Three (E)-2-[(bromophenyl)iminomethyl]-4-methoxyphenols

Abstract

The title compounds, (E)-2-[(2-bromophenyl)iminomethyl]-4-methoxyphenol, C14H12BrNO2, (I), (E)-2-[(3-bromophenyl)iminomethyl]-4-methoxyphenol, C14H12BrNO2, (II), and (E)2-[(4-bromophenyl)iminomethyl]-4-methoxyphenol, C14H12BrNO2, (III), adopt the phenol-imine tautomeric form. In all three structures, there are strong intramolecular O-H center dot center dot center dot N hydrogen bonds. Compound (I) has strong intermolecular hydrogen bonds, while compound (III) has weak intermolecular hydrogen bonds. In addition to these intermolecular interactions, C-H center dot center dot center dot pi interactions in (I) and (III), and pi-pi interactions in (I), play roles in the crystal packing. The dihedral angles between the aromatic rings are 15.34 (12), 6.1 (3) and 39.2 (14)degrees for (I), (II) and (III), respectively.