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

In the structure of the title compound, C14H12ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N—H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.

In the structure of the title compound, C 14 H 12 ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C O bond, while the meta-methyl group in the aniline ring is positioned anti to the N-H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1) , respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1) . The crystal structure is stabilized by N-HÁ Á ÁO hydrogen bonds, which give rise to infinite chains running along the c axis.
In (I), the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the anilino ring is positioned anti to the N-H bond, similar to that observed in 3-chloro-N-(3-methylphenyl)benzamide (I) (Rodrigues et al., 2011).
The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 38.7 (1)°, compared to the value of 77.4 (1)° in (II).
In the crystal structure, intermolecular N1-H1···O1 hydrogen bonds (Table 1) link the molecules into infinite chains running along the c-axis. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared by a method similar to the one described by Gowda et al. (2006). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.
Plate like colorless single crystals of the title compound used in the 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.

Refinement
All hydrogen atoms bound to carbon were placed in calculated positions with C-H distances of 0.93Å (C-aromatic), 0.96Å (C-methyl) and constrained to ride on their parent atoms. The amide H atom was located in a difference map and refined with the N-H distance restrained to 0.86 (1) Å. U iso (H) values were set at 1.2 U eq (C-aromatic, N) and 1.5 U eq (Cmethyl).

Computing details
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).    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.