3,8-Bis(4-chloro­phen­yl)-4,7-dimethyl­tricyclo­[4.2.2.02,5]deca-3,7-diene

Tomura, M.; Yamashita, Y.

doi:10.1107/S1600536808003206

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o545

doi:10.1107/S1600536808003206

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3,8-Bis(4-chlorophenyl)-4,7-dimethyltricyclo[4.2.2.0^2,5]deca-3,7-diene

Masaaki Tomura ^a ^* and Yoshiro Yamashita ^b

^aInstitute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and ^bDepartment of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan
^*Correspondence e-mail: tomura@ims.ac.jp

(Received 26 January 2008; accepted 29 January 2008; online 6 February 2008)

The title tricyclic diene, C₂₄H₂₂Cl₂, is the product of thermal ring-opening of a corresponding basketane (pentacyclo[4.4.0.0^2,5.0^3,8.0^4,7]decane) derivative. The cyclobutene ring is planar to within 0.0032 (12) Å and its geometry is normal. The two 4-chlorophenyl groups are oriented in an approximately face-to-face conformation with a dihedral angle of 44.14 (6)° between them. The 4-chlorophenyl group bonded to the cyclobutene ring lies almost in the plane of the cyclobutene ring, with a dihedral angle of 8.29 (17)° between the ring planes. The average intramolecular C⋯C distance between the two C=C bonds is 2.92 Å. In the crystal structure, the molecules are well separated with no close C—H⋯Cl or C—H⋯π intermolecular interactions.

Related literature

For the preparation of the title compound, see: Tezuka et al. (1976 ); Mukai et al. (1981 ). For cage compounds, see: Osawa & Yonemitsu (1992 ). For the crystal structures of compounds with a tricyclo[4.2.2.0^2,5]deca-3,7-diene skeleton, see: Lemley et al. (1976 ); Hanson (1981 ); Mehta et al. (1990 , 2003 ). For related literature, see: Allen (1984 , 2002 ); Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₂₂Cl₂
M_r = 381.32
Monoclinic, P 2₁ /c
a = 8.3389 (7) Å
b = 21.2224 (12) Å
c = 11.6074 (13) Å
β = 103.732 (7)°
V = 1995.5 (3) Å³
Z = 4
Cu Kα radiation
μ = 2.94 mm⁻¹
T = 295 (1) K
0.48 × 0.35 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.328, T_max = 0.484
4348 measured reflections
4070 independent reflections
2872 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections frequency: 120 min intensity decay: 1.3%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.160
S = 1.04
4070 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992 ); cell refinement: CAD-4 EXPRESS; data reduction: TEXSAN (Rigaku/MSC, 2000 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003206/sj2459sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003206/sj2459Isup2.hkl

checkCIF report

Comment top

There is considerable interest in the chemistry of highly strained polycyclic "cage" compounds (Osawa & Yonemitsu, 1992). The title tricyclic diene, (I), Fig 1, 3,8-bis(4-chlorophenyl)-4,7-dimethyltricyclo[4.2.2.0^2,5] deca-3,7-diene, C₂₄H₂₂Cl₂, is the product of thermal ring-opening of a corresponding basketane (pentacyclo[4.4.0.0^2,5.0^3,8.0^4,7]decane) and reverts to the basketane derivative quantitatively upon irradiation (Tezuka et al., 1976). A search for tricyclo[4.2.2.0^2,5]deca-3,7-diene skeleton in the Cambridge Structural Database (Version 5.29; Allen, 2002) gave only four examples, CTCYDD (Lemley et al., 1976), CNUNDC (Hanson, 1981), KEVGEX (Mehta et al., 1990) and GACFIA (Mehta et al., 2003).

Bond lengths and angles in the molecule are within the normal ranges (Allen et al., 1987) and the geometry of the cyclobutene ring is also similar to that of cyclobutene (Allen, 1984). The cyclobutene ring adopts a planar, rather than a puckered conformation, where the maximum deviation of the fitted atoms from the least-squares plane is 0.0032 (12) Å. The C3—C4 bond distance [1.562 (3) Å] in the cyclobutene ring is 1.8% shorter than the corresponding distance in the 2,3,4,5-tetrachloro derivative (Lemley et al., 1976). The two 4-chlorophenyl groups are oriented in an approximately face-to-face conformation with a dihedral angle of 44.14 (6)° between them. The 4-chlorophenyl group bonded to the cyclobutene ring lies almost in the plane of the cyclobutene ring with a dihedral angle of 8.29 (17)° between the ring planes. Upon irradiation, an intramolecular photocyclization occurs between the C1?C2 and C6?C7 bonds. Intramolecular C1···C6 and C2···C7 distances are 2.918 (3) and 2.921 (3) Å, respectively, and the dihedral angle between the cyclobutene plane (C1–C4) and the C5–C8 plane is 60.89 (12)°. In the crystal structure the molecules are well separated with no close C—H···Cl or C—H···π intermolecular interactions.

Related literature top

For the preparation of the title compound, see: Tezuka et al. (1976); Mukai et al. (1981). For cage compounds, see: Osawa & Yonemitsu (1992). For the crystal structures of compounds with the tricyclo[4.2.2.0^2,5]deca-3,7-diene skeleton, see: Lemley et al. (1976); Hanson (1981); Mehta et al. (1990, 2003). For other related literature, see: Allen (1984, 2002); Allen et al. (1987).

Experimental top

The compound (I) was synthesized according to a literature method (Tezuka et al., 1976; Mukai et al., 1981). Colorless crystals of (I) suitable for X-ray analysis were grown from a dichloromethane solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1992); data reduction: TEXSAN (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 20% probability displacement ellipsoids for non-H atoms. H atoms are shown as small spheres with arbitrary radii.

