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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m792.
Published online 2010 June 16. doi:  10.1107/S1600536810021884
PMCID: PMC3007050

Tricyclo­hex­yl{2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]acetato-κO}tin(IV)

Abstract

The title compound, [Sn(C6H11)3(C17H25O3S)], exists as a monomeric mol­ecule with the SnIV atom in a distorted tetra­hedral C3O coordination geometry. The presence of two bulky tert-butyl groups on the carboxyl­ate prevents any hydrogen-bonding inter­actions involving the hy­droxy group.

Related literature

For tricyclo­hexyl­tin carboxyl­ates, see: Tiekink (1991 [triangle]). For a triphenyl­tin analogue of the title compound, see: Lee et al. (2009 [triangle]). For other related structures, see: Alcock & Timms (1968 [triangle]); Keng et al. (2010 [triangle]); Ng & Kumar Das (1997 [triangle]); Thong et al. (2009 [triangle]); Zhang et al. (2007 [triangle]). For the preparation of the ligand, see: Yehye et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m792-scheme1.jpg

Experimental

Crystal data

  • [Sn(C6H11)3(C17H25O3S)]
  • M r = 677.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m792-efi1.jpg
  • a = 15.5048 (3) Å
  • b = 11.4261 (3) Å
  • c = 19.9794 (4) Å
  • β = 94.603 (2)°
  • V = 3528.12 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.81 mm−1
  • T = 296 K
  • 0.23 × 0.16 × 0.12 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.835, T max = 0.909
  • 32619 measured reflections
  • 8086 independent reflections
  • 4695 reflections with I > 2σ(I)
  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.117
  • S = 1.00
  • 8086 reflections
  • 368 parameters
  • H-atom parameters constrained
  • Δρmax = 0.65 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2010 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021884/hy2317sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021884/hy2317Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant Nos. PS342/2009C and RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Triorganotin carboxylates are either monomeric or polymeric, depending primarily on the types of organic groups bonded to the tin atom. Triphenyltin carboxylates generally adopt a five-coordinated tin geometry with carboxylate bridges linking adjacent molecules into a polymeric chain, whereas tricyclohexyltin carboxylates have discrete four-coordinated tin structures (Tiekink, 1991).

The title compound is another example of a four-coordinated tricyclohexyltin carboxylate, in which the SnIV atom is in a distorted tetrahedral geometry. The close proximity of the carboxylate O3 towards the Sn atom [Sn1···O3 = 2.897 (3) Å] contributes to the distortion of the geometry (Alcock & Timms, 1968).

Experimental

The title compound was prepared by refluxing 2-(3,5-di-tert-4-hydroxybenzyl)sulfanylacetic acid (0.39 g, 1 mmol) with tricyclohexyltin hydroxide (0.39 g, 1 mmol) in absolute ethanol for 2 h. Colourless crystals were obtained by slow evaporation of the solution at room temperature.

Refinement

H atoms were placed at calculated positions and treated as riding on their parent atoms, with C—H = 0.93 (aromatic), 0.98 (CH), 0.97 (CH2) and 0.96 (CH3) Å and O—H = 0.82 Å and with Uiso(H) = 1.2(1.5 for methyl and hydroxyl)Ueq(C,O).

Figures

Fig. 1.
The molecular structure of the title compound, showing the 30% probability displacement ellipsoids.

Crystal data

[Sn(C6H11)3(C17H25O3S)]F(000) = 1432
Mr = 677.56Dx = 1.276 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4134 reflections
a = 15.5048 (3) Åθ = 2.2–20.5°
b = 11.4261 (3) ŵ = 0.81 mm1
c = 19.9794 (4) ÅT = 296 K
β = 94.603 (2)°Prism, colourless
V = 3528.12 (14) Å30.23 × 0.16 × 0.12 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer8086 independent reflections
Radiation source: fine-focus sealed tube4695 reflections with I > 2σ(I)
graphiteRint = 0.068
[var phi] and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −20→20
Tmin = 0.835, Tmax = 0.909k = −14→14
32619 measured reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0472P)2 + 1.0822P] where P = (Fo2 + 2Fc2)/3
8086 reflections(Δ/σ)max = 0.002
368 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = −0.37 e Å3

