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Volume 69 
Part 9 
Page o1410  
September 2013  

Received 5 August 2013
Accepted 6 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.136
Data-to-parameter ratio = 21.2
Details
Open access

1-Allyl-3-chloro-5-nitro-1H-indazole

aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco,bDipartimento di Chimica 'G. Ciamician', Università degli Studi di Bologna, Via Selmi 2, I-40126 Bologna, Italy, 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

In the title compound, C10H8ClN3O2, the indazole ring system makes a dihedral angle of 7.9 (3)° with the plane through the nitro group. The allyl group is rotated out of the plane of the indazole ring system [N-N-C-C torsion angle = 104.28 (19)°]. In the crystal, molecules are linked by C-H...O hydrogen bonds, forming zigzag chains propagating along the b-axis direction.

Related literature

For the pharmacological activity of indazole derivatives, see: Baraldi et al. (2001[Baraldi, P. G., Balboni, G., Pavani, M. G., Spalluto, G., Tabrizi, M. A., Clercq, E. D., Balzarini, J., Bando, T., Sugiyama, H. & Romagnoli, R. (2001). J. Med. Chem. 44, 2536-2543.]); Rodgers et al. (1996[Rodgers, J. D., Johnson, B. L., Wang, H., Greenberg, R. A., Erickson-Viitanen, S., Klabe, R. M., Cordova, B. C., Rayer, M. M., Lam, G. N. & Chang, C. H. (1996). Bioorg. Med. Chem. Lett. 6, 2919-2924.]); Li et al. (2003[Li, X., Chu, S., Feher, V. A., Khalili, M., Nie, Z., Margosiak, S., Nikulin, V., Levin, J., Sparankle, K. G., Fedder, M. E., Almassy, R., Appelt, K. & Yager, K. M. (2003). J. Med. Chem. 46, 5663-5673.]); Lin et al. (2008[Lin, X., Busch-Petersen, J., Deng, J., Edwards, C., Zhang, Z. & Kerns, J. K. (2008). Synlett, 20, 3216-3220.]). For a similar compound, see: El Brahmi et al. (2012[El Brahmi, N., Benchidmi, M., Essassi, E. M., Ladeira, S. & El Ammari, L. (2012). Acta Cryst. E68, o3368.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8ClN3O2

  • Mr = 237.64

  • Monoclinic, P 21 /c

  • a = 13.3025 (6) Å

  • b = 11.2505 (5) Å

  • c = 7.3092 (3) Å

  • [beta] = 91.343 (2)°

  • V = 1093.59 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 296 K

  • 0.41 × 0.34 × 0.22 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS: Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.654, Tmax = 0.747

  • 14430 measured reflections

  • 3069 independent reflections

  • 1852 reflections with I > 2[sigma](I)

  • Rint = 0.046

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

  • wR(F2) = 0.136

  • S = 1.02

  • 3069 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 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
C6-H6...O2i 0.93 2.46 3.274 (2) 146
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\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: BT6927 ).


Acknowledgements

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

References

Baraldi, P. G., Balboni, G., Pavani, M. G., Spalluto, G., Tabrizi, M. A., Clercq, E. D., Balzarini, J., Bando, T., Sugiyama, H. & Romagnoli, R. (2001). J. Med. Chem. 44, 2536-2543.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El Brahmi, N., Benchidmi, M., Essassi, E. M., Ladeira, S. & El Ammari, L. (2012). Acta Cryst. E68, o3368.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Li, X., Chu, S., Feher, V. A., Khalili, M., Nie, Z., Margosiak, S., Nikulin, V., Levin, J., Sparankle, K. G., Fedder, M. E., Almassy, R., Appelt, K. & Yager, K. M. (2003). J. Med. Chem. 46, 5663-5673.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lin, X., Busch-Petersen, J., Deng, J., Edwards, C., Zhang, Z. & Kerns, J. K. (2008). Synlett, 20, 3216-3220.  [ISI] [CrossRef]
Rodgers, J. D., Johnson, B. L., Wang, H., Greenberg, R. A., Erickson-Viitanen, S., Klabe, R. M., Cordova, B. C., Rayer, M. M., Lam, G. N. & Chang, C. H. (1996). Bioorg. Med. Chem. Lett. 6, 2919-2924.  [CrossRef] [ChemPort]
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, o1410  [ doi:10.1107/S1600536813021995 ]

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