(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, 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 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.

SUBMITTER: Kelesoglu Z 

PROVIDER: S-EPMC2970385 | biostudies-other | 2009

REPOSITORIES: biostudies-other