Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[(<i>E</i>)-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2<i>H</i>)-one

Daoui, Said; Çınar, Emine Berrin; Kalai, Fouad El; Saddik, Rafik; Dege, Necmi; Karrouchi, Khalid; Benchat, N.

doi:10.1107/s2056989019015147

Cited by 8 publications

(1 citation statement)

References 18 publications

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“…The bond lengths in the N1-C15 chain (Table 1) are consistent with an alternation of double and single bonds while those in the amide fragment indicate strong -conjugation. The N1-N2 distance of 1.406 (4) A ˚agrees well with the values for related pyridazinones (Daoui, C ¸ınar et al, 2019;Daoui, Baydere et al, 2019). The conformation of the dihydropyridazine ring is close to a screw-boat [Â = 111.9 (6) , ' = 34.6 ( 6) ].…”

Section: Structural Commentarysupporting

confidence: 67%

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Daoui¹,

Muwafaq²,

Çınar³

et al. 2022

Acta Cryst E

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The pyridazine ring in the title compound, C20H17ClN2O3, adopts a screw-boat conformation. The whole molecule is flattened, the dihedral angles subtended by the least-squares plane of the central aromatic ring with those of the terminal benzene and pyridazine rings being 15.18 (19) and 11.23 (19)°, respectively. In the crystal, the molecules are linked by pairs of N—H...O bonds into centrosymmetric dimers and by C—H...π contacts into columns. The results of the Hirshfeld surface analysis show that the most prominent interactions are H...H, accounting for 36.5% of overall crystal packing, and H...O/O...H (18.6% contribution) contacts.

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Section: Structural Commentarysupporting

confidence: 67%

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Daoui¹,

Muwafaq²,

Çınar³

et al. 2022

Acta Cryst E

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Utilizing molecular geometry, pKa, NMR, and IR data to assess the accuracy of quantum mechanics-derived thermodynamic parameters in evaluating antioxidant activity

Metin,

Kawano

2024

Results in Chemistry

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Synthesis, crystal structure, DFT, Hirshfeld surface analysis, energy framework, docking and molecular dynamic simulations of ( E )-4-(4-methylbenzyl)-6-styrylpyridazin-3( 2H )-one as anticancer agent

Kalai

Çınar

Sert

et al. 2023

Journal of Biomolecular Structure and Dynamics

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Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[(E)-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2H)-one

Abstract: In the crystal, the molecules are linked by N—H⋯O and C—H⋯O interactions, forming a three-dimensional network. The theoretical geometrical parameters are in good agreement with XRD results.

Cited by 8 publications

References 18 publications

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Utilizing molecular geometry, pKa, NMR, and IR data to assess the accuracy of quantum mechanics-derived thermodynamic parameters in evaluating antioxidant activity

Synthesis, crystal structure, DFT, Hirshfeld surface analysis, energy framework, docking and molecular dynamic simulations of ( E )-4-(4-methylbenzyl)-6-styrylpyridazin-3( 2H )-one as anticancer agent

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Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[(E)-2-(thiophen-2-yl)ethenyl]-4,5-dihydropyridazin-3(2H)-one

Abstract: In the crystal, the mol­ecules are linked by N—H⋯O and C—H⋯O inter­actions, forming a three-dimensional network. The theoretical geometrical parameters are in good agreement with XRD results.

Cited by 8 publications

References 18 publications

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Utilizing molecular geometry, pKa, NMR, and IR data to assess the accuracy of quantum mechanics-derived thermodynamic parameters in evaluating antioxidant activity

Synthesis, crystal structure, DFT, Hirshfeld surface analysis, energy framework, docking and molecular dynamic simulations of ( E )-4-(4-methylbenzyl)-6-styrylpyridazin-3( 2H )-one as anticancer agent

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About

Abstract: In the crystal, the molecules are linked by N—H⋯O and C—H⋯O interactions, forming a three-dimensional network. The theoretical geometrical parameters are in good agreement with XRD results.