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The title compound, [Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2], contains the well known structural unit of four organotin units linked by O-atom bridges into a ladder-type centrosymmetric tetra­mer. The SnIV atoms are coordinated in distorted SnC2O3 trigonal–bipyramidal geometries.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052804/hb2613sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052804/hb2613Isup2.hkl
Contains datablock I

CCDC reference: 667255

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.036
  • wR factor = 0.077
  • Data-to-parameter ratio = 20.1

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O5 .. 5.12 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C36
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 5 Informative message, check

Comment top

Some organotin(IV) derivatives of sulfonates show antitumor activities (Chandrasekhar et al., 2003). In this paper, we report the structure of a new organotin sulfonate, [Sn4(Bz)8(L)2(OCH3)2(O)2], (I), where Bz = the benzyl group and L = p-toluenesulfonate.

Selected bond lengths for (I) are listed in Table 1. Both Sn(IV) atoms are five-coordinated in distorted trigonal–bipyramidal geometries. The exo tin atom (Sn1) is coordinated by two benzyl groups, one µ3-O2- anion, one µ2-OCH3- anion and one L O atom. The endo tin atom (Sn2) is coordinated by two benzyl groups, two µ3-O2- anions, one µ2-OCH3- anion and one L O atom. The four Sn(IV) atoms are connected by two µ3-O2- anions, generating the title Sn—O ladder structure. The p-toluenesulfonate anions and µ2-OCH3- anion are attached on both sides of the ladder.

Related literature top

For related literature, see: Chandrasekhar et al. (2003).

Experimental top

A solution of p-toluenesulfonic aicd (100 mmol) in water (20 ml) was added to a mixture of Ag2CO3 (50 mmol) in water (20 ml). After stirring for several minutes until no CO2 was given off, the white precipitate (AgL) was collected by removing the solvent in vacuo. Then a mixture of AgL (1.0 mmol) and Bz2SnCl2 (1.0 mmol) in CH2Cl2 (30 ml) were stirred continuously for 24 h at room temperature, the precipitate of AgCl was removed by filtration. Colourless blocks of (I) were obtained by evaporating the filtrate at room temperature.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.9and refined as riding atoms with C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate but not to tip.

Structure description top

Some organotin(IV) derivatives of sulfonates show antitumor activities (Chandrasekhar et al., 2003). In this paper, we report the structure of a new organotin sulfonate, [Sn4(Bz)8(L)2(OCH3)2(O)2], (I), where Bz = the benzyl group and L = p-toluenesulfonate.

Selected bond lengths for (I) are listed in Table 1. Both Sn(IV) atoms are five-coordinated in distorted trigonal–bipyramidal geometries. The exo tin atom (Sn1) is coordinated by two benzyl groups, one µ3-O2- anion, one µ2-OCH3- anion and one L O atom. The endo tin atom (Sn2) is coordinated by two benzyl groups, two µ3-O2- anions, one µ2-OCH3- anion and one L O atom. The four Sn(IV) atoms are connected by two µ3-O2- anions, generating the title Sn—O ladder structure. The p-toluenesulfonate anions and µ2-OCH3- anion are attached on both sides of the ladder.

For related literature, see: Chandrasekhar et al. (2003).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids drawn at the 20% probability level and all H atoms omitted for clarity. Symmetry code: (i) 2 - x, 2 - y, 1 - z.
Octabenzyldi-µ2-methanolato-di-µ3-oxido-bis(p- toluenesulfonato)tetratin(IV) top
Crystal data top
[Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2]F(000) = 1640
Mr = 1640.21Dx = 1.617 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 7979 reflections
a = 11.520 (5) Åθ = 1.6–28.4°
b = 11.302 (4) ŵ = 1.59 mm1
c = 26.219 (11) ÅT = 293 K
β = 99.409 (1)°Block, colourless
V = 3368 (2) Å30.43 × 0.15 × 0.13 mm
Z = 2
Data collection top
Bruker APEX CCD
diffractometer
5980 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
ω scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.747, Tmax = 0.820k = 1511
20431 measured reflectionsl = 2434
7979 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.029P)2 + 0.8649P]
where P = (Fo2 + 2Fc2)/3
7979 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 0.88 e Å3
Crystal data top
[Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2]V = 3368 (2) Å3
Mr = 1640.21Z = 2
Monoclinic, P21/nMo Kα radiation
a = 11.520 (5) ŵ = 1.59 mm1
b = 11.302 (4) ÅT = 293 K
c = 26.219 (11) Å0.43 × 0.15 × 0.13 mm
β = 99.409 (1)°
Data collection top
Bruker APEX CCD
diffractometer
7979 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5980 reflections with I > 2σ(I)
Tmin = 0.747, Tmax = 0.820Rint = 0.033
20431 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 1.04Δρmax = 0.74 e Å3
7979 reflectionsΔρmin = 0.88 e Å3
397 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
xyzUiso*/Ueq
C10.6175 (4)0.1697 (5)0.5096 (2)0.0794 (15)
H10.59400.13840.53910.095*
C20.5355 (4)0.1953 (5)0.4674 (3)0.0826 (17)
H20.45600.18210.46790.099*
C30.5714 (4)0.2403 (4)0.4247 (2)0.0740 (15)
H30.51610.25780.39570.089*
C40.6885 (4)0.2604 (3)0.42368 (17)0.0559 (11)
H40.71120.29230.39410.067*
C50.7735 (3)0.2341 (3)0.46587 (15)0.0395 (9)
C60.7349 (4)0.1900 (4)0.50868 (18)0.0570 (11)
H60.78960.17330.53800.068*
C70.9010 (3)0.2574 (3)0.46511 (14)0.0385 (9)
H7A0.90660.31230.43720.046*
H7B0.93350.29670.49720.046*
C81.2273 (4)0.2390 (4)0.37217 (17)0.0552 (11)
H81.20370.30510.38890.066*
C91.2649 (4)0.2526 (5)0.3254 (2)0.0735 (15)
H91.26620.32750.31080.088*
C101.3005 (4)0.1567 (6)0.30022 (18)0.0767 (15)
H101.32620.16630.26860.092*
C111.2983 (4)0.0470 (5)0.3216 (2)0.0715 (14)
H111.32240.01860.30460.086*
C121.2600 (4)0.0331 (4)0.36872 (17)0.0559 (11)
H121.25880.04200.38300.067*
