catena-Poly[[trimethyl­tin(IV)]-μ-2-phenyl­butano­ato]

Zhang, B.; Zhang, R.

doi:10.1107/S1600536810047835

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1627

https://doi.org/10.1107/S1600536810047835

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catena-Poly[[trimethyltin(IV)]-μ-2-phenylbutanoato]

Baoying 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 8 November 2010; accepted 17 November 2010; online 24 November 2010)

In the title polymeric coordination compound, [Sn(CH₃)₃(C₁₀H₁₁O₂)]_n, the Sn atom has a distorted trigonal–bipyramidal coordination geometry, with two O atoms of two symmetry-related carboxylate ligands in axial positions and three methyl groups in equatorial positions. In the crystal structure, carboxylate bridges link the metal atoms, forming zigzag chains parallel to the b axis.

Related literature

For the biological activity of organotin compounds, see: Dubey & Roy (2003 ). For a related structure, see: Ma et al. (2008 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₁₀H₁₁O₂)]
M_r = 326.98
Monoclinic, P 2₁ /c
a = 11.0872 (12) Å
b = 10.0385 (9) Å
c = 13.2736 (15) Å
β = 103.828 (1)°
V = 1434.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.77 mm⁻¹
T = 298 K
0.46 × 0.43 × 0.35 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.497, T_max = 0.577
6977 measured reflections
2512 independent reflections
2027 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.060
S = 1.14
2512 reflections
149 parameters
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.50 e Å⁻³

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/S1600536810047835/rz2525sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047835/rz2525Isup2.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 synthesized the title compound and present its crystal structure here.

The asymmetric unit of the title compound is shown in Fig. 1. An extended one-dimensional zigzag chain structure running parallel to the b axis is formed by the bridging role of the 2-phenyl-butyrate anions (Fig. 2). The Sn—O bond distances in the compound (Sn1—O1 = 2.446 (2) Å; Sn1—O2ⁱ = 2.173 (2) Å; symmetry code: (i): 1-x, 1/2+y, 1/2-z) 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 and the 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: Dubey & Roy (2003). For a related structure, see: Ma et al. (2008).

Experimental top

The reaction was carried out under a nitrogen atmosphere. 2-Phenyl-butyric acid (1 mmol) and sodium ethoxide (1 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 diethyl ether to yield colourless block-like crystals of the title compound (yield 78%). Anal. Calcd (%) for C₁₃H₂₀O₂Sn₁ (Mr = 328.05): C,47.75; H, 6.16. Found (%): C, 47.56; H, 6.29.

Structure description top

For the biological activity of organotin compounds, see: Dubey & Roy (2003). For a related structure, see: 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 50% probability displacement ellipsoids. H atoms are omitted for clarity.
	Fig. 2. Partial packing diagram of the title compound showing a polymeric chain parallel to the b axis. Hydrohen atoms are omitted for clarity.

