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

In the molecular structure of the title compound, C14H12ClNO, the meta-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 two aromatic rings make a dihedral angle of 77.4 (1)°. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010].

In the molecular structure of the title compound, C 14 H 12 ClNO, the meta-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 two aromatic rings make a dihedral angle of 77.4 (1) . In the crystal, the molecules are linked by N-HÁ Á ÁO hydrogen bonds, forming C(4) chains propagating in [010].
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD; 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: enCIFer (Allen et al., 2004). LK and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202-10) for financial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5712).
In (I), the meta-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, the N-H and C=O bonds in the C-NH-C(O)-C segment being anti to each other. Further, the two aromatic rings make the dihedral angle of 77.4 (1)°, compared to the values of 9.1 (2)° and 7.3 (3)°i n the two independent molecules of 3-chloro-N-(3-chlorophenyl)benzamide (Gowda et al., 2008).
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.
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
All H atoms were visible in difference maps and then treated as riding atoms with C-H distances of 0.93Å (C-aromatic), 0.96Å (C-methyl) and N-H = 0.86 Å. The U iso (H) values were set at 1.2 U eq (C-aromatic, N) and 1.5 U eq (C-methyl).