.0838 (9)	0.0071 (7)	0.0328 (7)	−0.0386 (8)
N1B	0.0512 (7)	0.0559 (7)	0.0515 (7)	0.0036 (6)	0.0193 (6)	−0.0078 (6)
C1B	0.0631 (9)	0.0493 (8)	0.0485 (8)	0.0005 (7)	0.0215 (7)	−0.0007 (6)
C2B	0.0890 (13)	0.0483 (9)	0.0545 (9)	0.0046 (8)	0.0130 (9)	0.0031 (7)
C3B	0.0738 (12)	0.0530 (10)	0.0747 (12)	0.0148 (8)	0.0006 (9)	−0.0112 (9)
C4B	0.0574 (10)	0.0694 (11)	0.0838 (13)	0.0104 (8)	0.0207 (9)	−0.0213 (10)
C5B	0.0566 (9)	0.0615 (9)	0.0513 (8)	−0.0019 (7)	0.0215 (7)	−0.0124 (7)
C6B	0.0453 (7)	0.0418 (7)	0.0403 (7)	−0.0045 (6)	0.0136 (5)	−0.0083 (5)
C7B	0.0446 (7)	0.0460 (7)	0.0411 (7)	−0.0079 (6)	0.0144 (6)	−0.0024 (6)
C8B	0.0467 (8)	0.0468 (8)	0.0444 (7)	0.0015 (6)	0.0151 (6)	0.0029 (6)
C9B	0.0457 (8)	0.0618 (9)	0.0448 (7)	0.0015 (7)	0.0158 (6)	0.0076 (6)
C10B	0.0545 (9)	0.0714 (11)	0.0585 (9)	−0.0060 (8)	0.0132 (7)	−0.0020 (8)
C11B	0.0608 (12)	0.1037 (16)	0.0744 (12)	−0.0245 (11)	0.0122 (9)	−0.0022 (11)
C12B	0.0458 (10)	0.142 (2)	0.0722 (12)	−0.0080 (12)	0.0143 (9)	0.0162 (13)
C13B	0.0539 (11)	0.1155 (18)	0.0886 (14)	0.0211 (11)	0.0244 (10)	0.0206 (13)
C14B	0.0551 (10)	0.0741 (11)	0.0800 (12)	0.0108 (8)	0.0237 (8)	0.0123 (9)
C15B	0.0511 (8)	0.0419 (7)	0.0505 (8)	−0.0018 (6)	0.0156 (6)	−0.0095 (6)
C16B	0.0626 (10)	0.0600 (9)	0.0495 (8)	−0.0010 (7)	0.0156 (7)	−0.0051 (7)
C17B	0.0586 (10)	0.0788 (12)	0.0632 (10)	0.0012 (9)	0.0053 (8)	−0.0069 (9)
C18B	0.0533 (10)	0.0784 (12)	0.0840 (13)	−0.0100 (9)	0.0184 (9)	−0.0175 (10)
C19B	0.0747 (12)	0.0613 (10)	0.0729 (11)	−0.0157 (9)	0.0325 (9)	−0.0030 (8)
C20B	0.0632 (10)	0.0523 (9)	0.0554 (9)	−0.0047 (7)	0.0154 (7)	0.0002 (7)

Geometric parameters (Å, º)

O1A—C7A	1.2109 (15)	O1B—C7B	1.2135 (16)
O2A—N1A	1.2848 (14)	O2B—N1B	1.2893 (15)
N1A—C8A	1.3160 (16)	N1B—C8B	1.3151 (18)
N1A—C15A	1.4534 (16)	N1B—C15B	1.4553 (18)
C1A—C2A	1.383 (2)	C1B—C2B	1.384 (2)
C1A—C6A	1.3881 (18)	C1B—C6B	1.387 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.374 (2)	C2B—C3B	1.366 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.378 (2)	C3B—C4B	1.377 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.377 (2)	C4B—C5B	1.382 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.3916 (18)	C5B—C6B	1.3894 (19)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4860 (18)	C6B—C7B	1.4790 (19)
