Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005989/gd1099sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005989/gd1099Isup2.hkl |
CCDC reference: 147630
Compound (I) was prepared by the halogen exchange reaction between Cl2Sn(CMe2CH2COMe)2 (Hutton & Oakes, 1976) and excess NaI in acetone solution. Crystals were obtained from solution in EtOH. The compound decomposed on heating at 444–445 K.
H atoms were placed in calculated positions and refined with a riding model. Maximum and minimum Δρ were found 1.01 Å from I1B and 0.87 Å from Sn1B, respectively.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[SnI2(C6H11O)2] | Z = 4 |
Mr = 570.79 | F(000) = 1064 |
Triclinic, P1 | Dx = 2.127 Mg m−3 |
a = 7.8655 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.8464 (4) Å | Cell parameters from 28392 reflections |
c = 16.4602 (4) Å | θ = 1.5–27.5° |
α = 108.0591 (14)° | µ = 4.89 mm−1 |
β = 102.0352 (14)° | T = 150 K |
γ = 90.0908 (14)° | Plate, colourless |
V = 1782.73 (8) Å3 | 0.12 × 0.10 × 0.05 mm |
Nonius KappaCCD area detector diffractometer | 8156 independent reflections |
Radiation source: Nonius FR591 rotating anode | 6019 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.5° |
ϕ and ω scans to fill the Ewald sphere | h = −10→9 |
Absorption correction: empirical (using intensity measurements) (SORTAV; Blessing, 1997) | k = −19→19 |
Tmin = 0.692, Tmax = 0.795 | l = −21→21 |
28392 measured reflections |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.100 | Calculated w = 1/[σ2(Fo2) + (0.0464P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
8156 reflections | Δρmax = 2.36 e Å−3 |
320 parameters | Δρmin = −1.62 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: heavy-atom method | Extinction coefficient: 0.00079 (12) |
[SnI2(C6H11O)2] | γ = 90.0908 (14)° |
Mr = 570.79 | V = 1782.73 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.8655 (2) Å | Mo Kα radiation |
b = 14.8464 (4) Å | µ = 4.89 mm−1 |
c = 16.4602 (4) Å | T = 150 K |
α = 108.0591 (14)° | 0.12 × 0.10 × 0.05 mm |
β = 102.0352 (14)° |
Nonius KappaCCD area detector diffractometer | 8156 independent reflections |
Absorption correction: empirical (using intensity measurements) (SORTAV; Blessing, 1997) | 6019 reflections with I > 2σ(I) |
Tmin = 0.692, Tmax = 0.795 | Rint = 0.069 |
28392 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.00 | Δρmax = 2.36 e Å−3 |
8156 reflections | Δρmin = −1.62 e Å−3 |
320 parameters |
