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Acta Cryst. (2009). E65, m1261    [ doi:10.1107/S1600536809038872 ]

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

L. Wen, H. Yin and W. Li

Abstract top

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.

Comment top

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.

Related literature top

For the biological activity of organotin compounds, see: Wang et al. (2007). For related structures, see: Wang et al. (2007); Ma et al. (2006).

Experimental top

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 top

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.

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of the one-dimensional extended chain structure in the title compound.
catena-Poly[[trimethyltin(IV)]-µ-2-(2-chlorophenyl)acetato] top
Crystal data top
[Sn(CH3)3(C8H6ClO2)]F(000) = 1312
Mr = 333.39Dx = 1.620 Mg m−3
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 mm−1
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 top
Siemens SMART CCD area-detector
diffractometer		4820 independent reflections
Radiation source: fine-focus sealed tube3411 reflections with I > 2σ(I)
graphiteRint = 0.056
φ 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 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.05 w = 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 Å−3
0 restraintsΔρmin = −0.92 e Å−3
Crystal data top
[Sn(CH3)3(C8H6ClO2)]V = 2734.1 (5) Å3
Mr = 333.39Z = 8
Monoclinic, P21/nMo Kα radiation
a = 7.0754 (9) ŵ = 2.05 mm−1
b = 28.306 (3) ÅT = 298 K
c = 13.6721 (15) Å0.49 × 0.32 × 0.15 mm
β = 93.117 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer		4820 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3411 reflections with I > 2σ(I)
Tmin = 0.434, Tmax = 0.749Rint = 0.056
14063 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.107Δρmax = 1.09 e Å−3
S = 1.05Δρmin = −0.92 e Å−3
4820 reflectionsAbsolute structure: ?
277 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Sn1—C172.107 (7)Sn2—C222.102 (7)
Sn1—C182.117 (7)Sn2—C202.113 (7)
Sn1—C192.120 (7)Sn2—C212.117 (7)
Sn1—O32.194 (4)Sn2—O22.207 (5)
Sn1—O12.396 (5)Sn2—O4i2.432 (5)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2.
Acknowledgements top

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'.

references
References top

Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem. 691, 1713–1721.

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