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

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

doi:10.1107/S1600536805042066

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

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

The title compound, C₃₂H₂₆N₂Cl₂, exists as the Z isomer. All three rings in the azabicylo[2.2.2]octane system adopt a boat conformation. Intermolecular C—H

Cl interactions form a dimer in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042066/cf6480sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042066/cf6480Isup2.hkl Contains datablock I

CCDC reference: 296526

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.005 Å
R factor = 0.055
wR factor = 0.163
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.99 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
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
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C21    -C26           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  CL2     ..       3.06 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C10    ..  CL2     ..       3.97 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 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
   7 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In continuation of our ongoing structural elucidation of azabicyclo[2.2.2]octane derivatives obtained from the Diels–Alder reaction, we report here the crystal structure of the title compound, (I).

The molecular geometry of (I) (Fig. 1), in terms of bond distances and angles, is in good agreement with that of similar structures (Sonar et al., 2004; Ravikumar et al., 2005a,b). The torsion angles C5—C6—C27—C28 = −176.2 (2)° and C5—C6—N2—C21 = 176.4 (2)° indicate a trans configuration, and hence the Z isomer. Due to the double-bond strain, the bond angles C4—C5—N2, C6—C27—C28 and C1—C6—C27 deviate from ideal values (Table 1).

All three six-membered rings of the azabicyclo[2.2.2]octane system adopt the expected boat conformation, with asymmetry parameters (Nardelli, 1983) ΔC_s(C1) = 0.009 (2), 0.017 (2), 0.027 (1) for the rings C1/C4–C8, N1/C1/C3/C4/C7/C8 and N1/C1/C3–C6, respectively. The C9–C14 phenyl ring and C15–C20 chlorophenyl ring make dihedral angles with the mean plane of atoms C1/C3/C4/N1 of the azabicyclo[2.2.2]octane cage of 30.7 (1) and 66.7 (1)°, respectively. Similarly, the dihedral angles are 77.9 (1) and 35.1 (1)°, respectively, for the C21–C26 phenyl ring and C28–C33 chlorophenyl ring with respect to the C1/C4/C5/C6 mean plane of the cage. The torsion angle C9—N1—C3—C15 is −90.2 (2)°, but N2—C5—C6—C27 is only 2.8 (4)°, as a consequence of the double bonds.

The crystal structure is stabilized by weak intermolecular C—H···Cl interactions (You et al., 2004) (Table 2). One of them leads to formation of a centrosymmetric dimer with a characteristic R₂²(26) motif (Bernstein et al., 1995) in the crystal packing (Fig. 2).

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). The mixture was stirred for 6 h. After completion of the reaction as indicated by thin-layer chromatography, the reaction was quenched with water, and the mixture diluted with CH₂Cl₂ (20 ml) and washed with water (10 ml). The aqueous layer was extracted with CH₂Cl₂ (2 x 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 eluent 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. A view of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the packing, showing the dimers. Dashed lines indicate C—H···Cl interactions.

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

Crystal data top

C₃₂H₂₆Cl₂N₂	F(000) = 1064
M_r = 509.45	D_x = 1.274 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.3560 (6) Å	Cell parameters from 5389 reflections
b = 10.0621 (4) Å	θ = 2.2–23.0°
c = 18.3872 (8) Å	µ = 0.27 mm⁻¹
β = 91.427 (1)°	T = 273 K
V = 2655.24 (19) Å³	Block, colorless
Z = 4	0.20 × 0.12 × 0.07 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3312 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
ω scans	h = −17→17
18622 measured reflections	k = −11→11
4657 independent reflections	l = −21→21

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0676P)² + 0.9266P] where P = (F_o² + 2F_c²)/3
4657 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₃₂H₂₆Cl₂N₂	V = 2655.24 (19) Å³
M_r = 509.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3560 (6) Å	µ = 0.27 mm⁻¹
b = 10.0621 (4) Å	T = 273 K
c = 18.3872 (8) Å	0.20 × 0.12 × 0.07 mm
β = 91.427 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3312 reflections with I > 2σ(I)
18622 measured reflections	R_int = 0.021
4657 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
4657 reflections	Δρ_min = −0.36 e Å⁻³
325 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
Cl1	0.30109 (8)	0.75288 (12)	1.07831 (7)	0.1443 (4)
Cl2	−0.06461 (8)	0.26491 (15)	0.54980 (6)	0.1609 (5)
N1	0.23800 (15)	0.1089 (2)	0.82629 (10)	0.0765 (6)
N2	−0.0294 (2)	0.1096 (3)	0.88518 (12)	0.0965 (7)
C1	0.2240 (2)	0.1253 (3)	0.90536 (13)	0.0943 (9)
H1	0.2695	0.1887	0.9257	0.113*
C3	0.16841 (17)	0.0202 (2)	0.79139 (12)	0.0702 (6)
H3	0.2020	−0.0553	0.7710	0.084*
C4	0.1036 (2)	−0.0345 (3)	0.84999 (13)	0.0822 (7)
H4	0.0575	−0.0956	0.8285	0.099*
C5	0.0568 (2)	0.0829 (3)	0.88407 (13)	0.0849 (8)
C6	0.1264 (2)	0.1770 (3)	0.91529 (13)	0.0878 (8)
C7	0.2350 (3)	−0.0082 (4)	0.94316 (17)	0.1224 (14)
H7A	0.2246	0.0015	0.9948	0.147*
H7B	0.2976	−0.0420	0.9370	0.147*
C8	0.1634 (3)	−0.1049 (4)	0.90932 (18)	0.1148 (12)
H8A	0.1234	−0.1384	0.9469	0.138*
H8B	0.1955	−0.1798	0.8882	0.138*
C9	0.32744 (18)	0.1111 (2)	0.79855 (15)	0.0767 (7)
C10	0.4076 (2)	0.1419 (3)	0.84034 (19)	0.1013 (10)
H10	0.4028	0.1599	0.8897	0.122*
C11	0.4941 (2)	0.1458 (3)	0.8082 (3)	0.1206 (13)
H11	0.5464	0.1674	0.8366	0.145*
C12	0.5043 (3)	0.1190 (4)	0.7370 (3)	0.1222 (12)
H12	0.5629	0.1209	0.7165	0.147*
C13	0.4273 (2)	0.0892 (4)	0.6959 (2)	0.1082 (10)
H13	0.4336	0.0707	0.6467	0.130*
C14	0.34048 (19)	0.0856 (3)	0.72519 (15)	0.0843 (7)
H14	0.2891	0.0658	0.6953	0.101*
C15	0.11243 (16)	0.0845 (2)	0.72970 (11)	0.0627 (6)
C16	0.0628 (2)	0.0058 (3)	0.68123 (14)	0.0848 (8)
H16	0.0666	−0.0861	0.6857	0.102*
C17	0.0080 (2)	0.0595 (4)	0.62641 (15)	0.1007 (10)
H17	−0.0254	0.0048	0.5944	0.121*
C18	0.00325 (19)	0.1946 (4)	0.61984 (14)	0.0916 (9)
C19	0.0515 (2)	0.2752 (3)	0.66644 (15)	0.0885 (8)
H19	0.0480	0.3670	0.6613	0.106*
C20	0.10592 (18)	0.2196 (2)	0.72163 (13)	0.0747 (7)
H20	0.1386	0.2749	0.7538	0.090*
C21	−0.0969 (2)	0.0246 (3)	0.85195 (16)	0.0916 (9)
C22	−0.1264 (3)	−0.0890 (5)	0.8840 (2)	0.1272 (13)
H22	−0.0977	−0.1170	0.9272	0.153*
C23	−0.1966 (4)	−0.1620 (5)	0.8546 (4)	0.156 (2)
H23	−0.2163	−0.2387	0.8779	0.187*
C24	−0.2391 (3)	−0.1230 (5)	0.7903 (4)	0.1541 (17)
H24	−0.2887	−0.1716	0.7707	0.185*
C25	−0.2077 (3)	−0.0112 (5)	0.7549 (3)	0.1422 (14)
H25	−0.2338	0.0133	0.7100	0.171*
C26	−0.1377 (3)	0.0633 (4)	0.78646 (19)	0.1107 (10)
H26	−0.1176	0.1403	0.7637	0.133*
C27	0.0997 (2)	0.2887 (3)	0.94778 (13)	0.0884 (8)
H27	0.0355	0.2981	0.9514	0.106*
C28	0.1539 (2)	0.3989 (3)	0.97868 (13)	0.0839 (8)
C29	0.1169 (2)	0.4684 (3)	1.03691 (15)	0.0919 (8)
H29	0.0602	0.4412	1.0553	0.110*
C30	0.1616 (2)	0.5756 (4)	1.06797 (16)	0.0997 (9)
H30	0.1360	0.6196	1.1072	0.120*
C31	0.2435 (2)	0.6164 (3)	1.04067 (17)	0.0978 (9)
C32	0.2818 (2)	0.5534 (4)	0.98267 (19)	0.1073 (10)
H32	0.3378	0.5832	0.9642	0.129*
C33	0.2369 (3)	0.4453 (4)	0.95173 (16)	0.0996 (10)
H33	0.2629	0.4029	0.9121	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1473 (9)	0.1385 (9)	0.1447 (9)	−0.0114 (6)	−0.0472 (7)	0.0042 (6)
Cl2	0.1312 (8)	0.2484 (15)	0.1006 (7)	0.0052 (8)	−0.0478 (6)	0.0461 (8)
N1	0.0879 (15)	0.0811 (13)	0.0596 (11)	0.0214 (11)	−0.0168 (10)	−0.0176 (10)
N2	0.117 (2)	0.1027 (18)	0.0697 (14)	0.0299 (16)	0.0035 (13)	−0.0125 (13)
C1	0.120 (2)	0.101 (2)	0.0602 (14)	0.0494 (17)	−0.0237 (14)	−0.0184 (14)
C3	0.0881 (16)	0.0626 (14)	0.0601 (13)	0.0133 (12)	0.0020 (12)	−0.0078 (11)
C4	0.110 (2)	0.0717 (15)	0.0657 (14)	0.0228 (14)	0.0140 (14)	0.0067 (12)
C5	0.114 (2)	0.0903 (19)	0.0507 (13)	0.0400 (17)	0.0078 (14)	0.0058 (13)
C6	0.118 (2)	0.0967 (19)	0.0482 (13)	0.0421 (18)	−0.0109 (13)	−0.0101 (13)
C7	0.168 (3)	0.134 (3)	0.0645 (17)	0.077 (3)	−0.0140 (19)	−0.0022 (18)
C8	0.157 (3)	0.103 (2)	0.084 (2)	0.055 (2)	0.019 (2)	0.0267 (18)
C9	0.0824 (17)	0.0603 (14)	0.0862 (17)	0.0179 (12)	−0.0203 (14)	−0.0133 (12)
C10	0.110 (2)	0.0806 (19)	0.111 (2)	0.0226 (17)	−0.0439 (19)	−0.0278 (16)
C11	0.082 (2)	0.096 (2)	0.182 (4)	0.0058 (17)	−0.045 (2)	−0.031 (2)
C12	0.092 (2)	0.113 (3)	0.161 (4)	−0.0116 (19)	−0.003 (2)	−0.018 (3)
C13	0.081 (2)	0.126 (3)	0.118 (2)	−0.0147 (18)	0.0060 (18)	−0.011 (2)
C14	0.0795 (17)	0.0922 (19)	0.0807 (17)	−0.0030 (14)	−0.0073 (13)	−0.0091 (14)
C15	0.0710 (14)	0.0647 (14)	0.0524 (12)	−0.0038 (11)	0.0011 (10)	−0.0054 (10)
C16	0.106 (2)	0.0803 (17)	0.0680 (16)	−0.0185 (15)	−0.0019 (14)	−0.0139 (13)
C17	0.101 (2)	0.136 (3)	0.0645 (16)	−0.035 (2)	−0.0138 (15)	−0.0139 (17)
C18	0.0750 (17)	0.135 (3)	0.0643 (16)	−0.0136 (17)	−0.0118 (13)	0.0165 (17)
C19	0.0914 (19)	0.0864 (18)	0.0868 (18)	−0.0060 (15)	−0.0159 (15)	0.0193 (15)
C20	0.0820 (16)	0.0698 (16)	0.0714 (15)	−0.0081 (12)	−0.0185 (12)	−0.0001 (12)
C21	0.109 (2)	0.091 (2)	0.0756 (18)	0.0270 (18)	0.0273 (16)	0.0046 (16)
C22	0.145 (3)	0.126 (3)	0.112 (3)	0.024 (3)	0.050 (3)	0.032 (2)
C23	0.152 (4)	0.123 (4)	0.196 (5)	0.005 (3)	0.076 (4)	0.041 (4)
C24	0.126 (3)	0.115 (3)	0.222 (6)	−0.021 (3)	0.018 (4)	−0.013 (4)
C25	0.156 (4)	0.122 (3)	0.147 (4)	−0.022 (3)	−0.025 (3)	0.005 (3)
C26	0.132 (3)	0.096 (2)	0.104 (2)	−0.008 (2)	−0.006 (2)	0.0112 (19)
C27	0.114 (2)	0.096 (2)	0.0550 (13)	0.0381 (17)	−0.0016 (14)	−0.0044 (14)
C28	0.104 (2)	0.0944 (19)	0.0531 (13)	0.0388 (17)	−0.0034 (14)	−0.0016 (13)
C29	0.0940 (19)	0.109 (2)	0.0729 (16)	0.0197 (17)	0.0023 (14)	−0.0172 (16)
C30	0.102 (2)	0.119 (3)	0.0779 (18)	0.0205 (19)	−0.0051 (17)	−0.0224 (17)
C31	0.104 (2)	0.106 (2)	0.0822 (19)	0.0237 (19)	−0.0208 (17)	0.0069 (17)
C32	0.102 (2)	0.122 (3)	0.098 (2)	0.023 (2)	0.0032 (19)	0.026 (2)
C33	0.117 (3)	0.116 (3)	0.0674 (17)	0.044 (2)	0.0165 (17)	0.0123 (17)

