N-(3-Chlorophenyl)-4-methylbenzamide hemihydrate

In the title compound, C14H12ClNO·0.5H2O, the water molecule is located on a twofold axis of symmetry. The meta-Cl atom in the aniline ring is positioned anti to the N—H bond. The two benzene rings make a dihedral angle of 40.40 (11)°. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, which link the molecules into chains along the a axis.

In the title compound, C 14 H 12 ClNOÁ0.5H 2 O, the water molecule is located on a twofold axis of symmetry. The meta-Cl atom in the aniline ring is positioned anti to the N-H bond. The two benzene rings make a dihedral angle of 40.40 (11) . The crystal structure is stabilized by intermolecular N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds, which link the molecules into chains along the a axis.
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 Slovak Ministry of Education 1/0679/11, the Research and Development Agency of Slovakia (APVV-0202-10) for financial support of this work 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 award of an RFSMS research fellowship.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2309).
In (I), the water molecule is in special position and connects the different molecules of the compound. Further, the meta-Cl atom 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 are anti to each other, similar to that observed in N-(2-chlorophenyl)-4-methylbenzamide (Rodrigues et al., 2011). The The packing of molecules linked by N1-H1N···O2 and O2-H2O···O1 hydrogen bonds into infinite chains 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 colourless single crystals of the title compound 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
The C-and N-bound hydrogen atoms were positioned with idealized geometry using a riding model with C-H distances of 0.93Å (C-aromatic), 0.96Å (C-methyl) and N-H = 0.86 Å. The water hydrogen atoms are symmetry related, were seen in difference Fourier maps and were refined as free. The U iso (H) values were set at 1.2U eq (C aromatic, N, O) and 1.5U eq (C methyl). The disordered methyl group was refined using constrain 138