(E)-3-(2-Chloro-phen-yl)-1-(4-chloro-phen-yl)prop-2-en-1-one.

The title compound, C(15)H(10)Cl(2)O, adopts an E configuration with respect to the C=C bond of the propenone unit. The dihedral angle between the two benzene rings is 32.4 (1)°. Intra-molecular C-H⋯O and C-H⋯Cl hydrogen bonds generate an S(5)S(5)S(5) motif. In addition, the crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related literature on chalcones, see: Fun et al. (2007 ▶); Patil et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H10Cl2O

M = 277.13

Orthorhombic,

a = 7.2777 (1) Å

b = 11.2686 (2) Å

c = 30.2365 (6) Å

V = 2479.68 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.51 mm−1

T = 100.0 (1) K

0.51 × 0.34 × 0.19 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.781, T max = 0.911

42713 measured reflections

5996 independent reflections

4413 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.05

5996 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015420/lh2627sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015420/lh2627Isup2.hkl

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

C15H10Cl2O	F000 = 1136
Mr = 277.13	Dx = 1.485 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8869 reflections
a = 7.2777 (1) Å	θ = 2.7–36.0º
b = 11.2686 (2) Å	µ = 0.51 mm−1
c = 30.2365 (6) Å	T = 100.0 (1) K
V = 2479.68 (7) Å3	Block, colourless
Z = 8	0.51 × 0.34 × 0.19 mm

Bruker SMART APEX2 CCD area-detector diffractometer	5996 independent reflections
Radiation source: fine-focus sealed tube	4413 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 100.0(1) K	θmax = 36.4º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −7→12
Tmin = 0.781, Tmax = 0.911	k = −17→18
42713 measured reflections	l = −50→48

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.6003P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
5996 reflections	Δρmax = 0.55 e Å−3
163 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.92678 (5)	0.49110 (3)	0.058017 (10)	0.02768 (8)
Cl2	1.06791 (4)	0.29033 (3)	0.406266 (11)	0.02816 (8)
O1	1.19326 (15)	0.53008 (8)	0.20697 (3)	0.0293 (2)
C1	0.99869 (17)	0.34415 (10)	0.06050 (4)	0.0217 (2)
C2	0.9725 (2)	0.27399 (11)	0.02335 (4)	0.0261 (2)
H2A	0.9233	0.3066	−0.0023	0.031*
C3	1.0200 (2)	0.15500 (11)	0.02468 (5)	0.0295 (3)
H3A	1.0032	0.1074	−0.0001	0.035*
C4	1.0934 (2)	0.10670 (11)	0.06340 (5)	0.0277 (3)
H4A	1.1250	0.0268	0.0644	0.033*
C5	1.11899 (19)	0.17750 (10)	0.10012 (4)	0.0247 (2)
H5A	1.1682	0.1443	0.1257	0.030*
C6	1.07237 (16)	0.29880 (10)	0.09989 (4)	0.0214 (2)
C7	1.10257 (17)	0.37394 (10)	0.13844 (4)	0.0229 (2)
H7A	1.1007	0.4555	0.1337	0.028*
C8	1.13268 (18)	0.33788 (10)	0.17986 (4)	0.0245 (2)
H8A	1.1364	0.2572	0.1863	0.029*
C9	1.16008 (17)	0.42575 (10)	0.21552 (4)	0.0226 (2)
C10	1.14122 (17)	0.38733 (10)	0.26259 (4)	0.0212 (2)
C11	1.10474 (19)	0.27011 (11)	0.27512 (4)	0.0258 (2)
H11A	1.0948	0.2116	0.2536	0.031*
C12	1.08325 (18)	0.24012 (11)	0.31927 (5)	0.0260 (2)
H12A	1.0583	0.1622	0.3274	0.031*
C13	1.09944 (16)	0.32798 (10)	0.35122 (4)	0.0227 (2)
C14	1.13629 (18)	0.44474 (11)	0.33986 (4)	0.0247 (2)
H14A	1.1471	0.5028	0.3616	0.030*
C15	1.15668 (18)	0.47343 (10)	0.29565 (4)	0.0239 (2)
H15A	1.1812	0.5516	0.2878	0.029*

	U11	U22	U33	U12	U13	U23
Cl1	0.03936 (18)	0.01927 (12)	0.02440 (15)	0.00338 (11)	0.00267 (12)	0.00341 (9)
Cl2	0.03176 (16)	0.02708 (15)	0.02565 (15)	−0.00451 (12)	0.00190 (11)	−0.00078 (10)
O1	0.0399 (5)	0.0181 (4)	0.0299 (5)	−0.0008 (4)	−0.0062 (4)	0.0006 (3)
C1	0.0255 (5)	0.0174 (4)	0.0223 (5)	−0.0004 (4)	0.0031 (4)	0.0014 (4)
C2	0.0355 (6)	0.0228 (5)	0.0201 (5)	−0.0030 (5)	0.0029 (5)	0.0015 (4)
C3	0.0414 (7)	0.0213 (5)	0.0260 (6)	−0.0050 (5)	0.0034 (5)	−0.0026 (4)
C4	0.0362 (7)	0.0171 (5)	0.0299 (6)	−0.0008 (5)	0.0012 (5)	−0.0016 (4)
C5	0.0283 (6)	0.0187 (5)	0.0272 (6)	0.0014 (5)	−0.0011 (5)	0.0006 (4)
C6	0.0219 (5)	0.0186 (5)	0.0236 (5)	−0.0010 (4)	0.0011 (4)	−0.0007 (4)
C7	0.0243 (5)	0.0181 (4)	0.0263 (6)	0.0003 (4)	−0.0021 (4)	−0.0009 (4)
C8	0.0283 (6)	0.0194 (5)	0.0258 (6)	0.0015 (4)	−0.0022 (5)	−0.0022 (4)
C9	0.0244 (5)	0.0182 (4)	0.0253 (6)	0.0022 (4)	−0.0042 (4)	−0.0015 (4)
C10	0.0217 (5)	0.0158 (4)	0.0262 (6)	0.0014 (4)	−0.0026 (4)	−0.0028 (4)
C11	0.0324 (6)	0.0178 (5)	0.0272 (6)	−0.0002 (5)	−0.0003 (5)	−0.0051 (4)
C12	0.0309 (6)	0.0174 (4)	0.0295 (6)	−0.0016 (4)	0.0018 (5)	−0.0020 (4)
C13	0.0223 (5)	0.0208 (5)	0.0251 (6)	−0.0002 (4)	−0.0007 (4)	−0.0015 (4)
C14	0.0281 (6)	0.0195 (5)	0.0264 (6)	−0.0012 (5)	−0.0032 (5)	−0.0039 (4)
C15	0.0274 (5)	0.0168 (4)	0.0275 (6)	−0.0004 (4)	−0.0045 (5)	−0.0019 (4)

Cl1—C1	1.7383 (12)	C7—H7A	0.9300
Cl2—C13	1.7330 (13)	C8—C9	1.4775 (17)
O1—C9	1.2277 (14)	C8—H8A	0.9300
C1—C2	1.3868 (18)	C9—C10	1.4939 (18)
C1—C6	1.4024 (17)	C10—C15	1.3975 (16)
C2—C3	1.3854 (18)	C10—C11	1.3997 (17)
C2—H2A	0.9300	C11—C12	1.3857 (19)
C3—C4	1.397 (2)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.3883 (18)
C4—C5	1.3800 (18)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.3860 (17)
C5—C6	1.4084 (16)	C14—C15	1.3834 (19)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.4574 (17)	C15—H15A	0.9300
C7—C8	1.3347 (18)
C2—C1—C6	122.19 (11)	C9—C8—H8A	119.9
C2—C1—Cl1	117.81 (10)	O1—C9—C8	120.97 (12)
C6—C1—Cl1	119.93 (9)	O1—C9—C10	119.75 (11)
C3—C2—C1	119.60 (12)	C8—C9—C10	119.25 (10)
C3—C2—H2A	120.2	C15—C10—C11	118.47 (12)
C1—C2—H2A	120.2	C15—C10—C9	118.22 (10)
C2—C3—C4	119.79 (12)	C11—C10—C9	123.29 (11)
C2—C3—H3A	120.1	C12—C11—C10	120.83 (11)
C4—C3—H3A	120.1	C12—C11—H11A	119.6
C5—C4—C3	120.04 (12)	C10—C11—H11A	119.6
C5—C4—H4A	120.0	C11—C12—C13	119.13 (11)
C3—C4—H4A	120.0	C11—C12—H12A	120.4
C4—C5—C6	121.64 (12)	C13—C12—H12A	120.4
C4—C5—H5A	119.2	C14—C13—C12	121.40 (12)
C6—C5—H5A	119.2	C14—C13—Cl2	119.73 (10)
C1—C6—C5	116.74 (11)	C12—C13—Cl2	118.85 (10)
C1—C6—C7	121.68 (10)	C15—C14—C13	118.81 (11)
C5—C6—C7	121.57 (11)	C15—C14—H14A	120.6
C8—C7—C6	126.75 (11)	C13—C14—H14A	120.6
C8—C7—H7A	116.6	C14—C15—C10	121.36 (11)
C6—C7—H7A	116.6	C14—C15—H15A	119.3
C7—C8—C9	120.19 (11)	C10—C15—H15A	119.3
C7—C8—H8A	119.9
C6—C1—C2—C3	0.0 (2)	C7—C8—C9—C10	163.02 (12)
Cl1—C1—C2—C3	−177.01 (11)	O1—C9—C10—C15	1.95 (18)
C1—C2—C3—C4	0.2 (2)	C8—C9—C10—C15	−176.18 (11)
C2—C3—C4—C5	−0.3 (2)	O1—C9—C10—C11	−179.57 (13)
C3—C4—C5—C6	0.2 (2)	C8—C9—C10—C11	2.31 (18)
C2—C1—C6—C5	−0.06 (18)	C15—C10—C11—C12	0.40 (19)
Cl1—C1—C6—C5	176.87 (10)	C9—C10—C11—C12	−178.08 (12)
C2—C1—C6—C7	178.80 (12)	C10—C11—C12—C13	−0.4 (2)
Cl1—C1—C6—C7	−4.27 (16)	C11—C12—C13—C14	0.09 (19)
C4—C5—C6—C1	−0.02 (19)	C11—C12—C13—Cl2	178.74 (10)
C4—C5—C6—C7	−178.88 (12)	C12—C13—C14—C15	0.16 (19)
C1—C6—C7—C8	164.24 (13)	Cl2—C13—C14—C15	−178.48 (10)
C5—C6—C7—C8	−17.0 (2)	C13—C14—C15—C10	−0.13 (19)
C6—C7—C8—C9	−179.71 (12)	C11—C10—C15—C14	−0.15 (19)
C7—C8—C9—O1	−15.08 (19)	C9—C10—C15—C14	178.41 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl1	0.93	2.65	3.0484 (12)	107
C7—H7A···O1	0.93	2.46	2.7973 (15)	101
C15—H15A···O1	0.93	2.46	2.7691 (15)	100
C12—H12A···O1i	0.93	2.59	3.2064 (16)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cl1	0.93	2.65	3.0484 (12)	107
C7—H7A⋯O1	0.93	2.46	2.7973 (15)	101
C15—H15A⋯O1	0.93	2.46	2.7691 (15)	100
C12—H12A⋯O1i	0.93	2.59	3.2064 (16)	125

Symmetry code: (i) .