S-Phenyl benzothioate

In the title compound, C13H10OS, the phenyl rings are inclined to one another by 51.12 (8)°. There is a short C—H⋯S contact in the molecule.In the crystal, molecules are linked via C—H⋯O hydrogen bonds forming chains along the a axis. Molecules are also linked by C—H⋯π and weak π–π interactions [centroid–centroid distance = 3.9543 (10) Å].


Related literature
The title compound was obtained by the reaction of thiophenolyate and benzoyl chloride in an alkaline medium. For background to the title compound, see: Reddy et al. (2010); Katritzky et al. (2007). For details of the Cambridge Structural Database, see: Allen (2002 Table 1 Hydrogen-bond geometry (Å , ).
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999 Reaction of thiophenolyate and benzyol chloride in alkaline medium was described previously by Reddy et al., 2010. We have repeated the preparation of this compound to be used as starting material in some of our research. Benzoylation of thiophenol afforded colorless crystals of the title compound (see scheme and Figure 1) suitable for single crystal X-ray analysis of which the structure is reported herein. Molecules of the title compound crystalizes in the P2 1 /c (Z=4) space group. All bond lengths are within their normal ranges (Allen, 2002). In the crystal packing several C-H···O/S/π interactions (see table 1, Fig. 2) as well as π-π stacking are observed (centroid to centroid distance = 3.9543 (10) Å, ring slippage = 1.366 Å).

Experimental
A mixture of sodium hydroxide (344 mg, 8.61 mmol) and thiophenol (0.9 ml, 8.61 mmol) were dissolved in methanol (22 ml) for about 10 minutes. Benzoyl chloride (1 ml) was added to it. The reaction mixture was stirred overnight and then poured into ice-cold water. Afterwards it was filtered and dried to afford the title compound as white crystals in 63% yield.

Refinement
All hydrogen atoms were positioned in geometrically idealized positions with C-H = 0.95 Å and were allowed to ride on their parent atoms with U iso (H) = 1.2U eq . A discrepant reflection (1 3 2) was removed in the final stages of refinement

Figure 1
A view of (1). Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Packing diagram of (1) showing the C-H···O/S/π interactions as well as the π-π stacking.  133.6, 129.5, 129.2, 128.7, 127.5, 127.3. 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 S1 0.66521 (