Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004214/ci6014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004214/ci6014Isup2.hkl |
CCDC reference: 162798
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.010 Å
- Disorder in main residue
- R factor = 0.022
- wR factor = 0.049
- Data-to-parameter ratio = 13.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
PLAT_213 Alert B Atom C206 has ADP max/min Ratio ........... 4.40
Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack 0.500 From the CIF: _refine_ls_abs_structure_Flack_su 0.020 Alert C Flack test results are ambiguous. PLAT_301 Alert C Main Residue Disorder ........................ 8.00 Perc. PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(207) - C(208) = 1.39 Ang. PLAT_731 Alert C Bond Calc 1.393(18), Rep 1.394(8) .... 2.25 s.u-Ratio C207 -C208 1.555 1.555 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.24 From the CIF: _reflns_number_total 8637 Count of symmetry unique reflns 7272 Completeness (_total/calc) 118.77% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1365 Fraction of Friedel pairs measured 0.188 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
4 Alert Level C = Please check
The title compound was obtained by refluxing for 6 h equimolar (10 mmol) quantities of thiophene-2-carboxylic acid and dibutyltin oxide in a solution of 200 ml chloroform and 50 ml e thanol. The generated azeotrope was distilled off and evaporated under vacuum. Crystals were obtained by recrystallization from an ethanol solution.
Two thiophene rings are disordered. The resolution of the data did not allow two distinct positions for the S and C atoms to be distinguished. Only one peak was found for each atom in the difference map. Thus, a C and an S atom were refined sharing the same position and the same displacement parameters and just refining the site occupation factor of the respective C and S atoms in order to determine the ratio of the different orientations, which turned out to be 0.760 (7) for C33 and S36, 0.240 (7) for S33 and C36, 0.808 (6) for C43 and S46, and 0.192 (6) for S43 and C46. All H atoms except those of the disordered atoms were located by difference Fourier synthesis and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or 1.5 Ueq(Cmethyl)] using a riding model with aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å or methylene C—H = 0.99 Å. One butyl group was refined with a disorder model for the three terminal atoms. Distance restraints of 1.52 (1) and 2.52 (1) Å were applied to the 1–2 and 1–3 C—C distances in the disordered group and for the residues C205, C206, C207 and C208. The ratio of the two twin components refined to 0.50 (2). The displacement ellipsoid of C206 is elongated perpendicular to the methylene chain, which might indicate disorder and pretends a too short C—C bond.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Siemens, 1991).
[Sn4O2(C5H3O2S)4(C4H9)8] | F(000) = 1480 |
Mr = 1472.19 | Dx = 1.555 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.495 (2) Å | Cell parameters from 492 reflections |
b = 17.324 (3) Å | θ = 1–25° |
c = 13.471 (2) Å | µ = 1.75 mm−1 |
β = 93.01 (1)° | T = 173 K |
V = 3145.0 (9) Å3 | Block, colourless |
Z = 2 | 0.46 × 0.42 × 0.34 mm |
Siemens CCD three-circle diffractometer | 8637 independent reflections |
Radiation source: fine-focus sealed tube | 7626 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ω scans | θmax = 27.2°, θmin = 1.5° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.470, Tmax = 0.550 | k = −21→10 |
12639 measured reflections | l = 0→16 |
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)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.049 | w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
8637 reflections | Δρmax = 0.47 e Å−3 |
653 parameters | Δρmin = −0.57 e Å−3 |
15 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.50 (2) |
[Sn4O2(C5H3O2S)4(C4H9)8] | V = 3145.0 (9) Å3 |
Mr = 1472.19 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 13.495 (2) Å | µ = 1.75 mm−1 |
b = 17.324 (3) Å | T = 173 K |
c = 13.471 (2) Å | 0.46 × 0.42 × 0.34 mm |
β = 93.01 (1)° |
Siemens CCD three-circle diffractometer | 8637 independent reflections |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | 7626 reflections with I > 2σ(I) |
Tmin = 0.470, Tmax = 0.550 | Rint = 0.015 |
12639 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.049 | Δρmax = 0.47 e Å−3 |
S = 0.96 | Δρmin = −0.57 e Å−3 |
8637 reflections | Absolute structure: Flack (1983) |
653 parameters | Absolute structure parameter: 0.50 (2) |
15 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.36159 (2) | 0.29767 (2) | 0.79329 (2) | 0.02546 (9) | |
O1 | 0.23474 (19) | 0.3359 (2) | 0.8546 (2) | 0.0255 (8) | |
Sn2 | 0.12516 (2) | 0.33406 (2) | 0.73123 (2) | 0.02596 (9) | |
O2 | 0.2512 (2) | 0.2946 (2) | 0.6701 (2) | 0.0276 (8) | |
Sn3 | 0.19353 (2) | 0.36318 (2) | 0.99338 (2) | 0.02758 (9) | |
Sn4 | 0.29313 (2) | 0.26249 (2) | 0.53360 (2) | 0.02974 (10) | |
O11 | 0.4517 (2) | 0.3124 (3) | 0.9376 (2) | 0.0405 (12) | |
C11 | 0.4297 (3) | 0.3142 (3) | 1.0261 (4) | 0.0308 (14) | |
O12 | 0.3455 (2) | 0.3315 (3) | 1.0568 (2) | 0.0477 (12) | |
C12 | 0.5072 (3) | 0.2920 (4) | 1.1025 (3) | 0.0304 (12) | |
