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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m4.
Published online 2009 December 4. doi:  10.1107/S1600536809051587
PMCID: PMC2980210

catena-Poly[[trimethyltin(IV)]-μ-2-methylbenzoato-κ2 O:O′]

Abstract

The polymeric structure of the title compound, [Sn(CH3)3(C8H7O2)]n, is composed of zigzag chains in which the tin(IV) atoms, coordinated by three methyl groups, are bridged by toluene-2-carboxyl­ate ligands via their O atoms. A slightly distorted trigonal-bipyramidal SnC3O2 coordination geometry arises for the metal, with the O atoms in the axial sites. Weak C—H(...)O hydrogen bonds help to stabilize the packing.

Related literature

For biological activity of tin complexes with carboxyl­ate ligands, see, for example: Shahzadi et al. (2007 [triangle]). For a related structure, see: Danish et al. (2009 [triangle]). For a review of the structural chemistry of tin(IV) complexes with carboxyl­ate ligands, see: Tiekink (1991 [triangle]).

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Object name is e-66-000m4-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)3(C8H7O2)]
  • M r = 298.93
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-000m4-efi1.jpg
  • a = 10.618 (2) Å
  • b = 10.046 (2) Å
  • c = 12.833 (3) Å
  • β = 112.39 (3)°
  • V = 1265.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.00 mm−1
  • T = 293 K
  • 0.42 × 0.12 × 0.09 mm

Data collection

  • Kuma KM-4 four circle diffractometer
  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.838, T max = 0.892
  • 3389 measured reflections
  • 3226 independent reflections
  • 2090 reflections with I > 2σ(I)
  • R int = 0.022
  • 3 standard reflections every 200 reflections
  • intensity decay: 6.4%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.118
  • S = 1.04
  • 3226 reflections
  • 131 parameters
  • H-atom parameters constrained
  • Δρmax = 1.37 e Å−3
  • Δρmin = −1.69 e Å−3

Data collection: KM-4 Software (Kuma, 1996 [triangle]); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051587/hb5258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051587/hb5258Isup2.hkl

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

supplementary crystallographic information

Comment

The structure of the title compound (I) is built of zigzag molecular chains in which trimethyl-tin units are bridged by toluene-3-carboxylate ligand molecules via both their carboxylate O atoms (Fig.1). The toluene ring is planar [r.m.s. 0.0068 (2) Å]. The carboxylic group makes with it a dihedral angle of 77.8 (2)°. A catenated molecular pattern is formed as shown in Fig. 2. Three methyl groups and the tin ion are coplanar [r.m.s. 0.0459 (2) Å]. The metal ion is shifted from the plane by 0.0918 (2) Å. Methyl C atoms form an equatorial plane of a trigonal bipyramid with the bridging carboxylate O atoms at the apices above and below this plane. The chains are kept together by weak hydrogen bonds in which methyl C atoms act as donors and the carboxylate O atoms in the adjacent chains -as acceptors. Weak intra-chain hydrogen bonds are also observed. Geometrical parameters of hydrogen bonds are listed in Table 1.

Experimental

0.01 mol of sodium ortho-toluate was suspended in 25 ml of dry chloroform contained in a round-bottom flask under argon; 0.01 mol of trimethyl-tin chloride was then added with constant stirring. The reacting mixtured was refluxed for 4 h under argon, cooled to room temperature and kept in an ice bath for 1 h. Sodium chloride formed during the reaction was removed by filtration. The filtrate was warmed with activated charcoal for 5 minutes, filtered through silica gel and concentrated to 10 ml. Crude crystals appeared in three days. Then, they were recrystalized from 3:1 chloroform/acetone mixture to yield colourless blocks of (I).

Refinement

The H atoms attached to toluene-ring C atoms and methyl C atoms were positioned geometrically and refined with a riding model.

Figures

Fig. 1.
A structural unit of (1) with 50% probability displacement ellipsoids.
Fig. 2.
Packing diagram of the structure.

Crystal data

[Sn(CH3)3(C8H7O2)]F(000) = 592
Mr = 298.93Dx = 1.569 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.618 (2) Åθ = 6–15°
b = 10.046 (2) ŵ = 2.00 mm1
c = 12.833 (3) ÅT = 293 K
β = 112.39 (3)°Block, colourless
V = 1265.7 (4) Å30.42 × 0.12 × 0.09 mm
Z = 4

Data collection

Kuma KM-4 four circle diffractometer2090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
graphiteθmax = 30.1°, θmin = 2.1°
profile data from ω/2θ scansh = 0→13
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)k = −13→0
Tmin = 0.838, Tmax = 0.892l = −17→15
3389 measured reflections3 standard reflections every 200 reflections
3226 independent reflections intensity decay: 6.4%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0777P)2 + 0.0604P] where P = (Fo2 + 2Fc2)/3
3226 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 1.37 e Å3
0 restraintsΔρmin = −1.69 e Å3

Special details

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)

xyzUiso*/Ueq
Sn10.67213 (3)0.58902 (3)0.23186 (2)0.04378 (12)
O10.8105 (3)0.7804 (3)0.2342 (4)0.0645 (9)
C11.0203 (4)0.7136 (4)0.2204 (4)0.0443 (8)
C70.9255 (4)0.8130 (4)0.2391 (3)0.0429 (8)
C41.1974 (6)0.5271 (6)0.1924 (6)0.0803 (17)
H41.25820.46650.18260.096*
C61.0906 (6)0.6253 (6)0.3062 (5)0.0651 (13)
H61.07920.62900.37450.078*
C51.1780 (6)0.5310 (7)0.2904 (6)0.0803 (17)
H51.22300.47070.34750.096*
C21.0385 (5)0.7088 (5)0.1204 (4)0.0632 (12)
C31.1262 (7)0.6142 (7)0.1067 (6)0.0825 (19)
H31.13740.60920.03830.099*
C80.9607 (9)0.8037 (9)0.0242 (6)0.110 (3)
H8A0.86460.78850.00110.165*
H8B0.98730.7881−0.03840.165*
H8C0.98130.89400.04940.165*
O20.9682 (3)0.9314 (3)0.2610 (3)0.0527 (7)
C120.5145 (5)0.7309 (5)0.1961 (6)0.0780 (17)
H12A0.54920.80980.23990.117*
H12B0.44200.69470.21470.117*
H12C0.48040.75290.11730.117*
C130.7115 (6)0.5114 (6)0.0940 (4)0.0725 (15)
H13A0.80340.53210.10310.109*
H13B0.64950.55040.02530.109*
H13C0.69940.41660.09090.109*
C110.7997 (7)0.5631 (6)0.4027 (5)0.0814 (18)
H11A0.84690.64480.43180.122*
H11B0.86460.49400.40900.122*
H11C0.74560.53880.44500.122*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.04404 (18)0.03127 (16)0.05657 (19)0.00215 (11)0.01979 (13)−0.00013 (11)
O10.0526 (18)0.0341 (15)0.118 (3)−0.0025 (13)0.0456 (18)−0.0094 (17)
C10.0366 (18)0.0333 (18)0.063 (2)−0.0039 (15)0.0193 (17)−0.0053 (16)
C70.045 (2)0.0317 (18)0.053 (2)0.0008 (15)0.0201 (17)−0.0006 (16)
C40.057 (3)0.063 (4)0.122 (5)0.017 (3)0.036 (3)−0.016 (3)
C60.061 (3)0.059 (3)0.072 (3)0.018 (2)0.022 (2)0.006 (2)
C50.063 (3)0.062 (4)0.108 (5)0.024 (3)0.024 (3)0.009 (3)
C20.066 (3)0.059 (3)0.073 (3)0.012 (2)0.036 (3)0.006 (2)
C30.079 (4)0.088 (4)0.100 (5)0.011 (3)0.056 (4)−0.015 (4)
C80.146 (7)0.121 (6)0.083 (4)0.050 (5)0.067 (4)0.033 (4)
O20.0473 (17)0.0323 (15)0.082 (2)−0.0026 (11)0.0282 (16)−0.0035 (13)
C120.055 (3)0.043 (2)0.135 (5)0.003 (2)0.034 (3)0.017 (3)
C130.099 (4)0.063 (3)0.067 (3)−0.021 (3)0.044 (3)−0.015 (3)
C110.084 (4)0.087 (4)0.055 (3)−0.026 (3)0.006 (3)0.001 (3)

Geometric parameters (Å, °)

Sn1—C112.108 (6)C2—C31.388 (7)
Sn1—C122.112 (5)C2—C81.530 (8)
Sn1—C132.116 (5)C3—H30.9300
Sn1—O2i2.200 (3)C8—H8A0.9600
Sn1—O12.413 (3)C8—H8B0.9600
O1—C71.243 (5)C8—H8C0.9600
C1—C21.370 (7)O2—Sn1ii2.200 (3)
C1—C61.389 (7)C12—H12A0.9600
C1—C71.500 (5)C12—H12B0.9600
C7—O21.266 (5)C12—H12C0.9600
C4—C51.351 (10)C13—H13A0.9600
C4—C31.383 (10)C13—H13B0.9600
C4—H40.9300C13—H13C0.9600
C6—C51.394 (8)C11—H11A0.9600
C6—H60.9300C11—H11B0.9600
C5—H50.9300C11—H11C0.9600
C11—Sn1—C12116.8 (3)C4—C3—C2121.5 (6)
C11—Sn1—C13124.8 (3)C4—C3—H3119.3
C12—Sn1—C13117.3 (3)C2—C3—H3119.3
C11—Sn1—O2i92.6 (2)C2—C8—H8A109.5
C12—Sn1—O2i90.09 (17)C2—C8—H8B109.5
C13—Sn1—O2i97.02 (17)H8A—C8—H8B109.5
C11—Sn1—O186.5 (2)C2—C8—H8C109.5
C12—Sn1—O183.88 (17)H8A—C8—H8C109.5
C13—Sn1—O189.46 (17)H8B—C8—H8C109.5
O2i—Sn1—O1172.68 (11)C7—O2—Sn1ii119.7 (3)
C7—O1—Sn1142.4 (3)Sn1—C12—H12A109.5
C2—C1—C6119.6 (4)Sn1—C12—H12B109.5
C2—C1—C7121.0 (4)H12A—C12—H12B109.5
C6—C1—C7119.3 (4)Sn1—C12—H12C109.5
O1—C7—O2121.4 (4)H12A—C12—H12C109.5
O1—C7—C1121.5 (3)H12B—C12—H12C109.5
O2—C7—C1117.1 (4)Sn1—C13—H13A109.5
C5—C4—C3119.4 (5)Sn1—C13—H13B109.5
C5—C4—H4120.3H13A—C13—H13B109.5
C3—C4—H4120.3Sn1—C13—H13C109.5
C1—C6—C5120.4 (6)H13A—C13—H13C109.5
C1—C6—H6119.8H13B—C13—H13C109.5
C5—C6—H6119.8Sn1—C11—H11A109.5
C4—C5—C6120.1 (6)Sn1—C11—H11B109.5
C4—C5—H5120.0H11A—C11—H11B109.5
C6—C5—H5120.0Sn1—C11—H11C109.5
C1—C2—C3119.0 (5)H11A—C11—H11C109.5
C1—C2—C8120.6 (5)H11B—C11—H11C109.5
C3—C2—C8120.4 (6)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13C···O1i0.962.663.271 (7)122
C4—H4···O2iii0.932.743.502 (6)140

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (iii) −x+5/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5258).

References

  • Danish, M., Tahir, M. N., Ahmad, N., Raza, A. R. & Ibrahim, M. (2009). Acta Cryst. E65, m609–m610. [PMC free article] [PubMed]
  • Kuma (1996). KM-4 Software Kuma Diffraction Ltd. Wrocław, Poland.
  • Kuma (2001). DATAPROC Kuma Diffraction Ltd. Wrocław, Poland.
  • Oxford Diffraction (2008). CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England
  • Shahzadi, S., Shahid, K. & Ali, S. (2007). Russ. J. Coord. Chem.33, 403–411.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tiekink, E. R. T. (1991). Appl. Organomet. Chem.5, 1–23.

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