Geometric parameters (Å, º) top

Cl1—C31	1.737 (4)	C15—C20	1.371 (3)
Cl2—C18	1.745 (3)	C15—C16	1.377 (3)
N1—C9	1.394 (3)	C16—C17	1.374 (4)
N1—C3	1.475 (3)	C16—H16	0.930
N1—C1	1.482 (3)	C17—C18	1.367 (5)
N2—C5	1.267 (4)	C17—H17	0.930
N2—C21	1.419 (4)	C18—C19	1.357 (4)
C1—C6	1.511 (4)	C19—C20	1.383 (3)
C1—C7	1.519 (5)	C19—H19	0.930
C1—H1	0.980	C20—H20	0.930
C3—C15	1.518 (3)	C21—C22	1.359 (5)
C3—C4	1.542 (4)	C21—C26	1.382 (4)
C3—H3	0.980	C22—C23	1.350 (7)
C4—C5	1.504 (4)	C22—H22	0.930
C4—C8	1.543 (4)	C23—C24	1.374 (7)
C4—H4	0.980	C23—H23	0.930
C5—C6	1.482 (4)	C24—C25	1.381 (6)
C6—C27	1.333 (4)	C24—H24	0.930
C7—C8	1.536 (5)	C25—C26	1.371 (5)
C7—H7A	0.970	C25—H25	0.930
C7—H7B	0.970	C26—H26	0.930
C8—H8A	0.970	C27—C28	1.462 (4)
C8—H8B	0.970	C27—H27	0.930
C9—C14	1.390 (4)	C28—C33	1.383 (4)
C9—C10	1.402 (4)	C28—C29	1.395 (4)
C10—C11	1.389 (5)	C29—C30	1.372 (4)
C10—H10	0.930	C29—H29	0.930
C11—C12	1.349 (5)	C30—C31	1.355 (4)
C11—H11	0.930	C30—H30	0.930
C12—C13	1.357 (5)	C31—C32	1.368 (5)
C12—H12	0.930	C32—C33	1.380 (5)
C13—C14	1.371 (4)	C32—H32	0.930
C13—H13	0.930	C33—H33	0.930
C14—H14	0.930

C9—N1—C3	118.08 (19)	C20—C15—C16	117.9 (2)
C9—N1—C1	120.4 (2)	C20—C15—C3	122.4 (2)
C3—N1—C1	112.8 (2)	C16—C15—C3	119.6 (2)
C5—N2—C21	121.5 (3)	C17—C16—C15	121.8 (3)
N1—C1—C6	107.79 (19)	C17—C16—H16	119.1
N1—C1—C7	109.6 (2)	C15—C16—H16	119.1
C6—C1—C7	109.6 (3)	C18—C17—C16	118.8 (3)
N1—C1—H1	109.9	C18—C17—H17	120.6
C6—C1—H1	109.9	C16—C17—H17	120.6
C7—C1—H1	109.9	C19—C18—C17	121.0 (3)
N1—C3—C15	114.08 (19)	C19—C18—Cl2	119.4 (3)
N1—C3—C4	109.0 (2)	C17—C18—Cl2	119.6 (2)
C15—C3—C4	110.9 (2)	C18—C19—C20	119.5 (3)
N1—C3—H3	107.5	C18—C19—H19	120.3
C15—C3—H3	107.5	C20—C19—H19	120.3
C4—C3—H3	107.5	C15—C20—C19	121.1 (2)
C5—C4—C3	107.1 (2)	C15—C20—H20	119.5
C5—C4—C8	108.2 (2)	C19—C20—H20	119.5
C3—C4—C8	108.9 (2)	C22—C21—C26	119.0 (4)
C5—C4—H4	110.8	C22—C21—N2	122.5 (4)
C3—C4—H4	110.8	C26—C21—N2	118.4 (3)
C8—C4—H4	110.8	C23—C22—C21	121.4 (4)
N2—C5—C6	120.6 (2)	C23—C22—H22	119.3
N2—C5—C4	128.3 (3)	C21—C22—H22	119.3
C6—C5—C4	111.0 (3)	C22—C23—C24	120.0 (5)
C27—C6—C5	120.9 (3)	C22—C23—H23	120.0
C27—C6—C1	128.5 (3)	C24—C23—H23	120.0
C5—C6—C1	110.6 (2)	C23—C24—C25	119.7 (5)
C1—C7—C8	108.3 (3)	C23—C24—H24	120.1
C1—C7—H7A	110.0	C25—C24—H24	120.1
C8—C7—H7A	110.0	C26—C25—C24	119.3 (5)
C1—C7—H7B	110.0	C26—C25—H25	120.3
C8—C7—H7B	110.0	C24—C25—H25	120.3
H7A—C7—H7B	108.4	C25—C26—C21	120.4 (4)
C7—C8—C4	110.5 (3)	C25—C26—H26	119.8
C7—C8—H8A	109.5	C21—C26—H26	119.8
C4—C8—H8A	109.5	C6—C27—C28	131.1 (3)
C7—C8—H8B	109.5	C6—C27—H27	114.5
C4—C8—H8B	109.5	C28—C27—H27	114.5
H8A—C8—H8B	108.1	C33—C28—C29	117.0 (3)
C14—C9—N1	120.0 (2)	C33—C28—C27	124.9 (3)
C14—C9—C10	116.4 (3)	C29—C28—C27	118.0 (3)
N1—C9—C10	123.6 (3)	C30—C29—C28	122.1 (3)
C11—C10—C9	120.2 (3)	C30—C29—H29	119.0
C11—C10—H10	119.9	C28—C29—H29	119.0
C9—C10—H10	119.9	C31—C30—C29	119.0 (3)
C12—C11—C10	121.9 (3)	C31—C30—H30	120.5
C12—C11—H11	119.1	C29—C30—H30	120.5
C10—C11—H11	119.1	C30—C31—C32	121.2 (3)
C11—C12—C13	118.5 (4)	C30—C31—Cl1	120.1 (3)
C11—C12—H12	120.7	C32—C31—Cl1	118.7 (3)
C13—C12—H12	120.7	C31—C32—C33	119.6 (3)
C12—C13—C14	121.6 (4)	C31—C32—H32	120.2
C12—C13—H13	119.2	C33—C32—H32	120.2
C14—C13—H13	119.2	C32—C33—C28	121.1 (3)
C13—C14—C9	121.5 (3)	C32—C33—H33	119.5
C13—C14—H14	119.3	C28—C33—H33	119.5
C9—C14—H14	119.3

C9—N1—C1—C6	156.0 (2)	N1—C9—C14—C13	178.9 (3)
C3—N1—C1—C6	−57.0 (3)	C10—C9—C14—C13	0.7 (4)
C9—N1—C1—C7	−84.8 (3)	N1—C3—C15—C20	−19.0 (3)
C3—N1—C1—C7	62.2 (3)	C4—C3—C15—C20	104.5 (3)
C9—N1—C3—C15	−90.2 (2)	N1—C3—C15—C16	163.7 (2)
C1—N1—C3—C15	122.0 (2)	C4—C3—C15—C16	−72.8 (3)
C9—N1—C3—C4	145.2 (2)	C20—C15—C16—C17	−0.3 (4)
C1—N1—C3—C4	−2.6 (3)	C3—C15—C16—C17	177.2 (2)
N1—C3—C4—C5	60.3 (3)	C15—C16—C17—C18	0.4 (4)
C15—C3—C4—C5	−66.1 (3)	C16—C17—C18—C19	−0.1 (5)
N1—C3—C4—C8	−56.5 (3)	C16—C17—C18—Cl2	179.0 (2)
C15—C3—C4—C8	177.1 (2)	C17—C18—C19—C20	−0.3 (5)
C21—N2—C5—C6	176.4 (2)	Cl2—C18—C19—C20	−179.5 (2)
C21—N2—C5—C4	0.3 (4)	C16—C15—C20—C19	−0.2 (4)
C3—C4—C5—N2	118.6 (3)	C3—C15—C20—C19	−177.5 (2)
C8—C4—C5—N2	−124.1 (3)	C18—C19—C20—C15	0.5 (4)
C3—C4—C5—C6	−57.8 (3)	C5—N2—C21—C22	79.1 (4)
C8—C4—C5—C6	59.5 (3)	C5—N2—C21—C26	−104.7 (3)
N2—C5—C6—C27	2.8 (4)	C26—C21—C22—C23	−2.3 (5)
C4—C5—C6—C27	179.5 (2)	N2—C21—C22—C23	173.9 (4)
N2—C5—C6—C1	−178.2 (2)	C21—C22—C23—C24	0.9 (7)
C4—C5—C6—C1	−1.5 (3)	C22—C23—C24—C25	2.0 (8)
N1—C1—C6—C27	−121.6 (3)	C23—C24—C25—C26	−3.4 (7)
C7—C1—C6—C27	119.2 (3)	C24—C25—C26—C21	2.1 (7)
N1—C1—C6—C5	59.5 (3)	C22—C21—C26—C25	0.8 (5)
C7—C1—C6—C5	−59.7 (3)	N2—C21—C26—C25	−175.6 (3)
N1—C1—C7—C8	−58.5 (3)	C5—C6—C27—C28	−176.2 (2)
C6—C1—C7—C8	59.6 (3)	C1—C6—C27—C28	5.0 (5)
C1—C7—C8—C4	−1.1 (4)	C6—C27—C28—C33	34.1 (4)
C5—C4—C8—C7	−57.8 (3)	C6—C27—C28—C29	−150.1 (3)
C3—C4—C8—C7	58.3 (3)	C33—C28—C29—C30	−1.9 (4)
C3—N1—C9—C14	29.8 (3)	C27—C28—C29—C30	−178.1 (3)
C1—N1—C9—C14	175.1 (2)	C28—C29—C30—C31	0.9 (5)
C3—N1—C9—C10	−152.1 (2)	C29—C30—C31—C32	0.5 (5)
C1—N1—C9—C10	−6.8 (4)	C29—C30—C31—Cl1	179.4 (2)
C14—C9—C10—C11	0.0 (4)	C30—C31—C32—C33	−0.7 (5)
N1—C9—C10—C11	−178.1 (3)	Cl1—C31—C32—C33	−179.6 (2)
C9—C10—C11—C12	−0.8 (5)	C31—C32—C33—C28	−0.4 (4)
C10—C11—C12—C13	0.8 (6)	C29—C28—C33—C32	1.6 (4)
C11—C12—C13—C14	−0.1 (6)	C27—C28—C33—C32	177.5 (3)
C12—C13—C14—C9	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ⁱ	0.93	2.78	3.706 (3)	177
C10—H10···Cl2ⁱⁱ	0.93	3.06	3.974 (3)	167

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₆Cl₂N₂
M_r	509.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	14.3560 (6), 10.0621 (4), 18.3872 (8)
β (°)	91.427 (1)
V (Å³)	2655.24 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.20 × 0.12 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18622, 4657, 3312
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.163, 1.04
No. of reflections	4657
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.36

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

Cl1—C31	1.737 (4)	N2—C5	1.267 (4)
Cl2—C18	1.745 (3)	C6—C27	1.333 (4)

N2—C5—C4	128.3 (3)	C6—C27—C28	131.1 (3)
C27—C6—C1	128.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ⁱ	0.93	2.78	3.706 (3)	177
C10—H10···Cl2ⁱⁱ	0.93	3.06	3.974 (3)	167

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1/2, −y+1/2, z+1/2.

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