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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 1| January 2013| Page m4
https://doi.org/10.1107/S160053681204888X

Hexa-μ2-acetato-hexa-n-butyl­hexa-μ3-oxido-tin(IV) toluene monosolvate

Martin Reichelta and Hans Reutera*

aInstitut für Chemie neuer Materialien, Anorganische Chemie II, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany
*Correspondence e-mail: hreuter@uni-osnabrueck.de

(Received 16 November 2012; accepted 28 November 2012; online 5 December 2012)

The title compound, [Sn6(C4H9)6(CH3COO)6O6]·C7H8, has one half-toluene mol­ecule and one half-organotin mol­ecule in the asymmetric unit. The latter is situated about an inversion centre and belongs to the class of hexa­meric monoorganooxo­tin carboxyl­ates with a hexa­gonal prismatic or `drum-like' motif of the central tin–oxygen core. Two Sn3O3 rings in a flat-chair conformation are linked via six Sn—O bonds and six bridging acetate groups. All Sn atoms have approximate octa­hedral coordination geometry. The Sn—O bonds which are trans to the alkyl group are significantly shorter than the others. One butyl group is disordered over two different sites, with occupancies of 0.9:0.1. Very large atomic displacement parameters of the toluene mol­ecule indicate an unresolvable disorder about the twofold axis.

Related literature

For an overview of the synthesis of organotin carboxyl­ates, see: Mehrotra & Bohra (1983[Mehrotra, R. C. & Bohra, R. (1983). In Metal Carboxylates. London, New York: Academic Press.]). For an overview on compositions and structure types of organotin carboxyl­ates, see: Tiekink (1991[Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.]). For structural details on hexa­meric, `drum-like' monoorganooxotin acetates, see: Day et al. (1988[Day, R. O., Chandrasekhar, V., Kumara Swamy, K. C., Burton, S. D. & Holmes, R. R. (1988). Inorg. Chem. 27, 2887-2893.]); Kuan et al. (2002[Kuan, F. S., Dakternieks, D. & Tiekink, E. R. T. (2002). Acta Cryst. E58, m301-m303.]); Beckmann et al. (2004[Beckmann, J., Dakternieks, D., Duthie, A., Thompson, L. & Tiekink, E. R. T. (2004). Acta Cryst. E60, m767-m768.]). For `ladder-type' monoorganooxotin carboxyl­ates, see: Day et al. (1988[Day, R. O., Chandrasekhar, V., Kumara Swamy, K. C., Burton, S. D. & Holmes, R. R. (1988). Inorg. Chem. 27, 2887-2893.]). For the static trans strengthening in alkyltin(IV) halides, see: Buslaev et al. (1989[Buslaev, Y. A., Kravchenko, E. A., Burtzev, M. Y. & Aslanov, L. A. (1989). Coord. Chem. Rev. 93, 185-204.]); Reuter & Puff (1992[Reuter, H. & Puff, H. (1992). J. Organomet. Chem. 424, 23-31.]).

[Scheme 1]

Experimental

Crystal data

  • [Sn6(C4H9)6(C2H3O2)6O6]·C7H8

  • Mr = 1597.21

  • Monoclinic, C 2/c

  • a = 23.4154 (8) Å

  • b = 15.5832 (6) Å

  • c = 16.1012 (6) Å

  • β = 93.926 (2)°

  • V = 5861.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.58 mm−1

  • T = 150 K

  • 0.30 × 0.22 × 0.10 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2 (including SAINT) and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.509, Tmax = 0.783

  • 76854 measured reflections

  • 6788 independent reflections

  • 5890 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.020

  • wR(F2) = 0.046

  • S = 1.05

  • 6788 reflections

  • 325 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Selected torsion angles (°)

Sn2—O2—Sn3—O1i −25.88 (11)
O2—Sn3—O1i—Sn1i 24.87 (11)
Sn3—O1i—Sn1i—O3i −24.64 (11)
O1i—Sn1i—O3i—Sn2 24.53 (11)
Sn1i—O3i—Sn2—O2 −24.89 (11)
O3i—Sn2—O2—Sn3 25.96 (11)
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 (including SAINT) and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 (including SAINT) and SADABS. Bruker AXS 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681204888X/fj2609sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681204888X/fj2609Isup2.hkl

checkCIF report


Comment top

The synthesis of organotin(IV) carboxylates is well established since a long time (Mehrotra & Bohra, 1983) and many of their crystal structures have been investigated into detail (Tiekink, 1991). Thus, in the case of triorganotin moieties R3Sn the corresponding carboxylates are of general formula R3Sn(O2CR') with (O2CR') representing the carboxylate ion. Diorganotin oxides, R2SnO, most often insoluble in indifferent organic solvents, can be easily dissolved in a large number of carboxylic acids, R'COOH, giving rise to the formation of carboxylates with a lot of different compositions and a tremendous diversity of molecular structures. Applying the same conditions to monoorganotin sesquioxides, RSnO1,5, also insoluble in non-complexing organic solvents results in the formation of monoorganooxotin carboxylates with "ladder"-type structures of composition (RSn)6O4(O2CR')10 (Day et al.,1988) or, more frequently, to hexanuclear compounds [RSnO(O2CR')]6. In the latter case, the structure is dominated by a hexagonal prismatic or "drum"-like arrangement of the tin-oxygen core as was demonstrated in the case of acetates (R' = CH3) for R = iPr (Kuan et al., 2002), R = tmsm (Beckmann et al., 2004), and R = Me (Day et al.,1988). By dissolving n-butylstannonic acid of idealized formula nBuSnO(OH) in a mixture of toluene/acetic acid and removing the resulting water by use of a Dean-Stark apparatus we were able to obtain single crystals of the corresponding R = n-butyl hexamer as the 1:1 toluene solvate, [nBuSnO(OAc)]6 x C7H8.

