(E)-2-[(2-Chlorophenyl)iminomethyl]-4-methylphenol

The molecule of the title compound, C14H12ClNO, adopts the enol–imine tautomeric form, with an intramolecular O—H⋯N hydrogen bond. In the molecule, the two benzene rings are twisted with respect to each other by 30.6 (2)°. The crystal structure is stabilized by intermolecular C—H⋯π interactions.

Cg1 is the centroid of the C1-C6 ring.

Comment
Most Schiff bases have antibacterial, anticanser, anti-inflam-matory and antitoxic properties (Williams, 1972). In addition, Schiff bases have been used extensively as ligands in the field of coordination chemistry (Garnovski et al., 1993). There is considerable interest in Schiff base complexes due to their striking anti-tumour activities (Zhou et al., 2000). Schiff base compounds show photochromism and thermochromism in the solid state by proton transfer from the hydroxyl Oatom to the imine N atom (Cohen et al., 1964;Hadjoudis et al., 1987). Photochromic compounds are of great interest for the control and measurement of radiation intensity, optical computers and display systems (Dürr & Bouas-Laurent et al., 1990).

Experimental
The title compound was prepared by reflux a mixture of a solution containing 5-methylsalicylaldehyde (0.05 g, 0.367 mmol) in 20 ml e thanol and a solution containing 2-kloranilin (0.0447 g, 0.367 mmol) in 20 ml e thanol. The reaction mixture was stirred for 2 h under reflux. The crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation (yield % 80).

Refinement
H atoms were positioned geometrically and treated using a riding model with C-H = 0.93, 0.96, 0.82 and 0.93 Å for CH, CH 3 , OH and CH (aromatic), respectively. U iso (H) = 1.5U eq (C) for methyl or 1.2U eq (C,N) for others.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability.  as large as those based on F, and R-factors based on ALL data will be even larger.