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All three independent mol­ecules in the triclinic modification of (O-iso­propyl di­thio­carbonato-S)­tri­phenyl­tin, [Sn(C6H5)3(C4H7OS2)], show tetrahedral coordination at their Sn atoms. Bond dimensions involving the Sn atoms are similar to those found in the monoclinic modification of the same compound. Two of the independent mol­ecules are related by a pseudo-translation allowing a stacking fault that reduces the intensities of h + k odd reflections.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000457/qb0127sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000457/qb0127Isup2.hkl
Contains datablock I

CCDC reference: 142932

Comment top

The structure of the title compound, (I), has a 0.8395:0.1605 (3) stacking fault over alternative origins (a + b)/2 apart that causes the h + k = 2n + 1 reflections to be scaled down by a factor of 0.6791 (5). The structure consists of three different layers perpendicular to c*, each containing two molecles per unit cell. The first two layers are related by a crystallographic inversion whereas the third contains inversion-related molecules. The asymmetric unit is one layer at approximately z = 1/3 that contains molecule a and molecule b [related by a pseudo-translation of (a + b)/2] and a third molecule (molecule c) of a different orientation at approximately z = 0. A pseudo-inversion at (1/4,1/4,1/2) relates the layers at z = ±1/3, and if it acts on the total substructure on one side of an interface at z = 1/2, the net result is a translation of the structure by (a + b)/2. The structure factors are changed to [(1 − a) + a(−1)h+k]F(hkl)o, where F(hkl)o is the structure for the idealized non-stacking-faulted structure and a the average fraction of structure that has been stacking faulted. This effect can be modeled by simply using two scale constants.

Bond dimensions involving the Sn atom are not statistically different among the three molecules, and they are similar to those found in the monoclinic modification (Tiekink & Winter, 1986). For both modifications, the tetrahedral geometry at Sn is distorted owing to an intramolecular Sn···O interaction. The interaction is somewhat shorter than those found in the two independent molecules of triclinic (P1) triphenyltin methoxyethylxanthate (Edwards et al., 1988). This structure is ordered with the two molecules related by a pseudo-inversion at (0.127, 0.215, 0.253).

Experimental top

Triphenyltin xanthate, (I), synthesized from reaction between triphenyltin chloride and potassium isopropylxanthate in ethanol, was treated with an equimolar quantity of 2,2'-bipyridine N,N'-dioxide in an attempt to synthesize triphenyltin isopropylxanthate.2,2'-bipyridine N,N'-dioxide in a sequel to the study on the quinoline N-oxide complex (Ng et al., 1995). The reagents were dissolved in a small volume of hot ethanol; slow cooling of the solution returned the xanthate. Elemental analysis: found: C 54.50, H 4.55%; calculated for C22H22OS2Sn: C 54.46, H 4.57%. The starting triphenyltin isopropylxanthate reactant exists as the monoclinic modification when recrystallized from ethanol.

Refinement top

Two scale constants were used in the refinement to allow for a stacking fault over origins (a+b)/2 apart. Difference maps were calculated with the effects of a stacking fault removed by setting Fo = [Yo/Yc]1/2 × Fc, where Fc is the calculated structure factor for the prototype, and Yo and Yc are the observed and calculated values of the intensity. Because reflections are weak for h + k odd, constraints and restraints were used in a refinement that only behaved when two scale constants were used. The modeling for the least-squares refinement used refineable local orthonormal coordinates available in RAELS96 (Rae, 1975, 1996) to describe the atoms in the unit cell. All phenyl groups were restrained to have a common set of local coordinates and to maintain local mm2 symmetry. Restraints were used to minimize differences in bond lengths involving molecule a and molecule b. Twelve different 15-parameter TLX parameterizations (Rae, 1984) were used for the ligand thermal motions, one set per ligand, and librations were initially centered on the relevant Sn atoms. Because of the pseudo translation relationship between molecule a and molecule b, the TLX thermal parameterizations were constrained to retain this relationship (Rae, 1984). These constraints were later removed but reimposed when it was found that variations in TLX parameters were relatively large, had little effect on the statistics and were of no apparent physical meaning. Individual anisotropic displacement parameters were used for the Sn atoms. The stacking fault creates a Sn1c atom at (1/2 − x, 1/2 − y, −z) which lies near atoms C20c and C22c, distorting the apparent geometry in an unconstrained ligand. The distances and angles involving C20c were therefore restrained to minimize their differences from the corresponding features of molecules a and b with little apparent consequence for refinement statistics. In the final cycle, 271 independent variables were used, and the shift/error ratio was less than 0.1 for all but the libration parameters of one ligand. The refinement was stable, the shift/error ratio being an artifact of considering variables one at a time. There is a well recognized singularity in the equations for TLS motion for atoms on a conic section, which is retained should a TLX model of 6 phenyl C atoms have its center of action at the center of the ring. Hydrogen atoms were included in geometrically sensible positions which were updated each refinement cycle. The thermal parameters of H atoms were evaluated using the TLX parameters associated with the atoms to which they are attached. Quoted errors are conditional on the appropriateness of the various constraints and restraints. Refinement statistics are presented in Table 2.

