Octa­methyldi-μ3-oxido-bis­(μ2-thio­phene-3-acetato-κ2O:O′)(thio­phene-3-acetato-κO)tetra­tin(IV)

Danish, M.; Tahir, M.N.; Ahmad, N.; Raza, A.R.; Ibrahim, M.

doi:10.1107/S1600536809015475

Octamethyldi-μ₃-oxido-bis(μ₂-thiophene-3-acetato-κ²O:O′)(thiophene-3-acetato-κO)tetratin(IV)

M. Danish, M. N. Tahir, N. Ahmad, A. R. Raza and M. Ibrahim

In the centrosymmetric title compound, [Sn₄(CH₃)₈(C₆H₅O₂S)₄O₂], the central four-membered planar ring (Sn₂O₂) makes dihedral angles of 66.28 (12) and 77.43 (11)° with the heterocyclic rings of the bridging and monodentate ligands, respectively. One Sn^IV atom adopts a distorted SnO₃C₂ trigonal-bipyramidal geometry, with both C atoms in equatorial sites and the other a grossly distorted SnO₄C₂ octahedral or irregular arrangement. In the crystal, the molecules are connected into pillar-like polymeric units making R₂²(12) ring motifs due to intermolecular C—H

O interactions. C–H

π interactions are also present. The O atoms of the chelating ligands and the S atom of the monodentate ligand are disordered over two sets of sites in a 0.65 (6):0.35 (6) ratio

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809015475/hb2953sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809015475/hb2953Isup2.hkl Contains datablock I

CCDC reference: 731202

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.024
wR factor = 0.059
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     --  C5      ..      10.05 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C14    --  C15     ..       7.60 su
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C15

Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn2    --  O4_a    ..       7.09 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C13    -   C16    ...       1.36 Ang.
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGC
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGC

Alert level G
PLAT301_ALERT_3_G Note Main Residue  Disorder ....................      10.00 Perc.

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

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

Comment top

In continuation to our interest with the tin chemistry in various forms (Danish et al., 1995, 1996), (Tahir et al., 1997a, 1997b), we report here the title compound (I), (Fig. 1).

The crystal structure of bis(dicyclohexylammonium 3-thienylacetate) (Ng et al., 2001) has been reported which shows disorder in the 3-thienylacetate unit. In our present complex the ligand is also in disorder. The O-atoms of chelating carboxylate are disordered over two sites with occupancy ratio of 0.65:0.35, whereas in other ligands the disorder is present at the S-atoms. In the title molecule symmetry related central four membered ring A (Sn2/O3/Sn2ⁱ/O3ⁱ; i = -x + 1, -y, -z + 1) is of course planar. The five membered rings B (C3—C5/S1/C6) and C (C13—C15/S2A/C16) are also planar. The dihedral angles between A/B, A/C and B/C are 66.28 (12)°, 77.43 (11)° and 71.23 (18)°, respectively. Due to intermolecular H-bonding, the stannoxanes are connected in pillar like polymeric form making R₂²(12) ring motifs (Bernstein et al., 1995), (Fig. 2). The molecules are also stabilized due to C–H···π interactions (Table 1).

Related literature top

For related structures, see: Danish et al. (1995, 1996); Ng et al. (2001); Tahir et al. (1997a,b). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

The complex was synthesized by refluxing (CH₃)₂SnO (1.66 g, 0.01 mol) and 3-thiopheneacetic acid (1.42 g, 0.01 mol) under argon, in toluene for 4–6 h. Water formed during the reaction was continuously removed by the use of Dean-Stark apparatus. The reaction mixture was brought to room temperature and then boiled with anhydrous activated charcoal and filtered through alumina column. Toluene was removed completely from the filtrate under vacuum. The solid mass thus obtained was purified by repeated crystallization from chloroform-ethanol (8:2) mixture, to obtain colourless prisms of (I).

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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are not shown for clarity.

