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

Lee, S.M.; Mohd Ali, H.; Lo, K.M.

doi:10.1107/S1600536810021884

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m792

doi:10.1107/S1600536810021884

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

See Mun Lee,^a Hapipah Mohd Ali ^a and Kong Mun Lo ^a ^*

^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 Sn^IV 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 ). 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

Crystal data

[Sn(C₆H₁₁)₃(C₁₇H₂₅O₃S)]
M_r = 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 ) 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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.117
S = 1.00
8086 reflections
368 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

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 Sn^IV 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.

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

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
M_r = 677.56	D_x = 1.276 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4134 reflections
a = 15.5048 (3) Å	θ = 2.2–20.5°
b = 11.4261 (3) Å	µ = 0.81 mm⁻¹
c = 19.9794 (4) Å	T = 296 K
β = 94.603 (2)°	Prism, colourless
V = 3528.12 (14) Å³	0.23 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	8086 independent reflections
Radiation source: fine-focus sealed tube	4695 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→20
T_min = 0.835, T_max = 0.909	k = −14→14
32619 measured reflections	l = −25→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0472P)² + 1.0822P] where P = (F_o² + 2F_c²)/3
8086 reflections	(Δ/σ)_max = 0.002
368 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Sn(C₆H₁₁)₃(C₁₇H₂₅O₃S)]	V = 3528.12 (14) Å³
M_r = 677.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.5048 (3) Å	µ = 0.81 mm⁻¹
b = 11.4261 (3) Å	T = 296 K
c = 19.9794 (4) Å	0.23 × 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)
T_min = 0.835, T_max = 0.909	R_int = 0.068
32619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	Δρ_max = 0.65 e Å⁻³
8086 reflections	Δρ_min = −0.37 e Å⁻³
368 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.675022 (18)	0.68259 (2)	0.423505 (14)	0.05384 (11)
S1	0.91268 (8)	0.32747 (11)	0.47742 (6)	0.0688 (3)
O1	0.81458 (19)	0.1966 (3)	0.78627 (15)	0.0712 (9)
H1	0.8495	0.1485	0.8025	0.107*
O2	0.70824 (19)	0.5181 (3)	0.46211 (15)	0.0656 (8)
C1	0.7760 (3)	0.4750 (4)	0.4374 (2)	0.0571 (10)
O3	0.8166 (2)	0.5278 (3)	0.39778 (18)	0.0897 (11)
C2	0.7988 (3)	0.3518 (3)	0.4606 (2)	0.0570 (11)
H2A	0.7766	0.2970	0.4263	0.068*
H2B	0.7703	0.3355	0.5010	0.068*
C3	0.9325 (3)	0.4088 (4)	0.5546 (2)	0.0637 (12)
H3A	0.9943	0.4217	0.5628	0.076*
H3B	0.9050	0.4848	0.5491	0.076*
C4	0.9002 (3)	0.3496 (3)	0.6156 (2)	0.0512 (10)
C9	0.9478 (2)	0.2609 (4)	0.64754 (19)	0.0500 (9)
H9	0.9989	0.2374	0.6302	0.060*
C8	0.9223 (2)	0.2053 (3)	0.70464 (19)	0.0474 (9)
