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-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (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-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 mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
Chemical context3,6-Di(pyridin-2-yl)pyridazine and its derivatives are aromatic heterocyclic organic compounds
(N3/C5–C9); Prpoxy = prop-2-en-1-yloxy] (Table 1) interactions link the molecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction (Figs. 2 and 3)
The syntheses of 3,6-di(pyridin-2-yl)pyridazine and its derivatives based on polyheterocycles have attracted considerable attention from pharmacists in the last few decades as they function as important pharmacophores in medicinal chemistry and pharmacology (Filali et al, 2019). 5-[3,6-Di(pyridin-2-yl)pyridazine-4-yl]-20-deoxyuridine-50-O-triphosphate can be used as a potential substrate for fluorescence detection and imaging of DNA (Kore et al, 2015)
Summary
3,6-Di(pyridin-2-yl)pyridazine and its derivatives are aromatic heterocyclic organic compounds. 5-[3,6-Di(pyridin-2-yl)pyridazine-4-yl]-20-deoxyuridine-50-O-triphosphate can be used as a potential substrate for fluorescence detection and imaging of DNA (Kore et al, 2015). The systems containing this moiety have shown remarkable corrosion inhibitory (Khadiri et al, 2016). Heterocyclic molecules such as 3,6-bis(20-pyridyl)-1,2,4,5tetrazine have been used in transition-metal chemistry (Kaim & Kohlmann, 1987). It is a bidentate chelate ligand popular in coordination chemistry and complexes of a wide range of metals, including iridium and palladium (Tsukada et al, 2001). Symmetry codes: (v) Àx þ 1; Ày þ 1; Àz þ 1; (vi) Àx þ 1; y þ 12; Àz þ 32
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