6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)eth­yl]-1H-imidazo[4,5-b]pyridin-2(3H)-one

Bel-Ghacham, H.; Kandri Rodi, Y.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810002679

Volume 66
Part 2
Page o456
February 2010

Received 20 January 2010
Accepted 21 January 2010
Online 27 January 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R = 0.038
wR = 0.077
Data-to-parameter ratio = 12.6
Details

6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-imidazo[4,5-b]pyridin-2(3H)-one

H. Bel-Ghacham,^a Y. Kandri Rodi,^a Natalie Saffon,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco,^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France,^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The title compound, C₁₁H₁₁BrN₄O₃, features an ethane fragment substituted with an almost planar (r.m.s. deviation = 0.019 Å) imidazo[4,5-b]pyridone ring system and an envelope-shaped oxazolidine unit on separate C atoms. The N-CH₂-CH₂-N torsion angle is 52.5 (4)°. In the crystal, pairs of molecules are linked by N-HO hydrogen bonds into centrosymmetric dimers.

Related literature

For the medicinal properties of imidazo[4,5-b]pyridines, see: Barraclough et al. (1990); Bianchi et al. (1983); Clark et al. (1978); Janssens et al. (1985); Temple et al. (1987).

Experimental

Crystal data

C₁₁H₁₁BrN₄O₃
M_r = 327.15
Monoclinic, C 2/c
a = 27.0174 (11) Å
b = 6.0141 (2) Å
c = 16.6121 (6) Å
= 110.343 (2)°
V = 2530.87 (16) Å³
Z = 8
Mo K radiation
= 3.26 mm^-1
T = 173 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.356, T_max = 0.854
9174 measured reflections
2224 independent reflections
1633 reflections with I > 2(I)
R_int = 0.062
Standard reflections: 0

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.077
S = 1.02
2224 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O3ⁱ	0.86 (1)	1.94 (1)	2.781 (4)	167 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5180 ).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Barraclough, P., Black, J. W., Cambridge, D., Collard, D., Firmin, D., Gerskowitch, V. P., Glen, R. C., Giles, H., Hill, A. P., Hull, R. A. D., Iyer, R., King, W. R., Kneen, C. O., Lindon, J. C., Nobbs, M. S., Randall, P., Shah, G. P., Smith, S., Vine, S. J., Whiting, M. V. & Williams, J. M. (1990). J. Med. Chem. 33, 2231-2239
Bianchi, M., Butti, A., Rossi, S., Barzaghi, F. & Marcaria, V. (1983). Eur. J. Med. Chem. Chim. Ther. 18, 501-506.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clark, R. L., Pessolano, A. A., Shen, T.-Y., Jocobus, D. P., Jones, H., Lotti, V. J. & Flataker, L. M. (1978). J. Med. Chem. 21, 965-978.
Janssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem. 28, 1943-1947.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Temple, C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem. 30, 1746-1751
Westrip, S. P. (2010). publCIF. In preparation.

organic compounds