C7A—C8A	1.5114 (17)	C7B—C8B	1.5206 (19)
C8A—C9A	1.4665 (17)	C8B—C9B	1.4655 (19)
C9A—C10A	1.3923 (19)	C9B—C10B	1.388 (2)
C9A—C14A	1.3945 (19)	C9B—C14B	1.394 (2)
C10A—C11A	1.386 (2)	C10B—C11B	1.383 (2)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.368 (3)	C11B—C12B	1.368 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.374 (3)	C12B—C13B	1.369 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.375 (2)	C13B—C14B	1.381 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C20A	1.3780 (19)	C15B—C20B	1.375 (2)
C15A—C16A	1.3786 (19)	C15B—C16B	1.380 (2)
C16A—C17A	1.377 (2)	C16B—C17B	1.376 (2)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.370 (2)	C17B—C18B	1.370 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.378 (2)	C18B—C19B	1.371 (3)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.381 (2)	C19B—C20B	1.383 (2)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—H20A	0.9300	C20B—H20B	0.9300
O2A—N1A—C8A	124.65 (11)	O2B—N1B—C8B	125.10 (13)
O2A—N1A—C15A	114.65 (10)	O2B—N1B—C15B	114.57 (12)
C8A—N1A—C15A	120.69 (10)	C8B—N1B—C15B	120.30 (12)
C2A—C1A—C6A	119.62 (14)	C2B—C1B—C6B	120.13 (15)
C2A—C1A—H1AA	120.2	C2B—C1B—H1BA	119.9
C6A—C1A—H1AA	120.2	C6B—C1B—H1BA	119.9
C3A—C2A—C1A	120.51 (14)	C3B—C2B—C1B	120.24 (16)
C3A—C2A—H2AA	119.7	C3B—C2B—H2BA	119.9
C1A—C2A—H2AA	119.7	C1B—C2B—H2BA	119.9
C2A—C3A—C4A	120.17 (14)	C2B—C3B—C4B	120.17 (16)
C2A—C3A—H3AA	119.9	C2B—C3B—H3BA	119.9
C4A—C3A—H3AA	119.9	C4B—C3B—H3BA	119.9
C5A—C4A—C3A	119.96 (15)	C3B—C4B—C5B	120.36 (16)
C5A—C4A—H4AA	120.0	C3B—C4B—H4BA	119.8
C3A—C4A—H4AA	120.0	C5B—C4B—H4BA	119.8
C4A—C5A—C6A	120.27 (14)	C4B—C5B—C6B	119.78 (16)
C4A—C5A—H5AA	119.9	C4B—C5B—H5BA	120.1
C6A—C5A—H5AA	119.9	C6B—C5B—H5BA	120.1
C1A—C6A—C5A	119.46 (12)	C1B—C6B—C5B	119.30 (14)
C1A—C6A—C7A	121.43 (12)	C1B—C6B—C7B	120.77 (13)
C5A—C6A—C7A	119.09 (12)	C5B—C6B—C7B	119.89 (13)
O1A—C7A—C6A	122.06 (11)	O1B—C7B—C6B	122.88 (13)
O1A—C7A—C8A	119.24 (12)	O1B—C7B—C8B	118.45 (13)
C6A—C7A—C8A	118.62 (11)	C6B—C7B—C8B	118.62 (11)
N1A—C8A—C9A	122.07 (11)	N1B—C8B—C9B	122.76 (13)
N1A—C8A—C7A	118.24 (11)	N1B—C8B—C7B	118.17 (12)
C9A—C8A—C7A	119.68 (11)	C9B—C8B—C7B	119.06 (12)
C10A—C9A—C14A	118.50 (13)	C10B—C9B—C14B	118.45 (15)
C10A—C9A—C8A	119.18 (12)	C10B—C9B—C8B	118.98 (14)
C14A—C9A—C8A	122.31 (12)	C14B—C9B—C8B	122.56 (15)
C11A—C10A—C9A	120.44 (15)	C11B—C10B—C9B	120.56 (18)
C11A—C10A—H10A	119.8	C11B—C10B—H10B	119.7
C9A—C10A—H10A	119.8	C9B—C10B—H10B	119.7
C12A—C11A—C10A	120.11 (17)	C12B—C11B—C10B	120.2 (2)
C12A—C11A—H11A	119.9	C12B—C11B—H11B	119.9
C10A—C11A—H11A	119.9	C10B—C11B—H11B	119.9
C11A—C12A—C13A	120.01 (15)	C11B—C12B—C13B	119.99 (18)
C11A—C12A—H12A	120.0	C11B—C12B—H12B	120.0
C13A—C12A—H12A	120.0	C13B—C12B—H12B	120.0
C12A—C13A—C14A	120.68 (16)	C12B—C13B—C14B	120.6 (2)
C12A—C13A—H13A	119.7	C12B—C13B—H13B	119.7
C14A—C13A—H13A	119.7	C14B—C13B—H13B	119.7
C13A—C14A—C9A	120.21 (16)	C13B—C14B—C9B	120.11 (19)
C13A—C14A—H14A	119.9	C13B—C14B—H14B	119.9
C9A—C14A—H14A	119.9	C9B—C14B—H14B	119.9
C20A—C15A—C16A	122.03 (13)	C20B—C15B—C16B	121.68 (14)
C20A—C15A—N1A	119.51 (12)	C20B—C15B—N1B	119.49 (13)
C16A—C15A—N1A	118.44 (12)	C16B—C15B—N1B	118.82 (13)
C17A—C16A—C15A	118.41 (14)	C17B—C16B—C15B	118.51 (16)
C17A—C16A—H16A	120.8	C17B—C16B—H16B	120.7
C15A—C16A—H16A	120.8	C15B—C16B—H16B	120.7
C18A—C17A—C16A	120.47 (15)	C18B—C17B—C16B	120.58 (16)
C18A—C17A—H17A	119.8	C18B—C17B—H17B	119.7
C16A—C17A—H17A	119.8	C16B—C17B—H17B	119.7
C17A—C18A—C19A	120.56 (15)	C17B—C18B—C19B	120.41 (17)
C17A—C18A—H18A	119.7	C17B—C18B—H18B	119.8
C19A—C18A—H18A	119.7	C19B—C18B—H18B	119.8
C18A—C19A—C20A	120.00 (15)	C18B—C19B—C20B	120.12 (16)
C18A—C19A—H19A	120.0	C18B—C19B—H19B	119.9
C20A—C19A—H19A	120.0	C20B—C19B—H19B	119.9
C15A—C20A—C19A	118.51 (13)	C15B—C20B—C19B	118.68 (15)
C15A—C20A—H20A	120.7	C15B—C20B—H20B	120.7
C19A—C20A—H20A	120.7	C19B—C20B—H20B	120.7
C6A—C1A—C2A—C3A	−0.8 (2)	C6B—C1B—C2B—C3B	−0.9 (2)
C1A—C2A—C3A—C4A	−0.2 (3)	C1B—C2B—C3B—C4B	0.3 (3)
C2A—C3A—C4A—C5A	1.0 (3)	C2B—C3B—C4B—C5B	0.8 (3)
C3A—C4A—C5A—C6A	−0.7 (2)	C3B—C4B—C5B—C6B	−1.3 (2)
C2A—C1A—C6A—C5A	1.1 (2)	C2B—C1B—C6B—C5B	0.5 (2)
C2A—C1A—C6A—C7A	−177.46 (13)	C2B—C1B—C6B—C7B	−177.48 (13)
C4A—C5A—C6A—C1A	−0.4 (2)	C4B—C5B—C6B—C1B	0.6 (2)
