Crystal structure and conformational analysis of 2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione

Abstract

In the structure of the title compound, C14H12O3, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalenedione ring. The ring-to-chain C—C—C—C torsion angles are 50.7 (3), −176.6 (2) and 4.9 (4)°. An intramolecular methyl–hydroxy C—H...O hydrogen bond is present. In the crystal, molecules are primarily connected by intermolecular O—H...O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R22(10)]. Also present is a weak intermolecular C—H...O hydrogen bond linking the dimers and a weak π–π ring interaction [ring centroid separation = 3.7862 (13) Å], giving layers parallel to (10-3).

Keywords

• crystal structure
• naphthoquinone derivative
• molecular conformation
• hydrogen bonding