supporting information


Acta Cryst. (2013). E69, m316    [ doi:10.1107/S1600536813012300 ]

(O-Methyl di­thio­carbonato-[kappa]S)tri­phenyl­tin(IV)

F. Javed, S. Ali, W. Shah, M. N. Tahir and H. Ullah

Abstract top

In the title compound, [Sn(C6H5)3(C2H3OS2)], the SnIV atom adopts a distorted SnC3S tetra­hedral coordination geometry. A short Sn...O contact [2.988 (4) Å] is also present. The phenyl rings are each disordered over two sets of sites with an occupancy ratio of 0.550 (8):0.450 (8). The crystal studied was found to be a racemic twin with a twin component ratio of 0.57 (18):0.43 (18).

Comment top

The crystal structure of (O-methyl dithiocarbonato-S)-triphenyl-tin(iv) (Ng & Rae, 2000) has been reported, which is related to title compound (I).

In (I) the coordination around tin atom is distorted tetrahedral with three C-atoms and an S-atom. The tin and coordinated sulpher atom is at a distance of -0.5497 (47) Å and -2.9805 (53) Å from the plane (C3A/C9A/C15A). The phenyl rings are disordered over two sites with occupancy ratio of 0.550 (8):0.450 (8). The dihedral angle between disordered rings (C3A–C8A)/(C3B–C8B), (C9A–C14A)/(C9B–C14B) and (C15A–C20A)/(C15B–C20B) is 19.2 (7)°, 8.3 (10)° and 14.1 (5)°, respectively. The O-methyl hydrogen carbonodithioate moiety (S1/C1/S2/O1/C2) is planar with r. m. s. deviation of 0.0326 Å and is oriented at a dihedral angle of 71.22 (19)° with the plane (C3A/C9A/C15A).

Related literature top

For a related structure, see: Ng & Rae (2000).

Experimental top

Potassium-O-methyl carrbonodithioate (10 mmol, 1.46 g) was dissolved in methanol and stirred for 30 min. Then triphenytin(IV) chloride was added dropwise and the reaction mixture was stirred for 7–8 h till white precipitates were appeared. The resultant mixture was filtered to remove KCl salt. The filtrate was rotary evaporated to get white solid mass and recrystalized from chloroform to obtaine colourless prisms of (I) in 85.33% yield.

Refinement top

There is a recamic twin with BASF value of 0.43147.

The benzene rings of triphenyl tin are disordered over two sites with occupancy ratio of 0.550 (8):0.450 (8) and were idealized as regular hexagons with C–C bond distance equal to 1.39 Å. The C-atoms of respective rings were treated as anisotropic with equal thermal parameters.

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.

