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Volume 68 
Part 1 
Page o132  
January 2012  

Received 13 November 2011
Accepted 5 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.133
Data-to-parameter ratio = 11.4
Details
Open access

5,6-Dimethylpyrazine-2,3-dicarboxylic acid

aBasis Department, Jilin Business and Technology College, Hao Yue Road No. 1606, Changchun, Jilin, People's Republic of China
Correspondence e-mail: liufuhong123@gmail.com

The asymmetric unit of the title compound, C8H8N2O4, consists of one complete molecule and a second molecule generated by the application of twofold axis. The mean planes of the two carboxyl groups attached to the pyrazine ring at neighboring positions are twisted by 10.8 (1) and 87.9 (1)° in the complete molecule and 43.0 (1)° in the symmetry-generated molecule. The crystal packing features O-H...N hydrogen bonds, which link the molecules into layers along [101].

Related literature

For the synthesis of the title compound, see Tsuda & Fujishima (1981[Tsuda, T. & Fujishima, K. (1981). Agric. Biol. Chem. 45, 2129-2130.]). For the structure of the hydrate of the title compound, see Vishweshwar et al. (2001[Vishweshwar, P., Nangia, A. & Lynch, V. M. (2001). Chem. Commun. pp. 179-180.], 2004[Vishweshwar, P., Jagadeesh Babu, N., Nangia, A., Mason, S. A., Puschmann, H., Mondal, R. & Howard, J. A. K. (2004). J. Phys. Chem. A, 43, 9406-9416.]). For a related compound containing pyrazine-2,3-dicarboxylic acid, see: Alborés & Rentschler (2009[Alborés, P. & Rentschler, E. (2009). Angew. Chem. Int. Ed. 48, 9366-9370.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8N2O4

  • Mr = 196.16

  • Monoclinic, C 2/c

  • a = 15.873 (3) Å

  • b = 14.057 (3) Å

  • c = 11.991 (2) Å

  • [beta] = 109.21 (3)°

  • V = 2526.6 (9) Å3

  • Z = 12

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Rigaku SCX-mini diffractometer

  • 10832 measured reflections

  • 2230 independent reflections

  • 1937 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.133

  • S = 1.07

  • 2230 reflections

  • 196 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N2i 0.82 (1) 2.04 2.845 (2) 167
O3-H3...N3ii 0.82 (1) 2.00 2.803 (2) 165
O5-H5...N1iii 0.82 (1) 2.06 2.874 (2) 169
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y, z-1.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2111 ).


Acknowledgements

The author thanks the Jilin Business and Technology College for financial support.

References

Alborés, P. & Rentschler, E. (2009). Angew. Chem. Int. Ed. 48, 9366-9370.  [ISI] [CSD] [CrossRef]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tsuda, T. & Fujishima, K. (1981). Agric. Biol. Chem. 45, 2129-2130.  [ChemPort]
Vishweshwar, P., Jagadeesh Babu, N., Nangia, A., Mason, S. A., Puschmann, H., Mondal, R. & Howard, J. A. K. (2004). J. Phys. Chem. A, 43, 9406-9416.  [ISI] [CSD] [CrossRef]
Vishweshwar, P., Nangia, A. & Lynch, V. M. (2001). Chem. Commun. pp. 179-180.  [CSD] [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o132  [ doi:10.1107/S1600536811052366 ]

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