(E)-3-(4-Bromo-phen-yl)-1-(3,4-dichloro-phen-yl)prop-2-en-1-one.

The mol-ecule of the title compound, C(15)H(9)BrCl(2)O, is shown to be the E isomer, with the 3,4-dichloro-benzoyl and p-bromo-phenyl substituents in trans positions with respect to the chalcone olefin bond. The mol-ecule is non-planar, the two aromatic rings forming a dihedral angle of 49.58 (1)°.

Related literature

For related literature on chalcones, see: Dhar (1981 ▶); Di Carlo et al. (1999 ▶); Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Sarojini et al. (2006 ▶). For related structures, see: Li et al. (2007 ▶, 2008 ▶); Wang et al. (2007 ▶); Tiang et al. (2007 ▶); Teh et al. (2006 ▶); Patil et al. (2006 ▶); Butcher et al. (2007 ▶).

Experimental

Crystal data

C15H9BrCl2O

M = 356.05

Triclinic,

a = 5.9370 (5) Å

b = 7.7365 (6) Å

c = 14.8254 (11) Å

α = 81.347 (6)°

β = 88.182 (6)°

γ = 88.315 (6)°

V = 672.66 (9) Å3

Z = 2

Mo Kα radiation

μ = 3.44 mm−1

T = 293 K

0.30 × 0.24 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.383, T max = 0.538

7411 measured reflections

3671 independent reflections

2762 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.100

S = 1.14

3671 reflections

209 parameters

All H-atom parameters refined

Δρmax = 0.61 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008162/ya2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008162/ya2083Isup2.hkl

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

C15H9BrCl2O	Z = 2
Mr = 356.05	F(000) = 352
Triclinic, P1	Dx = 1.758 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9370 (5) Å	Cell parameters from 2762 reflections
b = 7.7365 (6) Å	θ = 3.2–30.3°
c = 14.8254 (11) Å	µ = 3.44 mm−1
α = 81.347 (6)°	T = 293 K
β = 88.182 (6)°	Rectangular, pale yellow
γ = 88.315 (6)°	0.30 × 0.24 × 0.18 mm
V = 672.66 (9) Å3

Oxford Diffraction Xcalibur diffractometer	3671 independent reflections
Radiation source: fine-focus sealed tube	2762 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω–2θ scans	θmax = 30.3°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.383, Tmax = 0.538	k = −10→10
7411 measured reflections	l = −20→20

Refinement on F2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0232P)2 + 0.974P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.048	(Δ/σ)max = 0.002
wR(F2) = 0.100	Δρmax = 0.61 e Å−3
S = 1.14	Δρmin = −0.50 e Å−3
3671 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
209 parameters	Extinction coefficient: 0.0163 (13)
0 restraints

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.

	x	y	z	Uiso*/Ueq
H4	−0.733 (6)	−0.335 (4)	0.696 (2)	0.029 (9)*
H15	−0.435 (6)	−0.108 (4)	0.215 (2)	0.032 (9)*
H14	−0.208 (6)	0.023 (5)	0.096 (2)	0.038 (9)*
H1	−0.040 (6)	−0.628 (5)	0.737 (2)	0.039 (9)*
H12	0.256 (6)	0.100 (5)	0.275 (2)	0.044 (10)*
H6	−0.128 (6)	−0.465 (5)	0.599 (3)	0.047 (11)*
H9	−0.520 (6)	−0.192 (5)	0.370 (2)	0.041 (10)*
H11	0.024 (6)	−0.027 (5)	0.393 (3)	0.041 (10)*
H8	−0.193 (6)	−0.212 (5)	0.496 (2)	0.045 (10)*
Br1	0.22801 (7)	0.18580 (5)	0.07919 (2)	0.04765 (14)
Cl1	−0.73344 (15)	−0.48572 (14)	0.87746 (6)	0.0488 (2)
Cl2	−0.26813 (16)	−0.68518 (13)	0.90475 (6)	0.0491 (2)
C12	0.1124 (6)	0.0635 (5)	0.2638 (2)	0.0365 (7)
C13	0.0417 (5)	0.0773 (4)	0.1753 (2)	0.0339 (7)
C4	−0.5964 (6)	−0.3937 (4)	0.7036 (2)	0.0325 (7)
C3	−0.5425 (5)	−0.4813 (4)	0.7880 (2)	0.0308 (6)
C10	−0.2309 (5)	−0.0822 (4)	0.3167 (2)	0.0314 (7)
C6	−0.2335 (6)	−0.4685 (5)	0.6444 (2)	0.0377 (8)
C11	−0.0236 (6)	−0.0170 (5)	0.3342 (2)	0.0354 (7)
C5	−0.4425 (5)	−0.3860 (4)	0.6308 (2)	0.0321 (7)
C2	−0.3345 (5)	−0.5675 (4)	0.8006 (2)	0.0316 (6)
C9	−0.3824 (6)	−0.1641 (5)	0.3887 (2)	0.0358 (7)
C15	−0.2963 (6)	−0.0639 (5)	0.2264 (2)	0.0350 (7)
O1	−0.7120 (4)	−0.2757 (4)	0.52258 (17)	0.0547 (7)
C1	−0.1805 (6)	−0.5621 (5)	0.7283 (2)	0.0385 (8)
C7	−0.5123 (6)	−0.2916 (5)	0.5405 (2)	0.0374 (7)
C14	−0.1609 (6)	0.0134 (5)	0.1552 (2)	0.0375 (8)
C8	−0.3364 (6)	−0.2186 (5)	0.4749 (2)	0.0392 (8)

	U11	U22	U33	U12	U13	U23
Br1	0.0529 (2)	0.0481 (2)	0.0392 (2)	−0.00965 (17)	0.01013 (15)	0.00191 (15)
Cl1	0.0466 (5)	0.0615 (6)	0.0345 (4)	0.0011 (4)	0.0124 (3)	0.0022 (4)
Cl2	0.0572 (5)	0.0459 (5)	0.0403 (5)	0.0040 (4)	−0.0066 (4)	0.0064 (4)
C12	0.0330 (17)	0.0381 (19)	0.0386 (17)	−0.0066 (15)	−0.0010 (13)	−0.0049 (14)
C13	0.0387 (17)	0.0287 (17)	0.0320 (15)	0.0015 (14)	0.0051 (13)	0.0008 (12)
C4	0.0310 (16)	0.0332 (18)	0.0330 (16)	−0.0052 (14)	0.0002 (12)	−0.0027 (13)
C3	0.0339 (15)	0.0287 (16)	0.0297 (15)	−0.0068 (13)	0.0047 (12)	−0.0038 (12)
C10	0.0366 (16)	0.0291 (17)	0.0284 (15)	−0.0029 (13)	−0.0002 (12)	−0.0039 (12)
C6	0.0348 (17)	0.048 (2)	0.0325 (16)	−0.0062 (15)	0.0045 (13)	−0.0113 (14)
C11	0.0384 (17)	0.0394 (19)	0.0281 (15)	−0.0022 (15)	−0.0038 (13)	−0.0037 (13)
C5	0.0327 (15)	0.0360 (18)	0.0282 (15)	−0.0085 (14)	0.0007 (12)	−0.0052 (13)
C2	0.0393 (17)	0.0258 (16)	0.0303 (15)	−0.0007 (13)	−0.0054 (12)	−0.0055 (12)
C9	0.0367 (17)	0.0372 (19)	0.0332 (16)	−0.0062 (15)	−0.0016 (13)	−0.0034 (13)
C15	0.0344 (17)	0.0365 (19)	0.0343 (16)	−0.0055 (14)	−0.0047 (13)	−0.0040 (14)
O1	0.0375 (13)	0.085 (2)	0.0372 (13)	−0.0068 (14)	−0.0018 (10)	0.0060 (13)
C1	0.0371 (18)	0.039 (2)	0.0410 (18)	0.0011 (15)	−0.0018 (14)	−0.0100 (15)
C7	0.0401 (18)	0.042 (2)	0.0299 (16)	−0.0066 (15)	0.0000 (13)	−0.0042 (14)
C14	0.0461 (19)	0.040 (2)	0.0259 (15)	−0.0029 (16)	−0.0044 (13)	−0.0016 (13)
C8	0.0358 (17)	0.048 (2)	0.0328 (16)	−0.0096 (16)	−0.0014 (13)	−0.0006 (14)

Br1—C13	1.885 (3)	C6—C5	1.385 (5)
Cl1—C3	1.714 (3)	C6—H6	0.90 (4)
Cl2—C2	1.722 (3)	C11—H11	0.92 (4)
C12—C13	1.379 (5)	C5—C7	1.491 (4)
C12—C11	1.381 (4)	C2—C1	1.382 (5)
C12—H12	0.93 (4)	C9—C8	1.319 (5)
C13—C14	1.372 (5)	C9—H9	0.91 (4)
C4—C3	1.373 (4)	C15—C14	1.379 (4)
C4—C5	1.387 (4)	C15—H15	0.93 (3)
C4—H4	0.92 (3)	O1—C7	1.222 (4)
C3—C2	1.391 (4)	C1—H1	0.96 (4)
C10—C11	1.390 (5)	C7—C8	1.470 (4)
C10—C15	1.392 (4)	C14—H14	0.92 (4)
C10—C9	1.455 (4)	C8—H8	0.92 (4)
C6—C1	1.383 (5)
C13—C12—C11	119.3 (3)	C4—C5—C7	118.1 (3)
C13—C12—H12	119 (2)	C1—C2—C3	119.9 (3)
C11—C12—H12	121 (2)	C1—C2—Cl2	119.4 (3)
C14—C13—C12	121.6 (3)	C3—C2—Cl2	120.7 (2)
C14—C13—Br1	119.0 (2)	C8—C9—C10	127.7 (3)
C12—C13—Br1	119.3 (2)	C8—C9—H9	116 (2)
C3—C4—C5	120.6 (3)	C10—C9—H9	116 (2)
C3—C4—H4	120 (2)	C14—C15—C10	122.0 (3)
C5—C4—H4	120 (2)	C14—C15—H15	121 (2)
C4—C3—C2	120.0 (3)	C10—C15—H15	117 (2)
C4—C3—Cl1	119.8 (2)	C2—C1—C6	119.6 (3)
C2—C3—Cl1	120.2 (2)	C2—C1—H1	119 (2)
C11—C10—C15	117.9 (3)	C6—C1—H1	121 (2)
C11—C10—C9	122.8 (3)	O1—C7—C8	121.5 (3)
C15—C10—C9	119.3 (3)	O1—C7—C5	120.0 (3)
C1—C6—C5	120.8 (3)	C8—C7—C5	118.5 (3)
C1—C6—H6	117 (2)	C13—C14—C15	118.3 (3)
C5—C6—H6	122 (2)	C13—C14—H14	122 (2)
C12—C11—C10	120.8 (3)	C15—C14—H14	120 (2)
C12—C11—H11	119 (2)	C9—C8—C7	121.0 (3)
C10—C11—H11	120 (2)	C9—C8—H8	121 (2)
C6—C5—C4	119.1 (3)	C7—C8—H8	118 (2)
C6—C5—C7	122.9 (3)