2-[4-Benzyl-5-(2-furyl)-4H-1,2,4-triazol-3-ylsulfanyl]acetamide

In the title compound, C15H14N4O2S, the phenyl ring is inclined at 70.25 (6)° with respect to the approximately planar furyl–triazolsulfanyl–acetamide unit. In the crystal structure, molecules related by inversion centers form dimers via intermolecular N—H⋯O hydrogen bonds between acetamide groups, resulting in eight-membered rings with an R 2 2(8) motif. In addition, the other H atom of the acetamide group is involved in an intermolecular hydrogen bond with an N atom of the triazole ring, resulting in chains extended along the c axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a axis.

In the title compound, C 15 H 14 N 4 O 2 S, the phenyl ring is inclined at 70.25 (6) with respect to the approximately planar furyl-triazolsulfanyl-acetamide unit. In the crystal structure, molecules related by inversion centers form dimers via intermolecular N-HÁ Á ÁO hydrogen bonds between acetamide groups, resulting in eight-membered rings with an R 2 2 (8) motif. In addition, the other H atom of the acetamide group is involved in an intermolecular hydrogen bond with an N atom of the triazole ring, resulting in chains extended along the c axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a axis.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2638).

Comment
Derivatives of 1,2,4-triazole have significant importance for their broad-spectrum biological and pharmacological activities, such as fungicidal, herbicidal, anticonvulsant, antitumoral, inhibition of cholesterol (Chai et al., 2003;Kanazawa et al., 1988;Hashimoto et al., 1990). In addition, they have many applications in the agriculture domain (Altman & Solomost, 1993). In this paper, we report the synthesis and crystal structure of the title compound, (I).
The structure of the title compound ( Fig. 1) is composed of a phenyl ring that is inclined at 70.25 (6)° with respect to a somewhat planar furyl-triazol-thio-acetamide moiety. The mean-planes of the furyl and triazole rings lie at 8.34 (13)° with respect to each other while the atoms in the thioacetamide group (S1/C7/C8/O2/N4) also form a plane which is inclined at 9.48 (10) and 3.45 (12)°, respectively, with furyl and triazole rings. Bond distances and bond angles in (I) agree well with the corresponding bond distances and bond angles reported in compounds closely related to (I) (Zareef, Iqbal & Parvez, 2008;Öztürk et al., 2004;Yildirim et al., 2004;Dege et al., 2004); in all these compounds, the mean-planes of the phenyl rings and the furyl-triazole moieties lie close to right angles. The molecules of (I) lying about inversion centers form dimers as a result of intermolecular N-H···O type hydrogen bonding between acetamide groups; the resulting eight membered rings exhibit an R 2 2 (8)-type motif (Bernstein et al., 1994). The second H-atom of the acetamide group is involved in an intermolecular hydrogen bond with N2 of the triazole ring thus resulting in a chain structure along the c-axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a-axis (Fig. 2). The structure is further stabilized by non-classical intramolecular interactions of the type C-H···O (Table 1).

Refinement
Though all the H atoms could be distinguished in the difference Fourier map the H-atoms bonded to C-atoms were included at geometrically idealized positions and refined in riding-model approximation with the following constraints: aryl and methylene C-H distances were set to 0.95 and 0.99 Å, respectively; in all these instances U iso (H) = 1.2 U eq (C). The H-atoms supplementary materials sup-2 bonded to N4 were allowed to refine with U iso (H) = 1.2 U eq (N4). The final difference map was free of any chemically significant features. Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids plotted at 50% probability level.