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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m31.
Published online 2008 December 10. doi:  10.1107/S1600536808040804
PMCID: PMC2967878

Tris(O-cyclo­hexyl dithio­carbonato-κS)anti­mony(III)

Abstract

In the mol­ecule of the title compound, [Sb(C7H11OS2)3], the anti­mony(III) is coordinated by the S atoms of three O-alkyl xanthate groups acting as monodentate ligands, forming a distorted trigonal-pyramidal coordination.

Related literature

For the biological activity of anti­mony(III) complexes, see: Tiekink (2002 [triangle]); Wang et al. (2005 [triangle]). For a related structure, see: Baba et al. (2001 [triangle]).

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Object name is e-65-00m31-scheme1.jpg

Experimental

Crystal data

  • [Sb(C7H11OS2)3]
  • M r = 646.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m31-efi1.jpg
  • a = 9.4187 (12) Å
  • b = 18.866 (2) Å
  • c = 15.8583 (18) Å
  • β = 93.944 (2)°
  • V = 2811.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.45 mm−1
  • T = 298 (2) K
  • 0.30 × 0.25 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.664, T max = 0.773
  • 14030 measured reflections
  • 4946 independent reflections
  • 3183 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.127
  • S = 1.00
  • 4946 reflections
  • 280 parameters
  • 90 restraints
  • H-atom parameters constrained
  • Δρmax = 0.86 e Å−3
  • Δρmin = −0.60 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, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040804/rz2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040804/rz2271Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The coordination chemistry of antimony has both a practical and theoretical interest.The medicinal and cosmetic use of antimony complexes goes back at least to the Egyptians. Potassium antimony tartrate or tartar emetic was widely used until the early 1900s despite the somewhat toxic nature of the material. On the other hand, antimony complexes have been reported with good cytotoxicity and antitumor activities (Tiekink, 2002; Wang et al., 2005). As a part of our ongoing investigations in the field we have synthesized the title compound and determined its crystal structure.

In the title compound, the antomony(III) ion lies on a pseudo threefold axis (Fig. 1). The O-alkylxanthate ligands coordinate to the antimony(III) ion in a monodentate mode, with Sb—S distances ranging from 2.5072 (14) to 2.5140 (15) Å (Table 1), to form a trigonal pyramidal geometry. The separations between the Sb atom and the S atoms (S2, S4, S6) not involved in the coordination range from 2.9458 (16) to 3.0617 (17) Å. By taking into account these atoms, the coordination geometry may be described alternatively as distorted octahedral, in which the lone electron pair of the Sb atom projects out of the triangular face defined by the S2, S4 and S6 atoms, thereby elongating these bonds. The crystal packing (Fig. 2) is stabilized mainly by van der Waals interactions. The crystal structure of a similar compound ([Sb(C8H14NS2)3]) have been reported recently (Baba et al., 2001).

Experimental

The title compoud were prepared by reaction of antimony(III) chloride (0.114 g,0.5 mmol) with the corresponding sodium O-alkylxanthate (0.2974 g,1.5 mmol) in absolute benzene. After stirring for 7 h at room temperature, the yellow paste obtained ws filtered. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a n-hexane/dichloromethane (1:2 v/v) solution over a period of ten days (yield 90%; m.p. 450 K). Anal. Calcd (%) for C21H33O3S6Sb (Mr = 646.65): C, 39.00; H, 5.14; O, 7.42; S, 29.75; Sb, 18.82 Found (%): C, 39.02; H, 5.10; O, 7.40; S, 29.77; Sb, 18.79

Refinement

All H atoms were positioned geometrically (C—H = 0.97–0.98 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity.
Fig. 2.
Packing diagram of the title compound viewed approximately along the a axis. H atoms are omitted for clarity.

Crystal data

[Sb(C7H11OS2)3]F(000) = 1316
Mr = 646.58Dx = 1.528 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3706 reflections
a = 9.4187 (12) Åθ = 2.5–25.0°
b = 18.866 (2) ŵ = 1.45 mm1
c = 15.8583 (18) ÅT = 298 K
β = 93.944 (2)°Block, yellow
V = 2811.2 (6) Å30.30 × 0.25 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer4946 independent reflections
Radiation source: fine-focus sealed tube3183 reflections with I > 2σ(I)
graphiteRint = 0.071
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.664, Tmax = 0.773k = −15→22
14030 measured reflectionsl = −16→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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3
4946 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.86 e Å3
90 restraintsΔρmin = −0.60 e Å3

