metal-organic compounds
Triphenylbis[4-(trifluoromethyl)benzoato-κO]antimony(V)
aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: quanli99@126.com
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); Yin et al. (2008); Yu et al. (2004).
Experimental
Crystal data
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
10.1107/S1600536809017449/bh2229sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809017449/bh2229Isup2.hkl
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.
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
has been refined (1284 measured Friedel pairs), although not documented by authors.Data collection: SMART (Siemens, 1996); cell
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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Sb(C6H5)3(C8H4F3O2)2] | Dx = 1.554 Mg m−3 |
Mr = 731.27 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P62 | Cell parameters from 3513 reflections |
Hall symbol: P 62 | θ = 2.2–23.0° |
a = 12.9879 (10) Å | µ = 0.96 mm−1 |
c = 16.042 (2) Å | T = 298 K |
V = 2343.5 (4) Å3 | Block, colorless |
Z = 3 | 0.44 × 0.31 × 0.24 mm |
F(000) = 1092 |
Bruker SMART diffractometer | 2719 independent reflections |
Radiation source: fine-focus sealed tube | 1962 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→9 |
Tmin = 0.679, Tmax = 0.803 | k = −15→12 |
9708 measured reflections | l = −19→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0684P)2 + 2.131P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.026 |
2719 reflections | Δρmax = 0.90 e Å−3 |
233 parameters | Δρmin = −0.41 e Å−3 |
55 restraints | Absolute structure: Flack (1983), 1284 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (7) |
[Sb(C6H5)3(C8H4F3O2)2] | Z = 3 |
Mr = 731.27 | Mo Kα radiation |
Hexagonal, P62 | µ = 0.96 mm−1 |
a = 12.9879 (10) Å | T = 298 K |
c = 16.042 (2) Å | 0.44 × 0.31 × 0.24 mm |
V = 2343.5 (4) Å3 |
Bruker SMART diffractometer | 2719 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1962 reflections with I > 2σ(I) |
Tmin = 0.679, Tmax = 0.803 | Rint = 0.053 |
9708 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.145 | Δρmax = 0.90 e Å−3 |
S = 1.08 | Δρmin = −0.41 e Å−3 |
2719 reflections | Absolute structure: Flack (1983), 1284 Friedel pairs |
233 parameters | Absolute structure parameter: 0.04 (7) |
55 restraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sb1 | 1.0000 | 0.5000 | 0.10910 (15) | 0.0641 (3) | |
F1 | 0.2113 (17) | 0.1590 (11) | 0.182 (2) | 0.26 (2) | 0.62 (3) |
F2 | 0.241 (2) | 0.294 (3) | 0.2756 (10) | 0.25 (2) | 0.62 (3) |
F3 | 0.2382 (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) |
O1 | 0.8139 (5) | 0.4442 (5) | 0.1045 (4) | 0.0653 (16) | |
O2 | 0.8310 (6) | 0.4481 (7) | 0.2417 (4) | 0.092 (2) | |
C1 | 0.7700 (8) | 0.4310 (9) | 0.1798 (6) | 0.070 (3) | |
C2 | 0.6436 (8) | 0.3930 (8) | 0.1835 (6) | 0.065 (2) | |
C3 | 0.5766 (9) | 0.3813 (9) | 0.1133 (7) | 0.074 (3) | |
H3 | 0.6129 | 0.4011 | 0.0612 | 0.089* | |
C4 | 0.4582 (10) | 0.3412 (10) | 0.1200 (9) | 0.092 (3) | |
H4 | 0.4137 | 0.3321 | 0.0723 | 0.110* | |
C5 | 0.4034 (10) | 0.3138 (10) | 0.1967 (9) | 0.088 (3) | |
C6 | 0.4660 (10) | 0.3246 (12) | 0.2652 (8) | 0.102 (4) | |
H6 | 0.4287 | 0.3057 | 0.3170 | 0.122* | |
C7 | 0.5843 (9) | 0.3631 (12) | 0.2599 (7) | 0.098 (4) | |
H7 | 0.6266 | 0.3697 | 0.3082 | 0.117* | |
C8 | 0.2710 (11) | 0.2707 (11) | 0.2030 (8) | 0.136 (7) | |
C9 | 1.0390 (9) | 0.6667 (9) | 0.1536 (6) | 0.077 (3) | |
C10 | 1.0489 (11) | 0.6986 (11) | 0.2367 (6) | 0.108 (4) | |
H10 | 1.0400 | 0.6439 | 0.2776 | 0.130* | |
C11 | 1.0718 (14) | 0.8097 (13) | 0.2596 (12) | 0.157 (9) | |
H11 | 1.0778 | 0.8304 | 0.3156 | 0.189* | |
C12 | 1.0856 (16) | 0.8904 (16) | 0.1985 (12) | 0.159 (9) | |
H12 | 1.1002 | 0.9657 | 0.2134 | 0.191* | |
C13 | 1.0781 (13) | 0.8602 (11) | 0.1153 (12) | 0.146 (6) | |
H13 | 1.0888 | 0.9154 | 0.0744 | 0.176* | |
C14 | 1.0547 (11) | 0.7483 (10) | 0.0928 (8) | 0.102 (4) | |
H14 | 1.0496 | 0.7278 | 0.0368 | 0.122* | |
C15 | 1.0000 | 0.5000 | −0.0220 (6) | 0.053 (3) | |
C16 | 1.0867 (9) | 0.4904 (10) | −0.0660 (7) | 0.090 (3) | |
H16 | 1.1470 | 0.4863 | −0.0377 | 0.108* | |
C17 | 1.0832 (12) | 0.4871 (14) | −0.1517 (7) | 0.120 (5) | |
H17 | 1.1387 | 0.4757 | −0.1807 | 0.144* | |
C18 | 1.0000 | 0.5000 | −0.1948 (9) | 0.116 (7) | |
H18 | 1.0000 | 0.5000 | −0.2528 | 0.139* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sb1 | 0.0578 (5) | 0.0795 (7) | 0.0433 (3) | 0.0256 (5) | 0.000 | 0.000 |
F1 | 0.076 (11) | 0.068 (10) | 0.60 (7) | 0.003 (8) | −0.06 (3) | 0.05 (2) |
F2 | 0.15 (2) | 0.44 (6) | 0.22 (2) | 0.19 (3) | 0.083 (19) | 0.13 (3) |
F3 | 0.065 (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) |
O1 | 0.053 (3) | 0.088 (4) | 0.048 (3) | 0.030 (3) | 0.003 (3) | −0.003 (3) |
O2 | 0.051 (4) | 0.144 (7) | 0.054 (4) | 0.029 (4) | −0.005 (3) | 0.000 (4) |
C1 | 0.053 (6) | 0.086 (7) | 0.057 (5) | 0.024 (5) | −0.002 (4) | −0.005 (4) |
C2 | 0.058 (6) | 0.060 (6) | 0.062 (5) | 0.019 (5) | 0.000 (4) | −0.004 (4) |
C3 | 0.068 (6) | 0.084 (7) | 0.062 (5) | 0.033 (5) | −0.003 (6) | 0.003 (6) |
C4 | 0.075 (7) | 0.093 (8) | 0.105 (9) | 0.040 (6) | −0.027 (7) | 0.010 (7) |
C5 | 0.060 (7) | 0.071 (7) | 0.121 (10) | 0.024 (6) | 0.014 (7) | 0.024 (7) |
C6 | 0.068 (7) | 0.141 (11) | 0.077 (8) | 0.037 (7) | 0.017 (6) | 0.020 (8) |
