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Volume 69 
Part 11 
Page o1613  
November 2013  

Received 9 September 2013
Accepted 24 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.114
Data-to-parameter ratio = 12.3
Details
Open access

2,3-Bis(furan-2-yl)pyrazino­[2,3-f][1,10]phenanthroline

aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
Correspondence e-mail: cgzheng@jiangnan.edu.cn

The mol­ecule of the title compound, C22H12N4O2, is located on a twofold rotation axis. The dihedral angle between the furan and pyrazine rings is 34.8 (7)°, and that between the furan rings is 46.92 (7)°. A [pi]-[pi] stacking interaction occurs between adjacent pyrazino[2,3-f][1,10]phenanthroline units, with an interplanar distance of 3.5862 (12) Å.

Related literature

For the properties of 2,3-dithienyl­pyrazino­[2,3-f][1,10]phenanthroline, see: Bencini et al. (1999[Bencini, A., Bernardo, M. A., Bianchi, A., Fusi, V., Giorgi, C., Pina, F. & Valtancoli, B. (1999). Eur. J. Inorg. Chem. pp. 1911-1918.]); Li et al. (2010[Li, X. X., Guo, Y., Chi, H. J., Dong, Y. Z. & Hong, B. (2010). Mater. Chem. Phys. 123, 289-292.]). For the structure of 2,3-bis­(thio­phen-2-yl)pyrazino­[2,3-f][1,10]phenanthroline, see: Zheng et al. (2012[Zheng, C.-G., Kong, J., Zhang, P. & Dong, W.-X. (2012). Acta Cryst. E68, o1443.]) and for the structure of 3-carb­oxy­pyrazino­[2,3-f][1,10]-phenanthrolin-9-ium-2-carb­oxyl­ate see: Zhang et al. (2010[Zhang, X.-N., Fu, F., Li, D.-S. & Meng, C.-X. (2010). Acta Cryst. E66, o740.]).

[Scheme 1]

Experimental

Crystal data
  • C22H12N4O2

  • Mr = 364.36

  • Orthorhombic, P b c n

  • a = 7.0994 (14) Å

  • b = 25.014 (5) Å

  • c = 9.4083 (19) Å

  • V = 1670.8 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.26 × 0.21 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.983

  • 7791 measured reflections

  • 1565 independent reflections

  • 1382 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.114

  • S = 1.18

  • 1565 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6933 ).


Acknowledgements

The authors are grateful for financial support from the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.

References

Bencini, A., Bernardo, M. A., Bianchi, A., Fusi, V., Giorgi, C., Pina, F. & Valtancoli, B. (1999). Eur. J. Inorg. Chem. pp. 1911-1918.  [CrossRef]
Bruker (2005). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA.
Li, X. X., Guo, Y., Chi, H. J., Dong, Y. Z. & Hong, B. (2010). Mater. Chem. Phys. 123, 289-292.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zhang, X.-N., Fu, F., Li, D.-S. & Meng, C.-X. (2010). Acta Cryst. E66, o740.  [CrossRef] [IUCr Journals]
Zheng, C.-G., Kong, J., Zhang, P. & Dong, W.-X. (2012). Acta Cryst. E68, o1443.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1613  [ doi:10.1107/S160053681302641X ]

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