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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m349.
Published online 2008 January 16. doi:  10.1107/S1600536808000676
PMCID: PMC2960346

μ-Oxido-bis­[(chloro­acetato-κO)­triphenyl­anti­mony(V)]

Abstract

The Sb atom in the centrosymmetric title complex, [Sb2(C6H5)6(C2H2ClO2)2O], has a distorted trigonal–bipyramidal geometry. The bridging oxide O atom occupies one of the axial sites, while the O atom of the chloroacetate ligand occupies the other.

Related literature

For related literature, see: Gibbons & Sowerby (1998 [triangle]).

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Object name is e-64-0m349-scheme1.jpg

Experimental

Crystal data

  • [Sb2(C6H5)6(C2H2ClO2)2O]
  • M r = 909.07
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m349-efi1.jpg
  • a = 10.4950 (12) Å
  • b = 19.416 (2) Å
  • c = 9.2584 (10) Å
  • β = 95.383 (2)°
  • V = 1878.3 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.62 mm−1
  • T = 298 (2) K
  • 0.41 × 0.18 × 0.11 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.556, T max = 0.842
  • 8838 measured reflections
  • 3305 independent reflections
  • 2465 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.109
  • S = 1.00
  • 3305 reflections
  • 223 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 1.14 e Å−3
  • Δρmin = −1.07 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, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000676/sg2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000676/sg2199Isup2.hkl

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

Acknowledgments

We acknowledge the National Natural Science Fund of China (grant No. 20771053) and the Natural Science Fund of Shandong Province (2005ZX09) for financial support.

supplementary crystallographic information

Comment

Organoantimony esters of carboxylic acids are widely used as biocides, as fungicides and, in industry, as homogeneous catalysts. We have therefore synthesized the title compound, (I), and present its crystal structure here. The molecular structure of (I) is shown in Fig. 1. For a related structure see bis(triphenylantimony) trifluoroacetate [Sb(C6H5)3(O2C2F3)]2O (M. N. Gibbons & Sowerby, 1998).

The title compound comprises two (chloroacetyl)tris triphenylantimony units bridged by an oxygen dianion. Centrosymmetrically molecules are linked by short intermolecular C17—H17···Cl1 contacts [symmetry codes: -1 + x, +y, +z], and one-dimensional polymeric chains run parallel to the a axis, (Fig. 2.). The O—Sb—O angle is 176.64 (11)°. The Sb—O distances vary with the role oxygen atoms play in the structure, the terminal Sb1—O1 [2.197 (4) Å] bond being longer than bridging Sb1—O3 [1.9503 (4) Å] bond. (Table 1, Table 2,).

Experimental

Chloroactic acid (0.02 g, 0.2 mmol) and sodium methoxide (0.4 ml, 0.2 mmol) was added to a stirred solution of oxygen bridged bis(chloro) tris triphenylantimony) (0.16 g, 0.2 mmol) and toluene (20 ml). The reaction mixture was stirred at room temperature for 24 h. Crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum/dichloromethane (1:2 v/v) solution over a period of a week (yield 85%. m.p. 470k). Anal. Calcd (%) for C40H34O5Sb2Cl2(Mr = 909.08): C, 52.80; H, 3.72; O, 8.76; Cl, 7.76; Sb, 26.74. Found (%): C, 52.85; H, 3.77; O, 8.80; Cl, 7.80; Sb, 26.79

Refinement

The H atoms bound to aryl groups were idealized with a C—H = 0.93 Å. All other H atoms were also placed in idealized positions, with C—H = 0.97 Å, and treated as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, O) or 1.5 Ueq(C) for the methyl group.

Figures

Fig. 1.
The molecular structure, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Crystal packing, showing a extensity polymer chain, linked by C17—H17···Cl1 hydrogen bonds (dashed lines).

Crystal data

[Sb2(C6H5)6(C2H2Cl1O2)2O]F000 = 900
Mr = 909.07Dx = 1.607 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
a = 10.4950 (12) ÅCell parameters from 3131 reflections
b = 19.416 (2) Åθ = 2.1–24.7º
c = 9.2584 (10) ŵ = 1.62 mm1
β = 95.383 (2)ºT = 298 (2) K
V = 1878.3 (4) Å3Block, colourless
Z = 20.41 × 0.18 × 0.11 mm

Data collection

Bruker SMART diffractometer3305 independent reflections
Radiation source: fine-focus sealed tube2465 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −7→12
Tmin = 0.556, Tmax = 0.842k = −23→21
8838 measured reflectionsl = −10→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.109  w = 1/[σ2(Fo2) + (0.0489P)2 + 4.2337P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3305 reflectionsΔρmax = 1.14 e Å3
223 parametersΔρmin = −1.07 e Å3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
Sb10.14913 (3)0.054058 (18)0.45933 (4)0.04187 (15)
Cl10.5107 (3)0.17116 (18)0.2357 (4)0.1409 (11)
O10.3199 (4)0.1102 (2)0.4046 (5)0.0581 (11)
O20.2708 (6)0.2089 (3)0.5109 (6)0.0856 (16)
O30.00000.00000.50000.0530 (15)
C10.3341 (7)0.1745 (4)0.4368 (8)0.0679 (19)
C20.4414 (10)0.2112 (5)0.3674 (12)0.127 (4)
H2A0.50790.22210.44400.152*
H2B0.40760.25460.32860.152*
C30.2216 (5)0.0580 (3)0.6778 (6)0.0455 (13)
C40.2782 (7)−0.0004 (4)0.7389 (8)0.0693 (19)
H40.2832−0.04000.68340.083*
C50.3272 (8)−0.0002 (4)0.8811 (9)0.082 (2)
H50.3673−0.03940.92110.099*
C60.3175 (8)0.0574 (5)0.9647 (8)0.081 (2)
H60.34920.05691.06190.098*
C70.2617 (8)0.1152 (4)0.9058 (8)0.076 (2)
H70.25610.15440.96250.092*
C80.2134 (7)0.1160 (3)0.7628 (7)0.0642 (18)
H80.17510.15580.72300.077*
C90.2230 (6)−0.0235 (3)0.3337 (6)0.0448 (14)
C100.3500 (7)−0.0424 (4)0.3467 (8)0.0679 (19)
H100.4074−0.01950.41270.082*
C110.3925 (9)−0.0937 (4)0.2649 (11)0.093 (3)
H110.4781−0.10670.27690.112*
C120.3100 (10)−0.1264 (4)0.1649 (10)0.088 (3)
H120.3399−0.16090.10710.106*
C130.1843 (9)−0.1089 (4)0.1497 (9)0.088 (3)
H130.1280−0.13160.08210.105*
C140.1402 (7)−0.0574 (3)0.2346 (7)0.0609 (17)
H140.0539−0.04560.22470.073*
C150.0381 (5)0.1302 (3)0.3458 (6)0.0446 (13)
C16−0.0780 (6)0.1476 (3)0.3891 (7)0.0554 (16)
H16−0.10810.12570.46860.066*
C17−0.1512 (7)0.1976 (3)0.3149 (9)0.070 (2)
H17−0.22910.21060.34670.084*
C18−0.1096 (8)0.2278 (4)0.1957 (9)0.074 (2)
H18−0.16080.26020.14410.088*
C190.0063 (8)0.2112 (4)0.1511 (8)0.074 (2)
H190.03570.23280.07100.088*
C200.0798 (7)0.1616 (3)0.2265 (7)0.0619 (17)
H200.15860.14940.19590.074*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.0420 (2)0.0387 (2)0.0444 (2)−0.00671 (18)0.00144 (15)−0.00121 (18)
Cl10.1011 (19)0.184 (3)0.144 (3)−0.051 (2)0.0457 (18)−0.015 (2)
O10.059 (3)0.048 (2)0.068 (3)−0.019 (2)0.011 (2)−0.002 (2)
O20.099 (4)0.067 (3)0.094 (4)−0.022 (3)0.029 (3)−0.015 (3)
O30.041 (3)0.052 (3)0.066 (4)−0.016 (3)0.006 (3)0.003 (3)
C10.062 (4)0.068 (5)0.075 (5)−0.025 (4)0.014 (4)−0.007 (4)
C20.125 (7)0.114 (6)0.152 (8)−0.045 (6)0.065 (6)−0.035 (6)
C30.047 (3)0.046 (3)0.043 (3)−0.013 (3)0.003 (3)−0.001 (3)
C40.085 (5)0.051 (4)0.069 (5)−0.003 (4)−0.011 (4)0.003 (3)
C50.095 (6)0.078 (5)0.070 (5)0.004 (5)−0.018 (4)0.023 (4)
C60.089 (6)0.104 (7)0.049 (5)−0.023 (5)−0.008 (4)0.007 (5)
C70.098 (6)0.082 (5)0.049 (5)−0.007 (5)0.008 (4)−0.015 (4)
C80.079 (5)0.056 (4)0.058 (5)0.005 (4)0.010 (4)−0.003 (3)
C90.051 (4)0.041 (3)0.044 (3)−0.009 (3)0.011 (3)−0.003 (3)
C100.056 (4)0.070 (5)0.076 (5)0.000 (4)0.001 (4)−0.010 (4)
C110.082 (6)0.075 (6)0.128 (8)0.024 (5)0.032 (6)−0.006 (5)
C120.115 (7)0.055 (4)0.102 (7)0.003 (5)0.047 (6)−0.018 (4)
C130.102 (7)0.073 (5)0.090 (6)−0.029 (5)0.020 (5)−0.037 (5)
C140.059 (4)0.060 (4)0.064 (4)−0.010 (3)0.008 (3)−0.010 (3)
C150.049 (3)0.039 (3)0.046 (4)−0.003 (3)−0.002 (3)−0.002 (3)
C160.061 (4)0.043 (3)0.061 (4)−0.006 (3)0.000 (3)0.003 (3)
C170.065 (5)0.059 (4)0.083 (6)0.013 (4)−0.007 (4)−0.003 (4)
C180.089 (6)0.055 (4)0.072 (5)0.011 (4)−0.021 (4)0.007 (4)
C190.095 (6)0.069 (5)0.055 (5)−0.002 (4)−0.002 (4)0.014 (4)
C200.080 (5)0.063 (4)0.044 (4)0.000 (4)0.008 (3)0.010 (3)

Geometric parameters (Å, °)

Sb1—O31.9503 (4)C9—C141.371 (9)
Sb1—C32.095 (6)C9—C101.377 (9)
Sb1—C92.095 (6)C10—C111.353 (10)
Sb1—C152.101 (6)C10—H100.9300
Sb1—O12.197 (4)C11—C121.364 (12)
Cl1—C21.670 (9)C11—H110.9300
O1—C11.289 (8)C12—C131.357 (11)
O2—C11.201 (8)C12—H120.9300
O3—Sb1i1.9503 (4)C13—C141.379 (9)
C1—C21.525 (10)C13—H130.9300
C2—H2A0.9700C14—H140.9300
C2—H2B0.9700C15—C161.361 (8)
C3—C41.377 (8)C15—C201.368 (8)
C3—C81.382 (8)C16—C171.381 (9)
C4—C51.367 (10)C16—H160.9300
C4—H40.9300C17—C181.358 (10)
C5—C61.370 (11)C17—H170.9300
C5—H50.9300C18—C191.360 (10)
C6—C71.357 (10)C18—H180.9300
C6—H60.9300C19—C201.382 (9)
C7—C81.372 (10)C19—H190.9300
C7—H70.9300C20—H200.9300
C8—H80.9300
O3—Sb1—C393.36 (15)C3—C8—H8119.9
O3—Sb1—C993.77 (15)C14—C9—C10118.6 (6)
C3—Sb1—C9116.3 (2)C14—C9—Sb1118.2 (5)
O3—Sb1—C1593.31 (15)C10—C9—Sb1123.3 (5)
C3—Sb1—C15126.3 (2)C11—C10—C9121.0 (7)
C9—Sb1—C15116.4 (2)C11—C10—H10119.5
O3—Sb1—O1176.64 (11)C9—C10—H10119.5
C3—Sb1—O188.53 (19)C10—C11—C12120.1 (8)
C9—Sb1—O182.89 (19)C10—C11—H11120.0
C15—Sb1—O187.80 (19)C12—C11—H11120.0
C1—O1—Sb1120.4 (4)C13—C12—C11120.2 (7)
Sb1—O3—Sb1i180.00 (2)C13—C12—H12119.9
O2—C1—O1127.7 (6)C11—C12—H12119.9
O2—C1—C2116.8 (7)C12—C13—C14119.8 (8)
O1—C1—C2115.4 (7)C12—C13—H13120.1
C1—C2—Cl1118.7 (7)C14—C13—H13120.1
C1—C2—H2A107.6C9—C14—C13120.3 (7)
Cl1—C2—H2A107.6C9—C14—H14119.9
C1—C2—H2B107.6C13—C14—H14119.9
Cl1—C2—H2B107.6C16—C15—C20119.3 (6)
H2A—C2—H2B107.1C16—C15—Sb1119.8 (4)
C4—C3—C8119.0 (6)C20—C15—Sb1120.9 (5)
C4—C3—Sb1118.1 (5)C15—C16—C17120.0 (6)
C8—C3—Sb1122.9 (5)C15—C16—H16120.0
C5—C4—C3120.2 (7)C17—C16—H16120.0
C5—C4—H4119.9C18—C17—C16120.1 (7)
C3—C4—H4119.9C18—C17—H17119.9
C4—C5—C6120.3 (7)C16—C17—H17119.9
C4—C5—H5119.8C17—C18—C19120.6 (7)
C6—C5—H5119.8C17—C18—H18119.7
C7—C6—C5120.1 (7)C19—C18—H18119.7
C7—C6—H6120.0C18—C19—C20119.0 (7)
C5—C6—H6120.0C18—C19—H19120.5
C6—C7—C8120.2 (7)C20—C19—H19120.5
C6—C7—H7119.9C15—C20—C19120.9 (7)
C8—C7—H7119.9C15—C20—H20119.6
C7—C8—C3120.2 (7)C19—C20—H20119.6
C7—C8—H8119.9

Symmetry codes: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H17···Cl1ii0.932.933.592 (8)130

Symmetry codes: (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2199).

References

  • Gibbons, M. N. & Sowerby, D. B. (1998). J. Organomet. Chem.555, 271–278.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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