N-[(Methylsulfanyl)methyl]benzamide

In the title compound, C9H11NOS, the phenyl ring and formamide unit make a dihedral angle of 23.93 (14)°, whereas the (methylsulfanyl)methyl group is oriented at a dihedral angle of 61.31 (8)° with respect to the phenyl ring. There are intermolecular N—H⋯O hydrogen bonds, forming C(4) chains along the [010] direction. These polymeric chains are linked by C—H⋯O hydrogen bonds to form polymeric sheets in the (110) plane.

In the title compound, C 9 H 11 NOS, the phenyl ring and formamide unit make a dihedral angle of 23.93 (14) , whereas the (methylsulfanyl)methyl group is oriented at a dihedral angle of 61.31 (8) with respect to the phenyl ring. There are intermolecular N-HÁ Á ÁO hydrogen bonds, forming C(4) chains along the [010] direction. These polymeric chains are linked by C-HÁ Á ÁO hydrogen bonds to form polymeric sheets in the (110) plane.

Experimental
The title compound was prepared by adding a solution of benzamide (0.1 g, 0.078 mmol) in 3 ml of dimethyl sulphoxide (DMSO) to a solution of phthalic anhydride (0.1 g, 0.078 mmol) in DMSO (3 ml). The reaction mixture was heated to 353 K for 6 h. The organic and aqueous layers were separated and the latter was extracted with chloroform (3×15 ml).
The organic layer was concentrated in vacuo and the residue was purified by chromatography (silica gel, EtOAc/hexane= 1:4). The title compound was obtained as a colorless crystalline solid. Yield = 0.14 g, 70%, m.p = 365 K. Crystallization from a saturated chloroform solution at ambient temperature gave colourless prisms.

Refinement
The H-atoms were positioned geometrically (N-H = 0.86 Å, C-H = 0.93-0.97 Å) and refined as riding with U iso (H) = xU eq (C, N), where x = 1.5 for methyl groups and x = 1.2 for all other H-atoms.

N-[(methylsulfanyl)methyl]benzamide
Crystal data Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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.