Date Published: July 01, 2012
Publisher: International Union of Crystallography
Author(s): Abdullah M. Asiri, Hassan M. Faidallah, Khalid A. Alamry, Seik Weng Ng, Edward R. T. Tiekink.
In the title compound ethanol monosolvate, C23H21N3O2S·C2H5OH, the dihydropyrazole ring is twisted about the Csp3—Csp3 bond. Nevertheless, the ring approximates a plane (r.m.s. deviation for the fitted atoms = 0.132 Å) and forms dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the fused- and sulfonamide-benzene rings. As the dihydropyrazole C-bound phenyl group is roughly perpendicular to the dihydropyrazole ring [dihedral angle = 74.04 (15)°; the amino group is orientated to the same side of the molecule], to a first approximation, the molecule has a stunted T-shape. The cyclohexene ring adopts a half-chair conformation with the methylene C atom connected to the dihydropyrazole ring lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The components of the asymmetric unit are connected by an O—H⋯O hydrogen bond. Further links between molecules leading to a three-dimensional architecture are of the type N—H⋯O.
For a previous synthesis, see: Faidallah & Makki (1994 ▶). For the biological activity of related compounds, see: Faidallah et al. (2011 ▶). For the structure of the methyl analogue, see: Asiri et al. (2011 ▶).