Crystal structure and Hirshfeld surface analysis of 4-(2,6-di-chloro-benz-yl)-6-phenyl-pyridazin-3(2H)-one.

Fouad El Kali,Khalid Karrouchi,Noureddine Benchat,Rafik Saddik,Sevgi Kansiz,Said Daoui,Necmi Dege

doi:10.1107/s2056989019005139

Abstract

The asymmetric unit of the title compound, C17H12Cl2N2O, contains one independent mol-ecule. The mol-ecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2)° and the di-chloro-phenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)°. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules to form inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C-H⋯O inter-actions, forming layers parallel to the bc plane. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the mol-ecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H⋯H (31.4%), Cl⋯H/H⋯Cl (19.9%) and C⋯H/H⋯C (19%) contacts.

Highlights

Chemical contextPyridazinone derivatives are biologically active heterocyclic compounds (Akhtar et al, 2016)
Fouad El Kali,a* Sevgi Kansiz,b* Said Daoui,a Rafik Saddik,c Necmi Dege,b Khalid Karrouchid and Noureddine Benchata
The molecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2) and the dichlorophenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)

Summary

Chemical context

Pyridazinone derivatives are biologically active heterocyclic compounds (Akhtar et al, 2016). Diverse pyridazinone derivatives have been reported to possess a variety of biological activities (Thakur et al 2010; Asif et al 2015) such as antimicrobial (Sonmez et al 2006), anti-inflammatory (Abouzid et al 2008), analgesic (Gokce et al 2009), anti-HIV (Livermore et al 1993), antihypertensive (Siddiqui et al 2011), anticonvulsant (Sharma et al 2014), cardiotonic (Wang et al 2008), antihistaminic (Tao et al 2012), antidepressant (Boukharsa et al 2016), glucan synthase inhibitors (Zhou et al 2011), phosphodiesterase (PDE) inhibitors (Ochiai et al 2012) and herbicidal activity (Asif et al 2013). We report the synthesis and the crystal and molecular structures of the title compound, as well as an analysis of its Hirshfeld surfaces. Symmetry codes: (i) Àx; Ày þ 1; Àz þ 1; (ii) Àx; y þ 12; Àz þ 32

Structural commentary

Supramolecular features

Findings

Database survey