2,3-(3,6,9-Trioxaundecane-1,11-diyl­disulfan­yl)-1,4,5,8-tetra­thia­fulvalene-6,7-dicarbonitrile

Hou, R.-B.; Li, B.; Chen, T.; Yin, B.-Z.; Wu, L.-X.

doi:10.1107/S1600536810017587

Volume 66
Part 6
Page o1379
June 2010

Received 12 May 2010
Accepted 13 May 2010
Online 19 May 2010

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.003 Å
R = 0.032
wR = 0.088
Data-to-parameter ratio = 19.2
Details

2,3-(3,6,9-Trioxaundecane-1,11-diyldisulfanyl)-1,4,5,8-tetrathiafulvalene-6,7-dicarbonitrile

Rui-Bin Hou,^a Bao Li,^b Tie Chen,^a Bing-Zhu Yin ^a ^* and Li-Xin Wu ^b

^aKey Laboratory of Organism Functional Factors of the Changbai Mountain, Yanbian University, Ministry of Education, Yanji 133002, People's Republic of China, and ^bState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: zqcong@ybu.edu.cn

In the title compound, C₁₆H₁₆N₂O₃S₆, the two five-membered rings form a dihedral angle of 7.86 (9)°. Weak C-HN hydrogen bonds link the molecules to form a chain along c; the chains are further connected by weak C-HO hydrogen bonds to form a three-dimensional supramolecular network.

Related literature

For background to the use of dithiacrown ether annulated tetrathiafulvalenes as sensor molecules for various metal cations, see Moore et al. (2000); Otsubo & Ogura (1985). For the synthesis, see Yin et al. (2006). For a related structure, see Hou et al. (2009).

Experimental

Crystal data

C₁₆H₁₆N₂O₃S₆
M_r = 476.67
Triclinic, $[P \overline 1]$
a = 8.300 (5) Å
b = 9.186 (5) Å
c = 13.892 (10) Å
= 100.42 (3)°
= 92.31 (3)°
= 95.60 (2)°
V = 1035.0 (11) Å³
Z = 2
Mo K radiation
= 0.68 mm^-1
T = 290 K
0.13 × 0.12 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.917, T_max = 0.935
10214 measured reflections
4702 independent reflections
3936 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.088
S = 1.07
4702 reflections
245 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13AN1ⁱ	0.97	2.65	3.534 (3)	152
C14-H14AN1ⁱⁱ	0.97	2.74	3.691 (3)	168
C14-H14BO1ⁱⁱⁱ	0.97	2.64	3.401 (3)	136
C9-H9AO2^iv	0.97	2.57	3.406 (3)	144
C15-H15BO3^v	0.97	2.47	3.317 (2)	146
Symmetry codes: (i) x, y, z+1; (ii) -x, -y+2, -z; (iii) x-1, y, z; (iv) -x+1, -y+2, -z+1; (v) -x, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2773 ).

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010), the Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 2006184001) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Hou, R., Li, B., Yin, B. & Wu, L. (2009). Acta Cryst. E65, o1057.
Moore, A. J., Goldenberg, L. M., Bryce, M. R. & Petty, M. (2000). J. Org. Chem. 65, 8269-8276.
Otsubo, T. & Ogura, F. (1985). Bull. Chem. Soc. Jpn, 58, 1343-1344.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yin, B. Z., Wang, C. L., Chen, T. & Cong, Z. Q. (2006). Chin. Chem. Reagent, 28, 132-134.

organic compounds