2-Bromo-1,3-bis-(4-chloro-phen-yl)prop-2-en-1-one.

In the title compound, C(15)H(9)BrCl(2)O, the two benzene rings are twisted from each other with a dihedral angle of 47.33 (8)°. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.680 (2) Å], and by weak inter-molecular C-H⋯O and C-H⋯Cl inter-actions. Additionally, the crystal structure exhibits a short intra-molecular C-H⋯Br contact (H⋯Br = 2.69 Å).

Related literature

For background on chalcones as possible nonlinear optical materials, see: Harrison et al. (2006 ▶). For related structures with the same backbone and different substituents on the aromatic rings, see: Butcher et al. (2006 ▶, 2007 ▶); Dhanasekaran et al. (2007a ▶,b ▶); Fun et al. (2008 ▶).

Experimental

Crystal data

C15H9BrCl2O

M = 356.03

Monoclinic,

a = 7.7416 (3) Å

b = 9.7981 (4) Å

c = 9.6717 (3) Å

β = 109.075 (2)°

V = 693.34 (5) Å3

Z = 2

Mo Kα radiation

μ = 3.34 mm−1

T = 120 K

0.18 × 0.16 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.585, T max = 0.824

12526 measured reflections

3129 independent reflections

2873 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.079

S = 1.04

3129 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −0.46 e Å−3

Absolute structure: Flack (1983 ▶), 1434 Friedel pairs

Flack parameter: 0.044 (9)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶), SCALEPACK and SORTAV (Blessing, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903815X/lx2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903815X/lx2111Isup2.hkl

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

C15H9BrCl2O	F(000) = 352
Mr = 356.03	Dx = 1.705 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 13953 reflections
a = 7.7416 (3) Å	θ = 2.9–27.5°
b = 9.7981 (4) Å	µ = 3.34 mm−1
c = 9.6717 (3) Å	T = 120 K
β = 109.075 (2)°	Block, colourless
V = 693.34 (5) Å3	0.18 × 0.16 × 0.06 mm
Z = 2

Nonius KappaCCD diffractometer	3129 independent reflections
Radiation source: fine-focus sealed tube	2873 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −12→12
Tmin = 0.585, Tmax = 0.824	l = −12→12
12526 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0258P)2 + 0.5496P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3129 reflections	Δρmax = 1.20 e Å−3
172 parameters	Δρmin = −0.46 e Å−3
1 restraint	Absolute structure: Flack (1983), 1434 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.044 (9)

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
C1	0.5669 (5)	0.6271 (3)	0.7407 (4)	0.0255 (8)
H1	0.5761	0.5621	0.6706	0.031*
C2	0.6586 (5)	0.6046 (4)	0.8887 (4)	0.0266 (8)
H2	0.7296	0.5245	0.9206	0.032*
C3	0.6438 (4)	0.7025 (4)	0.9891 (3)	0.0241 (6)
C4	0.5385 (5)	0.8181 (4)	0.9458 (4)	0.0288 (8)
H4	0.5283	0.8825	1.0160	0.035*
C5	0.4479 (5)	0.8387 (4)	0.7982 (4)	0.0292 (8)
H5	0.3753	0.9182	0.7670	0.035*
C6	0.4622 (5)	0.7436 (3)	0.6945 (4)	0.0250 (8)
C7	0.3742 (5)	0.7800 (4)	0.5351 (4)	0.0277 (8)
C8	0.3109 (5)	0.6665 (4)	0.4271 (4)	0.0271 (8)
C9	0.2468 (5)	0.5475 (4)	0.4610 (4)	0.0252 (8)
H9	0.2575	0.5416	0.5615	0.030*
C10	0.1645 (5)	0.4256 (4)	0.3785 (4)	0.0237 (7)
C11	0.1567 (5)	0.3124 (4)	0.4629 (4)	0.0304 (8)
H11	0.2057	0.3188	0.5665	0.037*
C12	0.0786 (5)	0.1897 (4)	0.3994 (4)	0.0341 (9)
H12	0.0774	0.1119	0.4578	0.041*
C13	0.0028 (5)	0.1849 (4)	0.2478 (4)	0.0303 (8)
C14	0.0093 (5)	0.2951 (4)	0.1604 (4)	0.0316 (9)
H14	−0.0427	0.2890	0.0570	0.038*
C15	0.0928 (5)	0.4146 (4)	0.2258 (4)	0.0276 (8)
H15	0.1016	0.4899	0.1665	0.033*
O1	0.3501 (5)	0.8986 (3)	0.4961 (3)	0.0440 (8)
Cl1	0.76953 (13)	0.67976 (9)	1.17307 (9)	0.0352 (2)
Cl2	−0.10057 (15)	0.03386 (11)	0.16691 (12)	0.0460 (3)
Br1	0.31668 (5)	0.71253 (4)	0.23765 (4)	0.03793 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0331 (19)	0.0179 (17)	0.0270 (17)	−0.0089 (15)	0.0120 (15)	−0.0038 (14)
C2	0.0268 (18)	0.0234 (18)	0.0321 (19)	0.0006 (15)	0.0130 (15)	−0.0016 (15)
C3	0.0265 (15)	0.0222 (16)	0.0272 (14)	−0.0041 (17)	0.0138 (12)	−0.0040 (17)
C4	0.0303 (19)	0.0246 (18)	0.037 (2)	−0.0052 (16)	0.0185 (16)	−0.0088 (16)
C5	0.0298 (19)	0.0202 (18)	0.040 (2)	−0.0016 (15)	0.0142 (17)	−0.0070 (16)
C6	0.0219 (16)	0.023 (2)	0.0308 (17)	−0.0049 (13)	0.0095 (13)	0.0000 (14)
C7	0.0249 (18)	0.0258 (19)	0.0325 (19)	−0.0014 (15)	0.0094 (15)	0.0036 (16)
C8	0.0251 (17)	0.031 (2)	0.0248 (17)	−0.0008 (14)	0.0068 (14)	0.0095 (14)
C9	0.0223 (17)	0.0268 (19)	0.0232 (16)	0.0026 (15)	0.0028 (14)	−0.0031 (15)
C10	0.0208 (16)	0.0231 (18)	0.0252 (17)	−0.0012 (14)	0.0049 (14)	−0.0020 (14)
C11	0.038 (2)	0.031 (2)	0.0240 (17)	−0.0122 (17)	0.0122 (16)	−0.0030 (16)
C12	0.041 (2)	0.033 (2)	0.0329 (17)	−0.0120 (19)	0.0179 (16)	−0.0028 (18)
C13	0.0268 (17)	0.034 (2)	0.0318 (16)	−0.0077 (16)	0.0124 (14)	−0.0120 (17)
C14	0.0270 (19)	0.038 (2)	0.0254 (18)	0.0029 (16)	0.0022 (15)	−0.0114 (17)
C15	0.0248 (18)	0.0290 (19)	0.0282 (18)	0.0011 (15)	0.0077 (15)	−0.0005 (16)
O1	0.075 (2)	0.0152 (13)	0.0357 (15)	−0.0042 (14)	0.0097 (15)	0.0106 (12)
Cl1	0.0448 (5)	0.0336 (6)	0.0279 (4)	−0.0016 (4)	0.0131 (4)	−0.0049 (4)
Cl2	0.0468 (6)	0.0417 (6)	0.0522 (6)	−0.0183 (5)	0.0199 (5)	−0.0197 (5)
Br1	0.0425 (2)	0.0432 (2)	0.02831 (17)	−0.0063 (2)	0.01189 (14)	0.01032 (19)

C1—C6	1.387 (5)	C8—Br1	1.902 (3)
C1—C2	1.392 (5)	C9—C10	1.462 (5)
C1—H1	0.9500	C9—H9	0.9500
C2—C3	1.397 (5)	C10—C11	1.391 (5)
C2—H2	0.9500	C10—C15	1.402 (5)
C3—C4	1.378 (5)	C11—C12	1.395 (5)
C3—Cl1	1.741 (3)	C11—H11	0.9500
C4—C5	1.384 (5)	C12—C13	1.391 (5)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.399 (5)	C13—C14	1.382 (6)
C5—H5	0.9500	C13—Cl2	1.742 (4)
C6—C7	1.510 (5)	C14—C15	1.387 (6)
C7—O1	1.217 (5)	C14—H14	0.9500
C7—C8	1.495 (5)	C15—H15	0.9500
C8—C9	1.349 (5)
C6—C1—C2	120.6 (3)	C7—C8—Br1	113.0 (2)
C6—C1—H1	119.7	C8—C9—C10	134.7 (3)
C2—C1—H1	119.7	C8—C9—H9	112.7
C1—C2—C3	118.4 (3)	C10—C9—H9	112.7
C1—C2—H2	120.8	C11—C10—C15	118.7 (3)
C3—C2—H2	120.8	C11—C10—C9	115.2 (3)
C4—C3—C2	121.8 (3)	C15—C10—C9	126.1 (3)
C4—C3—Cl1	119.6 (3)	C10—C11—C12	121.6 (3)
C2—C3—Cl1	118.5 (3)	C10—C11—H11	119.2
C3—C4—C5	119.0 (3)	C12—C11—H11	119.2
C3—C4—H4	120.5	C13—C12—C11	117.8 (4)
C5—C4—H4	120.5	C13—C12—H12	121.1
C4—C5—C6	120.6 (3)	C11—C12—H12	121.1
C4—C5—H5	119.7	C14—C13—C12	122.1 (4)
C6—C5—H5	119.7	C14—C13—Cl2	119.5 (3)
C1—C6—C5	119.5 (3)	C12—C13—Cl2	118.4 (3)
C1—C6—C7	123.0 (3)	C13—C14—C15	119.1 (3)
C5—C6—C7	117.3 (3)	C13—C14—H14	120.5
O1—C7—C8	120.8 (3)	C15—C14—H14	120.5
O1—C7—C6	121.0 (3)	C14—C15—C10	120.7 (4)
C8—C7—C6	118.2 (3)	C14—C15—H15	119.7
C9—C8—C7	122.4 (3)	C10—C15—H15	119.7
C9—C8—Br1	124.4 (3)
C6—C1—C2—C3	−0.6 (5)	O1—C7—C8—Br1	31.2 (5)
C1—C2—C3—C4	1.4 (5)	C6—C7—C8—Br1	−151.1 (3)
C1—C2—C3—Cl1	−176.1 (3)	C7—C8—C9—C10	174.4 (4)
C2—C3—C4—C5	−1.3 (5)	Br1—C8—C9—C10	−1.5 (6)
Cl1—C3—C4—C5	176.2 (3)	C8—C9—C10—C11	165.5 (4)
C3—C4—C5—C6	0.2 (5)	C8—C9—C10—C15	−15.5 (7)
C2—C1—C6—C5	−0.4 (5)	C15—C10—C11—C12	−0.4 (6)
C2—C1—C6—C7	174.1 (3)	C9—C10—C11—C12	178.7 (3)
C4—C5—C6—C1	0.6 (5)	C10—C11—C12—C13	−2.0 (6)
C4—C5—C6—C7	−174.3 (3)	C11—C12—C13—C14	2.5 (5)
C1—C6—C7—O1	−149.5 (4)	C11—C12—C13—Cl2	−178.3 (3)
C5—C6—C7—O1	25.2 (5)	C12—C13—C14—C15	−0.5 (5)
C1—C6—C7—C8	32.8 (5)	Cl2—C13—C14—C15	−179.6 (3)
C5—C6—C7—C8	−152.5 (3)	C13—C14—C15—C10	−2.1 (5)
O1—C7—C8—C9	−145.1 (4)	C11—C10—C15—C14	2.5 (5)
C6—C7—C8—C9	32.6 (5)	C9—C10—C15—C14	−176.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.95	2.47	3.411 (5)	171
C11—H11···Cl1ii	0.95	2.81	3.619 (4)	143
C15—H15···Br1	0.95	2.69	3.377 (4)	129

Table 1

Selected torsion angles (°)

C6—C7—C8—C9	32.6 (5)
O1—C7—C8—Br1	31.2 (5)
C7—C8—C9—C10	174.4 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.95	2.47	3.411 (5)	171
C11—H11⋯Cl1ii	0.95	2.81	3.619 (4)	143
C15—H15⋯Br1	0.95	2.69	3.377 (4)	129

Symmetry codes: (i) ; (ii) .