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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m81.
Published online 2007 December 6. doi:  10.1107/S1600536807063623
PMCID: PMC2919292

catena-Poly[[tri-n-butyl­tin(IV)]-μ-2-thio­phene­acetato]

Abstract

The title compound, [Sn(C4H9)3(C6H5O2S)]n, possesses an infinite chain structure. The SnO2C3 centre has a distorted trigonal-bipyramidal geometry (τ = 0.145) with the O atoms in the axial positions. Atoms of the thio­phene group S1 and C4 are disordered over two sites The S atom and one C atom, with attached H atom, of the thiophene ring are disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

Related literature

For related literature see: Addison et al. (1984 [triangle]); Ma et al. (2006 [triangle]).

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Object name is e-64-00m81-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)3(C6H5O2S)]
  • M r = 431.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m81-efi1.jpg
  • a = 12.7657 (15) Å
  • b = 10.6970 (13) Å
  • c = 16.328 (2) Å
  • β = 100.435 (2)°
  • V = 2192.8 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.26 mm−1
  • T = 298 (2) K
  • 0.46 × 0.21 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.594, T max = 0.863
  • 8428 measured reflections
  • 3715 independent reflections
  • 2104 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.197
  • S = 1.10
  • 3715 reflections
  • 200 parameters
  • 483 restraints
  • H-atom parameters constrained
  • Δρmax = 0.96 e Å−3
  • Δρmin = −0.51 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063623/bv2084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063623/bv2084Isup2.hkl

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

Acknowledgments

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

supplementary crystallographic information

Comment

The title compound, (I) (Fig. 1), possesses an infinite one-dimensional chain structure arising from Sn—O bridges to the ligand. The Sn1—O1 distances of 2.183 (6) Å and Sn1—O2A [symmetry code: -x + 2,y - 1/2,-z + 1/2] distance 2.482 (7) Å, are similar to those reported for other organotin carboxylates (Ma et al., 2006). The Sn atom has distorted trigonal-bipyramidal geometry[τ = 0.145; Addison et al.,, 1984], with atoms O1 and O2A in axial positions [O1—Sn1—O2A = 171.3 (2) °] and the C atoms of the three butyl groups in equatorial positions. The sum of the equatorial C—Sn—C angles is 358.6 °, indicating approximate coplanarity for these atoms.

Experimental

The reaction was carried out under nitrogen atmosphere. 2-Thiopheneacetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of benzene(30 ml) in a Schlenk flask and stirred for 0.5 h. Tri-n-butyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1).(yield 80%; m.p. 457 K). Analysis calculated (%) for C18H32O2SSn (Mr = 431.19): C, 50.14; H, 7.48. found: C, 50.06; H, 7.53.

Refinement

During the refinement atoms S1 and C4 were found to be disordered over two sites, and the ratio of the occupancy factors refined to 0.729 (11):0.271 (11) and 0.271 (11):0.729 (11) for atoms S1:S1'and atoms C4:C4', respectively. H atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.97 Å for aromatic, methyl and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C) where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
Fig. 2.
The one-dimensional infinite chain structure of (I), H atoms have been omitted for clarity.

Crystal data

[Sn(C4H9)3(C6H5O2S)]F(000) = 888
Mr = 431.19Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.7657 (15) ÅCell parameters from 2306 reflections
b = 10.6970 (13) Åθ = 2.3–22.1°
c = 16.328 (2) ŵ = 1.26 mm1
β = 100.435 (2)°T = 298 K
V = 2192.8 (5) Å3Block, colourless
Z = 40.46 × 0.21 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer3715 independent reflections
Radiation source: fine-focus sealed tube2104 reflections with I > 2σ(I)
graphiteRint = 0.042
phi and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→15
Tmin = 0.594, Tmax = 0.863k = −12→12
8428 measured reflectionsl = −19→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.080P)2 + 4.0018P] where P = (Fo2 + 2Fc2)/3
3715 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.96 e Å3
483 restraintsΔρmin = −0.51 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Sn10.99480 (5)0.76650 (6)0.29167 (4)0.0663 (3)
O10.9550 (5)0.9174 (5)0.3707 (4)0.0663 (3)
O20.9708 (5)1.0734 (6)0.2834 (5)0.0845 (19)
S10.7850 (4)0.9564 (5)0.4888 (4)0.1199 (19)0.729 (11)
C4'0.7695 (14)1.001 (5)0.494 (2)0.1199 (19)0.271 (11)
H4'0.81670.98020.54260.144*0.271 (11)
C10.9465 (8)1.0331 (9)0.3486 (8)0.085 (2)
C20.9043 (8)1.1152 (9)0.4098 (7)0.091 (3)
H2A0.89841.20010.38860.109*
H2B0.95481.11570.46190.109*
C30.7953 (6)1.0734 (9)0.4269 (7)0.096 (3)
C40.6941 (9)1.094 (2)0.3728 (9)0.120 (3)0.729 (11)
H40.68441.13290.32100.144*0.729 (11)
S1'0.6898 (9)1.1447 (13)0.3827 (10)0.120 (3)0.271 (11)
C50.6121 (8)1.0451 (13)0.4115 (9)0.141 (4)
H50.53981.06300.39720.169*
C60.6597 (8)0.9649 (12)0.4754 (9)0.132 (4)
H60.62000.91970.50770.158*
C70.9691 (9)0.6340 (11)0.3839 (9)0.111 (3)
H7A1.00230.55500.37450.133*
H7B1.00100.66400.43880.133*
C80.8496 (10)0.6152 (15)0.3792 (10)0.152 (4)
H8A0.81800.69500.38910.182*
H8B0.81860.58900.32310.182*
C90.8204 (12)0.5212 (15)0.4396 (10)0.174 (6)
H9A0.85050.54690.49590.209*
H9B0.85080.44070.42960.209*
C100.7012 (12)0.5082 (19)0.4313 (12)0.219 (9)
H10A0.67920.42850.40720.329*
H10B0.66660.57360.39610.329*
H10C0.68190.51440.48530.329*
C110.8709 (9)0.8019 (12)0.1866 (9)0.117 (3)
H11A0.89160.87100.15450.140*
H11B0.86130.72870.15090.140*
C120.7657 (10)0.8333 (16)0.2144 (9)0.155 (4)
H12A0.75780.77930.26060.186*
H12B0.76910.91880.23450.186*
C130.6690 (12)0.820 (2)0.1477 (11)0.207 (7)
H13A0.67090.73940.12020.249*
H13B0.66850.88480.10630.249*
C140.5677 (14)0.829 (3)0.1860 (15)0.252 (10)
H14A0.55110.74790.20590.379*
H14B0.50950.85710.14450.379*
H14C0.57930.88680.23160.379*
C151.1571 (7)0.8270 (10)0.2960 (8)0.096 (3)
H15A1.17070.83120.23950.116*
H15B1.16480.91070.31900.116*
C161.2406 (7)0.7433 (11)0.3470 (10)0.125 (4)
H16A1.23300.65900.32490.150*
H16B1.22920.74080.40410.150*
C171.3543 (8)0.7906 (14)0.3454 (11)0.146 (5)
H17A1.36630.79180.28850.175*
H17B1.36190.87530.36680.175*
C181.4368 (12)0.7064 (18)0.3981 (14)0.209 (8)
H18A1.40310.63080.41150.313*
H18B1.46720.74910.44850.313*
H18C1.49190.68650.36730.313*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0755 (5)0.0549 (4)0.0733 (6)0.0017 (3)0.0260 (3)0.0032 (3)
O10.0755 (5)0.0549 (4)0.0733 (6)0.0017 (3)0.0260 (3)0.0032 (3)
O20.107 (4)0.061 (4)0.094 (5)−0.002 (3)0.042 (4)0.012 (3)
S10.123 (3)0.103 (3)0.144 (4)0.007 (2)0.054 (3)0.020 (3)
C4'0.123 (3)0.103 (3)0.144 (4)0.007 (2)0.054 (3)0.020 (3)
C10.092 (5)0.060 (4)0.111 (6)0.001 (4)0.037 (5)0.001 (5)
C20.113 (6)0.062 (5)0.107 (6)0.007 (5)0.046 (5)0.001 (5)
C30.100 (5)0.086 (5)0.115 (6)0.016 (5)0.050 (5)−0.003 (5)
C40.121 (5)0.106 (6)0.145 (5)0.026 (4)0.053 (4)0.010 (5)
S1'0.121 (5)0.106 (6)0.145 (5)0.026 (4)0.053 (4)0.010 (5)
C50.121 (7)0.148 (8)0.163 (8)0.017 (7)0.049 (7)0.004 (7)
C60.132 (7)0.128 (7)0.150 (8)−0.001 (6)0.067 (6)0.008 (7)
C70.131 (7)0.089 (6)0.122 (8)0.018 (6)0.047 (6)0.013 (6)
C80.162 (8)0.135 (8)0.159 (9)0.005 (7)0.033 (8)0.024 (7)
C90.174 (12)0.158 (11)0.192 (12)0.009 (10)0.034 (11)0.020 (11)
C100.163 (16)0.229 (19)0.25 (2)−0.001 (14)−0.001 (15)0.042 (18)
C110.113 (6)0.102 (6)0.137 (7)0.010 (5)0.024 (6)−0.005 (6)
C120.154 (8)0.141 (8)0.162 (8)0.005 (7)0.007 (7)0.015 (7)
C130.176 (12)0.204 (12)0.232 (13)0.012 (12)0.013 (12)0.016 (12)
C140.198 (18)0.31 (2)0.27 (2)0.017 (19)0.083 (17)−0.01 (2)
C150.086 (6)0.089 (6)0.121 (7)−0.008 (5)0.036 (5)−0.008 (5)
C160.083 (7)0.128 (9)0.160 (11)0.002 (6)0.009 (7)−0.027 (8)
C170.085 (8)0.160 (10)0.194 (12)0.001 (7)0.028 (8)−0.044 (10)
C180.124 (13)0.225 (17)0.27 (2)0.019 (13)0.006 (14)−0.028 (17)

Geometric parameters (Å, °)

Sn1—C72.136 (11)C9—C101.510 (9)
Sn1—C112.147 (13)C9—H9A0.9700
Sn1—C152.159 (10)C9—H9B0.9700
Sn1—O12.183 (6)C10—H10A0.9600
Sn1—O2i2.482 (7)C10—H10B0.9600
O1—C11.288 (11)C10—H10C0.9600
O2—C11.239 (12)C11—C121.531 (9)
O2—Sn1ii2.482 (7)C11—H11A0.9700
S1—C61.577 (11)C11—H11B0.9700
S1—C31.630 (9)C12—C131.497 (10)
C4'—C31.432 (9)C12—H12A0.9700
C4'—C61.432 (9)C12—H12B0.9700
C4'—H4'0.9300C13—C141.539 (10)
C1—C21.502 (14)C13—H13A0.9700
C2—C31.534 (8)C13—H13B0.9700
C2—H2A0.9700C14—H14A0.9600
C2—H2B0.9700C14—H14B0.9600
C3—C41.443 (9)C14—H14C0.9600
C3—S1'1.601 (13)C15—C161.519 (9)
C4—C51.418 (9)C15—H15A0.9700
C4—H40.9300C15—H15B0.9700
S1'—C51.585 (14)C16—C171.541 (9)
C5—C61.400 (9)C16—H16A0.9700
C5—H50.9300C16—H16B0.9700
C6—H60.9300C17—C181.527 (10)
C7—C81.526 (9)C17—H17A0.9700
C7—H7A0.9700C17—H17B0.9700
C7—H7B0.9700C18—H18A0.9600
C8—C91.502 (9)C18—H18B0.9600
C8—H8A0.9700C18—H18C0.9600
C8—H8B0.9700
C7—Sn1—C11119.7 (5)H8A—C8—H8B107.5
C7—Sn1—C15116.4 (4)C8—C9—C10111.6 (11)
C11—Sn1—C15122.5 (5)C8—C9—H9A109.3
C7—Sn1—O189.5 (4)C10—C9—H9A109.3
C11—Sn1—O197.2 (4)C8—C9—H9B109.3
C15—Sn1—O194.8 (3)C10—C9—H9B109.3
C7—Sn1—O2i81.9 (4)H9A—C9—H9B108.0
C11—Sn1—O2i85.5 (4)C9—C10—H10A109.5
C15—Sn1—O2i90.6 (3)C9—C10—H10B109.5
O1—Sn1—O2i171.3 (2)H10A—C10—H10B109.5
C1—O1—Sn1124.2 (7)C9—C10—H10C109.5
C1—O2—Sn1ii144.0 (7)H10A—C10—H10C109.5
C6—S1—C393.6 (5)H10B—C10—H10C109.5
C3—C4'—C6109.4 (8)C12—C11—Sn1111.1 (9)
C3—C4'—H4'125.3C12—C11—H11A109.4
C6—C4'—H4'125.3Sn1—C11—H11A109.4
O2—C1—O1123.6 (10)C12—C11—H11B109.4
O2—C1—C2122.9 (9)Sn1—C11—H11B109.4
O1—C1—C2113.5 (10)H11A—C11—H11B108.0
C1—C2—C3113.4 (9)C13—C12—C11114.4 (11)
C1—C2—H2A108.9C13—C12—H12A108.6
C3—C2—H2A108.9C11—C12—H12A108.6
C1—C2—H2B108.9C13—C12—H12B108.6
C3—C2—H2B108.9C11—C12—H12B108.6
H2A—C2—H2B107.7H12A—C12—H12B107.6
C4'—C3—C4104.3 (7)C12—C13—C14109.9 (12)
C4'—C3—C2129.8 (9)C12—C13—H13A109.7
C4—C3—C2125.8 (9)C14—C13—H13A109.7
C4'—C3—S1'108.2 (13)C12—C13—H13B109.7
C4—C3—S1'20.8 (11)C14—C13—H13B109.7
C2—C3—S1'119.7 (8)H13A—C13—H13B108.2
C4'—C3—S118 (3)C13—C14—H14A109.5
C4—C3—S1109.4 (7)C13—C14—H14B109.5
C2—C3—S1121.0 (7)H14A—C14—H14B109.5
S1'—C3—S1119.3 (7)C13—C14—H14C109.5
C5—C4—C3108.8 (7)H14A—C14—H14C109.5
C5—C4—H4125.6H14B—C14—H14C109.5
C3—C4—H4125.6C16—C15—Sn1114.6 (7)
C5—S1'—C393.8 (8)C16—C15—H15A108.6
C6—C5—C4107.6 (7)Sn1—C15—H15A108.6
C6—C5—S1'115.0 (8)C16—C15—H15B108.6
C4—C5—S1'21.0 (11)Sn1—C15—H15B108.6
C6—C5—H5126.2H15A—C15—H15B107.6
C4—C5—H5126.2C15—C16—C17111.5 (9)
S1'—C5—H5115.6C15—C16—H16A109.3
C5—C6—C4'105.8 (9)C17—C16—H16A109.3
C5—C6—S1115.6 (7)C15—C16—H16B109.3
C4'—C6—S119 (3)C17—C16—H16B109.3
C5—C6—H6122.2H16A—C16—H16B108.0
C4'—C6—H6129.0C18—C17—C16110.7 (11)
S1—C6—H6122.2C18—C17—H17A109.5
C8—C7—Sn1109.3 (8)C16—C17—H17A109.5
C8—C7—H7A109.8C18—C17—H17B109.5
Sn1—C7—H7A109.8C16—C17—H17B109.5
C8—C7—H7B109.8H17A—C17—H17B108.1
Sn1—C7—H7B109.8C17—C18—H18A109.5
H7A—C7—H7B108.3C17—C18—H18B109.5
C9—C8—C7114.8 (10)H18A—C18—H18B109.5
C9—C8—H8A108.6C17—C18—H18C109.5
C7—C8—H8A108.6H18A—C18—H18C109.5
C9—C8—H8B108.6H18B—C18—H18C109.5
C7—C8—H8B108.6

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2084).

References

  • Addison, A. W., Rao, T. N., Reedijk, J., Rijn, J. V. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356.
  • Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem., 691, 1713–1721.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997a). SHELXL97 andSHELXS97 University of Göttingen, Germany.
  • Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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