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The title compound, octa-n-butyl-1κ2C,2κ2C,3κ2C,4κ2C-di-μ3-oxo-1:2:3κ3O;2:3:4:κ3O-tetrakis­(thio­phene-2-carboxyl­ate)-1κO;1:2κ2O:O′;3:4κ2O:O′;4κO-tetratin(VI), [Sn4O2(C4H9)8(C5H3O2S)4], contains a planar Sn2O2 ring. The crystal structure is a racemic twin and shows pseudo-centrosymmetry. A previous structure determination of the title compound [Vatsa et al. (1990). J. Organomet. Chem. 396, 9–18] showed the same cell parameters but a centrosymmetric mol­ecule in space group P21/c.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004214/ci6014sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004214/ci6014Isup2.hkl
Contains datablock I

CCDC reference: 162798

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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


Amber Alert Alert Level B:
PLAT_213 Alert B Atom C206 has ADP max/min Ratio ........... 4.40
Yellow Alert 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

Comment top

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.

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A perspective view of the title compound with the atom-numbering scheme. Displacement ellipsoids are at the 30% probability level. H atoms and part two of the disordered atoms have been omitted for clarity.
octa-n-butyl-1κ2C,2κ2C,3κ2C,4κ2C-di-µ3-oxo- 1:2:3κ3O;2:3:4:κ3O-tetrakis(thiophene-2-carboxylate)- 1κO;1:2κ2O:O';3:4κ2O:O';4κO-tetratin(VI) top
Crystal data top
[Sn4O2(C5H3O2S)4(C4H9)8]F(000) = 1480
Mr = 1472.19Dx = 1.555 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 13.495 (2) ÅCell parameters from 492 reflections
b = 17.324 (3) Åθ = 1–25°
c = 13.471 (2) ŵ = 1.75 mm1
β = 93.01 (1)°T = 173 K
V = 3145.0 (9) Å3Block, colourless
Z = 20.46 × 0.42 × 0.34 mm
Data collection top
Siemens CCD three-circle
diffractometer
8637 independent reflections
Radiation source: fine-focus sealed tube7626 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 27.2°, θmin = 1.5°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.470, Tmax = 0.550k = 2110
12639 measured reflectionsl = 016
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-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 reflectionsΔρmax = 0.47 e Å3
653 parametersΔρmin = 0.57 e Å3
15 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.50 (2)
Crystal data top
[Sn4O2(C5H3O2S)4(C4H9)8]V = 3145.0 (9) Å3
Mr = 1472.19Z = 2
Monoclinic, P21Mo Kα radiation
a = 13.495 (2) ŵ = 1.75 mm1
b = 17.324 (3) ÅT = 173 K
c = 13.471 (2) Å0.46 × 0.42 × 0.34 mm
β = 93.01 (1)°
Data collection top
Siemens CCD three-circle
diffractometer
8637 independent reflections
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
7626 reflections with I > 2σ(I)
Tmin = 0.470, Tmax = 0.550Rint = 0.015
12639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.049Δρmax = 0.47 e Å3
S = 0.96Δρmin = 0.57 e Å3
8637 reflectionsAbsolute structure: Flack (1983)
653 parametersAbsolute structure parameter: 0.50 (2)
15 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.36159 (2)0.29767 (2)0.79329 (2)0.02546 (9)
O10.23474 (19)0.3359 (2)0.8546 (2)0.0255 (8)
Sn20.12516 (2)0.33406 (2)0.73123 (2)0.02596 (9)
O20.2512 (2)0.2946 (2)0.6701 (2)0.0276 (8)
Sn30.19353 (2)0.36318 (2)0.99338 (2)0.02758 (9)
Sn40.29313 (2)0.26249 (2)0.53360 (2)0.02974 (10)
O110.4517 (2)0.3124 (3)0.9376 (2)0.0405 (12)
C110.4297 (3)0.3142 (3)1.0261 (4)0.0308 (14)
O120.3455 (2)0.3315 (3)1.0568 (2)0.0477 (12)
C120.5072 (3)0.2920 (4)1.1025 (3)0.0304 (12)
S130.48102 (10)0.29016 (12)1.22583 (10)0.0485 (4)
C140.5976 (4)0.2620 (4)1.2579 (4)0.0487 (17)
H140.62170.25401.32470.058*
C150.6534 (4)0.2519 (4)1.1785 (4)0.0473 (17)
H150.72040.23481.18460.057*
C160.6045 (3)0.2688 (4)1.0858 (3)0.0318 (13)
H160.63270.26511.02290.038*
O210.0354 (2)0.3200 (3)0.5862 (2)0.0411 (12)
C210.0564 (4)0.3077 (4)0.4987 (4)0.0327 (14)
