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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): m1261.
Published online 2009 September 30. doi:  10.1107/S1600536809038872
PMCID: PMC2970316

catena-Poly[[trimethyl­tin(IV)]-μ-2-(2-chloro­phenyl)­acetato]

Abstract

In the title polymeric coordination compound, [Sn(CH3)3(C8H6ClO2)]n, the Sn atoms exhibit a distorted trigonal-bipyramidal geometry with the carboxyl­ate O atoms of the 2-chloro­phenyl­acetato ligands in axial positions and with the equatorial sites occupied by the three methyl groups. Adjacent Sn atoms are bridged by coordination to the two O atoms of each 2-chloro­phenyl­acetato ligand, forming a chain structure.

Related literature

For the biological activity of organotin compounds, see: Wang et al. (2007 [triangle]). 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-m1261-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)3(C8H6ClO2)]
  • M r = 333.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1261-efi1.jpg
  • a = 7.0754 (9) Å
  • b = 28.306 (3) Å
  • c = 13.6721 (15) Å
  • β = 93.117 (2)°
  • V = 2734.1 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.05 mm−1
  • T = 298 K
  • 0.49 × 0.32 × 0.15 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.434, T max = 0.749
  • 14063 measured reflections
  • 4820 independent reflections
  • 3411 reflections with I > 2σ(I)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.107
  • S = 1.05
  • 4820 reflections
  • 277 parameters
  • H-atom parameters constrained
  • Δρmax = 1.09 e Å−3
  • Δρmin = −0.92 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/S1600536809038872/sj2651sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038872/sj2651Isup2.hkl

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

Acknowledgments

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support. This work was also supported by the Shangdong ‘Tai-Shan Scholar Research Fund’.

supplementary crystallographic information

Comment

The chemistry of organotin(IV) derivatives is a subject of study with growing interest due to their significant antimicrobial properties as well as antitumor activities (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. The title compound, which is shown in Fig.1 forms an extended one-dimensional chain structure arising from Sn—O bridges formed by the 2-(2-chlorophenyl)acetato ligands. The Sn—O bond distances in the compound (Sn(1)—O(1) = 2.396 (5) Å; Sn(1)—O(3) = 2.194 (4) Å) 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 and three methyl groups in the equatorial positions and two O atoms of symmetry related carboxylate groups in the axial positions.

Experimental

The reaction was carried out under a nitrogen atmosphere. 2-(2-chlorophenyl)acetic 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 to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of dichloromethane/methanol (1:1) to yield colourless blocks of the title compound (yield 81%. m.p.390 K). Anal. Calcd (%) for C11H15Cl1O2Sn1 (Mr = 333.37): C,39.63; H, 4.54; Cl, 10.63. Found (%): C, 39.51; H, 4.64; Cl, 10.75.

Refinement

The 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, O) or 1.5 Ueq(C) for the methyl groups.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
Fig. 2.
A view of the one-dimensional extended chain structure in the title compound.

Crystal data

[Sn(CH3)3(C8H6ClO2)]F(000) = 1312
Mr = 333.39Dx = 1.620 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4326 reflections
a = 7.0754 (9) Åθ = 2.6–24.8°
b = 28.306 (3) ŵ = 2.05 mm1
c = 13.6721 (15) ÅT = 298 K
β = 93.117 (2)°Block, colourless
V = 2734.1 (5) Å30.49 × 0.32 × 0.15 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer4820 independent reflections
Radiation source: fine-focus sealed tube3411 reflections with I > 2σ(I)
graphiteRint = 0.056
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.434, Tmax = 0.749k = −33→33
14063 measured reflectionsl = −10→16

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0224P)2 + 9.0463P] where P = (Fo2 + 2Fc2)/3
4820 reflections(Δ/σ)max = 0.001
277 parametersΔρmax = 1.09 e Å3
0 restraintsΔρmin = −0.92 e Å3

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

xyzUiso*/Ueq
Sn10.02624 (7)0.138217 (16)0.88059 (3)0.04764 (16)
Sn20.20583 (7)0.212967 (17)1.21572 (3)0.04848 (16)
Cl10.4073 (6)0.03321 (16)1.1310 (3)0.1655 (15)
Cl2−0.2267 (4)0.14040 (10)0.36127 (15)0.0943 (8)
O10.1070 (7)0.14009 (16)1.0530 (3)0.0583 (13)
O20.1197 (7)0.13802 (16)1.2145 (3)0.0572 (13)
O3−0.0431 (7)0.13733 (16)0.7223 (3)0.0564 (13)
O4−0.1907 (7)0.20535 (18)0.7318 (3)0.0620 (14)
C10.0842 (11)0.1192 (3)1.1319 (5)0.0553 (19)
C20.0044 (13)0.0697 (3)1.1322 (6)0.073 (2)
H2A−0.13230.07201.13330.088*
H2B0.03280.05461.07100.088*
C30.0721 (17)0.0382 (3)1.2138 (7)0.079 (3)
C40.2486 (19)0.0191 (4)1.2200 (8)0.103 (3)
C50.316 (2)−0.0112 (4)1.2941 (10)0.127 (4)
H50.4382−0.02371.29750.153*
C60.184 (3)−0.0208 (4)1.3620 (10)0.121 (5)
H60.2224−0.04101.41310.145*
C70.001 (2)−0.0036 (4)1.3623 (9)0.115 (4)
H7−0.0816−0.01211.41000.138*
C8−0.0504 (18)0.0264 (3)1.2880 (8)0.100 (3)
H8−0.17080.03971.28610.120*
C9−0.1339 (10)0.1720 (3)0.6832 (5)0.0504 (18)
C10−0.1744 (10)0.1690 (3)0.5734 (5)0.0553 (19)
H10A−0.06900.15340.54430.066*
H10B−0.18370.20070.54690.066*
C11−0.3557 (10)0.1423 (2)0.5447 (5)0.0514 (18)
C12−0.3923 (11)0.1278 (3)0.4478 (6)0.062 (2)
C13−0.5520 (14)0.1049 (3)0.4182 (7)0.079 (3)
H13−0.57130.09580.35310.095*
C14−0.6863 (13)0.0950 (3)0.4838 (7)0.080 (3)
H14−0.79670.07920.46330.097*
C15−0.6576 (12)0.1084 (3)0.5797 (7)0.072 (2)
H15−0.74880.10200.62440.086*
C16−0.4919 (11)0.1317 (3)0.6100 (6)0.064 (2)
H16−0.47230.14030.67540.077*
C170.1855 (13)0.0758 (3)0.8683 (6)0.079 (3)
H17A0.28910.07590.91670.119*
H17B0.23380.07410.80410.119*
H17C0.10620.04890.87850.119*
C18−0.2588 (11)0.1335 (3)0.9193 (6)0.077 (2)
H18A−0.30860.10300.90120.115*
H18B−0.33220.15760.88550.115*
H18C−0.26490.13780.98870.115*
C190.1885 (11)0.2012 (3)0.8801 (5)0.069 (2)
H19A0.30350.19690.91960.103*
H19B0.11710.22660.90620.103*
H19C0.21830.20860.81410.103*
C20−0.0375 (10)0.2385 (3)1.1363 (6)0.067 (2)
H20A−0.00010.25601.08030.100*
H20B−0.10720.25881.17760.100*
H20C−0.11580.21241.11490.100*
C210.2034 (13)0.2164 (3)1.3703 (5)0.075 (3)
