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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1614.
Published online 2008 November 26. doi:  10.1107/S1600536808038567
PMCID: PMC2960123

cyclo-Hexa-μ2-diphenyl­acetato-κ12 O:O′-hexa-μ3-oxido-hexa­kis[phenyl­tin(IV)]

Abstract

In the cyclo­hexa­meric centrosymmetric title compound, [Sn6(C6H5)6(C14H11O2)6O6], each bridging oxide O atom is connected to three Sn atoms and each carboxyl­ate group bridges a pair of Sn atoms so that the three independent Sn atoms all adopt SnCO5 distorted octa­hedral geometries, resulting in a drum-shaped Sn6O6 core.

Related literature

For examples of drum-shaped cyclo­hexa­meric oxophenyl­tin(IV) carboxyl­ates, see: Alcock & Roe (1989 [triangle]); Chandrasekhar et al. (1985 [triangle]); Yin et al. (2003 [triangle]); Zhang et al. (2005 [triangle]). For reviews of organotin carboxyl­ates, see: Tiekink (1991 [triangle], 1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1614-scheme1.jpg

Experimental

Crystal data

  • [Sn6(C6H5)6(C14H11O2)6O6]
  • M r = 2538.11
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1614-efi1.jpg
  • a = 12.9375 (2) Å
  • b = 14.7406 (2) Å
  • c = 14.8043 (2) Å
  • α = 103.368 (1)°
  • β = 111.716 (1)°
  • γ = 92.582 (1)°
  • V = 2525.06 (6) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.53 mm−1
  • T = 112 (2) K
  • 0.25 × 0.20 × 0.17 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.701, T max = 0.781
  • 37375 measured reflections
  • 11415 independent reflections
  • 9692 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.117
  • S = 1.18
  • 11415 reflections
  • 541 parameters
  • H-atom parameters constrained
  • Δρmax = 0.94 e Å−3
  • Δρmin = −2.31 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038567/hb2814sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038567/hb2814Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Canterbury, New Zealand, for the diffraction measurements. We thank the Vice-President’s Office for Research Affairs of Shahid Beheshti University and the University of Malaya for supporting this work.

supplementary crystallographic information

Comment

The drum-shaped Sn6O6 core found for the title compound, (I), cyclohexameric [SnO(C6H5)[O2CCH(C6H5)2]6 or triphenyltin 2-hydroxy-3-phenylpropionate (Fig. 1) is similar to those seen in related structures (Alcock & Roe, 1989; Chandrasekhar et al., 1985; Yin et al., 2003; Zhang et al., 2005. For reviews of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental

Triphenyltin hydroxide (1.0 g, 2.7 mmol) and diphenylacetic acid (0.58 g, 2.7 mmol) were heated in toluene (100 ml) in a Dean-Stark water separator until all the water had been removed. The solvent was removed under reduced pressure to leave a white powder; colourless blocks of (I) were recrystallized from a mixture of hexane and diethyl ether (1:1 v/v) at 268 K (m.p. 370–371 K).

IR (KBr, cm-1): 1551 (CO, asym), 1412 (CO, sym), 566, 609 (Sn—C). 1HNMR (CDCl3): 2.21 (s, 1H),6.7–7.7 (20H, C6H5) p.p.m.. 13CNMR (CDCl3): 59.7 (CH), 128.4(Cmeta), 129.0 (Cpara), 136.8 (Cortho), 137.8(Cipso), 180.0 (CO) p.p.m.. 119SnNMR (CDCl3): -85.6 p.p.m.. Mass spectrum (m/e): 485 (M—Ph) [Ph3SnO2CCHPh]+.

Refinement

The aromatic rings were refined as rigid hexagons (C—C = 1.39 Å). The carbon-bound hydrogen atoms were placed in calculated positions (C—H = 0.95Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The deepest difference hole is 1 Å from Sn2.

Figures

Fig. 1.
View of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 70% probability level.

Crystal data

[Sn6(C6H5)6(C14H11O2)6O6]Z = 1
Mr = 2538.11F000 = 1260
Triclinic, P1Dx = 1.669 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 12.9375 (2) ÅCell parameters from 9896 reflections
b = 14.7406 (2) Åθ = 2.4–32.5º
c = 14.8043 (2) ŵ = 1.53 mm1
α = 103.368 (1)ºT = 112 (2) K
β = 111.716 (1)ºBlock, colorless
γ = 92.582 (1)º0.25 × 0.20 × 0.17 mm
V = 2525.06 (6) Å3

