Synthesis, Crystal structure, DFT investigation and Antimicrobial, Molecular docking studies of (E)-3-methoxy-N'-(1-phenylethylidene) benzohydrazide

Abstract

Hydrazone derivatives have drawn much attention because of their large pharmacological applications. In the present work, the compound (E)-3-methoxy-N'-(1-phenylethylidene) benzohydrazide (3-MAPHN), noted was synthesized, and its 3D structure was determined by X-ray crystallography. Structural characterization by X-ray crystallography was supported by Density Functional Theory (DFT) calculations. Intermolecular interactions in the crystal network were determined using Hirshfeld surface analyses. The optimized geometry analysis and HOMO-LUMO of the molecule were computed using the DFT-B3LYP method and 6-311++G (d,p) basis set. The compound has a Orthorhombic system and Pca21space group with the parameters of a = 8.1494(4) A˚, b = 10.5844(6) A˚,c = 16.3976(9) A˚, α = 90 °, β = 90 °, γ = 90 °.and Z = 4, V = 1414.40(13)˚A3. It forms an S(6) ring motif with an intermolecular N-H/O and C-H/O hydrogen bonds. Hirshfeld surface analysis and 2D fingerprint plots signify meaningful interactions in crystal packing [H-H (49.8%), C-H (24%), O-H (16.4%), N-H (3.9%), C-N (3.0%), C-O (2.4%) and C-C (0.5%) contacts]. Atomic charges were predicted using the Mulliken population analysis. The molecular electrostatic potential (MEP) picture was drawn using the same level of theory to visualize the chemical reactivity and charge distribution on the molecule. Antimicrobial activity and docking studies of 3-MAPHN revealed that the molecule posses antibacterial and fungal activity and the ability of drug resistance, respectively.