μ-3-Mercaptobenzoato-κ2O:S-bis­(triphenyl­tin)

Zhang, Q.-F.; Zhang, R.-F.; Ma, C.-L.

doi:10.1107/S1600536805027637

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μ-3-Mercaptobenzoato-κ²O:S-bis(triphenyltin)

Q.-F. Zhang, R.-F. Zhang and C.-L. Ma

The title complex, [Sn₂(C₆H₅)₆(C₇H₄O₂S)₂], is a binuclear triphenyltin derivate bridged by a 3-mercaptobenzoate anion. Both Sn atoms are four-coordinate and display distorted tetrahedral geometry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027637/xu6049sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027637/xu6049Isup2.hkl Contains datablock I

CCDC reference: 254165

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.027
wR factor = 0.071
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C42

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C38

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In recent years, organotin complexes have been attracting more and more attention for their wide industrial applications and biological activities (Duboy & Roy, 2003). In order to explore the relationships between the properties and structures, a larger number of organotin complexes have been prepared (Gielen, 2002). We report here the structure of the title binuclear Sn^IV complex, (I).

The molecular structure of (I) is shown in Fig. 1. The mercaptobenzoate anion bridges the Sn1 and Sn2 atoms to form the binuclear complex. Both Sn1 and Sn2 atoms are four coordinated in a distorted tetrahedron. The Sn—S and Sn—O bond distances (Table 1) are comparable to those found in [O,S-bis(triphenyltin(IV)-2-mercaptobenzoate] (Ng et al., 1989) and in (o-aminobenzoato-O)-triphenyltin (Swisher et al., 1984), respectively. The bond angles at the Sn2 atom range from 95.39 (12) to 114.37 (13)°, showing the degree of distortion from a tetrahedron.

Although the Sn2···O2 separation of 2.871 (3) Å is significantly shorter than the sum of van der Waals radii for Sn and O atoms, the normal C1—O1—Sn2 bond angle of 112.7 (2)° suggests no bonding between Sn2 and O2 atoms (Li et al., 2005).

Experimental top

The reaction was carried out under nitrogen atmosphere. 3-Mercaptobenzoic acid (0.154 g, 1 mmol) was added to a solution of benzene (20 ml) with sodium ethoxide (0.136 g, 2 mmol). After stirring for 10 min, triphenyltin chloride (0.770 g, 2 mmol) was added to the mixture. The mixture was kept at 313 K for 12 h. After cooling to room temperature, the solution was filtered. The solvent of the filtrate was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from ethanol. Colorless single crystals of (I) were obtained after 1 d. Yield 0.724 g, 85%. M.p. 414 K. Analysis calculated for C₄₃H₃₄O₂SSn₂: C 60.60, H 4.02%; found: C 60.55, H 4.05%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

µ-3-Mercaptobenzoato-κ²O:S-bis(triphenyltin) top

Crystal data top

[Sn₂(C₆H₅)₆(C₇H₄O₂S)₂]	F(000) = 1696
M_r = 852.14	D_x = 1.510 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8267 reflections
a = 10.383 (3) Å	θ = 2.3–26.2°
b = 17.997 (5) Å	µ = 1.42 mm⁻¹
c = 20.207 (6) Å	T = 298 K
β = 96.928 (5)°	Block, colorless
V = 3748 (2) Å³	0.48 × 0.25 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6639 independent reflections
Radiation source: fine-focus sealed tube	5151 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.548, T_max = 0.754	k = −21→21
19694 measured reflections	l = −24→15

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0327P)² + 1.9228P] where P = (F_o² + 2F_c²)/3
6639 reflections	(Δ/σ)_max = 0.002
433 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Sn₂(C₆H₅)₆(C₇H₄O₂S)₂]	V = 3748 (2) Å³
M_r = 852.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.383 (3) Å	µ = 1.42 mm⁻¹
b = 17.997 (5) Å	T = 298 K
c = 20.207 (6) Å	0.48 × 0.25 × 0.21 mm
β = 96.928 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6639 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5151 reflections with I > 2σ(I)
T_min = 0.548, T_max = 0.754	R_int = 0.021
19694 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	Δρ_max = 0.60 e Å⁻³
6639 reflections	Δρ_min = −0.32 e Å⁻³
433 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
Sn1	0.90635 (2)	0.821378 (13)	0.076812 (12)	0.05398 (8)
Sn2	0.37213 (2)	0.615230 (12)	0.239067 (12)	0.05391 (8)
O1	0.4894 (2)	0.64622 (13)	0.16928 (12)	0.0628 (6)
O2	0.4987 (3)	0.52617 (14)	0.14825 (14)	0.0802 (8)
S1	0.72236 (9)	0.79699 (6)	−0.00654 (5)	0.0678 (3)
C1	0.5258 (3)	0.5902 (2)	0.13545 (19)	0.0587 (9)
C2	0.5984 (3)	0.60973 (17)	0.07861 (17)	0.0517 (8)
C3	0.6292 (3)	0.68334 (17)	0.06666 (17)	0.0512 (8)
H3	0.6086	0.7202	0.0959	0.061*
C4	0.6901 (3)	0.70231 (19)	0.01163 (17)	0.0549 (8)
C5	0.7204 (4)	0.6458 (2)	−0.03095 (19)	0.0742 (11)
H5	0.7619	0.6574	−0.0679	0.089*
C6	0.6898 (4)	0.5732 (2)	−0.0190 (2)	0.0802 (12)
H6	0.7098	0.5361	−0.0482	0.096*
C7	0.6300 (3)	0.5549 (2)	0.0357 (2)	0.0664 (10)
H7	0.6107	0.5055	0.0438	0.080*
C8	0.8651 (3)	0.77874 (19)	0.17022 (17)	0.0543 (8)
C9	0.8213 (4)	0.8261 (2)	0.2156 (2)	0.0826 (12)
H9	0.8099	0.8761	0.2048	0.099*
C10	0.7936 (5)	0.8013 (3)	0.2770 (2)	0.1108 (18)
H10	0.7642	0.8345	0.3071	0.133*
C11	0.8094 (5)	0.7285 (4)	0.2934 (3)	0.1062 (17)
H11	0.7910	0.7117	0.3347	0.127*
C12	0.8521 (4)	0.6800 (3)	0.2491 (3)	0.0912 (14)
H12	0.8622	0.6300	0.2601	0.109*
C13	0.8806 (3)	0.7048 (2)	0.1877 (2)	0.0700 (10)
H13	0.9105	0.6714	0.1579	0.084*
C14	1.0713 (3)	0.77163 (18)	0.04122 (17)	0.0562 (8)
C15	1.1938 (4)	0.7820 (2)	0.0741 (2)	0.0700 (10)
H15	1.2040	0.8080	0.1142	0.084*
C16	1.3023 (4)	0.7546 (2)	0.0488 (3)	0.0893 (13)
H16	1.3845	0.7626	0.0715	0.107*
C17	1.2885 (5)	0.7161 (3)	−0.0090 (3)	0.0963 (14)
H17	1.3617	0.6981	−0.0261	0.116*
C18	1.1678 (5)	0.7031 (3)	−0.0427 (2)	0.0948 (14)
H18	1.1586	0.6757	−0.0820	0.114*
C19	1.0598 (4)	0.7317 (2)	−0.0173 (2)	0.0772 (11)
H19	0.9779	0.7237	−0.0403	0.093*
C20	0.9231 (3)	0.93956 (18)	0.08427 (16)	0.0539 (8)
C21	0.8156 (4)	0.9848 (2)	0.08379 (19)	0.0690 (10)
H21	0.7330	0.9639	0.0792	0.083*
C22	0.8300 (5)	1.0611 (2)	0.0901 (2)	0.0846 (13)
H22	0.7572	1.0914	0.0884	0.102*
C23	0.9519 (6)	1.0919 (2)	0.0988 (2)	0.0874 (13)
H23	0.9616	1.1430	0.1041	0.105*
C24	1.0573 (5)	1.0481 (3)	0.0996 (2)	0.0906 (14)
H24	1.1396	1.0693	0.1053	0.109*
C25	1.0445 (4)	0.9722 (2)	0.0921 (2)	0.0752 (11)
H25	1.1181	0.9427	0.0924	0.090*
C26	0.3420 (3)	0.72521 (18)	0.27340 (18)	0.0558 (8)
C27	0.2229 (4)	0.7573 (2)	0.2597 (2)	0.0731 (11)
H27	0.1539	0.7294	0.2392	0.088*
C28	0.2034 (4)	0.8307 (2)	0.2758 (3)	0.0936 (15)
H28	0.1220	0.8520	0.2651	0.112*
C29	0.3017 (4)	0.8719 (2)	0.3069 (2)	0.0798 (12)
H29	0.2878	0.9214	0.3173	0.096*
C30	0.4201 (4)	0.8409 (2)	0.3231 (2)	0.0799 (12)
H30	0.4874	0.8688	0.3452	0.096*
C31	0.4409 (4)	0.7678 (2)	0.3066 (2)	0.0735 (11)
H31	0.5224	0.7467	0.3179	0.088*
C32	0.4685 (3)	0.54400 (19)	0.31243 (18)	0.0559 (8)
C33	0.5182 (4)	0.5706 (2)	0.3740 (2)	0.0725 (11)
H33	0.5150	0.6213	0.3826	0.087*
C34	0.5726 (4)	0.5231 (3)	0.4231 (2)	0.0883 (13)
H34	0.6055	0.5421	0.4646	0.106*
C35	0.5785 (4)	0.4488 (3)	0.4116 (2)	0.0874 (13)
H35	0.6152	0.4171	0.4450	0.105*
C36	0.5303 (5)	0.4209 (2)	0.3505 (2)	0.0916 (14)
H36	0.5345	0.3702	0.3421	0.110*
C37	0.4751 (4)	0.4687 (2)	0.3012 (2)	0.0762 (11)
H37	0.4420	0.4496	0.2598	0.091*
C38	0.2008 (3)	0.56971 (17)	0.18667 (18)	0.0541 (8)
C39	0.1636 (4)	0.5823 (2)	0.12047 (19)	0.0673 (10)
H39	0.2157	0.6116	0.0966	0.081*
C40	0.0499 (4)	0.5525 (2)	0.0879 (2)	0.0831 (13)
H40	0.0262	0.5621	0.0429	0.100*
C41	−0.0256 (5)	0.5099 (3)	0.1215 (3)	0.1100 (19)
H41	−0.0995	0.4878	0.0994	0.132*
C42	0.0059 (5)	0.4990 (3)	0.1880 (3)	0.136 (2)
H42	−0.0489	0.4713	0.2116	0.163*
C43	0.1196 (4)	0.5288 (3)	0.2212 (2)	0.1006 (16)
H43	0.1404	0.5211	0.2668	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.05627 (15)	0.05466 (14)	0.05165 (15)	−0.00627 (10)	0.00911 (11)	−0.00023 (11)
Sn2	0.05288 (14)	0.04839 (14)	0.05929 (16)	−0.00380 (10)	0.00206 (11)	−0.00020 (11)
O1	0.0684 (15)	0.0534 (13)	0.0684 (16)	−0.0038 (12)	0.0160 (12)	−0.0025 (12)
O2	0.100 (2)	0.0535 (15)	0.089 (2)	−0.0082 (14)	0.0182 (16)	0.0051 (14)
S1	0.0677 (6)	0.0710 (6)	0.0616 (6)	−0.0069 (5)	−0.0044 (5)	0.0125 (5)
C1	0.053 (2)	0.052 (2)	0.068 (2)	−0.0018 (16)	−0.0051 (17)	0.0010 (18)
C2	0.0431 (17)	0.0510 (19)	0.060 (2)	−0.0004 (14)	−0.0003 (15)	−0.0060 (16)
C3	0.0425 (17)	0.0514 (19)	0.058 (2)	0.0017 (14)	−0.0011 (15)	−0.0064 (16)
C4	0.0463 (18)	0.062 (2)	0.054 (2)	−0.0049 (15)	−0.0052 (15)	−0.0048 (17)
C5	0.076 (3)	0.091 (3)	0.056 (2)	−0.021 (2)	0.0128 (19)	−0.019 (2)
