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Volume 69 
Part 7 
Page o1003  
July 2013  

Received 19 March 2013
Accepted 25 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.070
wR = 0.102
Data-to-parameter ratio = 15.0
Details
Open access

2-[(5-Methylthiophen-2-yl)methylidene]malononitrile

aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Puzhunan Road No.30 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: kaiguo@njut.edu.cn

There are two independent molecules in the asymmetric unit of the title compound, C9H6N2S, which is an intermediate compound of a cardiovascular drug. The two molecules are nearly planar, displaying dihedral angles of 3.5 (2) and 5.7 (2)° between the thiophene ring and the malononitrile moiety. In the crystal, C-H...N interactions lead to the formation of a sheet structure that packs in a parallel fashion.

Related literature

For a related structure, see: Altundas et al. (2011[Altundas, A., Ayvaz, S. & Logoglu, E. (2011). Med. Chem. Res. 20, 1-8.]). 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. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C9H6N2S

  • Mr = 174.22

  • Triclinic, [P \overline 1]

  • a = 9.1120 (18) Å

  • b = 9.9380 (2) Å

  • c = 10.1350 (2) Å

  • [alpha] = 81.10 (3)°

  • [beta] = 80.71 (3)°

  • [gamma] = 86.70 (3)°

  • V = 894.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.915, Tmax = 0.970

  • 3465 measured reflections

  • 3247 independent reflections

  • 1399 reflections with I > 2[sigma](I)

  • Rint = 0.081

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.102

  • S = 1.00

  • 3247 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...N2i 0.93 2.52 3.439 (6) 168
C6-H6A...N3ii 0.93 2.52 3.434 (6) 169
C12-H12A...N4iii 0.93 2.60 3.518 (6) 171
C15-H15A...N1i 0.93 2.51 3.430 (6) 170
Symmetry codes: (i) x, y, z+1; (ii) x+1, y-1, z-1; (iii) x, y, z-1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2229 ).


Acknowledgements

This research work was financially supported by School of Pharmaceutical Science, Nanjing University of Technology.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altundas, A., Ayvaz, S. & Logoglu, E. (2011). Med. Chem. Res. 20, 1-8.  [Web of Science] [CrossRef] [ChemPort]
Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1003  [ doi:10.1107/S1600536813014487 ]

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