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

xyzUiso*/Ueq
Sn10.675022 (18)0.68259 (2)0.423505 (14)0.05384 (11)
S10.91268 (8)0.32747 (11)0.47742 (6)0.0688 (3)
O10.81458 (19)0.1966 (3)0.78627 (15)0.0712 (9)
H10.84950.14850.80250.107*
O20.70824 (19)0.5181 (3)0.46211 (15)0.0656 (8)
C10.7760 (3)0.4750 (4)0.4374 (2)0.0571 (10)
O30.8166 (2)0.5278 (3)0.39778 (18)0.0897 (11)
C20.7988 (3)0.3518 (3)0.4606 (2)0.0570 (11)
H2A0.77660.29700.42630.068*
H2B0.77030.33550.50100.068*
C30.9325 (3)0.4088 (4)0.5546 (2)0.0637 (12)
H3A0.99430.42170.56280.076*
H3B0.90500.48480.54910.076*
C40.9002 (3)0.3496 (3)0.6156 (2)0.0512 (10)
C90.9478 (2)0.2609 (4)0.64754 (19)0.0500 (9)
H90.99890.23740.63020.060*
C80.9223 (2)0.2053 (3)0.70464 (19)0.0474 (9)
C70.8447 (3)0.2435 (4)0.72873 (19)0.0503 (9)
C60.7929 (2)0.3316 (3)0.6972 (2)0.0508 (10)
C50.8240 (3)0.3836 (3)0.6404 (2)0.0527 (10)
H50.79200.44320.61870.063*
C100.7064 (3)0.3702 (4)0.7228 (2)0.0593 (11)
C110.7205 (3)0.4203 (4)0.7944 (2)0.0813 (15)
H11A0.74740.36210.82380.122*
H11B0.66580.44200.80990.122*
H11C0.75720.48790.79400.122*
C130.6623 (3)0.4652 (4)0.6783 (3)0.0890 (16)
H13A0.70010.53150.67680.134*
H13B0.60950.48860.69650.134*
H13C0.64960.43510.63370.134*
C120.6446 (3)0.2650 (5)0.7238 (3)0.0836 (15)
H12A0.63770.23040.67990.125*
H12B0.58930.29090.73660.125*
H12C0.66810.20810.75560.125*
C140.9797 (3)0.1098 (4)0.7400 (2)0.0549 (10)
C161.0166 (4)0.1528 (5)0.8085 (2)0.0901 (16)
H16A1.05150.09250.83030.135*
H16B0.97000.17210.83550.135*
H16C1.05140.22110.80300.135*
C150.9297 (3)−0.0044 (4)0.7481 (3)0.0838 (15)
H15A0.8964−0.02240.70680.126*
H15B0.89160.00450.78340.126*
H15C0.9698−0.06680.75920.126*
C171.0558 (3)0.0774 (5)0.6999 (3)0.0928 (18)
H17A1.03450.05000.65630.139*
H17B1.08910.01670.72300.139*
H17C1.09160.14490.69530.139*
C180.6470 (3)0.6709 (4)0.31668 (19)0.0547 (10)
H180.60300.73040.30470.066*
C230.7229 (3)0.6982 (4)0.2761 (2)0.0698 (12)
H23A0.77000.64490.28910.084*
H23B0.74280.77710.28630.084*
C220.6995 (4)0.6874 (4)0.2010 (2)0.0835 (15)
H22A0.65880.74880.18670.100*
H22B0.75110.69800.17730.100*
C210.6598 (4)0.5699 (5)0.1829 (2)0.0835 (15)
H21A0.64260.56800.13510.100*
H21B0.70270.50910.19250.100*
C200.5826 (3)0.5459 (5)0.2212 (2)0.0797 (14)
H20A0.56040.46840.21000.096*
H20B0.53750.60230.20840.096*
C190.6063 (3)0.5537 (4)0.2967 (2)0.0658 (12)
H19A0.55470.54250.32030.079*
H19B0.64660.49140.31010.079*
C300.5538 (3)0.6957 (4)0.4699 (2)0.0628 (11)
H300.51750.63080.45230.075*
C350.5628 (3)0.6826 (5)0.5445 (2)0.0833 (15)
H35A0.60240.74180.56350.100*
H35B0.58760.60660.55580.100*
C310.5065 (3)0.8080 (4)0.4489 (2)0.0790 (14)
H31A0.49630.81000.40040.095*
H31B0.54230.87470.46280.095*
C240.7751 (3)0.8051 (4)0.4572 (3)0.0741 (13)
H240.81440.80780.42120.089*
C250.7395 (4)0.9250 (4)0.4611 (3)0.0963 (18)
H25A0.69520.92520.49280.116*
H25B0.71220.94640.41750.116*
C320.4200 (3)0.8167 (6)0.4804 (3)0.104 (2)
H32A0.39300.89100.46810.125*
H32B0.38200.75490.46250.125*
C290.8294 (4)0.7719 (5)0.5180 (3)0.1028 (19)
H29A0.85880.69890.50990.123*
H29B0.79280.75910.55450.123*
C280.8968 (4)0.8659 (5)0.5389 (4)0.119 (2)
H28A0.92510.84540.58230.142*
H28B0.94050.86670.50670.142*
C270.8600 (4)0.9832 (5)0.5428 (3)0.115 (2)
H27A0.82490.98660.58080.138*
H27B0.90661.03930.55060.138*
C260.8072 (4)1.0163 (5)0.4826 (4)0.116 (2)
H26A0.84441.02840.44650.139*
H26B0.77851.08980.49060.139*
C330.4306 (3)0.8070 (6)0.5543 (3)0.0961 (18)
H33A0.37420.80910.57210.115*
H33B0.46380.87310.57270.115*
C340.4763 (4)0.6944 (5)0.5756 (3)0.0945 (17)
H34A0.43960.62840.56200.113*
H34B0.48620.69270.62420.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.05522 (17)0.05444 (18)0.05190 (18)0.00493 (15)0.00459 (12)−0.00436 (15)
S10.0727 (7)0.0773 (8)0.0591 (7)0.0236 (7)0.0228 (6)0.0165 (6)
O10.0712 (19)0.082 (2)0.0642 (19)0.0205 (16)0.0254 (16)0.0273 (16)
O20.0657 (18)0.0605 (19)0.072 (2)0.0070 (15)0.0132 (15)−0.0017 (15)
C10.055 (3)0.060 (3)0.056 (3)0.000 (2)−0.005 (2)0.002 (2)
O30.086 (2)0.085 (2)0.102 (3)0.0218 (19)0.031 (2)0.043 (2)
C20.068 (3)0.048 (2)0.054 (3)0.001 (2)0.004 (2)−0.0021 (19)