C6	0.082 (3)	0.076 (3)	0.084 (3)	−0.012 (2)	0.017 (2)	−0.038 (2)
C7	0.062 (2)	0.052 (2)	0.083 (3)	−0.0054 (17)	0.003 (2)	−0.016 (2)
C8	0.0470 (18)	0.066 (2)	0.049 (2)	−0.0015 (16)	0.0042 (15)	0.0032 (17)
C9	0.100 (3)	0.086 (3)	0.066 (3)	0.014 (2)	0.026 (2)	0.008 (2)
C10	0.138 (5)	0.133 (5)	0.069 (3)	0.042 (4)	0.044 (3)	0.019 (3)
C11	0.095 (4)	0.151 (5)	0.079 (3)	0.026 (3)	0.034 (3)	0.050 (4)
C12	0.084 (3)	0.098 (3)	0.091 (4)	0.009 (3)	0.010 (3)	0.040 (3)
C13	0.062 (2)	0.079 (3)	0.069 (3)	0.0069 (19)	0.0061 (19)	0.010 (2)
C14	0.062 (2)	0.052 (2)	0.055 (2)	0.0004 (16)	0.0092 (17)	0.0040 (16)
C15	0.070 (3)	0.063 (2)	0.075 (3)	0.0054 (19)	0.000 (2)	−0.005 (2)
C16	0.066 (3)	0.081 (3)	0.120 (4)	0.011 (2)	0.008 (3)	−0.004 (3)
C17	0.084 (3)	0.098 (3)	0.111 (4)	0.024 (3)	0.030 (3)	0.001 (3)
C18	0.113 (4)	0.102 (3)	0.072 (3)	0.021 (3)	0.021 (3)	−0.020 (3)
C19	0.076 (3)	0.090 (3)	0.066 (3)	0.007 (2)	0.008 (2)	−0.008 (2)
C20	0.063 (2)	0.0517 (19)	0.048 (2)	−0.0083 (16)	0.0106 (16)	−0.0022 (15)
C21	0.069 (2)	0.074 (3)	0.063 (2)	−0.002 (2)	0.0043 (19)	−0.005 (2)
C22	0.105 (4)	0.071 (3)	0.075 (3)	0.020 (3)	0.003 (2)	−0.007 (2)
C23	0.127 (4)	0.059 (2)	0.078 (3)	−0.011 (3)	0.017 (3)	−0.002 (2)
C24	0.093 (3)	0.076 (3)	0.105 (4)	−0.029 (3)	0.023 (3)	−0.012 (3)
C25	0.067 (2)	0.066 (2)	0.095 (3)	−0.0096 (19)	0.020 (2)	−0.006 (2)
C26	0.053 (2)	0.0489 (18)	0.065 (2)	−0.0018 (15)	0.0069 (17)	−0.0017 (16)
C27	0.055 (2)	0.075 (3)	0.086 (3)	0.0001 (19)	−0.001 (2)	−0.019 (2)
C28	0.072 (3)	0.085 (3)	0.121 (4)	0.025 (2)	0.000 (3)	−0.027 (3)
C29	0.094 (3)	0.059 (2)	0.089 (3)	0.004 (2)	0.017 (3)	−0.012 (2)
C30	0.083 (3)	0.060 (2)	0.094 (3)	−0.017 (2)	0.003 (2)	−0.010 (2)
C31	0.057 (2)	0.058 (2)	0.102 (3)	−0.0029 (17)	−0.004 (2)	0.000 (2)
C32	0.0526 (19)	0.056 (2)	0.058 (2)	−0.0025 (16)	0.0040 (16)	0.0024 (17)
C33	0.075 (3)	0.066 (2)	0.074 (3)	−0.006 (2)	−0.004 (2)	0.002 (2)
C34	0.092 (3)	0.099 (3)	0.067 (3)	−0.005 (3)	−0.018 (2)	0.008 (3)
C35	0.090 (3)	0.093 (3)	0.076 (3)	0.020 (2)	−0.003 (2)	0.023 (3)
C36	0.121 (4)	0.065 (3)	0.086 (3)	0.021 (3)	0.004 (3)	0.008 (2)
C37	0.095 (3)	0.067 (2)	0.064 (3)	0.010 (2)	−0.002 (2)	0.000 (2)
C38	0.056 (2)	0.0458 (18)	0.058 (2)	−0.0069 (15)	−0.0028 (16)	0.0024 (16)
C39	0.078 (3)	0.059 (2)	0.065 (3)	−0.0098 (19)	0.008 (2)	−0.0053 (19)
C40	0.096 (3)	0.078 (3)	0.067 (3)	−0.001 (2)	−0.021 (2)	−0.010 (2)
C41	0.096 (4)	0.084 (3)	0.136 (5)	−0.033 (3)	−0.044 (3)	0.011 (3)
C42	0.109 (4)	0.128 (5)	0.160 (6)	−0.070 (4)	−0.030 (4)	0.059 (4)
C43	0.103 (3)	0.102 (3)	0.088 (3)	−0.045 (3)	−0.024 (3)	0.035 (3)

