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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 [sigma](C-C) = 0.002 Å
R = 0.021
wR = 0.049
Data-to-parameter ratio = 21.2
Details
Open access

1,5-Dibromo-2,4-dimethoxybenzene

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-H...O 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[Pahari, P. & Rohr, J. (2009). J. Org. Chem. 74, 2750-2754.]). For the synthesis of the title compound, see: Yang et al. (2009[Yang, L., Lu, Z. & Stahl, S. S. (2009). Chem. Commun. pp. 6460-6462.]). 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[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.]). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8Br2O2

  • Mr = 295.96

  • Monoclinic, P 21 /c

  • a = 7.7944 (2) Å

  • b = 8.5884 (4) Å

  • c = 14.7877 (4) Å

  • [beta] = 107.838 (1)°

  • V = 942.32 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.674, Tmax = 1.000

  • 15097 measured reflections

  • 2350 independent reflections

  • 2094 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.021

  • wR(F2) = 0.049

  • S = 1.08

  • 2350 reflections

  • 111 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7C...O1i 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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Pahari, P. & Rohr, J. (2009). J. Org. Chem. 74, 2750-2754.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [CSD] [CrossRef] [PubMed] [ChemPort]
Yang, L., Lu, Z. & Stahl, S. S. (2009). Chem. Commun. pp. 6460-6462.  [CrossRef]


Acta Cryst (2012). E68, o3479  [ doi:10.1107/S1600536812047848 ]

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