Research Article: 5,6-Dimethyl-4-(thio­phen-2-yl)-1H-pyrazolo­[3,4-b]pyridin-3-amine

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): Hatem A. Abdel-Aziz, Khalid A. Al-Rashood, Hazem A. Ghabbour, Suchada Chantrapromma, Hoong-Kun Fun.


In the title mol­ecule, C12H12N4S, the thio­phene ring is disordered over two orientations with a refined site-occupancy ratio of 0.777 (4):0.223 (4). The pyrazolo­pyridine ring system is essentially planar with an r.m.s. deviation of 0.0069 (3) Å and makes dihedral angles of 82.8 (2) and 72.6 (5)°, respectively, with the major and minor components of the thio­phene ring. In the crystal, mol­ecules are linked into a chain along the a axis by a pair of N—H⋯N(pyrazole) hydrogen bonds and a pair of N—H⋯N(pyridine) hydrogen bonds, both having a centrosymmetric R22(8) graph-set motif. A C—H⋯π inter­action is also present.

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For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to and bioactivity of pyrazole derivatives, see: Ali (2009 ▶); Bharate et al. (2008 ▶); Fu et al. (2010 ▶); Thumar & Patel (2011 ▶). For a related structure, see: Fun et al. (2011 ▶).