{5-Chloro-2-[(2-hydroxybenzylidene)amino]phenyl}(phenyl)methanone

The title Schiff base compound, C20H14ClNO2, adopts an E configuration about the azomethine bond. The phenol and chlorobenzene rings form dihedral angles of 84.71 (9) and 80.70 (8)°, respectively, with the phenyl ring and are twisted by 15.32 (8)° with respect to one another. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming columns parallel to the a axis.

The title Schiff base compound, C 20 H 14 ClNO 2 , adopts an E configuration about the azomethine bond. The phenol and chlorobenzene rings form dihedral angles of 84.71 (9) and 80.70 (8) , respectively, with the phenyl ring and are twisted by 15.32 (8) with respect to one another. The molecular conformation is stabilized by an intramolecular O-HÁ Á ÁN hydrogen bond, which forms an S(6) ring motif. In the crystal, molecules are linked by C-HÁ Á ÁO hydrogen bonds, forming columns parallel to the a axis.   Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) Àx þ 1; Ày; Àz þ 2; (ii) x À 1; y; z.

Comment
Schiff bases are well known ligands in coordination chemistry with a wide range of biological activities (Khan et al., 2009;Gerdemann et al., 2002;Samadhiya & Halve, 2001;Mallikarjun & Sangamesh, 1997;Fioravanti et al., 1995;Solomon & Lowery, 1993). The title compound was prepared as a part of our ongoing research on bioactive compounds.

Experimental
The synthesis of title compound was carried out by refluxing a mixture of salicylaldehyde (1 mol) and 2-amino-5-chlorobenzophenone (1 mol) in ethanol (50 ml) along with 3 drops of conc. H 2 SO 4 for 5 h at 343 K. After cooling the mixture was concentrated to one third under reduced pressure followed by addition of ethyl acetate (10 ml) and chloroforom (10 ml).
The mixture was kept at room temperature and yellow crystals were obtained after seven days. The crystalline product was collected, washed with methanol and dried to afford the title compound in 85% yield. Slow evaporation of a methanol solution afforded yellow crystals found suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.

Refinement
All C-bound H atoms were positioned geometrically with C-H = 0.93 Å, and constrained to ride on their parent atoms with U iso (H)= 1.2U eq (C). The hydroxy H atom atom was located in a difference Fourier map and refined isotropically. During the refinement, the C1···H2A separation was constrained to be 1.80 (2) Å. Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.