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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1503.
Published online 2008 November 8. doi:  10.1107/S1600536808033783
PMCID: PMC2959827

Bis(5-bromo­pyridine-2-carboxyl­ato-κO)triphenyl­anti­mony(V)

Abstract

In the title compound, [Sb(C6H5)3(C6H3BrNO2)2], the Sb center has a distorted trigonal–bipyramidal geometry, with two carboxyl­ate O atoms of two 5-bromo­pyridine-2-carboxyl­ate ligands in equatorial positions and three phenyl ligands in axial positions. The crystal structure is stabilized by C—H(...)Br hydrogen bonds and inter­molecular C—Br(...)π inter­actions [C(...)π = 3.57 (1) Å].

Related literature

For the synthesis and structures of related triphenyl­anti­mony compounds, see: Yin et al. (2008 [triangle]); Chaudhari et al. (2007 [triangle]); Mahon et al. (1998 [triangle]); Quan et al. (2008 [triangle]).

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Object name is e-64-m1503-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)3(C6H3BrNO2)2]
  • M r = 755.06
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1503-efi7.jpg
  • a = 20.597 (2) Å
  • b = 13.057 (1) Å
  • c = 20.541 (2) Å
  • V = 5524.2 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.93 mm−1
  • T = 298 (2) K
  • 0.43 × 0.37 × 0.20 mm

Data collection

  • Siemens SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.204, T max = 0.460
  • 5869 measured reflections
  • 2564 independent reflections
  • 1861 reflections with I > 2σ(I)
  • R int = 0.081

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.166
  • S = 1.01
  • 2564 reflections
  • 178 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 1.02 e Å−3
  • Δρmin = −0.86 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1172 Friedel pairs
  • Flack parameter: 0.02 (3)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033783/lx2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033783/lx2073Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The triphenylantimony compound containing the heterocyclic pyridine carboxylate skeleton show some potential biological activity (Yin et al., 2008) and we have synthesized the title compound (I) and report its crystal structure here.

As shown in Fig. 1, the Sb atom is five-coordinated by the three phenyl C atoms and the two carboxylate O atoms. The average distance of Sb—C (2.10 Å) in the (I) is shorter than the average distance of S—C (2.225 Å; Mahon et al., 1998). The average distance of Sb—O (2.146 Å) in the (I) is equal to the average distance of Sb—O (2.145 Å; Chaudhari et al., 2007). The crystal structure is stabilized by intermolecular C—H···Br hydrogen bonds (Fig. 2 and Table 1; symmetry code as in Fig. 2). In addition, the crystal structure exhibits C—Br···π interactions, with a C5—Br···Cgii separation of 3.57 (1) Å (Fig. 2; Cg is the centroid of the C7-C12 benzene ring, symmetry code as in Fig. 2).

Experimental

5-bromopyridine-2-carboxylic acid (0.061 g, 0.3 mmol) and sodium methoxide (0.6 ml, 0.3 mmol) was added to a stirring solution containing triphenylantimonydichloride (0.064 g, 0.15 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 is obtained. The solid was recrystallized from petroleum ether/dichoromethane (1:1) to give colorless crystals.

Refinement

All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) -x+1, -y+1, z.]
Fig. 2.
C—H···Br and C—Br···π interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (i) -x+1/2, -y+1/2, z; (ii) x, y-1, z; (iii)-x+1/2, -y+1/2, ...

Crystal data

[Sb(C6H5)3(C6H3BrNO2)2]F000 = 2944
Mr = 755.06Dx = 1.816 Mg m3
Orthorhombic, Fdd2Mo Kα radiation λ = 0.71073 Å
Hall symbol: f 2 -2dCell parameters from 2025 reflections
a = 20.597 (2) Åθ = 2.8–24.1º
b = 13.057 (1) ŵ = 3.93 mm1
c = 20.541 (2) ÅT = 298 (2) K
V = 5524.2 (9) Å3Block, colorless
Z = 80.43 × 0.37 × 0.20 mm

Data collection

Siemens SMART diffractometer2564 independent reflections
Radiation source: fine-focus sealed tube1861 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.081
Detector resolution: 20.0 pixels mm-1θmax = 26.0º
T = 298(2) Kθmin = 2.1º
[var phi] and ω scansh = −23→25
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)k = −16→12
Tmin = 0.204, Tmax = 0.460l = −24→25
5869 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.060  w = 1/[σ2(Fo2) + (0.0963P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.166(Δ/σ)max < 0.001
S = 1.01Δρmax = 1.02 e Å3
2564 reflectionsΔρmin = −0.86 e Å3
178 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 1172 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (3)
Secondary atom site location: difference Fourier map

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sb0.50000.50000.64254 (4)0.0395 (3)
Br0.38657 (9)−0.14610 (10)0.69850 (11)0.1021 (8)
N0.4328 (6)0.1462 (8)0.6388 (6)0.074 (3)
O10.4633 (4)0.3464 (5)0.6376 (4)0.0449 (17)
O20.4672 (5)0.3511 (7)0.7460 (5)0.064 (2)
C10.4568 (5)0.3068 (9)0.6937 (7)0.049 (3)
C20.4353 (5)0.1947 (9)0.6944 (7)0.052 (3)
C30.4223 (7)0.1484 (13)0.7532 (7)0.065 (4)
H30.42570.18600.79160.078*
C40.4047 (7)0.0490 (12)0.7557 (8)0.069 (4)
H40.39320.01780.79470.083*
C50.4046 (7)−0.0025 (8)0.6998 (8)0.064 (4)
C60.4174 (9)0.0468 (10)0.6421 (10)0.084 (5)
H60.41530.00940.60360.101*
C70.4109 (5)0.5538 (8)0.6790 (6)0.044 (3)
C80.3959 (7)0.5504 (11)0.7467 (7)0.065 (3)
H80.42560.52600.77700.078*
C90.3346 (8)0.5853 (12)0.7657 (9)0.069 (5)
H90.32350.58540.80960.083*
C100.2904 (7)0.6196 (10)0.7200 (10)0.071 (4)
H100.24950.64120.73350.085*
C110.3054 (7)0.6225 (11)0.6559 (9)0.074 (4)
H110.27530.64560.62550.089*
C120.3667 (6)0.5902 (9)0.6362 (7)0.058 (3)
H120.37760.59380.59230.070*
C130.50000.50000.5399 (8)0.043 (4)
C140.5053 (6)0.4088 (10)0.5057 (6)0.058 (3)
H140.50820.34670.52770.070*
C150.5062 (7)0.4116 (12)0.4393 (6)0.068 (4)
H150.51120.35080.41620.082*
C160.50000.50000.4066 (10)0.074 (6)
H160.50000.50000.36130.089*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb0.0407 (5)0.0310 (4)0.0468 (5)−0.0008 (5)0.0000.000
Br0.1069 (13)0.0400 (8)0.159 (2)−0.0140 (8)0.0465 (13)0.0023 (10)
N0.118 (10)0.045 (6)0.058 (7)−0.023 (6)0.010 (8)−0.004 (6)
O10.053 (4)0.029 (4)0.052 (5)−0.004 (3)−0.001 (4)−0.002 (4)
O20.084 (6)0.047 (5)0.060 (5)−0.011 (5)−0.010 (5)−0.005 (4)
C10.046 (6)0.038 (6)0.064 (8)−0.001 (5)−0.004 (6)−0.004 (6)
C20.050 (7)0.043 (6)0.064 (8)0.000 (5)0.010 (7)0.005 (6)
C30.078 (10)0.060 (9)0.057 (9)−0.007 (7)0.012 (8)0.005 (7)
C40.070 (9)0.052 (8)0.086 (11)0.009 (7)0.001 (8)0.017 (8)
C50.069 (9)0.023 (6)0.101 (12)−0.005 (5)0.014 (8)0.003 (8)
C60.123 (13)0.041 (7)0.089 (10)−0.010 (8)0.028 (12)−0.007 (9)
C70.039 (6)0.029 (5)0.064 (8)−0.004 (4)−0.004 (6)−0.004 (5)
C80.075 (9)0.067 (9)0.053 (8)−0.009 (8)0.005 (7)−0.009 (7)
C90.078 (10)0.054 (8)0.075 (10)−0.010 (8)0.046 (9)−0.017 (7)
C100.053 (8)0.049 (8)0.111 (14)0.002 (6)0.026 (9)−0.005 (8)
C110.052 (8)0.066 (9)0.105 (14)0.008 (6)−0.002 (9)0.004 (8)
C120.056 (7)0.052 (7)0.068 (8)−0.005 (5)−0.007 (7)−0.001 (6)
C130.052 (9)0.022 (7)0.056 (9)0.009 (7)0.0000.000
C140.068 (8)0.050 (7)0.057 (8)0.009 (6)−0.006 (7)0.003 (6)
C150.089 (10)0.067 (9)0.049 (7)0.022 (7)0.007 (8)−0.014 (6)
C160.085 (14)0.091 (16)0.045 (10)0.019 (12)0.0000.000

Geometric parameters (Å, °)

Sb—C72.103 (11)C7—C81.425 (19)
Sb—C7i2.103 (11)C8—C91.40 (2)
Sb—C132.108 (17)C8—H80.9300
Sb—O1i2.146 (7)C9—C101.38 (2)
Sb—O12.146 (7)C9—H90.9300
Br—C51.911 (10)C10—C111.35 (2)
N—C21.309 (16)C10—H100.9300
N—C61.337 (17)C11—C121.39 (2)
O1—C11.270 (16)C11—H110.9300
O2—C11.238 (16)C12—H120.9300
C1—C21.529 (17)C13—C14i1.387 (16)
C2—C31.377 (19)C13—C141.387 (16)
C3—C41.35 (2)C14—C151.364 (19)
C3—H30.9300C14—H140.9300
C4—C51.33 (2)C15—C161.342 (18)
C4—H40.9300C15—H150.9300
C5—C61.37 (2)C16—C15i1.342 (18)
C6—H60.9300C16—H160.9300
C7—C121.352 (17)
C7—Sb—C7i138.2 (7)C12—C7—C8120.0 (12)
C7—Sb—C13110.9 (3)C12—C7—Sb118.2 (10)
C7i—Sb—C13110.9 (3)C8—C7—Sb121.8 (10)
C7—Sb—O1i90.7 (3)C9—C8—C7117.3 (15)
C7i—Sb—O1i91.2 (4)C9—C8—H8121.4
C13—Sb—O1i87.3 (2)C7—C8—H8121.4
C7—Sb—O191.2 (4)C10—C9—C8120.7 (14)
C7i—Sb—O190.7 (3)C10—C9—H9119.6
C13—Sb—O187.3 (2)C8—C9—H9119.6
O1i—Sb—O1174.6 (5)C11—C10—C9121.2 (13)
C2—N—C6115.8 (13)C11—C10—H10119.4
C1—O1—Sb112.0 (7)C9—C10—H10119.4
O2—C1—O1125.4 (11)C10—C11—C12118.8 (15)
O2—C1—C2119.3 (12)C10—C11—H11120.6
O1—C1—C2115.3 (11)C12—C11—H11120.6
N—C2—C3123.1 (12)C7—C12—C11121.9 (15)
N—C2—C1117.8 (11)C7—C12—H12119.1
C3—C2—C1119.0 (13)C11—C12—H12119.1
C4—C3—C2120.5 (14)C14i—C13—C14119.1 (16)
C4—C3—H3119.7C14i—C13—Sb120.4 (8)
C2—C3—H3119.7C14—C13—Sb120.4 (8)
C5—C4—C3117.0 (14)C15—C14—C13119.0 (13)
C5—C4—H4121.5C15—C14—H14120.5
C3—C4—H4121.5C13—C14—H14120.5
C4—C5—C6120.4 (12)C16—C15—C14121.5 (14)
C4—C5—Br120.5 (12)C16—C15—H15119.2
C6—C5—Br119.0 (11)C14—C15—H15119.2
N—C6—C5123.0 (16)C15i—C16—C15119.8 (18)
N—C6—H6118.5C15i—C16—H16120.1
C5—C6—H6118.5C15—C16—H16120.1
C7—Sb—O1—C1−72.0 (8)C13—Sb—C7—C8172.8 (9)
C7i—Sb—O1—C166.3 (8)O1i—Sb—C7—C8−99.8 (11)
C13—Sb—O1—C1177.2 (7)O1—Sb—C7—C885.2 (10)
Sb—O1—C1—O23.2 (15)C12—C7—C8—C90.4 (19)
Sb—O1—C1—C2−176.0 (7)Sb—C7—C8—C9−178.2 (10)
C6—N—C2—C3−1(2)C7—C8—C9—C101(2)
C6—N—C2—C1176.3 (13)C8—C9—C10—C11−1(2)
O2—C1—C2—N−171.3 (13)C9—C10—C11—C120(2)
O1—C1—C2—N7.8 (15)C8—C7—C12—C11−1.8 (19)
O2—C1—C2—C35.8 (17)Sb—C7—C12—C11176.8 (10)
O1—C1—C2—C3−175.0 (12)C10—C11—C12—C72(2)
N—C2—C3—C4−1(2)C7—Sb—C13—C14i63.8 (7)
C1—C2—C3—C4−178.4 (12)C7i—Sb—C13—C14i−116.2 (7)
C2—C3—C4—C54(2)O1i—Sb—C13—C14i−25.9 (7)
C3—C4—C5—C6−5(2)O1—Sb—C13—C14i154.1 (7)
C3—C4—C5—Br175.5 (11)C7—Sb—C13—C14−116.2 (7)
C2—N—C6—C50(2)C7i—Sb—C13—C1463.8 (7)
C4—C5—C6—N3(3)O1i—Sb—C13—C14154.1 (7)
Br—C5—C6—N−177.5 (13)O1—Sb—C13—C14−25.9 (7)
C7i—Sb—C7—C12174.2 (9)C14i—C13—C14—C151.0 (10)
C13—Sb—C7—C12−5.8 (9)Sb—C13—C14—C15−179.0 (10)
O1i—Sb—C7—C1281.6 (9)C13—C14—C15—C16−2(2)
O1—Sb—C7—C12−93.3 (9)C14—C15—C16—C15i1.1 (10)
C7i—Sb—C7—C8−7.2 (9)

Symmetry codes: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10···Brii0.932.903.69 (2)144

Symmetry codes: (ii) −x+1/2, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2073).

References

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  • Mahon, M. F., Molloy, K. C., Omotowa, B. A. & Mesubi, M. A. (1998). J. Organomet. Chem.560, 95–101.
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