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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.014 Å
- R factor = 0.037
- wR factor = 0.127
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.89 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.891 Tmax scaled 0.441 Tmin scaled 0.340 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 18
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.