A Comprehensive Topological Analysis of a Novel Flavonoid Extracted from Brazilian Cerrado Plants

Abstract

AbstractEpicatechin is a bioactive compound that has several biological functions, and can be found in a number of Brazilian Cerrado plants. The compound (2R,3R)‐2‐(3,4‐dihydroxyphenyl)‐3,4‐dihydro‐2H‐1‐benzopyran‐3,5,7‐triol (EPC) was extracted from Salacia crassifolia and its molecular architecture and supramolecular arrangement were characterized by X‐ray diffraction and Hirshfeld Surface. Theoretical calculations such as QTAIM, frontier molecular orbital, MEP and infrared spectra assignments were calculated at M06‐2X/6‐311++G(d,p) basis set. MEP revealed most positive region around hydrogen atoms of the hydroxyl group. X‐ray diffraction and QTAIM results showed that EPC forms a tetramer linked by classical hydrogen bonds O–H…O due to the number of hydroxyl groups available. The crystalline packing and supramolecular arrangement are stabilized by non‐classical hydrogen C–H…O and C–H…π interactions.