Research Article: 3-[(N-Methyl­anilino)meth­yl]-5-(thio­phen-2-yl)-1,3,4-oxadiazole-2(3H)-thione

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Ali A. El-Emam, Mohamed A. Al-Omar, Hazem A. Ghabbour, Hoong-Kun Fun, Tze Shyang Chia.


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 π–π inter­actions [centroid–centroid distance = 3.589 (2) Å].

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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 ▶).