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

Ouzidan, Y.; Jasinski, J.P.; Butcher, R.J.; Golen, J.A.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S1600536811012669

Volume 67
Part 5
Page o1095
May 2011

Received 28 March 2011
Accepted 5 April 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 170 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.091
Data-to-parameter ratio = 17.4
Details

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

Younes Ouzidan,^a ^* Jerry P. Jasinski,^b Raymond J. Butcher,^c James A. Golen,^b El Mokhtar Essassi ^d and Lahcen El Ammari ^e

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco,^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,^dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Avenue Ibn Battouta, 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: ouzidan@yahoo.fr

In the title molecule, C₁₇H₁₅BrN₄O₂, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.015 (2) Å, and forms dihedral angles of 37.8 (2) and 35.5 (2)° with the phenyl and oxazolidine rings, respectively. The conformation adopted by the molecule is stabilized by an intramolecular [pi] [pi] interaction [centroid-centroid distance = 3.855(2) Å] between oxazolidine and phenyl rings. The crystal packing features intermolecular C-HN and C-HO interactions.

Related literature

For background to the medicinal chemistry of oxazolidin-2-ones and their application in asymmetric synthesis, see: Diekema & Jones (2000); Mukhtar & Wright (2004); Evans et al. (1993); Matsunaga et al. (2005). For similar compounds with an imidazo[4,5-b]pyridine group, see: Ouzidan et al. (2010a,b).

Experimental

Crystal data

C₁₇H₁₅BrN₄O₂
M_r = 387.24
Monoclinic, P 2₁ /n
a = 11.3553 (6) Å
b = 11.5915 (5) Å
c = 12.2542 (8) Å
= 98.685 (6)°
V = 1594.46 (15) Å³
Z = 4
Mo K radiation
= 2.60 mm^-1
T = 170 K
0.22 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction XcaliburE Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.599, T_max = 0.652
7850 measured reflections
3791 independent reflections
2839 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.091
S = 1.03
3791 reflections
218 parameters
H-atom parameters constrained
_max = 0.50 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4AN2ⁱ	0.95	2.61	3.544 (3)	168
C10-H10AN2ⁱⁱ	0.99	2.55	3.261 (3)	128
C15-H15AO1ⁱⁱⁱ	0.95	2.53	3.423 (3)	156
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2362 ).

Acknowledgements

JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Diekema, D. J. & Jones, R. N. (2000). Drugs, 59, 7-16.
Evans, D. A., Ny, H. P. & Rieger, D. L. (1993). J. Am. Chem. Soc. 115, 11446-11459.
Matsunaga, H., Ishizuka, T. & Kunieda, T. (2005). Tetrahedron, 61, 8073-8094.
Mukhtar, T. A. & Wright, G. D. (2004). Chem. Rev. 105, 529-542.
Ouzidan, Y., Kandri Rodi, Y., Obbade, S., Essassi, E. M. & Ng, S. W. (2010a). Acta Cryst. E66, o947.
Ouzidan, Y., Obbade, S., Capet, F., Essassi, E. M. & Ng, S. W. (2010b). Acta Cryst. E66, o946.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds