 | Acta Crystallographica Section E Acta Crystallographica Section E CRYSTALLOGRAPHIC COMMUNICATIONS |
journal menu
organic compounds
| CRYSTALLOGRAPHIC COMMUNICATIONS |
access2,3-Bis(methylsulfanyl)-1,4,5,8-tetrathiafulvalene
aKey Laboratory of Organism Functional Factors of the Changbai Mountain, Yanbian University, Ministry of Education, Yanji 133002, People's Republic of China
*Correspondence e-mail: zqcong@ybu.edu.cn
In the title compound, C8H8S6, the five-membered rings form a dihedral angle of 25.06 (9)°. In the absence of short intermolecular contacts, the molecules are packed by in the crystal.
Related literature
For applications of tetrathiafulvalenes, see: Wudl et al. (1972![[Wudl, F., Wobshall, D. & Hufnagel, E. J. (1972). J. Am. Chem. Soc. 94, 670-672.]](../../../../../../logos/arrows/e_arr.gif "Wudl, F., Wobshall, D. & Hufnagel, E. J. (1972). J. Am. Chem. Soc. 94, 670-672.")
); Jørgensen et al. (1994). For details of the synthesis, see: Fourmingué et al. (1993). For a related structure, see: Hou et al. (2010).
![[Scheme 1]](ng5069scheme1.gif)
Experimental
Crystal data
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell 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.
Supporting information
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810048580/ng5069sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048580/ng5069Isup2.hkl
The title compound was prepared according to literature (Fourmingué et al., 1993) and single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of dichloromethane and petroleum (60–90 °C) at room temperature.
Carbon-bound H-atoms were placed in calculated positions with C—H = 0.93 or 0.96 Å and were included in the in the riding model with Uiso(H) = 1.2 or 1.5 Ueq(C).
Tetrathiafulvalenes (TTFs) have attracted much interest due to their electron-donating ability, which have been used for the synthesis of new organic metals and superconductors (Wudl et al. 1972) and recently for supramolecular architectures (Jørgensen et al. 1994.). In this paper, we report the crystal structue of the title compound.
The title compound, as shown in Fig. 1, crystallizes in monoclinic system with the C2/c. All bond lengths and angles of the title compound are normal and comparable with those reported for the related structure (Hou et al., 2010). In the crystal, the molecules are packed by van der Waal's forces.
For applications of tetrathiafulvalenes, see: Wudl et al. (1972); Jørgensen et al. (1994). For details of the synthesis, see: Fourmingué et al. (1993). For a related structure, see: Hou et al. (2010)
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).
![[Figure 1]](./ng5069fig1thm.gif) | Fig. 1. The asymmetric of title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level. |
| C8H8S6 | F(000) = 1216 |
| Mr = 296.50 | Dx = 1.624 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 9674 reflections |
| a = 19.368 (11) Å | θ = 3.3–27.6° |
| b = 7.703 (4) Å | µ = 1.09 mm−1 |
| c = 17.150 (8) Å | T = 291 K |
| β = 108.59 (2)° | Block, yellow |
| V = 2425 (2) Å3 | 0.12 × 0.10 × 0.09 mm |
| Z = 8 |
| Rigaku R-AXIS RAPID diffractometer | 2773 independent reflections |
| Radiation source: fine-focus sealed tube | 2480 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.025 |
| ω scans | θmax = 27.5°, θmin = 3.3° |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −25→25 |
| Tmin = 0.881, Tmax = 0.909 | k = −10→9 |
