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Volume 66 
Part 7 
Page o1871  
July 2010  

Received 23 June 2010
Accepted 24 June 2010
Online 30 June 2010

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.064
wR = 0.254
Data-to-parameter ratio = 27.6
Details
Open access

Methyl 2,6-bis[(5-bromo-4,6-dimethoxypyrimidin-2-yl)oxy]benzoate

Hoong-Kun Fun,a*+ Jia Hao Goh,a++ Sankappa Rai,b Arun M. Isloorc and Prakash Shettyd

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104, India,cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and dDepartment of Printing, Manipal Institute of Technology, Manipal University, Manipal 576 104, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C20H18Br2N4O8, the interplanar angle of the pyrimidine rings is 75.1 (2)°. The central benzene ring is inclined at interplanar angles of 66.5 (2) and 71.9 (2)° with respect to the two pyrimidine rings. In the crystal structure, adjacent molecules are connected into two-molecule-thick arrays parallel to the bc plane via short Br...Br [3.5328 (12) Å] and Br...O [3.206 (3) and 3.301 (4) Å] interactions. A weak intermolecular [pi]-[pi] aromatic stacking interaction [centroid-centroid distance = 3.526 (3) Å] is also observed.

Related literature

For general background to and applications of the title compound, see: Koichiro et al. (1988[Koichiro, S., Shoji, K., Yasubumi, T., Takeshige, M. & Ryo, Y. (1988). Japan Patent 88-132167 (CA112:216956, 1998).]); He et al. (2007[He, Y.-Z., Li, Y.-X., Zhu, X.-L., Xi, Z., Niu, C., Wan, J., Zhang, L. & Yang, G.-F. (2007). J. Chem. Inf. Model. 47, 2335-2344.]); Li et al. (2006[Li, Y.-X., Luo, Y.-P., Xi, Z., Niu, C., He, Y.-Z. & Yang, G.-F. (2006). J. Agric. Food Chem. 54, 9135-9139.]); Gerorge (1983[Gerorge, L. (1983). US Patent No. 4 394 506.]). For closely related structures, see: Fun et al. (2010[Fun, H.-K., Goh, J. H., Rai, S., Isloor, A. M. & Shetty, P. (2010). Acta Cryst. E66, ci5115.]); Li & Luo (2006[Li, Y.-X. & Luo, Y.-P. (2006). Acta Cryst. E62, o1323-o1325.]).

[Scheme 1]

Experimental

Crystal data

  • C20H18Br2N4O8

  • Mr = 602.20

  • Monoclinic, C 2/c

  • a = 29.972 (5) Å

  • b = 8.1392 (12) Å

  • c = 23.061 (3) Å

  • [beta] = 123.120 (3)°

  • V = 4711.8 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.49 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.14 mm
Data collection

  • Bruker APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.549, Tmax = 0.640

  • 25204 measured reflections

  • 8438 independent reflections

  • 4458 reflections with I > 2[sigma](I)

  • Rint = 0.066
Refinement

  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.254

  • S = 1.02

  • 8438 reflections

  • 306 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.32 e Å-3

  • [Delta][rho]min = -1.56 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: HB5519 ).

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. AMI is grateful to the Head of the Chemistry Department and the Director, National Institute of Technology-Karnataka for their encouragement. AMI also thanks USM for a partially sponsored research visit to the X-ray Crystallography Unit, School of Physics, USM.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Goh, J. H., Rai, S., Isloor, A. M. & Shetty, P. (2010). Acta Cryst. E66, ci5115.
Gerorge, L. (1983). US Patent No. 4 394 506.
He, Y.-Z., Li, Y.-X., Zhu, X.-L., Xi, Z., Niu, C., Wan, J., Zhang, L. & Yang, G.-F. (2007). J. Chem. Inf. Model. 47, 2335-2344.  [CrossRef] [PubMed] [ChemPort]
Koichiro, S., Shoji, K., Yasubumi, T., Takeshige, M. & Ryo, Y. (1988). Japan Patent 88-132167 (CA112:216956, 1998).
Li, Y.-X. & Luo, Y.-P. (2006). Acta Cryst. E62, o1323-o1325.  [CSD] [CrossRef] [details]
Li, Y.-X., Luo, Y.-P., Xi, Z., Niu, C., He, Y.-Z. & Yang, G.-F. (2006). J. Agric. Food Chem. 54, 9135-9139.  [ISI] [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]

Acta Cryst (2010). E66, o1871  [ doi:10.1107/S1600536810024724 ]

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