Ethyl 2-(2,3,4,5,6-Penta­bromo­phen­yl)acetate

Sauer, A.M.; Mack, A.G.; Elnagar, H.Y.; Fronczek, F.R.

doi:10.1107/S1600536810025626

Volume 66
Part 8
Page o1994
August 2010

Received 3 June 2010
Accepted 29 June 2010
Online 14 July 2010

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.006 Å
R = 0.025
wR = 0.053
Data-to-parameter ratio = 24.6
Details

Ethyl 2-(2,3,4,5,6-Pentabromophenyl)acetate

Anne M. Sauer,^a Art G. Mack,^a Hassan Y. Elnagar ^a and Frank R. Fronczek ^b ^*

^aAlbemarle Process Development Center, Albemarle Corporation, PO Box 341, Baton Rouge, LA 70821, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound PBPEA, C₁₀H₇Br₅O₂, has its ethyl acetate portion nearly orthogonal to the benzene ring, with a C-C-C-C torsion angle of 88.3 (5)°. The packing involves an intermolecular contact with a BrBr distance of 3.491 (1) Å, having C-BrBr angles of 173.4 (2) and 106.0 (2)°. The crystal studied was an inversion twin.

Related literature

For synthetic procedures, see: Holmes & Lightner (1995); Adams & Thal (1941). For a description of the Cambridge Structural Database, see: Allen (2002). For related structures, see: Eriksson & Hu (2002a,b); Eriksson et al. (1999); Köppen et al. (2007); Krigbaum & Wildman (1971); Mrse et al. (2000); Pedireddi et al. (1994); Williams et al. (1985).

Experimental

Crystal data

C₁₀H₇Br₅O₂
M_r = 558.71
Monoclinic, C c
a = 4.6136 (10) Å
b = 22.548 (5) Å
c = 13.195 (2) Å
= 90.993 (11)°
V = 1372.4 (5) Å³
Z = 4
Mo K radiation
= 14.63 mm^-1
T = 90 K
0.25 × 0.12 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) T_min = 0.121, T_max = 0.273
10525 measured reflections
3863 independent reflections
3676 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.053
S = 1.17
3863 reflections
157 parameters
2 restraints
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.66 e Å^-3
Absolute structure: Flack (1983), 1846 Friedel pairs
Flack parameter: 0.467 (13)

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2038 ).

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

Adams, R. & Thal, A. F. (1941). Org. Synth. 1, 270-.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Eriksson, J., Eriksson, L. & Jakobsson, E. (1999). Acta Cryst. C55, 2169-2171.
Eriksson, L. & Hu, J. (2002a). Acta Cryst. E58, o794-o796.
Eriksson, L. & Hu, J. (2002b). Acta Cryst. E58, o1147-o1149.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Holmes, D. L. & Lightner, D. A. (1995). Tetrahedron, 51, 1607-1622.
Köppen, R., Emmerling, F. & Becker, R. (2007). Acta Cryst. E63, o585-o586.
Krigbaum, W. R. & Wildman, G. C. (1971). Acta Cryst. B27, 2353-2358.
Mrse, A. A., Watkins, S. F. & Fronczek, F. R. (2000). Acta Cryst. C56, e576-e577.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju, G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Williams, D. R., Gaston, R. D. & Horton, I. B. (1985). Tetrahedron Lett. 26, 1391-1394.

organic compounds