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

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ISSN: 2056-9890

Bis(1,1-di­methyl­guanidinium) tetra­aqua­di­methyl­tin(IV) bis­­(sulfate)

aDepartement de Chimie, Faculté de Sciences et Techniques, Universite Cheikh Anta, Diop, Dakar, Senegal, and bCNRS, Universite de Bordeaux, ICMCB, 87 avenue du Dr A. Schweitzer, Pessac F-33608, France
*Correspondence e-mail: mouhasboye@hotmail.com

(Received 9 December 2011; accepted 13 December 2011; online 21 December 2011)

Single crystals of the title salt, (C3H10N3)2[Sn(CH3)2(H2O)4](SO4)2, formed concomitantly with the already known [Sn(CH3)3]2SO4·2H2O. In the title structure, the SnIV atom displays a slightly distorted octa­hedral coordination geometry defined by four O water atoms in the equatorial positions and two methyl groups in the axial positions. In the crystal, various O—H⋯O and N—H⋯O hydrogen-bonding inter­actions between the organic cation and the coordinated water mol­ecules as donors and the sulfate O atoms as acceptors result in a three-dimensional structure. The SnIV atom is located on an inversion centre, resulting in half of the complex metal cation being in the asymmetric unit.

Related literature

For applications of tin-based materials, see: Molloy & Purcell (1986[Molloy, K. C. & Purcell, T. G. (1986). J. Organomet. Chem. 312, 167-176.]); Dutrecq et al. (1992[Dutrecq, A., Willem, R., Biesemans, M., Boualam, M., Meriem, A. & Gielen, M. (1992). Main Group Met. Chem. 15, 285-291.]); Gielen (2005[Gielen, M. (2005). Appl. Organomet. Chem. 19, 440-450.]). For oxoanion ligands, see: Boye & Diasse-Sarr (2007[Boye, M. S. & Diasse-Sarr, A. (2007). C. R. Chim. 10, 466-468.]) and references therein. For [(Sn(CH3)3)2SO4].2H2O, see: Molloy et al. (1989[Molloy, K. C., Quill, K., Cunningham, D., McArdle, P. & Higgins, T. (1989). J. Chem. Soc. Dalton Trans. pp 267-273.]).

[Scheme 1]

Experimental

Crystal data
  • (C3H10N3)2[Sn(CH3)2(H2O)4](SO4)2

  • Mr = 589.26

  • Monoclinic, P 21 /n

  • a = 6.683 (1) Å

  • b = 12.609 (2) Å

  • c = 13.469 (2) Å

  • β = 99.207 (10)°

  • V = 1120.4 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 293 K

  • 0.25 × 0.12 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.722, Tmax = 0.873

  • 13961 measured reflections

  • 4462 independent reflections

  • 3306 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.084

  • S = 1.07

  • 4462 reflections

  • 168 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.51 e Å−3

  • Δρmin = −1.17 e Å−3

Table 1
Selected bond lengths (Å)

Sn1—C1 2.094 (2)
Sn1—O3 2.2140 (16)
Sn1—O2 2.2240 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H22⋯O13i 0.79 (4) 1.90 (4) 2.680 (2) 169 (4)
O2—H12⋯O12ii 0.72 (4) 1.91 (4) 2.627 (2) 175 (4)
O3—H23⋯O11iii 0.73 (3) 1.91 (3) 2.629 (3) 168 (3)
O3—H13⋯O10iv 0.91 (3) 1.71 (3) 2.615 (2) 172 (3)
N2—H2N⋯O13v 0.79 (3) 2.10 (3) 2.887 (2) 174 (3)
N3—H3N⋯O12v 0.87 (3) 2.04 (3) 2.899 (3) 172 (2)
N2—H1N⋯O10iv 0.82 (3) 2.14 (3) 2.918 (3) 160 (2)
N3—H4N⋯O11vi 0.82 (3) 2.17 (3) 2.956 (3) 160 (3)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z; (iii) [x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (v) -x+2, -y+2, -z+1; (vi) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Nonius, 2003[Nonius (2003). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Tin-based materials are known to exhibit a wide panel of potential applications in domains as different as plastic stabilizers, reaction catalysts (Molloy & Purcell, 1986), phytosanitory products (Dutrecq et al., 1992) or medicinals (Gielen, 2005). In such context, any new tin-based molecular material description brings its contribution to the knowledge of organotin compounds diversity, revealing, for instance, the report of new crystal packings or coordination sphere geometries. To such aim, we focused on oxoanions, notably sulfate, to construct polymeric tin-based compounds (Boye & Diasse-Sarr, 2007). It has been previously reported that (Sn(CH3)3)2SO4.2H2O (Molloy et al., 1989) crystallizes in an orthorhombic unit cell with a three-dimensional network based on an O2SnC3 coordination sphere, with the SnIV cation directly coordinated to the O atoms of the sulfate anion. Allowing dimethyl guanidinium sulfate to react which trimethyltin chloride, we obtained the known compound and concomitantly also single crystals of the title compound, (C3H10N3)2[Sn(CH3)2(H2O)4](SO4)2, the structure of which is described here. It is notable that these two compounds are optically undistinguishable and that all attempts gave mixtures of single crystals.

The asymmetric unit of the title compound contains half of an [Sn(CH3)2(H2O)4]2+ cation with the SnIV cation located on an inversion centre, one dimethyl guanidinium cation and one sulfate anion. The SnIV cation is octahedrally coordinated to two methyl groups in axial and four oxygen atoms of water molecules in equatorial positions (Figure 1). This O4SnC2 environment constitutes the first major difference with the structure of the previously reported compound. The second one comes from the crystal packing itself (Figure 2), since sulfate anions are not coordinated to Sn. The O—S—O bonds angles [108.71 (11)° -110.27 (10)°] indicate a slight angular distorsion of the tetrahedral sulfate anion. The third major structural difference in comparison with the previously reported compound comes from the presence of additional dimethyl guanidinium cations. Dimethyl guanidinium and the complex metal cations are connected through hydrogen bonds to the sulfate O atoms (Table 2), resulting in a three-dimensional structure.

Related literature top

For applications of tin-based materials, see: Molloy & Purcell (1986); Dutrecq et al. (1992); Gielen (2005). For oxoanion ligands, see: Boye & Diasse-Sarr (2007), and references therein. For [(Sn(CH3)3)2SO4].2H2O, see: Molloy et al. (1989).

Experimental top

[Me2NC(=NH)NH2]2H2SO4 and SnMe3Cl are Aldrich chemicals used without further purification. The title derivative is obtained by mixing in an 1:1 ratio [Me2NC(=NH)NH2]2H2SO4 (0,61 g, 2,18 mmol) dissolved in methanol (40 ml) and a minimum of water (10 ml) and SnMe3Cl (0,43 g, 2,18 mmol) dissolved in dichloromethane. The mixture was stirred for around two hours at room temperature and by slow solvent evaporation gave prismatic crystals suitable for X-ray diffraction analysis. Apart from the title compound, (Sn(CH3)3)2SO4.2H2O crystals suitable for X-ray diffraction were also found in the same batch. The determined crystal structure is strictly the same as the one previously described. Crystals of both compounds are colourless (m.p.> 533 K) and present the same global shape and size. Only X-ray diffraction allowed to distinguish between these concomitant products.

The title compound was isolated according to the following reaction:

4[(Me2NC(=NH)NH2)2H2SO4] + 6SnMe3Cl + 8H2O

[SnMe2(H2O)4](SO4)2[Me2NC(=NH2)NH2]2 + 2(SnMe3)2SO4.2H2O + 6[Me2NC(=NH2)NH2]Cl + SnMe4

Refinement top

H atoms of water and guanidinium were forund from Fourier synthesis and were refined freely. H atoms of the methyl groups were placed geometrically and were allowed for free rotation, with Ueq(H) = 1.5Ueq(C). The highest peak and the deepest hole in the final Fourier synthesis are 1.76 Å from O12 and 0.70 Å from Sn1, respectively.

Computing details top

Data collection: COLLECT (Nonius, 2003); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular entities of the title compound showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code i) -x+1, -y+1, -z+1.]
[Figure 2] Fig. 2. Molecular packing, showing intermolecular hydrogen bonding interactions (blue lines) as viewed along the a axis.
(I) top
Crystal data top
C2H14O4Sn·2(C3H10N3)·2(O4S)F(000) = 604
Mr = 589.26Dx = 1.747 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 46680 reflections
a = 6.683 (1) Åθ = 1.0–33.7°
b = 12.609 (2) ŵ = 1.39 mm1
c = 13.469 (2) ÅT = 293 K
β = 99.207 (10)°Prism, colorless
V = 1120.4 (3) Å30.25 × 0.12 × 0.10 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
4462 independent reflections
Radiation source: fine-focus sealed tube3306 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ scans and ω scans with κ = 0θmax = 33.7°, θmin = 3.5°
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
h = 107
Tmin = 0.722, Tmax = 0.873k = 1919
13961 measured reflectionsl = 2021
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0378P)2 + 0.1746P]
where P = (Fo2 + 2Fc2)/3
4462 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 1.51 e Å3
0 restraintsΔρmin = 1.17 e Å3
Crystal data top
C2H14O4Sn·2(C3H10N3)·2(O4S)V = 1120.4 (3) Å3
Mr = 589.26Z = 2
Monoclinic, P21/nMo Kα radiation
a = 6.683 (1) ŵ = 1.39 mm1
b = 12.609 (2) ÅT = 293 K
c = 13.469 (2) Å0.25 × 0.12 × 0.10 mm
β = 99.207 (10)°
Data collection top
Nonius KappaCCD
diffractometer
4462 independent reflections
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
3306 reflections with I > 2σ(I)
Tmin = 0.722, Tmax = 0.873Rint = 0.048
13961 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 1.51 e Å3
4462 reflectionsΔρmin = 1.17 e Å3
168 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Sn10.50000.50000.50000.02430 (6)
S11.36662 (7)0.79887 (3)0.78817 (3)0.02461 (10)
O30.4232 (3)0.64310 (13)0.40639 (14)0.0413 (4)
O20.3228 (3)0.56250 (15)0.61365 (13)0.0411 (4)
N30.7496 (3)1.12233 (14)0.49706 (16)0.0375 (4)
N20.7117 (3)0.96848 (18)0.40651 (15)0.0356 (4)
N10.7856 (3)0.96105 (15)0.58016 (13)0.0342 (4)
C60.7503 (3)1.01623 (15)0.49489 (16)0.0280 (4)
C50.7904 (4)0.84580 (18)0.58146 (19)0.0426 (5)
H5A0.82830.82030.51990.064*
H5B0.65860.81910.58800.064*
H5C0.88750.82200.63730.064*
C40.8083 (5)1.0131 (2)0.67791 (19)0.0498 (7)
H4A0.70471.06600.67720.075*
H4B0.93921.04620.69190.075*
H4C0.79600.96150.72900.075*
C10.7679 (3)0.57383 (18)0.56804 (17)0.0379 (5)
H1A0.86470.52080.59490.057*
H1B0.73930.61900.62140.057*
H1C0.82230.61550.51900.057*
O121.3577 (3)0.75608 (13)0.68640 (12)0.0480 (5)
O111.5624 (3)0.77413 (14)0.84837 (16)0.0582 (5)
O131.3383 (3)0.91454 (10)0.78006 (11)0.0377 (3)
O101.2059 (3)0.75053 (12)0.83607 (13)0.0428 (4)
H220.263 (6)0.524 (3)0.645 (3)0.067 (11)*
H120.339 (5)0.615 (3)0.635 (2)0.063 (10)*
H230.321 (5)0.660 (2)0.384 (2)0.057 (10)*
H130.514 (5)0.681 (3)0.376 (2)0.067 (9)*
H2N0.696 (5)1.0045 (19)0.358 (3)0.043 (9)*
H1N0.703 (4)0.904 (2)0.4009 (19)0.042 (7)*
H4N0.810 (4)1.151 (2)0.548 (2)0.037 (7)*
H3N0.728 (4)1.156 (2)0.441 (2)0.039 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03122 (11)0.01843 (8)0.02355 (10)0.00060 (6)0.00527 (7)0.00027 (6)
S10.0327 (2)0.01763 (17)0.0236 (2)0.00150 (16)0.00469 (16)0.00042 (16)
O30.0357 (9)0.0342 (8)0.0545 (10)0.0034 (7)0.0090 (8)0.0185 (7)
O20.0610 (11)0.0258 (7)0.0428 (9)0.0059 (7)0.0273 (8)0.0057 (7)
N30.0541 (12)0.0269 (8)0.0303 (9)0.0011 (8)0.0028 (9)0.0010 (7)
