Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methylbenzyl)-6-oxo-3-phenyl-1,6-dihydropyriciazin-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)degrees, whereas the 4-methylbenzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)degrees. In the crystal, molecules are linked by pairs of O-H center dot center dot center dot O hydrogen bonds, forming inversion dimers with an R-2(2)(14) ring motif. The dimers are linked by C-H center dot center dot center dot 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 center dot center dot center dot H (48.4%), H center dot center dot center dot O/O center dot center dot center dot H (21.8%) and H center dot center dot center dot C/C center dot center dot center dot 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/6-311 G++(d,p) basis set.