2-Bromo­ethyl 2-chloro-6-methyl­quinoline-3-carboxyl­ate

Benzerka, S.; Bouraiou, A.; Bouacida, S.; Roisnel, T.; Belfaitah, A.

doi:10.1107/S1600536810010160

Volume 66
Part 4
Page o1006
April 2010

Received 1 March 2010
Accepted 18 March 2010
Online 31 March 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.092
Data-to-parameter ratio = 17.9
Details

2-Bromoethyl 2-chloro-6-methylquinoline-3-carboxylate

Saida Benzerka,^a Abdelmalek Bouraiou,^a ^* Sofiane Bouacida,^b Thierry Roisnel ^c and Ali Belfaitah ^a

^aLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria,^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine 25000, Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
Correspondence e-mail: bouraiou.abdelmalek@yahoo.fr

In the title compound, C₁₃H₁₁BrClNO₂, the two rings of the quinoline group are fused in an axial fashion at a dihedral angle of 1.28 (9)°. In the crystal, molecules are arranged in zigzag layers along the c axis. The crystal packing is stabilized by weak C-HO hydrogen bonds and intermolecular interactions between Br and O atoms [BrO= 3.076 (2) Å], resulting in the formation of a three-dimensional network.

Related literature

For our previous work on the preparation of quinoline derivatives, see: Benzerka et al. (2008); Ladraa et al. (2009, 2010). For radical bromination, see: Kikichi et al. (1998); Xu et al. (2003); Djerassi (1948); Newman & Lee (1972). For radical bromination of ketone and acetal functions, see: Marvell & Joncich (1951); Markees (1958).

Experimental

Crystal data

C₁₃H₁₁BrClNO₂
M_r = 328.59
Monoclinic, P 2₁ /n
a = 6.1740 (4) Å
b = 29.0515 (14) Å
c = 7.2875 (4) Å
= 99.167 (3)°
V = 1290.42 (13) Å³
Z = 4
Mo K radiation
= 3.39 mm^-1
T = 100 K
0.45 × 0.38 × 0.11 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.238, T_max = 0.689
11364 measured reflections
2938 independent reflections
2430 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.092
S = 1.02
2938 reflections
164 parameters
H-atom parameters constrained
_max = 0.74 e Å^-3
_min = -0.85 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13BO1ⁱ	0.97	2.41	3.347 (4)	162
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2201 ).

Acknowledgements

We are grateful to all personnel at the PHYSYNOR Laboratory, Université Mentouri-Constantine, for their assistance. Thanks are due to MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

References

Benzerka, S., Bouraiou, A., Bouacida, S., Rhouati, S. & Belfaitah, A. (2008). Acta Cryst. E64, o2089-o2090.
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Djerassi, C. (1948). Chem. Rev. 43, 271-317.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kikichi, D., Sakaguchi, S. & Ishii, Y. (1998). J. Org. Chem. 63, 6023-6026.
Ladraa, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2009). Acta Cryst. C65, o475-o478.
Ladraa, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2010). Acta Cryst. E66, o693.
Markees, D. G. (1958). J. Org. Chem. 23, 1490-1492.
Marvell, E. N. & Joncich, M. J. (1951). J. Am. Chem. Soc. 73, 973-975.
Newman, M. S. & Lee, L. F. (1972). J. Org. Chem. 37, 4468-4469.
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xu, F., Savary, K., Williams, J. M., Grabowski, E. J. J. & Reider, P. J. (2003). Tetrahedron Lett. 44, 1283-1286.

organic compounds