Synthesis, characterization, molecular structure determination by single crystal X-ray diffraction, and Hirshfeld surface analysis of 7-fluoro-6-morpholino-3-phenylquinolin-1-ium chloride salt and computational studies of its cation

Abstract

7-fluoro-6-morpholino-3-phenylquinolin-1-ium chloride 2 has been synthesized and characterised by various spectral and electrochemical studies besides its molecular structure determination by a single-crystal X-ray diffraction investigation. Computational studies by Austin Model-1 (AM1), SCF-MM2 and DFT/B3LYP to compare the structural data with the single crystal XRD data have been performed on the cation of 2. The compound is found to crystallize in a monoclinic system in space group P21/c with crystal data as a = 11.0497(4) Å, b = 8.8712 (3) Å, c = 17.5099 (5) Å, β = β = 97.605 (17), V = 1701.3 (10) Å3, Z = 4, density = 1.346 Mg/m3, F (000) = 720, T = 293 K. Hirshfeld surface plots and fingerprint plots are obtained on 2 which show hydrogen bond intermolecular interactions. Electrochemical studies reveal that 2 undergoes diffusion-controlled irreversible anodic electron transfer and that it fluoresces at 520 nm with an absorption at ∼ 430 nm. The molecular docking of 2 on EGFR-TK protein and its cell viability assay on hypopharyngeal cancer cell line (FaDu) through MTT assay promise a scope of using compound 2 as an anticancer drug.