2,6-Bis(2-chloro-benzyl-idene)cyclo-hexanone.

In the title mol-ecule, C(20)H(16)Cl(2)O, the central cyclo-hexa-none ring adopts an envelope conformation. The two aromatic rings form a dihedral angle of 30.0 (1)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds and short Cl⋯O contacts [3.213 (3) Å].

Related literature

For general background, see: Tanaka & Toda (2000 ▶). For a similar crystal structure, see: Brinda et al. (2007 ▶).

Experimental

Crystal data

C20H16Cl2O

M = 343.23

Orthorhombic,

a = 14.4004 (15) Å

b = 8.1553 (10) Å

c = 28.593 (3) Å

V = 3358.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.39 mm−1

T = 298 K

0.42 × 0.32 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.854, T max = 0.937

13876 measured reflections

2962 independent reflections

1762 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.06

2962 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT (Siemens, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007648/cv2518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007648/cv2518Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H16Cl2O	Dx = 1.358 Mg m−3
Mr = 343.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2653 reflections
a = 14.4004 (15) Å	θ = 2.8–43.8°
b = 8.1553 (10) Å	µ = 0.39 mm−1
c = 28.593 (3) Å	T = 298 K
V = 3358.0 (6) Å3	Needle, colourless
Z = 8	0.42 × 0.32 × 0.17 mm
F(000) = 1424

Bruker SMART APEX CCD area-detector diffractometer	2962 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
graphite	Rint = 0.064
phi and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→17
Tmin = 0.854, Tmax = 0.937	k = −8→9
13876 measured reflections	l = −29→34

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0353P)2 + 3.2692P] where P = (Fo2 + 2Fc2)/3
2962 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	1.01278 (6)	1.01596 (12)	0.34622 (3)	0.0568 (3)
Cl2	0.72695 (8)	0.83897 (15)	0.07162 (3)	0.0783 (4)
O1	0.86474 (15)	0.7337 (3)	0.22424 (7)	0.0515 (7)
C1	0.7861 (2)	0.7354 (4)	0.24087 (10)	0.0342 (8)
C2	0.7724 (2)	0.7802 (4)	0.29170 (10)	0.0347 (8)
C3	0.6741 (2)	0.8022 (5)	0.30951 (11)	0.0472 (9)
H3A	0.6726	0.8954	0.3306	0.057*
H3B	0.6567	0.7058	0.3273	0.057*
C4	0.6032 (2)	0.8289 (5)	0.27104 (11)	0.0455 (9)
H4A	0.6145	0.9334	0.2559	0.055*
H4B	0.5413	0.8313	0.2844	0.055*
C5	0.6099 (2)	0.6916 (4)	0.23542 (11)	0.0399 (8)
H5A	0.6006	0.5870	0.2509	0.048*
H5B	0.5615	0.7046	0.2122	0.048*
C6	0.7032 (2)	0.6928 (4)	0.21178 (10)	0.0335 (7)
C7	0.8490 (2)	0.8002 (4)	0.31767 (10)	0.0412 (8)
H7	0.9051	0.7861	0.3020	0.049*
C8	0.8563 (2)	0.8412 (5)	0.36743 (11)	0.0458 (9)
C9	0.9282 (2)	0.9410 (5)	0.38404 (11)	0.0485 (9)
C10	0.9346 (3)	0.9856 (6)	0.43068 (13)	0.0654 (12)
H10	0.9817	1.0555	0.4406	0.078*
C11	0.8710 (3)	0.9260 (7)	0.46211 (14)	0.0806 (15)
H11	0.8753	0.9550	0.4935	0.097*
C12	0.8011 (3)	0.8238 (7)	0.44739 (14)	0.0836 (15)
H12	0.7585	0.7832	0.4689	0.100*
C13	0.7935 (3)	0.7809 (6)	0.40090 (12)	0.0626 (12)
H13	0.7461	0.7108	0.3915	0.075*
C14	0.7172 (2)	0.6681 (4)	0.16580 (11)	0.0399 (8)
H14	0.7776	0.6812	0.1549	0.048*
C15	0.6467 (2)	0.6227 (4)	0.13110 (10)	0.0382 (8)
C16	0.6448 (2)	0.6917 (4)	0.08648 (11)	0.0444 (9)
C17	0.5785 (3)	0.6500 (5)	0.05364 (12)	0.0561 (10)
H17	0.5785	0.7002	0.0244	0.067*
C18	0.5126 (3)	0.5339 (5)	0.06440 (13)	0.0610 (11)
H18	0.4672	0.5062	0.0426	0.073*
C19	0.5141 (3)	0.4588 (5)	0.10758 (13)	0.0588 (11)
H19	0.4707	0.3781	0.1146	0.071*
C20	0.5795 (2)	0.5029 (4)	0.14024 (11)	0.0461 (9)
H20	0.5791	0.4515	0.1693	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0448 (5)	0.0640 (7)	0.0615 (6)	−0.0018 (5)	−0.0062 (5)	−0.0015 (5)
Cl2	0.1071 (9)	0.0832 (8)	0.0447 (5)	−0.0501 (7)	−0.0081 (6)	0.0118 (5)
O1	0.0311 (14)	0.086 (2)	0.0376 (13)	−0.0010 (13)	0.0065 (11)	0.0017 (12)
C1	0.0311 (19)	0.037 (2)	0.0346 (17)	0.0016 (15)	0.0042 (15)	0.0061 (14)
C2	0.0328 (19)	0.038 (2)	0.0338 (17)	−0.0009 (15)	0.0062 (14)	0.0039 (14)
C3	0.038 (2)	0.060 (3)	0.0431 (19)	−0.0041 (18)	0.0083 (16)	−0.0082 (17)
C4	0.0317 (19)	0.051 (2)	0.054 (2)	0.0072 (16)	0.0020 (16)	−0.0050 (18)
C5	0.0316 (19)	0.046 (2)	0.0419 (18)	−0.0017 (16)	0.0002 (15)	0.0013 (16)
C6	0.0296 (18)	0.037 (2)	0.0336 (17)	0.0031 (14)	0.0025 (14)	0.0066 (14)
C7	0.032 (2)	0.054 (2)	0.0376 (18)	0.0038 (16)	0.0037 (15)	0.0027 (16)
C8	0.045 (2)	0.058 (2)	0.0338 (18)	0.0056 (18)	−0.0014 (16)	−0.0029 (17)
C9	0.050 (2)	0.055 (3)	0.040 (2)	0.0114 (19)	−0.0070 (17)	−0.0024 (17)
C10	0.068 (3)	0.078 (3)	0.050 (2)	0.011 (2)	−0.011 (2)	−0.014 (2)
C11	0.085 (4)	0.120 (4)	0.036 (2)	0.017 (3)	−0.008 (2)	−0.015 (3)
C12	0.076 (3)	0.134 (5)	0.041 (2)	0.001 (3)	0.010 (2)	0.007 (3)
C13	0.058 (3)	0.091 (3)	0.039 (2)	−0.003 (2)	0.0029 (19)	0.006 (2)
C14	0.0346 (19)	0.045 (2)	0.0405 (19)	−0.0006 (16)	0.0013 (15)	0.0063 (16)
C15	0.0365 (19)	0.044 (2)	0.0337 (17)	0.0016 (16)	0.0025 (15)	−0.0040 (15)
C16	0.058 (2)	0.041 (2)	0.0345 (18)	−0.0080 (18)	0.0020 (16)	−0.0019 (15)
C17	0.077 (3)	0.060 (3)	0.0318 (18)	−0.007 (2)	−0.0099 (19)	−0.0037 (18)
C18	0.062 (3)	0.070 (3)	0.051 (2)	−0.014 (2)	−0.010 (2)	−0.015 (2)
C19	0.054 (2)	0.066 (3)	0.056 (2)	−0.018 (2)	0.004 (2)	−0.009 (2)
C20	0.049 (2)	0.053 (2)	0.0370 (18)	−0.0034 (19)	0.0034 (16)	0.0057 (17)

Cl1—C9	1.739 (4)	C9—C10	1.385 (5)
Cl2—C16	1.738 (3)	C10—C11	1.372 (6)
O1—C1	1.228 (3)	C10—H10	0.9300
C1—C6	1.496 (4)	C11—C12	1.374 (6)
C1—C2	1.511 (4)	C11—H11	0.9300
C2—C7	1.340 (4)	C12—C13	1.379 (5)
C2—C3	1.514 (4)	C12—H12	0.9300
C3—C4	1.517 (4)	C13—H13	0.9300
C3—H3A	0.9700	C14—C15	1.467 (4)
C3—H3B	0.9700	C14—H14	0.9300
C4—C5	1.517 (4)	C15—C16	1.395 (4)
C4—H4A	0.9700	C15—C20	1.400 (4)
C4—H4B	0.9700	C16—C17	1.381 (5)
C5—C6	1.504 (4)	C17—C18	1.376 (5)
C5—H5A	0.9700	C17—H17	0.9300
C5—H5B	0.9700	C18—C19	1.378 (5)
C6—C14	1.345 (4)	C18—H18	0.9300
C7—C8	1.465 (4)	C19—C20	1.374 (5)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.400 (5)	C20—H20	0.9300
C8—C13	1.405 (5)
Cl1···O1i	3.213 (3)
C9—Cl1—O1i	165.55 (13)	C10—C9—Cl1	117.4 (3)
O1—C1—C6	121.2 (3)	C8—C9—Cl1	120.8 (3)
O1—C1—C2	119.7 (3)	C11—C10—C9	119.6 (4)
C6—C1—C2	119.1 (3)	C11—C10—H10	120.2
C7—C2—C1	117.0 (3)	C9—C10—H10	120.2
C7—C2—C3	124.7 (3)	C10—C11—C12	120.2 (4)
C1—C2—C3	118.3 (3)	C10—C11—H11	119.9
C2—C3—C4	113.7 (3)	C12—C11—H11	119.9
C2—C3—H3A	108.8	C11—C12—C13	120.5 (4)
C4—C3—H3A	108.8	C11—C12—H12	119.8
C2—C3—H3B	108.8	C13—C12—H12	119.8
C4—C3—H3B	108.8	C12—C13—C8	121.1 (4)
H3A—C3—H3B	107.7	C12—C13—H13	119.4
C3—C4—C5	109.8 (3)	C8—C13—H13	119.4
C3—C4—H4A	109.7	C6—C14—C15	126.6 (3)
C5—C4—H4A	109.7	C6—C14—H14	116.7
C3—C4—H4B	109.7	C15—C14—H14	116.7
C5—C4—H4B	109.7	C16—C15—C20	116.0 (3)
H4A—C4—H4B	108.2	C16—C15—C14	122.0 (3)
C6—C5—C4	110.7 (3)	C20—C15—C14	121.9 (3)
C6—C5—H5A	109.5	C17—C16—C15	122.4 (3)
C4—C5—H5A	109.5	C17—C16—Cl2	118.3 (3)
C6—C5—H5B	109.5	C15—C16—Cl2	119.3 (3)
C4—C5—H5B	109.5	C18—C17—C16	119.6 (3)
H5A—C5—H5B	108.1	C18—C17—H17	120.2
C14—C6—C1	117.4 (3)	C16—C17—H17	120.2
C14—C6—C5	124.9 (3)	C17—C18—C19	119.7 (3)
C1—C6—C5	117.7 (3)	C17—C18—H18	120.2
C2—C7—C8	128.7 (3)	C19—C18—H18	120.2
C2—C7—H7	115.7	C20—C19—C18	120.2 (4)
C8—C7—H7	115.7	C20—C19—H19	119.9
C9—C8—C13	116.6 (3)	C18—C19—H19	119.9
C9—C8—C7	121.0 (3)	C19—C20—C15	122.0 (3)
C13—C8—C7	122.4 (3)	C19—C20—H20	119.0
C10—C9—C8	121.9 (4)	C15—C20—H20	119.0

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ii	0.93	2.51	3.352 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1i	0.93	2.51	3.352 (4)	151

Symmetry code: (i) .