N-{6-[(Z)-Benzyl­idene]-2,3-diphenyl-2-aza­bicyclo­[2.2.2]octan-5-yl­idene}aniline

Ravikumar, K.; Sridhar, B.; Mahesh, M.; Narayana Reddy, V.V.

doi:10.1107/S1600536805028849

N-{6-[(Z)-Benzylidene]-2,3-diphenyl-2-azabicyclo[2.2.2]octan-5-ylidene}aniline

K. Ravikumar, B. Sridhar, M. Mahesh and V. V. Narayana Reddy

The title compound, C₃₂H₂₈N₂, was obtained from the Diels-Alder reaction of N-benzylideneaniline and cyclohexen-2-one catalysed by zirconium tetrachloride. All three rings in the azabicyclo[2.2.2] ring system adopt boat conformations. The crystal packing is stabilized by van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028849/cv6565sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028849/cv6565Isup2.hkl Contains datablock I

CCDC reference: 287535

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Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C)= 0.002 Å
R factor = 0.049
wR factor = 0.134
Data-to-parameter ratio = 18.1

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No errors found in this datablock

Comment top

The presence of an isoquinuclidine ring system in a molecule is frequently associated with significant pharmacological properties (Iriepa et al., 2002). In addition, it also acts as a precursor for the synthesis of naturally occurring piperidine alkaloids of the prosopis family (Birkinshaw et al., 1988). The structure of the title compound, (I), is reported here as a part of our ongoing structural study of this series of compounds (Ravikumar et al., 2005).

The molecule of (I) consists of four planar benzene rings, two of which are directly connected to the azabicyclic system while the other two are connected through a double-bond linkage as an extended `arm' (Fig. 1). All the bond lengths and angles (Table 1) are in a good agreement with those found in related structures (Sonar et al., 2003, 2004).

The geometrical isomerism around the double bonds C6═C27 and C5═N3 affords the possibility of E and Z isomers. The C27—C28 bond is in a trans configuration with respect to the C5—C6 bond [C5—C6—C27—C28 = −172.43 (14)°]. Similarly, the N3—C21 bond is also in a trans disposition with respect to the C5—C6 bond [C6—C5—N3—C21 = 177.92 (13) Å]. The bond angles around atoms C6, C21 and C28 are close to the ideal value of 120°, while the C1—C6—C27 [128.2 (1)°] and N3—C5—C4 [127.4 (1)°] angles are more distorted, as a consequence of the strain induced by the C6═C27 and C5═N3 double-bond linkages. Atom N2 is in pyramidal configuration and the sum of the angles around the atom is 350.6 (1)°.

All three six-membered rings of the azabicyclo[2.2.2] system adopt the expected boat conformation, with asymmetry parameters (Nardelli, 1983) ΔC_s(C1) of 0.015 (1), 0.289 (1) and 0.002 (1) for the rings C3/N2/C1/C7/C8/C4, C1/C4–C8 and C1/N2/C3–C6, respectively. In the absence of H-atom-donating groups, the crystal packing (Fig. 2) is stabilized by van der Waals forces.

Experimental top

To a solution of N-benzylideneaniline (5.5 mmol) in CH₂Cl₂ (5 ml) at room temperature were sequentially added ZrCl₄ (10 mol%) and cyclohexen-2-one (5.5 mmol), and the mixture was stirred for 6 h. After completion of the reaction as indicated by thin-layer chromatography, the reaction was quenched with water, diluted with CH₂Cl₂ (20 ml) and washed with water (10 ml). The aqueous layer was extracted with CH₂Cl₂ (2 C 10 ml). The combined organic layers were dried over Na₂SO₄ and concentrated in vacuo to yield a dark -brown residue, which was purified by column chromatography using 2–10% ethyl acetate in hexane as eluant to obtain the pure product.

Computing details top

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: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. View of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A packing diagram of (I), viewed approximately down the b axis.

N-{2,3-diphenyl-6-[(Z)-phenylmethylidene]- 2-azabicyclo[2.2.2]oct-5-ylidene}-aniline top

Crystal data top

C₃₂H₂₈N₂	F(000) = 936
M_r = 440.56	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4667 reflections
a = 14.6209 (13) Å	θ = 2.4–27.4°
b = 9.5899 (9) Å	µ = 0.07 mm⁻¹
c = 17.9541 (16) Å	T = 273 K
β = 107.701 (2)°	Needle, colourless
V = 2398.2 (4) Å³	0.19 × 0.11 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 28.0°, θ_min = 2.4°
ω scans	h = −18→19
14781 measured reflections	k = −7→12
5570 independent reflections	l = −23→23

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0634P)² + 0.3708P] where P = (F_o² + 2F_c²)/3
5570 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₂H₂₈N₂	V = 2398.2 (4) Å³
M_r = 440.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6209 (13) Å	µ = 0.07 mm⁻¹
b = 9.5899 (9) Å	T = 273 K
c = 17.9541 (16) Å	0.19 × 0.11 × 0.09 mm
β = 107.701 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4256 reflections with I > 2σ(I)
14781 measured reflections	R_int = 0.021
5570 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
5570 reflections	Δρ_min = −0.20 e Å⁻³
307 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N2	0.20593 (7)	0.03442 (12)	0.29660 (6)	0.0376 (3)
N3	0.45718 (8)	0.00292 (15)	0.25162 (7)	0.0512 (3)
C1	0.21337 (9)	0.12376 (14)	0.23192 (7)	0.0393 (3)
H1	0.1516	0.1266	0.1905	0.047*
C3	0.29596 (9)	0.02325 (13)	0.36151 (7)	0.0338 (3)
H3	0.2855	0.0657	0.4079	0.041*
C4	0.37305 (9)	0.10938 (13)	0.33955 (7)	0.0355 (3)
H4	0.4347	0.1027	0.3809	0.043*
C5	0.38225 (9)	0.05212 (13)	0.26385 (7)	0.0375 (3)
C6	0.28961 (9)	0.06220 (14)	0.20068 (7)	0.0376 (3)
C7	0.24379 (11)	0.27157 (15)	0.26173 (8)	0.0475 (3)
H7A	0.1956	0.3130	0.2819	0.057*
H7B	0.2504	0.3295	0.2194	0.057*
C8	0.34053 (11)	0.26202 (14)	0.32702 (8)	0.0458 (3)
H8A	0.3885	0.3166	0.3127	0.055*
H8B	0.3338	0.2998	0.3752	0.055*
C9	0.11982 (9)	0.03119 (15)	0.31567 (8)	0.0419 (3)
C10	0.03930 (10)	0.10950 (19)	0.27615 (9)	0.0552 (4)
H10	0.0421	0.1695	0.2362	0.066*
C11	−0.04472 (11)	0.0985 (2)	0.29600 (11)	0.0719 (6)
H11	−0.0979	0.1508	0.2688	0.086*
C12	−0.05102 (13)	0.0121 (3)	0.35492 (12)	0.0787 (6)