catena-Poly[[trimethyltin(IV)]-µ-2-phenylbutanoato] top

Crystal data top

[Sn(CH₃)₃(C₁₀H₁₁O₂)]	F(000) = 656
M_r = 326.98	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3646 reflections
a = 11.0872 (12) Å	θ = 2.2–27.1°
b = 10.0385 (9) Å	µ = 1.77 mm⁻¹
c = 13.2736 (15) Å	T = 298 K
β = 103.828 (1)°	Block, colourless
V = 1434.5 (3) Å³	0.46 × 0.43 × 0.35 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2512 independent reflections
Radiation source: fine-focus sealed tube	2027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.497, T_max = 0.577	k = −11→11
6977 measured reflections	l = −15→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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0194P)² + 0.8554P] where P = (F_o² + 2F_c²)/3
2512 reflections	(Δ/σ)_max < 0.001
149 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₁₀H₁₁O₂)]	V = 1434.5 (3) Å³
M_r = 326.98	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0872 (12) Å	µ = 1.77 mm⁻¹
b = 10.0385 (9) Å	T = 298 K
c = 13.2736 (15) Å	0.46 × 0.43 × 0.35 mm
β = 103.828 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2512 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2027 reflections with I > 2σ(I)
T_min = 0.497, T_max = 0.577	R_int = 0.027
6977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 1.14	Δρ_max = 0.88 e Å⁻³
2512 reflections	Δρ_min = −0.50 e Å⁻³
149 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	0.44402 (2)	0.40204 (2)	0.201458 (18)	0.03753 (9)
O1	0.5747 (2)	0.2100 (2)	0.2682 (2)	0.0540 (7)
O2	0.6875 (2)	0.0565 (2)	0.3670 (2)	0.0491 (6)
C1	0.6678 (3)	0.1777 (3)	0.3364 (3)	0.0416 (8)
C2	0.7630 (3)	0.2802 (3)	0.3881 (3)	0.0429 (8)
H2	0.7332	0.3676	0.3597	0.052*
C3	0.8877 (3)	0.2555 (3)	0.3620 (3)	0.0398 (8)
C4	0.9310 (4)	0.3421 (4)	0.2984 (3)	0.0532 (10)
H4	0.8832	0.4157	0.2712	0.064*
C5	1.0441 (4)	0.3220 (5)	0.2740 (3)	0.0644 (12)
H5	1.0713	0.3812	0.2302	0.077*
C6	1.1157 (4)	0.2158 (4)	0.3139 (4)	0.0625 (11)
H6	1.1917	0.2023	0.2974	0.075*
C7	1.0759 (4)	0.1288 (4)	0.3784 (4)	0.0605 (11)
H7	1.1252	0.0568	0.4067	0.073*
C8	0.9617 (4)	0.1485 (4)	0.4013 (3)	0.0539 (10)
H8	0.9344	0.0882	0.4442	0.065*
C9	0.7729 (3)	0.2846 (4)	0.5052 (3)	0.0542 (10)
H9A	0.6904	0.2941	0.5171	0.065*
H9B	0.8071	0.2009	0.5358	0.065*
C10	0.8547 (4)	0.3992 (4)	0.5590 (4)	0.0714 (13)
H10A	0.9387	0.3852	0.5540	0.107*
H10B	0.8521	0.4025	0.6307	0.107*
H10C	0.8245	0.4818	0.5260	0.107*
C11	0.3315 (4)	0.2560 (4)	0.1071 (3)	0.0580 (11)
H11A	0.3437	0.1713	0.1416	0.087*
H11B	0.3542	0.2497	0.0419	0.087*
H11C	0.2457	0.2813	0.0952	0.087*
C12	0.4289 (4)	0.4269 (4)	0.3558 (3)	0.0585 (11)
H12A	0.5019	0.4708	0.3954	0.088*
H12B	0.4208	0.3413	0.3857	0.088*
H12C	0.3570	0.4800	0.3564	0.088*
C13	0.5938 (3)	0.4815 (4)	0.1461 (3)	0.0537 (10)
H13A	0.5620	0.5422	0.0902	0.081*
H13B	0.6373	0.4104	0.1218	0.081*
H13C	0.6496	0.5279	0.2014	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03457 (14)	0.03491 (14)	0.04067 (16)	0.00008 (11)	0.00416 (10)	−0.00243 (11)
O1	0.0432 (15)	0.0420 (14)	0.0667 (18)	0.0031 (12)	−0.0065 (13)	0.0054 (13)
O2	0.0419 (14)	0.0321 (13)	0.0641 (18)	−0.0046 (10)	−0.0052 (12)	0.0063 (12)
C1	0.037 (2)	0.038 (2)	0.049 (2)	0.0002 (15)	0.0094 (17)	−0.0024 (17)
C2	0.0395 (19)	0.0355 (19)	0.052 (2)	−0.0022 (15)	0.0075 (17)	0.0012 (17)
C3	0.0360 (18)	0.0355 (19)	0.044 (2)	−0.0047 (15)	0.0020 (16)	−0.0059 (16)
C4	0.050 (2)	0.049 (2)	0.060 (3)	−0.0004 (18)	0.012 (2)	0.008 (2)
C5	0.059 (3)	0.067 (3)	0.073 (3)	−0.006 (2)	0.027 (2)	0.008 (2)
C6	0.045 (2)	0.063 (3)	0.081 (3)	−0.004 (2)	0.019 (2)	−0.013 (2)
C7	0.049 (2)	0.051 (2)	0.080 (3)	0.0110 (19)	0.012 (2)	0.001 (2)
C8	0.053 (2)	0.047 (2)	0.062 (3)	0.0039 (18)	0.014 (2)	0.010 (2)
C9	0.053 (2)	0.056 (2)	0.054 (2)	0.001 (2)	0.0138 (19)	0.000 (2)
C10	0.083 (3)	0.067 (3)	0.063 (3)	−0.010 (2)	0.015 (2)	−0.022 (2)
C11	0.061 (2)	0.042 (2)	0.059 (3)	0.0054 (19)	−0.010 (2)	−0.0134 (19)
C12	0.064 (3)	0.066 (3)	0.048 (2)	−0.002 (2)	0.018 (2)	−0.002 (2)
C13	0.044 (2)	0.060 (2)	0.059 (3)	0.0031 (19)	0.017 (2)	0.010 (2)