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

xyzUiso*/Ueq
Sb10.23869 (4)0.14457 (2)0.75101 (2)0.04805 (16)
O10.2841 (5)−0.0631 (2)0.6250 (2)0.0678 (12)
O20.6257 (4)0.2720 (2)0.7766 (3)0.0686 (11)
O3−0.0197 (4)0.1350 (3)0.9707 (2)0.0710 (13)
S10.25550 (19)0.01168 (9)0.75366 (9)0.0625 (5)
S20.2947 (2)0.07274 (9)0.58338 (10)0.0703 (5)
S30.50432 (16)0.15233 (7)0.77844 (10)0.0522 (4)
S40.34846 (18)0.28996 (8)0.77444 (12)0.0685 (5)
S50.21960 (15)0.13712 (9)0.90767 (9)0.0551 (4)
S6−0.05683 (19)0.14457 (13)0.80641 (10)0.0940 (7)
C10.2778 (6)0.0043 (3)0.6466 (3)0.0556 (15)
C20.2862 (7)−0.0849 (3)0.5356 (3)0.0608 (17)
H20.3328−0.04870.50280.073*
C30.3659 (7)−0.1531 (4)0.5347 (4)0.0683 (19)
H3A0.3241−0.18690.57180.082*
H3B0.4641−0.14540.55520.082*
C40.3606 (7)−0.1822 (4)0.4458 (4)0.075 (2)
H4A0.4093−0.14990.40990.090*
H4B0.4096−0.22740.44590.090*
C50.2105 (7)−0.1918 (3)0.4107 (4)0.0684 (18)
H5A0.2105−0.20780.35260.082*
H5B0.1653−0.22810.44290.082*
C60.1273 (8)−0.1250 (4)0.4138 (4)0.088 (2)
H6A0.0287−0.13430.39520.106*
H6B0.1644−0.09060.37550.106*
C70.1347 (8)−0.0944 (4)0.5030 (4)0.079 (2)
H7A0.0861−0.04910.50250.095*
H7B0.0870−0.12610.54000.095*
C80.4972 (6)0.2437 (3)0.7757 (3)0.0487 (14)
C90.6450 (7)0.3490 (3)0.7713 (4)0.0678 (17)
H90.55880.37260.78840.081*
C100.7653 (11)0.3685 (4)0.8306 (6)0.119 (3)
H10A0.84860.34100.81870.143*
H10B0.74220.35830.88810.143*
C110.7964 (12)0.4479 (4)0.8213 (6)0.129 (3)
H11A0.71720.47500.84040.155*
H11B0.88050.46000.85710.155*
C120.8189 (10)0.4673 (5)0.7347 (7)0.129 (4)
H120.90010.48960.71740.154*
C130.6975 (12)0.4471 (4)0.6787 (5)0.123 (3)
H13A0.71610.45910.62100.148*
H13B0.61470.47370.69350.148*
C140.6660 (11)0.3674 (4)0.6843 (5)0.102 (2)
H14A0.58130.35590.64870.123*
H14B0.74490.34040.66450.123*
C150.0345 (6)0.1386 (3)0.8972 (3)0.0528 (15)
C16−0.1749 (6)0.1372 (4)0.9774 (4)0.0660 (19)
H16−0.22310.13280.92090.079*
C17−0.2112 (7)0.2063 (4)1.0141 (5)0.081 (2)
H17A−0.18500.24410.97670.097*
H17B−0.15760.21251.06800.097*
C18−0.3717 (7)0.2105 (4)1.0267 (5)0.094 (2)
H18A−0.39200.25391.05630.112*
H18B−0.42480.21140.97210.112*
C19−0.4176 (7)0.1482 (5)1.0765 (5)0.088 (2)
H19A−0.37460.15131.13380.106*
H19B−0.52010.14961.07940.106*
C20−0.3769 (8)0.0802 (4)1.0387 (5)0.086 (2)
H20A−0.42610.07520.98320.103*
H20B−0.40620.04131.07370.103*
C21−0.2153 (7)0.0760 (4)1.0305 (4)0.080 (2)
H21A−0.16510.07851.08590.096*
H21B−0.19090.03171.00410.096*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.0516 (3)0.0496 (3)0.0438 (2)−0.00345 (19)0.00902 (16)−0.0031 (2)
O10.111 (4)0.047 (3)0.047 (2)−0.013 (2)0.014 (2)−0.010 (2)
O20.061 (3)0.042 (2)0.103 (3)−0.003 (2)0.007 (2)0.001 (2)
O30.050 (3)0.125 (4)0.040 (2)0.001 (3)0.0127 (18)0.003 (2)
S10.0940 (13)0.0493 (10)0.0461 (8)−0.0114 (9)0.0185 (8)−0.0035 (8)
S20.1089 (14)0.0522 (11)0.0518 (9)−0.0140 (10)0.0208 (9)−0.0035 (8)
S30.0502 (9)0.0390 (8)0.0681 (9)0.0022 (7)0.0102 (7)−0.0032 (7)
S40.0612 (10)0.0473 (10)0.0995 (13)0.0073 (8)0.0244 (9)−0.0028 (9)
S50.0482 (9)0.0748 (11)0.0425 (7)−0.0002 (8)0.0054 (6)−0.0058 (8)
S60.0518 (10)0.185 (2)0.0455 (9)0.0012 (12)0.0042 (7)0.0083 (12)
C10.067 (4)0.046 (4)0.054 (4)−0.013 (3)0.010 (3)−0.009 (3)
C20.095 (5)0.051 (4)0.036 (3)−0.019 (4)0.005 (3)−0.008 (3)
C30.054 (4)0.086 (5)0.064 (4)0.001 (4)0.001 (3)−0.012 (4)
C40.070 (5)0.095 (6)0.062 (4)0.011 (4)0.012 (3)−0.019 (4)
C50.085 (5)0.054 (4)0.065 (4)0.001 (4)−0.001 (3)−0.019 (3)
C60.097 (6)0.092 (6)0.072 (5)0.019 (5)−0.020 (4)−0.021 (4)
C70.085 (5)0.085 (6)0.067 (4)0.038 (4)−0.005 (4)−0.021 (4)
C80.054 (4)0.047 (4)0.046 (3)0.000 (3)0.013 (3)−0.004 (3)
C90.072 (4)0.041 (4)0.091 (4)−0.009 (3)0.007 (3)0.005 (3)
C100.163 (7)0.068 (5)0.118 (6)−0.025 (5)−0.045 (5)0.002 (5)
C110.161 (7)0.068 (5)0.149 (6)−0.031 (5)−0.052 (6)−0.014 (5)
C120.090 (7)0.087 (7)0.213 (11)−0.048 (6)0.039 (7)0.014 (7)
C130.186 (7)0.078 (5)0.108 (5)−0.025 (5)0.020 (5)0.021 (5)
C140.166 (7)0.053 (4)0.087 (5)−0.024 (5)0.003 (5)0.002 (4)
C150.050 (3)0.058 (4)0.052 (3)−0.002 (3)0.015 (3)−0.003 (3)
C160.045 (4)0.112 (6)0.042 (3)0.000 (4)0.010 (3)0.003 (4)
C170.063 (5)0.066 (5)0.116 (6)−0.002 (4)0.024 (4)0.023 (5)
C180.061 (5)0.101 (7)0.122 (6)0.010 (4)0.023 (4)−0.001 (5)
C190.054 (4)0.139 (8)0.073 (5)−0.015 (5)0.018 (4)−0.008 (5)
C200.072 (5)0.106 (7)0.079 (5)−0.034 (5)0.002 (4)0.020 (5)
C210.071 (5)0.075 (5)0.096 (5)−0.012 (4)0.015 (4)−0.005 (4)

Geometric parameters (Å, °)

Sb1—S52.5072 (14)C9—C101.469 (10)
Sb1—S12.5123 (17)C9—H90.9800
Sb1—S32.5140 (15)C10—C111.535 (10)
O1—C11.320 (6)C10—H10A0.9700
O1—C21.477 (6)C10—H10B0.9700
O2—C81.322 (6)C11—C121.451 (11)
O2—C91.468 (7)C11—H11A0.9700
O3—C151.306 (6)C11—H11B0.9700
O3—C161.474 (7)C12—C131.449 (11)
S1—C11.731 (5)C12—H120.9300
S2—C11.649 (6)C13—C141.537 (10)
S3—C81.726 (6)C13—H13A0.9700
S4—C81.649 (6)C13—H13B0.9700
S5—C151.740 (6)C14—H14A0.9700
S6—C151.630 (6)C14—H14B0.9700
C2—C31.490 (8)C16—C171.475 (9)
C2—C71.496 (9)C16—C211.493 (9)
C2—H20.9800C16—H160.9800
C3—C41.511 (8)C17—C181.541 (9)
C3—H3A0.9700C17—H17A0.9700
C3—H3B0.9700C17—H17B0.9700
C4—C51.493 (8)C18—C191.497 (10)
C4—H4A0.9700C18—H18A0.9700
C4—H4B0.9700C18—H18B0.9700
C5—C61.487 (9)C19—C201.479 (10)
C5—H5A0.9700C19—H19A0.9700
C5—H5B0.9700C19—H19B0.9700
C6—C71.524 (8)C20—C211.538 (9)
C6—H6A0.9700C20—H20A0.9700
C6—H6B0.9700C20—H20B0.9700
C7—H7A0.9700C21—H21A0.9700
C7—H7B0.9700C21—H21B0.9700
C9—C141.450 (10)
S5—Sb1—S186.34 (5)H10A—C10—H10B108.3
S5—Sb1—S388.29 (5)C12—C11—C10112.3 (8)
S1—Sb1—S389.68 (5)C12—C11—H11A109.1
C1—O1—C2121.3 (5)C10—C11—H11A109.1
C8—O2—C9121.0 (5)C12—C11—H11B109.1
C15—O3—C16120.9 (4)C10—C11—H11B109.1
C1—S1—Sb194.3 (2)H11A—C11—H11B107.9
C8—S3—Sb191.0 (2)C13—C12—C11110.7 (7)
C15—S5—Sb192.54 (18)C13—C12—H12124.7
O1—C1—S2126.1 (4)C11—C12—H12124.7
O1—C1—S1110.0 (4)C12—C13—C14111.7 (8)
S2—C1—S1123.8 (3)C12—C13—H13A109.3
O1—C2—C3106.8 (5)C14—C13—H13A109.3
O1—C2—C7106.9 (5)C12—C13—H13B109.3
C3—C2—C7111.2 (5)C14—C13—H13B109.3
O1—C2—H2110.6H13A—C13—H13B107.9
C3—C2—H2110.6C9—C14—C13109.2 (6)
C7—C2—H2110.6C9—C14—H14A109.8
C2—C3—C4109.8 (5)C13—C14—H14A109.8
C2—C3—H3A109.7C9—C14—H14B109.8
C4—C3—H3A109.7C13—C14—H14B109.8
C2—C3—H3B109.7H14A—C14—H14B108.3
C4—C3—H3B109.7O3—C15—S6125.2 (4)
H3A—C3—H3B108.2O3—C15—S5111.4 (4)
C5—C4—C3111.2 (5)S6—C15—S5123.4 (3)
C5—C4—H4A109.4O3—C16—C17108.1 (5)
C3—C4—H4A109.4O3—C16—C21108.2 (5)
C5—C4—H4B109.4C17—C16—C21112.7 (5)
C3—C4—H4B109.4O3—C16—H16109.3
H4A—C4—H4B108.0C17—C16—H16109.3
C6—C5—C4111.8 (6)C21—C16—H16109.3
C6—C5—H5A109.2C16—C17—C18110.7 (6)
C4—C5—H5A109.2C16—C17—H17A109.5
C6—C5—H5B109.2C18—C17—H17A109.5
C4—C5—H5B109.2C16—C17—H17B109.5
H5A—C5—H5B107.9C18—C17—H17B109.5
C5—C6—C7111.1 (5)H17A—C17—H17B108.1
C5—C6—H6A109.4C19—C18—C17110.5 (6)
C7—C6—H6A109.4C19—C18—H18A109.6
C5—C6—H6B109.4C17—C18—H18A109.6
C7—C6—H6B109.4C19—C18—H18B109.6
H6A—C6—H6B108.0C17—C18—H18B109.6
C2—C7—C6110.4 (6)H18A—C18—H18B108.1
C2—C7—H7A109.6C20—C19—C18112.0 (6)
C6—C7—H7A109.6C20—C19—H19A109.2
C2—C7—H7B109.6C18—C19—H19A109.2
C6—C7—H7B109.6C20—C19—H19B109.2
H7A—C7—H7B108.1C18—C19—H19B109.2
O2—C8—S4124.3 (4)H19A—C19—H19B107.9
O2—C8—S3111.6 (4)C19—C20—C21111.3 (6)
S4—C8—S3124.1 (3)C19—C20—H20A109.4
C14—C9—O2108.5 (6)C21—C20—H20A109.4
C14—C9—C10113.6 (7)C19—C20—H20B109.4
O2—C9—C10107.6 (6)C21—C20—H20B109.4
C14—C9—H9109.0H20A—C20—H20B108.0
O2—C9—H9109.0C16—C21—C20107.5 (6)
C10—C9—H9109.0C16—C21—H21A110.2
C9—C10—C11109.0 (7)C20—C21—H21A110.2
C9—C10—H10A109.9C16—C21—H21B110.2
C11—C10—H10A109.9C20—C21—H21B110.2
C9—C10—H10B109.9H21A—C21—H21B108.5
C11—C10—H10B109.9

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2271).

References

  • Baba, I., Ibrahim, S., Farina, Y., Othman, A. H., Razak, I. A., Fun, H.-K. & Ng, S. W. (2001). Acta Cryst. E57, m39–m40.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Tiekink, E. R. T. (2002). Crit. Rev. Oncol. Hematol.42, 217-224. [PubMed]
  • Wang, G.-C., Lu, Y.-N., Xiao, J., Yu, L., Song, H.-B., Li, J.-S., Cui, J.-R., Wang, R.-Q. & Ran, F.-X. (2005). J. Organomet. Chem.690, 151–156.

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