Synthesis, crystal structure, DFT calculation and Hirshfeld surface analysis of N-(4-methyl phenyl)-2-(3-nitro-benzamido) benzamide

Abstract

A new bis amide N-(4-methylphenyl)-2-(3-nitrobenzamide) benzamide was synthesized from a ring-opening reaction of 2-(3-nitrophenyl)-4H-benzoxazin-4-one, with 4-methyl aniline in a shorten reaction time (1.0 min) and characterized using different spectroscopic techniques (FT-IR, 1H-NMR, 13C-NMR) and single-crystal X-ray diffraction (XRD). In the crystal lattice, the molecules are linked by N–H···O and C–H···O hydrogen bonds. The Hirshfeld surface analysis mapped over shape index, curvedness indices, dnorm revealed strong H...H and H...O/O...H and intermolecular connections a key contributors to crystal packing structure. Density functional theory (DFT) calculations were applied with B3LYP/6-311G(d) level to provide theoretical data along with HOMO-LUMO electronic energy with the MEP map. KEY WORDS: Benzamide, Crystal structure, DFT calculation, Hirshfeld surface Bull. Chem. Soc. Ethiop. 2024, 38(1), 229-239. DOI: https://dx.doi.org/10.4314/bcse.v38i1.17