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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): m656–m657.
Published online 2009 May 20. doi:  10.1107/S1600536809017449
PMCID: PMC2969530

Triphenyl­bis[4-(trifluoro­meth­yl)benzoato-κO]anti­mony(V)

Abstract

The title complex, [Sb(C6H5)3(C8H4F3O2)2], is located on a twofold axis defined by the metal center and two C atoms of a coordinated phenyl group. The environment of the Sb atom approximates a trigonal-bipyramidal geometry, with the axial positions occupied by the O atoms of symmetry-related 4-(trifluoro­meth­yl)benzoate ligands. In this ligand, the CF3 group is disordered by rotation about the C—C bond and the F atoms are distributed over two sets of sites with occupancies of 0.62 (3) and 0.38 (3). In the crystal, mol­ecules are assembled in a three-dimensional framework through weak C—H(...)O hydrogen bonds.

Related literature

For related Sb(V) structures, see: Sharutin et al. (2003 [triangle]); Yin et al. (2008 [triangle]); Yu et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m656-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)3(C8H4F3O2)2]
  • M r = 731.27
  • Hexagonal, An external file that holds a picture, illustration, etc.
Object name is e-65-0m656-efi2.jpg
  • a = 12.9879 (10) Å
  • c = 16.042 (2) Å
  • V = 2343.5 (4) Å3
  • Z = 3
  • Mo Kα radiation
  • μ = 0.96 mm−1
  • T = 298 K
  • 0.44 × 0.31 × 0.24 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.679, T max = 0.803
  • 9708 measured reflections
  • 2719 independent reflections
  • 1962 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.145
  • S = 1.08
  • 2719 reflections
  • 233 parameters
  • 55 restraints
  • H-atom parameters constrained
  • Δρmax = 0.90 e Å−3
  • Δρmin = −0.41 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1284 Friedel pairs
  • Flack parameter: 0.04 (7)

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: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017449/bh2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017449/bh2229Isup2.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

Some triorganoantimony(V) complexes with acetylferroceneoxime as ligand showed in vitro antitumor activity (Yin et al., 2008). The related title compound may show similar activity. The title complex is also related to triphenyl-bis(4-methylbenzoato-κO)-antimony(V), previously characterized (Sharutin et al., 2003), although both complexes are not isostructural and crystallize in different space groups.

The crystal structure of the title complex consists of isolated molecules which have C2 molecular symmetry. The 2-fold axis is defined by atoms Sb1/C15/C18. The coordination geometry around the antimony center is best described as a distorted trigonal bipyramid. Two carboxylate groups occupy the axial sites with O1—Sb1—-O1i angle being 176.0 (3)° [symmetry code: (i) 2 - x, 1 - y, z]. In the equatorial plane, the sum of angles C9—Sb1—C9i, C9—Sb1—C15 and C15—Sb1—C9i is 360.0°. The Sb1—O1 bond length, 2.150 (5) Å, is significantly different from the corresponding distance in [4-(C5H5FeC5H4)C6H4COO]2Sb(C6H4F-4)3, 2.087 (6) Å (Yu et al., 2004), but much shorter than the sum of the van der Waals radii for Sb and O, 3.2 Å. The Sb—C distances fall in the expected range found in the literature (Yu et al., 2004).

Experimental

4-Trifluoromethylbenzoic acid (0.152 g, 0.8 mmol) and sodium methoxide (0.8 mmol) were added to a stirring solution containing dichlorotriphenylantimony (0.172 g, 0.4 mmol) in toluene (25 ml). After refluxing for 8 h., a colorless solution was obtained and then filtered. The solvent was gradually removed by evaporation under vacuum until a white solid was obtained. The solid was recrystallized from petroleum ether/dichoromethane (1:1) to give colorless crystals of the title complex.

Refinement

H atoms were placed in calculated positions and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(carrier C). F atoms were found to be disordered over two positions: F1/F1', F2/F2' and F3/F3'. Their occupancies were refined with the sum constrained to unity, and converged to 0.62 (3) [F1/F2/F3] and 0.38 (3) [F1'/F2'/F3']. Geometry was restrained (restraints not given). The Flack parameter has been refined (1284 measured Friedel pairs), although not documented by authors.