C131.2238 (3)0.1290 (3)0.39479 (14)0.0368 (8)
C141.1905 (3)0.1172 (3)0.44700 (15)0.0424 (9)
H14A1.22910.04670.46270.051*
H14B1.22460.18400.46740.051*
C150.5976 (3)0.0233 (3)0.30526 (17)0.0513 (11)
H150.63080.09460.31800.062*
C160.5459 (4)0.0161 (4)0.25441 (18)0.0633 (13)
H160.54440.08190.23300.076*
C170.4961 (4)0.0893 (4)0.23504 (18)0.0659 (13)
H170.46170.09520.20050.079*
C180.4979 (4)0.1853 (4)0.26744 (17)0.0598 (12)
H180.46350.25610.25480.072*
C190.5501 (3)0.1771 (3)0.31809 (16)0.0498 (10)
H190.55080.24300.33940.060*
C200.6018 (3)0.0730 (3)0.33828 (15)0.0421 (9)
C210.6640 (3)0.0670 (3)0.39339 (15)0.0465 (10)
H21A0.65910.01290.40640.056*
H21B0.62550.11950.41470.056*
C221.0230 (4)0.1157 (4)0.28211 (18)0.0604 (12)
H221.09170.12280.30600.072*
C231.0255 (5)0.0580 (4)0.2367 (2)0.0750 (14)
H231.09650.02740.23000.090*
C240.9264 (6)0.0440 (4)0.20063 (19)0.0798 (16)
H240.92900.00300.17010.096*
C250.8232 (5)0.0918 (4)0.21050 (19)0.0741 (15)
H250.75490.08390.18640.089*
C260.8202 (4)0.1520 (4)0.25627 (17)0.0603 (12)
H260.74980.18500.26240.072*
C270.9203 (3)0.1637 (3)0.29309 (15)0.0435 (9)
C280.9156 (4)0.2233 (3)0.34408 (15)0.0543 (11)
H28A0.86860.29460.33770.065*
H28B0.99470.24700.35920.065*
C290.9053 (4)0.1259 (3)0.33632 (14)0.0498 (10)
H29A0.86280.08330.30750.075*
H29B0.86210.19560.34250.075*
H29C0.98110.14820.32880.075*
C300.8621 (3)0.4827 (3)0.53460 (15)0.0453 (9)
H300.93560.47070.52510.054*
C310.8547 (4)0.5357 (3)0.58147 (16)0.0509 (10)
H310.92310.55820.60330.061*
C320.7461 (4)0.5556 (4)0.59623 (18)0.0595 (12)
C330.6469 (4)0.5159 (4)0.56382 (19)0.0707 (14)
H330.57360.52520.57380.085*
C340.6540 (4)0.4622 (4)0.51658 (18)0.0634 (12)
H340.58640.43660.49510.076*
C350.7634 (3)0.4477 (3)0.50208 (15)0.0437 (9)
C360.7358 (5)0.6198 (4)0.6461 (2)0.0920 (18)
H36A0.81280.64140.66350.138*
H36B0.69900.56880.66800.138*
H36C0.68900.68980.63840.138*
O10.9200 (2)0.05216 (19)0.38134 (8)0.0369 (6)
O20.94751 (19)0.06087 (18)0.46365 (8)0.0309 (5)
O30.6557 (3)0.3742 (3)0.41211 (12)0.0726 (10)
O40.8481 (3)0.4679 (2)0.41599 (12)0.0740 (9)
O50.8325 (2)0.2759 (2)0.44978 (10)0.0483 (7)
Sn10.84442 (2)0.116534 (19)0.398869 (9)0.03191 (7)
Sn21.009325 (19)0.106902 (18)0.456013 (9)0.02769 (7)
S10.77362 (9)0.38944 (8)0.43973 (4)0.0467 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.056 (3)0.089 (4)0.100 (4)0.004 (3)0.031 (3)0.015 (3)
C20.033 (3)0.079 (4)0.135 (6)0.006 (2)0.012 (3)0.005 (4)
C30.043 (3)0.078 (3)0.091 (4)0.013 (2)0.019 (3)0.008 (3)
C40.054 (3)0.056 (3)0.053 (3)0.010 (2)0.004 (2)0.000 (2)
C50.039 (2)0.0277 (17)0.050 (2)0.0040 (14)0.0011 (18)0.0042 (16)
C60.043 (2)0.062 (3)0.065 (3)0.009 (2)0.007 (2)0.010 (2)
C70.042 (2)0.0266 (17)0.045 (2)0.0005 (14)0.0030 (17)0.0021 (15)
C80.054 (3)0.051 (2)0.063 (3)0.0043 (19)0.018 (2)0.009 (2)
C90.061 (3)0.089 (4)0.075 (4)0.002 (3)0.024 (3)0.038 (3)
C100.060 (3)0.136 (5)0.038 (3)0.012 (3)0.020 (2)0.011 (3)
C110.063 (3)0.094 (4)0.060 (3)0.011 (3)0.019 (3)0.021 (3)
C120.061 (3)0.054 (3)0.056 (3)0.006 (2)0.020 (2)0.009 (2)
C130.0265 (17)0.046 (2)0.038 (2)0.0017 (14)0.0069 (15)0.0002 (16)
C140.0313 (19)0.055 (2)0.041 (2)0.0035 (16)0.0082 (16)0.0006 (18)
C150.044 (2)0.046 (2)0.061 (3)0.0000 (18)0.001 (2)0.001 (2)
C160.059 (3)0.066 (3)0.062 (3)0.004 (2)0.002 (2)0.022 (2)
C170.058 (3)0.089 (4)0.044 (3)0.008 (2)0.011 (2)0.002 (2)
C180.055 (3)0.057 (3)0.060 (3)0.008 (2)0.011 (2)0.010 (2)
C190.048 (2)0.044 (2)0.053 (3)0.0027 (18)0.008 (2)0.0032 (19)
C200.034 (2)0.043 (2)0.046 (2)0.0010 (16)0.0008 (17)0.0018 (18)
C210.042 (2)0.047 (2)0.048 (2)0.0035 (17)0.0024 (19)0.0099 (19)
C220.058 (3)0.072 (3)0.051 (3)0.005 (2)0.009 (2)0.001 (2)
C230.084 (4)0.079 (3)0.070 (4)0.008 (3)0.037 (3)0.005 (3)
C240.129 (5)0.074 (3)0.044 (3)0.019 (3)0.038 (3)0.008 (2)
C250.082 (4)0.099 (4)0.039 (3)0.012 (3)0.001 (3)0.005 (3)
C260.060 (3)0.071 (3)0.050 (3)0.001 (2)0.011 (2)0.016 (2)
C270.053 (2)0.041 (2)0.039 (2)0.0054 (18)0.0135 (19)0.0079 (17)
C280.082 (3)0.040 (2)0.043 (2)0.011 (2)0.016 (2)0.0018 (18)
C290.070 (3)0.047 (2)0.030 (2)0.0069 (19)0.0003 (19)0.0088 (17)
C300.050 (2)0.038 (2)0.048 (3)0.0009 (17)0.009 (2)0.0003 (18)
C310.059 (3)0.048 (2)0.046 (3)0.0091 (19)0.009 (2)0.0073 (19)
C320.069 (3)0.054 (3)0.056 (3)0.000 (2)0.014 (3)0.006 (2)
C330.058 (3)0.089 (3)0.070 (4)0.011 (3)0.025 (3)0.013 (3)
C340.045 (3)0.079 (3)0.065 (3)0.009 (2)0.007 (2)0.012 (3)
C350.051 (2)0.037 (2)0.045 (2)0.0054 (17)0.0098 (19)0.0037 (17)
C360.127 (5)0.095 (4)0.062 (3)0.003 (3)0.041 (3)0.032 (3)
O10.0528 (15)0.0330 (12)0.0234 (13)0.0078 (11)0.0017 (11)0.0058 (10)
O20.0405 (13)0.0277 (11)0.0226 (12)0.0075 (10)0.0002 (10)0.0002 (9)
O30.068 (2)0.074 (2)0.065 (2)0.0164 (16)0.0195 (17)0.0156 (16)
O40.113 (3)0.0529 (18)0.064 (2)0.0100 (17)0.038 (2)0.0005 (15)
O50.0612 (17)0.0426 (14)0.0393 (15)0.0127 (12)0.0023 (13)0.0162 (12)
Sn10.03670 (14)0.03096 (13)0.02622 (13)0.00300 (10)0.00032 (10)0.00190 (10)
Sn20.03021 (12)0.02620 (12)0.02663 (12)0.00233 (9)0.00452 (9)0.00210 (9)
S10.0593 (6)0.0383 (5)0.0411 (6)0.0080 (4)0.0038 (5)0.0014 (4)
Geometric parameters (Å, º) top
C1—C21.363 (7)C22—H220.9300
C1—C61.376 (6)C23—C241.368 (7)
C1—H10.9300C23—H230.9300
C2—C31.354 (7)C24—C251.367 (7)
C2—H20.9300C24—H240.9300
C3—C41.372 (6)C25—C261.385 (6)
C3—H30.9300C25—H250.9300
C4—C51.384 (5)C26—C271.384 (5)
C4—H40.9300C26—H260.9300
C5—C61.367 (6)C27—C281.506 (5)
C5—C71.495 (5)C28—H28A0.9700
C6—H60.9300C28—H28B0.9700
C7—H7A0.9700C29—O11.432 (4)
C7—H7B0.9700C29—H29A0.9600
C8—C91.375 (6)C29—H29B0.9600
C8—C131.381 (5)C29—H29C0.9600
C8—H80.9300C30—C351.364 (5)
C9—C101.366 (7)C30—C311.382 (5)
C9—H90.9300C30—H300.9300
C10—C111.363 (7)C31—C321.387 (6)
C10—H100.9300C31—H310.9300
C11—C121.387 (6)C32—C331.383 (6)
C11—H110.9300C32—C361.517 (6)
C12—C131.381 (5)C33—C341.394 (6)
C12—H120.9300C33—H330.9300
C13—C141.486 (5)C34—C351.384 (6)
C14—H14A0.9700C34—H340.9300
C14—H14B0.9700C35—S11.784 (4)
C15—C161.371 (5)C36—H36A0.9600
C15—C201.387 (5)C36—H36B0.9600
C15—H150.9300C36—H36C0.9600
C16—C171.383 (6)Sn1—O12.176 (2)
C16—H160.9300Sn1—O22.008 (2)
C17—C181.376 (6)Sn1—O52.260 (2)
C17—H170.9300Sn1—C212.134 (4)
C18—C191.368 (5)Sn1—C282.140 (4)
C18—H180.9300Sn2—O22.047 (2)
C19—C201.384 (5)Sn2—O2i2.148 (2)
C19—H190.9300Sn2—O2i2.148 (2)
C20—C211.506 (5)Sn2—C72.146 (3)
C21—H21A0.9700Sn2—C142.142 (4)
C21—H21B0.9700O3—S11.442 (3)
C22—C231.362 (6)O4—S11.444 (3)
C22—C271.373 (6)O5—S11.455 (2)
C2—C1—C6120.2 (5)C23—C24—H24120.8
C2—C1—H1119.9C24—C25—C26120.2 (5)
C6—C1—H1119.9C24—C25—H25119.9
C3—C2—C1119.0 (5)C26—C25—H25119.9
C3—C2—H2120.5C27—C26—C25121.0 (5)
C1—C2—H2120.5C27—C26—H26119.5
C2—C3—C4120.9 (5)C25—C26—H26119.5
C2—C3—H3119.6C22—C27—C26117.6 (4)
C4—C3—H3119.6C22—C27—C28121.3 (4)
C3—C4—C5121.2 (5)C26—C27—C28121.0 (4)
C3—C4—H4119.4C27—C28—Sn1114.6 (2)
C5—C4—H4119.4C27—C28—H28A108.6
C6—C5—C4116.9 (4)Sn1—C28—H28A108.6
C6—C5—C7121.8 (3)C27—C28—H28B108.6
C4—C5—C7121.3 (4)Sn1—C28—H28B108.6
C5—C6—C1121.8 (4)H28A—C28—H28B107.6
C5—C6—H6119.1O1—C29—H29A109.5
C1—C6—H6119.1O1—C29—H29B109.5
C5—C7—Sn2116.9 (2)H29A—C29—H29B109.5
C5—C7—H7A108.1O1—C29—H29C109.5
Sn2—C7—H7A108.1H29A—C29—H29C109.5
C5—C7—H7B108.1H29B—C29—H29C109.5
Sn2—C7—H7B108.1C35—C30—C31121.0 (4)
H7A—C7—H7B107.3C35—C30—H30119.5
C9—C8—C13121.3 (4)C31—C30—H30119.5
C9—C8—H8119.3C30—C31—C32120.5 (4)
C13—C8—H8119.3C30—C31—H31119.7
C10—C9—C8120.3 (4)C32—C31—H31119.7
C10—C9—H9119.8C33—C32—C31117.9 (4)
C8—C9—H9119.8C33—C32—C36120.7 (5)
C11—C10—C9119.7 (4)C31—C32—C36121.3 (4)
C11—C10—H10120.1C32—C33—C34121.7 (5)
C9—C10—H10120.1C32—C33—H33119.2
C10—C11—C12119.9 (4)C34—C33—H33119.2
C10—C11—H11120.0C35—C34—C33119.0 (4)
C12—C11—H11120.0C35—C34—H34120.5
C13—C12—C11121.2 (4)C33—C34—H34120.5
C13—C12—H12119.4C30—C35—C34119.8 (4)
C11—C12—H12119.4C30—C35—S1120.5 (3)
C8—C13—C12117.4 (4)C34—C35—S1119.7 (3)
C8—C13—C14120.4 (3)C32—C36—H36A109.5
C12—C13—C14122.0 (3)C32—C36—H36B109.5
C13—C14—Sn2120.6 (2)H36A—C36—H36B109.5
C13—C14—H14A107.2C32—C36—H36C109.5
Sn2—C14—H14A107.2H36A—C36—H36C109.5
C13—C14—H14B107.2H36B—C36—H36C109.5
Sn2—C14—H14B107.2C29—O1—Sn2123.9 (2)
H14A—C14—H14B106.8C29—O1—Sn1133.3 (2)
C16—C15—C20121.7 (4)Sn2—O1—Sn1102.02 (9)
C16—C15—H15119.1Sn1—O2—Sn2112.00 (10)
C20—C15—H15119.1Sn1—O2—Sn2i139.81 (11)
C15—C16—C17119.8 (4)Sn2—O2—Sn2i106.98 (9)
C15—C16—H16120.1S1—O5—Sn1131.89 (15)
C17—C16—H16120.1O2—Sn1—C21114.17 (12)
C18—C17—C16119.3 (4)O2—Sn1—C28120.39 (14)
C18—C17—H17120.4C21—Sn1—C28125.36 (16)
C16—C17—H17120.4O2—Sn1—O172.69 (8)
C19—C18—C17120.4 (4)C21—Sn1—O1100.08 (13)
C19—C18—H18119.8C28—Sn1—O198.14 (13)
C17—C18—H18119.8O2—Sn1—O580.49 (9)
C18—C19—C20121.4 (4)C21—Sn1—O595.51 (13)
C18—C19—H19119.3C28—Sn1—O590.81 (13)
C20—C19—H19119.3O1—Sn1—O5152.67 (9)
C19—C20—C15117.4 (4)O2—Sn2—C14114.96 (12)
C19—C20—C21120.9 (3)O2—Sn2—C7120.35 (12)
C15—C20—C21121.7 (3)C14—Sn2—C7124.35 (13)
C20—C21—Sn1111.0 (3)O2—Sn2—O2i73.02 (9)
C20—C21—H21A109.4C14—Sn2—O2i92.74 (12)
Sn1—C21—H21A109.4C7—Sn2—O2i97.39 (11)
C20—C21—H21B109.4O2—Sn2—O172.54 (8)
Sn1—C21—H21B109.4C14—Sn2—O1104.19 (12)
H21A—C21—H21B108.0C7—Sn2—O197.42 (11)
C23—C22—C27121.0 (4)O2i—Sn2—O1145.45 (8)
C23—C22—H22119.5O3—S1—O4115.8 (2)
C27—C22—H22119.5O3—S1—O5111.00 (16)
C22—C23—C24121.6 (5)O4—S1—O5109.10 (19)
C22—C23—H23119.2O3—S1—C35107.8 (2)
C24—C23—H23119.2O4—S1—C35107.54 (18)
C25—C24—C23118.5 (5)O5—S1—C35104.95 (16)
C25—C24—H24120.8
C6—C1—C2—C30.3 (8)Sn2—O2—Sn1—O5178.26 (13)
C1—C2—C3—C40.2 (8)Sn2i—O2—Sn1—O513.22 (18)
C2—C3—C4—C50.8 (7)C20—C21—Sn1—O2160.3 (2)
C3—C4—C5—C61.5 (6)C20—C21—Sn1—C2822.7 (3)
C3—C4—C5—C7179.2 (4)C20—C21—Sn1—O184.9 (3)
C4—C5—C6—C11.7 (6)C20—C21—Sn1—O5117.6 (3)
C7—C5—C6—C1179.3 (4)C27—C28—Sn1—O2112.3 (3)
C2—C1—C6—C51.1 (7)C27—C28—Sn1—C2170.9 (4)
C6—C5—C7—Sn277.6 (4)C27—C28—Sn1—O137.7 (3)
C4—C5—C7—Sn2104.8 (3)C27—C28—Sn1—O5168.2 (3)
C13—C8—C9—C100.3 (7)C29—O1—Sn1—O2176.6 (3)
C8—C9—C10—C110.2 (8)Sn2—O1—Sn1—O26.36 (9)
C9—C10—C11—C120.1 (7)C29—O1—Sn1—C2164.2 (3)
C10—C11—C12—C130.0 (7)Sn2—O1—Sn1—C21105.98 (13)
C9—C8—C13—C120.3 (6)C29—O1—Sn1—C2864.0 (3)
C9—C8—C13—C14175.8 (4)Sn2—O1—Sn1—C28125.75 (14)
C11—C12—C13—C80.1 (6)C29—O1—Sn1—O5171.9 (3)
C11—C12—C13—C14175.6 (4)Sn2—O1—Sn1—O517.8 (3)
C8—C13—C14—Sn285.0 (4)S1—O5—Sn1—O2177.3 (2)
C12—C13—C14—Sn299.6 (4)S1—O5—Sn1—C2169.1 (2)
C20—C15—C16—C170.1 (7)S1—O5—Sn1—C2856.6 (3)
C15—C16—C17—C180.8 (7)S1—O5—Sn1—O1166.20 (17)
C16—C17—C18—C191.0 (7)Sn1—O2—Sn2—C14105.02 (14)
