Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one

The title pyridazinone derivative, C19H14Cl2N2O, an important pharmacophore with a wide variety of biological applications is not planar, the chlorophenyl and pyridazinone rings being almost perpendicular, subtending a dihedral angle of 85.73 (11)degrees. The phenyl ring of the styryl group is coplanar with the pyridazinone ring [1.47 (12)degrees]. In the crystal, N-H center dot center dot center dot O hydrogen bonds form inversion dimers with an R22 (8) ring motif and C-H center dot center dot center dot Cl hydrogen bonds also occur. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H center dot center dot center dot H (37.9%), C center dot center dot center dot H/H center dot center dot center dot C (18.7%), Cl center dot center dot center dot H/H center dot center dot center dot Cl (16.4%) and Cl center dot center dot center dot C/C center dot center dot center dot Cl (6.7%) contacts.

Automated summary

The pyridazinone derivative is not planar, with complex crystal packing primarily formed by hydrogen bonds and Hirshfeld surface analysis elucidating the intermolecular interactions. The key contributions to crystal packing are from H···H, C···H/H···C, Cl···H/H···Cl, and Cl···C/C···Cl contacts.