Bis­(chloro­acetato-κO)bis(trimethyl­silylmethyl)tin(IV)

Ding, R.-F.; Wang, Q.-B.

doi:10.1107/S1600536811028649

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1190

doi:10.1107/S1600536811028649

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Bis(chloroacetato-κO)bis(trimethylsilylmethyl)tin(IV)

Rui-Fang Ding ^a and Qi-Bao Wang ^a ^*

^aDepartment of Pharmacy, Jining Medical College, Xueyuan Road 669, Rizhao, People's Republic of China
^*Correspondence e-mail: wqb_wangqibao@163.com

(Received 12 June 2011; accepted 17 July 2011; online 2 August 2011)

In the title complex, [Sn(C₂H₂ClO₂)₂(C₄H₁₁Si)₂], the Sn^IV ion is coordinated in a distorted tetrahedral environment formed by two O atoms from two monodenate chloroacetato ligands and two C atoms from two trimethyl silyl ligands. Two further weak intramolecular Sn⋯O contacts [2.744 (2) and 2.655 (2) Å] are formed by the chloroacetato ligands.

Related literature

For a related structure, see: Parvez et al. (1997 ).

Experimental

Crystal data

[Sn(C₂H₂ClO₂)₂(C₄H₁₁Si)₂]
M_r = 480.10
Triclinic, $[P \overline 1]$
a = 10.258 (3) Å
b = 10.767 (3) Å
c = 10.808 (3) Å
α = 71.529 (2)°
β = 88.733 (3)°
γ = 74.457 (3)°
V = 1088.2 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.54 mm⁻¹
T = 293 K
0.28 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997) T_min = 0.673, T_max = 0.780
6849 measured reflections
3792 independent reflections
3311 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.089
S = 1.04
3792 reflections
197 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811028649/lh5269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028649/lh5269Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. The Sn^IV ion is coordinated in a distorted tetrahedral environment formed by two O atoms from two monodenate chloroacetato ligands and two C atoms from two trimethyl silyl ligands. There are two further weak intramolecular Sn···O contacts [2.744 (2) and 2.655 (2)Å] formed by the chloroacetato ligands. These weak contacts are also observed in a related structure (Parvez et al., 1997) but are longer in the title compound.

Related literature top

For a related structure, see: Parvez et al. (1997). AUTHOR: please resend scheme - file is corrupted

Experimental top

A mixture of bis(trimethylsilylmethyl) diphenyltin (0.447 g, 1.0 mmol) and dichloroacetic acid (0.251 g, 2.0 mmol) were gradually heated in a oil bath to 433K the temperature was maintained 20 min. After the reaction mixture had cooled to room temperature, hexane (50 ml) was added and the mixture to dissolve the solid. Cooling the filtered solution to room temperature gave colorless crystals 0.676 g suitable for X-ray analysis, yield 96.8%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are not shown.

Bis(chloroacetato-κO)bis(trimethylsilylmethyl)tin(IV) top

Crystal data top

[Sn(C₂H₂ClO₂)₂(C₄H₁₁Si)₂]	Z = 2
M_r = 480.10	F(000) = 484
Triclinic, P1	D_x = 1.465 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.258 (3) Å	Cell parameters from 4282 reflections
b = 10.767 (3) Å	θ = 2.4–26.2°
c = 10.808 (3) Å	µ = 1.54 mm⁻¹
α = 71.529 (2)°	T = 293 K
β = 88.733 (3)°	Block, colorless
γ = 74.457 (3)°	0.28 × 0.22 × 0.17 mm
V = 1088.2 (5) Å³

Data collection top

Bruker SMART CCD diffractometer	3792 independent reflections
Radiation source: fine-focus sealed tube	3311 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→12
T_min = 0.673, T_max = 0.780	k = −12→12
6849 measured reflections	l = −12→12

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0478P)² + 0.2466P] where P = (F_o² + 2F_c²)/3
3792 reflections	(Δ/σ)_max < 0.001
197 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Sn(C₂H₂ClO₂)₂(C₄H₁₁Si)₂]	γ = 74.457 (3)°
M_r = 480.10	V = 1088.2 (5) Å³
Triclinic, P1	Z = 2
a = 10.258 (3) Å	Mo Kα radiation
b = 10.767 (3) Å	µ = 1.54 mm⁻¹
c = 10.808 (3) Å	T = 293 K
α = 71.529 (2)°	0.28 × 0.22 × 0.17 mm
β = 88.733 (3)°

