Acta Cryst. (2007). E63, m2958 [ doi:10.1107/S1600536807055651 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-2-thiophene-2-acetato-![[kappa]](/logos/entities/kappa_rmgif.gif)
2O:O']The title compound, [Sn(CH3)3(C6H5O2S)]n, has an infinite chain structure. The SnO2C3 centre has a slightly distorted trigonal bipyramidal geometry with the O atoms in the axial positions.
The reaction was carried out under a nitrogen atmosphere. 2-Thiopheneacetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to 30 ml of benzene in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at 313 K·The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1 v/v) to yield colourless blocks of (I). Yield 80%; m.p. 452 K. Analysis calculated (%) for C9H14O2SSn: C 35.44; H 4.63%. found: C 35.37; H 4.71%.
The H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
![[Figure 1]](./hb2631fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Atom O2A is generated by the symmetry operation (1 − x, 1/2 + y, 3/2 − z). |
![[Figure 2]](./hb2631fig2thm.gif)
| Fig. 2. Part of the chain structure of (I), H atoms have been omitted for clarity. |
| [Sn(CH3)3(C6H5O2S)] | F000 = 600 |
| Mr = 304.95 | Dx = 1.642 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2389 reflections |
| a = 9.5179 (13) Å | θ = 2.6–25.8º |
| b = 10.1177 (14) Å | µ = 2.21 mm−1 |
| c = 13.2038 (18) Å | T = 298 (2) K |
| β = 104.039 (2)º | Block, colourless |
| V = 1233.5 (3) Å3 | 0.54 × 0.39 × 0.37 mm |
| Z = 4 |
| Siemens SMART CCD diffractometer | 2168 independent reflections |
| Radiation source: fine-focus sealed tube | 1622 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.032 |
| T = 298(2) K | θmax = 25.0º |
| ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.381, Tmax = 0.495 | k = −11→12 |
| 4898 measured reflections | l = −15→13 |
| 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)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.073P)2 + 1.6901P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.001 |
| 2168 reflections | Δρmax = 1.10 e Å−3 |
| 118 parameters | Δρmin = −0.62 e Å−3 |
| 18 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Sn(CH3)3(C6H5O2S)] | V = 1233.5 (3) Å3 |
| Mr = 304.95 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 9.5179 (13) Å | µ = 2.21 mm−1 |
| b = 10.1177 (14) Å | T = 298 (2) K |
| c = 13.2038 (18) Å | 0.54 × 0.39 × 0.37 mm |
| β = 104.039 (2)º |
| Siemens SMART CCD diffractometer | 2168 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1622 reflections with I > 2σ(I) |
| Tmin = 0.381, Tmax = 0.495 | Rint = 0.032 |
| 4898 measured reflections |
| R[F2 > 2σ(F2)] = 0.037 | 18 restraints |
| wR(F2) = 0.127 | H-atom parameters constrained |
| S = 1.00 | Δρmax = 1.10 e Å−3 |
| 2168 reflections | Δρmin = −0.62 e Å−3 |
| 118 parameters |
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.56253 (5) | 1.10603 (4) | 0.72279 (3) | 0.0566 (2) | |
| O1 | 0.7129 (5) | 0.9441 (5) | 0.7131 (5) | 0.0843 (15) | |
| O2 | 0.5752 (5) | 0.7961 (5) | 0.7658 (4) | 0.0794 (14) | |
| S1 | 0.9638 (3) | 0.8817 (2) | 0.6287 (2) | 0.1037 (8) | |
| C1 | 0.6853 (9) | 0.8260 (7) | 0.7362 (6) | 0.0735 (19) | |
| C2 | 0.7962 (9) | 0.7225 (8) | 0.7295 (7) | 0.093 (3) | |
| H2A | 0.7478 | 0.6374 | 0.7194 | 0.112* | |
| H2B | 0.8667 | 0.7193 | 0.7962 | 0.112* | |
| C3 | 0.8771 (7) | 0.7394 (7) | 0.6452 (6) | 0.0703 (18) | |
| C4 | 0.8965 (11) | 0.6402 (9) | 0.5751 (9) | 0.103 (3) | |
| H4 | 0.8577 | 0.5554 | 0.5706 | 0.123* | |
| C5 | 0.9859 (13) | 0.6919 (12) | 0.5122 (10) | 0.125 (3) | |
| H5 | 1.0093 | 0.6439 | 0.4585 | 0.150* | |
| C6 | 1.0323 (11) | 0.8122 (11) | 0.5361 (9) | 0.115 (3) | |
| H6 | 1.0972 | 0.8550 | 0.5047 | 0.138* | |
| C7 | 0.7008 (9) | 1.2365 (8) | 0.6666 (7) | 0.086 (2) | |
| H7A | 0.6764 | 1.2347 | 0.5917 | 0.129* | |
| H7B | 0.7996 | 1.2092 | 0.6925 | 0.129* | |
| H7C | 0.6889 | 1.3246 | 0.6901 | 0.129* | |
| C8 | 0.5859 (11) | 1.0867 (8) | 0.8854 (6) | 0.090 (3) | |
| H8A | 0.6722 | 1.1315 | 0.9219 | 0.136* | |
| H8B | 0.5926 | 0.9947 | 0.9039 | 0.136* | |
| H8C | 0.5034 | 1.1250 | 0.9041 | 0.136* | |
| C9 | 0.3859 (8) | 1.0250 (9) | 0.6101 (6) | 0.087 (2) | |
| H9A | 0.3962 | 1.0458 | 0.5414 | 0.130* | |
| H9B | 0.2970 | 1.0617 | 0.6196 | 0.130* | |
| H9C | 0.3847 | 0.9308 | 0.6185 | 0.130* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0716 (3) | 0.0419 (3) | 0.0623 (3) | −0.0046 (2) | 0.0279 (2) | −0.00282 (19) |
| O1 | 0.090 (3) | 0.044 (3) | 0.133 (5) | 0.005 (3) | 0.055 (3) | 0.007 (3) |
| O2 | 0.090 (4) | 0.052 (3) | 0.109 (4) | −0.003 (3) | 0.049 (3) | 0.003 (3) |
| S1 | 0.0950 (16) | 0.0907 (17) | 0.129 (2) | −0.0182 (13) | 0.0331 (15) | 0.0003 (14) |
| C1 | 0.088 (5) | 0.045 (4) | 0.093 (5) | −0.001 (4) | 0.033 (4) | 0.004 (4) |
| C2 | 0.102 (6) | 0.062 (5) | 0.127 (7) | 0.018 (4) | 0.051 (5) | 0.011 (5) |
| C3 | 0.058 (4) | 0.054 (4) | 0.100 (5) | 0.012 (3) | 0.020 (4) | 0.006 (4) |
| C4 | 0.110 (6) | 0.073 (5) | 0.140 (6) | 0.008 (4) | 0.058 (5) | −0.001 (5) |
| C5 | 0.140 (6) | 0.104 (6) | 0.149 (6) | 0.034 (6) | 0.072 (5) | −0.001 (6) |
| C6 | 0.110 (5) | 0.105 (6) | 0.148 (6) | 0.018 (5) | 0.067 (5) | 0.015 (6) |
| C7 | 0.108 (6) | 0.050 (4) | 0.112 (6) | −0.019 (4) | 0.053 (5) | 0.012 (4) |
| C8 | 0.128 (7) | 0.080 (6) | 0.064 (4) | 0.001 (5) | 0.024 (5) | −0.002 (4) |
| C9 | 0.096 (5) | 0.089 (6) | 0.074 (5) | −0.011 (5) | 0.019 (4) | −0.018 (4) |
| Sn1—C8 | 2.113 (8) | C4—C5 | 1.425 (14) |
| Sn1—C9 | 2.120 (7) | C4—H4 | 0.9300 |
| Sn1—C7 | 2.121 (7) | C5—C6 | 1.307 (14) |