H21A0.14780.24581.38910.112*
H21B0.33080.21451.39800.112*
H21C0.13060.19061.39390.112*
C220.4641 (10)0.2008 (3)1.1510 (6)0.071 (2)
H22A0.47500.16781.13560.107*
H22B0.56690.20991.19570.107*
H22C0.46840.21911.09200.107*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0547 (3)0.0418 (3)0.0458 (3)0.0031 (2)−0.0036 (2)−0.0021 (2)
Sn20.0490 (3)0.0512 (3)0.0451 (3)−0.0101 (2)0.0020 (2)−0.0036 (2)
Cl10.138 (3)0.195 (4)0.163 (3)0.045 (3)0.005 (3)0.002 (3)
Cl20.1043 (18)0.130 (2)0.0492 (12)−0.0172 (16)0.0086 (12)−0.0131 (13)
O10.083 (4)0.046 (3)0.045 (3)−0.007 (3)−0.002 (2)0.000 (2)
O20.083 (4)0.047 (3)0.041 (3)−0.015 (3)−0.001 (2)−0.003 (2)
O30.074 (3)0.049 (3)0.045 (3)0.017 (3)−0.008 (2)−0.007 (2)
O40.073 (4)0.058 (3)0.054 (3)0.022 (3)−0.009 (3)−0.005 (3)
C10.071 (5)0.046 (4)0.048 (4)−0.003 (4)−0.007 (4)0.001 (4)
C20.102 (7)0.057 (5)0.059 (5)−0.019 (5)−0.013 (5)0.001 (4)
C30.122 (9)0.044 (5)0.068 (6)−0.019 (5)−0.016 (6)−0.006 (4)
C40.145 (11)0.071 (7)0.088 (7)−0.001 (7)−0.021 (8)−0.002 (6)
C50.181 (14)0.084 (9)0.113 (10)0.012 (9)−0.035 (10)−0.006 (8)
C60.195 (16)0.064 (8)0.101 (10)−0.014 (9)−0.027 (10)0.006 (7)
C70.178 (14)0.078 (8)0.089 (8)−0.040 (9)−0.007 (9)−0.002 (7)
C80.153 (10)0.060 (6)0.084 (7)−0.026 (6)−0.011 (7)−0.003 (6)
C90.051 (4)0.057 (5)0.043 (4)0.007 (4)−0.002 (3)0.001 (4)
C100.055 (5)0.063 (5)0.047 (4)0.003 (4)−0.006 (3)−0.001 (4)
C110.050 (4)0.053 (5)0.051 (4)0.007 (3)−0.007 (3)0.000 (3)
C120.064 (5)0.061 (5)0.060 (5)0.002 (4)−0.009 (4)−0.010 (4)
C130.087 (7)0.074 (6)0.074 (6)−0.010 (5)−0.012 (5)−0.010 (5)
C140.077 (6)0.068 (6)0.094 (7)−0.012 (5)−0.012 (5)−0.002 (5)
C150.063 (5)0.070 (6)0.083 (6)−0.010 (4)0.008 (5)0.005 (5)
C160.068 (5)0.066 (5)0.058 (5)0.000 (4)0.000 (4)0.000 (4)
C170.106 (7)0.071 (6)0.060 (5)0.036 (5)−0.013 (5)−0.009 (4)
C180.059 (5)0.093 (7)0.078 (6)−0.008 (5)0.006 (4)0.006 (5)
C190.074 (5)0.075 (6)0.057 (5)−0.017 (4)0.000 (4)0.012 (4)
C200.050 (5)0.063 (5)0.086 (6)0.003 (4)0.001 (4)−0.010 (4)
C210.117 (7)0.068 (6)0.039 (4)−0.029 (5)0.005 (4)−0.004 (4)
C220.057 (5)0.082 (6)0.076 (5)−0.006 (4)0.006 (4)−0.003 (5)