Geometric parameters (Å, º) top

Sn1—C12	2.110 (4)	C6—H6	0.9300
Sn1—C13	2.125 (3)	C7—C8	1.385 (5)
Sn1—C11	2.128 (3)	C7—H7	0.9300
Sn1—O2ⁱ	2.173 (2)	C8—H8	0.9300
Sn1—O1	2.446 (2)	C9—C10	1.532 (5)
O1—C1	1.243 (4)	C9—H9A	0.9700
O2—C1	1.285 (4)	C9—H9B	0.9700
O2—Sn1ⁱⁱ	2.173 (2)	C10—H10A	0.9600
C1—C2	1.516 (5)	C10—H10B	0.9600
C2—C3	1.524 (5)	C10—H10C	0.9600
C2—C9	1.533 (5)	C11—H11A	0.9600
C2—H2	0.9800	C11—H11B	0.9600
C3—C4	1.376 (5)	C11—H11C	0.9600
C3—C8	1.376 (5)	C12—H12A	0.9600
C4—C5	1.384 (5)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600
C5—C6	1.359 (6)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—C7	1.368 (6)	C13—H13C	0.9600

C12—Sn1—C13	122.76 (17)	C8—C7—H7	120.2
C12—Sn1—C11	118.78 (16)	C3—C8—C7	121.4 (4)
C13—Sn1—C11	116.88 (17)	C3—C8—H8	119.3
C12—Sn1—O2ⁱ	96.92 (13)	C7—C8—H8	119.3
C13—Sn1—O2ⁱ	95.12 (12)	C10—C9—C2	112.7 (3)
C11—Sn1—O2ⁱ	90.26 (12)	C10—C9—H9A	109.1
C12—Sn1—O1	85.38 (13)	C2—C9—H9A	109.1
C13—Sn1—O1	88.69 (12)	C10—C9—H9B	109.1
C11—Sn1—O1	83.32 (12)	C2—C9—H9B	109.1
O2ⁱ—Sn1—O1	173.50 (8)	H9A—C9—H9B	107.8
C1—O1—Sn1	141.9 (2)	C9—C10—H10A	109.5
C1—O2—Sn1ⁱⁱ	119.8 (2)	C9—C10—H10B	109.5
O1—C1—O2	121.8 (3)	H10A—C10—H10B	109.5
O1—C1—C2	121.3 (3)	C9—C10—H10C	109.5
O2—C1—C2	116.9 (3)	H10A—C10—H10C	109.5
C1—C2—C3	111.0 (3)	H10B—C10—H10C	109.5
C1—C2—C9	110.6 (3)	Sn1—C11—H11A	109.5
C3—C2—C9	112.7 (3)	Sn1—C11—H11B	109.5
C1—C2—H2	107.4	H11A—C11—H11B	109.5
C3—C2—H2	107.4	Sn1—C11—H11C	109.5
C9—C2—H2	107.4	H11A—C11—H11C	109.5
C4—C3—C8	117.5 (3)	H11B—C11—H11C	109.5
C4—C3—C2	120.3 (3)	Sn1—C12—H12A	109.5
C8—C3—C2	122.1 (3)	Sn1—C12—H12B	109.5
C3—C4—C5	121.4 (4)	H12A—C12—H12B	109.5
C3—C4—H4	119.3	Sn1—C12—H12C	109.5
C5—C4—H4	119.3	H12A—C12—H12C	109.5
C6—C5—C4	120.0 (4)	H12B—C12—H12C	109.5
C6—C5—H5	120.0	Sn1—C13—H13A	109.5
C4—C5—H5	120.0	Sn1—C13—H13B	109.5
C5—C6—C7	120.0 (4)	H13A—C13—H13B	109.5
C5—C6—H6	120.0	Sn1—C13—H13C	109.5
C7—C6—H6	120.0	H13A—C13—H13C	109.5
C6—C7—C8	119.7 (4)	H13B—C13—H13C	109.5
C6—C7—H7	120.2

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)₃(C₁₀H₁₁O₂)]
M_r	326.98
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.0872 (12), 10.0385 (9), 13.2736 (15)
β (°)	103.828 (1)
V (Å³)	1434.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.77
Crystal size (mm)	0.46 × 0.43 × 0.35

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.497, 0.577
No. of measured, independent and observed [I > 2σ(I)] reflections	6977, 2512, 2027
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.060, 1.14
No. of reflections	2512
No. of parameters	149
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.50

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

Acknowledgements

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

References

Dubey, S. K. & Roy, U. (2003). Appl. Organomet. Chem. 17, 3–8. Web of Science CrossRef CAS Google Scholar
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Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar