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

In the title compound, C(15)H(10)BrClO, the dihedral angle between the mean planes of the benzene rings in the ortho-bromo- and para-chloro-substituted rings is 70.5 (6)°. The dihedral angles between the mean plane of the prop-2-en-1-one group and the mean planes of the benzene rings in the 4-chloro-phenyl and 2-bromo-phenyl rings are 14.9 (3) and 63.3 (8)°, respectively. In the crystal, inversion dimers linked by pairs of weak C-H⋯O interactions are observed as well as aromatic π-π stacking inter-actions.

Related literature

For the radical quenching properties of the phenol groups present in many chalcones, see: Dhar (1981 ▶). For the anti­cancer activity of chalcones, see: Dimmock et al. (1999 ▶) and for their anti­malarial activity, see: Troeberg et al. (2000 ▶). For their non-linear optical properties, see: Sarojini et al. (2006 ▶). For related structures, see: Fun et al. (2008 ▶); Li et al. (2009 ▶); Ng et al. (2006 ▶); Teh et al. (2007 ▶); Yang et al. (2006 ▶), Jasinski et al. (2009 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H10BrClO

M = 321.59

Monoclinic,

a = 5.7317 (6) Å

b = 9.3920 (7) Å

c = 23.6517 (18) Å

β = 91.231 (8)°

V = 1272.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 6.19 mm−1

T = 110 K

0.84 × 0.49 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.039, T max = 0.512

4362 measured reflections

2466 independent reflections

2275 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.05

2466 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −1.07 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021562/zl2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021562/zl2282Isup2.hkl

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

C15H10BrClO	F(000) = 640
Mr = 321.59	Dx = 1.678 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2738 reflections
a = 5.7317 (6) Å	θ = 4.7–74.2°
b = 9.3920 (7) Å	µ = 6.19 mm−1
c = 23.6517 (18) Å	T = 110 K
β = 91.231 (8)°	Plate, yellow
V = 1272.9 (2) Å3	0.84 × 0.49 × 0.13 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini R diffractometer	2466 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2275 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 10.5081 pixels mm-1	θmax = 74.2°, θmin = 5.1°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→10
Tmin = 0.039, Tmax = 0.512	l = −25→29
4362 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0875P)2 + 2.2371P] where P = (Fo2 + 2Fc2)/3
2466 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −1.07 e Å−3

Experimental. IR data (KBr) ν cm-1: 2837 cm-1, 2966 cm-1, (C—H al. str) 3061 cm-1, (C—H ar. str), 1655 cm-1 (C=O), 1584 cm-1 (C=C); 1254 cm-1 (C—O—C).

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
Br	−0.27391 (6)	0.44265 (4)	0.639317 (15)	0.02097 (17)
Cl	0.85133 (14)	0.88426 (9)	0.35152 (3)	0.0207 (2)
O	−0.2348 (4)	0.7916 (3)	0.62618 (11)	0.0207 (5)
C1	0.0767 (5)	0.6542 (3)	0.66371 (13)	0.0132 (6)
C2	−0.0160 (6)	0.5245 (4)	0.68014 (13)	0.0168 (7)
C3	0.0796 (7)	0.4490 (4)	0.72552 (15)	0.0228 (8)
H3A	0.0157	0.3598	0.7360	0.027*
C4	0.2681 (7)	0.5048 (4)	0.75513 (15)	0.0257 (8)
H4A	0.3305	0.4549	0.7869	0.031*
C5	0.3679 (6)	0.6328 (4)	0.73916 (14)	0.0230 (8)
H5A	0.4999	0.6697	0.7593	0.028*
C6	0.2715 (6)	0.7065 (4)	0.69309 (14)	0.0192 (7)
H6A	0.3399	0.7937	0.6816	0.023*
C7	−0.0380 (6)	0.7467 (3)	0.61912 (14)	0.0150 (6)
C8	0.0907 (6)	0.7835 (4)	0.56835 (13)	0.0163 (6)
H8A	0.0264	0.8560	0.5447	0.020*
C9	0.2903 (5)	0.7243 (3)	0.55238 (13)	0.0139 (6)
H9A	0.3548	0.6525	0.5763	0.017*
C10	0.4194 (5)	0.7595 (3)	0.50142 (13)	0.0143 (6)
C11	0.6205 (6)	0.6846 (4)	0.48865 (13)	0.0167 (7)
H11A	0.6685	0.6077	0.5122	0.020*
C12	0.7537 (6)	0.7200 (4)	0.44200 (14)	0.0173 (7)
H12A	0.8904	0.6676	0.4335	0.021*
C13	0.6820 (6)	0.8334 (4)	0.40819 (13)	0.0151 (6)
C14	0.4794 (6)	0.9079 (4)	0.41904 (14)	0.0189 (7)
H14A	0.4303	0.9836	0.3950	0.023*
C15	0.3494 (6)	0.8706 (4)	0.46533 (15)	0.0201 (7)
H15A	0.2100	0.9213	0.4728	0.024*

	U11	U22	U33	U12	U13	U23
Br	0.0157 (2)	0.0143 (2)	0.0329 (3)	−0.00300 (13)	0.00039 (15)	−0.00360 (12)
Cl	0.0199 (4)	0.0216 (4)	0.0206 (4)	−0.0025 (3)	0.0026 (3)	0.0022 (3)
O	0.0112 (12)	0.0199 (13)	0.0311 (12)	0.0037 (10)	0.0003 (9)	0.0024 (10)
C1	0.0071 (14)	0.0153 (15)	0.0173 (14)	0.0035 (12)	0.0011 (10)	−0.0007 (12)
C2	0.0191 (17)	0.0126 (15)	0.0187 (15)	0.0031 (13)	0.0017 (12)	−0.0013 (12)
C3	0.027 (2)	0.0180 (18)	0.0232 (16)	0.0062 (14)	0.0053 (14)	0.0054 (13)
C4	0.0289 (19)	0.030 (2)	0.0177 (15)	0.0130 (17)	−0.0004 (13)	0.0023 (14)
C5	0.0163 (17)	0.0297 (19)	0.0227 (16)	0.0080 (15)	−0.0047 (13)	−0.0056 (14)
C6	0.0130 (16)	0.0191 (17)	0.0255 (16)	0.0005 (13)	−0.0020 (12)	−0.0024 (13)
C7	0.0125 (15)	0.0094 (14)	0.0230 (15)	−0.0002 (12)	−0.0031 (11)	−0.0009 (12)
C8	0.0149 (16)	0.0143 (15)	0.0196 (15)	0.0009 (13)	−0.0029 (12)	0.0023 (12)
C9	0.0097 (15)	0.0122 (14)	0.0197 (14)	−0.0037 (12)	−0.0027 (11)	0.0012 (12)
C10	0.0113 (15)	0.0124 (15)	0.0190 (14)	−0.0022 (12)	−0.0030 (11)	−0.0017 (12)
C11	0.0143 (16)	0.0150 (15)	0.0207 (15)	−0.0005 (13)	−0.0045 (12)	0.0033 (12)
C12	0.0118 (15)	0.0161 (16)	0.0240 (15)	0.0016 (13)	−0.0021 (12)	−0.0005 (13)
C13	0.0121 (15)	0.0156 (16)	0.0176 (14)	−0.0046 (13)	−0.0019 (11)	−0.0022 (12)
C14	0.0186 (18)	0.0148 (15)	0.0232 (15)	0.0017 (14)	−0.0038 (12)	0.0030 (13)
C15	0.0187 (17)	0.0166 (17)	0.0249 (16)	0.0045 (14)	−0.0032 (13)	0.0011 (13)

Br—C2	1.910 (3)	C8—C9	1.334 (5)
Cl—C13	1.739 (3)	C8—H8A	0.9500
O—C7	1.219 (4)	C9—C10	1.466 (4)
C1—C2	1.388 (5)	C9—H9A	0.9500
C1—C6	1.392 (4)	C10—C11	1.389 (5)
C1—C7	1.506 (4)	C10—C15	1.402 (5)
C2—C3	1.389 (5)	C11—C12	1.395 (5)
C3—C4	1.378 (6)	C11—H11A	0.9500
C3—H3A	0.9500	C12—C13	1.389 (5)
C4—C5	1.387 (6)	C12—H12A	0.9500
C4—H4A	0.9500	C13—C14	1.384 (5)
C5—C6	1.395 (5)	C14—C15	1.383 (5)
C5—H5A	0.9500	C14—H14A	0.9500
C6—H6A	0.9500	C15—H15A	0.9500
C7—C8	1.464 (4)
C2—C1—C6	118.5 (3)	C7—C8—H8A	117.1
C2—C1—C7	122.6 (3)	C8—C9—C10	126.2 (3)
C6—C1—C7	118.6 (3)	C8—C9—H9A	116.9
C1—C2—C3	121.2 (3)	C10—C9—H9A	116.9
C1—C2—Br	120.6 (2)	C11—C10—C15	118.2 (3)
C3—C2—Br	118.3 (3)	C11—C10—C9	120.0 (3)
C4—C3—C2	119.4 (3)	C15—C10—C9	121.7 (3)
C4—C3—H3A	120.3	C10—C11—C12	121.5 (3)
C2—C3—H3A	120.3	C10—C11—H11A	119.3
C3—C4—C5	121.0 (3)	C12—C11—H11A	119.3
C3—C4—H4A	119.5	C13—C12—C11	118.5 (3)
C5—C4—H4A	119.5	C13—C12—H12A	120.7
C4—C5—C6	118.9 (3)	C11—C12—H12A	120.7
C4—C5—H5A	120.5	C14—C13—C12	121.3 (3)
C6—C5—H5A	120.5	C14—C13—Cl	119.3 (3)
C1—C6—C5	121.0 (3)	C12—C13—Cl	119.4 (3)
C1—C6—H6A	119.5	C15—C14—C13	119.2 (3)
C5—C6—H6A	119.5	C15—C14—H14A	120.4
O—C7—C8	120.9 (3)	C13—C14—H14A	120.4
O—C7—C1	119.7 (3)	C14—C15—C10	121.2 (3)
C8—C7—C1	119.4 (3)	C14—C15—H15A	119.4
C9—C8—C7	125.7 (3)	C10—C15—H15A	119.4
C9—C8—H8A	117.1
C6—C1—C2—C3	1.2 (5)	O—C7—C8—C9	−169.4 (3)
C7—C1—C2—C3	−172.9 (3)	C1—C7—C8—C9	11.8 (5)
C6—C1—C2—Br	−177.0 (2)	C7—C8—C9—C10	179.4 (3)
C7—C1—C2—Br	8.8 (4)	C8—C9—C10—C11	−177.2 (3)
C1—C2—C3—C4	0.8 (5)	C8—C9—C10—C15	4.7 (5)
Br—C2—C3—C4	179.0 (3)	C15—C10—C11—C12	1.4 (5)
C2—C3—C4—C5	−2.1 (6)	C9—C10—C11—C12	−176.8 (3)
C3—C4—C5—C6	1.3 (5)	C10—C11—C12—C13	0.4 (5)
C2—C1—C6—C5	−2.0 (5)	C11—C12—C13—C14	−2.0 (5)
C7—C1—C6—C5	172.4 (3)	C11—C12—C13—Cl	177.4 (2)
C4—C5—C6—C1	0.7 (5)	C12—C13—C14—C15	1.7 (5)
C2—C1—C7—O	60.4 (4)	Cl—C13—C14—C15	−177.7 (3)
C6—C1—C7—O	−113.7 (4)	C13—C14—C15—C10	0.2 (5)
C2—C1—C7—C8	−120.8 (3)	C11—C10—C15—C14	−1.7 (5)
C6—C1—C7—C8	65.1 (4)	C9—C10—C15—C14	176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Oi	0.95	2.44	3.319 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Oi	0.95	2.44	3.319 (4)	154

Symmetry code: (i) .