| 11301 measured reflections | l = −21→22 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.043P)2 + 2.0438P] where P = (Fo2 + 2Fc2)/3 |
| 2773 reflections | (Δ/σ)max = 0.006 |
| 129 parameters | Δρmax = 0.58 e Å−3 |
| 0 restraints | Δρmin = −0.66 e Å−3 |
| C8H8S6 | V = 2425 (2) Å3 |
| Mr = 296.50 | Z = 8 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 19.368 (11) Å | µ = 1.09 mm−1 |
| b = 7.703 (4) Å | T = 291 K |
| c = 17.150 (8) Å | 0.12 × 0.10 × 0.09 mm |
| β = 108.59 (2)° |
| Rigaku R-AXIS RAPID diffractometer | 2773 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2480 reflections with I > 2σ(I) |
| Tmin = 0.881, Tmax = 0.909 | Rint = 0.025 |
| 11301 measured reflections |
| R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.58 e Å−3 |
| 2773 reflections | Δρmin = −0.66 e Å−3 |
| 129 parameters |
Experimental. (See detailed section in the paper) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.02208 (11) | 0.7309 (3) | 1.15260 (11) | 0.0490 (5) | |
| H1 | −0.0004 | 0.7911 | 1.1849 | 0.059* | |
| C2 | 0.06543 (12) | 0.5980 (3) | 1.18273 (11) | 0.0494 (5) | |
| H2 | 0.0744 | 0.5615 | 1.2368 | 0.059* | |
| C3 | 0.07086 (9) | 0.6402 (2) | 1.03633 (10) | 0.0331 (3) | |
| C4 | 0.09038 (9) | 0.6398 (2) | 0.96816 (10) | 0.0348 (3) | |
| C5 | 0.12943 (10) | 0.7609 (2) | 0.84888 (10) | 0.0375 (4) | |
| C6 | 0.17548 (9) | 0.6286 (2) | 0.87949 (10) | 0.0381 (4) | |
| C7 | 0.18062 (13) | 1.0834 (3) | 0.83038 (14) | 0.0552 (5) | |
| H7A | 0.1538 | 1.1248 | 0.8651 | 0.083* | |
| H7B | 0.1850 | 1.1747 | 0.7941 | 0.083* | |
| H7C | 0.2283 | 1.0472 | 0.8638 | 0.083* | |
| C8 | 0.30945 (12) | 0.4634 (3) | 0.92717 (15) | 0.0608 (6) | |
| H8A | 0.3209 | 0.5384 | 0.9743 | 0.091* | |
| H8B | 0.3531 | 0.4385 | 0.9141 | 0.091* | |
| H8C | 0.2890 | 0.3571 | 0.9391 | 0.091* | |
| S1 | 0.00813 (3) | 0.79005 (6) | 1.05124 (3) | 0.04253 (13) | |
| S2 | 0.10518 (3) | 0.49359 (6) | 1.11799 (3) | 0.04402 (13) | |
| S3 | 0.05498 (2) | 0.78415 (6) | 0.88578 (3) | 0.04151 (13) | |
| S4 | 0.15503 (3) | 0.49566 (6) | 0.95261 (3) | 0.04458 (14) | |
| S5 | 0.13348 (3) | 0.90281 (7) | 0.77079 (3) | 0.05321 (15) | |
| S6 | 0.24524 (3) | 0.56800 (10) | 0.84168 (4) | 0.06234 (18) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0601 (12) | 0.0557 (12) | 0.0353 (9) | 0.0035 (9) | 0.0211 (8) | −0.0054 (8) |
| C2 | 0.0591 (11) | 0.0599 (13) | 0.0293 (9) | 0.0019 (10) | 0.0142 (8) | 0.0037 (8) |
| C3 | 0.0323 (7) | 0.0330 (8) | 0.0354 (8) | 0.0023 (6) | 0.0127 (6) | 0.0048 (6) |
| C4 | 0.0353 (8) | 0.0347 (9) | 0.0377 (8) | 0.0030 (6) | 0.0160 (7) | 0.0063 (6) |
| C5 | 0.0468 (9) | 0.0376 (9) | 0.0311 (8) | −0.0072 (7) | 0.0166 (7) | 0.0002 (6) |
| C6 | 0.0405 (8) | 0.0442 (10) | 0.0343 (8) | −0.0055 (7) | 0.0185 (7) | −0.0019 (7) |
| C7 | 0.0602 (12) | 0.0458 (12) | 0.0593 (13) | −0.0100 (10) | 0.0187 (10) | 0.0034 (9) |
| C8 | 0.0425 (11) | 0.0773 (16) | 0.0651 (14) | 0.0057 (10) | 0.0206 (10) | −0.0037 (12) |
| S1 | 0.0492 (3) | 0.0424 (3) | 0.0420 (2) | 0.01172 (19) | 0.0229 (2) | 0.00695 (18) |
| S2 | 0.0462 (3) | 0.0476 (3) | 0.0400 (2) | 0.01051 (19) | 0.0161 (2) | 0.01361 (18) |
| S3 | 0.0447 (2) | 0.0423 (3) | 0.0404 (2) | 0.00839 (19) | 0.01765 (19) | 0.01208 (18) |
| S4 | 0.0482 (3) | 0.0449 (3) | 0.0505 (3) | 0.0142 (2) | 0.0295 (2) | 0.01503 (19) |
| S5 | 0.0789 (4) | 0.0510 (3) | 0.0320 (2) | −0.0161 (3) | 0.0210 (2) | 0.00457 (19) |
| S6 | 0.0543 (3) | 0.0919 (5) | 0.0539 (3) | 0.0106 (3) | 0.0356 (3) | 0.0085 (3) |
| C1—C2 | 1.321 (3) | C5—S3 | 1.759 (2) |
| C1—S1 | 1.733 (2) | C6—S6 | 1.7386 (19) |
| C1—H1 | 0.9300 | C6—S4 | 1.7591 (18) |
| C2—S2 | 1.737 (2) | C7—S5 | 1.794 (2) |
| C2—H2 | 0.9300 | C7—H7A | 0.9600 |
| C3—C4 | 1.339 (2) | C7—H7B | 0.9600 |
| C3—S1 | 1.7525 (18) | C7—H7C | 0.9600 |
| C3—S2 | 1.7565 (17) | C8—S6 | 1.784 (2) |
| C4—S3 | 1.7565 (18) | C8—H8A | 0.9600 |
| C4—S4 | 1.7562 (18) | C8—H8B | 0.9600 |
| C5—C6 | 1.346 (3) | C8—H8C | 0.9600 |
| C5—S5 | 1.7498 (18) | ||
| C2—C1—S1 | 118.21 (15) | S5—C7—H7A | 109.5 |
| C2—C1—H1 | 120.9 | S5—C7—H7B | 109.5 |
| S1—C1—H1 | 120.9 | H7A—C7—H7B | 109.5 |
| C1—C2—S2 | 117.70 (15) | S5—C7—H7C | 109.5 |
| C1—C2—H2 | 121.1 | H7A—C7—H7C | 109.5 |
| S2—C2—H2 | 121.1 | H7B—C7—H7C | 109.5 |
| C4—C3—S1 | 122.09 (13) | S6—C8—H8A | 109.5 |
| C4—C3—S2 | 123.66 (14) | S6—C8—H8B | 109.5 |
| S1—C3—S2 | 114.26 (9) | H8A—C8—H8B | 109.5 |
| C3—C4—S3 | 123.67 (14) | S6—C8—H8C | 109.5 |
| C3—C4—S4 | 123.23 (13) | H8A—C8—H8C | 109.5 |
| S3—C4—S4 | 113.10 (10) | H8B—C8—H8C | 109.5 |
| C6—C5—S5 | 125.86 (14) | C1—S1—C3 | 94.57 (9) |
| C6—C5—S3 | 117.01 (13) | C2—S2—C3 | 94.58 (10) |
| S5—C5—S3 | 116.99 (11) | C4—S3—C5 | 94.04 (8) |
| C5—C6—S6 | 123.71 (14) | C4—S4—C6 | 94.24 (9) |
| C5—C6—S4 | 116.55 (14) | C5—S5—C7 | 100.79 (10) |
| S6—C6—S4 | 119.21 (11) | C6—S6—C8 | 103.63 (10) |
Experimental details
| Crystal data | |
| Chemical formula | C8H8S6 |
| Mr | 296.50 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 291 |
| a, b, c (Å) | 19.368 (11), 7.703 (4), 17.150 (8) |
| β (°) | 108.59 (2) |
| V (Å3) | 2425 (2) |
| Z | 8 |
| Radiation type | Mo Kα |
| µ (mm−1) | 1.09 |
| Crystal size (mm) | 0.12 × 0.10 × 0.09 |
| Data collection | |
| Diffractometer | Rigaku R-AXIS RAPID |
| Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
| Tmin, Tmax | 0.881, 0.909 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 11301, 2773, 2480 |
| Rint | 0.025 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.083, 1.03 |
| No. of reflections | 2773 |
| No. of parameters | 129 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.58, −0.66 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010), the Specialized Research Fund for the Doctoral Programme of Higher Education (grant No. 2006184001) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.
References
Fourmingué, M., Krebs, F. C. & Larsen, J. (1993). Synthesis, 5, 509–512. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hou, R.-B., Li, B., Yin, B.-Z. & Wu, L.-X. (2010). Acta Cryst. E66, o1044. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jørgensen, T., Hansen, T. K. & Becher, J. (1994). Chem. Soc. Rev. 23, 41–45. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wudl, F., Wobshall, D. & Hufnagel, E. J. (1972). J. Am. Chem. Soc. 94, 670–672. CrossRef CAS Web of Science Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
| CRYSTALLOGRAPHIC COMMUNICATIONS |
Tetrathiafulvalenes (TTFs) have attracted much interest due to their electron-donating ability, which have been used for the synthesis of new organic metals and superconductors (Wudl et al. 1972) and recently for supramolecular architectures (Jørgensen et al. 1994.). In this paper, we report the crystal structue of the title compound.
The title compound, as shown in Fig. 1, crystallizes in monoclinic system with the space group C2/c. All bond lengths and angles of the title compound are normal and comparable with those reported for the related structure (Hou et al., 2010). In the crystal, the molecules are packed by van der Waal's forces.