C17—C18—C19—C200.3 (7)Sn2i—O2—Sn2—C1485.01 (15)
C18—C19—C20—C150.6 (6)Sn1—O2—Sn2—C781.28 (16)
C18—C19—C20—C21177.0 (4)Sn2i—O2—Sn2—C788.68 (14)
C16—C15—C20—C190.8 (6)Sn1—O2—Sn2—O2i169.97 (18)
C16—C15—C20—C21176.8 (4)Sn2i—O2—Sn2—O2i0.0
C19—C20—C21—Sn188.0 (4)Sn1—O2—Sn2—O17.15 (10)
C15—C20—C21—Sn189.5 (4)Sn2i—O2—Sn2—O1177.12 (13)
C27—C22—C23—C240.9 (7)C13—C14—Sn2—O297.7 (3)
C22—C23—C24—C251.4 (8)C13—C14—Sn2—C788.9 (3)
C23—C24—C25—C260.5 (8)C13—C14—Sn2—O2i170.2 (3)
C24—C25—C26—C270.9 (7)C13—C14—Sn2—O120.6 (3)
C23—C22—C27—C260.4 (6)C5—C7—Sn2—O212.6 (3)
C23—C22—C27—C28177.5 (4)C5—C7—Sn2—C14174.4 (3)
C25—C26—C27—C221.3 (6)C5—C7—Sn2—O2i87.2 (3)
C25—C26—C27—C28176.6 (4)C5—C7—Sn2—O161.5 (3)
C22—C27—C28—Sn1100.3 (4)C29—O1—Sn2—O2177.7 (3)
C26—C27—C28—Sn177.5 (4)Sn1—O1—Sn2—O26.25 (9)
C35—C30—C31—C320.7 (6)C29—O1—Sn2—C1470.2 (3)
C30—C31—C32—C333.0 (6)Sn1—O1—Sn2—C14118.38 (13)
C30—C31—C32—C36176.5 (4)C29—O1—Sn2—C758.1 (3)
C31—C32—C33—C342.9 (7)Sn1—O1—Sn2—C7113.31 (13)
C36—C32—C33—C34176.6 (5)C29—O1—Sn2—O2i172.8 (2)
C32—C33—C34—C350.5 (7)Sn1—O1—Sn2—O2i1.4 (2)
C31—C30—C35—C341.8 (6)Sn1—O5—S1—O345.4 (3)
C31—C30—C35—S1175.4 (3)Sn1—O5—S1—O483.3 (2)
C33—C34—C35—C301.9 (6)Sn1—O5—S1—C35161.7 (2)
C33—C34—C35—S1175.3 (3)C30—C35—S1—O3173.1 (3)
Sn2—O2—Sn1—C2186.45 (16)C34—C35—S1—O34.1 (4)
Sn2i—O2—Sn1—C2178.6 (2)C30—C35—S1—O447.5 (4)
Sn2—O2—Sn1—C2896.43 (16)C34—C35—S1—O4129.6 (4)
Sn2i—O2—Sn1—C2898.5 (2)C30—C35—S1—O568.5 (3)
Sn2—O2—Sn1—O17.05 (10)C34—C35—S1—O5114.3 (3)
Sn2i—O2—Sn1—O1172.1 (2)
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula[Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2]
Mr1640.21
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.520 (5), 11.302 (4), 26.219 (11)
β (°) 99.409 (1)
V3)3368 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.59
Crystal size (mm)0.43 × 0.15 × 0.13
Data collection
DiffractometerBruker APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.747, 0.820
No. of measured, independent and
observed [I > 2σ(I)] reflections
20431, 7979, 5980
Rint0.033
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.077, 1.04
No. of reflections7979
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 0.88

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT (Bruker, 1999, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Selected bond lengths (Å) top
Sn1—O12.176 (2)Sn2—O22.047 (2)
Sn1—O22.008 (2)Sn2—O2i2.148 (2)
Sn1—O52.260 (2)Sn2—C72.146 (3)
Sn1—C212.134 (4)Sn2—C142.142 (4)
Sn1—C282.140 (4)
Symmetry code: (i) x+2, y, z+1.
 

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