Figures

Fig. 1.
The molecular structure of the title complex, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
A chain of molecules linked by C3—H3···O2#1 intermolecular hydrogen bonds (dashed lines) (symmetry code #1: 1 - y, x-y, z - 1/3).

Crystal data

[Sb(C6H5)3(C8H4F3O2)2]Dx = 1.554 Mg m3
Mr = 731.27Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P62Cell parameters from 3513 reflections
Hall symbol: P 62θ = 2.2–23.0°
a = 12.9879 (10) ŵ = 0.96 mm1
c = 16.042 (2) ÅT = 298 K
V = 2343.5 (4) Å3Block, colorless
Z = 30.44 × 0.31 × 0.24 mm
F(000) = 1092

Data collection

Bruker SMART diffractometer2719 independent reflections
Radiation source: fine-focus sealed tube1962 reflections with I > 2σ(I)
graphiteRint = 0.053
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→9
Tmin = 0.679, Tmax = 0.803k = −15→12
9708 measured reflectionsl = −19→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.145w = 1/[σ2(Fo2) + (0.0684P)2 + 2.131P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.026
2719 reflectionsΔρmax = 0.90 e Å3
233 parametersΔρmin = −0.41 e Å3
55 restraintsAbsolute structure: Flack (1983), 1284 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (7)

