Abstract
The title com-pound, C22H16N4O2, contains two pyridine rings and one meth-oxy-carbonyl-phenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of mol-ecules extending along the a-axis direction are formed by C-HMthy⋯OCarbx (Mthy = methyl and Carbx = carboxyl-ate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by C-HBnz⋯π(ring) (Bnz = benzene) inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (39.7%), H⋯C/C⋯H (27.5%), H⋯N/N⋯H (15.5%) and O⋯H/H⋯O (11.1%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, C-HMthy⋯OCarbx hydrogen-bond energies are 62.0 and 34.3 kJ mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
3,6-Bis(pyridin-2-yl)pyridazine derivatives are a versatile class of nitrogen-containing heterocyclic compounds and they constitute useful intermediates in organic syntheses
As a continuation of our research in the field of substituted 3,6-bis(pyridin-2-yl)pyridazine (Filali et al, 2019a,b), we report the synthesis, the molecular and crystal structures, along with the Hirshfeld surface analysis, the intermolecular interaction energies and the density functional theory (DFT) computational calculations carried out at
Inversion-related chains are connected into ribbons by C22—H22BÁ Á ÁO1iv hydrogen bonds (Table 1) and the ribbons are joined into stepped layers approximately parallel to (011) by inversion-related pairs of C19—H19Á Á ÁCg1i interactions, where Cg1 is the centroid of pyridine ring A (Table 1 and Fig. 2)
Summary
3,6-Bis(pyridin-2-yl)pyridazine derivatives are a versatile class of nitrogen-containing heterocyclic compounds and they constitute useful intermediates in organic syntheses. This nucleus is one of the important ligands in the field of coordination chemistry research. 5-[3,6-Bis(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) Systems containing this moiety showed remarkable corrosion inhibition (Khadiri et al, 2016). Heterocyclic molecules such as 3,6-bis(pyridin-2-yl)-1,2,4,5tetrazine have been used in transition-metal chemistry (Kaim & Kohlmann, 1987); this tetrazine is a bidentate chelating ligand popular in coordination chemistry and complexes of a wide range of metals, including iridium and palladium (Tsukada et al, 2001). The B3LYP/6-311G(d,p) level for a new 3,6-bis(pyridin-2yl)pyridazine, namely, methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate, (I)
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