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

Liu, F.-H.

doi:10.1107/S1600536811052366

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 (C-C) = 0.003 Å
R = 0.049
wR = 0.133
Data-to-parameter ratio = 11.4
Details

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

Fu-Hong Liu ^a ^*

^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-HN hydrogen bonds, which link the molecules into layers along [101].

Related literature

For the synthesis of the title compound, see Tsuda & Fujishima (1981). For the structure of the hydrate of the title compound, see Vishweshwar et al. (2001, 2004). For a related compound containing pyrazine-2,3-dicarboxylic acid, see: Alborés & Rentschler (2009).

Experimental

Crystal data

C₈H₈N₂O₄
M_r = 196.16
Monoclinic, C 2/c
a = 15.873 (3) Å
b = 14.057 (3) Å
c = 11.991 (2) Å
= 109.21 (3)°
V = 2526.6 (9) Å³
Z = 12
Mo K radiation
= 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(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.133
S = 1.07
2230 reflections
196 parameters
H-atom parameters constrained
_max = 0.63 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N2ⁱ	0.82 (1)	2.04	2.845 (2)	167
O3-H3N3ⁱⁱ	0.82 (1)	2.00	2.803 (2)	165
O5-H5N1ⁱⁱⁱ	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); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Tsuda, T. & Fujishima, K. (1981). Agric. Biol. Chem. 45, 2129-2130.
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.
Vishweshwar, P., Nangia, A. & Lynch, V. M. (2001). Chem. Commun. pp. 179-180.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds