4-(3-Chlorophenyl)-3-[(2,6-difluorobenzyl)sulfanyl]-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole

In the title compound, C24H20ClF2N3O3S, the essentially planar triazole ring (r.m.s. deviation = 0.001 Å) forms dihedral angles of 22.35 (10), 68.17 (10) and 42.01 (10)° with the mean planes of the trimethoxyphenyl, chlorophenyl and difluorophenyl rings, respectively. A weak intramolecular C—H⋯π interaction occurs. In the crystal, molecules are linked into sheets lying parallel to the bc plane by C—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features weak C—H⋯π interactions.

In the title compound, C 24 H 20 ClF 2 N 3 O 3 S, the essentially planar triazole ring (r.m.s. deviation = 0.001 Å ) forms dihedral angles of 22.35 (10), 68.17 (10) and 42.01 (10) with the mean planes of the trimethoxyphenyl, chlorophenyl and difluorophenyl rings, respectively. A weak intramolecular C-HÁ Á Á interaction occurs. In the crystal, molecules are linked into sheets lying parallel to the bc plane by C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds. The crystal packing also features weak C-HÁ Á Á interactions.

Comment
During the last few decades, a considerable attention has been devoted to the synthesis of [1, 2, 4] triazole derivatives possessing such diverse pharmacological properties as antimicrobial, anti-inflammatory (Zhou et al., 2007), analgesic antitumorial, antihypertensive (Chen et al., 2007), anticonvulsant and antiviral activities . Some 1, 2, 4triazoles are used as DNA cleaving agents and potassium channel activators. Introduction of fluorine atom in these compounds could alter the course of the pharmacological activities (Kalluraya et al., 2004). In particular, introduction of diflurophenyl substituted group in the moiety immensely increases the pharmacological as well liphophilicity effectiveness (Sunil et al., 2009). It is also observed that the amino and mercapto groups in triazoles are readily accessible nucleophilic centers (Chandrakantha et al., 2010).

Refinement
All the H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.99 Å. The U iso values were constrained to be 1.5U eq of the carrier atom for methyl H atoms and 1.2U eq for the remaining H atoms. A rotating group model was used for the methyl groups. Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.