Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020020/ya6140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020020/ya6140Isup2.hkl |
CCDC reference: 202277
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.034
- wR factor = 0.080
- Data-to-parameter ratio = 20.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Dimethylphenyltin iodide was obtained by the cleavage of the tin–phenyl bond by elemental iodine (Davison & Rakita, 1970; Amini et al., 1989). In an attempt to synthesize dimethylphenyltin benzoate, equimolar quantities of dimethylphenyltin iodide (0.35 g, 1 mmol) and silver benzoate (0.23 g, 1 mmol) were dissolved in ethanol to give a precipitate that was presumed to be silver iodide. The precipitate was removed and the solvent evaporated off to furnish a white material. Crystals (m.p. 514–515 K) were grown from a methanol–toluene solvent system. In the 1H NMR spectrum in CDCl3, the tin–methyl coupling constant was 90 Hz.
H atoms were positioned geometrically and were allowed to ride on their parent C atoms, with Uiso(H) = 1.2Ueq(C) for the aromatic C atoms and Uiso(H) = 1.5Ueq(C) for the methyl C atoms.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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.
[Sn4O2(CH3)8(C7H5O2)4] | F(000) = 1080 |
Mr = 1111.47 | Dx = 1.774 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4001 (6) Å | Cell parameters from 3680 reflections |
b = 20.952 (1) Å | θ = 1.9–27.5° |
c = 11.2920 (7) Å | µ = 2.42 mm−1 |
β = 110.671 (2)° | T = 293 K |
V = 2080.8 (2) Å3 | Prism, colorless |
Z = 2 | 0.15 × 0.05 × 0.03 mm |
Bruker CCD area-detector diffractometer | 4785 independent reflections |
Radiation source: rotating anode tube | 3723 reflections with I > 2σ(I)' |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.713, Tmax = 0.931 | k = −27→27 |
20323 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0227P)2 + 0.958P] where P = (Fo2 + 2Fc2)/3 |
4785 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
[Sn4O2(CH3)8(C7H5O2)4] | V = 2080.8 (2) Å3 |
Mr = 1111.47 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.4001 (6) Å | µ = 2.42 mm−1 |
b = 20.952 (1) Å | T = 293 K |
c = 11.2920 (7) Å | 0.15 × 0.05 × 0.03 mm |
β = 110.671 (2)° |
Bruker CCD area-detector diffractometer | 4785 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3723 reflections with I > 2σ(I)' |
Tmin = 0.713, Tmax = 0.931 | Rint = 0.041 |
20323 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.69 e Å−3 |
4785 reflections | Δρmin = −0.32 e Å−3 |
230 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.26923 (3) | 0.62434 (1) | 0.42276 (2) | 0.0486 (1) | |
Sn2 | 0.44818 (3) | 0.48241 (1) | 0.62079 (2) | 0.0470 (1) | |
O1 | 0.3761 (3) | 0.6262 (1) | 0.2815 (3) | 0.059 (1) | |
O2 | 0.2225 (4) | 0.7081 (1) | 0.2134 (3) | 0.066 (1) | |
O3 | 0.1815 (5) | 0.6088 (2) | 0.5801 (3) | 0.103 (1) | |
O4 | 0.2867 (5) | 0.5279 (2) | 0.6996 (4) | 0.099 (1) | |
O5 | 0.4060 (3) | 0.5477 (2) | 0.4790 (2) | 0.050 (1) | |
C1 | 0.3804 (6) | 0.7047 (2) | 0.5243 (5) | 0.084 (2) | |
C2 | 0.0514 (5) | 0.5969 (3) | 0.3013 (5) | 0.076 (1) | |
C3 | 0.2861 (5) | 0.4097 (2) | 0.5528 (5) | 0.077 (1) | |
C4 | 0.6196 (6) | 0.5197 (2) | 0.7790 (5) | 0.082 (2) | |
C5 | 0.3215 (5) | 0.6729 (2) | 0.2031 (4) | 0.053 (1) | |
C6 | 0.3864 (5) | 0.6817 (2) | 0.1003 (4) | 0.056 (1) | |
C7 | 0.5113 (6) | 0.6492 (3) | 0.0992 (5) | 0.081 (2) | |
C8 | 0.5698 (7) | 0.6579 (3) | 0.0035 (6) | 0.103 (2) | |
C9 | 0.5015 (8) | 0.7014 (4) | −0.0896 (5) | 0.099 (2) | |
C10 | 0.3756 (8) | 0.7343 (3) | −0.0908 (5) | 0.093 (2) | |
C11 | 0.3195 (6) | 0.7246 (2) | 0.0045 (4) | 0.074 (1) | |
C12 | 0.2023 (5) | 0.5747 (2) | 0.6735 (4) | 0.054 (1) | |
C13 | 0.1207 (4) | 0.5914 (2) | 0.7614 (3) | 0.046 (1) | |
C14 | 0.0156 (5) | 0.6409 (2) | 0.7312 (4) | 0.058 (1) | |
C15 | −0.0611 (5) | 0.6558 (2) | 0.8107 (4) | 0.068 (1) | |
C16 | −0.0330 (5) | 0.6228 (2) | 0.9215 (4) | 0.067 (1) | |
C17 | 0.0703 (5) | 0.5739 (2) | 0.9519 (4) | 0.064 (1) | |
C18 | 0.1463 (5) | 0.5581 (2) | 0.8717 (4) | 0.058 (1) | |
H1a | 0.3250 | 0.7205 | 0.5751 | 0.127* | |
H1b | 0.3859 | 0.7372 | 0.4662 | 0.127* | |
H1c | 0.4814 | 0.6931 | 0.5781 | 0.127* | |
H2a | 0.0557 | 0.5849 | 0.2206 | 0.114* | |
H2b | −0.0178 | 0.6319 | 0.2905 | 0.114* | |
H2c | 0.0169 | 0.5612 | 0.3374 | 0.114* | |
H3a | 0.1928 | 0.4277 | 0.4965 | 0.116* | |
H3b | 0.2684 | 0.3895 | 0.6227 | 0.116* | |
H3c | 0.3231 | 0.3787 | 0.5082 | 0.116* | |
H4a | 0.7170 | 0.5065 | 0.7780 | 0.123* | |
H4b | 0.6067 | 0.5043 | 0.8546 | 0.123* | |
H4c | 0.6138 | 0.5654 | 0.7770 | 0.123* | |
H7 | 0.5585 | 0.6206 | 0.1641 | 0.097* | |
H8 | 0.6537 | 0.6346 | 0.0026 | 0.124* | |
H9 | 0.5414 | 0.7087 | −0.1529 | 0.119* | |
H10 | 0.3283 | 0.7629 | −0.1557 | 0.111* | |
H11 | 0.2347 | 0.7475 | 0.0045 | 0.088* | |
H14 | −0.0027 | 0.6640 | 0.6569 | 0.070* | |
H15 | −0.1327 | 0.6885 | 0.7893 | 0.081* | |
H16 | −0.0839 | 0.6335 | 0.9758 | 0.081* | |
H17 | 0.0892 | 0.5514 | 1.0269 | 0.077* | |
H18 | 0.2154 | 0.5245 | 0.8924 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0533 (2) | 0.0505 (2) | 0.0476 (2) | 0.0109 (1) | 0.0248 (1) | 0.0051 (1) |
Sn2 | 0.0523 (2) | 0.0489 (2) | 0.0461 (2) | 0.0056 (1) | 0.0252 (1) | 0.0048 (1) |
O1 | 0.064 (2) | 0.066 (2) | 0.058 (2) | 0.013 (1) | 0.036 (1) | 0.014 (1) |
O2 | 0.073 (2) | 0.066 (2) | 0.067 (2) | 0.015 (2) | 0.034 (2) | 0.009 (2) |
O3 | 0.132 (3) | 0.128 (3) | 0.080 (2) | 0.060 (3) | 0.078 (2) | 0.043 (2) |
O4 | 0.132 (3) | 0.100 (3) | 0.102 (3) | 0.058 (3) | 0.087 (3) | 0.032 (2) |
O5 | 0.055 (2) | 0.053 (2) | 0.051 (2) | 0.015 (1) | 0.029 (1) | 0.011 (1) |
C1 | 0.107 (4) | 0.063 (3) | 0.075 (3) | 0.001 (3) | 0.022 (3) | −0.013 (3) |
C2 | 0.055 (3) | 0.102 (4) | 0.075 (3) | −0.007 (3) | 0.027 (2) | 0.001 (3) |
C3 | 0.060 (3) | 0.076 (3) | 0.096 (4) | −0.010 (2) | 0.028 (3) | 0.001 (3) |
C4 | 0.093 (4) | 0.075 (3) | 0.069 (3) | 0.002 (3) | 0.017 (3) | −0.014 (3) |
C5 | 0.061 (2) | 0.052 (2) | 0.050 (2) | −0.004 (2) | 0.023 (2) | −0.002 (2) |
C6 | 0.066 (3) | 0.056 (2) | 0.050 (2) | −0.014 (2) | 0.027 (2) | −0.004 (2) |
C7 | 0.086 (4) | 0.101 (4) | 0.072 (3) | 0.009 (3) | 0.048 (3) | 0.014 (3) |
C8 | 0.098 (4) | 0.140 (6) | 0.097 (4) | 0.001 (4) | 0.066 (4) | 0.005 (4) |
C9 | 0.113 (5) | 0.133 (5) | 0.072 (4) | −0.046 (4) | 0.057 (4) | −0.014 (4) |
C10 | 0.121 (5) | 0.102 (4) | 0.061 (3) | −0.022 (4) | 0.039 (3) | 0.013 (3) |
C11 | 0.096 (4) | 0.070 (3) | 0.058 (3) | −0.008 (3) | 0.031 (3) | 0.005 (2) |
C12 | 0.056 (2) | 0.062 (3) | 0.049 (2) | 0.001 (2) | 0.025 (2) | −0.007 (2) |
C13 | 0.050 (2) | 0.052 (2) | 0.040 (2) | −0.002 (2) | 0.022 (2) | −0.007 (2) |
C14 | 0.065 (3) | 0.061 (3) | 0.050 (2) | 0.006 (2) | 0.024 (2) | 0.003 (2) |
C15 | 0.060 (3) | 0.077 (3) | 0.072 (3) | 0.016 (2) | 0.031 (2) | −0.006 (3) |
C16 | 0.063 (3) | 0.085 (3) | 0.068 (3) | −0.002 (2) | 0.040 (2) | −0.015 (3) |
C17 | 0.079 (3) | 0.077 (3) | 0.048 (2) | 0.003 (2) | 0.036 (2) | 0.005 (2) |
C18 | 0.059 (2) | 0.065 (3) | 0.057 (2) | 0.012 (2) | 0.028 (2) | 0.004 (2) |
Sn1—C1 | 2.096 (5) | C15—C16 | 1.371 (6) |
Sn1—C2 | 2.103 (5) | C16—C17 | 1.368 (6) |
Sn1—O1 | 2.165 (3) | C17—C18 | 1.377 (5) |
Sn1—O3 | 2.232 (3) | C1—H1a | 0.9600 |
Sn1—O5 | 2.015 (2) | C1—H1b | 0.9600 |
Sn2—C3 | 2.099 (5) | C1—H1c | 0.9600 |
Sn2—C4 | 2.089 (5) | C2—H2a | 0.9600 |
Sn2—O1i | 2.800 (3) | C2—H2b | 0.9600 |
Sn2—O4 | 2.226 (3) | C2—H2c | 0.9600 |
Sn2—O5 | 2.035 (2) | C3—H3a | 0.9600 |
Sn2—O5i | 2.153 (2) | C3—H3b | 0.9600 |
O1—C5 | 1.296 (5) | C3—H3c | 0.9600 |
O2—C5 | 1.226 (5) | C4—H4a | 0.9600 |
O3—C12 | 1.231 (5) | C4—H4b | 0.9600 |
O4—C12 | 1.230 (5) | C4—H4c | 0.9600 |
C5—C6 | 1.502 (5) | C7—H7 | 0.9300 |
C6—C7 | 1.361 (7) | C8—H8 | 0.9300 |
C6—C11 | 1.376 (6) | C9—H9 | 0.9300 |
C7—C8 | 1.386 (7) | C10—H10 | 0.9300 |
C8—C9 | 1.369 (9) | C11—H11 | 0.9300 |
C9—C10 | 1.365 (9) | C14—H14 | 0.9300 |
C10—C11 | 1.370 (7) | C15—H15 | 0.9300 |
C12—C13 | 1.495 (5) | C16—H16 | 0.9300 |
C13—C18 | 1.374 (5) | C17—H17 | 0.9300 |
C13—C14 | 1.388 (6) | C18—H18 | 0.9300 |
C14—C15 | 1.372 (6) | ||
C1—Sn1—C2 | 139.4 (2) | C16—C15—C14 | 120.4 (4) |
C1—Sn1—O1 | 96.7 (2) | C17—C16—C15 | 119.9 (4) |
C1—Sn1—O3 | 86.3 (2) | C16—C17—C18 | 120.1 (4) |
C1—Sn1—O5 | 109.2 (2) | C13—C18—C17 | 120.6 (4) |
C2—Sn1—O1 | 97.0 (2) | Sn1—C1—H1a | 109.5 |
C2—Sn1—O3 | 86.0 (2) | Sn1—C1—H1b | 109.5 |
C2—Sn1—O5 | 110.7 (2) | H1a—C1—H1b | 109.5 |
O1—Sn1—O3 | 171.0 (1) | Sn1—C1—H1c | 109.5 |
O1—Sn1—O5 | 80.6 (1) | H1a—C1—H1c | 109.5 |
O3—Sn1—O5 | 90.4 (1) | H1b—C1—H1c | 109.5 |
C3—Sn2—C4 | 145.6 (2) | Sn1—C2—H2a | 109.5 |
C3—Sn2—O1i | 78.8 (2) | Sn1—C2—H2b | 109.5 |
C3—Sn2—O4 | 87.0 (2) | H2a—C2—H2b | 109.5 |
C3—Sn2—O5 | 106.6 (2) | Sn1—C2—H2c | 109.5 |
C3—Sn2—O5i | 96.3 (2) | H2a—C2—H2c | 109.5 |
C4—Sn2—O1i | 78.3 (2) | H2b—C2—H2c | 109.5 |
C4—Sn2—O4 | 85.8 (2) | Sn2—C3—H3a | 109.5 |
C4—Sn2—O5 | 107.4 (2) | Sn2—C3—H3b | 109.5 |
C4—Sn2—O5i | 96.6 (2) | H3a—C3—H3b | 109.5 |
O1i—Sn2—O4 | 125.5 (1) | Sn2—C3—H3c | 109.5 |
O1i—Sn2—O5 | 141.3 (1) | H3a—C3—H3c | 109.5 |
O1i—Sn2—O5i | 64.7 (1) | H3b—C3—H3c | 109.5 |
O4—Sn2—O5 | 93.2 (1) | Sn2—C4—H4a | 109.5 |
O4—Sn2—O5i | 169.8 (1) | Sn2—C4—H4b | 109.5 |
O5—Sn2—O5i | 76.6 (1) | H4a—C4—H4b | 109.5 |
C5—O1—Sn1 | 110.0 (2) | Sn2—C4—H4c | 109.5 |
C12—O3—Sn1 | 140.8 (3) | H4a—C4—H4c | 109.5 |
C12—O4—Sn2 | 135.9 (3) | H4b—C4—H4c | 109.5 |
Sn1—O5—Sn2 | 135.2 (1) | C6—C7—H7 | 119.2 |
Sn1—O5—Sn2i | 121.4 (1) | C8—C7—H7 | 119.2 |
Sn2—O5—Sn2i | 103.4 (1) | C9—C8—H8 | 120.7 |
O2—C5—O1 | 121.3 (4) | C7—C8—H8 | 120.7 |
O2—C5—C6 | 121.9 (4) | C10—C9—H9 | 119.5 |
O1—C5—C6 | 116.8 (4) | C8—C9—H9 | 119.5 |
C7—C6—C11 | 118.4 (4) | C9—C10—H10 | 120.3 |
C7—C6—C5 | 122.2 (4) | C11—C10—H10 | 120.3 |
C11—C6—C5 | 119.4 (4) | C10—C11—H11 | 119.4 |
C6—C7—C8 | 121.5 (5) | C6—C11—H11 | 119.4 |
C9—C8—C7 | 118.5 (6) | C15—C14—H14 | 119.9 |
C10—C9—C8 | 121.0 (5) | C13—C14—H14 | 119.9 |
C9—C10—C11 | 119.3 (6) | C16—C15—H15 | 119.8 |
C10—C11—C6 | 121.2 (5) | C14—C15—H15 | 119.8 |
O4—C12—O3 | 124.3 (4) | C17—C16—H16 | 120.1 |
O4—C12—C13 | 117.8 (4) | C15—C16—H16 | 120.1 |
O3—C12—C13 | 117.9 (4) | C16—C17—H17 | 120.0 |
C18—C13—C14 | 119.0 (3) | C18—C17—H17 | 120.0 |
C18—C13—C12 | 121.1 (4) | C13—C18—H18 | 119.7 |
C14—C13—C12 | 120.0 (4) | C17—C18—H18 | 119.7 |
C15—C14—C13 | 120.1 (4) | ||
O5—Sn1—O1—C5 | 178.5 (3) | Sn1—O1—C5—C6 | 178.7 (3) |
C1—Sn1—O1—C5 | −73.1 (3) | O2—C5—C6—C7 | 169.9 (5) |
C2—Sn1—O1—C5 | 68.6 (3) | O1—C5—C6—C7 | −9.6 (6) |
O5—Sn1—O3—C12 | 5.3 (6) | O2—C5—C6—C11 | −9.2 (6) |
C1—Sn1—O3—C12 | −103.9 (6) | O1—C5—C6—C11 | 171.3 (4) |
C2—Sn1—O3—C12 | 116.0 (6) | C11—C6—C7—C8 | −1.0 (8) |
O5—Sn2—O4—C12 | −0.7 (6) | C5—C6—C7—C8 | 179.9 (5) |
C4—Sn2—O4—C12 | 106.5 (6) | C6—C7—C8—C9 | 1.6 (9) |
C3—Sn2—O4—C12 | −107.2 (6) | C7—C8—C9—C10 | −2 (1) |
O5i—Sn2—O4—C12 | 2 (1) | C8—C9—C10—C11 | 1.7 (9) |
O1i—Sn2—O4—C12 | 178.9 (5) | C9—C10—C11—C6 | −1.0 (8) |
C1—Sn1—O5—Sn2 | 86.2 (3) | C7—C6—C11—C10 | 0.6 (7) |
C2—Sn1—O5—Sn2 | −85.9 (2) | C5—C6—C11—C10 | 179.8 (4) |
O1—Sn1—O5—Sn2 | −179.9 (2) | Sn2—O4—C12—O3 | 4.8 (9) |
O3—Sn1—O5—Sn2 | 0.0 (2) | Sn2—O4—C12—C13 | −174.7 (3) |
C1—Sn1—O5—Sn2i | −94.5 (2) | Sn1—O3—C12—O4 | −8.1 (9) |
C2—Sn1—O5—Sn2i | 93.4 (2) | Sn1—O3—C12—C13 | 171.5 (4) |
O1—Sn1—O5—Sn2i | −0.6 (1) | O4—C12—C13—C18 | 4.0 (6) |
O3—Sn1—O5—Sn2i | 179.3 (2) | O3—C12—C13—C18 | −175.6 (4) |
C4—Sn2—O5—Sn1 | −87.7 (3) | O4—C12—C13—C14 | −175.2 (4) |
C3—Sn2—O5—Sn1 | 86.7 (2) | O3—C12—C13—C14 | 5.3 (6) |
O5i—Sn2—O5—Sn1 | 179.4 (3) | C18—C13—C14—C15 | −0.1 (6) |
O4—Sn2—O5—Sn1 | −1.1 (2) | C12—C13—C14—C15 | 179.0 (4) |
O1i—Sn2—O5—Sn1 | 179.4 (1) | C13—C14—C15—C16 | 1.1 (7) |
C4—Sn2—O5—Sn2i | 92.9 (2) | C14—C15—C16—C17 | −1.2 (7) |
C3—Sn2—O5—Sn2i | −92.7 (2) | C15—C16—C17—C18 | 0.2 (7) |
O5i—Sn2—O5—Sn2i | 0.0 | C14—C13—C18—C17 | −0.8 (6) |
O4—Sn2—O5—Sn2i | 179.5 (2) | C12—C13—C18—C17 | −180.0 (4) |
O1i—Sn2—O5—Sn2i | 0.0 (2) | C16—C17—C18—C13 | 0.8 (7) |
Sn1—O1—C5—O2 | −0.8 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn4O2(CH3)8(C7H5O2)4] |
Mr | 1111.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 9.4001 (6), 20.952 (1), 11.2920 (7) |
β (°) | 110.671 (2) |
V (Å3) | 2080.8 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.42 |
Crystal size (mm) | 0.15 × 0.05 × 0.03 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.713, 0.931 |
No. of measured, independent and observed [I > 2σ(I)'] reflections | 20323, 4785, 3723 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.080, 1.01 |
No. of reflections | 4785 |
No. of parameters | 230 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.32 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Sn1—C1 | 2.096 (5) | Sn2—C4 | 2.089 (5) |
Sn1—C2 | 2.103 (5) | Sn2—O1i | 2.800 (3) |
Sn1—O1 | 2.165 (3) | Sn2—O4 | 2.226 (3) |
Sn1—O3 | 2.232 (3) | Sn2—O5 | 2.035 (2) |
Sn1—O5 | 2.015 (2) | Sn2—O5i | 2.153 (2) |
Sn2—C3 | 2.099 (5) | ||
C1—Sn1—C2 | 139.4 (2) | C3—Sn2—O5i | 96.3 (2) |
C1—Sn1—O1 | 96.7 (2) | C4—Sn2—O1i | 78.3 (2) |
C1—Sn1—O3 | 86.3 (2) | C4—Sn2—O4 | 85.8 (2) |
C1—Sn1—O5 | 109.2 (2) | C4—Sn2—O5 | 107.4 (2) |
C2—Sn1—O1 | 97.0 (2) | C4—Sn2—O5i | 96.6 (2) |
C2—Sn1—O3 | 86.0 (2) | O1i—Sn2—O4 | 125.5 (1) |
C2—Sn1—O5 | 110.7 (2) | O1i—Sn2—O5 | 141.3 (1) |
O1—Sn1—O3 | 171.0 (1) | O1i—Sn2—O5i | 64.7 (1) |
O1—Sn1—O5 | 80.6 (1) | O4—Sn2—O5 | 93.2 (1) |
O3—Sn1—O5 | 90.4 (1) | O4—Sn2—O5i | 169.8 (1) |
C3—Sn2—C4 | 145.6 (2) | O5—Sn2—O5i | 76.6 (1) |
C3—Sn2—O1i | 78.8 (2) | Sn1—O5—Sn2 | 135.2 (1) |
C3—Sn2—O4 | 87.0 (2) | Sn1—O5—Sn2i | 121.4 (1) |
C3—Sn2—O5 | 106.6 (2) | Sn2—O5—Sn2i | 103.4 (1) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
In the supramolecular self-assembled structures of dimeric 1,1,3,3-tetraorgano-1,3-dicarboxylatodistannoxanes, the monomeric R2(R'CO2)Sn—O—Sn(O2CR')R2 moieties are linked by two dative Sn← O interactions involving their distannoxanyl O atoms. The dative bond is unusually short in such organotin compounds, these being typically as short as the covalent Sn—O bond, so that the covalent and dative bonds are not readily distinguished (Ng et al., 1991; Haiduc & Edelmann, 1999). The most common of the four types of such tetranuclear aggregates has two bridging and two monodentate carboxylate groups, and one Sn atom is five-coordinated, whereas the other is six-coordinated. The benzoate derivative, bis(1,1,3,3-tetramethyl-1,3-dibenzoatodistannoxane), (I), adopts this centrosymmetric conformation (Fig. 1). The five-coordinated Sn atom has a bent C2Sn skeleton [C—Sn—C = 139.4 (2) Å], as does the six-coordinated Sn atom [C—Sn—C = 145.6 (2)°]. The five-coordinated Sn atom is bonded to a monodentate benzoate group, whose –CO2 unit displays single and double C—O bonds. The single-bond atom O1 acts as a bridging atom forming a relatively short bond with the five-coordinated Sn atom [Sn1—O1 = 2.165 (3) Å] and a very long bond with the six-coordinated Sn atom [O1—Sn2i 2.800 (3) Å; symmetry code: (i) 1 − x, 1 − y, 1 − z]. The double-bond atom O2 is engaged in a weak C—HAr···OCO interaction [C15···O2ii = 3.450 (6) Å and C—H···Oii = 165°; symmetry code: (ii) −1/2 + x, 3/2 − y, 1/2 + z], which links adjacent molecules into a layer structure (Fig. 2).
A number of the distannoxanes have been isolated as the products either from the condensation of a diorganotin oxide with two molar equivalents of the carboxylic acid, or from the metathetical reaction of a diorganotin halide with metal carboxylate (Tiekink, 1991a; Tiekink, 1994). The dicarboxylate that is initially formed is unstable with respect to hydrolysis to the distannoxane. An example is shown by dimethyltin diacetate, an air-sensitive compound (Lockhart et al., 1987) that can hydrolyze to the distannoxane (Lockhart et al., 1986). On the other hand, dimethyltin dibenzoate represents an exception as it is air-stable; the monomeric compound adopts a skew-trapezoidal bipyramidal geometry [C—Sn—C = 147.2 (7)°] (Tiekink, 1991b).