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Volume 69 
Part 9 
Page o1385  
September 2013  

Received 10 July 2013
Accepted 17 July 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.008 Å
R = 0.048
wR = 0.120
Data-to-parameter ratio = 18.7
Details
Open access

(E)-3-(4-Bromo-5-methylthiophen-2-yl)acrylonitrile

aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia,bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales, and cDepartment of Chemistry, College of Science for Women, University of Babylon, Babylon, Iraq
Correspondence e-mail: gelhiti@ksu.edu.sa

In the title structure, C8H6BrNS, the molecules are planar with the exception of the methyl H atoms. In the crystal, molecules are linked by intermolecular C-H...N interactions to form ribbons parallel to the b axis. Groups of ribbons are arranged in a herringbone pattern to form a layered structure parallel to the ab plane.

Related literature

For related structures and their applications, see: Perner et al. (2003[Perner, R. J., Gu, Y.-G., Lee, C.-H., Bayburt, E. K., McKie, J., Alexander, K. M., Kohlhaas, K. L., Wismer, C. T., Mikusa, J., Jarvis, M. F., Kowaluk, E. A. & Bhagwat, S. S. (2003). J. Med. Chem. 46, 5249-5257.]); Kose (2004[Kose, M. (2004). J. Photochem. Photobiol. A, 165, 97-102.]); Chandra et al. (2006[Chandra, R., Kung, M.-P. & Kung, H. F. (2006). Bioorg. Med. Chem. Lett. 16, 1350-1352.]); Zhao et al. (2009[Zhao, J., Huang, L., Cheng, K. & Zhang, Y. (2009). Tetrahedron Lett. 50, 2758-2761.]); Pu et al. (2010[Pu, S., Liu, W. & Liu, G. (2010). Dyes Pigm. 87, 1-9.]); Dinçalp et al. (2011[Dinçalp, H., Askar, Z., Zafer, C. & Içli, S. (2011). Dyes Pigm. 91, 182-191.]).

[Scheme 1]

Experimental

Crystal data
  • C8H6BrNS

  • Mr = 228.11

  • Orthorhombic, P 21 21 21

  • a = 6.1347 (5) Å

  • b = 7.1124 (3) Å

  • c = 19.8245 (13) Å

  • V = 864.99 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.92 mm-1

  • T = 150 K

  • 0.40 × 0.30 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: empirical (using intensity measurements) (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.243, Tmax = 0.639

  • 3294 measured reflections

  • 1910 independent reflections

  • 1769 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.120

  • S = 1.05

  • 1910 reflections

  • 102 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.74 e Å-3

  • [Delta][rho]min = -1.12 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 699 Friedel pairs

  • Absolute structure parameter: 0.03 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N1i 0.93 2.59 3.501 (8) 166
Symmetry code: (i) [-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CHEMDRAW Ultra (Cambridge Soft, 2001[Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5330 ).


Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding for this research through Research Group Project No. RGP-VPP-239.

References

Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.
Chandra, R., Kung, M.-P. & Kung, H. F. (2006). Bioorg. Med. Chem. Lett. 16, 1350-1352.  [CrossRef] [PubMed] [ChemPort]
Dinçalp, H., Askar, Z., Zafer, C. & Içli, S. (2011). Dyes Pigm. 91, 182-191.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kose, M. (2004). J. Photochem. Photobiol. A, 165, 97-102.  [CrossRef] [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Perner, R. J., Gu, Y.-G., Lee, C.-H., Bayburt, E. K., McKie, J., Alexander, K. M., Kohlhaas, K. L., Wismer, C. T., Mikusa, J., Jarvis, M. F., Kowaluk, E. A. & Bhagwat, S. S. (2003). J. Med. Chem. 46, 5249-5257.  [ISI] [CrossRef] [PubMed] [ChemPort]
Pu, S., Liu, W. & Liu, G. (2010). Dyes Pigm. 87, 1-9.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Zhao, J., Huang, L., Cheng, K. & Zhang, Y. (2009). Tetrahedron Lett. 50, 2758-2761.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1385  [ doi:10.1107/S1600536813019752 ]

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