3-Methylthiobenzamide

In the title compound, C8H9NS, the dihedral angle between the aromatic ring and the thioamide fragment is 36.0 (2)°. There are π-stacking interactions between coplanar aryl fragments, with a centroid–centroid separation of 3.658 (2) Å. In addition, there are intermolecular hydrogen bonds between the amino group and the S atoms.

In the title compound, C 8 H 9 NS, the dihedral angle between the aromatic ring and the thioamide fragment is 36.0 (2) . There are -stacking interactions between coplanar aryl fragments, with a centroid-centroid separation of 3.658 (2) Å . In addition, there are intermolecular hydrogen bonds between the amino group and the S atoms.

Comment
Thioamides are not only important intermediates in the synthesis of heterocyclic compounds but they also possess enormous biologically activities as reported in our previous articles (Khan et al., 2009a). In the present article, we report the crystal structure of 3-methylthiobenzamide, synthesized as a continuation of our previous work on the synthesis and biological screenings of five membered heterocycles (Akhtar et al., 2006(Akhtar et al., , 2007(Akhtar et al., , 2008Serwar et al., 2009).
There are two distinct hydrogen bonding interactions between the nitrogen and sulfur atoms. The first arranges the dimer with N···S distances of 3.422 (3)Å and the second links two thioamide dimers through another N···S interaction on the order of 3.455 (2) Å. These N-H···S hydrogen bonding interactions are similar to those seen in p-trifluoromethylbenzothioamide where the corresponding interactions are between 3.3735Å and 3.5133Å (Jian et al., 2006), in 4-chlorobenzothioamide where the N···S distances are 3.3769 (15)Å and 3.4527 (15)Å (Khan et al., 2009a) and in 4-bromobenzothioamide where the N···S distances are between 3.500 (2)Å and 3.605 (3) Å (Khan et al., 2009b).

Experimental
The title compound was synthesized from 3-methylbenzonitrile according to a reported procedure (Khan et al., 2009a). The recrystallization of the product from chloroform afforded crystals suitable for X-ray analysis.

Refinement
The hydrogen atoms were placed in geometrically idealized positions with C-H distances of 0.93Å (aromatic C-H), 0.96Å (methyl) and 0.86Å (amide N-H) and constrained to ride on the parent atom with U iso (H) = 1.2 U eq (C) for aromatic and amide protons or U iso (H) = 1.5 U eq (C methyl ). Fig. 1 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 Rfactors(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.