C30.056 (3)0.071 (3)0.064 (3)−0.012 (2)0.004 (2)0.018 (2)
C40.054 (2)0.047 (2)0.052 (2)−0.0078 (19)0.0037 (19)0.0063 (18)
C90.046 (2)0.055 (2)0.049 (2)0.0007 (19)0.0048 (18)0.006 (2)
C80.048 (2)0.048 (2)0.046 (2)−0.0017 (18)−0.0007 (17)0.0014 (18)
C70.053 (2)0.051 (2)0.047 (2)0.000 (2)0.0099 (18)0.0037 (19)
C60.052 (2)0.044 (2)0.056 (2)−0.0022 (19)0.0043 (18)0.0001 (19)
C50.057 (2)0.043 (2)0.056 (3)0.001 (2)−0.004 (2)0.0075 (19)
C100.054 (2)0.052 (2)0.073 (3)0.002 (2)0.010 (2)0.000 (2)
C110.072 (3)0.089 (4)0.085 (4)0.006 (3)0.021 (3)−0.020 (3)
C130.070 (3)0.080 (4)0.117 (4)0.025 (3)0.009 (3)0.019 (3)
C120.053 (3)0.077 (3)0.123 (4)−0.007 (3)0.015 (3)−0.004 (3)
C140.054 (2)0.057 (3)0.054 (3)0.007 (2)0.0040 (19)0.011 (2)
C160.104 (4)0.099 (4)0.063 (3)0.010 (3)−0.022 (3)0.013 (3)
C150.088 (4)0.059 (3)0.104 (4)0.008 (3)0.004 (3)0.017 (3)
C170.065 (3)0.116 (5)0.099 (4)0.038 (3)0.020 (3)0.033 (3)
C180.058 (2)0.056 (3)0.050 (2)0.009 (2)0.0044 (18)−0.003 (2)
C230.081 (3)0.067 (3)0.063 (3)−0.007 (2)0.009 (2)0.001 (2)
C220.112 (4)0.081 (4)0.059 (3)−0.007 (3)0.016 (3)0.011 (3)
C210.116 (4)0.082 (4)0.053 (3)0.014 (3)0.010 (3)−0.007 (3)
C200.089 (4)0.080 (3)0.067 (3)0.006 (3)−0.012 (3)−0.018 (3)
C190.064 (3)0.072 (3)0.062 (3)−0.005 (2)0.005 (2)−0.002 (2)
C300.061 (3)0.070 (3)0.059 (3)0.007 (2)0.011 (2)−0.005 (2)
C350.085 (3)0.099 (4)0.066 (3)0.020 (3)0.013 (3)0.016 (3)
C310.068 (3)0.096 (4)0.073 (3)0.020 (3)0.010 (2)0.010 (3)
C240.073 (3)0.068 (3)0.078 (3)−0.001 (3)−0.009 (2)−0.008 (3)
C250.096 (4)0.056 (3)0.129 (5)−0.008 (3)−0.039 (3)0.017 (3)
C320.073 (3)0.136 (6)0.105 (5)0.034 (4)0.017 (3)−0.007 (4)
C290.110 (4)0.062 (3)0.127 (5)0.010 (3)−0.044 (4)−0.002 (3)
C280.094 (4)0.085 (4)0.164 (6)0.008 (4)−0.066 (4)−0.015 (4)
C270.133 (5)0.082 (4)0.121 (5)−0.014 (4)−0.036 (4)−0.018 (4)
C260.113 (5)0.060 (3)0.164 (6)−0.015 (3)−0.045 (4)0.011 (4)
C330.076 (3)0.121 (5)0.095 (4)0.009 (3)0.026 (3)−0.023 (4)
C340.097 (4)0.113 (5)0.077 (4)−0.015 (4)0.037 (3)0.002 (3)

