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Acta Cryst. (2008). E64, m1303    [ doi:10.1107/S1600536808029656 ]

Triphenylbis(2,4,5-trifluoro-3-methoxybenzoato)antimony(V)

L. Wen, H. Yin, L. Quan and D. Wang

Abstract top

In the title compound, [Sb(C6H5)3(C8H4F3O3)2], the Sb atom lies on an inversion centre and exhibits a trigonal bipyramidal geometry with the axial positions occupied by the O atoms of two carboxylate groups and the equatorial positions occupied by C atoms of the phenyl groups. Intramolecular C-H...O hydrogen bonds stabilize the molecular conformation. In the crystal structure, molecules are connected by intermolecular C-H...O hydrogen-bonding interactions, forming a layer structure parallel to (\overline{2}01).

Comment top

In recent years organoantimony(V) derivatives have attracted considerable attention due to their significant antimicrobial properties as well as antitumor activities. We have therefore synthesized the title compound, and present its crystal structure here.

The molecular structure of the compound is shown in Fig.1 The Sb atom, which lies on an inversion centre, assumes a distorted trigonal bipyramidal coordination geometry, provided by three phenyl groups at the equatorial positions and two carboxylate groups at the axial positions. The Sb—O bond lengths in organoantimony compounds are extremely variable, ranging from 1.935 Å in triphenylstibine oxide (Ferguson et al. 1987) to 2.506 Å in tetraphenylstibonium benzenesulphonate hydrate (Ruether et al. 1985). The Sb1—O1 distance (2.132 (2) Å) in the title compound lies within this range. The Sb—C bond distances (Sb1—C9 = 2.122 (3) Å; Sb1—C15 = 2.118 (5) Å) fall in the normal range for Sb—C(phenyl) bonds (2.10–2.13 Å). The molecular conformation is stabilized by C—H···O hydrogen bonds. In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonds (Fig.2, Table 1,) into layers parallel to the (-2 0 1) plane.

Related literature top

For related structures, see: Ferguson et al. (1987); Ruether et al. (1985).

Experimental top

The reaction was carried out under nitrogen atmosphere. 3-Methoxyl-2,4,5-trifluorobenzoic acid (2 mmol) and sodium ethoxide (2.4 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenylantimony dichloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a dichloromethane/methanol (1:1 v/v) solution to yield colourless blocks of the title compound (yield 86%. m.p. 458 K). Anal. Calcd (%) for C34H23O6Sb1F6 (Mr = 763.27): C, 53.50; H, 3.04; F, 14.93; Sb, 15.95. Found (%): C, 53.55; H, 3.07; F, 14.89; Sb, 15.99

Refinement top

The H atoms were positioned geometrically, with methyl C—H distances of 0.96 Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, O) or 1.5 Ueq(C) for the methyl group.

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 compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Symmetry code: (A) = 1 - x, y, 3/2 - z.
[Figure 2] Fig. 2. View of the two-dimensional layer structure in the title compound. Intermolecular hydrogen bonds are shown as dashed lines. H atoms are omitted.
Triphenylbis(2,4,5-trifluoro-3-methoxybenzoato)antimony(V) top
Crystal data top
[Sb(C6H5)3(C8H4F3O3)2]F(000) = 1520
Mr = 763.27Dx = 1.599 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3589 reflections
a = 12.7970 (14) Åθ = 2.6–23.9°
b = 22.890 (2) ŵ = 0.95 mm−1
c = 12.5131 (10) ÅT = 293 K
β = 120.107 (2)°Block, colourless
V = 3170.9 (5) Å30.50 × 0.40 × 0.35 mm
Z = 4
Data collection top
Bruker SMART area-detector
diffractometer		2791 independent reflections
Radiation source: fine-focus sealed tube2338 reflections with I > 2σ(I)
graphiteRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→15
Tmin = 0.635, Tmax = 0.718k = −27→23
7869 measured reflectionsl = −14→14
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.053P)2 + 2.3063P]
where P = (Fo2 + 2Fc2)/3
2791 reflections(Δ/σ)max = 0.001
215 parametersΔρmax = 0.98 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Sb(C6H5)3(C8H4F3O3)2]V = 3170.9 (5) Å3
Mr = 763.27Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.7970 (14) ŵ = 0.95 mm−1
b = 22.890 (2) ÅT = 293 K
c = 12.5131 (10) Å0.50 × 0.40 × 0.35 mm
β = 120.107 (2)°
Data collection top
Bruker SMART area-detector
diffractometer		2791 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2338 reflections with I > 2σ(I)
Tmin = 0.635, Tmax = 0.718Rint = 0.036
7869 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.093Δρmax = 0.98 e Å−3
S = 1.01Δρmin = −0.37 e Å−3
2791 reflectionsAbsolute structure: ?
215 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sb10.50000.601220 (13)0.75000.04156 (14)
F10.2452 (3)0.54248 (11)0.8929 (3)0.0850 (8)
F2−0.0110 (3)0.65440 (19)0.9796 (3)0.1229 (13)
F30.0513 (3)0.75229 (15)0.9055 (3)0.1104 (11)
O10.3684 (2)0.59621 (10)0.8065 (2)0.0501 (6)
O20.3552 (2)0.69304 (12)0.7893 (3)0.0614 (7)
O30.0880 (4)0.54671 (19)0.9730 (4)0.1077 (13)
C10.3247 (3)0.64637 (17)0.8139 (3)0.0501 (9)
C20.2343 (3)0.64523 (17)0.8571 (3)0.0515 (9)
C30.2004 (4)0.59594 (19)0.8951 (4)0.0608 (11)
C40.1193 (4)0.5976 (2)0.9386 (5)0.0745 (14)
C50.0708 (4)0.6507 (3)0.9410 (5)0.0808 (15)
C60.1022 (4)0.7004 (3)0.9027 (5)0.0789 (14)
C70.1836 (3)0.6985 (2)0.8621 (4)0.0612 (10)
H70.20520.73270.83800.073*
C80.1418 (6)0.5380 (3)1.1036 (6)0.121 (2)
H8A0.22770.54251.14230.181*
H8B0.12330.49941.11920.181*
H8C0.11020.56631.13670.181*
C90.6319 (3)0.63273 (16)0.9264 (3)0.0455 (8)
C100.6261 (4)0.68703 (18)0.9726 (4)0.0609 (10)
H100.56230.71230.92570.073*
C110.7170 (4)0.7030 (2)1.0897 (4)0.0752 (13)
H110.71340.73901.12220.090*
C120.8122 (5)0.6661 (3)1.1582 (4)0.0837 (15)
H120.87360.67751.23600.100*
C130.8168 (4)0.6123 (3)1.1118 (5)0.0858 (15)
H130.88050.58701.15890.103*
C140.7263 (4)0.59551 (19)0.9947 (4)0.0675 (12)
H140.72980.55930.96290.081*
C150.50000.5087 (2)0.75000.0441 (11)
C160.4754 (4)0.47799 (17)0.8308 (4)0.0601 (10)
H160.45850.49810.88490.072*
C170.4761 (5)0.4175 (2)0.8306 (5)0.0791 (14)
H170.46030.39720.88530.095*
C180.50000.3873 (3)0.75000.085 (2)
H180.50000.34660.75000.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.0500 (2)0.0384 (2)0.0411 (2)0.0000.02652 (16)0.000
F10.107 (2)0.0643 (16)0.114 (2)−0.0008 (14)0.0786 (19)0.0110 (15)
F20.092 (2)0.195 (4)0.124 (3)0.005 (2)0.086 (2)−0.008 (3)
F30.105 (2)0.126 (3)0.121 (3)0.0416 (19)0.072 (2)−0.008 (2)
O10.0571 (15)0.0497 (15)0.0566 (16)0.0085 (11)0.0384 (13)0.0076 (12)
O20.0731 (17)0.0541 (16)0.0691 (19)0.0055 (14)0.0447 (15)0.0113 (14)
O30.117 (3)0.136 (3)0.097 (3)−0.050 (3)0.074 (2)−0.004 (3)
C10.048 (2)0.061 (2)0.042 (2)0.0083 (17)0.0229 (17)0.0064 (17)
C20.0451 (19)0.065 (2)0.047 (2)0.0059 (17)0.0252 (17)0.0075 (18)
C30.058 (2)0.073 (3)0.058 (3)0.001 (2)0.034 (2)0.000 (2)
C40.064 (3)0.105 (4)0.066 (3)−0.019 (3)0.041 (2)−0.001 (3)
C50.060 (3)0.128 (5)0.070 (3)0.004 (3)0.044 (2)−0.005 (3)
C60.064 (3)0.105 (4)0.073 (3)0.019 (3)0.038 (2)−0.010 (3)
C70.057 (2)0.071 (3)0.059 (2)0.007 (2)0.031 (2)0.004 (2)
C80.121 (5)0.135 (5)0.110 (5)−0.011 (4)0.061 (4)0.011 (5)
C90.052 (2)0.047 (2)0.041 (2)−0.0099 (16)0.0265 (16)−0.0040 (16)
C100.072 (3)0.055 (2)0.060 (3)−0.012 (2)0.036 (2)−0.010 (2)
C110.088 (3)0.080 (3)0.059 (3)−0.033 (3)0.039 (3)−0.023 (2)
C120.077 (3)0.116 (4)0.051 (3)−0.039 (3)0.027 (2)−0.027 (3)
C130.066 (3)0.113 (4)0.058 (3)0.007 (3)0.016 (2)0.006 (3)
C140.062 (3)0.077 (3)0.052 (3)0.003 (2)0.020 (2)−0.008 (2)
C150.048 (3)0.043 (3)0.040 (3)0.0000.022 (2)0.000
C160.082 (3)0.052 (2)0.056 (2)0.000 (2)0.042 (2)0.0034 (19)
C170.108 (4)0.054 (3)0.085 (4)−0.005 (3)0.056 (3)0.013 (2)
C180.116 (6)0.040 (3)0.102 (6)0.0000.056 (5)0.000
Geometric parameters (Å, °) top
Sb1—C152.118 (5)C8—H8B0.9600
Sb1—C92.122 (3)C8—H8C0.9600
Sb1—C9i2.122 (3)C9—C141.371 (5)
Sb1—O1i2.132 (2)C9—C101.388 (5)
Sb1—O12.132 (2)C10—C111.387 (6)
F1—C31.358 (5)C10—H100.9300
F2—C51.358 (5)C11—C121.372 (7)
F3—C61.364 (6)C11—H110.9300
O1—C11.301 (4)C12—C131.376 (7)
O2—C11.228 (4)C12—H120.9300
O3—C41.370 (6)C13—C141.391 (6)
O3—C81.434 (7)C13—H130.9300
C1—C21.504 (5)C14—H140.9300
C2—C31.376 (5)C15—C16i1.390 (4)
C2—C71.398 (5)C15—C161.390 (5)
C3—C41.393 (6)C16—C171.384 (6)
C4—C51.371 (7)C16—H160.9300
C5—C61.370 (8)C17—C181.378 (6)
C6—C71.369 (6)C17—H170.9300
C7—H70.9300C18—C17i1.378 (6)
C8—H8A0.9600C18—H180.9300
C15—Sb1—C9109.87 (10)H8A—C8—H8B109.5
C15—Sb1—C9i109.87 (10)O3—C8—H8C109.5
C9—Sb1—C9i140.3 (2)H8A—C8—H8C109.5
C15—Sb1—O1i86.91 (6)H8B—C8—H8C109.5
C9—Sb1—O1i90.84 (12)C14—C9—C10120.7 (4)
C9i—Sb1—O1i91.25 (12)C14—C9—Sb1115.4 (3)
C15—Sb1—O186.91 (6)C10—C9—Sb1123.8 (3)
C9—Sb1—O191.25 (12)C11—C10—C9118.9 (4)
C9i—Sb1—O190.84 (12)C11—C10—H10120.5
O1i—Sb1—O1173.83 (12)C9—C10—H10120.5
C1—O1—Sb1114.6 (2)C12—C11—C10120.7 (4)
C4—O3—C8115.3 (5)C12—C11—H11119.7
O2—C1—O1123.2 (3)C10—C11—H11119.7
O2—C1—C2120.3 (3)C11—C12—C13119.9 (4)
O1—C1—C2116.5 (3)C11—C12—H12120.0
C3—C2—C7117.8 (3)C13—C12—H12120.0
C3—C2—C1124.9 (4)C12—C13—C14120.2 (5)
C7—C2—C1117.3 (3)C12—C13—H13119.9
F1—C3—C2121.5 (3)C14—C13—H13119.9
F1—C3—C4116.0 (4)C9—C14—C13119.5 (4)
C2—C3—C4122.5 (4)C9—C14—H14120.2
O3—C4—C5122.7 (5)C13—C14—H14120.2
O3—C4—C3119.5 (5)C16i—C15—C16119.3 (5)
C5—C4—C3117.8 (4)C16i—C15—Sb1120.3 (2)
F2—C5—C6119.1 (5)C16—C15—Sb1120.3 (2)
F2—C5—C4120.0 (5)C17—C16—C15120.0 (4)
C6—C5—C4120.9 (4)C17—C16—H16120.0
F3—C6—C7119.9 (5)C15—C16—H16120.0
F3—C6—C5119.1 (4)C18—C17—C16120.5 (5)
C7—C6—C5121.0 (5)C18—C17—H17119.7
C6—C7—C2120.0 (4)C16—C17—H17119.7
C6—C7—H7120.0C17—C18—C17i119.6 (6)
C2—C7—H7120.0C17—C18—H18120.2
O3—C8—H8A109.5C17i—C18—H18120.2
O3—C8—H8B109.5
C15—Sb1—O1—C1−175.3 (2)C1—C2—C7—C6−178.9 (4)
C9—Sb1—O1—C174.9 (3)C15—Sb1—C9—C1425.4 (3)
C9i—Sb1—O1—C1−65.5 (3)C9i—Sb1—C9—C14−154.6 (3)
Sb1—O1—C1—O20.8 (5)O1i—Sb1—C9—C14−61.7 (3)
Sb1—O1—C1—C2−178.2 (2)O1—Sb1—C9—C14112.5 (3)
O2—C1—C2—C3−175.3 (4)C15—Sb1—C9—C10−154.6 (3)
O1—C1—C2—C33.8 (6)C9i—Sb1—C9—C1025.4 (3)
O2—C1—C2—C72.9 (5)O1i—Sb1—C9—C10118.3 (3)
O1—C1—C2—C7−178.1 (3)O1—Sb1—C9—C10−67.5 (3)
C7—C2—C3—F1179.9 (4)C14—C9—C10—C11−0.5 (6)
C1—C2—C3—F1−2.0 (6)Sb1—C9—C10—C11179.5 (3)
C7—C2—C3—C4−0.5 (6)C9—C10—C11—C121.0 (7)
C1—C2—C3—C4177.6 (4)C10—C11—C12—C13−1.4 (7)
C8—O3—C4—C5−77.2 (7)C11—C12—C13—C141.2 (8)
C8—O3—C4—C3105.1 (6)C10—C9—C14—C130.4 (7)
F1—C3—C4—O3−1.5 (7)Sb1—C9—C14—C13−179.6 (4)
C2—C3—C4—O3178.9 (4)C12—C13—C14—C9−0.7 (8)
F1—C3—C4—C5−179.3 (4)C9—Sb1—C15—C16i−119.9 (2)
C2—C3—C4—C51.1 (7)C9i—Sb1—C15—C16i60.1 (2)
O3—C4—C5—F20.6 (8)O1i—Sb1—C15—C16i−30.1 (2)
C3—C4—C5—F2178.3 (4)O1—Sb1—C15—C16i149.9 (2)
O3—C4—C5—C6−178.2 (5)C9—Sb1—C15—C1660.1 (2)
C3—C4—C5—C6−0.5 (8)C9i—Sb1—C15—C16−119.9 (2)
F2—C5—C6—F30.6 (7)O1i—Sb1—C15—C16149.9 (2)
C4—C5—C6—F3179.5 (5)O1—Sb1—C15—C16−30.1 (2)
F2—C5—C6—C7−179.5 (4)C16i—C15—C16—C170.3 (3)
C4—C5—C6—C7−0.7 (8)Sb1—C15—C16—C17−179.7 (3)
F3—C6—C7—C2−178.9 (4)C15—C16—C17—C18−0.6 (7)
C5—C6—C7—C21.3 (7)C16—C17—C18—C17i0.3 (3)
C3—C2—C7—C6−0.7 (6)
Symmetry codes: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O20.932.363.053 (5)131
C16—H16···O10.932.492.979 (5)113
C8—H8B···O3ii0.962.573.240 (7)127
C11—H11···O2iii0.932.513.255 (5)138
Symmetry codes: (ii) −x, −y+1, −z+2; (iii) x+1/2, −y+3/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O20.932.363.053 (5)131
C16—H16···O10.932.492.979 (5)113
C8—H8B···O3i0.962.573.240 (7)127
C11—H11···O2ii0.932.513.255 (5)138
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x+1/2, −y+3/2, z+1/2.
Acknowledgements top

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

references
References top

Ferguson, G., Glidewell, C., Kaitner, B., Lloyd, D. & Metcalfe, S. (1987). Acta Cryst. C43, 824–826.

Ruether, R., Huber, F. & Preut, H. (1985). J. Organomet. Chem. 295, 21–28.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.