3-[(4-Phenoxyphenyl)sulfanyl]-5-phenyl-1H-1,2,4-triazole

The title compound, C20H15N3OS, is V-shaped. In the 4-phenoxyphenyl group, the two rings are inclined to one another by 74.52 (13)°. These rings are inclined to the triazole ring by 72.20 (15) and 72.30 (15)°, respectively. The phenyl ring is inclined to the triazole ring by 10.85 (12)°. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming chains propagating along [010]. These chains are linked via pairs of C—H⋯S hydrogen bonds, forming sheets lying parallel to the ac plane.

The title compound, C 20 H 15 N 3 OS, is V-shaped. In the 4phenoxyphenyl group, the two rings are inclined to one another by 74.52 (13) . These rings are inclined to the triazole ring by 72.20 (15) and 72.30 (15) , respectively. The phenyl ring is inclined to the triazole ring by 10.85 (12) . In the crystal, molecules are linked via N-HÁ Á ÁN hydrogen bonds, forming chains propagating along [010]. These chains are linked via pairs of C-HÁ Á ÁS hydrogen bonds, forming sheets lying parallel to the ac plane.
This result is part of a larger research program that was supported by grants from the Ré gion Centre and the Labex IRON (ANR-11-LABX-0018-01). From a medicinal chemistry point of view, it is of great interest to develop efficient methods for the synthesis and the functionalization of 1,2,4-triazoles, as they are known to possess a wide range of biological activities, such as, as anticancer (Holla et al., 2002(Holla et al., , 2003 antitubercular (Walczak et al., 2004), antimicrobial (Zitouni et al., 2005Prasad et al., 2009;Wael et al., 2012), anticonvulsant (Almasirad et al., 2004), anti-inflammatory, analgesic (Amir & Shikha, 2004), antidepressant (Kane et al., 1988), and urease inhibitors (Akhtar et al., 2010). Thus, the synthesis of 1,2,4-triazoles and the investigation of their chemical and biological behaviour have acquired more importance in recent decades for these reasons.
Interestingly, working with sulfur-containing heterocycles may provide unexpected results and we report herein on the crystal structure of one derivative obtained within an unprecedented series of results (Ben Othman et al., 2014).
In the crystal, molecules are linked via N-H···N hydrogen bonds forming chains propagating along [010]; see Table 1 and Fig. 2. These chains are linked via pairs of C-H···S hydrogen bonds forming sheets lying parallel to the ac plane (Table 1 and Fig. 2).

Experimental
For the synthesis of the title compound, see Fig. 3. In a 25 ml flask, phenyl ZnBr solution in THF (1.5 mmol, 0.5M) was added drop wise under argon at room temperature to a solution of 3-Phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (0.5 mmol) in THF (5 ml), and the mixture was stirred for 25 min (see Fig 3). At the end of the reaction, the mixture was quenched with 15 mL of an aqueous solution of saturated NH 4 Cl, and extracted with CH 2 Cl 2 (2 × 20 ml). The extract was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluent 6:4 petroleum ether/AcOEt). The title compound was obtained as a white solid in

Refinement
The NH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 Å with U iso (H) = 1.2U eq (C).

Figure 1
The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
A perspective view along the b axis of the crystal pack of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for calrity).  The synthetic route of the title compound.