Computing details top

Data collection: CAD-4-PC (Kretschmar, 1994); cell refinement: CAD-4-PC (Enraf-Nonius, 1988); data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: RAELS96 (Rae, 1996); software used to prepare material for publication: RAELS96 (Rae, 1996).

iso-Propylxanthatotriphenyltin top
Crystal data top
[Sn(C6H5)3(C4H7OS2)]Z = 6
Mr = 485.21F(000) = 1464
Triclinic, P1Dx = 1.466 Mg m3
a = 10.3136 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.124 (1) ÅCell parameters from 25 reflections
c = 27.139 (3) Åθ = 14.5–15.0°
α = 100.346 (9)°µ = 1.36 mm1
β = 93.422 (7)°T = 298 K
γ = 97.605 (7)°Cube, light yellow
V = 3297.0 (6) Å30.43 × 0.43 × 0.43 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
8184 reflections with I > 3σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
ω scansh = 012
Absorption correction: ψ scan
[North et al. (1968) in WinGX (Farrugia, 1997)]
k = 1414
Tmin = 0.515, Tmax = 0.557l = 3232
12299 measured reflections3 standard reflections every 60 min
11586 independent reflections intensity decay: 2%
Refinement top
Refinement on FPrimary 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) = 0.090Part of TLX rigid body motions
S = 1.45 w = 1/[σ(F)2 + (0.04F)2]
11586 reflections(Δ/σ)max = 0.3
271 parametersΔρmax = 1.31 e Å3
33 restraintsΔρmin = 0.83 e Å3
Crystal data top
[Sn(C6H5)3(C4H7OS2)]γ = 97.605 (7)°
Mr = 485.21V = 3297.0 (6) Å3
Triclinic, P1Z = 6
a = 10.3136 (3) ÅMo Kα radiation
b = 12.124 (1) ŵ = 1.36 mm1
c = 27.139 (3) ÅT = 298 K
α = 100.346 (9)°0.43 × 0.43 × 0.43 mm
β = 93.422 (7)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
8184 reflections with I > 3σ(I)
Absorption correction: ψ scan
[North et al. (1968) in WinGX (Farrugia, 1997)]
Rint = 0.013
Tmin = 0.515, Tmax = 0.5573 standard reflections every 60 min
12299 measured reflections intensity decay: 2%
11586 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05033 restraints
wR(F2) = 0.090Part of TLX rigid body motions
S = 1.45(Δ/σ)max = 0.3
11586 reflectionsΔρmax = 1.31 e Å3
271 parametersΔρmin = 0.83 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn1a0.05401 (5)0.04852 (4)0.32132 (2)0.0508 (2)
S1a0.2730 (2)0.0788 (2)0.3507 (1)0.063 (1)
S2a0.3982 (2)0.0743 (2)0.4241 (1)0.072 (1)
O1a0.1910 (4)0.1328 (3)0.3766 (2)0.058 (1)
C1a0.0483 (5)0.2180 (3)0.2821 (2)0.050 (2)
C2a0.0331 (6)0.3039 (4)0.3080 (2)0.060 (3)
C3a0.0338 (6)0.4142 (3)0.2822 (2)0.073 (3)
C4a0.0497 (7)0.4371 (4)0.2310 (2)0.082 (3)
C5a0.0649 (7)0.3532 (5)0.2047 (2)0.086 (2)
C6a0.0642 (6)0.2428 (4)0.2304 (2)0.068 (1)
C7a0.0791 (5)0.0049 (4)0.3870 (2)0.054 (3)
C8a0.1748 (6)0.0973 (5)0.3908 (2)0.073 (2)
C9a0.2605 (5)0.1331 (5)0.4340 (2)0.089 (3)
C10a0.2494 (6)0.0760 (6)0.4729 (2)0.090 (4)
C11a0.1553 (7)0.0157 (6)0.4699 (2)0.097 (4)
C12a0.0695 (6)0.0516 (4)0.4266 (2)0.076 (4)
C13a0.0365 (5)0.0674 (4)0.2707 (2)0.055 (3)
C14a0.0842 (5)0.1022 (5)0.2551 (2)0.069 (2)
C15a0.0976 (6)0.1821 (5)0.2241 (2)0.083 (2)
C16a0.0098 (7)0.2260 (5)0.2090 (2)0.090 (3)
C17a0.1303 (6)0.1925 (5)0.2240 (2)0.098 (4)
C18a0.1437 (5)0.1127 (5)0.2551 (2)0.076 (3)
C19a0.2847 (5)0.0554 (4)0.3861 (2)0.057 (1)
C20a0.1823 (8)0.2532 (5)0.4015 (3)0.072 (1)
C21a0.0796 (10)0.2759 (7)0.4441 (3)0.090 (1)
C22a0.1551 (9)0.3209 (6)0.3603 (3)0.079 (1)
Sn1b0.45148 (5)0.44430 (4)0.32264 (2)0.0483 (2)
S1b0.2352 (2)0.4106 (2)0.3539 (1)0.063 (1)
S2b0.1034 (2)0.5718 (2)0.4211 (1)0.070 (1)
O1b0.3103 (4)0.6236 (3)0.3722 (2)0.058 (1)
C1b0.4689 (5)0.2732 (3)0.2888 (2)0.050 (2)
C2b0.4556 (6)0.1868 (4)0.3157 (2)0.062 (3)
C3b0.4609 (6)0.0757 (3)0.2922 (2)0.075 (3)
C4b0.4793 (7)0.0525 (3)0.2423 (2)0.079 (3)
C5b0.4926 (7)0.1368 (5)0.2151 (2)0.082 (2)
C6b0.4874 (6)0.2480 (4)0.2385 (2)0.066 (2)
C7b0.5851 (5)0.5101 (4)0.3874 (2)0.054 (3)
C8b0.6803 (6)0.6023 (5)0.3898 (2)0.076 (2)
C9b0.7656 (5)0.6419 (5)0.4330 (3)0.093 (3)
C10b0.7544 (6)0.5889 (6)0.4731 (2)0.089 (3)
C11b0.6607 (7)0.4974 (6)0.4714 (2)0.092 (4)
C12b0.5754 (6)0.4577 (4)0.4283 (2)0.073 (4)
C13b0.4463 (5)0.5457 (4)0.2661 (2)0.057 (3)
C14b0.5548 (5)0.6150 (5)0.2564 (2)0.065 (2)
C15b0.5457 (6)0.6798 (5)0.2192 (2)0.079 (2)
C16b0.4284 (7)0.6745 (6)0.1923 (2)0.094 (4)
C17b0.3198 (6)0.6064 (6)0.2014 (2)0.107 (5)
C18b0.3287 (5)0.5415 (5)0.2386 (2)0.083 (4)
C19b0.2183 (5)0.5481 (4)0.3843 (2)0.056 (1)
C20b0.3153 (8)0.7452 (5)0.3943 (3)0.070 (1)
C21b0.4131 (9)0.7734 (7)0.4385 (3)0.087 (1)
C22b0.3480 (9)0.8076 (6)0.3517 (3)0.079 (1)
Sn1c0.27912 (5)0.12792 (4)0.04668 (2)0.0486 (2)
S1c0.0956 (2)0.2174 (2)0.0800 (1)0.060 (1)
S2c0.0248 (2)0.4436 (2)0.0801 (1)0.075 (1)
O1c0.2013 (5)0.3498 (4)0.0256 (2)0.056 (1)
C1c0.2293 (5)0.0301 (4)0.0702 (2)0.053 (3)
C2c0.2281 (6)0.0334 (4)0.1206 (2)0.071 (4)
C3c0.1892 (7)0.1350 (6)0.1363 (2)0.091 (6)
C4c0.1521 (6)0.2319 (4)0.1015 (3)0.087 (5)
C5c0.1527 (6)0.2304 (4)0.0514 (2)0.083 (4)
C6c0.1916 (6)0.1288 (4)0.0356 (2)0.069 (3)
C7c0.4572 (4)0.2256 (4)0.0836 (2)0.050 (2)
C8c0.4591 (5)0.3324 (4)0.1117 (2)0.060 (2)
C9c0.5771 (6)0.3959 (4)0.1342 (2)0.072 (2)
C10c0.6913 (5)0.3518 (5)0.1283 (2)0.079 (3)
C11c0.6914 (4)0.2462 (6)0.1006 (2)0.079 (4)
C12c0.5735 (5)0.1826 (4)0.0781 (2)0.063 (3)
C13c0.2829 (5)0.1067 (4)0.0330 (2)0.053 (3)
C14c0.1716 (5)0.0674 (5)0.0652 (2)0.066 (4)
C15c0.1779 (6)0.0534 (5)0.1170 (2)0.085 (5)
C16c0.2954 (7)0.0790 (6)0.1359 (2)0.088 (5)
C17c0.4068 (6)0.1180 (5)0.1046 (2)0.081 (4)
C18c0.4006 (5)0.1320 (5)0.0528 (2)0.065 (3)
C19c0.1150 (7)0.3474 (6)0.0599 (3)0.054 (1)
C20c0.2287 (8)0.4487 (6)0.0007 (3)0.080 (1)
C21c0.3368 (9)0.5290 (7)0.0322 (4)0.104 (2)
C22c0.2552 (13)0.3978 (9)0.0526 (3)0.111 (1)
H1C2a0.02150.28690.34550.072
H1C3a0.02270.47630.30110.091
H1C4a0.05010.51630.21250.100
H1C5a0.07640.37080.16710.117
H1C6a0.07540.18120.21120.082
H1C8a0.18280.13910.36220.097
H1C9a0.32980.20040.43660.123
H1C10a0.31090.10180.50390.111
H1C11a0.14790.05710.49850.138
H1C12a0.00040.11890.42430.100
H1C14a0.16290.06990.26620.089
H1C15a0.18550.20710.21290.107
H1C16a0.00020.28330.18670.113
H1C17a0.20850.22520.21270.139
H1C18a0.23200.08810.26610.096
H1C20a0.26860.26680.41460.077
H1C21a0.10590.22780.46920.096
H2C21a0.00550.25750.43130.090
H3C21a0.06910.35770.46040.110
H1C22a0.22920.30000.33330.076
H2C22a0.14630.40370.37470.096
H3C22a0.07170.30340.34570.082
H1C2b0.44210.20400.35230.075
H1C3b0.45120.01320.31190.097
H1C4b0.48310.02740.22550.096
H1C5b0.50610.11900.17850.109
H1C6b0.49720.31000.21860.081
H1C8b0.68840.64110.36030.102
H1C9b0.83460.70900.43450.129
H1C10b0.81570.61740.50410.110
H1C11b0.65330.45910.50100.129
H1C12b0.50670.39060.42700.095
H1C14b0.64080.61870.27620.081
H1C15b0.62480.73000.21230.098
H1C16b0.42190.72110.16560.118
H1C17b0.23410.60310.18150.154
H1C18b0.24920.49150.24530.106
H1C20b0.22710.75940.40510.075
H1C21b0.38370.72870.46440.092
H2C21b0.50000.75430.42790.087
H3C21b0.42170.85620.45290.106
H1C22b0.27700.78340.32360.077
H2C22b0.35510.89110.36430.096
H3C22b0.43350.78910.33930.082
H1C2c0.25530.03770.14610.095
H1C3c0.18840.13700.17300.132
H1C4c0.12420.30480.11280.114
H1C5c0.12530.30180.02610.116
H1C6c0.19210.12750.00110.094
H1C8c0.37520.36460.11600.078
H1C9c0.57800.47340.15460.097
H1C10c0.77600.39740.14440.104
H1C11c0.77570.21450.09650.112
H1C12c0.57340.10510.05780.081
H1C14c0.08550.04870.05120.077
H1C15c0.09680.02480.14020.111
H1C16c0.29990.06900.17310.113
H1C17c0.49250.13650.11890.103
H1C18c0.48220.16060.02980.076
H1C20c0.14840.48660.00060.084
H1C21c0.30700.55610.06600.101
H2C21c0.41510.48960.03600.113
H3C21c0.36090.59520.01550.134
H1C22c0.17540.34580.06960.111
H2C22c0.27670.45990.07180.147
H3C22c0.33080.35430.05140.115
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn1a0.0499 (3)0.0448 (3)0.0560 (3)0.0070 (2)0.0018 (3)0.0059 (2)
S1a0.055 (1)0.044 (1)0.088 (1)0.000 (1)0.014 (1)0.009 (1)
S2a0.068 (1)0.075 (1)0.071 (1)0.002 (1)0.026 (1)0.010 (1)
O1a0.053 (1)0.046 (1)0.073 (1)0.003 (1)0.013 (1)0.006 (1)
C1a0.045 (3)0.052 (2)0.051 (3)0.004 (2)0.002 (2)0.009 (1)
C2a0.063 (4)0.054 (2)0.063 (4)0.010 (2)0.002 (3)0.014 (2)
C3a0.079 (5)0.054 (2)0.085 (4)0.013 (2)0.001 (4)0.010 (2)
C4a0.089 (4)0.062 (2)0.086 (3)0.018 (2)0.010 (3)0.006 (2)
C5a0.113 (5)0.076 (2)0.064 (2)0.032 (3)0.009 (2)0.007 (2)
C6a0.085 (3)0.067 (2)0.051 (2)0.020 (2)0.001 (2)0.005 (1)
C7a0.052 (3)0.050 (4)0.059 (3)0.012 (3)0.005 (2)0.008 (2)
C8a0.063 (3)0.071 (4)0.077 (2)0.007 (3)0.002 (2)0.008 (3)
C9a0.071 (3)0.094 (5)0.089 (3)0.004 (3)0.012 (2)0.003 (3)
C10a0.082 (4)0.102 (5)0.078 (3)0.020 (4)0.019 (3)0.004 (3)
C11a0.110 (6)0.104 (6)0.073 (3)0.012 (5)0.023 (3)0.020 (4)
C12a0.088 (4)0.075 (5)0.065 (2)0.006 (3)0.009 (2)0.022 (3)
C13a0.055 (5)0.054 (4)0.059 (3)0.012 (2)0.005 (2)0.011 (3)
C14a0.063 (4)0.077 (3)0.072 (2)0.009 (2)0.013 (2)0.022 (2)
C15a0.092 (4)0.081 (3)0.077 (3)0.000 (3)0.017 (3)0.026 (2)
C16a0.123 (5)0.078 (6)0.081 (4)0.022 (3)0.021 (3)0.034 (4)
C17a0.109 (4)0.112 (9)0.097 (5)0.048 (4)0.020 (3)0.056 (6)
C18a0.069 (5)0.092 (7)0.079 (4)0.029 (2)0.008 (2)0.037 (4)
C19a0.054 (1)0.049 (1)0.067 (1)0.002 (1)0.016 (1)0.008 (1)
C20a0.066 (1)0.048 (1)0.091 (1)0.004 (1)0.006 (1)0.002 (1)
C21a0.086 (2)0.066 (2)0.102 (2)0.010 (2)0.010 (1)0.007 (2)
C22a0.063 (1)0.048 (1)0.122 (2)0.008 (1)0.005 (1)0.018 (1)
Sn1b0.0470 (3)0.0443 (3)0.0544 (3)0.0058 (2)0.0040 (2)0.0115 (2)
S1b0.055 (1)0.044 (1)0.088 (1)0.000 (1)0.014 (1)0.009 (1)
S2b0.066 (1)0.071 (1)0.072 (1)0.003 (1)0.026 (1)0.008 (1)
O1b0.052 (1)0.045 (1)0.073 (1)0.003 (1)0.014 (1)0.007 (1)
C1b0.045 (3)0.052 (2)0.052 (3)0.004 (2)0.002 (2)0.010 (1)
C2b0.068 (4)0.054 (2)0.065 (4)0.010 (2)0.001 (4)0.016 (2)
C3b0.084 (6)0.054 (2)0.088 (5)0.013 (2)0.002 (5)0.014 (2)
C4b0.085 (4)0.060 (2)0.086 (4)0.018 (2)0.006 (3)0.002 (2)
C5b0.103 (4)0.074 (2)0.067 (2)0.029 (2)0.003 (2)0.001 (2)
C6b0.078 (3)0.066 (2)0.056 (2)0.018 (2)0.008 (2)0.008 (1)
C7b0.051 (3)0.050 (4)0.060 (3)0.011 (3)0.005 (2)0.007 (2)
C8b0.068 (3)0.071 (3)0.080 (2)0.011 (3)0.004 (2)0.010 (3)
C9b0.077 (3)0.093 (5)0.092 (3)0.010 (3)0.014 (2)0.001 (3)
C10b0.079 (3)0.100 (5)0.079 (3)0.017 (3)0.017 (2)0.006 (3)
C11b0.100 (5)0.103 (5)0.069 (3)0.013 (4)0.017 (3)0.015 (3)
C12b0.080 (4)0.074 (5)0.062 (2)0.007 (3)0.005 (2)0.018 (3)
C13b0.056 (5)0.056 (4)0.059 (3)0.011 (2)0.004 (2)0.011 (3)
C14b0.066 (4)0.065 (3)0.066 (2)0.007 (2)0.010 (2)0.016 (2)
C15b0.098 (4)0.071 (4)0.072 (3)0.008 (2)0.016 (2)0.023 (2)
C16b0.111 (6)0.103 (8)0.083 (4)0.027 (4)0.011 (3)0.045 (5)
C17b0.090 (7)0.153 (12)0.094 (5)0.021 (4)0.006 (3)0.065 (7)
C18b0.066 (7)0.112 (8)0.076 (4)0.006 (3)0.008 (3)0.038 (4)
C19b0.053 (1)0.047 (1)0.067 (1)0.002 (1)0.016 (1)0.007 (1)
C20b0.064 (1)0.046 (1)0.093 (1)0.004 (1)0.007 (1)0.001 (1)
C21b0.082 (2)0.061 (1)0.103 (2)0.009 (1)0.007 (1)0.006 (1)
C22b0.061 (1)0.050 (1)0.123 (2)0.008 (1)0.006 (1)0.023 (1)
Sn1c0.0511 (3)0.0454 (3)0.0499 (3)0.0052 (2)0.0090 (2)0.0106 (2)
S1c0.061 (2)0.062 (1)0.065 (2)0.015 (1)0.025 (1)0.023 (1)
S2c0.071 (2)0.064 (1)0.095 (2)0.025 (1)0.026 (1)0.013 (1)
O1c0.051 (2)0.054 (1)0.069 (2)0.010 (1)0.017 (1)0.021 (1)
C1c0.046 (5)0.044 (3)0.070 (5)0.008 (2)0.001 (4)0.010 (3)
C2c0.085 (6)0.057 (3)0.071 (7)0.010 (3)0.000 (4)0.015 (3)
C3c0.112 (11)0.075 (4)0.093 (8)0.011 (5)0.009 (6)0.037 (4)
C4c0.080 (8)0.060 (2)0.126 (8)0.002 (3)0.002 (5)0.040 (4)
C5c0.085 (6)0.044 (2)0.115 (6)0.002 (2)0.017 (5)0.014 (3)
C6c0.077 (5)0.046 (2)0.079 (4)0.009 (2)0.006 (4)0.005 (3)
C7c0.056 (4)0.051 (3)0.046 (3)0.004 (2)0.004 (2)0.016 (2)
C8c0.074 (3)0.057 (3)0.050 (3)0.011 (2)0.001 (2)0.011 (2)
C9c0.097 (4)0.058 (3)0.057 (3)0.006 (3)0.013 (3)0.015 (2)
C10c0.072 (3)0.093 (6)0.065 (4)0.018 (3)0.012 (3)0.029 (3)
C11c0.058 (3)0.112 (7)0.070 (5)0.013 (4)0.002 (2)0.022 (4)
C12c0.065 (3)0.070 (4)0.057 (3)0.018 (4)0.000 (2)0.014 (2)
C13c0.059 (5)0.047 (4)0.057 (3)0.011 (3)0.012 (2)0.013 (2)
C14c0.068 (5)0.065 (6)0.062 (3)0.009 (3)0.005 (2)0.007 (3)
C15c0.099 (6)0.092 (9)0.060 (3)0.019 (4)0.000 (3)0.004 (3)
C16c0.120 (7)0.091 (7)0.058 (3)0.027 (5)0.021 (3)0.013 (2)
C17c0.097 (6)0.081 (5)0.071 (3)0.019 (4)0.035 (3)0.017 (3)
C18c0.066 (5)0.063 (4)0.068 (3)0.013 (2)0.021 (2)0.014 (2)
C19c0.050 (2)0.053 (1)0.063 (2)0.012 (1)0.014 (1)0.014 (1)
C20c0.081 (2)0.067 (1)0.109 (3)0.016 (1)0.035 (2)0.044 (2)
C21c0.075 (3)0.062 (1)0.183 (6)0.002 (1)0.033 (3)0.044 (2)
C22c0.145 (5)0.108 (3)0.110 (3)0.043 (3)0.067 (3)0.068 (3)
H1C2a0.0960.0630.0630.0240.0010.020
H1C3a0.1150.0580.1060.0240.0060.020
H1C4a0.1150.0670.1070.0260.0150.015
H1C5a0.1820.1020.0650.0620.0140.016
H1C6a0.1250.0810.0470.0360.0070.011
H1C8a0.0930.0910.0930.0390.0110.025
H1C9a0.0970.1270.1160.0370.0250.002
H1C10a0.0990.1310.0890.0250.0320.011
H1C11a0.1740.1480.0860.0070.0450.046
H1C12a0.1260.0940.0770.0200.0200.044
H1C14a0.0590.1260.0970.0210.0230.049
H1C15a0.1020.1240.0980.0130.0230.046
H1C16a0.1680.0910.0960.0300.0310.048
H1C17a0.1380.1870.1410.0890.0360.107
H1C18a0.0630.1440.1030.0380.0090.065
H1C20a0.0750.0530.0920.0020.0120.011
H1C21a0.0980.0850.0860.0090.0090.007
H2C21a0.0750.0650.1170.0140.0140.008
H3C21a0.1070.0710.1260.0110.0180.020
H1C22a0.0600.0510.1160.0060.0090.025
H2C22a0.0760.0460.1590.0100.0040.015
H3C22a0.0590.0580.1280.0110.0080.031
H1C2b0.1040.0630.0670.0230.0100.026
H1C3b0.1260.0570.1140.0230.0160.026
H1C4b0.1090.0650.1070.0250.0100.009
H1C5b0.1640.0970.0690.0550.0140.004
H1C6b0.1150.0780.0580.0310.0270.017
H1C8b0.1010.0940.0970.0450.0140.029
H1C9b0.1080.1280.1230.0460.0300.006
H1C10b0.0950.1280.0890.0210.0290.014
H1C11b0.1560.1480.0780.0040.0360.038
H1C12b0.1150.0950.0710.0170.0140.039
H1C14b0.0610.1010.0820.0030.0080.033
H1C15b0.1210.0890.0850.0090.0210.032
H1C16b0.1460.1310.0980.0380.0170.066
H1C17b0.1020.2540.1300.0210.0200.117
H1C18b0.0660.1610.0920.0120.0200.058
H1C20b0.0710.0490.0950.0020.0130.007
H1C21b0.0940.0780.0870.0070.0060.009
H2C21b0.0720.0610.1160.0140.0110.008
H3C21b0.1020.0640.1300.0100.0150.019
H1C22b0.0610.0560.1160.0060.0100.030
H2C22b0.0730.0480.1610.0100.0020.024
H3C22b0.0590.0620.1280.0110.0110.035
H1C2c0.1440.0680.0700.0130.0070.008
