Synthesis, characterization, crystal structure and theoretical studies on 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol

The Schiff base compound, 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol, has been synthesized by a reaction of 5-bromosalicylaldehyde with 6-methyl-2-aminopyridine and characterized by elemental analyses, 1H-NMR spectroscopy and X-ray single-crystal diffraction. The title compound crystallizes in monoclinic system, space group P21/c, with a = 13.2721(12) Å, b = 4.5481(4) Ǻ, c = 19.972 (2) Ǻ, β = 96.653 (3)°, V = 1197.4 (2) Ǻ3 and Z = 4. The molecular geometry obtained from X-ray crystallography has been compared with that of the title compound in the ground state calculated by using the density function method (B3LYP) with 6/31G basis set. Calculated results show that DFT can well reproduce the structure of the title compound. The DFT results show that the molecule exists only in enol form. The molecular conformation of the title compound is stabilized by an intramolecular O1-H1·N1 hydrogen bond.