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

In the title compound, C(15)H(10)BrClO, the dihedral angle between mean planes of the bromo- and chloro-substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° in the structure with the Cl substituent in the meta position of the aromatic ring. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromo-phenyl and 3-chloro-phenyl rings are 28.7 (5) and 24.2 (4)°, respectively. In the crystal, weak inter-molecular C-H⋯π inter-actions occur.

Related literature

For a related structure, see: Ng et al. (2006 ▶).

Experimental

Crystal data

C15H10BrClO

M = 321.59

Triclinic,

a = 5.9197 (8) Å

b = 7.3391 (11) Å

c = 14.8171 (17) Å

α = 101.929 (11)°

β = 94.371 (10)°

γ = 93.299 (11)°

V = 626.22 (15) Å3

Z = 2

Cu Kα radiation

μ = 6.29 mm−1

T = 110 K

0.50 × 0.21 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.041, T max = 0.344

3868 measured reflections

2432 independent reflections

2312 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.164

S = 1.07

2432 reflections

163 parameters

H-atom parameters constrained

Δρmax = 1.78 e Å−3

Δρmin = −1.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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/S1600536809053446/bt5130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053446/bt5130Isup2.hkl

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

C15H10BrClO	Z = 2
Mr = 321.59	F(000) = 320
Triclinic, P1	Dx = 1.706 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.9197 (8) Å	Cell parameters from 3370 reflections
b = 7.3391 (11) Å	θ = 6.1–73.9°
c = 14.8171 (17) Å	µ = 6.29 mm−1
α = 101.929 (11)°	T = 110 K
β = 94.371 (10)°	Plate, colorless
γ = 93.299 (11)°	0.50 × 0.21 × 0.12 mm
V = 626.22 (15) Å3

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector	2432 independent reflections
Radiation source: fine-focus sealed tube	2312 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 10.5081 pixels mm-1	θmax = 74.0°, θmin = 6.1°
ω scans	h = −7→6
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→8
Tmin = 0.041, Tmax = 0.344	l = −18→18
3868 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1305P)2 + 0.5925P] where P = (Fo2 + 2Fc2)/3
2432 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 1.78 e Å−3
0 restraints	Δρmin = −1.28 e Å−3

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
Br1A	−0.10431 (6)	0.72017 (5)	0.94001 (2)	0.0266 (2)
Cl1A	0.58277 (16)	−0.04318 (14)	0.11075 (6)	0.0269 (3)
O1A	0.7080 (5)	0.2207 (4)	0.47588 (19)	0.0270 (6)
C12A	−0.0341 (6)	0.5947 (5)	0.7495 (3)	0.0205 (7)
H12A	−0.1777	0.6408	0.7378	0.025*
C1A	0.3919 (6)	0.1019 (5)	0.3683 (3)	0.0195 (7)
C2A	0.5227 (6)	0.0801 (5)	0.2923 (3)	0.0214 (7)
H2AA	0.6756	0.1315	0.2992	0.026*
C11A	0.0849 (6)	0.5125 (5)	0.6764 (3)	0.0215 (7)
H11A	0.0215	0.5019	0.6146	0.026*
C5A	0.0776 (6)	−0.0794 (5)	0.2713 (3)	0.0232 (8)
H5AA	−0.0727	−0.1364	0.2645	0.028*
C10A	0.2967 (6)	0.4452 (5)	0.6929 (3)	0.0207 (7)
C8A	0.3490 (7)	0.2931 (6)	0.5299 (3)	0.0245 (8)
H8AA	0.1944	0.3044	0.5110	0.029*
C14A	0.2701 (6)	0.5451 (5)	0.8595 (3)	0.0229 (7)
H14A	0.3318	0.5556	0.9216	0.027*
C3A	0.4245 (6)	−0.0180 (5)	0.2068 (3)	0.0200 (7)
C15A	0.3894 (6)	0.4648 (5)	0.7854 (2)	0.0210 (7)
H15A	0.5352	0.4227	0.7974	0.025*
C13A	0.0594 (7)	0.6090 (5)	0.8404 (2)	0.0200 (7)
C6A	0.1690 (6)	0.0229 (5)	0.3577 (3)	0.0214 (7)
H6AA	0.0799	0.0386	0.4091	0.026*
C7A	0.5018 (6)	0.2071 (5)	0.4605 (2)	0.0213 (7)
C9A	0.4280 (6)	0.3546 (5)	0.6187 (3)	0.0210 (7)
H9AA	0.5826	0.3381	0.6351	0.025*
C4A	0.2037 (6)	−0.0988 (5)	0.1951 (3)	0.0228 (7)
H4AA	0.1399	−0.1661	0.1360	0.027*

