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Volume 69 
Part 12 
Page o1855  
December 2013  

Received 22 November 2013
Accepted 26 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.074
Data-to-parameter ratio = 20.8
Details
Open access

2,2'-[(1,3,4-Thia­diazole-2,5-di­yl)bis­(sulfanedi­yl)]diaceto­nitrile

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C6H4N4S3, the 1,3,4-thia­diazole ring is essentially planar, with an r.m.s. deviation of 0.001 Å. The two N-C-S-C torsion angles in the mol­ecule are -23.41 (15) and 0.62 (14)°. One aceto­nitrile group is above the plane of the 1,3,4-thia­diazole ring and the other is below it, indicating syn and anti orientations. In the crystal, C-H...N hydrogen bonds link the molecules into ribbons along [010].

Related literature

For the broad spectrum of biological activities of thia­diazole-containing compounds, see: Padmavathi et al. (2009[Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44, 2106-2112.]); Karegoudar et al. (2008[Karegoudar, P., Prasad, D. J., Ashok, A., Mahalinga, M., Poojary, B. & Holla, B. S. (2008). Eur. J. Med. Chem. 43, 808-815.]); Wei et al. (2009[Wei, M. X., Feng, L., Li, X. Q., Zhou, X. Z. & Shao, Z. H. (2009). Eur. J. Med. Chem. 44, 3340-3344.]); Gupta et al. (2009[Gupta, A., Mishra, P., Pandeya, S. N., Kashaw, S. K., Kashaw, V. & Stables, J. P. (2009). Eur. J. Med. Chem. 44, 1100-1105.]); Pattanayak et al. (2009[Pattanayak, P., Sharma, R. & Sahoo, P. K. (2009). Med. Chem. Res. 18, 351-361.]); Cressier et al. (2009[Cressier, D., Prouillac, C., Hernandez, P., Amourette, C., Diserbo, M., Lion, C. & Rima, G. (2009). Bioorg. Med. Chem. 17, 5275-5284.]).

[Scheme 1]

Experimental

Crystal data
  • C6H4N4S3

  • Mr = 228.34

  • Monoclinic, P 21 /c

  • a = 8.5305 (7) Å

  • b = 14.2102 (11) Å

  • c = 7.8803 (6) Å

  • [beta] = 104.3810 (11)°

  • V = 925.32 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.76 mm-1

  • T = 150 K

  • 0.24 × 0.08 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.82, Tmax = 0.96

  • 16625 measured reflections

  • 2450 independent reflections

  • 2155 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.074

  • S = 1.05

  • 2450 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...N1i 0.99 2.60 3.407 (2) 139
C5-H5B...N3ii 0.99 2.35 3.267 (2) 153
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5363 ).


Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Sohag University for supporting this study.

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cressier, D., Prouillac, C., Hernandez, P., Amourette, C., Diserbo, M., Lion, C. & Rima, G. (2009). Bioorg. Med. Chem. 17, 5275-5284.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gupta, A., Mishra, P., Pandeya, S. N., Kashaw, S. K., Kashaw, V. & Stables, J. P. (2009). Eur. J. Med. Chem. 44, 1100-1105.  [CrossRef] [PubMed] [ChemPort]
Karegoudar, P., Prasad, D. J., Ashok, A., Mahalinga, M., Poojary, B. & Holla, B. S. (2008). Eur. J. Med. Chem. 43, 808-815.  [CrossRef] [PubMed] [ChemPort]
Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44, 2106-2112.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Pattanayak, P., Sharma, R. & Sahoo, P. K. (2009). Med. Chem. Res. 18, 351-361.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wei, M. X., Feng, L., Li, X. Q., Zhou, X. Z. & Shao, Z. H. (2009). Eur. J. Med. Chem. 44, 3340-3344.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1855  [ doi:10.1107/S1600536813032194 ]

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