3-Methylsulfanyl-5-phenyl-4H-1,2,4-triazol-4-amine–water (6/1)

In the title compound, 6C9H10N4S·H2O, the dihedral angle between the five-membered triazole ring and the phenyl ring is 44.33 (16)°. The solvent water molecule is disordered about a special position with symmetry and its occupancy cannot be greater than 0.1667. The crystal structure is stabilized by intermolecular N—H⋯N and C–H⋯N hydrogen bonds.

In the title compound, 6C 9 H 10 N 4 SÁH 2 O, the dihedral angle between the five-membered triazole ring and the phenyl ring is 44.33 (16) . The solvent water molecule is disordered about a special position with 3 symmetry and its occupancy cannot be greater than 0.1667. The crystal structure is stabilized by intermolecular N-HÁ Á ÁN and C-HÁ Á ÁN hydrogen bonds.
The water molecule is disordered about a threefold inversion axis such that the asymmetric unit comprises one C 9 H 10 N 4 S molecule and a water molecule with occupancy ca 0.167 The C-N bond lengths in the molecule lie in the range 1.302 (5)-1.364 (4) Å. These are longer than a typical double C=N bond [ca 1.269 (2) Å] (Xiang et al., 2004), but shorter than a C-N single bond [ca 1.443 (4) Å] (Jin et al., 2004), indicating a degree of electron delocalization in the triazole ring.
The crystal packing in (I), Fig. 2, is stabilized by intermolecular and intramolecular N-H···N and C-H···N hydrogen bonds, Table 1.

Refinement
H atoms bound to N and O atoms were found in difference Fourier maps and their distances restrainted to N-H = 0.86 (2)Å and O-H = 0.85 (2)Å with U iso = 1.2U eq (parent atom), respectively. All other H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of Csp 2 -H = 0.93 Å with U iso = 1.2 U eq (parent atom), C(methyl)-H = 0.96 Å with U iso = 1.5 U eq (parent atom).

Special details
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.