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Volume 69 
Part 3 
Page o394  
March 2013  

Received 7 February 2013
Accepted 12 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.183
Data-to-parameter ratio = 26.2
Details
Open access

2,3-Bis(thiophen-3-yl)quinoxaline

aDepartment of Chemistry, Central Connecticut State University, New Britain, CT 06053, USA
Correspondence e-mail: crundwellg@mail.ccsu.edu

In the title compound, C16H10N2S2, the thienyl rings are inclined to one another by 62.71 (10)°, and are inclined by 63.94 (8) and 21.35 (8)° to the quinoline mean plane [maximum deviation = 0.031 (2) Å]. In the crystal, the molecules pack in a herringbone pattern, with [pi]-[pi] stacking interactions [centroid-centroid distances = 3.7381 (15) and 3.7268 (15) Å].

Related literature

For the synthesis of the title compound, and the crystal structure of the 2,3-di(thiophen-2-yl)quinoxaline analogue, see: Crundwell et al. (2003[Crundwell, G., Sayers, D., Herron, S. R. & Kantardjieff, K. A. (2003). Acta Cryst. E59, o314-o315.]). For the structure of a similar compound, see: Cantalupo et al. (2010[Cantalupo, S. A., Crundwell, G. & Glagovich, N. (2010). Acta Cryst. E66, o2184.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10N2S2

  • Mr = 294.38

  • Monoclinic, P 21 /c

  • a = 15.966 (2) Å

  • b = 5.5741 (15) Å

  • c = 15.629 (4) Å

  • [beta] = 98.25 (2)°

  • V = 1376.5 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 293 K

  • 0.45 × 0.44 × 0.39 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.731, Tmax = 1.000

  • 30279 measured reflections

  • 4745 independent reflections

  • 2660 reflections with I > 2[sigma](I)

  • Rint = 0.087

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.183

  • S = 0.92

  • 4745 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: SU2562 ).


Acknowledgements

This research was funded by a CCSU-AAUP research grant.

References

Cantalupo, S. A., Crundwell, G. & Glagovich, N. (2010). Acta Cryst. E66, o2184.  [CSD] [CrossRef] [details]
Crundwell, G., Sayers, D., Herron, S. R. & Kantardjieff, K. A. (2003). Acta Cryst. E59, o314-o315.  [CSD] [CrossRef] [details]
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o394  [ doi:10.1107/S1600536813004248 ]

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