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Volume 68 
Part 12 
Page o3368  
December 2012  

Received 20 October 2012
Accepted 9 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.100
Data-to-parameter ratio = 15.5
Details
Open access

1-Allyl-6-nitro-1H-indazole

aLaboratoire de Chimie Organique Hétérocyclique URAC21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco,bLaboratoire de Chimie de Coordination, route de Narbonne, 31077 Toulouse, France, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: n_elbrahmi@yahoo.fr

The fused five- and six-membered rings in the title molecule, C10H9N3O2, are essentially coplanar, the largest deviation from the mean plane being 0.012 (1) Å for the C atom linked to the nitro group. The fused-ring system makes a dihedral angle of 11.34 (6)° with the nitro group, leading to a syn-periplanar conformation. The plane through the atoms forming the allyl group is nearly perpendicular to the indazole fused-ring system, as indicated by the dihedral angle of 73.3 (5)°. In the crystal, each molecule is linked to its symmetry equivalent about the center of inversion by pairs of non-classical C-H...O hydrogen bonds, forming an extended tape motif parallel to the (-12-1) plane.

Related literature

For the pharmacological and biochemical properties of substituted indazoles, see: Saczewski et al. (2008[Saczewski, F., Kornicka, A., Rybczyn'ska, A., Hudson, A. L., Miao, S. S., Gdaniec, M., Boblewski, K. & Lehmann, A. (2008). J. Med. Chem. 51, 3599-3608.]); Jones et al. (2009[Jones, L. H., Allan, G., Barba, O., Burt, C., Corbau, R., Dupont, T., Knöchel, T., Irving, S., Middleton, D. S., Mowbray, C. E., Perros, M., Ringrose, H., Swain, N. A., Webster, R., Westby, M. & Phillips, C. (2009). J. Med. Chem. 52, 1219-1223.]); 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.]). For compounds with similar structures, see: El Brahmi et al. (2009[El Brahmi, N., Mohamed, B., Essassi, E. M., Zouihri, H. & Ng, S. W. (2009). Acta Cryst. E65, o2320.], 2011[El Brahmi, N., Benchidmi, M., Essassi, E. M., Ladeira, S. & Ng, S. W. (2011). Acta Cryst. E67, o3260.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9N3O2

  • Mr = 203.20

  • Triclinic, [P \overline 1]

  • a = 4.3630 (16) Å

  • b = 8.3245 (7) Å

  • c = 13.541 (5) Å

  • [alpha] = 95.647 (2)°

  • [beta] = 98.46 (2)°

  • [gamma] = 97.770 (2)°

  • V = 478.5 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.38 × 0.29 × 0.27 mm

Data collection
  • Bruker Kappa APEXII Quazar area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.997

  • 8258 measured reflections

  • 2109 independent reflections

  • 1675 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.100

  • S = 1.06

  • 2109 reflections

  • 136 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.93 2.51 3.3973 (17) 160
C8-H8A...O1i 0.97 2.53 3.4475 (19) 157
C2-H2...O2ii 0.93 2.66 3.3911 (17) 136
Symmetry codes: (i) -x, -y, -z; (ii) -x+2, -y+1, -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.]) and Mercury (Macrae et al. 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: PK2452 ).


References

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.
El Brahmi, N., Benchidmi, M., Essassi, E. M., Ladeira, S. & Ng, S. W. (2011). Acta Cryst. E67, o3260.  [CSD] [CrossRef] [details]
El Brahmi, N., Mohamed, B., Essassi, E. M., Zouihri, H. & Ng, S. W. (2009). Acta Cryst. E65, o2320.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jones, L. H., Allan, G., Barba, O., Burt, C., Corbau, R., Dupont, T., Knöchel, T., Irving, S., Middleton, D. S., Mowbray, C. E., Perros, M., Ringrose, H., Swain, N. A., Webster, R., Westby, M. & Phillips, C. (2009). J. Med. Chem. 52, 1219-1223.  [ISI] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Saczewski, F., Kornicka, A., Rybczyn'ska, A., Hudson, A. L., Miao, S. S., Gdaniec, M., Boblewski, K. & Lehmann, A. (2008). J. Med. Chem. 51, 3599-3608.  [ISI] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3368  [ doi:10.1107/S1600536812046478 ]

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