Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003124/ci6102sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003124/ci6102Isup2.hkl |
CCDC reference: 182587
Key indicators
- Single-crystal X-ray study
- T = 168 K
- Mean (C-C) = 0.013 Å
- R factor = 0.060
- wR factor = 0.155
- Data-to-parameter ratio = 14.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Diphenylmethyltin iodide was synthesized from the cleavage of methyltriphenyltin by elemental iodine in low yield. The halide anion was exchanged for the trifluoroacetate ion by treatment with silver trifluoracetate; the synthesis was adapted from the synthesis of dimethylphenyltin acetate, which used dimethyldiphenyltin as the starting reagent (Amini et al., 1989). The disproportionation was carried out in methanol under an atmosphere of nitrogen. The silver iodide that resulted from the exhange reaction was removed by filtration, and the filtrate was treated with an equimolar (100% excess) quantity of 18-crown-6. The removal of the solvent gave the desired product, which was then purified by recrystallization from ethanol. The compound melts in the 370–376 K range. The formulation was established from satisfactory 1H NMR integral analysis. The water signal appeared as a broad peak at δ = 4.1 p.p.m.; 2J(Sn—H) = 70 Hz in CDCl3; 19F NMR = 75.6 p.p.m. The IR (KBr disk) showed peaks at 3400 (H2O), 1703, 1638 (CO) 542, 520 (Sn—C) cm-1.
Although the diffraction intensities were measured beyond θ = 25°, those after this limit were too weak to be of use in the refinement. The water H atoms placed in calculated positions and refined with Uiso = 0.05 Å2.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound with ellipsoids at the 50% probability level. |
[Sn(C2F3O2)(CH3)(C6H5)2(H2O)]2·C12H24O6 | Z = 1 |
Mr = 1102.23 | F(000) = 556 |
Triclinic, P1 | Dx = 1.535 Mg m−3 |
a = 9.3175 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0263 (11) Å | Cell parameters from 4178 reflections |
c = 12.1632 (12) Å | θ = 1.8–26.5° |
α = 106.156 (1)° | µ = 1.13 mm−1 |
β = 101.177 (1)° | T = 168 K |
γ = 107.211 (1)° | Plate, colorless |
V = 1192.5 (2) Å3 | 0.30 × 0.15 × 0.05 mm |
Siemens CCD area-detector diffractometer | 4135 independent reflections |
Radiation source: fine-focus sealed tube | 3066 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.729, Tmax = 0.946 | k = −12→14 |
13839 measured reflections | l = −14→14 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0872P)2] where P = (Fo2 + 2Fc2)/3 |
4135 reflections | (Δ/σ)max < 0.001 |
281 parameters | Δρmax = 1.55 e Å−3 |
0 restraints | Δρmin = −1.32 e Å−3 |
[Sn(C2F3O2)(CH3)(C6H5)2(H2O)]2·C12H24O6 | γ = 107.211 (1)° |
Mr = 1102.23 | V = 1192.5 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.3175 (9) Å | Mo Kα radiation |
b = 12.0263 (11) Å | µ = 1.13 mm−1 |
c = 12.1632 (12) Å | T = 168 K |
α = 106.156 (1)° | 0.30 × 0.15 × 0.05 mm |
β = 101.177 (1)° |
Siemens CCD area-detector diffractometer | 4135 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3066 reflections with I > 2σ(I) |
Tmin = 0.729, Tmax = 0.946 | Rint = 0.098 |
13839 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.55 e Å−3 |
4135 reflections | Δρmin = −1.32 e Å−3 |
281 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.15882 (6) | 0.30984 (5) | 0.14065 (5) | 0.0222 (2) | |
F1 | −0.2763 (7) | 0.1886 (7) | −0.2310 (5) | 0.081 (2) | |
F2 | −0.1263 (8) | 0.1615 (8) | −0.3368 (5) | 0.096 (3) | |
F3 | −0.2052 (8) | 0.0317 (6) | −0.2554 (6) | 0.082 (2) | |
O1 | −0.0289 (6) | 0.2026 (5) | −0.0304 (5) | 0.0340 (13) | |
O2 | 0.0926 (7) | 0.3131 (6) | −0.1304 (5) | 0.0452 (16) | |
O3 | 0.4611 (6) | 0.6993 (5) | 0.4266 (5) | 0.0359 (14) | |
O4 | 0.7000 (6) | 0.6137 (5) | 0.3691 (5) | 0.0367 (14) | |
O5 | 0.6665 (6) | 0.3819 (5) | 0.3940 (5) | 0.0352 (14) | |
O1w | 0.3702 (6) | 0.4305 (5) | 0.3349 (4) | 0.0289 (13) | |
H1w1 | 0.3969 | 0.5090 | 0.3655 | 0.050* | |
H1w2 | 0.4471 | 0.4102 | 0.3594 | 0.050* | |
C1 | 0.0391 (9) | 0.1932 (7) | 0.2268 (7) | 0.0284 (19) | |
C2 | 0.0819 (9) | 0.2291 (7) | 0.3535 (7) | 0.0269 (18) | |
H2 | 0.1665 | 0.3056 | 0.4019 | 0.032* | |
C3 | 0.0022 (9) | 0.1544 (8) | 0.4077 (7) | 0.033 (2) | |
H3 | 0.0320 | 0.1799 | 0.4927 | 0.039* | |
C4 | −0.1216 (10) | 0.0419 (8) | 0.3377 (8) | 0.036 (2) | |
H4 | −0.1764 | −0.0093 | 0.3749 | 0.043* | |
C5 | −0.1646 (10) | 0.0048 (8) | 0.2135 (7) | 0.037 (2) | |
H5 | −0.2488 | −0.0721 | 0.1659 | 0.044* | |
C6 | −0.0846 (9) | 0.0801 (8) | 0.1572 (7) | 0.0317 (19) | |
H6 | −0.1149 | 0.0540 | 0.0721 | 0.038* | |
C7 | 0.3449 (9) | 0.2637 (8) | 0.0835 (6) | 0.0268 (18) | |
C8 | 0.4253 (9) | 0.3201 (7) | 0.0133 (6) | 0.0290 (19) | |
H8 | 0.3930 | 0.3778 | −0.0147 | 0.035* | |
C9 | 0.5518 (10) | 0.2913 (9) | −0.0149 (7) | 0.039 (2) | |
