3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione

In the title molecule, C11H12N4S2, the dihedral angle between the triazole and benzene rings is 21.31 (5)°. A weak intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the crystal, pairs of N—H⋯S hydrogen bonds form inversion dimers. In addition, π–π interactions are observed between the benzene rings, with a centroid–centroid separation of 3.7599 (11) Å.

In the title molecule, C 11 H 12 N 4 S 2 , the dihedral angle between the triazole and benzene rings is 21.31 (5) . A weak intramolecular C-HÁ Á ÁS hydrogen bond generates an S(6) ring motif. In the crystal, pairs of N-HÁ Á ÁS hydrogen bonds form inversion dimers. In addition,interactions are observed between the benzene rings, with a centroid-centroid separation of 3.7599 (11) Å .
To this a few drops of conc.H 2 SO 4 was added as a catalyst and refluxed for 5 h on a water bath. The precipitate formed was filtered and recrystallized from mixture of methanol and dioxane (2:1) to yield the titled compound. The single crystals were grown from a solution of the titlr compound of methanol (mp. 355-357 K).

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent C/N atoms, with C-H distances of 0.93-0.96 Å and N-H distance of 0.86 Å; and with U iso (H) = 1.2U eq (C/N), except for the methyl groups where U iso (H) = 1.5U eq (C),.  (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figure 1
The molecular structure of the title compound with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.

Figure 2
The packing arrangement of molecules viewed along the a axis. Hydrogen bonds are shown as dashed lines.

3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione
Crystal data C 11 H 12 N 4 S 2 M r = 264.37 Triclinic, P1 Hall symbol: -P 1 a = 7.7873 (2) Å b = 9.5982 (2) Å c = 9.6041 (2) Å α = 76.608 (2) Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.