Syntheses, crystal structures, Hirshfeld surface analyses and energy frameworks of two 4-amino-anti-pyrine Schiff base compounds: (E)-4-{4-(di-ethyl-amino)-benzyl-ideneamino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one and (E)-4-(4-fluoro-benzyl-idene)amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2023-05, Vol.79 (Pt 6), p.538
• Main Authors: Shankar, M G, Kumaravel, R, Subashini, A, Ramamurthi, K, Kučeráková, Monika, Dušek, Michal, Stoeckli-Evans, Helen
• Format: Article
• Language: English
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989023004085

The title Schiff base compounds, C22H26N4O (I) and C18H16FN3O (II), were each synthesized by a single-step condensation reaction. The substituted benzyl-idene 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-amino-anti-pyrine 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 mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions to form layers lying parallel to (001). In the crystal of II, the mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds and C-H⋯π inter-actions, thereby forming layers lying parallel to (010). Hirshfeld surface analysis was employed to further qu-antify the inter-atomic inter-actions in the crystals of both compounds.The title Schiff base compounds, C22H26N4O (I) and C18H16FN3O (II), were each synthesized by a single-step condensation reaction. The substituted benzyl-idene 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-amino-anti-pyrine 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 mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions to form layers lying parallel to (001). In the crystal of II, the mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds and C-H⋯π inter-actions, thereby forming layers lying parallel to (010). Hirshfeld surface analysis was employed to further qu-antify the inter-atomic inter-actions in the crystals of both compounds.