4-Chloro-N-(2,6-dimethylphenyl)benzamide

The conformations of the N—H and C=O bonds in the structure of the title compound (N26DMP4CBA), C15H14ClNO, are anti to each other, similar to that observed in N-phenylbenzamide, N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. There are three molecules in the asymmetric unit of N26DMP4CBA. The central amide group is tilted with respect to the benzoyl ring by 45.2 (1)° in molecule 1, 21.2 (2)° in molecule 2 and 14.9 (2)° in molecule 3. The dihedral angles between the benzoyl and aniline rings are 39.9 (1), 51.0 (1) and 86.3 (3)° in molecules 1, 2 and 3, respectively. Intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains running along the [101] direction. One xylyl group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

The conformations of the N-H and C O bonds in the structure of the title compound (N26DMP4CBA), C 15 H 14 ClNO, are anti to each other, similar to that observed in N-phenylbenzamide, N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. There are three molecules in the asymmetric unit of N26DMP4CBA. The central amide group is tilted with respect to the benzoyl ring by 45.2 (1) in molecule 1, 21.2 (2) in molecule 2 and 14.9 (2) in molecule 3. The dihedral angles between the benzoyl and aniline rings are 39.9 (1), 51.0 (1) and 86.3 (3) in molecules 1, 2 and 3, respectively. Intermolecular N-HÁ Á ÁO hydrogen bonds link the molecules into infinite chains running along the [101] direction. One xylyl group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.
The intermolecular N-H···O hydrogen bonds link the molecules into infinite chains running along the [101] direction (Table 1).

Experimental
The title compound was prepared according to the literature method (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. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C-H = 0.96 Å (methyl) or 0.93 Å (aromatic) and N-H = 0.86 Å with U iso (H) = 1.2U eq (Caromatic or N) and with U iso (H) = 1.5U eq (Cmethyl).
The xylyl ring of the molecule 3 revealed excessively elongated displacement ellipsoids and therefore this ring (C48 to C55) as well as the C atoms attached to it were treated as disordered with two components marked A and B. The constraint of regular hexagon was applied and the two components A and B were treated using the tools (SAME and PART) available in SHELXL97 (Sheldrick, 2008). In the first stage of refinement, the site-occupation factors were refined to be 0.561 (4) for component A (atoms C48A to C55A) and 0.439 (4) for component B (atoms C48B to C55B) then they were fixed. Fig. 1

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 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.