Experimental. The only known problem with this structure is a checkcif level C alert questioning the appropriateness of the correction for absorption applied to the intensity data arising from a slight incompatibility between the reported crystal dimensions and the minimum and maximum transmission factors. The reported values faithfully replicate those provided by the EPSRC crystallographic service at Southampton and are not therefore under the control of the authors. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One reflection showing particularly bad agreement (0,0,1) omitted. H in calculated positions and refined with a riding model. |
x | y | z | Uiso*/Ueq | ||
Sn1A | 0.11370 (5) | −0.02131 (3) | 0.25486 (2) | 0.02026 (11) | |
I1A | 0.06194 (5) | 0.13162 (3) | 0.39941 (2) | 0.03335 (12) | |
I2A | −0.17183 (5) | −0.02428 (3) | 0.11437 (2) | 0.03248 (12) | |
O1A | 0.3556 (5) | −0.0673 (3) | 0.3484 (3) | 0.0378 (10) | |
C1A | 0.0007 (7) | −0.1339 (4) | 0.2945 (4) | 0.0279 (13) | |
C2A | 0.1156 (8) | −0.1303 (5) | 0.3823 (4) | 0.0339 (14) | |
H2A1 | 0.0765 | −0.0805 | 0.4290 | 0.041* | |
H2A2 | 0.0974 | −0.1918 | 0.3921 | 0.041* | |
C3A | 0.3057 (8) | −0.1110 (4) | 0.3917 (4) | 0.0310 (13) | |
C4A | 0.4330 (11) | −0.1416 (6) | 0.4571 (5) | 0.058 (2) | |
H4A1 | 0.5491 | −0.1122 | 0.4644 | 0.087* | |
H4A2 | 0.4358 | −0.2108 | 0.4366 | 0.087* | |
H4A3 | 0.3977 | −0.1218 | 0.5134 | 0.087* | |
C5A | −0.0011 (8) | −0.2294 (4) | 0.2260 (4) | 0.0357 (15) | |
H5A1 | 0.1178 | −0.2421 | 0.2185 | 0.054* | |
H5A2 | −0.0749 | −0.2290 | 0.1702 | 0.054* | |
H5A3 | −0.0476 | −0.2791 | 0.2448 | 0.054* | |
C6A | −0.1860 (8) | −0.1130 (5) | 0.3057 (5) | 0.0424 (16) | |
H6A1 | −0.2606 | −0.1166 | 0.2489 | 0.064* | |
H6A2 | −0.1854 | −0.0492 | 0.3471 | 0.064* | |
H6A3 | −0.2312 | −0.1599 | 0.3281 | 0.064* | |
O2A | 0.2440 (6) | −0.1430 (3) | 0.1536 (3) | 0.0356 (10) | |
C7A | 0.2984 (7) | 0.0573 (4) | 0.2115 (4) | 0.0255 (12) | |
C8A | 0.3089 (7) | −0.0055 (4) | 0.1199 (4) | 0.0276 (13) | |
H8A1 | 0.2109 | 0.0072 | 0.0772 | 0.033* | |
H8A2 | 0.4182 | 0.0137 | 0.1069 | 0.033* | |
C9A | 0.3039 (8) | −0.1091 (5) | 0.1054 (4) | 0.0325 (14) | |
C10A | 0.3651 (10) | −0.1713 (5) | 0.0297 (5) | 0.052 (2) | |
H10A | 0.3166 | −0.2366 | 0.0158 | 0.078* | |
H10B | 0.4927 | −0.1697 | 0.0441 | 0.078* | |
H10C | 0.3268 | −0.1491 | −0.0209 | 0.078* | |
C11A | 0.4753 (8) | 0.0726 (5) | 0.2748 (4) | 0.0331 (14) | |
H11A | 0.5569 | 0.1083 | 0.2565 | 0.050* | |
