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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m30.
Published online 2008 December 10. doi:  10.1107/S1600536808040798
PMCID: PMC2967877

catena-Poly[[trimethyl­tin(IV)]-μ-2,4,6-trichloro­benzoato]

Abstract

In the title compound, [Sn(CH3)3(C7H2Cl3O2)]n, the tin(IV) atom exhibits a slightly distorted trigonal-bipyramidal geometry with two O atoms of symmetry-related carboxyl­ate groups in the axial positions and three methyl groups in the equatorial positions. In the crystal structure, the metal atoms are linked by carboxyl­ate bridges into polymeric chains extending along the b axis.

Related literature

For related structures, see: Wang et al. (2007 [triangle]); Ma et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00m30-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)3(C7H2Cl3O2)]
  • M r = 388.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m30-efi2.jpg
  • a = 9.8457 (10) Å
  • b = 9.6891 (9) Å
  • c = 15.3028 (19) Å
  • β = 106.761 (1)°
  • V = 1397.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.38 mm−1
  • T = 298 (2) K
  • 0.42 × 0.18 × 0.08 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.434, T max = 0.832
  • 6983 measured reflections
  • 2469 independent reflections
  • 1996 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.085
  • S = 1.01
  • 2469 reflections
  • 145 parameters
  • H-atom parameters constrained
  • Δρmax = 0.68 e Å−3
  • Δρmin = −0.37 e Å−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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040798/rz2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040798/rz2273Isup2.hkl

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

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

Organoantin(IV) derivatives have recently attracted considerable attention due to the significant antimicrobial properties (Wang et al., 2007). As a part of our ongoing investigations in this field, we have synthesized the title compound and present its crystal structure here.

In the title compound (Fig. 1), the Sn—O bond distances (Table 1) are comparable to those found in related organotin carboxylates (Ma et al., 2006). The Sn atom assumes a slightly distorted trigonal-bipyramidal coordination geometry, provided by two O atoms of symmetry related carboxylate groups at the axial positions and three methyl groups at the equatorial positions. In the crystal structure, the metal atoms are linked by carboxylate bridges into polymeric chains extending along the b axis (Fig. 2).

Experimental

The reaction was carried out under nitrogen atmosphere. 2,4,6-Trichlorobenzoic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (1 mmol) was then added and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane/methanol (1:1 v/v) solution (yield 83%. m. p. 403K). Anal. Calcd (%) for C10H11Cl3O2Sn: C, 30.94; H, 2.86; O, 8.24; Sn, 30.58; Found (%): C, 30.89; H, 2.90; O, 8.31; Sn, 30.62.

Refinement

H atoms were positioned geometrically, with methyl C—H distances of 0.96 Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for the methyl groups.

Figures

Fig. 1.
The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity. Symmetry code: (A) = -x + 1,y + 1/2,-z + 1/2.
Fig. 2.
View of the one-dimensional chain structure extending along the b axis.

Crystal data

[Sn(CH3)3(C7H2Cl3O2)]F(000) = 752
Mr = 388.25Dx = 1.845 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3337 reflections
a = 9.8457 (10) Åθ = 2.5–27.6°
b = 9.6891 (9) ŵ = 2.38 mm1
c = 15.3028 (19) ÅT = 298 K
β = 106.761 (1)°Block, colourless
V = 1397.8 (3) Å30.42 × 0.18 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2469 independent reflections
Radiation source: fine-focus sealed tube1996 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→11
Tmin = 0.434, Tmax = 0.832k = −10→11
6983 measured reflectionsl = −18→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.048P)2 + 1.1107P] where P = (Fo2 + 2Fc2)/3
2469 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = −0.37 e Å3