Geometric parameters (Å, º) top

Sn1—S1	2.4295 (11)	C20—C21	1.380 (5)
Sn1—C8	2.128 (3)	C20—C25	1.382 (5)
Sn1—C14	2.133 (3)	C21—C22	1.385 (5)
Sn1—C20	2.138 (3)	C21—H21	0.9300
Sn2—O1	2.049 (2)	C22—C23	1.374 (6)
Sn2—O2	2.871 (3)	C22—H22	0.9300
Sn2—C26	2.133 (3)	C23—C24	1.348 (6)
Sn2—C32	2.118 (3)	C23—H23	0.9300
Sn2—C38	2.122 (3)	C24—C25	1.379 (5)
O1—C1	1.299 (4)	C24—H24	0.9300
O2—C1	1.221 (4)	C25—H25	0.9300
S1—C4	1.783 (4)	C26—C27	1.363 (5)
C1—C2	1.490 (5)	C26—C31	1.387 (5)
C2—C7	1.380 (5)	C27—C28	1.381 (5)
C2—C3	1.391 (4)	C27—H27	0.9300
C3—C4	1.387 (5)	C28—C29	1.354 (6)
C3—H3	0.9300	C28—H28	0.9300
C4—C5	1.392 (5)	C29—C30	1.355 (6)
C5—C6	1.373 (6)	C29—H29	0.9300
C5—H5	0.9300	C30—C31	1.380 (5)
C6—C7	1.372 (6)	C30—H30	0.9300
C6—H6	0.9300	C31—H31	0.9300
C7—H7	0.9300	C32—C33	1.374 (5)
C8—C9	1.369 (5)	C32—C37	1.378 (5)
C8—C13	1.381 (5)	C33—C34	1.379 (5)
C9—C10	1.382 (6)	C33—H33	0.9300
C9—H9	0.9300	C34—C35	1.361 (6)
C10—C11	1.356 (7)	C34—H34	0.9300
C10—H10	0.9300	C35—C36	1.370 (6)
C11—C12	1.362 (7)	C35—H35	0.9300
C11—H11	0.9300	C36—C37	1.387 (5)
C12—C13	1.383 (6)	C36—H36	0.9300
C12—H12	0.9300	C37—H37	0.9300
C13—H13	0.9300	C38—C39	1.366 (5)
C14—C15	1.375 (5)	C38—C43	1.372 (5)
C14—C19	1.377 (5)	C39—C40	1.389 (5)
C15—C16	1.383 (5)	C39—H39	0.9300
C15—H15	0.9300	C40—C41	1.339 (6)
C16—C17	1.349 (6)	C40—H40	0.9300
C16—H16	0.9300	C41—C42	1.358 (7)
C17—C18	1.373 (6)	C41—H41	0.9300
C17—H17	0.9300	C42—C43	1.394 (6)
C18—C19	1.387 (6)	C42—H42	0.9300
C18—H18	0.9300	C43—H43	0.9300
C19—H19	0.9300