H1C3c0.2000.1100.0990.0180.0210.054
H1C4c0.1070.0730.1710.0030.0030.063
H1C5c0.1430.0460.1450.0010.0370.005
H1C6c0.1400.0590.0760.0150.0060.001
H1C8c0.0920.0830.0610.0340.0010.002
H1C9c0.1500.0590.0710.0020.0290.008
H1C10c0.0870.1310.0830.0390.0250.041
H1C11c0.0650.1780.0960.0370.0030.022
H1C12c0.0960.0800.0700.0400.0060.006
H1C14c0.0640.0820.0770.0010.0030.002
H1C15c0.1160.1340.0700.0200.0150.006
H1C16c0.1630.1220.0590.0380.0270.015
H1C17c0.1140.1100.0920.0170.0570.021
H1C18c0.0600.0860.0840.0100.0210.012
H1C20c0.0890.0680.1090.0220.0250.045
H1C21c0.0750.0530.1710.0000.0060.018
H2C21c0.0650.0680.2110.0020.0340.044
H3C21c0.1010.0730.2460.0040.0570.071
H1C22c0.1660.1170.0760.0520.0410.053
H2C22c0.1990.1370.1520.0590.0980.102
H3C22c0.1380.1120.1280.0420.0870.069
Geometric parameters (Å, º) top
Sn1a—S1a2.443 (1)C8b—C9b1.393 (3)
Sn1a—C1a2.148 (3)C9b—C10b1.363 (3)
Sn1a—C7a2.131 (3)C10b—C11b1.363 (3)
Sn1a—C13a2.134 (3)C11b—C12b1.393 (3)
S1a—C19a1.758 (5)C13b—C14b1.376 (2)
S2a—C19a1.617 (5)C13b—C18b1.376 (2)
O1a—C19a1.326 (6)C14b—C15b1.393 (3)
O1a—C20a1.484 (6)C15b—C16b1.363 (3)
C1a—C2a1.376 (2)C16b—C17b1.363 (3)
C1a—C6a1.376 (2)C17b—C18b1.393 (3)
C2a—C3a1.393 (3)C20b—C21b1.480 (9)
C3a—C4a1.363 (3)C20b—C22b1.520 (9)
C4a—C5a1.363 (3)Sn1c—S1c2.444 (2)
C5a—C6a1.393 (3)Sn1c—C1c2.136 (4)
C7a—C8a1.376 (2)Sn1c—C7c2.135 (4)
C7a—C12a1.376 (2)Sn1c—C13c2.135 (4)
C8a—C9a1.393 (3)S1c—C19c1.750 (7)
C9a—C10a1.363 (3)S2c—C19c1.626 (7)
C10a—C11a1.363 (3)O1c—C19c1.326 (7)
C11a—C12a1.393 (3)O1c—C20c1.483 (6)
C13a—C14a1.376 (2)C1c—C2c1.376 (2)
C13a—C18a1.376 (2)C1c—C6c1.376 (2)
C14a—C15a1.393 (3)C2c—C3c1.393 (3)
C15a—C16a1.363 (3)C3c—C4c1.363 (3)
C16a—C17a1.363 (3)C4c—C5c1.363 (3)
C17a—C18a1.393 (3)C5c—C6c1.393 (3)
C20a—C21a1.481 (9)C7c—C8c1.376 (2)
C20a—C22a1.520 (9)C7c—C12c1.376 (2)
Sn1b—S1b2.444 (1)C8c—C9c1.393 (3)
Sn1b—C1b2.148 (3)C9c—C10c1.363 (3)
Sn1b—C7b2.131 (3)C10c—C11c1.363 (3)
Sn1b—C13b2.133 (3)C11c—C12c1.393 (3)
S1b—C19b1.757 (5)C13c—C14c1.376 (2)
S2b—C19b1.616 (5)C13c—C18c1.376 (2)
O1b—C19b1.328 (6)C14c—C15c1.393 (3)
O1b—C20b1.482 (6)C15c—C16c1.363 (3)
C1b—C2b1.376 (2)C16c—C17c1.363 (3)
C1b—C6b1.376 (2)C17c—C18c1.393 (3)
C2b—C3b1.393 (3)C20c—C21c1.490 (9)
C3b—C4b1.363 (3)C20c—C22c1.523 (9)
C4b—C5b1.363 (3)Sn1a—O1a2.995 (4)
C5b—C6b1.393 (3)Sn1b—O1b2.945 (4)
C7b—C8b1.376 (2)Sn1c—O1c3.045 (4)
C7b—C12b1.376 (2)
S1a—Sn1a—C1a98.3 (2)C7b—C8b—C9b120.5 (2)
S1a—Sn1a—C7a106.3 (2)C8b—C9b—C10b119.6 (2)
S1a—Sn1a—C13a113.5 (2)C9b—C10b—C11b120.8 (3)
C1a—Sn1a—C7a114.8 (2)C10b—C11b—C12b119.6 (2)
C1a—Sn1a—C13a110.4 (2)C7b—C12b—C11b120.5 (2)
C7a—Sn1a—C13a112.8 (2)Sn1b—C13b—C14b122.9 (3)
Sn1a—S1a—C19a101.9 (2)Sn1b—C13b—C18b118.1 (3)
C19a—O1a—C20a120.5 (5)C14b—C13b—C18b119.0 (2)
Sn1a—C1a—C2a120.9 (3)C13b—C14b—C15b120.5 (2)
Sn1a—C1a—C6a120.0 (3)C14b—C15b—C16b119.6 (2)
C2a—C1a—C6a119.0 (2)C15b—C16b—C17b120.8 (3)
C1a—C2a—C3a120.5 (2)C16b—C17b—C18b119.6 (2)
C2a—C3a—C4a119.6 (2)C13b—C18b—C17b120.5 (2)
C3a—C4a—C5a120.8 (3)S1b—C19b—S2b122.0 (3)
C4a—C5a—C6a119.6 (2)S1b—C19b—O1b110.4 (4)
C1a—C6a—C5a120.5 (2)S2b—C19b—O1b127.6 (4)
Sn1a—C7a—C8a120.5 (3)O1b—C20b—C21b108.1 (6)
Sn1a—C7a—C12a120.5 (3)O1b—C20b—C22b105.0 (5)
C8a—C7a—C12a119.0 (2)C21b—C20b—C22b115.0 (6)
C7a—C8a—C9a120.5 (2)S1c—Sn1c—C1c97.2 (2)
C8a—C9a—C10a119.6 (2)S1c—Sn1c—C7c108.1 (1)
C9a—C10a—C11a120.8 (3)S1c—Sn1c—C13c114.5 (1)
C10a—C11a—C12a119.6 (2)C1c—Sn1c—C7c114.0 (2)
C7a—C12a—C11a120.5 (2)C1c—Sn1c—C13c111.9 (2)
Sn1a—C13a—C14a120.1 (3)C7c—Sn1c—C13c110.6 (2)
Sn1a—C13a—C18a120.8 (3)Sn1c—S1c—C19c103.3 (2)
C14a—C13a—C18a119.0 (2)C19c—O1c—C20c121.5 (5)
C13a—C14a—C15a120.5 (2)Sn1c—C1c—C2c120.0 (3)
C14a—C15a—C16a119.6 (2)Sn1c—C1c—C6c121.0 (3)
C15a—C16a—C17a120.8 (3)C2c—C1c—C6c119.0 (2)
C16a—C17a—C18a119.6 (2)C1c—C2c—C3c120.5 (2)
C13a—C18a—C17a120.5 (2)C2c—C3c—C4c119.6 (2)
S1a—C19a—S2a121.7 (3)C3c—C4c—C5c120.8 (3)
S1a—C19a—O1a110.7 (4)C4c—C5c—C6c119.6 (2)
S2a—C19a—O1a127.6 (4)C1c—C6c—C5c120.5 (2)
O1a—C20a—C21a108.2 (6)Sn1c—C7c—C8c121.5 (3)
O1a—C20a—C22a105.1 (5)Sn1c—C7c—C12c119.4 (3)
C21a—C20a—C22a115.2 (6)C8c—C7c—C12c119.0 (2)
S1b—Sn1b—C1b99.0 (1)C7c—C8c—C9c120.5 (2)
S1b—Sn1b—C7b105.9 (2)C8c—C9c—C10c119.6 (2)
S1b—Sn1b—C13b110.5 (2)C9c—C10c—C11c120.8 (3)
C1b—Sn1b—C7b113.4 (2)C10c—C11c—C12c119.6 (2)
C1b—Sn1b—C13b109.8 (2)C7c—C12c—C11c120.5 (2)
C7b—Sn1b—C13b116.7 (2)Sn1c—C13c—C14c122.0 (3)
Sn1b—S1b—C19b100.9 (2)Sn1c—C13c—C18c119.0 (3)
C19b—O1b—C20b119.4 (5)C14c—C13c—C18c119.0 (2)
Sn1b—C1b—C2b121.6 (3)C13c—C14c—C15c120.5 (2)
Sn1b—C1b—C6b119.3 (3)C14c—C15c—C16c119.6 (2)
C2b—C1b—C6b119.0 (2)C15c—C16c—C17c120.8 (3)
C1b—C2b—C3b120.5 (2)C16c—C17c—C18c119.6 (2)
C2b—C3b—C4b119.6 (2)C13c—C18c—C17c120.5 (2)
C3b—C4b—C5b120.8 (3)S1c—C19c—S2c120.3 (4)
C4b—C5b—C6b119.6 (2)S1c—C19c—O1c111.5 (5)
C1b—C6b—C5b120.5 (2)S2c—C19c—O1c128.1 (5)
Sn1b—C7b—C8b122.6 (3)O1c—C20c—C21c107.3 (6)
Sn1b—C7b—C12b118.4 (3)O1c—C20c—C22c104.5 (5)
C8b—C7b—C12b119.0 (2)C21c—C20c—C22c117.4 (7)
C19a—S1a—Sn1a—C1a177.5 (2)C8b—C7b—Sn1b—C13b11.3 (4)
C19a—S1a—Sn1a—C7a58.6 (2)C12b—C7b—Sn1b—C13b168.8 (3)
C19a—S1a—Sn1a—C13a65.9 (2)C14b—C13b—Sn1b—S1b152.9 (3)
C2a—C1a—Sn1a—S1a73.4 (3)C18b—C13b—Sn1b—S1b26.8 (3)
C2a—C1a—Sn1a—C7a38.9 (4)C14b—C13b—Sn1b—C1b99.0 (4)
C2a—C1a—Sn1a—C13a167.7 (3)C18b—C13b—Sn1b—C1b81.3 (3)
C6a—C1a—Sn1a—S1a104.5 (3)C14b—C13b—Sn1b—C7b31.9 (4)
C6a—C1a—Sn1a—C7a143.2 (3)C18b—C13b—Sn1b—C7b147.8 (3)
C6a—C1a—Sn1a—C13a14.4 (4)S2b—C19b—S1b—Sn1b168.2 (2)
C8a—C7a—Sn1a—S1a132.6 (3)S1b—C19b—O1b—C20b180.8 (5)
C12a—C7a—Sn1a—S1a46.4 (3)S2b—C19b—O1b—C20b1.2 (6)
C8a—C7a—Sn1a—C1a119.9 (3)C21b—C20b—O1b—C19b96.5 (7)
C12a—C7a—Sn1a—C1a61.1 (4)C22b—C20b—O1b—C19b140.3 (5)
C8a—C7a—Sn1a—C13a7.7 (4)C19c—S1c—Sn1c—C1c176.1 (3)
C12a—C7a—Sn1a—C13a171.3 (3)C19c—S1c—Sn1c—C7c65.7 (3)
C14a—C13a—Sn1a—S1a173.1 (3)C19c—S1c—Sn1c—C13c58.1 (3)
C18a—C13a—Sn1a—S1a3.7 (4)C2c—C1c—Sn1c—S1c63.0 (3)
C14a—C13a—Sn1a—C1a77.7 (4)C6c—C1c—Sn1c—S1c113.6 (3)
C18a—C13a—Sn1a—C1a105.6 (3)C2c—C1c—Sn1c—C7c50.6 (4)
C14a—C13a—Sn1a—C7a52.2 (4)C6c—C1c—Sn1c—C7c132.9 (3)
C18a—C13a—Sn1a—C7a124.6 (3)C2c—C1c—Sn1c—C13c177.0 (3)
S2a—C19a—S1a—Sn1a166.1 (2)C6c—C1c—Sn1c—C13c6.4 (4)
S1a—C19a—O1a—C20a179.0 (5)C8c—C7c—Sn1c—S1c13.3 (3)
S2a—C19a—O1a—C20a0.7 (6)C12c—C7c—Sn1c—S1c168.7 (2)
C21a—C20a—O1a—C19a99.8 (7)C8c—C7c—Sn1c—C1c120.1 (3)
C22a—C20a—O1a—C19a136.7 (5)C12c—C7c—Sn1c—C1c61.8 (3)
C19b—S1b—Sn1b—C1b177.8 (2)C8c—C7c—Sn1c—C13c112.8 (3)
C19b—S1b—Sn1b—C7b60.2 (2)C12c—C7c—Sn1c—C13c65.2 (3)
C19b—S1b—Sn1b—C13b67.0 (2)C14c—C13c—Sn1c—S1c44.2 (3)
C2b—C1b—Sn1b—S1b54.9 (3)C18c—C13c—Sn1c—S1c136.5 (3)
C6b—C1b—Sn1b—S1b121.9 (3)C14c—C13c—Sn1c—C1c65.1 (4)
C2b—C1b—Sn1b—C7b56.8 (4)C18c—C13c—Sn1c—C1c114.2 (3)
C6b—C1b—Sn1b—C7b126.4 (3)C14c—C13c—Sn1c—C7c166.6 (3)
C2b—C1b—Sn1b—C13b170.6 (3)C18c—C13c—Sn1c—C7c14.1 (3)
C6b—C1b—Sn1b—C13b6.2 (4)S2c—C19c—S1c—Sn1c171.6 (4)
C8b—C7b—Sn1b—S1b134.8 (3)S1c—C19c—O1c—C20c176.4 (5)
C12b—C7b—Sn1b—S1b45.4 (3)S2c—C19c—O1c—C20c1.0 (10)
C8b—C7b—Sn1b—C1b117.8 (3)C21c—C20c—O1c—C19c89.2 (8)
C12b—C7b—Sn1b—C1b62.1 (4)C22c—C20c—O1c—C19c145.4 (8)

