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-methyl-benzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, mol-ecules 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 inter-molecular inter-actions 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. Mol-ecular orbital calculations providing electron-density plots of HOMO and LUMO mol-ecular orbitals and mol-ecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6-311 G++(d,p) basis set.
Highlights
Said Daoui,a Cemile Baydere,b* Fouad El Kalai,a* Lhassane Mahi,c Necmi Dege,b Khalid Karrouchid and Noureddine Benchata
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)
The dimers are linked by C—HÁ Á ÁO hydrogen bonds, generating ribbons propagating along the c-axis direction
Summary
Pyridazinone derivatives are important biologically active heterocyclic compounds (Dubey et al, 2015; Akhtar et al, 2016), which have been the subject of many studies because of their widespread biological activities, such as inflammatory (Barberot et al, 2018), antibacterial (El-Hashash et al, 2014), antidepressant (Boukharsa et al, 2016), antihypertensive (Demirayak et al, 2004), anti-HIV (Li et al, 2013), anticonvulsant (Partap et al, 2018), and their use as herbicidal agents (Asif, 2013). C10 of the pyridazine ring show the largest deviations from planarity (r.m.s. deviation = 0.0075 A ) in positive and negative directions [C10 = 0.0127 (11) Aand C9 = À0.0090 (11) A ]. The O3 C10 bond length of the pyridazinone carbonyl function is 1.2433 (19) Aand the N1—N2 bond length in the pyridazine ring is 1.3516 (19) A , both in accordance with values reported for related pyridazinones (El. Kalai et al, 2019a; Xu et al, 2005). In a continuation of our investigations of the molecular structures and Hirshfeld surfaces of new pyridazinone derivatives (Daoui et al, 2019a,b), we report on the synthesis and crystal and molecular structures of the title compound, 2-[5-(4-methylbenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin1-yl]acetic acid, as well as the analysis of the Hirshfeld surfaces. The phenyl (C1–C6) and pyridazine (C7–C10/N1/N2) rings are twisted relative to each other, making a dihedral
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