N20.0540 (12)0.0272 (8)0.0251 (9)0.0026 (8)0.0049 (8)0.0004 (8)
N10.0457 (11)0.0298 (8)0.0261 (8)0.0015 (8)0.0027 (7)0.0032 (7)
C60.0292 (10)0.0285 (9)0.0261 (9)0.0004 (7)0.0038 (7)0.0007 (7)
C50.0507 (14)0.0320 (10)0.0444 (13)0.0013 (9)0.0053 (10)0.0127 (10)
C40.0657 (18)0.0578 (16)0.0242 (11)0.0079 (12)0.0019 (11)0.0009 (10)
C10.0403 (12)0.0354 (11)0.0360 (11)0.0087 (9)0.0002 (9)0.0015 (9)
O120.0907 (14)0.0267 (7)0.0301 (8)0.0010 (8)0.0200 (8)0.0041 (6)
O110.0430 (10)0.0410 (9)0.0818 (13)0.0040 (7)0.0171 (9)0.0149 (9)
O130.0646 (10)0.0178 (6)0.0325 (7)0.0041 (6)0.0137 (7)0.0008 (5)
O100.0517 (10)0.0287 (7)0.0543 (10)0.0027 (7)0.0277 (8)0.0093 (7)
Geometric parameters (Å, º) top
Sn1—C1i2.094 (2)N3—H3N0.87 (3)
Sn1—C12.094 (2)N2—C61.322 (3)
Sn1—O32.2140 (16)N2—H2N0.79 (3)
Sn1—O3i2.2140 (16)N2—H1N0.82 (3)
Sn1—O22.2240 (17)N1—C61.331 (3)
Sn1—O2i2.2240 (17)N1—C51.453 (3)
S1—O111.4586 (18)N1—C41.457 (3)
S1—O121.4654 (16)C5—H5A0.9600
S1—O101.4710 (16)C5—H5B0.9600
S1—O131.4725 (14)C5—H5C0.9600
O3—H230.73 (3)C4—H4A0.9600
O3—H130.91 (3)C4—H4B0.9600
O2—H220.79 (4)C4—H4C0.9600
O2—H120.72 (4)C1—H1A0.9600
N3—C61.338 (3)C1—H1B0.9600
N3—H4N0.82 (3)C1—H1C0.9600
C1i—Sn1—C1180.0H4N—N3—H3N121 (3)
C1i—Sn1—O390.52 (8)C6—N2—H2N118 (2)
C1—Sn1—O389.48 (8)C6—N2—H1N122.5 (18)
C1i—Sn1—O3i89.48 (8)H2N—N2—H1N120 (3)
C1—Sn1—O3i90.52 (8)C6—N1—C5122.24 (19)
O3—Sn1—O3i180.000 (1)C6—N1—C4121.50 (19)
C1i—Sn1—O286.95 (9)C5—N1—C4116.14 (19)
C1—Sn1—O293.05 (9)N2—C6—N1121.39 (19)
O3—Sn1—O290.16 (7)N2—C6—N3118.3 (2)
O3i—Sn1—O289.84 (7)N1—C6—N3120.3 (2)
C1i—Sn1—O2i93.05 (9)N1—C5—H5A109.5
C1—Sn1—O2i86.95 (9)N1—C5—H5B109.5
O3—Sn1—O2i89.84 (7)H5A—C5—H5B109.5
O3i—Sn1—O2i90.16 (7)N1—C5—H5C109.5
O2—Sn1—O2i180.0H5A—C5—H5C109.5
O11—S1—O12109.87 (12)H5B—C5—H5C109.5
O11—S1—O10108.71 (11)N1—C4—H4A109.5
O12—S1—O10109.54 (11)N1—C4—H4B109.5
O11—S1—O13110.27 (10)H4A—C4—H4B109.5
O12—S1—O13108.05 (9)N1—C4—H4C109.5
O10—S1—O13110.40 (9)H4A—C4—H4C109.5
Sn1—O3—H23125 (3)H4B—C4—H4C109.5
Sn1—O3—H13125 (2)Sn1—C1—H1A109.5
H23—O3—H13108 (3)Sn1—C1—H1B109.5
Sn1—O2—H22121 (3)H1A—C1—H1B109.5
Sn1—O2—H12122 (3)Sn1—C1—H1C109.5
H22—O2—H12114 (3)H1A—C1—H1C109.5
C6—N3—H4N116.6 (19)H1B—C1—H1C109.5
C6—N3—H3N118.5 (18)
C5—N1—C6—N22.1 (3)C5—N1—C6—N3179.2 (2)
C4—N1—C6—N2173.8 (2)C4—N1—C6—N34.9 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H22···O13ii0.79 (4)1.90 (4)2.680 (2)169 (4)
O2—H12···O12iii0.72 (4)1.91 (4)2.627 (2)175 (4)
O3—H23···O11iv0.73 (3)1.91 (3)2.629 (3)168 (3)
O3—H13···O10v0.91 (3)1.71 (3)2.615 (2)172 (3)
N2—H2N···O13vi0.79 (3)2.10 (3)2.887 (2)174 (3)
N3—H3N···O12vi0.87 (3)2.04 (3)2.899 (3)172 (2)
N2—H1N···O10v0.82 (3)2.14 (3)2.918 (3)160 (2)
N3—H4N···O11vii0.82 (3)2.17 (3)2.956 (3)160 (3)
Symmetry codes: (ii) x+3/2, y1/2, z+3/2; (iii) x1, y, z; (iv) x3/2, y+3/2, z1/2; (v) x1/2, y+3/2, z1/2; (vi) x+2, y+2, z+1; (vii) x+5/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC2H14O4Sn·2(C3H10N3)·2(O4S)
Mr589.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)6.683 (1), 12.609 (2), 13.469 (2)
β (°) 99.207 (10)
V3)1120.4 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.25 × 0.12 × 0.10
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.722, 0.873
No. of measured, independent and
observed [I > 2σ(I)] reflections
13961, 4462, 3306
Rint0.048
(sin θ/λ)max1)0.782
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.084, 1.07
No. of reflections4462
No. of parameters168
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.51, 1.17

Computer programs: COLLECT (Nonius, 2003), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Sn1—C12.094 (2)Sn1—O22.2240 (17)
Sn1—O32.2140 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H22···O13i0.79 (4)1.90 (4)2.680 (2)169 (4)
O2—H12···O12ii0.72 (4)1.91 (4)2.627 (2)175 (4)
O3—H23···O11iii0.73 (3)1.91 (3)2.629 (3)168 (3)
O3—H13···O10iv0.91 (3)1.71 (3)2.615 (2)172 (3)
N2—H2N···O13v0.79 (3)2.10 (3)2.887 (2)174 (3)
N3—H3N···O12v0.87 (3)2.04 (3)2.899 (3)172 (2)
N2—H1N···O10iv0.82 (3)2.14 (3)2.918 (3)160 (2)
N3—H4N···O11vi0.82 (3)2.17 (3)2.956 (3)160 (3)
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x1, y, z; (iii) x3/2, y+3/2, z1/2; (iv) x1/2, y+3/2, z1/2; (v) x+2, y+2, z+1; (vi) x+5/2, y+1/2, z+3/2.
 

References

First citationBoye, M. S. & Diasse-Sarr, A. (2007). C. R. Chim. 10, 466–468.  Google Scholar
First citationDutrecq, A., Willem, R., Biesemans, M., Boualam, M., Meriem, A. & Gielen, M. (1992). Main Group Met. Chem. 15, 285–291.  CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGielen, M. (2005). Appl. Organomet. Chem. 19, 440–450.  Web of Science CrossRef CAS Google Scholar
First citationMolloy, K. C. & Purcell, T. G. (1986). J. Organomet. Chem. 312, 167–176.  CrossRef CAS Web of Science Google Scholar
First citationMolloy, K. C., Quill, K., Cunningham, D., McArdle, P. & Higgins, T. (1989). J. Chem. Soc. Dalton Trans. pp 267–273.  Google Scholar
First citationNonius (2003). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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