Octamethyldi-µ₃-oxido-bis(µ₂-thiophene-3-acetato- κ²O:O')(thiophene-3-acetato-κO)tetratin(IV) top

Crystal data top

[Sn₄(CH₃)₈(C₆H₅O₂S)₄O₂]	Z = 1
M_r = 1191.79	F(000) = 580
Triclinic, P1	D_x = 1.840 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7330 (5) Å	Cell parameters from 3441 reflections
b = 9.7403 (5) Å	θ = 2.2–25.5°
c = 12.0432 (6) Å	µ = 2.54 mm⁻¹
α = 85.407 (2)°	T = 296 K
β = 85.259 (1)°	Prism, colourless
γ = 71.256 (2)°	0.20 × 0.15 × 0.13 mm
V = 1075.74 (10) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	4012 independent reflections
Radiation source: fine-focus sealed tube	3441 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 7.80 pixels mm^-1	θ_max = 25.5°, θ_min = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.637, T_max = 0.719	l = −14→14
19310 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)] = 0.024	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0219P)² + 1.4193P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4012 reflections	Δρ_max = 0.84 e Å⁻³
250 parameters	Δρ_min = −0.65 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00156 (19)

Crystal data top

[Sn₄(CH₃)₈(C₆H₅O₂S)₄O₂]	γ = 71.256 (2)°
M_r = 1191.79	V = 1075.74 (10) Å³
Triclinic, P1	Z = 1
a = 9.7330 (5) Å	Mo Kα radiation
b = 9.7403 (5) Å	µ = 2.54 mm⁻¹
c = 12.0432 (6) Å	T = 296 K
α = 85.407 (2)°	0.20 × 0.15 × 0.13 mm
β = 85.259 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4012 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3441 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.719	R_int = 0.025
19310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.04	Δρ_max = 0.84 e Å⁻³
4012 reflections	Δρ_min = −0.65 e Å⁻³
250 parameters