3,8-Bis(4-chlorophenyl)-4,7-dimethyltricyclo[4.2.2.0^2,5]deca-3,7-diene top

Crystal data top

C₂₄H₂₂Cl₂	F(000) = 800
M_r = 381.32	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.3389 (7) Å	θ = 22.7–42.6°
b = 21.2224 (12) Å	µ = 2.94 mm⁻¹
c = 11.6074 (13) Å	T = 295 K
β = 103.732 (7)°	Block, colorless
V = 1995.5 (3) Å³	0.48 × 0.35 × 0.25 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2872 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	R_int = 0.021
Graphite monochromator	θ_max = 74.2°, θ_min = 4.2°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→26
T_min = 0.328, T_max = 0.484	l = −14→14
4348 measured reflections	3 standard reflections every 120 min
4070 independent reflections	intensity decay: 1.3%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0822P)² + 0.357P] where P = (F_o² + 2F_c²)/3
4070 reflections	(Δ/σ)_max = 0.007
237 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₂₂Cl₂	V = 1995.5 (3) Å³
M_r = 381.32	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.3389 (7) Å	µ = 2.94 mm⁻¹
b = 21.2224 (12) Å	T = 295 K
c = 11.6074 (13) Å	0.48 × 0.35 × 0.25 mm
β = 103.732 (7)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2872 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.021
T_min = 0.328, T_max = 0.484	3 standard reflections every 120 min
4348 measured reflections	intensity decay: 1.3%
4070 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
4070 reflections	Δρ_min = −0.33 e Å⁻³
237 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
Cl1	0.49013 (12)	0.19930 (4)	1.21790 (6)	0.1028 (3)
Cl2	1.19192 (12)	0.35095 (4)	0.98762 (11)	0.1347 (4)
C1	0.7177 (3)	0.00447 (11)	0.7920 (3)	0.0761 (7)
C2	0.6407 (3)	0.05850 (10)	0.8097 (2)	0.0661 (5)
C3	0.5989 (3)	0.07597 (11)	0.6796 (2)	0.0652 (5)
H3	0.4802	0.0750	0.6432	0.078*
C4	0.6896 (3)	0.01375 (11)	0.6609 (2)	0.0749 (7)
H4	0.6163	−0.0179	0.6144	0.090*
C5	0.8386 (3)	0.03011 (12)	0.6096 (2)	0.0753 (7)
H5	0.9014	−0.0079	0.6011	0.090*
C6	0.9467 (3)	0.07722 (11)	0.6897 (2)	0.0656 (5)
C7	0.8686 (2)	0.13047 (10)	0.70463 (19)	0.0600 (5)
C8	0.6880 (2)	0.13196 (11)	0.63804 (19)	0.0618 (5)
H8	0.6364	0.1719	0.6515	0.074*
C9	0.6785 (3)	0.12218 (14)	0.5049 (2)	0.0793 (7)
H9A	0.5639	0.1196	0.4614	0.095*
H9B	0.7290	0.1576	0.4743	0.095*
C10	0.7692 (3)	0.06101 (14)	0.4880 (2)	0.0858 (8)
H10A	0.8585	0.0704	0.4503	0.103*
H10B	0.6934	0.0323	0.4372	0.103*
C11	0.8109 (4)	−0.04637 (13)	0.8691 (3)	0.1037 (10)
H11A	0.9228	−0.0472	0.8609	0.156*
H11B	0.7596	−0.0863	0.8455	0.156*
H11C	0.8102	−0.0382	0.9503	0.156*
C12	1.1250 (3)	0.06200 (12)	0.7406 (3)	0.0787 (7)
H12A	1.1803	0.0985	0.7801	0.118*
H12B	1.1756	0.0497	0.6779	0.118*
H12C	1.1333	0.0281	0.7964	0.118*
C13	0.6085 (3)	0.09224 (10)	0.9117 (2)	0.0617 (5)
C14	0.5426 (3)	0.15260 (11)	0.8976 (2)	0.0721 (6)
H14	0.5194	0.1709	0.8227	0.086*
C15	0.5102 (3)	0.18636 (12)	0.9912 (2)	0.0759 (6)
H15	0.4683	0.2271	0.9798	0.091*
C16	0.5404 (3)	0.15904 (12)	1.1008 (2)	0.0710 (6)
C17	0.6047 (4)	0.09927 (14)	1.1188 (2)	0.0875 (8)
H17	0.6248	0.0809	1.1936	0.105*
C18	0.6390 (4)	0.06678 (12)	1.0248 (2)	0.0838 (7)
H18	0.6840	0.0266	1.0375	0.101*
C19	0.9420 (3)	0.18508 (10)	0.77687 (19)	0.0574 (5)
C20	0.9320 (3)	0.24474 (12)	0.7278 (2)	0.0772 (7)
H20	0.8739	0.2505	0.6496	0.093*
C21	1.0060 (4)	0.29581 (13)	0.7920 (3)	0.0924 (9)
H21	0.9986	0.3355	0.7573	0.111*
C22	1.0901 (3)	0.28762 (13)	0.9069 (3)	0.0810 (7)
C23	1.0954 (3)	0.23022 (14)	0.9607 (2)	0.0826 (7)
H23	1.1486	0.2256	1.0403	0.099*
C24	1.0210 (3)	0.17907 (12)	0.8956 (2)	0.0736 (6)
H24	1.0239	0.1400	0.9321	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1386 (7)	0.1011 (5)	0.0714 (4)	−0.0031 (5)	0.0303 (4)	−0.0133 (3)
Cl2	0.1042 (6)	0.0980 (6)	0.1974 (11)	−0.0306 (5)	0.0271 (6)	−0.0685 (6)
C1	0.0663 (14)	0.0549 (12)	0.1071 (19)	0.0000 (10)	0.0209 (13)	−0.0022 (12)
C2	0.0562 (12)	0.0574 (12)	0.0851 (15)	0.0019 (9)	0.0176 (11)	0.0013 (11)
C3	0.0487 (10)	0.0662 (12)	0.0783 (14)	0.0005 (9)	0.0103 (10)	−0.0110 (11)
C4	0.0571 (12)	0.0666 (14)	0.1002 (18)	−0.0060 (10)	0.0171 (12)	−0.0246 (13)
C5	0.0591 (12)	0.0737 (14)	0.0931 (17)	0.0031 (11)	0.0181 (12)	−0.0285 (13)
C6	0.0520 (11)	0.0691 (13)	0.0746 (14)	0.0025 (10)	0.0127 (10)	−0.0114 (11)
C7	0.0524 (11)	0.0636 (12)	0.0625 (12)	0.0005 (9)	0.0110 (9)	−0.0040 (9)
C8	0.0530 (11)	0.0680 (12)	0.0626 (12)	0.0069 (9)	0.0104 (9)	−0.0029 (10)
C9	0.0639 (13)	0.108 (2)	0.0635 (13)	0.0046 (13)	0.0109 (11)	−0.0095 (13)
C10	0.0675 (14)	0.113 (2)	0.0764 (16)	−0.0002 (14)	0.0156 (12)	−0.0309 (15)
C11	0.101 (2)	0.0642 (15)	0.150 (3)	0.0211 (14)	0.039 (2)	0.0158 (17)
C12	0.0565 (12)	0.0775 (15)	0.0983 (18)	0.0090 (11)	0.0107 (12)	−0.0098 (13)
C13	0.0554 (11)	0.0564 (11)	0.0729 (13)	0.0017 (9)	0.0141 (10)	0.0067 (10)
C14	0.0868 (16)	0.0643 (13)	0.0687 (13)	0.0126 (11)	0.0255 (12)	0.0139 (11)
C15	0.0925 (17)	0.0610 (13)	0.0795 (15)	0.0102 (12)	0.0308 (13)	0.0075 (11)
C16	0.0742 (14)	0.0717 (14)	0.0666 (13)	−0.0071 (11)	0.0157 (11)	−0.0029 (11)
C17	0.105 (2)	0.0858 (17)	0.0691 (15)	0.0102 (16)	0.0156 (14)	0.0184 (13)
C18	0.0937 (18)	0.0691 (15)	0.0869 (17)	0.0185 (13)	0.0180 (14)	0.0162 (13)
C19	0.0526 (10)	0.0575 (11)	0.0636 (12)	0.0002 (8)	0.0163 (9)	−0.0031 (9)
C20	0.0820 (16)	0.0708 (15)	0.0762 (15)	−0.0063 (12)	0.0137 (12)	0.0103 (12)
C21	0.095 (2)	0.0620 (14)	0.121 (2)	−0.0147 (13)	0.0270 (18)	0.0067 (15)
C22	0.0630 (14)	0.0708 (15)	0.112 (2)	−0.0092 (11)	0.0267 (14)	−0.0259 (15)
C23	0.0796 (17)	0.0903 (18)	0.0723 (15)	−0.0016 (13)	0.0067 (12)	−0.0191 (14)
C24	0.0837 (16)	0.0633 (13)	0.0685 (14)	−0.0029 (11)	0.0075 (12)	0.0006 (11)