S13 | 0.48102 (10) | 0.29016 (12) | 1.22583 (10) | 0.0485 (4) | |
C14 | 0.5976 (4) | 0.2620 (4) | 1.2579 (4) | 0.0487 (17) | |
H14 | 0.6217 | 0.2540 | 1.3247 | 0.058* | |
C15 | 0.6534 (4) | 0.2519 (4) | 1.1785 (4) | 0.0473 (17) | |
H15 | 0.7204 | 0.2348 | 1.1846 | 0.057* | |
C16 | 0.6045 (3) | 0.2688 (4) | 1.0858 (3) | 0.0318 (13) | |
H16 | 0.6327 | 0.2651 | 1.0229 | 0.038* | |
O21 | 0.0354 (2) | 0.3200 (3) | 0.5862 (2) | 0.0411 (12) | |
C21 | 0.0564 (4) | 0.3077 (4) | 0.4987 (4) | 0.0327 (14) | |
O22 | 0.1376 (2) | 0.2808 (3) | 0.4732 (3) | 0.0586 (14) | |
C22 | −0.0198 (3) | 0.3236 (4) | 0.4204 (3) | 0.0351 (14) | |
S23 | 0.00570 (11) | 0.31025 (14) | 0.29845 (11) | 0.0693 (7) | |
C24 | −0.1095 (4) | 0.3390 (5) | 0.2596 (4) | 0.071 (2) | |
H24 | −0.1319 | 0.3413 | 0.1916 | 0.085* | |
C25 | −0.1669 (4) | 0.3584 (5) | 0.3359 (4) | 0.0561 (19) | |
H25 | −0.2337 | 0.3752 | 0.3263 | 0.067* | |
C26 | −0.1173 (3) | 0.3513 (3) | 0.4311 (3) | 0.0246 (12) | |
H26 | −0.1454 | 0.3632 | 0.4925 | 0.029* | |
O31 | 0.0530 (2) | 0.3857 (2) | 0.9093 (2) | 0.0305 (9) | |
C31 | −0.0140 (4) | 0.4002 (4) | 0.9721 (4) | 0.0350 (14) | |
C32 | −0.1187 (3) | 0.4067 (4) | 0.9276 (4) | 0.0332 (14) | |
O32 | 0.0032 (3) | 0.4068 (3) | 1.0612 (3) | 0.0449 (11) | |
C33 | −0.1472 (3) | 0.4044 (3) | 0.8179 (4) | 0.080 (2) | 0.760 (7) |
H33 | −0.1067 | 0.3996 | 0.7626 | 0.096* | 0.760 (7) |
S33 | −0.1472 (3) | 0.4044 (3) | 0.8179 (4) | 0.080 (2) | 0.240 (7) |
C34 | −0.2571 (5) | 0.4116 (5) | 0.8208 (6) | 0.060 (2) | |
H34 | −0.2982 | 0.4097 | 0.7614 | 0.073* | |
C35 | −0.2968 (4) | 0.4208 (4) | 0.9102 (6) | 0.063 (2) | |
H35 | −0.3660 | 0.4266 | 0.9177 | 0.076* | |
S36 | −0.21139 (12) | 0.42118 (14) | 1.00797 (16) | 0.0522 (8) | 0.760 (7) |
C36 | −0.21139 (12) | 0.42118 (14) | 1.00797 (16) | 0.0522 (8) | 0.240 (7) |
H36 | −0.2140 | 0.4270 | 1.0779 | 0.063* | 0.240 (7) |
O41 | 0.4346 (2) | 0.2479 (2) | 0.6193 (2) | 0.0312 (9) | |
C41 | 0.5055 (3) | 0.2358 (3) | 0.5577 (4) | 0.0267 (13) | |
C42 | 0.6071 (3) | 0.2303 (3) | 0.6038 (4) | 0.0288 (13) | |
O42 | 0.4893 (2) | 0.2288 (3) | 0.4685 (3) | 0.0373 (10) | |
C43 | 0.6356 (3) | 0.2371 (3) | 0.7136 (3) | 0.0602 (17) | 0.808 (6) |
H43 | 0.5947 | 0.2444 | 0.7682 | 0.072* | 0.808 (6) |
S43 | 0.6356 (3) | 0.2371 (3) | 0.7136 (3) | 0.0602 (17) | 0.192 (6) |
C44 | 0.7467 (4) | 0.2290 (4) | 0.7124 (4) | 0.0456 (16) | |
H44 | 0.7875 | 0.2324 | 0.7719 | 0.055* | |
C45 | 0.7853 (4) | 0.2169 (4) | 0.6255 (4) | 0.0472 (18) | |
H45 | 0.8544 | 0.2102 | 0.6185 | 0.057* | |
S46 | 0.70183 (12) | 0.21435 (13) | 0.52853 (13) | 0.0471 (7) | 0.808 (6) |
C46 | 0.70183 (12) | 0.21435 (13) | 0.52853 (13) | 0.0471 (7) | 0.192 (6) |
H46 | 0.7060 | 0.2069 | 0.4590 | 0.057* | 0.192 (6) |
C101 | 0.4391 (3) | 0.3969 (3) | 0.7452 (4) | 0.0301 (13) | |
H10A | 0.5111 | 0.3855 | 0.7480 | 0.036* | |
H10B | 0.4183 | 0.4077 | 0.6749 | 0.036* | |
C102 | 0.4215 (4) | 0.4694 (4) | 0.8071 (4) | 0.0398 (15) | |
H10C | 0.4426 | 0.4589 | 0.8773 | 0.048* | |
H10D | 0.3496 | 0.4809 | 0.8043 | 0.048* | |
C103 | 0.4775 (5) | 0.5404 (4) | 0.7716 (5) | 0.061 (2) | |
H10E | 0.4721 | 0.5826 | 0.8205 | 0.073* | |
H10F | 0.5487 | 0.5275 | 0.7677 | 0.073* | |
C104 | 0.4365 (6) | 0.5679 (4) | 0.6701 (6) | 0.083 (2) | |
H10G | 0.4746 | 0.6126 | 0.6492 | 0.124* | |
H10H | 0.3667 | 0.5825 | 0.6743 | 0.124* | |
H10I | 0.4418 | 0.5262 | 0.6215 | 0.124* | |
C105 | 0.3615 (4) | 0.1759 (4) | 0.8209 (4) | 0.0412 (15) | |
H10J | 0.3134 | 0.1670 | 0.8726 | 0.049* | |
H10K | 0.3332 | 0.1513 | 0.7594 | 0.049* | |
C106 | 0.4512 (5) | 0.1314 (5) | 0.8512 (7) | 0.081 (3) | |
H10L | 0.4888 | 0.1609 | 0.9037 | 0.097* | |
H10M | 0.4934 | 0.1279 | 0.7935 | 0.097* | |
C107 | 0.4348 (8) | 0.0502 (5) | 0.8899 (8) | 0.097 (3) | |
H10N | 0.4990 | 0.0283 | 0.9152 | 0.117* | |
H10O | 0.3900 | 0.0522 | 0.9457 | 0.117* | |
C108 | 0.3917 (7) | 0.0007 (5) | 0.8115 (7) | 0.103 (3) | |
H10P | 0.3809 | −0.0510 | 0.8383 | 0.155* | |
H10Q | 0.4371 | −0.0025 | 0.7572 | 0.155* | |
H10R | 0.3282 | 0.0224 | 0.7864 | 0.155* | |
C201 | 0.0434 (4) | 0.2375 (4) | 0.7803 (4) | 0.0361 (14) | |
H20A | 0.0606 | 0.2287 | 0.8517 | 0.043* | |
H20B | −0.0283 | 0.2496 | 0.7732 | 0.043* | |
C202 | 0.0627 (5) | 0.1653 (4) | 0.7243 (5) | 0.0492 (17) | |
H20C | 0.1347 | 0.1539 | 0.7294 | 0.059* | |
H20D | 0.0429 | 0.1731 | 0.6532 | 0.059* | |
C203 | 0.0048 (6) | 0.0954 (5) | 0.7648 (6) | 0.077 (2) | |
H20E | 0.0280 | 0.0860 | 0.8347 | 0.092* | |
H20F | −0.0665 | 0.1087 | 0.7643 | 0.092* | |
C204 | 0.0162 (8) | 0.0246 (6) | 0.7082 (9) | 0.156 (5) | |
H20G | −0.0210 | −0.0171 | 0.7384 | 0.234* | |
H20H | 0.0866 | 0.0106 | 0.7086 | 0.234* | |
H20I | −0.0094 | 0.0325 | 0.6396 | 0.234* | |
C205 | 0.1255 (4) | 0.4545 (4) | 0.7082 (4) | 0.0433 (16) | |
H20J | 0.1266 | 0.4791 | 0.7745 | 0.052* | |
H20K | 0.1892 | 0.4676 | 0.6790 | 0.052* | |
C206 | 0.0464 (7) | 0.4922 (5) | 0.6465 (11) | 0.191 (7) | |
H20L | −0.0186 | 0.4742 | 0.6684 | 0.229* | |
H20M | 0.0518 | 0.4756 | 0.5767 | 0.229* | |
C207 | 0.0483 (8) | 0.5809 (5) | 0.6500 (11) | 0.170 (6) | |
H20N | −0.0157 | 0.6001 | 0.6204 | 0.203* | |
H20O | 0.0525 | 0.5970 | 0.7207 | 0.203* | |
C208 | 0.1246 (10) | 0.6171 (7) | 0.6021 (13) | 0.258 (11) | |
H20P | 0.1185 | 0.6732 | 0.6091 | 0.387* | |
H20Q | 0.1203 | 0.6034 | 0.5314 | 0.387* | |
