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Volume 69 
Part 2 
Pages o190-o191  
February 2013  

Received 6 December 2012
Accepted 27 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.077
Data-to-parameter ratio = 15.3
Details
Open access

Ethyl 3-[6-(4-methoxybenzenesulfonamido)-2H-indazol-2-yl]propanoate monohydrate

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: najat_abbassi@hotmail.com

In the title compound, C19H21N3O5S·H2O, the central indazole system is essentially planar (r.m.s. deviation = 0.012 Å), while both the benzene ring and the mean plane defined by the non-H atoms of the ethyl propionic ester unit (r.m.s. deviation = 0.087 Å) are nearly perpendicular to the indazole plane, as indicated by the dihedral angles of 82.45 (8) and 75.62 (8)°, respectively. Consequently, the molecule adopts a U-shaped geometry. In the crystal, the water molecule, which is linked to the indazole system by a strong O-H...N hydrogen bond, is also involved in two additional N-H...O and O-H...O interactions, which link the organic molecules into chains along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamides, see: Gadad et al. (2000[Gadad, A. K., Mahajanshetti, C. S., Nimbalkar, S. & Raichurkar, A. (2000). Eur. J. Med. Chem. 35, 853-857.]); Brzozowski et al. (2010[Brzozowski, Z., S1awinski, 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.]). For their antiproliferative activity 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.]); Bouissane et al. (2006[Bouissane, L., El Kazzouli, S., Léonce, S., Pffeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.]).

[Scheme 1]

Experimental

Crystal data
  • C19H21N3O5S·H2O

  • Mr = 421.46

  • Monoclinic, P 21

  • a = 9.0248 (3) Å

  • b = 8.7602 (3) Å

  • c = 13.1792 (4) Å

  • [beta] = 101.062 (2)°

  • V = 1022.58 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 296 K

  • 0.42 × 0.37 × 0.28 mm

Data collection
  • Bruker X8 APEX diffractometer

  • 10050 measured reflections

  • 4021 independent reflections

  • 3887 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.077

  • S = 1.05

  • 4021 reflections

  • 262 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1779 Friedel pairs

  • Flack parameter: 0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O6-H6A...N2 0.86 1.94 2.8029 (19) 176
N1-H1...O6i 0.81 1.95 2.7575 (19) 177
O6-H6B...O1ii 0.86 2.10 2.9094 (17) 156
Symmetry codes: (i) x, y+1, z; (ii) [-x+2, y-{\script{1\over 2}}, -z].

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: LR2095 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, 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.  [ISI] [CrossRef] [ChemPort] [PubMed]
Bouissane, L., El Kazzouli, S., Léonce, S., Pffeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.  [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Brzozowski, Z., S1awinski, J., Saczewski, F., Innocenti, A. & Supuran, C. T. (2010). Eur. J. Med. Chem. 45, 2396-2404.
Drew, J. (2000). Science, 287, 1960-964.  [ISI] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gadad, A. K., Mahajanshetti, C. S., Nimbalkar, S. & Raichurkar, A. (2000). Eur. J. Med. Chem. 35, 853-857.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o190-o191   [ doi:10.1107/S1600536812051975 ]

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