Crystal structure of 2-(5-bromo-2-hydroxybenzylidene)-2,3-dihydro-1H-indene-1,3-dione

Abstract

The title molecule, C16H9BrO3, deviates slightly from planarity. The benzene ring makes a dihedral angle of 1.02 (9)° with the plane defined by the five-membered ring of the indandione moiety. The latter exhibits a minute twist indicated by the dihedral angle of 0.47 (9)° between the planes of the five- and six-membered rings. An intramolecular C—H...O hydrogen bond between the attached benzene ring with one of the indandione carbonyl O atoms stabilizes the molecular conformation. In the crystal, the molecules form dimers across centres of inversionviapairwise O—H...O hydrogen bonds. The dimers form stacks running parallel to [010] and interact through π–π interactions between the five-membered ring of one molecule and the six-membered rings of the indandione moiety of an adjacent molecule [centroid-to-centroid distance = 3.5454 (10) Å].