H12	−0.1080	0.0051	0.3675	0.094*
C13	0.02768 (13)	−0.0636 (2)	0.39490 (11)	0.0722 (5)
H13	0.0243	−0.1215	0.4356	0.087*
C14	0.11214 (11)	−0.05574 (18)	0.37588 (9)	0.0553 (4)
H14	0.1646	−0.1090	0.4035	0.066*
C15	0.33078 (9)	−0.12452 (13)	0.38210 (7)	0.0362 (3)
C16	0.39373 (10)	−0.15106 (15)	0.45586 (8)	0.0442 (3)
H16	0.4110	−0.0793	0.4923	0.053*
C17	0.43094 (12)	−0.28273 (17)	0.47565 (10)	0.0606 (4)
H17	0.4728	−0.2997	0.5253	0.073*
C18	0.40612 (14)	−0.38906 (17)	0.42184 (11)	0.0695 (5)
H18	0.4319	−0.4777	0.4349	0.083*
C19	0.34342 (14)	−0.36447 (16)	0.34890 (10)	0.0625 (5)
H19	0.3262	−0.4368	0.3128	0.075*
C20	0.30581 (11)	−0.23289 (15)	0.32888 (8)	0.0478 (3)
H20	0.2634	−0.2169	0.2793	0.057*
C21	0.54531 (10)	−0.00095 (17)	0.31271 (8)	0.0476 (3)
C22	0.57350 (11)	−0.12182 (18)	0.35546 (9)	0.0543 (4)
H22	0.5328	−0.1986	0.3465	0.065*
C23	0.66219 (12)	−0.1283 (2)	0.41149 (10)	0.0630 (5)
H23	0.6801	−0.2090	0.4411	0.076*
C24	0.72403 (12)	−0.0176 (2)	0.42404 (10)	0.0667 (5)
H24	0.7843	−0.0236	0.4611	0.080*
C25	0.69645 (13)	0.1024 (2)	0.38157 (11)	0.0695 (5)
H25	0.7383	0.1779	0.3900	0.083*
C26	0.60721 (12)	0.1121 (2)	0.32648 (10)	0.0609 (4)
H26	0.5886	0.1944	0.2986	0.073*
C27	0.28157 (10)	0.02401 (15)	0.12750 (8)	0.0440 (3)
H27	0.3358	−0.0192	0.1214	0.053*
C28	0.20171 (10)	0.03870 (15)	0.05507 (8)	0.0440 (3)
C29	0.13521 (11)	0.14620 (16)	0.04082 (8)	0.0510 (4)
H29	0.1374	0.2103	0.0802	0.061*
C30	0.06598 (13)	0.15967 (19)	−0.03064 (9)	0.0619 (4)
H30	0.0222	0.2327	−0.0389	0.074*
C31	0.06099 (14)	0.0666 (2)	−0.08957 (10)	0.0701 (5)
H31	0.0139	0.0759	−0.1376	0.084*
C32	0.12573 (16)	−0.0398 (2)	−0.07714 (10)	0.0814 (6)
H32	0.1226	−0.1036	−0.1168	0.098*
C33	0.19572 (14)	−0.0532 (2)	−0.00612 (9)	0.0695 (5)
H33	0.2400	−0.1254	0.0011	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0319 (5)	0.0444 (6)	0.0351 (5)	0.0020 (4)	0.0081 (4)	0.0040 (4)
N3	0.0391 (6)	0.0715 (9)	0.0429 (6)	0.0072 (6)	0.0124 (5)	−0.0023 (6)
C1	0.0357 (7)	0.0446 (7)	0.0350 (6)	0.0066 (5)	0.0071 (5)	0.0041 (5)
C3	0.0330 (6)	0.0351 (6)	0.0327 (6)	0.0017 (5)	0.0090 (5)	−0.0004 (5)
C4	0.0331 (6)	0.0336 (6)	0.0369 (6)	−0.0005 (5)	0.0063 (5)	−0.0002 (5)
