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Volume 69 
Part 9 
Page o1398  
September 2013  

Received 1 August 2013
Accepted 2 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 21.0
Details
Open access

4-Methoxy-N-(1-methyl-1H-indazol-5-yl)benzenesulfonamide

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: hakima_chicha@yahoo.fr

The indazole ring system [maximum deviation = 0.013 (2) Å] of the title compound, C15H15N3O3S, makes a dihedral angle of 50.11 (7)° with the benzene ring. In the crystal, cohesion is provided by C-H...O and N-H...N hydrogen bonds, which link the molecules into chains propagating along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006[Bouissane, L., El Kazzouli, S., Leonce, S., Pfeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.]); El-Sayed et al. (2011[El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714-3720.]); Mustafa et al. (2012[Mustafa, G., Khan, I. U., Ashraf, M., Afzal, I., Shahzad, S. A. & Shafiq, M. (2012). Bioorg. Med. Chem. 20, 2535-2539.]). 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.]); Chicha et al. (2013[Chicha, H., Kouakou, A., Rakib, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1353.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15N3O3S

  • Mr = 317.36

  • Monoclinic, P 21 /n

  • a = 10.1069 (3) Å

  • b = 13.6178 (3) Å

  • c = 10.8530 (2) Å

  • [beta] = 90.777 (2)°

  • V = 1493.60 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 296 K

  • 0.39 × 0.33 × 0.23 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.651, Tmax = 0.747

  • 19007 measured reflections

  • 4178 independent reflections

  • 3232 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.125

  • S = 1.02

  • 4178 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.89 2.25 3.1335 (19) 176
C8-H8A...O1ii 0.96 2.49 3.391 (2) 157
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: BT6924 ).


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]
Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190-o191.  [CSD] [CrossRef] [ChemPort] [details]
Bouissane, L., El Kazzouli, S., Leonce, S., Pfeifer, 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.
Chicha, H., Kouakou, A., Rakib, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1353.  [CrossRef] [details]
El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714-3720.  [ISI] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mustafa, G., Khan, I. U., Ashraf, M., Afzal, I., Shahzad, S. A. & Shafiq, M. (2012). Bioorg. Med. Chem. 20, 2535-2539.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1398  [ doi:10.1107/S1600536813021624 ]

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