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The title compound, [Sn(C4H9)2(C5H3O2S)2], crystallizes with two mol­ecules in the asymmetric unit, differing just in the orientation of one of the n-butyl groups. The carboxyl­ate groups asymmetrically chelate the Sn atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100126X/cf6038sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100126X/cf6038Isup2.hkl
Contains datablock I

CCDC reference: 159706

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.024
  • wR factor = 0.061
  • Data-to-parameter ratio = 24.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 29.72 From the CIF: _reflns_number_total 10902 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 12046 Completeness (_total/calc) 90.50% Alert C: < 95% complete PLAT_301 Alert C Main residue disorder ........................ 14.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Organotin carboxylates have been the subject of several investigations in recent years (Meriem et al., 1990; Meunier-Pieret et al., 1993; Gielen et al., 1995). They are of interest because of their potential pharmaceutical applications, especially their significant antitumoral activity (Meriem et al., 1991). We have performed the crystal structure determination of the title compound, (I), in order to determine its conformation. It crystallizes with two molecules in the asymmetric unit, which differ only in the orientation of one n-butyl group. The thiophenecarboxylate groups binding the same Sn atom are nearly coplanar and are asymmetrically chelating.

Experimental top

The title compound was prepared by refluxing a suspension of 10 mmol dibutyltin oxide in a solution of 2-thiophenic acid in a mixture of 150 ml chloroform and 50 ml e thanol for 5 h. The product was distilled off and evaporated under vacuum. Crystals suitable for structure determination were obtained from an ethanol solution.

Refinement top

The two thiophene rings are disordered. The resolution of the data did not allow for distinguishing two distinct positions for the S and C atoms. Only one peak was found for each atom in the difference map. Thus, a C and an S atom were refined sharing the same position and the same displacement parameters, and just refining the site-occupation factor of the respective C and S atoms in order to determine the ratio of the different orientations, which turned out to be 0.644 (3) for S13 and C16, 0.810 (3) for S23 and C26, 0.760 (3) for S13A and C16A, and 0.904 (3) for S23A and C26A. All H atoms were located by difference Fourier synthesis and refined with fixed individual displacement parameters [U(H) = 1.2Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å or methylene C—H = 0.99 Å.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A perspective view of molecule 1 of the title compound with the atom-numbering scheme. Displacement ellipsoids are at the 50% probability level.
