1-Allyl-6-nitro-1H-indazole

Abstract

The fused five- and six-membered rings in the title mol­ecule, C10H9N3O2, are essentially coplanar, the largest deviation from the mean plane being 0.012 (1) Å for the C atom linked to the nitro group. The fused-ring system makes a dihedral angle of 11.34 (6)° with the nitro group, leading to a syn-periplanar conformation. The plane through the atoms forming the allyl group is nearly perpendicular to the indazole fused-ring system, as indicated by the dihedral angle of 73.3 (5)°. In the crystal, each mol­ecule is linked to its symmetry equivalent about the center of inversion by pairs of non-classical C—H⋯O hydrogen bonds, forming an extended tape motif parallel to the (-12-1) plane.

2-Allyl-7-nitro-2H-indazole

“…The indazole subunit in organic molecules is an important structure in many drug substances with a wide range of pharmacological effects: e.g., anti-tumor, anti-microbial, anti-platelet, anti-HIV, and anti-inflammatory (Baraldi et al, 2001;Li et al, 2003;Lee et al, 2001;Rodgers et al, 1996;Schmidt et al, 2008). The present work is a continuation of the investigation of the indazole derivatives published recently by our team (El Brahmi et al, 2012;Chicha et al, 2013).…”

1-Allyl-3-chloro-5-nitro-1H-indazole

“…E69, o1410 (Baraldi et al, 2001;Rodgers et al, 1996;Li et al, 2003;Lin et al, 2008). The present work is a contribution to the investigation of indazole derivatives (El Brahmi et al, 2012).…”

1-Methyl-5-nitro-3-phenyl-1H-indazole

“…They frequently comprise the core frame of numerous pharmaceutically active compounds, such as Lonidamine [1-(2,4-dichlorobenzyl)-1Hindazole-3-carboxylic acid] and Granisetron {1-methyl-N-[(1R,3R,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide}. The present paper is a continuation of our research work devoted to the development of the indazole derivatives with potential pharmacological activities (El Brahmi et al, 2011;El Brahmi et al, 2012).…”