Abstract
The asymmetric units of the title compounds both contain one nonplanar mol-ecule. In 4-benzyl-6-phenyl-4,5-di-hydro-pyridazin-3(2H)-one, C17H14N2O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-di-chloro-benz-yl)-6-oxo-3-phenyl-1,4,5,6-tetra-hydropyridazin-1-yl]acetate, C20H16Cl2N2O3, (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the di-chloro-benzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with an R 2 2(8) ring motif. In the crystal structure of (II), C-H⋯O hydrogen bonds generate dimers with R 1 2(7), R 2 2(16) and R 2 2(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H⋯H (48.2%), C⋯H/H⋯C (29.9%) and O⋯H/H⋯O (8.9%) contacts. For compound (II), H⋯H (34.4%), C⋯H/H⋯C (21.3%) and O⋯H/H⋯O (16.5%) inter-actions are the most important contributions.
Highlights
Said Dadou,a* Sevgi Kansiz,b* Said Daoui,a Fouad El Kalai,a Cemile Baydere,b Rafik Saddik,c Khalid Karrouchi,d Necmi Degeb and Noureddine Benchata
In 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one, C17H14N2O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9); the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)
In methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6tetrahydropyridazin-1-yl]acetate, C20H16Cl2N2O3, (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18), whereas the phenyl ring of the dichlorobenzyl group is inclined to the pyridazine ring by 79.61 (19)
Summary
Pyridazines are an important family of six-membered aromatic heterocycles (Akhtar et al, 2016). The chemistry of pyridazinones has been an interesting field of research for decades and this nitrogen-containing heterocycle has become a scaffold of choice for the development of potential drug candidates (Dubey & Bhosle, 2015). Pyridazinone is an important pharmacophore possessing a wide range of biological applications (Asif, 2014). A review of the literature revealed that substituted pyridazinones have received a lot of attention in recent years because of their significant potential as antimicrobial (Sonmez et al, 2006), antihypertensive (Siddiqui et al, 2011), antidepressant (Boukharsa et al, 2016), anti-HIV (Livermore et al, 1993) and anti-inflammatory (Barberot et al, 2018) agents.
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