N-(7-Ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide

The molecule of the title heterocyclic compound, C16H17N3O3S, is bent at the S atom with an C—SO2—NH—C torsion angle of 80.17 (8)°. The phenyl substituent at the S atom is rotated out of the plane of the 1H-indazole ring [interplanar angle = 46.24 (8)°]. In the crystal, intermolecular N—H⋯N and N—H⋯O hydrogen bonds build up a ribbon developing parallel to the b-axis direction. C—H⋯O hydrogen bonds link these ribbons, forming a layer parallel to the bc plane.

The molecule of the title heterocyclic compound, C 16 H 17 N 3 O 3 S, is bent at the S atom with an C-SO 2 -NH-C torsion angle of 80.17 (8) . The phenyl substituent at the S atom is rotated out of the plane of the 1H-indazole ring [interplanar angle = 46.24 (8) ]. In the crystal, intermolecular N-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds build up a ribbon developing parallel to the b-axis direction. C-HÁ Á ÁO hydrogen bonds link these ribbons, forming a layer parallel to the bc plane.   Table 1 Hydrogen-bond geometry (Å , ).

N-(7-Ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide
N. Abbassi, E. M. Rakib and H. Zouihri In the title compound, C 16 H 17 N 3 O 3 S, the molecule is bent at the S atom with an C-SO 2 -NH-C torsion angle of 80.17 (8)° (Fig. 1). In the crystal structure, intermolecular N-H···N and N-H···O hydrogen bonds build up a ribbon developping parallel to the b direction and the C-H···O link these reibons to form a two D layer parallel to the bc plane ( Fig. 2, Table 1).
The S atom has a distorted tetrahedral geometry [maximum deviation: O-S-O = 119.87 (9)°]. The phenyl substituent at S1 atom is rotated out of the plane of the 1H-indazol ring (the interplanar angles is 46.24 (8)°).

Experimental
A mixture of 4-nitroindazole (1.22 mmol) and anhydrous SnCl 2 (1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was heated at 60 °C for 2 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was made slightly basic (pH 7-8) by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate.
The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methylbenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with Ethyl acetate: Hexane 1:9).

Refinement
The H atoms bound to C were treated as riding with their parent atoms [C-H distances are 0.93Å for CH groups and 0.96Å for CH2 with U iso (H) = 1.2 U eq (C), and 0.97 Å for CH3 groups with U iso (H) = 1.5 U eq (C). The N2-H20 H atoms were treated as riding with U iso (H) = 1.2 U eq (N), and the N1-H10 H atoms were refined with restraints (d N-H = 0.88 (2) Å) and then were treated as riding in the last cycles of refinement.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Rfactors(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.202461 (