Abstract

In the title com-pound, C13H14N2O3, the dihydropyridazine ring (r.m.s. deviation= 0.166 Å) has a screw-boat conformation. The dihedral angle between its mean plane and the benzene ring is 0.77 (12)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds generate C(5) chains and N-H⋯O hydrogen bonds produce R 2 2(8) motifs. These types of inter-actions lead to the formation of layers parallel to (12). The three-dimensional network is achieved by C-H⋯O inter-actions, including R 2 4(8) motifs. Inter-molecular inter-actions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are by H⋯H (43.3%), H⋯C/C⋯H (19.3%), H⋯O/H⋯O (22.6%), C⋯N/N⋯C (3.0%) and H⋯N/N⋯H (5.8%) contacts. C-H⋯π inter-actions and aromatic π-π stacking inter-actions are not observed.

Highlights

  • Said Daoui,a* Cemile Baydere,b Fouad El Kalai,a Rafik Saddik,c Necmi Dege,b Khalid Karrouchid and Noureddine Benchata

  • The three-dimensional network is achieved by C—HÁ Á ÁO interactions, including R42(8) motifs

  • The most significant contributions to the crystal packing are by HÁ Á ÁH (43.3%), HÁ Á ÁC/CÁ Á ÁH (19.3%), HÁ Á ÁO/HÁ Á ÁO (22.6%), CÁ Á ÁN/NÁ Á ÁC (3.0%) and HÁ Á ÁN/NÁ Á ÁH (5.8%) contacts

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Summary

Chemical context

For decades the chemistry of pyridazinones has been an interesting field This nitrogen heterocycle became a scaffold of choice for the development of potential drug candidates (Akhtar et al, 2016; Dubey & Bhosle, 2015) because pyridazinone and its substituted derivatives are important pharmacophores possessing many different biological applications (Asif, 2014). Such compounds are used as anti-HIV (Livermore et al, 1993), antimicrobial (Sonmez et al, 2006), anticonvulsant (Partap et al, 2018), antihypertensive (Siddiqui et al, 2011), antidepressant (Boukharsa et al, 2016), analgesic (Gokce et al, 2009), anti-inflammatory (Barberot et al, 2018), antihistaminic (Tao et al 2012), cardiotonic (Wang et al, 2008) and herbicidal agents (Asif, 2013) or as glucan synthase inhibitors (Zhou et al, 2011). Oxystyryl)-4,5-dihydropyridazin-3(2H)-one, as well as an analysis of the Hirshfeld surfaces

Structural commentary
Supramolecular features
Database survey
Hirshfeld surface analysis
Synthesis and crystallization
Findings
Refinement
Full Text
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