O220.1376 (2)0.2808 (3)0.4732 (3)0.0586 (14)
C220.0198 (3)0.3236 (4)0.4204 (3)0.0351 (14)
S230.00570 (11)0.31025 (14)0.29845 (11)0.0693 (7)
C240.1095 (4)0.3390 (5)0.2596 (4)0.071 (2)
H240.13190.34130.19160.085*
C250.1669 (4)0.3584 (5)0.3359 (4)0.0561 (19)
H250.23370.37520.32630.067*
C260.1173 (3)0.3513 (3)0.4311 (3)0.0246 (12)
H260.14540.36320.49250.029*
O310.0530 (2)0.3857 (2)0.9093 (2)0.0305 (9)
C310.0140 (4)0.4002 (4)0.9721 (4)0.0350 (14)
C320.1187 (3)0.4067 (4)0.9276 (4)0.0332 (14)
O320.0032 (3)0.4068 (3)1.0612 (3)0.0449 (11)
C330.1472 (3)0.4044 (3)0.8179 (4)0.080 (2)0.760 (7)
H330.10670.39960.76260.096*0.760 (7)
S330.1472 (3)0.4044 (3)0.8179 (4)0.080 (2)0.240 (7)
C340.2571 (5)0.4116 (5)0.8208 (6)0.060 (2)
H340.29820.40970.76140.073*
C350.2968 (4)0.4208 (4)0.9102 (6)0.063 (2)
H350.36600.42660.91770.076*
S360.21139 (12)0.42118 (14)1.00797 (16)0.0522 (8)0.760 (7)
C360.21139 (12)0.42118 (14)1.00797 (16)0.0522 (8)0.240 (7)
H360.21400.42701.07790.063*0.240 (7)
O410.4346 (2)0.2479 (2)0.6193 (2)0.0312 (9)
C410.5055 (3)0.2358 (3)0.5577 (4)0.0267 (13)
C420.6071 (3)0.2303 (3)0.6038 (4)0.0288 (13)
O420.4893 (2)0.2288 (3)0.4685 (3)0.0373 (10)
C430.6356 (3)0.2371 (3)0.7136 (3)0.0602 (17)0.808 (6)
H430.59470.24440.76820.072*0.808 (6)
S430.6356 (3)0.2371 (3)0.7136 (3)0.0602 (17)0.192 (6)
C440.7467 (4)0.2290 (4)0.7124 (4)0.0456 (16)
H440.78750.23240.77190.055*
C450.7853 (4)0.2169 (4)0.6255 (4)0.0472 (18)
H450.85440.21020.61850.057*
S460.70183 (12)0.21435 (13)0.52853 (13)0.0471 (7)0.808 (6)
C460.70183 (12)0.21435 (13)0.52853 (13)0.0471 (7)0.192 (6)
H460.70600.20690.45900.057*0.192 (6)
C1010.4391 (3)0.3969 (3)0.7452 (4)0.0301 (13)
H10A0.51110.38550.74800.036*
H10B0.41830.40770.67490.036*
C1020.4215 (4)0.4694 (4)0.8071 (4)0.0398 (15)
H10C0.44260.45890.87730.048*
H10D0.34960.48090.80430.048*
C1030.4775 (5)0.5404 (4)0.7716 (5)0.061 (2)
H10E0.47210.58260.82050.073*
H10F0.54870.52750.76770.073*
C1040.4365 (6)0.5679 (4)0.6701 (6)0.083 (2)
H10G0.47460.61260.64920.124*
H10H0.36670.58250.67430.124*
H10I0.44180.52620.62150.124*
C1050.3615 (4)0.1759 (4)0.8209 (4)0.0412 (15)
H10J0.31340.16700.87260.049*
H10K0.33320.15130.75940.049*
C1060.4512 (5)0.1314 (5)0.8512 (7)0.081 (3)
H10L0.48880.16090.90370.097*
H10M0.49340.12790.79350.097*
C1070.4348 (8)0.0502 (5)0.8899 (8)0.097 (3)
H10N0.49900.02830.91520.117*
H10O0.39000.05220.94570.117*
C1080.3917 (7)0.0007 (5)0.8115 (7)0.103 (3)
H10P0.38090.05100.83830.155*
H10Q0.43710.00250.75720.155*
H10R0.32820.02240.78640.155*
C2010.0434 (4)0.2375 (4)0.7803 (4)0.0361 (14)
H20A0.06060.22870.85170.043*
H20B0.02830.24960.77320.043*
C2020.0627 (5)0.1653 (4)0.7243 (5)0.0492 (17)
H20C0.13470.15390.72940.059*
H20D0.04290.17310.65320.059*
C2030.0048 (6)0.0954 (5)0.7648 (6)0.077 (2)
H20E0.02800.08600.83470.092*
H20F0.06650.10870.76430.092*
C2040.0162 (8)0.0246 (6)0.7082 (9)0.156 (5)
H20G0.02100.01710.73840.234*
H20H0.08660.01060.70860.234*
H20I0.00940.03250.63960.234*
C2050.1255 (4)0.4545 (4)0.7082 (4)0.0433 (16)
H20J0.12660.47910.77450.052*
H20K0.18920.46760.67900.052*
C2060.0464 (7)0.4922 (5)0.6465 (11)0.191 (7)
H20L0.01860.47420.66840.229*
H20M0.05180.47560.57670.229*
C2070.0483 (8)0.5809 (5)0.6500 (11)0.170 (6)
H20N0.01570.60010.62040.203*
H20O0.05250.59700.72070.203*
C2080.1246 (10)0.6171 (7)0.6021 (13)0.258 (11)
H20P0.11850.67320.60910.387*
H20Q0.12030.60340.53140.387*
H20R0.18880.60030.63200.387*
C3010.1474 (4)0.2665 (4)1.0743 (4)0.0389 (14)
H30A0.16240.27681.14580.047*
H30B0.07440.26221.06430.047*
C3020.1913 (5)0.1911 (4)1.0500 (4)0.0545 (18)
H30C0.26440.19631.05340.065*
H30D0.17020.17760.98070.065*
C3030.1626 (6)0.1235 (4)1.1193 (6)0.078 (3)
H30E0.08940.12121.12170.093*
H30F0.18520.07411.09130.093*
C3040.2079 (8)0.1327 (6)1.2238 (6)0.109 (3)
H30G0.18780.08941.26490.163*
H30H0.18490.18121.25230.163*
H30I0.28040.13361.22200.163*
C3050.2345 (4)0.4780 (4)1.0278 (4)0.0428 (16)
