Crystal structure and DFT study of (E)-2-chloro-4-{[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]methyl}phenol acetonitrile hemisolvate

Abstract

The title Schiff base compound, C13H9ClN4O5·0.5CH3CN, crystallizes as an acetonitrile hemisolvate; the solvent molecule being located on a twofold rotation axis. The molecule is nearly planar, with a dihedral angle between the two benzene rings of 3.7 (2)°. The configuration about the C=N bond is E, and there is an intramolecular N—H...Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by O—H...O and N—H...O hydrogen bonds, forming layers lying parallel to (10\overline{1}). The layers are linked by C—H...Cl hydrogen bonds, forming a supramolecular framework. Within the framework there are offset π–π stacking interactions [intercentroid distance = 3.833 (2) Å] present involving inversion-related molecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-dinitrobenzene ring, and the HOMO–LUMO gap is found to be 0.13061 a.u.