supplementary materials


Acta Cryst. (2008). E64, m1614    [ doi:10.1107/S1600536808038567 ]

cyclo-Hexa-[mu]2-diphenylacetato-[kappa]12O:O'-hexa-[mu]3-oxido-hexakis[phenyltin(IV)]

M. M. Amini, T. Hajiashrafi, A. N. Kharat and S. W. Ng

Abstract top

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.

Comment top

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).

Related literature top

For examples of drum-shaped cyclohexameric oxophenyltin(IV) carboxylates, see: 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 top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 70% probability level.
cyclo-Hexa-µ2-diphenylacetato-κ12O:O'-hexa-µ3- oxido-hexakis[phenyltin(IV)] top
Crystal data top
[Sn6(C6H5)6(C14H11O2)6O6]Z = 1
Mr = 2538.11F(000) = 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 = 2.4–32.5°
c = 14.8043 (2) ŵ = 1.53 mm1
α = 103.368 (1)°T = 112 K
β = 111.716 (1)°Block, colorless
γ = 92.582 (1)°0.25 × 0.20 × 0.17 mm
V = 2525.06 (6) Å3
Data collection top
Bruker APEXII
diffractometer
11415 independent reflections
Radiation source: medium-focus sealed tube9692 reflections with I > 2σ(I)
graphiteRint = 0.041
φ and ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.701, Tmax = 0.781k = 1919
37375 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.8272P]
where P = (Fo2 + 2Fc2)/3
11415 reflections(Δ/σ)max = 0.001
541 parametersΔρmax = 0.94 e Å3
0 restraintsΔρmin = 2.31 e Å3
Crystal data top
[Sn6(C6H5)6(C14H11O2)6O6]γ = 92.582 (1)°
Mr = 2538.11V = 2525.06 (6) Å3
Triclinic, P1Z = 1
a = 12.9375 (2) ÅMo Kα radiation
b = 14.7406 (2) ŵ = 1.53 mm1
c = 14.8043 (2) ÅT = 112 K
α = 103.368 (1)°0.25 × 0.20 × 0.17 mm
β = 111.716 (1)°
Data collection top
Bruker APEXII
diffractometer
9692 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Rint = 0.041
Tmin = 0.701, Tmax = 0.781θmax = 27.5°
37375 measured reflectionsStandard reflections: 0
11415 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.118Δρmax = 0.94 e Å3
S = 1.18Δρmin = 2.31 e Å3
11415 reflectionsAbsolute structure: ?
541 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H100.01610.27030.54840.044*
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)
H240.07490.90720.28330.033*
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) top
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, °) top
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—C1985.5 (5)C10—C11—C12—C70.0
O7—Sn1—O1—C1940.0 (3)C8—C7—C12—C110.0
C1—Sn1—O1—C19148.5 (3)Sn2—C7—C12—C11175.7 (2)
O3—Sn1—O1—C19124.6 (3)O7i—Sn3—C13—C1448.36 (17)
Sn3i—Sn1—O1—C192.8 (3)O8—Sn3—C13—C1459.83 (17)
Sn2—Sn1—O1—C1961.0 (3)O2i—Sn3—C13—C14137.91 (16)
O9i—Sn1—O3—C3385.9 (4)O6—Sn3—C13—C14145.66 (16)
O8—Sn1—O3—C3338.3 (3)Sn1i—Sn3—C13—C1463.94 (19)
O7—Sn1—O3—C3339.1 (3)Sn2—Sn3—C13—C1474.62 (18)
C1—Sn1—O3—C33136.9 (3)O7i—Sn3—C13—C18130.11 (16)
O1—Sn1—O3—C33131.4 (3)O8—Sn3—C13—C18121.71 (16)
O7—Sn2—O4—C3335.7 (3)O2i—Sn3—C13—C1840.55 (16)
O9—Sn2—O4—C3386.0 (4)O6—Sn3—C13—C1835.87 (16)
O8—Sn2—O4—C3341.9 (3)Sn1i—Sn3—C13—C18114.53 (14)
C7—Sn2—O4—C33140.5 (3)Sn2—Sn3—C13—C18106.92 (15)
O5—Sn2—O4—C33128.5 (3)C18—C13—C14—C150.0
O7—Sn2—O5—C4770.5 (4)Sn3—C13—C14—C15178.5 (2)
O9—Sn2—O5—C4747.5 (3)C13—C14—C15—C160.0
O8—Sn2—O5—C4730.7 (3)C14—C15—C16—C170.0
C7—Sn2—O5—C47147.9 (3)C15—C16—C17—C180.0
O4—Sn2—O5—C47120.5 (3)C16—C17—C18—C130.0
O7i—Sn3—O6—C4786.2 (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—O121.4 (6)
O9—Sn3—O6—C4741.0 (3)Sn3i—O2—C19—C20156.3 (3)
O2i—Sn3—O6—C47127.0 (3)Sn1—O1—C19—O214.0 (6)
O9—Sn2—O7—Sn3i26.1 (2)Sn1—O1—C19—C20163.7 (2)
O8—Sn2—O7—Sn3i100.93 (18)O2—C19—C20—C2141.0 (5)
C7—Sn2—O7—Sn3i78.16 (18)O1—C19—C20—C21141.1 (3)
O4—Sn2—O7—Sn3i169.33 (18)O2—C19—C20—C2785.6 (4)
O5—Sn2—O7—Sn3i141.8 (2)O1—C19—C20—C2792.2 (4)
O9—Sn2—O7—Sn190.12 (11)C19—C20—C21—C2263.7 (4)
O8—Sn2—O7—Sn115.33 (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—C26119.0 (3)
O5—Sn2—O7—Sn125.6 (3)C26—C21—C22—C230.0
O9i—Sn1—O7—Sn2123.71 (12)C20—C21—C22—C23179.9 (3)
O8—Sn1—O7—Sn215.40 (10)C21—C22—C23—C240.0
O3—Sn1—O7—Sn274.21 (11)C22—C23—C24—C250.0
O1—Sn1—O7—Sn2152.62 (11)C23—C24—C25—C260.0
O9i—Sn1—O7—Sn3i15.61 (10)C24—C25—C26—C210.0
O8—Sn1—O7—Sn3i123.92 (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—C2811.7 (4)
O7i—Sn3—O8—Sn126.24 (19)C21—C20—C27—C28138.6 (2)
C13—Sn3—O8—Sn180.43 (17)C19—C20—C27—C32171.7 (2)
O9—Sn3—O8—Sn199.64 (17)C21—C20—C27—C3244.8 (3)
O2i—Sn3—O8—Sn1147.4 (2)C32—C27—C28—C290.0
O6—Sn3—O8—Sn1170.53 (17)C20—C27—C28—C29176.5 (3)
O7i—Sn3—O8—Sn288.14 (11)C27—C28—C29—C300.0
C13—Sn3—O8—Sn2165.20 (10)C28—C29—C30—C310.0
O9—Sn3—O8—Sn214.74 (10)C29—C30—C31—C320.0
O2i—Sn3—O8—Sn233.0 (3)C30—C31—C32—C270.0
O6—Sn3—O8—Sn275.09 (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—Sn388.47 (17)Sn1—O3—C33—C34176.8 (2)
O3—Sn1—O8—Sn3175.38 (17)Sn2—O4—C33—O34.8 (5)
O1—Sn1—O8—Sn3146.4 (3)Sn2—O4—C33—C34174.6 (2)
O9i—Sn1—O8—Sn289.33 (11)O3—C33—C34—C3546.6 (4)
O7—Sn1—O8—Sn215.27 (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—C41100.3 (4)
O1—Sn1—O8—Sn231.7 (4)C33—C34—C35—C3681.7 (3)
O7—Sn2—O8—Sn3120.03 (12)C41—C34—C35—C3642.7 (4)
O9—Sn2—O8—Sn314.98 (10)C33—C34—C35—C4098.8 (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—Sn172.15 (11)C36—C37—C38—C390.0
O5—Sn2—O8—Sn1151.16 (12)C37—C38—C39—C400.0
O7—Sn2—O9—Sn1i24.5 (2)C38—C39—C40—C350.0
O8—Sn2—O9—Sn1i98.97 (18)C36—C35—C40—C390.0
C7—Sn2—O9—Sn1i83.26 (18)C34—C35—C40—C39179.6 (3)
O4—Sn2—O9—Sn1i144.3 (3)C33—C34—C41—C4236.9 (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—C4690.5 (3)
C7—Sn2—O9—Sn3163.23 (10)C46—C41—C42—C430.0
O4—Sn2—O9—Sn330.8 (4)C34—C41—C42—C43178.6 (3)
O5—Sn2—O9—Sn372.36 (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—Sn1i74.24 (11)C44—C45—C46—C410.0
O6—Sn3—O9—Sn1i150.67 (11)C42—C41—C46—C450.0
O7i—Sn3—O9—Sn2122.79 (11)C34—C41—C46—C45178.7 (3)
O8—Sn3—O9—Sn214.67 (10)Sn3—O6—C47—O59.6 (6)
O2i—Sn3—O9—Sn2147.60 (11)Sn3—O6—C47—C48168.4 (2)
O6—Sn3—O9—Sn271.17 (11)Sn2—O5—C47—O613.1 (6)
Sn1i—Sn3—O9—Sn2138.16 (15)Sn2—O5—C47—C48165.0 (2)
O9i—Sn1—C1—C238.31 (19)O6—C47—C48—C4929.8 (5)
O8—Sn1—C1—C2147.65 (17)O5—C47—C48—C49151.9 (3)
O3—Sn1—C1—C2124.27 (17)O6—C47—C48—C5596.2 (4)
O1—Sn1—C1—C245.78 (17)O5—C47—C48—C5582.1 (4)
O9i—Sn1—C1—C6153.31 (15)C47—C48—C49—C5093.4 (3)
O8—Sn1—C1—C643.97 (16)C55—C48—C49—C5030.1 (4)
O3—Sn1—C1—C644.12 (15)C47—C48—C49—C5487.0 (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—C5168.79 (19)C48—C49—C54—C53179.6 (3)
O7—Sn2—C7—C846.94 (18)C47—C48—C55—C56147.7 (2)
O9—Sn2—C7—C8152.21 (16)C49—C48—C55—C5687.0 (3)
O4—Sn2—C7—C840.90 (17)C47—C48—C55—C6038.7 (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—C12134.79 (17)C55—C56—C57—C580.0
O5—Sn2—C7—C1255.78 (17)C56—C57—C58—C590.0
C12—C7—C8—C90.0C57—C58—C59—C600.0
Sn2—C7—C8—C9175.6 (2)C58—C59—C60—C550.0
C7—C8—C9—C100.0C56—C55—C60—C590.0
C8—C9—C10—C110.0C48—C55—C60—C59173.5 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å)
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Sn1—O9i2.070 (3)Sn2—O42.163 (3)
Sn1—O82.082 (3)Sn2—O52.171 (3)
Sn1—O72.094 (3)Sn2—C72.1250 (18)
Sn1—O32.153 (3)Sn3—O7i2.073 (3)
Sn1—O12.170 (3)Sn3—O82.076 (3)
Sn1—C12.1336 (18)Sn3—O92.125 (3)
Sn2—O72.072 (3)Sn3—O2i2.148 (3)
Sn2—O92.088 (3)Sn3—O62.158 (3)
Sn2—O82.089 (3)Sn3—C132.1181 (18)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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.

references
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