catena-Poly[[chloridodimethyl­tin(IV)]-μ-chloro­acetato-κ2O:O′]

Zhang, S.; Zhang, J.; Zhang, R.

doi:10.1107/S160053681104918X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1805

https://doi.org/10.1107/S160053681104918X

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catena-Poly[[chloridodimethyltin(IV)]-μ-chloroacetato-κ²O:O′]

Shaoliang Zhang,^a Junhong Zhang ^a and Rufen Zhang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: macl@lcu.edu.cn.

(Received 10 November 2011; accepted 18 November 2011; online 23 November 2011)

In the title polymeric coordination compound, [Sn(CH₃)₂(C₂H₂ClO₂)Cl]_n, the Sn atom has a distorted trigonal–bipyramidal geometry, with two O atoms of the ligands in axial positions and two methyl groups and one Cl atom in equatorial positions. Adjacent Sn atoms are bridged by the two O atoms of the carboxylate ligand, forming a chain structure along the a-axis direction.

Related literature

For the biological activity of organotin compounds, see: Dubey & Roy (2003 ). For related structures, see: Wang et al. (2007 ); Ma et al. (2008 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₂H₂ClO₂)Cl]
M_r = 277.69
Monoclinic, P 2₁ /c
a = 6.988 (3) Å
b = 9.948 (4) Å
c = 12.686 (6) Å
β = 98.891 (5)°
V = 871.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 3.48 mm⁻¹
T = 298 K
0.39 × 0.38 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.344, T_max = 0.623
4254 measured reflections
1527 independent reflections
1145 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 1.08
1527 reflections
84 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C3	2.089 (6)
Sn1—C4	2.100 (7)
Sn1—O1	2.152 (4)
Sn1—Cl2	2.352 (2)
Sn1—O2ⁱ	2.493 (5)
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: https://doi.org/10.1107/S160053681104918X/kp2369sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104918X/kp2369Isup2.hkl

checkCIF report

Comment top

In recent years, organotin compounds have been attracting more and more attention due to their wide range of industrial applications and biological activities (Dubey & Roy, 2003). As a part of our ongoing investigations in this field, we have synthesised the title compound and present its crystal structure here. The title compound (Fig. 1) forms an extended chain arising from Sn—O bridges formed by the chloroacetic acid ligands. The Sn—O bond distances in the compound (Sn1—O1 = 2.152 (4) Å; Sn1—O2 = 2.493 (5) Å;) are comparable to those found in a related organotin carboxylate (Ma et al., 2008). The Sn atom is five-coordinate in a slightly distorted trigonal-bipyramidal coordination geometry, provided by the methyl groups and chlorine atom in the equatorial positions and the two coordinated O atoms in the axial positions (Table 1).

Related literature top

For the biological activity of organotin compounds, see: Dubey & Roy (2003). For related structures, see: Wang et al. (2007); Ma et al. (2008).

Experimental top

The reaction was carried out under a nitrogen atmosphere. Chloroacetic acid (1 mmol) and sodium ethoxide (1 mmol) were added to a solution of benzene (30 mL) in a Schlenk flask with continuous stirring for 0.5 h. Then dimethyltin dichloride (1 mmol) was 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 crystallised from a solution of diethyl ether to yield colourless blocks of the title compound (yield 78%). Anal. Calcd (%) for C₄H₈Cl₂O₂Sn₁(Mr = 277.69) :C, 17.30; H, 2.90. Found (%): C, 17.55; H, 2.62.

Structure description top

For the biological activity of organotin compounds, see: Dubey & Roy (2003). For related structures, see: Wang et al. (2007); Ma et al. (2008).

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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. A view of the polymeric structure of the title compound.