Data collection

Bruker APEXII diffractometer11415 independent reflections
Radiation source: medium-focus sealed tube9692 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 112(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.4º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.701, Tmax = 0.781k = −19→19
37375 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.118  w = 1/[σ2(Fo2) + (0.0656P)2 + 0.8272P] where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.001
11415 reflectionsΔρmax = 0.94 e Å3
541 parametersΔρmin = −2.31 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sn10.53479 (2)0.665112 (17)0.603202 (18)0.00889 (7)
Sn20.41572 (2)0.479921 (17)0.623742 (18)0.00872 (7)
Sn30.65401 (2)0.436746 (17)0.615334 (18)0.00909 (7)
O10.4513 (2)0.78091 (19)0.5569 (2)0.0138 (6)
O20.3127 (2)0.70644 (19)0.4092 (2)0.0134 (6)
O30.4792 (2)0.71780 (18)0.7232 (2)0.0126 (5)
O40.3990 (2)0.58887 (18)0.7415 (2)0.0134 (6)
O50.4928 (2)0.42566 (19)0.7539 (2)0.0131 (5)
O60.6614 (2)0.40039 (19)0.7504 (2)0.0133 (6)
O70.3820 (2)0.57419 (18)0.53567 (19)0.0096 (5)
O80.5761 (2)0.54875 (18)0.65948 (19)0.0099 (5)
O90.4812 (2)0.37808 (18)0.54526 (19)0.0100 (5)
C10.68854 (19)0.75777 (16)0.69348 (17)0.0130 (8)
C20.7322 (2)0.82506 (19)0.66001 (16)0.0198 (9)
H20.70160.82370.59060.024*
C30.8206 (2)0.89432 (17)0.7281 (2)0.0286 (11)
H30.85040.94030.70530.034*
C40.8653 (2)0.89630 (19)0.8297 (2)0.0292 (11)
H40.92570.94360.87630.035*
C50.8216 (2)0.8290 (2)0.86321 (15)0.0335 (12)
H50.85220.83040.93260.040*
C60.7333 (2)0.75976 (19)0.79508 (19)0.0251 (10)
H60.70340.71380.81800.030*
C70.25612 (17)0.40475 (17)0.5900 (2)0.0135 (8)
C80.1648 (2)0.45162 (14)0.5880 (2)0.0214 (9)
H80.17170.51790.59720.026*
C90.06332 (19)0.4015 (2)0.5725 (3)0.0281 (11)
H90.00090.43360.57110.034*
C100.05322 (19)0.3045 (2)0.5590 (3)0.0364 (13)
H10−0.01610.27030.54840.044*
C110.1446 (2)0.25768 (14)0.5610 (3)0.0339 (12)
H110.13770.19140.55180.041*
C120.2460 (2)0.30777 (17)0.5765 (2)0.0229 (9)
H120.30850.27570.57790.028*
C130.82641 (15)0.49468 (18)0.68507 (19)0.0124 (7)
C140.86491 (19)0.57261 (18)0.66235 (19)0.0182 (8)
H140.81350.60120.61650.022*
C150.9786 (2)0.60878 (17)0.7066 (2)0.0259 (10)
H151.00490.66200.69110.031*
C161.05382 (16)0.5670 (2)0.7737 (2)0.0276 (10)
H161.13150.59170.80390.033*
C171.01532 (19)0.4891 (2)0.7964 (2)0.0262 (10)
H171.06670.46050.84220.031*
C180.9016 (2)0.45292 (16)0.7521 (2)0.0191 (9)
H180.87530.39970.76760.023*
C190.3723 (3)0.7794 (3)0.4741 (3)0.0126 (8)
C200.3523 (3)0.8741 (3)0.4514 (3)0.0135 (8)
H200.38330.92330.51750.016*
C210.22811 (16)0.88231 (19)0.40101 (19)0.0155 (8)
C220.1608 (2)0.82467 (17)0.30603 (19)0.0199 (9)
H220.19200.77890.27110.024*
C230.0479 (2)0.83396 (19)0.26215 (17)0.0267 (10)
H230.00190.79460.19720.032*
C240.00225 (16)0.9009 (2)0.3133 (2)0.0271 (10)
H24−0.07490.90720.28330.033*
C250.0695 (2)0.95852 (19)0.4082 (2)0.0264 (10)
H250.03841.00430.44320.032*
C260.1825 (2)0.94924 (18)0.45212 (16)0.0207 (9)
H260.22850.98860.51700.025*
C270.4212 (2)0.89411 (18)0.38980 (19)0.0149 (8)
C280.5037 (2)0.84157 (16)0.3770 (2)0.0194 (9)
H280.51750.78840.40350.023*
C290.5661 (2)0.86681 (19)0.3254 (2)0.0240 (9)
H290.62250.83090.31670.029*
C300.5459 (2)0.94460 (19)0.2867 (2)0.0251 (10)
H300.58850.96190.25140.030*
C310.4634 (2)0.99714 (16)0.2995 (2)0.0226 (9)
H310.44961.05030.27300.027*
C320.4010 (2)0.97190 (17)0.3511 (2)0.0189 (9)