C8—Sn1—C14	113.79 (13)	C14—C19—H19	119.3
C8—Sn1—C20	108.63 (13)	C18—C19—H19	119.3
C14—Sn1—C20	112.32 (13)	C21—C20—C25	118.4 (3)
C8—Sn1—S1	108.91 (9)	C21—C20—Sn1	121.8 (3)
C14—Sn1—S1	106.66 (10)	C25—C20—Sn1	119.7 (3)
C20—Sn1—S1	106.19 (9)	C20—C21—C22	120.3 (4)
O1—Sn2—C32	112.13 (12)	C20—C21—H21	119.8
O1—Sn2—C38	107.09 (12)	C22—C21—H21	119.8
C32—Sn2—C38	114.37 (13)	C23—C22—C21	120.0 (4)
O1—Sn2—C26	95.39 (12)	C23—C22—H22	120.0
C32—Sn2—C26	114.17 (14)	C21—C22—H22	120.0
C38—Sn2—C26	111.94 (13)	C24—C23—C22	120.0 (4)
O1—Sn2—O2	49.93 (8)	C24—C23—H23	120.0
C32—Sn2—O2	84.00 (11)	C22—C23—H23	120.0
C38—Sn2—O2	83.46 (11)	C23—C24—C25	120.7 (4)
C26—Sn2—O2	145.31 (11)	C23—C24—H24	119.7
C1—O1—Sn2	112.7 (2)	C25—C24—H24	119.7
C1—O2—Sn2	75.1 (2)	C24—C25—C20	120.5 (4)
C4—S1—Sn1	100.44 (11)	C24—C25—H25	119.7
O2—C1—O1	122.1 (4)	C20—C25—H25	119.7
O2—C1—C2	122.5 (3)	C27—C26—C31	117.7 (3)
O1—C1—C2	115.4 (3)	C27—C26—Sn2	119.5 (3)
C7—C2—C3	119.7 (3)	C31—C26—Sn2	122.7 (3)
C7—C2—C1	119.8 (3)	C26—C27—C28	120.9 (4)
C3—C2—C1	120.4 (3)	C26—C27—H27	119.6
C4—C3—C2	120.7 (3)	C28—C27—H27	119.6
C4—C3—H3	119.7	C29—C28—C27	120.6 (4)
C2—C3—H3	119.7	C29—C28—H28	119.7
C3—C4—C5	118.3 (3)	C27—C28—H28	119.7
C3—C4—S1	121.0 (3)	C28—C29—C30	119.8 (4)
C5—C4—S1	120.6 (3)	C28—C29—H29	120.1
C6—C5—C4	120.8 (4)	C30—C29—H29	120.1
C6—C5—H5	119.6	C29—C30—C31	119.9 (4)
C4—C5—H5	119.6	C29—C30—H30	120.0
C7—C6—C5	120.5 (4)	C31—C30—H30	120.0
C7—C6—H6	119.8	C30—C31—C26	121.0 (4)
C5—C6—H6	119.8	C30—C31—H31	119.5
C6—C7—C2	120.0 (4)	C26—C31—H31	119.5
C6—C7—H7	120.0	C33—C32—C37	118.2 (3)
C2—C7—H7	120.0	C33—C32—Sn2	121.1 (3)
C9—C8—C13	117.8 (4)	C37—C32—Sn2	120.6 (3)
C9—C8—Sn1	119.2 (3)	C32—C33—C34	120.8 (4)
C13—C8—Sn1	123.0 (3)	C32—C33—H33	119.6
C8—C9—C10	121.4 (4)	C34—C33—H33	119.6
C8—C9—H9	119.3	C35—C34—C33	120.6 (4)
C10—C9—H9	119.3	C35—C34—H34	119.7
C11—C10—C9	120.0 (5)	C33—C34—H34	119.7
C11—C10—H10	120.0	C34—C35—C36	119.8 (4)
C9—C10—H10	120.0	C34—C35—H35	120.1
C10—C11—C12	119.9 (4)	C36—C35—H35	120.1
C10—C11—H11	120.1	C35—C36—C37	119.6 (4)
C12—C11—H11	120.1	C35—C36—H36	120.2
C11—C12—C13	120.2 (4)	C37—C36—H36	120.2
C11—C12—H12	119.9	C32—C37—C36	121.1 (4)
C13—C12—H12	119.9	C32—C37—H37	119.5
C8—C13—C12	120.6 (4)	C36—C37—H37	119.5
C8—C13—H13	119.7	C39—C38—C43	118.0 (3)
C12—C13—H13	119.7	C39—C38—Sn2	123.0 (3)
C15—C14—C19	117.7 (4)	C43—C38—Sn2	118.9 (3)
C15—C14—Sn1	120.9 (3)	C38—C39—C40	121.6 (4)
C19—C14—Sn1	121.2 (3)	C38—C39—H39	119.2
C14—C15—C16	121.3 (4)	C40—C39—H39	119.2
C14—C15—H15	119.3	C41—C40—C39	119.9 (4)
C16—C15—H15	119.3	C41—C40—H40	120.1
C17—C16—C15	119.8 (4)	C39—C40—H40	120.1
C17—C16—H16	120.1	C40—C41—C42	119.9 (4)
C15—C16—H16	120.1	C40—C41—H41	120.0
C16—C17—C18	120.8 (4)	C42—C41—H41	120.0
C16—C17—H17	119.6	C41—C42—C43	120.7 (5)
C18—C17—H17	119.6	C41—C42—H42	119.7
C17—C18—C19	118.9 (4)	C43—C42—H42	119.7
C17—C18—H18	120.5	C38—C43—C42	119.9 (5)
C19—C18—H18	120.5	C38—C43—H43	120.0
C14—C19—C18	121.4 (4)	C42—C43—H43	120.0

