Chlorido(2-chloro­nicotinato)triphenyl­anti­mony(V)

Li Quan; Handong Yin; Daqi Wang

doi:10.1107/S1600536808029632

. 2008 Sep 20;64(Pt 10):m1302. doi: 10.1107/S1600536808029632

Chlorido(2-chloronicotinato)triphenylantimony(V)

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

PMCID: PMC2959277 PMID: 21201041

Abstract

In the title complex, [Sb(C₆H₅)₃(C₆H₃ClNO₂)Cl], the Sb center has a close to ideal trigonal-bipyramidal geometry, with the phenyl ligands in equatorial positions and the chloride and a carboxylate O atom in axial positions. Weak C—H⋯O contacts generate dimeric units via crystallographic inversion centres.

Related literature

For related structures, see: Yin et al. (2008 ▶); Chaudhari et al. (2007 ▶)

Experimental

Crystal data

[Sb(C₆H₅)₃(C₆H₃ClNO₂)Cl]
M _r = 545.04
Monoclinic,
a = 11.9580 (9) Å
b = 15.4428 (18) Å
c = 12.0264 (15) Å
β = 94.291 (2)°
V = 2214.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 298 (2) K
0.45 × 0.41 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.550, T _max = 0.584 (expected range = 0.516–0.547)
10922 measured reflections
3893 independent reflections
3149 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.071
S = 1.00
3893 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.39 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/S1600536808029632/si2109sup1.cif

e-64-m1302-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029632/si2109Isup2.hkl

e-64-m1302-Isup2.hkl^{(190.9KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Sb1—C19	2.107 (3)
Sb1—C13	2.111 (3)
Sb1—C7	2.111 (3)
Sb1—O1	2.114 (2)
Sb1—Cl2	2.4921 (8)

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C19—Sb1—C13	137.38 (12)
C19—Sb1—C7	114.05 (12)
C13—Sb1—C7	108.55 (12)
O1—Sb1—Cl2	177.56 (6)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.93	2.59	3.346 (4)	139

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Symmetry code: (i) Inline graphic .

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

The triphenylantimony(V) acetylferroceneoxime structure shows some in vitro antitumor activity (Yin et al. 2008). The title compound may show similar activities. A similar compound was synthesized (Chaudhari et al.2007). The crystal structure of complex I (Fig. 1) consists of dimeric units, (Fig. 2) generated through weak intermolecular C—H···O hydrogen bonds via crystallographic inversion centres (Table 2). The sum of the equatorial angles C7—Sb1—C13, C13—Sb1—C19 and C19—Sb1—C7 is 359.98° and the corresponding axial angle Cl2—Sb1—O1 is 177.56 (6)° (Table 1). The distance Sb—O1 2.114 (2) Å is shorter than the range of short Sb—O distances 2.119 (3) - 2.133 (3) Å, and shorter than the range of the long Sb—O distances between 3.012 (6) and 3.112 (4) Å from related literature (Chaudhari et al.2007). The Sb1—O2 distance of 2.898 (2) Å in the title complex is shorter than the sum of the van der Waals radii for Sb and O (3.2 Å), but much longer than the covalent bond Sb–O1 (2.114 (2) Å). So it can be considered that atom O2 does not make any significant contact with the Sb1 atom.

Experimental

2-chloronicotinic acid (0.044 g, 0.4 mmol) and sodium methoxide (0.8 ml, 0.4 mmol) was added to a stirring solution containing triphenylantimonydichloride (0.172 g, 0.4 mmol) in toluene (25 ml). After refluxing for 8 h, the colorless solution was obtained and then filtered. The solvent was gradually removed by evaporation under vacuum until the white solid was obtained. The solid was recrystallized from petroleum ether/dichoromethane (1:1) to give colorless crystals.