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: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. Only the major part of atoms of disordered group are shown for clarity.
(O-Methyl dithiocarbonato-κS)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C2H3OS2)]F(000) = 912
Mr = 457.15Dx = 1.515 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3341 reflections
a = 17.4400 (9) Åθ = 2.8–26.0°
b = 8.4734 (4) ŵ = 1.49 mm1
c = 15.6069 (9) ÅT = 296 K
β = 119.626 (2)°Prism, white
V = 2004.82 (19) Å30.28 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3483 independent reflections
Radiation source: fine-focus sealed tube3341 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 8.00 pixels mm-1θmax = 26.0°, θmin = 2.8°
ω scansh = 2120
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1010
Tmin = 0.683, Tmax = 0.763l = 1919
7166 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.055 w = 1/[σ2(Fo2) + (0.0246P)2 + 2.1104P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3483 reflectionsΔρmax = 0.44 e Å3
112 parametersΔρmin = 0.29 e Å3
2 restraintsAbsolute structure: Flack (1983), 1387 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.43 (18)
Crystal data top
[Sn(C6H5)3(C2H3OS2)]V = 2004.82 (19) Å3
Mr = 457.15Z = 4
Monoclinic, CcMo Kα radiation
a = 17.4400 (9) ŵ = 1.49 mm1
b = 8.4734 (4) ÅT = 296 K
c = 15.6069 (9) Å0.28 × 0.22 × 0.18 mm
β = 119.626 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3483 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3341 reflections with I > 2σ(I)
Tmin = 0.683, Tmax = 0.763Rint = 0.014
7166 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.055Δρmax = 0.44 e Å3
S = 1.04Δρmin = 0.29 e Å3
3483 reflectionsAbsolute structure: Flack (1983), 1387 Friedel pairs
112 parametersAbsolute structure parameter: 0.43 (18)
2 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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*/UeqOcc. (<1)
Sn10.01045 (1)0.18518 (2)0.25080 (1)0.0459 (1)
S10.10922 (8)0.30516 (13)0.10239 (9)0.0611 (4)
S20.11228 (15)0.6208 (2)0.02348 (15)0.1128 (7)
O10.0289 (2)0.4577 (4)0.1408 (3)0.0687 (11)
C10.0567 (3)0.4711 (5)0.0901 (3)0.0581 (14)
C20.0828 (4)0.5909 (7)0.1467 (5)0.106 (3)
C3A0.0722 (5)0.3677 (6)0.3576 (5)0.0589 (8)0.550 (8)
C4A0.1594 (5)0.3461 (6)0.4305 (5)0.0589 (8)0.550 (8)
C5A0.2039 (4)0.4656 (8)0.4982 (5)0.0589 (8)0.550 (8)
C6A0.1611 (4)0.6067 (6)0.4930 (4)0.0589 (8)0.550 (8)
C7A0.0738 (4)0.6283 (6)0.4200 (5)0.0589 (8)0.550 (8)
C8A0.0294 (4)0.5088 (8)0.3523 (5)0.0589 (8)0.550 (8)
C9A0.0659 (5)0.0278 (10)0.2859 (7)0.0590 (9)0.550 (8)
C10A0.0786 (6)0.0702 (8)0.3640 (6)0.0590 (9)0.550 (8)
C11A0.1305 (5)0.0234 (8)0.3883 (5)0.0590 (9)0.550 (8)
C12A0.1697 (4)0.1594 (7)0.3345 (5)0.0590 (9)0.550 (8)
C13A0.1570 (4)0.2018 (7)0.2564 (5)0.0590 (9)0.550 (8)
C14A0.1051 (5)0.1081 (10)0.2320 (6)0.0590 (9)0.550 (8)
C15A0.0947 (4)0.0647 (8)0.2102 (5)0.0576 (8)0.550 (8)
C16A0.0687 (3)0.0619 (8)0.1104 (5)0.0576 (8)0.550 (8)
C17A0.1207 (4)0.0140 (7)0.0785 (4)0.0576 (8)0.550 (8)
C18A0.1987 (3)0.0872 (7)0.1464 (5)0.0576 (8)0.550 (8)
C19A0.2247 (3)0.0844 (8)0.2462 (4)0.0576 (8)0.550 (8)
C20A0.1727 (4)0.0084 (8)0.2780 (4)0.0576 (8)0.550 (8)
C16B0.0959 (5)0.0687 (10)0.1263 (6)0.0576 (8)0.450 (8)
C17B0.1575 (6)0.0144 (9)0.1123 (6)0.0576 (8)0.450 (8)
C18B0.2203 (5)0.1074 (9)0.1878 (7)0.0576 (8)0.450 (8)
C19B0.2215 (4)0.1172 (9)0.2773 (6)0.0576 (8)0.450 (8)
C20B0.1598 (5)0.0341 (10)0.2913 (5)0.0576 (8)0.450 (8)
C5B0.1948 (4)0.5125 (9)0.4774 (7)0.0589 (8)0.450 (8)
C6B0.1388 (5)0.6235 (7)0.4831 (6)0.0589 (8)0.450 (8)
C7B0.0479 (5)0.6058 (9)0.4259 (6)0.0589 (8)0.450 (8)
C8B0.0130 (4)0.4772 (10)0.3630 (7)0.0589 (8)0.450 (8)
C9B0.0674 (6)0.0296 (11)0.2813 (9)0.0590 (9)0.450 (8)
C10B0.0998 (6)0.0581 (9)0.3453 (7)0.0590 (9)0.450 (8)
C11B0.1561 (5)0.0502 (9)0.3528 (6)0.0590 (9)0.450 (8)
C12B0.1800 (5)0.1870 (8)0.2963 (6)0.0590 (9)0.450 (8)
C13B0.1476 (6)0.2155 (9)0.2323 (6)0.0590 (9)0.450 (8)
C14B0.0913 (7)0.1072 (12)0.2248 (8)0.0590 (9)0.450 (8)
C15B0.0970 (5)0.0588 (10)0.2158 (7)0.0576 (8)0.450 (8)
C4B0.1599 (6)0.3839 (8)0.4144 (7)0.0589 (8)0.450 (8)
C3B0.0690 (6)0.3662 (8)0.3572 (6)0.0589 (8)0.450 (8)
H20A0.190050.006560.344780.0691*0.550 (8)
H19A0.276900.133330.291540.0691*0.550 (8)
H6A0.190810.686600.538250.0706*0.550 (8)
H7A0.045200.722660.416470.0706*0.550 (8)
H8A0.028970.523270.303480.0706*0.550 (8)
H10A0.052410.161160.399970.0708*0.550 (8)
H11A0.139030.004910.440550.0708*0.550 (8)
H12A0.204410.222040.350750.0708*0.550 (8)
H13A0.183170.292730.220360.0708*0.550 (8)
H14A0.096540.136480.179780.0708*0.550 (8)
H16A0.016510.110880.065040.0691*0.550 (8)
H17A0.103350.015890.011810.0691*0.550 (8)
H18A0.233550.137990.125060.0691*0.550 (8)
H2A0.071690.617820.081810.1596*
H2B0.143930.564200.187420.1596*
H2C0.068660.679270.174830.1596*
H4A0.188070.251750.434040.0706*0.550 (8)
H5A0.262240.451140.547030.0706*0.550 (8)
H4B0.197330.309580.410600.0706*0.450 (8)
H5B0.255560.524230.515680.0706*0.450 (8)
H6B0.162130.709490.525260.0706*0.450 (8)
H7B0.010460.680100.429750.0706*0.450 (8)
H8B0.047780.465450.324670.0706*0.450 (8)
H10B0.083780.149630.383130.0708*0.450 (8)
H11B0.177720.031120.395610.0708*0.450 (8)
H12B0.217620.259450.301270.0708*0.450 (8)
H13B0.163590.307040.194450.0708*0.450 (8)
H14B0.069660.126300.181980.0708*0.450 (8)
H16B0.053840.130820.075760.0691*0.450 (8)
H17B0.156740.007830.052350.0691*0.450 (8)
H18B0.261550.162940.178370.0691*0.450 (8)
H19B0.263460.179390.327800.0691*0.450 (8)
H20B0.160560.040740.351210.0691*0.450 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0445 (1)0.0449 (1)0.0519 (1)0.0026 (2)0.0266 (1)0.0031 (2)
S10.0473 (6)0.0687 (7)0.0598 (7)0.0047 (5)0.0208 (5)0.0035 (5)
S20.1330 (16)0.0839 (10)0.0928 (11)0.0212 (10)0.0338 (11)0.0371 (9)
O10.071 (2)0.0609 (18)0.078 (2)0.0144 (15)0.0398 (18)0.0013 (15)
C10.074 (3)0.052 (2)0.050 (2)0.000 (2)0.032 (2)0.0010 (17)
C20.104 (4)0.085 (4)0.144 (5)0.036 (3)0.072 (4)0.005 (4)
C3A0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C4A0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C5A0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C6A0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C7A0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C8A0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C9A0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C10A0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C11A0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C12A0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C13A0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C14A0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C15A0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C16A0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C17A0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C18A0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C19A0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C20A0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C16B0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C17B0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C18B0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C19B0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C20B0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C5B0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C6B0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C7B0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C8B0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C9B0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C10B0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C11B0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C12B0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C13B0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C14B0.0570 (14)0.0649 (12)0.0597 (18)0.0151 (10)0.0324 (12)0.0040 (11)
C15B0.0493 (13)0.0652 (13)0.0660 (17)0.0020 (11)0.0344 (13)0.0058 (12)
C4B0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
C3B0.0513 (14)0.0497 (13)0.0659 (14)0.0040 (10)0.0216 (12)0.0055 (10)
Geometric parameters (Å, º) top
Sn1—S12.4444 (13)C16B—C17B1.389 (14)
Sn1—C3A2.134 (6)C17A—C18A1.390 (9)
Sn1—C9A2.138 (10)C17B—C18B1.390 (12)
Sn1—C15A2.127 (8)C18A—C19A1.391 (9)
Sn1—C3B2.116 (8)C18B—C19B1.389 (13)
Sn1—C9B2.109 (11)C19A—C20A1.389 (10)
Sn1—C15B2.130 (10)C19B—C20B1.391 (12)
S1—C11.740 (5)C2—H2A0.9600
S2—C11.623 (5)C2—H2B0.9600
O1—C11.304 (7)C2—H2C0.9600
O1—C21.442 (8)C4A—H4A0.9300
C3A—C4A1.389 (12)C4B—H4B0.9300
C3A—C8A1.390 (10)C5A—H5A0.9300
C3B—C4B1.391 (15)C5B—H5B0.9300
C3B—C8B1.391 (13)C6A—H6A0.9300
C4A—C5A1.390 (9)C6B—H6B0.9300
C4B—C5B1.390 (12)C7A—H7A0.9300
C5A—C6A1.390 (9)C7B—H7B0.9300
C5B—C6B1.390 (12)C8A—H8A0.9300
C6A—C7A1.391 (10)C8B—H8B0.9300
C6B—C7B1.391 (13)C10A—H10A0.9300
C7A—C8A1.390 (9)C10B—H10B0.9300
C7B—C8B1.390 (12)C11A—H11A0.9300
C9A—C14A1.390 (12)C11B—H11B0.9300
C9A—C10A1.390 (13)C12A—H12A0.9300
C9B—C14B1.390 (15)C12B—H12B0.9300
C9B—C10B1.390 (16)C13A—H13A0.9300
C10A—C11A1.390 (13)C13B—H13B0.9300
C10B—C11B1.391 (14)C14A—H14A0.9300
C11A—C12A1.390 (9)C14B—H14B0.9300
C11B—C12B1.390 (11)C16A—H16A0.9300
C12A—C13A1.390 (10)C16B—H16B0.9300
C12B—C13B1.390 (14)C17A—H17A0.9300
C13A—C14A1.391 (12)C17B—H17B0.9300
C13B—C14B1.391 (16)C18A—H18A0.9300
C15A—C16A1.391 (10)C18B—H18B0.9300
C15A—C20A1.390 (10)C19A—H19A0.9300
C15B—C20B1.390 (12)C19B—H19B0.9300
C15B—C16B1.390 (13)C20A—H20A0.9300
C16A—C17A1.389 (10)C20B—H20B0.9300
S1—Sn1—C3A107.67 (18)O1—C2—H2B109.00
S1—Sn1—C9A98.9 (3)O1—C2—H2C109.00
S1—Sn1—C15A108.02 (19)H2A—C2—H2B109.00
S1—Sn1—C3B107.3 (2)H2A—C2—H2C109.00
S1—Sn1—C9B97.5 (3)H2B—C2—H2C109.00
S1—Sn1—C15B110.3 (3)C3A—C4A—H4A120.00
C3A—Sn1—C9A112.9 (3)C5A—C4A—H4A120.00
C3A—Sn1—C15A115.1 (3)C5B—C4B—H4B120.00
C9A—Sn1—C15A112.7 (3)C3B—C4B—H4B120.00
C3B—Sn1—C9B113.0 (4)C6A—C5A—H5A120.00
C3B—Sn1—C15B115.9 (4)C4A—C5A—H5A120.00
C9B—Sn1—C15B111.1 (4)C6B—C5B—H5B120.00
Sn1—S1—C1101.02 (16)C4B—C5B—H5B120.00
C1—O1—C2119.0 (4)C7A—C6A—H6A120.00
S1—C1—S2121.5 (3)C5A—C6A—H6A120.00
S1—C1—O1111.7 (3)C7B—C6B—H6B120.00
S2—C1—O1126.8 (4)C5B—C6B—H6B120.00
Sn1—C3A—C4A118.0 (4)C8A—C7A—H7A120.00
Sn1—C3A—C8A121.9 (6)C6A—C7A—H7A120.00
C4A—C3A—C8A120.0 (6)C6B—C7B—H7B120.00
Sn1—C3B—C8B117.4 (7)C8B—C7B—H7B120.00
C4B—C3B—C8B120.0 (7)C7A—C8A—H8A120.00
Sn1—C3B—C4B122.5 (7)C3A—C8A—H8A120.00
C3A—C4A—C5A120.0 (6)C7B—C8B—H8B120.00
C3B—C4B—C5B120.0 (9)C3B—C8B—H8B120.00
C4A—C5A—C6A120.0 (7)C11A—C10A—H10A120.00
C4B—C5B—C6B120.0 (9)C9A—C10A—H10A120.00
C5A—C6A—C7A120.0 (5)C11B—C10B—H10B120.00
C5B—C6B—C7B120.0 (7)C9B—C10B—H10B120.00
C6A—C7A—C8A120.0 (6)C12A—C11A—H11A120.00
C6B—C7B—C8B120.0 (8)C10A—C11A—H11A120.00
C3A—C8A—C7A120.0 (7)C12B—C11B—H11B120.00
C3B—C8B—C7B120.0 (8)C10B—C11B—H11B120.00
Sn1—C9A—C10A116.9 (6)C11A—C12A—H12A120.00
Sn1—C9A—C14A122.9 (7)C13A—C12A—H12A120.00
C10A—C9A—C14A120.1 (9)C11B—C12B—H12B120.00
C10B—C9B—C14B120.0 (10)C13B—C12B—H12B120.00
Sn1—C9B—C10B126.1 (7)C14A—C13A—H13A120.00
Sn1—C9B—C14B113.8 (9)C12A—C13A—H13A120.00
C9A—C10A—C11A120.0 (7)C14B—C13B—H13B120.00
C9B—C10B—C11B120.0 (8)C12B—C13B—H13B120.00
C10A—C11A—C12A120.0 (7)C13A—C14A—H14A120.00
C10B—C11B—C12B120.0 (9)C9A—C14A—H14A120.00
C11A—C12A—C13A120.0 (7)C13B—C14B—H14B120.00
C11B—C12B—C13B120.0 (8)C9B—C14B—H14B120.00
C12A—C13A—C14A120.0 (6)C17A—C16A—H16A120.00
C12B—C13B—C14B120.0 (8)C15A—C16A—H16A120.00
C9A—C14A—C13A119.9 (8)C17B—C16B—H16B120.00
