1-(4-Bromo-phen-yl)-2-(2-chloro-phen-oxy)ethanone.

In the title compound, C14H10BrClO2, a twofold halogenated derivative of phenyl-ated phenyl-oxyethanone, the least-squares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17)°. In the crystal, C-H⋯O contacts connect the mol-ecules into chains along the b-axis direction.

Related literature

For the biological properties of phen­oxy­acetic acid derivatives, see: Ali & Shaharyar (2007 ▶); Kunsch et al. (2005 ▶); Iqbal et al. (2007 ▶); Sato et al. (2002 ▶); Kitagawa et al. (1991 ▶); Bicking et al. (1976 ▶); Osborne et al. (1955 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H10BrClO2

M = 325.58

Monoclinic,

a = 15.2653 (8) Å

b = 4.5541 (2) Å

c = 23.7336 (9) Å

β = 129.135 (2)°

V = 1279.80 (10) Å3

Z = 4

Mo Kα radiation

μ = 3.41 mm−1

T = 200 K

0.36 × 0.07 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.377, T max = 0.811

15447 measured reflections

3040 independent reflections

1953 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.125

S = 1.02

3040 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −1.04 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204785X/rz5023sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204785X/rz5023Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204785X/rz5023Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204785X/rz5023Isup4.cml

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

C14H10BrClO2	F(000) = 648
Mr = 325.58	Dx = 1.690 Mg m−3
Monoclinic, P21/c	Melting point = 388–387 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.2653 (8) Å	Cell parameters from 8161 reflections
b = 4.5541 (2) Å	θ = 2.7–28.2°
c = 23.7336 (9) Å	µ = 3.41 mm−1
β = 129.135 (2)°	T = 200 K
V = 1279.80 (10) Å3	Needle, colourless
Z = 4	0.36 × 0.07 × 0.06 mm

Bruker APEXII CCD diffractometer	3040 independent reflections
Radiation source: fine-focus sealed tube	1953 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→17
Tmin = 0.377, Tmax = 0.811	k = −5→6
15447 measured reflections	l = −28→31

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0791P)2 + 0.0906P] where P = (Fo2 + 2Fc2)/3
3040 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −1.04 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.47277 (3)	0.61050 (9)	0.417783 (13)	0.05712 (18)
Cl1	−0.03928 (6)	−0.09989 (17)	−0.16076 (3)	0.0401 (2)
O1	0.07748 (15)	0.1858 (5)	−0.02338 (8)	0.0382 (5)
O2	0.27246 (18)	−0.0310 (6)	0.09698 (10)	0.0438 (5)
C1	0.1230 (2)	0.3184 (8)	0.04422 (12)	0.0369 (7)
H1A	0.0676	0.3028	0.0528	0.044*
H1B	0.1366	0.5294	0.0424	0.044*
C2	0.2335 (2)	0.1727 (7)	0.10682 (12)	0.0306 (6)
C11	0.1262 (2)	0.2570 (7)	−0.05457 (12)	0.0324 (7)
C12	0.0776 (2)	0.1275 (7)	−0.12175 (12)	0.0316 (6)
C13	0.1196 (3)	0.1825 (8)	−0.15782 (14)	0.0428 (8)
H13	0.0856	0.0939	−0.2036	0.051*
C14	0.2109 (3)	0.3659 (8)	−0.12732 (16)	0.0483 (9)
H14	0.2412	0.4013	−0.1515	0.058*
C15	0.2582 (3)	0.4979 (9)	−0.06159 (15)	0.0453 (8)
H15	0.3198	0.6292	−0.0413	0.054*
C16	0.2173 (2)	0.4421 (8)	−0.02466 (14)	0.0403 (7)
H16	0.2520	0.5310	0.0212	0.048*
C21	0.2890 (2)	0.2917 (7)	0.18133 (11)	0.0290 (6)
C22	0.3935 (2)	0.1744 (8)	0.23899 (13)	0.0373 (7)
H22	0.4271	0.0270	0.2298	0.045*
C23	0.4487 (2)	0.2704 (8)	0.30945 (13)	0.0398 (7)
H23	0.5207	0.1938	0.3485	0.048*
C24	0.3973 (2)	0.4787 (8)	0.32182 (12)	0.0361 (7)
C25	0.2928 (2)	0.5983 (7)	0.26559 (13)	0.0379 (7)
H25	0.2582	0.7413	0.2751	0.046*
C26	0.2403 (2)	0.5033 (8)	0.19527 (12)	0.0332 (6)
H26	0.1696	0.5854	0.1561	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.0536 (2)	0.0768 (4)	0.02415 (17)	−0.00832 (17)	0.01652 (15)	−0.01059 (11)
Cl1	0.0349 (3)	0.0493 (6)	0.0267 (3)	−0.0069 (3)	0.0150 (3)	−0.0092 (2)
O1	0.0282 (8)	0.0587 (16)	0.0232 (8)	−0.0105 (9)	0.0142 (7)	−0.0105 (8)
O2	0.0493 (12)	0.0416 (16)	0.0369 (10)	0.0035 (11)	0.0255 (9)	−0.0058 (9)
C1	0.0286 (12)	0.054 (2)	0.0227 (10)	0.0008 (13)	0.0136 (9)	−0.0059 (11)
C2	0.0279 (11)	0.036 (2)	0.0276 (11)	−0.0055 (12)	0.0171 (9)	−0.0044 (10)
C11	0.0263 (11)	0.043 (2)	0.0243 (10)	0.0033 (12)	0.0143 (9)	0.0022 (10)
C12	0.0290 (12)	0.035 (2)	0.0242 (10)	0.0031 (11)	0.0134 (9)	0.0024 (9)
C13	0.0496 (16)	0.049 (2)	0.0318 (12)	0.0052 (15)	0.0265 (12)	0.0039 (12)
C14	0.0552 (19)	0.054 (3)	0.0468 (16)	0.0000 (16)	0.0372 (15)	0.0092 (13)
C15	0.0404 (15)	0.046 (2)	0.0441 (15)	−0.0032 (15)	0.0242 (13)	0.0077 (14)
C16	0.0327 (13)	0.047 (2)	0.0289 (12)	−0.0016 (13)	0.0134 (11)	−0.0006 (11)
C21	0.0240 (11)	0.0334 (19)	0.0255 (10)	−0.0054 (11)	0.0137 (9)	−0.0034 (10)
C22	0.0246 (11)	0.050 (2)	0.0313 (12)	0.0016 (12)	0.0148 (10)	0.0000 (11)
C23	0.0249 (11)	0.055 (2)	0.0288 (11)	0.0004 (13)	0.0121 (9)	0.0036 (12)
C24	0.0320 (12)	0.050 (2)	0.0208 (10)	−0.0104 (13)	0.0141 (10)	−0.0063 (10)
C25	0.0343 (13)	0.047 (2)	0.0276 (12)	−0.0023 (13)	0.0171 (10)	−0.0071 (10)
C26	0.0265 (12)	0.041 (2)	0.0256 (11)	−0.0014 (12)	0.0133 (9)	−0.0028 (10)