H30J0.24480.48151.10100.051*
H30K0.29980.48730.99970.051*
C3060.1667 (4)0.5439 (4)0.9945 (4)0.0419 (16)
H30L0.10230.53801.02580.050*
H30M0.15380.54090.92160.050*
C3070.2099 (5)0.6231 (4)1.0212 (5)0.058 (2)
H30N0.22470.62561.09390.070*
H30O0.27310.62980.98810.070*
C3080.1409 (5)0.6875 (5)0.9910 (6)0.071 (2)
H30P0.17140.73701.01040.106*
H30Q0.07840.68141.02400.106*
H30R0.12780.68640.91880.106*
C4010.2607 (4)0.1442 (4)0.5065 (5)0.0524 (18)
H40A0.20860.12950.55200.063*
H40B0.23040.14080.43820.063*
C4020.3378 (5)0.0843 (4)0.5154 (5)0.059 (2)
H40C0.36890.08570.58360.071*
H40D0.39000.09640.46880.071*
C4030.3003 (5)0.0036 (5)0.4943 (6)0.074 (2)
H40E0.26890.00290.42620.089*
H40F0.24770.00770.54070.089*
C4040.3753 (6)0.0614 (5)0.5021 (7)0.100 (3)
H40G0.34280.11010.48310.149*
H40H0.40290.06500.57070.149*
H40I0.42890.05100.45760.149*
C4050.3322 (5)0.3606 (4)0.4487 (4)0.0583 (19)
H40J0.40250.37300.46650.070*
H40K0.32820.34550.37780.070*
C4060.2728 (6)0.4336 (4)0.4584 (6)0.104 (3)
H40L0.30380.46580.51220.125*0.517 (16)
H40M0.20500.41990.47700.125*0.517 (16)
H40N0.26590.44470.52980.125*0.483 (16)
H40O0.20550.42580.42710.125*0.483 (16)
C4710.2644 (9)0.4791 (9)0.3606 (12)0.123 (9)0.517 (16)
H47A0.23810.44490.30660.148*0.517 (16)
H47B0.21700.52220.36710.148*0.517 (16)
C4720.3217 (11)0.5029 (5)0.4088 (9)0.060 (5)0.483 (16)
H47C0.29360.55130.43430.072*0.483 (16)
H47D0.39380.50270.42690.072*0.483 (16)
C4810.3632 (11)0.5109 (13)0.3337 (14)0.101 (8)0.517 (16)
H48A0.35510.53990.27130.152*0.517 (16)
H48B0.40980.46830.32550.152*0.517 (16)
H48C0.38910.54530.38670.152*0.517 (16)
C4820.3061 (16)0.5008 (12)0.2980 (8)0.081 (7)0.483 (16)
H48D0.33810.54570.26920.122*0.483 (16)
H48E0.23480.50190.27980.122*0.483 (16)
H48F0.33510.45340.27230.122*0.483 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02083 (16)0.0302 (2)0.02557 (17)0.00244 (16)0.00295 (13)0.00175 (16)
O10.0223 (15)0.033 (2)0.0214 (15)0.0013 (16)0.0008 (13)0.0059 (16)
Sn20.02052 (16)0.0318 (3)0.02571 (17)0.00237 (15)0.00290 (13)0.00017 (16)
O20.0229 (16)0.036 (2)0.0238 (15)0.0035 (17)0.0036 (13)0.0032 (17)
Sn30.02515 (17)0.0340 (3)0.02380 (17)0.00534 (16)0.00305 (14)0.00103 (16)
Sn40.02604 (18)0.0383 (3)0.02497 (17)0.00659 (17)0.00221 (14)0.00421 (17)
O110.0307 (19)0.068 (4)0.0229 (18)0.003 (2)0.0012 (15)0.005 (2)
C110.026 (3)0.032 (4)0.033 (3)0.004 (2)0.006 (2)0.004 (3)
O120.0341 (19)0.075 (4)0.0338 (19)0.022 (2)0.0014 (16)0.001 (2)
C120.032 (3)0.037 (4)0.022 (2)0.002 (2)0.003 (2)0.002 (2)
S130.0400 (7)0.0726 (13)0.0328 (7)0.0049 (8)0.0019 (6)0.0017 (8)
C140.046 (3)0.066 (5)0.033 (3)0.008 (3)0.013 (2)0.011 (3)
C150.030 (3)0.067 (5)0.044 (3)0.010 (3)0.002 (2)0.000 (3)
C160.023 (2)0.042 (4)0.029 (2)0.001 (2)0.007 (2)0.005 (3)
O210.0289 (18)0.069 (4)0.0250 (18)0.0027 (19)0.0046 (14)0.0050 (19)
C210.029 (3)0.035 (4)0.033 (3)0.002 (3)0.001 (2)0.004 (3)
O220.0297 (19)0.103 (4)0.041 (2)0.023 (2)0.0110 (17)0.024 (2)
C220.028 (3)0.047 (4)0.030 (3)0.002 (2)0.001 (2)0.002 (3)
S230.0455 (9)0.128 (2)0.0344 (8)0.0156 (10)0.0019 (6)0.0060 (10)
C240.053 (4)0.132 (8)0.026 (3)0.006 (4)0.012 (3)0.007 (4)
C250.035 (3)0.084 (6)0.048 (3)0.011 (4)0.006 (3)0.004 (4)
C260.020 (2)0.033 (4)0.020 (2)0.002 (2)0.0036 (18)0.001 (2)
O310.0210 (17)0.042 (3)0.0293 (18)0.0060 (17)0.0040 (15)0.0014 (17)
C310.032 (3)0.032 (4)0.042 (3)0.008 (3)0.010 (3)0.003 (3)
C320.020 (3)0.029 (4)0.051 (3)0.004 (2)0.006 (2)0.002 (3)
O320.044 (2)0.059 (3)0.032 (2)0.014 (2)0.0080 (17)0.003 (2)
C330.046 (3)0.053 (4)0.138 (5)0.004 (2)0.029 (3)0.022 (3)
S330.046 (3)0.053 (4)0.138 (5)0.004 (2)0.029 (3)0.022 (3)
C340.044 (4)0.055 (6)0.080 (5)0.008 (4)0.012 (4)0.011 (4)
C350.023 (3)0.058 (5)0.108 (6)0.003 (3)0.000 (3)0.010 (5)
S360.0270 (10)0.0627 (18)0.0684 (15)0.0113 (9)0.0158 (9)0.0178 (12)
C360.0270 (10)0.0627 (18)0.0684 (15)0.0113 (9)0.0158 (9)0.0178 (12)
