Crystal structure, Hirshfeld surface analysis and DFT studies of N-(4-acetylphenyl)quinoline-3-carboxamide

Abstract

Crystalline organic compound, N-(4-acetylphenyl)quinoline-3-carboxamide (4) was readily prepared using our previously reported experimental procedure by the reaction of quinoline-3-carboxylic acid (1) with thionyl chloride to generate the acid chloride in situ followed by the coupling itself with 4-aminoacetophenone (3). This report describes the in-depth structural analysis thereof. The spectral characterization was done using FT-IR, 1H-NMR, 13C-NMR and UV-Vis spectroscopy, while its 3D-structure confirmed unambiguously by single crystal X-ray diffraction. The title compound crystallizes in the monoclinic system with the P21/c space group, Z = 4. The crystal packing is mainly controlled by N–H•••O, and C–H•••O hydrogen bond interactions. Molecular geometry optimizations were conducted using the DFT method at the B3LYP/6-31G+(d,p) level of theory and the theoretical UV-Vis spectrum was found to be in good agreement with the experimental spectrum.