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Volume 69 
Part 7 
Pages o1029-o1030  
July 2013  

Received 14 May 2013
Accepted 27 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.035
wR = 0.089
Data-to-parameter ratio = 16.4
Details
Open access

6-Bromo-1,3-bis[(1,3-dioxolan-2-yl)methyl]-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

In the title compound, C14H16BrN3O5, the N atoms adjacent to the carbonyl group in the five-membered ring are substituted by (1,3-dioxolan-2-yl)methyl groups. The fused ring system is essentially planar, with the largest deviation from the mean plane being 0.014 (2) Å for the C atom bearing the Br atom. The first oxolane ring, attached on the side of the N atom belonging to the pyridine ring, has an envelope conformation with one of the O atoms as the flap, whereas the second oxolane ring displays a twisted boat conformation. The two oxolane rings display envelope and twisted boat conformations. In the crystal, molecules are linked by C-H...O hydrogen bonds, building chains parallel to the a-axis direction.

Related literature

For the biological activity of imidazopyridine derivatives, see: Temple et al. (1987[Temple, J. C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem. 30, 1746-1751.]); Barraclough et al. (1990[Barraclough, P., et al. (1990). J. Med. Chem. 33, 2231-2239.]); Janssens et al. (1985[Janssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem. 28, 1943-1947.]); Liu et al. (2008[Liu, L., Xu, P., Zhou, L. & Lei, P. S. (2008). Chin. Chem. Lett. 19, 1-4.]); Bavetsias et al. (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.]); Coates et al. (1993[Coates, W. J., Connolly, B., Dhanak, D., Flynn, S. T. & Worby, A. (1993). J. Med. Chem. 36, 1387-1392.]); For the chemistry of synthetic dyes, see: Ryabukhin et al. (2006[Ryabukhin, S. V., Plaskon, A. S., Volochnyuk, D. M. & Tolmachev, A. A. (2006). Synthesis, 21, 3715-3726.]); Schiffmann et al. (2006[Schiffmann, R., Neugebauer, A. & Klein, C. D. (2006). J. Med. Chem. 49, 511-522.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16BrN3O5

  • Mr = 386.21

  • Monoclinic, P 21 /n

  • a = 5.1144 (1) Å

  • b = 17.8029 (4) Å

  • c = 16.5365 (5) Å

  • [beta] = 97.009 (2)°

  • V = 1494.42 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.78 mm-1

  • T = 296 K

  • 0.15 × 0.07 × 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 = 0.674, Tmax = 0.936

  • 13392 measured reflections

  • 3421 independent reflections

  • 2632 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.089

  • S = 1.02

  • 3421 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10B...O2i 0.97 2.36 3.291 (4) 160
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: FJ2631 ).


References

Barraclough, P., et al. (1990). J. Med. Chem. 33, 2231-2239.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
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.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Coates, W. J., Connolly, B., Dhanak, D., Flynn, S. T. & Worby, A. (1993). J. Med. Chem. 36, 1387-1392.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Janssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem. 28, 1943-1947.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Liu, L., Xu, P., Zhou, L. & Lei, P. S. (2008). Chin. Chem. Lett. 19, 1-4.  [CrossRef] [ChemPort]
Ryabukhin, S. V., Plaskon, A. S., Volochnyuk, D. M. & Tolmachev, A. A. (2006). Synthesis, 21, 3715-3726.
Schiffmann, R., Neugebauer, A. & Klein, C. D. (2006). J. Med. Chem. 49, 511-522.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
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]
Temple, J. C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem. 30, 1746-1751.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1029-o1030   [ doi:10.1107/S1600536813014591 ]

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