Acta Cryst. (2008). E64, m115 [ doi:10.1107/S1600536807063829 ]
The asymmetric unit of the title compound, [Sn3(CH3)6S3], contains two molecules with twist-boat conformations. There are intermolecular S
H (2.929 Å), SS (3.433 Å), SC (3.465 Å) and CH (2.898 Å) interactions in addition to prominent intermolecular SnS interactions of 3.692 and 3.769 Å.
To a stirring 20 ml me thanolic solution of K2emda(1 mmol) was added, 15 ml me thanolic solution of dimethyltin(IV) chloride (1 mmol). The mixture was additionally stirred for 2 h. Whole solvent was vacuum evaporated toobtain solid residue. To this 20 ml chloroform was added and suction filteredto discard KCl. The orange coloured solution thus obtained was layered with methanol to afford yellow crystals.
Data collection: Collect (Nonius, 1997-2000); cell refinement: HKL and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
![[Figure 1]](./sg2203fig1thm.gif)
| Fig. 1. ORTEP plot of tris(dimethyltin sulfide) at the 30% probability level. |
![[Figure 2]](./sg2203fig2thm.gif)
| Fig. 2. Unit cell packing of tris(dimethyltin sulfide) showing Sn···S, S···S, S···H, S···C and C···H interactions. |
| [Sn3(CH3)6S3] | Dx = 2.257 Mg m−3 |
| Mr = 542.45 | Melting point: 148 K |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| a = 14.826 (1) Å | Cell parameters from 24000 reflections |
| b = 12.814 (1) Å | θ = 2.9–27.5º |
| c = 17.744 (1) Å | µ = 5.01 mm−1 |
| β = 108.706 (1)º | T = 150 (2) K |
| V = 3192.94 (4) Å3 | Block, yellow |
| Z = 8 | 0.25 × 0.25 × 0.20 mm |
| F000 = 2016 |
| Nonius KappaCCD diffractometer | 9326 independent reflections |
| Radiation source: fine-focus sealed tube | 8221 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.046 |
| T = 150(2) K | θmax = 30.1º |
| 363 1.6 degree images with φ andω scans | θmin = 3.2º |
| Absorption correction: multi-scan (SORTAV; Blessing 1995) | h = −19→20 |
| Tmin = 0.311, Tmax = 0.361 | k = −17→18 |
| 78537 measured reflections | l = −24→24 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
| wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0287P)2 + 3.7599P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.15 | (Δ/σ)max = 0.002 |
| 9326 reflections | Δρmax = 0.93 e Å−3 |
| 229 parameters | Δρmin = −1.69 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Sn3(CH3)6S3] | V = 3192.94 (4) Å3 |
| Mr = 542.45 | Z = 8 |
| Monoclinic, P21/n | Mo Kα |
| a = 14.826 (1) Å | µ = 5.01 mm−1 |
| b = 12.814 (1) Å | T = 150 (2) K |
| c = 17.744 (1) Å | 0.25 × 0.25 × 0.20 mm |
| β = 108.706 (1)º |
| Nonius KappaCCD diffractometer | 9326 independent reflections |
| Absorption correction: multi-scan (SORTAV; Blessing 1995) | 8221 reflections with I > 2σ(I) |
| Tmin = 0.311, Tmax = 0.361 | Rint = 0.046 |
| 78537 measured reflections |
| R[F2 > 2σ(F2)] = 0.030 | 229 parameters |
| wR(F2) = 0.067 | H-atom parameters constrained |
| S = 1.15 | Δρmax = 0.93 e Å−3 |
| 9326 reflections | Δρmin = −1.69 e Å−3 |
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 | ||
| Sn1 | 0.407801 (14) | −0.393311 (15) | 0.330468 (12) | 0.02220 (5) | |
| Sn2 | 0.292630 (16) | −0.244657 (15) | 0.143631 (12) | 0.02433 (5) | |
| Sn3 | 0.260380 (14) | −0.539580 (15) | 0.143724 (12) | 0.02231 (5) | |
| Sn4 | 0.595000 (14) | 0.105237 (15) | 0.215469 (13) | 0.02279 (5) | |
| Sn5 | 0.775307 (14) | 0.255910 (15) | 0.373674 (12) | 0.02168 (5) | |
| Sn6 | 0.784610 (16) | −0.045519 (16) | 0.370081 (13) | 0.02807 (5) | |
| S1 | 0.38690 (6) | −0.21710 (6) | 0.28053 (5) | 0.02717 (15) | |
| S2 | 0.34811 (6) | −0.40429 (6) | 0.10117 (5) | 0.02742 (16) | |
| S3 | 0.26038 (5) | −0.48569 (6) | 0.27553 (4) | 0.02501 (14) | |
| S4 | 0.73866 (6) | 0.00869 (6) | 0.23204 (5) | 0.02779 (15) | |
| S5 | 0.74693 (8) | 0.10168 (6) | 0.44061 (5) | 0.03455 (19) | |
| S6 | 0.63617 (6) | 0.28120 (6) | 0.25940 (5) | 0.02786 (15) | |
| C1 | 0.5255 (3) | −0.4688 (3) | 0.3101 (3) | 0.0405 (8) | |
| H1A | 0.5840 | −0.4305 | 0.3374 | 0.061* | |
| H1B | 0.5160 | −0.4705 | 0.2528 | 0.061* | |
| H1C | 0.5306 | −0.5403 | 0.3306 | 0.061* | |
| C2 | 0.4245 (3) | −0.3748 (3) | 0.4546 (2) | 0.0427 (9) | |
| H2A | 0.4120 | −0.4415 | 0.4764 | 0.064* | |
| H2B | 0.3794 | −0.3222 | 0.4609 | 0.064* | |
| H2C | 0.4896 | −0.3522 | 0.4832 | 0.064* | |
| C3 | 0.1441 (2) | −0.2544 (3) | 0.1283 (2) | 0.0361 (8) | |
| H3A | 0.1203 | −0.1853 | 0.1360 | 0.054* | |
| H3B | 0.1340 | −0.3032 | 0.1673 | 0.054* | |
| H3C | 0.1100 | −0.2793 | 0.0744 | 0.054* | |
| C4 | 0.3309 (3) | −0.1254 (3) | 0.0757 (2) | 0.0411 (9) | |
| H4A | 0.2846 | −0.1239 | 0.0220 | 0.062* | |
| H4B | 0.3945 | −0.1398 | 0.0724 | 0.062* | |
| H4C | 0.3313 | −0.0577 | 0.1014 | 0.062* | |
| C5 | 0.1159 (2) | −0.5364 (3) | 0.06916 (19) | 0.0285 (6) | |
| H5A | 0.0969 | −0.6062 | 0.0472 | 0.043* | |
| H5B | 0.1090 | −0.4869 | 0.0256 | 0.043* | |
| H5C | 0.0753 | −0.5146 | 0.1003 | 0.043* | |
| C6 | 0.3447 (2) | −0.6776 (2) | 0.1555 (2) | 0.0298 (6) | |
| H6A | 0.3090 | −0.7375 | 0.1655 | 0.045* | |
| H6B | 0.4038 | −0.6693 | 0.2000 | 0.045* | |
| H6C | 0.3598 | −0.6892 | 0.1063 | 0.045* | |
| C7 | 0.5300 (3) | 0.1155 (3) | 0.0895 (2) | 0.0423 (9) | |
| H7A | 0.5087 | 0.0461 | 0.0680 | 0.063* | |
| H7B | 0.5763 | 0.1425 | 0.0655 | 0.063* | |
| H7C | 0.4751 | 0.1627 | 0.0774 | 0.063* | |
| C8 | 0.5078 (3) | 0.0398 (3) | 0.2777 (3) | 0.0429 (9) | |
| H8A | 0.4453 | 0.0737 | 0.2603 | 0.064* | |
| H8B | 0.5379 | 0.0506 | 0.3350 | 0.064* | |
