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Volume 69 
Part 8 
Page o1353  
August 2013  

Received 23 July 2013
Accepted 24 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.122
Data-to-parameter ratio = 19.0
Details
Open access

N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-methoxybenzenesulfonamide hemihydrate

aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: hakima_chicha@yahoo.fr

The fused five- and six-membered rings in the title compound, C17H16ClN3O3S·0.5H2O, are practically coplanar, with the maximum deviation from the mean plane being 0.057 (3) Å for the C atom bound to the exocyclic N atom. The indazole system makes a dihedral angle of 66.18 (12)° with the plane through the benzene ring, and it is nearly perpendicular to the allyl group, as indicated by the N-N-C-C torsion angle of 79.2 (3)°. In the crystal, the water molecule, lying on a twofold axis, forms O-H...N and accepts N-H...O hydrogen bonds. Additional C-H...O hydrogen bonds contribute to the formation of a chain along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010[Brzozowski, Z., Slawinski, J., Saczewski, F., Innocenti, A. & Supuran, C. T. (2010). Eur. J. Med. Chem. 45, 2396-2404.]); Drew (2000[Drew, J. (2000). Science, 287, 1960-964.]); Garaj et al. (2005[Garaj, V., Puccetti, L., Fasolis, G., Winum, J. Y., Montero, J. L., Scozzafava, A., Vullo, D., Innocenti, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3102-3108.]); Lopez et al. (2010[Lopez, M., Bornaghi, L. F., Innocenti, A., Vullo, D., Charman, S. A., Supuran, C. T. & Poulsen, S.-A. (2010). J. Med. Chem. 53, 2913-2926.]). For similar compounds, see: Abbassi et al. (2012[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.], 2013[Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190-o191.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16ClN3O3S·0.5H2O

  • Mr = 386.86

  • Monoclinic, C 2/c

  • a = 23.5515 (9) Å

  • b = 8.9081 (3) Å

  • c = 20.8278 (8) Å

  • [beta] = 122.628 (2)°

  • V = 3680.1 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 296 K

  • 0.41 × 0.38 × 0.27 mm

Data collection
  • Bruker X8 APEX diffractometer

  • 20391 measured reflections

  • 4389 independent reflections

  • 2740 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.122

  • S = 1.02

  • 4389 reflections

  • 231 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O4i 0.83 2.04 2.875 (2) 174
O4-H4...N2 0.87 2.00 2.822 (2) 158
C7-H7...O3ii 0.93 2.37 3.288 (3) 170
Symmetry codes: (i) x, y+1, z; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5244 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS and CNRST) for the X-ray measurements.

References

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.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190-o191.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Brzozowski, Z., Slawinski, J., Saczewski, F., Innocenti, A. & Supuran, C. T. (2010). Eur. J. Med. Chem. 45, 2396-2404.  [CrossRef] [ChemPort] [PubMed]
Drew, J. (2000). Science, 287, 1960-964.  [Web of Science] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Garaj, V., Puccetti, L., Fasolis, G., Winum, J. Y., Montero, J. L., Scozzafava, A., Vullo, D., Innocenti, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3102-3108.  [CrossRef] [PubMed] [ChemPort]
Lopez, M., Bornaghi, L. F., Innocenti, A., Vullo, D., Charman, S. A., Supuran, C. T. & Poulsen, S.-A. (2010). J. Med. Chem. 53, 2913-2926.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1353  [ doi:10.1107/S1600536813020606 ]

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