Title of article :
Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate
Author/Authors :
Dadou, Said Laboratory of Applied Chemistry and Environment (LCAE) - Faculty of Sciences, Morocco , Kansiz, Sevgi Department of Physics - Faculty of Arts and Sciences - Ondokuz Mayıs University, Turkey , Daoui, Said Laboratory of Applied Chemistry and Environment (LCAE) - Faculty of Sciences, Morocco , Kalai, Fouad El Laboratory of Applied Chemistry and Environment (LCAE) - Faculty of Sciences, Morocco , Baydere, Cemile Department of Physics - Faculty of Arts and Sciences - Ondokuz Mayıs University, Turkey , Saddik, Rafik Laboratory of Organic Synthesis, Extraction and Valorization, Faculty of Sciences - Ain Chok - University Hassan II - Casablanca, Rabat, Morocco , Karrouchi, Khalid Laboratory of Plant Chemistry, - Organic and Bioorganic Synthesis - URAC23, Faculty of Science, B.P. 1014, GEOPAC Research Center - Mohammed V University, Rabat, Morocco , Dege, Necmi Department of Physics - Faculty of Arts and Sciences - Ondokuz Mayıs University, Turkey , Benchat, Noureddine Laboratory of Applied Chemistry and Environment (LCAE) - Faculty of Sciences, Morocco
Abstract :
The asymmetric units of the title compounds both contain one nonplanar molecule. In 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one, C17H14N2O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate, C20H16Cl2N2O3, (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the dichlorobenzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers with an R22(8) ring motif. In the crystal structure of (II), C—H⋯O hydrogen bonds generate dimers with R12(7), R22(16) and R22(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H⋯H (48.2%), C⋯H/H⋯C (29.9%) and O⋯H/H⋯O (8.9%) contacts. For compound (II), H⋯H (34.4%), C⋯H/H⋯C (21.3%) and O⋯H/H⋯O (16.5%) interactions are the most important contributions.
Keywords :
crystal structure , pyridazine , hydrogen bonding , Hirshfeld surface analysis
Journal title :
Acta Crystallographica Section E: Crystallographic Communications