2,4-Bis(2-methyl-phen-yl)-3-aza-bicyclo[3.3.1]nonan-9-one O-methyl-oxime.

The mol-ecule of the title compound, C(23)H(28)N(2)O, exists in a twin-chair conformation, with equatorial orientation of the ortho-tolyl groups on both sides of the secondary amino group. The title oxime compound and its ketone precursor 2,4-bis-(2-methyl-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one exhibit similar stereochemistries, with the orientation of the o-tolyl rings almost identical in both compounds. In the title compound, the tolyl rings are at an angle of 23.77 (3)° with respect to one another; the angle in the precursor is 29.4 (1)° [Vijayalakshmi, Parthasarathi, Venkatraj & Jeyaraman (2000 ▶), Acta Cryst. C56, 1240-1241]. The cyclo-hexane ring and the oxime ether are disordered over two alternative orientations, with a refined site-occupancy ratio of 0.813 (2):0.186 (4). The crystal structure of the title compound is stabilized by inter-molecular N-H⋯π inter-actions.

Related literature

For the synthesis and biological activities of oxime derivatives of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Parthiban et al. (2009a ▶,b ▶, 2010a ▶,b ▶); Jeyaraman & Avila (1981 ▶). For related structures with similar conformations, see: Vijayalakshmi et al. (2000 ▶); Parthiban et al. (2009c ▶,d ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C23H28N2O

M = 348.47

Monoclinic,

a = 6.9700 (9) Å

b = 15.3476 (16) Å

c = 18.354 (2) Å

β = 94.622 (4)°

V = 1957.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.32 × 0.27 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.989

