3-(Adamantan-1-yl)-4-benzyl-1H-1,2,4-triazole-5(4H)-thione

The title compound, C19H23N3S, is a functionalized triazoline-3-thione derivative. The benzyl ring is almost normal to the planar 1,2,4-triazole ring (r.m.s. deviation = 0.007 Å) with a dihedral angle of 86.90 (7)°. In the crystal, molecules are linked by pairs of N—H⋯S hydrogen bonds, forming inversion dimers that enclose R 2 2(8) loops. The crystal packing is further stabilized by weak C—H⋯π interactions that link adjacent dimeric units into supramolecular chains extending along the a-axis direction.

The title compound, C 19 H 23 N 3 S, is a functionalized triazoline-3-thione derivative. The benzyl ring is almost normal to the planar 1,2,4-triazole ring (r.m.s. deviation = 0.007 Å ) with a dihedral angle of 86.90 (7) . In the crystal, molecules are linked by pairs of N-HÁ Á ÁS hydrogen bonds, forming inversion dimers that enclose R 2 2 (8) loops. The crystal packing is further stabilized by weak C-HÁ Á Á interactions that link adjacent dimeric units into supramolecular chains extending along the a-axis direction.

Experimental
A mixture of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), benzyl isothiocyanate (1.49 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for one hour and the solvent was distilled off in vacuo. Aqueous sodium hydroxide solution (10%, 15 ml) was added to the residue and the mixture was heated under reflux for 2 h. then filtered hot. On cooling, the mixture was acidified with hydrochloric acid and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 2.93 g (90%) of the title compound (C 19

Refinement
The nitrogen-bound H-atom was located in a difference Fourier map and was refined freely. Other H atoms were positioned geometrically (C=H 0.93-0.98 Å) and refined using a riding model with U iso (H) = 1.2 U eq (C) or 1.5 U eq (C) for methyl H atoms. A rotating group model was used for the methyl group.  The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.

Special details
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 matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1