Data collection top

Bruker SMART CCD diffractometer	3792 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3311 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.780	R_int = 0.029
6849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	Δρ_max = 0.66 e Å⁻³
3792 reflections	Δρ_min = −0.47 e Å⁻³
197 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	−0.01272 (2)	0.16291 (2)	0.24712 (2)	0.04461 (12)
Cl1	−0.12820 (13)	0.38500 (12)	−0.28104 (11)	0.0775 (3)
Cl2	0.21959 (14)	0.16555 (14)	0.68827 (12)	0.0881 (4)
Si1	0.30636 (12)	−0.02143 (12)	0.20680 (13)	0.0655 (3)
Si2	−0.32332 (11)	0.38179 (11)	0.26896 (12)	0.0557 (3)
O1	0.0062 (3)	0.3146 (3)	0.0762 (2)	0.0587 (7)
O2	−0.1018 (3)	0.2024 (3)	−0.0036 (3)	0.0728 (8)
O3	0.0812 (3)	0.2754 (3)	0.3262 (2)	0.0551 (6)
O4	0.0642 (3)	0.1058 (3)	0.4965 (3)	0.0639 (7)
C1	−0.0506 (4)	0.2954 (4)	−0.0207 (4)	0.0553 (9)
C2	−0.0398 (5)	0.3963 (4)	−0.1488 (4)	0.0705 (12)
H2A	0.0552	0.3833	−0.1664	0.085*
H2B	−0.0745	0.4872	−0.1429	0.085*
C3	0.1012 (4)	0.2083 (4)	0.4492 (4)	0.0490 (8)
C4	0.1715 (5)	0.2691 (5)	0.5255 (4)	0.0690 (11)
H4A	0.1115	0.3560	0.5250	0.083*
H4B	0.2517	0.2865	0.4823	0.083*
C5	0.1288 (4)	−0.0193 (3)	0.2482 (4)	0.0522 (9)
H5A	0.1332	−0.0846	0.3349	0.063*
H5B	0.0918	−0.0536	0.1881	0.063*
C6	0.3067 (8)	0.0900 (10)	0.0410 (8)	0.273 (9)
H6A	0.3984	0.0795	0.0158	0.409*
H6B	0.2665	0.1829	0.0367	0.409*
H6C	0.2555	0.0668	−0.0173	0.409*
C7	0.4046 (5)	−0.1965 (5)	0.2236 (7)	0.1012 (18)
H7A	0.3617	−0.2310	0.1687	0.152*
H7B	0.4086	−0.2530	0.3130	0.152*
H7C	0.4949	−0.1971	0.1978	0.152*
C8	0.3879 (6)	0.0365 (10)	0.3186 (11)	0.214 (6)
H8A	0.4825	0.0230	0.3034	0.320*
H8B	0.3783	−0.0146	0.4073	0.320*
H8C	0.3458	0.1316	0.3039	0.320*
C9	−0.2193 (4)	0.2046 (4)	0.2868 (4)	0.0571 (9)
H9A	−0.2643	0.1716	0.2309	0.069*
H9B	−0.2242	0.1491	0.3761	0.069*
C10	−0.3256 (6)	0.4976 (5)	0.0999 (5)	0.0943 (17)
H10A	−0.3485	0.4573	0.0389	0.141*
H10B	−0.2377	0.5125	0.0842	0.141*
H10C	−0.3918	0.5831	0.0890	0.141*
C11	−0.4989 (5)	0.3740 (6)	0.3089 (7)	0.106 (2)
H11A	−0.5310	0.3297	0.2563	0.158*
H11B	−0.5572	0.4647	0.2911	0.158*
H11C	−0.4991	0.3235	0.3997	0.158*
C12	−0.2531 (6)	0.4483 (6)	0.3835 (6)	0.0938 (17)
H12A	−0.3184	0.5282	0.3900	0.141*
H12B	−0.1716	0.4711	0.3516	0.141*
H12C	−0.2329	0.3801	0.4682	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04811 (17)	0.03622 (16)	0.04990 (18)	−0.00954 (11)	0.00200 (11)	−0.01605 (11)
Cl1	0.0991 (9)	0.0731 (7)	0.0580 (6)	−0.0221 (6)	−0.0174 (6)	−0.0180 (5)
Cl2	0.1022 (9)	0.0869 (8)	0.0676 (7)	−0.0131 (7)	−0.0258 (6)	−0.0234 (6)
Si1	0.0532 (6)	0.0532 (6)	0.0860 (8)	−0.0106 (5)	0.0203 (6)	−0.0210 (6)
Si2	0.0491 (6)	0.0472 (6)	0.0674 (7)	−0.0030 (5)	−0.0021 (5)	−0.0221 (5)
O1	0.0770 (18)	0.0549 (15)	0.0437 (14)	−0.0206 (13)	0.0012 (13)	−0.0131 (12)
O2	0.099 (2)	0.0588 (18)	0.0646 (18)	−0.0337 (16)	0.0015 (16)	−0.0157 (14)
O3	0.0723 (17)	0.0488 (14)	0.0472 (15)	−0.0191 (12)	−0.0033 (12)	−0.0169 (12)
O4	0.0792 (19)	0.0548 (16)	0.0637 (17)	−0.0303 (14)	0.0067 (14)	−0.0177 (13)
C1	0.068 (2)	0.043 (2)	0.052 (2)	−0.0127 (18)	0.0034 (18)	−0.0148 (17)
C2	0.106 (3)	0.065 (3)	0.046 (2)	−0.038 (2)	−0.005 (2)	−0.0133 (19)
C3	0.049 (2)	0.0449 (19)	0.056 (2)	−0.0107 (16)	0.0041 (16)	−0.0215 (17)
C4	0.093 (3)	0.067 (3)	0.056 (2)	−0.033 (2)	−0.004 (2)	−0.022 (2)
C5	0.057 (2)	0.0384 (18)	0.059 (2)	−0.0105 (16)	0.0070 (17)	−0.0167 (16)
C6	0.148 (7)	0.238 (11)	0.212 (10)	0.066 (7)	0.128 (7)	0.121 (8)
C7	0.073 (3)	0.077 (3)	0.155 (6)	−0.008 (3)	0.024 (3)	−0.051 (4)
C8	0.067 (4)	0.272 (12)	0.420 (17)	−0.044 (5)	0.025 (7)	−0.276 (13)
C9	0.050 (2)	0.0434 (19)	0.074 (3)	−0.0112 (16)	0.0034 (18)	−0.0165 (18)
C10	0.097 (4)	0.063 (3)	0.089 (4)	0.008 (3)	−0.012 (3)	−0.004 (3)
C11	0.058 (3)	0.084 (4)	0.174 (6)	−0.010 (3)	0.024 (3)	−0.049 (4)
C12	0.095 (4)	0.094 (4)	0.106 (4)	−0.010 (3)	−0.002 (3)	−0.064 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.088 (3)	C4—H4B	0.9700
Sn1—C5	2.102 (3)	C5—H5A	0.9700
Sn1—O3	2.108 (2)	C5—H5B	0.9700
Sn1—C9	2.108 (4)	C6—H6A	0.9600
Cl1—C2	1.762 (4)	C6—H6B	0.9600
Cl2—C4	1.755 (4)	C6—H6C	0.9600
Si1—C6	1.814 (7)	C7—H7A	0.9600
Si1—C8	1.831 (7)	C7—H7B	0.9600
Si1—C7	1.837 (5)	C7—H7C	0.9600
Si1—C5	1.862 (4)	C8—H8A	0.9600
Si2—C10	1.854 (5)	C8—H8B	0.9600
Si2—C12	1.855 (5)	C8—H8C	0.9600
Si2—C11	1.860 (5)	C9—H9A	0.9700
Si2—C9	1.871 (4)	C9—H9B	0.9700
O1—C1	1.306 (5)	C10—H10A	0.9600
O2—C1	1.214 (5)	C10—H10B	0.9600
O3—C3	1.287 (4)	C10—H10C	0.9600
O4—C3	1.217 (4)	C11—H11A	0.9600
C1—C2	1.488 (5)	C11—H11B	0.9600
C2—H2A	0.9700	C11—H11C	0.9600
C2—H2B	0.9700	C12—H12A	0.9600
C3—C4	1.500 (5)	C12—H12B	0.9600
C4—H4A	0.9700	C12—H12C	0.9600

