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Acta Cryst. (2008). E64, m349    [ doi:10.1107/S1600536808000676 ]

[mu]-Oxido-bis[(chloroacetato-[kappa]O)triphenylantimony(V)]

L. Quan, H. Yin and D. Wang

Abstract top

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.

Comment top

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,).

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Crystal packing, showing a extensity polymer chain, linked by C17—H17···Cl1 hydrogen bonds (dashed lines).
µ-Oxido-bis[(chloroacetato-κO)triphenylantimony(V)] top
Crystal data top
[Sb2(C6H5)6(C2H2Cl1O2)2O]F000 = 900
Mr = 909.07Dx = 1.607 Mg m−3
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 mm−1
β = 95.383 (2)ºT = 298 (2) K
V = 1878.3 (4) Å3Block, colourless
Z = 20.41 × 0.18 × 0.11 mm
Data collection top
Bruker SMART
diffractometer		3305 independent reflections
Radiation source: fine-focus sealed tube2465 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 25.0º
φ 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 top
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 Å−3
223 parametersΔρmin = −1.07 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Sb2(C6H5)6(C2H2Cl1O2)2O]V = 1878.3 (4) Å3
Mr = 909.07Z = 2
Monoclinic, P21/cMo Kα
a = 10.4950 (12) ŵ = 1.62 mm−1
b = 19.416 (2) ÅT = 298 (2) K
c = 9.2584 (10) Å0.41 × 0.18 × 0.11 mm
β = 95.383 (2)º
Data collection top
Bruker SMART
diffractometer		3305 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2465 reflections with I > 2σ(I)
Tmin = 0.556, Tmax = 0.842Rint = 0.035
8838 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0406 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.00Δρmax = 1.14 e Å−3
3305 reflectionsΔρmin = −1.07 e Å−3
223 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···Cl1ii0.932.933.592 (8)130
Symmetry codes: (ii) x−1, y, z.
Table 1
Selected geometric parameters (Å, °) top
Sb1—O31.9503 (4)O3—Sb1i1.9503 (4)
Sb1—O12.197 (4)
O3—Sb1—O1176.64 (11)Sb1—O3—Sb1i180.00 (2)
Symmetry codes: (i) −x, −y, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···Cl1ii0.932.933.592 (8)130
Symmetry codes: (ii) x−1, y, z.
Acknowledgements top

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

references
References top

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.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.