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Volume 69 
Part 8 
Page o1272  
August 2013  

Received 24 June 2013
Accepted 29 June 2013
Online 17 July 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.132
Data-to-parameter ratio = 19.1
Details
Open access

3,4-Dimethylthieno[2,3-b]thiophene-2,5-dicarbonitrile

aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia,bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia- 21321 Alexandria, Egypt, and cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

The asymmetric unit of the title compound, C10H6N2S2, contains two crystallographically independent but conformationally similar molecules. The fused thiophene ring cores are almost planar [maximum deviation = 0.027 (3) Å] with the thiophene rings forming dihedral angles of 0.5 (4)° in one molecule and 1.91 (4)° in the other. The crystal packing is stabilized only by van der Waals interactions.

Related literature

For the biological activity of thiophene derivatives, see: Mabkhot et al. (2013[Mabkhot, Y. N., Barakat, A., Al-Majid, A. & Choudhary, M. I. (2013). Int. J. Mol. Sci. 14, 5712-5722.]); Mishra et al. (2011[Mishra, R., Jha, K. K., Kumar, S. & Tomer, S. (2011). Pharma Chem. 3, 38-54.]). For the synthesis of fused heterocyclic compounds, see: Cornel & Kirsch (2001[Cornel, A. & Kirsch, G. (2001). J. Heterocycl. Chem. 38, 1167-1171.]); Mashraqui et al. (1999[Mashraqui, S. H., Hariharasubrahmanian, H. & Kumar, S. (1999). Synthesis, pp. 2030-2033.]). For crystal data for related thiophene compounds, see: Gunasekaran et al. (2009[Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.]); Mashraqui et al. (2004[Mashraqui, S. H., Asharf, M., Hariharasubrahmanian, H., Kellogg, R. K. & Meetsma, A. (2004). J. Mol. Struct. 689, 107-113.]).

[Scheme 1]

Experimental

Crystal data
  • C10H6N2S2

  • Mr = 218.31

  • Triclinic, [P \overline 1]

  • a = 7.2573 (11) Å

  • b = 10.1538 (15) Å

  • c = 13.665 (2) Å

  • [alpha] = 94.467 (3)°

  • [beta] = 99.120 (4)°

  • [gamma] = 95.850 (4)°

  • V = 984.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 273 K

  • 0.37 × 0.15 × 0.11 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.838, Tmax = 0.947

  • 13821 measured reflections

  • 4912 independent reflections

  • 3074 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.132

  • S = 0.99

  • 4912 reflections

  • 257 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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: RZ5077 ).


Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at the King Saud University (Riyadh) for funding this study through the research grant No. RGP-VPP-007.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cornel, A. & Kirsch, G. (2001). J. Heterocycl. Chem. 38, 1167-1171.  [CrossRef]
Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.  [CSD] [CrossRef] [IUCr Journals]
Mabkhot, Y. N., Barakat, A., Al-Majid, A. & Choudhary, M. I. (2013). Int. J. Mol. Sci. 14, 5712-5722.  [CrossRef] [ChemPort] [PubMed]
Mashraqui, S. H., Asharf, M., Hariharasubrahmanian, H., Kellogg, R. K. & Meetsma, A. (2004). J. Mol. Struct. 689, 107-113.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Mashraqui, S. H., Hariharasubrahmanian, H. & Kumar, S. (1999). Synthesis, pp. 2030-2033.  [CrossRef]
Mishra, R., Jha, K. K., Kumar, S. & Tomer, S. (2011). Pharma Chem. 3, 38-54.  [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1272  [ doi:10.1107/S1600536813017960 ]

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