4,8,9,10-Tetrakis(4-chloro­phenyl)-1,3-di­aza­adamantan-6-one

Krishnakumar, R.V.; Nandhini, M.S.; Vijayakumar, V.; Natarajan, S.; Sundaravadivelu, M.; Perumal, S.; Mostad, A.

doi:10.1107/S1600536801013277

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4,8,9,10-Tetrakis(4-chlorophenyl)-1,3-diazaadamantan-6-one

R. V. Krishnakumar, M. S. Nandhini, V. Vijayakumar, S. Natarajan, M. Sundaravadivelu, S. Perumal and A. Mostad

In the title compound, C₃₂H₂₄Cl₄N₂O, all four six-membered rings which constitute the diazaadamantanone cage adopt chair conformations. The crystal structure is stabilized by Cl

Cl interactions and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013277/ci6033sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013277/ci6033Isup2.hkl Contains datablock I

CCDC reference: 172213

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.061
wR factor = 0.149
Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



WEIGH_01  Alert C Extra text has been found in the
          _refine_ls_weighting_scheme field. This should be in the
          _refine_ls_weighting_details field.
          Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+8.0771P] where P =
          Weighting scheme identified as calc


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The present X-ray investigations on the title compound, 4,8,9,10-tetrakis(4-chlorophenyl)-1,3-diazaadamantan-6-one, (I), was carried out with a view to observing possible differences in the crystal and molecular structures upon exchange of substituents and obtain some information about the nature of specific substituent or specific interactions. Moreover, crystallographic investigations on symmetrically shaped molecules are expected to provide insights into the nature and strength of intermolecular interactions and their role in effecting symmetry carry-over from the free state to the solid. Recently, the crystal structure of a methoxy-substituted analogue of the title compound, 4,8,9,10-tetrakis(4-methoxyphenyl)-1,3-diazaadamantan-6-one benzene solvate, was elucidated in our laboratory (Krishnakumar et al., 2001).

Fig. 1 shows the crystallographic numbering scheme adopted. No significant differences in the geometry of the diazaadamantanone cage are seen as it is known to be inherently rigid and symmetrical. All four six-membered rings which constitute the diazaadamantanone cage adopt chair conformations, which is the most preferred conformation for adamantanones, irrespective of substitutions. A molecular fit of (I) with its methoxy-substituted analogue shows a near perfect fit, except for a slight rotation of the two axially substituted phenyl rings. Thus, it seems that there is no loss of molecular symmetry as a result of chloro substitution, though the molecule does not lie across the mirror plane as in the case of the methoxy-substituted analogue.

It is known that the regular hexagonal geometry of benzene is perturbed when the ring is substituted with strong electron-donating or electron-withdrawing groups (Domenicano & Murray-Rust, 1979; Domenicano et al., 1983). However, in the title compound, the chloro substituent does not play any significant role in deforming the phenyl rings.

The crystal packing is stabilized by Cl···Cl interactions (Fig. 2) in addition to C—H···O hydrogen bonds. The two short Cl···Cl distances observed are: Cl47···Cl77(1 - x, y + 1/2, -z + 3/2) = 3.466 (3) Å and Cl67···Cl77(x - 1, y + 1, z) = 3.346 (3) Å. These values are significantly shorter than the sum of the van der Waals radii and demonstrate the special nature of Cl···Cl interactions (Schmidt, 1971; Williams & Hsu, 1985) and their dominant role in determining the packing modes in crystal structures.

Experimental top

Colourless single crystals of the title compound were obtained as transparent needles by slow evaporation of a benzene solution at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. ORTEP diagram (XP; Siemens, 1990) with displacement ellipsoids drawn at the 50% probability level showing the atom-numbering scheme adopted.
	Fig. 2. Packing of the molecules viewed down the a axis. Cl···Cl interactions are shown as dashed lines. H atoms have been omitted for clarity.

4,8,9,10-Tetrakis(4-chlorophenyl)-1,3-diazaadamantan-6-one top

Crystal data top

C₃₂H₂₄Cl₄N₂O	F(000) = 1224
M_r = 594.33	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
a = 6.818 (3) Å	Cell parameters from 25 reflections
b = 13.288 (4) Å	θ = 10–25°
c = 30.670 (14) Å	µ = 4.12 mm⁻¹
β = 94.47 (3)°	T = 293 K
V = 2770 (2) Å³	Needles, colourless
Z = 4	0.34 × 0.22 × 0.18 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	3549 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 70.1°, θ_min = 2.9°
/w–2/q scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
T_min = 0.42, T_max = 0.48	l = −37→37
5739 measured reflections	2 standard reflections every 200 reflections
5268 independent reflections	intensity decay: 2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.149	Calculated w = 1/[σ²(F_o²) + 8.0771P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max < 0.001
5268 reflections	Δρ_max = 0.37 e Å⁻³
353 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00100 (5)

Crystal data top

C₃₂H₂₄Cl₄N₂O	V = 2770 (2) Å³
M_r = 594.33	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 6.818 (3) Å	µ = 4.12 mm⁻¹
b = 13.288 (4) Å	T = 293 K
c = 30.670 (14) Å	0.34 × 0.22 × 0.18 mm
β = 94.47 (3)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	3549 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.036
T_min = 0.42, T_max = 0.48	2 standard reflections every 200 reflections
5739 measured reflections	intensity decay: 2%
5268 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.16	Δρ_max = 0.37 e Å⁻³
5268 reflections	Δρ_min = −0.40 e Å⁻³
353 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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.2913 (5)	0.7303 (3)	0.58381 (11)	0.0366 (8)
O11	−0.1514 (4)	0.6354 (3)	0.64983 (11)	0.0537 (9)
C2	0.4423 (6)	0.7662 (3)	0.61705 (13)	0.0371 (10)
H2A	0.4675	0.8368	0.6117	0.045*
H2B	0.5634	0.7297	0.6137	0.045*
N3	0.3890 (5)	0.7546 (3)	0.66238 (11)	0.0365 (8)
C4	0.2101 (6)	0.8164 (3)	0.66696 (13)	0.0360 (9)
H4	0.2430	0.8849	0.6582	0.043*
C41	0.1532 (6)	0.8238 (3)	0.71392 (14)	0.0401 (10)
C42	−0.0375 (7)	0.8098 (4)	0.72520 (16)	0.0479 (12)
H42	−0.1371	0.7977	0.7033	0.057*
C43	−0.0832 (7)	0.8133 (4)	0.76859 (16)	0.0517 (12)
H43	−0.2115	0.8028	0.7759	0.062*
C44	0.0651 (8)	0.8326 (4)	0.80042 (16)	0.0522 (13)
C45	0.2534 (8)	0.8519 (4)	0.79013 (16)	0.0584 (14)
H45	0.3512	0.8674	0.8119	0.070*
C46	0.2954 (7)	0.8478 (4)	0.74690 (16)	0.0508 (12)
H46	0.4227	0.8616	0.7397	0.061*
Cl47	0.0100 (2)	0.82985 (13)	0.85482 (4)	0.0755 (5)
C5	0.0418 (6)	0.7804 (4)	0.63387 (14)	0.0414 (11)
H5	−0.0782	0.8196	0.6368	0.050*
C6	0.1101 (6)	0.7893 (3)	0.58664 (14)	0.0403 (10)
H6	0.0083	0.7574	0.5669	0.048*
C61	0.1382 (6)	0.8948 (4)	0.56972 (15)	0.0427 (11)
C62	0.0758 (7)	0.9813 (4)	0.58954 (16)	0.0524 (13)
H62	0.0093	0.9759	0.6148	0.063*
C63	0.1099 (8)	1.0758 (4)	0.57272 (18)	0.0604 (14)
H63	0.0678	1.1334	0.5865	0.073*
C64	0.2068 (7)	1.0826 (4)	0.53553 (18)	0.0542 (13)
C65	0.2617 (7)	0.9987 (4)	0.51338 (17)	0.0535 (13)
H65	0.3200	1.0049	0.4871	0.064*
C66	0.2287 (7)	0.9048 (4)	0.53099 (16)	0.0507 (12)
H66	0.2679	0.8475	0.5166	0.061*
Cl67	0.2628 (2)	1.20020 (11)	0.51462 (6)	0.0817 (5)
C7	0.2472 (6)	0.6241 (3)	0.59039 (14)	0.0393 (10)
H7	0.1318	0.6076	0.5706	0.047*
C71	0.4142 (6)	0.5568 (3)	0.57784 (14)	0.0394 (10)
C72	0.5537 (7)	0.5921 (4)	0.55083 (14)	0.0435 (11)
H72	0.5487	0.6589	0.5418	0.052*
C73	0.6987 (7)	0.5307 (4)	0.53709 (15)	0.0477 (12)
H73	0.7910	0.5557	0.5191	0.057*
C74	0.7059 (7)	0.4317 (4)	0.55018 (15)	0.0470 (11)
C75	0.5678 (7)	0.3935 (4)	0.57610 (16)	0.0541 (13)
H75	0.5714	0.3260	0.5842	0.065*
C76	0.4244 (7)	0.4560 (4)	0.58989 (16)	0.0477 (12)
H76	0.3320	0.4302	0.6077	0.057*
Cl77	0.8883 (2)	0.35305 (12)	0.53312 (5)	0.0693 (4)
C8	0.1875 (6)	0.6072 (3)	0.63831 (13)	0.0368 (10)
H8	0.1605	0.5360	0.6436	0.044*
C9	0.3605 (6)	0.6450 (3)	0.66923 (13)	0.0353 (9)
H9	0.4777	0.6127	0.6590	0.042*
C91	0.3596 (6)	0.6161 (3)	0.71697 (14)	0.0385 (10)
C92	0.1952 (7)	0.5834 (4)	0.73677 (16)	0.0472 (11)
H92	0.0764	0.5753	0.7201	0.057*
C93	0.2061 (8)	0.5625 (4)	0.78117 (16)	0.0544 (13)
H93	0.0951	0.5402	0.7942	0.065*
C94	0.3804 (8)	0.5746 (4)	0.80584 (16)	0.0541 (13)
C95	0.5459 (7)	0.6029 (4)	0.78700 (17)	0.0574 (14)
H95	0.6652	0.6083	0.8037	0.069*
C96	0.5349 (7)	0.6236 (4)	0.74250 (15)	0.0485 (12)
H96	0.6481	0.6429	0.7296	0.058*
Cl97	0.3921 (3)	0.55127 (16)	0.86172 (5)	0.0923 (6)
C10	0.0069 (6)	0.6700 (3)	0.64207 (13)	0.0373 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0326 (18)	0.039 (2)	0.0379 (19)	0.0042 (16)	0.0006 (15)	0.0019 (16)
O11	0.0305 (16)	0.065 (2)	0.066 (2)	−0.0058 (16)	0.0064 (15)	0.0058 (18)
C2	0.033 (2)	0.040 (2)	0.038 (2)	0.0004 (19)	0.0055 (18)	0.0039 (19)
N3	0.0328 (18)	0.038 (2)	0.0385 (19)	0.0022 (15)	0.0040 (15)	0.0036 (16)
