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Acta Cryst. (2009). E65, m808    [ doi:10.1107/S1600536809023150 ]

catena-Poly[[triphenyltin(IV)]-[mu]-2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]acetato-[kappa]2O:O']

S. M. Lee, K. M. Lo, H. Mohd Ali and W. T. Robinson

Abstract top

The title compound, [Sn(C6H5)3(C17H25O3S)]n, comprises two symmetry-independent five-coordinated triphenyltin molecules which are linked by carboxylate bridges into a polymeric chain. The SnIV atom is in a distorted trans-C3SnO2 trigonal-bipyramidal geometry. The presence of two bulky tert-butyl groups on the benzene ring prevents any hydrogen-bonding interactions involving the hydroxyl substituents.

Comment top

Organotin carboxylates have received much attention due to their extensive applications in different fields of science, including biological activity (Yehye et al., 2009). Triorganotin carboxylates are either monomeric or polymeric, depending on the steric bulk of the organic substituents. In the case of polymeric structures, the asymmetric triorganotin fragments are linked by strong carboxylate bridges (Tiekink, 1991; Parvez et al. 2002; Zhang et al., 2007).

The structure of the title compound, (I), contains two symmetry unrelated triphenyltin units which form a polymeric chain by strong carboxylate bridges. The tin atom in the polymeric unit adopts the trigonal bipyramidal geometry in which the axial positions are occupied by the carboxylate-O atoms of the adjacent 2-(3,5-di-tert-4-hydroxybenzyl)sulfanylacetate ligands. The Sn—O bond distances of 2.186 (2) Å, 2.452 (2) Å and 2.151 (2) Å, 2.384 (2) Å are in good agreement with values reported for many polymeric triorganotin carboxylates (Tiekink, 1991).

Related literature top

For chemical background, see: Yehye et al. (2009). For related structures, see: Tiekink (1991); Parvez et al. (2002); Zhang et al. (2007).

Experimental top

Compound (I) was prepared by refluxing 2-(3,5-di-tert-4-hydroxybenzyl)sulfanylacetic acid (0.39 g, 1 mmol) with triphenyltin hydroxide (0.37 g, 1 mmol) in absolute ethanol for 2 h. Colourless crystals were obtained by slow evaporation at room temperature.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95 to 0.99; O–H 0.84 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C,N,O).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the asymmetric unit in (I) drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
catena-Poly[[triphenyltin(IV)]-µ-2-[(3,5-di-tert-butyl- 4-hydroxybenzyl)sulfanyl]acetato-κ2O:O'] top
Crystal data top
[Sn(C6H5)3(C17H25O3S)]F(000) = 2720
Mr = 1318.84Dx = 1.387 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7156 reflections
a = 23.1141 (3) Åθ = 2.3–27.8°
b = 10.6933 (1) ŵ = 0.91 mm−1
c = 26.4904 (3) ÅT = 100 K
β = 105.318 (1)°Plate, colourless
V = 6314.92 (12) Å30.33 × 0.12 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		14430 independent reflections
Radiation source: fine-focus sealed tube9830 reflections with I > 2σ(I)
graphiteRint = 0.058
φ and ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −30→30
Tmin = 0.754, Tmax = 0.960k = −13→13
46753 measured reflectionsl = −34→34
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0347P)2 + 5.3025P]
where P = (Fo2 + 2Fc2)/3
14430 reflections(Δ/σ)max = 0.003
735 parametersΔρmax = 0.91 e Å−3
0 restraintsΔρmin = −0.60 e Å−3
Crystal data top
[Sn(C6H5)3(C17H25O3S)]V = 6314.92 (12) Å3
Mr = 1318.84Z = 4
Monoclinic, P21/nMo Kα radiation
a = 23.1141 (3) ŵ = 0.91 mm−1
b = 10.6933 (1) ÅT = 100 K
c = 26.4904 (3) Å0.33 × 0.12 × 0.05 mm
β = 105.318 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		14430 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		9830 reflections with I > 2σ(I)
Tmin = 0.754, Tmax = 0.960Rint = 0.058
46753 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.91 e Å−3
S = 1.01Δρmin = −0.60 e Å−3
14430 reflectionsAbsolute structure: ?
