Synthesis and structure of 4-{[(E)-(7-meth-oxy-1,3-benzodioxol-5-yl)methyl-idene]amino}-1,5-dimethyl-2-phenyl-2,3-di-hydro-1 H-pyrazol-3-one

Charmaine Arderne; Marthe Carine Djuide Fotsing; Derek Tantoh Ndinteh

doi:10.1107/S2056989021000797

Synthesis and structure of 4-{[(E)-(7-meth-oxy-1,3-benzodioxol-5-yl)methyl-idene]amino}-1,5-dimethyl-2-phenyl-2,3-di-hydro-1 H-pyrazol-3-one

Acta Crystallogr E Crystallogr Commun. 2021 Jan 29;77(Pt 2):200-203. doi: 10.1107/S2056989021000797. eCollection 2021 Feb 1.

Authors

Charmaine Arderne¹, Marthe Carine Djuide Fotsing², Derek Tantoh Ndinteh²

Affiliations

¹ Department of Chemical Sciences, Research Centre for Synthesis and Catalysis, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg, 2006, South Africa.
² Department of Chemical Sciences, University of Johannesburg, PO Box 17011, Doornfontein, Johannesburg, 2028, South Africa.

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.

Keywords: 4-aminoantipyrine; 4-aminophenazone; Schiff bases; crystal structure.

Grants and funding

This work was funded by NRF Thuthuka Programme grant 117946 to C Arderne. NRF Postdoctoral Scarce Skills Fellowship grant 11670 to M. C. D. Fotsing.