Received 29 July 2013
aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco,bDepartment of Pharmaceutical Chemistry, Institute of Pharmacy, University of Hamburg, Hamburg, Germany, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP. 1014, Rabat, Morocco
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C17H17N3O3.0.5H2O, the indazole system makes a dihedral angle of 46.19 (8)° with the plane through the benzene ring and is nearly perpendicular to the allyl group, as indicated by the dihedral angle of 81.2 (3)°. In the crystal, the water molecule, disordered over two sites related by an inversion center, forms O-HN bridges between indazole N atoms of two sulfonamide molecules. It is also connected via N-HO interaction to the third sulfonamide molecule; however, due to the water molecule disorder, only every second molecule of sulfonamide participates in this interaction. This missing interaction results in a slight disorder of the sulfonamide S,O and N atoms which are split over two sites with half occupancy. With the help of C-HO hydrogen bonds, the molecules are further connected into a three-dimensional network.
For the pharmacological activity of sulfonamides, see: Bouissane et al. (2006); Supuran & Scozzafava (2003); Smith & Jones (2008); Scozzafava et al. (2003). For their antiproliferative activity, see: Abbassi et al. (2012, 2013).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2590 ).
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240-249.
Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190-o191.
Bouissane, L., El Kazzouli, S., Leonce, S., Pffeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Scozzafava, A., Owa, T., Mastrolorenzo, A. & Supuran, C. T. (2003). Curr. Med. Chem. 10, 925-953.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, D. A. & Jones, R. M. (2008). Curr. Opin. Drug Discov. Devel. 11, 72-79.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Supuran, C. T. & Scozzafava, A. (2003). Med. Res. Rev. 23, 535-558.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.