O410.0244 (17)0.038 (3)0.0317 (18)0.0028 (17)0.0029 (14)0.0021 (18)
C410.024 (3)0.024 (4)0.033 (3)0.002 (2)0.003 (2)0.002 (2)
C420.023 (2)0.030 (4)0.035 (3)0.003 (2)0.006 (2)0.008 (3)
O420.033 (2)0.049 (3)0.030 (2)0.0075 (19)0.0015 (15)0.0058 (19)
C430.035 (2)0.057 (4)0.086 (3)0.007 (2)0.021 (2)0.001 (3)
S430.035 (2)0.057 (4)0.086 (3)0.007 (2)0.021 (2)0.001 (3)
C440.035 (3)0.053 (5)0.048 (3)0.004 (3)0.010 (3)0.011 (3)
C450.023 (3)0.063 (6)0.055 (4)0.010 (3)0.001 (3)0.006 (4)
S460.0268 (9)0.0709 (17)0.0440 (11)0.0106 (8)0.0043 (7)0.0038 (10)
C460.0268 (9)0.0709 (17)0.0440 (11)0.0106 (8)0.0043 (7)0.0038 (10)
C1010.028 (3)0.035 (4)0.028 (3)0.004 (2)0.001 (2)0.005 (3)
C1020.047 (3)0.033 (4)0.039 (3)0.008 (3)0.007 (3)0.002 (3)
C1030.075 (5)0.046 (5)0.063 (4)0.004 (4)0.014 (4)0.006 (4)
C1040.126 (7)0.042 (5)0.081 (6)0.007 (4)0.014 (5)0.002 (4)
C1050.046 (4)0.032 (4)0.046 (3)0.002 (3)0.010 (3)0.003 (3)
C1060.056 (5)0.058 (7)0.125 (7)0.007 (4)0.025 (5)0.026 (6)
C1070.145 (9)0.030 (6)0.115 (8)0.011 (6)0.007 (6)0.010 (5)
C1080.119 (7)0.057 (7)0.138 (9)0.022 (5)0.053 (6)0.043 (6)
C2010.035 (3)0.040 (4)0.034 (3)0.008 (3)0.005 (2)0.000 (3)
C2020.048 (4)0.039 (5)0.060 (4)0.011 (3)0.002 (3)0.004 (3)
C2030.104 (6)0.041 (5)0.085 (6)0.005 (5)0.006 (5)0.009 (5)
C2040.215 (13)0.068 (8)0.185 (13)0.040 (8)0.016 (10)0.007 (8)
C2050.057 (4)0.039 (5)0.034 (3)0.009 (3)0.001 (3)0.008 (3)
C2060.146 (11)0.042 (8)0.38 (2)0.019 (7)0.065 (12)0.084 (11)
C2070.142 (10)0.068 (10)0.30 (2)0.032 (8)0.025 (11)0.053 (11)
C2080.247 (17)0.184 (18)0.36 (3)0.043 (13)0.195 (18)0.096 (17)
C3010.039 (3)0.037 (4)0.041 (3)0.010 (3)0.009 (2)0.004 (3)
C3020.072 (4)0.052 (5)0.041 (3)0.007 (4)0.018 (3)0.004 (3)
C3030.121 (7)0.033 (6)0.082 (6)0.012 (5)0.029 (5)0.016 (4)
C3040.190 (9)0.070 (7)0.067 (6)0.024 (7)0.011 (6)0.019 (5)
C3050.036 (3)0.053 (5)0.039 (3)0.005 (3)0.003 (3)0.008 (3)
C3060.043 (3)0.033 (5)0.051 (4)0.006 (3)0.009 (3)0.003 (3)
C3070.081 (5)0.031 (5)0.065 (4)0.010 (4)0.023 (4)0.016 (4)
C3080.086 (5)0.031 (5)0.100 (6)0.003 (4)0.036 (5)0.001 (4)
C4010.051 (4)0.038 (5)0.067 (4)0.001 (3)0.001 (3)0.028 (4)
C4020.052 (4)0.045 (6)0.081 (5)0.000 (4)0.019 (4)0.001 (4)
C4030.063 (5)0.060 (7)0.101 (6)0.006 (4)0.014 (4)0.017 (5)
C4040.088 (6)0.056 (7)0.158 (9)0.000 (5)0.043 (6)0.005 (6)
C4050.068 (4)0.057 (5)0.052 (4)0.016 (4)0.027 (3)0.016 (4)
C4060.114 (7)0.087 (8)0.118 (8)0.055 (6)0.059 (6)0.041 (6)
C4710.075 (13)0.21 (3)0.082 (16)0.044 (14)0.005 (11)0.026 (16)
C4720.069 (11)0.049 (12)0.063 (10)0.010 (9)0.014 (9)0.018 (8)
C4810.089 (14)0.099 (18)0.11 (2)0.001 (12)0.015 (12)0.047 (14)
C4820.098 (17)0.087 (17)0.059 (11)0.006 (14)0.001 (11)0.015 (11)
Geometric parameters (Å, º) top
Sn1—O12.049 (3)C108—H10Q0.9800
Sn1—C1012.132 (5)C108—H10R0.9800
Sn1—C1052.142 (6)C201—C2021.490 (9)
Sn1—O22.172 (3)C201—H20A0.9900
Sn1—O112.253 (3)C201—H20B0.9900
O1—Sn32.034 (3)C202—C2031.556 (10)
O1—Sn22.166 (3)C202—H20C0.9900
Sn2—O22.046 (3)C202—H20D0.9900
Sn2—C2052.110 (6)C203—C2041.457 (12)
Sn2—C2012.128 (5)C203—H20E0.9900
Sn2—O212.258 (3)C203—H20F0.9900
O2—Sn42.030 (3)C204—H20G0.9800
Sn3—C3052.110 (7)C204—H20H0.9800
Sn3—C3012.109 (6)C204—H20I0.9800
Sn3—O312.192 (3)C205—C2061.472 (8)
Sn3—O122.248 (3)C205—H20J0.9900
Sn4—C4012.122 (7)C205—H20K0.9900
Sn4—C4052.130 (6)C206—C2071.536 (8)
Sn4—O412.194 (3)C206—H20L0.9900
Sn4—O222.234 (3)C206—H20M0.9900
O11—C111.244 (5)C207—C2081.394 (8)
C11—O121.265 (5)C207—H20N0.9900
C11—C121.479 (6)C207—H20O0.9900
C12—C161.402 (6)C208—H20P0.9800
C12—S131.717 (4)C208—H20Q0.9800
S13—C141.682 (6)C208—H20R0.9800
C14—C151.351 (7)C301—C3021.479 (8)
C14—H140.9500C301—H30A0.9900
C15—C161.412 (7)C301—H30B0.9900
C15—H150.9500C302—C3031.559 (9)
C16—H160.9500C302—H30C0.9900
O21—C211.245 (6)C302—H30D0.9900
C21—O221.255 (6)C303—C3041.514 (11)
C21—C221.461 (7)C303—H30E0.9900
C22—C261.415 (6)C303—H30F0.9900
C22—S231.711 (5)C304—H30G0.9800
S23—C241.689 (6)C304—H30H0.9800
C24—C251.360 (8)C304—H30I0.9800
C24—H240.9500C305—C3061.517 (9)
C25—C261.420 (7)C305—H30J0.9900
C25—H250.9500C305—H30K0.9900
C26—H260.9500C306—C3071.526 (9)
O31—C311.296 (6)C306—H30L0.9900
C31—O321.216 (6)C306—H30M0.9900
C31—C321.509 (7)C307—C3081.496 (10)
C32—C331.508 (7)C307—H30N0.9900
C32—S361.716 (5)C307—H30O0.9900
C33—C341.491 (7)C308—H30P0.9800
C33—H330.9500C308—H30Q0.9800
C34—C351.352 (9)C308—H30R0.9800
C34—H340.9500C401—C4021.471 (9)
C35—S361.704 (7)C401—H40A0.9900
C35—H350.9500C401—H40B0.9900
O41—C411.316 (5)C402—C4031.508 (11)
C41—O421.216 (6)C402—H40C0.9900
C41—C421.479 (7)C402—H40D0.9900
C42—C431.513 (7)C403—C4041.513 (11)
C42—S461.695 (5)C403—H40E0.9900
C43—C441.507 (6)C403—H40F0.9900
C43—H430.9500C404—H40G0.9800
C44—C451.323 (8)C404—H40H0.9800
C44—H440.9500C404—H40I0.9800
C45—S461.680 (6)C405—C4061.505 (7)
C45—H450.9500C405—H40J0.9900
C101—C1021.532 (8)C405—H40K0.9900
C101—H10A0.9900C406—C4711.535 (9)
C101—H10B0.9900C406—C4721.539 (8)
C102—C1031.533 (9)C406—H40L0.9900
C102—H10C0.9900C406—H40M0.9901
C102—H10D0.9900C406—H40N0.9900
C103—C1041.524 (9)C406—H40O0.9901
C103—H10E0.9900C471—C4811.505 (10)
C103—H10F0.9900C471—H40O1.5375
C104—H10G0.9800C471—H47A0.9900
C104—H10H0.9800C471—H47B0.9900
C104—H10I0.9800C472—C4821.498 (9)
C105—C1061.474 (8)C472—H40L1.5641
C105—H10J0.9900C472—H47C0.9900
C105—H10K0.9900C472—H47D0.9900
C106—C1071.520 (10)C481—H48A0.9800
C106—H10L0.9900C481—H48B0.9800
C106—H10M0.9900C481—H48C0.9800
C107—C1081.457 (12)C482—H48D0.9800
C107—H10N0.9900C482—H48E0.9800
C107—H10O0.9900C482—H48F0.9800
C108—H10P0.9800
O1—Sn1—C101107.19 (18)C203—C202—H20C109.3
O1—Sn1—C105103.91 (18)C201—C202—H20D109.3
C101—Sn1—C105148.4 (2)C203—C202—H20D109.3
O1—Sn1—O276.22 (11)H20C—C202—H20D107.9
C101—Sn1—O296.63 (17)C204—C203—C202113.8 (7)
C105—Sn1—O295.8 (2)C204—C203—H20E108.8
O1—Sn1—O1192.31 (12)C202—C203—H20E108.8
C101—Sn1—O1185.40 (17)C204—C203—H20F108.8
C105—Sn1—O1188.1 (2)C202—C203—H20F108.8
O2—Sn1—O11168.45 (12)H20E—C203—H20F107.7
Sn3—O1—Sn1136.05 (14)C203—C204—H20G109.5
Sn3—O1—Sn2120.00 (13)C203—C204—H20H109.5
Sn1—O1—Sn2103.73 (12)H20G—C204—H20H109.5
O2—Sn2—C205105.25 (19)C203—C204—H20I109.5
O2—Sn2—C201108.50 (19)H20G—C204—H20I109.5
C205—Sn2—C201146.0 (2)H20H—C204—H20I109.5
O2—Sn2—O176.42 (11)C206—C205—Sn2121.0 (5)
C205—Sn2—O195.26 (19)C206—C205—H20J107.1
C201—Sn2—O196.74 (17)Sn2—C205—H20J107.1
O2—Sn2—O2192.03 (12)C206—C205—H20K107.1
C205—Sn2—O2189.1 (2)Sn2—C205—H20K107.1
C201—Sn2—O2185.46 (17)H20J—C205—H20K106.8
O1—Sn2—O21168.36 (12)C205—C206—C207114.6 (8)
Sn4—O2—Sn2137.17 (15)C205—C206—H20L108.6
Sn4—O2—Sn1119.10 (13)C207—C206—H20L108.6
Sn2—O2—Sn1103.63 (12)C205—C206—H20M108.6
O1—Sn3—C305109.88 (19)C207—C206—H20M108.6
O1—Sn3—C301113.12 (19)H20L—C206—H20M107.6
C305—Sn3—C301135.7 (2)C208—C207—C206116.6 (9)
O1—Sn3—O3180.62 (11)C208—C207—H20N108.2
C305—Sn3—O3198.98 (19)C206—C207—H20N108.2
C301—Sn3—O3197.88 (17)C208—C207—H20O108.2
O1—Sn3—O1290.26 (11)C206—C207—H20O108.2
C305—Sn3—O1285.6 (2)H20N—C207—H20O107.3
C301—Sn3—O1284.14 (18)C207—C208—H20P109.5
O31—Sn3—O12170.74 (12)C207—C208—H20Q109.5
O2—Sn4—C401110.8 (2)H20P—C208—H20Q109.5
O2—Sn4—C405110.9 (2)C207—C208—H20R109.5
C401—Sn4—C405137.1 (3)H20P—C208—H20R109.5
O2—Sn4—O4180.27 (12)H20Q—C208—H20R109.5
C401—Sn4—O4198.3 (2)C302—C301—Sn3117.0 (4)
C405—Sn4—O4198.2 (2)C302—C301—H30A108.0
O2—Sn4—O2289.42 (12)Sn3—C301—H30A108.0
C401—Sn4—O2283.9 (2)C302—C301—H30B108.0
C405—Sn4—O2286.9 (2)Sn3—C301—H30B108.0
O41—Sn4—O22169.59 (12)H30A—C301—H30B107.3
C11—O11—Sn1133.2 (3)C301—C302—C303114.6 (5)
O11—C11—O12125.7 (4)C301—C302—H30C108.6
O11—C11—C12117.6 (4)C303—C302—H30C108.6
O12—C11—C12116.7 (4)C301—C302—H30D108.6
C11—O12—Sn3138.6 (3)C303—C302—H30D108.6
C16—C12—C11126.7 (4)H30C—C302—H30D107.6
C16—C12—S13113.0 (3)C304—C303—C302112.1 (7)
C11—C12—S13120.2 (3)C304—C303—H30E109.2
C14—S13—C1290.9 (2)C302—C303—H30E109.2
C15—C14—S13112.8 (4)C304—C303—H30F109.2
C15—C14—H14123.6C302—C303—H30F109.2
S13—C14—H14123.6H30E—C303—H30F107.9
C14—C15—C16114.7 (5)C303—C304—H30G109.5
C14—C15—H15122.6C303—C304—H30H109.5
C16—C15—H15122.6H30G—C304—H30H109.5
C12—C16—C15108.5 (4)C303—C304—H30I109.5
C12—C16—H16125.8H30G—C304—H30I109.5
C15—C16—H16125.8H30H—C304—H30I109.5
C21—O21—Sn2134.3 (3)C306—C305—Sn3119.8 (4)
O21—C21—O22124.7 (5)C306—C305—H30J107.4
O21—C21—C22117.7 (4)Sn3—C305—H30J107.4
O22—C21—C22117.6 (4)C306—C305—H30K107.4
C21—O22—Sn4140.3 (3)Sn3—C305—H30K107.4
C26—C22—C21127.8 (4)H30J—C305—H30K106.9
C26—C22—S23112.2 (3)C305—C306—C307112.9 (5)
C21—C22—S23119.9 (4)C305—C306—H30L109.0
C24—S23—C2291.7 (3)C307—C306—H30L109.0
C25—C24—S23113.0 (4)C305—C306—H30M109.0
C25—C24—H24123.5C307—C306—H30M109.0
S23—C24—H24123.5H30L—C306—H30M107.8
C24—C25—C26113.6 (5)C308—C307—C306112.4 (6)
C24—C25—H25123.2C308—C307—H30N109.1
C26—C25—H25123.2C306—C307—H30N109.1
C22—C26—C25109.5 (4)C308—C307—H30O109.1
C22—C26—H26125.3C306—C307—H30O109.1
C25—C26—H26125.3H30N—C307—H30O107.9
C31—O31—Sn3108.2 (3)C307—C308—H30P109.5
O32—C31—O31124.0 (5)C307—C308—H30Q109.5
O32—C31—C32120.8 (4)H30P—C308—H30Q109.5
O31—C31—C32115.2 (5)C307—C308—H30R109.5
C33—C32—C31125.0 (4)H30P—C308—H30R109.5
C33—C32—S36117.7 (4)H30Q—C308—H30R109.5
C31—C32—S36117.3 (4)C402—C401—Sn4122.0 (5)
C34—C33—C32100.1 (5)C402—C401—H40A106.8
C34—C33—H33130.0Sn4—C401—H40A106.8
C32—C33—H33130.0C402—C401—H40B106.8
C35—C34—C33118.3 (6)Sn4—C401—H40B106.8
C35—C34—H34120.8H40A—C401—H40B106.7
C33—C34—H34120.8C401—C402—C403114.2 (6)
C34—C35—S36113.9 (4)C401—C402—H40C108.7
C34—C35—H35123.0C403—C402—H40C108.7
S36—C35—H35123.0C401—C402—H40D108.7
C35—S36—C3289.9 (3)C403—C402—H40D108.7
C41—O41—Sn4109.1 (3)H40C—C402—H40D107.6
O42—C41—O41122.7 (4)C402—C403—C404117.3 (7)
O42—C41—C42121.6 (4)C402—C403—H40E108.0
O41—C41—C42115.7 (4)C404—C403—H40E108.0
C41—C42—C43126.0 (4)C402—C403—H40F108.0
C41—C42—S46118.1 (4)C404—C403—H40F108.0
C43—C42—S46115.9 (3)H40E—C403—H40F107.2
C44—C43—C42100.6 (4)C403—C404—H40G109.5
C44—C43—H43129.7C403—C404—H40H109.5
C42—C43—H43129.7H40G—C404—H40H109.5
C45—C44—C43117.5 (5)C403—C404—H40I109.5
C45—C44—H44121.2H40G—C404—H40I109.5
C43—C44—H44121.2H40H—C404—H40I109.5
C44—C45—S46114.4 (4)C406—C405—Sn4118.4 (4)
C44—C45—H45122.8C406—C405—H40J107.7
S46—C45—H45122.8Sn4—C405—H40J107.7
C45—S46—C4291.5 (3)C406—C405—H40K107.7
C102—C101—Sn1113.8 (3)Sn4—C405—H40K107.7
C102—C101—H10A108.8H40J—C405—H40K107.1
Sn1—C101—H10A108.8C405—C406—C471111.9 (7)
C102—C101—H10B108.8C405—C406—C472112.0 (6)
Sn1—C101—H10B108.8C471—C406—C47240.6 (7)
H10A—C101—H10B107.7C405—C406—H40L109.3
C101—C102—C103113.2 (5)C471—C406—H40L110.4
C101—C102—H10C108.9C472—C406—H40L72.8
C103—C102—H10C108.9C405—C406—H40M108.9
C101—C102—H10D108.9C471—C406—H40M108.3
C103—C102—H10D108.9C472—C406—H40M136.0
H10C—C102—H10D107.7H40L—C406—H40M108.0
C104—C103—C102111.7 (6)C405—C406—H40N108.9
C104—C103—H10E109.3C471—C406—H40N136.7
C102—C103—H10E109.3C472—C406—H40N109.5
C104—C103—H10F109.3H40L—C406—H40N40.2
C102—C103—H10F109.3H40M—C406—H40N70.4
H10E—C103—H10F108.0C405—C406—H40O109.2
C103—C104—H10G109.5C471—C406—H40O71.4
C103—C104—H10H109.5C472—C406—H40O109.1
H10G—C104—H10H109.5H40L—C406—H40O136.9
C103—C104—H10I109.5H40M—C406—H40O40.2
H10G—C104—H10I109.5H40N—C406—H40O108.0
H10H—C104—H10I109.5C481—C471—C406111.6 (9)
C106—C105—Sn1123.7 (5)C481—C471—H40O148.5
C106—C105—H10J106.4C406—C471—H40O37.6
Sn1—C105—H10J106.4C481—C471—H47A109.3
C106—C105—H10K106.4C406—C471—H47A109.3
Sn1—C105—H10K106.4H40O—C471—H47A83.8
H10J—C105—H10K106.5C481—C471—H47B109.3
C105—C106—C107116.6 (7)C406—C471—H47B109.3
C105—C106—H10L108.1H40O—C471—H47B92.6
C107—C106—H10L108.1H47A—C471—H47B108.0
C105—C106—H10M108.1C482—C472—C406111.9 (9)
C107—C106—H10M108.1C482—C472—H40L149.0
H10L—C106—H10M107.3C406—C472—H40L37.2
C108—C107—C106110.9 (8)C482—C472—H47C109.2
C108—C107—H10N109.5C406—C472—H47C109.2
C106—C107—H10N109.5H40L—C472—H47C87.7
C108—C107—H10O109.5C482—C472—H47D109.2
C106—C107—H10O109.5C406—C472—H47D109.2
H10N—C107—H10O108.1H40L—C472—H47D88.7
C107—C108—H10P109.5H47C—C472—H47D107.9
C107—C108—H10Q109.5C471—C481—H48A109.5
H10P—C108—H10Q109.5C471—C481—H48B109.5
C107—C108—H10R109.5H48A—C481—H48B109.5
H10P—C108—H10R109.5C471—C481—H48C109.5
H10Q—C108—H10R109.5H48A—C481—H48C109.5
C202—C201—Sn2113.3 (3)H48B—C481—H48C109.5
C202—C201—H20A108.9C472—C482—H48D109.5
Sn2—C201—H20A108.9C472—C482—H48E109.5
C202—C201—H20B108.9H48D—C482—H48E109.5
Sn2—C201—H20B108.9C472—C482—H48F109.5
H20A—C201—H20B107.7H48D—C482—H48F109.5
C201—C202—C203111.8 (5)H48E—C482—H48F109.5
C201—C202—H20C109.3
C101—Sn1—O1—Sn393.6 (3)S23—C24—C25—C260.7 (9)
C105—Sn1—O1—Sn380.9 (3)C21—C22—C26—C25179.8 (7)
O2—Sn1—O1—Sn3173.6 (3)S23—C22—C26—C251.2 (7)
O11—Sn1—O1—Sn37.7 (3)C24—C25—C26—C221.2 (9)
C101—Sn1—O1—Sn292.13 (19)O1—Sn3—O31—C31172.9 (4)
C105—Sn1—O1—Sn293.4 (2)C305—Sn3—O31—C3178.2 (4)
O2—Sn1—O1—Sn20.66 (18)C301—Sn3—O31—C3160.7 (4)
O11—Sn1—O1—Sn2178.02 (16)Sn3—O31—C31—O326.2 (8)
Sn3—O1—Sn2—O2174.72 (18)Sn3—O31—C31—C32172.3 (4)
Sn1—O1—Sn2—O20.70 (19)O32—C31—C32—C33176.0 (6)
Sn3—O1—Sn2—C20580.8 (2)O31—C31—C32—C335.5 (9)
Sn1—O1—Sn2—C205103.8 (2)O32—C31—C32—S361.6 (8)
Sn3—O1—Sn2—C20167.3 (2)O31—C31—C32—S36176.9 (4)
Sn1—O1—Sn2—C201108.2 (2)C31—C32—C33—C34178.8 (6)
Sn3—O1—Sn2—O21167.5 (7)S36—C32—C33—C343.5 (6)
Sn1—O1—Sn2—O217.9 (9)C32—C33—C34—C352.7 (8)
C205—Sn2—O2—Sn484.9 (3)C33—C34—C35—S361.0 (9)
C201—Sn2—O2—Sn490.6 (3)C34—C35—S36—C321.1 (6)
O1—Sn2—O2—Sn4176.7 (3)C33—C32—S36—C352.9 (5)
O21—Sn2—O2—Sn44.7 (3)C31—C32—S36—C35179.3 (5)
C205—Sn2—O2—Sn191.2 (2)O2—Sn4—O41—C41170.0 (4)
C201—Sn2—O2—Sn193.3 (2)C401—Sn4—O41—C4180.1 (4)
O1—Sn2—O2—Sn10.66 (18)C405—Sn4—O41—C4160.1 (4)
O21—Sn2—O2—Sn1179.21 (17)O22—Sn4—O41—C41178.4 (9)
O1—Sn1—O2—Sn4177.62 (19)Sn4—O41—C41—O424.8 (7)
C101—Sn1—O2—Sn471.5 (2)Sn4—O41—C41—C42175.8 (4)
C105—Sn1—O2—Sn479.5 (2)O42—C41—C42—C43179.2 (6)
O11—Sn1—O2—Sn4171.0 (7)O41—C41—C42—C430.3 (8)
O1—Sn1—O2—Sn20.70 (19)O42—C41—C42—S460.2 (8)
C101—Sn1—O2—Sn2105.4 (2)O41—C41—C42—S46179.7 (4)
C105—Sn1—O2—Sn2103.6 (2)C41—C42—C43—C44178.5 (6)
O11—Sn1—O2—Sn25.9 (9)S46—C42—C43—C442.0 (6)
Sn1—O1—Sn3—C30584.1 (3)C42—C43—C44—C451.9 (8)
Sn2—O1—Sn3—C305102.3 (2)C43—C44—C45—S461.2 (8)
Sn1—O1—Sn3—C30185.0 (3)C44—C45—S46—C420.1 (6)
Sn2—O1—Sn3—C30188.6 (2)C41—C42—S46—C45179.1 (5)
Sn1—O1—Sn3—O31179.6 (3)C43—C42—S46—C451.4 (5)
Sn2—O1—Sn3—O316.0 (2)O1—Sn1—C101—C10229.7 (4)
Sn1—O1—Sn3—O121.3 (3)C105—Sn1—C101—C102140.1 (4)
Sn2—O1—Sn3—O12172.3 (2)O2—Sn1—C101—C102107.3 (4)
Sn2—O2—Sn4—C40186.7 (3)O11—Sn1—C101—C10261.3 (4)
Sn1—O2—Sn4—C40197.7 (3)Sn1—C101—C102—C103179.9 (4)
Sn2—O2—Sn4—C40582.9 (3)C101—C102—C103—C10468.1 (7)
Sn1—O2—Sn4—C40592.7 (3)O1—Sn1—C105—C106139.6 (6)
Sn2—O2—Sn4—O41178.0 (3)C101—Sn1—C105—C10630.4 (8)
Sn1—O2—Sn4—O412.41 (19)O2—Sn1—C105—C106143.2 (6)
Sn2—O2—Sn4—O223.5 (3)O11—Sn1—C105—C10647.6 (6)
Sn1—O2—Sn4—O22179.1 (2)Sn1—C105—C106—C107166.7 (6)
O1—Sn1—O11—C1123.4 (5)C105—C106—C107—C10865.7 (11)
C101—Sn1—O11—C11130.5 (5)O2—Sn2—C201—C20226.3 (4)
C105—Sn1—O11—C1180.4 (5)C205—Sn2—C201—C202145.9 (4)
O2—Sn1—O11—C1129.8 (11)O1—Sn2—C201—C202104.2 (4)
Sn1—O11—C11—O1223.4 (9)O21—Sn2—C201—C20264.3 (4)
Sn1—O11—C11—C12154.6 (4)Sn2—C201—C202—C203177.9 (5)
O11—C11—O12—Sn32.3 (10)C201—C202—C203—C204176.2 (7)
C12—C11—O12—Sn3175.8 (4)O2—Sn2—C205—C206117.3 (8)
O1—Sn3—O12—C119.2 (6)C201—Sn2—C205—C20655.0 (9)
C305—Sn3—O12—C11100.7 (7)O1—Sn2—C205—C206165.3 (8)
C301—Sn3—O12—C11122.4 (7)O21—Sn2—C205—C20625.5 (8)
O11—C11—C12—C160.0 (9)Sn2—C205—C206—C207171.0 (7)
O12—C11—C12—C16178.2 (6)C205—C206—C207—C20871.6 (18)
O11—C11—C12—S13177.9 (4)O1—Sn3—C301—C30228.6 (5)
O12—C11—C12—S130.3 (8)C305—Sn3—C301—C302136.7 (5)
C16—C12—S13—C141.8 (5)O31—Sn3—C301—C302111.7 (5)
C11—C12—S13—C14180.0 (5)O12—Sn3—C301—C30259.2 (5)
