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Acta Cryst. (2011). E67, m664    [ doi:10.1107/S1600536811015741 ]

Tris(2-chlorobenzyl)[3-(4-methylphenyl)prop-2-enoato-[kappa]O]tin(IV)

T. C. Keng, K. M. Lo and S. W. Ng

Abstract top

The SnIV atom in the title compound, [Sn(C7H6Cl)3(C10H9O2)], exists in a tetrahedral geometry [[Sigma] C-Sn-C = 341.5 (4)°]. If the doubly bonded carbonyl O atom is taken into account for the coordination sphere of Sn [Sn...O = 2.808 (2) Å], the coordination geometry can be described as a cis-pentagonal bipyramid.

Comment top

Trialkyltin carboxylates generally adopt five-coordinate, carboxylate-bridged structures (Ng et al., 1986), as exemplified by tribenzyltin acetate, which is polymeric with a short and a long Sn–O bond [2.131 (2), 2.559 (2) Å] (Ferguson et al., 1995). In the present 4-cinnamate (Scheme I), the Sn atom adopts a tetrahedral arrangment only. As noted from the sum of C–Sn–C angles at Sn, [Σ C–Sn–C 341.5 (4) °] the geometry is distorted owing to the proximity of the carbonyl O atom [Sn···O 2.808 (2) Å], but a better explanation of the lower coordination status may be attributed to crowding by the three Cl atoms.

Related literature top

Trialkyltin(IV) carboxylates generally are generally five-coordinate, carboxylate-bridged polymers; see: Ng et al. (1986). For the structure of tribenzyltin acetate, see: Ferguson et al. (1995).

