Date Published: June 01, 2011
Publisher: International Union of Crystallography
Author(s): R. J. Butcher, M. Akkurt, S. Samshuddin, B. Narayana, H. S. Yathirajan.
In the title compound, C25H16F2N2O, the pyrazole ring is almost planar (r.m.s. deviation = 0.028 Å) and makes a dihedral angle of 5.86 (11)° with the indazole benzene ring. The dihedral angle between the pyrazole ring and the unsubstituted phenyl ring is 28.19 (11)°. The dihedral angles between the unsubstituted phenyl and the two fluorophenyl groups are 57.69 (10) and 18.01 (10)°. In the crystal, molecules are linked by intermolecular N—H⋯O and C—H⋯F interactions, forming infinite chains along the b axis with graph-set motif R32(19). The crystal structure is further consolidated by π–π stacking [centroid–centroid distances = 3.5916 (13) and 3.6890 (13) Å] and C—H⋯π interactions.
For the pharmacological activity of indazole derivatives, see: Beylin et al. (1991 ▶); George et al. (1998 ▶); Jain et al. (1987 ▶); Palazzo et al. (1966 ▶); Popat et al. (2003 ▶); Roman (1990 ▶). For related structures, see: van der Helm et al. (1979 ▶); Fun et al. (2010 ▶). For hybridization and electron delocalization around N atoms, see: Susindran et al. (2010 ▶); Jin et al. (2004 ▶). For graph-set analysis, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).