Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-phenylpyridazin-3(2H)-one

Abstract

The asymmetric unit of the title compound, C17H12Cl2N2O, contains one independent molecule. The molecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2)° and the dichlorophenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)°. In the crystal, pairs of N—H...O hydrogen bonds link the molecules to form inversion dimers with an R22(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the bc plane. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the molecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (31.4%), Cl...H/H...Cl (19.9%) and C...H/H...C (19%) contacts.

Keywords

• crystal structure
• pyridazin
• hydrogen bonding
• π–π interactions
• Hirshfeld surface analysis