fac-(2-Amido­ethyl-κ2C1,O)aqua­tri­chlorido­tin(IV) 1,4,7,10,13,16-hexa­oxacyclo­octa­decane (2/1)

Wardell, S.M.S.V.; Harrison, W.T.A.; Tiekink, E.R.T.; Lima, G.M. de; Wardell, J.L.

doi:10.1107/S1600536810005908

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages m312-m313

doi:10.1107/S1600536810005908

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fac-(2-Amidoethyl-κ²C¹,O)aquatrichloridotin(IV) 1,4,7,10,13,16-hexaoxacyclooctadecane (2/1)

Solange M. S. V. Wardell,^a William T. A. Harrison,^b Edward R. T. Tiekink,^c ^* Geraldo M. de Lima ^d and James L. Wardell ^e ‡

^aCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3NY, Scotland, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dDepartamento de Quimica, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil, and ^eCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 10 February 2010; accepted 13 February 2010; online 20 February 2010)

The asymmetric unit of the title compound, [Sn(C₃H₆NO)Cl₃(H₂O)]₂·C₁₂H₂₄O₆, comprises a six-coordinate tin complex and a 18-crown-6 molecule, the latter disposed about a centre of inversion. The tin atom is coordinated by three Cl atoms, that define a facial arrangement, a chelating C-,O- ligand, and a water molecule. The resulting CCl₃O₂ donor set defines a distorted octahedral geometry. The tin-bound aqua ligand forms O—H⋯O hydrogen bonds to the centrosymmetric 18-crown-6 molecule, resulting in a tri-molecular aggregate. These assemble into a supramolecular chain along the a axis being connected by N—H⋯O hydrogen bonds.

Related literature

For background to amidoethyl tin compounds, see: Hutton & Oakes (1976 ). For the use of organotin compounds as PVC stabilisers, see: Lanigen & Weinberg (1976 ). For the crystal structures of amidoethyltin compounds, see: Harrison et al. (1979 ); Tiekink et al. (2006 ). For the crystal structures of alkyloxycarbonylethyltin compounds, see: de Lima et al. (2009 ); Milne et al. (2005 ). For a review on tin–crown ether compounds, see: Cusack & Smith (1990 ). For related structures of organotin(IV) and tin(IV) halide complexes with crown ethers, see: Cusack et al. (1983 ); Amini et al. (1984 , 2002 ); Russo et al. (1984 ); Valle et al. (1984 , 1985 ); Rivarola et al. (1986 ); Bott et al. (1987 ); Mitra et al. (1993 ); Yap et al. (1996 ); Wolff et al. (2009 ).

Experimental

Crystal data

[Sn(C₃H₆NO)Cl₃(H₂O)]₂·C₁₂H₂₄O₆
M_r = 894.64
Monoclinic, P 2₁ /n
a = 10.1260 (2) Å
b = 10.0893 (3) Å
c = 15.8229 (4) Å
β = 105.814 (2)°
V = 1555.35 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.17 mm⁻¹
T = 120 K
0.20 × 0.18 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.638, T_max = 0.746
19526 measured reflections
3555 independent reflections
2981 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.090
S = 1.12
3555 reflections
184 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −1.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯O4	0.84 (2)	1.96 (2)	2.784 (3)	166 (3)
O1w—H2w⋯O2	0.84 (3)	2.01 (3)	2.839 (3)	169 (4)
N1—H1n⋯O3ⁱ	0.88 (3)	2.51 (3)	3.061 (4)	121 (2)
N1—H2n⋯Cl1ⁱⁱ	0.88 (3)	2.68 (3)	3.516 (3)	161 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810005908/lh2997sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005908/lh2997Isup2.hkl