Geometric parameters (Å, º) top

Cl1—C16	1.739 (3)	C11—H11A	0.9600
Cl2—C22	1.740 (3)	C11—H11B	0.9600
C1—C2	1.353 (3)	C11—H11C	0.9600
C1—C11	1.496 (4)	C12—H12A	0.9600
C1—C4	1.496 (4)	C12—H12B	0.9600
C2—C13	1.462 (3)	C12—H12C	0.9600
C2—C3	1.513 (3)	C13—C18	1.386 (3)
C3—C8	1.538 (3)	C13—C14	1.388 (3)
C3—C4	1.562 (3)	C14—C15	1.381 (3)
C3—H3	0.9800	C14—H14	0.9300
C4—C5	1.540 (3)	C15—C16	1.366 (3)
C4—H4	0.9800	C15—H15	0.9300
C5—C6	1.510 (3)	C16—C17	1.374 (4)
C5—C10	1.539 (4)	C17—C18	1.377 (4)
C5—H5	0.9800	C17—H17	0.9300
C6—C7	1.336 (3)	C18—H18	0.9300
C6—C12	1.499 (3)	C19—C20	1.383 (3)
C7—C19	1.476 (3)	C19—C24	1.385 (3)
C7—C8	1.521 (3)	C20—C21	1.376 (4)
C8—C9	1.543 (3)	C20—H20	0.9300
C8—H8	0.9800	C21—C22	1.363 (4)
C9—C10	1.538 (4)	C21—H21	0.9300
C9—H9A	0.9700	C22—C23	1.365 (4)
C9—H9B	0.9700	C23—C24	1.383 (3)
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700	C24—H24	0.9300

C2—C1—C11	135.9 (3)	C1—C11—H11A	109.5
C2—C1—C4	94.5 (2)	C1—C11—H11B	109.5
C11—C1—C4	129.5 (2)	H11A—C11—H11B	109.5
C1—C2—C13	136.3 (2)	C1—C11—H11C	109.5
C1—C2—C3	93.5 (2)	H11A—C11—H11C	109.5
C13—C2—C3	130.17 (19)	H11B—C11—H11C	109.5
C2—C3—C8	119.23 (18)	C6—C12—H12A	109.5
C2—C3—C4	85.80 (18)	C6—C12—H12B	109.5
C8—C3—C4	108.89 (17)	H12A—C12—H12B	109.5
C2—C3—H3	113.3	C6—C12—H12C	109.5
C8—C3—H3	113.3	H12A—C12—H12C	109.5
C4—C3—H3	113.3	H12B—C12—H12C	109.5
C1—C4—C5	118.5 (2)	C18—C13—C14	116.7 (2)
C1—C4—C3	86.23 (18)	C18—C13—C2	123.2 (2)
C5—C4—C3	109.0 (2)	C14—C13—C2	120.0 (2)
C1—C4—H4	113.4	C15—C14—C13	122.2 (2)
C5—C4—H4	113.4	C15—C14—H14	118.9
C3—C4—H4	113.4	C13—C14—H14	118.9
C6—C5—C10	108.8 (2)	C16—C15—C14	119.0 (2)
C6—C5—C4	109.20 (19)	C16—C15—H15	120.5
C10—C5—C4	106.8 (2)	C14—C15—H15	120.5
C6—C5—H5	110.6	C15—C16—C17	120.9 (2)
C10—C5—H5	110.6	C15—C16—Cl1	119.6 (2)
C4—C5—H5	110.6	C17—C16—Cl1	119.5 (2)
C7—C6—C12	126.8 (2)	C16—C17—C18	119.3 (2)
C7—C6—C5	113.71 (19)	C16—C17—H17	120.4
C12—C6—C5	119.4 (2)	C18—C17—H17	120.4
C6—C7—C19	126.06 (19)	C17—C18—C13	122.0 (2)
C6—C7—C8	113.95 (19)	C17—C18—H18	119.0
C19—C7—C8	119.98 (18)	C13—C18—H18	119.0
C7—C8—C3	108.55 (18)	C20—C19—C24	117.5 (2)
C7—C8—C9	108.40 (18)	C20—C19—C7	120.6 (2)
C3—C8—C9	107.24 (19)	C24—C19—C7	121.9 (2)
C7—C8—H8	110.8	C21—C20—C19	121.5 (2)
C3—C8—H8	110.8	C21—C20—H20	119.2
C9—C8—H8	110.8	C19—C20—H20	119.2
C10—C9—C8	109.4 (2)	C22—C21—C20	119.3 (3)
C10—C9—H9A	109.8	C22—C21—H21	120.3
C8—C9—H9A	109.8	C20—C21—H21	120.3
C10—C9—H9B	109.8	C21—C22—C23	121.0 (2)
C8—C9—H9B	109.8	C21—C22—Cl2	120.0 (2)
H9A—C9—H9B	108.3	C23—C22—Cl2	119.0 (2)
C9—C10—C5	109.39 (19)	C22—C23—C24	119.2 (2)
C9—C10—H10A	109.8	C22—C23—H23	120.4
C5—C10—H10A	109.8	C24—C23—H23	120.4
C9—C10—H10B	109.8	C23—C24—C19	121.2 (2)
C5—C10—H10B	109.8	C23—C24—H24	119.4
H10A—C10—H10B	108.2	C19—C24—H24	119.4

C11—C1—C2—C13	−1.7 (5)	C4—C3—C8—C9	61.1 (2)
C4—C1—C2—C13	−177.6 (3)	C7—C8—C9—C10	54.9 (3)
C11—C1—C2—C3	176.4 (3)	C3—C8—C9—C10	−62.1 (2)
C4—C1—C2—C3	0.50 (19)	C8—C9—C10—C5	0.1 (3)
C1—C2—C3—C8	−109.8 (2)	C6—C5—C10—C9	−55.6 (3)
C13—C2—C3—C8	68.5 (3)	C4—C5—C10—C9	62.2 (3)
C1—C2—C3—C4	−0.48 (18)	C1—C2—C13—C18	−9.6 (4)
C13—C2—C3—C4	177.8 (2)	C3—C2—C13—C18	172.8 (2)
C2—C1—C4—C5	109.1 (2)	C1—C2—C13—C14	171.1 (3)
C11—C1—C4—C5	−67.2 (3)	C3—C2—C13—C14	−6.5 (4)
C2—C1—C4—C3	−0.48 (18)	C18—C13—C14—C15	0.7 (4)
C11—C1—C4—C3	−176.8 (3)	C2—C13—C14—C15	−179.9 (2)
C2—C3—C4—C1	0.43 (16)	C13—C14—C15—C16	−1.5 (4)
C8—C3—C4—C1	119.93 (19)	C14—C15—C16—C17	1.1 (4)
C2—C3—C4—C5	−118.5 (2)	C14—C15—C16—Cl1	−176.6 (2)
C8—C3—C4—C5	1.0 (3)	C15—C16—C17—C18	0.1 (4)
C1—C4—C5—C6	−41.3 (3)	Cl1—C16—C17—C18	177.8 (2)
C3—C4—C5—C6	54.8 (3)	C16—C17—C18—C13	−0.9 (5)
C1—C4—C5—C10	−158.8 (2)	C14—C13—C18—C17	0.5 (4)
C3—C4—C5—C10	−62.6 (2)	C2—C13—C18—C17	−178.8 (3)
C10—C5—C6—C7	57.9 (3)	C6—C7—C19—C20	125.7 (3)
C4—C5—C6—C7	−58.3 (3)	C8—C7—C19—C20	−54.0 (3)
C10—C5—C6—C12	−120.4 (2)	C6—C7—C19—C24	−55.3 (3)
C4—C5—C6—C12	123.4 (2)	C8—C7—C19—C24	125.1 (2)
C12—C6—C7—C19	−1.3 (4)	C24—C19—C20—C21	3.9 (4)
C5—C6—C7—C19	−179.5 (2)	C7—C19—C20—C21	−177.0 (2)
C12—C6—C7—C8	178.3 (2)	C19—C20—C21—C22	−0.5 (4)
C5—C6—C7—C8	0.2 (3)	C20—C21—C22—C23	−3.1 (4)
C6—C7—C8—C3	58.3 (3)	C20—C21—C22—Cl2	177.3 (2)
C19—C7—C8—C3	−122.0 (2)	C21—C22—C23—C24	3.2 (4)
C6—C7—C8—C9	−57.9 (3)	Cl2—C22—C23—C24	−177.2 (2)
C19—C7—C8—C9	121.8 (2)	C22—C23—C24—C19	0.3 (4)
C2—C3—C8—C7	40.1 (3)	C20—C19—C24—C23	−3.7 (4)
C4—C3—C8—C7	−55.8 (2)	C7—C19—C24—C23	177.2 (2)
C2—C3—C8—C9	156.98 (19)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂Cl₂
M_r	381.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.3389 (7), 21.2224 (12), 11.6074 (13)
β (°)	103.732 (7)
V (Å³)	1995.5 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.94
Crystal size (mm)	0.48 × 0.35 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.328, 0.484
No. of measured, independent and observed [I > 2σ(I)] reflections	4348, 4070, 2872
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.160, 1.04
No. of reflections	4070
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.33

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1992), TEXSAN (Rigaku/MSC, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Acknowledgements

We thank the Instrument Center of the Institute for Molecular Science for the X-ray structure analysis.

References

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