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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m26.
Published online 2007 December 6. doi:  10.1107/S1600536807061715
PMCID: PMC2914916

catena-Poly[[trimethyl­tin(IV)]-μ-quinaldato]

Abstract

The title compound, [Sn(CH3)3(C10H6NO2)]n, forms an extended one-dimensional chain structure. There are two independent SnIV ions, both of which are in slightly distorted trigonal-bipyramidal coordination environments with two symmetry-related O atoms in the axial sites. In each case, the SnIV ion and one of the three equatorial C atoms lie on a crystallographic twofold axis.

Related literature

A series of new triorganotin(IV) pyridine­dicarboxyl­ates has been synthesized by the reaction of trimethyl­tin(IV), triphenyl­tin(IV) or tribenzyl­tin(IV) chloride with 2,6(3,5 or 2,5)-H2pdc (pdc = pyridine­dicarboxyl­ate), see: Ma et al. (2006 [triangle])

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Object name is e-64-00m26-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)3(C10H6NO2)]
  • M r = 335.95
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m26-efi2.jpg
  • a = 7.0487 (14) Å
  • b = 25.011 (2) Å
  • c = 15.587 (2) Å
  • V = 2748.0 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.85 mm−1
  • T = 298 (2) K
  • 0.49 × 0.48 × 0.37 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.464, T max = 0.548 (expected range = 0.428–0.504)
  • 7068 measured reflections
  • 2439 independent reflections
  • 2251 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.055
  • S = 1.00
  • 2439 reflections
  • 156 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.24 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1036 Friedel pairs
  • Flack parameter: −0.06 (3)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061715/lh2573sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061715/lh2573Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

supplementary crystallographic information

Comment

Organotin esters of carboxylic acids are widely used as biocides, fungicides and in industry as homogeneous catalysts. Studies on organotin complexes containing carboxylate ligands with an additional donor atom (e.g N, O or S) that is available for coordinating to an Sn atom have revealed that new structural types may lead to different activities. We have therefore synthesized the title compound, (I), and present its crystal structure here. The title compound, (Fig. 1), forms an extended one-dimensional chain structure arising from Sn—O bridges to ligands. The Sn—O distances in (I) (Table 1), are similar to those in related organotin carboxylates (Ma et al., 2006). The two independent SnIV atoms are in slightly distorted trigonal-bipyramidal coordination geometries, with the O atoms in axial positions and three C atoms of three methyl groups in equatorial positions.

Experimental

The reaction was carried out under N2 atmosphere. Quinaldic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to 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 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1).(yield 83%; m.p. 447 K). Analysis calculated (%) for C13H15NO2Sn (Mr = 335.95): C, 46.47; H, 4.50; N, 4.17. found: C, 46.39; H, 4.62; N, 4.21.

Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C) where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Figures

Fig. 1.
The molecular structure showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity [symmetry code: (A) x, -y + 1, -z + 1; (B) -x + 1, y, -z + 1/2].
Fig. 2.
The extended chain structure of with H atoms omitted for clarity.

Crystal data

[Sn(CH3)3(C10H6NO2)]F000 = 1328
Mr = 335.95Dx = 1.624 Mg m3
Orthorhombic, C2221Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2c 2Cell parameters from 5374 reflections
a = 7.0487 (14) Åθ = 2.6–28.0º
b = 25.011 (2) ŵ = 1.85 mm1
c = 15.587 (2) ÅT = 298 (2) K
V = 2748.0 (7) Å3Block, colourless
Z = 80.49 × 0.48 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer2439 independent reflections
Radiation source: fine-focus sealed tube2251 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.464, Tmax = 0.548k = −29→29
7068 measured reflectionsl = −9→18

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.021  w = 1/[σ2(Fo2) + (0.0295P)2 + 1.3697P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.055(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.40 e Å3
2439 reflectionsΔρmin = −0.23 e Å3
156 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1036 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.06 (3)

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

xyzUiso*/UeqOcc. (<1)
Sn10.85035 (5)0.50000.50000.04229 (10)
Sn20.50000.597822 (12)0.25000.04016 (10)
N10.7684 (4)0.69843 (12)0.3468 (2)0.0435 (7)
O10.8632 (4)0.58995 (10)0.48310 (17)0.0540 (7)
O20.7139 (4)0.59014 (11)0.35911 (18)0.0558 (7)
C10.7965 (6)0.61356 (14)0.4183 (2)0.0425 (9)
C20.8264 (5)0.67348 (14)0.4162 (2)0.0398 (8)
C30.9083 (5)0.69858 (14)0.4871 (3)0.0480 (9)
H30.94650.67860.53440.058*
C40.9317 (6)0.75282 (14)0.4862 (4)0.0557 (12)
H40.98580.77040.53270.067*
C50.8716 (6)0.78169 (15)0.4128 (3)0.0520 (10)
C60.7940 (6)0.75296 (15)0.3438 (3)0.0455 (9)
C70.7360 (7)0.78067 (17)0.2691 (3)0.0655 (13)
H70.68600.76200.22270.079*
C80.7539 (7)0.83512 (19)0.2655 (5)0.0775 (17)
H80.71580.85340.21650.093*
C90.8285 (9)0.86342 (19)0.3346 (4)0.0766 (16)
H90.83710.90050.33150.092*
C100.8888 (7)0.83802 (17)0.4062 (4)0.0686 (14)
H100.94160.85750.45100.082*
C111.0067 (9)0.48610 (17)0.3861 (3)0.0718 (13)
H11A1.14000.48760.39860.108*
H11B0.97560.51300.34450.108*
H11C0.97550.45140.36380.108*
C120.5506 (8)0.50000.50000.0627 (15)
H12A0.50520.49320.44300.094*0.50
H12B0.50520.53420.51910.094*0.50
H12C0.50520.47260.53800.094*0.50
C130.50000.51249 (17)0.25000.0531 (13)
H13A0.59430.49970.21060.080*0.50
H13B0.37740.49970.23280.080*0.50
H13C0.52830.49970.30660.080*0.50
C140.6981 (9)0.63265 (19)0.1663 (3)0.0655 (14)
H14A0.76750.60500.13720.098*
H14B0.78440.65450.19850.098*
H14C0.63280.65430.12490.098*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.04158 (19)0.04241 (18)0.04287 (19)0.0000.0000.00532 (19)
Sn20.0528 (2)0.03181 (16)0.03584 (17)0.0000.00173 (17)0.000
N10.0400 (17)0.0416 (16)0.0489 (18)0.0011 (14)−0.0024 (13)0.0032 (15)
O10.0703 (17)0.0394 (13)0.0524 (17)−0.0040 (12)−0.0230 (15)0.0057 (12)
O20.0699 (19)0.0420 (15)0.0554 (17)−0.0057 (14)−0.0224 (15)0.0013 (13)
C10.046 (2)0.0386 (18)0.043 (2)0.0006 (16)−0.0050 (18)0.0004 (16)
C20.037 (2)0.0371 (17)0.045 (2)0.0010 (16)−0.0021 (16)0.0000 (16)
C30.052 (2)0.0444 (19)0.048 (2)0.0020 (16)−0.0093 (19)0.0040 (19)
C40.060 (3)0.0467 (19)0.061 (3)−0.0059 (18)−0.009 (2)−0.008 (2)
C50.045 (2)0.041 (2)0.071 (3)−0.0004 (18)0.011 (2)−0.004 (2)
C60.037 (2)0.0382 (19)0.061 (3)0.0052 (16)0.0081 (19)0.0097 (18)
C70.060 (3)0.060 (2)0.076 (4)0.006 (2)−0.003 (2)0.020 (2)
C80.063 (3)0.058 (3)0.111 (5)0.009 (2)0.002 (3)0.036 (3)
C90.064 (4)0.043 (2)0.122 (5)0.001 (2)0.013 (4)0.018 (3)
C100.068 (3)0.040 (2)0.097 (4)−0.007 (2)0.015 (3)−0.008 (2)
C110.077 (3)0.067 (3)0.072 (3)0.010 (3)0.034 (3)0.012 (2)
C120.044 (3)0.079 (4)0.065 (3)0.0000.0000.018 (4)
C130.070 (4)0.036 (3)0.054 (3)0.000−0.009 (3)0.000
C140.078 (4)0.066 (3)0.052 (3)−0.008 (3)0.017 (3)0.007 (2)

Geometric parameters (Å, °)

