metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages m656-m657

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

(Received 5 May 2009; accepted 9 May 2009; online 20 May 2009)

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[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.]); Yin et al. (2008[Yin, H. D., Quan, L. & Li, L. W. (2008). Inorg. Chem. Commun. 11, 1121-1124.]); Yu et al. (2004[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.]).

[Scheme 1]

Experimental

Crystal data
  • [Sb(C6H5)3(C8H4F3O2)2]

  • Mr = 731.27

  • Hexagonal, P 62

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.679, Tmax = 0.803

  • 9708 measured reflections

  • 2719 independent reflections

  • 1962 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1284 Friedel pairs

  • Flack parameter: 0.04 (7)

Table 1
Selected geometric parameters (Å, °)

Sb1—C9 2.087 (10)
Sb1—C15 2.103 (10)
Sb1—O1 2.150 (5)
C9—Sb1—C9i 140.0 (5)
C9—Sb1—C15 110.0 (3)
O1—Sb1—O1i 176.0 (3)
Symmetry code: (i) -x+2, -y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O2ii 0.93 2.55 3.304 (13) 138
Symmetry code: (ii) [-y+1, x-y, z-{\script{1\over 3}}].

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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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).
Triphenylbis[4-(trifluoromethyl)benzoato-κO]antimony(V) top
Crystal data top
[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 top
Bruker SMART
diffractometer
2719 independent reflections
Radiation source: fine-focus sealed tube1962 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 159
Tmin = 0.679, Tmax = 0.803k = 1512
9708 measured reflectionsl = 1918
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)] = 0.058H-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 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 methodsAbsolute structure parameter: 0.04 (7)
Crystal data top
[Sb(C6H5)3(C8H4F3O2)2]Z = 3
Mr = 731.27Mo Kα radiation
Hexagonal, P62µ = 0.96 mm1
a = 12.9879 (10) ÅT = 298 K
c = 16.042 (2) Å0.44 × 0.31 × 0.24 mm
V = 2343.5 (4) Å3
Data collection top
Bruker SMART
diffractometer
2719 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1962 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.803Rint = 0.053
9708 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.145Δρmax = 0.90 e Å3
S = 1.08Δρmin = 0.41 e Å3
2719 reflectionsAbsolute structure: Flack (1983), 1284 Friedel pairs
233 parametersAbsolute structure parameter: 0.04 (7)
55 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
C151.00000.50000.0220 (6)0.053 (3)
C161.0867 (9)0.4904 (10)0.0660 (7)0.090 (3)
H161.14700.48630.03770.108*
C171.0832 (12)0.4871 (14)0.1517 (7)0.120 (5)
H171.13870.47570.18070.144*
C181.00000.50000.1948 (9)0.116 (7)
H181.00000.50000.25280.139*
Atomic displacement parameters (Å2) top
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, º) top
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 code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2ii0.932.553.304 (13)138
Symmetry code: (ii) y+1, xy, z1/3.

Experimental details

Crystal data
Chemical formula[Sb(C6H5)3(C8H4F3O2)2]
Mr731.27
Crystal system, space groupHexagonal, P62
Temperature (K)298
a, c (Å)12.9879 (10), 16.042 (2)
V3)2343.5 (4)
Z3
Radiation typeMo Kα
µ (mm1)0.96
Crystal size (mm)0.44 × 0.31 × 0.24
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.679, 0.803
No. of measured, independent and
observed [I > 2σ(I)] reflections
9708, 2719, 1962
Rint0.053
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.145, 1.08
No. of reflections2719
No. of parameters233
No. of restraints55
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.90, 0.41
Absolute structureFlack (1983), 1284 Friedel pairs
Absolute structure parameter0.04 (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).

Selected geometric parameters (Å, º) top
Sb1—C92.087 (10)Sb1—O12.150 (5)
Sb1—C9i2.087 (10)Sb1—O1i2.150 (5)
Sb1—C152.103 (10)
C9—Sb1—C9i140.0 (5)C9i—Sb1—C15110.0 (3)
C9—Sb1—C15110.0 (3)O1—Sb1—O1i176.0 (3)
Symmetry code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2ii0.932.553.304 (13)138.3
Symmetry code: (ii) y+1, xy, z1/3.
 

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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Volume 65| Part 6| June 2009| Pages m656-m657
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