1,5-Dibromo-2,4-dimeth­oxy­benzene

Vijesh, A.M.; Isloor, A.M.; Gerber, T.; Brecht, B. van; Betz, R.

doi:10.1107/S1600536812047848

Volume 68
Part 12
Page o3479
December 2012

Received 2 November 2012
Accepted 21 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.021
wR = 0.049
Data-to-parameter ratio = 21.2
Details

1,5-Dibromo-2,4-dimethoxybenzene

A. M. Vijesh,^a Arun M. Isloor,^b Thomas Gerber,^c Benjamin van Brecht ^c and Richard Betz ^c ^*

^aGITAM University, Department of Engineering Chemistry, GIT, Rushikonda, Visakhapatnam, A.P. 530 045, India,^bNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C₈H₈Br₂O₂, all non-H atoms lie essentially in a common plane (r.m.s deviation of all fitted non-H atoms = 0.0330 Å). In the crystal, weak C-HO hydrogen bonds connect the molecules, forming chains which extend along the b-axis direction.

Related literature

For background to the pharmacological importance of the title compound, see: Pahari & Rohr (2009). For the synthesis of the title compound, see: Yang et al. (2009). For a report listing the crystal structure of 1-bromo-5-chloro-2,4-dimethoxybenzene but entered incorrectly as the title compound in the CSD (TASBAR), see: Yang et al. (2005). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₈Br₂O₂
M_r = 295.96
Monoclinic, P 2₁ /c
a = 7.7944 (2) Å
b = 8.5884 (4) Å
c = 14.7877 (4) Å
= 107.838 (1)°
V = 942.32 (6) Å³
Z = 4
Mo K radiation
= 8.56 mm^-1
T = 200 K
0.47 × 0.46 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.674, T_max = 1.000
15097 measured reflections
2350 independent reflections
2094 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.021
wR(F²) = 0.049
S = 1.08
2350 reflections
111 parameters
H-atom parameters constrained
_max = 0.55 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7CO1ⁱ	0.98	2.70	3.632 (3)	160
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2243 ).

Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Pahari, P. & Rohr, J. (2009). J. Org. Chem. 74, 2750-2754.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yang, Y., Escobedo, J. O., Wong, A., Schowalter, C. M., Touchy, M. C., Jiao, L., Crowe, W. E., Fronczek, F. R. & Strongin, R. M. (2005). J. Org. Chem. 70, 6907-6912.
Yang, L., Lu, Z. & Stahl, S. S. (2009). Chem. Commun. pp. 6460-6462.

organic compounds