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	0.18885 (2)	0.25808 (2)	0.45386 (2)	0.0444 (1)
Sn2	0.48666 (2)	−0.09190 (2)	0.39587 (2)	0.0446 (1)
S1	0.27895 (18)	−0.25877 (16)	−0.05837 (11)	0.0934 (5)
S2A	0.3409 (3)	0.25077 (19)	0.99888 (15)	0.1310 (8)	0.635
O1A	0.1177 (13)	0.137 (3)	0.333 (2)	0.076 (4)	0.65 (6)
O2A	0.3179 (12)	−0.023 (3)	0.2610 (14)	0.065 (4)	0.65 (6)
O3	0.3779 (2)	0.0937 (2)	0.47382 (18)	0.0410 (7)
O4	0.2813 (3)	0.3298 (3)	0.5913 (2)	0.0584 (9)
O5	0.0925 (4)	0.5232 (4)	0.5897 (3)	0.1044 (16)
C1	0.1856 (4)	0.0434 (4)	0.2645 (3)	0.0497 (12)
C2	0.0913 (4)	0.0161 (4)	0.1808 (3)	0.0562 (12)
C3	0.1613 (4)	−0.1092 (4)	0.1087 (3)	0.0532 (12)
C4	0.1850 (5)	−0.2556 (5)	0.1418 (4)	0.0771 (19)
C5	0.2468 (5)	−0.3522 (5)	0.0595 (4)	0.0719 (16)
C6	0.2094 (6)	−0.0968 (5)	0.0020 (4)	0.0756 (19)
C7	0.2415 (5)	0.4034 (5)	0.3342 (4)	0.0789 (17)
C8	0.0351 (4)	0.1981 (5)	0.5611 (4)	0.0822 (18)
C9	0.3936 (5)	−0.2493 (5)	0.4656 (5)	0.089 (2)
C10	0.6134 (5)	−0.0291 (5)	0.2633 (3)	0.0712 (16)
C11	0.2064 (5)	0.4535 (4)	0.6276 (3)	0.0628 (14)
C12	0.2698 (6)	0.5070 (5)	0.7194 (4)	0.0832 (19)
C13	0.2700 (5)	0.4165 (4)	0.8259 (3)	0.0607 (14)
C14	0.1451 (6)	0.4020 (6)	0.8834 (4)	0.0840 (19)
C15	0.1689 (6)	0.3121 (5)	0.9827 (4)	0.0761 (19)
C16	0.3894 (5)	0.3378 (6)	0.8800 (4)	0.0839 (19)
S2B	0.3409 (3)	0.25077 (19)	0.99888 (15)	0.1310 (8)	0.365
O2B	0.283 (5)	−0.0624 (18)	0.299 (4)	0.065 (7)	0.35 (6)
O1B	0.156 (5)	0.168 (2)	0.296 (3)	0.062 (7)	0.35 (6)
H2A	0.00668	0.00014	0.22101	0.0672*
H4	0.16091	−0.28575	0.21394	0.0921*
H5	0.26718	−0.45241	0.06791	0.0864*
H7A	0.19235	0.40649	0.26765	0.1183*
H7B	0.34458	0.37212	0.31712	0.1183*
H6A	0.20504	−0.00826	−0.03533	0.0906*
H2B	0.05705	0.10329	0.13256	0.0672*
H8B	0.05988	0.09419	0.56672	0.1230*
H8C	−0.05934	0.23970	0.53209	0.1230*
H9A	0.30262	−0.20216	0.50480	0.1329*
H9B	0.45826	−0.31449	0.51661	0.1329*
H9C	0.37745	−0.30285	0.40721	0.1329*
H10A	0.67382	0.01893	0.29210	0.1063*
H10B	0.55061	0.03594	0.21106	0.1063*
H10C	0.67335	−0.11358	0.22649	0.1063*
H12A	0.36857	0.50390	0.69644	0.0997*
H12B	0.21327	0.60710	0.73188	0.0997*
H14	0.05271	0.44812	0.85838	0.1013*
H15	0.09708	0.29176	1.03071	0.0912*
H16A	0.48440	0.33181	0.85601	0.1007*
H7C	0.21167	0.49849	0.36272	0.1183*
H8A	0.03409	0.23280	0.63361	0.1230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0437 (1)	0.0386 (1)	0.0463 (2)	−0.0034 (1)	−0.0056 (1)	−0.0128 (1)
Sn2	0.0470 (1)	0.0397 (1)	0.0452 (2)	−0.0066 (1)	−0.0063 (1)	−0.0177 (1)
S1	0.1234 (11)	0.0908 (9)	0.0681 (8)	−0.0294 (8)	−0.0098 (7)	−0.0323 (7)
S2A	0.206 (2)	0.0932 (11)	0.0868 (11)	−0.0321 (12)	−0.0320 (12)	−0.0049 (9)
O1A	0.058 (4)	0.088 (8)	0.084 (8)	−0.016 (4)	−0.007 (4)	−0.050 (7)
O2A	0.054 (4)	0.091 (10)	0.051 (5)	−0.015 (4)	−0.010 (3)	−0.032 (5)
O3	0.0391 (11)	0.0368 (12)	0.0424 (12)	−0.0025 (9)	−0.0042 (9)	−0.0133 (9)
O4	0.0644 (16)	0.0503 (14)	0.0575 (16)	−0.0070 (12)	−0.0136 (12)	−0.0216 (12)
O5	0.099 (3)	0.078 (2)	0.108 (3)	0.0243 (19)	−0.031 (2)	−0.036 (2)
C1	0.056 (2)	0.051 (2)	0.047 (2)	−0.0207 (18)	−0.0110 (17)	−0.0073 (17)
C2	0.063 (2)	0.057 (2)	0.052 (2)	−0.0193 (18)	−0.0162 (18)	−0.0092 (17)
C3	0.061 (2)	0.057 (2)	0.049 (2)	−0.0237 (18)	−0.0167 (17)	−0.0112 (17)
C4	0.103 (4)	0.065 (3)	0.073 (3)	−0.041 (3)	0.002 (3)	−0.008 (2)
C5	0.095 (3)	0.052 (2)	0.077 (3)	−0.033 (2)	0.002 (2)	−0.019 (2)
C6	0.116 (4)	0.063 (3)	0.052 (3)	−0.030 (3)	−0.016 (2)	−0.010 (2)
C7	0.099 (3)	0.062 (3)	0.059 (3)	−0.006 (2)	0.000 (2)	0.008 (2)
C8	0.051 (2)	0.075 (3)	0.117 (4)	−0.019 (2)	0.014 (2)	−0.008 (3)
C9	0.066 (3)	0.067 (3)	0.143 (5)	−0.033 (2)	−0.002 (3)	−0.016 (3)
C10	0.088 (3)	0.065 (3)	0.047 (2)	−0.008 (2)	0.007 (2)	−0.0032 (19)
C11	0.083 (3)	0.049 (2)	0.054 (2)	−0.013 (2)	−0.009 (2)	−0.0174 (18)
C12	0.137 (4)	0.069 (3)	0.058 (3)	−0.047 (3)	−0.012 (3)	−0.021 (2)
C13	0.077 (3)	0.059 (2)	0.052 (2)	−0.024 (2)	−0.005 (2)	−0.0255 (19)
C14	0.076 (3)	0.085 (3)	0.095 (4)	−0.028 (3)	0.009 (3)	−0.032 (3)
C15	0.095 (4)	0.067 (3)	0.072 (3)	−0.037 (3)	0.017 (3)	−0.013 (2)
C16	0.076 (3)	0.098 (4)	0.079 (3)	−0.022 (3)	−0.008 (2)	−0.032 (3)
S2B	0.206 (2)	0.0932 (11)	0.0868 (11)	−0.0321 (12)	−0.0320 (12)	−0.0049 (9)
O2B	0.075 (12)	0.052 (7)	0.076 (15)	−0.021 (5)	−0.033 (12)	−0.012 (7)
O1B	0.076 (15)	0.047 (7)	0.062 (11)	−0.011 (6)	−0.025 (9)	−0.021 (6)

Geometric parameters (Å, º) top

Sn1—O1A	2.23 (2)	C3—C6	1.341 (6)
Sn1—O3	2.031 (2)	C4—C5	1.384 (7)
Sn1—O4	2.207 (3)	C11—C12	1.512 (7)
Sn1—C7	2.088 (5)	C12—C13	1.497 (6)
Sn1—C8	2.091 (4)	C13—C16	1.355 (7)
Sn1—O1B	2.24 (4)	C13—C14	1.390 (8)
Sn2—O2A	2.312 (17)	C14—C15	1.414 (7)
Sn2—O3	2.0366 (19)	C2—H2A	0.9700
Sn2—C9	2.106 (5)	C2—H2B	0.9700
Sn2—C10	2.109 (4)	C4—H4	0.9300
Sn2—O3ⁱ	2.127 (2)	C5—H5	0.9300
Sn2—O4ⁱ	2.670 (3)	C6—H6A	0.9300
Sn2—O2B	2.31 (5)	C7—H7A	0.9600
Sn2—Sn2ⁱ	3.2694 (4)	C7—H7B	0.9600
S1—C5	1.686 (5)	C7—H7C	0.9600
S1—C6	1.701 (5)	C8—H8A	0.9600
S2A—C15	1.609 (7)	C8—H8B	0.9600
S2A—C16	1.715 (5)	C8—H8C	0.9600
S2B—C16	1.715 (5)	C9—H9A	0.9600
S2B—C15	1.609 (7)	C9—H9B	0.9600
O1A—C1	1.26 (3)	C9—H9C	0.9600
O1B—C1	1.24 (2)	C10—H10A	0.9600
O2A—C1	1.240 (19)	C10—H10B	0.9600
O2B—C1	1.23 (3)	C10—H10C	0.9600
O4—C11	1.281 (5)	C12—H12A	0.9700
O5—C11	1.204 (6)	C12—H12B	0.9700
C1—C2	1.511 (5)	C14—H14	0.9300
C2—C3	1.498 (5)	C15—H15	0.9300
C3—C4	1.399 (6)	C16—H16A	0.9300

O1A—Sn1—O3	91.9 (6)	C3—C4—C5	115.2 (4)
O1A—Sn1—O4	167.3 (7)	S1—C5—C4	109.0 (3)
O1A—Sn1—C7	95.5 (6)	S1—C6—C3	113.4 (3)
O1A—Sn1—C8	82.7 (5)	O4—C11—C12	116.3 (4)
O3—Sn1—O4	77.69 (9)	O4—C11—O5	121.5 (4)
O3—Sn1—C7	104.94 (15)	O5—C11—C12	122.2 (4)
O3—Sn1—C8	104.92 (14)	C11—C12—C13	111.4 (4)
O1B—Sn1—O3	90.8 (9)	C12—C13—C14	124.0 (5)
O4—Sn1—C7	94.25 (15)	C12—C13—C16	125.7 (5)
O4—Sn1—C8	92.93 (15)	C14—C13—C16	110.4 (4)
O1B—Sn1—O4	164.9 (12)	C13—C14—C15	115.1 (5)
C7—Sn1—C8	150.12 (18)	S2A—C15—C14	108.6 (4)
O1B—Sn1—C7	79.1 (9)	S2B—C15—C14	108.6 (4)
O1B—Sn1—C8	99.6 (11)	S2A—C16—C13	110.5 (4)
O2A—Sn2—O3	89.1 (6)	S2B—C16—C13	110.5 (4)
O2A—Sn2—C9	90.5 (6)	C1—C2—H2A	108.00
O2A—Sn2—C10	80.5 (4)	C1—C2—H2B	108.00
Sn2ⁱ—Sn2—O2A	128.1 (6)	C3—C2—H2A	108.00
O2A—Sn2—O3ⁱ	164.4 (7)	C3—C2—H2B	108.00
O2A—Sn2—O4ⁱ	128.2 (6)	H2A—C2—H2B	107.00
O3—Sn2—C9	105.78 (15)	C3—C4—H4	122.00
O3—Sn2—C10	105.39 (14)	C5—C4—H4	122.00
O2B—Sn2—O3	89.1 (7)	S1—C5—H5	126.00
Sn2ⁱ—Sn2—O3	39.25 (6)	C4—C5—H5	125.00
O3—Sn2—O3ⁱ	76.53 (8)	S1—C6—H6A	123.00
O3—Sn2—O4ⁱ	142.67 (8)	C3—C6—H6A	123.00
C9—Sn2—C10	147.33 (19)	Sn1—C7—H7A	109.00
O2B—Sn2—C9	73.5 (9)	Sn1—C7—H7B	110.00
Sn2ⁱ—Sn2—C9	105.84 (16)	Sn1—C7—H7C	109.00
O3ⁱ—Sn2—C9	99.16 (16)	H7A—C7—H7B	109.00
O4ⁱ—Sn2—C9	78.01 (15)	H7A—C7—H7C	109.00
O2B—Sn2—C10	97.5 (12)	H7B—C7—H7C	109.00
Sn2ⁱ—Sn2—C10	104.38 (12)	Sn1—C8—H8A	109.00
O3ⁱ—Sn2—C10	97.34 (14)	Sn1—C8—H8B	109.00
O4ⁱ—Sn2—C10	83.18 (14)	Sn1—C8—H8C	109.00
Sn2ⁱ—Sn2—O2B	127.4 (8)	H8A—C8—H8B	110.00
O2B—Sn2—O3ⁱ	161.6 (11)	H8A—C8—H8C	109.00
O2B—Sn2—O4ⁱ	126.4 (5)	H8B—C8—H8C	109.00
Sn2ⁱ—Sn2—O3ⁱ	37.29 (5)	Sn2—C9—H9A	109.00
Sn2ⁱ—Sn2—O4ⁱ	103.52 (6)	Sn2—C9—H9B	109.00
O3ⁱ—Sn2—O4ⁱ	66.28 (8)	Sn2—C9—H9C	109.00
C5—S1—C6	92.5 (2)	H9A—C9—H9B	109.00
C15—S2A—C16	95.4 (3)	H9A—C9—H9C	109.00
C15—S2B—C16	95.4 (3)	H9B—C9—H9C	110.00
Sn1—O1A—C1	133.2 (11)	Sn2—C10—H10A	109.00
Sn1—O1B—C1	134 (2)	Sn2—C10—H10B	109.00
Sn2—O2A—C1	132.8 (12)	Sn2—C10—H10C	109.00
Sn2—O2B—C1	134 (2)	H10A—C10—H10B	109.00
Sn2—O3—Sn2ⁱ	103.47 (9)	H10A—C10—H10C	110.00
Sn1—O3—Sn2ⁱ	120.70 (10)	H10B—C10—H10C	110.00
Sn1—O3—Sn2	135.83 (11)	C11—C12—H12A	109.00
Sn2ⁱ—O4—C11	149.5 (3)	C11—C12—H12B	109.00
Sn1—O4—Sn2ⁱ	95.14 (9)	C13—C12—H12A	109.00
Sn1—O4—C11	115.4 (3)	C13—C12—H12B	109.00
O1A—C1—O2A	125.9 (13)	H12A—C12—H12B	108.00
O1A—C1—C2	114.1 (9)	C13—C14—H14	122.00
O2A—C1—C2	120.0 (10)	C15—C14—H14	122.00
O1B—C1—O2B	125 (3)	S2A—C15—H15	126.00
O1B—C1—C2	118 (2)	C14—C15—H15	126.00
O2B—C1—C2	116.6 (18)	S2B—C15—H15	126.00
C1—C2—C3	116.3 (3)	S2A—C16—H16A	125.00
C2—C3—C4	125.4 (4)	C13—C16—H16A	125.00
C2—C3—C6	124.6 (4)	S2B—C16—H16A	125.00
C4—C3—C6	110.0 (4)