H320.34461.00780.35980.023*
C330.4280 (3)0.6769 (3)0.7630 (3)0.0110 (7)
C340.3966 (3)0.7386 (3)0.8440 (3)0.0131 (8)
H340.37710.69680.88160.016*
C350.4958 (2)0.81260 (17)0.92017 (18)0.0152 (8)
C360.5220 (2)0.89622 (19)0.89992 (17)0.0242 (10)
H360.47820.90820.83750.029*
C370.6122 (3)0.96228 (16)0.9709 (2)0.0311 (11)
H370.63011.01940.95710.037*
C380.6763 (2)0.94472 (19)1.0622 (2)0.0322 (11)
H380.73790.98991.11080.039*
C390.6501 (2)0.8611 (2)1.08246 (17)0.0322 (11)
H390.69390.84911.14480.039*
C400.5599 (2)0.79503 (16)1.0114 (2)0.0253 (10)
H400.54200.73791.02530.030*
C410.29135 (18)0.78216 (19)0.79501 (19)0.0138 (8)
C420.2700 (2)0.8122 (2)0.7083 (2)0.0235 (10)
H420.32100.80490.67550.028*
C430.1739 (2)0.8529 (2)0.66953 (19)0.0290 (11)
H430.15930.87340.61030.035*
C440.09925 (19)0.8636 (2)0.7175 (2)0.0267 (10)
H440.03360.89140.69100.032*
C450.1206 (2)0.8335 (2)0.8042 (2)0.0235 (9)
H450.06960.84080.83700.028*
C460.2167 (2)0.7928 (2)0.84299 (17)0.0196 (9)
H460.23130.77230.90230.023*
C470.5914 (3)0.4068 (3)0.7913 (3)0.0128 (7)
C480.6309 (3)0.3932 (3)0.8978 (3)0.0147 (8)
H480.56420.36360.90480.018*
C490.72011 (19)0.32657 (17)0.9159 (2)0.0163 (8)
C500.8342 (2)0.36122 (15)0.9587 (2)0.0242 (10)
H500.85830.42710.97690.029*
C510.91314 (17)0.2995 (2)0.9748 (2)0.0306 (11)
H510.99110.32311.00410.037*
C520.8779 (2)0.20305 (19)0.9482 (2)0.0296 (11)
H520.93190.16080.95920.035*
C530.7638 (3)0.16840 (14)0.9054 (2)0.0282 (11)
H530.73980.10250.88720.034*
C540.68492 (18)0.23016 (18)0.8892 (2)0.0226 (9)
H540.60690.20650.86000.027*
C550.6707 (2)0.49094 (15)0.97491 (17)0.0147 (8)
C560.6557 (2)0.50229 (16)1.06492 (19)0.0197 (9)
H560.61520.45271.07480.024*
C570.7000 (2)0.58622 (19)1.14048 (16)0.0238 (10)
H570.68980.59401.20200.029*
C580.7593 (2)0.65881 (16)1.12602 (18)0.0233 (9)
H580.78960.71621.17770.028*
C590.7743 (2)0.64746 (16)1.0360 (2)0.0241 (10)
H590.81480.69711.02610.029*
C600.7300 (2)0.56353 (18)0.96046 (16)0.0214 (9)
H600.74020.55580.89890.026*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01146 (13)0.00818 (13)0.00688 (13)0.00179 (9)0.00281 (10)0.00295 (9)
Sn20.01089 (13)0.00863 (13)0.00698 (13)0.00201 (9)0.00306 (10)0.00332 (10)
Sn30.01056 (13)0.00959 (13)0.00707 (13)0.00261 (9)0.00233 (10)0.00380 (10)
O10.0171 (14)0.0137 (14)0.0097 (13)0.0059 (11)0.0033 (11)0.0041 (11)
O20.0154 (13)0.0118 (13)0.0122 (14)0.0021 (11)0.0039 (11)0.0039 (11)
O30.0164 (13)0.0117 (13)0.0096 (13)0.0007 (10)0.0063 (11)0.0011 (10)
O40.0196 (14)0.0097 (13)0.0127 (14)0.0023 (11)0.0083 (12)0.0026 (11)
O50.0135 (13)0.0172 (14)0.0094 (13)0.0036 (11)0.0027 (11)0.0076 (11)
O60.0139 (13)0.0185 (14)0.0100 (13)0.0042 (11)0.0042 (11)0.0085 (11)
O70.0117 (12)0.0084 (12)0.0089 (13)0.0015 (10)0.0038 (10)0.0028 (10)
O80.0110 (12)0.0101 (13)0.0078 (12)0.0018 (10)0.0015 (10)0.0045 (10)
O90.0126 (13)0.0103 (13)0.0080 (13)0.0044 (10)0.0037 (10)0.0039 (10)
C10.0140 (18)0.0089 (18)0.0132 (19)0.0000 (14)0.0042 (15)−0.0003 (15)
C20.018 (2)0.020 (2)0.024 (2)0.0037 (16)0.0083 (18)0.0112 (18)
C30.021 (2)0.018 (2)0.047 (3)0.0009 (17)0.011 (2)0.013 (2)
C40.013 (2)0.027 (3)0.036 (3)−0.0017 (18)0.001 (2)0.001 (2)
C50.027 (3)0.043 (3)0.018 (2)−0.007 (2)0.000 (2)0.001 (2)
C60.022 (2)0.033 (3)0.016 (2)−0.0050 (19)0.0012 (18)0.0092 (19)
C70.0144 (18)0.0158 (19)0.0081 (18)−0.0014 (15)0.0024 (15)0.0032 (15)
C80.016 (2)0.025 (2)0.023 (2)0.0041 (17)0.0072 (18)0.0052 (18)