C7 | 0.069 (7) | 0.154 (12) | 0.054 (6) | 0.044 (7) | 0.004 (5) | 0.000 (6) |
C8 | 0.068 (10) | 0.116 (15) | 0.21 (2) | 0.032 (10) | 0.009 (12) | 0.062 (14) |
C9 | 0.055 (6) | 0.082 (7) | 0.085 (7) | 0.027 (6) | 0.013 (5) | −0.002 (6) |
C10 | 0.086 (8) | 0.109 (10) | 0.100 (9) | 0.026 (7) | 0.016 (7) | −0.040 (7) |
C11 | 0.097 (11) | 0.147 (16) | 0.17 (2) | 0.019 (11) | 0.027 (12) | −0.087 (15) |
C12 | 0.108 (13) | 0.096 (13) | 0.23 (3) | 0.016 (11) | 0.036 (15) | −0.056 (14) |
C13 | 0.107 (11) | 0.098 (11) | 0.21 (2) | 0.030 (9) | 0.033 (14) | 0.001 (13) |
C14 | 0.097 (9) | 0.074 (8) | 0.118 (11) | 0.031 (7) | 0.015 (8) | −0.007 (8) |
C15 | 0.048 (7) | 0.067 (8) | 0.032 (5) | 0.019 (6) | 0.000 | 0.000 |
C16 | 0.079 (7) | 0.141 (9) | 0.056 (6) | 0.060 (7) | −0.012 (5) | −0.019 (7) |
C17 | 0.115 (10) | 0.216 (16) | 0.061 (7) | 0.106 (11) | −0.005 (6) | −0.034 (8) |
C18 | 0.097 (13) | 0.22 (2) | 0.037 (7) | 0.083 (14) | 0.000 | 0.000 |
Sb1—C9 | 2.087 (10) | C6—C7 | 1.359 (15) |
Sb1—C9i | 2.087 (10) | C6—H6 | 0.9300 |
Sb1—C15 | 2.103 (10) | C7—H7 | 0.9300 |
Sb1—O1 | 2.150 (5) | C9—C14 | 1.377 (9) |
Sb1—O1i | 2.150 (5) | C9—C10 | 1.383 (9) |
F1—C8 | 1.302 (9) | C10—C11 | 1.370 (9) |
F2—C8 | 1.310 (10) | C10—H10 | 0.9300 |
F3—C8 | 1.328 (9) | C11—C12 | 1.380 (10) |
F1'—C8 | 1.317 (10) | C11—H11 | 0.9300 |
F2'—C8 | 1.323 (10) | C12—C13 | 1.380 (10) |
F3'—C8 | 1.341 (10) | C12—H12 | 0.9300 |
O1—C1 | 1.311 (11) | C13—C14 | 1.376 (9) |
O2—C1 | 1.219 (10) | C13—H13 | 0.9300 |
C1—C2 | 1.459 (13) | C14—H14 | 0.9300 |
C2—C3 | 1.386 (14) | C15—C16i | 1.386 (12) |
C2—C7 | 1.395 (13) | C15—C16 | 1.386 (12) |
C3—C4 | 1.359 (14) | C16—C17 | 1.375 (16) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.375 (18) | C17—C18 | 1.362 (16) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.333 (17) | C18—C17i | 1.362 (16) |
C5—C8 | 1.522 (16) | C18—H18 | 0.9300 |
C9—Sb1—C9i | 140.0 (5) | F2—C8—F2' | 133 (2) |
C9—Sb1—C15 | 110.0 (3) | F1'—C8—F2' | 110.0 (16) |
C9i—Sb1—C15 | 110.0 (3) | F3'—C8—F2' | 102.1 (13) |
C9—Sb1—O1 | 90.6 (3) | F1—C8—F2' | 47.2 (14) |
C9i—Sb1—O1 | 90.8 (3) | F3—C8—F2' | 56.8 (15) |
C15—Sb1—O1 | 88.02 (16) | F2—C8—C5 | 112.6 (15) |
C9—Sb1—O1i | 90.8 (3) | F1'—C8—C5 | 116.3 (18) |
C9i—Sb1—O1i | 90.6 (3) | F3'—C8—C5 | 108.6 (13) |
C15—Sb1—O1i | 88.02 (16) | F1—C8—C5 | 109.0 (13) |
O1—Sb1—O1i | 176.0 (3) | F3—C8—C5 | 111.0 (11) |
C1—O1—Sb1 | 110.8 (6) | F2'—C8—C5 | 114.2 (18) |
O2—C1—O1 | 121.7 (9) | C14—C9—C10 | 119.7 (11) |
O2—C1—C2 | 123.2 (8) | C14—C9—Sb1 | 115.0 (7) |
O1—C1—C2 | 115.1 (8) | C10—C9—Sb1 | 125.3 (9) |
C3—C2—C7 | 117.0 (9) | C11—C10—C9 | 120.8 (13) |
C3—C2—C1 | 122.8 (9) | C11—C10—H10 | 119.6 |
C7—C2—C1 | 120.1 (9) | C9—C10—H10 | 119.6 |
C4—C3—C2 | 120.4 (11) | C10—C11—C12 | 119.1 (17) |
C4—C3—H3 | 119.8 | C10—C11—H11 | 120.4 |
C2—C3—H3 | 119.8 | C12—C11—H11 | 120.4 |
C3—C4—C5 | 120.7 (11) | C13—C12—C11 | 120.5 (18) |
C3—C4—H4 | 119.7 | C13—C12—H12 | 119.8 |
C5—C4—H4 | 119.7 | C11—C12—H12 | 119.8 |
C6—C5—C4 | 120.1 (11) | C14—C13—C12 | 120.0 (16) |
C6—C5—C8 | 120.1 (12) | C14—C13—H13 | 120.0 |
C4—C5—C8 | 119.8 (12) | C12—C13—H13 | 120.0 |
C5—C6—C7 | 120.2 (11) | C9—C14—C13 | 119.8 (13) |
C5—C6—H6 | 119.9 | C9—C14—H14 | 120.1 |
C7—C6—H6 | 119.9 | C13—C14—H14 | 120.1 |
C6—C7—C2 | 121.6 (11) | C16i—C15—C16 | 118.8 (12) |
C6—C7—H7 | 119.2 | C16i—C15—Sb1 | 120.6 (6) |
C2—C7—H7 | 119.2 | C16—C15—Sb1 | 120.6 (6) |
F2—C8—F1' | 46.9 (16) | C17—C16—C15 | 119.7 (10) |
F2—C8—F3' | 60.8 (14) | C17—C16—H16 | 120.1 |
F1'—C8—F3' | 104.1 (14) | C15—C16—H16 | 120.1 |
F2—C8—F1 | 114.2 (14) | C18—C17—C16 | 121.3 (11) |
F1'—C8—F1 | 135 (2) | C18—C17—H17 | 119.3 |
F3'—C8—F1 | 58.8 (14) | C16—C17—H17 | 119.3 |
F2—C8—F3 | 106.8 (13) | C17—C18—C17i | 118.9 (15) |
F1'—C8—F3 | 61.8 (19) | C17—C18—H18 | 120.5 |
F3'—C8—F3 | 140.1 (15) | C17i—C18—H18 | 120.5 |
F1—C8—F3 | 102.8 (12) |
Symmetry code: (i) −x+2, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2ii | 0.93 | 2.55 | 3.304 (13) | 138 |
Symmetry code: (ii) −y+1, x−y, z−1/3. |
Experimental details
Crystal data | |
Chemical formula | [Sb(C6H5)3(C8H4F3O2)2] |
Mr | 731.27 |
Crystal system, space group | Hexagonal, P62 |
Temperature (K) | 298 |
a, c (Å) | 12.9879 (10), 16.042 (2) |
V (Å3) | 2343.5 (4) |
Z | 3 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.44 × 0.31 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.679, 0.803 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9708, 2719, 1962 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.145, 1.08 |
No. of reflections | 2719 |
No. of parameters | 233 |
No. of restraints | 55 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.90, −0.41 |
Absolute structure | Flack (1983), 1284 Friedel pairs |
Absolute structure parameter | 0.04 (7) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).
Sb1—C9 | 2.087 (10) | Sb1—O1 | 2.150 (5) |
Sb1—C9i | 2.087 (10) | Sb1—O1i | 2.150 (5) |
Sb1—C15 | 2.103 (10) | ||
C9—Sb1—C9i | 140.0 (5) | C9i—Sb1—C15 | 110.0 (3) |
C9—Sb1—C15 | 110.0 (3) | O1—Sb1—O1i | 176.0 (3) |
Symmetry code: (i) −x+2, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2ii | 0.93 | 2.55 | 3.304 (13) | 138.3 |
Symmetry code: (ii) −y+1, x−y, z−1/3. |
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
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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).