735 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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*/Ueq
Sn10.910774 (10)1.12298 (2)0.143808 (9)0.01987 (7)
Sn20.844590 (10)0.61317 (2)0.124459 (9)0.01865 (6)
O10.43868 (12)0.6917 (3)0.10995 (13)0.0361 (7)
H10.44060.61700.12000.054*
O20.85157 (11)0.9306 (2)0.12252 (10)0.0234 (6)
O30.78885 (11)0.7715 (2)0.09407 (10)0.0248 (6)
O41.33300 (12)0.4480 (3)0.15895 (14)0.0507 (9)
H41.35210.50370.17890.076*
O50.89756 (10)0.4208 (2)0.14556 (9)0.0212 (5)
O60.97151 (11)0.2825 (2)0.16497 (10)0.0238 (6)
S10.68509 (4)0.95913 (9)0.08727 (4)0.0254 (2)
S21.07276 (4)0.46546 (9)0.21041 (4)0.0272 (2)
C10.80231 (15)0.8877 (3)0.09626 (14)0.0209 (7)
C20.75315 (15)0.9722 (3)0.06523 (15)0.0230 (8)
H2A0.74400.94970.02770.028*
H2B0.76731.05990.06900.028*
C30.64945 (16)0.8224 (3)0.05085 (14)0.0227 (8)
H3A0.63950.84040.01290.027*
H3B0.67770.75100.05810.027*
C40.59296 (15)0.7880 (3)0.06610 (13)0.0207 (8)
C50.55189 (15)0.8788 (3)0.07229 (13)0.0227 (8)
H50.55950.96400.06620.027*
C60.50024 (16)0.8484 (3)0.08713 (14)0.0221 (8)
C70.48971 (16)0.7211 (4)0.09447 (15)0.0258 (8)
C80.52889 (16)0.6268 (3)0.08767 (14)0.0240 (8)
C90.58075 (16)0.6635 (3)0.07387 (14)0.0242 (8)
H90.60850.60130.06970.029*
C100.45783 (16)0.9504 (4)0.09774 (15)0.0256 (8)
C110.39367 (16)0.9309 (4)0.06322 (16)0.0313 (9)
H11A0.37940.84780.06990.047*
H11B0.39350.93750.02630.047*
H11C0.36720.99490.07150.047*
C120.45897 (17)0.9485 (4)0.15577 (15)0.0330 (10)
H12A0.49990.96480.17700.049*
H12B0.44580.86630.16480.049*
H12C0.43191.01310.16260.049*
C130.47751 (18)1.0811 (4)0.08518 (17)0.0336 (10)
H13A0.45041.14380.09320.050*
H13B0.47621.08580.04800.050*
H13C0.51851.09710.10630.050*
C140.51615 (17)0.4867 (4)0.09642 (16)0.0305 (9)
C150.5637 (2)0.4028 (4)0.08419 (19)0.0408 (11)
H15A0.60310.42390.10750.061*
H15B0.56450.41520.04770.061*
H15C0.55440.31520.08950.061*
C160.4552 (2)0.4450 (4)0.06023 (19)0.0444 (12)
H16A0.45390.46490.02380.067*
H16B0.42270.48910.07010.067*
H16C0.45040.35470.06380.067*
C170.5170 (2)0.4630 (4)0.15427 (17)0.0391 (11)
H17A0.51200.37340.15960.059*
H17B0.48420.50940.16270.059*
H17C0.55540.49110.17710.059*
C180.98565 (16)1.0026 (3)0.17101 (14)0.0219 (8)
C190.98579 (17)0.9159 (3)0.21037 (15)0.0269 (9)
H190.95240.91180.22490.032*
C201.03377 (19)0.8360 (4)0.22860 (16)0.0346 (10)
H201.03330.77770.25550.042*
C211.08251 (19)0.8412 (4)0.20758 (17)0.0397 (11)
H211.11530.78560.21970.048*
C221.08343 (18)0.9270 (4)0.16914 (17)0.0365 (10)
H221.11710.93080.15500.044*
C231.03558 (16)1.0082 (4)0.15078 (15)0.0278 (9)
H231.03681.06760.12440.033*
C240.88567 (15)1.1508 (3)0.06164 (14)0.0214 (8)
C250.90572 (18)1.0625 (4)0.03130 (16)0.0304 (9)
H250.92920.99360.04780.037*
C260.89162 (19)1.0745 (4)−0.02270 (16)0.0352 (10)
H260.90561.0141−0.04300.042*
C270.85748 (19)1.1736 (4)−0.04711 (17)0.0374 (10)
H270.84821.1820−0.08410.045*
C280.83697 (19)1.2603 (4)−0.01776 (16)0.0357 (10)
H280.81291.3281−0.03460.043*
C290.85112 (17)1.2494 (4)0.03653 (15)0.0296 (9)
H290.83691.31030.05650.035*
C300.86841 (15)1.1538 (3)0.20472 (14)0.0201 (8)
C310.90234 (17)1.2129 (3)0.24995 (14)0.0258 (8)
H310.94151.24230.25130.031*
C320.87923 (18)1.2292 (4)0.29295 (15)0.0311 (9)
H320.90241.27070.32330.037*
C330.82320 (18)1.1858 (4)0.29177 (16)0.0325 (10)
H330.80761.19720.32120.039*
C340.78947 (16)1.1258 (4)0.24807 (15)0.0313 (9)
H340.75061.09570.24740.038*
C350.81167 (16)1.1088 (4)0.20505 (15)0.0267 (8)
H350.78811.06610.17520.032*
C360.95145 (15)0.3923 (3)0.16535 (14)0.0207 (8)
C370.99361 (15)0.4947 (4)0.19353 (15)0.0242 (8)
H37A0.98250.51490.22620.029*
H37B0.98580.57050.17130.029*
C381.08468 (16)0.4698 (4)0.14585 (15)0.0345 (10)
H38A1.06420.39790.12510.041*
H38B1.06730.54760.12780.041*
C391.15088 (17)0.4648 (4)0.14936 (15)0.0300 (9)
C401.17645 (17)0.3574 (4)0.13547 (15)0.0319 (9)
H401.15170.28670.12360.038*
C411.23752 (17)0.3501 (4)0.13841 (15)0.0299 (9)
C421.27254 (17)0.4565 (4)0.15695 (17)0.0338 (10)
C431.24881 (17)0.5674 (4)0.17203 (16)0.0304 (9)
C441.18727 (17)0.5676 (4)0.16737 (16)0.0318 (9)
H441.16950.64100.17690.038*
C451.26454 (19)0.2303 (4)0.12188 (17)0.0363 (10)
C461.2171 (2)0.1292 (5)0.1035 (2)0.0577 (14)
H46A1.19980.10660.13230.087*
H46B1.23550.05530.09240.087*
H46C1.18530.16090.07400.087*
C471.3130 (2)0.1754 (5)0.16756 (19)0.0512 (13)
H47A1.34540.23640.17930.077*
H47B1.32910.09890.15610.077*
H47C1.29550.15590.19650.077*
C481.2906 (2)0.2593 (5)0.0759 (2)0.0566 (14)
H48A1.25870.29000.04640.085*
H48B1.30810.18310.06560.085*
H48C1.32180.32330.08640.085*
C491.28762 (18)0.6834 (4)0.19216 (17)0.0347 (10)
C501.3375 (2)0.6528 (5)0.2423 (2)0.0594 (15)
H50A1.35820.73010.25680.089*
H50B1.36640.59490.23370.089*
H50C1.31970.61410.26820.089*
C511.3139 (2)0.7366 (5)0.1493 (2)0.0556 (14)
H51A1.28120.76210.11930.083*
H51B1.33830.67250.13830.083*
H51C1.33900.80920.16300.083*
C521.2512 (2)0.7903 (4)0.20762 (19)0.0437 (11)
H52A1.21930.81590.17700.065*
H52B1.27770.86160.22030.065*
H52C1.23350.76170.23530.065*
C530.85574 (15)0.6475 (3)0.20566 (14)0.0218 (8)
C540.86807 (15)0.5479 (4)0.24119 (15)0.0263 (9)
H540.87320.46620.22900.032*
C550.87288 (17)0.5667 (4)0.29420 (16)0.0321 (10)
H550.88170.49850.31800.039*
C560.86483 (18)0.6842 (4)0.31174 (16)0.0330 (10)
H560.86900.69750.34800.040*
C570.85087 (18)0.7825 (4)0.27763 (16)0.0333 (10)
H570.84430.86300.29030.040*
C580.84617 (17)0.7656 (4)0.22424 (15)0.0292 (9)
H580.83650.83430.20080.035*
C590.77265 (15)0.4907 (3)0.08986 (15)0.0226 (8)
C600.75968 (17)0.3891 (3)0.11778 (17)0.0296 (9)
H600.77990.38030.15380.036*
C610.71789 (19)0.3009 (4)0.0939 (2)0.0439 (12)
H610.70940.23200.11340.053*
C620.68839 (19)0.3129 (5)0.0415 (2)0.0501 (14)
H620.66030.25090.02490.060*
C630.69929 (19)0.4135 (5)0.01317 (19)0.0467 (13)
H630.67840.4223−0.02270.056*
C640.74144 (17)0.5028 (4)0.03773 (17)0.0353 (10)
H640.74880.57300.01840.042*
C650.90345 (16)0.6477 (3)0.07627 (14)0.0213 (8)
C660.94946 (17)0.7339 (4)0.08737 (16)0.0287 (9)
H660.95600.78290.11830.034*
C670.98644 (19)0.7502 (4)0.05405 (18)0.0374 (10)
H671.01810.80970.06240.045*
C680.9774 (2)0.6811 (4)0.00956 (18)0.0438 (12)
H681.00280.6920−0.01310.053*
C690.9313 (2)0.5950 (5)−0.00272 (18)0.0517 (13)
H690.92440.5476−0.03410.062*
C700.8953 (2)0.5781 (4)0.03055 (17)0.0418 (11)
H700.86410.51750.02210.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02171 (13)0.01705 (13)0.02198 (13)0.00369 (10)0.00778 (10)0.00160 (10)
Sn20.01963 (12)0.01487 (12)0.02168 (13)−0.00021 (10)0.00586 (9)0.00112 (10)
O10.0296 (15)0.0267 (16)0.059 (2)0.0013 (12)0.0243 (14)0.0093 (14)
O20.0244 (14)0.0190 (13)0.0269 (15)−0.0012 (11)0.0069 (11)0.0014 (11)
O30.0237 (13)0.0138 (13)0.0354 (16)−0.0001 (10)0.0049 (11)−0.0008 (11)
O40.0245 (16)0.052 (2)0.081 (3)−0.0008 (15)0.0221 (16)−0.0155 (18)
O50.0225 (13)0.0173 (13)0.0250 (14)0.0013 (10)0.0084 (11)0.0029 (10)
O60.0231 (13)0.0176 (13)0.0329 (15)0.0035 (11)0.0114 (11)0.0003 (11)
S10.0238 (5)0.0209 (5)0.0328 (6)−0.0008 (4)0.0096 (4)−0.0053 (4)
S20.0194 (5)0.0323 (6)0.0296 (5)0.0014 (4)0.0062 (4)0.0005 (4)
C10.0237 (18)0.0189 (18)0.0231 (19)0.0033 (16)0.0116 (15)0.0008 (16)
C20.0216 (18)0.0185 (19)0.030 (2)0.0000 (15)0.0090 (16)0.0005 (16)
C30.0251 (19)0.0186 (19)0.024 (2)−0.0011 (15)0.0062 (15)−0.0049 (15)
C40.0235 (18)0.0217 (19)0.0168 (18)−0.0011 (15)0.0051 (14)0.0002 (14)
C50.0268 (19)0.0188 (18)0.0209 (18)−0.0011 (16)0.0035 (14)0.0025 (15)
C60.0216 (18)0.0212 (19)0.0218 (19)0.0043 (15)0.0026 (15)0.0036 (15)
C70.0220 (19)0.024 (2)0.032 (2)−0.0014 (16)0.0090 (16)0.0035 (17)
C80.0276 (19)0.0189 (19)0.027 (2)−0.0001 (16)0.0091 (15)0.0027 (16)
C90.028 (2)0.0216 (19)0.023 (2)0.0036 (16)0.0063 (16)−0.0002 (15)
C100.0211 (19)0.023 (2)0.031 (2)0.0038 (15)0.0045 (16)−0.0017 (16)
C110.025 (2)0.029 (2)0.038 (2)0.0053 (17)0.0044 (17)0.0006 (18)
C120.028 (2)0.041 (3)0.031 (2)0.0006 (18)0.0106 (18)−0.0063 (19)
C130.033 (2)0.021 (2)0.045 (3)0.0070 (17)0.0080 (19)−0.0033 (18)
C140.033 (2)0.021 (2)0.038 (2)0.0013 (17)0.0098 (18)0.0037 (17)
C150.051 (3)0.020 (2)0.057 (3)0.0020 (19)0.024 (2)0.005 (2)
C160.046 (3)0.024 (2)0.056 (3)−0.005 (2)0.000 (2)0.000 (2)
C170.044 (3)0.027 (2)0.048 (3)0.0013 (19)0.015 (2)0.008 (2)
C180.0234 (19)0.0185 (18)0.023 (2)0.0012 (15)0.0052 (15)−0.0038 (15)
C190.029 (2)0.025 (2)0.027 (2)0.0020 (16)0.0097 (17)−0.0002 (16)
C200.046 (3)0.030 (2)0.025 (2)0.0119 (19)0.0031 (19)0.0026 (17)
C210.036 (2)0.042 (3)0.037 (3)0.020 (2)0.003 (2)−0.008 (2)
C220.024 (2)0.048 (3)0.038 (3)0.0068 (19)0.0082 (18)−0.009 (2)
C230.027 (2)0.028 (2)0.029 (2)−0.0023 (17)0.0084 (16)−0.0023 (17)
C240.0211 (18)0.0227 (19)0.0224 (19)−0.0035 (15)0.0093 (15)−0.0002 (15)
C250.034 (2)0.027 (2)0.033 (2)0.0020 (17)0.0140 (18)−0.0005 (17)
C260.043 (2)0.035 (2)0.031 (2)0.000 (2)0.017 (2)−0.0073 (19)
C270.043 (3)0.046 (3)0.024 (2)−0.007 (2)0.0098 (19)−0.0023 (19)
C280.041 (2)0.035 (2)0.028 (2)0.0103 (19)0.0031 (18)0.0034 (19)
C290.036 (2)0.028 (2)0.026 (2)0.0018 (18)0.0123 (17)−0.0006 (17)
C300.0221 (18)0.0184 (18)0.0203 (19)0.0042 (14)0.0062 (14)0.0010 (14)
C310.030 (2)0.022 (2)0.026 (2)−0.0007 (16)0.0086 (16)0.0038 (16)
C320.039 (2)0.031 (2)0.021 (2)−0.0049 (18)0.0030 (17)−0.0035 (17)
C330.037 (2)0.039 (3)0.025 (2)0.0041 (19)0.0135 (18)0.0001 (18)
C340.0233 (19)0.043 (3)0.030 (2)0.0026 (19)0.0118 (16)−0.0023 (19)
C350.028 (2)0.026 (2)0.025 (2)0.0037 (17)0.0054 (16)−0.0042 (17)
C360.0204 (17)0.024 (2)0.0206 (18)0.0048 (15)0.0101 (14)0.0055 (15)
C370.0190 (18)0.025 (2)0.029 (2)0.0006 (15)0.0069 (15)−0.0011 (16)
C380.022 (2)0.053 (3)0.029 (2)−0.0011 (19)0.0082 (17)−0.002 (2)
C390.024 (2)0.042 (3)0.026 (2)0.0005 (18)0.0099 (16)−0.0040 (18)
C400.029 (2)0.036 (2)0.030 (2)−0.0060 (18)0.0075 (17)−0.0019 (18)
C410.031 (2)0.033 (2)0.026 (2)0.0037 (17)0.0098 (17)−0.0025 (17)
C420.023 (2)0.043 (3)0.038 (3)0.0008 (18)0.0123 (18)−0.001 (2)
C430.027 (2)0.030 (2)0.036 (2)0.0010 (17)0.0118 (18)−0.0007 (18)
C440.027 (2)0.033 (2)0.038 (2)−0.0001 (17)0.0125 (18)−0.0041 (19)
C450.042 (2)0.036 (2)0.034 (2)0.011 (2)0.0147 (19)−0.0034 (19)
C460.065 (3)0.042 (3)0.064 (4)0.006 (3)0.012 (3)−0.019 (3)
C470.060 (3)0.047 (3)0.044 (3)0.023 (2)0.009 (2)0.000 (2)
C480.082 (4)0.046 (3)0.053 (3)0.023 (3)0.038 (3)0.004 (3)
C490.028 (2)0.032 (2)0.043 (3)−0.0039 (18)0.0092 (19)−0.0010 (19)
C500.053 (3)0.041 (3)0.069 (4)0.002 (2)−0.010 (3)−0.011 (3)
C510.047 (3)0.054 (3)0.075 (4)−0.006 (3)0.032 (3)0.006 (3)
C520.046 (3)0.035 (3)0.051 (3)−0.003 (2)0.014 (2)−0.003 (2)
C530.0162 (17)0.027 (2)0.024 (2)−0.0027 (15)0.0077 (14)−0.0017 (15)
C540.0212 (19)0.028 (2)0.030 (2)0.0053 (16)0.0062 (16)0.0013 (17)
C550.029 (2)0.043 (3)0.026 (2)0.0063 (19)0.0107 (17)0.0104 (19)
C560.032 (2)0.047 (3)0.022 (2)−0.005 (2)0.0116 (17)−0.0035 (19)
C570.036 (2)0.033 (2)0.033 (2)−0.0068 (19)0.0141 (18)−0.0088 (19)
C580.032 (2)0.026 (2)0.029 (2)−0.0043 (17)0.0073 (17)−0.0037 (17)
C590.0195 (18)0.0143 (18)0.034 (2)0.0053 (14)0.0064 (15)−0.0015 (15)
C600.030 (2)0.019 (2)0.043 (2)0.0006 (17)0.0153 (18)−0.0036 (18)
C610.035 (2)0.024 (2)0.079 (4)−0.0054 (19)0.025 (2)−0.012 (2)
C620.026 (2)0.040 (3)0.083 (4)−0.008 (2)0.013 (2)−0.033 (3)
C630.028 (2)0.055 (3)0.047 (3)0.012 (2)−0.010 (2)−0.018 (2)
C640.030 (2)0.028 (2)0.042 (3)0.0047 (18)−0.0007 (18)0.0014 (19)
C650.0267 (19)0.0184 (19)0.0204 (19)0.0008 (15)0.0093 (15)0.0024 (14)
C660.035 (2)0.022 (2)0.032 (2)−0.0001 (17)0.0136 (18)−0.0034 (17)
C670.038 (2)0.030 (2)0.052 (3)−0.0051 (19)0.025 (2)0.000 (2)
C680.054 (3)0.047 (3)0.041 (3)−0.001 (2)0.031 (2)0.002 (2)
C690.076 (4)0.056 (3)0.031 (3)−0.013 (3)0.028 (2)−0.014 (2)
C700.052 (3)0.043 (3)0.034 (3)−0.019 (2)0.018 (2)−0.012 (2)
Geometric parameters (Å, °) top
Sn1—C242.120 (4)C30—C311.398 (5)
Sn1—C302.122 (4)C30—C351.399 (5)
Sn1—C182.124 (3)C31—C321.391 (5)
Sn1—O6i2.186 (2)C31—H310.9500
Sn1—O22.452 (2)C32—C331.369 (5)
Sn2—C592.125 (4)C32—H320.9500
Sn2—C652.129 (4)C33—C341.372 (5)
Sn2—C532.130 (4)C33—H330.9500
Sn2—O32.151 (2)C34—C351.380 (5)
Sn2—O52.384 (2)C34—H340.9500
O1—C71.384 (4)C35—H350.9500
O1—H10.8400C36—C371.524 (5)
O2—C11.254 (4)C37—H37A0.9900
O3—C11.279 (4)C37—H37B0.9900
O4—C421.387 (4)C38—C391.509 (5)
O4—H40.8400C38—H38A0.9900
O5—C361.254 (4)C38—H38B0.9900
O6—C361.264 (4)C39—C401.385 (6)
O6—Sn1ii2.186 (2)C39—C441.390 (5)
S1—C21.822 (4)C40—C411.395 (5)
S1—C31.824 (4)C40—H400.9500
S2—C371.792 (3)C41—C421.407 (6)
S2—C381.803 (4)C41—C451.538 (5)
C1—C21.513 (5)C42—C431.408 (6)
C2—H2A0.9900C43—C441.395 (5)
C2—H2B0.9900C43—C491.542 (6)
C3—C41.511 (5)C44—H440.9500
C3—H3A0.9900C45—C481.526 (6)
C3—H3B0.9900C45—C461.526 (6)
C4—C91.388 (5)C45—C471.532 (6)
C4—C51.397 (5)C46—H46A0.9800
C5—C61.391 (5)C46—H46B0.9800
C5—H50.9500C46—H46C0.9800
C6—C71.405 (5)C47—H47A0.9800
C6—C101.541 (5)C47—H47B0.9800
C7—C81.399 (5)C47—H47C0.9800
C8—C91.399 (5)C48—H48A0.9800
C8—C141.555 (5)C48—H48B0.9800
C9—H90.9500C48—H48C0.9800
C10—C121.531 (5)C49—C511.531 (6)
C10—C131.533 (5)C49—C521.538 (6)
C10—C111.537 (5)C49—C501.547 (6)
C11—H11A0.9800C50—H50A0.9800
C11—H11B0.9800C50—H50B0.9800
C11—H11C0.9800C50—H50C0.9800
C12—H12A0.9800C51—H51A0.9800
C12—H12B0.9800C51—H51B0.9800
C12—H12C0.9800C51—H51C0.9800
C13—H13A0.9800C52—H52A0.9800
C13—H13B0.9800C52—H52B0.9800
C13—H13C0.9800C52—H52C0.9800
C14—C151.519 (6)C53—C581.394 (5)
C14—C161.546 (5)C53—C541.400 (5)
C14—C171.548 (6)C54—C551.394 (5)
C15—H15A0.9800C54—H540.9500
C15—H15B0.9800C55—C561.369 (6)
C15—H15C0.9800C55—H550.9500
C16—H16A0.9800C56—C571.368 (6)
C16—H16B0.9800C56—H560.9500
C16—H16C0.9800C57—C581.401 (5)
C17—H17A0.9800C57—H570.9500
C17—H17B0.9800C58—H580.9500
C17—H17C0.9800C59—C641.385 (5)
C18—C191.394 (5)C59—C601.391 (5)
C18—C231.396 (5)C60—C611.379 (5)
C19—C201.382 (5)C60—H600.9500
C19—H190.9500C61—C621.381 (7)
C20—C211.383 (6)C61—H610.9500
C20—H200.9500C62—C631.372 (7)
C21—C221.375 (6)C62—H620.9500
C21—H210.9500C63—C641.396 (6)
C22—C231.389 (5)C63—H630.9500
C22—H220.9500C64—H640.9500
C23—H230.9500C65—C661.379 (5)
C24—C291.382 (5)C65—C701.391 (5)
C24—C251.396 (5)C66—C671.392 (6)
C25—C261.387 (6)C66—H660.9500
C25—H250.9500C67—C681.359 (6)
C26—C271.376 (6)C67—H670.9500
C26—H260.9500C68—C691.380 (6)
C27—C281.372 (6)C68—H680.9500
C27—H270.9500C69—C701.374 (6)
C28—C291.393 (5)C69—H690.9500
C28—H280.9500C70—H700.9500
C29—H290.9500
C24—Sn1—C30134.63 (13)C32—C31—H31119.7
C24—Sn1—C18114.26 (14)C30—C31—H31119.7
C30—Sn1—C18109.53 (14)C33—C32—C31120.3 (4)
C24—Sn1—O6i97.85 (12)C33—C32—H32119.8
C30—Sn1—O6i94.48 (12)C31—C32—H32119.8
C18—Sn1—O6i88.59 (12)C32—C33—C34120.1 (4)
C24—Sn1—O284.09 (11)C32—C33—H33120.0
C30—Sn1—O287.90 (11)C34—C33—H33120.0
C18—Sn1—O285.69 (11)C33—C34—C35120.4 (4)
O6i—Sn1—O2174.26 (8)C33—C34—H34119.8
C59—Sn2—C65113.54 (14)C35—C34—H34119.8
C59—Sn2—C53114.45 (14)C34—C35—C30120.9 (3)
C65—Sn2—C53130.52 (13)C34—C35—H35119.5
C59—Sn2—O390.04 (11)C30—C35—H35119.5
C65—Sn2—O393.07 (12)O5—C36—O6123.2 (3)
C53—Sn2—O398.22 (12)O5—C36—C37117.8 (3)
C59—Sn2—O582.19 (11)O6—C36—C37118.9 (3)
C65—Sn2—O585.43 (11)C36—C37—S2118.4 (3)
C53—Sn2—O589.67 (11)C36—C37—H37A107.7
O3—Sn2—O5170.70 (9)S2—C37—H37A107.7
C7—O1—H1109.5C36—C37—H37B107.7
C1—O2—Sn1143.5 (2)S2—C37—H37B107.7
C1—O3—Sn2129.3 (2)H37A—C37—H37B107.1
C42—O4—H4109.5C39—C38—S2110.3 (3)
C36—O5—Sn2134.3 (2)C39—C38—H38A109.6
C36—O6—Sn1ii121.0 (2)S2—C38—H38A109.6
C2—S1—C3101.51 (17)C39—C38—H38B109.6
C37—S2—C3899.24 (18)S2—C38—H38B109.6
O2—C1—O3123.7 (3)H38A—C38—H38B108.1
O2—C1—C2121.6 (3)C40—C39—C44119.0 (4)
O3—C1—C2114.6 (3)C40—C39—C38120.7 (4)
C1—C2—S1111.6 (3)C44—C39—C38120.3 (4)
C1—C2—H2A109.3C39—C40—C41121.9 (4)
S1—C2—H2A109.3C39—C40—H40119.1
C1—C2—H2B109.3C41—C40—H40119.1
S1—C2—H2B109.3C40—C41—C42117.0 (4)
H2A—C2—H2B108.0C40—C41—C45120.8 (4)
C4—C3—S1110.8 (2)C42—C41—C45122.2 (4)
C4—C3—H3A109.5O4—C42—C41116.2 (4)
S1—C3—H3A109.5O4—C42—C43120.5 (4)
C4—C3—H3B109.5C41—C42—C43123.3 (4)
S1—C3—H3B109.5C44—C43—C42116.2 (4)
H3A—C3—H3B108.1C44—C43—C49121.0 (4)
C9—C4—C5118.6 (3)C42—C43—C49122.8 (3)
C9—C4—C3119.8 (3)C39—C44—C43122.6 (4)
C5—C4—C3121.6 (3)C39—C44—H44118.7
C6—C5—C4122.1 (3)C43—C44—H44118.7
C6—C5—H5118.9C48—C45—C46107.0 (4)
C4—C5—H5118.9C48—C45—C47110.3 (4)
C5—C6—C7117.3 (3)C46—C45—C47107.2 (4)
C5—C6—C10121.4 (3)C48—C45—C41109.5 (4)
C7—C6—C10121.2 (3)C46—C45—C41111.6 (4)
O1—C7—C8120.4 (3)C47—C45—C41111.2 (4)
O1—C7—C6117.0 (3)C45—C46—H46A109.5
C8—C7—C6122.6 (3)C45—C46—H46B109.5
C9—C8—C7117.4 (3)H46A—C46—H46B109.5
C9—C8—C14121.2 (3)C45—C46—H46C109.5
C7—C8—C14121.4 (3)H46A—C46—H46C109.5
C4—C9—C8122.0 (3)H46B—C46—H46C109.5
C4—C9—H9119.0C45—C47—H47A109.5
C8—C9—H9119.0C45—C47—H47B109.5
C12—C10—C13107.6 (3)H47A—C47—H47B109.5
C12—C10—C11110.7 (3)C45—C47—H47C109.5
C13—C10—C11106.8 (3)H47A—C47—H47C109.5
C12—C10—C6109.3 (3)H47B—C47—H47C109.5
C13—C10—C6111.5 (3)C45—C48—H48A109.5
C11—C10—C6110.8 (3)C45—C48—H48B109.5
C10—C11—H11A109.5H48A—C48—H48B109.5
C10—C11—H11B109.5C45—C48—H48C109.5
H11A—C11—H11B109.5H48A—C48—H48C109.5
C10—C11—H11C109.5H48B—C48—H48C109.5
H11A—C11—H11C109.5C51—C49—C52105.9 (4)
H11B—C11—H11C109.5C51—C49—C43110.6 (4)
C10—C12—H12A109.5C52—C49—C43112.4 (3)
C10—C12—H12B109.5C51—C49—C50111.3 (4)
H12A—C12—H12B109.5C52—C49—C50105.4 (4)
C10—C12—H12C109.5C43—C49—C50111.1 (4)
H12A—C12—H12C109.5C49—C50—H50A109.5
H12B—C12—H12C109.5C49—C50—H50B109.5
C10—C13—H13A109.5H50A—C50—H50B109.5
C10—C13—H13B109.5C49—C50—H50C109.5
H13A—C13—H13B109.5H50A—C50—H50C109.5
C10—C13—H13C109.5H50B—C50—H50C109.5
H13A—C13—H13C109.5C49—C51—H51A109.5
H13B—C13—H13C109.5C49—C51—H51B109.5