C7	0.8447 (3)	0.2435 (4)	0.72873 (19)	0.0503 (9)
C6	0.7929 (2)	0.3316 (3)	0.6972 (2)	0.0508 (10)
C5	0.8240 (3)	0.3836 (3)	0.6404 (2)	0.0527 (10)
H5	0.7920	0.4432	0.6187	0.063*
C10	0.7064 (3)	0.3702 (4)	0.7228 (2)	0.0593 (11)
C11	0.7205 (3)	0.4203 (4)	0.7944 (2)	0.0813 (15)
H11A	0.7474	0.3621	0.8238	0.122*
H11B	0.6658	0.4420	0.8099	0.122*
H11C	0.7572	0.4879	0.7940	0.122*
C13	0.6623 (3)	0.4652 (4)	0.6783 (3)	0.0890 (16)
H13A	0.7001	0.5315	0.6768	0.134*
H13B	0.6095	0.4886	0.6965	0.134*
H13C	0.6496	0.4351	0.6337	0.134*
C12	0.6446 (3)	0.2650 (5)	0.7238 (3)	0.0836 (15)
H12A	0.6377	0.2304	0.6799	0.125*
H12B	0.5893	0.2909	0.7366	0.125*
H12C	0.6681	0.2081	0.7556	0.125*
C14	0.9797 (3)	0.1098 (4)	0.7400 (2)	0.0549 (10)
C16	1.0166 (4)	0.1528 (5)	0.8085 (2)	0.0901 (16)
H16A	1.0515	0.0925	0.8303	0.135*
H16B	0.9700	0.1721	0.8355	0.135*
H16C	1.0514	0.2211	0.8030	0.135*
C15	0.9297 (3)	−0.0044 (4)	0.7481 (3)	0.0838 (15)
H15A	0.8964	−0.0224	0.7068	0.126*
H15B	0.8916	0.0045	0.7834	0.126*
H15C	0.9698	−0.0668	0.7592	0.126*
C17	1.0558 (3)	0.0774 (5)	0.6999 (3)	0.0928 (18)
H17A	1.0345	0.0500	0.6563	0.139*
H17B	1.0891	0.0167	0.7230	0.139*
H17C	1.0916	0.1449	0.6953	0.139*
C18	0.6470 (3)	0.6709 (4)	0.31668 (19)	0.0547 (10)
H18	0.6030	0.7304	0.3047	0.066*
C23	0.7229 (3)	0.6982 (4)	0.2761 (2)	0.0698 (12)
H23A	0.7700	0.6449	0.2891	0.084*
H23B	0.7428	0.7771	0.2863	0.084*
C22	0.6995 (4)	0.6874 (4)	0.2010 (2)	0.0835 (15)
H22A	0.6588	0.7488	0.1867	0.100*
H22B	0.7511	0.6980	0.1773	0.100*
C21	0.6598 (4)	0.5699 (5)	0.1829 (2)	0.0835 (15)
H21A	0.6426	0.5680	0.1351	0.100*
H21B	0.7027	0.5091	0.1925	0.100*
C20	0.5826 (3)	0.5459 (5)	0.2212 (2)	0.0797 (14)
H20A	0.5604	0.4684	0.2100	0.096*
H20B	0.5375	0.6023	0.2084	0.096*
C19	0.6063 (3)	0.5537 (4)	0.2967 (2)	0.0658 (12)
H19A	0.5547	0.5425	0.3203	0.079*
H19B	0.6466	0.4914	0.3101	0.079*
C30	0.5538 (3)	0.6957 (4)	0.4699 (2)	0.0628 (11)
H30	0.5175	0.6308	0.4523	0.075*
C35	0.5628 (3)	0.6826 (5)	0.5445 (2)	0.0833 (15)
H35A	0.6024	0.7418	0.5635	0.100*
H35B	0.5876	0.6066	0.5558	0.100*
C31	0.5065 (3)	0.8080 (4)	0.4489 (2)	0.0790 (14)
H31A	0.4963	0.8100	0.4004	0.095*
H31B	0.5423	0.8747	0.4628	0.095*
C24	0.7751 (3)	0.8051 (4)	0.4572 (3)	0.0741 (13)
H24	0.8144	0.8078	0.4212	0.089*
C25	0.7395 (4)	0.9250 (4)	0.4611 (3)	0.0963 (18)
H25A	0.6952	0.9252	0.4928	0.116*
H25B	0.7122	0.9464	0.4175	0.116*
C32	0.4200 (3)	0.8167 (6)	0.4804 (3)	0.104 (2)
H32A	0.3930	0.8910	0.4681	0.125*
H32B	0.3820	0.7549	0.4625	0.125*
C29	0.8294 (4)	0.7719 (5)	0.5180 (3)	0.1028 (19)
H29A	0.8588	0.6989	0.5099	0.123*
H29B	0.7928	0.7591	0.5545	0.123*
C28	0.8968 (4)	0.8659 (5)	0.5389 (4)	0.119 (2)
H28A	0.9251	0.8454	0.5823	0.142*
H28B	0.9405	0.8667	0.5067	0.142*
C27	0.8600 (4)	0.9832 (5)	0.5428 (3)	0.115 (2)
H27A	0.8249	0.9866	0.5808	0.138*
H27B	0.9066	1.0393	0.5506	0.138*
C26	0.8072 (4)	1.0163 (5)	0.4826 (4)	0.116 (2)
H26A	0.8444	1.0284	0.4465	0.139*
H26B	0.7785	1.0898	0.4906	0.139*