H11B | 0.5198 | 0.0110 | 0.2745 | 0.050* | |
H11C | 0.4630 | 0.1085 | 0.3340 | 0.050* | |
C12A | 0.2304 (8) | 0.1521 (4) | 0.2075 (4) | 0.0348 (14) | |
H12A | 0.2260 | 0.1926 | 0.2666 | 0.052* | |
H12B | 0.1132 | 0.1414 | 0.1698 | 0.052* | |
H12C | 0.3083 | 0.1834 | 0.1836 | 0.052* | |
Sn1B | 0.32888 (5) | 0.52263 (3) | 0.74656 (2) | 0.02034 (11) | |
I1B | 0.16777 (5) | 0.52768 (3) | 0.88798 (2) | 0.03311 (12) | |
I2B | 0.15322 (5) | 0.36794 (3) | 0.60251 (2) | 0.03290 (12) | |
O1B | 0.5463 (5) | 0.6459 (3) | 0.8471 (3) | 0.0330 (9) | |
C1B | 0.5515 (7) | 0.4457 (4) | 0.7914 (4) | 0.0256 (12) | |
C2B | 0.6441 (8) | 0.5097 (5) | 0.8822 (4) | 0.0317 (14) | |
H2B1 | 0.5842 | 0.4984 | 0.9258 | 0.038* | |
H2B2 | 0.7647 | 0.4904 | 0.8950 | 0.038* | |
C3B | 0.6521 (8) | 0.6123 (4) | 0.8942 (4) | 0.0307 (14) | |
C4B | 0.7825 (9) | 0.6758 (5) | 0.9695 (5) | 0.0492 (19) | |
H4B1 | 0.7575 | 0.7421 | 0.9769 | 0.074* | |
H4B2 | 0.8997 | 0.6658 | 0.9582 | 0.074* | |
H4B3 | 0.7762 | 0.6612 | 1.0229 | 0.074* | |
C5B | 0.6712 (7) | 0.4291 (4) | 0.7266 (4) | 0.0312 (14) | |
H5B1 | 0.7669 | 0.3918 | 0.7435 | 0.047* | |
H5B2 | 0.7188 | 0.4904 | 0.7272 | 0.047* | |
H5B3 | 0.6045 | 0.3945 | 0.6676 | 0.047* | |
C6B | 0.4871 (8) | 0.3507 (4) | 0.7962 (4) | 0.0329 (14) | |
H6B1 | 0.5859 | 0.3201 | 0.8208 | 0.049* | |
H6B2 | 0.4315 | 0.3096 | 0.7372 | 0.049* | |
H6B3 | 0.4024 | 0.3617 | 0.8337 | 0.049* | |
O2B | 0.4908 (5) | 0.5684 (3) | 0.6528 (3) | 0.0366 (10) | |
C7B | 0.1774 (7) | 0.6324 (4) | 0.7044 (4) | 0.0262 (12) | |
C8B | 0.2174 (8) | 0.6287 (5) | 0.6172 (4) | 0.0353 (15) | |
H8B1 | 0.1389 | 0.5781 | 0.5704 | 0.042* | |
H8B2 | 0.1895 | 0.6897 | 0.6068 | 0.042* | |
C9B | 0.4002 (8) | 0.6109 (4) | 0.6087 (4) | 0.0329 (14) | |
C10B | 0.4718 (11) | 0.6402 (6) | 0.5430 (5) | 0.056 (2) | |
H10D | 0.4950 | 0.7093 | 0.5633 | 0.084* | |
H10E | 0.3871 | 0.6207 | 0.4868 | 0.084* | |
H10F | 0.5805 | 0.6097 | 0.5357 | 0.084* | |
C11B | 0.2354 (9) | 0.7295 (4) | 0.7719 (4) | 0.0376 (15) | |
H11D | 0.1682 | 0.7780 | 0.7534 | 0.056* | |
H11E | 0.3597 | 0.7437 | 0.7771 | 0.056* | |
H11F | 0.2157 | 0.7295 | 0.8288 | 0.056* | |
C12B | −0.0174 (7) | 0.6108 (5) | 0.6929 (4) | 0.0367 (15) | |
H12D | −0.0824 | 0.6573 | 0.6701 | 0.055* | |
H12E | −0.0428 | 0.6145 | 0.7496 | 0.055* | |
H12F | −0.0521 | 0.5469 | 0.6516 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1A | 0.0228 (2) | 0.0186 (2) | 0.0211 (2) | 0.00286 (15) | 0.00440 (15) | 0.00891 (16) |
