1. Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate
- Author
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Mouad Filali, Nada Kheira Sebbar, Tuncer Hökelek, Joel T. Mague, Lhoussaine El Ghayati, El Mestafa El Hadrami, and A. Ben-Tama
- Subjects
pyridine ,crystal structure ,Crystal structure ,010402 general chemistry ,010403 inorganic & nuclear chemistry ,Ring (chemistry) ,01 natural sciences ,Research Communications ,Pyridazine ,Crystal ,chemistry.chemical_compound ,symbols.namesake ,Pyridine ,c—h...π(ring) interaction ,General Materials Science ,hydrogen bond ,Crystallography ,Hydrogen bond ,Hirshfeld surface ,General Chemistry ,Condensed Matter Physics ,0104 chemical sciences ,pyridazine ,chemistry ,QD901-999 ,symbols ,C—H⋯π(ring) interaction ,Density functional theory ,van der Waals force - 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.
- Published
- 2019
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