C4A—C5A—C6A—C7A	178.23 (13)	C4B—C5B—C6B—C7B	178.58 (14)
C1A—C6A—C7A—O1A	150.36 (14)	C1B—C6B—C7B—O1B	154.62 (14)
C5A—C6A—C7A—O1A	−28.24 (19)	C5B—C6B—C7B—O1B	−23.3 (2)
C1A—C6A—C7A—C8A	−26.38 (18)	C1B—C6B—C7B—C8B	−22.70 (19)
C5A—C6A—C7A—C8A	155.02 (12)	C5B—C6B—C7B—C8B	159.33 (13)
O2A—N1A—C8A—C9A	−3.4 (2)	O2B—N1B—C8B—C9B	−3.8 (2)
C15A—N1A—C8A—C9A	174.95 (12)	C15B—N1B—C8B—C9B	173.99 (13)
O2A—N1A—C8A—C7A	175.77 (13)	O2B—N1B—C8B—C7B	177.04 (14)
C15A—N1A—C8A—C7A	−5.91 (18)	C15B—N1B—C8B—C7B	−5.19 (19)
O1A—C7A—C8A—N1A	123.45 (14)	O1B—C7B—C8B—N1B	117.74 (15)
C6A—C7A—C8A—N1A	−59.72 (16)	C6B—C7B—C8B—N1B	−64.82 (17)
O1A—C7A—C8A—C9A	−57.39 (17)	O1B—C7B—C8B—C9B	−61.47 (18)
C6A—C7A—C8A—C9A	119.44 (13)	C6B—C7B—C8B—C9B	115.97 (14)
N1A—C8A—C9A—C10A	146.12 (13)	N1B—C8B—C9B—C10B	146.54 (15)
C7A—C8A—C9A—C10A	−33.01 (17)	C7B—C8B—C9B—C10B	−34.29 (19)
N1A—C8A—C9A—C14A	−34.76 (19)	N1B—C8B—C9B—C14B	−34.6 (2)
C7A—C8A—C9A—C14A	146.12 (13)	C7B—C8B—C9B—C14B	144.53 (15)
C14A—C9A—C10A—C11A	1.6 (2)	C14B—C9B—C10B—C11B	1.8 (2)
C8A—C9A—C10A—C11A	−179.28 (13)	C8B—C9B—C10B—C11B	−179.38 (15)
C9A—C10A—C11A—C12A	−2.0 (2)	C9B—C10B—C11B—C12B	−2.4 (3)
C10A—C11A—C12A—C13A	0.5 (3)	C10B—C11B—C12B—C13B	0.6 (3)
C11A—C12A—C13A—C14A	1.4 (3)	C11B—C12B—C13B—C14B	1.8 (3)
C12A—C13A—C14A—C9A	−1.9 (2)	C12B—C13B—C14B—C9B	−2.3 (3)
C10A—C9A—C14A—C13A	0.4 (2)	C10B—C9B—C14B—C13B	0.6 (2)
C8A—C9A—C14A—C13A	−178.76 (14)	C8B—C9B—C14B—C13B	−178.25 (16)
O2A—N1A—C15A—C20A	115.55 (14)	O2B—N1B—C15B—C20B	113.53 (16)
C8A—N1A—C15A—C20A	−62.92 (17)	C8B—N1B—C15B—C20B	−64.47 (19)
O2A—N1A—C15A—C16A	−62.80 (17)	O2B—N1B—C15B—C16B	−64.88 (18)
C8A—N1A—C15A—C16A	118.73 (14)	C8B—N1B—C15B—C16B	117.12 (15)
C20A—C15A—C16A—C17A	1.7 (2)	C20B—C15B—C16B—C17B	1.5 (2)
N1A—C15A—C16A—C17A	179.98 (13)	N1B—C15B—C16B—C17B	179.83 (14)
C15A—C16A—C17A—C18A	−0.6 (2)	C15B—C16B—C17B—C18B	−0.8 (3)
C16A—C17A—C18A—C19A	−0.8 (3)	C16B—C17B—C18B—C19B	0.0 (3)
C17A—C18A—C19A—C20A	1.3 (3)	C17B—C18B—C19B—C20B	0.3 (3)
C16A—C15A—C20A—C19A	−1.2 (2)	C16B—C15B—C20B—C19B	−1.2 (2)
N1A—C15A—C20A—C19A	−179.51 (12)	N1B—C15B—C20B—C19B	−179.57 (14)
C18A—C19A—C20A—C15A	−0.3 (2)	C18B—C19B—C20B—C15B	0.3 (2)