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Volume 68 
Part 11 
Page o3220  
November 2012  

Received 4 October 2012
Accepted 19 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.039
wR = 0.110
Data-to-parameter ratio = 16.4
Details
Open access

5,6-Dimethylpyrazine-2,3-dicarbonitrile

aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran, and bDepartment of Chemistry, University of Toronto, 80 St Geroge St, Toronto, Ontario, Canada M5S 3H6
Correspondence e-mail: alough@chem.utoronto.ca

The asymmetric unit of the title compound, C8H6N4, contains two almost planar independent molecules (r.m.s. deviations = 0.026 and 0.030 Å). The crystal studied was a non-merohedral twin with the components in a 0.513 (2):0.487 (2) ratio.

Related literature

For applications of pyrazine compounds and their derivatives, see: He et al. (2003[He, W., Meyers, M. R., Hanney, B., Sapada, A., Blider, g., Galzeinski, H., Amin, D., Needle, S. Page, K., Jayyosi, Z. & Perrone, H. (2003). Bioorg. Med. Chem. Lett. 13, 3097-3100.]); Yadav et al. (2008[Yadav, J. S., Reddy, B. V. S., Premalatha, K. & Shankar, K. S. (2008). Synthesis, pp. 3787-3792.]). For the synthesis, see: Bardajee et al. (2012[Bardajee, G. R., Malakooti, R., Jamia, F., Parsaei, Z. & Atashin, H. (2012). Catal. Commun. 27, 49-53.]). For related structures, see: Hökelek et al. (2009[Hökelek, T., Yalçin, E., Seferoglu, Z. & Sahin, E. (2009). Acta Cryst. E65, o2225.]); Donzello et al. (2004[Donzello, M. P., Ou, Z., Monacelli, F., Ricciardi, G., Rizzoli, C., Ercolani, C. & Kadish, K. H. (2004). Inorg. Chem. 43, 8626-8636.]); Cristiano et al. (2007[Cristiano, R., Westphal, E., Bechtold, I. H., Bortoluzzi, A. J. & Gallardo, H. (2007). Tetrahedron, 63, 2851-2858.]).

[Scheme 1]

Experimental

Crystal data
  • C8H6N4

  • Mr = 158.17

  • Monoclinic, C 2/c

  • a = 24.183 (2) Å

  • b = 9.210 (1) Å

  • c = 18.761 (2) Å

  • [beta] = 130.151 (2)°

  • V = 3193.8 (6) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.28 × 0.22 × 0.18 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.711, Tmax = 0.746

  • 7543 measured reflections

  • 3650 independent reflections

  • 2927 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.110

  • S = 1.05

  • 3650 reflections

  • 222 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6967 ).


Acknowledgements

GRB is thankful to PNU for funding of this study and the University of Toronto thanks NSERC Canada for funding.

References

Bardajee, G. R., Malakooti, R., Jamia, F., Parsaei, Z. & Atashin, H. (2012). Catal. Commun. 27, 49-53.  [CrossRef] [ChemPort]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cristiano, R., Westphal, E., Bechtold, I. H., Bortoluzzi, A. J. & Gallardo, H. (2007). Tetrahedron, 63, 2851-2858.  [ISI] [CSD] [CrossRef] [ChemPort]
Donzello, M. P., Ou, Z., Monacelli, F., Ricciardi, G., Rizzoli, C., Ercolani, C. & Kadish, K. H. (2004). Inorg. Chem. 43, 8626-8636.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
He, W., Meyers, M. R., Hanney, B., Sapada, A., Blider, g., Galzeinski, H., Amin, D., Needle, S. Page, K., Jayyosi, Z. & Perrone, H. (2003). Bioorg. Med. Chem. Lett. 13, 3097-3100.  [CrossRef] [PubMed] [ChemPort]
Hökelek, T., Yalçin, E., Seferoglu, Z. & Sahin, E. (2009). Acta Cryst. E65, o2225.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yadav, J. S., Reddy, B. V. S., Premalatha, K. & Shankar, K. S. (2008). Synthesis, pp. 3787-3792.  [ISI] [CrossRef]


Acta Cryst (2012). E68, o3220  [ doi:10.1107/S1600536812043474 ]

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