I1A | 0.0493 (3) | 0.0240 (2) | 0.0250 (2) | 0.00642 (18) | 0.01022 (17) | 0.00400 (16) |
I2A | 0.0269 (2) | 0.0417 (3) | 0.0280 (2) | 0.00377 (18) | −0.00081 (15) | 0.01439 (18) |
O1A | 0.030 (2) | 0.045 (3) | 0.044 (3) | 0.004 (2) | −0.0034 (19) | 0.030 (2) |
C1A | 0.034 (3) | 0.025 (3) | 0.030 (3) | 0.002 (3) | 0.005 (2) | 0.019 (3) |
C2A | 0.045 (4) | 0.036 (4) | 0.029 (3) | −0.002 (3) | 0.007 (3) | 0.022 (3) |
C3A | 0.044 (4) | 0.022 (3) | 0.028 (3) | 0.009 (3) | 0.004 (3) | 0.013 (3) |
C4A | 0.068 (5) | 0.054 (5) | 0.052 (5) | −0.001 (4) | −0.016 (4) | 0.036 (4) |
C5A | 0.042 (4) | 0.022 (3) | 0.044 (4) | −0.005 (3) | 0.008 (3) | 0.013 (3) |
C6A | 0.042 (4) | 0.040 (4) | 0.059 (4) | 0.000 (3) | 0.022 (3) | 0.027 (4) |
O2A | 0.047 (3) | 0.027 (2) | 0.038 (2) | 0.008 (2) | 0.021 (2) | 0.010 (2) |
C7A | 0.026 (3) | 0.026 (3) | 0.029 (3) | 0.006 (2) | 0.008 (2) | 0.012 (3) |
C8A | 0.022 (3) | 0.033 (3) | 0.028 (3) | 0.006 (2) | 0.008 (2) | 0.009 (3) |
C9A | 0.027 (3) | 0.040 (4) | 0.027 (3) | 0.008 (3) | 0.005 (2) | 0.004 (3) |
C10A | 0.066 (5) | 0.041 (4) | 0.041 (4) | −0.005 (4) | 0.024 (4) | −0.006 (3) |
C11A | 0.029 (3) | 0.033 (4) | 0.040 (4) | 0.000 (3) | 0.008 (3) | 0.015 (3) |
C12A | 0.043 (4) | 0.023 (3) | 0.050 (4) | 0.007 (3) | 0.016 (3) | 0.025 (3) |
Sn1B | 0.0219 (2) | 0.0189 (2) | 0.0213 (2) | 0.00041 (15) | 0.00304 (15) | 0.00912 (16) |
I1B | 0.0310 (2) | 0.0446 (3) | 0.0290 (2) | 0.00362 (18) | 0.01157 (16) | 0.01597 (19) |
I2B | 0.0439 (2) | 0.0228 (2) | 0.0261 (2) | −0.00591 (17) | 0.00019 (17) | 0.00429 (16) |
O1B | 0.034 (2) | 0.025 (2) | 0.034 (2) | −0.0017 (18) | −0.0028 (18) | 0.0079 (19) |
C1B | 0.021 (3) | 0.028 (3) | 0.034 (3) | 0.006 (2) | 0.008 (2) | 0.017 (3) |
C2B | 0.028 (3) | 0.043 (4) | 0.028 (3) | 0.004 (3) | 0.003 (2) | 0.018 (3) |
C3B | 0.028 (3) | 0.036 (4) | 0.030 (3) | 0.005 (3) | 0.011 (3) | 0.010 (3) |
C4B | 0.038 (4) | 0.042 (4) | 0.046 (4) | 0.003 (3) | −0.011 (3) | −0.004 (3) |
C5B | 0.023 (3) | 0.032 (3) | 0.040 (3) | 0.010 (3) | 0.009 (3) | 0.012 (3) |
C6B | 0.036 (3) | 0.027 (3) | 0.046 (4) | 0.008 (3) | 0.008 (3) | 0.026 (3) |
O2B | 0.036 (2) | 0.045 (3) | 0.042 (3) | 0.006 (2) | 0.0141 (19) | 0.029 (2) |
C7B | 0.028 (3) | 0.023 (3) | 0.030 (3) | 0.000 (2) | 0.005 (2) | 0.013 (3) |
C8B | 0.049 (4) | 0.031 (4) | 0.028 (3) | 0.005 (3) | 0.001 (3) | 0.017 (3) |
C9B | 0.048 (4) | 0.022 (3) | 0.032 (3) | 0.000 (3) | 0.012 (3) | 0.010 (3) |
C10B | 0.084 (6) | 0.051 (5) | 0.056 (5) | 0.015 (4) | 0.037 (4) | 0.033 (4) |
