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, 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.

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate

“…A 4-[(prop-2-en-1-yloxy)methyl]phenyl analogue has been reported (Filali et al, 2019a). Three other metal complexes coordinated by 3,6-bis(pyridin-2-yl)pyridazine have also been reported, namely aquabis[3,6-bis(pyridin-2-yl)pyridazine- research communications (Showrilu et al, 2017), tetrakis[-3,6-di(pyridin-2-yl)pyridazine]bis(hydroxo)bis(-aqua)tetranickel(II) hexanitrate tetradecahydrate (Marino et al, 2019) and catena-[[ 2 -3,6-bis(pyridin-2yl)pyridazine]bis(-2-azido)dizaidodicopper monohydrate] (Mastropietro et al, 2013).…”