(2E,6E)-2,6-Bis(2,6-dichloro-benzyl-idene)-cyclo-hexa-none.

The title compound, C(20)H(14)Cl(4)O, was prepared by the reaction of 2,6-dichloro-benzaldehyde and cyclo-hexa-none. In the mol-ecule, the central cyclo-hexa-none ring adopts an envelope conformation, while the terminal benzene rings make a dihedral angle of 57.87 (9)°.

Related literature

For background and applications of aryl­idene cyclo­alkanones, see: Deli et al. (1984 ▶); Nakano et al. (1987 ▶); Kawamata et al. (1996 ▶); Dimmock et al. (2003 ▶); Raj et al. (2003 ▶); Gangadhara (1995 ▶). For related structures, see: Yu et al. (2000 ▶); Zhou (2007 ▶).

Experimental

Crystal data

C20H14Cl4O

M = 412.11

Orthorhombic,

a = 17.917 (4) Å

b = 7.3094 (15) Å

c = 14.093 (3) Å

V = 1845.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 120 K

0.6 × 0.35 × 0.33 mm

Data collection

Stoe IPDS 2T diffractometer

13510 measured reflections

4946 independent reflections

4682 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.071

S = 1.04

4946 reflections

226 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 2369 Friedel pairs

Flack parameter: 0.01 (4)

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006629/xu5466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006629/xu5466Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006629/xu5466Isup3.cml

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

C20H14Cl4O	F(000) = 840
Mr = 412.11	Dx = 1.483 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4949 reflections
a = 17.917 (4) Å	θ = 2.3–29.2°
b = 7.3094 (15) Å	µ = 0.65 mm−1
c = 14.093 (3) Å	T = 120 K
V = 1845.7 (7) Å3	Needle, yellow
Z = 4	0.6 × 0.35 × 0.33 mm

Stoe IPDS 2T diffractometer	4682 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 29.2°, θmin = 2.3°
rotation method scans	h = −24→24
13510 measured reflections	k = −8→10
4946 independent reflections	l = −19→19

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0318P)2 + 0.5994P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4946 reflections	Δρmax = 0.25 e Å−3
226 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 2369 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (4)

