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Volume 69 
Part 9 
Page o1471  
September 2013  

Received 24 July 2013
Accepted 20 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.134
Data-to-parameter ratio = 21.3
Details
Open access

4-Methyl-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, 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

In the title compound, C15H15N3O2S, the fused ring system is close to planar, the largest deviation from the mean plane being 0.030 (2) Å, and makes a dihedral angle of 48.84 (9)° with the benzene ring belonging to the methylbenzenesulfonamide moiety. In the crystal, molecules are connected through N-H...N hydrogen bonds and weak C-H...O contacts, forming a two-dimensional network parallel to (001).

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006[Bouissane, L., El Kazzouli, S., Léonce, S., Pfeiffer, B., Rakib, E. M., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.]); 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.]); 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
  • C15H15N3O2S

  • Mr = 301.36

  • Monoclinic, P 21 /c

  • a = 8.0026 (3) Å

  • b = 12.8195 (4) Å

  • c = 14.1321 (4) Å

  • [beta] = 91.602 (2)°

  • V = 1449.24 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 296 K

  • 0.43 × 0.36 × 0.28 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.992

  • 17896 measured reflections

  • 4048 independent reflections

  • 2703 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.134

  • S = 1.02

  • 4048 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.88 2.21 3.065 (2) 166
C3-H3...O2ii 0.93 2.53 3.277 (2) 137
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, 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: BH2482 ).


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., Léonce, S., Pfeiffer, B., Rakib, E. M., 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]
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, o1471  [ doi:10.1107/S1600536813023398 ]

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