Synthesis and crystal structure analysis of substituted 2-(3-(hydroxymethyl)quinolin-2-yl)phenol derivatives

Abstract

► Two novel quinoline derivatives were synthesized. ► The compounds are analyzed by IR, 1 H NMR, and Mass spectra. ► The structures were determined by X-ray diffraction method. ► Compound 1 has two conformers in the asymmetric unit with different hydrogen bonding. ► Compound 2 forms a helical structure with O–H⋯O and O–H⋯N synthons. Two novel quinoline derivatives e.g. 2-(3-(hydroxymethyl)-7-methylquinolin-2-yl)phenol ( 1 ) and 2-(3-(hydroxymethyl)-6-methoxyquinolin-2-yl)phenol ( 2 ) were synthesized. These compounds were characterized by IR, 1 H NMR and mass spectroscopy. Thermal analyses (DSC and TGA) and PXRD patterns were collected for the supporting data. Finally the crystal structures were solved by single crystal X-ray diffraction data and the structures were analyzed in terms of supramolecular interactions. Compound 1 consists of two symmetry independent molecules in the asymmetric unit. These two molecules are conformational isomers ( A and B ) and form different hydrogen bonding in the crystal structure. The Hirshfeld surfaces and associated 2D fingerprint plots were analyzed to differentiate the two conformers ( A and B ). Compound 2 form a helical structure with O–H⋯O and O–H⋯N hydrogen bond synthons along the c -axis.