3-Chloro-N-(2-methylphenyl)benzamide

In the molecular structure of the title compound, C14H12ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N—H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48 (5)°]. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which link the molecules into chains along the b axis.

In the molecular structure of the title compound, C 14 H 12 ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N-H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48 (5) ]. The crystal structure is stabilized by N-HÁ Á ÁO hydrogen bonds, which link the molecules into chains along the b axis.

Experimental
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2320).

Comment
The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003;Gowda et al., 2000;Rodrigues et al., 2011;Saeed et al., 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda et al., 1996), in the present work, the crystal structure In the crystal structure, intermolecular N-H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.
Rod like colorless single crystals of the title compound used in x-ray diffraction studies were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.