Synthesis, crystal structure, DFT and Hirshfeld surface analysis of 4-fluoro-N-(1,3-dioxoisoindolin-2-yl)benzamide

Abstract

The 4-fluoro-N-(1,3-dioxoisoindolin-2-yl)benzamide was synthesized by the reaction of 4-fluorobenzohydrazide with phthalic anhydride in acetic acid. The compound was characterized by analytical instruments like FT-IR and NMR. The three-dimensional structure of the title compound was further confirmed by single-crystal X-ray diffraction study. In addition to the experimental study, theoretical calculations were performed to explore the molecular structure in order to analyze experimental and theoretical findings. The title compound crystallizes in the monoclinic space group P21/n as determined by the X-ray diffraction investigation, crystal data for C15H9FN2O3·H2O: a = 14.094(6) Å, b = 7.248(3) Å, c = 14.517(6) Å, β = 105.116(14)°, V = 1431.6(10) Å3, Z = 4, T = 298(2) K, μ(MoKα) = 0.112 mm-1, Dcalc = 1.402 g/cm3, 37521 reflections measured (4.684° ≤ 2Θ ≤ 60.6°), 4225 unique (Rint = 0.0517, Rsigma = 0.0311) that were used in all calculations. The final R1 was 0.0537 (I > 2σ(I)) and wR2 was 0.1501 (all data). The N-H···O and O-H···O hydrogen bonds linking molecules in the crystal form a three-dimensional framework structure. The electronic states and molecular properties of the title compound were determined using computational studies, like density functional theory and Hirshfeld surface analysis.

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“…However, the docking of compound C21 with PDB ID: 3HY3 provided different results ( Supplementary Figure S4 ). C10 interacted by forming a conventional hydrogen bond with TRP109 and hydrophobic interactions (Pi-Pi Stacked, Pi-Pi T-shaped, Alkyl, and Pi-Alkyl) with TYR83, TRP109, PRO81, MET90, TYR152, TYR153, and LYS150 ( Supplementary Table S4 ) ( Elancheran et al, 2023a ).…”

“…Very useful information about the compounds can be provided by Frontier molecular orbitals (FMO) such as electronegativity, stability, reactivity, and chemical hardness and softness ( Elancheran et al, 2023b ). The HOMO and LUMO parameters are used to compute the chemical reactivity descriptors and to assess the molecular reactivity ( Al-Janabi et al, 2021 ).…”