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Volume 67 
Part 8 
Page o1998  
August 2011  

Received 22 June 2011
Accepted 25 June 2011
Online 9 July 2011

[sj5172sup1]
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Key indicators
Single-crystal X-ray study
T = 571 K
Mean [sigma](C-C) = 0.006 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 15.9
Details
Open access

3-Allyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one

Siham Dahmani,a* Youssef Kandri Rodi,a Santiago V. Luis,b Michael Boltec and Lahcen El Ammarid

aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco,bDepartamento de Quimica Inorganica & Organica, ESTCE, Universitat Jaume I, E-12080 Castellon, Spain,cInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: s_dahmani12@yahoo.fr

In the molecule of the title compound, C9H8BrN3O, the fused-ring system is almost planar, the largest deviation from the mean plane being 0.008 (3) Å. The plane through the atoms forming the allyl group is roughly perpendicular to the imidazo[4,5-b]pyridin-2-one system, as indicated by the dihedral angle between them of 70.28 (11)°. In the crystal, each molecule is linked to its symmetry equivalent about the center of inversion by a pair of strong N-H...O hydrogen bond, forming inversion dimers.

Related literature

For background to the biological activity of imidazopyridines, see: Chen & Dost (1992[Chen, S. T. & Dost, G. (1992). (Merck) US Patent 5 132 216.]); Cappelli et al. (2006[Cappelli, A., Mohr, G. P., Giuliani, G., Galeazzi, S., Anzini, M., Mennuni, L., Ferrari, F., Macoves, F., Krienrath, E. M., Langer, T., Valoti, M., Giorgi, G. & Vomero, S. (2006). J. Med. Chem. 49, 6451-6464.]); Weier et al. (1993[Weier, R. M., Khanna, I. K., Stealey, M. A. & Julien, J. (1993). US Patent 5 262 426.], 1994[Weier, R. M., Khanna, I. K., Lentz, K., Stealey, M. A. & Julien, J. (1994). (Searle) US Patent 5 359 073.]); Kulkarni & Newman (2007[Kulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987-2991.]). For background to their pharmacological activity, see: Bavetsias et al. (2007[Bavetsias, V., Sun, C., Bouloc, N., Reynisson, J., Workman, P., Linardopoulos, S. & McDonald, E. (2007). Bioorg. Med. Chem. 17, 6567-6571.], 2010[Bavetsias, V., Large, J. M., Sun, C., Bouloc, N., Kosmopoulou, M., Matteucci, M., Wilsher, N. E., Martins, V., Reynisson, J., Atrash, B., Faisal, A., Urban, F., Valenti, M. & Brandon, A. H. (2010). J. Med. Chem. 53, 5213-5228.]).

[Scheme 1]

Experimental

Crystal data

  • C9H8BrN3O

  • Mr = 254.09

  • Triclinic, [P \overline 1]

  • a = 4.5138 (5) Å

  • b = 9.7750 (9) Å

  • c = 11.5717 (11) Å

  • [alpha] = 78.748 (2)°

  • [beta] = 82.526 (3)°

  • [gamma] = 86.038 (2)°

  • V = 496.00 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 4.11 mm-1

  • T = 571 K

  • 0.60 × 0.19 × 0.04 mm
Data collection

  • Bruker CCD three-circle diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.192, Tmax = 0.850

  • 3086 measured reflections

  • 2019 independent reflections

  • 1683 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.127

  • S = 1.09

  • 2019 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 1.95 2.798 (4) 168
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5172 ).

References

Bavetsias, V., Large, J. M., Sun, C., Bouloc, N., Kosmopoulou, M., Matteucci, M., Wilsher, N. E., Martins, V., Reynisson, J., Atrash, B., Faisal, A., Urban, F., Valenti, M. & Brandon, A. H. (2010). J. Med. Chem. 53, 5213-5228.  [ISI] [CrossRef] [ChemPort] [PubMed]
Bavetsias, V., Sun, C., Bouloc, N., Reynisson, J., Workman, P., Linardopoulos, S. & McDonald, E. (2007). Bioorg. Med. Chem. 17, 6567-6571.  [ChemPort]
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cappelli, A., Mohr, G. P., Giuliani, G., Galeazzi, S., Anzini, M., Mennuni, L., Ferrari, F., Macoves, F., Krienrath, E. M., Langer, T., Valoti, M., Giorgi, G. & Vomero, S. (2006). J. Med. Chem. 49, 6451-6464.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chen, S. T. & Dost, G. (1992). (Merck) US Patent 5 132 216.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Kulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987-2991.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Weier, R. M., Khanna, I. K., Lentz, K., Stealey, M. A. & Julien, J. (1994). (Searle) US Patent 5 359 073.
Weier, R. M., Khanna, I. K., Stealey, M. A. & Julien, J. (1993). US Patent 5 262 426.

Acta Cryst (2011). E67, o1998  [ doi:10.1107/S1600536811025037 ]

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