(μ-2,3-Dibromo­succinato-κ2 O 1:O 4)bis­[methano­lato-κO)triphenyl­anti­mony(V)]

Li Quan; Handong Yin; Wenfu Fu

doi:10.1107/S1600536811016114

. 2011 May 7;67(Pt 6):m713. doi: 10.1107/S1600536811016114

(μ-2,3-Dibromosuccinato-κ² O ¹:O ⁴)bis[methanolato-κO)triphenylantimony(V)]

Li Quan ^a,^b,^c, Handong Yin ^c, Wenfu Fu ^a,^*

PMCID: PMC3120583 PMID: 21754613

Abstract

In the title molecule, [Sb₂(C₆H₅)₆(C₄H₄Br₂O₄)(CH₃O)₂], two [Sb(CH₃O)Ph₃]⁺ units are linked by the two carboxylate O atoms of a meso-2,3-dibromosuccinate bridging ligand, forming a dinuclear compound. The Sb^IV atom is five-coordinated in a slightly distorted trigonal–bipyramid geometry by phenyl C atoms in the equatorial positions and two O atoms in the axial positions. C—H⋯O interactions link the molecules into a two-dimensional network parallel to (010). The —CH— group of the centrosymmetric 2,3-dibromosuccinate anion is disordered over two sites in a 0.6:0.4 ratio.

Related literature

For the synthesis and structural characteristics of related organophenylantimony compounds, see: Yin et al. (2008 ▶).

Experimental

Crystal data

[Sb₂(C₆H₅)₆(C₄H₂Br₂O₄)(CH₃O)₂]
M _r = 1042.04
Triclinic,
a = 8.707 (8) Å
b = 9.872 (8) Å
c = 12.779 (10) Å
α = 103.74 (2)°
β = 97.93 (2)°
γ = 100.45 (2)°
V = 1030.3 (15) Å³
Z = 1
Mo Kα radiation
μ = 3.29 mm⁻¹
T = 298 K
0.22 × 0.16 × 0.13 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.531, T _max = 0.674
5379 measured reflections
3582 independent reflections
2582 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.131
S = 1.00
3582 reflections
240 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.10 e Å⁻³
Δρ_min = −0.68 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016114/jh2282sup1.cif

e-67-0m713-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016114/jh2282Isup2.hkl

e-67-0m713-Isup2.hkl^{(175.6KB, hkl)}

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

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

Sb1—O3	1.996 (5)
Sb1—C15	2.118 (7)
Sb1—C3	2.119 (7)
Sb1—C9	2.122 (7)
Sb1—O1	2.177 (4)

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O3—Sb1—C15	92.7 (2)
O3—Sb1—C3	87.8 (2)
O3—Sb1—C9	93.9 (3)
C15—Sb1—C9	119.3 (3)
C3—Sb1—C9	113.2 (3)
O3—Sb1—O1	176.33 (19)
C15—Sb1—O1	90.7 (2)
C3—Sb1—O1	91.2 (2)
C9—Sb1—O1	83.2 (2)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2ⁱ	0.93	2.50	3.388 (11)	161
C17—H17⋯O3ⁱⁱ	0.93	2.59	3.435 (10)	152

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

Acknowledgments

We acknowledge the National Natural Science Foundation of China for support (grant Nos. 20771053 and 20773059).

supplementary crystallographic information

Comment

The similar compound of organotin from meso-2,3-dibromosuccinic acid was synthesized by Professor Yin (Yin et al., 2008). The Sb atom is five-coordinated (Figure 1) with an average Sb-C distance of 2.120 A° almost equal to the average Sn-C distance of 2.123 A° and average Sb-O distance of 2.087 A° much shorter than 2.182 A° of Sn-O distance (Yin et al., 2008). The feature in the solid state structure is the 2D network structure infinitely linked by C19-H19···O2 (2.496 A° of H19···O2) and C17-H17···O3 (2.585 A° of H17···O3) interactions (Figure 2), while the organotin give a 3D network triorganitin(iv) polymer (Yin et al., 2008). The title unit is sited in a symmetrical center, and the coordination environment around the antimony atom is described as a slightly distorted trigonal bipyramid with three carbon atoms from the discrete phenyls in equatorial positions and two oxygen atoms occupying the axial positions with O1-Sb1-O2 angle 176.33 (19)°. The SbC₃ unit is planar (the sum of the C-Sb-C angle is 359.9 °) and the O-Sb-C angles are in the range of 83.2 (2)/93.9 (3)°.

Experimental

2,3-dibromosuccinic acid (0.276 g, 1.00 mmol) was added to the solution of sodium methoxide (0.108 g, 2.00 mmol) in methanol (15 ml), and the mixture was refluxed with stirring for 30 min. Triphenylantimony chloride (0.423 g, 1.00 mmol) in toluene (25 ml) was then added to the mixture, and the reaction was allowed to continue for 8h under refluxing. After cooling down to room temperature, teh resulting solution was filtered. The solvent was removed by evaporation under vacuum leaving a coloeless solid. The product was recrystallized from dichloromethane/petroleum ether.