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C4H7OS2)]
Mr485.21
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.3136 (3), 12.124 (1), 27.139 (3)
α, β, γ (°)100.346 (9), 93.422 (7), 97.605 (7)
V3)3297.0 (6)
Z6
Radiation typeMo Kα
µ (mm1)1.36
Crystal size (mm)0.43 × 0.43 × 0.43
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
[North et al. (1968) in WinGX (Farrugia, 1997)]
Tmin, Tmax0.515, 0.557
No. of measured, independent and
observed [I > 3σ(I)] reflections
12299, 11586, 8184
Rint0.013
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.090, 1.45
No. of reflections11586
No. of parameters271
No. of restraints33
H-atom treatmentPart of TLX rigid body motions
(Δ/σ)max0.3
Δρmax, Δρmin (e Å3)1.31, 0.83

Computer programs: CAD-4-PC (Kretschmar, 1994), CAD-4-PC (Enraf-Nonius, 1988), XCAD4 (Harms, 1997), SHELXS97 (Sheldrick, 1997), RAELS96 (Rae, 1996).

Selected geometric parameters (Å, º) top
Sn1a—S1a2.443 (1)Sn1b—C7b2.131 (3)
Sn1a—C1a2.148 (3)Sn1b—C13b2.133 (3)
Sn1a—C7a2.131 (3)Sn1c—S1c2.444 (2)
Sn1a—C13a2.134 (3)Sn1c—C1c2.136 (4)
Sn1b—S1b2.444 (1)Sn1c—C7c2.135 (4)
Sn1b—C1b2.148 (3)Sn1c—C13c2.135 (4)
S1a—Sn1a—C1a98.3 (2)C1b—Sn1b—C13b109.8 (2)
S1a—Sn1a—C7a106.3 (2)C7b—Sn1b—C13b116.7 (2)
S1a—Sn1a—C13a113.5 (2)S1c—Sn1c—C1c97.2 (2)
C1a—Sn1a—C7a114.8 (2)S1c—Sn1c—C7c108.1 (1)
C1a—Sn1a—C13a110.4 (2)S1c—Sn1c—C13c114.5 (1)
C7a—Sn1a—C13a112.8 (2)C1c—Sn1c—C7c114.0 (2)
S1b—Sn1b—C7b105.9 (2)C1c—Sn1c—C13c111.9 (2)
S1b—Sn1b—C13b110.5 (2)C7c—Sn1c—C13c110.6 (2)
C1b—Sn1b—C7b113.4 (2)
Refinement statistics top
ClassaNumberR(F)R(F2)wRGoF<|F2|>b
147410.0400.0880.0561.181000
229270.0880.1380.1101.82145
1 and 276680.0500.0930.0751.46676
339180.6740.9840.4531.287
Notes: an uncorrelated 4% error in |F(h)| was included along with counting statistics for evaluating weights. (a) Class 1: reflections with h + k = 2n and I(h) > 3σ[I(h)]; class 2: reflections with h + k = 2n + 1 and I(h) > 3σ[I(h)]; class 3: reflections with I(h) < 3σ[I(h)]. (b) Scaled relative to 1000 for class 1.
 

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