Experimental top

Tri(2-chlorobenzyl)tin hydroxide was first prepared by the base hydrolysis of tri(2-chlorobenzyl)tin chloride with 10% sodium hydroxide solution. The hydroxide (0.51 g, 1 mmol) and 4-methylcinnamic acid(0.16 g, 1 mmol) were heated in ethanol (100 ml) until the reactants dissolved completely. The solution was then filtered and a white crystalline solid was obtained upon slow evaporation of the solvent.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Sn(C7H6Cl)3(C10H9O2) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Tris(2-chlorobenzyl)[3-(4-methylphenyl)prop-2-enoato-κO]tin(IV) top
Crystal data top
[Sn(C7H6Cl)3(C10H9O2)]Z = 2
Mr = 656.57F(000) = 660
Triclinic, P1Dx = 1.494 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3162 (1) ÅCell parameters from 9997 reflections
b = 11.0056 (1) Åθ = 2.2–28.3°
c = 13.7555 (2) ŵ = 1.18 mm−1
α = 78.7708 (6)°T = 100 K
β = 72.3135 (5)°Block, colorless
γ = 86.5793 (6)°0.45 × 0.35 × 0.25 mm
V = 1459.44 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer		6689 independent reflections
Radiation source: fine-focus sealed tube6056 reflections with I > 2σ(I)
graphiteRint = 0.013
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.620, Tmax = 0.758k = −14→14
14046 measured reflectionsl = −17→17
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0634P)2 + 1.0785P]
where P = (Fo2 + 2Fc2)/3
6689 reflections(Δ/σ)max = 0.001
335 parametersΔρmax = 1.36 e Å−3
0 restraintsΔρmin = −0.82 e Å−3
Crystal data top
[Sn(C7H6Cl)3(C10H9O2)]γ = 86.5793 (6)°
Mr = 656.57V = 1459.44 (3) Å3
Triclinic, P1Z = 2
a = 10.3162 (1) ÅMo Kα radiation
b = 11.0056 (1) ŵ = 1.18 mm−1
c = 13.7555 (2) ÅT = 100 K
α = 78.7708 (6)°0.45 × 0.35 × 0.25 mm
β = 72.3135 (5)°
Data collection top
Bruker SMART APEX
diffractometer		6689 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6056 reflections with I > 2σ(I)
Tmin = 0.620, Tmax = 0.758Rint = 0.013
14046 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.106Δρmax = 1.36 e Å−3
S = 0.98Δρmin = −0.82 e Å−3
6689 reflectionsAbsolute structure: ?
335 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.383309 (18)0.774804 (17)0.811076 (15)0.05269 (8)
Cl20.58120 (11)1.00795 (12)0.60420 (9)0.0934 (3)
Cl10.04588 (12)0.81930 (10)0.97866 (11)0.0949 (3)
Cl30.50987 (14)0.66211 (14)1.04853 (12)0.1139 (4)
O10.5625 (2)0.6896 (3)0.7465 (2)0.0774 (7)
O20.4393 (3)0.6160 (3)0.6664 (3)0.0927 (8)
C10.2555 (3)0.6245 (3)0.9107 (3)0.0632 (8)
H1A0.30460.54550.90110.076*
H1B0.23930.63280.98380.076*
C20.1212 (3)0.6180 (3)0.8916 (2)0.0540 (6)
C30.0931 (4)0.5256 (3)0.8458 (3)0.0753 (9)
H30.16190.46700.82370.090*
C4−0.0327 (5)0.5163 (4)0.8311 (4)0.0891 (12)
H4−0.04950.45130.79990.107*
C5−0.1332 (4)0.6008 (4)0.8614 (3)0.0832 (11)
H5−0.21910.59520.85050.100*
C6−0.1093 (3)0.6922 (3)0.9070 (3)0.0723 (9)
H6−0.17840.75060.92890.087*
C70.0171 (3)0.6997 (3)0.9215 (3)0.0585 (7)
C80.3016 (4)0.8905 (3)0.6984 (3)0.0687 (8)
H8A0.35030.87260.62870.082*
H8B0.20460.86940.71400.082*
C90.3128 (3)1.0257 (3)0.6962 (2)0.0602 (7)
C100.2005 (4)1.0943 (4)0.7405 (4)0.0845 (11)
H100.11461.05480.77260.101*
C110.2124 (6)1.2202 (4)0.7383 (4)0.1025 (15)
H110.13461.26530.76950.123*
C120.3324 (6)1.2788 (4)0.6925 (5)0.1064 (16)
H120.33821.36530.68940.128*
C130.4454 (5)1.2142 (4)0.6505 (4)0.0890 (12)
H130.53091.25460.61960.107*
C140.4341 (4)1.0893 (3)0.6535 (3)0.0642 (7)
C150.4668 (4)0.8857 (4)0.8909 (3)0.0728 (9)
H15A0.56070.85750.88740.087*
H15B0.47160.97310.85440.087*
C160.3859 (3)0.8796 (3)1.0022 (2)0.0595 (7)
C170.2901 (4)0.9715 (3)1.0334 (3)0.0714 (9)
H170.27681.03910.98260.086*
C180.2151 (4)0.9657 (4)1.1353 (4)0.0850 (11)
H180.15091.02911.15400.102*
C190.2315 (5)0.8716 (5)1.2091 (4)0.0937 (13)
H190.17970.86921.27960.112*
C200.3234 (5)0.7785 (4)1.1826 (3)0.0888 (12)
H200.33500.71171.23450.107*
C210.3985 (4)0.7830 (3)1.0797 (3)0.0681 (8)
C220.5477 (4)0.6218 (3)0.6857 (3)0.0745 (10)
C230.6762 (4)0.5491 (4)0.6446 (3)0.0814 (10)
H230.75080.55260.67090.098*
C240.6864 (4)0.4838 (4)0.5760 (3)0.0765 (9)
H240.61300.48620.54740.092*
C250.8045 (3)0.4042 (3)0.5373 (3)0.0677 (8)
C260.8045 (4)0.3506 (5)0.4566 (4)0.0935 (13)
H260.73260.36780.42610.112*
C270.9073 (5)0.2718 (6)0.4184 (5)0.1090 (18)
H270.90540.23730.36070.131*
C281.0116 (4)0.2411 (4)0.4593 (4)0.0848 (12)
C291.0152 (4)0.2971 (5)0.5390 (3)0.0881 (12)
H291.08810.27990.56840.106*
C300.9129 (4)0.3788 (4)0.5774 (3)0.0830 (11)
H300.91760.41790.63200.100*
C311.1227 (6)0.1511 (5)0.4187 (6)0.144 (3)
H31A1.08190.07880.40770.216*
H31B1.17290.12460.46940.216*
H31C1.18530.19190.35280.216*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04486 (12)0.05104 (12)0.05715 (13)−0.00428 (8)−0.01183 (8)−0.00238 (8)
Cl20.0703 (6)0.1004 (7)0.0886 (6)0.0104 (5)−0.0013 (5)−0.0074 (5)
Cl10.0817 (6)0.0811 (6)0.1307 (9)0.0014 (5)−0.0253 (6)−0.0513 (6)
Cl30.1010 (8)0.1149 (9)0.1186 (9)0.0513 (7)−0.0362 (7)−0.0146 (7)
O10.0512 (12)0.0772 (16)0.0937 (18)0.0023 (11)−0.0073 (12)−0.0152 (14)
O20.095 (2)0.0801 (18)0.107 (2)0.0082 (15)−0.0302 (17)−0.0286 (16)
C10.0472 (14)0.0567 (16)0.0752 (19)−0.0017 (12)−0.0153 (14)0.0082 (14)
C20.0491 (14)0.0467 (13)0.0571 (15)−0.0045 (11)−0.0084 (12)0.0011 (11)
C30.073 (2)0.0644 (19)0.083 (2)−0.0018 (16)−0.0114 (18)−0.0208 (17)
C40.097 (3)0.089 (3)0.088 (3)−0.024 (2)−0.026 (2)−0.026 (2)
C50.068 (2)0.093 (3)0.090 (3)−0.020 (2)−0.031 (2)−0.002 (2)
C60.0517 (16)0.0675 (19)0.091 (2)−0.0009 (14)−0.0166 (16)−0.0058 (17)
C70.0512 (15)0.0496 (14)0.0696 (18)−0.0047 (11)−0.0118 (13)−0.0075 (13)
C80.082 (2)0.0557 (16)0.077 (2)−0.0067 (15)−0.0395 (18)−0.0059 (15)
C90.0667 (18)0.0540 (15)0.0601 (16)−0.0020 (13)−0.0249 (14)−0.0006 (13)
C100.068 (2)0.078 (2)0.097 (3)0.0055 (18)−0.019 (2)−0.003 (2)
C110.108 (4)0.073 (3)0.116 (4)0.025 (3)−0.020 (3)−0.022 (2)
C120.130 (4)0.056 (2)0.123 (4)0.006 (2)−0.027 (3)−0.013 (2)
C130.099 (3)0.063 (2)0.095 (3)−0.015 (2)−0.020 (2)−0.0021 (19)
C140.0670 (18)0.0592 (17)0.0602 (17)0.0011 (14)−0.0155 (14)−0.0023 (13)
C150.071 (2)0.085 (2)0.0625 (18)−0.0279 (18)−0.0212 (16)−0.0016 (16)
C160.0558 (16)0.0635 (17)0.0624 (17)−0.0124 (13)−0.0260 (13)−0.0024 (13)
C170.074 (2)0.0535 (16)0.093 (3)−0.0059 (15)−0.0395 (19)−0.0059 (16)
C180.073 (2)0.076 (2)0.104 (3)−0.0016 (18)−0.016 (2)−0.030 (2)
C190.092 (3)0.101 (3)0.077 (2)−0.005 (2)−0.004 (2)−0.023 (2)
C200.102 (3)0.092 (3)0.062 (2)0.003 (2)−0.021 (2)0.0042 (19)
C210.0612 (18)0.073 (2)0.0683 (19)0.0097 (15)−0.0239 (15)−0.0036 (15)
C220.0569 (18)0.0645 (19)0.082 (2)0.0040 (15)−0.0003 (17)−0.0009 (17)
C230.071 (2)0.088 (3)0.086 (3)−0.0059 (19)−0.0226 (19)−0.016 (2)
C240.075 (2)0.074 (2)0.073 (2)−0.0107 (17)−0.0158 (18)−0.0010 (17)
C250.0546 (17)0.0608 (17)0.0699 (19)−0.0012 (13)0.0012 (14)−0.0012 (15)
C260.065 (2)0.124 (4)0.097 (3)0.000 (2)−0.024 (2)−0.034 (3)
C270.077 (3)0.137 (4)0.124 (4)−0.012 (3)−0.011 (3)−0.077 (4)
C280.064 (2)0.067 (2)0.104 (3)−0.0097 (16)0.011 (2)−0.026 (2)
C290.062 (2)0.108 (3)0.083 (3)0.008 (2)−0.0141 (19)−0.007 (2)
C300.081 (2)0.101 (3)0.065 (2)0.003 (2)−0.0105 (18)−0.030 (2)
C310.088 (3)0.096 (4)0.204 (7)0.008 (3)0.035 (4)−0.054 (4)
Geometric parameters (Å, °) top
Sn1—O12.050 (2)C13—H130.9500
Sn1—C82.152 (3)C15—C161.496 (5)
Sn1—C12.152 (3)C15—H15A0.9900
Sn1—C152.158 (3)C15—H15B0.9900
Cl2—C141.735 (4)C16—C211.382 (4)
Cl1—C71.741 (3)C16—C171.405 (5)
Cl3—C211.736 (4)C17—C181.372 (6)
O1—C221.270 (5)C17—H170.9500
O2—C221.234 (5)C18—C191.344 (7)
C1—C21.494 (4)C18—H180.9500
C1—H1A0.9900C19—C201.379 (6)
C1—H1B0.9900C19—H190.9500
C2—C71.375 (4)C20—C211.385 (5)
C2—C31.383 (5)C20—H200.9500
C3—C41.385 (6)C22—C231.520 (5)
C3—H30.9500C23—C241.270 (6)
C4—C51.375 (7)C23—H230.9500
C4—H40.9500C24—C251.482 (5)
C5—C61.355 (6)C24—H240.9500
C5—H50.9500C25—C261.355 (6)
C6—C71.386 (5)C25—C301.382 (6)
C6—H60.9500C26—C271.373 (7)
C8—C91.493 (4)C26—H260.9500
C8—H8A0.9900C27—C281.356 (7)
C8—H8B0.9900C27—H270.9500
C9—C141.378 (5)C28—C291.369 (7)
C9—C101.388 (5)C28—C311.515 (6)
C10—C111.392 (6)C29—C301.391 (6)
C10—H100.9500C29—H290.9500
C11—C121.345 (8)C30—H300.9500
C11—H110.9500C31—H31A0.9800
C12—C131.360 (7)C31—H31B0.9800
C12—H120.9500C31—H31C0.9800
C13—C141.378 (5)
O1—Sn1—C8113.63 (14)C16—C15—H15A108.9
O1—Sn1—C1103.75 (11)Sn1—C15—H15A108.9
C8—Sn1—C1115.95 (13)C16—C15—H15B108.9
O1—Sn1—C1596.09 (14)Sn1—C15—H15B108.9
C8—Sn1—C15110.81 (14)H15A—C15—H15B107.7
C1—Sn1—C15114.71 (14)C21—C16—C17116.3 (3)
C22—O1—Sn1111.2 (2)C21—C16—C15122.3 (3)
C2—C1—Sn1114.3 (2)C17—C16—C15121.4 (3)
C2—C1—H1A108.7C18—C17—C16121.5 (4)
Sn1—C1—H1A108.7C18—C17—H17119.3
C2—C1—H1B108.7C16—C17—H17119.3
Sn1—C1—H1B108.7C19—C18—C17120.8 (4)
H1A—C1—H1B107.6C19—C18—H18119.6
C7—C2—C3116.0 (3)C17—C18—H18119.6
C7—C2—C1122.6 (3)C18—C19—C20120.0 (4)
C3—C2—C1121.3 (3)C18—C19—H19120.0
C2—C3—C4121.8 (4)C20—C19—H19120.0
C2—C3—H3119.1C19—C20—C21119.5 (4)
C4—C3—H3119.1C19—C20—H20120.2
C5—C4—C3120.1 (4)C21—C20—H20120.2
C5—C4—H4120.0C16—C21—C20121.9 (4)