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

xyzUiso*/Ueq
Sn10.41662 (3)0.26723 (3)0.24850 (2)0.03954 (13)
Cl10.13395 (13)−0.14643 (14)0.30795 (8)0.0553 (3)
Cl2−0.17245 (14)−0.41671 (14)0.00986 (9)0.0685 (4)
Cl30.21742 (14)−0.04603 (14)−0.01909 (8)0.0589 (3)
O10.2441 (3)0.1152 (3)0.1981 (2)0.0436 (7)
O20.4091 (3)−0.0438 (3)0.2076 (2)0.0483 (8)
C10.2834 (4)−0.0058 (4)0.1860 (3)0.0368 (9)
C20.1682 (4)−0.1073 (4)0.1414 (3)0.0357 (9)
C30.0947 (4)−0.1793 (4)0.1922 (3)0.0379 (9)
C4−0.0092 (5)−0.2761 (4)0.1529 (3)0.0416 (10)
H4−0.0557−0.32480.18810.050*
C5−0.0410 (5)−0.2974 (4)0.0609 (3)0.0429 (11)
C60.0256 (5)−0.2269 (4)0.0067 (3)0.0449 (11)
H60.0004−0.2414−0.05600.054*
C70.1307 (4)−0.1341 (4)0.0483 (3)0.0396 (10)
C80.2673 (5)0.4245 (5)0.2502 (4)0.0582 (13)
H8A0.31620.50440.28090.087*
H8B0.20230.39170.28180.087*
H8C0.21580.44840.18870.087*
C90.4924 (6)0.2466 (5)0.1337 (3)0.0510 (12)
H9A0.58670.20920.15230.077*
H9B0.49380.33550.10620.077*
H9C0.43120.18570.09020.077*
C100.5129 (6)0.1758 (6)0.3770 (3)0.0617 (14)
H10A0.60220.13590.37700.093*
H10B0.45200.10510.38860.093*
H10C0.52830.24490.42380.093*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.03773 (19)0.0345 (2)0.0475 (2)−0.00090 (12)0.01410 (14)−0.00256 (13)
Cl10.0537 (7)0.0745 (9)0.0398 (7)−0.0114 (6)0.0167 (5)−0.0052 (6)
Cl20.0641 (8)0.0599 (8)0.0692 (9)−0.0214 (7)−0.0003 (6)−0.0076 (7)
Cl30.0717 (8)0.0616 (8)0.0511 (7)−0.0064 (6)0.0300 (6)0.0062 (6)
O10.0357 (15)0.0308 (16)0.066 (2)−0.0010 (12)0.0176 (14)−0.0100 (14)
O20.0367 (17)0.0375 (17)0.068 (2)0.0041 (13)0.0106 (14)0.0015 (15)
C10.038 (2)0.034 (2)0.040 (2)−0.0021 (18)0.0155 (19)0.0017 (18)
C20.035 (2)0.028 (2)0.042 (2)0.0022 (17)0.0089 (18)−0.0017 (18)
C30.040 (2)0.037 (2)0.038 (2)−0.0023 (19)0.0133 (19)−0.0009 (19)
C40.038 (2)0.036 (2)0.051 (3)−0.0047 (18)0.012 (2)0.003 (2)
C50.039 (2)0.033 (2)0.051 (3)−0.0032 (19)0.005 (2)−0.007 (2)
C60.049 (3)0.045 (3)0.038 (3)0.004 (2)0.009 (2)−0.005 (2)
C70.041 (2)0.035 (2)0.045 (3)0.0037 (18)0.0144 (19)0.0031 (19)
C80.045 (3)0.045 (3)0.086 (4)−0.004 (2)0.022 (3)−0.019 (3)
C90.055 (3)0.052 (3)0.051 (3)−0.002 (2)0.023 (2)0.001 (2)
C100.078 (4)0.056 (3)0.047 (3)−0.014 (3)0.011 (3)0.004 (2)

Geometric parameters (Å, °)

