2,3-Dibromo-1,3-bis-(4-chloro-phen-yl)propan-1-one.

In the title compound, C(15)H(10)Br(2)Cl(2)O, the terminal benzene rings make a dihedral angle of 31.1 (2)° with each other. In the crystal, mol-ecules are stacked along the a axis and consolidated by C-H⋯π inter-actions. Short Cl⋯Cl [3.1140 (17) Å] and Br⋯Cl [3.4565 (13) Å] contacts are observed.

Related literature

For general background to and the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Opletalova & Sedivy (1999 ▶); Nowakowska (2007 ▶). For the preparation of the title compound, see: Rai et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C15H10Br2Cl2O

M = 436.95

Orthorhombic,

a = 5.7599 (3) Å

b = 17.1233 (8) Å

c = 30.1983 (13) Å

V = 2978.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 5.79 mm−1

T = 100 K

0.52 × 0.48 × 0.34 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.154, T max = 0.241

16656 measured reflections

4100 independent reflections

3459 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.130

S = 1.12

4100 reflections

181 parameters

H-atom parameters constrained

Δρmax = 1.58 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045022/is2626sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045022/is2626Isup2.hkl

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

C15H10Br2Cl2O	F(000) = 1696
Mr = 436.95	Dx = 1.949 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7210 reflections
a = 5.7599 (3) Å	θ = 2.5–29.4°
b = 17.1233 (8) Å	µ = 5.79 mm−1
c = 30.1983 (13) Å	T = 100 K
V = 2978.4 (2) Å3	Block, light yellow
Z = 8	0.52 × 0.48 × 0.34 mm

Bruker SMART APEXII CCD area-detector diffractometer	4100 independent reflections
Radiation source: fine-focus sealed tube	3459 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 29.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→6
Tmin = 0.154, Tmax = 0.241	k = −23→22
16656 measured reflections	l = −41→41

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0496P)2 + 11.6475P] where P = (Fo2 + 2Fc2)/3
4100 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 1.58 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	−0.01792 (9)	0.49293 (3)	0.070047 (16)	0.03500 (14)
Br2	0.29597 (8)	0.43618 (3)	0.207223 (14)	0.02966 (13)
Cl1	−0.0272 (2)	0.08541 (7)	0.01691 (4)	0.0361 (3)
Cl2	−0.3932 (2)	0.76965 (7)	0.21154 (4)	0.0309 (2)
O1	0.4810 (6)	0.3947 (2)	0.10860 (12)	0.0343 (8)
C1	−0.0300 (8)	0.2749 (3)	0.09337 (15)	0.0274 (9)
H1A	−0.1334	0.3006	0.1120	0.033*
C2	−0.0933 (8)	0.2049 (3)	0.07360 (15)	0.0279 (9)
H2A	−0.2362	0.1821	0.0798	0.034*
C3	0.0597 (8)	0.1696 (3)	0.04456 (15)	0.0281 (9)
C4	0.2787 (8)	0.2004 (3)	0.03566 (15)	0.0277 (9)
H4A	0.3794	0.1756	0.0161	0.033*
C5	0.3415 (8)	0.2684 (3)	0.05661 (14)	0.0267 (9)
H5A	0.4885	0.2891	0.0517	0.032*
C6	0.1892 (8)	0.3070 (3)	0.08517 (14)	0.0248 (8)
C7	0.2737 (8)	0.3804 (3)	0.10644 (15)	0.0275 (9)
C8	0.0953 (8)	0.4392 (3)	0.12362 (15)	0.0283 (9)
H8A	−0.0327	0.4120	0.1384	0.034*
C9	0.2020 (8)	0.4987 (3)	0.15432 (15)	0.0298 (9)
H9A	0.3422	0.5197	0.1403	0.036*
C10	0.0499 (8)	0.5659 (3)	0.16830 (15)	0.0292 (9)
C11	0.1231 (8)	0.6422 (3)	0.16112 (15)	0.0292 (9)
H11A	0.2644	0.6513	0.1471	0.035*
C12	−0.0117 (8)	0.7051 (3)	0.17457 (15)	0.0287 (9)
H12A	0.0393	0.7559	0.1698	0.034*
C13	−0.2224 (8)	0.6915 (3)	0.19510 (14)	0.0270 (9)
C14	−0.2990 (8)	0.6163 (3)	0.20252 (15)	0.0297 (9)
H14A	−0.4406	0.6077	0.2165	0.036*
C15	−0.1632 (8)	0.5529 (3)	0.18901 (16)	0.0299 (9)
H15A	−0.2148	0.5021	0.1938	0.036*

	U11	U22	U33	U12	U13	U23
Br1	0.0440 (3)	0.0307 (2)	0.0303 (2)	0.0071 (2)	−0.0066 (2)	0.00027 (18)
Br2	0.0316 (2)	0.0294 (2)	0.0280 (2)	0.00218 (17)	−0.00372 (17)	0.00071 (17)
Cl1	0.0440 (6)	0.0255 (5)	0.0389 (6)	−0.0021 (5)	0.0046 (5)	−0.0068 (4)
Cl2	0.0337 (6)	0.0292 (5)	0.0298 (5)	0.0063 (4)	0.0013 (4)	−0.0044 (4)
O1	0.0270 (16)	0.0321 (18)	0.0438 (19)	0.0008 (13)	0.0030 (14)	−0.0076 (14)
C1	0.026 (2)	0.029 (2)	0.028 (2)	0.0040 (17)	0.0015 (17)	−0.0029 (16)
C2	0.026 (2)	0.027 (2)	0.030 (2)	0.0007 (17)	0.0002 (18)	0.0005 (17)
C3	0.036 (2)	0.023 (2)	0.025 (2)	0.0025 (18)	−0.0001 (18)	−0.0002 (16)
C4	0.033 (2)	0.024 (2)	0.027 (2)	0.0034 (18)	0.0016 (18)	−0.0005 (16)
C5	0.026 (2)	0.029 (2)	0.0254 (19)	0.0017 (17)	0.0035 (17)	0.0029 (16)
C6	0.025 (2)	0.026 (2)	0.0229 (18)	0.0006 (16)	0.0006 (16)	−0.0011 (16)
C7	0.031 (2)	0.024 (2)	0.027 (2)	0.0023 (17)	0.0016 (18)	−0.0017 (16)
C8	0.030 (2)	0.022 (2)	0.032 (2)	−0.0006 (17)	0.0004 (18)	0.0007 (17)
C9	0.028 (2)	0.031 (2)	0.031 (2)	−0.0003 (18)	−0.0003 (18)	−0.0021 (18)
C10	0.029 (2)	0.028 (2)	0.030 (2)	−0.0005 (18)	−0.0007 (18)	−0.0037 (17)
C11	0.026 (2)	0.030 (2)	0.031 (2)	0.0004 (18)	0.0027 (18)	−0.0051 (18)
C12	0.033 (2)	0.024 (2)	0.029 (2)	−0.0001 (18)	0.0002 (19)	−0.0018 (17)
C13	0.032 (2)	0.023 (2)	0.0254 (19)	0.0044 (17)	−0.0053 (18)	−0.0014 (16)
C14	0.026 (2)	0.032 (2)	0.032 (2)	0.0006 (18)	0.0003 (18)	−0.0002 (18)
C15	0.031 (2)	0.022 (2)	0.037 (2)	0.0021 (17)	0.0011 (19)	−0.0038 (17)

Br1—C8	1.972 (5)	C7—C8	1.529 (6)
Br2—C9	1.997 (5)	C8—C9	1.508 (6)
Cl1—C3	1.740 (5)	C8—H8A	0.9800
Cl2—C13	1.733 (5)	C9—C10	1.507 (6)
O1—C7	1.221 (6)	C9—H9A	0.9800
C1—C2	1.389 (6)	C10—C11	1.390 (7)
C1—C6	1.399 (6)	C10—C15	1.395 (7)
C1—H1A	0.9300	C11—C12	1.389 (6)
C2—C3	1.382 (6)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.382 (7)
C3—C4	1.393 (7)	C12—H12A	0.9300
C4—C5	1.374 (6)	C13—C14	1.380 (6)
C4—H4A	0.9300	C14—C15	1.399 (6)
C5—C6	1.397 (6)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.493 (6)
C2—C1—C6	120.0 (4)	Br1—C8—H8A	110.3
C2—C1—H1A	120.0	C10—C9—C8	116.8 (4)
C6—C1—H1A	120.0	C10—C9—Br2	110.0 (3)
C3—C2—C1	118.9 (4)	C8—C9—Br2	103.9 (3)
C3—C2—H2A	120.6	C10—C9—H9A	108.6
C1—C2—H2A	120.6	C8—C9—H9A	108.6
C2—C3—C4	122.3 (4)	Br2—C9—H9A	108.6
C2—C3—Cl1	118.9 (4)	C11—C10—C15	119.1 (4)
C4—C3—Cl1	118.8 (3)	C11—C10—C9	119.9 (4)
C5—C4—C3	118.1 (4)	C15—C10—C9	121.0 (4)
C5—C4—H4A	121.0	C12—C11—C10	120.9 (4)
C3—C4—H4A	121.0	C12—C11—H11A	119.6
C4—C5—C6	121.3 (4)	C10—C11—H11A	119.6
C4—C5—H5A	119.3	C13—C12—C11	119.5 (4)
C6—C5—H5A	119.3	C13—C12—H12A	120.3
C5—C6—C1	119.4 (4)	C11—C12—H12A	120.3
C5—C6—C7	117.3 (4)	C14—C13—C12	120.7 (4)
C1—C6—C7	123.2 (4)	C14—C13—Cl2	119.5 (4)
O1—C7—C6	120.7 (4)	C12—C13—Cl2	119.8 (4)
O1—C7—C8	120.5 (4)	C13—C14—C15	119.9 (4)
C6—C7—C8	118.8 (4)	C13—C14—H14A	120.1
C9—C8—C7	112.3 (4)	C15—C14—H14A	120.1
C9—C8—Br1	108.9 (3)	C10—C15—C14	119.9 (4)
C7—C8—Br1	104.5 (3)	C10—C15—H15A	120.0
C9—C8—H8A	110.3	C14—C15—H15A	120.0
C7—C8—H8A	110.3
C6—C1—C2—C3	−2.6 (7)	C7—C8—C9—C10	171.9 (4)
C1—C2—C3—C4	2.4 (7)	Br1—C8—C9—C10	56.6 (5)
C1—C2—C3—Cl1	−175.7 (3)	C7—C8—C9—Br2	−66.8 (4)
C2—C3—C4—C5	−0.3 (7)	Br1—C8—C9—Br2	178.0 (2)
Cl1—C3—C4—C5	177.8 (3)	C8—C9—C10—C11	−124.5 (5)
C3—C4—C5—C6	−1.6 (7)	Br2—C9—C10—C11	117.4 (4)
C4—C5—C6—C1	1.4 (7)	C8—C9—C10—C15	56.4 (6)
C4—C5—C6—C7	179.9 (4)	Br2—C9—C10—C15	−61.7 (5)
C2—C1—C6—C5	0.8 (7)	C15—C10—C11—C12	0.5 (7)
C2—C1—C6—C7	−177.6 (4)	C9—C10—C11—C12	−178.6 (4)
C5—C6—C7—O1	−19.2 (6)	C10—C11—C12—C13	−0.5 (7)
C1—C6—C7—O1	159.2 (5)	C11—C12—C13—C14	0.4 (7)
C5—C6—C7—C8	158.0 (4)	C11—C12—C13—Cl2	−179.4 (4)
C1—C6—C7—C8	−23.5 (6)	C12—C13—C14—C15	−0.3 (7)
O1—C7—C8—C9	−17.8 (6)	Cl2—C13—C14—C15	179.5 (4)
C6—C7—C8—C9	164.9 (4)	C11—C10—C15—C14	−0.5 (7)
O1—C7—C8—Br1	100.1 (5)	C9—C10—C15—C14	178.6 (4)
C6—C7—C8—Br1	−77.2 (4)	C13—C14—C15—C10	0.4 (7)

Cg1 is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cg1i	0.93	2.96	3.638 (5)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg1i	0.93	2.96	3.638 (5)	131

Symmetry code: (i) .