C3—C4—H4120.0C16—C21—Cl3119.8 (3)
C6—C5—C4119.7 (4)C20—C21—Cl3118.3 (3)
C6—C5—H5120.2O2—C22—O1122.3 (3)
C4—C5—H5120.2O2—C22—C23125.8 (4)
C5—C6—C7119.4 (4)O1—C22—C23111.9 (4)
C5—C6—H6120.3C24—C23—C22121.7 (4)
C7—C6—H6120.3C24—C23—H23119.1
C2—C7—C6123.1 (3)C22—C23—H23119.1
C2—C7—Cl1118.5 (2)C23—C24—C25124.7 (4)
C6—C7—Cl1118.4 (3)C23—C24—H24117.6
C9—C8—Sn1113.4 (2)C25—C24—H24117.6
C9—C8—H8A108.9C26—C25—C30117.6 (4)
Sn1—C8—H8A108.9C26—C25—C24116.8 (4)
C9—C8—H8B108.9C30—C25—C24125.6 (4)
Sn1—C8—H8B108.9C25—C26—C27120.6 (4)
H8A—C8—H8B107.7C25—C26—H26119.7
C14—C9—C10115.9 (3)C27—C26—H26119.7
C14—C9—C8122.7 (3)C28—C27—C26122.9 (4)
C10—C9—C8121.3 (3)C28—C27—H27118.5
C11—C10—C9120.8 (4)C26—C27—H27118.5
C11—C10—H10119.6C27—C28—C29117.1 (4)
C9—C10—H10119.6C27—C28—C31122.6 (5)
C12—C11—C10121.0 (4)C29—C28—C31120.2 (5)
C12—C11—H11119.5C28—C29—C30120.5 (4)
C10—C11—H11119.5C28—C29—H29119.7
C11—C12—C13120.0 (4)C30—C29—H29119.7
C11—C12—H12120.0C29—C30—C25121.1 (4)
C13—C12—H12120.0C29—C30—H30119.5
C14—C13—C12119.1 (4)C25—C30—H30119.5
C14—C13—H13120.5C28—C31—H31A109.5
C12—C13—H13120.5C28—C31—H31B109.5
C9—C14—C13123.2 (4)H31A—C31—H31B109.5
C9—C14—Cl2118.7 (3)C28—C31—H31C109.5
C13—C14—Cl2118.1 (3)H31A—C31—H31C109.5
C16—C15—Sn1113.5 (2)H31B—C31—H31C109.5
C8—Sn1—O1—C22−59.1 (3)C12—C13—C14—Cl2−177.4 (4)
C1—Sn1—O1—C2267.7 (3)O1—Sn1—C15—C16−131.5 (3)
C15—Sn1—O1—C22−175.0 (3)C8—Sn1—C15—C16110.3 (3)
O1—Sn1—C1—C2−126.3 (2)C1—Sn1—C15—C16−23.3 (3)
C8—Sn1—C1—C2−1.0 (3)Sn1—C15—C16—C2181.2 (4)
C15—Sn1—C1—C2130.2 (3)Sn1—C15—C16—C17−97.3 (3)
Sn1—C1—C2—C7−73.8 (3)C21—C16—C17—C181.0 (5)
Sn1—C1—C2—C3108.5 (3)C15—C16—C17—C18179.6 (3)
C7—C2—C3—C4−0.1 (5)C16—C17—C18—C190.2 (6)
C1—C2—C3—C4177.7 (4)C17—C18—C19—C20−0.7 (7)
C2—C3—C4—C50.6 (7)C18—C19—C20—C210.1 (8)
C3—C4—C5—C6−0.9 (7)C17—C16—C21—C20−1.6 (5)
C4—C5—C6—C70.6 (6)C15—C16—C21—C20179.8 (4)
C3—C2—C7—C6−0.2 (5)C17—C16—C21—Cl3177.8 (3)
C1—C2—C7—C6−178.0 (3)C15—C16—C21—Cl3−0.9 (5)
C3—C2—C7—Cl1−179.4 (3)C19—C20—C21—C161.1 (7)
C1—C2—C7—Cl12.8 (4)C19—C20—C21—Cl3−178.3 (4)
C5—C6—C7—C2−0.1 (6)Sn1—O1—C22—O23.4 (5)
C5—C6—C7—Cl1179.2 (3)Sn1—O1—C22—C23−174.9 (2)
O1—Sn1—C8—C9−108.4 (3)O2—C22—C23—C247.7 (7)
C1—Sn1—C8—C9131.5 (3)O1—C22—C23—C24−174.0 (4)
C15—Sn1—C8—C9−1.5 (3)C22—C23—C24—C25−175.8 (3)
Sn1—C8—C9—C1474.2 (4)C23—C24—C25—C26−173.6 (4)
Sn1—C8—C9—C10−103.9 (4)C23—C24—C25—C307.5 (6)
C14—C9—C10—C111.5 (6)C30—C25—C26—C271.5 (7)
C8—C9—C10—C11179.8 (4)C24—C25—C26—C27−177.5 (4)
C9—C10—C11—C120.6 (8)C25—C26—C27—C281.4 (8)
C10—C11—C12—C13−2.2 (9)C26—C27—C28—C29−3.1 (8)
C11—C12—C13—C141.6 (8)C26—C27—C28—C31178.2 (5)
C10—C9—C14—C13−2.2 (5)C27—C28—C29—C301.9 (7)
C8—C9—C14—C13179.6 (4)C31—C28—C29—C30−179.4 (4)
C10—C9—C14—Cl2175.9 (3)C28—C29—C30—C250.9 (7)
C8—C9—C14—Cl2−2.4 (4)C26—C25—C30—C29−2.7 (6)
C12—C13—C14—C90.7 (7)C24—C25—C30—C29176.3 (4)
Acknowledgements top

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

references
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