Crystal Structure, Hirshfeld Surface Analysis And Inter­Action Energy And Dft Studies Of Methyl 4-[3,6-Bis­(Pyridin-2-Yl)Pyridazin-4-Yl]Benzoate

Abstract

The pyridazine ring deviates slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of mol­ecules extending along the a-axis direction are formed by C—HMthy⋯OCarbx (Mthy = methyl and Carbx = carboxyl­ate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by inversion-related C—HBnz⋯π(ring) inter­actions., The title com­pound, C22H16N4O2, contains two pyridine rings and one meth­oxy­carbonyl­phenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of mol­ecules extending along the a-axis direction are formed by C—HMthy⋯OCarbx (Mthy = methyl and Carbx = carboxyl­ate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by C—HBnz⋯π(ring) (Bnz = benzene) inter­actions. 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%) inter­actions. Hydrogen-bonding and van der Waals inter­actions are the dominant inter­actions 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 com­pared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.