Received 28 March 2012
In the title compound, C14H13N3OS2, the thiophene ring is disordered over two orientations by ca 180° about the C-C bond axis linking the ring to the rest of the molecule, with a site-occupancy ratio of 0.651 (5):0.349 (5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2 (5), 4.6 (11) and 47.70 (7)° with the major and minor parts of the disordered thiophene ring and the terminal phenyl ring, respectively. In the crystal, no significant intermolecular hydrogen bonds are observed. The crystal packing is stabilized by - interactions [centroid-centroid distance = 3.589 (2) Å].
For the biological activity of 1,3,4-oxadiazole derivatives, see: Navarrete-Vázquez et al. (2007); Kadi et al. (2007); Padmavathi et al. (2009); El-Emam et al. (2004); Al-Deeb et al. (2006). For the synthesis of the title compound, see: Al-Omar (2010). For related 1,3,4-oxadiazole structures, see: Fun et al. (2011); El-Emam et al. (2012).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5107 ).
AAEE, MAAO and HAG thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, for financial support. HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.
Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40-47.
Al-Omar, M. A. (2010). Molecules, 15, 502-514.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.
El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795.
Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372.
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.
Navarrete-Vázquez, G., Molina-Salinas, G. M., Duarte-Fajardo, Z. V., Vargas-Villarreal, J., Estrada-Soto, S. & Gonzàlez-Salazar, F. (2007). Bioorg. Med. Chem. 15, 5502-5508.
Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44, 2106-2112.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.