Abstract
In the solid state, the title compound, C20H19N3O2, adopts the keto-amine tautomeric form, with the H atom attached to the N atom, which participates in an intra-molecular N-H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π-π stacking inter-actions [centroid-centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.
Highlights
The title compound, C20H19N3O2, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H O hydrogen bond with an S(6) ring motif
The dihedral angles between the pyrazole ring and the phenyl and benzene rings are
Schiff bases derived from acyl pyrazones and aromatic amines have been prepared as antimicrobial agents (Parmar et al, 2015) and as ligands for the formation of metal-ion complexes (Jayarajan et al, 2010; Moorjani et al, 2010)
Summary
The chemistry of pyrazolone derivatives has attracted much attention because of their interesting structural properties and applications in diverse areas. Pyrazolone derivatives are used as starting materials for the synthesis of biologically active compounds. Schiff base compounds have received considerable attention for many years, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al, 2007), catalysis (Chen et al, 2008) and biological processes (May et al, 2004). O-hydroxy Schiff bases exhibit two possible tautomeric forms, the enol–imine and keto–amine forms. A compound similar to the title compound, 5-methyl-2-phenyl-4{1-[(pyridin-2-ylmethyl)-amino]-ethylidene}-2,4-dihydro-pyrazol-3-one derived from acyl pyrazolone and aliphatic amine was reported to possesses the amino-one structure (Amarasekara et al, 2009). The dashed line shows the intramolecular N—H O hydrogen bond
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