4-(2H-1,3-Benzodioxol-5-yl)-1-(4-methyl-phenyl)-1H-pyrazol-5-amine

Abstract

In the title compound, C17H15N3O2, two independent mol-ecules (A and B) comprise the asymmetric unit. The major conformational difference arises in the relative orientation of the pyrazole ring amine and dioxole substituents which are anti in A and syn in B. The five-membered dioxole ring in each mol-ecule has an envelope conformation with the methyl-ene C atom as the flap. The mean plane through the benzodioxole and benzene groups make dihedral angles of 31.67 (8) and 68.22 (9)°, respectively, with the pyrazole ring in A; the equivalent values for B are 47.18 (7) and 49.08 (9)°. In the crystal, supra-molecular zigzag chains along the b-axis direction arise as a result of N-H⋯N hydrogen bonding. These are consolidated into supra-molecular double chains via C-H⋯O and C-H⋯π inter-actions.

Fig. 1.

The molecular structure of the two independent molecules comprising the asymmetric unit of the title compound (I), showing the atom labelling. Displacement ellipsoids are drawn at the 35% probability level.

Fig. 2.

Overlay diagram of the N1- and inverted N2-containing molecules (red and blue, respectively), where the pyrazole rings have been superimposed.

Fig. 3.

View of the supramolecular zigzag chain along the b axis in compound (I), mediated by N—H···N hydrogen bonds (dashed lines; see Table 1 for details).

Fig. 4.

A view in projection along the b axis of the crystal packing of compound (I). The N—H···N, C—H···O (obscured) and C—H···π interactions are shown as dashed lines (see Table 1 for details).