Crystal structure of N-(3-chloro-1-methyl-1H-indazol-5-yl)-4-methoxybenzenesulfonamide

In the title compound, C15H14ClN3O3S, the dihedral angle between the planes of the indazole ring system (r.m.s. deviation = 0.007 Å) and the benzene ring is 89.05 (7)°. The methoxy C atom deviates from its attached ring by 0.196 (3) Å. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops. The dimers are connected into [010] chains by C—H⋯O interactions.

The molecule of the title compound is built up from two fused five-and six-membered rings (N1 N2 C2 to C8) almost coplanar, with a maximum deviation of 0.010 (2) Å for C5 atom (Fig.1). The dihedral angle between the indazol system and the plane through the benzene ring (C9 to C14) is of 89.05 (7)°.
The cohesion of the crystal structure is ensured by N3-H3N···O2 hydrogen bonds between molecules forming dimers, which are linked together by C5-H5···O3 interaction and forming [010] chains as shown in Fig.2 and Table 1.

S2. Experimental
A mixture of 1-methyl-3-chloro-5-nitroindazole (1.22 mmol) and anhydrous SnCl2 (1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was heated at 60 °C for 6 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-methoxybenzenesulfonyl chloride (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 2:8). The title compound was recrystallized from ethanol solution. Yield: 56%, PF: 140-142°C.

S3. Refinement
H atoms were located in a difference map and treated as riding with C-H = 0.96 Å, C-H = 0.93 Å, and N-H = 0.86 Å for methyl, aromatic CH and NH, respectively. All hydrogen with U iso (H) = 1.2 U eq (aromatic, NH) and U iso (H) = 1.5 U eq for methyl.
supporting information

Figure 1
Molecular structure of the title compound with displacement ellipsoids drawn 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.