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

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: handongyin@163.com

(Received 13 November 2008; accepted 3 December 2008; online 10 December 2008)

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[Tiekink, E. R. T. (2002). Crit. Rev. Oncol. Hematol. 42, 217-224.]); Wang et al. (2005[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.]). For a related structure, see: Baba et al. (2001[Baba, I., Ibrahim, S., Farina, Y., Othman, A. H., Razak, I. A., Fun, H.-K. & Ng, S. W. (2001). Acta Cryst. E57, m39-m40.]).

[Scheme 1]

Experimental

Crystal data
  • [Sb(C7H11OS2)3]

  • Mr = 646.58

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.664, Tmax = 0.773

  • 14030 measured reflections

  • 4946 independent reflections

  • 3183 reflections with I > 2σ(I)

  • Rint = 0.071

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Sb1—S5 2.5072 (14)
Sb1—S1 2.5123 (17)
Sb1—S3 2.5140 (15)

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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

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, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed approximately along the a axis. H atoms are omitted for clarity.
Tris(O-cyclohexyl dithiocarbonato-κS)antimony(III) top
Crystal data top
[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 top
Bruker SMART CCD area-detector
diffractometer
4946 independent reflections
Radiation source: fine-focus sealed tube3183 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ϕ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.664, Tmax = 0.773k = 1522
14030 measured reflectionsl = 1618
Refinement top
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 = 1.00 w = 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
Crystal data top
[Sb(C7H11OS2)3]V = 2811.2 (6) Å3
Mr = 646.58Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.4187 (12) ŵ = 1.45 mm1
b = 18.866 (2) ÅT = 298 K
c = 15.8583 (18) Å0.30 × 0.25 × 0.18 mm
β = 93.944 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4946 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3183 reflections with I > 2σ(I)
Tmin = 0.664, Tmax = 0.773Rint = 0.071
14030 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04790 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.00Δρmax = 0.86 e Å3
4946 reflectionsΔρmin = 0.60 e Å3
280 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
O30.0197 (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)
S60.05683 (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)
H20.33280.04870.50280.073*
C30.3659 (7)0.1531 (4)0.5347 (4)0.0683 (19)
H3A0.32410.18690.57180.082*
H3B0.46410.14540.55520.082*
C40.3606 (7)0.1822 (4)0.4458 (4)0.075 (2)
H4A0.40930.14990.40990.090*
H4B0.40960.22740.44590.090*
C50.2105 (7)0.1918 (3)0.4107 (4)0.0684 (18)
H5A0.21050.20780.35260.082*
H5B0.16530.22810.44290.082*
C60.1273 (8)0.1250 (4)0.4138 (4)0.088 (2)
H6A0.02870.13430.39520.106*
H6B0.16440.09060.37550.106*
C70.1347 (8)0.0944 (4)0.5030 (4)0.079 (2)
H7A0.08610.04910.50250.095*
H7B0.08700.12610.54000.095*
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)
C160.1749 (6)0.1372 (4)0.9774 (4)0.0660 (19)
H160.22310.13280.92090.079*
C170.2112 (7)0.2063 (4)1.0141 (5)0.081 (2)
H17A0.18500.24410.97670.097*
H17B0.15760.21251.06800.097*
C180.3717 (7)0.2105 (4)1.0267 (5)0.094 (2)
H18A0.39200.25391.05630.112*
H18B0.42480.21140.97210.112*
C190.4176 (7)0.1482 (5)1.0765 (5)0.088 (2)
H19A0.37460.15131.13380.106*
H19B0.52010.14961.07940.106*
C200.3769 (8)0.0802 (4)1.0387 (5)0.086 (2)
H20A0.42610.07520.98320.103*
H20B0.40620.04131.07370.103*
C210.2153 (7)0.0760 (4)1.0305 (4)0.080 (2)
H21A0.16510.07851.08590.096*
H21B0.19090.03171.00410.096*
Atomic displacement parameters (Å2) top
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, º) top
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

Experimental details

Crystal data
Chemical formula[Sb(C7H11OS2)3]
Mr646.58
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.4187 (12), 18.866 (2), 15.8583 (18)
β (°) 93.944 (2)
V3)2811.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.30 × 0.25 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.664, 0.773
No. of measured, independent and
observed [I > 2σ(I)] reflections
14030, 4946, 3183
Rint0.071
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.00
No. of reflections4946
No. of parameters280
No. of restraints90
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.86, 0.60

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Sb1—S52.5072 (14)S3—C81.726 (6)
Sb1—S12.5123 (17)S4—C81.649 (6)
Sb1—S32.5140 (15)S5—C151.740 (6)
S1—C11.731 (5)S6—C151.630 (6)
S2—C11.649 (6)
 

Acknowledgements

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

References

First citationBaba, I., Ibrahim, S., Farina, Y., Othman, A. H., Razak, I. A., Fun, H.-K. & Ng, S. W. (2001). Acta Cryst. E57, m39–m40.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationTiekink, E. R. T. (2002). Crit. Rev. Oncol. Hematol. 42, 217-224.  Web of Science CrossRef PubMed Google Scholar
First citationWang, 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.  Web of Science CSD CrossRef CAS Google Scholar

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