Crystal Structure, Hirshfeld Surface Analysis And Inter­Action Energy And Dft Studies Of 4-[(Prop-2-En-1-Yl­Oxy)Meth­Yl]-3,6-Bis­(Pyridin-2-Yl)Pyridazine

Abstract

The title compound consists of a 3,6-bis­(pyridin-2-yl)pyridazine unit linked to a 4-[(prop-2-en-1-yl­oxy)meth­yl] moiety. The pyridine-2-yl rings are rotated slightly out of the plane of the pyridazine ring. In the crystal, C—H⋯N hydrogen bonds and C—H⋯π inter­actions link the mol­ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction., The title compound, C18H16N4O, consists of a 3,6-bis­(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl­oxy)meth­yl] 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—HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C—HPrp­oxy⋯π (Prp­oxy = prop-2-en-1-yl­oxy) inter­actions link the mol­ecules, 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 inter­actions being the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPyrd⋯NPyrdz 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 mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.