Syntheses, crystal structures, Hirshfeld surface analyses and energy frameworks of two 4-aminoantipyrine Schiff base compounds: (E)-4-{[4-(diethylamino)benzylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one and (E)-4-[(4-fluorobenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title Schiff base compounds, C22H26N4O (I) and C18H16FN3O (II), were each synthesized by a single-step condensation reaction. The substituted benzylidene ring is inclined to the pyrazole ring mean planes by 22.92   (7) ° in I and 12.70   (9) ° in II. The phenyl ring of the 4-aminoantipyrine unit is inclined to the pyrazole ring mean plane by 54.87   (7) ° in I and by 60.44   (8) ° in II. In the crystal of I, the molecules are linked by C — H...O hydrogen bonds and C — H... π interactions to form layers lying parallel to (001). In the crystal of II, the molecules are linked by C — H...O and C — H...F hydrogen bonds and C — H... π interactions, thereby forming layers lying parallel to (010). Hirshfeld surface analysis was employed to further quantify the interatomic interactions in the crystals of both compounds.

Source: Acta Crystallographica Section E - May 12, 2023 Category: Chemistry Authors: Shankar, M.G. Kumaravel, R. Subashini, A. Ramamurthi, K. Ku č er á kov á , M. Du š ek, M. Stoeckli-Evans, H. Tags: crystal structure 4-aminoantipyrine Hirshfeld surface analysis energy frameworks research communications Source Type: research