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Volume 70 
Part 1 
Page o101  
January 2014  

Received 19 December 2013
Accepted 20 December 2013
Online 24 December 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.125
Data-to-parameter ratio = 14.9
Details
Open access

1-(4-Methyl­phenyl­sulfon­yl)-5,6-di­nitro-1H-indazole

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: b_oulemda@yahoo.fr

In the title compound, C14H10N4O6S, the indazole ring system is almost perpendicular to the tosyl ring, as indicated by the dihedral angle of 89.40 (9)° between their planes. The dihedral angles between the indazole system and the nitro groups are 57.0 (3) and 31.9 (3)°. In the crystal, mol­ecules are linked by C-H...O inter­actions, forming chains running along [100].

Related literature

For the biological activity of sulfonamides, see: Schmidt et al. (2008[Schmidt, A., Beutler, A. & Snovydovych, B. (2008). Eur. J. Org. Chem. 24, 4073-4095.]); Liu et al. (2004[Liu, Y., Yang, J. & Liu, Q. (2004). Chem. Pharm. Bull. 52, 454-455.]); Ali et al. (2008[Ali, Z., Ferreira, D., Carvalho, P., Avery, M. A. & Khan, I. A. (2008). J. Nat. Prod. 71, 1111-1112.]); Patel et al. (1999[Patel, M., Rodgers, J. D., McHugh, R. J. Jr, Johnson, B. L., Cordova, B. C., Klaba, R. M., Bacheler, L. T., Erickson-Viitanen, S. & Ko, S. S. (1999). Bioorg. Med. Chem. Lett. 9, 3217-3220.]); Mosti et al. (2000[Mosti, L., Menozzi, G., Fossa, P., Filippelli, W., Gessi, S., Rinaldi, B. & Falcone, G. (2000). Arzneim. Forsch. Drug. Res. 50, 963-972.]); Bouissane et al. (2006[Bouissane, L., El Kazzouli, S., Leonce, S., Pffeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.]); 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.]). For the structures of similar compounds, see: Abbassi et al. (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
  • C14H10N4O6S

  • Mr = 362.32

  • Triclinic, [P \overline 1]

  • a = 7.4125 (3) Å

  • b = 8.5371 (3) Å

  • c = 13.0825 (5) Å

  • [alpha] = 90.401 (2)°

  • [beta] = 95.707 (2)°

  • [gamma] = 111.302 (2)°

  • V = 766.66 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 296 K

  • 0.42 × 0.35 × 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 = 0.693, Tmax = 0.747

  • 19101 measured reflections

  • 3383 independent reflections

  • 2984 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.125

  • S = 1.07

  • 3383 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 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
C5-H5...O5i 0.93 2.61 3.175 (2) 120
Symmetry code: (i) 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: BT6953 ).


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.  [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]
Ali, Z., Ferreira, D., Carvalho, P., Avery, M. A. & Khan, I. A. (2008). J. Nat. Prod. 71, 1111-1112.  [CrossRef] [PubMed] [ChemPort]
Bouissane, L., El Kazzouli, S., Leonce, 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.
Chicha, H., Kouakou, A., Rakib, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1353.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Liu, Y., Yang, J. & Liu, Q. (2004). Chem. Pharm. Bull. 52, 454-455.  [CrossRef] [PubMed] [ChemPort]
Mosti, L., Menozzi, G., Fossa, P., Filippelli, W., Gessi, S., Rinaldi, B. & Falcone, G. (2000). Arzneim. Forsch. Drug. Res. 50, 963-972.  [ChemPort]
Patel, M., Rodgers, J. D., McHugh, R. J. Jr, Johnson, B. L., Cordova, B. C., Klaba, R. M., Bacheler, L. T., Erickson-Viitanen, S. & Ko, S. S. (1999). Bioorg. Med. Chem. Lett. 9, 3217-3220.  [CrossRef] [PubMed] [ChemPort]
Schmidt, A., Beutler, A. & Snovydovych, B. (2008). Eur. J. Org. Chem. 24, 4073-4095.  [CrossRef]
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 (2014). E70, o101  [ doi:10.1107/S1600536813034326 ]

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