3-[1-(4-Isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C14H19N3S, the dihedral angle between the mean planes of the five- and six-membered rings is 74.69 (4)°. Pairs of intermolecular N—H⋯S interactions link neighbouring molecules into dimers with R 2 2(8) ring motifs. These dimers are then linked together by the same type of interactions into an infinite one-dimensional chain along the b axis.

In the title compound, C 14 H 19 N 3 S, the dihedral angle between the mean planes of the five-and six-membered rings is 74.69 (4) . Pairs of intermolecular N-HÁ Á ÁS interactions link neighbouring molecules into dimers with R 2 2 (8) ring motifs. These dimers are then linked together by the same type of interactions into an infinite one-dimensional chain along the b axis.

Comment
The 1,2,4-triazole nucleus has been incorporated into a wide variety of therapeutically interesting compounds. Several compounds containing 1,2,4-triazole rings are well known as drugs. For example, fluconazole is used as an antimicrobial drug (Shujuan et al., 2004), while vorozole, letrozole and anastrozole are non-steroidal drugs used for the threatment of cancer (Clemons et al., 2004) and loreclezole is used as an anticonvulsant (Johnston et al., 2002). Similarly substituted derivatives of triazole possess comprehensive bioactivities such as antimicrobial, anti-inflammatory, analgesic, antihypertensive, anticonvulsant and antiviral activities (Wei et al., 2007). Due to the progress that occurs in dealing with the chemistry of 1,2,4-triazoles as well as their biological activity, we synthesized and reported the crystal structure of the title compound.
The title compound, Fig. 1, comprises a single molcule in the asymmetric unit. The dihedral angle between the mean planes of the five-and six-membered rings is 74.69 (4)°. Pairs of intermolecular N-H···S interactions link neighbouring molecules into dimers with R 2 2 (8) ring motifs (Bernstein et al., 1995). These dimers are linked together into an infinite 1-D chains along the b axis.

Experimental
A mixture of 2-[2-(4-isobutylphenyl)propanoyl]hydrazinecarbothioamide (0.01 mole) and 10% KOH (10 ml) was refluxed for 3 h. After the mixture was cooled to room temperature, it was then neutralized by the gradual addition of glacial acetic acid. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Crystals suitable for X-ray analysis were obtained from ethanol solution by slow evaporation (Yield 71%; m.p.

Refinement
Hydrogen atoms bound to N1 and N2 were located from the difference Fourier map and refined freely; see Table. 1. The rest of the H atoms were positioned geometrically and refined with a riding model approximation with C-H = 0.95-1.00 Å and U iso (H) = 1.2 & 1.5 U eq (C). A rotating group model were used for the methyl groups. The highest peak (0.71 e. Å -3 ) is located 0.71 Å from C4 and the deepest hole (-0.29 e. Å -3 ) is located 1.07 Å from N2.
Figures Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms.

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.