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

Abstract

In the title compound, C21H12Br2N2O3, a 1,4-diaroyl pyrazole derivative, the dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and benzene rings, and the naphthalene ring system and benzene ring are 50.0 (2), 51.1 (2) and 1.34 (16)°, respectively. The phenolic proton forms an intramolecular O—H...O hydrogen bond with the adjacent carbonyl O atom. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming inversion dimers. The dimers are linked by C—H...Br hydrogen bonds, forming double stranded chains along [01-1]. The chains are linked by π–π interactions between the pyrazole rings and between the naphthalene and benzene rings [centroid–centroid distances = 3.592 (4) and 3.632 (4) Å, respectively].

Keywords

• crystal structure
• diaroyl pyrazole
• cyclization
• stacking interaction
• C—H...O hydrogen bonding