4-[(E)-2-Furylmethyleneamino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

In the title molecule, C13H10N4OS, the triazole ring makes dihedral angles of 16.14 (9) and 58.51 (11)°, respectively, with the phenyl and furan rings. Intramolecular C—H⋯N hydrogen bonds generate S(5) and S(6) ring motifs. In the crystal structure, centrosymmetrically related molecules are linked via N—H⋯S hydrogen bonds to form dimeric pairs, which are interlinked via C—H⋯O and C—H⋯π interactions.

In the title molecule, C 13 H 10 N 4 OS, the triazole ring makes dihedral angles of 16.14 (9) and 58.51 (11) , respectively, with the phenyl and furan rings. Intramolecular C-HÁ Á ÁN hydrogen bonds generate S(5) and S(6) ring motifs. In the crystal structure, centrosymmetrically related molecules are linked via N-HÁ Á ÁS hydrogen bonds to form dimeric pairs, which are interlinked via C-HÁ Á ÁO and C-HÁ Á Á interactions.
Bond lengths and angles in the title molecule ( Fig. 1) are found to have normal values (Allen et al., 1987). The furan ring is planar to within ±0.002 (2) Å and the triazole ring is also planar with a maximum deviation of 0.016 (2) Å for atom C1. The triazole and phenyl rings are twisted away from each other by an angle of 16.14 (9)°. The dihedral angle between the furan and triazole rings is 58.51 (11)°. Intramolecular C-H···N hydrogen bonds generate S(5) and S(6) ring motifs (Bernstein et al., 1995).
The crystal structure is stabilized by intermolecular C-H···O and N-H···S hydrogen bonds together with C-H···π interactions involving the phenyl ring. The centrosymmetrically related molecules are linked by N-H···S hydrogen bonds to form a dimeric pair (Fig. 2) which are interlinked via C-H···O hydrogen bonds.

Refinement
The N-bound H atom was located in a difference map and refined with a N-H distance restraint of 0.85 (1) Å. C-bound H atoms were positioned geometrically [C-H = 0.93%A] and refined using a riding model, with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Special details
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. 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 Rfactors(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.