2-Benzoylmethyl-4-[(2-benzylideneethylidene)amino]-5-(2-thienylmethyl)-2H-1,2,4-triazol-3(4H)-one

In the molecule of the title compound, C24H20N4O2S, the dihedral angle between the triazole and thiophene rings is 66.80 (4)° and the dihedral angle between the two benzene rings is 63.37 (4)°. An intramolecular C—H⋯O interaction results in the formation of a six-membered ring. A π⋯π contact between the benzene rings, [centroid–centroid distance = 3.918 (2) Å] may stabilize the structure. Weak C—H⋯π interactions are also present. The S, C and H atoms of the thiophene ring are disordered over two positions and were refined with occupancies of 0.654 (3) and 0.346 (3).


Comment
The 1,2,4-triazole compounds posses important pharmacological activities such as antifungal and antiviral activities. Examples of such compounds bearing the 1,2,4-triazole residues are fluconazole, the powerful azole antifungal agent as well as the potent antiviral N-nucleoside ribavirin (Tsukuda et al., 1998;Ünver et al., 2008). The 1,2,4-triazole nucleus is associated with diverse pharmacological activities such as antibacterial, hypoglycemic, antihypertensive, analgesic and specific magnetic properties (Colanceska-Ragenovic et al., 2001;Zhu et al., 2000). It was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatase inhibitors very useful for preventing breast cancer (Goss & Strasser-Weippl, 2004;Santen, 2003). There are antimicrobial agents having different structures are frequently used in treatment of microbial infections. However, there is an increasing resistance to these drugs.
Moreover, some of azole derivatives used as common antibiotics, such as Amphotericin B posses a toxic effect on humans as well as their antimicrobial effects (Clemons et al., 2004). We report herein the crystal structure of the title compound.
In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges.
In the triazole ring, N2-C3 [1.292 (3)  Intramolecular C-H···O interaction results in the formation of a six-membered ring having envelope conformation, with atom O1 displaced by 0.300 (3) Å from the plane of the other ring atoms.

Refinement
The S, C and H atoms of the thiophene ring were disordered. During the refinement process, the disordered atoms were refined with occupancies of 0.654 (3) and 0.346 (3). H atoms were positioned geometrically, with C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C).
Figures Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.  Fig. 1