4-Chloro-N-(3,5-dimethylphenyl)benzamide

In the molecular structure of the title compound, C15H14ClNO, the amide group forms dihedral angles of 15.8 (2) and 27.2 (2)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (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 molecular structure of the title compound, C 15 H 14 ClNO, the amide group forms dihedral angles of 15.8 (2) and 27.2 (2) , respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (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 the title compound, one of the m-methyl groups in the aniline ring is positioned syn to the N-H bond, while the other m-methyl group is positioned anti to the N-H bond, the latter and the C═O bond being anti to each other, similar to that observed in 4-chloro-N-(3-methylphenyl)benzamide (Rodrigues et al., 2011).
In the title compound, the amide group forms dihedral angles of 15.8 (2)° and 27.2 (2)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (1)°.

Experimental
The title compound was prepared by a method similar to the one described by Rodrigues et al. (2011). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.
Plate like colourless single crystals of the title compound used in the X-ray diffraction studies were obtained by slow evaporation of the solvent from its ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

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

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