C90.014 (2)0.041 (3)0.026 (2)0.0023 (19)0.0073 (19)0.004 (2)
C100.020 (2)0.040 (3)0.042 (3)−0.010 (2)0.013 (2)−0.001 (2)
C110.032 (3)0.018 (2)0.047 (3)−0.008 (2)0.016 (2)0.002 (2)
C120.019 (2)0.019 (2)0.028 (2)−0.0007 (17)0.0087 (19)0.0024 (19)
C130.0104 (17)0.0141 (19)0.0092 (18)−0.0002 (14)0.0019 (15)0.0001 (15)
C140.020 (2)0.019 (2)0.015 (2)0.0026 (16)0.0057 (17)0.0055 (16)
C150.023 (2)0.027 (2)0.022 (2)−0.0082 (19)0.0044 (19)0.0063 (19)
C160.016 (2)0.030 (3)0.029 (3)−0.0046 (18)0.0028 (19)0.007 (2)
C170.019 (2)0.031 (3)0.023 (2)0.0042 (18)−0.0002 (19)0.009 (2)
C180.016 (2)0.021 (2)0.018 (2)0.0036 (16)0.0019 (17)0.0083 (17)
C190.0186 (19)0.0099 (18)0.0139 (19)0.0043 (15)0.0100 (16)0.0057 (15)
C200.019 (2)0.0084 (18)0.0128 (19)0.0036 (14)0.0042 (16)0.0045 (15)
C210.021 (2)0.0121 (18)0.017 (2)0.0066 (15)0.0079 (17)0.0109 (16)
C220.022 (2)0.020 (2)0.019 (2)0.0054 (17)0.0058 (18)0.0083 (17)
C230.022 (2)0.030 (3)0.025 (2)0.0009 (19)0.0019 (19)0.013 (2)
C240.018 (2)0.033 (3)0.039 (3)0.0088 (19)0.012 (2)0.023 (2)
C250.031 (2)0.029 (2)0.036 (3)0.018 (2)0.025 (2)0.018 (2)
C260.028 (2)0.022 (2)0.018 (2)0.0093 (18)0.0118 (19)0.0110 (18)
C270.021 (2)0.0121 (19)0.0077 (18)0.0009 (15)0.0019 (16)0.0023 (15)
C280.024 (2)0.020 (2)0.019 (2)0.0044 (17)0.0095 (18)0.0122 (17)
C290.025 (2)0.025 (2)0.025 (2)0.0061 (18)0.013 (2)0.0077 (19)
C300.032 (2)0.026 (2)0.019 (2)−0.0058 (19)0.013 (2)0.0078 (19)
C310.034 (3)0.014 (2)0.018 (2)−0.0019 (18)0.0069 (19)0.0075 (17)
C320.027 (2)0.0126 (19)0.016 (2)0.0045 (16)0.0068 (18)0.0035 (16)
C330.0087 (17)0.0133 (18)0.0081 (17)0.0033 (14)−0.0006 (14)0.0039 (14)
C340.0191 (19)0.0112 (18)0.0121 (19)0.0032 (15)0.0090 (16)0.0038 (15)
C350.021 (2)0.0142 (19)0.0115 (19)0.0063 (16)0.0082 (16)0.0026 (15)
C360.030 (2)0.023 (2)0.019 (2)−0.0032 (18)0.0095 (19)0.0062 (18)
C370.038 (3)0.020 (2)0.031 (3)−0.007 (2)0.016 (2)−0.001 (2)
C380.026 (2)0.026 (3)0.030 (3)−0.004 (2)0.004 (2)−0.006 (2)
C390.029 (3)0.029 (3)0.024 (3)0.003 (2)−0.002 (2)0.000 (2)
C400.029 (2)0.019 (2)0.022 (2)0.0017 (18)0.004 (2)0.0071 (18)
C410.0173 (19)0.0116 (18)0.0108 (19)0.0031 (15)0.0044 (16)0.0017 (15)
C420.029 (2)0.029 (2)0.021 (2)0.0147 (19)0.0125 (19)0.0161 (19)
C430.031 (3)0.031 (3)0.028 (3)0.011 (2)0.010 (2)0.017 (2)
C440.020 (2)0.022 (2)0.034 (3)0.0067 (18)0.004 (2)0.008 (2)
C450.015 (2)0.023 (2)0.031 (3)−0.0003 (17)0.0101 (19)0.0030 (19)
C460.022 (2)0.017 (2)0.021 (2)0.0020 (17)0.0113 (18)0.0029 (17)
C470.0169 (19)0.0115 (18)0.0088 (18)0.0006 (14)0.0034 (15)0.0036 (14)
C480.0181 (19)0.017 (2)0.0113 (19)0.0032 (15)0.0059 (16)0.0084 (16)
C490.020 (2)0.022 (2)0.0089 (18)0.0070 (16)0.0044 (16)0.0078 (16)
C500.023 (2)0.023 (2)0.025 (2)0.0062 (18)0.0064 (19)0.0068 (19)
C510.022 (2)0.037 (3)0.029 (3)0.011 (2)0.004 (2)0.009 (2)
C520.036 (3)0.037 (3)0.022 (2)0.022 (2)0.012 (2)0.015 (2)
C530.049 (3)0.019 (2)0.021 (2)0.007 (2)0.015 (2)0.0088 (19)
C540.031 (2)0.020 (2)0.014 (2)0.0013 (18)0.0056 (18)0.0063 (17)
C550.0140 (19)0.018 (2)0.0118 (19)0.0049 (15)0.0035 (15)0.0062 (16)
C560.023 (2)0.023 (2)0.017 (2)0.0051 (17)0.0092 (18)0.0099 (17)
C570.026 (2)0.034 (3)0.012 (2)0.0097 (19)0.0071 (18)0.0056 (18)
C580.023 (2)0.022 (2)0.017 (2)0.0037 (17)0.0023 (18)−0.0001 (18)
C590.025 (2)0.022 (2)0.023 (2)−0.0017 (18)0.0083 (19)0.0046 (19)
C600.029 (2)0.021 (2)0.016 (2)0.0020 (18)0.0095 (18)0.0069 (17)

Geometric parameters (Å, °)

Sn1—O9i2.070 (3)C23—H230.9500
Sn1—O82.082 (3)C24—C251.3900
Sn1—O72.094 (3)C24—H240.9500
Sn1—O32.153 (3)C25—C261.3900
Sn1—O12.170 (3)C25—H250.9500
Sn1—C12.1336 (18)C26—H260.9500
Sn2—O72.072 (3)C27—C281.3900
Sn2—O92.088 (3)C27—C321.3900
Sn2—O82.089 (3)C28—C291.3900
Sn2—O42.163 (3)C28—H280.9500
Sn2—O52.171 (3)C29—C301.3900
Sn2—C72.1250 (18)C29—H290.9500
Sn3—O7i2.073 (3)C30—C311.3900
Sn3—O82.076 (3)C30—H300.9500
Sn3—O92.125 (3)C31—C321.3900
Sn3—O2i2.148 (3)C31—H310.9500
Sn3—O62.158 (3)C32—H320.9500
Sn3—C132.1181 (18)C33—C341.523 (5)
O1—C191.267 (5)C34—C351.531 (4)
O2—C191.255 (5)C34—C411.535 (4)
O2—Sn3i2.148 (3)C34—H341.0000
O3—C331.252 (5)C35—C361.3900
O4—C331.266 (4)C35—C401.3900
O5—C471.261 (5)C36—C371.3900
O6—C471.257 (5)C36—H360.9500
O7—Sn3i2.073 (3)C37—C381.3900
O9—Sn1i2.070 (3)C37—H370.9500
C1—C21.3900C38—C391.3900
C1—C61.3900C38—H380.9500
C2—C31.3900C39—C401.3900
C2—H20.9500C39—H390.9500
C3—C41.3900C40—H400.9500
C3—H30.9500C41—C421.3900
C4—C51.3900C41—C461.3900
C4—H40.9500C42—C431.3900
C5—C61.3900C42—H420.9500
C5—H50.9500C43—C441.3900
C6—H60.9500C43—H430.9500
C7—C81.3900C44—C451.3900
C7—C121.3900C44—H440.9500
C8—C91.3900C45—C461.3900
C8—H80.9500C45—H450.9500
C9—C101.3900C46—H460.9500
C9—H90.9500C47—C481.532 (5)
C10—C111.3900C48—C491.538 (4)
C10—H100.9500C48—C551.543 (4)
C11—C121.3900C48—H481.0000
C11—H110.9500C49—C501.3900
C12—H120.9500C49—C541.3900
C13—C141.3900C50—C511.3900
C13—C181.3900C50—H500.9500
C14—C151.3900C51—C521.3900
C14—H140.9500C51—H510.9500
C15—C161.3900C52—C531.3900
C15—H150.9500C52—H520.9500
C16—C171.3900C53—C541.3900
C16—H160.9500C53—H530.9500
C17—C181.3900C54—H540.9500
C17—H170.9500C55—C561.3900
C18—H180.9500C55—C601.3900
C19—C201.522 (5)C56—C571.3900
C20—C211.524 (4)C56—H560.9500
C20—C271.554 (4)C57—C581.3900
C20—H201.0000C57—H570.9500
C21—C221.3900C58—C591.3900
C21—C261.3900C58—H580.9500
C22—C231.3900C59—C601.3900
C22—H220.9500C59—H590.9500
C23—C241.3900C60—H600.9500
O9i—Sn1—O8104.81 (10)C17—C18—H18120.0
O9i—Sn1—O778.30 (10)C13—C18—H18120.0
O8—Sn1—O777.31 (10)O2—C19—O1125.2 (4)
O9i—Sn1—C1110.39 (10)O2—C19—C20118.3 (3)
O8—Sn1—C198.50 (10)O1—C19—C20116.5 (3)
O7—Sn1—C1171.19 (10)C19—C20—C21113.3 (3)
O9i—Sn1—O3155.57 (10)C19—C20—C27109.1 (3)
O8—Sn1—O388.52 (10)C21—C20—C27112.9 (3)
O7—Sn1—O384.99 (10)C19—C20—H20107.1
C1—Sn1—O387.17 (10)C21—C20—H20107.1
O9i—Sn1—O184.06 (10)C27—C20—H20107.1
O8—Sn1—O1163.51 (10)C22—C21—C26120.0
O7—Sn1—O191.25 (10)C22—C21—C20121.4 (2)
C1—Sn1—O191.14 (10)C26—C21—C20118.6 (2)
O3—Sn1—O178.56 (10)C23—C22—C21120.0
O9i—Sn1—Sn3i40.85 (7)C23—C22—H22120.0
O8—Sn1—Sn3i100.18 (7)C21—C22—H22120.0
O7—Sn1—Sn3i39.51 (7)C24—C23—C22120.0
C1—Sn1—Sn3i149.24 (7)C24—C23—H23120.0
O3—Sn1—Sn3i117.45 (7)C22—C23—H23120.0
O1—Sn1—Sn3i77.25 (7)C23—C24—C25120.0
O9i—Sn1—Sn2100.89 (7)C23—C24—H24120.0
O8—Sn1—Sn239.88 (7)C25—C24—H24120.0
O7—Sn1—Sn239.46 (7)C26—C25—C24120.0
C1—Sn1—Sn2134.14 (7)C26—C25—H25120.0
O3—Sn1—Sn276.13 (7)C24—C25—H25120.0
O1—Sn1—Sn2125.52 (7)C25—C26—C21120.0
Sn3i—Sn1—Sn273.199 (8)C25—C26—H26120.0
O7—Sn2—O9101.76 (10)C21—C26—H26120.0
O7—Sn2—O877.64 (10)C28—C27—C32120.0
O9—Sn2—O878.04 (10)C28—C27—C20123.3 (2)
O7—Sn2—C7104.87 (10)C32—C27—C20116.6 (2)
O9—Sn2—C7100.46 (10)C29—C28—C27120.0
O8—Sn2—C7177.34 (10)C29—C28—H28120.0
O7—Sn2—O487.45 (10)C27—C28—H28120.0
O9—Sn2—O4162.12 (10)C28—C29—C30120.0
O8—Sn2—O489.21 (10)C28—C29—H29120.0
C7—Sn2—O491.78 (10)C30—C29—H29120.0
O7—Sn2—O5159.26 (10)C31—C30—C29120.0
O9—Sn2—O587.69 (10)C31—C30—H30120.0
O8—Sn2—O586.49 (10)C29—C30—H30120.0
C7—Sn2—O591.27 (10)C32—C31—C30120.0
O4—Sn2—O578.98 (10)C32—C31—H31120.0
O7i—Sn3—O8104.46 (10)C30—C31—H31120.0
O7i—Sn3—C13102.46 (10)C31—C32—C27120.0
O8—Sn3—C13102.73 (10)C31—C32—H32120.0
O7i—Sn3—O977.53 (10)C27—C32—H32120.0
O8—Sn3—O977.49 (10)O3—C33—O4125.9 (4)
C13—Sn3—O9179.77 (11)O3—C33—C34117.2 (3)
O7i—Sn3—O2i88.73 (10)O4—C33—C34116.9 (3)
O8—Sn3—O2i155.77 (10)C33—C34—C35111.4 (3)
C13—Sn3—O2i93.90 (10)C33—C34—C41110.1 (3)
O9—Sn3—O2i85.87 (10)C35—C34—C41112.7 (3)
O7i—Sn3—O6160.60 (10)C33—C34—H34107.5
O8—Sn3—O685.71 (10)C35—C34—H34107.5
C13—Sn3—O691.05 (10)C41—C34—H34107.5
O9—Sn3—O688.91 (10)C36—C35—C40120.0
O2i—Sn3—O676.39 (10)C36—C35—C34121.4 (2)
O7i—Sn3—Sn1i39.98 (7)C40—C35—C34118.6 (2)
O8—Sn3—Sn1i100.15 (7)C37—C36—C35120.0
C13—Sn3—Sn1i140.36 (7)C37—C36—H36120.0
O9—Sn3—Sn1i39.57 (7)C35—C36—H36120.0
O2i—Sn3—Sn1i76.81 (7)C36—C37—C38120.0
O6—Sn3—Sn1i122.72 (7)C36—C37—H37120.0
O7i—Sn3—Sn299.93 (7)C38—C37—H37120.0
O8—Sn3—Sn239.57 (7)C39—C38—C37120.0
C13—Sn3—Sn2140.41 (8)C39—C38—H38120.0
O9—Sn3—Sn239.79 (7)C37—C38—H38120.0
O2i—Sn3—Sn2118.92 (7)C40—C39—C38120.0
O6—Sn3—Sn277.22 (7)C40—C39—H39120.0
Sn1i—Sn3—Sn273.224 (8)C38—C39—H39120.0
C19—O1—Sn1128.6 (2)C39—C40—C35120.0
C19—O2—Sn3i129.8 (3)C39—C40—H40120.0
C33—O3—Sn1131.7 (2)C35—C40—H40120.0
C33—O4—Sn2128.0 (2)C42—C41—C46120.0
C47—O5—Sn2129.2 (2)C42—C41—C34123.3 (2)
C47—O6—Sn3129.6 (3)C46—C41—C34116.7 (2)
Sn2—O7—Sn3i134.38 (13)C41—C42—C43120.0
Sn2—O7—Sn1100.58 (11)C41—C42—H42120.0
Sn3i—O7—Sn1100.51 (11)C43—C42—H42120.0
Sn3—O8—Sn1130.74 (13)C42—C43—C44120.0
Sn3—O8—Sn2101.15 (11)C42—C43—H43120.0
Sn1—O8—Sn2100.40 (11)C44—C43—H43120.0
Sn1i—O9—Sn2134.17 (13)C45—C44—C43120.0
Sn1i—O9—Sn399.58 (10)C45—C44—H44120.0
Sn2—O9—Sn399.57 (11)C43—C44—H44120.0
C2—C1—C6120.0C44—C45—C46120.0
C2—C1—Sn1123.29 (14)C44—C45—H45120.0
C6—C1—Sn1115.69 (13)C46—C45—H45120.0
C1—C2—C3120.0C45—C46—C41120.0
C1—C2—H2120.0C45—C46—H46120.0
C3—C2—H2120.0C41—C46—H46120.0
C4—C3—C2120.0O6—C47—O5126.3 (4)
C4—C3—H3120.0O6—C47—C48116.8 (3)
C2—C3—H3120.0O5—C47—C48116.9 (3)
C3—C4—C5120.0C47—C48—C49112.2 (3)
C3—C4—H4120.0C47—C48—C55108.7 (3)
C5—C4—H4120.0C49—C48—C55113.2 (3)
C4—C5—C6120.0C47—C48—H48107.5
C4—C5—H5120.0C49—C48—H48107.5
C6—C5—H5120.0C55—C48—H48107.5
C5—C6—C1120.0C50—C49—C54120.0
C5—C6—H6120.0C50—C49—C48121.2 (2)
C1—C6—H6120.0C54—C49—C48118.8 (2)
C8—C7—C12120.0C49—C50—C51120.0
C8—C7—Sn2121.10 (14)C49—C50—H50120.0
C12—C7—Sn2118.76 (13)C51—C50—H50120.0
C7—C8—C9120.0C52—C51—C50120.0
C7—C8—H8120.0C52—C51—H51120.0
C9—C8—H8120.0C50—C51—H51120.0
C8—C9—C10120.0C51—C52—C53120.0
C8—C9—H9120.0C51—C52—H52120.0
C10—C9—H9120.0C53—C52—H52120.0
C9—C10—C11120.0C54—C53—C52120.0
C9—C10—H10120.0C54—C53—H53120.0
C11—C10—H10120.0C52—C53—H53120.0
C12—C11—C10120.0C53—C54—C49120.0
C12—C11—H11120.0C53—C54—H54120.0