[Figure 2] Fig. 2. A perspective view of molecule 2 of the title compound with the atom-numbering scheme. Displacement ellipsoids are at the 50% probability level.
(I) top
Crystal data top
[Sn(C4H9)2(C5H3O2S)2]F(000) = 1968
Mr = 487.18Dx = 1.529 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.238 (2) ÅCell parameters from 507 reflections
b = 21.984 (3) Åθ = 2–25°
c = 10.586 (1) ŵ = 1.42 mm1
β = 94.051 (6)°T = 173 K
V = 4233.8 (8) Å3Plate, colourless
Z = 80.50 × 0.40 × 0.20 mm
Data collection top
Siemens CCD three-circle
diffractometer
10902 independent reflections
Radiation source: fine-focus sealed tube9631 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 29.7°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 2422
Tmin = 0.537, Tmax = 0.764k = 3030
76863 measured reflectionsl = 1314
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0258P)2 + 2.4763P]
where P = (Fo2 + 2Fc2)/3
10902 reflections(Δ/σ)max = 0.005
455 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.78 e Å3
Crystal data top
[Sn(C4H9)2(C5H3O2S)2]V = 4233.8 (8) Å3
Mr = 487.18Z = 8
Monoclinic, P21/cMo Kα radiation
a = 18.238 (2) ŵ = 1.42 mm1
b = 21.984 (3) ÅT = 173 K
c = 10.586 (1) Å0.50 × 0.40 × 0.20 mm
β = 94.051 (6)°
Data collection top
Siemens CCD three-circle
diffractometer
10902 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
9631 reflections with I > 2σ(I)
Tmin = 0.537, Tmax = 0.764Rint = 0.023
76863 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.061H-atom parameters constrained
S = 1.13Δρmax = 0.40 e Å3
10902 reflectionsΔρmin = 0.78 e Å3
455 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*/UeqOcc. (<1)
Sn10.501346 (7)0.549230 (5)0.697233 (11)0.02574 (4)
C10.55128 (12)0.61700 (9)0.58945 (19)0.0357 (4)
H1A0.57960.59670.52500.043*
H1B0.51210.64130.54400.043*
C20.60231 (13)0.65987 (10)0.6663 (2)0.0434 (5)
H2A0.57580.67740.73610.052*
H2B0.64480.63650.70430.052*
C30.63022 (16)0.71117 (12)0.5863 (3)0.0624 (8)
H3A0.58770.73470.54890.075*
H3B0.65630.69360.51590.075*
C40.6820 (2)0.75408 (17)0.6622 (5)0.1042 (15)
H4A0.69800.78640.60680.156*
H4B0.72500.73130.69730.156*
H4C0.65640.77210.73150.156*
C50.40527 (11)0.49600 (9)0.71251 (18)0.0314 (4)
H5A0.36610.51170.65160.038*
H5B0.41590.45370.68780.038*
C60.37637 (11)0.49528 (9)0.84445 (18)0.0306 (4)
H6A0.41670.48320.90690.037*
H6B0.36070.53690.86610.037*
C70.31183 (12)0.45182 (10)0.8547 (2)0.0375 (4)
H7A0.27160.46350.79160.045*
H7B0.32760.41010.83440.045*
C80.28321 (15)0.45226 (13)0.9853 (2)0.0549 (6)
H8A0.24210.42370.98770.082*
H8B0.26640.49331.00500.082*
H8C0.32260.44011.04800.082*
C110.46916 (10)0.62570 (8)0.88453 (17)0.0278 (4)
O110.51788 (7)0.58315 (6)0.88488 (12)0.0302 (3)
O120.42940 (8)0.63754 (6)0.78720 (13)0.0328 (3)
C120.46302 (11)0.65913 (8)1.00314 (18)0.0302 (4)
S130.40735 (5)0.71787 (3)1.01286 (8)0.0433 (2)0.644 (3)
C130.40735 (5)0.71787 (3)1.01286 (8)0.0433 (2)0.356 (3)
H130.37450.73750.95230.052*0.356 (3)
C140.42816 (16)0.73016 (11)1.1604 (3)0.0594 (7)
H140.40690.76221.20570.071*
C150.47784 (17)0.69185 (14)1.2145 (2)0.0582 (7)
H150.49350.69451.30180.070*
C160.50737 (7)0.64471 (5)1.13063 (10)0.0449 (4)0.644 (3)
H160.54340.61421.14970.054*0.644 (3)
S160.50737 (7)0.64471 (5)1.13063 (10)0.0449 (4)0.356 (3)
C210.59713 (10)0.45790 (8)0.66479 (18)0.0286 (4)
O210.58977 (8)0.49180 (6)0.76250 (13)0.0340 (3)
O220.55689 (8)0.46560 (6)0.56619 (13)0.0356 (3)
C220.65352 (10)0.41046 (9)0.67363 (19)0.0307 (4)
S230.70905 (4)0.40042 (3)0.80543 (7)0.0449 (2)0.810 (3)
C230.70905 (4)0.40042 (3)0.80543 (7)0.0449 (2)0.190 (3)
H230.71390.42050.88500.054*0.190 (3)
C240.75216 (14)0.34224 (12)0.7443 (3)0.0581 (7)
H240.79070.32040.78930.070*
C250.72720 (13)0.32879 (11)0.6244 (3)0.0525 (6)
H250.74730.29660.57770.063*
C260.66775 (8)0.36677 (7)0.57191 (14)0.0429 (5)0.810 (3)
H260.64320.36420.48990.051*0.810 (3)
S260.66775 (8)0.36677 (7)0.57191 (14)0.0429 (5)0.190 (3)
Sn1A0.029665 (7)0.565324 (6)0.163891 (13)0.03255 (4)
C1A0.07450 (12)0.60125 (11)0.1006 (2)0.0453 (5)
H1A10.09850.57260.03850.054*
H1A20.10540.60350.17370.054*
C2A0.07283 (15)0.66212 (15)0.0414 (4)0.0878 (12)
H2A10.04150.65940.03100.105*
H2A20.04810.69020.10390.105*
C3A0.14330 (15)0.69036 (14)0.0050 (4)0.0681 (8)
H3A10.16800.66230.06760.082*
H3A20.17470.69300.06730.082*
C4A0.1417 (2)0.75031 (19)0.0630 (6)0.144 (3)
H4A10.19200.76330.08830.215*
H4A20.11300.74860.13780.215*
H4A30.11900.77940.00200.215*
C5A0.09980 (12)0.49052 (10)0.2132 (2)0.0404 (5)
H5A10.06990.45290.20770.048*
H5A20.13660.48730.14910.048*
C6A0.14039 (13)0.49262 (11)0.3428 (2)0.0466 (5)
H6A10.10460.49020.40870.056*
H6A20.16690.53180.35330.056*
C7A0.19533 (16)0.44001 (13)0.3604 (3)0.0564 (7)
H7A10.16910.40120.34280.068*
H7A20.23300.44430.29810.068*
C8A0.2326 (2)0.43768 (18)0.4907 (4)0.0972 (14)
H8A10.26650.40300.49700.146*
H8A20.19560.43300.55280.146*
H8A30.26010.47540.50760.146*
C11A0.02769 (11)0.61650 (10)0.39223 (19)0.0362 (4)
O11A0.06495 (8)0.63297 (6)0.29839 (13)0.0355 (3)
O12A0.01238 (10)0.57071 (8)0.38301 (16)0.0483 (4)
C12A0.03493 (12)0.65429 (10)0.50643 (19)0.0378 (4)
S13A0.08783 (4)0.71696 (3)0.51435 (7)0.0455 (2)0.760 (3)
C13A0.08783 (4)0.71696 (3)0.51435 (7)0.0455 (2)0.240 (3)
H13A0.11760.73640.45620.055*0.240 (3)
C14A0.06871 (17)0.73209 (13)0.6612 (2)0.0577 (7)
H14A0.08880.76590.70780.069*
C15A0.02224 (19)0.69224 (17)0.7086 (2)0.0711 (9)
H15A0.00910.69540.79360.085*
C16A0.00750 (12)0.64397 (9)0.62584 (16)0.0715 (7)0.760 (3)
H16A0.04340.61410.64120.086*0.760 (3)
S16A0.00750 (12)0.64397 (9)0.62584 (16)0.0715 (7)0.240 (3)
C21A0.10004 (11)0.58179 (9)0.04998 (19)0.0328 (4)
O21A0.10536 (8)0.61338 (7)0.05319 (13)0.0362 (3)
O22A0.05288 (8)0.54076 (7)0.06439 (15)0.0413 (3)
C22A0.15133 (10)0.59471 (9)0.14670 (19)0.0330 (4)
S23A0.21863 (3)0.64827 (3)0.12090 (6)0.04180 (19)0.904 (3)
C23A0.21863 (3)0.64827 (3)0.12090 (6)0.04180 (19)0.096 (3)
