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Volume 69 
Part 7 
Page o1157  
July 2013  

Received 13 June 2013
Accepted 20 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.057
Data-to-parameter ratio = 25.1
Details
Open access

2-(1,3-Dithiol-2-ylidene)-1,3-dithiole-4-carbaldehyde

aYoungstown State University, One University Plaza, Youngstown, OH 44555-3663, USA, and bDepartment of Chemistry, University of Bremen, Leobener Strasse, NW 2C, D-28359 Bremen, Germany
Correspondence e-mail: vazov@uni-bremen.de

The structure of the title compound, C7H4OS4, at 100 K has orthorhombic symmetry. In the crystal, tetrathiafulvalene molecules form [pi]-stacks along the a axis, with a stacking distance of 3.4736 (6) Å. Along the b axis, parallel stacks are interconnected with each other through a network of weak C-H...O hydrogen bonds and short S...S contacts [3.4813 (7) Å]. Additional short S...S contacts [3.4980 (9) Å] join parallel stacks along the c axis.

Related literature

For tetrathiafulvalene derivatives and their applications, see: Yamada & Sugimoto (2004[Yamada, J. & Sugimoto, T. (2004). In TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalenes. Berlin, Heidelberg, New York: Springer-Verlag.]); Segura & Martín (2001[Segura, J. L. & Martín, N. (2001). Angew. Chem. Int. Ed. 40, 1372-1409.]). For a review on synthetic chemistry of tetrathiafulvalenes, see: Fabre (2004[Fabre, J. M. (2004). Chem. Rev. 104, 5133-5150.]). For a previous synthesis of the title compound, see: Garín et al. (1994[Garín, J., Orduna, J., Uriel, S., Moore, A. J., Bryce, M. R., Wegener, S., Yufit, D. S. & Howard, A. K. (1994). Synthesis, pp. 489-493.]). For reviews on `weak' non-classical hydrogen bonding, see: Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]); Desiraju (2005[Desiraju, G. R. (2005). Chem. Commun. pp. 2995-3001.]). For reviews on halogen-halogen contacts, see: Metrangolo et al. (2008[Metrangolo, P., Meyer, F., Pilati, T., Resnati, G. & Terraneo, G. (2008). Angew. Chem. Int. Ed. 47, 6114-6127.]).

[Scheme 1]

Experimental

Crystal data
  • C7H4OS4

  • Mr = 232.34

  • Orthorhombic, P 21 21 21

  • a = 3.8466 (3) Å

  • b = 7.4052 (7) Å

  • c = 30.577 (3) Å

  • V = 870.99 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.03 mm-1

  • T = 100 K

  • 0.50 × 0.21 × 0.13 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.675, Tmax = 0.746

  • 6998 measured reflections

  • 2734 independent reflections

  • 2663 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.057

  • S = 1.13

  • 2734 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.]), 1024 Friedel pairs

  • Flack parameter: 0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O1i 0.95 2.38 3.228 (3) 149
C3-H3...O1i 0.95 2.69 3.445 (3) 137
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany.]) and SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2488 ).


Acknowledgements

The authors are grateful to Dr C. Vande Velde (Karel de Grote University College, Antwerp, Belgium) for helpful discussions. The X-ray diffractometer (MZ) was funded by NSF grant No. 0087210, Ohio Board of Regents grant CAP-491 and Youngstown State University.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (2005). Chem. Commun. pp. 2995-3001.  [CrossRef]
Fabre, J. M. (2004). Chem. Rev. 104, 5133-5150.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Garín, J., Orduna, J., Uriel, S., Moore, A. J., Bryce, M. R., Wegener, S., Yufit, D. S. & Howard, A. K. (1994). Synthesis, pp. 489-493.
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.  [Web of Science] [CrossRef] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Metrangolo, P., Meyer, F., Pilati, T., Resnati, G. & Terraneo, G. (2008). Angew. Chem. Int. Ed. 47, 6114-6127.  [Web of Science] [CrossRef] [ChemPort]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Segura, J. L. & Martín, N. (2001). Angew. Chem. Int. Ed. 40, 1372-1409.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany.
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [Web of Science] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yamada, J. & Sugimoto, T. (2004). In TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalenes. Berlin, Heidelberg, New York: Springer-Verlag.


Acta Cryst (2013). E69, o1157  [ doi:10.1107/S160053681301711X ]

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