Experimental details

Crystal data
Chemical formula	[Sn₂(C₆H₅)₆(C₇H₄O₂S)₂]
M_r	852.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.383 (3), 17.997 (5), 20.207 (6)
β (°)	96.928 (5)
V (Å³)	3748 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.48 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.548, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	19694, 6639, 5151
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.071, 1.00
No. of reflections	6639
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.32

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected geometric parameters (Å, º) top

Sn1—S1	2.4295 (11)	Sn2—O1	2.049 (2)
Sn1—C8	2.128 (3)	Sn2—C26	2.133 (3)
Sn1—C14	2.133 (3)	Sn2—C32	2.118 (3)
Sn1—C20	2.138 (3)	Sn2—C38	2.122 (3)

C8—Sn1—C14	113.79 (13)	O1—Sn2—C32	112.13 (12)
C8—Sn1—C20	108.63 (13)	O1—Sn2—C38	107.09 (12)
C14—Sn1—C20	112.32 (13)	C32—Sn2—C38	114.37 (13)
C8—Sn1—S1	108.91 (9)	O1—Sn2—C26	95.39 (12)
C14—Sn1—S1	106.66 (10)	C32—Sn2—C26	114.17 (14)
C20—Sn1—S1	106.19 (9)	C38—Sn2—C26	111.94 (13)

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