12742 measured reflections

4416 independent reflections

2070 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.169

S = 1.01

4416 reflections

288 parameters

38 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043436/zl2305sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043436/zl2305Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H28N2O	F(000) = 752
Mr = 348.47	Dx = 1.183 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2129 reflections
a = 6.9700 (9) Å	θ = 2.2–20.4°
b = 15.3476 (16) Å	µ = 0.07 mm−1
c = 18.354 (2) Å	T = 298 K
β = 94.622 (4)°	Block, colourless
V = 1957.0 (4) Å3	0.32 × 0.27 × 0.15 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4416 independent reflections
Radiation source: fine-focus sealed tube	2070 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.977, Tmax = 0.989	k = −20→13
12742 measured reflections	l = −24→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.1996P] where P = (Fo2 + 2Fc2)/3
4416 reflections	(Δ/σ)max < 0.001
288 parameters	Δρmax = 0.14 e Å−3
38 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.6085 (3)	0.86925 (11)	0.08349 (9)	0.0470 (5)
C1	0.5497 (3)	0.81766 (13)	0.14551 (11)	0.0461 (6)
H1	0.4087	0.8169	0.1428	0.055*
C7	0.5361 (3)	0.83350 (13)	0.01217 (12)	0.0497 (6)
H7	0.3953	0.8317	0.0100	0.060*
C9	0.6212 (3)	0.85822 (13)	0.21810 (12)	0.0462 (6)
C10	0.7833 (3)	0.91132 (15)	0.22295 (13)	0.0563 (6)
H10	0.8457	0.9223	0.1810	0.068*
C11	0.8540 (4)	0.94796 (17)	0.28793 (14)	0.0663 (7)
H11	0.9614	0.9840	0.2895	0.080*
C12	0.7663 (4)	0.93131 (18)	0.34982 (15)	0.0704 (8)
H12	0.8140	0.9552	0.3942	0.084*
C13	0.6056 (4)	0.87857 (17)	0.34608 (14)	0.0670 (8)
H13	0.5467	0.8670	0.3887	0.080*
C14	0.5287 (3)	0.84220 (15)	0.28101 (13)	0.0533 (6)
C15	0.5949 (3)	0.88982 (14)	−0.05005 (12)	0.0485 (6)
C16	0.4936 (3)	0.88717 (14)	−0.11942 (13)	0.0554 (6)
C17	0.5643 (4)	0.93407 (17)	−0.17588 (13)	0.0654 (7)
H17	0.4987	0.9317	−0.2220	0.078*
C18	0.7258 (4)	0.98333 (18)	−0.16638 (15)	0.0737 (8)
H18	0.7717	1.0131	−0.2056	0.088*
C19	0.8199 (4)	0.9886 (2)	−0.09852 (15)	0.0850 (9)
H19	0.9277	1.0241	−0.0907	0.102*
C20	0.7563 (4)	0.94157 (17)	−0.04161 (14)	0.0716 (8)
H20	0.8242	0.9448	0.0040	0.086*
C21	0.3492 (4)	0.78778 (18)	0.28148 (15)	0.0799 (9)
H21A	0.2570	0.8069	0.2431	0.120*