C5	0.0372 (7)	0.0373 (7)	0.0383 (7)	−0.0002 (5)	0.0118 (5)	0.0031 (5)
C6	0.0366 (7)	0.0392 (7)	0.0361 (6)	0.0013 (5)	0.0096 (5)	0.0034 (5)
C7	0.0536 (8)	0.0401 (7)	0.0479 (8)	0.0115 (6)	0.0140 (6)	0.0070 (6)
C8	0.0523 (8)	0.0326 (7)	0.0501 (8)	−0.0009 (6)	0.0121 (6)	−0.0003 (6)
C9	0.0347 (7)	0.0517 (8)	0.0387 (7)	−0.0040 (6)	0.0102 (5)	−0.0097 (6)
C10	0.0386 (8)	0.0805 (11)	0.0438 (8)	0.0066 (7)	0.0083 (6)	−0.0078 (7)
C11	0.0338 (8)	0.1176 (16)	0.0598 (10)	0.0055 (9)	0.0078 (7)	−0.0215 (11)
C12	0.0431 (9)	0.1252 (18)	0.0745 (12)	−0.0230 (10)	0.0281 (9)	−0.0323 (12)
C13	0.0601 (11)	0.0953 (14)	0.0696 (11)	−0.0240 (10)	0.0325 (9)	−0.0060 (10)
C14	0.0462 (8)	0.0661 (10)	0.0559 (9)	−0.0088 (7)	0.0192 (7)	0.0006 (7)
C15	0.0351 (6)	0.0342 (7)	0.0393 (7)	0.0005 (5)	0.0116 (5)	0.0020 (5)
C16	0.0462 (8)	0.0394 (7)	0.0423 (7)	0.0031 (6)	0.0066 (6)	−0.0011 (6)
C17	0.0660 (10)	0.0466 (9)	0.0547 (9)	0.0108 (8)	−0.0033 (7)	0.0062 (7)
C18	0.0855 (13)	0.0349 (8)	0.0755 (11)	0.0135 (8)	0.0060 (10)	0.0047 (8)
C19	0.0826 (12)	0.0345 (8)	0.0624 (10)	−0.0016 (7)	0.0100 (9)	−0.0076 (7)
C20	0.0550 (9)	0.0385 (7)	0.0440 (7)	−0.0026 (6)	0.0063 (6)	−0.0013 (6)
C21	0.0357 (7)	0.0677 (10)	0.0420 (7)	0.0067 (7)	0.0154 (6)	−0.0056 (7)
C22	0.0474 (8)	0.0618 (10)	0.0531 (8)	0.0079 (7)	0.0146 (7)	−0.0064 (7)
C23	0.0555 (10)	0.0795 (12)	0.0518 (9)	0.0258 (9)	0.0128 (7)	−0.0058 (8)
C24	0.0382 (8)	0.1091 (16)	0.0495 (9)	0.0112 (9)	0.0086 (7)	−0.0188 (10)
C25	0.0469 (9)	0.0960 (15)	0.0671 (11)	−0.0145 (9)	0.0194 (8)	−0.0160 (10)
C26	0.0504 (9)	0.0744 (11)	0.0593 (9)	−0.0005 (8)	0.0191 (7)	0.0014 (8)
C27	0.0404 (7)	0.0503 (8)	0.0414 (7)	0.0056 (6)	0.0127 (6)	0.0000 (6)
C28	0.0462 (8)	0.0500 (8)	0.0352 (7)	0.0008 (6)	0.0114 (6)	−0.0010 (6)
C29	0.0595 (9)	0.0500 (8)	0.0396 (7)	0.0058 (7)	0.0095 (6)	−0.0027 (6)
C30	0.0665 (10)	0.0631 (10)	0.0482 (9)	0.0154 (8)	0.0056 (7)	0.0028 (8)
C31	0.0784 (12)	0.0746 (12)	0.0413 (8)	0.0070 (10)	−0.0059 (8)	−0.0032 (8)
C32	0.1044 (16)	0.0809 (14)	0.0438 (9)	0.0205 (12)	−0.0001 (9)	−0.0199 (9)
C33	0.0815 (12)	0.0735 (12)	0.0472 (9)	0.0273 (10)	0.0102 (8)	−0.0094 (8)

