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Acta Cryst. (2008). E64, m1302    [ doi:10.1107/S1600536808029632 ]

Chlorido(2-chloronicotinato)triphenylantimony(V)

L. Quan, H. Yin and D. Wang

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93 Å, with Uiso(H) = 1.2 Ueq(C).

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 (I) with atom labels and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A dimer linked by C20—H20···O2i hydrogen bonds (dashed lines) (symmetry code i: 1 - x,-y,1 - z).
Chlorido(2-chloronicotinato)triphenylantimony(V) top
Crystal data top
[Sb(C6H5)3(C6H3ClNO2)Cl]F(000) = 1080
Mr = 545.04Dx = 1.635 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5771 reflections
a = 11.9580 (9) Åθ = 2.3–28.0°
b = 15.4428 (18) ŵ = 1.51 mm−1
c = 12.0264 (15) ÅT = 298 K
β = 94.291 (2)°Block, colorless
V = 2214.6 (4) Å30.45 × 0.41 × 0.40 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		3893 independent reflections
Radiation source: fine-focus sealed tube3149 reflections with I > 2σ(I)
graphiteRint = 0.026
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→14
Tmin = 0.550, Tmax = 0.584k = −17→18
10922 measured reflectionsl = −14→10
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.4912P]
where P = (Fo2 + 2Fc2)/3
3893 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.39 e Å−3
Crystal data top
[Sb(C6H5)3(C6H3ClNO2)Cl]V = 2214.6 (4) Å3
Mr = 545.04Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.9580 (9) ŵ = 1.51 mm−1
b = 15.4428 (18) ÅT = 298 K
c = 12.0264 (15) Å0.45 × 0.41 × 0.40 mm
β = 94.291 (2)°
Data collection top
Bruker SMART CCD
diffractometer		3893 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3149 reflections with I > 2σ(I)
Tmin = 0.550, Tmax = 0.584Rint = 0.026
10922 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.071Δρmax = 0.52 e Å−3
S = 1.00Δρmin = −0.39 e Å−3
3893 reflectionsAbsolute structure: ?
271 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sb10.523870 (16)0.223556 (12)0.600425 (16)0.03369 (9)
Cl10.55909 (9)−0.11472 (6)0.80420 (9)0.0663 (3)
Cl20.45726 (7)0.27660 (6)0.41124 (6)0.0467 (2)
N10.6489 (3)−0.0695 (2)0.9960 (3)0.0674 (9)
O10.58192 (17)0.17341 (13)0.75786 (17)0.0412 (5)
O20.5294 (2)0.04741 (15)0.68384 (19)0.0534 (6)
C10.5703 (2)0.0892 (2)0.7620 (3)0.0389 (7)
C20.6110 (3)−0.0368 (2)0.8986 (3)0.0472 (8)
C30.6124 (2)0.0507 (2)0.8723 (3)0.0390 (7)
C40.6553 (3)0.1057 (2)0.9560 (3)0.0526 (9)
H40.65810.16500.94310.063*
C50.6938 (3)0.0727 (3)1.0584 (3)0.0671 (11)
H50.72200.10921.11530.081*
C60.6895 (4)−0.0142 (3)1.0742 (4)0.0746 (13)
H60.7163−0.03631.14310.090*
C70.5622 (3)0.34849 (19)0.6637 (3)0.0382 (7)
C80.6477 (3)0.3615 (2)0.7465 (3)0.0498 (9)
H80.69010.31510.77530.060*
C90.6690 (3)0.4453 (2)0.7860 (3)0.0584 (10)
H90.72690.45490.84060.070*
C100.6060 (4)0.5124 (2)0.7453 (3)0.0629 (11)
H100.62140.56800.77190.075*
C110.5199 (4)0.4995 (2)0.6655 (3)0.0657 (11)
H110.47580.54590.63950.079*
C120.4988 (3)0.4171 (2)0.6237 (3)0.0537 (9)
H120.44140.40840.56830.064*
C130.3560 (2)0.1945 (2)0.6294 (3)0.0363 (7)
C140.3242 (3)0.2102 (2)0.7346 (3)0.0527 (9)
H140.37710.22640.79140.063*
C150.2124 (3)0.2015 (3)0.7553 (3)0.0649 (11)
H150.18950.21360.82590.078*
C160.1358 (3)0.1752 (3)0.6727 (3)0.0584 (10)
H160.06090.16930.68720.070*
C170.1683 (3)0.1575 (3)0.5685 (3)0.0612 (10)
H170.11580.13830.51310.073*
C180.2789 (3)0.1682 (2)0.5453 (3)0.0510 (9)
H180.30100.15780.47400.061*
C190.6570 (3)0.1635 (2)0.5247 (2)0.0388 (7)
C200.6410 (3)0.0945 (2)0.4541 (3)0.0559 (9)
H200.57010.07010.44090.067*
C210.7306 (4)0.0614 (3)0.4028 (3)0.0727 (12)
H210.72020.01440.35480.087*
C220.8339 (4)0.0967 (3)0.4217 (4)0.0769 (14)
H220.89420.07350.38740.092*
C230.8497 (3)0.1667 (3)0.4913 (4)0.0723 (13)
H230.92060.19130.50260.087*
C240.7621 (3)0.2011 (3)0.5444 (3)0.0544 (9)
H240.77290.24820.59220.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.03589 (13)0.02844 (13)0.03649 (13)−0.00131 (9)0.00101 (9)0.00020 (9)
Cl10.0809 (7)0.0349 (5)0.0805 (7)−0.0049 (5)−0.0123 (5)0.0016 (5)
Cl20.0547 (5)0.0472 (5)0.0381 (4)0.0028 (4)0.0029 (4)0.0067 (4)
N10.078 (2)0.055 (2)0.067 (2)0.0044 (18)−0.0095 (18)0.0224 (18)
O10.0499 (12)0.0300 (12)0.0424 (12)−0.0017 (10)−0.0044 (10)0.0024 (10)
O20.0722 (16)0.0367 (13)0.0488 (14)−0.0085 (12)−0.0122 (12)0.0001 (11)
C10.0393 (17)0.0341 (18)0.0429 (18)−0.0006 (14)0.0007 (14)−0.0014 (15)
C20.0437 (18)0.043 (2)0.055 (2)0.0016 (16)−0.0005 (16)0.0041 (17)
C30.0362 (16)0.0378 (18)0.0423 (18)0.0015 (14)−0.0006 (13)0.0010 (14)
C40.061 (2)0.045 (2)0.050 (2)−0.0025 (17)−0.0085 (17)0.0012 (17)
C50.077 (3)0.071 (3)0.049 (2)−0.002 (2)−0.017 (2)−0.001 (2)
C60.091 (3)0.077 (3)0.052 (2)0.005 (3)−0.018 (2)0.017 (2)
C70.0446 (17)0.0273 (16)0.0438 (18)−0.0015 (14)0.0103 (15)−0.0004 (14)
C80.061 (2)0.037 (2)0.051 (2)−0.0001 (17)−0.0046 (17)−0.0006 (16)
C90.069 (2)0.051 (2)0.054 (2)−0.012 (2)−0.0057 (19)−0.0107 (18)
C100.093 (3)0.033 (2)0.063 (3)−0.009 (2)0.007 (2)−0.0060 (18)
C110.092 (3)0.036 (2)0.068 (3)0.012 (2)−0.005 (2)−0.0024 (19)
C120.063 (2)0.038 (2)0.058 (2)0.0060 (17)−0.0044 (18)−0.0056 (17)
C130.0349 (16)0.0318 (17)0.0420 (18)0.0006 (13)0.0026 (14)0.0061 (13)
C140.048 (2)0.066 (3)0.045 (2)−0.0009 (18)0.0041 (16)−0.0008 (17)
C150.055 (2)0.087 (3)0.055 (2)0.000 (2)0.0178 (19)0.001 (2)
C160.0376 (18)0.065 (3)0.074 (3)0.0008 (18)0.0122 (19)0.013 (2)
C170.0403 (19)0.076 (3)0.067 (3)−0.0089 (19)−0.0027 (18)−0.002 (2)
C180.0430 (19)0.062 (2)0.048 (2)−0.0040 (18)0.0016 (16)−0.0052 (18)
C190.0426 (17)0.0341 (17)0.0398 (17)0.0059 (14)0.0038 (14)0.0010 (14)
C200.069 (2)0.041 (2)0.058 (2)−0.0052 (18)0.0049 (19)−0.0097 (17)
C210.101 (3)0.054 (3)0.065 (3)0.023 (3)0.024 (2)−0.009 (2)
C220.075 (3)0.090 (4)0.068 (3)0.042 (3)0.024 (2)0.011 (3)
C230.041 (2)0.101 (4)0.075 (3)0.012 (2)0.004 (2)0.006 (3)
C240.0442 (19)0.064 (2)0.055 (2)0.0044 (18)−0.0025 (17)−0.0053 (18)
Geometric parameters (Å, °) top
Sb1—C192.107 (3)C11—C121.385 (5)
Sb1—C132.111 (3)C11—H110.9300
Sb1—C72.111 (3)C12—H120.9300
Sb1—O12.114 (2)C13—C141.369 (5)
Sb1—Cl22.4921 (8)C13—C181.377 (4)
Cl1—C21.736 (4)C14—C151.385 (5)
N1—C21.324 (4)C14—H140.9300
N1—C61.335 (5)C15—C161.361 (5)
O1—C11.309 (4)C15—H150.9300
O2—C11.213 (4)C16—C171.367 (5)
C1—C31.506 (4)C16—H160.9300
C2—C31.389 (5)C17—C181.382 (5)
C3—C41.386 (5)C17—H170.9300
C4—C51.380 (5)C18—H180.9300
C4—H40.9300C19—C201.367 (5)
C5—C61.356 (6)C19—C241.390 (5)
C5—H50.9300C20—C211.374 (5)
C6—H60.9300C20—H200.9300
C7—C121.369 (5)C21—C221.354 (6)
C7—C81.388 (4)C21—H210.9300
C8—C91.394 (5)C22—C231.371 (6)
C8—H80.9300C22—H220.9300
C9—C101.351 (5)C23—C241.373 (5)
C9—H90.9300C23—H230.9300
C10—C111.369 (5)C24—H240.9300
C10—H100.9300
C19—Sb1—C13137.38 (12)C10—C11—C12119.7 (4)
C19—Sb1—C7114.05 (12)C10—C11—H11120.1
C13—Sb1—C7108.55 (12)C12—C11—H11120.1
C19—Sb1—O191.02 (10)C7—C12—C11120.2 (3)
C13—Sb1—O191.53 (10)C7—C12—H12119.9
C7—Sb1—O187.95 (10)C11—C12—H12119.9
C19—Sb1—Cl287.14 (8)C14—C13—C18120.9 (3)
C13—Sb1—Cl288.72 (8)C14—C13—Sb1116.6 (2)
C7—Sb1—Cl294.27 (9)C18—C13—Sb1122.3 (2)
O1—Sb1—Cl2177.56 (6)C13—C14—C15119.2 (4)
C2—N1—C6117.5 (3)C13—C14—H14120.4
C1—O1—Sb1111.67 (19)C15—C14—H14120.4
O2—C1—O1122.5 (3)C16—C15—C14120.2 (4)
O2—C1—C3124.1 (3)C16—C15—H15119.9
O1—C1—C3113.4 (3)C14—C15—H15119.9
N1—C2—C3124.3 (3)C15—C16—C17120.5 (3)
N1—C2—Cl1113.3 (3)C15—C16—H16119.8
C3—C2—Cl1122.4 (3)C17—C16—H16119.8
C4—C3—C2116.2 (3)C16—C17—C18120.2 (3)
C4—C3—C1118.6 (3)C16—C17—H17119.9
C2—C3—C1125.2 (3)C18—C17—H17119.9
C5—C4—C3120.1 (4)C13—C18—C17119.0 (3)
C5—C4—H4119.9C13—C18—H18120.5
C3—C4—H4119.9C17—C18—H18120.5
C6—C5—C4118.5 (4)C20—C19—C24121.0 (3)
C6—C5—H5120.7C20—C19—Sb1122.5 (3)
C4—C5—H5120.7C24—C19—Sb1116.4 (2)
N1—C6—C5123.3 (4)C19—C20—C21119.4 (4)
N1—C6—H6118.3C19—C20—H20120.3
C5—C6—H6118.3C21—C20—H20120.3
C12—C7—C8119.9 (3)C22—C21—C20120.5 (4)
C12—C7—Sb1118.8 (2)C22—C21—H21119.8
C8—C7—Sb1121.3 (2)C20—C21—H21119.8
C7—C8—C9119.0 (3)C21—C22—C23120.2 (4)
C7—C8—H8120.5C21—C22—H22119.9
C9—C8—H8120.5C23—C22—H22119.9
C10—C9—C8120.4 (4)C22—C23—C24120.9 (4)
C10—C9—H9119.8C22—C23—H23119.5
C8—C9—H9119.8C24—C23—H23119.5
C9—C10—C11120.8 (4)C23—C24—C19118.0 (4)
C9—C10—H10119.6C23—C24—H24121.0
C11—C10—H10119.6C19—C24—H24121.0
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C20—H20···O2i0.932.593.346 (4)139.
Symmetry codes: (i) −x+1, −y, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Sb1—C192.107 (3)Sb1—O12.114 (2)
Sb1—C132.111 (3)Sb1—Cl22.4921 (8)
Sb1—C72.111 (3)
C19—Sb1—C13137.38 (12)C13—Sb1—C7108.55 (12)
C19—Sb1—C7114.05 (12)O1—Sb1—Cl2177.56 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C20—H20···O2i0.932.593.346 (4)139.
Symmetry codes: (i) −x+1, −y, −z+1.
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

Chaudhari, K. R., Jain, V. K., Sagoria, V. S. & Tiekink, E. R. T. (2007). J. Organomet. Chem. 692, 4928–4932.

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.

Yin, H. D., Quan, L. & Li, L. W. (2008). Inorg. Chem. Commun. 11, 1122–1125.