Abstract
In the title compound, C20H19N3O4, the dihedral angles between the central pyrazole ring and the pendant phenyl and substituted benzene rings are 50.95 (8) and 3.25 (12)°, respectively, and an intra-molecular C-H⋯O link generates an S(6) ring. The benzodioxolyl ring adopts a shallow envelope conformation with the methyl-ene C atom as the flap. In the crystal, the mol-ecules are linked by non-classical C-H⋯O inter-actions, which generate a three-dimensional network. Solvent-accessible voids run down the c-axis direction and the residual electron density in these voids was modelled during the refinement process using the SQUEEZE algorithm [Spek (2015 ▸). Acta Cryst. C71, 9-18] within the structural checking program PLATON.
Highlights
Compounds such as 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole) and its Schiff base analogues are chemically attractive because of the various biological properties they possess, their synthetic flexibility and their selectivity and sensitivity towards metal ions (Keskioglu et al, 2008)
Platinum(II) complexes of Schiff bases have been reported as potential anti-cancer agents
Structural commentary The title compound (I) crystallizes in the monoclinic centrosymmetric space group C2/c, and the asymmetric unit consists of one non-planar independent molecule
Summary
Compounds such as 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole) and its Schiff base analogues are chemically attractive because of the various biological properties they possess, their synthetic flexibility and their selectivity and sensitivity towards metal ions (Keskioglu et al, 2008). Pyrazol-3-one Schiff bases can be obtained from the condensation of 4-aminophenazone or 4-aminoantipyrine (4-AAP) and the corresponding carbonyl compound (Sakthivel et al, 2020). Schiff bases can find applications in analytical chemistry, material sciences and in various biological fields. Various 4-AAP derivatives have several biological applications and 4-AAP Schiff bases from the condensation with para-methoxycinnamaldehyde display antimicrobial activity against a large spectrum of microorganisms (Obasi et al, 2016). Platinum(II) complexes of Schiff bases have been reported as potential anti-cancer agents. Some of these complexes have a better toxicity than that of Cisplatin (Li et al, 2013). As part of our studies in this area, the title compound, C20H19N3O4, was obtained from 4-AAP and myristicin aldehyde and its crystal structure determined. The voids can be seen in the packing arrangement (Fig. 2)
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