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

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

doi:10.1107/S1600536808040798

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m30

doi:10.1107/S1600536808040798

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

Liyuan Wen,^a Handong Yin,^a ^* Wenkuan Li ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 15 November 2008; accepted 3 December 2008; online 10 December 2008)

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 ); Ma et al. (2006 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₇H₂Cl₃O₂)]
M_r = 388.25
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.085
S = 1.01
2469 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C9	2.107 (5)
Sn1—C10	2.116 (5)
Sn1—C8	2.123 (4)
Sn1—O1	2.212 (3)
Sn1—O2ⁱ	2.467 (3)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

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

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

checkCIF report

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.

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

	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.

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

Crystal data top

[Sn(CH₃)₃(C₇H₂Cl₃O₂)]	F(000) = 752
M_r = 388.25	D_x = 1.845 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3337 reflections
a = 9.8457 (10) Å	θ = 2.5–27.6°
b = 9.6891 (9) Å	µ = 2.38 mm⁻¹
c = 15.3028 (19) Å	T = 298 K
β = 106.761 (1)°	Block, colourless
V = 1397.8 (3) Å³	0.42 × 0.18 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2469 independent reflections
Radiation source: fine-focus sealed tube	1996 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.434, T_max = 0.832	k = −10→11
6983 measured reflections	l = −18→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.048P)² + 1.1107P] where P = (F_o² + 2F_c²)/3
2469 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₇H₂Cl₃O₂)]	V = 1397.8 (3) Å³
M_r = 388.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8457 (10) Å	µ = 2.38 mm⁻¹
b = 9.6891 (9) Å	T = 298 K
c = 15.3028 (19) Å	0.42 × 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)
T_min = 0.434, T_max = 0.832	R_int = 0.025
6983 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.01	Δρ_max = 0.68 e Å⁻³
2469 reflections	Δρ_min = −0.37 e Å⁻³
145 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.41662 (3)	0.26723 (3)	0.24850 (2)	0.03954 (13)
Cl1	0.13395 (13)	−0.14643 (14)	0.30795 (8)	0.0553 (3)
Cl2	−0.17245 (14)	−0.41671 (14)	0.00986 (9)	0.0685 (4)
Cl3	0.21742 (14)	−0.04603 (14)	−0.01909 (8)	0.0589 (3)
O1	0.2441 (3)	0.1152 (3)	0.1981 (2)	0.0436 (7)
O2	0.4091 (3)	−0.0438 (3)	0.2076 (2)	0.0483 (8)
C1	0.2834 (4)	−0.0058 (4)	0.1860 (3)	0.0368 (9)
C2	0.1682 (4)	−0.1073 (4)	0.1414 (3)	0.0357 (9)
C3	0.0947 (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	−0.3248	0.1881	0.050*
C5	−0.0410 (5)	−0.2974 (4)	0.0609 (3)	0.0429 (11)
C6	0.0256 (5)	−0.2269 (4)	0.0067 (3)	0.0449 (11)
H6	0.0004	−0.2414	−0.0560	0.054*
C7	0.1307 (4)	−0.1341 (4)	0.0483 (3)	0.0396 (10)
C8	0.2673 (5)	0.4245 (5)	0.2502 (4)	0.0582 (13)
H8A	0.3162	0.5044	0.2809	0.087*
H8B	0.2023	0.3917	0.2818	0.087*
H8C	0.2158	0.4484	0.1887	0.087*
C9	0.4924 (6)	0.2466 (5)	0.1337 (3)	0.0510 (12)
H9A	0.5867	0.2092	0.1523	0.077*
H9B	0.4938	0.3355	0.1062	0.077*
H9C	0.4312	0.1857	0.0902	0.077*
C10	0.5129 (6)	0.1758 (6)	0.3770 (3)	0.0617 (14)
H10A	0.6022	0.1359	0.3770	0.093*
H10B	0.4520	0.1051	0.3886	0.093*
H10C	0.5283	0.2449	0.4238	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03773 (19)	0.0345 (2)	0.0475 (2)	−0.00090 (12)	0.01410 (14)	−0.00256 (13)
Cl1	0.0537 (7)	0.0745 (9)	0.0398 (7)	−0.0114 (6)	0.0167 (5)	−0.0052 (6)
Cl2	0.0641 (8)	0.0599 (8)	0.0692 (9)	−0.0214 (7)	−0.0003 (6)	−0.0076 (7)
Cl3	0.0717 (8)	0.0616 (8)	0.0511 (7)	−0.0064 (6)	0.0300 (6)	0.0062 (6)
O1	0.0357 (15)	0.0308 (16)	0.066 (2)	−0.0010 (12)	0.0176 (14)	−0.0100 (14)
O2	0.0367 (17)	0.0375 (17)	0.068 (2)	0.0041 (13)	0.0106 (14)	0.0015 (15)
C1	0.038 (2)	0.034 (2)	0.040 (2)	−0.0021 (18)	0.0155 (19)	0.0017 (18)
C2	0.035 (2)	0.028 (2)	0.042 (2)	0.0022 (17)	0.0089 (18)	−0.0017 (18)
C3	0.040 (2)	0.037 (2)	0.038 (2)	−0.0023 (19)	0.0133 (19)	−0.0009 (19)
C4	0.038 (2)	0.036 (2)	0.051 (3)	−0.0047 (18)	0.012 (2)	0.003 (2)
C5	0.039 (2)	0.033 (2)	0.051 (3)	−0.0032 (19)	0.005 (2)	−0.007 (2)
C6	0.049 (3)	0.045 (3)	0.038 (3)	0.004 (2)	0.009 (2)	−0.005 (2)
C7	0.041 (2)	0.035 (2)	0.045 (3)	0.0037 (18)	0.0144 (19)	0.0031 (19)
C8	0.045 (3)	0.045 (3)	0.086 (4)	−0.004 (2)	0.022 (3)	−0.019 (3)
C9	0.055 (3)	0.052 (3)	0.051 (3)	−0.002 (2)	0.023 (2)	0.001 (2)
C10	0.078 (4)	0.056 (3)	0.047 (3)	−0.014 (3)	0.011 (3)	0.004 (2)

