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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1450.
Published online 2009 October 28. doi:  10.1107/S160053680904361X
PMCID: PMC2971123

Bis(dimethyl sulfoxide-κO)bis­(mercapto­acetato-κ2 O,S)tin(IV)


In the title compound, [Sn(C2H2O2S)2(C2H6OS)2], the mercaptoacetato ligands chelate to SnIV through S and one O atoms. The metal centre is also coordinated by two dimethyl sulfoxide (DMSO) ligands through the O atom, leading to an overall distorted octahedral coordination environment for the SnIV atom. The mol­ecular adduct lies on a twofold rotation axis.

Related literature

For related structures of tin–mercaptoacetates, see: Holmes et al. (1988 [triangle]); Song et al. (1998 [triangle]); Ng et al. (1996 [triangle]); Zhang et al. (2006 [triangle]); Song et al. (2005 [triangle]); Wu et al. (2000 [triangle]); Zhong et al. (2004a [triangle],b [triangle], 2005a [triangle],b [triangle]). For the chemistry of tin compounds, see: Smith (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1450-scheme1.jpg


Crystal data

  • [Sn(C2H2O2S)2(C2H6OS)2]
  • M r = 455.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1450-efi1.jpg
  • a = 13.3460 (17) Å
  • b = 8.2706 (7) Å
  • c = 14.9053 (18) Å
  • β = 107.124 (5)°
  • V = 1572.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.17 mm−1
  • T = 130 K
  • 0.20 × 0.15 × 0.15 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.671, T max = 0.737
  • 5801 measured reflections
  • 1800 independent reflections
  • 1718 reflections with I > 2σ(I)
  • R int = 0.021


  • R[F 2 > 2σ(F 2)] = 0.020
  • wR(F 2) = 0.047
  • S = 1.10
  • 1800 reflections
  • 87 parameters
  • H-atom parameters constrained
  • Δρmax = 0.75 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904361X/ng2673sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904361X/ng2673Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


The author is grateful for financial support from the Scientific Research Fund of Zhejiang Provincial Education Department (grant No. 20070358), the Analysis and Testing Foundation of Zhejiang Province (grant Nos. 2008 F70034 and 2008 F70053) and the Young Scientists Fund of the Key Laboratory of Advanced Textile Materials and Manufacturing Technology of the Ministry of Education (grant No. 2007QN01).

supplementary crystallographic information


Compared with organotin compounds, inorganic compounds of tin are also important in industry applications, for example, electroplating, ceramic glazes and pigments,heterogeneous catalysts, gas sensors, and so on. (Smith et al., 1998) Perhaps the most important recent development in tin (iv) chemistry has been the increase in studies of the solid state properties of tin (iv) compounds. Sn(SCH2CH2S)2 could act as a typical Lewis acid and reveal to be a electron acceptor. And many structures have been reported to exhibit the reaction of Sn(SCH2CH2S)2 and ligands. (Wu et al., 2000; Holmes et al., 1988) Here, the S-contained chelated ligand is mercapto acetic acid but not 1,2-ethanedithiol ligand, and the solvent DMSO act as the second ligand.

The title compound, Sn(C2H2O2S)2(DMSO)2, is a mononuclear structure and crystallizes in monoclinic form in the space group C2/c. As shown in Figure 1, the asymmetric unit is composed of half tin atom, one mercaptoacetato and one DMSO ligand. According to a C2 symmetry axis pass the tin (iv) site, a mononuclear structure is present. In which, two mercaptoacetato ligands coordinates to SnIV through S and one O atoms. The metal centre is also coordinated by two dimethyl sulfoxide ligands through O atom, froming a SnO4S2 distorted octahedronal coordianted sphere. Around the metal centre, two mercaptoacetato ligands adopt cis chelated mode to form a SnO2S2 distorted equatorial plan. And other two DMSO ligands join on it from two polars of the coordinated sphere, also with cis mode around the metal centre.