C10—C11—H11120.0C49—C54—H54120.0
C11—C12—C7120.0C56—C55—C60120.0
C11—C12—H12120.0C56—C55—C48118.2 (2)
C7—C12—H12120.0C60—C55—C48121.5 (2)
C14—C13—C18120.0C55—C56—C57120.0
C14—C13—Sn3120.39 (13)C55—C56—H56120.0
C18—C13—Sn3119.59 (13)C57—C56—H56120.0
C13—C14—C15120.0C58—C57—C56120.0
C13—C14—H14120.0C58—C57—H57120.0
C15—C14—H14120.0C56—C57—H57120.0
C16—C15—C14120.0C57—C58—C59120.0
C16—C15—H15120.0C57—C58—H58120.0
C14—C15—H15120.0C59—C58—H58120.0
C15—C16—C17120.0C60—C59—C58120.0
C15—C16—H16120.0C60—C59—H59120.0
C17—C16—H16120.0C58—C59—H59120.0
C18—C17—C16120.0C59—C60—C55120.0
C18—C17—H17120.0C59—C60—H60120.0
C16—C17—H17120.0C55—C60—H60120.0
C17—C18—C13120.0
O9i—Sn1—O1—C1938.1 (3)C9—C10—C11—C120.0
O8—Sn1—O1—C19−85.5 (5)C10—C11—C12—C70.0
O7—Sn1—O1—C19−40.0 (3)C8—C7—C12—C110.0
C1—Sn1—O1—C19148.5 (3)Sn2—C7—C12—C11175.7 (2)
O3—Sn1—O1—C19−124.6 (3)O7i—Sn3—C13—C1448.36 (17)
Sn3i—Sn1—O1—C19−2.8 (3)O8—Sn3—C13—C14−59.83 (17)
Sn2—Sn1—O1—C19−61.0 (3)O2i—Sn3—C13—C14137.91 (16)
O9i—Sn1—O3—C3385.9 (4)O6—Sn3—C13—C14−145.66 (16)
O8—Sn1—O3—C33−38.3 (3)Sn1i—Sn3—C13—C1463.94 (19)
O7—Sn1—O3—C3339.1 (3)Sn2—Sn3—C13—C14−74.62 (18)
C1—Sn1—O3—C33−136.9 (3)O7i—Sn3—C13—C18−130.11 (16)
O1—Sn1—O3—C33131.4 (3)O8—Sn3—C13—C18121.71 (16)
O7—Sn2—O4—C33−35.7 (3)O2i—Sn3—C13—C18−40.55 (16)
O9—Sn2—O4—C3386.0 (4)O6—Sn3—C13—C1835.87 (16)
O8—Sn2—O4—C3341.9 (3)Sn1i—Sn3—C13—C18−114.53 (14)
C7—Sn2—O4—C33−140.5 (3)Sn2—Sn3—C13—C18106.92 (15)
O5—Sn2—O4—C33128.5 (3)C18—C13—C14—C150.0
O7—Sn2—O5—C47−70.5 (4)Sn3—C13—C14—C15−178.5 (2)
O9—Sn2—O5—C4747.5 (3)C13—C14—C15—C160.0
O8—Sn2—O5—C47−30.7 (3)C14—C15—C16—C170.0
C7—Sn2—O5—C47147.9 (3)C15—C16—C17—C180.0
O4—Sn2—O5—C47−120.5 (3)C16—C17—C18—C130.0
O7i—Sn3—O6—C47−86.2 (4)C14—C13—C18—C170.0
O8—Sn3—O6—C4736.5 (3)Sn3—C13—C18—C17178.47 (19)
C13—Sn3—O6—C47139.2 (3)Sn3i—O2—C19—O1−21.4 (6)
O9—Sn3—O6—C47−41.0 (3)Sn3i—O2—C19—C20156.3 (3)
O2i—Sn3—O6—C47−127.0 (3)Sn1—O1—C19—O214.0 (6)
O9—Sn2—O7—Sn3i26.1 (2)Sn1—O1—C19—C20−163.7 (2)
O8—Sn2—O7—Sn3i100.93 (18)O2—C19—C20—C2141.0 (5)
C7—Sn2—O7—Sn3i−78.16 (18)O1—C19—C20—C21−141.1 (3)
O4—Sn2—O7—Sn3i−169.33 (18)O2—C19—C20—C27−85.6 (4)
O5—Sn2—O7—Sn3i141.8 (2)O1—C19—C20—C2792.2 (4)
O9—Sn2—O7—Sn1−90.12 (11)C19—C20—C21—C22−63.7 (4)
O8—Sn2—O7—Sn1−15.33 (10)C27—C20—C21—C2260.9 (3)
C7—Sn2—O7—Sn1165.57 (10)C19—C20—C21—C26116.3 (3)
O4—Sn2—O7—Sn174.41 (11)C27—C20—C21—C26−119.0 (3)
O5—Sn2—O7—Sn125.6 (3)C26—C21—C22—C230.0
O9i—Sn1—O7—Sn2123.71 (12)C20—C21—C22—C23−179.9 (3)
O8—Sn1—O7—Sn215.40 (10)C21—C22—C23—C240.0
O3—Sn1—O7—Sn2−74.21 (11)C22—C23—C24—C250.0
O1—Sn1—O7—Sn2−152.62 (11)C23—C24—C25—C260.0
O9i—Sn1—O7—Sn3i−15.61 (10)C24—C25—C26—C210.0
O8—Sn1—O7—Sn3i−123.92 (12)C22—C21—C26—C250.0
O3—Sn1—O7—Sn3i146.47 (11)C20—C21—C26—C25179.9 (3)
O1—Sn1—O7—Sn3i68.07 (11)C19—C20—C27—C28−11.7 (4)
O7i—Sn3—O8—Sn1−26.24 (19)C21—C20—C27—C28−138.6 (2)
C13—Sn3—O8—Sn180.43 (17)C19—C20—C27—C32171.7 (2)
O9—Sn3—O8—Sn1−99.64 (17)C21—C20—C27—C3244.8 (3)
O2i—Sn3—O8—Sn1−147.4 (2)C32—C27—C28—C290.0
O6—Sn3—O8—Sn1170.53 (17)C20—C27—C28—C29−176.5 (3)
O7i—Sn3—O8—Sn288.14 (11)C27—C28—C29—C300.0
C13—Sn3—O8—Sn2−165.20 (10)C28—C29—C30—C310.0
O9—Sn3—O8—Sn214.74 (10)C29—C30—C31—C320.0