O3—Sn1—O1A—C1	−29 (2)	C10—Sn2—Sn2ⁱ—O2Aⁱ	−90.9 (6)
C7—Sn1—O1A—C1	76 (2)	C10—Sn2—Sn2ⁱ—O3ⁱ	−83.16 (16)
C8—Sn1—O1A—C1	−134 (2)	C10—Sn2—Sn2ⁱ—C9ⁱ	12.55 (19)
O1A—Sn1—O3—Sn2	11.1 (6)	C10—Sn2—Sn2ⁱ—C10ⁱ	180.0 (2)
O1A—Sn1—O3—Sn2ⁱ	−168.5 (6)	O3ⁱ—Sn2—Sn2ⁱ—O3	180.00 (14)
O4—Sn1—O3—Sn2	−176.29 (17)	O3ⁱ—Sn2—Sn2ⁱ—O4	176.85 (11)
O4—Sn1—O3—Sn2ⁱ	4.13 (11)	O4ⁱ—Sn2—Sn2ⁱ—O3	−176.85 (11)
C7—Sn1—O3—Sn2	−85.1 (2)	O4ⁱ—Sn2—Sn2ⁱ—O4	180.00 (8)
C7—Sn1—O3—Sn2ⁱ	95.29 (17)	O3—Sn2—O3ⁱ—Sn1ⁱ	−179.70 (13)
C8—Sn1—O3—Sn2	94.0 (2)	O3—Sn2—O3ⁱ—Sn2ⁱ	0.00 (10)
C8—Sn1—O3—Sn2ⁱ	−85.63 (17)	C9—Sn2—O3ⁱ—Sn1ⁱ	76.14 (17)
O3—Sn1—O4—C11	178.3 (3)	C9—Sn2—O3ⁱ—Sn2ⁱ	−104.16 (16)
O3—Sn1—O4—Sn2ⁱ	−2.84 (8)	C10—Sn2—O3ⁱ—Sn1ⁱ	−75.56 (16)
C7—Sn1—O4—C11	73.9 (3)	C10—Sn2—O3ⁱ—Sn2ⁱ	104.14 (15)
C7—Sn1—O4—Sn2ⁱ	−107.23 (15)	O2A—Sn2—O4ⁱ—Sn1ⁱ	170.4 (6)
C8—Sn1—O4—C11	−77.1 (3)	O2A—Sn2—O4ⁱ—C11ⁱ	−7.7 (8)
C8—Sn1—O4—Sn2ⁱ	101.80 (14)	O3—Sn2—O4ⁱ—Sn1ⁱ	−8.27 (18)
O3—Sn2—O2A—C1	−35 (2)	O3—Sn2—O4ⁱ—C11ⁱ	173.7 (5)
C9—Sn2—O2A—C1	71 (2)	C9—Sn2—O4ⁱ—Sn1ⁱ	−108.63 (18)
C10—Sn2—O2A—C1	−140 (2)	C9—Sn2—O4ⁱ—C11ⁱ	73.3 (5)
Sn2ⁱ—Sn2—O2A—C1	−39 (2)	C10—Sn2—O4ⁱ—Sn1ⁱ	98.23 (15)
O4ⁱ—Sn2—O2A—C1	146.3 (19)	C10—Sn2—O4ⁱ—C11ⁱ	−79.9 (5)
O2A—Sn2—O3—Sn1	6.5 (5)	C6—S1—C5—C4	−0.7 (4)
O2A—Sn2—O3—Sn2ⁱ	−173.9 (5)	C5—S1—C6—C3	−0.3 (5)
C9—Sn2—O3—Sn1	−83.8 (2)	C16—S2A—C15—C14	0.2 (4)
C9—Sn2—O3—Sn2ⁱ	95.88 (17)	C15—S2A—C16—C13	0.0 (4)
C10—Sn2—O3—Sn1	86.34 (19)	Sn1—O1A—C1—O2A	13 (3)
C10—Sn2—O3—Sn2ⁱ	−94.03 (15)	Sn1—O1A—C1—C2	−166.7 (15)
Sn2ⁱ—Sn2—O3—Sn1	−179.6 (2)	Sn2—O2A—C1—O1A	29 (3)
O3ⁱ—Sn2—O3—Sn1	−179.63 (17)	Sn2—O2A—C1—C2	−152.2 (14)
O3ⁱ—Sn2—O3—Sn2ⁱ	0.00 (8)	Sn1—O4—C11—O5	1.2 (5)
O4ⁱ—Sn2—O3—Sn1	−174.57 (12)	Sn1—O4—C11—C12	−178.2 (3)
O4ⁱ—Sn2—O3—Sn2ⁱ	5.06 (18)	Sn2ⁱ—O4—C11—O5	−176.6 (3)
O2A—Sn2—Sn2ⁱ—O3	7.8 (6)	Sn2ⁱ—O4—C11—C12	4.0 (7)
O2A—Sn2—Sn2ⁱ—O4	4.6 (6)	O1A—C1—C2—C3	−171.2 (13)
O2A—Sn2—Sn2ⁱ—O2Aⁱ	−180.0 (8)	O2A—C1—C2—C3	9.5 (13)
