Crystal Structure, Hirshfeld Surface Analysis and DFT Studies of 2-[5-(4-Methyl-Benz-yl)-6-Oxo-3-Phenyl-1,6-Di-Hydro-Pyridazin-1-yl]acetic Acid

Abstract

The title pyridazinone derivative, C20H18N2O3, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55(12)°, whereas the 4-methylbenzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97(10)°. In the crystal, molecules are linked by pairs of O - H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(14) ring motif. The dimers are linked by C - H⋯O hydrogen bonds, generating ribbons propagating along the c-axis direction. The intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. They revealed that the most significant contributions to the crystal packing are from H⋯H (48.4%), H⋯O/O⋯H (21.8%) and H⋯C/C⋯H (20.4%) contacts. Molecular orbital calculations providing electron-density plots of HOMO and LUMO molecular orbitals and molecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6-311G++(d,p) basis set. © Acta Cryst. 2019.