C33	0.4306 (3)	0.8070 (6)	0.5543 (3)	0.0961 (18)
H33A	0.3742	0.8091	0.5721	0.115*
H33B	0.4638	0.8731	0.5727	0.115*
C34	0.4763 (4)	0.6944 (5)	0.5756 (3)	0.0945 (17)
H34A	0.4396	0.6284	0.5620	0.113*
H34B	0.4862	0.6927	0.6242	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.05522 (17)	0.05444 (18)	0.05190 (18)	0.00493 (15)	0.00459 (12)	−0.00436 (15)
S1	0.0727 (7)	0.0773 (8)	0.0591 (7)	0.0236 (7)	0.0228 (6)	0.0165 (6)
O1	0.0712 (19)	0.082 (2)	0.0642 (19)	0.0205 (16)	0.0254 (16)	0.0273 (16)
O2	0.0657 (18)	0.0605 (19)	0.072 (2)	0.0070 (15)	0.0132 (15)	−0.0017 (15)
C1	0.055 (3)	0.060 (3)	0.056 (3)	0.000 (2)	−0.005 (2)	0.002 (2)
O3	0.086 (2)	0.085 (2)	0.102 (3)	0.0218 (19)	0.031 (2)	0.043 (2)
C2	0.068 (3)	0.048 (2)	0.054 (3)	0.001 (2)	0.004 (2)	−0.0021 (19)
C3	0.056 (3)	0.071 (3)	0.064 (3)	−0.012 (2)	0.004 (2)	0.018 (2)
C4	0.054 (2)	0.047 (2)	0.052 (2)	−0.0078 (19)	0.0037 (19)	0.0063 (18)
C9	0.046 (2)	0.055 (2)	0.049 (2)	0.0007 (19)	0.0048 (18)	0.006 (2)
C8	0.048 (2)	0.048 (2)	0.046 (2)	−0.0017 (18)	−0.0007 (17)	0.0014 (18)
C7	0.053 (2)	0.051 (2)	0.047 (2)	0.000 (2)	0.0099 (18)	0.0037 (19)
C6	0.052 (2)	0.044 (2)	0.056 (2)	−0.0022 (19)	0.0043 (18)	0.0001 (19)
C5	0.057 (2)	0.043 (2)	0.056 (3)	0.001 (2)	−0.004 (2)	0.0075 (19)
C10	0.054 (2)	0.052 (2)	0.073 (3)	0.002 (2)	0.010 (2)	0.000 (2)
C11	0.072 (3)	0.089 (4)	0.085 (4)	0.006 (3)	0.021 (3)	−0.020 (3)
C13	0.070 (3)	0.080 (4)	0.117 (4)	0.025 (3)	0.009 (3)	0.019 (3)
C12	0.053 (3)	0.077 (3)	0.123 (4)	−0.007 (3)	0.015 (3)	−0.004 (3)
C14	0.054 (2)	0.057 (3)	0.054 (3)	0.007 (2)	0.0040 (19)	0.011 (2)
C16	0.104 (4)	0.099 (4)	0.063 (3)	0.010 (3)	−0.022 (3)	0.013 (3)
C15	0.088 (4)	0.059 (3)	0.104 (4)	0.008 (3)	0.004 (3)	0.017 (3)
C17	0.065 (3)	0.116 (5)	0.099 (4)	0.038 (3)	0.020 (3)	0.033 (3)
C18	0.058 (2)	0.056 (3)	0.050 (2)	0.009 (2)	0.0044 (18)	−0.003 (2)
C23	0.081 (3)	0.067 (3)	0.063 (3)	−0.007 (2)	0.009 (2)	0.001 (2)
C22	0.112 (4)	0.081 (4)	0.059 (3)	−0.007 (3)	0.016 (3)	0.011 (3)
C21	0.116 (4)	0.082 (4)	0.053 (3)	0.014 (3)	0.010 (3)	−0.007 (3)
C20	0.089 (4)	0.080 (3)	0.067 (3)	0.006 (3)	−0.012 (3)	−0.018 (3)
C19	0.064 (3)	0.072 (3)	0.062 (3)	−0.005 (2)	0.005 (2)	−0.002 (2)
C30	0.061 (3)	0.070 (3)	0.059 (3)	0.007 (2)	0.011 (2)	−0.005 (2)
C35	0.085 (3)	0.099 (4)	0.066 (3)	0.020 (3)	0.013 (3)	0.016 (3)
C31	0.068 (3)	0.096 (4)	0.073 (3)	0.020 (3)	0.010 (2)	0.010 (3)
C24	0.073 (3)	0.068 (3)	0.078 (3)	−0.001 (3)	−0.009 (2)	−0.008 (3)
C25	0.096 (4)	0.056 (3)	0.129 (5)	−0.008 (3)	−0.039 (3)	0.017 (3)
C32	0.073 (3)	0.136 (6)	0.105 (5)	0.034 (4)	0.017 (3)	−0.007 (4)
C29	0.110 (4)	0.062 (3)	0.127 (5)	0.010 (3)	−0.044 (4)	−0.002 (3)
C28	0.094 (4)	0.085 (4)	0.164 (6)	0.008 (4)	−0.066 (4)	−0.015 (4)
C27	0.133 (5)	0.082 (4)	0.121 (5)	−0.014 (4)	−0.036 (4)	−0.018 (4)
C26	0.113 (5)	0.060 (3)	0.164 (6)	−0.015 (3)	−0.045 (4)	0.011 (4)
C33	0.076 (3)	0.121 (5)	0.095 (4)	0.009 (3)	0.026 (3)	−0.023 (4)
C34	0.097 (4)	0.113 (5)	0.077 (4)	−0.015 (4)	0.037 (3)	0.002 (3)

