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Volume 69 
Part 11 
Page o1612  
November 2013  

Received 20 September 2013
Accepted 30 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.083
Data-to-parameter ratio = 18.5
Details
Open access

S,S'-Butane-1,4-diyl bis­(benzene­carbo­thio­ate)

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, C18H18O2S2, which lies on an inversion center, adopts a gauche+-trans-trans-trans-gauche- (g+tttg-) conformation in the S-CH2-CH2-CH2-CH2-S bond sequence. In the crystal, mol­ecules are packed in a herringbone arrangement through inter­molecular C-H...[pi] inter­actions.

Related literature

For crystal structures and conformations of C6H5C(=O)S(CH2)nSC(=O)C6H5 (n = 2, 3, 5, 7, 9), see: for example, Deguire & Brisse (1988[Deguire, S. & Brisse, F. (1988). Can. J. Chem. 66, 341-347.]); Leblanc & Brisse (1992[Leblanc, C. & Brisse, F. (1992). Can. J. Chem. 70, 900-909.]); Abe & Sasanuma (2012[Abe, D. & Sasanuma, Y. (2012). Polym. Chem. 3, 1576-1587.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18O2S2

  • Mr = 330.44

  • Monoclinic, P 21 /c

  • a = 13.2230 (14) Å

  • b = 4.8903 (5) Å

  • c = 13.2638 (15) Å

  • [beta] = 106.897 (1)°

  • V = 820.67 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 173 K

  • 0.30 × 0.30 × 0.05 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.908, Tmax = 0.984

  • 4326 measured reflections

  • 1845 independent reflections

  • 1626 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.05

  • 1845 reflections

  • 100 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C4-H4...Cg1i 0.95 3.09 3.8810 (15) 141
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: 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 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: IS5305 ).


Acknowledgements

We thank Dr Masu and Dr Yagishita of the Center for Analytical Instrumentation, Chiba University, for helpful advice on 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. (2012). Polym. Chem. 3, 1576-1587.  [CrossRef] [ChemPort]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deguire, S. & Brisse, F. (1988). Can. J. Chem. 66, 341-347.  [CrossRef] [ChemPort] [Web of Science]
Leblanc, C. & Brisse, F. (1992). Can. J. Chem. 70, 900-909.  [CrossRef] [ChemPort] [Web of Science]
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]
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]


Acta Cryst (2013). E69, o1612  [ doi:10.1107/S1600536813026822 ]

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