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

In the title compound ethanol monosolvate, C23H21N3O2S·C2H5OH, the dihydropyrazole ring is twisted about the Csp 3—Csp 3 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.

In the title compound ethanol monosolvate, C 23 H 21 N 3 O 2 SÁ-C 2 H 5 OH, the dihydropyrazole ring is twisted about the Csp 3 -Csp 3 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-HÁ Á ÁO hydrogen bond. Further links between molecules leading to a three-dimensional architecture are of the type N-HÁ Á ÁO.

Tiekink Comment
The title compound, (I), reported previously in the literature (Faidallah & Makki, 1994), comprises a benzenesulfonamide unit which is grafted to a chemotherapeutic heterocycle pyrazole derivative, and therefore is a compound which is anticipated to exhibit enhanced activities .
In (I), Fig. 1, pyrazole ring is twisted about the C10-C11 bond (r.m.s. deviation for the fitted atoms = 0.132 Å). The cyclohexene ring adopts a half-chair conformation with the C9 atom lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The fused-ring-and sulfonamide-benzene rings form dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the least-squares plane through the pyrazole ring. By contrast, the pyrazole-C-bound phenyl group is almost perpendicular to the pyrazole ring, forming a dihedral angle of 74.04 (15)°, so that to a first approximation, the molecule has a stunted T-shape. The sulfonamide-amino group is orientated to the same side of the molecule as the pyrazole-C-bound benzene ring. While the sulfonamide-O1 atom is almost co-planar with the benzene ring, the O1-S1-C21-C20 torsion angle is -168.51 (17)°, the O2 atom is somewhat splayed [O2-S1-C21 -C20 = -38.9 (2)°]. In the structure of the compound where the pyrazole-C-bound substituent is methyl rather than phenyl, the molecule has a shallow bowl-shaped conformation (Asiri et al., 2011).
The asymmetric unit comprises the organic molecule and a ethanol molecule of solvation with the primary connection between them being a O-H···O hydrogen bond, Table 1. Each amino-H forms a hydrogen bond to an oxygen atom so that each oxygen atom in the structure functions as an acceptor, Table 1, and that a three-dimensional architecture results,

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.