5-Hydroxy-7-methoxy-4H-chromen-4-one

Abstract

The mol­ecular conformation of the title compound, C10H8O4, isolated from Laretia acualis, is stabilized by a strong intra­molecular hydrogen bond between the hydroxyl and carbonyl groups. The crystal packing shows π–π stacking inter­actions. The chromene (4H-1-benzopyran-4-one) unit is essentially planar.

Use of π–π forces to steer the assembly of chromone derivatives into hydrogen bonded supramolecular layers: crystal structures and Hirshfeld surface analyses

“…With different substituents at the 5,7-and 2,7-position, the contribution of H/H interactions to the Hirshfeld Surface increases steadily up to well over 52% in 2 with a corresponding decrease in the contribution to 35% in GIRWAG. 39 Fig. 8 indicates that the molecular interactions in chromones are predominantly of the H/H and O/H types, which can account for 55% in SIMNEA 42 to 74.4% in 1.…”

“…8 indicates that the molecular interactions in chromones are predominantly of the H/H and O/H types, which can account for 55% in SIMNEA 42 to 74.4% in 1. The contribution of O/H interactions varies from 14% in REBHEM 40 to 35% in GIRWAG 39 and can be attributed to various substitutions on the benzopyran moiety, which in turn facilitates the formation of different supramolecular synthons, leading to diverse crystal packing arrangements.…”