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.

Keywords

• crystal structure
• pyridine
• pyridazine
• π-stacking
• DFT
• Hirshfeld surface