3-Chloro-N-phenylbenzamide

In the title compound, C13H10ClNO, the meta-chloro group on the benzoyl ring is positioned syn to the C=O bond. The two aromatic rings make a dihedral angle of 88.5 (3)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into 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). PH 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: DS2154).
In (I), the meta-chloro group in the benzoyl ring is positioned syn to the C=O bond, while the N-H and C=O bonds in the C-NH-C(O)-C segment are anti to each other, similar to that observed in 3-Chloro-N-(3-chlorophenyl)-benzamide (II) (Gowda et al., 2008). Further, the two aromatic rings in (I) make the dihedral angle of 88.5 (3)°.
In the crystal structure, intermolecular N-H···O hydrogen bonds 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 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.
Rod 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.