catena-Poly[[chloridodimethyltin(IV)]-µ-chloroacetato- κ²O:O'] top

Crystal data top

[Sn(CH₃)₂(C₂H₂ClO₂)Cl]	F(000) = 528
M_r = 277.69	D_x = 2.117 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1496 reflections
a = 6.988 (3) Å	θ = 3.0–25.4°
b = 9.948 (4) Å	µ = 3.48 mm⁻¹
c = 12.686 (6) Å	T = 298 K
β = 98.891 (5)°	Block, colourless
V = 871.3 (7) Å³	0.39 × 0.38 × 0.15 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	1527 independent reflections
Radiation source: fine-focus sealed tube	1145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
phi and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.344, T_max = 0.623	k = −10→11
4254 measured reflections	l = −13→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0422P)²] where P = (F_o² + 2F_c²)/3
1527 reflections	(Δ/σ)_max = 0.006
84 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₂H₂ClO₂)Cl]	V = 871.3 (7) Å³
M_r = 277.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.988 (3) Å	µ = 3.48 mm⁻¹
b = 9.948 (4) Å	T = 298 K
c = 12.686 (6) Å	0.39 × 0.38 × 0.15 mm
β = 98.891 (5)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1527 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1145 reflections with I > 2σ(I)
T_min = 0.344, T_max = 0.623	R_int = 0.057
4254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.08	Δρ_max = 0.76 e Å⁻³
1527 reflections	Δρ_min = −0.85 e Å⁻³
84 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	0.57933 (7)	0.15030 (4)	0.27295 (3)	0.0368 (2)
Cl1	0.8748 (3)	−0.36021 (16)	0.41225 (19)	0.0634 (6)
Cl2	0.8014 (3)	0.32389 (17)	0.32699 (17)	0.0570 (5)
O1	0.7885 (7)	0.0210 (4)	0.3651 (4)	0.0494 (13)
O2	0.6022 (7)	−0.1521 (4)	0.3121 (4)	0.0491 (13)
C1	0.7549 (11)	−0.1063 (6)	0.3580 (5)	0.0376 (16)
C2	0.9233 (11)	−0.1869 (6)	0.4116 (6)	0.0480 (19)
H2A	0.9576	−0.1560	0.4846	0.058*
H2B	1.0337	−0.1714	0.3753	0.058*
C3	0.6184 (11)	0.0809 (7)	0.1223 (5)	0.052 (2)
H3A	0.5372	0.0040	0.1036	0.078*
H3B	0.7515	0.0561	0.1235	0.078*
H3C	0.5844	0.1507	0.0705	0.078*
C4	0.3673 (12)	0.1411 (7)	0.3734 (6)	0.058 (2)
H4A	0.3176	0.2296	0.3823	0.087*
H4B	0.4237	0.1059	0.4416	0.087*
H4C	0.2637	0.0834	0.3421	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0406 (4)	0.0330 (3)	0.0351 (3)	−0.0031 (2)	0.0000 (2)	−0.0039 (2)
Cl1	0.0525 (14)	0.0306 (10)	0.0986 (17)	0.0054 (8)	−0.0153 (11)	0.0021 (9)
Cl2	0.0574 (14)	0.0351 (9)	0.0700 (13)	−0.0061 (8)	−0.0164 (10)	−0.0051 (9)
O1	0.056 (3)	0.028 (2)	0.056 (3)	0.007 (2)	−0.016 (2)	0.007 (2)
O2	0.041 (3)	0.039 (3)	0.060 (3)	−0.002 (2)	−0.018 (2)	−0.002 (2)
C1	0.044 (5)	0.031 (4)	0.038 (4)	−0.002 (3)	0.008 (3)	−0.004 (3)
C2	0.049 (5)	0.029 (4)	0.061 (5)	−0.004 (3)	−0.006 (4)	−0.002 (3)
C3	0.053 (5)	0.065 (5)	0.039 (4)	−0.007 (4)	0.011 (3)	−0.016 (4)
C4	0.059 (6)	0.066 (5)	0.052 (5)	0.009 (4)	0.017 (4)	0.005 (4)

Geometric parameters (Å, º) top

Sn1—C3	2.089 (6)	C1—C2	1.498 (10)
Sn1—C4	2.100 (7)	C2—H2A	0.9700
Sn1—O1	2.152 (4)	C2—H2B	0.9700
Sn1—Cl2	2.352 (2)	C3—H3A	0.9600
Sn1—O2ⁱ	2.493 (5)	C3—H3B	0.9600
Cl1—C2	1.757 (6)	C3—H3C	0.9600
O1—C1	1.289 (7)	C4—H4A	0.9600
O2—C1	1.221 (8)	C4—H4B	0.9600
O2—Sn1ⁱⁱ	2.493 (5)	C4—H4C	0.9600

C3—Sn1—C4	138.1 (3)	Cl1—C2—H2A	109.0
C3—Sn1—O1	97.2 (2)	C1—C2—H2B	109.0
C4—Sn1—O1	97.4 (3)	Cl1—C2—H2B	109.0
C3—Sn1—Cl2	109.6 (2)	H2A—C2—H2B	107.8
C4—Sn1—Cl2	110.5 (2)	Sn1—C3—H3A	109.5
O1—Sn1—Cl2	85.32 (13)	Sn1—C3—H3B	109.5
C3—Sn1—O2ⁱ	89.7 (2)	H3A—C3—H3B	109.5
C4—Sn1—O2ⁱ	86.4 (2)	Sn1—C3—H3C	109.5
O1—Sn1—O2ⁱ	164.60 (16)	H3A—C3—H3C	109.5
Cl2—Sn1—O2ⁱ	79.39 (13)	H3B—C3—H3C	109.5
C1—O1—Sn1	116.6 (5)	Sn1—C4—H4A	109.5
C1—O2—Sn1ⁱⁱ	148.1 (4)	Sn1—C4—H4B	109.5
O2—C1—O1	122.4 (7)	H4A—C4—H4B	109.5
O2—C1—C2	125.7 (6)	Sn1—C4—H4C	109.5
O1—C1—C2	111.8 (6)	H4A—C4—H4C	109.5
C1—C2—Cl1	112.9 (5)	H4B—C4—H4C	109.5
C1—C2—H2A	109.0

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)₂(C₂H₂ClO₂)Cl]
M_r	277.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.988 (3), 9.948 (4), 12.686 (6)
β (°)	98.891 (5)
V (Å³)	871.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.48
Crystal size (mm)	0.39 × 0.38 × 0.15

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.344, 0.623
No. of measured, independent and observed [I > 2σ(I)] reflections	4254, 1527, 1145
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 1.08
No. of reflections	1527
No. of parameters	84
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.85

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

Selected bond lengths (Å) top

Sn1—C3	2.089 (6)	Sn1—Cl2	2.352 (2)
Sn1—C4	2.100 (7)	Sn1—O2ⁱ	2.493 (5)
Sn1—O1	2.152 (4)

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

Acknowledgements

We thank the National Natural Science Foundation of China (20971096) for financial support.

References

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