4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

Abstract

The asymmetric unit of the title compound, 2C 15 H 15 N 3 O 3 SÁH 2 O, comprises two crystallographically independent organic molecules and one water molecule, all in general positions. Each organic molecule comprises an indazolyl system linked through a sulfonamide group to a methoxybenzene ring. The most important difference between the two organic molecules is the dihedral angle between the fused-ring system and the methoxybenzene ring, which is 56.32 (7) in one molecule and 35.35 (8) in the other. In the crystal, the organic and water molecules are connected into supramolecular chains along the c axis through O-HÁ Á ÁN, O-HÁ Á ÁO, N-HÁ Á ÁO and N--HÁ Á ÁN hydrogen bonds; in addition, a -interaction between pyrazolyl rings [inter-centroid separation = 3.7547 (12) Å ] is noted. Structure descriptionSulfonamides and their derivatives constitute an important class of therapeutic agents that exhibit a broad spectrum of pharmacological profiles, such as anti-bacterial, diuretic, hypoglycaemic, anti-thyroid, anti-viral, anti-inflammatory and anti-parasitic activities among others (Ranjith et al., 2014;Shah et al., 2013;Scozzafava et al., 2013;Greig et al., 2013). In our previous work, we have found that indazoles bearing arylsulfonamide groups showed anti-proliferative activity against human (colon and prostate) and murine (leukaemia) cell lines (Abbassi et al., 2012(Abbassi et al., , 2014Bouissane, et al., 2006).The asymmetric unit of the title compound contains two independent organic molecules and one water molecule, as shown in Fig. 1. The fused five-and six-membered rings of each molecule are almost coplanar, with the maximum deviation from the mean plane being 0.020 (2) Å for the C12 atom and 0.022 (2) Å for the C27 atom in the first and data reports second molecules, respectively. The dihedral angles between the indazolyl system and the methoxybenzene ring are 56.32 (7) and 35.35 (8) in the first and second molecules, respectively.In the crystal, the organic molecules are connected through the water molecule by O7-H7AÁ Á ÁN6, O7-H7BÁ Á ÁO2, N1-HN1Á Á ÁO7 and N4-HN4Á Á ÁN3 hydrogen bonds (Table 1), in addition to -interactions between pyrazole rings as shown in Fig. 2. Synthesis and crystallizationA mixture of 1-methyl-7-nitroindazole (1.22 mmol) and anhydrous SnCl 2 (1.1 g, 6.1 mmol) in ethanethiol (25 ml) was heated at 308 K for 4 h. After reduction, the starting material had been consumed and the solution was allowed to cool. The pH of the solution was made slightly basic (pH = 7-8) by addition of 5% aqueous potassium bicarbonate. Extraction with EtOAc followed. 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 (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture had been concentrated in vacuo, the resulting residue was purified by flash chromatography (elution was with EtOAc/hexane 1:9). The title compoun...