(Dimethyl sulfoxide-κO)di­phenyl­(3-thioxo-3H-1,2-dithiole-4,5-dithiol­ato-κ2S4,S5)tin(IV)

Comerlato, N.M.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809047904

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1592-m1593

doi:10.1107/S1600536809047904

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(Dimethyl sulfoxide-κO)diphenyl(3-thioxo-3H-1,2-dithiole-4,5-dithiolato-κ²S⁴,S⁵)tin(IV)

Nadia M. Comerlato,^a Edward R. T. Tiekink,^b ^* James L. Wardell ^c ‡ and Solange M. S. V. Wardell ^d

^aDepartamento de Química Inorgânica, Instituto de Química, Universidade, Federal do Rio de Janeiro, CP 68563, 21941-909 Rio de Janeiro, RJ, Brazil, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and ^dCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 7 November 2009; accepted 11 November 2009; online 18 November 2009)

The Sn atom in the title compound, [Sn(C₆H₅)₂(C₃S₅)(C₂H₆OS)], exists within a distorted trigonal-bipyramidal geometry defined by two S atoms of the 1,2-dithiole-3-thione-4,5-dithiolate dianion, two ipso-C atoms from the phenyl groups, and the O atom of the dimethyl sulfoxide molecule. In this description, one of the S atoms and the O occupy axial positions. In the crystal, centrosymmetrically related molecules associate via pairs of C—H⋯S contacts, forming dimeric aggregates.

Related literature

For background to the synthesis of dmt compounds, see: Steimecke et al. (1982 ). For related crystal structures, see: Aupers et al. (1998 ); Khan et al. (1998 ); Chohan et al. (1999 ); Bordinhão et al. (2006 , 2008 ); Comerlato et al. (2008 ). For additional analysis of geometry, see: Addison et al. (1984 ).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₃S₅)(C₂H₆OS)]
M_r = 547.35
Monoclinic, P 2₁ /n
a = 11.1420 (5) Å
b = 15.7237 (6) Å
c = 11.9646 (6) Å
β = 96.892 (2)°
V = 2080.97 (16) Å³
Z = 4
Mo Kα radiation
μ = 1.83 mm⁻¹
T = 120 K
0.24 × 0.16 × 0.10 mm

Data collection

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.536, T_max = 0.746
22729 measured reflections
4770 independent reflections
3906 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.088
S = 1.06
4770 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn—C4	2.130 (3)
Sn—C10	2.133 (3)
Sn—O1	2.311 (2)
Sn—S1	2.4357 (9)
Sn—S2	2.5582 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯S2ⁱ	0.95	2.71	3.599 (4)	157
Symmetry code: (i) -x+2, -y, -z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047904/hb5220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047904/hb5220Isup2.hkl

checkCIF report

Comment top

While several structures of (1,3-dithiole-2-thione-4,5-dithiolato)tin, [Sn-dmit], and (1,3-dithiole-2-one-4,5-dithiolato)tin [Sn-dmio] complexes have been reported (e.g., Comerlato et al., 2008), similar (1,2-dithiole-3-thione-4,5-dithiolato)tin complexes have been essentially neglected, with only one systematic study known (Bordinhão et al., 2006; Bordinhão et al., 2008); see Fig. 1 for chemical structures of dmit, dmio and dmt. The poor solubility of 1,2-dithiole-3-thione-4,5-dithiolato (dmt) complexes has been put forward as a major cause for the limited number of their reported crystal structures. Attempts to obtain good crystals of Ph₂Sn(dmt), prepared from reaction of Na₂(dmt) and Ph₂SnCl₂ in MeOH solution, failed as only amorphous material was obtained. However, crystallization of Ph₂Sn(dmt) from a DMSO/MeOH solution produced crystals of the DMSO solvate, (I), suitable for the X-Ray study reported herein.

As compounds, R₂Sn(dmit) and R₂Sn(dmio), having non-functionalized alkyl or aryl R groups (e.g., R = Me, Et, Bu or Ph), are aggregated in both the solid–state and in non-coordinating solvents as a consequence of intermolecular Sn···S interactions., it is assumed that the R₂Sn(dmt) analogues are similarly aggregated. The formation of adducts such as [Ph₂Sn(dmt)(dmso)] will generally provide coordinatively saturated tin centres and hence result in appreciably more soluble species having essentially non-interacting cations and anions. Structures of ionic species, [Q][R₂Sn(dmit)X] and [Q][R₂Sn(dmio)X] [Q+ = onium cation, X = halide or pseudohalide], with 5-coordinate tin have also been determined (Chohan et al., 1999; Khan et al., 1998; Aupers et al., 1998).

The Sn atom in (1) is five-coordinate, existing within a C₂OS₂ donor set defined by a chelating dmt ligand, two ipso-C atoms and the O atom derived from the DMSO molecule, Fig. 2. The coordination geometry is based on a trigonal bipyramid with the S2–Sn–O1 axial angle being 166.52 (6) °. As expected, the Sn–S1_equatorial distance of 2.4357 (9) Å is shorter than the Sn–S2_axial distance of 2.5582 (9) Å. The coordination geometry is distorted towards trigonal bipyramidal (TP). This is quantified by the value of τ = 0.72, which compares with the ideal values of 1.0 and 0.0 for TP and square pyramidal, respectively (Addison et al., 1984).

The most prominent intermolecular interaction connecting molecules is of the type C–H···S and these occur between centrosymmetric pairs to form loosely associated dimers, Table 1 and Fig. 3.

Related literature top

For background to the synthesis of dmt compounds, see: Steimecke et al. (1982). For related crystal structures, see: Aupers et al. (1998); Khan et al. (1998); Chohan et al. (1999); Bordinhão et al. (2006); Bordinhão et al. (2008); Comerlato et al. (2008). For additional analysis of geometry, see: Addison et al. (1984).

Experimental top

To a stirred suspension of 4,5-bis(benzoylthio)-1,2-dithiole-3-thione (Steimecke et al., 1982) (410 mg, 1 mmol) in methanol (10 ml), under argon, was added a sodium methoxide solution prepared from sodium (150 mg, 6.75 mmol) and methanol (10 ml). To the resulting purple solution of Na₂dmt was added with stirring a methanolic solution of Ph₂SnCl₂ (345 mg, 1 mmol). The reaction mixture was stirred for 1 h, rotary evaporated and the residue washed well with water. The solid residue (535 mg) was dissolved in a mixture of DMSO and MeOH (ca v:v 3:1) and left to slowly recrystallize to give (I); m.pt. 428–431 K (dec.) IR (KBr, cm^-1): 1061 (ν C—S), 950, 941 (ν S—O), 910, 827, 720 (ν C=S).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Preparation of the title compound.
	Fig. 2. Molecular structure (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 3. Supramolecular dimer in (I) mediated by C–H···S contacts (orange dashed lines). Colour code: Sn, orange; S, yellow;O, red; C, grey; and H, green.

(Dimethyl sulfoxide-κO)diphenyl(3-thioxo-3H-1,2-dithiole-4,5-dithiolato- κ²S⁴,S⁵)tin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₃S₅)(C₂H₆OS)]	F(000) = 1088
M_r = 547.35	D_x = 1.747 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 44319 reflections
a = 11.1420 (5) Å	θ = 2.9–27.5°
b = 15.7237 (6) Å	µ = 1.83 mm⁻¹
c = 11.9646 (6) Å	T = 120 K
β = 96.892 (2)°	Block, yellow
V = 2080.97 (16) Å³	0.24 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	4770 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3906 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −20→19
T_min = 0.536, T_max = 0.746	l = −15→15
22729 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0404P)² + 1.7706P] where P = (F_o² + 2F_c²)/3
4770 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₃S₅)(C₂H₆OS)]	V = 2080.97 (16) Å³
M_r = 547.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1420 (5) Å	µ = 1.83 mm⁻¹
b = 15.7237 (6) Å	T = 120 K
c = 11.9646 (6) Å	0.24 × 0.16 × 0.10 mm
β = 96.892 (2)°

Data collection top

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	4770 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3906 reflections with I > 2σ(I)
T_min = 0.536, T_max = 0.746	R_int = 0.057
22729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	Δρ_max = 0.85 e Å⁻³
4770 reflections	Δρ_min = −1.26 e Å⁻³
228 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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 > 2σ(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
Sn	0.823308 (19)	0.079364 (13)	0.201486 (19)	0.01886 (9)
S1	0.64254 (8)	0.07006 (5)	0.29688 (7)	0.02196 (18)
S2	0.68225 (8)	0.10256 (6)	0.01905 (8)	0.0263 (2)
S3	0.42347 (8)	0.12813 (5)	−0.02069 (8)	0.0266 (2)
S4	0.30214 (8)	0.12492 (6)	0.09713 (8)	0.0302 (2)
S5	0.35612 (8)	0.08574 (6)	0.33685 (9)	0.0301 (2)
S6	0.89763 (8)	0.13614 (5)	0.46902 (8)	0.0264 (2)
O1	0.9096 (2)	0.06287 (13)	0.38570 (19)	0.0218 (5)
C1	0.5279 (3)	0.09377 (19)	0.1865 (3)	0.0210 (7)
C2	0.5481 (3)	0.1063 (2)	0.0763 (3)	0.0226 (7)
C3	0.4068 (3)	0.0995 (2)	0.2126 (3)	0.0249 (7)
C4	0.8953 (3)	−0.0427 (2)	0.1706 (3)	0.0199 (7)
C5	1.0061 (3)	−0.0547 (2)	0.1308 (3)	0.0291 (8)
H5	1.0562	−0.0073	0.1200	0.035*
C6	1.0440 (3)	−0.1366 (2)	0.1067 (3)	0.0349 (9)
H6	1.1200	−0.1448	0.0798	0.042*
C7	0.9712 (3)	−0.2061 (2)	0.1217 (3)	0.0327 (9)
H7	0.9965	−0.2616	0.1037	0.039*
C8	0.8622 (3)	−0.1945 (2)	0.1626 (3)	0.0277 (8)
H8	0.8126	−0.2423	0.1735	0.033*
C9	0.8241 (3)	−0.1133 (2)	0.1883 (3)	0.0216 (7)
H9	0.7495	−0.1059	0.2179	0.026*
C10	0.9274 (3)	0.1927 (2)	0.1953 (3)	0.0212 (7)
C11	1.0477 (3)	0.1947 (2)	0.2438 (3)	0.0260 (7)
H11	1.0842	0.1443	0.2758	0.031*
C12	1.1145 (3)	0.2691 (2)	0.2459 (3)	0.0331 (9)
H12	1.1963	0.2698	0.2792	0.040*
C13	1.0608 (4)	0.3427 (2)	0.1990 (4)	0.0376 (10)
H13	1.1055	0.3943	0.2023	0.045*
C14	0.9438 (4)	0.3415 (2)	0.1480 (3)	0.0350 (9)
H14	0.9085	0.3919	0.1147	0.042*
C15	0.8763 (3)	0.2666 (2)	0.1450 (3)	0.0270 (8)
H15	0.7956	0.2658	0.1087	0.032*
C16	1.0469 (3)	0.1532 (2)	0.5361 (3)	0.0351 (9)
H16A	1.0823	0.0987	0.5628	0.053*
H16B	1.0443	0.1917	0.6002	0.053*
H16C	1.0962	0.1785	0.4824	0.053*
C17	0.8353 (4)	0.0869 (3)	0.5831 (4)	0.0423 (10)
H17A	0.7533	0.0670	0.5574	0.064*
H17B	0.8326	0.1281	0.6441	0.064*
H17C	0.8858	0.0384	0.6105	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01908 (13)	0.01369 (12)	0.02314 (14)	0.00039 (8)	−0.00013 (9)	0.00187 (8)
S1	0.0222 (4)	0.0193 (4)	0.0241 (5)	0.0009 (3)	0.0015 (3)	0.0028 (3)
S2	0.0210 (4)	0.0330 (5)	0.0243 (5)	0.0008 (3)	0.0000 (4)	0.0059 (4)
S3	0.0213 (4)	0.0276 (4)	0.0293 (5)	0.0011 (3)	−0.0039 (4)	0.0000 (4)
S4	0.0194 (4)	0.0347 (5)	0.0356 (5)	0.0019 (4)	−0.0007 (4)	−0.0036 (4)
S5	0.0259 (5)	0.0298 (5)	0.0360 (6)	−0.0008 (3)	0.0096 (4)	−0.0007 (4)
S6	0.0326 (5)	0.0183 (4)	0.0263 (5)	0.0038 (3)	−0.0041 (4)	−0.0022 (3)
O1	0.0270 (13)	0.0153 (11)	0.0224 (13)	0.0015 (9)	0.0004 (10)	−0.0005 (9)
C1	0.0199 (16)	0.0128 (15)	0.0292 (19)	0.0002 (12)	−0.0021 (14)	−0.0015 (13)
C2	0.0222 (17)	0.0168 (15)	0.0276 (19)	0.0021 (13)	−0.0011 (14)	−0.0005 (13)
C3	0.0210 (17)	0.0190 (16)	0.034 (2)	−0.0001 (13)	−0.0012 (15)	−0.0006 (14)
C4	0.0210 (16)	0.0172 (15)	0.0203 (17)	0.0019 (13)	−0.0024 (13)	0.0010 (13)
C5	0.0271 (19)	0.0246 (17)	0.036 (2)	0.0000 (14)	0.0059 (16)	0.0053 (16)
C6	0.031 (2)	0.041 (2)	0.035 (2)	0.0111 (17)	0.0121 (17)	0.0045 (17)
C7	0.044 (2)	0.0218 (17)	0.032 (2)	0.0098 (16)	0.0041 (17)	−0.0024 (15)
C8	0.039 (2)	0.0174 (16)	0.0254 (19)	−0.0013 (14)	0.0002 (16)	0.0044 (14)
C9	0.0221 (17)	0.0195 (16)	0.0222 (18)	−0.0016 (13)	−0.0013 (14)	0.0008 (13)
C10	0.0257 (17)	0.0170 (15)	0.0216 (18)	−0.0003 (13)	0.0063 (14)	−0.0002 (13)
C11	0.0243 (17)	0.0233 (17)	0.030 (2)	−0.0018 (14)	0.0027 (15)	−0.0018 (14)
C12	0.029 (2)	0.034 (2)	0.038 (2)	−0.0086 (16)	0.0099 (17)	−0.0065 (17)
C13	0.049 (3)	0.0236 (18)	0.045 (2)	−0.0145 (17)	0.026 (2)	−0.0081 (17)
C14	0.050 (2)	0.0178 (17)	0.041 (2)	0.0041 (16)	0.021 (2)	0.0026 (16)
C15	0.0300 (19)	0.0197 (16)	0.032 (2)	0.0039 (14)	0.0051 (15)	0.0014 (14)
C16	0.035 (2)	0.033 (2)	0.034 (2)	−0.0047 (16)	−0.0112 (17)	0.0022 (17)
C17	0.049 (3)	0.049 (3)	0.031 (2)	−0.0049 (19)	0.012 (2)	−0.0018 (18)

