N-{3-(4-Methyl­phen­yl)-6-[(Z)-(4-methylphen­yl)methyl­idene]-2-phen­yl-2-aza­bicyclo­[2.2.2]oct-5-ylidene}aniline

The title compound, C₃₄H₃₂N₂, is formed as a result of the Diels-Alder reaction of N-benzyl­ideneaniline and cyclo­hexen-2-one, catalyzed by zirconium tetra­chloride. The mol­ecule exists as the Z isomer. All three rings in the aza­bicyclo­[2.2.2]octa­ne system adopt boat conformations. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.127
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.75 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.03 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C28    -   C33     ..       5.32 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C21    -C26           1.37 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N-{3-(4-methylphenyl)-6-[(Z)-(4-methylphenyl)methylidene]-2-phenyl- 2-azabicyclo[2.2.2]oct-5-ylidene}aniline

Crystal data

C34H32N2	F(000) = 1000
Mr = 468.62	Dx = 1.174 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6129 reflections
a = 14.1805 (8) Å	θ = 2.2–24.2°
b = 10.1822 (5) Å	µ = 0.07 mm^−1
c = 18.3636 (10) Å	T = 273 K
β = 91.080 (1)°	Block, colourless
V = 2651.0 (2) Å^3	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω scans	h = −16→16
18613 measured reflections	k = −12→12
4659 independent reflections	l = −21→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 0.3061P] where P = (Fo^2 + 2Fc^2)/3
4659 reflections	(Δ/σ)max < 0.001
357 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.71505 (12)	0.38772 (17)	0.40618 (8)	0.0734 (5)
H1	0.7604	0.3263	0.4284	0.071 (4)*
C3	0.66310 (10)	0.48530 (14)	0.28981 (7)	0.0579 (4)
H3	0.6976	0.5588	0.2684	0.056 (4)*
C4	0.59598 (11)	0.54247 (15)	0.34694 (8)	0.0651 (4)
H4	0.5499	0.6014	0.3236	0.071 (4)*
C5	0.54673 (12)	0.42925 (15)	0.38259 (7)	0.0665 (4)
C6	0.61605 (12)	0.33703 (16)	0.41473 (7)	0.0689 (4)
C7	0.72396 (15)	0.52217 (19)	0.44225 (9)	0.0923 (6)
H7A	0.7877	0.5552	0.4374	0.092 (5)*
H7B	0.7105	0.5152	0.4937	0.100 (6)*
C8	0.65378 (15)	0.61628 (19)	0.40515 (10)	0.0895 (6)
H8A	0.6120	0.6528	0.4411	0.105 (6)*
H8B	0.6876	0.6881	0.3828	0.089 (5)*
C9	0.82342 (10)	0.39463 (13)	0.30092 (8)	0.0631 (4)
C10	0.90187 (13)	0.36186 (16)	0.34405 (11)	0.0810 (5)
H10	0.8946	0.3441	0.3933	0.088 (6)*
C11	0.99038 (14)	0.35556 (19)	0.31406 (15)	0.0991 (7)
H11	1.0418	0.3332	0.3437	0.114 (7)*
C12	1.00428 (15)	0.3812 (2)	0.24244 (15)	0.1028 (7)
H12	1.0643	0.3766	0.2231	0.118 (7)*
C13	0.92841 (13)	0.4138 (2)	0.19973 (12)	0.0933 (6)
H13	0.9370	0.4322	0.1507	0.124 (8)*
C14	0.83960 (12)	0.42003 (16)	0.22766 (9)	0.0733 (4)
H14	0.7890	0.4417	0.1970	0.070 (4)*
C15	0.60893 (9)	0.41726 (13)	0.22888 (7)	0.0540 (3)
C16	0.55872 (11)	0.49098 (16)	0.17852 (8)	0.0710 (4)
H16	0.5603	0.5821	0.1817	0.089 (5)*
C17	0.50637 (12)	0.4323 (2)	0.12367 (9)	0.0823 (5)
H17	0.4728	0.4846	0.0907	0.098 (6)*
C18	0.50268 (11)	0.2980 (2)	0.11656 (8)	0.0766 (5)
C19	0.55261 (12)	0.22529 (18)	0.16675 (9)	0.0798 (5)
H19	0.5514	0.1342	0.1634	0.096 (6)*
C20	0.60472 (11)	0.28331 (15)	0.22220 (8)	0.0687 (4)
H20	0.6374	0.2308	0.2555	0.072 (4)*
C21	0.39163 (12)	0.48831 (17)	0.34999 (9)	0.0724 (4)
C22	0.36100 (18)	0.6039 (2)	0.37983 (12)	0.1000 (6)
H22	0.3895	0.6357	0.4223	0.113 (7)*
C23	0.2883 (2)	0.6730 (3)	0.34709 (19)	0.1251 (9)
H23	0.2681	0.7518	0.3671	0.153 (10)*
C24	0.2460 (2)	0.6256 (3)	0.2854 (2)	0.1343 (10)
H24	0.1944	0.6691	0.2648	0.173 (12)*
C25	0.27950 (19)	0.5143 (3)	0.25392 (17)	0.1282 (9)
H25	0.2532	0.4852	0.2100	0.164 (11)*
C26	0.35083 (15)	0.4457 (2)	0.28599 (11)	0.0962 (6)
H26	0.3723	0.3690	0.2644	0.121 (7)*
C27	0.58946 (12)	0.22512 (16)	0.44637 (7)	0.0700 (4)
H27	0.5245	0.2141	0.4491	0.065 (4)*
C28	0.64467 (11)	0.11731 (15)	0.47740 (7)	0.0661 (4)
C29	0.60943 (12)	0.04931 (18)	0.53685 (9)	0.0748 (4)
H29	0.5524	0.0756	0.5564	0.093 (6)*
C30	0.65659 (12)	−0.05543 (18)	0.56735 (9)	0.0792 (5)
H30	0.6315	−0.0973	0.6076	0.084 (5)*
C31	0.74014 (13)	−0.09967 (17)	0.53953 (9)	0.0773 (5)
C32	0.77434 (14)	−0.0349 (2)	0.47935 (10)	0.0858 (5)
H32	0.8302	−0.0636	0.4589	0.090 (6)*
C33	0.72795 (13)	0.07119 (18)	0.44891 (9)	0.0777 (5)
H33	0.7531	0.1125	0.4085	0.089 (5)*
C34	0.79197 (18)	−0.2143 (2)	0.57324 (14)	0.1087 (7)
H34A	0.8396	−0.2442	0.5407	0.148 (10)*
H34B	0.7483	−0.2844	0.5820	0.179 (12)*
H34C	0.8210	−0.1875	0.6185	0.162 (11)*
C35	0.44783 (17)	0.2326 (3)	0.05490 (13)	0.1189 (8)
H35A	0.4858	0.2301	0.0122	0.193 (13)*
H35B	0.3913	0.2815	0.0446	0.173 (12)*
H35C	0.4316	0.1446	0.0688	0.210 (17)*
N2	0.73230 (8)	0.40051 (12)	0.32742 (6)	0.0629 (3)
N3	0.45867 (11)	0.40624 (14)	0.38483 (7)	0.0797 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0849 (11)	0.0818 (11)	0.0528 (8)	−0.0278 (9)	−0.0132 (7)	0.0146 (7)
C3	0.0686 (8)	0.0531 (8)	0.0522 (8)	−0.0080 (6)	0.0026 (6)	0.0070 (6)
C4	0.0809 (10)	0.0593 (8)	0.0553 (8)	−0.0107 (8)	0.0074 (7)	−0.0026 (7)
C5	0.0833 (11)	0.0715 (10)	0.0448 (7)	−0.0189 (8)	0.0029 (7)	−0.0013 (7)
C6	0.0850 (10)	0.0774 (10)	0.0441 (7)	−0.0252 (8)	−0.0051 (7)	0.0064 (7)
C7	0.1166 (15)	0.1046 (14)	0.0552 (9)	−0.0513 (12)	−0.0074 (9)	−0.0016 (9)
C8	0.1159 (15)	0.0820 (12)	0.0711 (11)	−0.0306 (11)	0.0104 (11)	−0.0175 (9)
C9	0.0675 (9)	0.0499 (8)	0.0714 (9)	−0.0096 (7)	−0.0100 (7)	0.0051 (7)
C10	0.0787 (11)	0.0685 (10)	0.0948 (13)	−0.0097 (8)	−0.0202 (9)	0.0200 (9)
C11	0.0738 (12)	0.0763 (12)	0.146 (2)	0.0026 (9)	−0.0267 (13)	0.0174 (12)
C12	0.0712 (13)	0.0964 (14)	0.141 (2)	0.0080 (10)	0.0126 (13)	0.0024 (14)
C13	0.0748 (12)	0.1072 (15)	0.0983 (14)	0.0059 (10)	0.0137 (10)	−0.0013 (11)
C14	0.0686 (10)	0.0804 (11)	0.0708 (10)	0.0022 (8)	−0.0008 (8)	0.0032 (8)
C15	0.0593 (8)	0.0553 (8)	0.0475 (7)	0.0035 (6)	0.0035 (6)	0.0042 (6)
C16	0.0874 (11)	0.0658 (10)	0.0598 (9)	0.0124 (8)	−0.0015 (8)	0.0074 (7)
C17	0.0844 (11)	0.1038 (14)	0.0584 (9)	0.0213 (10)	−0.0123 (8)	0.0080 (9)
C18	0.0645 (9)	0.1054 (14)	0.0598 (9)	0.0044 (9)	−0.0044 (7)	−0.0124 (9)
C19	0.0863 (11)	0.0686 (11)	0.0841 (11)	0.0009 (8)	−0.0117 (9)	−0.0154 (9)
C20	0.0780 (10)	0.0582 (9)	0.0691 (9)	0.0066 (7)	−0.0156 (8)	0.0016 (7)
C21	0.0765 (10)	0.0773 (11)	0.0639 (9)	−0.0156 (8)	0.0099 (8)	0.0072 (8)
C22	0.1258 (17)	0.0968 (15)	0.0784 (12)	−0.0113 (13)	0.0287 (12)	−0.0152 (11)
C23	0.122 (2)	0.0964 (17)	0.158 (2)	0.0202 (16)	0.0497 (19)	0.0005 (17)
C24	0.1055 (19)	0.108 (2)	0.189 (3)	0.0154 (15)	−0.0125 (19)	0.021 (2)
C25	0.138 (2)	0.0979 (17)	0.147 (2)	0.0088 (15)	−0.0525 (18)	0.0029 (16)
C26	0.1128 (15)	0.0790 (12)	0.0960 (14)	0.0035 (11)	−0.0224 (12)	−0.0080 (11)
C27	0.0784 (10)	0.0813 (11)	0.0502 (8)	−0.0228 (8)	−0.0017 (7)	0.0057 (7)
C28	0.0726 (9)	0.0760 (10)	0.0497 (8)	−0.0229 (8)	−0.0022 (7)	0.0016 (7)
C29	0.0715 (10)	0.0875 (11)	0.0656 (9)	−0.0134 (9)	0.0037 (8)	0.0165 (8)
C30	0.0816 (11)	0.0902 (12)	0.0656 (10)	−0.0198 (10)	−0.0028 (8)	0.0183 (9)
C31	0.0827 (11)	0.0774 (11)	0.0714 (10)	−0.0136 (9)	−0.0098 (9)	−0.0033 (8)
C32	0.0819 (12)	0.0943 (13)	0.0813 (12)	−0.0099 (10)	0.0094 (9)	−0.0127 (10)
C33	0.0920 (12)	0.0850 (12)	0.0564 (9)	−0.0214 (10)	0.0090 (8)	−0.0004 (8)
C34	0.1186 (17)	0.0925 (15)	0.1142 (17)	0.0075 (14)	−0.0148 (15)	0.0029 (13)
C35	0.0978 (16)	0.170 (3)	0.0876 (15)	−0.0107 (17)	−0.0220 (12)	−0.0353 (15)
N2	0.0664 (7)	0.0692 (8)	0.0527 (6)	−0.0119 (6)	−0.0084 (5)	0.0115 (6)
N3	0.0843 (10)	0.0897 (10)	0.0652 (8)	−0.0220 (8)	0.0008 (7)	0.0135 (7)

Geometric parameters (Å, º)

C1—N2	1.4770 (19)	C18—C19	1.369 (2)
C1—C6	1.507 (2)	C18—C35	1.516 (2)
C1—C7	1.525 (2)	C19—C20	1.380 (2)
C1—H1	0.9800	C19—H19	0.9300
C3—N2	1.4695 (18)	C20—H20	0.9300
C3—C15	1.5132 (19)	C21—C26	1.371 (2)
C3—C4	1.544 (2)	C21—C22	1.372 (3)
C3—H3	0.9800	C21—N3	1.410 (2)
C4—C5	1.504 (2)	C22—C23	1.377 (3)
C4—C8	1.532 (2)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.359 (4)
C5—N3	1.272 (2)	C23—H23	0.9300
C5—C6	1.475 (2)	C24—C25	1.362 (4)
C6—C27	1.337 (2)	C24—H24	0.9300
C7—C8	1.532 (3)	C25—C26	1.355 (3)
C7—H7A	0.9700	C25—H25	0.9300
C7—H7B	0.9700	C26—H26	0.9300
C8—H8A	0.9700	C27—C28	1.458 (2)
C8—H8B	0.9700	C27—H27	0.9300
C9—N2	1.3907 (19)	C28—C33	1.383 (2)
C9—C14	1.393 (2)	C28—C29	1.393 (2)
C9—C10	1.394 (2)	C29—C30	1.373 (2)
C10—C11	1.382 (3)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.375 (2)
C11—C12	1.359 (3)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.383 (2)
C12—C13	1.361 (3)	C31—C34	1.506 (3)
C12—H12	0.9300	C32—C33	1.377 (3)
C13—C14	1.370 (2)	C32—H32	0.9300
C13—H13	0.9300	C33—H33	0.9300
C14—H14	0.9300	C34—H34A	0.9600
C15—C20	1.371 (2)	C34—H34B	0.9600
C15—C16	1.3787 (19)	C34—H34C	0.9600
C16—C17	1.376 (2)	C35—H35A	0.9600
C16—H16	0.9300	C35—H35B	0.9600
C17—C18	1.375 (3)	C35—H35C	0.9600
C17—H17	0.9300
N2—C1—C6	107.70 (11)	C19—C18—C35	121.1 (2)
N2—C1—C7	109.41 (12)	C17—C18—C35	121.74 (19)
C6—C1—C7	109.39 (16)	C18—C19—C20	121.90 (16)
N2—C1—H1	110.1	C18—C19—H19	119.1
C6—C1—H1	110.1	C20—C19—H19	119.1
C7—C1—H1	110.1	C15—C20—C19	120.93 (14)
N2—C3—C15	113.82 (11)	C15—C20—H20	119.5
N2—C3—C4	108.47 (11)	C19—C20—H20	119.5
C15—C3—C4	111.36 (11)	C26—C21—C22	118.8 (2)
N2—C3—H3	107.7	C26—C21—N3	118.13 (16)
C15—C3—H3	107.7	C22—C21—N3	122.88 (18)
C4—C3—H3	107.7	C21—C22—C23	120.2 (2)
C5—C4—C8	108.61 (13)	C21—C22—H22	119.9
C5—C4—C3	107.70 (12)	C23—C22—H22	119.9
C8—C4—C3	109.31 (13)	C24—C23—C22	119.8 (2)
C5—C4—H4	110.4	C24—C23—H23	120.1
C8—C4—H4	110.4	C22—C23—H23	120.1
C3—C4—H4	110.4	C23—C24—C25	119.8 (3)
N3—C5—C6	121.14 (14)	C23—C24—H24	120.1
N3—C5—C4	128.27 (15)	C25—C24—H24	120.1
C6—C5—C4	110.53 (14)	C26—C25—C24	120.5 (3)
C27—C6—C5	121.70 (15)	C26—C25—H25	119.7
C27—C6—C1	127.47 (16)	C24—C25—H25	119.7
C5—C6—C1	110.83 (13)	C25—C26—C21	120.6 (2)
C1—C7—C8	108.69 (14)	C25—C26—H26	119.7
C1—C7—H7A	110.0	C21—C26—H26	119.7
C8—C7—H7A	110.0	C6—C27—C28	131.14 (16)
C1—C7—H7B	110.0	C6—C27—H27	114.4
C8—C7—H7B	110.0	C28—C27—H27	114.4
H7A—C7—H7B	108.3	C33—C28—C29	116.69 (16)
C4—C8—C7	109.76 (15)	C33—C28—C27	124.33 (14)
C4—C8—H8A	109.7	C29—C28—C27	118.84 (15)
C7—C8—H8A	109.7	C30—C29—C28	121.78 (17)
C4—C8—H8B	109.7	C30—C29—H29	119.1
C7—C8—H8B	109.7	C28—C29—H29	119.1
H8A—C8—H8B	108.2	C29—C30—C31	121.30 (16)
N2—C9—C14	120.06 (13)	C29—C30—H30	119.4
N2—C9—C10	123.26 (15)	C31—C30—H30	119.4
C14—C9—C10	116.68 (16)	C30—C31—C32	117.27 (17)
C11—C10—C9	120.40 (19)	C30—C31—C34	121.22 (18)
C11—C10—H10	119.8	C32—C31—C34	121.50 (19)
C9—C10—H10	119.8	C33—C32—C31	121.77 (18)
C12—C11—C10	121.75 (18)	C33—C32—H32	119.1
C12—C11—H11	119.1	C31—C32—H32	119.1
C10—C11—H11	119.1	C32—C33—C28	121.16 (15)
C11—C12—C13	118.51 (19)	C32—C33—H33	119.4
C11—C12—H12	120.7	C28—C33—H33	119.4
C13—C12—H12	120.7	C31—C34—H34A	109.5
C12—C13—C14	121.2 (2)	C31—C34—H34B	109.5
C12—C13—H13	119.4	H34A—C34—H34B	109.5
C14—C13—H13	119.4	C31—C34—H34C	109.5
C13—C14—C9	121.47 (17)	H34A—C34—H34C	109.5
C13—C14—H14	119.3	H34B—C34—H34C	109.5
C9—C14—H14	119.3	C18—C35—H35A	109.5
C20—C15—C16	117.43 (14)	C18—C35—H35B	109.5
C20—C15—C3	122.85 (12)	H35A—C35—H35B	109.5
C16—C15—C3	119.69 (13)	C18—C35—H35C	109.5
C17—C16—C15	121.27 (16)	H35A—C35—H35C	109.5
C17—C16—H16	119.4	H35B—C35—H35C	109.5
C15—C16—H16	119.4	C9—N2—C3	118.52 (11)
C18—C17—C16	121.36 (15)	C9—N2—C1	120.73 (12)
C18—C17—H17	119.3	C3—N2—C1	112.99 (12)
C16—C17—H17	119.3	C5—N3—C21	122.00 (13)
C19—C18—C17	117.11 (15)
N2—C3—C4—C5	−60.88 (15)	C3—C15—C20—C19	178.44 (14)
C15—C3—C4—C5	65.12 (15)	C18—C19—C20—C15	−0.4 (3)
N2—C3—C4—C8	56.94 (16)	C26—C21—C22—C23	2.2 (3)
C15—C3—C4—C8	−177.06 (12)	N3—C21—C22—C23	−173.09 (18)
C8—C4—C5—N3	120.97 (18)	C21—C22—C23—C24	0.7 (4)
C3—C4—C5—N3	−120.76 (17)	C22—C23—C24—C25	−3.9 (4)
C8—C4—C5—C6	−61.56 (16)	C23—C24—C25—C26	4.2 (4)
C3—C4—C5—C6	56.71 (15)	C24—C25—C26—C21	−1.2 (4)
N3—C5—C6—C27	1.0 (2)	C22—C21—C26—C25	−2.0 (3)
C4—C5—C6—C27	−176.64 (13)	N3—C21—C26—C25	173.5 (2)
N3—C5—C6—C1	−178.95 (14)	C5—C6—C27—C28	175.92 (14)
C4—C5—C6—C1	3.36 (17)	C1—C6—C27—C28	−4.1 (3)
N2—C1—C6—C27	119.23 (16)	C6—C27—C28—C33	−37.1 (2)
C7—C1—C6—C27	−121.95 (18)	C6—C27—C28—C29	147.31 (17)
N2—C1—C6—C5	−60.78 (17)	C33—C28—C29—C30	2.2 (2)
C7—C1—C6—C5	58.04 (16)	C27—C28—C29—C30	178.16 (15)
N2—C1—C7—C8	57.59 (19)	C28—C29—C30—C31	−1.3 (3)
C6—C1—C7—C8	−60.17 (17)	C29—C30—C31—C32	−0.4 (2)
C5—C4—C8—C7	57.61 (18)	C29—C30—C31—C34	179.78 (17)
C3—C4—C8—C7	−59.63 (17)	C30—C31—C32—C33	1.1 (3)
C1—C7—C8—C4	2.33 (19)	C34—C31—C32—C33	−179.08 (18)
N2—C9—C10—C11	178.88 (15)	C31—C32—C33—C28	−0.1 (3)
C14—C9—C10—C11	0.0 (2)	C29—C28—C33—C32	−1.5 (2)
C9—C10—C11—C12	0.3 (3)	C27—C28—C33—C32	−177.21 (15)
C10—C11—C12—C13	0.0 (3)	C14—C9—N2—C3	−26.36 (19)
C11—C12—C13—C14	−0.4 (3)	C10—C9—N2—C3	154.75 (14)
C12—C13—C14—C9	0.7 (3)	C14—C9—N2—C1	−173.51 (14)
N2—C9—C14—C13	−179.37 (15)	C10—C9—N2—C1	7.6 (2)
C10—C9—C14—C13	−0.4 (2)	C15—C3—N2—C9	89.35 (15)
N2—C3—C15—C20	17.26 (19)	C4—C3—N2—C9	−146.09 (12)
C4—C3—C15—C20	−105.73 (16)	C15—C3—N2—C1	−121.08 (12)
N2—C3—C15—C16	−164.80 (12)	C4—C3—N2—C1	3.48 (15)
C4—C3—C15—C16	72.21 (16)	C6—C1—N2—C9	−154.66 (13)
C20—C15—C16—C17	0.0 (2)	C7—C1—N2—C9	86.53 (18)
C3—C15—C16—C17	−178.04 (14)	C6—C1—N2—C3	56.53 (16)
C15—C16—C17—C18	−0.5 (3)	C7—C1—N2—C3	−62.29 (17)
C16—C17—C18—C19	0.6 (3)	C6—C5—N3—C21	−175.42 (14)
C16—C17—C18—C35	−177.96 (18)	C4—C5—N3—C21	1.8 (2)
C17—C18—C19—C20	−0.1 (3)	C26—C21—N3—C5	103.9 (2)
C35—C18—C19—C20	178.44 (18)	C22—C21—N3—C5	−80.8 (2)
C16—C15—C20—C19	0.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N2	0.93	2.54	2.881 (2)	102
C27—H27···N3	0.93	2.46	2.835 (2)	104