Research Article: 4-(3-Phenyl-3,3a,4,5-tetra­hydro-2H-benzo[g]indazol-2-yl)benzene­sulfonamide ethanol monosolvate

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.

Partial Text

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 ▶).




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