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Volume 69 
Part 1 
Page o65  
January 2013  

Received 10 November 2012
Accepted 3 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.121
Data-to-parameter ratio = 19.8
Details
Open access

4-(5-Chlorothiophen-2-yl)-1,2,3-selenadiazole

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India,bDepartment of Chemistry, Sri Sarada College for Women (Autonomus), Fairlands, Salem 636 016, India, and cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C6H3ClN2SSe, the selenadiazole and chlorothiophene rings are almost coplanar [dihedral angle = 5.24 (15)°]. In the crystal, C-H...N interactions link the molecules into chains extending along the b-axis direction. C-H...[pi] interactions also occur.

Related literature

For the biological activity of selenadiazole derivatives, see: El-Bahaie et al. (1990[El-Bahaie, S., Assy, M. G. & Hassanien, M. M. (1990). Pharmazie, 45, 791-793.]); El-Kashef et al. (1986[El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27-30.]); Padmavathi et al. (2002[Padmavathi, V., Sumathi, R. P. & Padmaja, A. (2002). J. Ecobiol. 14, 9-12.]); Plano et al. (2010[Plano, D., Moreno, E., Font, M., Encio, I., Palop, J. A. & Sanmartin, C. (2010). Arch. Pharm. Chem. Life Sci. 10, 680-691.]); Stadtman (1991[Stadtman, T. C. (1991). J. Biol. Chem. 266, 16257-16260.]); Velusamy et al. (2005[Velusamy, M., Justin Thomas, K. R., Lin, J. T. & Wen, Y. S. (2005). Tetrahedron Lett. 46, 7647-7651.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C6H3ClN2SSe

  • Mr = 249.57

  • Monoclinic, P 21 /c

  • a = 6.0412 (3) Å

  • b = 19.5870 (11) Å

  • c = 7.2010 (4) Å

  • [beta] = 110.257 (3)°

  • V = 799.38 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 5.22 mm-1

  • T = 293 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.330, Tmax = 0.391

  • 7064 measured reflections

  • 1978 independent reflections

  • 1558 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.121

  • S = 1.01

  • 1978 reflections

  • 100 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...N1i 0.93 2.62 3.545 (5) 171
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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.]); 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: BT6854 ).


Acknowledgements

The authors thank the TBI Consultancy, University of Madras, India, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Bahaie, S., Assy, M. G. & Hassanien, M. M. (1990). Pharmazie, 45, 791-793.  [ChemPort] [PubMed]
El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27-30.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Padmavathi, V., Sumathi, R. P. & Padmaja, A. (2002). J. Ecobiol. 14, 9-12.  [ChemPort]
Plano, D., Moreno, E., Font, M., Encio, I., Palop, J. A. & Sanmartin, C. (2010). Arch. Pharm. Chem. Life Sci. 10, 680-691.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stadtman, T. C. (1991). J. Biol. Chem. 266, 16257-16260.  [PubMed] [ChemPort]
Velusamy, M., Justin Thomas, K. R., Lin, J. T. & Wen, Y. S. (2005). Tetrahedron Lett. 46, 7647-7651.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o65  [ doi:10.1107/S1600536812049549 ]

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