N-[(4-Amino-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-methylbenzamide

In the title compound, C11H13N5OS, the dihedral angle between the triazole ring and the benzene ring is 84.21 (7)°. The amino group adopts a pyramidal configuration. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular structure and generates an S(8) ring. In the crystal, molecules are linked by intermolecular N—H⋯O, N—H⋯S, N—H⋯N and C—H⋯S hydrogen bonds into layers lying parallel to the bc plane. The crystal structure is further stabilized by aromatic π–π stacking interactions [centroid–centroid distance = 3.3330 (7) Å].


Experimental
A mixture of {[(4-methylphenyl)carbonyl]amino}acetic acid (1.93 g, 0.01 mol) and thiocarbohydrazide (1.0 g, 0.01 mol) was taken in a round bottomed flask fitted with a reflux condenser. The mixture was then fused on oil bath for 1 h. The reaction mass was slowly cooled to room temperature and the solid mass was treated with NaHCO 3 solution. The separated solid was collected by filtration and dried. Recrystallization was done from a mixture of ethanol-dioxane to yield colourless blocks of (I). Yield: 2.0 g, 76.0%, m.p. = 493-494 K.

Refinement
N-bound hydrogen atoms were located from the difference Fourier map and refined freely. The rest of the hydrogen atoms were positioned geometrically and refined using a riding model. A rotating group model was used for the methyl group.
Figures Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance mat- as those based on F, and R-factors based on ALL data will be even larger.