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

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Filali M., Sebbar N. K., HÖKELEK T., Mague J. T., Chakroune S., Ben-Tama A., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.1321-1331, 2019 (ESCI) identifier identifier identifier


The title compound, C18H16N40, 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-y1 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 Hard "Npyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C HPrpoxy" " "rr (Prpoxy = prop-2en-l-yloxy) interactions link the molecules, forming deeply corrugated layers approximately parallel to the be 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" " "NI 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.