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

xyzUiso*/UeqOcc. (<1)
Sb11.00000.50000.10910 (15)0.0641 (3)
F10.2113 (17)0.1590 (11)0.182 (2)0.26 (2)0.62 (3)
F20.241 (2)0.294 (3)0.2756 (10)0.25 (2)0.62 (3)
F30.2382 (14)0.3226 (13)0.1459 (10)0.127 (8)0.62 (3)
F1'0.242 (3)0.3496 (19)0.228 (3)0.23 (3)0.38 (3)
F2'0.209 (3)0.215 (3)0.1356 (11)0.24 (3)0.38 (3)
F3'0.2233 (18)0.1848 (16)0.2607 (10)0.096 (9)0.38 (3)
O10.8139 (5)0.4442 (5)0.1045 (4)0.0653 (16)
O20.8310 (6)0.4481 (7)0.2417 (4)0.092 (2)
C10.7700 (8)0.4310 (9)0.1798 (6)0.070 (3)
C20.6436 (8)0.3930 (8)0.1835 (6)0.065 (2)
C30.5766 (9)0.3813 (9)0.1133 (7)0.074 (3)
H30.61290.40110.06120.089*
C40.4582 (10)0.3412 (10)0.1200 (9)0.092 (3)
H40.41370.33210.07230.110*
C50.4034 (10)0.3138 (10)0.1967 (9)0.088 (3)
C60.4660 (10)0.3246 (12)0.2652 (8)0.102 (4)
H60.42870.30570.31700.122*
C70.5843 (9)0.3631 (12)0.2599 (7)0.098 (4)
H70.62660.36970.30820.117*
C80.2710 (11)0.2707 (11)0.2030 (8)0.136 (7)
C91.0390 (9)0.6667 (9)0.1536 (6)0.077 (3)
C101.0489 (11)0.6986 (11)0.2367 (6)0.108 (4)
H101.04000.64390.27760.130*
C111.0718 (14)0.8097 (13)0.2596 (12)0.157 (9)
H111.07780.83040.31560.189*
C121.0856 (16)0.8904 (16)0.1985 (12)0.159 (9)
H121.10020.96570.21340.191*
C131.0781 (13)0.8602 (11)0.1153 (12)0.146 (6)
H131.08880.91540.07440.176*
C141.0547 (11)0.7483 (10)0.0928 (8)0.102 (4)
H141.04960.72780.03680.122*
C151.00000.5000−0.0220 (6)0.053 (3)
C161.0867 (9)0.4904 (10)−0.0660 (7)0.090 (3)
H161.14700.4863−0.03770.108*
C171.0832 (12)0.4871 (14)−0.1517 (7)0.120 (5)
H171.13870.4757−0.18070.144*
C181.00000.5000−0.1948 (9)0.116 (7)
H181.00000.5000−0.25280.139*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.0578 (5)0.0795 (7)0.0433 (3)0.0256 (5)0.0000.000
F10.076 (11)0.068 (10)0.60 (7)0.003 (8)−0.06 (3)0.05 (2)
F20.15 (2)0.44 (6)0.22 (2)0.19 (3)0.083 (19)0.13 (3)
F30.065 (9)0.100 (11)0.22 (2)0.043 (8)−0.020 (10)−0.016 (11)
F1'0.11 (3)0.083 (18)0.50 (9)0.047 (16)0.09 (5)0.03 (4)
F2'0.074 (17)0.37 (7)0.20 (4)0.06 (3)−0.015 (17)0.15 (4)
F3'0.053 (11)0.092 (16)0.109 (16)0.011 (10)0.013 (10)−0.009 (11)
O10.053 (3)0.088 (4)0.048 (3)0.030 (3)0.003 (3)−0.003 (3)
O20.051 (4)0.144 (7)0.054 (4)0.029 (4)−0.005 (3)0.000 (4)
C10.053 (6)0.086 (7)0.057 (5)0.024 (5)−0.002 (4)−0.005 (4)
C20.058 (6)0.060 (6)0.062 (5)0.019 (5)0.000 (4)−0.004 (4)
C30.068 (6)0.084 (7)0.062 (5)0.033 (5)−0.003 (6)0.003 (6)
C40.075 (7)0.093 (8)0.105 (9)0.040 (6)−0.027 (7)0.010 (7)
C50.060 (7)0.071 (7)0.121 (10)0.024 (6)0.014 (7)0.024 (7)
C60.068 (7)0.141 (11)0.077 (8)0.037 (7)0.017 (6)0.020 (8)
C70.069 (7)0.154 (12)0.054 (6)0.044 (7)0.004 (5)0.000 (6)
C80.068 (10)0.116 (15)0.21 (2)0.032 (10)0.009 (12)0.062 (14)
C90.055 (6)0.082 (7)0.085 (7)0.027 (6)0.013 (5)−0.002 (6)
C100.086 (8)0.109 (10)0.100 (9)0.026 (7)0.016 (7)−0.040 (7)
C110.097 (11)0.147 (16)0.17 (2)0.019 (11)0.027 (12)−0.087 (15)
C120.108 (13)0.096 (13)0.23 (3)0.016 (11)0.036 (15)−0.056 (14)
C130.107 (11)0.098 (11)0.21 (2)0.030 (9)0.033 (14)0.001 (13)
C140.097 (9)0.074 (8)0.118 (11)0.031 (7)0.015 (8)−0.007 (8)
C150.048 (7)0.067 (8)0.032 (5)0.019 (6)0.0000.000
C160.079 (7)0.141 (9)0.056 (6)0.060 (7)−0.012 (5)−0.019 (7)
C170.115 (10)0.216 (16)0.061 (7)0.106 (11)−0.005 (6)−0.034 (8)
C180.097 (13)0.22 (2)0.037 (7)0.083 (14)0.0000.000

Geometric parameters (Å, °)

Sb1—C92.087 (10)C6—C71.359 (15)
Sb1—C9i2.087 (10)C6—H60.9300
Sb1—C152.103 (10)C7—H70.9300
Sb1—O12.150 (5)C9—C141.377 (9)
Sb1—O1i2.150 (5)C9—C101.383 (9)
F1—C81.302 (9)C10—C111.370 (9)
F2—C81.310 (10)C10—H100.9300
F3—C81.328 (9)C11—C121.380 (10)
F1'—C81.317 (10)C11—H110.9300
F2'—C81.323 (10)C12—C131.380 (10)
F3'—C81.341 (10)C12—H120.9300
O1—C11.311 (11)C13—C141.376 (9)
O2—C11.219 (10)C13—H130.9300
C1—C21.459 (13)C14—H140.9300
C2—C31.386 (14)C15—C16i1.386 (12)
C2—C71.395 (13)C15—C161.386 (12)
C3—C41.359 (14)C16—C171.375 (16)
C3—H30.9300C16—H160.9300
C4—C51.375 (18)C17—C181.362 (16)
C4—H40.9300C17—H170.9300
C5—C61.333 (17)C18—C17i1.362 (16)
C5—C81.522 (16)C18—H180.9300
C9—Sb1—C9i140.0 (5)F2—C8—F2'133 (2)
C9—Sb1—C15110.0 (3)F1'—C8—F2'110.0 (16)
C9i—Sb1—C15110.0 (3)F3'—C8—F2'102.1 (13)
C9—Sb1—O190.6 (3)F1—C8—F2'47.2 (14)
C9i—Sb1—O190.8 (3)F3—C8—F2'56.8 (15)
C15—Sb1—O188.02 (16)F2—C8—C5112.6 (15)
C9—Sb1—O1i90.8 (3)F1'—C8—C5116.3 (18)
C9i—Sb1—O1i90.6 (3)F3'—C8—C5108.6 (13)
C15—Sb1—O1i88.02 (16)F1—C8—C5109.0 (13)
O1—Sb1—O1i176.0 (3)F3—C8—C5111.0 (11)
C1—O1—Sb1110.8 (6)F2'—C8—C5114.2 (18)
O2—C1—O1121.7 (9)C14—C9—C10119.7 (11)
O2—C1—C2123.2 (8)C14—C9—Sb1115.0 (7)
O1—C1—C2115.1 (8)C10—C9—Sb1125.3 (9)
C3—C2—C7117.0 (9)C11—C10—C9120.8 (13)
C3—C2—C1122.8 (9)C11—C10—H10119.6
C7—C2—C1120.1 (9)C9—C10—H10119.6
C4—C3—C2120.4 (11)C10—C11—C12119.1 (17)
C4—C3—H3119.8C10—C11—H11120.4
C2—C3—H3119.8C12—C11—H11120.4
C3—C4—C5120.7 (11)C13—C12—C11120.5 (18)
C3—C4—H4119.7C13—C12—H12119.8
C5—C4—H4119.7C11—C12—H12119.8
C6—C5—C4120.1 (11)C14—C13—C12120.0 (16)
C6—C5—C8120.1 (12)C14—C13—H13120.0
C4—C5—C8119.8 (12)C12—C13—H13120.0
C5—C6—C7120.2 (11)C9—C14—C13119.8 (13)
C5—C6—H6119.9C9—C14—H14120.1
C7—C6—H6119.9C13—C14—H14120.1
C6—C7—C2121.6 (11)C16i—C15—C16118.8 (12)
C6—C7—H7119.2C16i—C15—Sb1120.6 (6)
C2—C7—H7119.2C16—C15—Sb1120.6 (6)
F2—C8—F1'46.9 (16)C17—C16—C15119.7 (10)
F2—C8—F3'60.8 (14)C17—C16—H16120.1
F1'—C8—F3'104.1 (14)C15—C16—H16120.1
F2—C8—F1114.2 (14)C18—C17—C16121.3 (11)
F1'—C8—F1135 (2)C18—C17—H17119.3
F3'—C8—F158.8 (14)C16—C17—H17119.3
F2—C8—F3106.8 (13)C17—C18—C17i118.9 (15)
F1'—C8—F361.8 (19)C17—C18—H18120.5
F3'—C8—F3140.1 (15)C17i—C18—H18120.5
F1—C8—F3102.8 (12)

Symmetry codes: (i) −x+2, −y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O2ii0.932.553.304 (13)138

Symmetry codes: (ii) −y+1, xy, z−1/3.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2229).

References

  • Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sharutin, V. V., Sharutina, O. K., Pakusina, A. P., Platonova, T. P., Smirnova, S. V., Pushilin, M. A. & Gerasimenko, A. V. (2003). Russ. J. Coord. Chem.29, 780–789.
  • 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.
  • Yin, H. D., Quan, L. & Li, L. W. (2008). Inorg. Chem. Commun.11, 1121–1124.
  • Yu, L., Ma, Y.-Q., Liu, R.-C., Wang, G.-C., Li, J.-S., Du, G.-H. & Hu, J.-J. (2004). Polyhedron, 23, 823–829.

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