H21B	0.2956	0.7940	0.3278	0.120*
H21C	0.3804	0.7277	0.2738	0.120*
C23	0.3094 (4)	0.8366 (2)	−0.13412 (16)	0.0958 (11)
H23A	0.3383	0.7757	−0.1376	0.144*
H23B	0.2439	0.8561	−0.1792	0.144*
H23C	0.2285	0.8459	−0.0949	0.144*
C2	0.6198 (9)	0.7228 (3)	0.1364 (2)	0.0452 (10)	0.814 (5)
H2	0.5669	0.6871	0.1743	0.054*	0.814 (5)
C3	0.8388 (9)	0.7096 (8)	0.1418 (3)	0.0547 (14)	0.814 (5)
H3A	0.8937	0.7353	0.1871	0.066*	0.814 (5)
H3B	0.8661	0.6476	0.1439	0.066*	0.814 (5)
C4	0.9363 (12)	0.7491 (12)	0.0785 (4)	0.0608 (14)	0.814 (5)
H4A	1.0673	0.7275	0.0795	0.073*	0.814 (5)
H4B	0.9421	0.8119	0.0844	0.073*	0.814 (5)
C5	0.8307 (10)	0.7274 (7)	0.0047 (3)	0.0628 (12)	0.814 (5)
H5A	0.8582	0.6675	−0.0075	0.075*	0.814 (5)
H5B	0.8804	0.7643	−0.0323	0.075*	0.814 (5)
C6	0.6115 (9)	0.7394 (2)	0.0025 (2)	0.0491 (10)	0.814 (5)
H6	0.5532	0.7158	−0.0438	0.059*	0.814 (5)
C8	0.5378 (8)	0.6901 (3)	0.0635 (2)	0.0475 (11)	0.814 (5)
C2B	0.621 (4)	0.7216 (11)	0.1560 (11)	0.0452 (10)	0.186 (5)
H2B	0.5691	0.6932	0.1980	0.054*	0.186 (5)
C3B	0.843 (4)	0.715 (4)	0.1583 (18)	0.0547 (14)	0.186 (5)
H3C	0.8985	0.7459	0.2011	0.066*	0.186 (5)
H3D	0.8799	0.6543	0.1636	0.066*	0.186 (5)
C4B	0.928 (6)	0.751 (6)	0.091 (2)	0.0608 (14)	0.186 (5)
H4C	1.0571	0.7279	0.0894	0.073*	0.186 (5)
H4D	0.9406	0.8141	0.0970	0.073*	0.186 (5)
C5B	0.814 (5)	0.733 (4)	0.0191 (17)	0.0628 (12)	0.186 (5)
H5C	0.8508	0.6755	0.0023	0.075*	0.186 (5)
H5D	0.8504	0.7749	−0.0167	0.075*	0.186 (5)
C6B	0.594 (5)	0.7349 (11)	0.0214 (12)	0.0491 (10)	0.186 (5)
H6B	0.5385	0.7044	−0.0223	0.059*	0.186 (5)
C8B	0.546 (4)	0.6829 (17)	0.0853 (12)	0.0475 (11)	0.186 (5)
N2	0.4164 (5)	0.6292 (2)	0.0473 (2)	0.0555 (9)	0.814 (5)
O1	0.3550 (4)	0.59007 (17)	0.11187 (14)	0.0658 (9)	0.814 (5)
C22	0.2246 (7)	0.5220 (3)	0.0898 (3)	0.0928 (17)	0.814 (5)
H22A	0.1227	0.5449	0.0570	0.139*	0.814 (5)
H22B	0.1715	0.4978	0.1320	0.139*	0.814 (5)
H22C	0.2916	0.4773	0.0654	0.139*	0.814 (5)
N2B	0.427 (2)	0.6218 (8)	0.0948 (8)	0.048 (4)	0.186 (5)
O1B	0.3413 (16)	0.5918 (7)	0.0264 (5)	0.060 (3)	0.186 (5)
C22B	0.220 (3)	0.5208 (13)	0.0398 (10)	0.087 (7)	0.186 (5)
H22D	0.2958	0.4735	0.0608	0.130*	0.186 (5)
H22E	0.1535	0.5021	−0.0054	0.130*	0.186 (5)
H22F	0.1277	0.5384	0.0731	0.130*	0.186 (5)
H1N	0.563 (4)	0.927 (2)	0.0881 (15)	0.104*

