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Volume 69 
Part 6 
Page o859  
June 2013  

Received 9 April 2013
Accepted 3 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.081
Data-to-parameter ratio = 14.3
Details
Open access

(2E)-1-(5-Bromothiophen-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one

aDepartment of Physics, Govt. Science College, Hassan 573 201, Karnataka, India,bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570005, Karnataka, India,cInstitute of Pharmacy, GITAM University, Visakhapatnam-45, Andhrapradesh, India, and dDepartment of Physics, P. G. Department of Physics, LVD College, Raichur 584103, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C13H8BrClOS, the thiophene and phenyl rings are inclined by 40.69 (11)° to each other. The crystal structure is characterized by C-H...[pi] interactions, which link the molecules into broad layers parallel to (100). Short Br...Cl contacts [3.698 (1) Å] link these layers along [100].

Related literature

For general background to chalcones, see: Chun et al. (2001[Chun, N. L., Hsin, K. H., Horng, H. K., Mei, F. H., Hsien, C. L., Ya, L. C., Mei, I. C., Jaw, J. K., Jih, P. W. & Che, M. T. (2001). Drug Dev. Res. 53, 9-14.]); Horng et al. (2003[Horng, H. K., Lo, T. T., Kun, L. Y., Cheng, T. L., Jih, P. W. & Chun, N. L. (2003). Bioorg. Med. Chem. 1, 105-111.]); Lopez et al. (2001[Lopez, S. N., Castelli, M. V., Zacchino, S. A., Dominguez, J. N., Lobo, G., Charris, C. J., Cortés, J. C., Ribas, J. C., Devia, C., Rodríguez, A. M. & Enriz, R. D. (2001). Bioorg. Med. Chem. 9, 1999-2013.]); Mei et al. (2003[Mei, L., Prapon, W., Simon, L. C., Agnes, L. C. T. & Mei, L. G. (2003). Bioorg. Med. Chem. 11, 2729-2738.]). For related structures, see: Vepuri et al. (2012[Vepuri, S. B., Devarajegowda, H. C., Jeyaseelan, S., Anbazhagan, S. & Prasad, Y. R. (2012). Acta Cryst. E68, o3456.]); Li & Su (1993[Li, Z. & Su, G. (1993). Acta Cryst. C49, 1075-1077.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8BrClOS

  • Mr = 327.61

  • Monoclinic, P 21 /c

  • a = 15.235 (3) Å

  • b = 13.959 (3) Å

  • c = 5.9153 (11) Å

  • [beta] = 93.259 (3)°

  • V = 1255.9 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.63 mm-1

  • T = 293 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 14247 measured reflections

  • 3032 independent reflections

  • 2204 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.081

  • S = 1.05

  • 3032 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5-C10 ring.

D-H...A D-H H...A D...A D-H...A
C10-H10...Cg2i 0.93 2.87 3.557 (3) 132
C16-H16...Cg2ii 0.93 2.96 3.480 (3) 117
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2505 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his constant support and for the data collection.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chun, N. L., Hsin, K. H., Horng, H. K., Mei, F. H., Hsien, C. L., Ya, L. C., Mei, I. C., Jaw, J. K., Jih, P. W. & Che, M. T. (2001). Drug Dev. Res. 53, 9-14.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Horng, H. K., Lo, T. T., Kun, L. Y., Cheng, T. L., Jih, P. W. & Chun, N. L. (2003). Bioorg. Med. Chem. 1, 105-111.
Li, Z. & Su, G. (1993). Acta Cryst. C49, 1075-1077.  [CrossRef] [details]
Lopez, S. N., Castelli, M. V., Zacchino, S. A., Dominguez, J. N., Lobo, G., Charris, C. J., Cortés, J. C., Ribas, J. C., Devia, C., Rodríguez, A. M. & Enriz, R. D. (2001). Bioorg. Med. Chem. 9, 1999-2013.  [PubMed] [ChemPort]
Mei, L., Prapon, W., Simon, L. C., Agnes, L. C. T. & Mei, L. G. (2003). Bioorg. Med. Chem. 11, 2729-2738.  [PubMed]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Vepuri, S. B., Devarajegowda, H. C., Jeyaseelan, S., Anbazhagan, S. & Prasad, Y. R. (2012). Acta Cryst. E68, o3456.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o859  [ doi:10.1107/S1600536813012063 ]

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