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

Liyuan Wen; Handong Yin; Li Quan; Daqi Wang

doi:10.1107/S1600536808029656

. 2008 Sep 20;64(Pt 10):m1303. doi: 10.1107/S1600536808029656

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

Liyuan Wen ^a, Handong Yin ^a,^*, Li Quan ^a, Daqi Wang ^a

PMCID: PMC2959366 PMID: 21201042

Abstract

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 ( Inline graphic 01).

Related literature

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

Experimental

Crystal data

[Sb(C₆H₅)₃(C₈H₄F₃O₃)₂]
M _r = 763.27
Monoclinic,
a = 12.7970 (14) Å
b = 22.890 (2) Å
c = 12.5131 (10) Å
β = 120.107 (2)°
V = 3170.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 293 (2) K
0.50 × 0.40 × 0.35 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.635, T _max = 0.718
7869 measured reflections
2791 independent reflections
2338 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.092
S = 1.01
2791 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029656/rz2246sup1.cif

e-64-m1303-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029656/rz2246Isup2.hkl

e-64-m1303-Isup2.hkl^{(137.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.93	2.36	3.053 (5)	131
C16—H16⋯O1	0.93	2.49	2.979 (5)	113
C8—H8B⋯O3ⁱ	0.96	2.57	3.240 (7)	127
C11—H11⋯O2ⁱⁱ	0.93	2.51	3.255 (5)	138

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Symmetry codes: (i) Inline graphic ; (ii) .

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

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.

Experimental

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