Geometric parameters (Å, º) top

N2—C9	1.4020 (17)	C16—C17	1.378 (2)
N2—C3	1.4729 (15)	C16—H16	0.9300
N2—C1	1.4735 (17)	C17—C18	1.375 (2)
N3—C5	1.2717 (17)	C17—H17	0.9300
N3—C21	1.4160 (18)	C18—C19	1.372 (2)
C1—C6	1.5119 (18)	C18—H18	0.9300
C1—C7	1.533 (2)	C19—C20	1.380 (2)
C1—H1	0.9800	C19—H19	0.9300
C3—C15	1.5131 (17)	C20—H20	0.9300
C3—C4	1.5422 (17)	C21—C22	1.382 (2)
C3—H3	0.9800	C21—C26	1.385 (2)
C4—C5	1.5093 (18)	C22—C23	1.380 (2)
C4—C8	1.5344 (18)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.369 (3)
C5—C6	1.4819 (17)	C23—H23	0.9300
C6—C27	1.3343 (18)	C24—C25	1.372 (3)
C7—C8	1.541 (2)	C24—H24	0.9300
C7—H7A	0.9700	C25—C26	1.380 (2)
C7—H7B	0.9700	C25—H25	0.9300
C8—H8A	0.9700	C26—H26	0.9300
C8—H8B	0.9700	C27—C28	1.4666 (18)
C9—C10	1.395 (2)	C27—H27	0.9300
C9—C14	1.396 (2)	C28—C29	1.386 (2)
C10—C11	1.383 (2)	C28—C33	1.390 (2)
C10—H10	0.9300	C29—C30	1.378 (2)
C11—C12	1.369 (3)	C29—H29	0.9300
C11—H11	0.9300	C30—C31	1.369 (2)
C12—C13	1.366 (3)	C30—H30	0.9300
C12—H12	0.9300	C31—C32	1.363 (3)
C13—C14	1.380 (2)	C31—H31	0.9300
C13—H13	0.9300	C32—C33	1.377 (2)
C14—H14	0.9300	C32—H32	0.9300
C15—C20	1.3836 (18)	C33—H33	0.9300
C15—C16	1.3872 (18)

C9—N2—C3	117.26 (10)	C20—C15—C16	118.72 (12)
C9—N2—C1	119.49 (10)	C20—C15—C3	122.43 (11)
C3—N2—C1	113.80 (10)	C16—C15—C3	118.78 (11)
C5—N3—C21	120.31 (12)	C17—C16—C15	120.64 (13)
N2—C1—C6	107.74 (10)	C17—C16—H16	119.7
N2—C1—C7	110.22 (10)	C15—C16—H16	119.7
C6—C1—C7	108.80 (11)	C18—C17—C16	119.94 (14)
N2—C1—H1	110.0	C18—C17—H17	120.0
C6—C1—H1	110.0	C16—C17—H17	120.0
C7—C1—H1	110.0	C19—C18—C17	120.01 (14)
N2—C3—C15	114.51 (10)	C19—C18—H18	120.0
N2—C3—C4	107.79 (10)	C17—C18—H18	120.0
C15—C3—C4	110.26 (10)	C18—C19—C20	120.25 (15)
N2—C3—H3	108.0	C18—C19—H19	119.9
C15—C3—H3	108.0	C20—C19—H19	119.9
C4—C3—H3	108.0	C19—C20—C15	120.44 (13)
C5—C4—C8	108.88 (11)	C19—C20—H20	119.8
C5—C4—C3	107.91 (10)	C15—C20—H20	119.8
C8—C4—C3	109.30 (10)	C22—C21—C26	119.26 (14)
C5—C4—H4	110.2	C22—C21—N3	119.98 (14)
C8—C4—H4	110.2	C26—C21—N3	120.59 (15)
C3—C4—H4	110.2	C23—C22—C21	119.89 (16)
N3—C5—C6	121.80 (12)	C23—C22—H22	120.1
N3—C5—C4	127.43 (12)	C21—C22—H22	120.1
C6—C5—C4	110.76 (11)	C24—C23—C22	120.82 (17)
C27—C6—C5	121.47 (12)	C24—C23—H23	119.6
C27—C6—C1	128.19 (12)	C22—C23—H23	119.6
C5—C6—C1	110.31 (11)	C23—C24—C25	119.46 (15)
C1—C7—C8	108.21 (10)	C23—C24—H24	120.3
C1—C7—H7A	110.1	C25—C24—H24	120.3
C8—C7—H7A	110.1	C24—C25—C26	120.59 (18)
C1—C7—H7B	110.1	C24—C25—H25	119.7
C8—C7—H7B	110.1	C26—C25—H25	119.7
H7A—C7—H7B	108.4	C25—C26—C21	119.97 (18)
C4—C8—C7	109.88 (11)	C25—C26—H26	120.0
C4—C8—H8A	109.7	C21—C26—H26	120.0
C7—C8—H8A	109.7	C6—C27—C28	130.91 (13)
C4—C8—H8B	109.7	C6—C27—H27	114.5
C7—C8—H8B	109.7	C28—C27—H27	114.5
H8A—C8—H8B	108.2	C29—C28—C33	116.96 (13)
C10—C9—C14	117.47 (13)	C29—C28—C27	124.03 (13)
C10—C9—N2	123.06 (13)	C33—C28—C27	118.80 (13)
C14—C9—N2	119.46 (13)	C30—C29—C28	121.14 (14)
C11—C10—C9	120.40 (17)	C30—C29—H29	119.4
C11—C10—H10	119.8	C28—C29—H29	119.4
C9—C10—H10	119.8	C31—C30—C29	120.67 (16)
C12—C11—C10	121.28 (17)	C31—C30—H30	119.7
C12—C11—H11	119.4	C29—C30—H30	119.7
C10—C11—H11	119.4	C32—C31—C30	119.35 (15)
C13—C12—C11	118.96 (16)	C32—C31—H31	120.3
C13—C12—H12	120.5	C30—C31—H31	120.3
C11—C12—H12	120.5	C31—C32—C33	120.33 (16)
C12—C13—C14	121.02 (19)	C31—C32—H32	119.8
C12—C13—H13	119.5	C33—C32—H32	119.8
C14—C13—H13	119.5	C32—C33—C28	121.55 (16)
C13—C14—C9	120.87 (17)	C32—C33—H33	119.2
C13—C14—H14	119.6	C28—C33—H33	119.2
C9—C14—H14	119.6

