3-Bromo-6-nitro-1-(prop-2-ynyl)-1H-indazole

Abstract

In the title compound, C10H6BrN3O2, the indazole fused-ring system is nearly planar (r.m.s. deviation = 0.008 Å); its nitro substituent is nearly coplanar with the fused ring [dihedral angle = 4.5 (2)°]. In the crystal, adjacent mol­ecules are linked by weak acetyl­ene–nitro C—H⋯O hydrogen bonds, generating a helical chain running along the b axis.

2-(4-Nitrobenzylidene)malononitrile

“…The nitro group is close to being coplanar with the benzene ring (dihedral angle = 8.8 (3)°), which is consistent with previous studies (El Brahmi et al, 2011;Mehdi et al, 2010;Ouzidan et al, 2011;Raza et al, 2010). In addition, the benzylidenemalononitrile moiety is nearly planar with a maximum deviation of 0.129 (2))Å for atom N2 (Karthikeyan et al, 2011).…”

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

“…Moreover, the dihedral angle of 11.34 (6)° between the fused ring system and the nitro group lead to a synperiplanar conformation. The structure of the 1-Allyl-6-nitro-indazole is similar to that reported for the following molecules: 1allyl-3-chloro-6-nitro-1H-indazole and 3-bromo-6-nitro-1-(prop-2-ynyl)-1H-indazole (El Brahmi et al 2009, 2011.…”

“…For the pharmacological and biochemical properties of substituted indazoles, see: Saczewski et al (2008); Jones et al (2009); Bouissane et al (2006). For compounds with similar structures, see: El Brahmi et al (2009Brahmi et al ( , 2011.…”

5-Nitro-1-(prop-2-yn-1-yl)-1H-indazole

“…This is undoubtedly due to a broad variety of biological functions of indazole derivatives such as anti-inflammatory (Schmidt et al, 2008), antibacterial (Shafakat Ali et al, 2012) and antitumor activities (Abbassi et al, 2014). The present work is a continuation of our work on indazole derivatives (El Brahmi et al, 2011). In contrast to 1-(5-nitro-1H-indazol-1-yl)ethanone, the nitro group here is within a degree of planarity with the indazole moiety ( Fig.…”