| H8C | 0.5001 | −0.0352 | 0.2665 | 0.064* | |
| C9 | 0.7751 (3) | 0.3803 (2) | 0.4535 (2) | 0.0313 (7) | |
| H9A | 0.7892 | 0.3526 | 0.5075 | 0.047* | |
| H9B | 0.7123 | 0.4138 | 0.4371 | 0.047* | |
| H9C | 0.8236 | 0.4318 | 0.4525 | 0.047* | |
| C10 | 0.9028 (3) | 0.2408 (3) | 0.3437 (2) | 0.0364 (8) | |
| H10A | 0.9176 | 0.3075 | 0.3233 | 0.055* | |
| H10B | 0.8942 | 0.1869 | 0.3027 | 0.055* | |
| H10C | 0.9554 | 0.2209 | 0.3912 | 0.055* | |
| C11 | 0.6965 (3) | −0.1716 (3) | 0.3834 (2) | 0.0416 (9) | |
| H11A | 0.7122 | −0.2347 | 0.3589 | 0.062* | |
| H11B | 0.6295 | −0.1537 | 0.3573 | 0.062* | |
| H11C | 0.7075 | −0.1843 | 0.4401 | 0.062* | |
| C12 | 0.9340 (3) | −0.0702 (3) | 0.4128 (2) | 0.0425 (9) | |
| H12A | 0.9538 | −0.0860 | 0.4698 | 0.064* | |
| H12B | 0.9667 | −0.0072 | 0.4040 | 0.064* | |
| H12C | 0.9503 | −0.1289 | 0.3842 | 0.064* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.02077 (10) | 0.02012 (10) | 0.02404 (10) | 0.00078 (7) | 0.00487 (8) | 0.00072 (7) |
| Sn2 | 0.02967 (11) | 0.01939 (10) | 0.02465 (10) | 0.00053 (7) | 0.00974 (8) | 0.00356 (7) |
| Sn3 | 0.02227 (10) | 0.01899 (9) | 0.02482 (10) | 0.00015 (7) | 0.00638 (8) | −0.00101 (7) |
| Sn4 | 0.02074 (10) | 0.02090 (10) | 0.02697 (11) | −0.00286 (7) | 0.00798 (8) | −0.00433 (7) |
| Sn5 | 0.02387 (10) | 0.01951 (10) | 0.02113 (10) | 0.00017 (7) | 0.00645 (8) | −0.00146 (7) |
| Sn6 | 0.03327 (12) | 0.01932 (10) | 0.02936 (11) | −0.00007 (8) | 0.00690 (9) | 0.00062 (8) |
| S1 | 0.0324 (4) | 0.0176 (3) | 0.0293 (4) | −0.0025 (3) | 0.0070 (3) | −0.0022 (3) |
| S2 | 0.0326 (4) | 0.0234 (4) | 0.0311 (4) | −0.0020 (3) | 0.0171 (3) | −0.0019 (3) |
| S3 | 0.0253 (3) | 0.0250 (4) | 0.0266 (3) | −0.0048 (3) | 0.0110 (3) | −0.0019 (3) |
| S4 | 0.0304 (4) | 0.0268 (4) | 0.0287 (4) | 0.0056 (3) | 0.0129 (3) | −0.0016 (3) |
| S5 | 0.0580 (6) | 0.0244 (4) | 0.0275 (4) | 0.0035 (3) | 0.0225 (4) | 0.0037 (3) |
| S6 | 0.0296 (4) | 0.0178 (3) | 0.0299 (4) | 0.0010 (3) | 0.0008 (3) | 0.0002 (3) |
| C1 | 0.0286 (17) | 0.040 (2) | 0.054 (2) | 0.0095 (15) | 0.0137 (16) | 0.0019 (17) |
| C2 | 0.053 (2) | 0.048 (2) | 0.0230 (16) | −0.0027 (18) | 0.0071 (16) | −0.0010 (15) |
| C3 | 0.0268 (17) | 0.0341 (18) | 0.043 (2) | 0.0044 (13) | 0.0058 (15) | −0.0018 (14) |
| C4 | 0.064 (3) | 0.0281 (17) | 0.040 (2) | 0.0004 (17) | 0.0280 (19) | 0.0102 (14) |
| C5 | 0.0243 (14) | 0.0335 (16) | 0.0260 (15) | 0.0020 (12) | 0.0056 (12) | 0.0023 (12) |
| C6 | 0.0322 (16) | 0.0234 (14) | 0.0351 (16) | 0.0051 (12) | 0.0126 (13) | 0.0015 (12) |
| C7 | 0.038 (2) | 0.050 (2) | 0.0300 (18) | 0.0039 (16) | −0.0020 (15) | −0.0081 (15) |
| C8 | 0.0358 (19) | 0.042 (2) | 0.059 (2) | −0.0133 (16) | 0.0270 (18) | −0.0004 (17) |