Geometric parameters (Å, º) top

Sn1—O2	2.081 (3)	C18—C19	1.520 (6)
Sn1—C18	2.148 (4)	C18—H18	0.9800
Sn1—C24	2.157 (5)	C23—C22	1.521 (6)
Sn1—C30	2.166 (4)	C23—H23A	0.9700
S1—C2	1.792 (4)	C23—H23B	0.9700
S1—C3	1.806 (5)	C22—C21	1.509 (6)
O1—C7	1.383 (4)	C22—H22A	0.9700
O1—H1	0.8200	C22—H22B	0.9700
O2—C1	1.294 (5)	C21—C20	1.497 (7)
C1—O3	1.211 (5)	C21—H21A	0.9700
C1—C2	1.515 (6)	C21—H21B	0.9700
C2—H2A	0.9700	C20—C19	1.526 (6)
C2—H2B	0.9700	C20—H20A	0.9700
C3—C4	1.514 (5)	C20—H20B	0.9700
C3—H3A	0.9700	C19—H19A	0.9700
C3—H3B	0.9700	C19—H19B	0.9700
C4—C5	1.373 (5)	C30—C35	1.493 (6)
C4—C9	1.380 (5)	C30—C31	1.520 (6)
C9—C8	1.390 (5)	C30—H30	0.9800
C9—H9	0.9300	C35—C34	1.530 (7)
C8—C7	1.401 (5)	C35—H35A	0.9700
C8—C14	1.542 (5)	C35—H35B	0.9700
C7—C6	1.405 (5)	C31—C32	1.529 (6)
C6—C5	1.400 (5)	C31—H31A	0.9700
C6—C10	1.538 (5)	C31—H31B	0.9700
C5—H5	0.9300	C24—C29	1.471 (7)
C10—C13	1.529 (6)	C24—C25	1.481 (6)
C10—C12	1.538 (6)	C24—H24	0.9800
C10—C11	1.540 (6)	C25—C26	1.517 (7)
C11—H11A	0.9600	C25—H25A	0.9700
C11—H11B	0.9600	C25—H25B	0.9700
C11—H11C	0.9600	C32—C33	1.478 (7)
C13—H13A	0.9600	C32—H32A	0.9700
C13—H13B	0.9600	C32—H32B	0.9700
C13—H13C	0.9600	C29—C28	1.533 (8)
C12—H12A	0.9600	C29—H29A	0.9700
C12—H12B	0.9600	C29—H29B	0.9700
C12—H12C	0.9600	C28—C27	1.461 (8)
C14—C16	1.521 (6)	C28—H28A	0.9700
C14—C17	1.524 (6)	C28—H28B	0.9700
C14—C15	1.533 (6)	C27—C26	1.449 (7)
C16—H16A	0.9600	C27—H27A	0.9700
C16—H16B	0.9600	C27—H27B	0.9700
C16—H16C	0.9600	C26—H26A	0.9700
C15—H15A	0.9600	C26—H26B	0.9700
C15—H15B	0.9600	C33—C34	1.513 (7)
C15—H15C	0.9600	C33—H33A	0.9700
C17—H17A	0.9600	C33—H33B	0.9700
C17—H17B	0.9600	C34—H34A	0.9700
C17—H17C	0.9600	C34—H34B	0.9700
C18—C23	1.513 (6)

