2,3-Bis(thio­phen-3-yl)quinoxaline

Crundwell, G.; Freitas, J. de

doi:10.1107/S1600536813004248

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.183
Data-to-parameter ratio = 26.2
Details

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

Guy Crundwell ^a ^* and Jorge de Freitas ^a

^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). For the structure of a similar compound, see: Cantalupo et al. (2010).

Experimental

Crystal data

C₁₆H₁₀N₂S₂
M_r = 294.38
Monoclinic, P 2₁ /c
a = 15.966 (2) Å
b = 5.5741 (15) Å
c = 15.629 (4) Å
= 98.25 (2)°
V = 1376.5 (6) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.731, T_max = 1.000
30279 measured reflections
4745 independent reflections
2660 reflections with I > 2(I)
R_int = 0.087

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.183
S = 0.92
4745 reflections
181 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_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); 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: 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.
Crundwell, G., Sayers, D., Herron, S. R. & Kantardjieff, K. A. (2003). Acta Cryst. E59, o314-o315.
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds