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Volume 69 
Part 6 
Page o962  
June 2013  

Received 14 May 2013
Accepted 18 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.085
Data-to-parameter ratio = 17.0
Details
Open access

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

aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco,bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France,cUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France,dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue, Ibn Batouta, Rabat , Morocco, and eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: amal_haoudi@yahoo.fr

The fused imidazole and pyridine rings in the title compound, C13H10BrN3O, are linked to a benzyl group. The fused ring system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å. The phenyl ring is not coplanar with the fused ring system, as indicated by the dihedral angle of 67.04 (12)°. In the crystal, molecules are linked by pairs of N-H...O hydrogen bonds, forming inversion dimers.

Related literature

For the biological activity of imidazopyridine derivatives, see: Chen & Dost (1992[Chen, S. T. & Dost, G. (1992). (Merck) US Patent 5132216.]); 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. (1994[Weier, R. M., Khanna, I. K., Lentz, K., Stealey, M. A. & Julien, J. (1994). (Searle) US Patent 5359073.]); Kulkarni & Newman (2007[Kulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987-2991.]); 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
  • C13H10BrN3O

  • Mr = 304.15

  • Triclinic, [P \overline 1]

  • a = 4.2399 (2) Å

  • b = 10.4463 (4) Å

  • c = 14.5144 (6) Å

  • [alpha] = 107.611 (2)°

  • [beta] = 90.628 (3)°

  • [gamma] = 99.784 (3)°

  • V = 602.49 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.40 mm-1

  • T = 296 K

  • 0.26 × 0.19 × 0.02 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.472, Tmax = 0.935

  • 13819 measured reflections

  • 2772 independent reflections

  • 2169 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.085

  • S = 1.06

  • 2772 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H14...O1i 0.86 1.95 2.789 (3) 166
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: FJ2630 ).


Acknowledgements

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

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 (2009). APEX2, SAINT-Plus and SADABS. 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] [CSD] [CrossRef] [PubMed] [ChemPort]
Chen, S. T. & Dost, G. (1992). (Merck) US Patent 5132216.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987-2991.  [CrossRef] [PubMed] [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]
Weier, R. M., Khanna, I. K., Lentz, K., Stealey, M. A. & Julien, J. (1994). (Searle) US Patent 5359073.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o962  [ doi:10.1107/S1600536813013780 ]

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