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

Ueda, K.; Suzuki, K.; Kunimoto, K.; Yoza, K.

doi:10.1107/S1600536811051518

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 (C-C) = 0.009 Å
Disorder in main residue
R = 0.061
wR = 0.107
Data-to-parameter ratio = 14.5
Details

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

Kazumasa Ueda,^a,^b ^* Kenta Suzuki,^b Kei Kunimoto ^b and Kenji Yoza ^c

^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 SS [3.33 (2), 3.434 (3), 3.444 (2), 3.503 (2), 3.519 (3) and 3.53 (4) Å] and SH [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, 2000); Wang et al. (2005, 2007); Hiraoka et al. (2005); Fujiwara et al. (2006, 2007); Ueda & Yoza (2009a,b,c). For the synthesis, see: Ueda et al. (2010). For van der Waals radii, see: Bondi (1964).

Experimental

Crystal data

C₉H₄S₇
M_r = 336.54
Monoclinic, P 2₁
a = 17.669 (5) Å
b = 3.9110 (11) Å
c = 18.380 (5) Å
= 108.177 (4)°
V = 1206.8 (6) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.894, T_max = 0.975
6965 measured reflections
4975 independent reflections
3396 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.107
S = 0.98
4975 reflections
344 parameters
421 restraints
H-atom parameters constrained
_max = 0.63 e Å^-3
_min = -0.52 e Å^-3
Absolute structure: Flack (1983), 1849 Friedel pairs
Flack parameter: -0.18 (18)

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XCIF (Bruker, 2010).

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.
Bruker (2010). APEX2, SAINT, XCIF. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T. & Nakazumi, H. (2006). J. Low Temp. Phys. 142, 405-408.
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.
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.
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.
Ueda, K., Suzuki, K., Suzuki, K., Yoza, K. & Ishida, T. (2010). Phys. B (Amsterdam), 405, S69-S74.
Ueda, K. & Yoza, K. (2009a). Acta Cryst. E65, o2716.
Ueda, K. & Yoza, K. (2009b). Acta Cryst. E65, o2831.
Ueda, K. & Yoza, K. (2009c). Acta Cryst. E65, o2920.
Wang, M., Fujiwara, H., Sugimoto, T., Noguchi, S. & Ishida, T. (2005). Inorg. Chem. 44, 1184-1186.
Wang, M., Xiao, X., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Mori, T. & Katori, H. A. (2007). Inorg. Chem. 46, 3049-3056.

organic compounds