Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone

Abstract

The title compound, C9H10O3, is a bioactive secondary metabolite, isolated from the endophytic fungus Nodulisporium sp. The compound exhibits an intra­molecular O—H⋯O hydrogen bond between the phenolic H atom and the carbonyl O atom of the adjacent acetyl group. In the crystal, mol­ecules are linked by hydrogen bonds involving the 4-phenolic H atom and a symmetry-related carbonyl O atom of a neighboring mol­ecule, resulting in extended supra­molecular chains along the a-axis direction. Aromatic π–π stacking inter­actions between the nearly parallel benzene rings of adjacent chains [centroid–centroid distance = 3.7478 (8) Å] further stabilize the three-dimensional supra­molecular framework.