C12—S13—C14—C152.0 (6)Sn3—C301—C302—C303174.1 (5)
S13—C14—C15—C161.7 (8)C301—C302—C303—C30468.5 (9)
C11—C12—C16—C15179.2 (6)O1—Sn3—C305—C30684.6 (4)
S13—C12—C16—C151.2 (7)C301—Sn3—C305—C306109.7 (5)
C14—C15—C16—C120.3 (9)O31—Sn3—C305—C3061.4 (4)
O2—Sn2—O21—C2112.1 (6)O12—Sn3—C305—C306173.3 (4)
C205—Sn2—O21—C2193.2 (6)Sn3—C305—C306—C307177.2 (4)
C201—Sn2—O21—C21120.5 (6)C305—C306—C307—C308178.1 (5)
O1—Sn2—O21—C2119.0 (12)O2—Sn4—C401—C402101.7 (5)
Sn2—O21—C21—O2218.7 (10)C405—Sn4—C401—C40292.6 (6)
Sn2—O21—C21—C22163.1 (4)O41—Sn4—C401—C40219.0 (6)
O21—C21—O22—Sn417.0 (12)O22—Sn4—C401—C402171.2 (6)
C22—C21—O22—Sn4164.8 (5)Sn4—C401—C402—C403179.4 (5)
O2—Sn4—O22—C218.6 (7)C401—C402—C403—C404179.9 (7)
C401—Sn4—O22—C21119.6 (7)O2—Sn4—C405—C40637.4 (7)
C405—Sn4—O22—C21102.4 (7)C401—Sn4—C405—C406128.3 (6)
O41—Sn4—O22—C2116.9 (15)O41—Sn4—C405—C406120.1 (6)
O21—C21—C22—C260.7 (10)O22—Sn4—C405—C40650.8 (6)
O22—C21—C22—C26177.7 (6)Sn4—C405—C406—C471147.0 (7)
O21—C21—C22—S23178.2 (5)Sn4—C405—C406—C472169.1 (7)
O22—C21—C22—S233.5 (9)C405—C406—C471—C48167.3 (18)
C26—C22—S23—C240.7 (6)C472—C406—C471—C48131.5 (14)
C21—C22—S23—C24179.8 (6)C405—C406—C472—C48276.7 (15)
C22—S23—C24—C250.0 (7)C471—C406—C472—C48221.7 (13)

Experimental details

Crystal data
Chemical formula[Sn4O2(C5H3O2S)4(C4H9)8]
Mr1472.19
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)13.495 (2), 17.324 (3), 13.471 (2)
β (°) 93.01 (1)
V3)3145.0 (9)
Z2
Radiation typeMo Kα
µ (mm1)1.75
Crystal size (mm)0.46 × 0.42 × 0.34
Data collection
DiffractometerSiemens CCD three-circle
diffractometer
Absorption correctionEmpirical
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.470, 0.550
No. of measured, independent and
observed [I > 2σ(I)] reflections
12639, 8637, 7626
Rint0.015
(sin θ/λ)max1)0.644
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.049, 0.96
No. of reflections8637
No. of parameters653
No. of restraints15
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.57
Absolute structureFlack (1983)
Absolute structure parameter0.50 (2)

Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Siemens, 1991).

Selected geometric parameters (Å, º) top
Sn1—O12.049 (3)Sn3—O312.192 (3)
Sn1—C1012.132 (5)Sn3—O122.248 (3)
Sn1—C1052.142 (6)Sn4—C4012.122 (7)
Sn1—O22.172 (3)Sn4—C4052.130 (6)
Sn1—O112.253 (3)Sn4—O412.194 (3)
O1—Sn32.034 (3)Sn4—O222.234 (3)
O1—Sn22.166 (3)O11—C111.244 (5)
Sn2—O22.046 (3)C11—O121.265 (5)
Sn2—C2052.110 (6)O21—C211.245 (6)
Sn2—C2012.128 (5)C21—O221.255 (6)
Sn2—O212.258 (3)O31—C311.296 (6)
O2—Sn42.030 (3)C31—O321.216 (6)
Sn3—C3052.110 (7)O41—C411.316 (5)
Sn3—C3012.109 (6)C41—O421.216 (6)
O1—Sn1—C101107.19 (18)C305—Sn3—C301135.7 (2)
O1—Sn1—C105103.91 (18)O1—Sn3—O3180.62 (11)
C101—Sn1—C105148.4 (2)C305—Sn3—O3198.98 (19)
O1—Sn1—O276.22 (11)C301—Sn3—O3197.88 (17)
C101—Sn1—O296.63 (17)O1—Sn3—O1290.26 (11)
C105—Sn1—O295.8 (2)C305—Sn3—O1285.6 (2)
O1—Sn1—O1192.31 (12)C301—Sn3—O1284.14 (18)
C101—Sn1—O1185.40 (17)O31—Sn3—O12170.74 (12)
C105—Sn1—O1188.1 (2)O2—Sn4—C401110.8 (2)
O2—Sn1—O11168.45 (12)O2—Sn4—C405110.9 (2)
Sn3—O1—Sn1136.05 (14)C401—Sn4—C405137.1 (3)
Sn3—O1—Sn2120.00 (13)O2—Sn4—O4180.27 (12)
Sn1—O1—Sn2103.73 (12)C401—Sn4—O4198.3 (2)
O2—Sn2—C205105.25 (19)C405—Sn4—O4198.2 (2)
O2—Sn2—C201108.50 (19)O2—Sn4—O2289.42 (12)
C205—Sn2—C201146.0 (2)C401—Sn4—O2283.9 (2)
O2—Sn2—O176.42 (11)C405—Sn4—O2286.9 (2)
C205—Sn2—O195.26 (19)O41—Sn4—O22169.59 (12)
C201—Sn2—O196.74 (17)C11—O11—Sn1133.2 (3)
O2—Sn2—O2192.03 (12)O11—C11—O12125.7 (4)
C205—Sn2—O2189.1 (2)C11—O12—Sn3138.6 (3)
C201—Sn2—O2185.46 (17)C21—O21—Sn2134.3 (3)
O1—Sn2—O21168.36 (12)O21—C21—O22124.7 (5)
Sn4—O2—Sn2137.17 (15)C21—O22—Sn4140.3 (3)
Sn4—O2—Sn1119.10 (13)C31—O31—Sn3108.2 (3)
Sn2—O2—Sn1103.63 (12)C41—O41—Sn4109.1 (3)
O1—Sn3—C305109.88 (19)C102—C101—Sn1113.8 (3)
O1—Sn3—C301113.12 (19)
 

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