H23A0.23310.67470.05250.050*0.096 (3)
C24A0.24926 (13)0.63554 (13)0.2657 (2)0.0500 (6)
H24A0.28990.65650.29670.060*
C25A0.21049 (14)0.59288 (12)0.3330 (2)0.0489 (6)
H25A0.22090.58160.41650.059*
C26A0.15167 (11)0.56576 (11)0.26722 (19)0.0543 (7)0.904 (3)
H26A0.11930.53450.29850.065*0.904 (3)
S26A0.15167 (11)0.56576 (11)0.26722 (19)0.0543 (7)0.096 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03083 (7)0.02344 (6)0.02275 (6)0.00177 (5)0.00043 (4)0.00081 (4)
C10.0463 (12)0.0294 (10)0.0324 (10)0.0031 (8)0.0089 (8)0.0009 (8)
C20.0410 (12)0.0384 (11)0.0516 (13)0.0084 (9)0.0099 (10)0.0066 (10)
C30.0619 (16)0.0400 (13)0.090 (2)0.0107 (12)0.0353 (15)0.0032 (13)
C40.078 (2)0.065 (2)0.173 (4)0.0387 (19)0.035 (3)0.020 (2)
C50.0357 (10)0.0308 (9)0.0272 (9)0.0038 (7)0.0013 (7)0.0010 (7)
C60.0335 (10)0.0274 (9)0.0309 (9)0.0027 (7)0.0021 (7)0.0014 (7)
C70.0365 (11)0.0371 (11)0.0385 (11)0.0075 (8)0.0008 (8)0.0019 (8)
C80.0497 (14)0.0688 (17)0.0472 (14)0.0256 (12)0.0101 (11)0.0021 (12)
C110.0332 (9)0.0220 (8)0.0287 (9)0.0038 (7)0.0063 (7)0.0003 (7)
O110.0373 (7)0.0269 (6)0.0263 (6)0.0048 (5)0.0014 (5)0.0046 (5)
O120.0386 (7)0.0272 (7)0.0325 (7)0.0009 (5)0.0008 (6)0.0023 (5)
C120.0367 (10)0.0229 (8)0.0322 (9)0.0017 (7)0.0105 (8)0.0024 (7)
S130.0495 (5)0.0311 (4)0.0503 (5)0.0073 (3)0.0109 (3)0.0054 (3)
C130.0495 (5)0.0311 (4)0.0503 (5)0.0073 (3)0.0109 (3)0.0054 (3)
C140.0703 (17)0.0368 (12)0.0757 (18)0.0063 (12)0.0369 (15)0.0236 (12)
C150.0755 (18)0.0691 (18)0.0314 (11)0.0183 (15)0.0132 (11)0.0107 (11)
C160.0619 (8)0.0368 (6)0.0372 (6)0.0022 (5)0.0116 (5)0.0058 (4)
S160.0619 (8)0.0368 (6)0.0372 (6)0.0022 (5)0.0116 (5)0.0058 (4)
C210.0300 (9)0.0246 (9)0.0313 (9)0.0002 (7)0.0035 (7)0.0010 (7)
O210.0373 (7)0.0322 (7)0.0316 (7)0.0084 (6)0.0039 (6)0.0061 (5)
O220.0429 (8)0.0348 (7)0.0284 (7)0.0072 (6)0.0026 (6)0.0011 (5)
C220.0284 (9)0.0271 (9)0.0365 (10)0.0003 (7)0.0022 (7)0.0005 (7)
S230.0462 (4)0.0408 (4)0.0456 (4)0.0116 (3)0.0120 (3)0.0041 (3)
C230.0462 (4)0.0408 (4)0.0456 (4)0.0116 (3)0.0120 (3)0.0041 (3)
C240.0419 (13)0.0422 (13)0.088 (2)0.0109 (10)0.0114 (13)0.0051 (13)
C250.0421 (13)0.0398 (13)0.0779 (18)0.0056 (10)0.0205 (12)0.0118 (12)
C260.0455 (8)0.0404 (8)0.0442 (8)0.0057 (6)0.0126 (6)0.0024 (6)
S260.0455 (8)0.0404 (8)0.0442 (8)0.0057 (6)0.0126 (6)0.0024 (6)
Sn1A0.02985 (7)0.03253 (7)0.03535 (7)0.00594 (5)0.00273 (5)0.00042 (5)
C1A0.0316 (11)0.0509 (13)0.0532 (13)0.0024 (9)0.0020 (9)0.0016 (10)
C2A0.0365 (14)0.0596 (18)0.164 (4)0.0089 (13)0.0137 (18)0.039 (2)
C3A0.0424 (14)0.0568 (17)0.104 (2)0.0032 (12)0.0052 (14)0.0003 (16)
C4A0.064 (2)0.080 (3)0.280 (7)0.004 (2)0.038 (3)0.071 (4)
C5A0.0438 (12)0.0347 (11)0.0421 (11)0.0014 (9)0.0015 (9)0.0031 (9)
C6A0.0466 (13)0.0453 (13)0.0461 (13)0.0032 (10)0.0095 (10)0.0071 (10)
C7A0.0564 (16)0.0546 (15)0.0560 (15)0.0120 (12)0.0110 (12)0.0079 (12)
C8A0.108 (3)0.089 (3)0.086 (3)0.043 (2)0.049 (2)0.020 (2)
C11A0.0346 (10)0.0390 (11)0.0352 (10)0.0021 (8)0.0042 (8)0.0051 (8)
O11A0.0391 (8)0.0361 (7)0.0320 (7)0.0064 (6)0.0069 (6)0.0028 (6)
O12A0.0497 (9)0.0487 (9)0.0477 (9)0.0125 (7)0.0112 (7)0.0037 (7)
C12A0.0365 (11)0.0433 (12)0.0337 (10)0.0093 (9)0.0039 (8)0.0049 (8)
S13A0.0467 (4)0.0476 (4)0.0419 (4)0.0067 (3)0.0010 (3)0.0110 (3)
C13A0.0467 (4)0.0476 (4)0.0419 (4)0.0067 (3)0.0010 (3)0.0110 (3)
C14A0.0727 (18)0.0550 (15)0.0430 (13)0.0248 (14)0.0130 (12)0.0125 (11)
C15A0.087 (2)0.099 (2)0.0282 (12)0.0326 (19)0.0104 (13)0.0042 (13)
C16A0.0938 (15)0.0734 (12)0.0461 (9)0.0015 (10)0.0046 (9)0.0101 (8)
S16A0.0938 (15)0.0734 (12)0.0461 (9)0.0015 (10)0.0046 (9)0.0101 (8)
C21A0.0285 (9)0.0359 (10)0.0337 (10)0.0002 (8)0.0003 (7)0.0001 (8)
O21A0.0358 (7)0.0380 (8)0.0351 (7)0.0086 (6)0.0052 (6)0.0039 (6)
O22A0.0366 (8)0.0437 (8)0.0435 (8)0.0115 (6)0.0034 (6)0.0056 (7)
C22A0.0275 (9)0.0363 (10)0.0347 (10)0.0010 (7)0.0005 (7)0.0011 (8)
S23A0.0353 (3)0.0528 (4)0.0372 (3)0.0112 (2)0.0016 (2)0.0018 (2)
C23A0.0353 (3)0.0528 (4)0.0372 (3)0.0112 (2)0.0016 (2)0.0018 (2)
C24A0.0380 (12)0.0670 (16)0.0459 (13)0.0030 (11)0.0095 (10)0.0089 (11)
C25A0.0487 (13)0.0594 (15)0.0394 (12)0.0071 (11)0.0095 (10)0.0016 (11)
C26A0.0463 (11)0.0716 (15)0.0456 (11)0.0115 (9)0.0076 (8)0.0075 (9)
S26A0.0463 (11)0.0716 (15)0.0456 (11)0.0115 (9)0.0076 (8)0.0075 (9)
Geometric parameters (Å, º) top
Sn1—C12.1209 (19)Sn1A—C1A2.122 (2)
Sn1—C52.1227 (19)Sn1A—C5A2.126 (2)
Sn1—O112.1233 (13)Sn1A—O11A2.1268 (14)
Sn1—O212.1248 (13)Sn1A—O21A2.1503 (14)
Sn1—O222.5553 (14)Sn1A—O12A2.4967 (17)
Sn1—O122.5641 (14)Sn1A—O22A2.5407 (16)
C1—C21.519 (3)C1A—C2A1.479 (4)
C1—H1A0.990C1A—H1A10.990
C1—H1B0.990C1A—H1A20.990
C2—C31.519 (3)C2A—C3A1.480 (4)
C2—H2A0.990C2A—H2A10.990
C2—H2B0.990C2A—H2A20.990
C3—C41.523 (4)C3A—C4A1.455 (5)
C3—H3A0.990C3A—H3A10.990
C3—H3B0.990C3A—H3A20.990
C4—H4A0.980C4A—H4A10.980
C4—H4B0.980C4A—H4A20.980
C4—H4C0.980C4A—H4A30.980
C5—C61.527 (3)C5A—C6A1.513 (3)
C5—H5A0.990C5A—H5A10.990
C5—H5B0.990C5A—H5A20.990
C6—C71.526 (3)C6A—C7A1.533 (3)
C6—H6A0.990C6A—H6A10.990
C6—H6B0.990C6A—H6A20.990
C7—C81.512 (3)C7A—C8A1.495 (4)
C7—H7A0.990C7A—H7A10.990
C7—H7B0.990C7A—H7A20.990
C8—H8A0.980C8A—H8A10.980
C8—H8B0.980C8A—H8A20.980
C8—H8C0.980C8A—H8A30.980
C11—O121.245 (2)C11A—O12A1.244 (3)
C11—O111.290 (2)C11A—O11A1.294 (2)
C11—C121.466 (2)C11A—C12A1.465 (3)
C12—C161.556 (2)C12A—C16A1.545 (3)
C12—S131.650 (2)C12A—S13A1.681 (2)
S13—C141.604 (3)S13A—C14A1.651 (3)
C14—C151.336 (4)C14A—C15A1.341 (5)
C14—H140.950C14A—H14A0.950
C15—C161.490 (3)C15A—C16A1.456 (4)
C15—H150.950C15A—H15A0.950
C16—H160.950C16A—H16A0.950
C21—O221.244 (2)C21A—O22A1.248 (2)
C21—O211.290 (2)C21A—O21A1.292 (2)
C21—C221.463 (3)C21A—C22A1.463 (3)
C22—C261.480 (2)C22A—C26A1.426 (3)
C22—S231.680 (2)C22A—S23A1.709 (2)
S23—C241.656 (3)S23A—C24A1.692 (3)
C24—C251.351 (4)C24A—C25A1.348 (4)
C24—H240.950C24A—H24A0.950
C25—C261.448 (3)C25A—C26A1.448 (3)
C25—H250.950C25A—H25A0.950
C26—H260.950C26A—H26A0.950
C1—Sn1—C5144.73 (8)C5A—Sn1A—O11A103.18 (7)
C1—Sn1—O11102.62 (7)C1A—Sn1A—O21A103.88 (8)
C5—Sn1—O11100.71 (6)C5A—Sn1A—O21A96.64 (8)
C1—Sn1—O21104.33 (7)O11A—Sn1A—O21A81.13 (5)
C5—Sn1—O21105.02 (7)C1A—Sn1A—O12A87.08 (8)
O11—Sn1—O2181.38 (5)C5A—Sn1A—O12A91.57 (8)
C1—Sn1—O2290.67 (7)O11A—Sn1A—O12A56.16 (5)
C5—Sn1—O2290.33 (6)O21A—Sn1A—O12A137.24 (5)
O11—Sn1—O22136.47 (5)C1A—Sn1A—O22A89.10 (8)
O21—Sn1—O2255.12 (5)C5A—Sn1A—O22A86.07 (7)
C1—Sn1—O1285.32 (7)O11A—Sn1A—O22A136.26 (5)
C5—Sn1—O1286.69 (6)O21A—Sn1A—O22A55.22 (5)
O11—Sn1—O1255.19 (5)O12A—Sn1A—O22A167.55 (5)
O21—Sn1—O12136.53 (5)C2A—C1A—Sn1A115.21 (17)
O22—Sn1—O12168.34 (4)C2A—C1A—H1A1108.5
C2—C1—Sn1114.70 (14)Sn1A—C1A—H1A1108.5
C2—C1—H1A108.6C2A—C1A—H1A2108.5
Sn1—C1—H1A108.6Sn1A—C1A—H1A2108.5
C2—C1—H1B108.6H1A1—C1A—H1A2107.5
Sn1—C1—H1B108.6C1A—C2A—C3A118.5 (2)
H1A—C1—H1B107.6C1A—C2A—H2A1107.7
C3—C2—C1112.3 (2)C3A—C2A—H2A1107.7
C3—C2—H2A109.1C1A—C2A—H2A2107.7
C1—C2—H2A109.1C3A—C2A—H2A2107.7
C3—C2—H2B109.1H2A1—C2A—H2A2107.1
C1—C2—H2B109.1C4A—C3A—C2A118.5 (3)
H2A—C2—H2B107.9C4A—C3A—H3A1107.7
C2—C3—C4112.7 (3)C2A—C3A—H3A1107.7
C2—C3—H3A109.1C4A—C3A—H3A2107.7
C4—C3—H3A109.1C2A—C3A—H3A2107.7
C2—C3—H3B109.1H3A1—C3A—H3A2107.1
C4—C3—H3B109.1C3A—C4A—H4A1109.5
H3A—C3—H3B107.8C3A—C4A—H4A2109.5
C3—C4—H4A109.5H4A1—C4A—H4A2109.5
C3—C4—H4B109.5C3A—C4A—H4A3109.5
H4A—C4—H4B109.5H4A1—C4A—H4A3109.5
C3—C4—H4C109.5H4A2—C4A—H4A3109.5
H4A—C4—H4C109.5C6A—C5A—Sn1A116.52 (15)
H4B—C4—H4C109.5C6A—C5A—H5A1108.2
C6—C5—Sn1114.55 (12)Sn1A—C5A—H5A1108.2
C6—C5—H5A108.6C6A—C5A—H5A2108.2
Sn1—C5—H5A108.6Sn1A—C5A—H5A2108.2
C6—C5—H5B108.6H5A1—C5A—H5A2107.3
Sn1—C5—H5B108.6C5A—C6A—C7A111.1 (2)
H5A—C5—H5B107.6C5A—C6A—H6A1109.4
C7—C6—C5112.90 (16)C7A—C6A—H6A1109.4
C7—C6—H6A109.0C5A—C6A—H6A2109.4
C5—C6—H6A109.0C7A—C6A—H6A2109.4
C7—C6—H6B109.0H6A1—C6A—H6A2108.0
C5—C6—H6B109.0C8A—C7A—C6A112.9 (2)
H6A—C6—H6B107.8C8A—C7A—H7A1109.0
C8—C7—C6112.26 (17)C6A—C7A—H7A1109.0
C8—C7—H7A109.2C8A—C7A—H7A2109.0
C6—C7—H7A109.2C6A—C7A—H7A2109.0
C8—C7—H7B109.2H7A1—C7A—H7A2107.8
C6—C7—H7B109.2C7A—C8A—H8A1109.5
H7A—C7—H7B107.9C7A—C8A—H8A2109.5
C7—C8—H8A109.5H8A1—C8A—H8A2109.5
C7—C8—H8B109.5C7A—C8A—H8A3109.5
H8A—C8—H8B109.5H8A1—C8A—H8A3109.5
C7—C8—H8C109.5H8A2—C8A—H8A3109.5
H8A—C8—H8C109.5O12A—C11A—O11A120.2 (2)
H8B—C8—H8C109.5O12A—C11A—C12A122.81 (19)
O12—C11—O11120.99 (17)O11A—C11A—C12A116.95 (19)
O12—C11—C12121.93 (17)O12A—C11A—Sn1A68.48 (12)
O11—C11—C12117.08 (17)O11A—C11A—Sn1A51.78 (10)
C11—O11—Sn1101.52 (11)C12A—C11A—Sn1A168.58 (15)
C11—O12—Sn182.28 (11)C11A—O11A—Sn1A99.66 (12)
C11—C12—C16125.04 (15)C11A—O12A—Sn1A83.91 (12)
C11—C12—S13122.02 (15)C11A—C12A—C16A124.80 (19)
C16—C12—S13112.94 (12)C11A—C12A—S13A121.59 (16)
C14—S13—C1295.06 (13)C16A—C12A—S13A113.49 (15)
C15—C14—S13114.70 (19)C14A—S13A—C12A93.06 (14)
C15—C14—H14122.6C15A—C14A—S13A113.7 (2)
S13—C14—H14122.6C15A—C14A—H14A123.2
C14—C15—C16116.5 (2)S13A—C14A—H14A123.2
C14—C15—H15121.8C14A—C15A—C16A118.0 (2)
C16—C15—H15121.8C14A—C15A—H15A121.0
C15—C16—C12100.80 (15)C16A—C15A—H15A121.0
C15—C16—H16129.6C15A—C16A—C12A101.4 (2)
C12—C16—H16129.6C15A—C16A—H16A129.3
O22—C21—O21120.37 (17)C12A—C16A—H16A129.3
O22—C21—C22121.39 (17)O22A—C21A—O21A120.10 (18)
O21—C21—C22118.24 (17)O22A—C21A—C22A121.60 (18)
C21—O21—Sn1101.67 (11)O21A—C21A—C22A118.28 (17)
C21—O22—Sn182.85 (11)C21A—O21A—Sn1A100.59 (12)
C21—C22—C26125.09 (16)C21A—O22A—Sn1A83.68 (12)
C21—C22—S23121.78 (15)C26A—C22A—C21A125.66 (19)
C26—C22—S23113.12 (13)C26A—C22A—S23A113.71 (16)
C24—S23—C2292.99 (12)C21A—C22A—S23A120.64 (15)
C25—C24—S23113.47 (19)C24A—S23A—C22A91.18 (11)
C25—C24—H24123.3C25A—C24A—S23A113.57 (19)
S23—C24—H24123.3C25A—C24A—H24A123.2
C24—C25—C26115.3 (2)S23A—C24A—H24A123.2
C24—C25—H25122.3C24A—C25A—C26A114.3 (2)
C26—C25—H25122.3C24A—C25A—H25A122.9
C25—C26—C22105.09 (16)C26A—C25A—H25A122.9
C25—C26—H26127.5C22A—C26A—C25A107.3 (2)
C22—C26—H26127.5C22A—C26A—H26A126.4
C1A—Sn1A—C5A151.09 (9)C25A—C26A—H26A126.4
C1A—Sn1A—O11A99.96 (8)
C5—Sn1—C1—C2146.55 (15)O21A—Sn1A—C5A—C6A98.79 (18)
O11—Sn1—C1—C216.27 (17)O12A—Sn1A—C5A—C6A39.16 (18)
O21—Sn1—C1—C267.91 (16)O22A—Sn1A—C5A—C6A153.08 (18)
O22—Sn1—C1—C2121.94 (16)Sn1A—C5A—C6A—C7A173.53 (18)
O12—Sn1—C1—C269.03 (16)C5A—C6A—C7A—C8A175.7 (3)
Sn1—C1—C2—C3174.13 (16)C1A—Sn1A—C11A—O12A76.97 (14)
C1—C2—C3—C4179.5 (2)C5A—Sn1A—C11A—O12A76.69 (14)
C1—Sn1—C5—C6131.66 (15)O11A—Sn1A—C11A—O12A178.4 (2)
O11—Sn1—C5—C60.92 (15)O21A—Sn1A—C11A—O12A176.96 (12)
O21—Sn1—C5—C682.93 (14)O22A—Sn1A—C11A—O12A176.26 (19)
O22—Sn1—C5—C6136.73 (14)C1A—Sn1A—C11A—O11A104.59 (13)
O12—Sn1—C5—C654.56 (14)C5A—Sn1A—C11A—O11A101.76 (13)
Sn1—C5—C6—C7174.48 (14)O21A—Sn1A—C11A—O11A1.48 (14)
C5—C6—C7—C8179.2 (2)O12A—Sn1A—C11A—O11A178.4 (2)
O12—C11—O11—Sn11.7 (2)O22A—Sn1A—C11A—O11A5.3 (3)
C12—C11—O11—Sn1178.39 (13)C1A—Sn1A—C11A—C12A95.0 (8)
C1—Sn1—O11—C1175.91 (12)C5A—Sn1A—C11A—C12A111.4 (7)
C5—Sn1—O11—C1177.45 (12)O11A—Sn1A—C11A—C12A9.6 (7)
O21—Sn1—O11—C11178.77 (12)O21A—Sn1A—C11A—C12A11.1 (8)
O22—Sn1—O11—C11179.43 (10)O12A—Sn1A—C11A—C12A171.9 (8)
O12—Sn1—O11—C110.84 (10)O22A—Sn1A—C11A—C12A4.3 (9)
O11—C11—O12—Sn11.36 (16)O12A—C11A—O11A—Sn1A1.7 (2)
C12—C11—O12—Sn1178.69 (17)C12A—C11A—O11A—Sn1A177.87 (15)
C1—Sn1—O12—C11109.76 (12)C1A—Sn1A—O11A—C11A78.75 (14)
C5—Sn1—O12—C11104.62 (11)C5A—Sn1A—O11A—C11A83.79 (14)
O11—Sn1—O12—C110.86 (10)O21A—Sn1A—O11A—C11A178.59 (13)
O21—Sn1—O12—C113.83 (14)O12A—Sn1A—O11A—C11A0.87 (12)
O22—Sn1—O12—C11180.0 (2)O22A—Sn1A—O11A—C11A177.99 (11)
O12—C11—C12—C16176.28 (16)O11A—C11A—O12A—Sn1A1.42 (19)
O11—C11—C12—C163.8 (3)C12A—C11A—O12A—Sn1A178.11 (19)
O12—C11—C12—S134.6 (3)C1A—Sn1A—O12A—C11A103.16 (14)
O11—C11—C12—S13175.40 (14)C5A—Sn1A—O12A—C11A105.75 (14)
C11—C12—S13—C14179.81 (17)O11A—Sn1A—O12A—C11A0.90 (12)
C16—C12—S13—C140.94 (16)O21A—Sn1A—O12A—C11A4.21 (17)
C12—S13—C14—C150.1 (2)O22A—Sn1A—O12A—C11A175.4 (2)
S13—C14—C15—C161.1 (3)O12A—C11A—C12A—C16A2.4 (3)
C14—C15—C16—C121.6 (3)O11A—C11A—C12A—C16A177.12 (18)
C11—C12—C16—C15179.26 (19)Sn1A—C11A—C12A—C16A168.6 (6)
S13—C12—C16—C151.51 (18)O12A—C11A—C12A—S13A178.35 (17)
O22—C21—O21—Sn10.8 (2)O11A—C11A—C12A—S13A1.2 (3)
C22—C21—O21—Sn1179.00 (14)Sn1A—C11A—C12A—S13A7.3 (9)
C1—Sn1—O21—C2180.99 (13)C11A—C12A—S13A—C14A179.62 (18)
C5—Sn1—O21—C2179.24 (13)C16A—C12A—S13A—C14A4.02 (17)
O11—Sn1—O21—C21178.10 (12)C12A—S13A—C14A—C15A0.8 (2)
O22—Sn1—O21—C210.39 (11)S13A—C14A—C15A—C16A2.9 (3)
O12—Sn1—O21—C21179.44 (10)C14A—C15A—C16A—C12A5.3 (3)
O21—C21—O22—Sn10.63 (17)C11A—C12A—C16A—C15A178.2 (2)
C22—C21—O22—Sn1179.13 (17)S13A—C12A—C16A—C15A5.6 (2)
C1—Sn1—O22—C21107.48 (12)O22A—C21A—O21A—Sn1A7.0 (2)
C5—Sn1—O22—C21107.78 (12)C22A—C21A—O21A—Sn1A171.80 (15)
O11—Sn1—O22—C211.77 (15)C1A—Sn1A—O21A—C21A82.59 (14)
O21—Sn1—O22—C210.40 (11)C5A—Sn1A—O21A—C21A76.89 (13)
O12—Sn1—O22—C21177.2 (2)O11A—Sn1A—O21A—C21A179.26 (13)
O22—C21—C22—C261.5 (3)O12A—Sn1A—O21A—C21A176.47 (11)
O21—C21—C22—C26178.26 (17)O22A—Sn1A—O21A—C21A3.62 (11)
O22—C21—C22—S23178.98 (15)O21A—C21A—O22A—Sn1A5.87 (18)
O21—C21—C22—S231.3 (3)C22A—C21A—O22A—Sn1A172.90 (18)
C21—C22—S23—C24179.18 (18)C1A—Sn1A—O22A—C21A111.35 (14)
C26—C22—S23—C240.39 (17)C5A—Sn1A—O22A—C21A97.17 (13)
C22—S23—C24—C250.5 (2)O11A—Sn1A—O22A—C21A7.83 (16)
S23—C24—C25—C260.5 (3)O21A—Sn1A—O22A—C21A3.71 (11)
C24—C25—C26—C220.2 (3)O12A—Sn1A—O22A—C21A176.6 (2)
C21—C22—C26—C25179.36 (19)O22A—C21A—C22A—C26A3.4 (3)
S23—C22—C26—C250.20 (19)O21A—C21A—C22A—C26A177.80 (19)
C5A—Sn1A—C1A—C2A156.5 (3)O22A—C21A—C22A—S23A176.37 (16)
O11A—Sn1A—C1A—C2A60.6 (3)O21A—C21A—C22A—S23A2.4 (3)
O21A—Sn1A—C1A—C2A22.6 (3)C26A—C22A—S23A—C24A0.42 (17)
O12A—Sn1A—C1A—C2A115.5 (3)C21A—C22A—S23A—C24A179.78 (18)
O22A—Sn1A—C1A—C2A76.3 (3)C22A—S23A—C24A—C25A0.4 (2)
Sn1A—C1A—C2A—C3A179.9 (3)S23A—C24A—C25A—C26A1.2 (3)
C1A—C2A—C3A—C4A179.9 (4)C21A—C22A—C26A—C25A179.1 (2)
C1A—Sn1A—C5A—C6A126.0 (2)S23A—C22A—C26A—C25A1.1 (2)
O11A—Sn1A—C5A—C6A16.38 (19)C24A—C25A—C26A—C22A1.4 (3)

Experimental details

Crystal data
Chemical formula[Sn(C4H9)2(C5H3O2S)2]
Mr487.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)18.238 (2), 21.984 (3), 10.586 (1)
β (°) 94.051 (6)
V3)4233.8 (8)
Z8
Radiation typeMo Kα
µ (mm1)1.42
Crystal size (mm)0.50 × 0.40 × 0.20
Data collection
DiffractometerSiemens CCD three-circle
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.537, 0.764
No. of measured, independent and
observed [I > 2σ(I)] reflections
76863, 10902, 9631
Rint0.023
(sin θ/λ)max1)0.698
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.061, 1.13
No. of reflections10902
No. of parameters455
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.78

Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.

Selected bond lengths (Å) top
Sn1—O112.1233 (13)Sn1A—O11A2.1268 (14)
Sn1—O212.1248 (13)Sn1A—O21A2.1503 (14)
Sn1—O222.5553 (14)Sn1A—O12A2.4967 (17)
Sn1—O122.5641 (14)Sn1A—O22A2.5407 (16)
 

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