O2—Sn1—C18	109.65 (13)	C18—C23—H23B	109.2
O2—Sn1—C24	108.65 (15)	C22—C23—H23B	109.2
C18—Sn1—C24	115.72 (18)	H23A—C23—H23B	107.9
O2—Sn1—C30	95.82 (14)	C21—C22—C23	111.7 (4)
C18—Sn1—C30	108.43 (16)	C21—C22—H22A	109.3
C24—Sn1—C30	116.65 (18)	C23—C22—H22A	109.3
C2—S1—C3	100.3 (2)	C21—C22—H22B	109.3
C7—O1—H1	109.5	C23—C22—H22B	109.3
C1—O2—Sn1	112.7 (3)	H22A—C22—H22B	107.9
O3—C1—O2	122.7 (4)	C20—C21—C22	111.5 (4)
O3—C1—C2	122.8 (4)	C20—C21—H21A	109.3
O2—C1—C2	114.4 (4)	C22—C21—H21A	109.3
C1—C2—S1	113.8 (3)	C20—C21—H21B	109.3
C1—C2—H2A	108.8	C22—C21—H21B	109.3
S1—C2—H2A	108.8	H21A—C21—H21B	108.0
C1—C2—H2B	108.8	C21—C20—C19	110.8 (4)
S1—C2—H2B	108.8	C21—C20—H20A	109.5
H2A—C2—H2B	107.7	C19—C20—H20A	109.5
C4—C3—S1	114.4 (3)	C21—C20—H20B	109.5
C4—C3—H3A	108.7	C19—C20—H20B	109.5
S1—C3—H3A	108.7	H20A—C20—H20B	108.1
C4—C3—H3B	108.7	C18—C19—C20	111.9 (4)
S1—C3—H3B	108.7	C18—C19—H19A	109.2
H3A—C3—H3B	107.6	C20—C19—H19A	109.2
C5—C4—C9	119.0 (4)	C18—C19—H19B	109.2
C5—C4—C3	121.0 (4)	C20—C19—H19B	109.2
C9—C4—C3	120.1 (4)	H19A—C19—H19B	107.9
C4—C9—C8	122.6 (4)	C35—C30—C31	111.3 (4)
C4—C9—H9	118.7	C35—C30—Sn1	113.9 (3)
C8—C9—H9	118.7	C31—C30—Sn1	110.9 (3)
C9—C8—C7	116.6 (3)	C35—C30—H30	106.7
C9—C8—C14	120.5 (3)	C31—C30—H30	106.7
C7—C8—C14	122.9 (3)	Sn1—C30—H30	106.7
O1—C7—C8	121.4 (3)	C30—C35—C34	112.5 (4)
O1—C7—C6	115.6 (3)	C30—C35—H35A	109.1
C8—C7—C6	123.0 (3)	C34—C35—H35A	109.1
C5—C6—C7	116.4 (3)	C30—C35—H35B	109.1
C5—C6—C10	120.9 (4)	C34—C35—H35B	109.1
C7—C6—C10	122.6 (3)	H35A—C35—H35B	107.8
C4—C5—C6	122.4 (4)	C30—C31—C32	111.2 (4)
C4—C5—H5	118.8	C30—C31—H31A	109.4
C6—C5—H5	118.8	C32—C31—H31A	109.4
C13—C10—C6	111.8 (4)	C30—C31—H31B	109.4
C13—C10—C12	108.2 (4)	C32—C31—H31B	109.4
C6—C10—C12	110.0 (4)	H31A—C31—H31B	108.0
C13—C10—C11	107.4 (4)	C29—C24—C25	112.7 (4)
C6—C10—C11	110.6 (3)	C29—C24—Sn1	116.1 (4)
C12—C10—C11	108.7 (4)	C25—C24—Sn1	110.8 (3)
C10—C11—H11A	109.5	C29—C24—H24	105.4
C10—C11—H11B	109.5	C25—C24—H24	105.4
H11A—C11—H11B	109.5	Sn1—C24—H24	105.4
C10—C11—H11C	109.5	C24—C25—C26	113.5 (5)
H11A—C11—H11C	109.5	C24—C25—H25A	108.9
H11B—C11—H11C	109.5	C26—C25—H25A	108.9
C10—C13—H13A	109.5	C24—C25—H25B	108.9
C10—C13—H13B	109.5	C26—C25—H25B	108.9
H13A—C13—H13B	109.5	H25A—C25—H25B	107.7
C10—C13—H13C	109.5	C33—C32—C31	112.1 (5)
H13A—C13—H13C	109.5	C33—C32—H32A	109.2
H13B—C13—H13C	109.5	C31—C32—H32A	109.2
C10—C12—H12A	109.5	C33—C32—H32B	109.2
C10—C12—H12B	109.5	C31—C32—H32B	109.2
H12A—C12—H12B	109.5	H32A—C32—H32B	107.9
C10—C12—H12C	109.5	C24—C29—C28	112.1 (5)
H12A—C12—H12C	109.5	C24—C29—H29A	109.2
H12B—C12—H12C	109.5	C28—C29—H29A	109.2
C16—C14—C17	107.5 (4)	C24—C29—H29B	109.2
C16—C14—C15	109.7 (4)	C28—C29—H29B	109.2
C17—C14—C15	105.5 (4)	H29A—C29—H29B	107.9
C16—C14—C8	110.2 (4)	C27—C28—C29	113.4 (5)
C17—C14—C8	111.9 (3)	C27—C28—H28A	108.9
C15—C14—C8	111.9 (3)	C29—C28—H28A	108.9
C14—C16—H16A	109.5	C27—C28—H28B	108.9
C14—C16—H16B	109.5	C29—C28—H28B	108.9
H16A—C16—H16B	109.5	H28A—C28—H28B	107.7
C14—C16—H16C	109.5	C26—C27—C28	113.0 (5)
H16A—C16—H16C	109.5	C26—C27—H27A	109.0
H16B—C16—H16C	109.5	C28—C27—H27A	109.0
C14—C15—H15A	109.5	C26—C27—H27B	109.0
C14—C15—H15B	109.5	C28—C27—H27B	109.0
H15A—C15—H15B	109.5	H27A—C27—H27B	107.8
C14—C15—H15C	109.5	C27—C26—C25	112.8 (5)
H15A—C15—H15C	109.5	C27—C26—H26A	109.0
H15B—C15—H15C	109.5	C25—C26—H26A	109.0
C14—C17—H17A	109.5	C27—C26—H26B	109.0
C14—C17—H17B	109.5	C25—C26—H26B	109.0
H17A—C17—H17B	109.5	H26A—C26—H26B	107.8
C14—C17—H17C	109.5	C32—C33—C34	110.9 (5)
H17A—C17—H17C	109.5	C32—C33—H33A	109.5
H17B—C17—H17C	109.5	C34—C33—H33A	109.5
C23—C18—C19	111.4 (3)	C32—C33—H33B	109.5
C23—C18—Sn1	114.5 (3)	C34—C33—H33B	109.5
C19—C18—Sn1	111.3 (3)	H33A—C33—H33B	108.1
C23—C18—H18	106.4	C33—C34—C35	111.5 (4)
C19—C18—H18	106.4	C33—C34—H34A	109.3
Sn1—C18—H18	106.4	C35—C34—H34A	109.3
C18—C23—C22	112.2 (4)	C33—C34—H34B	109.3
C18—C23—H23A	109.2	C35—C34—H34B	109.3
C22—C23—H23A	109.2	H34A—C34—H34B	108.0

C18—Sn1—O2—C1	60.5 (3)	C30—Sn1—C18—C23	162.2 (3)
C24—Sn1—O2—C1	−66.9 (3)	O2—Sn1—C18—C19	33.1 (3)
C30—Sn1—O2—C1	172.5 (3)	C24—Sn1—C18—C19	156.4 (3)
Sn1—O2—C1—O3	2.4 (5)	C30—Sn1—C18—C19	−70.4 (3)
Sn1—O2—C1—C2	−176.0 (3)	C19—C18—C23—C22	52.1 (5)
O3—C1—C2—S1	41.6 (6)	Sn1—C18—C23—C22	179.5 (3)
O2—C1—C2—S1	−140.0 (3)	C18—C23—C22—C21	−53.4 (6)
C3—S1—C2—C1	72.6 (3)	C23—C22—C21—C20	55.6 (6)
C2—S1—C3—C4	74.6 (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—C9	79.7 (4)	Sn1—C18—C19—C20	177.6 (3)
C5—C4—C9—C8	−0.9 (6)	C21—C20—C19—C18	55.5 (5)
C3—C4—C9—C8	178.4 (4)	O2—Sn1—C30—C35	56.5 (4)
C4—C9—C8—C7	0.2 (6)	C18—Sn1—C30—C35	169.5 (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—C6	1.3 (6)	C24—Sn1—C30—C31	68.8 (4)
C14—C8—C7—C6	179.0 (4)	C31—C30—C35—C34	52.7 (6)
O1—C7—C6—C5	177.5 (4)	Sn1—C30—C35—C34	179.1 (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—C32	178.9 (4)
C8—C7—C6—C10	178.0 (4)	O2—Sn1—C24—C29	−22.1 (5)
C9—C4—C5—C6	0.2 (6)	C18—Sn1—C24—C29	−145.9 (4)
C3—C4—C5—C6	−179.2 (4)	C30—Sn1—C24—C29	84.7 (4)
C7—C6—C5—C4	1.2 (6)	O2—Sn1—C24—C25	−152.3 (4)
C10—C6—C5—C4	−178.7 (4)	C18—Sn1—C24—C25	83.9 (4)
C5—C6—C10—C13	1.4 (6)	C30—Sn1—C24—C25	−45.5 (4)
C7—C6—C10—C13	−178.6 (4)	C29—C24—C25—C26	49.7 (7)
C5—C6—C10—C12	121.6 (4)	Sn1—C24—C25—C26	−178.3 (4)
C7—C6—C10—C12	−58.3 (5)	C30—C31—C32—C33	55.7 (7)
C5—C6—C10—C11	−118.3 (4)	C25—C24—C29—C28	−49.2 (7)
C7—C6—C10—C11	61.7 (5)	Sn1—C24—C29—C28	−178.5 (4)
C9—C8—C14—C16	112.1 (4)	C24—C29—C28—C27	50.5 (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—C25	51.1 (9)
C7—C8—C14—C17	174.8 (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—C15	56.7 (5)	C32—C33—C34—C35	54.8 (7)
O2—Sn1—C18—C23	−94.4 (3)	C30—C35—C34—C33	−53.6 (6)
C24—Sn1—C18—C23	28.9 (4)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₁₁)₃(C₁₇H₂₅O₃S)]
M_r	677.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.5048 (3), 11.4261 (3), 19.9794 (4)
β (°)	94.603 (2)
V (Å³)	3528.12 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.23 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.835, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	32619, 8086, 4695
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.117, 1.00
No. of reflections	8086
No. of parameters	368
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O2	2.081 (3)	Sn1—C24	2.157 (5)
Sn1—C18	2.148 (4)	Sn1—C30	2.166 (4)

Acknowledgements

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

References

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