C11B | 0.050 (4) | 0.026 (3) | 0.039 (4) | 0.008 (3) | 0.010 (3) | 0.014 (3) |
C12B | 0.027 (3) | 0.032 (4) | 0.050 (4) | 0.002 (3) | 0.000 (3) | 0.017 (3) |
Sn1A—C1A | 2.219 (6) | Sn1B—C1B | 2.215 (5) |
Sn1A—C7A | 2.220 (6) | Sn1B—C7B | 2.218 (6) |
Sn1A—O1A | 2.428 (4) | Sn1B—O2B | 2.435 (4) |
Sn1A—O2A | 2.438 (4) | Sn1B—O1B | 2.439 (4) |
Sn1A—I1A | 2.8354 (5) | Sn1B—I2B | 2.8378 (5) |
Sn1A—I2A | 2.8572 (5) | Sn1B—I1B | 2.8551 (5) |
O1A—C3A | 1.218 (7) | O1B—C3B | 1.230 (7) |
C1A—C5A | 1.511 (8) | C1B—C2B | 1.527 (8) |
C1A—C2A | 1.522 (8) | C1B—C6B | 1.527 (8) |
C1A—C6A | 1.538 (8) | C1B—C5B | 1.529 (8) |
C2A—C3A | 1.489 (9) | C2B—C3B | 1.474 (9) |
C3A—C4A | 1.491 (9) | C3B—C4B | 1.490 (9) |
O2A—C9A | 1.227 (7) | O2B—C9B | 1.227 (7) |
C7A—C12A | 1.522 (8) | C7B—C8B | 1.517 (8) |
C7A—C11A | 1.523 (8) | C7B—C11B | 1.521 (8) |
C7A—C8A | 1.527 (7) | C7B—C12B | 1.525 (8) |
C8A—C9A | 1.480 (9) | C8B—C9B | 1.489 (9) |
C9A—C10A | 1.475 (8) | C9B—C10B | 1.491 (9) |
C1A—Sn1A—C7A | 160.4 (2) | C1B—Sn1B—C7B | 161.1 (2) |
C1A—Sn1A—O1A | 74.67 (18) | C1B—Sn1B—O2B | 90.18 (17) |
C7A—Sn1A—O1A | 90.28 (17) | C7B—Sn1B—O2B | 75.15 (17) |
C1A—Sn1A—O2A | 89.19 (18) | C1B—Sn1B—O1B | 74.74 (18) |
C7A—Sn1A—O2A | 74.66 (17) | C7B—Sn1B—O1B | 89.86 (18) |
O1A—Sn1A—O2A | 75.67 (15) | O2B—Sn1B—O1B | 75.37 (14) |
C1A—Sn1A—I1A | 95.55 (15) | C1B—Sn1B—I2B | 97.10 (15) |
C7A—Sn1A—I1A | 97.15 (14) | C7B—Sn1B—I2B | 94.90 (15) |
O1A—Sn1A—I1A | 90.51 (11) | O2B—Sn1B—I2B | 90.57 (11) |
O2A—Sn1A—I1A | 163.68 (11) | O1B—Sn1B—I2B | 163.49 (10) |
C1A—Sn1A—I2A | 96.87 (15) | C1B—Sn1B—I1B | 93.98 (14) |
C7A—Sn1A—I2A | 94.22 (14) | C7B—Sn1B—I1B | 96.75 (14) |
O1A—Sn1A—I2A | 163.11 (11) | O2B—Sn1B—I1B | 162.56 (11) |
O2A—Sn1A—I2A | 89.82 (11) | O1B—Sn1B—I1B | 89.39 (10) |
I1A—Sn1A—I2A | 105.037 (16) | I2B—Sn1B—I1B | 105.675 (16) |
C3A—O1A—Sn1A | 111.8 (4) | C3B—O1B—Sn1B | 110.3 (4) |
C5A—C1A—C2A | 111.6 (5) | C2B—C1B—C6B | 110.3 (5) |
C5A—C1A—C6A | 109.7 (5) | C2B—C1B—C5B | 111.3 (5) |
C2A—C1A—C6A | 109.5 (5) | C6B—C1B—C5B | 110.1 (5) |
C5A—C1A—Sn1A | 109.9 (4) | C2B—C1B—Sn1B | 106.2 (4) |
C2A—C1A—Sn1A | 106.1 (4) | C6B—C1B—Sn1B | 110.5 (4) |
C6A—C1A—Sn1A | 110.0 (4) | C5B—C1B—Sn1B | 108.4 (4) |
C3A—C2A—C1A | 115.6 (5) | C3B—C2B—C1B | 115.6 (5) |
O1A—C3A—C2A | 119.8 (5) | O1B—C3B—C2B | 121.1 (6) |
O1A—C3A—C4A | 120.6 (6) | O1B—C3B—C4B | 120.4 (6) |
C2A—C3A—C4A | 119.5 (6) | C2B—C3B—C4B | 118.3 (6) |
C9A—O2A—Sn1A | 110.4 (4) | C9B—O2B—Sn1B | 110.8 (4) |
C12A—C7A—C11A | 110.4 (5) | C8B—C7B—C11B | 110.5 (5) |
C12A—C7A—C8A | 109.8 (5) | C8B—C7B—C12B | 109.8 (5) |
C11A—C7A—C8A | 111.1 (4) | C11B—C7B—C12B | 110.2 (5) |
C12A—C7A—Sn1A | 110.6 (4) | C8B—C7B—Sn1B | 106.1 (4) |
C11A—C7A—Sn1A | 109.1 (4) | C11B—C7B—Sn1B | 109.5 (4) |
C8A—C7A—Sn1A | 105.7 (4) | C12B—C7B—Sn1B | 110.7 (4) |
C9A—C8A—C7A | 116.1 (5) | C9B—C8B—C7B | 115.9 (5) |
O2A—C9A—C10A | 120.5 (6) | O2B—C9B—C8B | 120.5 (5) |
O2A—C9A—C8A | 120.7 (5) | O2B—C9B—C10B | 119.2 (6) |
C10A—C9A—C8A | 118.8 (6) | C8B—C9B—C10B | 120.2 (6) |
C1A—Sn1A—O1A—C3A | −16.9 (4) | C1B—Sn1B—O1B—C3B | −19.1 (4) |
C7A—Sn1A—O1A—C3A | 175.9 (4) | C7B—Sn1B—O1B—C3B | 172.0 (4) |
O2A—Sn1A—O1A—C3A | −110.0 (4) | O2B—Sn1B—O1B—C3B | −113.4 (4) |
I1A—Sn1A—O1A—C3A | 78.8 (4) | I2B—Sn1B—O1B—C3B | −81.0 (5) |
I2A—Sn1A—O1A—C3A | −78.4 (6) | I1B—Sn1B—O1B—C3B | 75.2 (4) |
C7A—Sn1A—C1A—C5A | −52.9 (8) | C7B—Sn1B—C1B—C2B | 63.8 (7) |
O1A—Sn1A—C1A—C5A | −94.0 (4) | O2B—Sn1B—C1B—C2B | 102.2 (4) |
O2A—Sn1A—C1A—C5A | −18.7 (4) | O1B—Sn1B—C1B—C2B | 27.5 (3) |
I1A—Sn1A—C1A—C5A | 177.0 (4) | I2B—Sn1B—C1B—C2B | −167.2 (3) |
I2A—Sn1A—C1A—C5A | 71.1 (4) | I1B—Sn1B—C1B—C2B | −60.8 (3) |
C7A—Sn1A—C1A—C2A | 67.9 (8) | C7B—Sn1B—C1B—C6B | −176.6 (5) |
O1A—Sn1A—C1A—C2A | 26.8 (4) | O2B—Sn1B—C1B—C6B | −138.1 (4) |
O2A—Sn1A—C1A—C2A | 102.1 (4) | O1B—Sn1B—C1B—C6B | 147.1 (4) |
I1A—Sn1A—C1A—C2A | −62.2 (4) | I2B—Sn1B—C1B—C6B | −47.5 (4) |
I2A—Sn1A—C1A—C2A | −168.2 (4) | I1B—Sn1B—C1B—C6B | 58.9 (4) |
C7A—Sn1A—C1A—C6A | −173.8 (5) | C7B—Sn1B—C1B—C5B | −55.9 (8) |
O1A—Sn1A—C1A—C6A | 145.1 (4) | O2B—Sn1B—C1B—C5B | −17.4 (4) |
O2A—Sn1A—C1A—C6A | −139.5 (4) | O1B—Sn1B—C1B—C5B | −92.2 (4) |
I1A—Sn1A—C1A—C6A | 56.1 (4) | I2B—Sn1B—C1B—C5B | 73.2 (4) |
I2A—Sn1A—C1A—C6A | −49.8 (4) | I1B—Sn1B—C1B—C5B | 179.5 (4) |
C5A—C1A—C2A—C3A | 81.5 (6) | C6B—C1B—C2B—C3B | −157.2 (5) |
C6A—C1A—C2A—C3A | −156.8 (5) | C5B—C1B—C2B—C3B | 80.3 (6) |
Sn1A—C1A—C2A—C3A | −38.2 (6) | Sn1B—C1B—C2B—C3B | −37.5 (6) |
Sn1A—O1A—C3A—C2A | 0.4 (7) | Sn1B—O1B—C3B—C2B | 3.7 (6) |
Sn1A—O1A—C3A—C4A | −176.7 (5) | Sn1B—O1B—C3B—C4B | −171.2 (5) |
C1A—C2A—C3A—O1A | 26.1 (8) | C1B—C2B—C3B—O1B | 23.0 (8) |
C1A—C2A—C3A—C4A | −156.7 (6) | C1B—C2B—C3B—C4B | −161.9 (5) |
C1A—Sn1A—O2A—C9A | 170.0 (4) | C1B—Sn1B—O2B—C9B | 175.5 (4) |
C7A—Sn1A—O2A—C9A | −21.3 (4) | C7B—Sn1B—O2B—C9B | −16.5 (4) |
O1A—Sn1A—O2A—C9A | −115.7 (4) | O1B—Sn1B—O2B—C9B | −110.3 (4) |
I1A—Sn1A—O2A—C9A | −82.8 (5) | I2B—Sn1B—O2B—C9B | 78.4 (4) |
I2A—Sn1A—O2A—C9A | 73.1 (4) | I1B—Sn1B—O2B—C9B | −80.5 (5) |
C1A—Sn1A—C7A—C12A | −177.3 (5) | C1B—Sn1B—C7B—C8B | 66.5 (8) |
O1A—Sn1A—C7A—C12A | −137.9 (4) | O2B—Sn1B—C7B—C8B | 26.4 (4) |
O2A—Sn1A—C7A—C12A | 147.1 (4) | O1B—Sn1B—C7B—C8B | 101.3 (4) |
I1A—Sn1A—C7A—C12A | −47.3 (4) | I2B—Sn1B—C7B—C8B | −62.9 (4) |
I2A—Sn1A—C7A—C12A | 58.4 (4) | I1B—Sn1B—C7B—C8B | −169.3 (4) |
C1A—Sn1A—C7A—C11A | −55.6 (8) | C1B—Sn1B—C7B—C11B | −52.8 (8) |
O1A—Sn1A—C7A—C11A | −16.2 (4) | O2B—Sn1B—C7B—C11B | −92.8 (4) |
O2A—Sn1A—C7A—C11A | −91.3 (4) | O1B—Sn1B—C7B—C11B | −18.0 (4) |
I1A—Sn1A—C7A—C11A | 74.3 (4) | I2B—Sn1B—C7B—C11B | 177.9 (4) |
I2A—Sn1A—C7A—C11A | −179.9 (4) | I1B—Sn1B—C7B—C11B | 71.4 (4) |
C1A—Sn1A—C7A—C8A | 64.0 (7) | C1B—Sn1B—C7B—C12B | −174.5 (5) |
O1A—Sn1A—C7A—C8A | 103.3 (3) | O2B—Sn1B—C7B—C12B | 145.5 (4) |
O2A—Sn1A—C7A—C8A | 28.3 (3) | O1B—Sn1B—C7B—C12B | −139.7 (4) |
I1A—Sn1A—C7A—C8A | −166.1 (3) | I2B—Sn1B—C7B—C12B | 56.2 (4) |
I2A—Sn1A—C7A—C8A | −60.4 (3) | I1B—Sn1B—C7B—C12B | −50.3 (4) |
C12A—C7A—C8A—C9A | −156.6 (5) | C11B—C7B—C8B—C9B | 81.0 (6) |
C11A—C7A—C8A—C9A | 80.9 (6) | C12B—C7B—C8B—C9B | −157.2 (5) |
Sn1A—C7A—C8A—C9A | −37.4 (5) | Sn1B—C7B—C8B—C9B | −37.6 (6) |
Sn1A—O2A—C9A—C10A | −170.5 (5) | Sn1B—O2B—C9B—C8B | 0.3 (7) |
Sn1A—O2A—C9A—C8A | 6.8 (7) | Sn1B—O2B—C9B—C10B | −176.4 (5) |
C7A—C8A—C9A—O2A | 20.8 (8) | C7B—C8B—C9B—O2B | 25.8 (9) |
C7A—C8A—C9A—C10A | −161.9 (6) | C7B—C8B—C9B—C10B | −157.4 (6) |
Experimental details
Crystal data | |
Chemical formula | [SnI2(C6H11O)2] |
Mr | 570.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 7.8655 (2), 14.8464 (4), 16.4602 (4) |
α, β, γ (°) | 108.0591 (14), 102.0352 (14), 90.0908 (14) |
V (Å3) | 1782.73 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.89 |
Crystal size (mm) | 0.12 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Nonius KappaCCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.692, 0.795 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28392, 8156, 6019 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.100, 1.00 |
No. of reflections | 8156 |
No. of parameters | 320 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.36, −1.62 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Compound (I) | Compound (II)a | ||
Molecule A | Molecule B | ||
Sn1-C1 | 2.219 (6) | 2.215 (5) | 2.123 (10) |
Sn1-C7 | 2.220 (6) | 2.218 (6) | 2.144 (11) |
Sn1-O1 | 2.428 (4) | 2.439 (4) | 2.522 (8) |
Sn1-O2 | 2.438 (4) | 2.435 (4) | 2.528 (7) |
Sn1-I1 | 2.8354 (5) | 2.8551 (5) | 2.7775 (12) |