C15—C14—C16106.9 (4)H51A—C51—H51B109.5
C15—C14—C17107.1 (3)C49—C51—H51C109.5
C16—C14—C17109.7 (4)H51A—C51—H51C109.5
C15—C14—C8111.1 (3)H51B—C51—H51C109.5
C16—C14—C8111.3 (3)C49—C52—H52A109.5
C17—C14—C8110.6 (3)C49—C52—H52B109.5
C14—C15—H15A109.5H52A—C52—H52B109.5
C14—C15—H15B109.5C49—C52—H52C109.5
H15A—C15—H15B109.5H52A—C52—H52C109.5
C14—C15—H15C109.5H52B—C52—H52C109.5
H15A—C15—H15C109.5C58—C53—C54118.4 (3)
H15B—C15—H15C109.5C58—C53—Sn2121.6 (3)
C14—C16—H16A109.5C54—C53—Sn2119.8 (3)
C14—C16—H16B109.5C55—C54—C53121.0 (4)
H16A—C16—H16B109.5C55—C54—H54119.5
C14—C16—H16C109.5C53—C54—H54119.5
H16A—C16—H16C109.5C56—C55—C54119.5 (4)
H16B—C16—H16C109.5C56—C55—H55120.2
C14—C17—H17A109.5C54—C55—H55120.2
C14—C17—H17B109.5C57—C56—C55120.7 (4)
H17A—C17—H17B109.5C57—C56—H56119.6
C14—C17—H17C109.5C55—C56—H56119.6
H17A—C17—H17C109.5C56—C57—C58120.6 (4)
H17B—C17—H17C109.5C56—C57—H57119.7
C19—C18—C23118.5 (3)C58—C57—H57119.7
C19—C18—Sn1119.8 (3)C53—C58—C57119.7 (4)
C23—C18—Sn1121.7 (3)C53—C58—H58120.1
C20—C19—C18121.0 (4)C57—C58—H58120.1
C20—C19—H19119.5C64—C59—C60118.3 (4)
C18—C19—H19119.5C64—C59—Sn2121.0 (3)
C19—C20—C21119.9 (4)C60—C59—Sn2120.4 (3)
C19—C20—H20120.1C61—C60—C59120.9 (4)
C21—C20—H20120.1C61—C60—H60119.6
C22—C21—C20119.9 (4)C59—C60—H60119.6
C22—C21—H21120.1C60—C61—C62119.9 (5)
C20—C21—H21120.1C60—C61—H61120.1
C21—C22—C23120.6 (4)C62—C61—H61120.1
C21—C22—H22119.7C63—C62—C61120.6 (4)
C23—C22—H22119.7C63—C62—H62119.7
C22—C23—C18120.1 (4)C61—C62—H62119.7
C22—C23—H23120.0C62—C63—C64119.2 (4)
C18—C23—H23120.0C62—C63—H63120.4
C29—C24—C25118.4 (3)C64—C63—H63120.4
C29—C24—Sn1124.6 (3)C59—C64—C63121.1 (4)
C25—C24—Sn1117.0 (3)C59—C64—H64119.4
C26—C25—C24120.5 (4)C63—C64—H64119.4
C26—C25—H25119.7C66—C65—C70117.6 (4)
C24—C25—H25119.7C66—C65—Sn2124.5 (3)
C27—C26—C25120.4 (4)C70—C65—Sn2117.9 (3)
C27—C26—H26119.8C65—C66—C67121.1 (4)
C25—C26—H26119.8C65—C66—H66119.4
C28—C27—C26119.6 (4)C67—C66—H66119.4
C28—C27—H27120.2C68—C67—C66120.1 (4)
C26—C27—H27120.2C68—C67—H67119.9
C27—C28—C29120.5 (4)C66—C67—H67119.9
C27—C28—H28119.8C67—C68—C69120.0 (4)
C29—C28—H28119.8C67—C68—H68120.0
C24—C29—C28120.6 (4)C69—C68—H68120.0
C24—C29—H29119.7C70—C69—C68119.8 (4)
C28—C29—H29119.7C70—C69—H69120.1
C31—C30—C35117.7 (3)C68—C69—H69120.1
C31—C30—Sn1117.0 (3)C69—C70—C65121.5 (4)
C35—C30—Sn1125.0 (3)C69—C70—H70119.3
C32—C31—C30120.6 (4)C65—C70—H70119.3
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Acknowledgements top

We thank the University of Malaya (grant Nos. PS072/2007 C and PS320/2008 C) for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Parvez, M., Ali, S., Ahmad, S., Bhatti, M. H. & Mazhar, M. (2002). Acta Cryst. C58, m334–m335.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23.

Yehye, W. A., Ariffin, A. & Ng, S. W. (2009). Acta Cryst. E65, o730.

Zhang, X., Song, H., Li, Q., Liu, X. & Tang, L. (2007). Polyhedron, 26, 3743–3749.