Geometric parameters (Å, º) top

Sn—C4	2.130 (3)	C7—C8	1.375 (5)
Sn—C10	2.133 (3)	C7—H7	0.9500
Sn—O1	2.311 (2)	C8—C9	1.392 (5)
Sn—S1	2.4357 (9)	C8—H8	0.9500
Sn—S2	2.5582 (9)	C9—H9	0.9500
S1—C1	1.764 (3)	C10—C11	1.396 (5)
S2—C2	1.718 (3)	C10—C15	1.398 (5)
S3—C2	1.734 (3)	C11—C12	1.386 (5)
S3—S4	2.0674 (13)	C11—H11	0.9500
S4—C3	1.744 (4)	C12—C13	1.390 (6)
S5—C3	1.667 (4)	C12—H12	0.9500
S6—O1	1.540 (2)	C13—C14	1.372 (6)
S6—C16	1.778 (4)	C13—H13	0.9500
S6—C17	1.781 (4)	C14—C15	1.395 (5)
C1—C2	1.379 (5)	C14—H14	0.9500
C1—C3	1.423 (5)	C15—H15	0.9500
C4—C5	1.388 (5)	C16—H16A	0.9800
C4—C9	1.395 (5)	C16—H16B	0.9800
C5—C6	1.396 (5)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.384 (5)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800

C4—Sn—C10	121.97 (12)	C6—C7—H7	120.0
C4—Sn—O1	86.68 (10)	C7—C8—C9	120.3 (3)
C10—Sn—O1	87.79 (10)	C7—C8—H8	119.8
C4—Sn—S1	112.16 (9)	C9—C8—H8	119.8
C10—Sn—S1	123.38 (9)	C8—C9—C4	120.2 (3)
O1—Sn—S1	79.58 (6)	C8—C9—H9	119.9
C4—Sn—S2	100.73 (9)	C4—C9—H9	119.9
C10—Sn—S2	97.58 (9)	C11—C10—C15	118.8 (3)
O1—Sn—S2	166.52 (6)	C11—C10—Sn	120.2 (2)
S1—Sn—S2	87.16 (3)	C15—C10—Sn	121.0 (2)
C1—S1—Sn	101.66 (12)	C12—C11—C10	120.9 (3)
C2—S2—Sn	98.03 (12)	C12—C11—H11	119.6
C2—S3—S4	94.35 (12)	C10—C11—H11	119.6
C3—S4—S3	96.65 (12)	C11—C12—C13	119.5 (4)
O1—S6—C16	104.84 (17)	C11—C12—H12	120.3
O1—S6—C17	104.05 (17)	C13—C12—H12	120.3
C16—S6—C17	98.6 (2)	C14—C13—C12	120.5 (3)
S6—O1—Sn	118.36 (12)	C14—C13—H13	119.7
C2—C1—C3	117.9 (3)	C12—C13—H13	119.7
C2—C1—S1	124.0 (3)	C13—C14—C15	120.3 (3)
C3—C1—S1	118.0 (3)	C13—C14—H14	119.9
C1—C2—S2	128.8 (3)	C15—C14—H14	119.9
C1—C2—S3	117.3 (3)	C14—C15—C10	120.0 (3)
S2—C2—S3	113.9 (2)	C14—C15—H15	120.0
C1—C3—S5	128.2 (3)	C10—C15—H15	120.0
C1—C3—S4	113.7 (3)	S6—C16—H16A	109.5
S5—C3—S4	118.1 (2)	S6—C16—H16B	109.5
C5—C4—C9	119.3 (3)	H16A—C16—H16B	109.5
C5—C4—Sn	123.5 (2)	S6—C16—H16C	109.5
C9—C4—Sn	117.2 (2)	H16A—C16—H16C	109.5
C4—C5—C6	120.0 (3)	H16B—C16—H16C	109.5
C4—C5—H5	120.0	S6—C17—H17A	109.5
C6—C5—H5	120.0	S6—C17—H17B	109.5
C7—C6—C5	120.3 (3)	H17A—C17—H17B	109.5
C7—C6—H6	119.9	S6—C17—H17C	109.5
C5—C6—H6	119.9	H17A—C17—H17C	109.5
C8—C7—C6	119.9 (3)	H17B—C17—H17C	109.5
C8—C7—H7	120.0

