2-[(E)-(5-Chloro-2-methylphenyl)iminomethyl]-4-methylphenol

In the molecule of the title Schiff base compound, C15H14ClNO, the two benzene rings are twisted with respect to each other, with a dihedral angle of 35.0 (3)°; an intramolecular O—H⋯N hydrogen bond occurs. In the crystal, weak C—H⋯π interactions between methyl groups and chlorophenyl rings link the molecules into supramolecular chains running along the a axis.

In the molecule of the title Schiff base compound, C 15 H 14 ClNO, the two benzene rings are twisted with respect to each other, with a dihedral angle of 35.0 (3) ; an intramolecular O-HÁ Á ÁN hydrogen bond occurs. In the crystal, weak C-HÁ Á Á interactions between methyl groups and chlorophenyl rings link the molecules into supramolecular chains running along the a axis.   Table 1 Hydrogen-bond geometry (Å , ).

Related literature
Cg1 is the centroid of the C9-C14 benzene ring.
The author acknowledges Lishui University for financial support. The molecular structure of title compound shows an E configuration, with a C9-N1═C8-C6 torsion angle of 0.26 (4)°. The bond distance of N1═C8 at 1.284 (3)Å is a typical double bond. It is noteworthy that H1 atom bonded to O1 is involved in an O1-H1···N1 intramolecular hydrogen bond, which results in formation of a six-membered ring ( Fig. 1). The dihedral angle between the two planes of the chlorophyenyl ring and methylphenol ring is 35.0 (3)°.

Experimental
A mixture of 5-chloro-2-methylaniline (1.42g, 10.0 mmol), 3-methyl-2-hydroxybenzaldehyde (1.36g, 10.0 mmol) in 50.0 ml CH 2 Cl 2 was fluxed under an Ar atmosphere for about 6 h to gain a yellow precipitate. The product was collected by filtration and washed with cold ethanol to give the Schiff base compound (2.25g in 86% yield). The yellow single crystals suitable for X-ray analysis were crystallized from CH 2 Cl 2 /absolute ethanol (3/2) systems by slow evaporation of solvents at room temperature over a week. Elemental analysis. Calc. for C 15 H 14 ClNO: C 69.36, H, 6.43%; Found C 69.92, H 6.80%.

Refinement
Hydroxy H atom was located in a difference Fourier map and positional parameters were refined freely, U iso (H) = 1.5U eq (O). Other H atoms were fixed geometrically and treated as riding with C-H = 0.96 Å (methyl) or 0.93 Å (aromatic), U iso (H) = 1.2U eq (C) for aromatic H atoms or U iso (H) = 1.5U eq (C) for methyl H atoms.

Figure 2
Thermal ellipsoid plot of the title compound. Ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radius. Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.