Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of methyl 4-[3,6-bis-(pyridin-2-yl)pyridazin-4-yl]benzoate.

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??(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.

SUBMITTER: Filali M 

PROVIDER: S-EPMC6829718 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature