4-Amino-3-(p-tolyloxymethyl)-1H-1,2,4-triazole-5(4H)-thione

In the title triazole compound, C10H12N4OS, the triazole ring is essentially planar [maximum deviation = 0.009 (1) Å] and forms a dihedral angle of 5.78 (4)° with the benzene ring. In the crystal structure, molecules are linked into dimers by centrosymmetric N—H⋯S interactions. These dimers are linked into two-molecule-wide tapes by N—H⋯N and S⋯S [3.2634 (3) Å] interactions. In addition, they are further interconnected by weak N—H⋯S interactions into sheets parallel to the ab plane. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions.

In the title triazole compound, C 10 H 12 N 4 OS, the triazole ring is essentially planar [maximum deviation = 0.009 (1) Å ] and forms a dihedral angle of 5.78 (4) with the benzene ring. In the crystal structure, molecules are linked into dimers by centrosymmetric N-HÁ Á ÁS interactions. These dimers are linked into two-molecule-wide tapes by N-HÁ Á ÁN and SÁ Á ÁS [3.2634 (3) Å ] interactions. In addition, they are further interconnected by weak N-HÁ Á ÁS interactions into sheets parallel to the ab plane. The crystal structure is further stabilized by weak intermolecular C-HÁ Á Á interactions.
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  Comment 1,2,4-Triazole and its derivatives were reported to exhibit various pharmacological activities such as anti-microbial, analgesic, anti-inflammatory, anti-cancer and anti-oxidant properties (Amir et al., 2008;Kuş et al., 2008;Krzysztof et al., 2008;Padmavathi et al., 2008). Some of the present day drugs such as Ribavirin (anti-viral agent), Rizatriptan (anti-migraine agent), Alprazolam (anxiolytic agent), Fluconazole and Itraconazole (anti-fungal agents) are the best examples for potent molecules possessing the triazole nucleus. The amino and mercapto groups of thio-substituted 1,2,4-triazole serve as readily accessible nucleophilic centers for the preparation of N-bridged heterocycles. In view of their biological importance, we have synthesized the title compound (I) to study its crystal structure.
Experimental P-Cresoloxyacetyl hydrazine (18.0 g, 0.10 mol) was added slowly to a solution of potassium hydroxide (8.4 g, 0.15 mol) in ethanol (150 ml). The resulting mixture was stirred well until a clear solution was obtained. Carbon disulphide (11.4 g, 0.15 mol) was added drop-wise and the contents were stirred vigorously. Further stirring was continued for 24 h. The resulting mixture was diluted with ether (100 ml) and the precipitate formed was collected by filtration, washed with dry ether and dried at 65 °C under vacuum. It was used for the next step without any purification.
A mixture of the above synthesized potassium dithiocarbazinate (29.4 g, 0.10 mol), hydrazine hydrate (99 %, 0.20 mol) and water (2 ml) was heated gently to boil for 30 minutes. Heating was continued until the evacuation of hydrogen sulphide ceased. The reaction mixture was cooled to room temperature, diluted with water (100 ml) and acidified with HCl. The solid mass that separated was collected by filtration, washed with water and dried. Recrystallization was achieved from ethanol (Conti, 1964). The yield was 14.63 g, 62 %. M.p. 461-463 K.

Refinement
All the H atoms were located from difference Fourier map [range of C-H = 0.894 (15) -1.011 (12) Å] and allowed to refine freely. Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 > 2sigma(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.