Geometric parameters (Å, °)

Sn1—C172.107 (7)C10—C111.522 (9)
Sn1—C182.117 (7)C10—H10A0.9700
Sn1—C192.120 (7)C10—H10B0.9700
Sn1—O32.194 (4)C11—C161.381 (10)
Sn1—O12.396 (5)C11—C121.397 (10)
Sn2—C222.102 (7)C12—C131.345 (11)
Sn2—C202.113 (7)C13—C141.371 (12)
Sn2—C212.117 (7)C13—H130.9300
Sn2—O22.207 (5)C14—C151.369 (11)
Sn2—O4i2.432 (5)C14—H140.9300
Cl1—C41.746 (12)C15—C161.389 (11)
Cl2—C121.747 (8)C15—H150.9300
O1—C11.249 (8)C16—H160.9300
O2—C11.263 (8)C17—H17A0.9600
O3—C91.273 (8)C17—H17B0.9600
O4—C91.235 (8)C17—H17C0.9600
O4—Sn2ii2.432 (5)C18—H18A0.9600
C1—C21.510 (10)C18—H18B0.9600
C2—C31.487 (11)C18—H18C0.9600
C2—H2A0.9700C19—H19A0.9600
C2—H2B0.9700C19—H19B0.9600
C3—C41.359 (14)C19—H19C0.9600
C3—C81.411 (13)C20—H20A0.9600
C4—C51.395 (15)C20—H20B0.9600
C5—C61.380 (17)C20—H20C0.9600
C5—H50.9300C21—H21A0.9600
C6—C71.387 (17)C21—H21B0.9600
C6—H60.9300C21—H21C0.9600
C7—C81.358 (14)C22—H22A0.9600
C7—H70.9300C22—H22B0.9600
C8—H80.9300C22—H22C0.9600
C9—C101.515 (9)
C17—Sn1—C18119.2 (4)C9—C10—H10B108.9
C17—Sn1—C19114.4 (4)C11—C10—H10B108.9
C18—Sn1—C19125.2 (3)H10A—C10—H10B107.7
C17—Sn1—O390.2 (2)C16—C11—C12116.7 (7)
C18—Sn1—O394.6 (3)C16—C11—C10123.3 (6)
C19—Sn1—O395.6 (2)C12—C11—C10120.0 (7)
C17—Sn1—O189.8 (2)C13—C12—C11122.4 (8)
C18—Sn1—O186.3 (3)C13—C12—Cl2118.5 (7)
C19—Sn1—O183.4 (2)C11—C12—Cl2119.1 (6)
O3—Sn1—O1178.93 (18)C12—C13—C14120.1 (8)
C22—Sn2—C20122.9 (3)C12—C13—H13119.9
C22—Sn2—C21118.9 (3)C14—C13—H13119.9
C20—Sn2—C21116.5 (3)C15—C14—C13119.9 (8)
C22—Sn2—O294.9 (3)C15—C14—H14120.1
C20—Sn2—O296.2 (3)C13—C14—H14120.1
C21—Sn2—O292.0 (2)C14—C15—C16119.7 (8)
C22—Sn2—O4i86.0 (3)C14—C15—H15120.1
C20—Sn2—O4i87.3 (2)C16—C15—H15120.1
C21—Sn2—O4i83.4 (2)C11—C16—C15121.2 (7)
O2—Sn2—O4i175.08 (16)C11—C16—H16119.4
C1—O1—Sn1143.5 (5)C15—C16—H16119.4
C1—O2—Sn2117.0 (4)Sn1—C17—H17A109.5
C9—O3—Sn1119.0 (4)Sn1—C17—H17B109.5
C9—O4—Sn2ii141.7 (5)H17A—C17—H17B109.5
O1—C1—O2122.9 (7)Sn1—C17—H17C109.5
O1—C1—C2120.6 (6)H17A—C17—H17C109.5
O2—C1—C2116.5 (6)H17B—C17—H17C109.5
C3—C2—C1116.9 (7)Sn1—C18—H18A109.5
C3—C2—H2A108.1Sn1—C18—H18B109.5
C1—C2—H2A108.1H18A—C18—H18B109.5
C3—C2—H2B108.1Sn1—C18—H18C109.5
C1—C2—H2B108.1H18A—C18—H18C109.5
H2A—C2—H2B107.3H18B—C18—H18C109.5
C4—C3—C8117.4 (10)Sn1—C19—H19A109.5
C4—C3—C2122.9 (10)Sn1—C19—H19B109.5
C8—C3—C2119.8 (10)H19A—C19—H19B109.5
C3—C4—C5124.7 (13)Sn1—C19—H19C109.5
C3—C4—Cl1119.3 (9)H19A—C19—H19C109.5
C5—C4—Cl1116.0 (12)H19B—C19—H19C109.5
C6—C5—C4113.0 (14)Sn2—C20—H20A109.5
C6—C5—H5123.5Sn2—C20—H20B109.5
C4—C5—H5123.5H20A—C20—H20B109.5
C5—C6—C7127.0 (13)Sn2—C20—H20C109.5
C5—C6—H6116.5H20A—C20—H20C109.5
C7—C6—H6116.5H20B—C20—H20C109.5
C8—C7—C6115.4 (13)Sn2—C21—H21A109.5
C8—C7—H7122.3Sn2—C21—H21B109.5
C6—C7—H7122.3H21A—C21—H21B109.5
C7—C8—C3122.5 (12)Sn2—C21—H21C109.5
C7—C8—H8118.8H21A—C21—H21C109.5
C3—C8—H8118.8H21B—C21—H21C109.5
O4—C9—O3122.4 (6)Sn2—C22—H22A109.5
O4—C9—C10121.7 (6)Sn2—C22—H22B109.5
O3—C9—C10115.9 (6)H22A—C22—H22B109.5
C9—C10—C11113.2 (6)Sn2—C22—H22C109.5
C9—C10—H10A108.9H22A—C22—H22C109.5
C11—C10—H10A108.9H22B—C22—H22C109.5
C17—Sn1—O1—C1−67.1 (9)Cl1—C4—C5—C6179.9 (9)
C18—Sn1—O1—C152.3 (9)C4—C5—C6—C7−0.1 (19)
C19—Sn1—O1—C1178.4 (9)C5—C6—C7—C8−1.2 (19)
O3—Sn1—O1—C1−159 (9)C6—C7—C8—C32.0 (15)
C22—Sn2—O2—C1−66.8 (6)C4—C3—C8—C7−1.6 (14)
C20—Sn2—O2—C157.1 (6)C2—C3—C8—C7177.3 (8)
C21—Sn2—O2—C1174.0 (6)Sn2ii—O4—C9—O3160.1 (5)
O4i—Sn2—O2—C1−167 (2)Sn2ii—O4—C9—C10−22.1 (12)
C17—Sn1—O3—C9−174.5 (6)Sn1—O3—C9—O4−2.7 (9)
C18—Sn1—O3—C966.2 (6)Sn1—O3—C9—C10179.3 (4)
C19—Sn1—O3—C9−60.0 (6)O4—C9—C10—C11−91.2 (9)
O1—Sn1—O3—C9−83 (10)O3—C9—C10—C1186.7 (8)
Sn1—O1—C1—O2−163.3 (5)C9—C10—C11—C1614.6 (10)
Sn1—O1—C1—C214.4 (13)C9—C10—C11—C12−166.5 (7)
Sn2—O2—C1—O14.5 (10)C16—C11—C12—C130.3 (11)
Sn2—O2—C1—C2−173.3 (5)C10—C11—C12—C13−178.7 (8)
O1—C1—C2—C3148.0 (8)C16—C11—C12—Cl2179.6 (6)
O2—C1—C2—C3−34.2 (11)C10—C11—C12—Cl20.6 (10)
C1—C2—C3—C4−72.9 (11)C11—C12—C13—C140.1 (13)
C1—C2—C3—C8108.2 (9)Cl2—C12—C13—C14−179.1 (7)
C8—C3—C4—C50.2 (15)C12—C13—C14—C15−0.1 (14)
C2—C3—C4—C5−178.7 (9)C13—C14—C15—C16−0.4 (13)
C8—C3—C4—Cl1−179.1 (7)C12—C11—C16—C15−0.8 (11)
C2—C3—C4—Cl12.0 (13)C10—C11—C16—C15178.1 (7)
C3—C4—C5—C60.6 (17)C14—C15—C16—C110.9 (12)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2651).

References

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