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

In the title compound, C14H12ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08 (18)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite chains running along the a axis.

In the title compound, C 14 H 12 ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08 (18) . In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into infinite chains running along the a axis.
In the title compound, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, similar to that observed in 2-chloro-N-(3-methylphenyl)benzamide (I) (Rodrigues et al., 2012). The ortho-methyl group in the anilino ring is also positioned syn to the N-H bond, in contrast to the anti conformation observed between the meta-methyl group and the N -H bond in (I).
The central amide core -NH-C(=O)-group is twisted by 58.77 (27)° and 56.30 (28)° out of the planes of the 2-chlorophenyl and 2-methylphenyl rings, respectively, while the two aromatic rings make only a dihedral angle of 4.08 (18)°, compared to the value of 38.7 (1)° in (I) In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into infinite chains running along the a-axis. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared by the method similar to the one described by Gowda et al. (2000). 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 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
Hydrogen atoms were placed in calculated positions with C-H distances of 0.93 Å (C-aromatic), 0.96 Å (C-methyl) and constrained to ride on their parent atoms. The amide H atom was visible in a difference map and refined with the N-H distance restrained to 0.860 (2) Å. The Uiso(H) values were set at 1.2Ueq (C-aromatic) or 1.5Ueq (C-methyl).

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.