Crystal structure of (4Z)-4-{[(2-chlorophenyl)amino](furan-2-yl)methylidene}-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one

Abstract

In the title compound, C21H16ClN3O2, the pyrazolone ring and the O=C—C=C—N mean plane [maximum deviation = 0.022 (2) Å] are nearly coplanar, making a dihedral angle 4.56 (8)°, while the phenyl and pyrazole rings subtend a dihedral angle of 19.75 (8)°. The compound is in the enamine–keto form and its structure is stabilized by an intramolecular N—H...O hydrogen bond. In the crystal, molecules are linked via C—H...N hydrogen bonds, forming chains along [010]. Between the chains there are π–π interactions [inter-centroid distances = 3.3902 (9) and 3.5956 (11) Å], linking the chains to form sheets parallel to (10-1).

Keywords

• crystal structure
• pyrazolone
• 4-acylpyrazolone
• o-chloroaniline
• hydrogen bonding