O2A—Sn2—Sn2ⁱ—O3ⁱ	−172.2 (6)	C1—C2—C3—C4	78.1 (5)
O2A—Sn2—Sn2ⁱ—C9ⁱ	−76.5 (6)	C1—C2—C3—C6	−102.5 (5)
O2A—Sn2—Sn2ⁱ—C10ⁱ	90.9 (6)	C2—C3—C4—C5	177.7 (4)
O3—Sn2—Sn2ⁱ—O4	−3.15 (11)	C6—C3—C4—C5	−1.7 (6)
O3—Sn2—Sn2ⁱ—O2Aⁱ	172.2 (6)	C2—C3—C6—S1	−178.3 (3)
O3—Sn2—Sn2ⁱ—O3ⁱ	−180.00 (14)	C4—C3—C6—S1	1.2 (6)
O3—Sn2—Sn2ⁱ—C9ⁱ	−84.29 (17)	C3—C4—C5—S1	1.5 (6)
O3—Sn2—Sn2ⁱ—C10ⁱ	83.16 (16)	O4—C11—C12—C13	−68.4 (5)
C9—Sn2—Sn2ⁱ—O3	−95.71 (17)	O5—C11—C12—C13	112.2 (5)
C9—Sn2—Sn2ⁱ—O4	−98.86 (15)	C11—C12—C13—C14	−61.4 (6)
C9—Sn2—Sn2ⁱ—O2Aⁱ	76.5 (6)	C11—C12—C13—C16	118.7 (5)
C9—Sn2—Sn2ⁱ—O3ⁱ	84.29 (17)	C12—C13—C14—C15	−179.6 (4)
C9—Sn2—Sn2ⁱ—C9ⁱ	−180.0 (2)	C16—C13—C14—C15	0.3 (6)
C9—Sn2—Sn2ⁱ—C10ⁱ	−12.55 (19)	C12—C13—C16—S2A	179.8 (4)
C10—Sn2—Sn2ⁱ—O3	96.85 (16)	C14—C13—C16—S2A	−0.2 (5)
C10—Sn2—Sn2ⁱ—O4	93.70 (15)	C13—C14—C15—S2A	−0.4 (6)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O5ⁱⁱ	0.96	2.58	3.103 (6)	115
C5—H5···CgCⁱⁱⁱ	0.93	2.83	3.513 (5)	131
C10—H10C···CgCⁱ	0.96	2.80	3.697 (5)	156

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	[Sn₄(CH₃)₈(C₆H₅O₂S)₄O₂]
M_r	1191.79
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.7330 (5), 9.7403 (5), 12.0432 (6)
α, β, γ (°)	85.407 (2), 85.259 (1), 71.256 (2)
V (Å³)	1075.74 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.20 × 0.15 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.637, 0.719
No. of measured, independent and observed [I > 2σ(I)] reflections	19310, 4012, 3441
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.059, 1.04
No. of reflections	4012
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.65

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Sn1—O1A	2.23 (2)	Sn2—O3	2.0366 (19)
Sn1—O3	2.031 (2)	Sn2—C9	2.106 (5)
Sn1—O4	2.207 (3)	Sn2—C10	2.109 (4)
Sn1—C7	2.088 (5)	Sn2—O3ⁱ	2.127 (2)
Sn1—C8	2.091 (4)	Sn2—O4ⁱ	2.670 (3)
Sn2—O2A	2.312 (17)