Geometric parameters (Å, °)

Sn1—O22.081 (3)C18—C191.520 (6)
Sn1—C182.148 (4)C18—H180.9800
Sn1—C242.157 (5)C23—C221.521 (6)
Sn1—C302.166 (4)C23—H23A0.9700
S1—C21.792 (4)C23—H23B0.9700
S1—C31.806 (5)C22—C211.509 (6)
O1—C71.383 (4)C22—H22A0.9700
O1—H10.8200C22—H22B0.9700
O2—C11.294 (5)C21—C201.497 (7)
C1—O31.211 (5)C21—H21A0.9700
C1—C21.515 (6)C21—H21B0.9700
C2—H2A0.9700C20—C191.526 (6)
C2—H2B0.9700C20—H20A0.9700
C3—C41.514 (5)C20—H20B0.9700
C3—H3A0.9700C19—H19A0.9700
C3—H3B0.9700C19—H19B0.9700
C4—C51.373 (5)C30—C351.493 (6)
C4—C91.380 (5)C30—C311.520 (6)
C9—C81.390 (5)C30—H300.9800
C9—H90.9300C35—C341.530 (7)
C8—C71.401 (5)C35—H35A0.9700
C8—C141.542 (5)C35—H35B0.9700
C7—C61.405 (5)C31—C321.529 (6)
C6—C51.400 (5)C31—H31A0.9700
C6—C101.538 (5)C31—H31B0.9700
C5—H50.9300C24—C291.471 (7)
C10—C131.529 (6)C24—C251.481 (6)
C10—C121.538 (6)C24—H240.9800
C10—C111.540 (6)C25—C261.517 (7)
C11—H11A0.9600C25—H25A0.9700
C11—H11B0.9600C25—H25B0.9700
C11—H11C0.9600C32—C331.478 (7)
C13—H13A0.9600C32—H32A0.9700
C13—H13B0.9600C32—H32B0.9700
C13—H13C0.9600C29—C281.533 (8)
C12—H12A0.9600C29—H29A0.9700
C12—H12B0.9600C29—H29B0.9700
C12—H12C0.9600C28—C271.461 (8)
C14—C161.521 (6)C28—H28A0.9700
C14—C171.524 (6)C28—H28B0.9700
C14—C151.533 (6)C27—C261.449 (7)
C16—H16A0.9600C27—H27A0.9700
C16—H16B0.9600C27—H27B0.9700
C16—H16C0.9600C26—H26A0.9700
C15—H15A0.9600C26—H26B0.9700
C15—H15B0.9600C33—C341.513 (7)
C15—H15C0.9600C33—H33A0.9700
C17—H17A0.9600C33—H33B0.9700
C17—H17B0.9600C34—H34A0.9700
C17—H17C0.9600C34—H34B0.9700
C18—C231.513 (6)
O2—Sn1—C18109.65 (13)C18—C23—H23B109.2
O2—Sn1—C24108.65 (15)C22—C23—H23B109.2
C18—Sn1—C24115.72 (18)H23A—C23—H23B107.9
O2—Sn1—C3095.82 (14)C21—C22—C23111.7 (4)
C18—Sn1—C30108.43 (16)C21—C22—H22A109.3
C24—Sn1—C30116.65 (18)C23—C22—H22A109.3
C2—S1—C3100.3 (2)C21—C22—H22B109.3
C7—O1—H1109.5C23—C22—H22B109.3
C1—O2—Sn1112.7 (3)H22A—C22—H22B107.9
O3—C1—O2122.7 (4)C20—C21—C22111.5 (4)
O3—C1—C2122.8 (4)C20—C21—H21A109.3
O2—C1—C2114.4 (4)C22—C21—H21A109.3
C1—C2—S1113.8 (3)C20—C21—H21B109.3
C1—C2—H2A108.8C22—C21—H21B109.3
S1—C2—H2A108.8H21A—C21—H21B108.0
C1—C2—H2B108.8C21—C20—C19110.8 (4)
S1—C2—H2B108.8C21—C20—H20A109.5
H2A—C2—H2B107.7C19—C20—H20A109.5
C4—C3—S1114.4 (3)C21—C20—H20B109.5
C4—C3—H3A108.7C19—C20—H20B109.5
S1—C3—H3A108.7H20A—C20—H20B108.1
C4—C3—H3B108.7C18—C19—C20111.9 (4)
S1—C3—H3B108.7C18—C19—H19A109.2
H3A—C3—H3B107.6C20—C19—H19A109.2
C5—C4—C9119.0 (4)C18—C19—H19B109.2
C5—C4—C3121.0 (4)C20—C19—H19B109.2
C9—C4—C3120.1 (4)H19A—C19—H19B107.9
C4—C9—C8122.6 (4)C35—C30—C31111.3 (4)
C4—C9—H9118.7C35—C30—Sn1113.9 (3)
C8—C9—H9118.7C31—C30—Sn1110.9 (3)
C9—C8—C7116.6 (3)C35—C30—H30106.7
C9—C8—C14120.5 (3)C31—C30—H30106.7
C7—C8—C14122.9 (3)Sn1—C30—H30106.7
O1—C7—C8121.4 (3)C30—C35—C34112.5 (4)
O1—C7—C6115.6 (3)C30—C35—H35A109.1
C8—C7—C6123.0 (3)C34—C35—H35A109.1
C5—C6—C7116.4 (3)C30—C35—H35B109.1
C5—C6—C10120.9 (4)C34—C35—H35B109.1
C7—C6—C10122.6 (3)H35A—C35—H35B107.8
C4—C5—C6122.4 (4)C30—C31—C32111.2 (4)
C4—C5—H5118.8C30—C31—H31A109.4
C6—C5—H5118.8C32—C31—H31A109.4
C13—C10—C6111.8 (4)C30—C31—H31B109.4
C13—C10—C12108.2 (4)C32—C31—H31B109.4
C6—C10—C12110.0 (4)H31A—C31—H31B108.0
C13—C10—C11107.4 (4)C29—C24—C25112.7 (4)
C6—C10—C11110.6 (3)C29—C24—Sn1116.1 (4)
C12—C10—C11108.7 (4)C25—C24—Sn1110.8 (3)
C10—C11—H11A109.5C29—C24—H24105.4
C10—C11—H11B109.5C25—C24—H24105.4
H11A—C11—H11B109.5Sn1—C24—H24105.4
C10—C11—H11C109.5C24—C25—C26113.5 (5)
H11A—C11—H11C109.5C24—C25—H25A108.9
H11B—C11—H11C109.5C26—C25—H25A108.9
C10—C13—H13A109.5C24—C25—H25B108.9
C10—C13—H13B109.5C26—C25—H25B108.9
H13A—C13—H13B109.5H25A—C25—H25B107.7
C10—C13—H13C109.5C33—C32—C31112.1 (5)
H13A—C13—H13C109.5C33—C32—H32A109.2
H13B—C13—H13C109.5C31—C32—H32A109.2
C10—C12—H12A109.5C33—C32—H32B109.2
C10—C12—H12B109.5C31—C32—H32B109.2
H12A—C12—H12B109.5H32A—C32—H32B107.9
C10—C12—H12C109.5C24—C29—C28112.1 (5)
H12A—C12—H12C109.5C24—C29—H29A109.2
H12B—C12—H12C109.5C28—C29—H29A109.2
C16—C14—C17107.5 (4)C24—C29—H29B109.2
C16—C14—C15109.7 (4)C28—C29—H29B109.2
C17—C14—C15105.5 (4)H29A—C29—H29B107.9
C16—C14—C8110.2 (4)C27—C28—C29113.4 (5)
C17—C14—C8111.9 (3)C27—C28—H28A108.9
C15—C14—C8111.9 (3)C29—C28—H28A108.9
C14—C16—H16A109.5C27—C28—H28B108.9
C14—C16—H16B109.5C29—C28—H28B108.9
H16A—C16—H16B109.5H28A—C28—H28B107.7
C14—C16—H16C109.5C26—C27—C28113.0 (5)
H16A—C16—H16C109.5C26—C27—H27A109.0
H16B—C16—H16C109.5C28—C27—H27A109.0
C14—C15—H15A109.5C26—C27—H27B109.0
C14—C15—H15B109.5C28—C27—H27B109.0
H15A—C15—H15B109.5H27A—C27—H27B107.8
C14—C15—H15C109.5C27—C26—C25112.8 (5)
H15A—C15—H15C109.5C27—C26—H26A109.0
H15B—C15—H15C109.5C25—C26—H26A109.0
C14—C17—H17A109.5C27—C26—H26B109.0
C14—C17—H17B109.5C25—C26—H26B109.0
H17A—C17—H17B109.5H26A—C26—H26B107.8
C14—C17—H17C109.5C32—C33—C34110.9 (5)
H17A—C17—H17C109.5C32—C33—H33A109.5
H17B—C17—H17C109.5C34—C33—H33A109.5
C23—C18—C19111.4 (3)C32—C33—H33B109.5
C23—C18—Sn1114.5 (3)C34—C33—H33B109.5
C19—C18—Sn1111.3 (3)H33A—C33—H33B108.1
C23—C18—H18106.4C33—C34—C35111.5 (4)
C19—C18—H18106.4C33—C34—H34A109.3
Sn1—C18—H18106.4C35—C34—H34A109.3
C18—C23—C22112.2 (4)C33—C34—H34B109.3
C18—C23—H23A109.2C35—C34—H34B109.3
C22—C23—H23A109.2H34A—C34—H34B108.0
C18—Sn1—O2—C160.5 (3)C30—Sn1—C18—C23162.2 (3)
C24—Sn1—O2—C1−66.9 (3)O2—Sn1—C18—C1933.1 (3)
C30—Sn1—O2—C1172.5 (3)C24—Sn1—C18—C19156.4 (3)
Sn1—O2—C1—O32.4 (5)C30—Sn1—C18—C19−70.4 (3)
Sn1—O2—C1—C2−176.0 (3)C19—C18—C23—C2252.1 (5)
O3—C1—C2—S141.6 (6)Sn1—C18—C23—C22179.5 (3)
O2—C1—C2—S1−140.0 (3)C18—C23—C22—C21−53.4 (6)
C3—S1—C2—C172.6 (3)C23—C22—C21—C2055.6 (6)
C2—S1—C3—C474.6 (3)C22—C21—C20—C19−56.4 (6)
S1—C3—C4—C5−101.0 (4)C23—C18—C19—C20−53.3 (5)
S1—C3—C4—C979.7 (4)Sn1—C18—C19—C20177.6 (3)
C5—C4—C9—C8−0.9 (6)C21—C20—C19—C1855.5 (5)
C3—C4—C9—C8178.4 (4)O2—Sn1—C30—C3556.5 (4)
C4—C9—C8—C70.2 (6)C18—Sn1—C30—C35169.5 (3)
C4—C9—C8—C14−177.6 (4)C24—Sn1—C30—C35−57.8 (4)
C9—C8—C7—O1−178.1 (4)O2—Sn1—C30—C31−176.9 (3)
C14—C8—C7—O1−0.3 (6)C18—Sn1—C30—C31−64.0 (3)
C9—C8—C7—C61.3 (6)C24—Sn1—C30—C3168.8 (4)
C14—C8—C7—C6179.0 (4)C31—C30—C35—C3452.7 (6)
O1—C7—C6—C5177.5 (4)Sn1—C30—C35—C34179.1 (4)
C8—C7—C6—C5−1.9 (6)C35—C30—C31—C32−53.2 (6)
O1—C7—C6—C10−2.6 (6)Sn1—C30—C31—C32178.9 (4)
C8—C7—C6—C10178.0 (4)O2—Sn1—C24—C29−22.1 (5)
C9—C4—C5—C60.2 (6)C18—Sn1—C24—C29−145.9 (4)
C3—C4—C5—C6−179.2 (4)C30—Sn1—C24—C2984.7 (4)
C7—C6—C5—C41.2 (6)O2—Sn1—C24—C25−152.3 (4)
C10—C6—C5—C4−178.7 (4)C18—Sn1—C24—C2583.9 (4)
C5—C6—C10—C131.4 (6)C30—Sn1—C24—C25−45.5 (4)
C7—C6—C10—C13−178.6 (4)C29—C24—C25—C2649.7 (7)
C5—C6—C10—C12121.6 (4)Sn1—C24—C25—C26−178.3 (4)
C7—C6—C10—C12−58.3 (5)C30—C31—C32—C3355.7 (7)
C5—C6—C10—C11−118.3 (4)C25—C24—C29—C28−49.2 (7)
C7—C6—C10—C1161.7 (5)Sn1—C24—C29—C28−178.5 (4)
C9—C8—C14—C16112.1 (4)C24—C29—C28—C2750.5 (8)
C7—C8—C14—C16−65.6 (5)C29—C28—C27—C26−51.6 (9)
C9—C8—C14—C17−7.5 (6)C28—C27—C26—C2551.1 (9)
C7—C8—C14—C17174.8 (4)C24—C25—C26—C27−50.4 (8)
C9—C8—C14—C15−125.6 (4)C31—C32—C33—C34−56.3 (7)
C7—C8—C14—C1556.7 (5)C32—C33—C34—C3554.8 (7)
O2—Sn1—C18—C23−94.4 (3)C30—C35—C34—C33−53.6 (6)
C24—Sn1—C18—C2328.9 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2317).

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