H9 | 0.6037 | 0.3284 | −0.0629 | 0.047* | |
C10 | 0.6025 (10) | 0.2075 (9) | 0.0276 (8) | 0.044 (2) | |
H10 | 0.6900 | 0.1894 | 0.0103 | 0.053* | |
C11 | 0.5218 (11) | 0.1511 (9) | 0.0960 (8) | 0.043 (2) | |
H11 | 0.5546 | 0.0936 | 0.1239 | 0.051* | |
C12 | 0.3950 (9) | 0.1777 (7) | 0.1237 (7) | 0.0316 (19) | |
H12 | 0.3418 | 0.1380 | 0.1697 | 0.038* | |
C13 | 0.1264 (10) | 0.4815 (8) | 0.1567 (8) | 0.039 (2) | |
H13a | 0.1671 | 0.5145 | 0.0991 | 0.059* | |
H13b | 0.1833 | 0.5417 | 0.2383 | 0.059* | |
H13c | 0.0139 | 0.4670 | 0.1399 | 0.059* | |
C14 | −0.0153 (10) | 0.2312 (7) | −0.1237 (7) | 0.0289 (19) | |
C15 | −0.1568 (11) | 0.1516 (9) | −0.2380 (7) | 0.039 (2) | |
C16 | 0.5851 (10) | 0.7671 (8) | 0.3917 (8) | 0.041 (2) | |
H16a | 0.6764 | 0.8214 | 0.4636 | 0.049* | |
H16b | 0.5500 | 0.8210 | 0.3532 | 0.049* | |
C17 | 0.6334 (10) | 0.6801 (9) | 0.3057 (8) | 0.041 (2) | |
H17a | 0.5409 | 0.6208 | 0.2366 | 0.049* | |
H17b | 0.7122 | 0.7277 | 0.2751 | 0.049* | |
C18 | 0.7476 (11) | 0.5251 (9) | 0.2940 (8) | 0.042 (2) | |
H18a | 0.8359 | 0.5688 | 0.2687 | 0.051* | |
H18b | 0.6587 | 0.4683 | 0.2213 | 0.051* | |
C19 | 0.7984 (10) | 0.4525 (9) | 0.3659 (8) | 0.042 (2) | |
H19a | 0.8409 | 0.3955 | 0.3193 | 0.050* | |
H19b | 0.8827 | 0.5105 | 0.4409 | 0.050* | |
C20 | 0.7046 (11) | 0.2952 (9) | 0.4451 (9) | 0.046 (2) | |
H20a | 0.7947 | 0.3414 | 0.5193 | 0.055* | |
H20b | 0.7353 | 0.2374 | 0.3875 | 0.055* | |
C21 | 0.5656 (11) | 0.2230 (8) | 0.4731 (8) | 0.044 (2) | |
H21a | 0.4711 | 0.1888 | 0.4023 | 0.053* | |
H21b | 0.5837 | 0.1522 | 0.4914 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0195 (3) | 0.0209 (3) | 0.0266 (3) | 0.0059 (2) | 0.0076 (2) | 0.0103 (2) |
F1 | 0.051 (4) | 0.106 (6) | 0.066 (4) | 0.047 (4) | −0.008 (3) | −0.002 (4) |
F2 | 0.078 (5) | 0.148 (7) | 0.033 (3) | 0.007 (5) | 0.013 (3) | 0.031 (4) |
F3 | 0.092 (5) | 0.039 (4) | 0.070 (4) | 0.001 (4) | −0.027 (4) | 0.012 (3) |
O1 | 0.032 (3) | 0.038 (4) | 0.026 (3) | 0.006 (3) | 0.003 (2) | 0.013 (3) |
O2 | 0.032 (4) | 0.059 (5) | 0.048 (4) | 0.010 (3) | 0.011 (3) | 0.032 (3) |
O3 | 0.032 (3) | 0.023 (3) | 0.045 (3) | 0.003 (3) | 0.007 (3) | 0.012 (3) |
O4 | 0.033 (3) | 0.043 (4) | 0.029 (3) | 0.009 (3) | 0.004 (3) | 0.014 (3) |
O5 | 0.032 (3) | 0.031 (3) | 0.042 (3) | 0.013 (3) | 0.009 (3) | 0.013 (3) |
O1w | 0.020 (3) | 0.024 (3) | 0.033 (3) | 0.003 (2) | 0.002 (2) | 0.005 (2) |
