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Acta Cryst. (2008). E64, m26    [ doi:10.1107/S1600536807061715 ]

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

H. Wang, H. Yin and D. Wang

Abstract top

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.

Comment top

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.

Related literature top

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)

Experimental top

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 top

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.

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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] 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].
[Figure 2] Fig. 2. The extended chain structure of with H atoms omitted for clarity.
catena-Poly[[trimethyltin(IV)]-µ-quinaldato] top
Crystal data top
[Sn(CH3)3(C10H6NO2)]F000 = 1328
Mr = 335.95Dx = 1.624 Mg m−3
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 mm−1
c = 15.587 (2) ÅT = 298 (2) K
V = 2748.0 (7) Å3Block, colourless
Z = 80.49 × 0.48 × 0.37 mm
Data collection top
Bruker SMART CCD
diffractometer		2439 independent reflections
Radiation source: fine-focus sealed tube2251 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 25.0º
φ 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 top
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 Å−3
2439 reflectionsΔρmin = −0.23 e Å−3
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)
Crystal data top
[Sn(CH3)3(C10H6NO2)]V = 2748.0 (7) Å3
Mr = 335.95Z = 8
Orthorhombic, C2221Mo Kα
a = 7.0487 (14) ŵ = 1.85 mm−1
b = 25.011 (2) ÅT = 298 (2) K
c = 15.587 (2) Å0.49 × 0.48 × 0.37 mm
Data collection top
Bruker SMART CCD
diffractometer		2439 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2251 reflections with I > 2σ(I)
Tmin = 0.464, Tmax = 0.548Rint = 0.035
7068 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.055Δρmax = 0.40 e Å−3
S = 1.00Δρmin = −0.23 e Å−3
2439 reflectionsAbsolute structure: Flack (1983), 1036 Friedel pairs
156 parametersFlack parameter: −0.06 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Table 1
Selected geometric parameters (Å, °) top
Sn1—C122.113 (5)Sn2—C142.100 (5)
Sn1—C112.118 (4)Sn2—C132.134 (4)
Sn1—O12.267 (2)Sn2—O22.281 (3)
C12—Sn1—C11121.36 (18)C14ii—Sn2—C14131.0 (3)
C11i—Sn1—C11117.3 (4)C14—Sn2—C13114.51 (14)
O1—Sn1—O1i175.41 (15)O2—Sn2—O2ii170.34 (14)
Symmetry codes: (i) x, −y+1, −z+1; (ii) −x+1, y, −z+1/2.
Acknowledgements top

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

references
References top

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.