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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 [sigma](C-C) = 0.005 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 18.7
Details
Open access

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

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-H...O 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[Ali, M. A. & Shaharyar, M. (2007). Bioorg. Med. Chem. 15, 1896-1902.]); Kunsch et al. (2005[Kunsch, C., Luchoomun, J., Chen, X. L., Dodd, G. L., Karu, K. S., Meng, C. Q., Marino, E. M., Olliff, L. K., Piper, J. D., Qiu, F. H., Sikorski, J. A., Somers, P. K., Suen, K.-L., Thomas, S., Whalen, A. M., Wasserman, M. A. & Sundell, C. L. (2005). J. Pharmacol. Exp. Ther. 313, 492-501.]); Iqbal et al. (2007[Iqbal, A., Siddiqui, H. L., Ashraf, C. M., Ahmad, M. & Weaver, G. W. (2007). Molecules, 12, 245-254.]); Sato et al. (2002[Sato, S., Komoto, T., Kanamaru, Y., Kawamoto, N., Okada, T., Kaiho, T., Mogi, M., Morimoto, S., Umehara, N., Koda, T., Miyashita, A., Sakamoto, T., Niino, Y. & Oka, T. (2002). Chem. Pharm. Bull. 50, 292-297.]); Kitagawa et al. (1991[Kitagawa, M., Yamamoto, K., Katakura, S., Kanno, H., Yamada, K., Nagahara, T. & Tanaka, M. (1991). Chem. Pharm. Bull. (Tokyo), 39, 2681-2690.]); Bicking et al. (1976[Bicking, J. B., Robb, C. M., Watson, L. S. & Cragoe, E. J. Jr (1976). J. Med. Chem. 19, 544-547.]); Osborne et al. (1955[Osborne, D. J., Blackman, G. E., Novoa, S., Sudzuki, F. & Powell, R. G. (1955). J. Exp. Bot. 6, 392-408.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10BrClO2

  • Mr = 325.58

  • Monoclinic, P 21 /c

  • a = 15.2653 (8) Å

  • b = 4.5541 (2) Å

  • c = 23.7336 (9) Å

  • [beta] = 129.135 (2)°

  • V = 1279.80 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.377, Tmax = 0.811

  • 15447 measured reflections

  • 3040 independent reflections

  • 1953 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.125

  • S = 1.02

  • 3040 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -1.04 e Å-3

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) x, y+1, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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

Ali, M. A. & Shaharyar, M. (2007). Bioorg. Med. Chem. 15, 1896-1902.  [CrossRef] [PubMed] [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bicking, J. B., Robb, C. M., Watson, L. S. & Cragoe, E. J. Jr (1976). J. Med. Chem. 19, 544-547.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Iqbal, A., Siddiqui, H. L., Ashraf, C. M., Ahmad, M. & Weaver, G. W. (2007). Molecules, 12, 245-254.  [CrossRef] [PubMed] [ChemPort]
Kitagawa, M., Yamamoto, K., Katakura, S., Kanno, H., Yamada, K., Nagahara, T. & Tanaka, M. (1991). Chem. Pharm. Bull. (Tokyo), 39, 2681-2690.  [CrossRef] [PubMed] [ChemPort]
Kunsch, C., Luchoomun, J., Chen, X. L., Dodd, G. L., Karu, K. S., Meng, C. Q., Marino, E. M., Olliff, L. K., Piper, J. D., Qiu, F. H., Sikorski, J. A., Somers, P. K., Suen, K.-L., Thomas, S., Whalen, A. M., Wasserman, M. A. & Sundell, C. L. (2005). J. Pharmacol. Exp. Ther. 313, 492-501.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Osborne, D. J., Blackman, G. E., Novoa, S., Sudzuki, F. & Powell, R. G. (1955). J. Exp. Bot. 6, 392-408.  [CrossRef] [ChemPort]
Sato, S., Komoto, T., Kanamaru, Y., Kawamoto, N., Okada, T., Kaiho, T., Mogi, M., Morimoto, S., Umehara, N., Koda, T., Miyashita, A., Sakamoto, T., Niino, Y. & Oka, T. (2002). Chem. Pharm. Bull. 50, 292-297.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3478  [ doi:10.1107/S160053681204785X ]

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