| C9 | 0.0403 (18) | 0.0248 (15) | 0.0263 (15) | 0.0008 (13) | 0.0071 (14) | −0.0085 (12) |
| C10 | 0.0282 (17) | 0.0370 (18) | 0.049 (2) | 0.0013 (13) | 0.0187 (15) | 0.0021 (15) |
| C11 | 0.051 (2) | 0.0274 (17) | 0.041 (2) | −0.0122 (16) | 0.0082 (17) | 0.0065 (14) |
| C12 | 0.0344 (19) | 0.046 (2) | 0.039 (2) | 0.0020 (16) | −0.0001 (15) | −0.0160 (17) |
| Sn1—C1 | 2.125 (3) | C3—H3A | 0.9800 |
| Sn1—C2 | 2.149 (4) | C3—H3B | 0.9800 |
| Sn1—S3 | 2.4005 (8) | C3—H3C | 0.9800 |
| Sn1—S1 | 2.4090 (8) | C4—H4A | 0.9800 |
| Sn2—C4 | 2.133 (3) | C4—H4B | 0.9800 |
| Sn2—C3 | 2.133 (4) | C4—H4C | 0.9800 |
| Sn2—S1 | 2.4086 (8) | C5—H5A | 0.9800 |
| Sn2—S2 | 2.4136 (8) | C5—H5B | 0.9800 |
| Sn3—C5 | 2.126 (3) | C5—H5C | 0.9800 |
| Sn3—C6 | 2.136 (3) | C6—H6A | 0.9800 |
| Sn3—S2 | 2.4284 (8) | C6—H6B | 0.9800 |
| Sn3—S3 | 2.4386 (8) | C6—H6C | 0.9800 |
| Sn4—C8 | 2.123 (3) | C7—H7A | 0.9800 |
| Sn4—C7 | 2.135 (4) | C7—H7B | 0.9800 |
| Sn4—S4 | 2.3982 (8) | C7—H7C | 0.9800 |
| Sn4—S6 | 2.3999 (8) | C8—H8A | 0.9800 |
| Sn5—C10 | 2.131 (3) | C8—H8B | 0.9800 |
| Sn5—C9 | 2.133 (3) | C8—H8C | 0.9800 |
| Sn5—S6 | 2.4060 (8) | C9—H9A | 0.9800 |
| Sn5—S5 | 2.4112 (8) | C9—H9B | 0.9800 |
| Sn6—C12 | 2.121 (4) | C9—H9C | 0.9800 |
| Sn6—C11 | 2.138 (3) | C10—H10A | 0.9800 |
| Sn6—S4 | 2.4240 (8) | C10—H10B | 0.9800 |
| Sn6—S5 | 2.4259 (8) | C10—H10C | 0.9800 |
| C1—H1A | 0.9800 | C11—H11A | 0.9800 |
| C1—H1B | 0.9800 | C11—H11B | 0.9800 |
| C1—H1C | 0.9800 | C11—H11C | 0.9800 |
| C2—H2A | 0.9800 | C12—H12A | 0.9800 |
| C2—H2B | 0.9800 | C12—H12B | 0.9800 |
| C2—H2C | 0.9800 | C12—H12C | 0.9800 |
| C1—Sn1—C2 | 113.19 (17) | Sn2—C3—H3C | 109.5 |
| C1—Sn1—S3 | 113.37 (11) | H3A—C3—H3C | 109.5 |
| C2—Sn1—S3 | 105.13 (12) | H3B—C3—H3C | 109.5 |
| C1—Sn1—S1 | 112.33 (11) | Sn2—C4—H4A | 109.5 |
| C2—Sn1—S1 | 103.44 (12) | Sn2—C4—H4B | 109.5 |
| S3—Sn1—S1 | 108.66 (3) | H4A—C4—H4B | 109.5 |
| C4—Sn2—C3 | 114.88 (16) | Sn2—C4—H4C | 109.5 |
| C4—Sn2—S1 | 106.94 (12) | H4A—C4—H4C | 109.5 |
| C3—Sn2—S1 | 112.25 (11) | H4B—C4—H4C | 109.5 |
| C4—Sn2—S2 | 104.57 (11) | Sn3—C5—H5A | 109.5 |
| C3—Sn2—S2 | 110.58 (10) | Sn3—C5—H5B | 109.5 |
| S1—Sn2—S2 | 107.06 (3) | H5A—C5—H5B | 109.5 |
| C5—Sn3—C6 | 121.18 (13) | Sn3—C5—H5C | 109.5 |
| C5—Sn3—S2 | 109.01 (9) | H5A—C5—H5C | 109.5 |
| C6—Sn3—S2 | 105.44 (9) | H5B—C5—H5C | 109.5 |
| C5—Sn3—S3 | 106.35 (9) | Sn3—C6—H6A | 109.5 |
| C6—Sn3—S3 | 108.70 (9) | Sn3—C6—H6B | 109.5 |
| S2—Sn3—S3 | 105.12 (3) | H6A—C6—H6B | 109.5 |
| C8—Sn4—C7 | 115.01 (17) | Sn3—C6—H6C | 109.5 |
| C8—Sn4—S4 | 113.41 (12) | H6A—C6—H6C | 109.5 |
| C7—Sn4—S4 | 104.21 (11) | H6B—C6—H6C | 109.5 |
| C8—Sn4—S6 | 109.64 (11) | Sn4—C7—H7A | 109.5 |
| C7—Sn4—S6 | 105.33 (11) | Sn4—C7—H7B | 109.5 |
| S4—Sn4—S6 | 108.75 (3) | H7A—C7—H7B | 109.5 |
| C10—Sn5—C9 | 115.11 (15) | Sn4—C7—H7C | 109.5 |
| C10—Sn5—S6 | 113.04 (11) | H7A—C7—H7C | 109.5 |
| C9—Sn5—S6 | 105.97 (10) | H7B—C7—H7C | 109.5 |
| C10—Sn5—S5 | 110.93 (10) | Sn4—C8—H8A | 109.5 |
| C9—Sn5—S5 | 104.36 (10) | Sn4—C8—H8B | 109.5 |
| S6—Sn5—S5 | 106.72 (3) | H8A—C8—H8B | 109.5 |
| C12—Sn6—C11 | 116.90 (17) | Sn4—C8—H8C | 109.5 |
| C12—Sn6—S4 | 109.05 (12) | H8A—C8—H8C | 109.5 |
| C11—Sn6—S4 | 110.17 (11) | H8B—C8—H8C | 109.5 |
| C12—Sn6—S5 | 108.57 (10) | Sn5—C9—H9A | 109.5 |
| C11—Sn6—S5 | 106.29 (12) | Sn5—C9—H9B | 109.5 |
| S4—Sn6—S5 | 105.18 (3) | H9A—C9—H9B | 109.5 |
| Sn2—S1—Sn1 | 101.43 (3) | Sn5—C9—H9C | 109.5 |
| Sn2—S2—Sn3 | 103.76 (3) | H9A—C9—H9C | 109.5 |
| Sn1—S3—Sn3 | 104.42 (3) | H9B—C9—H9C | 109.5 |
| Sn4—S4—Sn6 | 102.86 (3) | Sn5—C10—H10A | 109.5 |
| Sn5—S5—Sn6 | 106.13 (3) | Sn5—C10—H10B | 109.5 |
| Sn4—S6—Sn5 | 101.96 (3) | H10A—C10—H10B | 109.5 |
| Sn1—C1—H1A | 109.5 | Sn5—C10—H10C | 109.5 |
| Sn1—C1—H1B | 109.5 | H10A—C10—H10C | 109.5 |
| H1A—C1—H1B | 109.5 | H10B—C10—H10C | 109.5 |
| Sn1—C1—H1C | 109.5 | Sn6—C11—H11A | 109.5 |
| H1A—C1—H1C | 109.5 | Sn6—C11—H11B | 109.5 |
| H1B—C1—H1C | 109.5 | H11A—C11—H11B | 109.5 |
| Sn1—C2—H2A | 109.5 | Sn6—C11—H11C | 109.5 |
| Sn1—C2—H2B | 109.5 | H11A—C11—H11C | 109.5 |
| H2A—C2—H2B | 109.5 | H11B—C11—H11C | 109.5 |
| Sn1—C2—H2C | 109.5 | Sn6—C12—H12A | 109.5 |
| H2A—C2—H2C | 109.5 | Sn6—C12—H12B | 109.5 |
| H2B—C2—H2C | 109.5 | H12A—C12—H12B | 109.5 |
| Sn2—C3—H3A | 109.5 | Sn6—C12—H12C | 109.5 |
| Sn2—C3—H3B | 109.5 | H12A—C12—H12C | 109.5 |
| H3A—C3—H3B | 109.5 | H12B—C12—H12C | 109.5 |
Authors are grateful to the CSIR, New Delhi, for financial assistance in the form of a JRF (AK) and a CSIR Project (NS).
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Tris(dimethyltin sulfide),1,1,3,3,5,5-hexamethyl-cyclo-1,3,5-tristannathiane was the unexpected product in our attempt to synthesizing dimethyltin(emda) (emda = 1-ethoxycarbonyl-1-methylcarbonyl-2,2-dithiolate) (see Experimental). The literature reports that the compound crystallizes in monoclinic (P21/c; Jacobsen & Krebs, 1977), tetragonal (P4; Menzebach & Bleckmann,1975) and tetragonal (P42212; Farina et al., 2001) modifications. The monoclinic modification was refined in the P21/c space group. However, the checking program PLATON (Spek, 2003) finds P21/n space group which is now being authenticated in the present study. In the monoclinic unit cell the molecules are linked by Sn···S interaction of 3.692 and 3.796 Å, S···H interaction of 2.929 Å, S···S interaction of 3.433 Å, S···C interaction of 3.465 Å and C···H interaction of 2.898 Å.