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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: kmlo@um.edu.my

(Received 27 May 2010; accepted 8 June 2010; online 16 June 2010)

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[Tiekink, E. R. T. (1991). Appl. Org. Chem. 5, 1-23.]). For a triphenyl­tin analogue of the title compound, see: Lee et al. (2009[Lee, S. M., Lo, K. M., Mohd Ali, H. & Robinson, W. T. (2009). Acta Cryst. E65, m808.]). For other related structures, see: Alcock & Timms (1968[Alcock, N. W. & Timms, R. E. (1968). J. Chem. Soc. A, pp. 1876-1878.]); Keng et al. (2010[Keng, T. C., Lo, K. M. & Ng, S. W. (2010). Acta Cryst. E66, m307.]); Ng & Kumar Das (1997[Ng, S. W. & Kumar Das, V. G. (1997). Acta Cryst. C53, 548-549.]); Thong et al. (2009[Thong, P. Y., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m490.]); Zhang et al. (2007[Zhang, X., Song, H., Li, Q., Liu, X. & Tang, L. (2007). Polyhedron, 26, 3743-3749.]). For the preparation of the ligand, see: Yehye et al. (2009[Yehye, W. A., Ariffin, A. & Ng, S. W. (2009). Acta Cryst. E65, o730.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H11)3(C17H25O3S)]

  • Mr = 677.56

  • Monoclinic, P 21 /c

  • 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.835, Tmax = 0.909

  • 32619 measured reflections

  • 8086 independent reflections

  • 4695 reflections with I > 2σ(I)

  • Rint = 0.068

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Sn1—O2 2.081 (3)
Sn1—C18 2.148 (4)
Sn1—C24 2.157 (5)
Sn1—C30 2.166 (4)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the 30% probability displacement ellipsoids.
Tricyclohexyl{2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]acetato- κO}tin(IV) top
Crystal data top
[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 top
Bruker APEXII CCD
diffractometer
8086 independent reflections
Radiation source: fine-focus sealed tube4695 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ϕ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2020
Tmin = 0.835, Tmax = 0.909k = 1414
32619 measured reflectionsl = 2525
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.00 w = 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
Crystal data top
[Sn(C6H11)3(C17H25O3S)]V = 3528.12 (14) Å3
Mr = 677.56Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.5048 (3) ŵ = 0.81 mm1
b = 11.4261 (3) ÅT = 296 K
c = 19.9794 (4) Å0.23 × 0.16 × 0.12 mm
β = 94.603 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
8086 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4695 reflections with I > 2σ(I)
Tmin = 0.835, Tmax = 0.909Rint = 0.068
32619 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.00Δρmax = 0.65 e Å3
8086 reflectionsΔρmin = 0.37 e Å3
368 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H15A0.89640.02240.70680.126*
H15B0.89160.00450.78340.126*
H15C0.96980.06680.75920.126*
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) top
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, º) top
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—C166.9 (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—C1970.4 (3)
Sn1—O2—C1—C2176.0 (3)C19—C18—C23—C2252.1 (5)
O3—C1—C2—S141.6 (6)Sn1—C18—C23—C22179.5 (3)
O2—C1—C2—S1140.0 (3)C18—C23—C22—C2153.4 (6)
C3—S1—C2—C172.6 (3)C23—C22—C21—C2055.6 (6)
C2—S1—C3—C474.6 (3)C22—C21—C20—C1956.4 (6)
S1—C3—C4—C5101.0 (4)C23—C18—C19—C2053.3 (5)
S1—C3—C4—C979.7 (4)Sn1—C18—C19—C20177.6 (3)
C5—C4—C9—C80.9 (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—C14177.6 (4)C24—Sn1—C30—C3557.8 (4)
C9—C8—C7—O1178.1 (4)O2—Sn1—C30—C31176.9 (3)
C14—C8—C7—O10.3 (6)C18—Sn1—C30—C3164.0 (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—C51.9 (6)C35—C30—C31—C3253.2 (6)
O1—C7—C6—C102.6 (6)Sn1—C30—C31—C32178.9 (4)
C8—C7—C6—C10178.0 (4)O2—Sn1—C24—C2922.1 (5)
C9—C4—C5—C60.2 (6)C18—Sn1—C24—C29145.9 (4)
C3—C4—C5—C6179.2 (4)C30—Sn1—C24—C2984.7 (4)
C7—C6—C5—C41.2 (6)O2—Sn1—C24—C25152.3 (4)
C10—C6—C5—C4178.7 (4)C18—Sn1—C24—C2583.9 (4)
C5—C6—C10—C131.4 (6)C30—Sn1—C24—C2545.5 (4)
C7—C6—C10—C13178.6 (4)C29—C24—C25—C2649.7 (7)
C5—C6—C10—C12121.6 (4)Sn1—C24—C25—C26178.3 (4)
C7—C6—C10—C1258.3 (5)C30—C31—C32—C3355.7 (7)
C5—C6—C10—C11118.3 (4)C25—C24—C29—C2849.2 (7)
C7—C6—C10—C1161.7 (5)Sn1—C24—C29—C28178.5 (4)
C9—C8—C14—C16112.1 (4)C24—C29—C28—C2750.5 (8)
C7—C8—C14—C1665.6 (5)C29—C28—C27—C2651.6 (9)
C9—C8—C14—C177.5 (6)C28—C27—C26—C2551.1 (9)
C7—C8—C14—C17174.8 (4)C24—C25—C26—C2750.4 (8)
C9—C8—C14—C15125.6 (4)C31—C32—C33—C3456.3 (7)
C7—C8—C14—C1556.7 (5)C32—C33—C34—C3554.8 (7)
O2—Sn1—C18—C2394.4 (3)C30—C35—C34—C3353.6 (6)
C24—Sn1—C18—C2328.9 (4)

Experimental details

Crystal data
Chemical formula[Sn(C6H11)3(C17H25O3S)]
Mr677.56
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)15.5048 (3), 11.4261 (3), 19.9794 (4)
β (°) 94.603 (2)
V3)3528.12 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.81
Crystal size (mm)0.23 × 0.16 × 0.12
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.835, 0.909
No. of measured, independent and
observed [I > 2σ(I)] reflections
32619, 8086, 4695
Rint0.068
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.117, 1.00
No. of reflections8086
No. of parameters368
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.65, 0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Sn1—O22.081 (3)Sn1—C242.157 (5)
Sn1—C182.148 (4)Sn1—C302.166 (4)
 

Acknowledgements

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

References

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