C1 | 0.025 (4) | 0.031 (5) | 0.031 (4) | 0.013 (4) | 0.010 (4) | 0.010 (4) |
C2 | 0.020 (4) | 0.029 (5) | 0.030 (4) | 0.006 (4) | 0.008 (3) | 0.011 (4) |
C3 | 0.029 (5) | 0.036 (5) | 0.026 (4) | 0.002 (4) | 0.008 (4) | 0.011 (4) |
C4 | 0.032 (5) | 0.032 (5) | 0.048 (5) | 0.004 (4) | 0.022 (4) | 0.022 (4) |
C5 | 0.029 (5) | 0.026 (5) | 0.035 (5) | −0.008 (4) | 0.006 (4) | 0.003 (4) |
C6 | 0.027 (5) | 0.033 (5) | 0.033 (4) | 0.009 (4) | 0.004 (4) | 0.015 (4) |
C7 | 0.024 (4) | 0.034 (5) | 0.022 (4) | 0.011 (4) | 0.008 (3) | 0.007 (3) |
C8 | 0.029 (5) | 0.027 (5) | 0.024 (4) | 0.006 (4) | 0.002 (3) | 0.007 (3) |
C9 | 0.028 (5) | 0.052 (6) | 0.034 (5) | 0.009 (5) | 0.014 (4) | 0.012 (4) |
C10 | 0.029 (5) | 0.052 (6) | 0.042 (5) | 0.015 (5) | 0.012 (4) | 0.004 (5) |
C11 | 0.046 (6) | 0.050 (6) | 0.040 (5) | 0.032 (5) | 0.010 (4) | 0.013 (4) |
C12 | 0.033 (5) | 0.024 (5) | 0.033 (5) | 0.009 (4) | 0.005 (4) | 0.008 (4) |
C13 | 0.044 (6) | 0.031 (5) | 0.045 (5) | 0.015 (4) | 0.006 (4) | 0.019 (4) |
C14 | 0.034 (5) | 0.022 (5) | 0.032 (5) | 0.011 (4) | 0.010 (4) | 0.012 (4) |
C15 | 0.041 (5) | 0.053 (7) | 0.028 (5) | 0.021 (5) | 0.011 (4) | 0.020 (4) |
C16 | 0.035 (5) | 0.032 (6) | 0.052 (6) | 0.002 (4) | 0.004 (4) | 0.028 (5) |
C17 | 0.030 (5) | 0.049 (6) | 0.041 (5) | 0.002 (5) | 0.003 (4) | 0.031 (5) |
C18 | 0.036 (5) | 0.047 (6) | 0.037 (5) | 0.005 (5) | 0.016 (4) | 0.012 (4) |
C19 | 0.029 (5) | 0.045 (6) | 0.046 (5) | 0.011 (5) | 0.010 (4) | 0.013 (4) |
C20 | 0.052 (6) | 0.045 (6) | 0.052 (6) | 0.032 (5) | 0.015 (5) | 0.020 (5) |
C21 | 0.053 (6) | 0.029 (6) | 0.055 (6) | 0.016 (5) | 0.016 (5) | 0.019 (4) |
Sn1—C1 | 2.158 (8) | C7—C8 | 1.421 (11) |
Sn1—C7 | 2.149 (7) | C8—C9 | 1.400 (11) |
Sn1—C13 | 2.135 (8) | C8—H8 | 0.95 |
Sn1—O1 | 2.193 (5) | C9—C10 | 1.408 (13) |
Sn1—O1w | 2.483 (5) | C9—H9 | 0.95 |
F1—C15 | 1.325 (10) | C10—C11 | 1.405 (13) |
F2—C15 | 1.316 (10) | C10—H10 | 0.95 |
F3—C15 | 1.317 (11) | C11—C12 | 1.389 (11) |
O1—C14 | 1.292 (9) | C11—H11 | 0.95 |
O2—C14 | 1.216 (10) | C12—H12 | 0.95 |
O3—C16 | 1.416 (10) | C13—H13a | 0.98 |
O3—C21i | 1.430 (10) | C13—H13b | 0.98 |
O4—C18 | 1.436 (10) | C13—H13c | 0.98 |
O4—C17 | 1.437 (10) | C14—C15 | 1.545 (12) |
O5—C19 | 1.433 (10) | C16—C17 | 1.498 (12) |
O5—C20 | 1.447 (10) | C16—H16a | 0.99 |
O1w—H1w1 | 0.85 | C16—H16b | 0.99 |
O1w—H1w2 | 0.85 | C17—H17a | 0.99 |