The asymmetric unit of the title compound consists of a centrosymmetric hexamer (Fig. 1) with i at (1/4,3/4,0) and a toluene molecule of site symmetry 2. As usual for the constitution (Fig. 2) of the drum, the six-membered tin-oxygen rings forming the bases are not planar but adopt a flat chair-conformation with the torsion angles listed in Tab. 1. Both rings are rotated through 60° against each other so that each oxygen atom bonds to a tin atom of the adjacent ring. The six sides of the drum consist of tin oxygen trapezoids with small angles at tin [77.88 (6)° - 78.34 (6)°, mean value 78.0 (2)°] and larger ones at oxygen [99.79 (6)° - 100.55 (6)°, mean value 100.1 (3)°]. These four-membered rings are also non-planar but bent [18.19 (5)°-18.99 (4)°] along the O···O diagonals that are 2.625 (2) - 2.636 (2) Å long in contrast to the Sn··· Sn diagonals that are much more longer [3.1980 (2) - 3.2041 (2) Å]. Both tin atoms of these six four-membered tin oxygen rings are bridged by acetate groups with carbon oxygen distances that are almost equal [1.256 (3) - 1.267 (3) Å, mean value 1.263 (5) Å] indicating their symmetrical coordination mode (Fig. 3).

In summary, all tin atoms are octahedrally coordinated by the n-butyl ligand, three oxygen atoms of the drum and two oxygen atoms of two different acetate groups (Fig. 2). The distortions of the octahedra can be described by carbon-tin-oxygen axes that are slightly bent [175.48 (7)° - 177.18 (8)°], and bond angles of the organic groups to their cis-oriented neighboring oxygen atoms that are considerably widened [91.90 (7)° - 100.53 (8)°].

While the tin-carbon bonds are very similar [2.125 (2) to 2.129 (2) Å, mean value: 2.128 (2) Å] tin-oxygen bond lengths fall into two clearly different groups. The longer ones [2.162 (2) - 2.172 (2) Å, mean value: 2.167 (5) Å] are those to the bridging acetate groups. The narrow range is in correspondence with the narrow range of carbon oxygen bonds, described above, indicating a symmetrical bonding of the acetate groups. The shorter ones [2.080 (2) - 2.097 (2) Å] arise from the µ3-oxygen atoms within the drum. They can be subdivided into those that are trans to the organic ligand and significantly shorter [2.080 (2) - 2.085 (2) Å, mean value: 2.083 (3) Å] and those that are somewhat longer arising from the corresponding cis-oriented oxygen atoms [2.0882 (2) - 2.0969 (2) Å, mean value: 2.092 (4) Å]. This strengthening although less marked is similar to the static trans-strengthening observed in the case of alkyl tin halides (Buslaev et al., 1989), Reuter & Puff, 1992).

Intermolecular interactions of the cylindrical hexamers are limited to van-der-Waals ones because the accessibility of the polar tin-oxygen core is restricted (Fig. 4). As a result of these weak interactions, molecules are arranged in planar hexagonal nets (Fig. 5a) with two different orientations of the drum (Fig. 5b). Between these nets large apolar channels with large cavities exist (Fig. 6a) which partially are fulfilled by the solvent molecules (Fig. 6b).

Related literature top

For an overview on the synthesis of organotin carboxylates, see: Mehrotra & Bohra (1983). For an overview on compositions and structure types of organotin carboxylates, see: Tiekink (1991). For structural details on hexameric, "drum"-like monoorganooxotin acetates, see: Day et al. (1988), Kuan et al. (2002), Beckmann et al. (2004). For "ladder" type monoorganooxotin carboxylates, see: Day et al. (1988). For the static trans strengthening in alkyl tin(IV) halides, see: Buslaev et al. (1989); Reuter & Puff (1992).

Experimental top

1.24 g (6 mmol) n-butylstannonic acid (Gelest, Inc.) and 0.36 g (6 mmol) glacial acetic acid (Fluka) were dissolved in 120 ml toluene. The mixture was heated under reflux for 6 h. The water formed in the reaction was removed by a Dean-Stark apparatus. The reaction mixture was filtered and the solvent evaporated overnight at room temperature. After evaporation colourless block shaped crystals was obtained.

1H-NMR (Bruker AVANCE DPX, 250 MHz, CDCl3) δ [p.p.m.]: 0.91 (t, 3H, CH3); 1.57–1.75 (m, 2H); 1.18–1.55 (m, 4H); 2.09 (s, 3H, CH3COO).

{1H}-13C-NMR (Bruker AVANCE DPX, 250 MHz, CDCl3) δ [p.p.m.], nJ(13C-119/117Sn) [Hz]: 26.74 (α-CH2, n = 1, 1191.9/1139.0); 27.02 (β-CH2, n = 2, 57.4); 26.48 (γ-CH2, n = 3, 195.9/187.6); 13.48 (CH3, n = 4, 14.8); 24.22 (CH3—COO); 179.64 (CH3—COO, n = 2, 30.3).

A suitable single-crystal was selected under a polarization microsope and mounted on a 50 µm MicroMesh MiTeGen MicromountTM using FROMBLIN Y perfluoropolyether (LVAC 16/6, Aldrich).