	U11	U22	U33	U12	U13	U23
Br1A	0.0240 (3)	0.0339 (3)	0.0202 (3)	0.00673 (19)	0.00381 (18)	0.0001 (2)
Cl1A	0.0292 (5)	0.0316 (5)	0.0200 (5)	0.0051 (4)	0.0061 (3)	0.0036 (4)
O1A	0.0217 (13)	0.0343 (15)	0.0224 (14)	0.0029 (12)	0.0001 (10)	0.0010 (11)
C12A	0.0183 (16)	0.0213 (17)	0.0211 (17)	−0.0020 (13)	−0.0003 (13)	0.0044 (14)
C1A	0.0205 (17)	0.0196 (17)	0.0191 (17)	0.0030 (13)	0.0014 (13)	0.0057 (13)
C2A	0.0207 (17)	0.0211 (17)	0.0213 (17)	0.0032 (14)	−0.0002 (13)	0.0026 (14)
C11A	0.0230 (17)	0.0209 (17)	0.0195 (17)	−0.0015 (14)	−0.0015 (13)	0.0039 (13)
C5A	0.0174 (16)	0.0211 (17)	0.030 (2)	−0.0020 (13)	−0.0039 (14)	0.0061 (15)
C10A	0.0222 (18)	0.0199 (17)	0.0194 (17)	−0.0032 (14)	−0.0003 (14)	0.0050 (13)
C8A	0.0228 (18)	0.0278 (19)	0.0217 (18)	0.0016 (14)	0.0005 (14)	0.0033 (15)
C14A	0.0227 (18)	0.0233 (18)	0.0213 (17)	−0.0006 (14)	−0.0019 (14)	0.0036 (14)
C3A	0.0201 (17)	0.0211 (18)	0.0197 (17)	0.0058 (13)	0.0029 (13)	0.0047 (14)
C15A	0.0179 (16)	0.0258 (18)	0.0192 (17)	0.0022 (13)	0.0018 (13)	0.0045 (14)
C13A	0.0252 (18)	0.0181 (17)	0.0155 (17)	0.0027 (14)	0.0045 (14)	−0.0006 (13)
C6A	0.0208 (17)	0.0239 (18)	0.0208 (18)	0.0013 (14)	0.0034 (13)	0.0075 (14)
C7A	0.0239 (17)	0.0218 (17)	0.0187 (17)	0.0006 (14)	0.0017 (14)	0.0061 (14)
C9A	0.0203 (17)	0.0208 (17)	0.0218 (18)	−0.0003 (14)	0.0008 (14)	0.0055 (14)
C4A	0.0240 (18)	0.0218 (17)	0.0203 (17)	0.0035 (14)	−0.0043 (14)	0.0008 (14)

