Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055651/hb2631sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055651/hb2631Isup2.hkl |
CCDC reference: 672623
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).
[Sn(CH3)3(C6H5O2S)] | F(000) = 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 = 2.6–25.8° |
b = 10.1177 (14) Å | µ = 2.21 mm−1 |
c = 13.2038 (18) Å | T = 298 K |
β = 104.039 (2)° | 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) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 25.0°, θmin = 2.2° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.073P)2 + 1.6901P] where P = (Fo2 + 2Fc2)/3 |
2168 reflections | (Δ/σ)max = 0.001 |
118 parameters | Δρmax = 1.10 e Å−3 |
18 restraints | Δρmin = −0.63 e Å−3 |
[Sn(CH3)3(C6H5O2S)] | V = 1233.5 (3) Å3 |
Mr = 304.95 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.5179 (13) Å | µ = 2.21 mm−1 |
b = 10.1177 (14) Å | T = 298 K |
c = 13.2038 (18) Å | 0.54 × 0.39 × 0.37 mm |
β = 104.039 (2)° |
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 = −0.63 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. |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)3(C6H5O2S)] |
Mr | 304.95 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 9.5179 (13), 10.1177 (14), 13.2038 (18) |
β (°) | 104.039 (2) |
V (Å3) | 1233.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.21 |
Crystal size (mm) | 0.54 × 0.39 × 0.37 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.381, 0.495 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4898, 2168, 1622 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.127, 1.00 |
No. of reflections | 2168 |
No. of parameters | 118 |
No. of restraints | 18 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.10, −0.63 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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 code: (i) −x+1, y+1/2, −z+3/2. |
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.