Ethane-1,2-diyl bis­(benzene­dithio­ate)

Abe, D.; Sasanuma, Y.; Sato, H.

doi:10.1107/S1600536811010245

Volume 67
Part 4
Page o961
April 2011

Received 8 March 2011
Accepted 18 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R = 0.030
wR = 0.079
Data-to-parameter ratio = 15.3
Details

Ethane-1,2-diyl bis(benzenedithioate)

Daisuke Abe,^a Yuji Sasanuma ^a ^* and Hiroyasu Sato ^b

^aDepartment of Applied Chemistry and Biotechnology, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan, and ^bApplication Laboratory, Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima-shi, Tokyo 196-8666, Japan
Correspondence e-mail: sasanuma@faculty.chiba-u.jp

In the crystal structure, the title compound, C₁₆H₁₄S₄, is located on an inversion center and exhibits a gauche⁺-trans-gauche^- conformation in the S-CH₂-CH₂-S bond sequence. The S-C=S plane makes a dihedral angle of 30.63 (17)° with the phenyl ring. An intermolecular C-H [pi] interaction is observed.

Related literature

For crystal structures and conformations of related compounds with S-CH₂-CH₂-S bond sequences, see: for example, Takahashi et al. (1968); Deguire & Brisse (1988); Sasanuma & Watanabe (2006).

Experimental

Crystal data

C₁₆H₁₄S₄
M_r = 334.53
Monoclinic, P 2₁ /c
a = 11.5431 (7) Å
b = 8.74071 (16) Å
c = 8.93720 (16) Å
= 122.3772 (7)°
V = 761.54 (5) Å³
Z = 2
Cu K radiation
= 5.60 mm^-1
T = 93 K
0.32 × 0.27 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.195, T_max = 0.639
8415 measured reflections
1389 independent reflections
1292 reflections with F² > 2(F²)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.079
S = 1.14
1389 reflections
91 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C8-H8ACg1ⁱ	0.99	2.65	3.451 (1)	138
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku Americas & Rigaku, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2686 ).

Acknowledgements

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

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Deguire, S. & Brisse, F. (1988). Can. J. Chem. 66, 341-347.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku Americas & Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sasanuma, Y. & Watanabe, A. (2006). Macromolecules, 39, 1646-1656.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Takahashi, Y., Tadokoro, H. & Chatani, Y. (1968). J. Macromol. Sci. Phys. B2, 361-367.

organic compounds