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Volume 68 
Part 1 
Page o52  
January 2012  

Received 12 October 2011
Accepted 30 November 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.009 Å
Disorder in main residue
R = 0.061
wR = 0.107
Data-to-parameter ratio = 14.5
Details
Open access

2,5-Bis(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione

aDivision of Basic Engineering, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu, Shizuoka 432-8561, Japan,bDepartment of Materials Science and Chemical Engineering, Graduate School of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu, Shizuoka 432-8561, Japan, and cBruker AXS Co. Ltd, Moriya-cho 3-9, Kanagawa-ku, Kanagawa, Kanagawa 221-0022, Japan
Correspondence e-mail: tkueda@ipc.shizuoka.ac.jp

The asymmetric unit of the title compound, C9H4S7, contains two independent molecules, in one of which the central five-membered ring is disordered over two orientations in a 0.924 (3):0.076 (3) ratio. The molecular skeleton is almost planar: the average distance of the atoms from their mean plane is 0.128 (7) Å in the ordered molecule, and 0.088 (5) and 0.123 (2) Å in the major and minor disorder components, respectively. The ordered and disordered molecules form separate columns by stacking along the b axis. Adjacent columns interact via short S...S [3.33 (2), 3.434 (3), 3.444 (2), 3.503 (2), 3.519 (3) and 3.53 (4) Å] and S...H [2.814 (2), 2.87 (7), 2.92 (2), 2.9269 (18), 2.93 (2), 2.94 (2), 2.939 (2), 2.967 (2) and 2.974 (1) Å] contacts.

Related literature

For background to 2,5-di(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione derivatives, see: Iwamatsu et al. (1999[Iwamatsu, M., Kominami, T., Ueda, K., Sugimoto, T., Fujita, H. & Adachi, T. (1999). Chem. Lett. pp. 329-330.], 2000[Iwamatsu, M., Kominami, T., Ueda, K., Sugimoto, T., Adachi, T., Fujita, H., Yoshino, H., Mizuno, Y., Murata, K. & Shiro, M. (2000). Inorg. Chem. 39, 3810-3815.]); Wang et al. (2005[Wang, M., Fujiwara, H., Sugimoto, T., Noguchi, S. & Ishida, T. (2005). Inorg. Chem. 44, 1184-1186.], 2007[Wang, M., Xiao, X., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Mori, T. & Katori, H. A. (2007). Inorg. Chem. 46, 3049-3056.]); Hiraoka et al. (2005[Hiraoka, T., Kamada, Y., Matsumoto, T., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Nakazumi, H. & Katori, H. A. (2005). J. Mater. Chem. 15, 3479-3487.]); Fujiwara et al. (2006[Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T. & Nakazumi, H. (2006). J. Low Temp. Phys. 142, 405-408.], 2007[Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T., Nakazumi, H., Teramura, M., Yokogawa, K., Yasuzuka, S. & Murata, K. (2007). Multifunctional Conducting Molecular Materials, edited by G. Saito, F. Wudl, R. C. Haddon, K. Tanigaki, T. Enoki, H. E. Katz & M. Maesato, pp. 161-164. Cambridge: RSC Publishing.]); Ueda & Yoza (2009a[Ueda, K. & Yoza, K. (2009a). Acta Cryst. E65, o2716.],b[Ueda, K. & Yoza, K. (2009b). Acta Cryst. E65, o2831.],c[Ueda, K. & Yoza, K. (2009c). Acta Cryst. E65, o2920.]). For the synthesis, see: Ueda et al. (2010[Ueda, K., Suzuki, K., Suzuki, K., Yoza, K. & Ishida, T. (2010). Phys. B (Amsterdam), 405, S69-S74.]). For van der Waals radii, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]).

[Scheme 1]

Experimental

Crystal data
  • C9H4S7

  • Mr = 336.54

  • Monoclinic, P 21

  • a = 17.669 (5) Å

  • b = 3.9110 (11) Å

  • c = 18.380 (5) Å

  • [beta] = 108.177 (4)°

  • V = 1206.8 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.27 mm-1

  • T = 93 K

  • 0.09 × 0.02 × 0.02 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Götingen, Germany.]) Tmin = 0.894, Tmax = 0.975

  • 6965 measured reflections

  • 4975 independent reflections

  • 3396 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.107

  • S = 0.98

  • 4975 reflections

  • 344 parameters

  • 421 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1849 Friedel pairs

  • Flack parameter: -0.18 (18)

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT, XCIF. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT, XCIF. 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: 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: XCIF (Bruker, 2010[Bruker (2010). APEX2, SAINT, XCIF. Bruker AXS Inc., Madison, Wisconsin, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2030 ).


References

Bondi, A. (1964). J. Phys. Chem. 68, 441-451.  [CrossRef] [ChemPort] [ISI]
Bruker (2010). APEX2, SAINT, XCIF. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T. & Nakazumi, H. (2006). J. Low Temp. Phys. 142, 405-408.  [ISI] [CrossRef]
Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T., Nakazumi, H., Teramura, M., Yokogawa, K., Yasuzuka, S. & Murata, K. (2007). Multifunctional Conducting Molecular Materials, edited by G. Saito, F. Wudl, R. C. Haddon, K. Tanigaki, T. Enoki, H. E. Katz & M. Maesato, pp. 161-164. Cambridge: RSC Publishing.
Hiraoka, T., Kamada, Y., Matsumoto, T., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Nakazumi, H. & Katori, H. A. (2005). J. Mater. Chem. 15, 3479-3487.  [ISI] [CSD] [CrossRef] [ChemPort]
Iwamatsu, M., Kominami, T., Ueda, K., Sugimoto, T., Adachi, T., Fujita, H., Yoshino, H., Mizuno, Y., Murata, K. & Shiro, M. (2000). Inorg. Chem. 39, 3810-3815.  [CrossRef] [PubMed] [ChemPort]
Iwamatsu, M., Kominami, T., Ueda, K., Sugimoto, T., Fujita, H. & Adachi, T. (1999). Chem. Lett. pp. 329-330.
Sheldrick, G. M. (1996). SADABS. University of Götingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Ueda, K., Suzuki, K., Suzuki, K., Yoza, K. & Ishida, T. (2010). Phys. B (Amsterdam), 405, S69-S74.  [CrossRef] [ChemPort]
Ueda, K. & Yoza, K. (2009a). Acta Cryst. E65, o2716.  [CrossRef] [details]
Ueda, K. & Yoza, K. (2009b). Acta Cryst. E65, o2831.  [CSD] [CrossRef] [details]
Ueda, K. & Yoza, K. (2009c). Acta Cryst. E65, o2920.  [CSD] [CrossRef] [details]
Wang, M., Fujiwara, H., Sugimoto, T., Noguchi, S. & Ishida, T. (2005). Inorg. Chem. 44, 1184-1186.  [ISI] [CrossRef] [PubMed] [ChemPort]
Wang, M., Xiao, X., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Mori, T. & Katori, H. A. (2007). Inorg. Chem. 46, 3049-3056.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o52  [ doi:10.1107/S1600536811051518 ]

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