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Volume 69 
Part 11 
Pages o1603-o1604  
November 2013  

Received 24 September 2013
Accepted 28 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.142
Data-to-parameter ratio = 18.4
Details
Open access

2-Allyl-7-nitro-2H-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: assoman_k@yahoo.fr

The asymmetric unit of the title compound, C10H9N3O2, contains two independent mol­ecules linked by a C-H...N hydrogen bond. Each mol­ecule has a similar conformation, being built up from fused five- and six-membered rings, each linked to an ally and nitro group, respectively. The indazole ring system makes dihedral angles of 2.7 (2) and 2.2 (2)°, respectively, with the plane through the nitro group. The allyl group is nearly perpendicular to the indazole system, as indicated by the N-N-C-C torsion angles of -75.3 (2) and -82.2 (2)°, this being the most important difference between the conformations of the two mol­ecules. In the crystal, mol­ecules are linked by C-H...O and [pi]-[pi] [inter-centroid distance = 3.6225 (8) Å] inter­actions to form a three-dimensional network.

Related literature

For pharmacological effects of indazole derivatives, see: Baraldi et al. (2001[Baraldi, P. G., Balbonic, 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.]); 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.]); Lee et al. (2001[Lee, F.-Y., Lien, J.-C., Huang, L.-J., Huang, T.-M., Tsai, S.-C., Teng, C.-M., Wu, C.-C., Cheng, F.-C. & Kuo, S.-C. (2001). J. Med. Chem. 44, 3746-3749.]); 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.]); Schmidt et al. (2008[Schmidt, A., Beutler, A. & Snovydovych, B. (2008). Eur. J. Org. Chem. pp. 4073-4095.]). For similar compounds, see: El Brahmi et al. (2012[El Brahmi, N., Benchidmi, M., Essassi, E. M., Ladeira, S. & El Ammari, L. (2012). Acta Cryst. E68, o3368.]); Chicha et al. (2013[Chicha, H., Rakib, E. M., Spinelli, D., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1410.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9N3O2

  • Mr = 203.20

  • Triclinic, [P \overline 1]

  • a = 8.1848 (3) Å

  • b = 8.3253 (4) Å

  • c = 16.3194 (6) Å

  • [alpha] = 84.168 (2)°

  • [beta] = 85.653 (2)°

  • [gamma] = 60.843 (2)°

  • V = 965.64 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.42 × 0.29 × 0.17 mm

Data collection
  • Bruker X8 APEX diffractometer

  • 22310 measured reflections

  • 4980 independent reflections

  • 4107 reflections with I > 2[sigma](I)

  • Rint = 0.028

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

  • wR(F2) = 0.142

  • S = 1.04

  • 4980 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10A...N2 0.93 2.60 2.907 (3) 100
C5-H5...O1i 0.93 2.49 3.4004 (19) 165
C8-H8A...O4ii 0.97 2.45 3.205 (2) 134
C15-H15...O4i 0.93 2.49 3.3986 (19) 167
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: TK5258 ).


Acknowledgements

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

References

Baraldi, P. G., Balbonic, 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.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chicha, H., Rakib, E. M., Spinelli, D., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1410.  [CSD] [CrossRef] [IUCr Journals]
El Brahmi, N., Benchidmi, M., Essassi, E. M., Ladeira, S. & El Ammari, L. (2012). Acta Cryst. E68, o3368.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lee, F.-Y., Lien, J.-C., Huang, L.-J., Huang, T.-M., Tsai, S.-C., Teng, C.-M., Wu, C.-C., Cheng, F.-C. & Kuo, S.-C. (2001). J. Med. Chem. 44, 3746-3749.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
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.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
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]
Schmidt, A., Beutler, A. & Snovydovych, B. (2008). Eur. J. Org. Chem. pp. 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 (2013). E69, o1603-o1604   [ doi:10.1107/S1600536813026743 ]

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