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-idene]amino}-1,5-dimethyl-2-phenyl-1 H-pyrazol-3(2 H)-one and (E)-4-[(4-fluoro-benzyl-idene)amino]-1,5-dimethyl-2-phenyl-1 H-pyrazol-3(2 H)-one

M G Shankar; R Kumaravel; A Subashini; K Ramamurthi; Monika Kučeráková; Michal Dušek; Helen Stoeckli-Evans

doi:10.1107/S2056989023004085

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-idene]amino}-1,5-dimethyl-2-phenyl-1 H-pyrazol-3(2 H)-one and (E)-4-[(4-fluoro-benzyl-idene)amino]-1,5-dimethyl-2-phenyl-1 H-pyrazol-3(2 H)-one

Acta Crystallogr E Crystallogr Commun. 2023 May 12;79(Pt 6):538-544. doi: 10.1107/S2056989023004085. eCollection 2023 May 1.

Authors

M G Shankar¹, R Kumaravel², A Subashini¹, K Ramamurthi³, Monika Kučeráková⁴, Michal Dušek⁴, Helen Stoeckli-Evans⁵

Affiliations

¹ PG and Research Department of Physics, Srimad Andavan Arts Science College (Autonomous), Affiliated to Bharathidasan University, Tiruchirappalli - 620 005, Tamilnadu, India.
² Department of Physics, Annapoorana Engineering College, Salem - 636 308, Tamilnadu, India.
³ Crystal Growth and Thin Film Laboratory, Department of Physics, Bharathidasan University, Tiruchirappalli - 620024, Tamilnadu, India.
⁴ Institute of Physics ASCR, Na Slovance 2, 182 21 Praha 8, Czech Republic.
⁵ Institute of Physics, University of Neuchâtel, rue Emile-Argand 11, 2000 Neuchâtel, Switzerland.

Abstract

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.

Keywords: 4-aminoantipyrine; Hirshfeld surface analysis; crystal structure; energy frameworks.