Methyl 2-[4-(trifluoromethyl)phenylsulfanyl]benzoate

In the title compound, C15H13F3O2S, the dihedral angle between the benzene rings is 79.5 (1)°. The ester group is twisted by 7.6 (1)° from the mean plane of the adjacent benzene ring. Disorder was modeled over two sites for one F atom of the trifluoromethyl group with an occupancy ratio of 0.54 (6):0.46 (6). In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (101). The networks are linked via C—H⋯π interactions, leading to the formation of a three-dimensional supramolecular structure.

In the title compound, C 15 H 13 F 3 O 2 S, the dihedral angle between the benzene rings is 79.5 (1) . The ester group is twisted by 7.6 (1) from the mean plane of the adjacent benzene ring. Disorder was modeled over two sites for one F atom of the trifluoromethyl group with an occupancy ratio of 0.54 (6):0.46 (6). In the crystal, molecules are linked via weak C-HÁ Á ÁO hydrogen bonds, forming two-dimensional networks lying parallel to (101). The networks are linked via C-HÁ Á Á interactions, leading to the formation of a threedimensional supramolecular structure.   Table 1 Hydrogen-bond geometry (Å , ).

Experimental
Cg is the centroid of the C2-C7 benzene ring. TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for women, Mysore, for giving permission to do research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

Comment
The title compound,C 15 H 13 F 3 O 2 S, is a methyl ester derivative of the starting material for the synthesis of the flupentixol  et al., 2011b). In view of the importance of flupentixol, we report herein on the crystal structure of the title compound a methyl ester derivative of the starting material for the synthesis of the flupentixol.
In the crystal, molecules are linked via C-H···O hydrogen bonds forming two-dimensional networks lying parallel to (101). These networks are linked via C-H···π interactions leading to the formation of a three-dimensional supramolecular structure (Table 1 and Fig. 2).

Experimental
The reactant 2-(4-Trifluoromethylphenylsulfanyl)benzoic acid (I) was obtained as a gift sample from R. L. Fine Chem, Bengaluru, India. 10 g of (I) [0.0335 mol] was dissolved in 50 ml of methanol, followed by the addition of 1 ml of 98% sulphuric acid and the mixture was refluxed for 8 hours at 338 K. The methanol was distilled off and 100 ml of 10% Na 2 CO 3 solution was added and the mixture stirred for 5 min. This was then extracted with dichloromethane and then the solvent was removed by distillation. The product formed was recrystallized from methanol giving colourless block-like crystals of the title compound (M.p. = 413-418 K).

Refinement
All of the H atoms were placed in their calculated positions and refined using the riding model approximation: C-H = 0.93 Å (CH) and 0.96 Å (CH 3 ), with U iso (H) = 1.5 eq (C-methyl) and = 1.     Table 1 for details; disordered atom F3A, and H atoms not involved in hydrogen bonding, have been omitted for clarity].

Special details
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.