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Volume 69 
Part 11 
Page o1636  
November 2013  

Received 7 October 2013
Accepted 8 October 2013
Online 12 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 14.8
Details
Open access

Butane-1,4-diyl bis­(benzene­carbodi­thio­ate)

aDepartment of Applied Chemistry and Biotechnology, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Correspondence e-mail: sasanuma@faculty.chiba-u.jp

The title compound, C18H18S4, which lies on an inversion center, adopts a trans-gauche+-trans-gauche--trans (tg+tg-t) conformation of the S-CH2-CH2-CH2-CH2-S bond sequence. In the crystal, a [pi]-[pi] inter­action with a centroid-centroid distance of 3.8797 (16) Å is observed.

Related literature

For crystal structures and conformations of C6H5C(=S)S(CH2)2SC(=S)C6H5 and C6H5C(=O)S(CH2)4SC(=O)C6H5, see: Abe et al. (2011[Abe, D., Sasanuma, Y. & Sato, H. (2011). Acta Cryst. E67, o961.], 2013[Abe, D. & Sasanuma, Y. (2013). Acta Cryst. E69, o1612.]). For related compounds, see: Sawanobori et al. (2001[Sawanobori, M., Sasanuma, Y. & Kaito, A. (2001). Macromolecules, 34, 8321-8329.]); Sasanuma et al. (2002[Sasanuma, Y., Ohta, H., Touma, I., Matoba, H., Hayashi, Y. & Kaito, A. (2001). Macromolecules, 35, 3748-3761.]). For the synthesis of piperidinium di­thio­benzoate, see: Kato et al. (1973[Kato, S., Mitani, T. & Mizuta, M. (1973). Int. J. Sulfur Chem. 8, 359-366.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18S4

  • Mr = 362.56

  • Monoclinic, P 21 /n

  • a = 11.0205 (6) Å

  • b = 7.2535 (5) Å

  • c = 11.3090 (7) Å

  • [beta] = 110.805 (2)°

  • V = 845.06 (9) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 5.09 mm-1

  • T = 173 K

  • 0.40 × 0.20 × 0.01 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.235, Tmax = 0.951

  • 4872 measured reflections

  • 1480 independent reflections

  • 1468 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.100

  • S = 1.13

  • 1480 reflections

  • 100 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2. 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.]) 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5312 ).


Acknowledgements

We thank Dr Masu and Dr Yagishita of the Center for Analytical Instrumentation, Chiba University, for helpful advice about the X-ray diffraction measurements. This study was partly supported by a Grant-in-Aid for Scientific Research (C) (22550190) from the Japan Society for the Promotion of Science.

References

Abe, D., Sasanuma, Y. & Sato, H. (2011). Acta Cryst. E67, o961.  [CSD] [CrossRef] [IUCr Journals]
Abe, D. & Sasanuma, Y. (2013). Acta Cryst. E69, o1612.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Kato, S., Mitani, T. & Mizuta, M. (1973). Int. J. Sulfur Chem. 8, 359-366.  [ChemPort]
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]
Sasanuma, Y., Ohta, H., Touma, I., Matoba, H., Hayashi, Y. & Kaito, A. (2001). Macromolecules, 35, 3748-3761.  [Web of Science] [CrossRef]
Sawanobori, M., Sasanuma, Y. & Kaito, A. (2001). Macromolecules, 34, 8321-8329.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1636  [ doi:10.1107/S1600536813027529 ]

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