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	0.23181 (3)	1.40628 (7)	0.99333 (3)	0.03179 (11)
Cl3	−0.14648 (3)	0.88978 (7)	0.82912 (3)	0.03028 (10)
Cl4	0.05216 (3)	0.35099 (7)	0.89917 (4)	0.03460 (11)
Cl2	0.30403 (3)	0.77001 (7)	1.16748 (4)	0.03902 (13)
C12	0.04419 (9)	0.8310 (2)	0.91901 (11)	0.0196 (3)
O1	0.04467 (7)	0.94480 (19)	1.07669 (9)	0.0237 (3)
C6	0.27374 (10)	1.0891 (2)	1.07795 (12)	0.0211 (3)
C13	0.07918 (9)	0.9234 (2)	1.00226 (12)	0.0185 (3)
C7	0.19499 (9)	1.0268 (2)	1.07289 (12)	0.0199 (3)
H7	0.1686	1.0178	1.1295	0.024*
C9	0.19554 (9)	0.9844 (3)	0.89597 (12)	0.0253 (3)
H9A	0.2490	0.9679	0.9032	0.030*
H9B	0.1872	1.1026	0.8666	0.030*
C15	−0.05043 (9)	0.6110 (2)	0.85940 (12)	0.0209 (3)
C5	0.32884 (10)	0.9818 (3)	1.12039 (12)	0.0252 (4)
C18	−0.11451 (11)	0.3989 (3)	0.71361 (15)	0.0317 (4)
H18	−0.1354	0.3295	0.6651	0.038*
C8	0.15938 (9)	0.9827 (2)	0.99274 (12)	0.0186 (3)
C1	0.29745 (11)	1.2584 (3)	1.04280 (12)	0.0253 (4)
C16	−0.02454 (10)	0.4355 (3)	0.83722 (14)	0.0246 (3)
C10	0.16500 (10)	0.8350 (3)	0.83127 (13)	0.0278 (4)
H10A	0.1873	0.8457	0.7688	0.033*
H10B	0.1777	0.7157	0.8568	0.033*
C19	−0.14239 (10)	0.5721 (3)	0.73292 (14)	0.0281 (4)
H19	−0.1820	0.6191	0.6979	0.034*
C11	0.08055 (10)	0.8530 (3)	0.82365 (12)	0.0260 (4)
H11A	0.0681	0.9721	0.7978	0.031*
H11B	0.0615	0.7605	0.7806	0.031*
C3	0.42366 (10)	1.2027 (3)	1.08876 (13)	0.0318 (4)
H3	0.4733	1.2393	1.0916	0.038*
C14	−0.01489 (9)	0.7245 (2)	0.93404 (12)	0.0211 (3)
H14	−0.0350	0.7210	0.9948	0.025*
C20	−0.11038 (10)	0.6741 (3)	0.80531 (12)	0.0222 (3)
C17	−0.05563 (11)	0.3289 (3)	0.76625 (15)	0.0295 (4)
H17	−0.0373	0.2122	0.7541	0.035*
C4	0.40302 (11)	1.0347 (3)	1.12538 (14)	0.0296 (4)
H4	0.4384	0.9584	1.1530	0.036*
C2	0.37123 (11)	1.3166 (3)	1.04810 (13)	0.0298 (4)