All chemicals were obtained from commercial sources and were used as received. The title compound was handily synthesized by a solution reaction from mercapto acetic acid. HSCH2COOH (56 mg, 0.6 mmol) and NaOH (50 mg, 1.2 mmol) was dissolved in 10 ml of water. To this solution was added a 5 ml aqueous solution of SnCl4.5H2O (106 mg, 0.3 mmol) at room temperature. Amount of white precipitates were gradually formed and colected by filtrating and washing with water. Then they were dissolved in 5 ml DMSO and the filtration was slowly evaperated at room temperature. After several days, a great deal of colorless crystals were obtained, yield about 113 mg (83% on tin).


The structure was solved using direct methods and refined by full-matrix least-squares techniques. All non-hydrogen atoms were assigned anisotropic displacement parameters in the refinement. All hydrogen atoms were added at calculated positions and refined using a riding model. The structure was refined on F2 using SHELXTL97 software package(Sheldrick et al., 2008) without any unusual events.


Fig. 1.
Structure and labeling of the title compound, with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii.
Fig. 2.
The packing diagram viewed along the b-direction.

Crystal data

[Sn(C2H2O2S)2(C2H6OS)2]F(000) = 904
Mr = 455.14Dx = 1.923 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 2229 reflections
a = 13.3460 (17) Åθ = 3.1–27.5°
b = 8.2706 (7) ŵ = 2.17 mm1
c = 14.9053 (18) ÅT = 130 K
β = 107.124 (5)°Prism, white
V = 1572.3 (3) Å30.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer1800 independent reflections
Radiation source: fine-focus sealed tube1718 reflections with I > 2σ(I)
graphiteRint = 0.021
Detector resolution: 14.6306 pixels mm-1θmax = 27.5°, θmin = 3.2°
CCD_Profile_fitting scansh = −11→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −10→10
Tmin = 0.671, Tmax = 0.737l = −19→19
5801 measured reflections


Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0207P)2 + 2.5592P] where P = (Fo2 + 2Fc2)/3
1800 reflections(Δ/σ)max = 0.001
87 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = −0.43 e Å3

Special details

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)

Sn10.00000.20692 (2)0.75000.01316 (7)
S1−0.04306 (4)0.02254 (7)0.61815 (4)0.02162 (12)
S20.22228 (4)0.12036 (6)0.71261 (3)0.01444 (11)
O1−0.04086 (11)0.39054 (17)0.65158 (10)0.0164 (3)
O2−0.13288 (14)0.4586 (2)0.50766 (10)0.0285 (4)
O30.16014 (11)0.24764 (18)0.75112 (10)0.0179 (3)
C1−0.09221 (16)0.3555 (3)0.56564 (14)0.0194 (4)
C2−0.1050 (2)0.1784 (3)0.53429 (16)0.0296 (5)
C30.22763 (19)0.2033 (3)0.60389 (15)0.0239 (5)
C40.35322 (16)0.1546 (3)0.78190 (16)0.0215 (4)

Atomic displacement parameters (Å2)

Sn10.00996 (10)0.01364 (11)0.01662 (10)0.0000.00506 (7)0.000
S10.0191 (3)0.0178 (3)0.0260 (3)0.0000 (2)0.0035 (2)−0.0068 (2)
S20.0111 (2)0.0132 (2)0.0194 (2)0.00096 (18)0.00510 (19)−0.00037 (17)
O10.0143 (7)0.0163 (7)0.0177 (6)−0.0018 (6)0.0033 (6)0.0011 (5)
O20.0319 (9)0.0303 (9)0.0192 (7)0.0098 (7)0.0013 (7)0.0025 (7)
O30.0106 (7)0.0193 (7)0.0259 (7)−0.0017 (6)0.0086 (6)−0.0053 (6)
C10.0132 (10)0.0253 (11)0.0206 (10)0.0041 (8)0.0063 (8)−0.0018 (8)
C20.0264 (12)0.0304 (13)0.0231 (11)0.0113 (10)−0.0065 (10)−0.0076 (9)
C30.0250 (12)0.0303 (12)0.0180 (9)0.0026 (9)0.0088 (9)0.0008 (9)
C40.0117 (10)0.0217 (10)0.0280 (11)0.0037 (8)0.0013 (9)−0.0023 (9)

Geometric parameters (Å, °)

Sn1—O1i2.0699 (14)O2—C11.222 (3)
Sn1—O12.0699 (14)C1—C21.531 (3)
Sn1—O32.1587 (14)C2—H2B0.9900
Sn1—O3i2.1587 (14)C2—H2A0.9900
Sn1—S12.4193 (6)C3—H3A0.9800
Sn1—S1i2.4193 (6)C3—H3B0.9800
S1—C21.817 (2)C3—H3C0.9800
S2—O31.5511 (15)C4—H4A0.9800
S2—C41.771 (2)C4—H4B0.9800
S2—C31.780 (2)C4—H4C0.9800
O1—C11.295 (2)
O1i—Sn1—O185.61 (8)O2—C1—O1122.6 (2)
O1i—Sn1—O380.01 (6)O2—C1—C2117.72 (19)
O1—Sn1—O386.83 (6)O1—C1—C2119.67 (19)
O1i—Sn1—O3i86.83 (6)C1—C2—S1118.77 (16)
O1—Sn1—O3i80.01 (6)C1—C2—H2B107.6
O3—Sn1—O3i162.05 (8)S1—C2—H2B107.6
O1i—Sn1—S1171.18 (4)C1—C2—H2A107.6
O1—Sn1—S186.38 (4)S1—C2—H2A107.6
O3—Sn1—S195.88 (4)H2B—C2—H2A107.1
O3i—Sn1—S195.41 (4)S2—C3—H3A109.5
O1i—Sn1—S1i86.38 (4)S2—C3—H3B109.5
O1—Sn1—S1i171.18 (4)H3A—C3—H3B109.5
O3—Sn1—S1i95.41 (4)S2—C3—H3C109.5
O3i—Sn1—S1i95.88 (4)H3A—C3—H3C109.5
S1—Sn1—S1i101.85 (3)H3B—C3—H3C109.5
C2—S1—Sn193.60 (8)S2—C4—H4A109.5
O3—S2—C4102.64 (9)S2—C4—H4B109.5
O3—S2—C3104.15 (10)H4A—C4—H4B109.5
C4—S2—C399.90 (11)S2—C4—H4C109.5
C1—O1—Sn1119.26 (14)H4A—C4—H4C109.5
S2—O3—Sn1121.82 (8)H4B—C4—H4C109.5
O1i—Sn1—S1—C2−36.3 (3)C3—S2—O3—Sn1106.14 (12)
O1—Sn1—S1—C2−11.53 (10)O1i—Sn1—O3—S2161.54 (11)
O3—Sn1—S1—C2−97.96 (10)O1—Sn1—O3—S2−112.37 (10)
O3i—Sn1—S1—C268.06 (10)O3i—Sn1—O3—S2−155.05 (10)
S1i—Sn1—S1—C2165.24 (9)S1—Sn1—O3—S2−26.35 (10)
O1i—Sn1—O1—C1−169.37 (17)S1i—Sn1—O3—S276.19 (10)
O3—Sn1—O1—C1110.43 (15)Sn1—O1—C1—O2168.26 (17)
O3i—Sn1—O1—C1−81.82 (15)Sn1—O1—C1—C2−10.7 (3)
S1—Sn1—O1—C114.32 (14)O2—C1—C2—S1178.66 (18)
S1i—Sn1—O1—C1−144.6 (2)O1—C1—C2—S1−2.3 (3)
C4—S2—O3—Sn1−150.07 (11)Sn1—S1—C2—C110.8 (2)

Symmetry codes: (i) −x, y, −z+3/2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2673).


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