Refinement top

The n-butyl group at Sn3 is statistically disordered resulting in two different conformations with occupancies 0.9/0.1. In order to get a reliable structure model carbon-carbon bonds of the minor part were restraint to a common refined value of 1.516(x) Å and their anisotropic displacement parameters fit to those of the corresponding carbon atoms of the major part. Although the hydrogen atoms of the non-disordered carbon atoms could clearly identified in difference Fourier synthesis, all were idealized and refined at calculated positions riding on the carbon atoms with C—H distances of 0.98 Å (–CH3), 0.98 (–CH2–) and 0.95 Å (Haromatic). Carbon atoms of the solvent molecule show high anisotropic displacement parameters as a result of high thermal motion or more probably as a result of its statistic disorder about the twofold axis giving rise to unusual bond lengths and angles.

Structure description top

The synthesis of organotin(IV) carboxylates is well established since a long time (Mehrotra & Bohra, 1983) and many of their crystal structures have been investigated into detail (Tiekink, 1991). Thus, in the case of triorganotin moieties R3Sn the corresponding carboxylates are of general formula R3Sn(O2CR') with (O2CR') representing the carboxylate ion. Diorganotin oxides, R2SnO, most often insoluble in indifferent organic solvents, can be easily dissolved in a large number of carboxylic acids, R'COOH, giving rise to the formation of carboxylates with a lot of different compositions and a tremendous diversity of molecular structures. Applying the same conditions to monoorganotin sesquioxides, RSnO1,5, also insoluble in non-complexing organic solvents results in the formation of monoorganooxotin carboxylates with "ladder"-type structures of composition (RSn)6O4(O2CR')10 (Day et al.,1988) or, more frequently, to hexanuclear compounds [RSnO(O2CR')]6. In the latter case, the structure is dominated by a hexagonal prismatic or "drum"-like arrangement of the tin-oxygen core as was demonstrated in the case of acetates (R' = CH3) for R = iPr (Kuan et al., 2002), R = tmsm (Beckmann et al., 2004), and R = Me (Day et al.,1988). By dissolving n-butylstannonic acid of idealized formula nBuSnO(OH) in a mixture of toluene/acetic acid and removing the resulting water by use of a Dean-Stark apparatus we were able to obtain single crystals of the corresponding R = n-butyl hexamer as the 1:1 toluene solvate, [nBuSnO(OAc)]6 x C7H8.

The asymmetric unit of the title compound consists of a centrosymmetric hexamer (Fig. 1) with i at (1/4,3/4,0) and a toluene molecule of site symmetry 2. As usual for the constitution (Fig. 2) of the drum, the six-membered tin-oxygen rings forming the bases are not planar but adopt a flat chair-conformation with the torsion angles listed in Tab. 1. Both rings are rotated through 60° against each other so that each oxygen atom bonds to a tin atom of the adjacent ring. The six sides of the drum consist of tin oxygen trapezoids with small angles at tin [77.88 (6)° - 78.34 (6)°, mean value 78.0 (2)°] and larger ones at oxygen [99.79 (6)° - 100.55 (6)°, mean value 100.1 (3)°]. These four-membered rings are also non-planar but bent [18.19 (5)°-18.99 (4)°] along the O···O diagonals that are 2.625 (2) - 2.636 (2) Å long in contrast to the Sn··· Sn diagonals that are much more longer [3.1980 (2) - 3.2041 (2) Å]. Both tin atoms of these six four-membered tin oxygen rings are bridged by acetate groups with carbon oxygen distances that are almost equal [1.256 (3) - 1.267 (3) Å, mean value 1.263 (5) Å] indicating their symmetrical coordination mode (Fig. 3).

In summary, all tin atoms are octahedrally coordinated by the n-butyl ligand, three oxygen atoms of the drum and two oxygen atoms of two different acetate groups (Fig. 2). The distortions of the octahedra can be described by carbon-tin-oxygen axes that are slightly bent [175.48 (7)° - 177.18 (8)°], and bond angles of the organic groups to their cis-oriented neighboring oxygen atoms that are considerably widened [91.90 (7)° - 100.53 (8)°].

While the tin-carbon bonds are very similar [2.125 (2) to 2.129 (2) Å, mean value: 2.128 (2) Å] tin-oxygen bond lengths fall into two clearly different groups. The longer ones [2.162 (2) - 2.172 (2) Å, mean value: 2.167 (5) Å] are those to the bridging acetate groups. The narrow range is in correspondence with the narrow range of carbon oxygen bonds, described above, indicating a symmetrical bonding of the acetate groups. The shorter ones [2.080 (2) - 2.097 (2) Å] arise from the µ3-oxygen atoms within the drum. They can be subdivided into those that are trans to the organic ligand and significantly shorter [2.080 (2) - 2.085 (2) Å, mean value: 2.083 (3) Å] and those that are somewhat longer arising from the corresponding cis-oriented oxygen atoms [2.0882 (2) - 2.0969 (2) Å, mean value: 2.092 (4) Å]. This strengthening although less marked is similar to the static trans-strengthening observed in the case of alkyl tin halides (Buslaev et al., 1989), Reuter & Puff, 1992).

Intermolecular interactions of the cylindrical hexamers are limited to van-der-Waals ones because the accessibility of the polar tin-oxygen core is restricted (Fig. 4). As a result of these weak interactions, molecules are arranged in planar hexagonal nets (Fig. 5a) with two different orientations of the drum (Fig. 5b). Between these nets large apolar channels with large cavities exist (Fig. 6a) which partially are fulfilled by the solvent molecules (Fig. 6b).

For an overview on the synthesis of organotin carboxylates, see: Mehrotra & Bohra (1983). For an overview on compositions and structure types of organotin carboxylates, see: Tiekink (1991). For structural details on hexameric, "drum"-like monoorganooxotin acetates, see: Day et al. (1988), Kuan et al. (2002), Beckmann et al. (2004). For "ladder" type monoorganooxotin carboxylates, see: Day et al. (1988). For the static trans strengthening in alkyl tin(IV) halides, see: Buslaev et al. (1989); Reuter & Puff (1992).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Ball-and-stick model of title compound with the atomic numbering scheme used; with exception of the hydrogen atoms, which are shown as spheres with common isotropic radius, all other atoms are represented as thermal displacement ellipsoids showing the 50% probability level of the corresponding atom; the statistically disordered n-butyl group of Sn3 is shown in case the major (90%) one at Sn3 and in case of the minor one (10%) at Sn3i; symmetry code: (i) -x + 1/2, -y + 3/2, -z.
[Figure 2] Fig. 2. Ball-and-stick model of the central, drum-like tin-oxygen core of the title compound showing the flat chair-like conformation of the six-membered tin-oxygen rings of the as well as the non-planarity of the tin-oxygen trapezoids; with exception of the hydrogen atoms, which are shown as spheres with common isotropic radius, all other atoms are represented as thermal displacement ellipsoids showing the 50% probability level of the corresponding atom; in cases of the octahedrally coordinated the additional bonds are drawn as shortened sticks to visualize their orientation.
[Figure 3] Fig. 3. Ball-and-stick model of the octahedral coordination sphere of Sn1; with exception of the hydrogen atoms, which are shown as spheres with common isotropic radius, all other atoms are represented as thermal displacement ellipsoids showing the 50% probability level of the corresponding atom; in cases (nBu, µ3-O, O2CCH3) that atoms form additional bonds these are drawn as shortened sticks to show the orientation.
[Figure 4] Fig. 4. Space-filling model of the title compound showing the cylindrical shape of the molecule with the belt of acetate groups surrounding the central tin-oxygen framework and its coverage through the n-butyl groups.
[Figure 5] Fig. 5. Detail of the three-dimensional arrangement of the hexameric molecules, showing the sheets (top view above, side view below) formed by van-der Waals interaction.
[Figure 6] Fig. 6. Detail of the three-dimensional arrangement of the hexameric molecules, showing the stacking of the sheets and the open space between them (above, a) and its filling by the toluene molecules (below, b).
Hexa-µ2-acetato-hexa-n-butylhexa-µ3-oxido-tin(IV) toluene monosolvate top
Crystal data top
[Sn6(C4H9)6(C2H3O2)6O6]·C7H8F(000) = 3128
Mr = 1597.21Dx = 1.810 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9091 reflections
a = 23.4154 (8) Åθ = 2.6–30.0°
b = 15.5832 (6) ŵ = 2.58 mm−1
c = 16.1012 (6) ÅT = 150 K
β = 93.926 (2)°Block, colourless
