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.

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?? (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.

SUBMITTER: Filali M 

PROVIDER: S-EPMC6727048 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature