4-{5-[(2-Bromobenzyl)sulfanyl]-1H-tetrazol-1-yl}benzoic acid

In the title compound, C15H11BrN4O2S, the tetrazole ring makes dihedral angles of 45.97 (10) and 75.41 (1)°, respectively, with the benzoyl and bromobenzene rings while the dihedral angle between the benzene rings is 73.77 (1)°. In the crystal, molecules are linked through O—H⋯ N and C—H⋯ O hydrogen bonds, giving infinite chains in both the [110] and [1-10] directions. These chains are further connected by C—Br⋯π and C—O⋯π interactions and also by π–π stacking between tetrazole rings [centroid–centroid distance = 3.312 (1) Å], generating a three-dimensional network.

In the title compound, C 15 H 11 BrN 4 O 2 S, the tetrazole ring makes dihedral angles of 45.97 (10) and 75.41 (1) , respectively, with the benzoyl and bromobenzene rings while the dihedral angle between the benzene rings is 73.77 (1) . In the crystal, molecules are linked through O-HÁ Á Á N and C-HÁ Á Á O hydrogen bonds, giving infinite chains in both the [110] and [110] directions. These chains are further connected by C-BrÁ Á Á and C-OÁ Á Á interactions and also bystacking between tetrazole rings [centroid-centroid distance = 3.312 (1) Å ], generating a three-dimensional network.
This molecule has been identified as a PPAR gamma ligand candidate in a virtual screening study. The Peroxisome Proliferator-Activated Receptor, isoform gamma, is a transcription factor that regulates the expression of genes involved in glucose and lipid metabolism (Nolte et al., 1998). Our group recently described the crystal structure of a similar compound, evaluated as a PPARgligand in a competition assay (Mafud et al., 2013). Since tetrazoles are already known to have glucose lowering effects in vivo (Kees et al., 1989), in this virtual screening we chose some different representative molecules to evaluate the affinities and the extent of receptor activation. Here, we report the crystal structure of the title compound.

Experimental
A colourless single-crystal of the title compound was selected from the sample as supplied (Pharmeks Ltd.) without recrystallization.

Refinement
The hydroxyl H atom was located in a difference Fourier map and refined with U iso (H) = 1.5Ueq(O). The C-bound H atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 and 0.97 Å, for CH and CH 2 respectively, with U iso (H) = 1.2Ueq(C).

Figure 1
Perspective view of the molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.  A view along the a axis of the crystal packing of the title compound.  (Dwiggins, 1975) is used with some modification Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq