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

El Brahmi, N.; Benchidmi, M.; Essassi, E.M.; Ladeira, S.; El Ammari, L.

doi:10.1107/S1600536812046478

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 (C-C) = 0.002 Å
R = 0.034
wR = 0.100
Data-to-parameter ratio = 15.5
Details

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

Nabil El Brahmi,^a ^* Mohammed Benchidmi,^a El Mokhtar Essassi,^a Sonia Ladeira ^b and Lahcen El Ammari ^c

^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-HO 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); Jones et al. (2009); Bouissane et al. (2006). For compounds with similar structures, see: El Brahmi et al. (2009, 2011).

Experimental

Crystal data

C₁₀H₉N₃O₂
M_r = 203.20
Triclinic, $[P \overline 1]$
a = 4.3630 (16) Å
b = 8.3245 (7) Å
c = 13.541 (5) Å
= 95.647 (2)°
= 98.46 (2)°
= 97.770 (2)°
V = 478.5 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.957, T_max = 0.997
8258 measured reflections
2109 independent reflections
1675 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.100
S = 1.06
2109 reflections
136 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.93	2.51	3.3973 (17)	160
C8-H8AO1ⁱ	0.97	2.53	3.4475 (19)	157
C2-H2O2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al. 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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.
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.
El Brahmi, N., Mohamed, B., Essassi, E. M., Zouihri, H. & Ng, S. W. (2009). Acta Cryst. E65, o2320.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

References