| Sn1—O1 | 2.200 (5) | C5—H5 | 0.9300 |
| Sn1—O2i | 2.353 (5) | C6—H6 | 0.9300 |
| O1—C1 | 1.276 (9) | C7—H7A | 0.9600 |
| O2—C1 | 1.242 (8) | C7—H7B | 0.9600 |
| O2—Sn1ii | 2.353 (5) | C7—H7C | 0.9600 |
| S1—C6 | 1.674 (10) | C8—H8A | 0.9600 |
| S1—C3 | 1.699 (8) | C8—H8B | 0.9600 |
| C1—C2 | 1.505 (10) | C8—H8C | 0.9600 |
| C2—C3 | 1.509 (10) | C9—H9A | 0.9600 |
| C2—H2A | 0.9700 | C9—H9B | 0.9600 |
| C2—H2B | 0.9700 | C9—H9C | 0.9600 |
| C3—C4 | 1.408 (12) | ||
| C8—Sn1—C9 | 123.2 (4) | C3—C4—H4 | 125.9 |
| C8—Sn1—C7 | 119.5 (4) | C5—C4—H4 | 125.9 |
| C9—Sn1—C7 | 116.7 (3) | C6—C5—C4 | 114.6 (10) |
| C8—Sn1—O1 | 94.6 (3) | C6—C5—H5 | 122.7 |
| C9—Sn1—O1 | 95.0 (3) | C4—C5—H5 | 122.7 |
| C7—Sn1—O1 | 88.6 (3) | C5—C6—S1 | 113.5 (8) |
| C8—Sn1—O2i | 86.2 (3) | C5—C6—H6 | 123.3 |
| C9—Sn1—O2i | 90.1 (3) | S1—C6—H6 | 123.3 |
| C7—Sn1—O2i | 85.2 (3) | Sn1—C7—H7A | 109.5 |
| O1—Sn1—O2i | 173.28 (17) | Sn1—C7—H7B | 109.5 |
| C1—O1—Sn1 | 120.6 (4) | H7A—C7—H7B | 109.5 |
| C1—O2—Sn1ii | 138.2 (5) | Sn1—C7—H7C | 109.5 |
| C6—S1—C3 | 91.4 (5) | H7A—C7—H7C | 109.5 |
| O2—C1—O1 | 122.8 (7) | H7B—C7—H7C | 109.5 |
| O2—C1—C2 | 120.4 (7) | Sn1—C8—H8A | 109.5 |
| O1—C1—C2 | 116.8 (7) | Sn1—C8—H8B | 109.5 |
| C1—C2—C3 | 117.0 (7) | H8A—C8—H8B | 109.5 |
| C1—C2—H2A | 108.0 | Sn1—C8—H8C | 109.5 |
| C3—C2—H2A | 108.0 | H8A—C8—H8C | 109.5 |
| C1—C2—H2B | 108.0 | H8B—C8—H8C | 109.5 |
| C3—C2—H2B | 108.0 | Sn1—C9—H9A | 109.5 |
| H2A—C2—H2B | 107.3 | Sn1—C9—H9B | 109.5 |
| C4—C3—C2 | 125.1 (7) | H9A—C9—H9B | 109.5 |
| C4—C3—S1 | 112.0 (6) | Sn1—C9—H9C | 109.5 |
| C2—C3—S1 | 122.8 (6) | H9A—C9—H9C | 109.5 |
| C3—C4—C5 | 108.3 (9) | H9B—C9—H9C | 109.5 |
| Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
| Sn1—C8 | 2.113 (8) | Sn1—O1 | 2.200 (5) |
| Sn1—C9 | 2.120 (7) | Sn1—O2i | 2.353 (5) |
| Sn1—C7 | 2.121 (7) |
| Symmetry codes: (i) −x+1, y+1/2, −z+3/2. |
We acknowledge the financial support of the Shandong Province Science Foundation, and the State Key Laboratory of Crystalline Materials, Shandong University, China.
Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem. 691, 1713–1721.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
Siemens (1996). SMART and SAINT. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA.
The title compound, (I) (Fig. 1), possesses an infinite one-dimensional chain structure arising from Sn—O bridges to the ligand. The Sn—O distances in (I) (Table 1) are similar to those in related organotin carboxylates (Ma et al., 2006). The Sn atom has distorted trigonal-bipyramidal geometry, with the O atoms in axial positions [O1—Sn1—O2i = 173.28 (17) °] and the C atoms of the three methyl groups in equatorial positions. The sum of the equatorial C—Sn—C angles is 359.4 °, indicating near coplanarity for these atoms.