(E)-3-[(3-Bromophenyl)iminomethyl]benzene-1,2-diol: a combined X-ray and computational structural study

Abstract

The title compound, C(13)H(10)BrNO(2), exists as an enol-imine form in the crystal and adopts an E configuration with respect to the C=N double bond. The molecule is close to planar, with a dihedral angle of 6.88 (14)degrees between the aromatic rings. Intramolecular O-H center dot center dot center dot N and O-H center dot center dot center dot O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by intermolecular O-H center dot center dot center dot O hydrogen-bond interactions, forming R(2)(2)(10) and R(2)(2)(20) chains along [100]. ab initio Hartree-Fock (HF), density-functional theory (DFT) and semi-empirical (AM1 and PM3) calculations and full-geometry optimizations were also performed. Although there are some discrepancies between the experimental and calculated parameters, caused presumably by the O-H center dot center dot center dot O hydrogen-bond interactions, there is an acceptable general agreement between them.