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Acta Cryst. (2009). E65, m30    [ doi:10.1107/S1600536808040798 ]

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

L. Wen, H. Yin, W. Li and D. Wang

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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.

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 the compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity. Symmetry code: (A) = -x + 1,y + 1/2,-z + 1/2.
[Figure 2] Fig. 2. View of the one-dimensional chain structure extending along the b axis.
catena-Poly[[trimethyltin(IV)]-µ-2,4,6-trichlorobenzoato] top
Crystal data top
[Sn(CH3)3(C7H2Cl3O2)]F(000) = 752
Mr = 388.25Dx = 1.845 Mg m−3
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 mm−1
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 top
Bruker SMART CCD area-detector
diffractometer		2469 independent reflections
Radiation source: fine-focus sealed tube1996 reflections with I > 2σ(I)
graphiteRint = 0.025
φ 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 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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.01 w = 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 Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Sn(CH3)3(C7H2Cl3O2)]V = 1397.8 (3) Å3
Mr = 388.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8457 (10) ŵ = 2.38 mm−1
b = 9.6891 (9) ÅT = 298 K
c = 15.3028 (19) Å0.42 × 0.18 × 0.08 mm
β = 106.761 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2469 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1996 reflections with I > 2σ(I)
Tmin = 0.434, Tmax = 0.832Rint = 0.025
6983 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.085Δρmax = 0.68 e Å−3
S = 1.01Δρmin = −0.37 e Å−3
2469 reflectionsAbsolute structure: ?
145 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Sn1—C92.107 (5)Sn1—O12.212 (3)
Sn1—C102.116 (5)Sn1—O2i2.467 (3)
Sn1—C82.123 (4)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
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

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.

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.