metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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[Dubey, S. K. & Roy, U. (2003). Appl. Organomet. Chem. 17, 3-8.]). For a related structure, see: Ma et al. (2008[Ma, C., Wang, Q. & Zhang, R. (2008). Eur. J. Inorg. Chem. pp. 1926-1934.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(CH3)3(C10H11O2)]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.497, Tmax = 0.577

  • 6977 measured reflections

  • 2512 independent reflections

  • 2027 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.060

  • S = 1.14

  • 2512 reflections

  • 149 parameters

  • H-atom parameters constrained

  • Δρmax = 0.88 e Å−3

  • Δρmin = −0.50 e Å−3

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The H atoms were positioned geometrically, with methyl C—H distances of 0.96Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for the methyl groups.

Structure description 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.

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
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity.
[Figure 2] 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
Mr = 326.98Dx = 1.514 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3646 reflections
a = 11.0872 (12) Åθ = 2.2–27.1°
b = 10.0385 (9) ŵ = 1.77 mm1
c = 13.2736 (15) ÅT = 298 K
β = 103.828 (1)°Block, colourless
V = 1434.5 (3) Å30.46 × 0.43 × 0.35 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
2512 independent reflections
Radiation source: fine-focus sealed tube2027 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
phi and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1310
Tmin = 0.497, Tmax = 0.577k = 1111
6977 measured reflectionsl = 1515
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0194P)2 + 0.8554P]
where P = (Fo2 + 2Fc2)/3
2512 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.88 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
[Sn(CH3)3(C10H11O2)]V = 1434.5 (3) Å3
Mr = 326.98Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.0872 (12) ŵ = 1.77 mm1
b = 10.0385 (9) ÅT = 298 K
c = 13.2736 (15) Å0.46 × 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)
Tmin = 0.497, Tmax = 0.577Rint = 0.027
6977 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.14Δρmax = 0.88 e Å3
2512 reflectionsΔρmin = 0.50 e Å3
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
xyzUiso*/Ueq
Sn10.44402 (2)0.40204 (2)0.201458 (18)0.03753 (9)
O10.5747 (2)0.2100 (2)0.2682 (2)0.0540 (7)
O20.6875 (2)0.0565 (2)0.3670 (2)0.0491 (6)
C10.6678 (3)0.1777 (3)0.3364 (3)0.0416 (8)
C20.7630 (3)0.2802 (3)0.3881 (3)0.0429 (8)
H20.73320.36760.35970.052*
C30.8877 (3)0.2555 (3)0.3620 (3)0.0398 (8)
C40.9310 (4)0.3421 (4)0.2984 (3)0.0532 (10)
H40.88320.41570.27120.064*
C51.0441 (4)0.3220 (5)0.2740 (3)0.0644 (12)
H51.07130.38120.23020.077*
C61.1157 (4)0.2158 (4)0.3139 (4)0.0625 (11)
H61.19170.20230.29740.075*
C71.0759 (4)0.1288 (4)0.3784 (4)0.0605 (11)
H71.12520.05680.40670.073*
C80.9617 (4)0.1485 (4)0.4013 (3)0.0539 (10)
H80.93440.08820.44420.065*
C90.7729 (3)0.2846 (4)0.5052 (3)0.0542 (10)
H9A0.69040.29410.51710.065*
H9B0.80710.20090.53580.065*
C100.8547 (4)0.3992 (4)0.5590 (4)0.0714 (13)
H10A0.93870.38520.55400.107*
H10B0.85210.40250.63070.107*
H10C0.82450.48180.52600.107*
C110.3315 (4)0.2560 (4)0.1071 (3)0.0580 (11)
H11A0.34370.17130.14160.087*
H11B0.35420.24970.04190.087*
H11C0.24570.28130.09520.087*
C120.4289 (4)0.4269 (4)0.3558 (3)0.0585 (11)
H12A0.50190.47080.39540.088*
H12B0.42080.34130.38570.088*
H12C0.35700.48000.35640.088*
C130.5938 (3)0.4815 (4)0.1461 (3)0.0537 (10)
H13A0.56200.54220.09020.081*
H13B0.63730.41040.12180.081*
H13C0.64960.52790.20140.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03457 (14)0.03491 (14)0.04067 (16)0.00008 (11)0.00416 (10)0.00243 (11)
O10.0432 (15)0.0420 (14)0.0667 (18)0.0031 (12)0.0065 (13)0.0054 (13)
O20.0419 (14)0.0321 (13)0.0641 (18)0.0046 (10)0.0052 (12)0.0063 (12)
C10.037 (2)0.038 (2)0.049 (2)0.0002 (15)0.0094 (17)0.0024 (17)
C20.0395 (19)0.0355 (19)0.052 (2)0.0022 (15)0.0075 (17)0.0012 (17)
C30.0360 (18)0.0355 (19)0.044 (2)0.0047 (15)0.0020 (16)0.0059 (16)
C40.050 (2)0.049 (2)0.060 (3)0.0004 (18)0.012 (2)0.008 (2)
C50.059 (3)0.067 (3)0.073 (3)0.006 (2)0.027 (2)0.008 (2)
C60.045 (2)0.063 (3)0.081 (3)0.004 (2)0.019 (2)0.013 (2)
C70.049 (2)0.051 (2)0.080 (3)0.0110 (19)0.012 (2)0.001 (2)
C80.053 (2)0.047 (2)0.062 (3)0.0039 (18)0.014 (2)0.010 (2)
C90.053 (2)0.056 (2)0.054 (2)0.001 (2)0.0138 (19)0.000 (2)
C100.083 (3)0.067 (3)0.063 (3)0.010 (2)0.015 (2)0.022 (2)
C110.061 (2)0.042 (2)0.059 (3)0.0054 (19)0.010 (2)0.0134 (19)
C120.064 (3)0.066 (3)0.048 (2)0.002 (2)0.018 (2)0.002 (2)
C130.044 (2)0.060 (2)0.059 (3)0.0031 (19)0.017 (2)0.010 (2)
Geometric parameters (Å, º) top
Sn1—C122.110 (4)C6—H60.9300
Sn1—C132.125 (3)C7—C81.385 (5)
Sn1—C112.128 (3)C7—H70.9300
Sn1—O2i2.173 (2)C8—H80.9300
Sn1—O12.446 (2)C9—C101.532 (5)
O1—C11.243 (4)C9—H9A0.9700
O2—C11.285 (4)C9—H9B0.9700
O2—Sn1ii2.173 (2)C10—H10A0.9600
C1—C21.516 (5)C10—H10B0.9600
C2—C31.524 (5)C10—H10C0.9600
C2—C91.533 (5)C11—H11A0.9600
C2—H20.9800C11—H11B0.9600
C3—C41.376 (5)C11—H11C0.9600
C3—C81.376 (5)C12—H12A0.9600
C4—C51.384 (5)C12—H12B0.9600
C4—H40.9300C12—H12C0.9600
C5—C61.359 (6)C13—H13A0.9600
C5—H50.9300C13—H13B0.9600
C6—C71.368 (6)C13—H13C0.9600
C12—Sn1—C13122.76 (17)C8—C7—H7120.2
C12—Sn1—C11118.78 (16)C3—C8—C7121.4 (4)
C13—Sn1—C11116.88 (17)C3—C8—H8119.3
C12—Sn1—O2i96.92 (13)C7—C8—H8119.3
C13—Sn1—O2i95.12 (12)C10—C9—C2112.7 (3)
C11—Sn1—O2i90.26 (12)C10—C9—H9A109.1
C12—Sn1—O185.38 (13)C2—C9—H9A109.1
C13—Sn1—O188.69 (12)C10—C9—H9B109.1
C11—Sn1—O183.32 (12)C2—C9—H9B109.1
O2i—Sn1—O1173.50 (8)H9A—C9—H9B107.8
C1—O1—Sn1141.9 (2)C9—C10—H10A109.5
C1—O2—Sn1ii119.8 (2)C9—C10—H10B109.5
O1—C1—O2121.8 (3)H10A—C10—H10B109.5
O1—C1—C2121.3 (3)C9—C10—H10C109.5
O2—C1—C2116.9 (3)H10A—C10—H10C109.5
C1—C2—C3111.0 (3)H10B—C10—H10C109.5
C1—C2—C9110.6 (3)Sn1—C11—H11A109.5
C3—C2—C9112.7 (3)Sn1—C11—H11B109.5
C1—C2—H2107.4H11A—C11—H11B109.5
C3—C2—H2107.4Sn1—C11—H11C109.5
C9—C2—H2107.4H11A—C11—H11C109.5
C4—C3—C8117.5 (3)H11B—C11—H11C109.5
C4—C3—C2120.3 (3)Sn1—C12—H12A109.5
C8—C3—C2122.1 (3)Sn1—C12—H12B109.5
C3—C4—C5121.4 (4)H12A—C12—H12B109.5
C3—C4—H4119.3Sn1—C12—H12C109.5
C5—C4—H4119.3H12A—C12—H12C109.5
C6—C5—C4120.0 (4)H12B—C12—H12C109.5
C6—C5—H5120.0Sn1—C13—H13A109.5
C4—C5—H5120.0Sn1—C13—H13B109.5
C5—C6—C7120.0 (4)H13A—C13—H13B109.5
C5—C6—H6120.0Sn1—C13—H13C109.5
C7—C6—H6120.0H13A—C13—H13C109.5
C6—C7—C8119.7 (4)H13B—C13—H13C109.5
C6—C7—H7120.2
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Sn(CH3)3(C10H11O2)]
Mr326.98
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.0872 (12), 10.0385 (9), 13.2736 (15)
β (°) 103.828 (1)
V3)1434.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.77
Crystal size (mm)0.46 × 0.43 × 0.35
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.497, 0.577
No. of measured, independent and
observed [I > 2σ(I)] reflections
6977, 2512, 2027
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.060, 1.14
No. of reflections2512
No. of parameters149
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationDubey, S. K. & Roy, U. (2003). Appl. Organomet. Chem. 17, 3–8.  Web of Science CrossRef CAS Google Scholar
First citationMa, C., Wang, Q. & Zhang, R. (2008). Eur. J. Inorg. Chem. pp. 1926–1934.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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