1-(4-Bromo­phen­yl)-2-(2-chloro­phen­oxy)ethanone

Shenvi, S.S.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S160053681204785X

Volume 68
Part 12
Page o3478
December 2012

Received 10 November 2012
Accepted 21 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.005 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 18.7
Details

1-(4-Bromophenyl)-2-(2-chlorophenoxy)ethanone

Seema S. Shenvi,^a Arun M. Isloor,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Surathkal, Mangalore 575 025, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C₁₄H₁₀BrClO₂, a twofold halogenated derivative of phenylated phenyloxyethanone, the least-squares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17)°. In the crystal, C-HO contacts connect the molecules 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_r = 325.58
Monoclinic, P 2₁ /c
a = 15.2653 (8) Å
b = 4.5541 (2) Å
c = 23.7336 (9) Å
= 129.135 (2)°
V = 1279.80 (10) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.125
S = 1.02
3040 reflections
163 parameters
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -1.04 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1BO2ⁱ	0.99	2.57	3.457 (4)	149
C16-H16O2ⁱ	0.95	2.57	3.425 (4)	150
Symmetry code: (i) x, y+1, z.

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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5023 ).

Acknowledgements

AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for a Young Scientist award.

References

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organic compounds