C1—C6 | 1.396 (11) | C17—H17b | 0.99 |
C1—C2 | 1.417 (10) | C18—C19 | 1.503 (13) |
C2—C3 | 1.385 (11) | C18—H18a | 0.99 |
C2—H2 | 0.95 | C18—H18b | 0.99 |
C3—C4 | 1.393 (11) | C19—H19a | 0.99 |
C3—H3 | 0.95 | C19—H19b | 0.99 |
C4—C5 | 1.388 (11) | C20—C21 | 1.489 (13) |
C4—H4 | 0.95 | C20—H20a | 0.99 |
C5—C6 | 1.411 (12) | C20—H20b | 0.99 |
C5—H5 | 0.95 | C21—O3i | 1.430 (10) |
C6—H6 | 0.95 | C21—H21a | 0.99 |
C7—C12 | 1.416 (11) | C21—H21b | 0.99 |
C1—Sn1—C7 | 115.0 (3) | C7—C12—H12 | 119.9 |
C1—Sn1—C13 | 118.8 (3) | Sn1—C13—H13a | 109.5 |
C1—Sn1—O1 | 91.2 (3) | Sn1—C13—H13b | 109.5 |
C1—Sn1—O1w | 88.4 (2) | H13a—C13—H13b | 109.5 |
C7—Sn1—C13 | 124.4 (3) | Sn1—C13—H13c | 109.5 |
C7—Sn1—O1 | 97.4 (2) | H13a—C13—H13c | 109.5 |
C7—Sn1—O1w | 82.9 (2) | H13b—C13—H13c | 109.5 |
C13—Sn1—O1 | 94.6 (3) | O2—C14—O1 | 127.8 (8) |
C13—Sn1—O1w | 85.5 (3) | O2—C14—C15 | 117.8 (7) |
O1—Sn1—O1w | 179.6 (2) | O1—C14—C15 | 114.4 (7) |
C14—O1—Sn1 | 119.1 (5) | F2—C15—F3 | 106.0 (8) |
C16—O3—C21i | 112.1 (7) | F2—C15—F1 | 106.0 (8) |
C18—O4—C17 | 112.5 (6) | F3—C15—F1 | 108.4 (8) |
C19—O5—C20 | 111.0 (6) | F2—C15—C14 | 113.3 (8) |
Sn1—O1w—H1w1 | 120.0 | F3—C15—C14 | 112.8 (7) |
Sn1—O1w—H1w2 | 124.4 | F1—C15—C14 | 109.9 (7) |
H1w1—O1w—H1w2 | 109.6 | O3—C16—C17 | 110.5 (7) |
C6—C1—C2 | 118.7 (7) | O3—C16—H16a | 109.5 |
C6—C1—Sn1 | 119.7 (6) | C17—C16—H16a | 109.5 |
C2—C1—Sn1 | 121.5 (6) | O3—C16—H16b | 109.5 |
C3—C2—C1 | 120.9 (7) | C17—C16—H16b | 109.5 |
C3—C2—H2 | 119.5 | H16a—C16—H16b | 108.1 |
C1—C2—H2 | 119.5 | O4—C17—C16 | 107.8 (7) |
C2—C3—C4 | 120.1 (7) | O4—C17—H17a | 110.1 |
C2—C3—H3 | 119.9 | C16—C17—H17a | 110.1 |
C4—C3—H3 | 119.9 | O4—C17—H17b | 110.1 |
C5—C4—C3 | 119.8 (7) | C16—C17—H17b | 110.1 |
C5—C4—H4 | 120.1 | H17a—C17—H17b | 108.5 |
C3—C4—H4 | 120.1 | O4—C18—C19 | 107.6 (7) |
C4—C5—C6 | 120.7 (8) | O4—C18—H18a | 110.2 |
C4—C5—H5 | 119.7 | C19—C18—H18a | 110.2 |
C6—C5—H5 | 119.7 | O4—C18—H18b | 110.2 |
C1—C6—C5 | 119.8 (8) | C19—C18—H18b | 110.2 |
C1—C6—H6 | 120.1 | H18a—C18—H18b | 108.5 |
C5—C6—H6 | 120.1 | O5—C19—C18 | 109.7 (7) |
C12—C7—C8 | 118.6 (7) | O5—C19—H19a | 109.7 |
C12—C7—Sn1 | 117.9 (6) | C18—C19—H19a | 109.7 |
C8—C7—Sn1 | 123.3 (6) | O5—C19—H19b | 109.7 |
C9—C8—C7 | 120.4 (8) | C18—C19—H19b | 109.7 |
C9—C8—H8 | 119.8 | H19a—C19—H19b | 108.2 |
C7—C8—H8 | 119.8 | O5—C20—C21 | 109.8 (7) |
C8—C9—C10 | 120.4 (8) | O5—C20—H20a | 109.7 |
C8—C9—H9 | 119.8 | C21—C20—H20a | 109.7 |
C10—C9—H9 | 119.8 | O5—C20—H20b | 109.7 |
C11—C10—C9 | 119.0 (8) | C21—C20—H20b | 109.7 |
C11—C10—H10 | 120.5 | H20a—C20—H20b | 108.2 |
C9—C10—H10 | 120.5 | O3i—C21—C20 | 110.6 (7) |
C12—C11—C10 | 121.4 (8) | O3i—C21—H21a | 109.5 |
C12—C11—H11 | 119.3 | C20—C21—H21a | 109.5 |
C10—C11—H11 | 119.3 | O3i—C21—H21b | 109.5 |
C11—C12—C7 | 120.2 (8) | C20—C21—H21b | 109.5 |
C11—C12—H12 | 119.9 | H21a—C21—H21b | 108.1 |
C13—Sn1—O1—C14 | 63.4 (6) | O1w—Sn1—C7—C8 | −102.5 (6) |
C7—Sn1—O1—C14 | −62.1 (6) | C12—C7—C8—C9 | −0.3 (11) |
C1—Sn1—O1—C14 | −177.5 (6) | Sn1—C7—C8—C9 | 176.2 (6) |
C13—Sn1—C1—C6 | 109.9 (6) | C7—C8—C9—C10 | −1.0 (12) |
C7—Sn1—C1—C6 | −84.7 (6) | C8—C9—C10—C11 | 1.6 (13) |
O1—Sn1—C1—C6 | 14.0 (6) | C9—C10—C11—C12 | −0.9 (13) |
O1w—Sn1—C1—C6 | −166.1 (6) | C10—C11—C12—C7 | −0.4 (13) |
C13—Sn1—C1—C2 | −69.3 (7) | C8—C7—C12—C11 | 0.9 (11) |
C7—Sn1—C1—C2 | 96.0 (6) | Sn1—C7—C12—C11 | −175.7 (6) |
O1—Sn1—C1—C2 | −165.3 (6) | Sn1—O1—C14—O2 | 0.2 (11) |
O1w—Sn1—C1—C2 | 14.6 (6) | Sn1—O1—C14—C15 | −178.4 (5) |
C6—C1—C2—C3 | −0.5 (11) | O2—C14—C15—F2 | 16.0 (11) |
Sn1—C1—C2—C3 | 178.8 (6) | O1—C14—C15—F2 | −165.2 (8) |
C1—C2—C3—C4 | 0.3 (12) | O2—C14—C15—F3 | 136.5 (8) |
C2—C3—C4—C5 | 0.1 (13) | O1—C14—C15—F3 | −44.7 (10) |
C3—C4—C5—C6 | −0.3 (13) | O2—C14—C15—F1 | −102.4 (9) |
C2—C1—C6—C5 | 0.3 (11) | O1—C14—C15—F1 | 76.4 (9) |
Sn1—C1—C6—C5 | −179.0 (6) | C21i—O3—C16—C17 | 167.5 (7) |
C4—C5—C6—C1 | 0.0 (13) | C18—O4—C17—C16 | 178.7 (7) |
C13—Sn1—C7—C12 | 153.5 (6) | O3—C16—C17—O4 | −65.7 (9) |
C1—Sn1—C7—C12 | −10.9 (7) | C17—O4—C18—C19 | −174.0 (7) |
O1—Sn1—C7—C12 | −105.8 (6) | C20—O5—C19—C18 | 170.2 (7) |
O1w—Sn1—C7—C12 | 73.9 (6) | O4—C18—C19—O5 | 64.4 (9) |
C13—Sn1—C7—C8 | −23.0 (8) | C19—O5—C20—C21 | −179.8 (7) |
C1—Sn1—C7—C8 | 172.6 (6) | O5—C20—C21—O3i | −71.2 (9) |
O1—Sn1—C7—C8 | 77.8 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O3 | 0.85 | 2.05 | 2.901 (7) | 176 |
O1w—H1w2···O5 | 0.85 | 2.15 | 2.983 (7) | 166 |
Experimental details
Crystal data | |
Chemical formula | [Sn(C2F3O2)(CH3)(C6H5)2(H2O)]2·C12H24O6 |
Mr | 1102.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 168 |
a, b, c (Å) | 9.3175 (9), 12.0263 (11), 12.1632 (12) |
α, β, γ (°) | 106.156 (1), 101.177 (1), 107.211 (1) |
V (Å3) | 1192.5 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.13 |
Crystal size (mm) | 0.30 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.729, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13839, 4135, 3066 |
Rint | 0.098 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.155, 1.02 |
No. of reflections | 4135 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.55, −1.32 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Sn1—C1 | 2.158 (8) | Sn1—O1 | 2.193 (5) |
Sn1—C7 | 2.149 (7) | Sn1—O1w | 2.483 (5) |
Sn1—C13 | 2.135 (8) | ||
C1—Sn1—C7 | 115.0 (3) | C7—Sn1—O1 | 97.4 (2) |
C1—Sn1—C13 | 118.8 (3) | C7—Sn1—O1w | 82.9 (2) |
C1—Sn1—O1 | 91.2 (3) | C13—Sn1—O1 | 94.6 (3) |
C1—Sn1—O1w | 88.4 (2) | C13—Sn1—O1w | 85.5 (3) |
C7—Sn1—C13 | 124.4 (3) | O1—Sn1—O1w | 179.6 (2) |
Triorganotin(IV) carboxylates commonly exist as either four-coordinate tetrahedral molecules or five-coordinate carboxylate-bridge polymers (Ng et al., 1988; Tiekink, 1991, 1994). Within the triphenyltin carboxylate class, a small number of compounds have sufficiently enhanced Lewis acidicity and they can form complexes with oxygen-donor ligands (Ng, 1998, 1999; Ng & Kumar Das, 1997). For the strongly electron-withdrawing trifluoroacetate anion in particular, the resulting triphenyltin trifluoroacetate is able to accept water into its coordination sphere, and it has been isolated as an 'outer-sphere coordination' complex with 1,10-phenanthroline (Ng et al., 1996). The studies on outer-sphere coordination complexes of hydrated triorganotin carboxylates are now extended to the title mixed alkyldiaryltin analog, methyldiphenyltin trifluoracetate, but with 18-crown-6 as the entity that interacts with the Sn atom through the coordinated water molecule.
The Sn atom in the title compound, (I), is five-coordinate in a trans-C3SnO2 trigonal-bipyramidal environment. The two organotin entities are located on opposite sides of the crown ether, across a center-of-symmetry that lies in the middle of the crown ether. The Sn atom lies out of the equatorial plane by 0.168 (1) Å in the direction of the carboxyl O atom [Sn← O = 2.483 (5) Å]; the C1—C6 phenyl ring is tilted by 77.3 (3)° with respect to the equatorial plane whereas the other phenyl ring, C7—C12, is tilted by 18.4 (3)°. The O—H···O hydrogen-bonding interactions involve only four of the six O atoms in the crown ether [Owater···Ocrown ether = 2.901 (7) and 2.983 (7) Å].