C9—N2—C1—C6	−154.80 (11)	C11—C12—C13—C14	−1.0 (3)
C3—N2—C1—C6	59.66 (13)	C12—C13—C14—C9	0.7 (3)
C9—N2—C1—C7	86.62 (14)	C10—C9—C14—C13	0.3 (2)
C3—N2—C1—C7	−58.93 (13)	N2—C9—C14—C13	−178.53 (15)
C9—N2—C3—C15	89.29 (14)	N2—C3—C15—C20	24.50 (18)
C1—N2—C3—C15	−124.35 (11)	C4—C3—C15—C20	−97.26 (14)
C9—N2—C3—C4	−147.61 (11)	N2—C3—C15—C16	−158.66 (12)
C1—N2—C3—C4	−1.25 (14)	C4—C3—C15—C16	79.58 (15)
N2—C3—C4—C5	−58.23 (12)	C20—C15—C16—C17	0.2 (2)
C15—C3—C4—C5	67.43 (12)	C3—C15—C16—C17	−176.72 (14)
N2—C3—C4—C8	60.03 (13)	C15—C16—C17—C18	0.4 (3)
C15—C3—C4—C8	−174.31 (10)	C16—C17—C18—C19	−0.8 (3)
C21—N3—C5—C6	177.92 (13)	C17—C18—C19—C20	0.7 (3)
C21—N3—C5—C4	−0.8 (2)	C18—C19—C20—C15	−0.1 (3)
C8—C4—C5—N3	120.09 (15)	C16—C15—C20—C19	−0.4 (2)
C3—C4—C5—N3	−121.38 (15)	C3—C15—C20—C19	176.46 (14)
C8—C4—C5—C6	−58.72 (14)	C5—N3—C21—C22	96.93 (18)
C3—C4—C5—C6	59.81 (13)	C5—N3—C21—C26	−87.88 (18)
N3—C5—C6—C27	−2.1 (2)	C26—C21—C22—C23	0.5 (2)
C4—C5—C6—C27	176.75 (13)	N3—C21—C22—C23	175.75 (13)
N3—C5—C6—C1	179.76 (13)	C21—C22—C23—C24	−1.7 (2)
C4—C5—C6—C1	−1.35 (15)	C22—C23—C24—C25	1.5 (3)
N2—C1—C6—C27	124.37 (15)	C23—C24—C25—C26	−0.1 (3)
C7—C1—C6—C27	−116.14 (15)	C24—C25—C26—C21	−1.2 (3)
N2—C1—C6—C5	−57.69 (13)	C22—C21—C26—C25	0.9 (2)
C7—C1—C6—C5	61.80 (13)	N3—C21—C26—C25	−174.28 (14)
N2—C1—C7—C8	58.07 (14)	C5—C6—C27—C28	−172.43 (14)
C6—C1—C7—C8	−59.86 (14)	C1—C6—C27—C28	5.3 (3)
C5—C4—C8—C7	58.81 (14)	C6—C27—C28—C29	30.1 (3)
C3—C4—C8—C7	−58.84 (14)	C6—C27—C28—C33	−155.41 (17)
C1—C7—C8—C4	0.14 (16)	C33—C28—C29—C30	0.7 (2)
C3—N2—C9—C10	144.28 (13)	C27—C28—C29—C30	175.24 (15)
C1—N2—C9—C10	−0.10 (19)	C28—C29—C30—C31	0.1 (3)
C3—N2—C9—C14	−36.97 (18)	C29—C30—C31—C32	−0.3 (3)
C1—N2—C9—C14	178.64 (12)	C30—C31—C32—C33	−0.3 (3)
C14—C9—C10—C11	−0.9 (2)	C31—C32—C33—C28	1.1 (3)
N2—C9—C10—C11	177.88 (14)	C29—C28—C33—C32	−1.3 (3)
C9—C10—C11—C12	0.6 (3)	C27—C28—C33—C32	−176.17 (18)
C10—C11—C12—C13	0.4 (3)

Experimental details

Crystal data
Chemical formula	C₃₂H₂₈N₂
M_r	440.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.6209 (13), 9.5899 (9), 17.9541 (16)
β (°)	107.701 (2)
V (Å³)	2398.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.19 × 0.11 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14781, 5570, 4256
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.134, 1.05
No. of reflections	5570
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXL97.

Selected geometric parameters (Å, º) top

N2—C1	1.4735 (17)	C5—C6	1.4819 (17)
N3—C5	1.2717 (17)	C6—C27	1.3343 (18)
C1—C6	1.5119 (18)

N3—C5—C6	121.80 (12)	C26—C21—N3	120.59 (15)
C27—C6—C5	121.47 (12)	C29—C28—C33	116.96 (13)
C22—C21—N3	119.98 (14)	C29—C28—C27	124.03 (13)

C1—N2—C9—C10	−0.10 (19)	C5—N3—C21—C22	96.93 (18)
C4—C3—C15—C16	79.58 (15)	C6—C27—C28—C29	30.1 (3)

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N-{6-[(Z)-Benzyl­idene]-2,3-diphenyl-2-aza­bicyclo­[2.2.2]octan-5-yl­idene}aniline

Supporting information

Key indicators

checkCIF/PLATON results

N-{6-[(Z)-Benzylidene]-2,3-diphenyl-2-azabicyclo[2.2.2]octan-5-ylidene}aniline