Crystal structure, Hirshfeld surface analysis and HOMO–LUMO analysis of (E)-4-bromo-N′-(4-methoxybenzylidene)benzohydrazide

Abstract

The title Schiff base compound, C15H13BrN2O2, displays an E configuration with respect to the C=N double bond, which forms a dihedral angle of 58.06 (9)° with the benzene ring. In the crystal, the molecules are linked into chains parallel to the b axis by N—H...O and C—H...O hydrogen bonds, giving rise to rings with an R21(6) graph-set motif. The chains are further linked into a three-dimensional network by C—H...π interactions. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C...H (33.2%), H...H (27.7%), Br...H/H...Br (14.2%) and O...H/H...O (13.6%) interactions. The title compound has also been characterized by frontier molecular orbital analysis.

Keywords

• crystal structure
• Schiff base
• intermolecular interactions
• Hirshfeld surface analysis
• HOMO–LUMO calculation