C4	0.036 (2)	0.033 (2)	0.040 (2)	0.0033 (18)	0.0052 (18)	0.0026 (18)
C41	0.044 (3)	0.036 (2)	0.041 (2)	0.004 (2)	0.006 (2)	0.0011 (19)
C42	0.045 (3)	0.052 (3)	0.048 (3)	0.005 (2)	0.009 (2)	−0.003 (2)
C43	0.050 (3)	0.053 (3)	0.054 (3)	0.005 (2)	0.016 (2)	0.001 (2)
C44	0.066 (3)	0.050 (3)	0.042 (3)	0.013 (3)	0.013 (2)	−0.003 (2)
C45	0.061 (3)	0.070 (4)	0.043 (3)	−0.001 (3)	0.000 (2)	−0.009 (3)
C46	0.047 (3)	0.053 (3)	0.053 (3)	−0.007 (2)	0.004 (2)	−0.007 (2)
Cl47	0.0914 (11)	0.0922 (11)	0.0449 (7)	0.0117 (9)	0.0180 (7)	−0.0045 (7)
C5	0.035 (2)	0.049 (3)	0.041 (2)	0.008 (2)	0.0059 (19)	0.005 (2)
C6	0.039 (2)	0.043 (3)	0.038 (2)	0.007 (2)	0.0002 (19)	0.001 (2)
C61	0.038 (2)	0.044 (3)	0.045 (3)	0.010 (2)	−0.003 (2)	0.002 (2)
C62	0.054 (3)	0.058 (3)	0.046 (3)	0.018 (3)	0.008 (2)	0.007 (2)
C63	0.073 (4)	0.044 (3)	0.064 (3)	0.017 (3)	0.006 (3)	0.004 (3)
C64	0.049 (3)	0.048 (3)	0.065 (3)	0.006 (2)	−0.003 (3)	0.016 (3)
C65	0.041 (3)	0.062 (3)	0.058 (3)	0.005 (2)	0.007 (2)	0.014 (3)
C66	0.048 (3)	0.054 (3)	0.051 (3)	0.012 (2)	0.010 (2)	0.006 (2)
Cl67	0.0757 (10)	0.0542 (9)	0.1157 (14)	0.0005 (7)	0.0107 (9)	0.0261 (9)
C7	0.037 (2)	0.040 (2)	0.041 (2)	−0.0010 (19)	0.0019 (19)	−0.004 (2)
C71	0.039 (2)	0.041 (2)	0.039 (2)	0.002 (2)	0.0012 (19)	−0.002 (2)
C72	0.054 (3)	0.040 (3)	0.038 (2)	0.002 (2)	0.011 (2)	0.000 (2)
C73	0.049 (3)	0.058 (3)	0.037 (2)	0.004 (2)	0.011 (2)	−0.003 (2)
C74	0.046 (3)	0.056 (3)	0.039 (2)	0.011 (2)	0.004 (2)	−0.005 (2)
C75	0.063 (3)	0.044 (3)	0.057 (3)	0.009 (2)	0.013 (3)	0.002 (2)
C76	0.048 (3)	0.044 (3)	0.053 (3)	0.002 (2)	0.015 (2)	0.007 (2)
Cl77	0.0754 (9)	0.0760 (10)	0.0588 (8)	0.0304 (8)	0.0194 (7)	−0.0013 (7)
C8	0.035 (2)	0.039 (2)	0.036 (2)	−0.0010 (19)	0.0033 (18)	0.0031 (19)
C9	0.031 (2)	0.037 (2)	0.039 (2)	0.0016 (18)	0.0055 (17)	0.0044 (19)
C91	0.039 (2)	0.034 (2)	0.043 (2)	0.0019 (19)	0.0033 (19)	0.0072 (19)
C92	0.037 (2)	0.048 (3)	0.058 (3)	0.000 (2)	0.006 (2)	0.009 (2)
C93	0.052 (3)	0.059 (3)	0.054 (3)	−0.005 (3)	0.016 (2)	0.017 (3)
C94	0.060 (3)	0.056 (3)	0.047 (3)	0.005 (3)	0.008 (2)	0.015 (2)
C95	0.047 (3)	0.072 (4)	0.052 (3)	0.001 (3)	−0.003 (2)	0.015 (3)
C96	0.039 (3)	0.059 (3)	0.048 (3)	−0.004 (2)	0.002 (2)	0.012 (2)
Cl97	0.0928 (12)	0.1329 (16)	0.0516 (8)	0.0040 (11)	0.0078 (8)	0.0351 (9)
C10	0.030 (2)	0.048 (3)	0.034 (2)	0.0002 (19)	−0.0010 (17)	−0.0024 (19)

Geometric parameters (Å, º) top

N1—C7	1.460 (5)	C64—Cl67	1.743 (5)
N1—C2	1.471 (5)	C65—C66	1.386 (7)
N1—C6	1.471 (5)	C65—H65	0.9300
O11—C10	1.213 (5)	C66—H66	0.9300
C2—N3	1.472 (5)	C7—C71	1.520 (6)
C2—H2A	0.9700	C7—C8	1.571 (6)
C2—H2B	0.9700	C7—H7	0.9800
N3—C4	1.486 (5)	C71—C76	1.390 (6)
N3—C9	1.487 (5)	C71—C72	1.390 (6)
C4—C41	1.524 (6)	C72—C73	1.373 (6)
C4—C5	1.547 (6)	C72—H72	0.9300
C4—H4	0.9800	C73—C74	1.375 (7)
C41—C46	1.383 (6)	C73—H73	0.9300
C41—C42	1.384 (6)	C74—C75	1.376 (7)
C42—C43	1.391 (6)	C74—Cl77	1.736 (5)
C42—H42	0.9300	C75—C76	1.375 (6)
C43—C44	1.374 (7)	C75—H75	0.9300
C43—H43	0.9300	C76—H76	0.9300
C44—C45	1.370 (7)	C8—C10	1.499 (6)
C44—Cl47	1.739 (5)	C8—C9	1.539 (6)
C45—C46	1.379 (7)	C8—H8	0.9800
C45—H45	0.9300	C9—C91	1.514 (6)
C46—H46	0.9300	C9—H9	0.9800
C5—C10	1.511 (6)	C91—C96	1.381 (6)
C5—C6	1.560 (6)	C91—C92	1.386 (6)
C5—H5	0.9800	C92—C93	1.386 (6)
C6—C61	1.513 (6)	C92—H92	0.9300
C6—H6	0.9800	C93—C94	1.368 (7)
C61—C62	1.383 (6)	C93—H93	0.9300
C61—C66	1.387 (6)	C94—C95	1.360 (7)
C62—C63	1.384 (7)	C94—Cl97	1.737 (5)
C62—H62	0.9300	C95—C96	1.388 (6)
C63—C64	1.365 (7)	C95—H95	0.9300
C63—H63	0.9300	C96—H96	0.9300
C64—C65	1.372 (7)

C7—N1—C2	111.0 (3)	C66—C65—H65	120.7
C7—N1—C6	108.9 (3)	C65—C66—C61	121.1 (5)
C2—N1—C6	109.4 (3)	C65—C66—H66	119.5
N1—C2—N3	114.2 (3)	C61—C66—H66	119.5
N1—C2—H2A	108.7	N1—C7—C71	111.5 (4)
N3—C2—H2A	108.7	N1—C7—C8	109.7 (3)
N1—C2—H2B	108.7	C71—C7—C8	114.0 (4)
N3—C2—H2B	108.7	N1—C7—H7	107.1
H2A—C2—H2B	107.6	C71—C7—H7	107.1
C2—N3—C4	107.2 (3)	C8—C7—H7	107.1
C2—N3—C9	106.3 (3)	C76—C71—C72	117.5 (4)
C4—N3—C9	114.2 (3)	C76—C71—C7	121.5 (4)
N3—C4—C41	113.4 (3)	C72—C71—C7	120.9 (4)
N3—C4—C5	109.9 (3)	C73—C72—C71	121.6 (4)
C41—C4—C5	114.2 (3)	C73—C72—H72	119.2
N3—C4—H4	106.3	C71—C72—H72	119.2
C41—C4—H4	106.3	C72—C73—C74	119.3 (4)
C5—C4—H4	106.3	C72—C73—H73	120.4
C46—C41—C42	117.8 (4)	C74—C73—H73	120.4
C46—C41—C4	119.4 (4)	C73—C74—C75	120.8 (4)
C42—C41—C4	122.8 (4)	C73—C74—Cl77	119.9 (4)
C41—C42—C43	121.3 (5)	C75—C74—Cl77	119.4 (4)
C41—C42—H42	119.3	C76—C75—C74	119.3 (5)
C43—C42—H42	119.3	C76—C75—H75	120.3
C44—C43—C42	118.6 (5)	C74—C75—H75	120.3
C44—C43—H43	120.7	C75—C76—C71	121.5 (4)
C42—C43—H43	120.7	C75—C76—H76	119.3
C45—C44—C43	121.5 (5)	C71—C76—H76	119.3
C45—C44—Cl47	120.1 (4)	C10—C8—C9	111.5 (4)
C43—C44—Cl47	118.4 (4)	C10—C8—C7	105.5 (3)
C44—C45—C46	118.9 (5)	C9—C8—C7	106.7 (3)
C44—C45—H45	120.6	C10—C8—H8	111.0
C46—C45—H45	120.6	C9—C8—H8	111.0
C45—C46—C41	121.7 (5)	C7—C8—H8	111.0
C45—C46—H46	119.1	N3—C9—C91	113.3 (3)
C41—C46—H46	119.1	N3—C9—C8	109.6 (3)
C10—C5—C4	108.0 (3)	C91—C9—C8	116.9 (3)
C10—C5—C6	106.9 (4)	N3—C9—H9	105.3
C4—C5—C6	109.0 (3)	C91—C9—H9	105.3
C10—C5—H5	110.9	C8—C9—H9	105.3
C4—C5—H5	110.9	C96—C91—C92	117.9 (4)
C6—C5—H5	110.9	C96—C91—C9	117.5 (4)
N1—C6—C61	110.1 (4)	C92—C91—C9	124.6 (4)
N1—C6—C5	109.1 (3)	C91—C92—C93	120.7 (5)
C61—C6—C5	116.3 (4)	C91—C92—H92	119.7
N1—C6—H6	106.9	C93—C92—H92	119.7
C61—C6—H6	106.9	C94—C93—C92	119.8 (5)
C5—C6—H6	106.9	C94—C93—H93	120.1
C62—C61—C66	118.0 (5)	C92—C93—H93	120.1
C62—C61—C6	124.6 (4)	C95—C94—C93	120.8 (5)
C66—C61—C6	117.3 (4)	C95—C94—Cl97	119.5 (4)
C61—C62—C63	121.6 (5)	C93—C94—Cl97	119.7 (4)
C61—C62—H62	119.2	C94—C95—C96	119.3 (5)
C63—C62—H62	119.2	C94—C95—H95	120.4
C64—C63—C62	118.5 (5)	C96—C95—H95	120.4
C64—C63—H63	120.7	C91—C96—C95	121.4 (4)
C62—C63—H63	120.7	C91—C96—H96	119.3
C63—C64—C65	122.0 (5)	C95—C96—H96	119.3
C63—C64—Cl67	120.0 (4)	O11—C10—C8	123.6 (4)
C65—C64—Cl67	118.0 (4)	O11—C10—C5	123.7 (4)
C64—C65—C66	118.7 (5)	C8—C10—C5	112.7 (4)
C64—C65—H65	120.7

C7—N1—C2—N3	−58.3 (5)	C2—N1—C7—C8	54.9 (4)
C6—N1—C2—N3	61.9 (4)	C6—N1—C7—C8	−65.5 (4)
N1—C2—N3—C4	−61.8 (4)	N1—C7—C71—C76	166.1 (4)
N1—C2—N3—C9	60.8 (4)	C8—C7—C71—C76	41.1 (6)
C2—N3—C4—C41	−172.0 (4)	N1—C7—C71—C72	−19.2 (6)
C9—N3—C4—C41	70.5 (5)	C8—C7—C71—C72	−144.2 (4)
C2—N3—C4—C5	59.0 (4)	C76—C71—C72—C73	−1.2 (7)
C9—N3—C4—C5	−58.5 (4)	C7—C71—C72—C73	−176.1 (4)
N3—C4—C41—C46	48.4 (6)	C71—C72—C73—C74	0.3 (7)
C5—C4—C41—C46	175.2 (4)	C72—C73—C74—C75	1.2 (7)
N3—C4—C41—C42	−133.3 (4)	C72—C73—C74—Cl77	−180.0 (4)
C5—C4—C41—C42	−6.4 (6)	C73—C74—C75—C76	−1.7 (8)
C46—C41—C42—C43	−4.0 (7)	Cl77—C74—C75—C76	179.5 (4)
C4—C41—C42—C43	177.6 (4)	C74—C75—C76—C71	0.7 (8)
C41—C42—C43—C44	1.0 (8)	C72—C71—C76—C75	0.7 (7)
C42—C43—C44—C45	2.4 (8)	C7—C71—C76—C75	175.6 (4)
C42—C43—C44—Cl47	−176.4 (4)	N1—C7—C8—C10	61.1 (4)
C43—C44—C45—C46	−2.6 (8)	C71—C7—C8—C10	−173.0 (4)
Cl47—C44—C45—C46	176.2 (4)	N1—C7—C8—C9	−57.5 (4)
C44—C45—C46—C41	−0.7 (8)	C71—C7—C8—C9	68.4 (5)
C42—C41—C46—C45	3.9 (7)	C2—N3—C9—C91	164.3 (3)
C4—C41—C46—C45	−177.6 (5)	C4—N3—C9—C91	−77.7 (4)
N3—C4—C5—C10	57.2 (4)	C2—N3—C9—C8	−63.2 (4)
C41—C4—C5—C10	−71.4 (4)	C4—N3—C9—C8	54.9 (4)
N3—C4—C5—C6	−58.6 (4)	C10—C8—C9—N3	−52.1 (4)
C41—C4—C5—C6	172.8 (4)	C7—C8—C9—N3	62.7 (4)
C7—N1—C6—C61	−166.8 (4)	C10—C8—C9—C91	78.6 (5)
C2—N1—C6—C61	71.7 (4)	C7—C8—C9—C91	−166.7 (4)
C7—N1—C6—C5	64.4 (4)	N3—C9—C91—C96	−69.2 (5)
C2—N1—C6—C5	−57.1 (4)	C8—C9—C91—C96	162.0 (4)
C10—C5—C6—N1	−59.5 (4)	N3—C9—C91—C92	110.5 (5)
C4—C5—C6—N1	57.0 (5)	C8—C9—C91—C92	−18.4 (6)
C10—C5—C6—C61	175.2 (4)	C96—C91—C92—C93	2.4 (7)
C4—C5—C6—C61	−68.3 (5)	C9—C91—C92—C93	−177.3 (4)
N1—C6—C61—C62	−136.6 (5)	C91—C92—C93—C94	0.2 (8)
C5—C6—C61—C62	−11.9 (7)	C92—C93—C94—C95	−2.8 (8)
N1—C6—C61—C66	45.1 (5)	C92—C93—C94—Cl97	178.4 (4)
C5—C6—C61—C66	169.8 (4)	C93—C94—C95—C96	2.6 (9)
C66—C61—C62—C63	−3.0 (7)	Cl97—C94—C95—C96	−178.6 (4)
C6—C61—C62—C63	178.7 (5)	C92—C91—C96—C95	−2.5 (7)
C61—C62—C63—C64	0.3 (8)	C9—C91—C96—C95	177.2 (5)
C62—C63—C64—C65	3.4 (8)	C94—C95—C96—C91	0.1 (8)
C62—C63—C64—Cl67	−177.1 (4)	C9—C8—C10—O11	−125.5 (4)
C63—C64—C65—C66	−4.2 (8)	C7—C8—C10—O11	119.0 (5)
Cl67—C64—C65—C66	176.2 (4)	C9—C8—C10—C5	56.1 (5)
C64—C65—C66—C61	1.4 (7)	C7—C8—C10—C5	−59.4 (4)
C62—C61—C66—C65	2.2 (7)	C4—C5—C10—O11	124.0 (4)
C6—C61—C66—C65	−179.5 (4)	C6—C5—C10—O11	−118.8 (5)
C2—N1—C7—C71	−72.4 (4)	C4—C5—C10—C8	−57.7 (4)
C6—N1—C7—C71	167.1 (3)	C6—C5—C10—C8	59.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O11ⁱ	0.98	2.58	3.428 (5)	144
C2—H2B···O11ⁱ	0.97	2.50	3.357 (5)	148

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₄Cl₄N₂O
M_r	594.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.818 (3), 13.288 (4), 30.670 (14)
β (°)	94.47 (3)
V (Å³)	2770 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.12
Crystal size (mm)	0.34 × 0.22 × 0.18

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.42, 0.48
No. of measured, independent and observed [I > 2σ(I)] reflections	5739, 5268, 3549
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.149, 1.16
No. of reflections	5268
No. of parameters	353
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.40

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O11ⁱ	0.98	2.58	3.428 (5)	144
C2—H2B···O11ⁱ	0.97	2.50	3.357 (5)	148

Symmetry code: (i) x+1, y, z.

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