Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chloro-phen-yl)-2-oxoeth-oxy]phen-yl}ethen-yl)-4,5-di-hydro-pyridazin-3(2 H)-one

Said Daoui; Israa Muwafaq; Emine Berrin Çınar; Abdulmalik Abudunia; Necmi Dege; Noureddine Benchat; Khalid Karrouchi

doi:10.1107/S205698902101238X

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chloro-phen-yl)-2-oxoeth-oxy]phen-yl}ethen-yl)-4,5-di-hydro-pyridazin-3(2 H)-one

Acta Crystallogr E Crystallogr Commun. 2022 Jan 1;78(Pt 1):8-11. doi: 10.1107/S205698902101238X.

Authors

Said Daoui¹, Israa Muwafaq², Emine Berrin Çınar², Abdulmalik Abudunia³, Necmi Dege², Noureddine Benchat¹, Khalid Karrouchi⁴

Affiliations

¹ Laboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohammed I University, 60000 Oujda, Morocco.
² Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, 55200, Turkey.
³ Department of Pharmacology, Faculty of Clinical Pharmacy, University of Medical and Applied Sciences, Yemen.
⁴ Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco.

Abstract

The pyridazine ring in the title compound, C₂₀H₁₇ClN₂O₃, adopts a screw-boat conformation. The whole mol-ecule 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 mol-ecules 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 inter-actions are H⋯H, accounting for 36.5% of overall crystal packing, and H⋯O/O⋯H (18.6% contribution) contacts.

Keywords: Hirshfeld surface; crystal structure; dihydropyridazin; hydrogen bonding.

Grants and funding

This work was funded by Ondokuz Mayis Üniversitesi grant PYO.FEN.1906.19.001.