Br1—C24	1.887 (2)	C14—H14	0.9500
Cl1—C12	1.740 (3)	C15—C16	1.383 (4)
O1—C11	1.379 (3)	C15—H15	0.9500
O1—C1	1.419 (3)	C16—H16	0.9500
O2—C2	1.202 (4)	C21—C26	1.378 (4)
C1—C2	1.526 (4)	C21—C22	1.396 (4)
C1—H1A	0.9900	C22—C23	1.385 (4)
C1—H1B	0.9900	C22—H22	0.9500
C2—C21	1.499 (3)	C23—C24	1.376 (5)
C11—C16	1.380 (4)	C23—H23	0.9500
C11—C12	1.395 (3)	C24—C25	1.391 (4)
C12—C13	1.379 (4)	C25—C26	1.388 (3)
C13—C14	1.375 (5)	C25—H25	0.9500
C13—H13	0.9500	C26—H26	0.9500
C14—C15	1.376 (5)
C11—O1—C1	117.5 (2)	C14—C15—H15	119.5
O1—C1—C2	111.6 (2)	C16—C15—H15	119.5
O1—C1—H1A	109.3	C11—C16—C15	119.9 (3)
C2—C1—H1A	109.3	C11—C16—H16	120.1
O1—C1—H1B	109.3	C15—C16—H16	120.1
C2—C1—H1B	109.3	C26—C21—C22	119.2 (2)
H1A—C1—H1B	108.0	C26—C21—C2	123.2 (2)
O2—C2—C21	121.9 (2)	C22—C21—C2	117.6 (3)
O2—C2—C1	121.7 (2)	C23—C22—C21	120.7 (3)
C21—C2—C1	116.5 (2)	C23—C22—H22	119.6
O1—C11—C16	125.3 (2)	C21—C22—H22	119.6
O1—C11—C12	115.8 (2)	C24—C23—C22	118.7 (2)
C16—C11—C12	118.9 (2)	C24—C23—H23	120.6
C13—C12—C11	120.8 (3)	C22—C23—H23	120.6
C13—C12—Cl1	120.0 (2)	C23—C24—C25	121.9 (2)
C11—C12—Cl1	119.2 (2)	C23—C24—Br1	118.72 (19)
C14—C13—C12	119.9 (3)	C25—C24—Br1	119.4 (2)
C14—C13—H13	120.1	C26—C25—C24	118.3 (3)
C12—C13—H13	120.1	C26—C25—H25	120.9
C13—C14—C15	119.6 (3)	C24—C25—H25	120.9
C13—C14—H14	120.2	C21—C26—C25	121.1 (2)
C15—C14—H14	120.2	C21—C26—H26	119.4
C14—C15—C16	121.0 (3)	C25—C26—H26	119.4
C11—O1—C1—C2	−77.1 (3)	C14—C15—C16—C11	−1.5 (6)
O1—C1—C2—O2	−0.8 (4)	O2—C2—C21—C26	−172.8 (3)
O1—C1—C2—C21	−179.2 (2)	C1—C2—C21—C26	5.6 (4)
C1—O1—C11—C16	1.5 (4)	O2—C2—C21—C22	5.4 (4)
C1—O1—C11—C12	−178.6 (3)	C1—C2—C21—C22	−176.2 (3)
O1—C11—C12—C13	−179.8 (3)	C26—C21—C22—C23	−0.6 (4)
C16—C11—C12—C13	0.1 (4)	C2—C21—C22—C23	−178.9 (3)
O1—C11—C12—Cl1	1.5 (4)	C21—C22—C23—C24	1.6 (5)
C16—C11—C12—Cl1	−178.6 (2)	C22—C23—C24—C25	−1.1 (5)
C11—C12—C13—C14	0.3 (5)	C22—C23—C24—Br1	−179.8 (2)
Cl1—C12—C13—C14	179.0 (3)	C23—C24—C25—C26	−0.3 (5)
C12—C13—C14—C15	−1.3 (5)	Br1—C24—C25—C26	178.4 (2)
C13—C14—C15—C16	1.9 (6)	C22—C21—C26—C25	−0.8 (4)
O1—C11—C16—C15	−179.6 (3)	C2—C21—C26—C25	177.3 (3)
C12—C11—C16—C15	0.5 (5)	C24—C25—C26—C21	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.99	2.57	3.457 (4)	149
C16—H16···O2i	0.95	2.57	3.425 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2i	0.99	2.57	3.457 (4)	149
C16—H16⋯O2i	0.95	2.57	3.425 (4)	150

Symmetry code: (i) .