Synthesis, characterization crystal and molecular structure studies of 5-(3-Methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one: Hirshfeld surface analysis and DFT calculations

Abstract

Abstract Benzodiazepines derivatives have been reported for their broad spectrum of biological applications. These derivatives are also being investigated for their supporting activity against human cancers. The title compound 5-(3-Methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one has been synthesized, characterized using 1H NMR, 13C NMR, IR techniques and finally the structure was confirmed by single crystal X-ray diffraction studies. The single crystals of the compound were obtained using ethanol as crystallization solvent. The compound C18H18N2O2 crystallizes in the orthorhombic crystal system with P212121 space group. The crystal structure of the title compound is stabilized by N H···O intermolecular hydrogen bond and π···π interactions. The structure also exhibits one dimensional chain stacking along a-axis through intermolecular interactions. These molecular interactions were then quantified using Hirshfeld surface analysis to understand their nature of involvement in interaction with other molecules. The analysis of the fingerprint plots revealed that the H…H (58.7%) interactions has the major contribution to the total molecular surface. Further, the electronic properties of the title compound were studied by computing the frontier molecular orbital energies using density functional theory calculations with B3LYP/6-311 + G (d, p) level basis set. Finally, the molecular electrostatic potential map was generated and the chemical reactive sites were identified to understand the molecular surface properties.