V = 5861.3 (4) Å30.30 × 0.22 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		6788 independent reflections
Radiation source: fine-focus sealed tube5890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −30→28
Tmin = 0.509, Tmax = 0.783k = −20→19
76854 measured reflectionsl = −20→21
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)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0188P)2 + 9.9195P]
where P = (Fo2 + 2Fc2)/3
6788 reflections(Δ/σ)max = 0.002
325 parametersΔρmax = 0.65 e Å−3
6 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[Sn6(C4H9)6(C2H3O2)6O6]·C7H8V = 5861.3 (4) Å3
Mr = 1597.21Z = 4
Monoclinic, C2/cMo Kα radiation
a = 23.4154 (8) ŵ = 2.58 mm−1
b = 15.5832 (6) ÅT = 150 K
c = 16.1012 (6) Å0.30 × 0.22 × 0.10 mm
β = 93.926 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		6788 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		5890 reflections with I > 2σ(I)
Tmin = 0.509, Tmax = 0.783Rint = 0.035
76854 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0206 restraints
wR(F2) = 0.046H-atom parameters constrained
S = 1.05Δρmax = 0.65 e Å−3
6788 reflectionsΔρmin = −0.61 e Å−3
325 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*/UeqOcc. (<1)
Sn10.218624 (6)0.777418 (9)0.142503 (8)0.01627 (4)
Sn20.343645 (6)0.788062 (10)0.073955 (8)0.01612 (4)
Sn30.238831 (6)0.599363 (9)0.049412 (8)0.01573 (4)
O10.26833 (6)0.86006 (10)0.07422 (8)0.0175 (3)
O20.28513 (6)0.69761 (10)0.11156 (8)0.0172 (3)
O30.17758 (6)0.69645 (10)0.05325 (9)0.0171 (3)
O40.27161 (7)0.81598 (10)0.25130 (9)0.0228 (4)
O50.35980 (7)0.81837 (10)0.20439 (9)0.0223 (4)
C40.32520 (11)0.82347 (14)0.26131 (13)0.0208 (5)
C50.35026 (11)0.84157 (18)0.34786 (14)0.0309 (6)
H5A0.39160.83100.35070.064 (3)*
H5B0.33240.80400.38740.064 (3)*
H5C0.34320.90160.36200.064 (3)*
O60.39045 (7)0.90787 (10)0.06712 (9)0.0212 (3)
O70.33111 (7)0.98846 (10)−0.01633 (9)0.0204 (3)
C60.37742 (10)0.97521 (15)0.02701 (13)0.0194 (5)
C70.42114 (11)1.04577 (16)0.03037 (15)0.0276 (5)
H7A0.44791.0365−0.01300.064 (3)*
H7B0.44221.04580.08510.064 (3)*
H7C0.40191.10110.02120.064 (3)*
O80.21456 (7)0.55655 (10)0.17029 (9)0.0223 (3)
O90.19702 (7)0.68149 (10)0.23257 (9)0.0229 (4)
C80.20029 (10)0.60108 (15)0.23140 (13)0.0202 (5)
C90.18485 (12)0.55366 (17)0.30800 (14)0.0303 (6)
H9A0.19540.58840.35740.064 (3)*
H9B0.20550.49900.31180.064 (3)*
H9C0.14350.54270.30470.064 (3)*
C110.14968 (11)0.86040 (16)0.16782 (16)0.0282 (6)
H11A0.12210.86130.11840.053 (3)*
H11B0.12970.83600.21460.053 (3)*
C120.16665 (11)0.95254 (16)0.18958 (15)0.0273 (5)
H12A0.19030.95270.24290.053 (3)*
H12B0.19050.97510.14610.053 (3)*
C130.11608 (13)1.01168 (18)0.1972 (2)0.0445 (8)
H13A0.09440.99260.24450.053 (3)*
H13B0.09031.00720.14590.053 (3)*
C140.13350 (16)1.10523 (19)0.2104 (2)0.0563 (10)
H14A0.15841.11030.26160.053 (3)*
H14B0.09921.14040.21510.053 (3)*
H14C0.15411.12500.16300.053 (3)*
C210.41783 (11)0.70950 (17)0.07025 (15)0.0288 (6)
H21A0.43230.69620.12810.110 (5)*
H21B0.40670.65460.04270.110 (5)*
C220.46616 (13)0.7496 (2)0.0248 (2)0.0513 (9)
H22A0.47880.80290.05400.110 (5)*
H22B0.45130.7655−0.03220.110 (5)*
C230.51778 (14)0.6905 (2)0.0190 (3)0.0629 (10)
H23A0.54950.7237−0.00300.110 (5)*
H23B0.53060.67070.07560.110 (5)*
C240.50580 (17)0.6140 (3)−0.0354 (3)0.0911 (16)
H24A0.47390.5814−0.01490.110 (5)*
H24B0.53990.5775−0.03430.110 (5)*
H24C0.49580.6329−0.09260.110 (5)*
C310.30603 (10)0.50768 (13)0.04935 (14)0.0229 (5)0.90
H31A0.32640.5160−0.00190.050 (3)*0.90
H31B0.33360.52000.09730.050 (3)*0.90
C320.28870 (13)0.41416 (12)0.05386 (19)0.0290 (7)0.90
H32A0.26400.39940.00350.050 (3)*0.90
H32B0.26600.40560.10290.050 (3)*0.90
C330.33987 (14)0.35436 (16)0.0603 (2)0.0412 (9)0.90
H33A0.36090.36010.00930.050 (3)*0.90
H33B0.36600.37220.10810.050 (3)*0.90
C340.32403 (17)0.26092 (18)0.0712 (2)0.0549 (10)0.90
H34A0.30200.25480.12050.050 (3)*0.90
H34B0.35900.22630.07830.050 (3)*0.90
H34C0.30090.24120.02180.050 (3)*0.90
C350.30603 (10)0.50768 (13)0.04935 (14)0.0229 (5)0.10
H35A0.33530.52820.01250.050 (3)*0.10
H35B0.32440.50280.10640.050 (3)*0.10
C360.2853 (11)0.4198 (7)0.0203 (18)0.0290 (7)0.10
H36A0.25320.40330.05400.050 (3)*0.10
H36B0.26950.4254−0.03810.050 (3)*0.10
C370.3279 (15)0.346 (2)0.0239 (18)0.0412 (9)0.10
H37A0.35910.3610−0.01220.050 (3)*0.10
H37B0.30840.29470.00020.050 (3)*0.10
C380.3546 (15)0.324 (2)0.1096 (16)0.0549 (10)0.10
H38A0.36730.37670.13860.050 (3)*0.10
H38B0.38750.28620.10400.050 (3)*0.10
H38C0.32630.29480.14160.050 (3)*0.10
C410.5000−0.0820 (4)0.25000.100 (2)
H41A0.4606−0.10300.25180.150*0.50
H41B0.5231−0.10300.29890.150*0.50
H41C0.5163−0.10300.19930.150*0.50
C420.50000.0141 (4)0.25000.0587 (14)
C430.54010 (18)0.0576 (4)0.2095 (3)0.0852 (15)
H430.56790.02700.18090.102*
C440.5404 (3)0.1462 (5)0.2097 (5)0.152 (4)
H440.56860.17670.18200.182*
C450.50000.1894 (7)0.25000.192 (8)
H450.50000.25040.25000.230*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01857 (9)0.01607 (9)0.01429 (7)0.00037 (6)0.00206 (6)−0.00086 (5)
Sn20.01640 (9)0.01663 (9)0.01515 (7)0.00063 (6)−0.00022 (5)0.00075 (5)
Sn30.01802 (9)0.01440 (8)0.01468 (7)0.00077 (6)0.00034 (5)0.00074 (5)
O10.0203 (8)0.0183 (8)0.0139 (7)0.0016 (7)0.0006 (6)0.0007 (6)
O20.0191 (9)0.0152 (8)0.0174 (7)−0.0001 (6)0.0011 (6)0.0006 (6)
O30.0183 (8)0.0176 (8)0.0153 (7)0.0017 (7)0.0011 (6)−0.0001 (6)
O40.0257 (10)0.0258 (9)0.0170 (8)−0.0023 (7)0.0014 (6)−0.0034 (6)
O50.0232 (9)0.0251 (9)0.0182 (8)−0.0016 (7)−0.0017 (6)−0.0006 (6)
C40.0278 (15)0.0144 (12)0.0197 (11)0.0004 (10)−0.0025 (9)0.0003 (8)
C50.0328 (15)0.0413 (16)0.0180 (11)−0.0001 (13)−0.0033 (10)−0.0061 (10)
O60.0219 (9)0.0190 (9)0.0224 (8)−0.0017 (7)−0.0022 (6)0.0021 (6)
O70.0201 (9)0.0190 (9)0.0215 (8)−0.0008 (7)−0.0026 (6)0.0011 (6)
C60.0226 (13)0.0199 (13)0.0160 (10)−0.0010 (10)0.0050 (9)−0.0032 (8)
C70.0275 (14)0.0239 (14)0.0308 (13)−0.0069 (11)−0.0017 (10)0.0029 (10)
O80.0306 (9)0.0197 (9)0.0168 (7)−0.0008 (7)0.0029 (6)0.0020 (6)
O90.0318 (10)0.0205 (9)0.0170 (8)−0.0015 (7)0.0063 (6)0.0001 (6)
C80.0182 (12)0.0245 (14)0.0178 (11)−0.0024 (10)0.0013 (8)0.0020 (9)
C90.0407 (16)0.0284 (14)0.0227 (12)−0.0011 (12)0.0077 (10)0.0058 (10)
C110.0246 (14)0.0245 (14)0.0358 (14)0.0031 (11)0.0037 (10)−0.0072 (10)
C120.0314 (15)0.0227 (13)0.0275 (12)0.0040 (11)−0.0004 (10)−0.0052 (10)
C130.0445 (19)0.0307 (17)0.0562 (19)0.0132 (14)−0.0109 (14)−0.0158 (13)
C140.079 (3)0.0328 (18)0.054 (2)0.0212 (17)−0.0220 (18)−0.0145 (14)
C210.0253 (14)0.0320 (15)0.0292 (13)0.0101 (11)0.0033 (10)0.0035 (10)
C220.0278 (17)0.0427 (19)0.086 (2)0.0041 (14)0.0221 (16)−0.0081 (17)
C230.0265 (18)0.061 (2)0.103 (3)0.0036 (16)0.0147 (18)−0.023 (2)
C240.043 (2)0.077 (3)0.155 (5)0.006 (2)0.027 (3)−0.050 (3)
C310.0211 (13)0.0236 (13)0.0239 (11)0.0047 (10)0.0001 (9)0.0029 (9)
C320.0305 (16)0.0216 (15)0.0356 (17)0.0049 (12)0.0078 (14)0.0064 (12)
C330.038 (2)0.0326 (18)0.055 (2)0.0124 (16)0.0152 (18)0.0107 (18)
C340.076 (3)0.033 (2)0.059 (2)0.0217 (19)0.030 (2)0.0140 (16)
C350.0211 (13)0.0236 (13)0.0239 (11)0.0047 (10)0.0001 (9)0.0029 (9)
C360.0305 (16)0.0216 (15)0.0356 (17)0.0049 (12)0.0078 (14)0.0064 (12)
C370.038 (2)0.0326 (18)0.055 (2)0.0124 (16)0.0152 (18)0.0107 (18)
