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

Crystalline organic compound, N-(4-acetylphenyl)quinoline-3-carboxamide (4) was readily prepared us-ing 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 char-acterization was done using FT-IR, H-1-NMR, C-13-NMR and UV-Vis spectroscopy, while its 3D-structure confirmed unambiguously by single crystal X-ray diffraction. The title compound crystallizes in the mon-oclinic system with the P2(1)/c space group, Z = 4. The crystal packing is mainly controlled by N-H center dot center dot center dot O, and C-H center dot center dot center dot 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. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

The organo-crystalline compound N-(4-acetylphenyl)quinoline-3-carboxamide (4) was successfully synthesized and its structure was characterized using various spectroscopic methods and single crystal X-ray diffraction. Geometrical optimizations and theoretical UV-Vis spectrum analysis were carried out, showing good agreement with experimental results.