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Volume 69 
Part 3 
Page o350  
March 2013  

Received 16 January 2013
Accepted 22 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.043
wR = 0.086
Data-to-parameter ratio = 13.7
Details
Open access

2-(4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)malononitrile

aDepartment of Chemistry, American University in Cairo, PO Box 74, New Cairo 11835, Egypt, and bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: w.harrison@abdn.ac.uk

In the title compound, C12H7N3OS, the essentially planar thiazole ring (r.m.s. deviation = 0.022 Å) forms dihedral angles of 84.88 (9) and 1.8 (3)° with the phenyl ring and the -C(CN)2 group (r.m.s. deviation = 0.003 Å), respectively. The molecule has approximate local Cs symmetry. In the crystal, molecules are linked via C-H...N hydrogen bonds, forming chains propagating along [101]. The crystal studied was found to be an inversion twin with a refined 0.63 (1):0.37 (1) domain ratio.

Related literature

For background to 1,3-thiazolidin-4-ones and their properties, see: Singh et al. (1981[Singh, S. P., Parmar, S. S., Raman, K. & Stenberg, V. I. (1981). Chem. Rev. 81, 175-203.]); Liesen et al. (2010[Liesen, A. P., Aquino, T. M., Carvalho, C. S., Lima, V. T., Araujo, J. M., Lima, J. G., Faria, A. R., Melo, E. J. T., Alves, A. J., Alves, E. W., Alves, A. Q. & Goes, A. S. (2010). Eur. J. Med. Chem. 45, 3685-3691.]); Kocabalkanli et al. (2001[Kocabalkanli, A., Ates, A. & Otuk, G. (2001). Arch. Pharm. Pharm. Med. Chem. 334, 35-39.]); Kumar et al. (2007[Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.]). For further synthetic details, see: Mohareb et al. (2012[Mohareb, R. M., El-Sayed, N. & Abdelaziz, M. A. (2012). Molecules, 17, 8449-8463.]). For a related structure, see: Pomés Hernández et al. (1996[Pomés Hernández, R., Duque Rodríguez, J., Novoa de Armas, H. & Toscano, R. A. (1996). Acta Cryst. C52, 1731-1733.]).

[Scheme 1]

Experimental

Crystal data
  • C12H7N3OS

  • Mr = 241.27

  • Monoclinic, C c

  • a = 17.0305 (8) Å

  • b = 9.5638 (6) Å

  • c = 7.1651 (4) Å

  • [beta] = 104.199 (4)°

  • V = 1131.37 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 298 K

  • 0.20 × 0.13 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 2136 measured reflections

  • 2136 independent reflections

  • 1397 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.086

  • S = 1.01

  • 2136 reflections

  • 156 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 835 Friedel pairs

  • Flack parameter: 0.37 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...N2i 0.93 2.62 3.504 (5) 159
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: 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 (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.]), SCALEPACK and SORTAV (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]); 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5577 ).


Acknowledgements

The authors would like to thank the American University in Cairo for providing financial support to complete this work.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
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]
Kocabalkanli, A., Ates, A. & Otuk, G. (2001). Arch. Pharm. Pharm. Med. Chem. 334, 35-39.  [CrossRef] [ChemPort]
Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.  [CrossRef] [PubMed] [ChemPort]
Liesen, A. P., Aquino, T. M., Carvalho, C. S., Lima, V. T., Araujo, J. M., Lima, J. G., Faria, A. R., Melo, E. J. T., Alves, A. J., Alves, E. W., Alves, A. Q. & Goes, A. S. (2010). Eur. J. Med. Chem. 45, 3685-3691.  [ISI] [CrossRef] [ChemPort] [PubMed]
Mohareb, R. M., El-Sayed, N. & Abdelaziz, M. A. (2012). Molecules, 17, 8449-8463.  [CrossRef] [ChemPort] [PubMed]
Nonius (1998). 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.
Pomés Hernández, R., Duque Rodríguez, J., Novoa de Armas, H. & Toscano, R. A. (1996). Acta Cryst. C52, 1731-1733.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, S. P., Parmar, S. S., Raman, K. & Stenberg, V. I. (1981). Chem. Rev. 81, 175-203.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o350  [ doi:10.1107/S160053681300216X ]

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