C9B—C14B—C13B120.0 (11)C15B—C16B—H16B120.00
Sn1—C15A—C16A116.8 (5)C16A—C17A—H17A120.00
C16A—C15A—C20A120.0 (7)C18A—C17A—H17A120.00
Sn1—C15A—C20A123.2 (5)C18B—C17B—H17B120.00
Sn1—C15B—C20B115.4 (7)C16B—C17B—H17B120.00
C16B—C15B—C20B120.0 (9)C19A—C18A—H18A120.00
Sn1—C15B—C16B124.6 (7)C17A—C18A—H18A120.00
C15A—C16A—C17A120.0 (6)C19B—C18B—H18B120.00
C15B—C16B—C17B120.0 (8)C17B—C18B—H18B120.00
C16A—C17A—C18A120.0 (6)C20A—C19A—H19A120.00
C16B—C17B—C18B120.0 (8)C18A—C19A—H19A120.00
C17A—C18A—C19A120.0 (6)C20B—C19B—H19B120.00
C17B—C18B—C19B120.0 (9)C18B—C19B—H19B120.00
C18A—C19A—C20A120.0 (6)C19A—C20A—H20A120.00
C18B—C19B—C20B120.0 (7)C15A—C20A—H20A120.00
C15A—C20A—C19A120.1 (5)C15B—C20B—H20B120.00
C15B—C20B—C19B120.0 (8)C19B—C20B—H20B120.00
O1—C2—H2A109.00
C3A—Sn1—S1—C146.2 (3)Sn1—C3A—C4A—C5A176.3 (6)
C9A—Sn1—S1—C1163.8 (3)C8A—C3A—C4A—C5A0.0 (12)
C15A—Sn1—S1—C178.7 (3)Sn1—C3A—C8A—C7A176.2 (6)
S1—Sn1—C3A—C4A155.3 (6)C4A—C3A—C8A—C7A0.1 (12)
S1—Sn1—C3A—C8A20.9 (7)C3A—C4A—C5A—C6A0.1 (12)
C9A—Sn1—C3A—C4A96.6 (7)C4A—C5A—C6A—C7A0.1 (11)
C9A—Sn1—C3A—C8A87.2 (7)C5A—C6A—C7A—C8A0.0 (11)
C15A—Sn1—C3A—C4A34.8 (7)C6A—C7A—C8A—C3A0.1 (11)
C15A—Sn1—C3A—C8A141.4 (6)Sn1—C9A—C10A—C11A177.4 (6)
S1—Sn1—C9A—C10A104.6 (7)C14A—C9A—C10A—C11A0.0 (14)
S1—Sn1—C9A—C14A72.7 (8)Sn1—C9A—C14A—C13A177.3 (6)
C3A—Sn1—C9A—C10A8.9 (8)C10A—C9A—C14A—C13A0.1 (13)
C3A—Sn1—C9A—C14A173.8 (7)C9A—C10A—C11A—C12A0.0 (13)
C15A—Sn1—C9A—C10A141.5 (7)C10A—C11A—C12A—C13A0.0 (11)
C15A—Sn1—C9A—C14A41.2 (9)C11A—C12A—C13A—C14A0.0 (11)
S1—Sn1—C15A—C16A3.9 (6)C12A—C13A—C14A—C9A0.1 (12)
S1—Sn1—C15A—C20A175.7 (5)Sn1—C15A—C16A—C17A179.7 (5)
C3A—Sn1—C15A—C16A124.3 (5)C20A—C15A—C16A—C17A0.0 (10)
C3A—Sn1—C15A—C20A55.4 (7)Sn1—C15A—C20A—C19A179.7 (5)
C9A—Sn1—C15A—C16A104.2 (6)C16A—C15A—C20A—C19A0.1 (11)
C9A—Sn1—C15A—C20A76.1 (7)C15A—C16A—C17A—C18A0.0 (10)
Sn1—S1—C1—S2161.2 (3)C16A—C17A—C18A—C19A0.0 (10)
Sn1—S1—C1—O118.0 (4)C17A—C18A—C19A—C20A0.0 (10)
C2—O1—C1—S1174.0 (4)C18A—C19A—C20A—C15A0.1 (10)
C2—O1—C1—S25.1 (7)

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C2H3OS2)]
Mr457.15
Crystal system, space groupMonoclinic, Cc
Temperature (K)296
a, b, c (Å)17.4400 (9), 8.4734 (4), 15.6069 (9)
β (°) 119.626 (2)
V3)2004.82 (19)
Z4
Radiation typeMo Kα
µ (mm1)1.49
Crystal size (mm)0.28 × 0.22 × 0.18
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.683, 0.763
No. of measured, independent and
observed [I > 2σ(I)] reflections
7166, 3483, 3341
Rint0.014
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.055, 1.04
No. of reflections3483
No. of parameters112
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.29
Absolute structureFlack (1983), 1387 Friedel pairs
Absolute structure parameter0.43 (18)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

 
Acknowledgements top

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.