Geometric parameters (Å, º) top

Sn1—C9	2.107 (5)	C4—C5	1.366 (6)
Sn1—C10	2.116 (5)	C4—H4	0.9300
Sn1—C8	2.123 (4)	C5—C6	1.377 (7)
Sn1—O1	2.212 (3)	C6—C7	1.380 (6)
Sn1—O2ⁱ	2.467 (3)	C6—H6	0.9300
Cl1—C3	1.730 (4)	C8—H8A	0.9600
Cl2—C5	1.744 (4)	C8—H8B	0.9600
Cl3—C7	1.740 (4)	C8—H8C	0.9600
O1—C1	1.265 (5)	C9—H9A	0.9600
O2—C1	1.241 (5)	C9—H9B	0.9600
O2—Sn1ⁱⁱ	2.467 (3)	C9—H9C	0.9600
C1—C2	1.508 (5)	C10—H10A	0.9600
C2—C7	1.390 (6)	C10—H10B	0.9600
C2—C3	1.392 (6)	C10—H10C	0.9600
C3—C4	1.390 (6)

C9—Sn1—C10	124.3 (2)	C6—C5—Cl2	118.7 (4)
C9—Sn1—C8	119.4 (2)	C5—C6—C7	118.0 (4)
C10—Sn1—C8	114.6 (2)	C5—C6—H6	121.0
C9—Sn1—O1	93.83 (16)	C7—C6—H6	121.0
C10—Sn1—O1	97.96 (16)	C6—C7—C2	122.4 (4)
C8—Sn1—O1	91.00 (15)	C6—C7—Cl3	118.5 (4)
C9—Sn1—O2ⁱ	84.92 (15)	C2—C7—Cl3	119.1 (3)
C10—Sn1—O2ⁱ	88.16 (16)	Sn1—C8—H8A	109.5
C8—Sn1—O2ⁱ	83.90 (15)	Sn1—C8—H8B	109.5
O1—Sn1—O2ⁱ	173.28 (10)	H8A—C8—H8B	109.5
C1—O1—Sn1	115.6 (2)	Sn1—C8—H8C	109.5
C1—O2—Sn1ⁱⁱ	148.7 (3)	H8A—C8—H8C	109.5
O2—C1—O1	124.0 (4)	H8B—C8—H8C	109.5
O2—C1—C2	119.3 (4)	Sn1—C9—H9A	109.5
O1—C1—C2	116.6 (3)	Sn1—C9—H9B	109.5
C7—C2—C3	116.9 (4)	H9A—C9—H9B	109.5
C7—C2—C1	121.9 (4)	Sn1—C9—H9C	109.5
C3—C2—C1	121.2 (4)	H9A—C9—H9C	109.5
C4—C3—C2	122.1 (4)	H9B—C9—H9C	109.5
C4—C3—Cl1	119.1 (3)	Sn1—C10—H10A	109.5
C2—C3—Cl1	118.7 (3)	Sn1—C10—H10B	109.5
C5—C4—C3	118.0 (4)	H10A—C10—H10B	109.5
C5—C4—H4	121.0	Sn1—C10—H10C	109.5
C3—C4—H4	121.0	H10A—C10—H10C	109.5
C4—C5—C6	122.6 (4)	H10B—C10—H10C	109.5
C4—C5—Cl2	118.8 (4)

C9—Sn1—O1—C1	61.1 (3)	C1—C2—C3—Cl1	2.0 (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—C5	178.2 (3)
Sn1ⁱⁱ—O2—C1—O1	154.5 (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—O2	6.1 (5)	C4—C5—C6—C7	1.7 (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—C7	96.3 (5)	C5—C6—C7—Cl3	179.1 (3)
O2—C1—C2—C3	96.8 (5)	C3—C2—C7—C6	0.2 (6)
O1—C1—C2—C3	−84.0 (5)	C1—C2—C7—C6	179.9 (4)
C7—C2—C3—C4	1.5 (6)	C3—C2—C7—Cl3	179.3 (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.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₇H₂Cl₃O₂)]
M_r	388.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.8457 (10), 9.6891 (9), 15.3028 (19)
β (°)	106.761 (1)
V (Å³)	1397.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.38
Crystal size (mm)	0.42 × 0.18 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.434, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	6983, 2469, 1996
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.085, 1.01
No. of reflections	2469
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.37

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—C9	2.107 (5)	Sn1—O1	2.212 (3)
Sn1—C10	2.116 (5)	Sn1—O2ⁱ	2.467 (3)
Sn1—C8	2.123 (4)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

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

References

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