Br1A—C13A	1.896 (4)	C5A—H5AA	0.9500
Cl1A—C3A	1.747 (4)	C10A—C15A	1.413 (5)
O1A—C7A	1.219 (5)	C10A—C9A	1.463 (5)
C12A—C11A	1.388 (6)	C8A—C9A	1.339 (5)
C12A—C13A	1.398 (5)	C8A—C7A	1.487 (5)
C12A—H12A	0.9500	C8A—H8AA	0.9500
C1A—C6A	1.395 (5)	C14A—C13A	1.387 (5)
C1A—C2A	1.402 (5)	C14A—C15A	1.396 (5)
C1A—C7A	1.503 (5)	C14A—H14A	0.9500
C2A—C3A	1.387 (5)	C3A—C4A	1.387 (5)
C2A—H2AA	0.9500	C15A—H15A	0.9500
C11A—C10A	1.396 (5)	C6A—H6AA	0.9500
C11A—H11A	0.9500	C9A—H9AA	0.9500
C5A—C4A	1.388 (6)	C4A—H4AA	0.9500
C5A—C6A	1.395 (5)
C11A—C12A—C13A	119.4 (3)	C15A—C14A—H14A	120.7
C11A—C12A—H12A	120.3	C2A—C3A—C4A	122.0 (3)
C13A—C12A—H12A	120.3	C2A—C3A—Cl1A	119.4 (3)
C6A—C1A—C2A	120.2 (3)	C4A—C3A—Cl1A	118.6 (3)
C6A—C1A—C7A	121.8 (3)	C14A—C15A—C10A	121.1 (3)
C2A—C1A—C7A	117.9 (3)	C14A—C15A—H15A	119.5
C3A—C2A—C1A	118.7 (3)	C10A—C15A—H15A	119.5
C3A—C2A—H2AA	120.7	C14A—C13A—C12A	121.5 (3)
C1A—C2A—H2AA	120.7	C14A—C13A—Br1A	119.2 (3)
C12A—C11A—C10A	120.8 (3)	C12A—C13A—Br1A	119.3 (3)
C12A—C11A—H11A	119.6	C1A—C6A—C5A	119.6 (3)
C10A—C11A—H11A	119.6	C1A—C6A—H6AA	120.2
C4A—C5A—C6A	120.7 (3)	C5A—C6A—H6AA	120.2
C4A—C5A—H5AA	119.6	O1A—C7A—C8A	122.6 (3)
C6A—C5A—H5AA	119.6	O1A—C7A—C1A	120.2 (3)
C11A—C10A—C15A	118.7 (4)	C8A—C7A—C1A	117.2 (3)
C11A—C10A—C9A	123.1 (3)	C8A—C9A—C10A	125.6 (4)
C15A—C10A—C9A	118.2 (3)	C8A—C9A—H9AA	117.2
C9A—C8A—C7A	120.4 (4)	C10A—C9A—H9AA	117.2
C9A—C8A—H8AA	119.8	C3A—C4A—C5A	118.8 (3)
C7A—C8A—H8AA	119.8	C3A—C4A—H4AA	120.6
C13A—C14A—C15A	118.5 (3)	C5A—C4A—H4AA	120.6
C13A—C14A—H14A	120.7
C6A—C1A—C2A—C3A	1.2 (5)	C7A—C1A—C6A—C5A	−177.6 (3)
C7A—C1A—C2A—C3A	179.4 (3)	C4A—C5A—C6A—C1A	−1.9 (6)
C13A—C12A—C11A—C10A	−0.4 (6)	C9A—C8A—C7A—O1A	−14.5 (6)
C12A—C11A—C10A—C15A	−0.9 (6)	C9A—C8A—C7A—C1A	166.1 (4)
C12A—C11A—C10A—C9A	179.0 (3)	C6A—C1A—C7A—O1A	155.6 (4)
C1A—C2A—C3A—C4A	−1.7 (5)	C2A—C1A—C7A—O1A	−22.6 (5)
C1A—C2A—C3A—Cl1A	178.8 (3)	C6A—C1A—C7A—C8A	−25.0 (5)
C13A—C14A—C15A—C10A	−1.3 (6)	C2A—C1A—C7A—C8A	156.8 (3)
C11A—C10A—C15A—C14A	1.7 (6)	C7A—C8A—C9A—C10A	178.5 (3)
C9A—C10A—C15A—C14A	−178.1 (3)	C11A—C10A—C9A—C8A	−13.4 (6)
C15A—C14A—C13A—C12A	0.0 (6)	C15A—C10A—C9A—C8A	166.4 (4)
C15A—C14A—C13A—Br1A	−179.5 (3)	C2A—C3A—C4A—C5A	0.4 (5)
C11A—C12A—C13A—C14A	0.8 (6)	Cl1A—C3A—C4A—C5A	179.8 (3)
C11A—C12A—C13A—Br1A	−179.7 (3)	C6A—C5A—C4A—C3A	1.4 (6)
C2A—C1A—C6A—C5A	0.6 (5)

Cg1 is the centroid of the C1A–C6A ring and Cg2 is the centroid of the C10A–C15A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···Cg2i	0.95	2.97	3.588 (4)	124
C5A—H5AA···Cg2ii	0.95	2.84	3.463 (4)	124
C12A—H12A···Cg1iii	0.95	2.83	3.527 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯Cg2i	0.95	2.97	3.588 (4)	124
C5A—H5AA⋯Cg2ii	0.95	2.84	3.463 (4)	124
C12A—H12A⋯Cg1iii	0.95	2.83	3.527 (4)	131

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1A–C6A ring and Cg2 is the centroid of the C10A–C15A ring.