2-Benzyliminomethyl-6-bromo-4-chlorophenol

The title molecule, C14H11BrClNO, adopts a trans configuration with respect to the C=N double bond. The dihedral angle between the two aromatic rings is 70.4 (5)°. An intramolecular O—H⋯N hydrogen bond is observed between the hydroxyl and imine groups.

The title molecule, C 14 H 11 BrClNO, adopts a trans configuration with respect to the C N double bond. The dihedral angle between the two aromatic rings is 70.4 (5) . An intramolecular O-HÁ Á ÁN hydrogen bond is observed between the hydroxyl and imine groups.   Table 1 Hydrogen-bond geometry (Å , ). supporting information Acta Cryst. (2008). E64, o1734 [doi:10.1107/S1600536808024884] 2-Benzyliminomethyl-6-bromo-4-chlorophenol Xiao-Hua Pu S1. Comment Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. As an extension of the work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

Related literature
Bond lengths in the title molecule ( Fig. 1) have normal values (Allen et al.,1987). The C1═N1 bond length of 1.267 (9) Å conforms to the value for a double bond. The dihedral angle between the two aromatic rings is 70.4 (5)°. As expected, the molecule adopts a trans configuration about the C═N bond [C8-N1-C1-C2 = -178.6 (6)°]. An intramolecular O -H···N hydrogen bond is observed between hydroxyl and imine groups (Table 1).

S2. Experimental
3-Bromine-5-chlorosalicylaldehyde (0.1 mmol, 23.55 mg) and 1-benzylamine (0.1 mmol, 10.7 mg) were added to methanol (10 ml). The mixture was stirred for 30 min at room temperature to give a clear brown solution. After allowing the resulting solution to stand in air for 7 d, yellow block-shaped crystals of the title compound were formed on slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl 2 (yield 54%). Analysis found: C 51.76, H 4.0%; calculated for C 14 H 11 Br Cl N O : C 51.77, H 3.39%.

Figure 1
The molecular structure of the title compound, showing 30% probability ellipsoids. The dashed line represents a hydrogen bond.

Figure 2
The crystal packing of the title compound, viewed down the b axis. 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 > σ(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.