Acta Cryst. (2009). E65, o2410-o2411  [ doi:10.1107/S1600536809035053 ]

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

Z. Kelesoglu, O. Büyükgüngör, Ç. Albayrak and M. Odabasoglu

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 molecule is close to planar, with a dihedral angle of 6.88 (14)° between the aromatic rings. Intramolecular O-HN and O-HO hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by intermolecular O-HO hydrogen-bond interactions, forming R₂²(10) and R₂²(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-HO hydrogen-bond interactions, there is an acceptable general agreement between them.

Online 9 September 2009

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