O2i—Sn3—O8—Sn2−33.0 (3)C30—C31—C32—C270.0
O6—Sn3—O8—Sn2−75.09 (11)C28—C27—C32—C310.0
O9i—Sn1—O8—Sn325.36 (19)C20—C27—C32—C31176.8 (3)
O7—Sn1—O8—Sn399.42 (17)Sn1—O3—C33—O42.6 (6)
C1—Sn1—O8—Sn3−88.47 (17)Sn1—O3—C33—C34−176.8 (2)
O3—Sn1—O8—Sn3−175.38 (17)Sn2—O4—C33—O3−4.8 (5)
O1—Sn1—O8—Sn3146.4 (3)Sn2—O4—C33—C34174.6 (2)
O9i—Sn1—O8—Sn2−89.33 (11)O3—C33—C34—C35−46.6 (4)
O7—Sn1—O8—Sn2−15.27 (10)O4—C33—C34—C35133.9 (3)
C1—Sn1—O8—Sn2156.85 (11)O3—C33—C34—C4179.2 (4)
O3—Sn1—O8—Sn269.93 (11)O4—C33—C34—C41−100.3 (4)
O1—Sn1—O8—Sn231.7 (4)C33—C34—C35—C3681.7 (3)
O7—Sn2—O8—Sn3−120.03 (12)C41—C34—C35—C36−42.7 (4)
O9—Sn2—O8—Sn3−14.98 (10)C33—C34—C35—C40−98.8 (3)
O4—Sn2—O8—Sn3152.40 (11)C41—C34—C35—C40136.9 (2)
O5—Sn2—O8—Sn373.40 (11)C40—C35—C36—C370.0
O7—Sn2—O8—Sn115.41 (10)C34—C35—C36—C37179.6 (3)
O9—Sn2—O8—Sn1120.47 (12)C35—C36—C37—C380.0
O4—Sn2—O8—Sn1−72.15 (11)C36—C37—C38—C390.0
O5—Sn2—O8—Sn1−151.16 (12)C37—C38—C39—C400.0
O7—Sn2—O9—Sn1i−24.5 (2)C38—C39—C40—C350.0
O8—Sn2—O9—Sn1i−98.97 (18)C36—C35—C40—C390.0
C7—Sn2—O9—Sn1i83.26 (18)C34—C35—C40—C39−179.6 (3)
O4—Sn2—O9—Sn1i−144.3 (3)C33—C34—C41—C42−36.9 (4)
O5—Sn2—O9—Sn1i174.13 (18)C35—C34—C41—C4288.1 (3)
O7—Sn2—O9—Sn389.02 (11)C33—C34—C41—C46144.5 (3)
O8—Sn2—O9—Sn314.54 (10)C35—C34—C41—C46−90.5 (3)
C7—Sn2—O9—Sn3−163.23 (10)C46—C41—C42—C430.0
O4—Sn2—O9—Sn3−30.8 (4)C34—C41—C42—C43−178.6 (3)
O5—Sn2—O9—Sn3−72.36 (11)C41—C42—C43—C440.0
O7i—Sn3—O9—Sn1i15.37 (10)C42—C43—C44—C450.0
O8—Sn3—O9—Sn1i123.49 (11)C43—C44—C45—C460.0
O2i—Sn3—O9—Sn1i−74.24 (11)C44—C45—C46—C410.0
O6—Sn3—O9—Sn1i−150.67 (11)C42—C41—C46—C450.0
O7i—Sn3—O9—Sn2−122.79 (11)C34—C41—C46—C45178.7 (3)
O8—Sn3—O9—Sn2−14.67 (10)Sn3—O6—C47—O59.6 (6)
O2i—Sn3—O9—Sn2147.60 (11)Sn3—O6—C47—C48−168.4 (2)
O6—Sn3—O9—Sn271.17 (11)Sn2—O5—C47—O6−13.1 (6)
Sn1i—Sn3—O9—Sn2−138.16 (15)Sn2—O5—C47—C48165.0 (2)
O9i—Sn1—C1—C238.31 (19)O6—C47—C48—C49−29.8 (5)
O8—Sn1—C1—C2147.65 (17)O5—C47—C48—C49151.9 (3)
O3—Sn1—C1—C2−124.27 (17)O6—C47—C48—C5596.2 (4)
O1—Sn1—C1—C2−45.78 (17)O5—C47—C48—C55−82.1 (4)
O9i—Sn1—C1—C6−153.31 (15)C47—C48—C49—C5093.4 (3)
O8—Sn1—C1—C6−43.97 (16)C55—C48—C49—C50−30.1 (4)
O3—Sn1—C1—C644.12 (15)C47—C48—C49—C54−87.0 (3)
O1—Sn1—C1—C6122.61 (15)C55—C48—C49—C54149.5 (2)
C6—C1—C2—C30.0C54—C49—C50—C510.0
Sn1—C1—C2—C3167.9 (2)C48—C49—C50—C51179.6 (3)
C1—C2—C3—C40.0C49—C50—C51—C520.0
C2—C3—C4—C50.0C50—C51—C52—C530.0
C3—C4—C5—C60.0C51—C52—C53—C540.0
C4—C5—C6—C10.0C52—C53—C54—C490.0
C2—C1—C6—C50.0C50—C49—C54—C530.0
Sn1—C1—C6—C5−168.79 (19)C48—C49—C54—C53−179.6 (3)
O7—Sn2—C7—C8−46.94 (18)C47—C48—C55—C56147.7 (2)
O9—Sn2—C7—C8−152.21 (16)C49—C48—C55—C56−87.0 (3)
O4—Sn2—C7—C840.90 (17)C47—C48—C55—C60−38.7 (4)
O5—Sn2—C7—C8119.91 (17)C49—C48—C55—C6086.7 (3)
O7—Sn2—C7—C12137.38 (16)C60—C55—C56—C570.0
O9—Sn2—C7—C1232.10 (17)C48—C55—C56—C57173.8 (3)
O4—Sn2—C7—C12−134.79 (17)C55—C56—C57—C580.0
O5—Sn2—C7—C12−55.78 (17)C56—C57—C58—C590.0
C12—C7—C8—C90.0C57—C58—C59—C600.0
Sn2—C7—C8—C9−175.6 (2)C58—C59—C60—C550.0
C7—C8—C9—C100.0C56—C55—C60—C590.0
C8—C9—C10—C110.0C48—C55—C60—C59−173.5 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2814).

References

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