C380.076 (3)0.033 (2)0.059 (2)0.0217 (19)0.030 (2)0.0140 (16)
C410.057 (4)0.095 (6)0.143 (7)0.000−0.031 (4)0.000
C420.041 (3)0.085 (4)0.046 (3)0.000−0.018 (2)0.000
C430.050 (3)0.138 (5)0.064 (3)−0.024 (3)−0.0227 (19)0.014 (3)
C440.103 (6)0.153 (8)0.184 (7)−0.064 (5)−0.090 (5)0.086 (6)
C450.141 (12)0.086 (8)0.32 (2)0.000−0.161 (13)0.000
Geometric parameters (Å, º) top
Sn1—O12.0969 (15)C14—H14A0.9800
Sn1—O22.0800 (15)C14—H14B0.9800
Sn1—O32.0957 (15)C14—H14C0.9800
Sn1—O42.1614 (15)C21—C221.523 (4)
Sn1—O92.1665 (15)C21—H21A0.9900
Sn1—C112.129 (2)C21—H21B0.9900
Sn2—O12.0903 (15)C22—C231.527 (4)
Sn2—O22.0843 (15)C22—H22A0.9900
Sn2—O3i2.0882 (14)C22—H22B0.9900
Sn2—O52.1606 (15)C23—C241.494 (5)
Sn2—O62.1715 (15)C23—H23A0.9900
Sn2—C212.129 (2)C23—H23B0.9900
Sn3—O1i2.0845 (14)C24—H24A0.9800
Sn3—O22.0909 (15)C24—H24B0.9800
Sn3—O32.0885 (15)C24—H24C0.9800
Sn3—O7i2.1724 (15)C31—C321.516 (2)
Sn3—O82.1697 (14)C31—H31A0.9900
Sn3—C312.125 (2)C31—H31B0.9900
O1—Sn3i2.0845 (14)C32—C331.516 (2)
O3—Sn2i2.0882 (14)C32—H32A0.9900
O4—C41.260 (3)C32—H32B0.9900
O5—C41.267 (3)C33—C341.516 (2)
C4—C51.501 (3)C33—H33A0.9900
C5—H5A0.9800C33—H33B0.9900
C5—H5B0.9800C34—H34A0.9800
C5—H5C0.9800C34—H34B0.9800
O6—C61.259 (3)C34—H34C0.9800
O7—C61.266 (3)C36—C371.516 (2)
O7—Sn3i2.1724 (15)C36—H36A0.9900
C6—C71.501 (3)C36—H36B0.9900
C7—H7A0.9800C37—C381.516 (2)
C7—H7B0.9800C37—H37A0.9900
C7—H7C0.9800C37—H37B0.9900
O8—C81.267 (3)C38—H38A0.9800
O9—C81.256 (3)C38—H38B0.9800
C8—C91.503 (3)C38—H38C0.9800
C9—H9A0.9800C41—C421.498 (8)
C9—H9B0.9800C41—H41A0.9800
C9—H9C0.9800C41—H41B0.9800
C11—C121.524 (3)C41—H41C0.9800
C11—H11A0.9900C42—C43ii1.360 (5)
C11—H11B0.9900C42—C431.360 (5)
C12—C131.512 (4)C43—C441.381 (9)
C12—H12A0.9900C43—H430.9500
C12—H12B0.9900C44—C451.362 (10)
C13—C141.525 (4)C44—H440.9500
C13—H13A0.9900C45—C44ii1.362 (10)
C13—H13B0.9900C45—H450.9500
O2—Sn1—O377.96 (6)C13—C12—C11113.6 (2)
O2—Sn1—O177.88 (6)C13—C12—H12A108.9
O3—Sn1—O1104.78 (6)C11—C12—H12A108.9
O2—Sn1—C11177.18 (8)C13—C12—H12B108.9
O3—Sn1—C11100.30 (8)C11—C12—H12B108.9
O1—Sn1—C11100.53 (8)H12A—C12—H12B107.7
O2—Sn1—O487.87 (6)C12—C13—C14113.0 (3)
O3—Sn1—O4159.07 (6)C12—C13—H13A109.0
O1—Sn1—O486.89 (6)C14—C13—H13A109.0
C11—Sn1—O494.39 (8)C12—C13—H13B109.0
O2—Sn1—O987.75 (6)C14—C13—H13B109.0
O3—Sn1—O985.78 (6)H13A—C13—H13B107.8
O1—Sn1—O9159.73 (6)C13—C14—H14A109.5
C11—Sn1—O994.36 (8)C13—C14—H14B109.5
O4—Sn1—O978.27 (6)H14A—C14—H14B109.5
O2—Sn2—O3i104.24 (6)C13—C14—H14C109.5
O2—Sn2—O177.93 (6)H14A—C14—H14C109.5
O3i—Sn2—O178.22 (5)H14B—C14—H14C109.5
O2—Sn2—C2199.96 (8)C22—C21—Sn2114.34 (19)
O3i—Sn2—C21100.30 (8)C22—C21—H21A108.7
O1—Sn2—C21176.96 (8)Sn2—C21—H21A108.7
O2—Sn2—O586.58 (6)C22—C21—H21B108.7
O3i—Sn2—O5160.42 (6)Sn2—C21—H21B108.7
O1—Sn2—O588.41 (6)H21A—C21—H21B107.6
C21—Sn2—O593.67 (8)C21—C22—C23113.6 (3)
O2—Sn2—O6160.09 (6)C21—C22—H22A108.9
O3i—Sn2—O686.44 (6)C23—C22—H22A108.9
O1—Sn2—O688.13 (6)C21—C22—H22B108.9
C21—Sn2—O694.44 (8)C23—C22—H22B108.9
O5—Sn2—O678.81 (6)H22A—C22—H22B107.7
O1i—Sn3—O378.34 (6)C24—C23—C22113.5 (3)
O1i—Sn3—O2103.89 (6)C24—C23—H23A108.9
O3—Sn3—O277.88 (6)C22—C23—H23A108.9
O1i—Sn3—C31102.40 (7)C24—C23—H23B108.9
O3—Sn3—C31175.48 (7)C22—C23—H23B108.9
O2—Sn3—C3197.63 (7)H23A—C23—H23B107.7
O1i—Sn3—O8160.23 (6)C23—C24—H24A109.5
O3—Sn3—O888.49 (6)C23—C24—H24B109.5
O2—Sn3—O887.42 (6)H24A—C24—H24B109.5
C31—Sn3—O891.90 (7)C23—C24—H24C109.5
O1i—Sn3—O7i86.96 (6)H24A—C24—H24C109.5
O3—Sn3—O7i87.47 (6)H24B—C24—H24C109.5
O2—Sn3—O7i159.40 (6)C32—C31—Sn3116.47 (17)
C31—Sn3—O7i97.01 (7)C32—C31—H31A108.2
O8—Sn3—O7i77.69 (6)Sn3—C31—H31A108.2
Sn3i—O1—Sn2100.00 (6)C32—C31—H31B108.2
Sn3i—O1—Sn1132.51 (7)Sn3—C31—H31B108.2
Sn2—O1—Sn199.79 (6)H31A—C31—H31B107.3
Sn1—O2—Sn2100.55 (6)C31—C32—C33112.4 (3)
Sn1—O2—Sn3100.39 (6)C31—C32—H32A109.1
Sn2—O2—Sn3133.30 (7)C33—C32—H32A109.1
Sn2i—O3—Sn399.94 (6)C31—C32—H32B109.1
Sn2i—O3—Sn1132.08 (7)C33—C32—H32B109.1
Sn3—O3—Sn199.95 (6)H32A—C32—H32B107.9
C4—O4—Sn1129.87 (14)C34—C33—C32113.6 (3)
C4—O5—Sn2129.71 (15)C34—C33—H33A108.9
O4—C4—O5125.6 (2)C32—C33—H33A108.9
O4—C4—C5117.3 (2)C34—C33—H33B108.9
O5—C4—C5117.0 (2)C32—C33—H33B108.9
C4—C5—H5A109.5H33A—C33—H33B107.7
C4—C5—H5B109.5C37—C36—H36A107.8
H5A—C5—H5B109.5C37—C36—H36B107.8
C4—C5—H5C109.5H36A—C36—H36B107.1
H5A—C5—H5C109.5C36—C37—C38116 (3)
H5B—C5—H5C109.5C36—C37—H37A108.3
C6—O6—Sn2129.60 (15)C38—C37—H37A108.3
C6—O7—Sn3i129.45 (14)C36—C37—H37B108.3
O6—C6—O7126.0 (2)C38—C37—H37B108.3
O6—C6—C7116.8 (2)H37A—C37—H37B107.4
O7—C6—C7117.2 (2)C37—C38—H38A109.5
C6—C7—H7A109.5C37—C38—H38B109.5
C6—C7—H7B109.5H38A—C38—H38B109.5
H7A—C7—H7B109.5C37—C38—H38C109.5
C6—C7—H7C109.5H38A—C38—H38C109.5
H7A—C7—H7C109.5H38B—C38—H38C109.5
H7B—C7—H7C109.5C42—C41—H41A109.5
C8—O8—Sn3128.85 (14)C42—C41—H41B109.5
C8—O9—Sn1131.40 (14)H41A—C41—H41B109.5
O9—C8—O8125.3 (2)C42—C41—H41C109.5
O9—C8—C9117.4 (2)H41A—C41—H41C109.5
O8—C8—C9117.3 (2)H41B—C41—H41C109.5
C8—C9—H9A109.5C43ii—C42—C43120.3 (7)
C8—C9—H9B109.5C43ii—C42—C41119.9 (3)
H9A—C9—H9B109.5C43—C42—C41119.9 (3)
C8—C9—H9C109.5C42—C43—C44120.0 (6)
H9A—C9—H9C109.5C42—C43—H43120.0
H9B—C9—H9C109.5C44—C43—H43120.0
C12—C11—Sn1115.28 (17)C45—C44—C43119.5 (9)
C12—C11—H11A108.5C45—C44—H44120.2
Sn1—C11—H11A108.5C43—C44—H44120.2
C12—C11—H11B108.5C44ii—C45—C44120.7 (12)
Sn1—C11—H11B108.5C44ii—C45—H45119.7
H11A—C11—H11B107.5C44—C45—H45119.7
Sn2—O2—Sn3—O1i−25.88 (11)O1i—Sn1i—O3i—Sn224.53 (11)
O2—Sn3—O1i—Sn1i24.87 (11)Sn1i—O3i—Sn2—O2−24.89 (11)
Sn3—O1i—Sn1i—O3i−24.64 (11)O3i—Sn2—O2—Sn325.96 (11)
Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula[Sn6(C4H9)6(C2H3O2)6O6]·C7H8
Mr1597.21
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)23.4154 (8), 15.5832 (6), 16.1012 (6)
β (°) 93.926 (2)
V (Å3)5861.3 (4)
Z4
Radiation typeMo Kα
µ (mm−1)2.58
Crystal size (mm)0.30 × 0.22 × 0.10
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.509, 0.783
No. of measured, independent and
observed [I > 2σ(I)] reflections		76854, 6788, 5890
Rint0.035
(sin θ/λ)max (Å−1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.020, 0.046, 1.05
No. of reflections6788
No. of parameters325
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.65, −0.61

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008).

Selected torsion angles (º) top
Sn2—O2—Sn3—O1i−25.88 (11)O1i—Sn1i—O3i—Sn224.53 (11)
O2—Sn3—O1i—Sn1i24.87 (11)Sn1i—O3i—Sn2—O2−24.89 (11)
Sn3—O1i—Sn1i—O3i−24.64 (11)O3i—Sn2—O2—Sn325.96 (11)
Symmetry code: (i) −x+1/2, −y+3/2, −z.
 

References

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 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2 (including SAINT) and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBuslaev, Y. A., Kravchenko, E. A., Burtzev, M. Y. & Aslanov, L. A. (1989). Coord. Chem. Rev. 93, 185–204.  CrossRef CAS Web of Science Google Scholar
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 First citationMehrotra, R. C. & Bohra, R. (1983). In Metal Carboxylates. London, New York: Academic Press.  Google Scholar
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ISSN: 2056-9890
Volume 69| Part 1| January 2013| Page m4
https://doi.org/10.1107/S160053681204888X
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