Received 17 August 2009
In the title compound, C12H11N3O2S, the pyridine ring is inclined to the thiophene ring, forming a dihedral angle of 34.96 (7)°. The mean plane through the hydrazide unit forms dihedral angles of 21.57 (8) and 53.08 (8)°, respectively, with the pyridine and thiophene rings. The two O atoms are twisted away from each other, as indicated by the C-N-N-C torsion angle of -81.27 (15)°. In the crystal structure, molecules are linked into an extended three-dimensional network by intermolecular N-HN, N-HO and C-HO hydrogen bonds. The crystal structure also features a short SO [3.2686 (10) Å] interaction and a weak intermolecular C-H interaction.
For general background to and application of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden et al. (2000). For the preparation of the title compound, see: Besra et al. (1993). For bond-length data, see: Allen et al. (1987). For a closely related structure, see: Naveenkumar et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: IS2451 ).
This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). HSNK and JHG thank USM for the award of a USM Fellowship.
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