Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[(E)-2-(thio-phen-2-yl)ethenyl]-4,5-di-hydro-pyridazin-3(2 H)-one

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

doi:10.1107/S2056989019015147

Crystal structure, Hirshfeld surface analysis and DFT studies of 6-[(E)-2-(thio-phen-2-yl)ethenyl]-4,5-di-hydro-pyridazin-3(2 H)-one

Acta Crystallogr E Crystallogr Commun. 2019 Nov 15;75(Pt 12):1880-1883. doi: 10.1107/S2056989019015147. eCollection 2019 Dec 1.

Authors

Said Daoui¹, Emine Berrin Çınar², Fouad El Kalai¹, Rafik Saddik³, Necmi Dege², Khalid Karrouchi⁴, Noureddine Benchat¹

Affiliations

¹ Laboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohamed I University, 60000 Oujda, Morocco.
² Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs, University, Samsun, Turkey.
³ Laboratory of Organic Synthesis, Extraction and Valorization, Faculty of Sciences, Ain Chok, University Hassan II, Casablanca, Rabat, Morocco.
⁴ Laboratory of Plant Chemistry, Organic and Bioorganic Synthesis, URAC23, Faculty of Science, BP 1014, GEOPAC Research Center, Mohammed V University, Rabat, Morocco.

Abstract

In the title compound, C₁₀H₁₀N₂OS, the five atoms of the thio-phene ring are essentially coplanar (r.m.s. deviation = 0.0037 Å) and the pyridazine ring is non-planar. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into 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 theoretical geometric parameters are in good agreement with XRD results. The inter-molecular inter-actions were investigated using a Hirshfeld surface analysis and two-dimensional fingerprint plots. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H⋯H (39.7%), C⋯H/H⋯C (17.3%) and O⋯H/H⋯O (16.8%) contacts.

Keywords: DFT; crystal structure; dihydropyridazine; molecular electrostatic potential; pyridazine; thiophen.

Grants and funding

This work was funded by Ondokuz Mayis Üniversitesi grant PYO.FEN1906.19.001.