(E)-2-[(4-Chloro-phen-yl)imino-meth-yl]-5-methoxy-phenol and (E)-2-[(2-chloro-phen-yl)imino-meth-yl]-5-methoxy-phenol: X-ray and DFT-calculated structures

Abstract

The crystal structures of the title 4-chloro-phenyl, (I), and 2-chloro-phenyl, (II), compounds, both C14H12ClNO 2, have been determined using X-ray diffraction techniques and the mol-ecular structures have also been optimized at the B3LYP/6-31 G(d,p) level using density functional theory (DFT). The X-ray study shows that the title compounds both have strong intra-molecular O - H?N hydrogen bonds and that the crystal networks are primarily determined by weak C - H?? and van der Waals inter-actions. The strong intra-molecular O - H?N hydrogen bond is evidence of the preference for the phenol-imine tautomeric form in the solid state. The IR spectra of the compounds were recorded experimentally and also calculated for comparison. The results from both the experiment and theoretical calculations are compared in this study. © 2009 International Union of Crystallography.