Abstract
The title compound, C17H15N3O2, is a monoclinic polymorph (P21/c with Z' = 1) of the previously reported triclinic (P-1 with Z' = 2) form [Gajera et al. (2013 ▸). Acta Cryst. E69, o736-o737]. The mol-ecule 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 mol-ecule has a twisted conformation. The five-membered dioxolyl ring has an envelope conformation with the methyl-ene C atom being the flap. The relative disposition of the amino and dioxolyl substituents is syn. One of the independent mol-ecules 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, mol-ecules assemble into supra-molecular helical chains via amino-pyrazolyl N-H⋯N hydrogen bonds. These are linked into layers via C-H⋯π inter-actions, and layers stack along the a axis with no specific inter-actions between them.
Highlights
In the crystal structure of the monoclinic form, molecules assemble into supramolecular helical chains via amino–pyrazolyl N—H N hydrogen bonds
It is the broad range of biological activities, such as antidepressant, anti-anxiety, anti-fungal, anti-bacterial, antidiabetic, anti-cancer, etc. (Tanitame et al, 2004; Chimenti et al, 2006; Ding et al.,2009; Shen et al, 2011; Deng et al, 2012), that continues to inspire interest in compounds containing the amino-substituted pyrazole unit. It was in this context that the crystal structure of 4-(2H-1,3-benzodioxol-5-yl)-1-(4-methylphenyl)-1H-pyrazol-5-amine (I) was originally determined (Gajera et al, 2013)
During scale up, crystals of the monoclinic form were isolated from recrystallization of (I)
Summary
It is the broad range of biological activities, such as antidepressant, anti-anxiety, anti-fungal, anti-bacterial, antidiabetic, anti-cancer, etc. (Tanitame et al, 2004; Chimenti et al., 2006; Ding et al.,2009; Shen et al, 2011; Deng et al, 2012), that continues to inspire interest in compounds containing the amino-substituted pyrazole unit. (Tanitame et al, 2004; Chimenti et al., 2006; Ding et al.,2009; Shen et al, 2011; Deng et al, 2012), that continues to inspire interest in compounds containing the amino-substituted pyrazole unit. It was in this context that the crystal structure of 4-(2H-1,3-benzodioxol-5-yl)-1-(4-methylphenyl)-1H-pyrazol-5-amine (I) was originally determined (Gajera et al, 2013). The crystal and molecular structures of the monoclinic form of (I), hereafter (mI), are described and compared with the triclinic polymorph, (tI). The molecular structure of the molecule found in the monoclinic polymorph showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level
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