2-(1,3-Benzothiazol-2-ylsulfanyl)-1-phenylethanone

In the molecule of the title compound, C15H11NOS2, the 1,3-benzothiazole ring is oriented at a dihedral angle of 6.61 (6)° with respect to the phenyl ring. In the crystal structure, intermolecular C—H⋯O interactions link the molecules in a herring-bone arrangement along the b axis and π–π contacts between the thiazole and phenyl rings [centroid–centroid distance = 3.851 (1) Å] may further stabilize the structure.

In the molecule of the title compound, C 15 H 11 NOS 2 , the 1,3benzothiazole ring is oriented at a dihedral angle of 6.61 (6) with respect to the phenyl ring. In the crystal structure, intermolecular C-HÁ Á ÁO interactions link the molecules in a herring-bone arrangement along the b axis andcontacts between the thiazole and phenyl rings [centroid-centroid distance = 3.851 (1) Å ] may further stabilize the structure.   et al., 1995;Fuju et al., 1988;Ni et al., 2006). In addition, β-keto-sulfones can be converted into optically active β-hydroxy-sulfones, halomethyl and dihalomethyl sulfones. Halomethyl and dihalomethyl sulfones are very good α-carbanion stabilizing substituents and precursors for the preparation of alkenes, aziridines, epoxides and β-hydroxy-sulfones. Haloalkyl sulfones are useful in preventing aquatic organisms from attaching to fishing nets and ship hulls (Grossert et al., 1984;Oishi et al., 1988;Antane et al., 2004). They also possess other biological properties such as herbicidal, bactericidal antifungal and insecticidal. Recently sulfone-linked heterocycles were prepared and have been showed antimicrobial activity (Padmavathi et al., 2008). We prepared the title compound as a precursor for the synthesis of gem-difluoromethylene-containing heterocycle, and reported herein its crystal structure.

Related literature
In the molecule of the title compound, (Fig. 1), the benzothiazole ring is oriented with respect to the phenyl ring at a dihedral angle of 6.61 (6)°. In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules in herringbone mode along the b axis ( Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contact between the thiazole and phenyl rings, Cg1-Cg2 i , [symmetry code: (i) x -1, y, z, where Cg1 and Cg2 are centroids of the rings (S1/N1/C1/C6/C7) and (C1-C6), respectively] may further stabilize the structure, with centroid-centroid distance of 3.851 (1) Å.

Experimental
For the preparation of the title compound, sodium carbonate (4.5 mmol) was added to a stirred solution of 2-mercaptobenzothiazole (3 mmol) in ethanol (15 ml) and water (15 ml) and stirred at room temperature for 30 min. α-Bromoacetophenone (3 mmol) was added to the reaction mixture and stirring was continued for 1h. The reaction was monitored by TLC and after 60 min showed the complete disappearance of the starting material. The reaction mixture was poured into HCl (1M, 100 ml) containing crushed ice (50 g). The product was filtered under vacuum and filtrate washed with ice-cold ethanol (10 ml) and water (10 ml

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.
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.