(O-Methyl di­thio­carbonato-κS)tri­phenyl­tin(IV)

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

doi:10.1107/S1600536813012300

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page m316

doi:10.1107/S1600536813012300

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(O-Methyl dithiocarbonato-κS)triphenyltin(IV)

Fatima Javed,^a Saqib Ali,^a Wajid Shah,^b M. Nawaz Tahir ^c ^* and Hameed Ullah ^d

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, ^bDepartment of Chemistry, University of Hazara, K.P.K, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dDepartment of Chemistry, Hazara University, Mansehra, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 May 2013; accepted 6 May 2013; online 15 May 2013)

In the title compound, [Sn(C₆H₅)₃(C₂H₃OS₂)], the Sn^IV 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).

Related literature

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

Experimental

Crystal data

[Sn(C₆H₅)₃(C₂H₃OS₂)]
M_r = 457.15
Monoclinic, C c
a = 17.4400 (9) Å
b = 8.4734 (4) Å
c = 15.6069 (9) Å
β = 119.626 (2)°
V = 2004.82 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.683, T_max = 0.763
7166 measured reflections
3483 independent reflections
3341 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.055
S = 1.04
3483 reflections
112 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1387 Friedel pairs
Flack parameter: 0.43 (18)

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012300/hb7077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012300/hb7077Isup2.hkl

checkCIF report

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.

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

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
M_r = 457.15	D_x = 1.515 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3341 reflections
a = 17.4400 (9) Å	θ = 2.8–26.0°
b = 8.4734 (4) Å	µ = 1.49 mm⁻¹
c = 15.6069 (9) Å	T = 296 K
β = 119.626 (2)°	Prism, white
V = 2004.82 (19) Å³	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3483 independent reflections
Radiation source: fine-focus sealed tube	3341 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 2.8°
ω scans	h = −21→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.683, T_max = 0.763	l = −19→19
7166 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0246P)² + 2.1104P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3483 reflections	Δρ_max = 0.44 e Å⁻³
112 parameters	Δρ_min = −0.29 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1387 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (18)

Crystal data top

[Sn(C₆H₅)₃(C₂H₃OS₂)]	V = 2004.82 (19) Å³
M_r = 457.15	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 17.4400 (9) Å	µ = 1.49 mm⁻¹
b = 8.4734 (4) Å	T = 296 K
c = 15.6069 (9) Å	0.28 × 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)
T_min = 0.683, T_max = 0.763	R_int = 0.014
7166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.055	Δρ_max = 0.44 e Å⁻³
S = 1.04	Δρ_min = −0.29 e Å⁻³
3483 reflections	Absolute structure: Flack (1983), 1387 Friedel pairs
112 parameters	Absolute 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.01045 (1)	0.18518 (2)	0.25080 (1)	0.0459 (1)
S1	−0.10922 (8)	0.30516 (13)	0.10239 (9)	0.0611 (4)
S2	−0.11228 (15)	0.6208 (2)	0.02348 (15)	0.1128 (7)
O1	0.0289 (2)	0.4577 (4)	0.1408 (3)	0.0687 (11)
C1	−0.0567 (3)	0.4711 (5)	0.0901 (3)	0.0581 (14)
C2	0.0828 (4)	0.5909 (7)	0.1467 (5)	0.106 (3)
C3A	0.0722 (5)	0.3677 (6)	0.3576 (5)	0.0589 (8)	0.550 (8)
C4A	0.1594 (5)	0.3461 (6)	0.4305 (5)	0.0589 (8)	0.550 (8)
C5A	0.2039 (4)	0.4656 (8)	0.4982 (5)	0.0589 (8)	0.550 (8)
C6A	0.1611 (4)	0.6067 (6)	0.4930 (4)	0.0589 (8)	0.550 (8)
C7A	0.0738 (4)	0.6283 (6)	0.4200 (5)	0.0589 (8)	0.550 (8)
C8A	0.0294 (4)	0.5088 (8)	0.3523 (5)	0.0589 (8)	0.550 (8)
C9A	−0.0659 (5)	0.0278 (10)	0.2859 (7)	0.0590 (9)	0.550 (8)
C10A	−0.0786 (6)	0.0702 (8)	0.3640 (6)	0.0590 (9)	0.550 (8)
C11A	−0.1305 (5)	−0.0234 (8)	0.3883 (5)	0.0590 (9)	0.550 (8)
C12A	−0.1697 (4)	−0.1594 (7)	0.3345 (5)	0.0590 (9)	0.550 (8)
C13A	−0.1570 (4)	−0.2018 (7)	0.2564 (5)	0.0590 (9)	0.550 (8)
C14A	−0.1051 (5)	−0.1081 (10)	0.2320 (6)	0.0590 (9)	0.550 (8)
C15A	0.0947 (4)	0.0647 (8)	0.2102 (5)	0.0576 (8)	0.550 (8)
C16A	0.0687 (3)	0.0619 (8)	0.1104 (5)	0.0576 (8)	0.550 (8)
C17A	0.1207 (4)	−0.0140 (7)	0.0785 (4)	0.0576 (8)	0.550 (8)
C18A	0.1987 (3)	−0.0872 (7)	0.1464 (5)	0.0576 (8)	0.550 (8)
C19A	0.2247 (3)	−0.0844 (8)	0.2462 (4)	0.0576 (8)	0.550 (8)
C20A	0.1727 (4)	−0.0084 (8)	0.2780 (4)	0.0576 (8)	0.550 (8)
C16B	0.0959 (5)	0.0687 (10)	0.1263 (6)	0.0576 (8)	0.450 (8)
C17B	0.1575 (6)	−0.0144 (9)	0.1123 (6)	0.0576 (8)	0.450 (8)
C18B	0.2203 (5)	−0.1074 (9)	0.1878 (7)	0.0576 (8)	0.450 (8)
C19B	0.2215 (4)	−0.1172 (9)	0.2773 (6)	0.0576 (8)	0.450 (8)
C20B	0.1598 (5)	−0.0341 (10)	0.2913 (5)	0.0576 (8)	0.450 (8)
C5B	0.1948 (4)	0.5125 (9)	0.4774 (7)	0.0589 (8)	0.450 (8)
C6B	0.1388 (5)	0.6235 (7)	0.4831 (6)	0.0589 (8)	0.450 (8)
C7B	0.0479 (5)	0.6058 (9)	0.4259 (6)	0.0589 (8)	0.450 (8)
C8B	0.0130 (4)	0.4772 (10)	0.3630 (7)	0.0589 (8)	0.450 (8)
C9B	−0.0674 (6)	0.0296 (11)	0.2813 (9)	0.0590 (9)	0.450 (8)
C10B	−0.0998 (6)	0.0581 (9)	0.3453 (7)	0.0590 (9)	0.450 (8)
C11B	−0.1561 (5)	−0.0502 (9)	0.3528 (6)	0.0590 (9)	0.450 (8)
C12B	−0.1800 (5)	−0.1870 (8)	0.2963 (6)	0.0590 (9)	0.450 (8)
C13B	−0.1476 (6)	−0.2155 (9)	0.2323 (6)	0.0590 (9)	0.450 (8)
C14B	−0.0913 (7)	−0.1072 (12)	0.2248 (8)	0.0590 (9)	0.450 (8)
C15B	0.0970 (5)	0.0588 (10)	0.2158 (7)	0.0576 (8)	0.450 (8)
C4B	0.1599 (6)	0.3839 (8)	0.4144 (7)	0.0589 (8)	0.450 (8)
C3B	0.0690 (6)	0.3662 (8)	0.3572 (6)	0.0589 (8)	0.450 (8)
H20A	0.19005	−0.00656	0.34478	0.0691*	0.550 (8)
H19A	0.27690	−0.13333	0.29154	0.0691*	0.550 (8)
H6A	0.19081	0.68660	0.53825	0.0706*	0.550 (8)
H7A	0.04520	0.72266	0.41647	0.0706*	0.550 (8)
H8A	−0.02897	0.52327	0.30348	0.0706*	0.550 (8)
H10A	−0.05241	0.16116	0.39997	0.0708*	0.550 (8)
H11A	−0.13903	0.00491	0.44055	0.0708*	0.550 (8)
H12A	−0.20441	−0.22204	0.35075	0.0708*	0.550 (8)
H13A	−0.18317	−0.29273	0.22036	0.0708*	0.550 (8)
H14A	−0.09654	−0.13648	0.17978	0.0708*	0.550 (8)
H16A	0.01651	0.11088	0.06504	0.0691*	0.550 (8)
H17A	0.10335	−0.01589	0.01181	0.0691*	0.550 (8)