H2	0.3850	1.4306	1.0246	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0347 (2)	0.0280 (2)	0.0326 (2)	−0.00606 (18)	−0.00506 (19)	0.0103 (2)
Cl3	0.0346 (2)	0.0290 (2)	0.0272 (2)	0.00852 (18)	−0.00735 (18)	−0.00764 (19)
Cl4	0.0329 (2)	0.0303 (2)	0.0406 (3)	0.00904 (18)	−0.0048 (2)	−0.0030 (2)
Cl2	0.0393 (2)	0.0295 (2)	0.0483 (3)	−0.0027 (2)	−0.0170 (2)	0.0103 (2)
C12	0.0205 (7)	0.0212 (8)	0.0172 (7)	0.0006 (6)	−0.0003 (6)	−0.0023 (6)
O1	0.0229 (6)	0.0316 (7)	0.0167 (5)	−0.0022 (5)	0.0025 (4)	−0.0034 (5)
C6	0.0233 (7)	0.0252 (8)	0.0147 (6)	−0.0025 (6)	−0.0014 (6)	−0.0006 (6)
C13	0.0185 (7)	0.0214 (7)	0.0157 (7)	0.0020 (6)	0.0008 (6)	0.0017 (6)
C7	0.0214 (7)	0.0217 (7)	0.0166 (7)	−0.0015 (6)	−0.0011 (6)	0.0020 (6)
C9	0.0218 (8)	0.0344 (10)	0.0197 (7)	−0.0056 (7)	0.0038 (7)	−0.0032 (8)
C15	0.0188 (7)	0.0219 (8)	0.0219 (7)	−0.0041 (6)	0.0023 (6)	−0.0011 (6)
C5	0.0273 (9)	0.0279 (9)	0.0204 (8)	−0.0009 (7)	−0.0027 (7)	−0.0023 (7)
C18	0.0259 (9)	0.0345 (10)	0.0348 (10)	−0.0081 (8)	0.0025 (7)	−0.0151 (9)
C8	0.0196 (7)	0.0193 (7)	0.0169 (6)	−0.0001 (6)	0.0001 (6)	0.0010 (6)
C1	0.0267 (8)	0.0313 (9)	0.0179 (7)	−0.0039 (7)	−0.0008 (6)	0.0017 (7)
C16	0.0228 (7)	0.0228 (8)	0.0283 (9)	−0.0013 (6)	0.0026 (7)	−0.0026 (7)
C10	0.0276 (8)	0.0360 (10)	0.0197 (7)	−0.0038 (7)	0.0050 (7)	−0.0068 (8)
C19	0.0233 (8)	0.0340 (10)	0.0270 (9)	−0.0018 (7)	−0.0015 (7)	−0.0090 (8)
C11	0.0289 (8)	0.0331 (10)	0.0160 (7)	−0.0077 (7)	0.0011 (7)	−0.0018 (7)
C3	0.0220 (8)	0.0518 (12)	0.0216 (8)	−0.0093 (8)	0.0008 (7)	−0.0069 (8)
C14	0.0212 (7)	0.0233 (8)	0.0187 (7)	−0.0006 (7)	−0.0001 (6)	−0.0014 (6)
C20	0.0217 (8)	0.0232 (8)	0.0216 (8)	−0.0014 (7)	0.0017 (6)	−0.0040 (6)
C17	0.0281 (9)	0.0241 (9)	0.0362 (10)	−0.0048 (7)	0.0066 (8)	−0.0085 (8)
C4	0.0232 (8)	0.0412 (11)	0.0243 (8)	0.0021 (8)	−0.0063 (7)	−0.0062 (8)
C2	0.0299 (9)	0.0386 (10)	0.0210 (8)	−0.0137 (8)	0.0032 (7)	0.0017 (8)

Cl1—C1	1.743 (2)	C5—C4	1.386 (3)
Cl3—C20	1.7370 (19)	C18—C17	1.388 (3)
Cl4—C16	1.7414 (19)	C18—C19	1.388 (3)
Cl2—C5	1.742 (2)	C18—H18	0.9300
C12—C14	1.331 (2)	C1—C2	1.391 (3)
C12—C13	1.492 (2)	C16—C17	1.385 (3)
C12—C11	1.502 (2)	C10—C11	1.523 (3)
O1—C13	1.228 (2)	C10—H10A	0.9700
C6—C5	1.396 (3)	C10—H10B	0.9700
C6—C1	1.399 (3)	C19—C20	1.388 (2)
C6—C7	1.484 (2)	C19—H19	0.9300
C13—C8	1.507 (2)	C11—H11A	0.9700
C7—C8	1.337 (2)	C11—H11B	0.9700
C7—H7	0.9300	C3—C2	1.380 (3)
C9—C8	1.510 (2)	C3—C4	1.382 (3)
C9—C10	1.524 (3)	C3—H3	0.9300
C9—H9A	0.9700	C14—H14	0.9300
C9—H9B	0.9700	C17—H17	0.9300
C15—C20	1.396 (2)	C4—H4	0.9300
C15—C16	1.399 (3)	C2—H2	0.9300
C15—C14	1.483 (2)
C14—C12—C13	118.29 (15)	C15—C16—Cl4	118.34 (14)
C14—C12—C11	123.35 (15)	C11—C10—C9	109.69 (15)
C13—C12—C11	118.23 (14)	C11—C10—H10A	109.7
C5—C6—C1	115.73 (17)	C9—C10—H10A	109.7
C5—C6—C7	121.37 (17)	C11—C10—H10B	109.7
C1—C6—C7	122.89 (16)	C9—C10—H10B	109.7
O1—C13—C12	121.19 (15)	H10A—C10—H10B	108.2
O1—C13—C8	121.32 (16)	C18—C19—C20	119.04 (18)
C12—C13—C8	117.45 (14)	C18—C19—H19	120.5
C8—C7—C6	124.63 (15)	C20—C19—H19	120.5
C8—C7—H7	117.7	C12—C11—C10	111.02 (15)
C6—C7—H7	117.7	C12—C11—H11A	109.4
C8—C9—C10	112.35 (15)	C10—C11—H11A	109.4
C8—C9—H9A	109.1	C12—C11—H11B	109.4
C10—C9—H9A	109.1	C10—C11—H11B	109.4
C8—C9—H9B	109.1	H11A—C11—H11B	108.0
C10—C9—H9B	109.1	C2—C3—C4	120.58 (18)
H9A—C9—H9B	107.9	C2—C3—H3	119.7
C20—C15—C16	115.85 (16)	C4—C3—H3	119.7
C20—C15—C14	122.20 (16)	C12—C14—C15	123.77 (15)
C16—C15—C14	121.93 (16)	C12—C14—H14	118.1
C4—C5—C6	122.88 (19)	C15—C14—H14	118.1
C4—C5—Cl2	118.28 (15)	C19—C20—C15	122.83 (18)
C6—C5—Cl2	118.83 (14)	C19—C20—Cl3	118.41 (14)
C17—C18—C19	120.36 (18)	C15—C20—Cl3	118.76 (13)
C17—C18—H18	119.8	C16—C17—C18	118.97 (18)
C19—C18—H18	119.8	C16—C17—H17	120.5
C7—C8—C13	116.69 (15)	C18—C17—H17	120.5
C7—C8—C9	123.82 (15)	C3—C4—C5	119.07 (19)
C13—C8—C9	119.47 (14)	C3—C4—H4	120.5
C2—C1—C6	122.69 (18)	C5—C4—H4	120.5
C2—C1—Cl1	118.25 (16)	C3—C2—C1	119.02 (19)
C6—C1—Cl1	119.03 (14)	C3—C2—H2	120.5
C17—C16—C15	122.94 (18)	C1—C2—H2	120.5
C17—C16—Cl4	118.69 (15)
C14—C12—C13—O1	−20.1 (3)	C14—C15—C16—Cl4	−0.5 (2)
C11—C12—C13—O1	163.96 (17)	C8—C9—C10—C11	55.7 (2)
C14—C12—C13—C8	157.57 (16)	C17—C18—C19—C20	0.2 (3)
C11—C12—C13—C8	−18.4 (2)	C14—C12—C11—C10	−132.96 (18)
C5—C6—C7—C8	−112.5 (2)	C13—C12—C11—C10	42.8 (2)
C1—C6—C7—C8	68.8 (3)	C9—C10—C11—C12	−61.2 (2)
C1—C6—C5—C4	−2.0 (3)	C13—C12—C14—C15	−173.89 (16)
C7—C6—C5—C4	179.24 (17)	C11—C12—C14—C15	1.8 (3)
C1—C6—C5—Cl2	179.18 (13)	C20—C15—C14—C12	−92.9 (2)
C7—C6—C5—Cl2	0.4 (2)	C16—C15—C14—C12	85.4 (2)
C6—C7—C8—C13	−179.65 (16)	C18—C19—C20—C15	0.7 (3)
C6—C7—C8—C9	2.1 (3)	C18—C19—C20—Cl3	−179.49 (15)
O1—C13—C8—C7	12.3 (2)	C16—C15—C20—C19	−0.8 (3)
C12—C13—C8—C7	−165.39 (16)	C14—C15—C20—C19	177.55 (17)
O1—C13—C8—C9	−169.41 (17)	C16—C15—C20—Cl3	179.37 (13)
C12—C13—C8—C9	12.9 (2)	C14—C15—C20—Cl3	−2.3 (2)
C10—C9—C8—C7	146.11 (18)	C15—C16—C17—C18	0.8 (3)
C10—C9—C8—C13	−32.1 (2)	Cl4—C16—C17—C18	−176.99 (15)
C5—C6—C1—C2	0.9 (3)	C19—C18—C17—C16	−0.9 (3)
C7—C6—C1—C2	179.69 (17)	C2—C3—C4—C5	0.2 (3)
C5—C6—C1—Cl1	−177.17 (13)	C6—C5—C4—C3	1.4 (3)
C7—C6—C1—Cl1	1.6 (2)	Cl2—C5—C4—C3	−179.70 (14)
C20—C15—C16—C17	0.1 (3)	C4—C3—C2—C1	−1.2 (3)
C14—C15—C16—C17	−178.32 (17)	C6—C1—C2—C3	0.6 (3)
C20—C15—C16—Cl4	177.86 (13)	Cl1—C1—C2—C3	178.73 (14)