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
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) |
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.