H18A	0.23355	−0.13799	0.12506	0.0691*	0.550 (8)
H2A	0.07169	0.61782	0.08181	0.1596*
H2B	0.14393	0.56420	0.18742	0.1596*
H2C	0.06866	0.67927	0.17483	0.1596*
H4A	0.18807	0.25175	0.43404	0.0706*	0.550 (8)
H5A	0.26224	0.45114	0.54703	0.0706*	0.550 (8)
H4B	0.19733	0.30958	0.41060	0.0706*	0.450 (8)
H5B	0.25556	0.52423	0.51568	0.0706*	0.450 (8)
H6B	0.16213	0.70949	0.52526	0.0706*	0.450 (8)
H7B	0.01046	0.68010	0.42975	0.0706*	0.450 (8)
H8B	−0.04778	0.46545	0.32467	0.0706*	0.450 (8)
H10B	−0.08378	0.14963	0.38313	0.0708*	0.450 (8)
H11B	−0.17772	−0.03112	0.39561	0.0708*	0.450 (8)
H12B	−0.21762	−0.25945	0.30127	0.0708*	0.450 (8)
H13B	−0.16359	−0.30704	0.19445	0.0708*	0.450 (8)
H14B	−0.06966	−0.12630	0.18198	0.0708*	0.450 (8)
H16B	0.05384	0.13082	0.07576	0.0691*	0.450 (8)
H17B	0.15674	−0.00783	0.05235	0.0691*	0.450 (8)
H18B	0.26155	−0.16294	0.17837	0.0691*	0.450 (8)
H19B	0.26346	−0.17939	0.32780	0.0691*	0.450 (8)
H20B	0.16056	−0.04074	0.35121	0.0691*	0.450 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0445 (1)	0.0449 (1)	0.0519 (1)	−0.0026 (2)	0.0266 (1)	−0.0031 (2)
S1	0.0473 (6)	0.0687 (7)	0.0598 (7)	−0.0047 (5)	0.0208 (5)	0.0035 (5)
S2	0.1330 (16)	0.0839 (10)	0.0928 (11)	0.0212 (10)	0.0338 (11)	0.0371 (9)
O1	0.071 (2)	0.0609 (18)	0.078 (2)	−0.0144 (15)	0.0398 (18)	0.0013 (15)
C1	0.074 (3)	0.052 (2)	0.050 (2)	0.000 (2)	0.032 (2)	−0.0010 (17)
C2	0.104 (4)	0.085 (4)	0.144 (5)	−0.036 (3)	0.072 (4)	−0.005 (4)
C3A	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C4A	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C5A	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C6A	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C7A	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C8A	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C9A	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C10A	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C11A	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C12A	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C13A	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C14A	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C15A	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C16A	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C17A	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C18A	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C19A	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C20A	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C16B	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C17B	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C18B	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C19B	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C20B	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C5B	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C6B	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C7B	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C8B	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C9B	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C10B	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C11B	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C12B	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C13B	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C14B	0.0570 (14)	0.0649 (12)	0.0597 (18)	−0.0151 (10)	0.0324 (12)	−0.0040 (11)
C15B	0.0493 (13)	0.0652 (13)	0.0660 (17)	−0.0020 (11)	0.0344 (13)	−0.0058 (12)
C4B	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)
C3B	0.0513 (14)	0.0497 (13)	0.0659 (14)	0.0040 (10)	0.0216 (12)	−0.0055 (10)

Geometric parameters (Å, º) top

Sn1—S1	2.4444 (13)	C16B—C17B	1.389 (14)
Sn1—C3A	2.134 (6)	C17A—C18A	1.390 (9)
Sn1—C9A	2.138 (10)	C17B—C18B	1.390 (12)
Sn1—C15A	2.127 (8)	C18A—C19A	1.391 (9)
Sn1—C3B	2.116 (8)	C18B—C19B	1.389 (13)
Sn1—C9B	2.109 (11)	C19A—C20A	1.389 (10)
Sn1—C15B	2.130 (10)	C19B—C20B	1.391 (12)
S1—C1	1.740 (5)	C2—H2A	0.9600
S2—C1	1.623 (5)	C2—H2B	0.9600
O1—C1	1.304 (7)	C2—H2C	0.9600
O1—C2	1.442 (8)	C4A—H4A	0.9300
C3A—C4A	1.389 (12)	C4B—H4B	0.9300
C3A—C8A	1.390 (10)	C5A—H5A	0.9300
C3B—C4B	1.391 (15)	C5B—H5B	0.9300
C3B—C8B	1.391 (13)	C6A—H6A	0.9300
C4A—C5A	1.390 (9)	C6B—H6B	0.9300
C4B—C5B	1.390 (12)	C7A—H7A	0.9300
C5A—C6A	1.390 (9)	C7B—H7B	0.9300
C5B—C6B	1.390 (12)	C8A—H8A	0.9300
C6A—C7A	1.391 (10)	C8B—H8B	0.9300
C6B—C7B	1.391 (13)	C10A—H10A	0.9300
C7A—C8A	1.390 (9)	C10B—H10B	0.9300
C7B—C8B	1.390 (12)	C11A—H11A	0.9300
C9A—C14A	1.390 (12)	C11B—H11B	0.9300
C9A—C10A	1.390 (13)	C12A—H12A	0.9300
C9B—C14B	1.390 (15)	C12B—H12B	0.9300
C9B—C10B	1.390 (16)	C13A—H13A	0.9300
C10A—C11A	1.390 (13)	C13B—H13B	0.9300
C10B—C11B	1.391 (14)	C14A—H14A	0.9300
C11A—C12A	1.390 (9)	C14B—H14B	0.9300
C11B—C12B	1.390 (11)	C16A—H16A	0.9300
C12A—C13A	1.390 (10)	C16B—H16B	0.9300
C12B—C13B	1.390 (14)	C17A—H17A	0.9300
C13A—C14A	1.391 (12)	C17B—H17B	0.9300
C13B—C14B	1.391 (16)	C18A—H18A	0.9300
C15A—C16A	1.391 (10)	C18B—H18B	0.9300
C15A—C20A	1.390 (10)	C19A—H19A	0.9300
C15B—C20B	1.390 (12)	C19B—H19B	0.9300
C15B—C16B	1.390 (13)	C20A—H20A	0.9300
C16A—C17A	1.389 (10)	C20B—H20B	0.9300

S1—Sn1—C3A	107.67 (18)	O1—C2—H2B	109.00
S1—Sn1—C9A	98.9 (3)	O1—C2—H2C	109.00
S1—Sn1—C15A	108.02 (19)	H2A—C2—H2B	109.00
S1—Sn1—C3B	107.3 (2)	H2A—C2—H2C	109.00
S1—Sn1—C9B	97.5 (3)	H2B—C2—H2C	109.00
S1—Sn1—C15B	110.3 (3)	C3A—C4A—H4A	120.00
C3A—Sn1—C9A	112.9 (3)	C5A—C4A—H4A	120.00
C3A—Sn1—C15A	115.1 (3)	C5B—C4B—H4B	120.00
C9A—Sn1—C15A	112.7 (3)	C3B—C4B—H4B	120.00
C3B—Sn1—C9B	113.0 (4)	C6A—C5A—H5A	120.00
C3B—Sn1—C15B	115.9 (4)	C4A—C5A—H5A	120.00
C9B—Sn1—C15B	111.1 (4)	C6B—C5B—H5B	120.00
Sn1—S1—C1	101.02 (16)	C4B—C5B—H5B	120.00
C1—O1—C2	119.0 (4)	C7A—C6A—H6A	120.00
S1—C1—S2	121.5 (3)	C5A—C6A—H6A	120.00
S1—C1—O1	111.7 (3)	C7B—C6B—H6B	120.00
S2—C1—O1	126.8 (4)	C5B—C6B—H6B	120.00
Sn1—C3A—C4A	118.0 (4)	C8A—C7A—H7A	120.00
Sn1—C3A—C8A	121.9 (6)	C6A—C7A—H7A	120.00
C4A—C3A—C8A	120.0 (6)	C6B—C7B—H7B	120.00
Sn1—C3B—C8B	117.4 (7)	C8B—C7B—H7B	120.00
C4B—C3B—C8B	120.0 (7)	C7A—C8A—H8A	120.00
Sn1—C3B—C4B	122.5 (7)	C3A—C8A—H8A	120.00
C3A—C4A—C5A	120.0 (6)	C7B—C8B—H8B	120.00
C3B—C4B—C5B	120.0 (9)	C3B—C8B—H8B	120.00
C4A—C5A—C6A	120.0 (7)	C11A—C10A—H10A	120.00
C4B—C5B—C6B	120.0 (9)	C9A—C10A—H10A	120.00
C5A—C6A—C7A	120.0 (5)	C11B—C10B—H10B	120.00
C5B—C6B—C7B	120.0 (7)	C9B—C10B—H10B	120.00
C6A—C7A—C8A	120.0 (6)	C12A—C11A—H11A	120.00
C6B—C7B—C8B	120.0 (8)	C10A—C11A—H11A	120.00
C3A—C8A—C7A	120.0 (7)	C12B—C11B—H11B	120.00
C3B—C8B—C7B	120.0 (8)	C10B—C11B—H11B	120.00
Sn1—C9A—C10A	116.9 (6)	C11A—C12A—H12A	120.00
Sn1—C9A—C14A	122.9 (7)	C13A—C12A—H12A	120.00
C10A—C9A—C14A	120.1 (9)	C11B—C12B—H12B	120.00
C10B—C9B—C14B	120.0 (10)	C13B—C12B—H12B	120.00
Sn1—C9B—C10B	126.1 (7)	C14A—C13A—H13A	120.00
Sn1—C9B—C14B	113.8 (9)	C12A—C13A—H13A	120.00
C9A—C10A—C11A	120.0 (7)	C14B—C13B—H13B	120.00
C9B—C10B—C11B	120.0 (8)	C12B—C13B—H13B	120.00
C10A—C11A—C12A	120.0 (7)	C13A—C14A—H14A	120.00
C10B—C11B—C12B	120.0 (9)	C9A—C14A—H14A	120.00
C11A—C12A—C13A	120.0 (7)	C13B—C14B—H14B	120.00
C11B—C12B—C13B	120.0 (8)	C9B—C14B—H14B	120.00
C12A—C13A—C14A	120.0 (6)	C17A—C16A—H16A	120.00
C12B—C13B—C14B	120.0 (8)	C15A—C16A—H16A	120.00
C9A—C14A—C13A	119.9 (8)	C17B—C16B—H16B	120.00
C9B—C14B—C13B	120.0 (11)	C15B—C16B—H16B	120.00
Sn1—C15A—C16A	116.8 (5)	C16A—C17A—H17A	120.00
C16A—C15A—C20A	120.0 (7)	C18A—C17A—H17A	120.00
Sn1—C15A—C20A	123.2 (5)	C18B—C17B—H17B	120.00
Sn1—C15B—C20B	115.4 (7)	C16B—C17B—H17B	120.00
C16B—C15B—C20B	120.0 (9)	C19A—C18A—H18A	120.00
Sn1—C15B—C16B	124.6 (7)	C17A—C18A—H18A	120.00
C15A—C16A—C17A	120.0 (6)	C19B—C18B—H18B	120.00
C15B—C16B—C17B	120.0 (8)	C17B—C18B—H18B	120.00
C16A—C17A—C18A	120.0 (6)	C20A—C19A—H19A	120.00
C16B—C17B—C18B	120.0 (8)	C18A—C19A—H19A	120.00
C17A—C18A—C19A	120.0 (6)	C20B—C19B—H19B	120.00
C17B—C18B—C19B	120.0 (9)	C18B—C19B—H19B	120.00
C18A—C19A—C20A	120.0 (6)	C19A—C20A—H20A	120.00
C18B—C19B—C20B	120.0 (7)	C15A—C20A—H20A	120.00
C15A—C20A—C19A	120.1 (5)	C15B—C20B—H20B	120.00
C15B—C20B—C19B	120.0 (8)	C19B—C20B—H20B	120.00
O1—C2—H2A	109.00

C3A—Sn1—S1—C1	46.2 (3)	Sn1—C3A—C4A—C5A	176.3 (6)
C9A—Sn1—S1—C1	163.8 (3)	C8A—C3A—C4A—C5A	0.0 (12)
C15A—Sn1—S1—C1	−78.7 (3)	Sn1—C3A—C8A—C7A	−176.2 (6)
S1—Sn1—C3A—C4A	−155.3 (6)	C4A—C3A—C8A—C7A	−0.1 (12)
S1—Sn1—C3A—C8A	20.9 (7)	C3A—C4A—C5A—C6A	0.1 (12)
C9A—Sn1—C3A—C4A	96.6 (7)	C4A—C5A—C6A—C7A	−0.1 (11)
C9A—Sn1—C3A—C8A	−87.2 (7)	C5A—C6A—C7A—C8A	0.0 (11)
C15A—Sn1—C3A—C4A	−34.8 (7)	C6A—C7A—C8A—C3A	0.1 (11)
C15A—Sn1—C3A—C8A	141.4 (6)	Sn1—C9A—C10A—C11A	177.4 (6)
S1—Sn1—C9A—C10A	−104.6 (7)	C14A—C9A—C10A—C11A	0.0 (14)
S1—Sn1—C9A—C14A	72.7 (8)	Sn1—C9A—C14A—C13A	−177.3 (6)
C3A—Sn1—C9A—C10A	8.9 (8)	C10A—C9A—C14A—C13A	−0.1 (13)
C3A—Sn1—C9A—C14A	−173.8 (7)	C9A—C10A—C11A—C12A	0.0 (13)
C15A—Sn1—C9A—C10A	141.5 (7)	C10A—C11A—C12A—C13A	0.0 (11)
C15A—Sn1—C9A—C14A	−41.2 (9)	C11A—C12A—C13A—C14A	0.0 (11)
S1—Sn1—C15A—C16A	−3.9 (6)	C12A—C13A—C14A—C9A	0.1 (12)
S1—Sn1—C15A—C20A	175.7 (5)	Sn1—C15A—C16A—C17A	179.7 (5)
C3A—Sn1—C15A—C16A	−124.3 (5)	C20A—C15A—C16A—C17A	0.0 (10)
C3A—Sn1—C15A—C20A	55.4 (7)	Sn1—C15A—C20A—C19A	−179.7 (5)
C9A—Sn1—C15A—C16A	104.2 (6)	C16A—C15A—C20A—C19A	−0.1 (11)
C9A—Sn1—C15A—C20A	−76.1 (7)	C15A—C16A—C17A—C18A	0.0 (10)
Sn1—S1—C1—S2	−161.2 (3)	C16A—C17A—C18A—C19A	0.0 (10)
Sn1—S1—C1—O1	18.0 (4)	C17A—C18A—C19A—C20A	0.0 (10)
C2—O1—C1—S1	−174.0 (4)	C18A—C19A—C20A—C15A	0.1 (10)
C2—O1—C1—S2	5.1 (7)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₂H₃OS₂)]
M_r	457.15
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	17.4400 (9), 8.4734 (4), 15.6069 (9)
β (°)	119.626 (2)
V (Å³)	2004.82 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.683, 0.763
No. of measured, independent and observed [I > 2σ(I)] reflections	7166, 3483, 3341
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.055, 1.04
No. of reflections	3483
No. of parameters	112
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.29
Absolute structure	Flack (1983), 1387 Friedel pairs
Absolute structure parameter	0.43 (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

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.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ng, S. W. & Rae, A. D. (2000). Acta Cryst. C56, e47–e48. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar