Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 4-[(prop-2-en-1-yl-oxy)meth-yl]-3,6-bis-(pyridin-2-yl)pyridazine

Mouad Filali; Nada Kheira Sebbar; Tuncer Hökelek; Joel T Mague; Said Chakroune; Abdessalam Ben-Tama; El Mestafa El Hadrami

doi:10.1107/S2056989019011186

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 4-[(prop-2-en-1-yl-oxy)meth-yl]-3,6-bis-(pyridin-2-yl)pyridazine

Acta Crystallogr E Crystallogr Commun. 2019 Aug 20;75(Pt 9):1321-1326. doi: 10.1107/S2056989019011186. eCollection 2019 Sep 1.

Authors

Mouad Filali¹, Nada Kheira Sebbar^{2

3}, Tuncer Hökelek⁴, Joel T Mague⁵, Said Chakroune¹, Abdessalam Ben-Tama¹, El Mestafa El Hadrami¹

Affiliations

¹ Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco.
² Laboratoire de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco.
³ Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
⁴ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
⁵ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

Abstract

The title compound, C₁₈H₁₆N₄O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-H_Pyrd⋯N_Pyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-H_Prp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-H_Pyrd⋯N_Pyrdz hydrogen-bond energy is 64.3 kJ mol^-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Keywords: DFT; Hirshfeld surface; crystal structure; pyridazine; pyridine; π-stacking.

Grants and funding

This work was funded by National Science Foundation grant 1228232. Tulane University grant . Hacettepe University Scientific Research Project Unit grant 013 D04 602 004 to T. Hökelek.