	U11	U22	U33	U12	U13	U23
N1	0.0589 (12)	0.0416 (10)	0.0405 (11)	−0.0091 (9)	0.0041 (9)	−0.0006 (9)
C1	0.0432 (13)	0.0455 (12)	0.0500 (14)	−0.0055 (10)	0.0066 (10)	0.0049 (11)
C7	0.0505 (14)	0.0450 (13)	0.0526 (15)	−0.0115 (10)	−0.0024 (11)	−0.0044 (11)
C9	0.0466 (14)	0.0456 (13)	0.0471 (14)	0.0057 (10)	0.0077 (11)	0.0050 (10)
C10	0.0569 (15)	0.0651 (15)	0.0479 (15)	−0.0076 (12)	0.0104 (12)	−0.0052 (12)
C11	0.0605 (17)	0.0771 (18)	0.0612 (18)	−0.0052 (14)	0.0041 (14)	−0.0142 (14)
C12	0.082 (2)	0.0784 (19)	0.0500 (17)	0.0130 (16)	0.0007 (15)	−0.0095 (14)
C13	0.080 (2)	0.0710 (17)	0.0530 (17)	0.0211 (15)	0.0244 (14)	0.0091 (14)
C14	0.0569 (15)	0.0541 (14)	0.0503 (15)	0.0102 (12)	0.0142 (12)	0.0102 (12)
C15	0.0528 (14)	0.0475 (13)	0.0445 (14)	−0.0041 (11)	0.0006 (11)	−0.0035 (11)
C16	0.0612 (16)	0.0500 (14)	0.0529 (15)	0.0001 (12)	−0.0074 (12)	−0.0072 (12)
C17	0.083 (2)	0.0656 (17)	0.0454 (15)	0.0104 (15)	−0.0069 (14)	−0.0010 (13)
C18	0.077 (2)	0.0842 (19)	0.0602 (18)	−0.0015 (16)	0.0084 (16)	0.0196 (15)
C19	0.071 (2)	0.105 (2)	0.077 (2)	−0.0352 (17)	−0.0080 (16)	0.0304 (18)
C20	0.0695 (19)	0.0869 (19)	0.0552 (16)	−0.0322 (15)	−0.0137 (14)	0.0161 (14)
C21	0.074 (2)	0.086 (2)	0.084 (2)	−0.0038 (16)	0.0332 (16)	0.0165 (16)
C23	0.095 (2)	0.102 (2)	0.083 (2)	−0.0286 (19)	−0.0386 (18)	0.0025 (17)
C2	0.0569 (16)	0.0393 (12)	0.040 (3)	−0.0069 (11)	0.011 (2)	0.0081 (16)
C3	0.0604 (17)	0.051 (2)	0.052 (4)	0.0061 (13)	0.002 (2)	−0.005 (3)
C4	0.0500 (17)	0.0626 (19)	0.071 (4)	0.0018 (15)	0.012 (2)	−0.005 (4)
C5	0.075 (2)	0.057 (2)	0.060 (3)	0.0040 (18)	0.025 (2)	−0.008 (3)
C6	0.067 (2)	0.0449 (14)	0.035 (3)	−0.0150 (13)	0.007 (2)	−0.0068 (14)
C8	0.0547 (16)	0.0316 (15)	0.055 (3)	−0.0055 (13)	0.001 (2)	0.004 (2)
C2B	0.0569 (16)	0.0393 (12)	0.040 (3)	−0.0069 (11)	0.011 (2)	0.0081 (16)
C3B	0.0604 (17)	0.051 (2)	0.052 (4)	0.0061 (13)	0.002 (2)	−0.005 (3)
C4B	0.0500 (17)	0.0626 (19)	0.071 (4)	0.0018 (15)	0.012 (2)	−0.005 (4)
C5B	0.075 (2)	0.057 (2)	0.060 (3)	0.0040 (18)	0.025 (2)	−0.008 (3)
C6B	0.067 (2)	0.0449 (14)	0.035 (3)	−0.0150 (13)	0.007 (2)	−0.0068 (14)
C8B	0.0547 (16)	0.0316 (15)	0.055 (3)	−0.0055 (13)	0.001 (2)	0.004 (2)
N2	0.069 (2)	0.0400 (19)	0.057 (2)	−0.0111 (15)	0.003 (2)	0.010 (2)
O1	0.074 (2)	0.0531 (17)	0.0686 (18)	−0.0232 (13)	−0.0030 (13)	0.0137 (12)
C22	0.082 (3)	0.066 (2)	0.126 (4)	−0.041 (2)	−0.020 (3)	0.017 (3)
N2B	0.073 (10)	0.029 (8)	0.042 (8)	−0.011 (6)	0.004 (8)	0.008 (7)
O1B	0.085 (8)	0.045 (6)	0.047 (6)	−0.028 (5)	−0.003 (5)	−0.002 (5)
C22B	0.096 (13)	0.070 (10)	0.090 (14)	−0.050 (9)	−0.018 (13)	0.000 (12)