C4—Sn—S1—C1	−105.26 (14)	O1—Sn—C4—C5	−94.0 (3)
C10—Sn—S1—C1	92.39 (15)	S1—Sn—C4—C5	−171.4 (3)
O1—Sn—S1—C1	172.71 (12)	S2—Sn—C4—C5	97.3 (3)
S2—Sn—S1—C1	−4.83 (10)	C10—Sn—C4—C9	173.5 (2)
C4—Sn—S2—C2	116.74 (14)	O1—Sn—C4—C9	88.2 (3)
C10—Sn—S2—C2	−118.59 (14)	S1—Sn—C4—C9	10.8 (3)
O1—Sn—S2—C2	−5.7 (3)	S2—Sn—C4—C9	−80.5 (2)
S1—Sn—S2—C2	4.72 (11)	C9—C4—C5—C6	1.4 (5)
C2—S3—S4—C3	−1.58 (16)	Sn—C4—C5—C6	−176.4 (3)
C16—S6—O1—Sn	−130.43 (17)	C4—C5—C6—C7	0.3 (6)
C17—S6—O1—Sn	126.56 (19)	C5—C6—C7—C8	−1.3 (6)
C4—Sn—O1—S6	177.97 (16)	C6—C7—C8—C9	0.5 (6)
C10—Sn—O1—S6	55.76 (16)	C7—C8—C9—C4	1.2 (5)
S1—Sn—O1—S6	−68.78 (13)	C5—C4—C9—C8	−2.2 (5)
S2—Sn—O1—S6	−58.2 (3)	Sn—C4—C9—C8	175.8 (3)
Sn—S1—C1—C2	4.4 (3)	C4—Sn—C10—C11	−42.9 (3)
Sn—S1—C1—C3	−176.2 (2)	O1—Sn—C10—C11	41.8 (3)
C3—C1—C2—S2	−179.4 (3)	S1—Sn—C10—C11	117.8 (2)
S1—C1—C2—S2	0.0 (5)	S2—Sn—C10—C11	−150.6 (3)
C3—C1—C2—S3	0.1 (4)	C4—Sn—C10—C15	138.4 (3)
S1—C1—C2—S3	179.45 (17)	O1—Sn—C10—C15	−136.9 (3)
Sn—S2—C2—C1	−4.1 (3)	S1—Sn—C10—C15	−60.9 (3)
Sn—S2—C2—S3	176.36 (15)	S2—Sn—C10—C15	30.7 (3)
S4—S3—C2—C1	1.1 (3)	C15—C10—C11—C12	2.3 (5)
S4—S3—C2—S2	−179.35 (16)	Sn—C10—C11—C12	−176.4 (3)
C2—C1—C3—S5	178.8 (3)	C10—C11—C12—C13	−0.1 (6)
S1—C1—C3—S5	−0.6 (4)	C11—C12—C13—C14	−1.8 (6)
C2—C1—C3—S4	−1.6 (4)	C12—C13—C14—C15	1.4 (6)
S1—C1—C3—S4	179.03 (17)	C13—C14—C15—C10	0.9 (5)
S3—S4—C3—C1	2.0 (2)	C11—C10—C15—C14	−2.7 (5)
S3—S4—C3—S5	−178.38 (18)	Sn—C10—C15—C14	176.0 (3)
C10—Sn—C4—C5	−8.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S2ⁱ	0.95	2.71	3.599 (4)	157

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₃S₅)(C₂H₆OS)]
M_r	547.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	11.1420 (5), 15.7237 (6), 11.9646 (6)
β (°)	96.892 (2)
V (Å³)	2080.97 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.83
Crystal size (mm)	0.24 × 0.16 × 0.10

Data collection
Diffractometer	Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.536, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	22729, 4770, 3906
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.088, 1.06
No. of reflections	4770
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −1.26

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Sn—C4	2.130 (3)	Sn—S1	2.4357 (9)
Sn—C10	2.133 (3)	Sn—S2	2.5582 (9)
Sn—O1	2.311 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S2ⁱ	0.95	2.71	3.599 (4)	157

Symmetry code: (i) −x+2, −y, −z.

Footnotes

‡Additional correspondence author: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

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