H20R | 0.1888 | 0.6003 | 0.6320 | 0.387* | |
C301 | 0.1474 (4) | 0.2665 (4) | 1.0743 (4) | 0.0389 (14) | |
H30A | 0.1624 | 0.2768 | 1.1458 | 0.047* | |
H30B | 0.0744 | 0.2622 | 1.0643 | 0.047* | |
C302 | 0.1913 (5) | 0.1911 (4) | 1.0500 (4) | 0.0545 (18) | |
H30C | 0.2644 | 0.1963 | 1.0534 | 0.065* | |
H30D | 0.1702 | 0.1776 | 0.9807 | 0.065* | |
C303 | 0.1626 (6) | 0.1235 (4) | 1.1193 (6) | 0.078 (3) | |
H30E | 0.0894 | 0.1212 | 1.1217 | 0.093* | |
H30F | 0.1852 | 0.0741 | 1.0913 | 0.093* | |
C304 | 0.2079 (8) | 0.1327 (6) | 1.2238 (6) | 0.109 (3) | |
H30G | 0.1878 | 0.0894 | 1.2649 | 0.163* | |
H30H | 0.1849 | 0.1812 | 1.2523 | 0.163* | |
H30I | 0.2804 | 0.1336 | 1.2220 | 0.163* | |
C305 | 0.2345 (4) | 0.4780 (4) | 1.0278 (4) | 0.0428 (16) | |
H30J | 0.2448 | 0.4815 | 1.1010 | 0.051* | |
H30K | 0.2998 | 0.4873 | 0.9997 | 0.051* | |
C306 | 0.1667 (4) | 0.5439 (4) | 0.9945 (4) | 0.0419 (16) | |
H30L | 0.1023 | 0.5380 | 1.0258 | 0.050* | |
H30M | 0.1538 | 0.5409 | 0.9216 | 0.050* | |
C307 | 0.2099 (5) | 0.6231 (4) | 1.0212 (5) | 0.058 (2) | |
H30N | 0.2247 | 0.6256 | 1.0939 | 0.070* | |
H30O | 0.2731 | 0.6298 | 0.9881 | 0.070* | |
C308 | 0.1409 (5) | 0.6875 (5) | 0.9910 (6) | 0.071 (2) | |
H30P | 0.1714 | 0.7370 | 1.0104 | 0.106* | |
H30Q | 0.0784 | 0.6814 | 1.0240 | 0.106* | |
H30R | 0.1278 | 0.6864 | 0.9188 | 0.106* | |
C401 | 0.2607 (4) | 0.1442 (4) | 0.5065 (5) | 0.0524 (18) | |
H40A | 0.2086 | 0.1295 | 0.5520 | 0.063* | |
H40B | 0.2304 | 0.1408 | 0.4382 | 0.063* | |
C402 | 0.3378 (5) | 0.0843 (4) | 0.5154 (5) | 0.059 (2) | |
H40C | 0.3689 | 0.0857 | 0.5836 | 0.071* | |
H40D | 0.3900 | 0.0964 | 0.4688 | 0.071* | |
C403 | 0.3003 (5) | 0.0036 (5) | 0.4943 (6) | 0.074 (2) | |
H40E | 0.2689 | 0.0029 | 0.4262 | 0.089* | |
H40F | 0.2477 | −0.0077 | 0.5407 | 0.089* | |
C404 | 0.3753 (6) | −0.0614 (5) | 0.5021 (7) | 0.100 (3) | |
H40G | 0.3428 | −0.1101 | 0.4831 | 0.149* | |
H40H | 0.4029 | −0.0650 | 0.5707 | 0.149* | |
H40I | 0.4289 | −0.0510 | 0.4576 | 0.149* | |
C405 | 0.3322 (5) | 0.3606 (4) | 0.4487 (4) | 0.0583 (19) | |
H40J | 0.4025 | 0.3730 | 0.4665 | 0.070* | |
H40K | 0.3282 | 0.3455 | 0.3778 | 0.070* | |
C406 | 0.2728 (6) | 0.4336 (4) | 0.4584 (6) | 0.104 (3) | |
H40L | 0.3038 | 0.4658 | 0.5122 | 0.125* | 0.517 (16) |
H40M | 0.2050 | 0.4199 | 0.4770 | 0.125* | 0.517 (16) |
H40N | 0.2659 | 0.4447 | 0.5298 | 0.125* | 0.483 (16) |
H40O | 0.2055 | 0.4258 | 0.4271 | 0.125* | 0.483 (16) |
C471 | 0.2644 (9) | 0.4791 (9) | 0.3606 (12) | 0.123 (9) | 0.517 (16) |
H47A | 0.2381 | 0.4449 | 0.3066 | 0.148* | 0.517 (16) |
H47B | 0.2170 | 0.5222 | 0.3671 | 0.148* | 0.517 (16) |
C472 | 0.3217 (11) | 0.5029 (5) | 0.4088 (9) | 0.060 (5) | 0.483 (16) |
H47C | 0.2936 | 0.5513 | 0.4343 | 0.072* | 0.483 (16) |
H47D | 0.3938 | 0.5027 | 0.4269 | 0.072* | 0.483 (16) |
C481 | 0.3632 (11) | 0.5109 (13) | 0.3337 (14) | 0.101 (8) | 0.517 (16) |
H48A | 0.3551 | 0.5399 | 0.2713 | 0.152* | 0.517 (16) |
H48B | 0.4098 | 0.4683 | 0.3255 | 0.152* | 0.517 (16) |
H48C | 0.3891 | 0.5453 | 0.3867 | 0.152* | 0.517 (16) |
C482 | 0.3061 (16) | 0.5008 (12) | 0.2980 (8) | 0.081 (7) | 0.483 (16) |
H48D | 0.3381 | 0.5457 | 0.2692 | 0.122* | 0.483 (16) |
H48E | 0.2348 | 0.5019 | 0.2798 | 0.122* | 0.483 (16) |
H48F | 0.3351 | 0.4534 | 0.2723 | 0.122* | 0.483 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02083 (16) | 0.0302 (2) | 0.02557 (17) | 0.00244 (16) | 0.00295 (13) | 0.00175 (16) |
O1 | 0.0223 (15) | 0.033 (2) | 0.0214 (15) | 0.0013 (16) | 0.0008 (13) | −0.0059 (16) |
Sn2 | 0.02052 (16) | 0.0318 (3) | 0.02571 (17) | 0.00237 (15) | 0.00290 (13) | −0.00017 (16) |
O2 | 0.0229 (16) | 0.036 (2) | 0.0238 (15) | 0.0035 (17) | 0.0036 (13) | −0.0032 (17) |
Sn3 | 0.02515 (17) | 0.0340 (3) | 0.02380 (17) | 0.00534 (16) | 0.00305 (14) | −0.00103 (16) |
Sn4 | 0.02604 (18) | 0.0383 (3) | 0.02497 (17) | 0.00659 (17) | 0.00221 (14) | −0.00421 (17) |
O11 | 0.0307 (19) | 0.068 (4) | 0.0229 (18) | 0.003 (2) | 0.0012 (15) | 0.005 (2) |
C11 | 0.026 (3) | 0.032 (4) | 0.033 (3) | 0.004 (2) | −0.006 (2) | 0.004 (3) |
O12 | 0.0341 (19) | 0.075 (4) | 0.0338 (19) | 0.022 (2) | −0.0014 (16) | −0.001 (2) |
C12 | 0.032 (3) | 0.037 (4) | 0.022 (2) | −0.002 (2) | −0.003 (2) | 0.002 (2) |
S13 | 0.0400 (7) | 0.0726 (13) | 0.0328 (7) | 0.0049 (8) | 0.0019 (6) | 0.0017 (8) |
C14 | 0.046 (3) | 0.066 (5) | 0.033 (3) | 0.008 (3) | −0.013 (2) | 0.011 (3) |
C15 | 0.030 (3) | 0.067 (5) | 0.044 (3) | 0.010 (3) | −0.002 (2) | 0.000 (3) |
C16 | 0.023 (2) | 0.042 (4) | 0.029 (2) | 0.001 (2) | −0.007 (2) | 0.005 (3) |
O21 | 0.0289 (18) | 0.069 (4) | 0.0250 (18) | 0.0027 (19) | −0.0046 (14) | −0.0050 (19) |
C21 | 0.029 (3) | 0.035 (4) | 0.033 (3) | −0.002 (3) | −0.001 (2) | −0.004 (3) |
O22 | 0.0297 (19) | 0.103 (4) | 0.041 (2) | 0.023 (2) | −0.0110 (17) | −0.024 (2) |
C22 | 0.028 (3) | 0.047 (4) | 0.030 (3) | 0.002 (2) | −0.001 (2) | 0.002 (3) |
S23 | 0.0455 (9) | 0.128 (2) | 0.0344 (8) | 0.0156 (10) | 0.0019 (6) | −0.0060 (10) |
C24 | 0.053 (4) | 0.132 (8) | 0.026 (3) | −0.006 (4) | −0.012 (3) | 0.007 (4) |
C25 | 0.035 (3) | 0.084 (6) | 0.048 (3) | 0.011 (4) | −0.006 (3) | 0.004 (4) |
C26 | 0.020 (2) | 0.033 (4) | 0.020 (2) | 0.002 (2) | −0.0036 (18) | 0.001 (2) |
O31 | 0.0210 (17) | 0.042 (3) | 0.0293 (18) | 0.0060 (17) | 0.0040 (15) | 0.0014 (17) |
C31 | 0.032 (3) | 0.032 (4) | 0.042 (3) | 0.008 (3) | 0.010 (3) | −0.003 (3) |
C32 | 0.020 (3) | 0.029 (4) | 0.051 (3) | 0.004 (2) | 0.006 (2) | 0.002 (3) |
O32 | 0.044 (2) | 0.059 (3) | 0.032 (2) | 0.014 (2) | 0.0080 (17) | 0.003 (2) |
C33 | 0.046 (3) | 0.053 (4) | 0.138 (5) | 0.004 (2) | −0.029 (3) | −0.022 (3) |
S33 | 0.046 (3) | 0.053 (4) | 0.138 (5) | 0.004 (2) | −0.029 (3) | −0.022 (3) |
C34 | 0.044 (4) | 0.055 (6) | 0.080 (5) | 0.008 (4) | −0.012 (4) | −0.011 (4) |
C35 | 0.023 (3) | 0.058 (5) | 0.108 (6) | −0.003 (3) | 0.000 (3) | 0.010 (5) |
S36 | 0.0270 (10) | 0.0627 (18) | 0.0684 (15) | 0.0113 (9) | 0.0158 (9) | 0.0178 (12) |
C36 | 0.0270 (10) | 0.0627 (18) | 0.0684 (15) | 0.0113 (9) | 0.0158 (9) | 0.0178 (12) |
O41 | 0.0244 (17) | 0.038 (3) | 0.0317 (18) | 0.0028 (17) | 0.0029 (14) | −0.0021 (18) |
C41 | 0.024 (3) | 0.024 (4) | 0.033 (3) | 0.002 (2) | 0.003 (2) | −0.002 (2) |
C42 | 0.023 (2) | 0.030 (4) | 0.035 (3) | 0.003 (2) | 0.006 (2) | 0.008 (3) |
O42 | 0.033 (2) | 0.049 (3) | 0.030 (2) | 0.0075 (19) | 0.0015 (15) | −0.0058 (19) |
C43 | 0.035 (2) | 0.057 (4) | 0.086 (3) | 0.007 (2) | −0.021 (2) | 0.001 (3) |
S43 | 0.035 (2) | 0.057 (4) | 0.086 (3) | 0.007 (2) | −0.021 (2) | 0.001 (3) |
C44 | 0.035 (3) | 0.053 (5) | 0.048 (3) | −0.004 (3) | −0.010 (3) | 0.011 (3) |
C45 | 0.023 (3) | 0.063 (6) | 0.055 (4) | 0.010 (3) | 0.001 (3) | 0.006 (4) |
S46 | 0.0268 (9) | 0.0709 (17) | 0.0440 (11) | 0.0106 (8) | 0.0043 (7) | 0.0038 (10) |
C46 | 0.0268 (9) | 0.0709 (17) | 0.0440 (11) | 0.0106 (8) | 0.0043 (7) | 0.0038 (10) |
C101 | 0.028 (3) | 0.035 (4) | 0.028 (3) | −0.004 (2) | 0.001 (2) | 0.005 (3) |
C102 | 0.047 (3) | 0.033 (4) | 0.039 (3) | −0.008 (3) | 0.007 (3) | −0.002 (3) |
C103 | 0.075 (5) | 0.046 (5) | 0.063 (4) | −0.004 (4) | 0.014 (4) | −0.006 (4) |
C104 | 0.126 (7) | 0.042 (5) | 0.081 (6) | −0.007 (4) | 0.014 (5) | 0.002 (4) |
C105 | 0.046 (4) | 0.032 (4) | 0.046 (3) | 0.002 (3) | 0.010 (3) | 0.003 (3) |
C106 | 0.056 (5) | 0.058 (7) | 0.125 (7) | 0.007 (4) | −0.025 (5) | 0.026 (6) |
C107 | 0.145 (9) | 0.030 (6) | 0.115 (8) | −0.011 (6) | −0.007 (6) | 0.010 (5) |
C108 | 0.119 (7) | 0.057 (7) | 0.138 (9) | 0.022 (5) | 0.053 (6) | 0.043 (6) |
C201 | 0.035 (3) | 0.040 (4) | 0.034 (3) | −0.008 (3) | 0.005 (2) | 0.000 (3) |
C202 | 0.048 (4) | 0.039 (5) | 0.060 (4) | −0.011 (3) | 0.002 (3) | 0.004 (3) |
C203 | 0.104 (6) | 0.041 (5) | 0.085 (6) | −0.005 (5) | 0.006 (5) | 0.009 (5) |
C204 | 0.215 (13) | 0.068 (8) | 0.185 (13) | −0.040 (8) | 0.016 (10) | 0.007 (8) |
C205 | 0.057 (4) | 0.039 (5) | 0.034 (3) | 0.009 (3) | 0.001 (3) | 0.008 (3) |
C206 | 0.146 (11) | 0.042 (8) | 0.38 (2) | −0.019 (7) | −0.065 (12) | 0.084 (11) |
C207 | 0.142 (10) | 0.068 (10) | 0.30 (2) | 0.032 (8) | −0.025 (11) | 0.053 (11) |
C208 | 0.247 (17) | 0.184 (18) | 0.36 (3) | 0.043 (13) | 0.195 (18) | 0.096 (17) |
C301 | 0.039 (3) | 0.037 (4) | 0.041 (3) | 0.010 (3) | 0.009 (2) | 0.004 (3) |
C302 | 0.072 (4) | 0.052 (5) | 0.041 (3) | 0.007 (4) | 0.018 (3) | −0.004 (3) |
C303 | 0.121 (7) | 0.033 (6) | 0.082 (6) | 0.012 (5) | 0.029 (5) | 0.016 (4) |
C304 | 0.190 (9) | 0.070 (7) | 0.067 (6) | 0.024 (7) | 0.011 (6) | 0.019 (5) |
C305 | 0.036 (3) | 0.053 (5) | 0.039 (3) | 0.005 (3) | 0.003 (3) | −0.008 (3) |
C306 | 0.043 (3) | 0.033 (5) | 0.051 (4) | −0.006 (3) | 0.009 (3) | −0.003 (3) |
C307 | 0.081 (5) | 0.031 (5) | 0.065 (4) | −0.010 (4) | 0.023 (4) | −0.016 (4) |
C308 | 0.086 (5) | 0.031 (5) | 0.100 (6) | 0.003 (4) | 0.036 (5) | −0.001 (4) |
C401 | 0.051 (4) | 0.038 (5) | 0.067 (4) | 0.001 (3) | 0.001 (3) | −0.028 (4) |
C402 | 0.052 (4) | 0.045 (6) | 0.081 (5) | 0.000 (4) | 0.019 (4) | −0.001 (4) |
C403 | 0.063 (5) | 0.060 (7) | 0.101 (6) | −0.006 (4) | 0.014 (4) | −0.017 (5) |
C404 | 0.088 (6) | 0.056 (7) | 0.158 (9) | 0.000 (5) | 0.043 (6) | −0.005 (6) |
C405 | 0.068 (4) | 0.057 (5) | 0.052 (4) | 0.016 (4) | 0.027 (3) | 0.016 (4) |
C406 | 0.114 (7) | 0.087 (8) | 0.118 (8) | 0.055 (6) | 0.059 (6) | 0.041 (6) |
C471 | 0.075 (13) | 0.21 (3) | 0.082 (16) | 0.044 (14) | −0.005 (11) | 0.026 (16) |
C472 | 0.069 (11) | 0.049 (12) | 0.063 (10) | 0.010 (9) | 0.014 (9) | 0.018 (8) |
C481 | 0.089 (14) | 0.099 (18) | 0.11 (2) | −0.001 (12) | −0.015 (12) | 0.047 (14) |
C482 | 0.098 (17) | 0.087 (17) | 0.059 (11) | −0.006 (14) | −0.001 (11) | 0.015 (11) |
Sn1—O1 | 2.049 (3) | C108—H10Q | 0.9800 |
Sn1—C101 | 2.132 (5) | C108—H10R | 0.9800 |
Sn1—C105 | 2.142 (6) | C201—C202 | 1.490 (9) |
Sn1—O2 | 2.172 (3) | C201—H20A | 0.9900 |
Sn1—O11 | 2.253 (3) | C201—H20B | 0.9900 |
O1—Sn3 | 2.034 (3) | C202—C203 | 1.556 (10) |
O1—Sn2 | 2.166 (3) | C202—H20C | 0.9900 |
Sn2—O2 | 2.046 (3) | C202—H20D | 0.9900 |
Sn2—C205 | 2.110 (6) | C203—C204 | 1.457 (12) |
Sn2—C201 | 2.128 (5) | C203—H20E | 0.9900 |
Sn2—O21 | 2.258 (3) | C203—H20F | 0.9900 |
O2—Sn4 | 2.030 (3) | C204—H20G | 0.9800 |
Sn3—C305 | 2.110 (7) | C204—H20H | 0.9800 |
Sn3—C301 | 2.109 (6) | C204—H20I | 0.9800 |
Sn3—O31 | 2.192 (3) | C205—C206 | 1.472 (8) |
Sn3—O12 | 2.248 (3) | C205—H20J | 0.9900 |
Sn4—C401 | 2.122 (7) | C205—H20K | 0.9900 |
Sn4—C405 | 2.130 (6) | C206—C207 | 1.536 (8) |
Sn4—O41 | 2.194 (3) | C206—H20L | 0.9900 |
Sn4—O22 | 2.234 (3) | C206—H20M | 0.9900 |
O11—C11 | 1.244 (5) | C207—C208 | 1.394 (8) |
C11—O12 | 1.265 (5) | C207—H20N | 0.9900 |
C11—C12 | 1.479 (6) | C207—H20O | 0.9900 |
C12—C16 | 1.402 (6) | C208—H20P | 0.9800 |
C12—S13 | 1.717 (4) | C208—H20Q | 0.9800 |
S13—C14 | 1.682 (6) | C208—H20R | 0.9800 |
C14—C15 | 1.351 (7) | C301—C302 | 1.479 (8) |
C14—H14 | 0.9500 | C301—H30A | 0.9900 |
C15—C16 | 1.412 (7) | C301—H30B | 0.9900 |
C15—H15 | 0.9500 | C302—C303 | 1.559 (9) |
C16—H16 | 0.9500 | C302—H30C | 0.9900 |
O21—C21 | 1.245 (6) | C302—H30D | 0.9900 |
C21—O22 | 1.255 (6) | C303—C304 | 1.514 (11) |
C21—C22 | 1.461 (7) | C303—H30E | 0.9900 |
C22—C26 | 1.415 (6) | C303—H30F | 0.9900 |
C22—S23 | 1.711 (5) | C304—H30G | 0.9800 |
S23—C24 | 1.689 (6) | C304—H30H | 0.9800 |
C24—C25 | 1.360 (8) | C304—H30I | 0.9800 |
C24—H24 | 0.9500 | C305—C306 | 1.517 (9) |
C25—C26 | 1.420 (7) | C305—H30J | 0.9900 |
C25—H25 | 0.9500 | C305—H30K | 0.9900 |
C26—H26 | 0.9500 | C306—C307 | 1.526 (9) |
O31—C31 | 1.296 (6) | C306—H30L | 0.9900 |
C31—O32 | 1.216 (6) | C306—H30M | 0.9900 |
C31—C32 | 1.509 (7) | C307—C308 | 1.496 (10) |
C32—C33 | 1.508 (7) | C307—H30N | 0.9900 |
C32—S36 | 1.716 (5) | C307—H30O | 0.9900 |
C33—C34 | 1.491 (7) | C308—H30P | 0.9800 |
C33—H33 | 0.9500 | C308—H30Q | 0.9800 |
C34—C35 | 1.352 (9) | C308—H30R | 0.9800 |
C34—H34 | 0.9500 | C401—C402 | 1.471 (9) |
C35—S36 | 1.704 (7) | C401—H40A | 0.9900 |
C35—H35 | 0.9500 | C401—H40B | 0.9900 |
O41—C41 | 1.316 (5) | C402—C403 | 1.508 (11) |
C41—O42 | 1.216 (6) | C402—H40C | 0.9900 |
C41—C42 | 1.479 (7) | C402—H40D | 0.9900 |
C42—C43 | 1.513 (7) | C403—C404 | 1.513 (11) |
C42—S46 | 1.695 (5) | C403—H40E | 0.9900 |
C43—C44 | 1.507 (6) | C403—H40F | 0.9900 |
C43—H43 | 0.9500 | C404—H40G | 0.9800 |
C44—C45 | 1.323 (8) | C404—H40H | 0.9800 |
C44—H44 | 0.9500 | C404—H40I | 0.9800 |
C45—S46 | 1.680 (6) | C405—C406 | 1.505 (7) |
C45—H45 | 0.9500 | C405—H40J | 0.9900 |
C101—C102 | 1.532 (8) | C405—H40K | 0.9900 |
C101—H10A | 0.9900 | C406—C471 | 1.535 (9) |
C101—H10B | 0.9900 | C406—C472 | 1.539 (8) |
C102—C103 | 1.533 (9) | C406—H40L | 0.9900 |
C102—H10C | 0.9900 | C406—H40M | 0.9901 |
C102—H10D | 0.9900 | C406—H40N | 0.9900 |
C103—C104 | 1.524 (9) | C406—H40O | 0.9901 |
C103—H10E | 0.9900 | C471—C481 | 1.505 (10) |
C103—H10F | 0.9900 | C471—H40O | 1.5375 |
C104—H10G | 0.9800 | C471—H47A | 0.9900 |
C104—H10H | 0.9800 | C471—H47B | 0.9900 |
C104—H10I | 0.9800 | C472—C482 | 1.498 (9) |
C105—C106 | 1.474 (8) | C472—H40L | 1.5641 |
C105—H10J | 0.9900 | C472—H47C | 0.9900 |
C105—H10K | 0.9900 | C472—H47D | 0.9900 |
C106—C107 | 1.520 (10) | C481—H48A | 0.9800 |
C106—H10L | 0.9900 | C481—H48B | 0.9800 |
C106—H10M | 0.9900 | C481—H48C | 0.9800 |
C107—C108 | 1.457 (12) | C482—H48D | 0.9800 |
C107—H10N | 0.9900 | C482—H48E | 0.9800 |
C107—H10O | 0.9900 | C482—H48F | 0.9800 |
C108—H10P | 0.9800 | ||
O1—Sn1—C101 | 107.19 (18) | C203—C202—H20C | 109.3 |
O1—Sn1—C105 | 103.91 (18) | C201—C202—H20D | 109.3 |
C101—Sn1—C105 | 148.4 (2) | C203—C202—H20D | 109.3 |
O1—Sn1—O2 | 76.22 (11) | H20C—C202—H20D | 107.9 |
C101—Sn1—O2 | 96.63 (17) | C204—C203—C202 | 113.8 (7) |
C105—Sn1—O2 | 95.8 (2) | C204—C203—H20E | 108.8 |
O1—Sn1—O11 | 92.31 (12) | C202—C203—H20E | 108.8 |
C101—Sn1—O11 | 85.40 (17) | C204—C203—H20F | 108.8 |
C105—Sn1—O11 | 88.1 (2) | C202—C203—H20F | 108.8 |
O2—Sn1—O11 | 168.45 (12) | H20E—C203—H20F | 107.7 |
Sn3—O1—Sn1 | 136.05 (14) | C203—C204—H20G | 109.5 |
Sn3—O1—Sn2 | 120.00 (13) | C203—C204—H20H | 109.5 |
Sn1—O1—Sn2 | 103.73 (12) | H20G—C204—H20H | 109.5 |
O2—Sn2—C205 | 105.25 (19) | C203—C204—H20I | 109.5 |
O2—Sn2—C201 | 108.50 (19) | H20G—C204—H20I | 109.5 |
C205—Sn2—C201 | 146.0 (2) | H20H—C204—H20I | 109.5 |
O2—Sn2—O1 | 76.42 (11) | C206—C205—Sn2 | 121.0 (5) |
C205—Sn2—O1 | 95.26 (19) | C206—C205—H20J | 107.1 |
C201—Sn2—O1 | 96.74 (17) | Sn2—C205—H20J | 107.1 |
O2—Sn2—O21 | 92.03 (12) | C206—C205—H20K | 107.1 |
C205—Sn2—O21 | 89.1 (2) | Sn2—C205—H20K | 107.1 |
C201—Sn2—O21 | 85.46 (17) | H20J—C205—H20K | 106.8 |
O1—Sn2—O21 | 168.36 (12) | C205—C206—C207 | 114.6 (8) |
Sn4—O2—Sn2 | 137.17 (15) | C205—C206—H20L | 108.6 |
Sn4—O2—Sn1 | 119.10 (13) | C207—C206—H20L | 108.6 |
Sn2—O2—Sn1 | 103.63 (12) | C205—C206—H20M | 108.6 |
O1—Sn3—C305 | 109.88 (19) | C207—C206—H20M | 108.6 |
O1—Sn3—C301 | 113.12 (19) | H20L—C206—H20M | 107.6 |
C305—Sn3—C301 | 135.7 (2) | C208—C207—C206 | 116.6 (9) |
O1—Sn3—O31 | 80.62 (11) | C208—C207—H20N | 108.2 |
C305—Sn3—O31 | 98.98 (19) | C206—C207—H20N | 108.2 |
C301—Sn3—O31 | 97.88 (17) | C208—C207—H20O | 108.2 |
O1—Sn3—O12 | 90.26 (11) | C206—C207—H20O | 108.2 |
C305—Sn3—O12 | 85.6 (2) | H20N—C207—H20O | 107.3 |
C301—Sn3—O12 | 84.14 (18) | C207—C208—H20P | 109.5 |
O31—Sn3—O12 | 170.74 (12) | C207—C208—H20Q | 109.5 |
O2—Sn4—C401 | 110.8 (2) | H20P—C208—H20Q | 109.5 |
O2—Sn4—C405 | 110.9 (2) | C207—C208—H20R | 109.5 |
C401—Sn4—C405 | 137.1 (3) | H20P—C208—H20R | 109.5 |
O2—Sn4—O41 | 80.27 (12) | H20Q—C208—H20R | 109.5 |
C401—Sn4—O41 | 98.3 (2) | C302—C301—Sn3 | 117.0 (4) |
C405—Sn4—O41 | 98.2 (2) | C302—C301—H30A | 108.0 |
O2—Sn4—O22 | 89.42 (12) | Sn3—C301—H30A | 108.0 |
C401—Sn4—O22 | 83.9 (2) | C302—C301—H30B | 108.0 |
C405—Sn4—O22 | 86.9 (2) | Sn3—C301—H30B | 108.0 |
O41—Sn4—O22 | 169.59 (12) | H30A—C301—H30B | 107.3 |
C11—O11—Sn1 | 133.2 (3) | C301—C302—C303 | 114.6 (5) |
