(E)-3-[(3-Bromo-phen-yl)imino-meth-yl]benzene-1,2-diol: A combined X-ray and computational structural study

Abstract

The title compound, C13H10BrNO2, exists as an enol-imine form in the crystal and adopts an E configuration with respect to the C=N double bond. The mol-ecule is close to planar, with a dihedral angle of 6.88 (14)° between the aromatic rings. Intra-molecular O- H?N and O- H?O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by inter-molecular O- H?O hydrogen-bond inter-actions, 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?O hydrogen-bond inter-actions, there is an acceptable general agreement between them.