N1—C7	1.470 (3)	C2—C3	1.536 (5)
N1—C1	1.472 (3)	C2—H2	0.9800
N1—H1N	0.94 (3)	C3—C4	1.519 (5)
C1—C9	1.518 (3)	C3—H3A	0.9700
C1—C2	1.549 (4)	C3—H3B	0.9700
C1—C2B	1.563 (15)	C4—C5	1.525 (5)
C1—H1	0.9800	C4—H4A	0.9700
C7—C15	1.515 (3)	C4—H4B	0.9700
C7—C6	1.552 (4)	C5—C6	1.536 (5)
C7—C6B	1.570 (15)	C5—H5A	0.9700
C7—H7	0.9800	C5—H5B	0.9700
C9—C14	1.389 (3)	C6—C8	1.477 (4)
C9—C10	1.390 (3)	C6—H6	0.9800
C10—C11	1.374 (3)	C8—N2	1.280 (5)
C10—H10	0.9300	C2B—C8B	1.483 (16)
C11—C12	1.357 (4)	C2B—C3B	1.548 (17)
C11—H11	0.9300	C2B—H2B	0.9800
C12—C13	1.380 (4)	C3B—C4B	1.513 (17)
C12—H12	0.9300	C3B—H3C	0.9700
C13—C14	1.386 (3)	C3B—H3D	0.9700
C13—H13	0.9300	C4B—C5B	1.520 (17)
C14—C21	1.505 (3)	C4B—H4C	0.9700
C15—C20	1.375 (3)	C4B—H4D	0.9700
C15—C16	1.406 (3)	C5B—C6B	1.543 (17)
C16—C17	1.385 (3)	C5B—H5C	0.9700
C16—C23	1.506 (3)	C5B—H5D	0.9700
C17—C18	1.355 (4)	C6B—C8B	1.478 (16)
C17—H17	0.9300	C6B—H6B	0.9800
C18—C19	1.362 (3)	C8B—N2B	1.275 (16)
C18—H18	0.9300	N2—O1	1.424 (4)
C19—C20	1.372 (3)	O1—C22	1.422 (4)
C19—H19	0.9300	C22—H22A	0.9600
C20—H20	0.9300	C22—H22B	0.9600
C21—H21A	0.9600	C22—H22C	0.9600
C21—H21B	0.9600	N2B—O1B	1.422 (13)
C21—H21C	0.9600	O1B—C22B	1.414 (14)
C23—H23A	0.9600	C22B—H22D	0.9600
C23—H23B	0.9600	C22B—H22E	0.9600
C23—H23C	0.9600	C22B—H22F	0.9600
C2—C8	1.499 (4)
C7—N1—C1	113.01 (16)	C3—C2—H2	108.0
C7—N1—H1N	109.5 (17)	C1—C2—H2	108.0
C1—N1—H1N	108.5 (18)	C4—C3—C2	113.6 (5)
N1—C1—C9	111.47 (17)	C4—C3—H3A	108.8
N1—C1—C2	108.2 (2)	C2—C3—H3A	108.8
C9—C1—C2	113.3 (2)	C4—C3—H3B	108.8
N1—C1—C2B	119.8 (10)	C2—C3—H3B	108.8
C9—C1—C2B	101.5 (8)	H3A—C3—H3B	107.7
N1—C1—H1	107.9	C3—C4—C5	112.3 (5)
C9—C1—H1	107.9	C3—C4—H4A	109.2
C2—C1—H1	107.9	C5—C4—H4A	109.2
C2B—C1—H1	107.7	C3—C4—H4B	109.2
N1—C7—C15	111.35 (17)	C5—C4—H4B	109.2
N1—C7—C6	110.8 (2)	H4A—C4—H4B	107.9
C15—C7—C6	109.3 (2)	C4—C5—C6	113.9 (5)
N1—C7—C6B	101.4 (9)	C4—C5—H5A	108.8
C15—C7—C6B	123.3 (9)	C6—C5—H5A	108.8
N1—C7—H7	108.5	C4—C5—H5B	108.8
C15—C7—H7	108.5	C6—C5—H5B	108.8
C6—C7—H7	108.5	H5A—C5—H5B	107.7
C6B—C7—H7	102.9	C8—C6—C5	108.9 (4)
C14—C9—C10	118.7 (2)	C8—C6—C7	104.3 (3)
C14—C9—C1	121.0 (2)	C5—C6—C7	117.0 (5)
C10—C9—C1	120.3 (2)	C8—C6—H6	108.8
C11—C10—C9	121.9 (2)	C5—C6—H6	108.8
C11—C10—H10	119.1	C7—C6—H6	108.8
C9—C10—H10	119.1	N2—C8—C6	117.6 (4)
C12—C11—C10	119.7 (3)	N2—C8—C2	130.4 (4)
C12—C11—H11	120.1	C6—C8—C2	112.0 (3)
C10—C11—H11	120.1	C8B—C2B—C3B	106.1 (18)
C11—C12—C13	119.2 (3)	C8B—C2B—C1	100.6 (16)
C11—C12—H12	120.4	C3B—C2B—C1	112 (3)
C13—C12—H12	120.4	C8B—C2B—H2B	112.5
C12—C13—C14	122.4 (2)	C3B—C2B—H2B	112.5
C12—C13—H13	118.8	C1—C2B—H2B	112.5
C14—C13—H13	118.8	C4B—C3B—C2B	114 (2)
C13—C14—C9	118.1 (2)	C4B—C3B—H3C	108.7
C13—C14—C21	118.8 (2)	C2B—C3B—H3C	108.7
C9—C14—C21	123.0 (2)	C4B—C3B—H3D	108.7
