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

Abstract

A second polymorph (monoclinic with Z′ = 1) of the title compound is reported in which the conformation resembles one of the independent mol­ecules of the original triclinic polymorph ( Z′ = 2).

Abstract

The title compound, C ₁₇H ₁₅N ₃O ₂, is a monoclinic polymorph ( P2 ₁/ c with Z′ = 1) of the previously reported triclinic ( P-1 with Z′ = 2) form [Gajera et al. (2013 ▸). Acta Cryst. E 69, o736–o737]. The mol­ecule in the monoclinic polymorph features a central pyrazolyl ring with an N-bound p-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 is syn. One of the independent mol­ecules in the triclinic form has a similar syn disposition but the other has an anti arrangement of these substituents. In the crystal structure of the monoclinic form, mol­ecules assemble into supra­molecular helical chains via amino–pyrazolyl N—H⋯N hydrogen bonds. These are linked into layers via C—H⋯π inter­actions, and layers stack along the a axis with no specific inter­actions between them.