O11—C11—O12 | 125.7 (4) | C301—C302—H30C | 108.6 |
O11—C11—C12 | 117.6 (4) | C303—C302—H30C | 108.6 |
O12—C11—C12 | 116.7 (4) | C301—C302—H30D | 108.6 |
C11—O12—Sn3 | 138.6 (3) | C303—C302—H30D | 108.6 |
C16—C12—C11 | 126.7 (4) | H30C—C302—H30D | 107.6 |
C16—C12—S13 | 113.0 (3) | C304—C303—C302 | 112.1 (7) |
C11—C12—S13 | 120.2 (3) | C304—C303—H30E | 109.2 |
C14—S13—C12 | 90.9 (2) | C302—C303—H30E | 109.2 |
C15—C14—S13 | 112.8 (4) | C304—C303—H30F | 109.2 |
C15—C14—H14 | 123.6 | C302—C303—H30F | 109.2 |
S13—C14—H14 | 123.6 | H30E—C303—H30F | 107.9 |
C14—C15—C16 | 114.7 (5) | C303—C304—H30G | 109.5 |
C14—C15—H15 | 122.6 | C303—C304—H30H | 109.5 |
C16—C15—H15 | 122.6 | H30G—C304—H30H | 109.5 |
C12—C16—C15 | 108.5 (4) | C303—C304—H30I | 109.5 |
C12—C16—H16 | 125.8 | H30G—C304—H30I | 109.5 |
C15—C16—H16 | 125.8 | H30H—C304—H30I | 109.5 |
C21—O21—Sn2 | 134.3 (3) | C306—C305—Sn3 | 119.8 (4) |
O21—C21—O22 | 124.7 (5) | C306—C305—H30J | 107.4 |
O21—C21—C22 | 117.7 (4) | Sn3—C305—H30J | 107.4 |
O22—C21—C22 | 117.6 (4) | C306—C305—H30K | 107.4 |
C21—O22—Sn4 | 140.3 (3) | Sn3—C305—H30K | 107.4 |
C26—C22—C21 | 127.8 (4) | H30J—C305—H30K | 106.9 |
C26—C22—S23 | 112.2 (3) | C305—C306—C307 | 112.9 (5) |
C21—C22—S23 | 119.9 (4) | C305—C306—H30L | 109.0 |
C24—S23—C22 | 91.7 (3) | C307—C306—H30L | 109.0 |
C25—C24—S23 | 113.0 (4) | C305—C306—H30M | 109.0 |
C25—C24—H24 | 123.5 | C307—C306—H30M | 109.0 |
S23—C24—H24 | 123.5 | H30L—C306—H30M | 107.8 |
C24—C25—C26 | 113.6 (5) | C308—C307—C306 | 112.4 (6) |
C24—C25—H25 | 123.2 | C308—C307—H30N | 109.1 |
C26—C25—H25 | 123.2 | C306—C307—H30N | 109.1 |
C22—C26—C25 | 109.5 (4) | C308—C307—H30O | 109.1 |
C22—C26—H26 | 125.3 | C306—C307—H30O | 109.1 |
C25—C26—H26 | 125.3 | H30N—C307—H30O | 107.9 |
C31—O31—Sn3 | 108.2 (3) | C307—C308—H30P | 109.5 |
O32—C31—O31 | 124.0 (5) | C307—C308—H30Q | 109.5 |
O32—C31—C32 | 120.8 (4) | H30P—C308—H30Q | 109.5 |
O31—C31—C32 | 115.2 (5) | C307—C308—H30R | 109.5 |
C33—C32—C31 | 125.0 (4) | H30P—C308—H30R | 109.5 |
C33—C32—S36 | 117.7 (4) | H30Q—C308—H30R | 109.5 |
C31—C32—S36 | 117.3 (4) | C402—C401—Sn4 | 122.0 (5) |
C34—C33—C32 | 100.1 (5) | C402—C401—H40A | 106.8 |
C34—C33—H33 | 130.0 | Sn4—C401—H40A | 106.8 |
C32—C33—H33 | 130.0 | C402—C401—H40B | 106.8 |
C35—C34—C33 | 118.3 (6) | Sn4—C401—H40B | 106.8 |
C35—C34—H34 | 120.8 | H40A—C401—H40B | 106.7 |
C33—C34—H34 | 120.8 | C401—C402—C403 | 114.2 (6) |
C34—C35—S36 | 113.9 (4) | C401—C402—H40C | 108.7 |
C34—C35—H35 | 123.0 | C403—C402—H40C | 108.7 |
S36—C35—H35 | 123.0 | C401—C402—H40D | 108.7 |
C35—S36—C32 | 89.9 (3) | C403—C402—H40D | 108.7 |
C41—O41—Sn4 | 109.1 (3) | H40C—C402—H40D | 107.6 |
O42—C41—O41 | 122.7 (4) | C402—C403—C404 | 117.3 (7) |
O42—C41—C42 | 121.6 (4) | C402—C403—H40E | 108.0 |
O41—C41—C42 | 115.7 (4) | C404—C403—H40E | 108.0 |
C41—C42—C43 | 126.0 (4) | C402—C403—H40F | 108.0 |
C41—C42—S46 | 118.1 (4) | C404—C403—H40F | 108.0 |
C43—C42—S46 | 115.9 (3) | H40E—C403—H40F | 107.2 |
C44—C43—C42 | 100.6 (4) | C403—C404—H40G | 109.5 |
C44—C43—H43 | 129.7 | C403—C404—H40H | 109.5 |
C42—C43—H43 | 129.7 | H40G—C404—H40H | 109.5 |
C45—C44—C43 | 117.5 (5) | C403—C404—H40I | 109.5 |
C45—C44—H44 | 121.2 | H40G—C404—H40I | 109.5 |
C43—C44—H44 | 121.2 | H40H—C404—H40I | 109.5 |
C44—C45—S46 | 114.4 (4) | C406—C405—Sn4 | 118.4 (4) |
C44—C45—H45 | 122.8 | C406—C405—H40J | 107.7 |
S46—C45—H45 | 122.8 | Sn4—C405—H40J | 107.7 |
C45—S46—C42 | 91.5 (3) | C406—C405—H40K | 107.7 |
C102—C101—Sn1 | 113.8 (3) | Sn4—C405—H40K | 107.7 |
C102—C101—H10A | 108.8 | H40J—C405—H40K | 107.1 |
Sn1—C101—H10A | 108.8 | C405—C406—C471 | 111.9 (7) |
C102—C101—H10B | 108.8 | C405—C406—C472 | 112.0 (6) |
Sn1—C101—H10B | 108.8 | C471—C406—C472 | 40.6 (7) |
H10A—C101—H10B | 107.7 | C405—C406—H40L | 109.3 |
C101—C102—C103 | 113.2 (5) | C471—C406—H40L | 110.4 |
C101—C102—H10C | 108.9 | C472—C406—H40L | 72.8 |
C103—C102—H10C | 108.9 | C405—C406—H40M | 108.9 |
C101—C102—H10D | 108.9 | C471—C406—H40M | 108.3 |
C103—C102—H10D | 108.9 | C472—C406—H40M | 136.0 |
H10C—C102—H10D | 107.7 | H40L—C406—H40M | 108.0 |
C104—C103—C102 | 111.7 (6) | C405—C406—H40N | 108.9 |
C104—C103—H10E | 109.3 | C471—C406—H40N | 136.7 |
C102—C103—H10E | 109.3 | C472—C406—H40N | 109.5 |
C104—C103—H10F | 109.3 | H40L—C406—H40N | 40.2 |
C102—C103—H10F | 109.3 | H40M—C406—H40N | 70.4 |
H10E—C103—H10F | 108.0 | C405—C406—H40O | 109.2 |
C103—C104—H10G | 109.5 | C471—C406—H40O | 71.4 |
C103—C104—H10H | 109.5 | C472—C406—H40O | 109.1 |
H10G—C104—H10H | 109.5 | H40L—C406—H40O | 136.9 |
C103—C104—H10I | 109.5 | H40M—C406—H40O | 40.2 |
H10G—C104—H10I | 109.5 | H40N—C406—H40O | 108.0 |
H10H—C104—H10I | 109.5 | C481—C471—C406 | 111.6 (9) |
C106—C105—Sn1 | 123.7 (5) | C481—C471—H40O | 148.5 |
C106—C105—H10J | 106.4 | C406—C471—H40O | 37.6 |
Sn1—C105—H10J | 106.4 | C481—C471—H47A | 109.3 |
C106—C105—H10K | 106.4 | C406—C471—H47A | 109.3 |
Sn1—C105—H10K | 106.4 | H40O—C471—H47A | 83.8 |
H10J—C105—H10K | 106.5 | C481—C471—H47B | 109.3 |
C105—C106—C107 | 116.6 (7) | C406—C471—H47B | 109.3 |
C105—C106—H10L | 108.1 | H40O—C471—H47B | 92.6 |
C107—C106—H10L | 108.1 | H47A—C471—H47B | 108.0 |
C105—C106—H10M | 108.1 | C482—C472—C406 | 111.9 (9) |
C107—C106—H10M | 108.1 | C482—C472—H40L | 149.0 |
H10L—C106—H10M | 107.3 | C406—C472—H40L | 37.2 |
C108—C107—C106 | 110.9 (8) | C482—C472—H47C | 109.2 |
C108—C107—H10N | 109.5 | C406—C472—H47C | 109.2 |
C106—C107—H10N | 109.5 | H40L—C472—H47C | 87.7 |
C108—C107—H10O | 109.5 | C482—C472—H47D | 109.2 |
C106—C107—H10O | 109.5 | C406—C472—H47D | 109.2 |
H10N—C107—H10O | 108.1 | H40L—C472—H47D | 88.7 |
C107—C108—H10P | 109.5 | H47C—C472—H47D | 107.9 |
C107—C108—H10Q | 109.5 | C471—C481—H48A | 109.5 |
H10P—C108—H10Q | 109.5 | C471—C481—H48B | 109.5 |
C107—C108—H10R | 109.5 | H48A—C481—H48B | 109.5 |
H10P—C108—H10R | 109.5 | C471—C481—H48C | 109.5 |
H10Q—C108—H10R | 109.5 | H48A—C481—H48C | 109.5 |
C202—C201—Sn2 | 113.3 (3) | H48B—C481—H48C | 109.5 |
C202—C201—H20A | 108.9 | C472—C482—H48D | 109.5 |
Sn2—C201—H20A | 108.9 | C472—C482—H48E | 109.5 |
C202—C201—H20B | 108.9 | H48D—C482—H48E | 109.5 |
Sn2—C201—H20B | 108.9 | C472—C482—H48F | 109.5 |
H20A—C201—H20B | 107.7 | H48D—C482—H48F | 109.5 |
C201—C202—C203 | 111.8 (5) | H48E—C482—H48F | 109.5 |
C201—C202—H20C | 109.3 | ||
C101—Sn1—O1—Sn3 | −93.6 (3) | S23—C24—C25—C26 | 0.7 (9) |
C105—Sn1—O1—Sn3 | 80.9 (3) | C21—C22—C26—C25 | −179.8 (7) |
O2—Sn1—O1—Sn3 | 173.6 (3) | S23—C22—C26—C25 | 1.2 (7) |
O11—Sn1—O1—Sn3 | −7.7 (3) | C24—C25—C26—C22 | −1.2 (9) |
C101—Sn1—O1—Sn2 | 92.13 (19) | O1—Sn3—O31—C31 | 172.9 (4) |
C105—Sn1—O1—Sn2 | −93.4 (2) | C305—Sn3—O31—C31 | −78.2 (4) |
O2—Sn1—O1—Sn2 | −0.66 (18) | C301—Sn3—O31—C31 | 60.7 (4) |
O11—Sn1—O1—Sn2 | 178.02 (16) | Sn3—O31—C31—O32 | 6.2 (8) |
Sn3—O1—Sn2—O2 | −174.72 (18) | Sn3—O31—C31—C32 | −172.3 (4) |
Sn1—O1—Sn2—O2 | 0.70 (19) | O32—C31—C32—C33 | 176.0 (6) |
Sn3—O1—Sn2—C205 | 80.8 (2) | O31—C31—C32—C33 | −5.5 (9) |
Sn1—O1—Sn2—C205 | −103.8 (2) | O32—C31—C32—S36 | −1.6 (8) |
Sn3—O1—Sn2—C201 | −67.3 (2) | O31—C31—C32—S36 | 176.9 (4) |
Sn1—O1—Sn2—C201 | 108.2 (2) | C31—C32—C33—C34 | 178.8 (6) |
Sn3—O1—Sn2—O21 | −167.5 (7) | S36—C32—C33—C34 | −3.5 (6) |
Sn1—O1—Sn2—O21 | 7.9 (9) | C32—C33—C34—C35 | 2.7 (8) |
C205—Sn2—O2—Sn4 | −84.9 (3) | C33—C34—C35—S36 | −1.0 (9) |
C201—Sn2—O2—Sn4 | 90.6 (3) | C34—C35—S36—C32 | −1.1 (6) |
O1—Sn2—O2—Sn4 | −176.7 (3) | C33—C32—S36—C35 | 2.9 (5) |
O21—Sn2—O2—Sn4 | 4.7 (3) | C31—C32—S36—C35 | −179.3 (5) |
C205—Sn2—O2—Sn1 | 91.2 (2) | O2—Sn4—O41—C41 | −170.0 (4) |
C201—Sn2—O2—Sn1 | −93.3 (2) | C401—Sn4—O41—C41 | 80.1 (4) |
O1—Sn2—O2—Sn1 | −0.66 (18) | C405—Sn4—O41—C41 | −60.1 (4) |
O21—Sn2—O2—Sn1 | −179.21 (17) | O22—Sn4—O41—C41 | −178.4 (9) |
O1—Sn1—O2—Sn4 | 177.62 (19) | Sn4—O41—C41—O42 | −4.8 (7) |
C101—Sn1—O2—Sn4 | 71.5 (2) | Sn4—O41—C41—C42 | 175.8 (4) |
C105—Sn1—O2—Sn4 | −79.5 (2) | O42—C41—C42—C43 | −179.2 (6) |
O11—Sn1—O2—Sn4 | 171.0 (7) | O41—C41—C42—C43 | 0.3 (8) |
O1—Sn1—O2—Sn2 | 0.70 (19) | O42—C41—C42—S46 | 0.2 (8) |
C101—Sn1—O2—Sn2 | −105.4 (2) | O41—C41—C42—S46 | 179.7 (4) |
C105—Sn1—O2—Sn2 | 103.6 (2) | C41—C42—C43—C44 | −178.5 (6) |
O11—Sn1—O2—Sn2 | −5.9 (9) | S46—C42—C43—C44 | 2.0 (6) |
Sn1—O1—Sn3—C305 | 84.1 (3) | C42—C43—C44—C45 | −1.9 (8) |
Sn2—O1—Sn3—C305 | −102.3 (2) | C43—C44—C45—S46 | 1.2 (8) |
Sn1—O1—Sn3—C301 | −85.0 (3) | C44—C45—S46—C42 | 0.1 (6) |
Sn2—O1—Sn3—C301 | 88.6 (2) | C41—C42—S46—C45 | 179.1 (5) |
Sn1—O1—Sn3—O31 | −179.6 (3) | C43—C42—S46—C45 | −1.4 (5) |
Sn2—O1—Sn3—O31 | −6.0 (2) | O1—Sn1—C101—C102 | 29.7 (4) |
Sn1—O1—Sn3—O12 | −1.3 (3) | C105—Sn1—C101—C102 | −140.1 (4) |
Sn2—O1—Sn3—O12 | 172.3 (2) | O2—Sn1—C101—C102 | 107.3 (4) |
Sn2—O2—Sn4—C401 | −86.7 (3) | O11—Sn1—C101—C102 | −61.3 (4) |
Sn1—O2—Sn4—C401 | 97.7 (3) | Sn1—C101—C102—C103 | −179.9 (4) |
Sn2—O2—Sn4—C405 | 82.9 (3) | C101—C102—C103—C104 | 68.1 (7) |
Sn1—O2—Sn4—C405 | −92.7 (3) | O1—Sn1—C105—C106 | −139.6 (6) |
Sn2—O2—Sn4—O41 | 178.0 (3) | C101—Sn1—C105—C106 | 30.4 (8) |
Sn1—O2—Sn4—O41 | 2.41 (19) | O2—Sn1—C105—C106 | 143.2 (6) |
Sn2—O2—Sn4—O22 | −3.5 (3) | O11—Sn1—C105—C106 | −47.6 (6) |
Sn1—O2—Sn4—O22 | −179.1 (2) | Sn1—C105—C106—C107 | 166.7 (6) |
O1—Sn1—O11—C11 | 23.4 (5) | C105—C106—C107—C108 | 65.7 (11) |
C101—Sn1—O11—C11 | 130.5 (5) | O2—Sn2—C201—C202 | −26.3 (4) |
C105—Sn1—O11—C11 | −80.4 (5) | C205—Sn2—C201—C202 | 145.9 (4) |
O2—Sn1—O11—C11 | 29.8 (11) | O1—Sn2—C201—C202 | −104.2 (4) |
Sn1—O11—C11—O12 | −23.4 (9) | O21—Sn2—C201—C202 | 64.3 (4) |
Sn1—O11—C11—C12 | 154.6 (4) | Sn2—C201—C202—C203 | 177.9 (5) |
O11—C11—O12—Sn3 | 2.3 (10) | C201—C202—C203—C204 | 176.2 (7) |
C12—C11—O12—Sn3 | −175.8 (4) | O2—Sn2—C205—C206 | 117.3 (8) |
O1—Sn3—O12—C11 | 9.2 (6) | C201—Sn2—C205—C206 | −55.0 (9) |
C305—Sn3—O12—C11 | −100.7 (7) | O1—Sn2—C205—C206 | −165.3 (8) |
C301—Sn3—O12—C11 | 122.4 (7) | O21—Sn2—C205—C206 | 25.5 (8) |
O11—C11—C12—C16 | 0.0 (9) | Sn2—C205—C206—C207 | 171.0 (7) |
O12—C11—C12—C16 | 178.2 (6) | C205—C206—C207—C208 | 71.6 (18) |
O11—C11—C12—S13 | −177.9 (4) | O1—Sn3—C301—C302 | 28.6 (5) |
O12—C11—C12—S13 | 0.3 (8) | C305—Sn3—C301—C302 | −136.7 (5) |
C16—C12—S13—C14 | 1.8 (5) | O31—Sn3—C301—C302 | 111.7 (5) |
C11—C12—S13—C14 | 180.0 (5) | O12—Sn3—C301—C302 | −59.2 (5) |
C12—S13—C14—C15 | −2.0 (6) | Sn3—C301—C302—C303 | 174.1 (5) |
S13—C14—C15—C16 | 1.7 (8) | C301—C302—C303—C304 | −68.5 (9) |
C11—C12—C16—C15 | −179.2 (6) | O1—Sn3—C305—C306 | 84.6 (4) |
S13—C12—C16—C15 | −1.2 (7) | C301—Sn3—C305—C306 | −109.7 (5) |
C14—C15—C16—C12 | −0.3 (9) | O31—Sn3—C305—C306 | 1.4 (4) |
O2—Sn2—O21—C21 | −12.1 (6) | O12—Sn3—C305—C306 | 173.3 (4) |
C205—Sn2—O21—C21 | 93.2 (6) | Sn3—C305—C306—C307 | −177.2 (4) |
C201—Sn2—O21—C21 | −120.5 (6) | C305—C306—C307—C308 | −178.1 (5) |
O1—Sn2—O21—C21 | −19.0 (12) | O2—Sn4—C401—C402 | −101.7 (5) |
Sn2—O21—C21—O22 | 18.7 (10) | C405—Sn4—C401—C402 | 92.6 (6) |
Sn2—O21—C21—C22 | −163.1 (4) | O41—Sn4—C401—C402 | −19.0 (6) |
O21—C21—O22—Sn4 | −17.0 (12) | O22—Sn4—C401—C402 | 171.2 (6) |
C22—C21—O22—Sn4 | 164.8 (5) | Sn4—C401—C402—C403 | 179.4 (5) |
O2—Sn4—O22—C21 | 8.6 (7) | C401—C402—C403—C404 | −179.9 (7) |
C401—Sn4—O22—C21 | 119.6 (7) | O2—Sn4—C405—C406 | −37.4 (7) |
C405—Sn4—O22—C21 | −102.4 (7) | C401—Sn4—C405—C406 | 128.3 (6) |
O41—Sn4—O22—C21 | 16.9 (15) | O41—Sn4—C405—C406 | −120.1 (6) |
O21—C21—C22—C26 | −0.7 (10) | O22—Sn4—C405—C406 | 50.8 (6) |
O22—C21—C22—C26 | 177.7 (6) | Sn4—C405—C406—C471 | −147.0 (7) |
O21—C21—C22—S23 | 178.2 (5) | Sn4—C405—C406—C472 | 169.1 (7) |
O22—C21—C22—S23 | −3.5 (9) | C405—C406—C471—C481 | −67.3 (18) |
C26—C22—S23—C24 | −0.7 (6) | C472—C406—C471—C481 | 31.5 (14) |
C21—C22—S23—C24 | −179.8 (6) | C405—C406—C472—C482 | 76.7 (15) |
C22—S23—C24—C25 | 0.0 (7) | C471—C406—C472—C482 | −21.7 (13) |
Experimental details
Crystal data | |
Chemical formula | [Sn4O2(C5H3O2S)4(C4H9)8] |
Mr | 1472.19 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 13.495 (2), 17.324 (3), 13.471 (2) |
β (°) | 93.01 (1) |
V (Å3) | 3145.0 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.75 |
Crystal size (mm) | 0.46 × 0.42 × 0.34 |
Data collection | |
Diffractometer | Siemens CCD three-circle diffractometer |
Absorption correction | Empirical (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.470, 0.550 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12639, 8637, 7626 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.644 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.049, 0.96 |
No. of reflections | 8637 |
No. of parameters | 653 |
No. of restraints | 15 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.57 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.50 (2) |
Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Siemens, 1991).
Sn1—O1 | 2.049 (3) | Sn3—O31 | 2.192 (3) |
Sn1—C101 | 2.132 (5) | Sn3—O12 | 2.248 (3) |
Sn1—C105 | 2.142 (6) | Sn4—C401 | 2.122 (7) |
Sn1—O2 | 2.172 (3) | Sn4—C405 | 2.130 (6) |
Sn1—O11 | 2.253 (3) | Sn4—O41 | 2.194 (3) |
O1—Sn3 | 2.034 (3) | Sn4—O22 | 2.234 (3) |
O1—Sn2 | 2.166 (3) | O11—C11 | 1.244 (5) |
Sn2—O2 | 2.046 (3) | C11—O12 | 1.265 (5) |
Sn2—C205 | 2.110 (6) | O21—C21 | 1.245 (6) |
Sn2—C201 | 2.128 (5) | C21—O22 | 1.255 (6) |
Sn2—O21 | 2.258 (3) | O31—C31 | 1.296 (6) |
O2—Sn4 | 2.030 (3) | C31—O32 | 1.216 (6) |
Sn3—C305 | 2.110 (7) | O41—C41 | 1.316 (5) |
Sn3—C301 | 2.109 (6) | C41—O42 | 1.216 (6) |
O1—Sn1—C101 | 107.19 (18) | C305—Sn3—C301 | 135.7 (2) |
O1—Sn1—C105 | 103.91 (18) | O1—Sn3—O31 | 80.62 (11) |
C101—Sn1—C105 | 148.4 (2) | C305—Sn3—O31 | 98.98 (19) |
O1—Sn1—O2 | 76.22 (11) | C301—Sn3—O31 | 97.88 (17) |
C101—Sn1—O2 | 96.63 (17) | O1—Sn3—O12 | 90.26 (11) |
C105—Sn1—O2 | 95.8 (2) | C305—Sn3—O12 | 85.6 (2) |
O1—Sn1—O11 | 92.31 (12) | C301—Sn3—O12 | 84.14 (18) |
C101—Sn1—O11 | 85.40 (17) | O31—Sn3—O12 | 170.74 (12) |
C105—Sn1—O11 | 88.1 (2) | O2—Sn4—C401 | 110.8 (2) |
O2—Sn1—O11 | 168.45 (12) | O2—Sn4—C405 | 110.9 (2) |
Sn3—O1—Sn1 | 136.05 (14) | C401—Sn4—C405 | 137.1 (3) |
Sn3—O1—Sn2 | 120.00 (13) | O2—Sn4—O41 | 80.27 (12) |
Sn1—O1—Sn2 | 103.73 (12) | C401—Sn4—O41 | 98.3 (2) |
O2—Sn2—C205 | 105.25 (19) | C405—Sn4—O41 | 98.2 (2) |
O2—Sn2—C201 | 108.50 (19) | O2—Sn4—O22 | 89.42 (12) |
C205—Sn2—C201 | 146.0 (2) | C401—Sn4—O22 | 83.9 (2) |
O2—Sn2—O1 | 76.42 (11) | C405—Sn4—O22 | 86.9 (2) |
C205—Sn2—O1 | 95.26 (19) | O41—Sn4—O22 | 169.59 (12) |
C201—Sn2—O1 | 96.74 (17) | C11—O11—Sn1 | 133.2 (3) |
O2—Sn2—O21 | 92.03 (12) | O11—C11—O12 | 125.7 (4) |
C205—Sn2—O21 | 89.1 (2) | C11—O12—Sn3 | 138.6 (3) |
C201—Sn2—O21 | 85.46 (17) | C21—O21—Sn2 | 134.3 (3) |
O1—Sn2—O21 | 168.36 (12) | O21—C21—O22 | 124.7 (5) |
Sn4—O2—Sn2 | 137.17 (15) | C21—O22—Sn4 | 140.3 (3) |
Sn4—O2—Sn1 | 119.10 (13) | C31—O31—Sn3 | 108.2 (3) |
Sn2—O2—Sn1 | 103.63 (12) | C41—O41—Sn4 | 109.1 (3) |
O1—Sn3—C305 | 109.88 (19) | C102—C101—Sn1 | 113.8 (3) |
O1—Sn3—C301 | 113.12 (19) |
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The success of cisplatin as an antitumour agent has led to the investigation of antitumour activity in a variety of organotin complexes (Huber et al., 1989; Tiekink, 1991). Some di-n-butyltin complexes have been synthesized and tested; and some of them have been found to be more active in vitro than cisplatin (Et-touhami et al., 1991; Gielen, 1994). To continue this investigation, we have recently reported the crystal structure of di-n-butylbis(thiophene-2-carboxylato-O,O')tin(IV) (Yahyi et al., 2001).
The crystal structure determination of the title complex, (I), was carried out in order to determine the constitution of the reaction product. Compound (I) contains a planar Sn2O2 ring. The other two Sn atoms and the carboxyl groups lie in the plane of this ring. A previous structure determination of (I) (Vatsa et al., 1990) showed the same cell parameters but a centrosymmetric molecule in space group P21/c. At low temperature, however, we discovered (I) to be a racemic twin showing pseudo-centrosymmetry.