A monoclinic polymorph of 4-(2H-1,3-benzodioxol-5-yl)-1-(4-methylphenyl)-1H-pyrazol-5-amine

Abstract

The title compound, C17H15N3O2, is a monoclinic polymorph (P21/cwithZ′ = 1) of the previously reported triclinic (P-1 withZ′ = 2) form [Gajeraet al.(2013).Acta Cryst.E69, o736–o737]. The molecule in the monoclinic polymorph features a central pyrazolyl ring with an N-boundp-tolyl group and a C-bound 1,3-benzodioxolyl fused-ring system on either side of the C atom bearing the amino group. The dihedral angles between the central ring and the N- and C-bound rings are 50.06 (5) and 27.27 (5)°, respectively. The angle between the pendent rings is 77.31 (4)°, indicating the molecule has a twisted conformation. The five-membered dioxolyl ring has an envelope conformation with the methylene C atom being the flap. The relative disposition of the amino and dioxolyl substituents issyn. One of the independent molecules in the triclinic form has a similarsyndisposition but the other has anantiarrangement of these substituents. In the crystal structure of the monoclinic form, molecules assemble into supramolecular helical chainsviaamino–pyrazolyl N—H...N hydrogen bonds. These are linked into layersviaC—H...π interactions, and layers stack along theaaxis with no specific interactions between them.