O1—Sn1—C5	107.45 (13)	H5A—C5—H5B	106.9
O1—Sn1—O3	79.95 (10)	Si1—C6—H6A	109.5
C5—Sn1—O3	109.82 (13)	Si1—C6—H6B	109.5
O1—Sn1—C9	107.52 (13)	H6A—C6—H6B	109.5
C5—Sn1—C9	131.13 (15)	Si1—C6—H6C	109.5
O3—Sn1—C9	109.00 (13)	H6A—C6—H6C	109.5
C6—Si1—C8	108.8 (6)	H6B—C6—H6C	109.5
C6—Si1—C7	110.4 (4)	Si1—C7—H7A	109.5
C8—Si1—C7	107.7 (3)	Si1—C7—H7B	109.5
C6—Si1—C5	109.7 (3)	H7A—C7—H7B	109.5
C8—Si1—C5	110.8 (3)	Si1—C7—H7C	109.5
C7—Si1—C5	109.4 (2)	H7A—C7—H7C	109.5
C10—Si2—C12	108.7 (3)	H7B—C7—H7C	109.5
C10—Si2—C11	109.7 (3)	Si1—C8—H8A	109.5
C12—Si2—C11	109.7 (3)	Si1—C8—H8B	109.5
C10—Si2—C9	111.1 (2)	H8A—C8—H8B	109.5
C12—Si2—C9	110.1 (2)	Si1—C8—H8C	109.5
C11—Si2—C9	107.5 (2)	H8A—C8—H8C	109.5
C1—O1—Sn1	107.4 (2)	H8B—C8—H8C	109.5
C3—O3—Sn1	104.6 (2)	Si2—C9—Sn1	121.39 (19)
O2—C1—O1	121.8 (4)	Si2—C9—H9A	107.0
O2—C1—C2	126.1 (4)	Sn1—C9—H9A	107.0
O1—C1—C2	112.1 (3)	Si2—C9—H9B	107.0
C1—C2—Cl1	114.0 (3)	Sn1—C9—H9B	107.0
C1—C2—H2A	108.8	H9A—C9—H9B	106.7
Cl1—C2—H2A	108.8	Si2—C10—H10A	109.5
C1—C2—H2B	108.8	Si2—C10—H10B	109.5
Cl1—C2—H2B	108.8	H10A—C10—H10B	109.5
H2A—C2—H2B	107.7	Si2—C10—H10C	109.5
O4—C3—O3	121.6 (3)	H10A—C10—H10C	109.5
O4—C3—C4	124.6 (4)	H10B—C10—H10C	109.5
O3—C3—C4	113.8 (3)	Si2—C11—H11A	109.5
C3—C4—Cl2	113.7 (3)	Si2—C11—H11B	109.5
C3—C4—H4A	108.8	H11A—C11—H11B	109.5
Cl2—C4—H4A	108.8	Si2—C11—H11C	109.5
C3—C4—H4B	108.8	H11A—C11—H11C	109.5
Cl2—C4—H4B	108.8	H11B—C11—H11C	109.5
H4A—C4—H4B	107.7	Si2—C12—H12A	109.5
Si1—C5—Sn1	120.42 (18)	Si2—C12—H12B	109.5
Si1—C5—H5A	107.2	H12A—C12—H12B	109.5
Sn1—C5—H5A	107.2	Si2—C12—H12C	109.5
Si1—C5—H5B	107.2	H12A—C12—H12C	109.5
Sn1—C5—H5B	107.2	H12B—C12—H12C	109.5

C5—Sn1—O1—C1	75.3 (3)	O3—C3—C4—Cl2	−171.7 (3)
O3—Sn1—O1—C1	−176.9 (3)	C6—Si1—C5—Sn1	−61.1 (5)
C9—Sn1—O1—C1	−70.0 (3)	C8—Si1—C5—Sn1	59.1 (5)
O1—Sn1—O3—C3	−176.4 (2)	C7—Si1—C5—Sn1	177.7 (3)
C5—Sn1—O3—C3	−71.3 (2)	O1—Sn1—C5—Si1	45.7 (2)
C9—Sn1—O3—C3	78.4 (2)	O3—Sn1—C5—Si1	−39.7 (3)
Sn1—O1—C1—O2	−0.3 (5)	C9—Sn1—C5—Si1	179.58 (19)
Sn1—O1—C1—C2	−178.5 (3)	C10—Si2—C9—Sn1	58.6 (3)
O2—C1—C2—Cl1	7.5 (6)	C12—Si2—C9—Sn1	−62.0 (3)
O1—C1—C2—Cl1	−174.5 (3)	C11—Si2—C9—Sn1	178.6 (3)
Sn1—O3—C3—O4	−2.1 (4)	O1—Sn1—C9—Si2	−42.7 (3)
Sn1—O3—C3—C4	178.5 (3)	C5—Sn1—C9—Si2	−176.64 (19)
O4—C3—C4—Cl2	9.0 (6)	O3—Sn1—C9—Si2	42.4 (3)

Experimental details

Crystal data
Chemical formula	[Sn(C₂H₂ClO₂)₂(C₄H₁₁Si)₂]
M_r	480.10
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.258 (3), 10.767 (3), 10.808 (3)
α, β, γ (°)	71.529 (2), 88.733 (3), 74.457 (3)
V (Å³)	1088.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.54
Crystal size (mm)	0.28 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.673, 0.780
No. of measured, independent and observed [I > 2σ(I)] reflections	6849, 3792, 3311
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.089, 1.04
No. of reflections	3792
No. of parameters	197
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.47

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Shandong Province Natural Science Foundation (No. ZR2010BL031).

References

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