5,6-Dimethyl­pyrazine-2,3-dicarbonitrile

Bardajee, G.R.; Lough, A.J.; Winnik, M.A.

doi:10.1107/S1600536812043474

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 (C-C) = 0.004 Å
R = 0.039
wR = 0.110
Data-to-parameter ratio = 16.4
Details

5,6-Dimethylpyrazine-2,3-dicarbonitrile

Ghasem Rezanejade Bardajee,^a Alan J. Lough ^b ^* and Mitchell A. Winnik ^b

^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); Yadav et al. (2008). For the synthesis, see: Bardajee et al. (2012). For related structures, see: Hökelek et al. (2009); Donzello et al. (2004); Cristiano et al. (2007).

Experimental

Crystal data

C₈H₆N₄
M_r = 158.17
Monoclinic, C 2/c
a = 24.183 (2) Å
b = 9.210 (1) Å
c = 18.761 (2) Å
= 130.151 (2)°
V = 3193.8 (6) Å³
Z = 16
Mo K radiation
= 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) T_min = 0.711, T_max = 0.746
7543 measured reflections
3650 independent reflections
2927 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.110
S = 1.05
3650 reflections
222 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.21 e Å^-3

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
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.
Donzello, M. P., Ou, Z., Monacelli, F., Ricciardi, G., Rizzoli, C., Ercolani, C. & Kadish, K. H. (2004). Inorg. Chem. 43, 8626-8636.
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.
Hökelek, T., Yalçin, E., Seferoglu, Z. & Sahin, E. (2009). Acta Cryst. E65, o2225.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yadav, J. S., Reddy, B. V. S., Premalatha, K. & Shankar, K. S. (2008). Synthesis, pp. 3787-3792.

organic compounds