Crystal structure of (3,5-dichloro-2-hydroxyphen-yl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone

The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11)degrees, respectively. The phenolic proton forms an intramolecular O-H center dot center dot center dot O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the molecules are linked through stacking interactions between the pyrazole rings [centroid-centroid distances = 3.546 (3)] and between the naphthalene ring system and the phenyl ring [centroid-centroid distances = 3.609 (4)angstrom] along the a-axis direction. The molecules are further connected through C-H center dot center dot center dot O hydrogen bonds, forming inversion dimers.