Sn1—C92.107 (5)C4—C51.366 (6)
Sn1—C102.116 (5)C4—H40.9300
Sn1—C82.123 (4)C5—C61.377 (7)
Sn1—O12.212 (3)C6—C71.380 (6)
Sn1—O2i2.467 (3)C6—H60.9300
Cl1—C31.730 (4)C8—H8A0.9600
Cl2—C51.744 (4)C8—H8B0.9600
Cl3—C71.740 (4)C8—H8C0.9600
O1—C11.265 (5)C9—H9A0.9600
O2—C11.241 (5)C9—H9B0.9600
O2—Sn1ii2.467 (3)C9—H9C0.9600
C1—C21.508 (5)C10—H10A0.9600
C2—C71.390 (6)C10—H10B0.9600
C2—C31.392 (6)C10—H10C0.9600
C3—C41.390 (6)
C9—Sn1—C10124.3 (2)C6—C5—Cl2118.7 (4)
C9—Sn1—C8119.4 (2)C5—C6—C7118.0 (4)
C10—Sn1—C8114.6 (2)C5—C6—H6121.0
C9—Sn1—O193.83 (16)C7—C6—H6121.0
C10—Sn1—O197.96 (16)C6—C7—C2122.4 (4)
C8—Sn1—O191.00 (15)C6—C7—Cl3118.5 (4)
C9—Sn1—O2i84.92 (15)C2—C7—Cl3119.1 (3)
C10—Sn1—O2i88.16 (16)Sn1—C8—H8A109.5
C8—Sn1—O2i83.90 (15)Sn1—C8—H8B109.5
O1—Sn1—O2i173.28 (10)H8A—C8—H8B109.5
C1—O1—Sn1115.6 (2)Sn1—C8—H8C109.5
C1—O2—Sn1ii148.7 (3)H8A—C8—H8C109.5
O2—C1—O1124.0 (4)H8B—C8—H8C109.5
O2—C1—C2119.3 (4)Sn1—C9—H9A109.5
O1—C1—C2116.6 (3)Sn1—C9—H9B109.5
C7—C2—C3116.9 (4)H9A—C9—H9B109.5
C7—C2—C1121.9 (4)Sn1—C9—H9C109.5
C3—C2—C1121.2 (4)H9A—C9—H9C109.5
C4—C3—C2122.1 (4)H9B—C9—H9C109.5
C4—C3—Cl1119.1 (3)Sn1—C10—H10A109.5
C2—C3—Cl1118.7 (3)Sn1—C10—H10B109.5
C5—C4—C3118.0 (4)H10A—C10—H10B109.5
C5—C4—H4121.0Sn1—C10—H10C109.5
C3—C4—H4121.0H10A—C10—H10C109.5
C4—C5—C6122.6 (4)H10B—C10—H10C109.5
C4—C5—Cl2118.8 (4)
C9—Sn1—O1—C161.1 (3)C1—C2—C3—Cl12.0 (5)
C10—Sn1—O1—C1−64.4 (3)C2—C3—C4—C5−1.5 (7)
C8—Sn1—O1—C1−179.3 (3)Cl1—C3—C4—C5178.2 (3)
Sn1ii—O2—C1—O1154.5 (4)C3—C4—C5—C6−0.1 (7)
Sn1ii—O2—C1—C2−26.3 (8)C3—C4—C5—Cl2−179.2 (3)
Sn1—O1—C1—O26.1 (5)C4—C5—C6—C71.7 (7)
Sn1—O1—C1—C2−173.0 (3)Cl2—C5—C6—C7−179.2 (3)
O2—C1—C2—C7−82.9 (5)C5—C6—C7—C2−1.8 (7)
O1—C1—C2—C796.3 (5)C5—C6—C7—Cl3179.1 (3)
O2—C1—C2—C396.8 (5)C3—C2—C7—C60.2 (6)
O1—C1—C2—C3−84.0 (5)C1—C2—C7—C6179.9 (4)
C7—C2—C3—C41.5 (6)C3—C2—C7—Cl3179.3 (3)
C1—C2—C3—C4−178.2 (4)C1—C2—C7—Cl3−1.0 (5)
C7—C2—C3—Cl1−178.3 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2273).

References

  • Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem., 691, 1713-1721.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Wang, H., Yin, H. & Wang, D. (2007). Acta Cryst. E63, m2955.

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