C20—C15—C16	117.7 (2)	C2B—C3B—H3D	108.7
C20—C15—C7	120.9 (2)	H3C—C3B—H3D	107.6
C16—C15—C7	121.3 (2)	C3B—C4B—C5B	115 (2)
C17—C16—C15	118.7 (2)	C3B—C4B—H4C	108.5
C17—C16—C23	118.9 (2)	C5B—C4B—H4C	108.5
C15—C16—C23	122.4 (2)	C3B—C4B—H4D	108.5
C18—C17—C16	122.4 (2)	C5B—C4B—H4D	108.5
C18—C17—H17	118.8	H4C—C4B—H4D	107.5
C16—C17—H17	118.8	C4B—C5B—C6B	115 (2)
C17—C18—C19	119.0 (3)	C4B—C5B—H5C	108.5
C17—C18—H18	120.5	C6B—C5B—H5C	108.5
C19—C18—H18	120.5	C4B—C5B—H5D	108.5
C18—C19—C20	120.2 (3)	C6B—C5B—H5D	108.5
C18—C19—H19	119.9	H5C—C5B—H5D	107.5
C20—C19—H19	119.9	C8B—C6B—C5B	107.3 (19)
C19—C20—C15	122.0 (2)	C8B—C6B—C7	122.3 (19)
C19—C20—H20	119.0	C5B—C6B—C7	105 (3)
C15—C20—H20	119.0	C8B—C6B—H6B	107.0
C14—C21—H21A	109.5	C5B—C6B—H6B	107.0
C14—C21—H21B	109.5	C7—C6B—H6B	107.0
H21A—C21—H21B	109.5	N2B—C8B—C6B	134 (2)
C14—C21—H21C	109.5	N2B—C8B—C2B	111.2 (19)
H21A—C21—H21C	109.5	C6B—C8B—C2B	113.1 (16)
H21B—C21—H21C	109.5	C8—N2—O1	110.7 (4)
C16—C23—H23A	109.5	C22—O1—N2	107.5 (3)
C16—C23—H23B	109.5	C8B—N2B—O1B	110.5 (14)
H23A—C23—H23B	109.5	C22B—O1B—N2B	108.2 (11)
C16—C23—H23C	109.5	O1B—C22B—H22D	109.5
H23A—C23—H23C	109.5	O1B—C22B—H22E	109.5
H23B—C23—H23C	109.5	H22D—C22B—H22E	109.5
C8—C2—C3	108.6 (4)	O1B—C22B—H22F	109.5
C8—C2—C1	108.1 (3)	H22D—C22B—H22F	109.5
C3—C2—C1	116.0 (6)	H22E—C22B—H22F	109.5
C8—C2—H2	108.0
C7—N1—C1—C9	−178.06 (17)	C17—C18—C19—C20	2.8 (5)
C7—N1—C1—C2	56.7 (3)	C18—C19—C20—C15	−1.6 (5)
C1—N1—C7—C15	178.36 (18)	C16—C15—C20—C19	−0.9 (4)
C1—N1—C7—C6	−59.8 (3)	C7—C15—C20—C19	175.5 (3)
N1—C1—C9—C14	155.62 (19)	N1—C1—C2—C8	−56.6 (4)
C2—C1—C9—C14	−82.1 (3)	C9—C1—C2—C8	179.3 (3)
N1—C1—C9—C10	−25.4 (3)	N1—C1—C2—C3	65.6 (4)
C2—C1—C9—C10	97.0 (3)	C9—C1—C2—C3	−58.5 (4)
C14—C9—C10—C11	0.1 (3)	C8—C2—C3—C4	53.6 (8)
C1—C9—C10—C11	−178.9 (2)	C1—C2—C3—C4	−68.4 (8)
C9—C10—C11—C12	1.1 (4)	C2—C3—C4—C5	−46.2 (12)
C10—C11—C12—C13	−0.9 (4)	C3—C4—C5—C6	45.7 (13)
C11—C12—C13—C14	−0.5 (4)	C4—C5—C6—C8	−53.0 (9)
C12—C13—C14—C9	1.7 (4)	C4—C5—C6—C7	64.9 (9)
C12—C13—C14—C21	−178.0 (2)	N1—C7—C6—C8	59.8 (4)
C10—C9—C14—C13	−1.4 (3)	C15—C7—C6—C8	−177.2 (3)
C1—C9—C14—C13	177.60 (19)	N1—C7—C6—C5	−60.6 (4)
C10—C9—C14—C21	178.3 (2)	C15—C7—C6—C5	62.4 (4)
C1—C9—C14—C21	−2.7 (3)	C5—C6—C8—N2	−119.0 (6)
N1—C7—C15—C20	25.6 (3)	C7—C6—C8—N2	115.4 (6)
C6—C7—C15—C20	−97.1 (3)	C5—C6—C8—C2	62.0 (6)
N1—C7—C15—C16	−158.2 (2)	C7—C6—C8—C2	−63.6 (5)
C6—C7—C15—C16	79.1 (3)	C3—C2—C8—N2	118.8 (8)
C20—C15—C16—C17	2.1 (3)	C1—C2—C8—N2	−114.6 (6)
C7—C15—C16—C17	−174.2 (2)	C3—C2—C8—C6	−62.4 (6)
C20—C15—C16—C23	−176.7 (3)	C1—C2—C8—C6	64.2 (6)
C7—C15—C16—C23	7.0 (4)	C6—C8—N2—O1	−178.2 (4)
C15—C16—C17—C18	−1.0 (4)	C2—C8—N2—O1	0.6 (8)
C23—C16—C17—C18	177.9 (3)	C8—N2—O1—C22	−178.6 (5)
C16—C17—C18—C19	−1.5 (4)