1-Bromo-4-chloro-2,5-dimethoxy­benzene

Song, Y.; Parkin, S.; Lehmler, H.-J.

doi:10.1107/S1600536810000504

Volume 66
Part 2
Page o339
February 2010

Received 15 December 2009
Accepted 5 January 2010
Online 13 January 2010

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.030
wR = 0.069
Data-to-parameter ratio = 16.7
Details

1-Bromo-4-chloro-2,5-dimethoxybenzene

Yang Song,^a Sean Parkin ^b and Hans-Joachim Lehmler ^c ^*

^aCollege of Pharmaceutical Sciences, Southwest University, Chong Qing 400716, People's Republic of China,^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506-0055, USA, and ^cDepartment of Occupational and Environmental Health, The University of Iowa, 100 Oakdale Campus, 124 IREH, Iowa City, IA 52242-5000, USA
Correspondence e-mail: hans-joachim-lehmler@uiowa.edu

The molecule of the title compound, C₈H₈BrClO₂, sits on a crystallographic inversion centre, which ensures that the halogen sites are disordered, with exactly 50% Br and 50% Cl at each halogen site. The inversion renders the two methoxy groups equivalent. These groups lie almost in the plane of the aromatic ring system, making dihedral angles of 8.8 (4)° to the ring.

Related literature

For the synthesis of PCBs and PCB metabolites using the Suzuki coupling reaction, see: Lehmler & Robertson (2001); Song et al. (2008). For similar structures of halogenated methoxy-benzenes, see: Rissanen et al. (1988); Telu et al. (2008) and literature cited therein. For general background about PCBs, see: Hansen (1999); Robertson & Hansen (2001).

Experimental

Crystal data

C₈H₈BrClO₂
M_r = 251.50
Monoclinic, P 2₁ /n
a = 6.3804 (7) Å
b = 8.2586 (10) Å
c = 8.6337 (11) Å
= 90.853 (6)°
V = 454.89 (9) Å³
Z = 2
Mo K radiation
= 4.77 mm^-1
T = 90 K
0.25 × 0.22 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.310, T_max = 0.350
1938 measured reflections
1021 independent reflections
824 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.069
S = 1.04
1021 reflections
61 parameters
2 restraints
H-atom parameters constrained
_max = 0.57 e Å^-3
_min = -0.49 e Å^-3

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX97 and local procedures.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2231 ).

Acknowledgements

This research was supported by grants ES05605, ES012475, ES013661 from the National Institute of Environmental Health Sciences, NIH, (HJL) and SWUB2008077 from the Science Foundation of Southwest University, China (YS).

References

Hansen, L. G. (1999). The ortho side of PCBs: Occurrence and disposition. Boston: Kluwer Academic Publishers.
Lehmler, H.-J. & Robertson, L. W. (2001). Chemosphere, 45, 1119-1127.
Nonius (1998). COLLECT. Nonius BV, Delft,The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by Carter, C. W. Jr & Sweet, R. M. pp. 307-326. New York: Academic Press.
Rissanen, K., Valkonen, J. & Mannila, B. (1988). Acta Cryst. C44, 682-684.
Robertson, L. W. & Hansen, L. G. (2001). Recent advances in the environmental toxicology and health effects of PCBs. University Press of Kentucky, Lexington.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, Y., Buettner, G. R., Parkin, S., Wagner, B. A., Robertson, L. W. & Lehmler, H.-J. (2008). J. Org. Chem. 73, 8296-8304.
Telu, S., Parkin, S., Robertson, L. W. & Lehmler, H.-J. (2008). Acta Cryst. E64, o424.

organic compounds