Sn1—C122.113 (5)C5—C101.418 (6)
Sn1—C11i2.118 (4)C6—C71.415 (6)
Sn1—C112.118 (4)C7—C81.369 (6)
Sn1—O12.267 (2)C7—H70.9300
Sn1—O1i2.267 (2)C8—C91.392 (9)
Sn2—C14ii2.100 (5)C8—H80.9300
Sn2—C142.100 (5)C9—C101.352 (8)
Sn2—C132.134 (4)C9—H90.9300
Sn2—O22.281 (3)C10—H100.9300
Sn2—O2ii2.281 (3)C11—H11A0.9600
N1—C21.315 (5)C11—H11B0.9600
N1—C61.377 (5)C11—H11C0.9600
O1—C11.261 (4)C12—H12A0.9600
O2—C11.238 (5)C12—H12B0.9600
C1—C21.514 (5)C12—H12C0.9600
C2—C31.395 (5)C13—H13A0.9600
C3—C41.367 (5)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C4—C51.418 (7)C14—H14A0.9600
C4—H40.9300C14—H14B0.9600
C5—C61.404 (6)C14—H14C0.9600
C12—Sn1—C11i121.36 (18)N1—C6—C7118.4 (4)
C12—Sn1—C11121.36 (18)C5—C6—C7119.5 (4)
C11i—Sn1—C11117.3 (4)C8—C7—C6119.6 (5)
C12—Sn1—O192.29 (7)C8—C7—H7120.2
C11i—Sn1—O185.04 (13)C6—C7—H7120.2
C11—Sn1—O192.56 (14)C7—C8—C9120.6 (5)
C12—Sn1—O1i92.29 (7)C7—C8—H8119.7
C11i—Sn1—O1i92.56 (14)C9—C8—H8119.7
C11—Sn1—O1i85.04 (13)C10—C9—C8121.2 (4)
O1—Sn1—O1i175.41 (15)C10—C9—H9119.4
C14ii—Sn2—C14131.0 (3)C8—C9—H9119.4
C14ii—Sn2—C13114.51 (14)C9—C10—C5120.0 (5)
C14—Sn2—C13114.51 (14)C9—C10—H10120.0
C14ii—Sn2—O290.63 (17)C5—C10—H10120.0
C14—Sn2—O293.37 (18)Sn1—C11—H11A109.5
C13—Sn2—O285.17 (7)Sn1—C11—H11B109.5
C14ii—Sn2—O2ii93.37 (18)H11A—C11—H11B109.5
C14—Sn2—O2ii90.63 (17)Sn1—C11—H11C109.5
C13—Sn2—O2ii85.17 (7)H11A—C11—H11C109.5
O2—Sn2—O2ii170.34 (14)H11B—C11—H11C109.5
C2—N1—C6117.2 (3)Sn1—C12—H12A109.5
C1—O1—Sn1122.9 (2)Sn1—C12—H12B109.5
C1—O2—Sn2145.8 (3)H12A—C12—H12B109.5
O2—C1—O1123.4 (3)Sn1—C12—H12C109.5
O2—C1—C2121.2 (3)H12A—C12—H12C109.5
O1—C1—C2115.4 (3)H12B—C12—H12C109.5
N1—C2—C3124.5 (3)Sn2—C13—H13A109.5
N1—C2—C1116.4 (3)Sn2—C13—H13B109.5
C3—C2—C1119.1 (3)H13A—C13—H13B109.5
C4—C3—C2119.2 (4)Sn2—C13—H13C109.5
C4—C3—H3120.4H13A—C13—H13C109.5
C2—C3—H3120.4H13B—C13—H13C109.5
C3—C4—C5118.5 (4)Sn2—C14—H14A109.5
C3—C4—H4120.7Sn2—C14—H14B109.5
C5—C4—H4120.7H14A—C14—H14B109.5
C6—C5—C4118.3 (3)Sn2—C14—H14C109.5
C6—C5—C10119.1 (4)H14A—C14—H14C109.5
C4—C5—C10122.6 (4)H14B—C14—H14C109.5
N1—C6—C5122.1 (4)

Symmetry codes: (i) x, −y+1, −z+1; (ii) −x+1, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2573).

References

  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem.691, 1713–1721.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997a). SHELXL97 andSHELXS97. University of Göttingen, Germany.
  • Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography