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Volume 66 
Part 11 
Page o2931  
November 2010  

Received 3 October 2010
Accepted 19 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.128
Data-to-parameter ratio = 13.0
Details
Open access

5,5'-Diphenyl-2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(1,3,4-oxadiazole)

aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China,bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China, and cLiaoyang Supervision and Examination Station of Product Quality, Liaoning Liaoyang 111000, People's Republic of China
Correspondence e-mail: zhao_submit@yahoo.com.cn

The complete molecule of the title compound, C20H18N4O2S2, is generated by crystallographic inversion symmetry. The benzene ring is almost coplanar with the oxadiazole ring [dihedral angle = 7.2 (2)°].

Related literature

Functionalized 1,3,4-oxadiazole derivatives are of interest because of their biological activity and their wide applications in medicine, coordination chemistry and their use as organic electroluminescent (EL) devices, since these compounds possess good electron-accepting properties, see: Bentiss et al. (2000[Bentiss, F., Traisnel, M. & Lagrenee, M. (2000). Corros. Sci. 42, 127-146.]); Hughes & Bryce (2005[Hughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94-107.]); Navidpour et al. (2006[Navidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507-2517.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N4O2S2

  • Mr = 410.50

  • Monoclinic, P 21 /c

  • a = 12.202 (2) Å

  • b = 5.9317 (12) Å

  • c = 13.518 (3) Å

  • [beta] = 104.04 (3)°

  • V = 949.2 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.942, Tmax = 0.964

  • 7030 measured reflections

  • 1661 independent reflections

  • 1323 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.128

  • S = 1.10

  • 1661 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). 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: ZS2072 ).


Acknowledgements

We gratefully acknowledge support of this project by the Key Laboratory Project of Liaoning Province (No. 2008S127) and by the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

References

Bentiss, F., Traisnel, M. & Lagrenee, M. (2000). Corros. Sci. 42, 127-146.  [CrossRef] [ChemPort]
Hughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94-107.  [ISI] [CrossRef] [ChemPort]
Navidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507-2517.  [CrossRef] [PubMed] [ChemPort]
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o2931  [ doi:10.1107/S1600536810042315 ]

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