Sn1-I2 | 2.8572 (5) | 2.8378 (5) | 2.7801 (11) |
C1-Sn1-O1 | 74.67 (18) | 74.74 (18) | 72.8 (3) |
C7-Sn1-O2 | 74.66 (17) | 75.15 (17) | 73.9 (4) |
O1-Sn1-O2 | 75.67 (15) | 75.37 (14) | 86.6 (3) |
C1-Sn1-C7 | 160.4 (2) | 161.1 (2) | 144.0 (5) |
O2-Sn1-I1 | 163.68 (11) | 162.56 (11) | 173.7 (2) |
O1-Sn1-I2 | 163.11 (11) | 163.49 (10) | 173.5 (2) |
I1-Sn1-I2 | 105.037 (16) | 105.675 (16) | 98.52 (3) |
a Corresponding parameters for (II) (Balasubramanian et al., 1997). |
3-(Halostannyl)propanoic esters, so called estertin compounds, such as X2Sn(CH2CH2CO2R)2 and X3SnCH2CH2CO2R, have been known for almost 25 years (Hutton & Oakes, 1976). The initial interest in these compounds as precursors of PVC stabilizers has long since waned, but interest persists in their coordination chemistry (Balasubramanian et al., 1997, and references therein). (3-Halostannyl)alkanones, e.g. X2Sn(CR2CH2COR)2, have been known for a similar period (Hutton & Oakes, 1976), but have been less extensively investigated, especially in regard to their coordination chemistry. Comparison of the structures of the title compound, I2Sn(CMe2CH2COMe)2, (I), now reported, and that of I2Sn(CH2CH2CO2Me)2, (II), reported previously by Balasubramanian et al. (1997), allows the relative donor abilities of the intramolecular ester and ketone groups to be assessed. \sch
Both (I) and (II) exist as molecular compounds, but with different degrees of octahedral distortion. The organic groups act as C,O-chelating ligands, with the O atoms trans to the cis-iodides. Selected geometric parameters for both compounds are listed in Table 1.
The ketone group in (I) is a stronger donor than the ester group in (II), as shown by the shorter Sn—O bonds and the longer Sn—I bonds. For comparison, Sn—I bond lengths in four-coordinate tetrahedral diorganotin diiodides are in the range 2.649–2.719 Å (Balasubramanian et al., 1997). Longer Sn—I bond lengths [2.965 (1) and 3.009 (1) Å] were found in octahedral [(p-MeC6H4){2,6-(Me2NCH2)2C6H3—C,N,N''}SnI2], but here the iodides were in a trans arrangement (Jastrzebski et al., 1991).
The chelate bite angles in (I) [74.66 (17)–75.15 (17)°] are slightly larger than those in (II) [73.9 (4) and 72.8 (3)°; Balasubramanian et al., 1997]. The bite angles result in octahedral distortions and there are significant differences between the C—Sn—C angles in (I) and (II): 144.0 (5)° in (II), and 160.4 (2) and 163.1 (2)° in the two independent molecules of (I).