checkCIF report

Comment top

Functionally substituted-alkyl-tin compounds, X₃SnCR₂CH₂COY and X₂Sn(CR₂CH₂COY)₂ (X = halide, R = H or alkyl; Y = OR', R' or NH₂, R' = alkyl or aryl), are available from reactions, first reported in the 1970's (Hutton & Oakes, 1976), of R₂C=CHCOY, HX and SnX₂ (for X₃SnCR₂CH₂COY compounds) or HX and tin (for X₂Sn(CR₂CH₂COY)₂ compounds). Original interest with these compounds was primarily concerned with their industrial potential as precursors of PVC stabilizers (Lanigen & Weinberg, 1976) but also with regard to their coordination chemistry. Although the potential for use in PVC stabilization has not been realized commercially, the interest in the coordination chemistry, especially of compounds containing SnCR₂CH₂CO₂R moieties, has been maintained over the succeeding decades: of particular interest has been the coordination modes of the CR₂CH₂COY ligands (de Lima et al., 2009; Milne et al., 2005; Harrison et al., 1979). Much less study has been made of amidoethyl-tin species. i.e., tin compounds containing the CH₂CH₂CONH₂ group. Only two structures of amidoethyltin derivatives have been previously reported, namely of (H₂NHCOCH₂CH₂-C,O)₂SnCl₂ (Harrison et al., 1979) and (H₂NCOCH₂CH₂-C,O)(ClCH₂CH₂CONH₂-O)SnCl₃ (Tiekink et al., 2006). We now wish to report the crystal structure of fac-aqua-trichloro(2-amidoethyl-C,O)tin 1,4,7,10,13,16-hexaoxacyclooctadecane (2/1), (I). Crown ether complexes of tin and organotin halides have been variously reported (Cusack et al. 1983; Amini et al., 1984; Valle et al., 1984; Russo et al., 1984; Valle et al., 1985; Rivarola et al., 1986; Bott et al., 1987; Cusack & Smith, 1990; Mitra et al., 1993; Yap et al., 1996; Amini et al., 2002; Wolff et al., 2009).

The asymmetric unit of (I) comprises a tin complex and half a 18-crown-6 molecule as the latter is situated about a centre of inversion, Fig. 1. The tin atom is coordinated by three Cl atoms, that define a facial arrangement, a C-,O-chelating ligand, and an aqua ligand. The resulting CCl₃O₂ donor set defines a distorted octahedral geometry. The Cl atoms trans to O-donors form longer Sn–Cl bond distances [Sn–Cl2 = 2.4208 (9) and Sn–Cl3 = 2.4329 (9) Å] than the Cl atom trans to the C1 atom [Sn–Cl1 = 2.3800 (9) Å]. The five-membered SnC₃O chelate ring is not planar as seen in the values of the Sn–C1–C2–C3 and C1–C2–C3–O1 torsion angles of 24.0 (4) and -15.9 (5) °, respectively.

The components of the structure are connected via O_aqua–H···O_ether hydrogen bonds to form a tri-molecular aggregate, Table 1 and Fig. 1. These in turn are connected via N–H···O_ether hydrogen bonds so that all ether-O atoms participate in hydrogen bonding interactions, Table 1. The resulting supramolecular aggregate is a linear chain formed along the a axis, Fig. 2. These are connected into the 3-D crystal structure via N–H···Cl interactions, Fig. 3.

Related literature top

For background to amidoethyl tin compounds, see: Hutton & Oakes (1976). For the use of organotin compounds as PVC stabilisers, see: Lanigen & Weinberg (1976). For the crystal structures of amidoethyltin compounds, see: Harrison et al. (1979); Tiekink et al. (2006). For the crystal structures of alkyloxycarbonylethyltin compounds, see: de Lima et al. (2009); Milne et al. (2005). For a review on tin–crown ether compounds, see: Cusack & Smith (1990). For related structures of organotin(IV) and tin(IV) halide complexes with crown ethers, see: Cusack et al. (1983); Amini et al. (1984, 2002); Russo et al. (1984); Valle et al. (1984, 1985); Rivarola et al. (1986); Bott et al. (1987); Cusa Mitra et al. (1993); Yap et al. (1996); Wolff et al. (2009).

Experimental top

The reaction between SnCl₂, H₂C═CHCONH₂ and gaseous HCl in diethyl ether, as previously reported (Tiekink et al., 2006), produced (H₂NCOCH₂CH₂-C,O)(ClCH₂CH₂CONH₂-O)SnCl₃. Solutions of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) (0.26 g, 1 mmol) in EtOH (15 ml) and (H₂NCOCH₂CH₂-C,O)(ClCH₂CH₂CONH₂-O)SnCl₃ (0.40 g, 1 mmol) in EtOH (20 ml) were mixed and gently heated for 15 min. The reaction mixture was cooled and maintained at room temperature. The crystals which slowly appeared on evaporation of the solvent were harvested after 1 week. M.pt.: partial sublimation at 463 K with complete melting at 469-471 K. IR (KBr, cm^-1): 3441, 3349, 3273, 2919(br), 1650, 1573, 1456, 1352, 1297, 1254, 1094, 1037, 958, 915, 844, 702, 564.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of a tri-molecular aggregate in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. A view of a supramolecular chain in (I), aligned along the a axis, whereby the tri-molecular aggregates sustained by O–H···O hydrogen bonds (orange dashed lines) illustrated in Fig. 1, are connected via N–H···O hydrogen bonds (blue dashed lines). Colour code: Sn, orange; Cl, cyan; O, red; N, blue; C, grey; and H, green.
	Fig. 3. View in projection down the a axis of the unit cell contents in (I). The N–H···Cl interactions connecting the supramolecular chains illustrated in Fig. 2 are shown as green dashed lines. Colour code: Sn, orange; Cl, cyan; O, red; N, blue; C, grey; and H, green.

fac-(2-Amidoethyl-κ²C¹,O)aquatrichloridotin(IV)–1,4,7,10,13,16-hexaoxacyclooctadecane (2/1) top

Crystal data top

[Sn(C₃H₆NO)Cl₃(H₂O)]₂·C₁₂H₂₄O₆	F(000) = 888
M_r = 894.64	D_x = 1.910 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9442 reflections
a = 10.1260 (2) Å	θ = 2.9–27.5°
b = 10.0893 (3) Å	µ = 2.17 mm⁻¹
c = 15.8229 (4) Å	T = 120 K
β = 105.814 (2)°	Prism, colourless
V = 1555.35 (7) Å³	0.20 × 0.18 × 0.02 mm
Z = 2

Data collection top

Nonius KappaCCD area-detector diffractometer	3555 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2981 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.062
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −13→13
T_min = 0.638, T_max = 0.746	l = −20→20
19526 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
3555 reflections	(Δ/σ)_max = 0.002
184 parameters	Δρ_max = 0.81 e Å⁻³
6 restraints	Δρ_min = −1.31 e Å⁻³

Crystal data top

[Sn(C₃H₆NO)Cl₃(H₂O)]₂·C₁₂H₂₄O₆	V = 1555.35 (7) Å³
M_r = 894.64	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1260 (2) Å	µ = 2.17 mm⁻¹
b = 10.0893 (3) Å	T = 120 K
c = 15.8229 (4) Å	0.20 × 0.18 × 0.02 mm
β = 105.814 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3555 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2981 reflections with I > 2σ(I)
T_min = 0.638, T_max = 0.746	R_int = 0.062
19526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	6 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.81 e Å⁻³
3555 reflections	Δρ_min = −1.31 e Å⁻³
184 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

	x	y	z	U_iso*/U_eq
Sn	0.78251 (2)	0.23444 (2)	0.571426 (15)	0.01204 (10)
Cl1	0.77631 (9)	0.37992 (9)	0.68869 (6)	0.0199 (2)
Cl2	0.64299 (9)	0.07335 (9)	0.62109 (6)	0.0231 (2)
Cl3	0.99961 (8)	0.13617 (9)	0.65225 (6)	0.0200 (2)
O1	0.5890 (2)	0.3331 (2)	0.49675 (15)	0.0146 (5)
O1W	0.8950 (2)	0.4054 (2)	0.53264 (16)	0.0139 (5)
H1W	0.859 (3)	0.436 (4)	0.4824 (12)	0.021*
H2W	0.922 (4)	0.471 (2)	0.565 (2)	0.021*
N1	0.4259 (3)	0.3257 (3)	0.3687 (2)	0.0217 (7)
H1N	0.377 (3)	0.386 (3)	0.387 (2)	0.033*
H2N	0.396 (4)	0.290 (4)	0.3164 (14)	0.033*
C1	0.7646 (3)	0.1561 (3)	0.4426 (2)	0.0155 (7)
H1A	0.8272	0.2038	0.4148	0.019*
H1B	0.7894	0.0610	0.4465	0.019*
C2	0.6165 (3)	0.1739 (4)	0.3884 (2)	0.0191 (8)
H2A	0.6154	0.1925	0.3267	0.023*
H2B	0.5663	0.0899	0.3890	0.023*
C3	0.5422 (3)	0.2844 (3)	0.4209 (2)	0.0157 (7)
O2	1.0228 (2)	0.6214 (2)	0.63876 (15)	0.0146 (5)
O3	0.7765 (2)	0.6756 (2)	0.51861 (15)	0.0146 (5)
O4	0.7319 (2)	0.4951 (2)	0.37156 (15)	0.0140 (5)
C4	0.9395 (4)	0.7297 (3)	0.6529 (3)	0.0172 (8)
H4A	0.9985	0.8011	0.6861	0.021*
H4B	0.8774	0.6993	0.6877	0.021*
C5	0.8571 (4)	0.7812 (3)	0.5659 (3)	0.0175 (8)
H5A	0.7967	0.8541	0.5745	0.021*
H5B	0.9190	0.8161	0.5323	0.021*
C6	0.7026 (3)	0.7148 (4)	0.4323 (2)	0.0165 (7)
H6A	0.7659	0.7537	0.4012	0.020*
H6B	0.6326	0.7820	0.4349	0.020*
C7	0.6351 (3)	0.5932 (3)	0.3852 (2)	0.0156 (7)
H7A	0.5772	0.5525	0.4195	0.019*
H7B	0.5741	0.6196	0.3274	0.019*
C8	1.1285 (3)	0.5885 (3)	0.7162 (2)	0.0148 (7)
H8A	1.0876	0.5676	0.7648	0.018*
H8B	1.1917	0.6646	0.7342	0.018*
C9	0.7943 (3)	0.5295 (3)	0.3033 (2)	0.0149 (7)
H9A	0.8578	0.6050	0.3223	0.018*
H9B	0.7227	0.5562	0.2498	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01329 (15)	0.01173 (14)	0.01132 (15)	−0.00019 (8)	0.00373 (10)	0.00053 (9)
Cl1	0.0273 (5)	0.0190 (5)	0.0138 (5)	0.0020 (4)	0.0062 (4)	−0.0027 (3)
Cl2	0.0223 (4)	0.0194 (5)	0.0303 (5)	−0.0025 (4)	0.0118 (4)	0.0071 (4)
Cl3	0.0157 (4)	0.0195 (5)	0.0227 (5)	0.0027 (3)	0.0018 (4)	0.0049 (4)
O1	0.0164 (12)	0.0174 (13)	0.0101 (12)	0.0007 (10)	0.0036 (10)	−0.0028 (10)
O1W	0.0189 (12)	0.0094 (12)	0.0121 (13)	0.0002 (10)	0.0023 (10)	0.0026 (10)
N1	0.0165 (15)	0.0297 (19)	0.0176 (17)	0.0027 (14)	0.0023 (13)	−0.0074 (14)
C1	0.0176 (17)	0.0149 (18)	0.0152 (18)	0.0015 (14)	0.0062 (14)	−0.0013 (14)
C2	0.0167 (18)	0.024 (2)	0.017 (2)	−0.0039 (15)	0.0054 (15)	−0.0063 (16)
C3	0.0115 (16)	0.0186 (18)	0.0194 (19)	−0.0020 (14)	0.0084 (14)	0.0025 (15)
O2	0.0135 (11)	0.0160 (12)	0.0129 (13)	0.0015 (9)	0.0011 (9)	−0.0024 (9)
O3	0.0142 (12)	0.0128 (12)	0.0154 (13)	0.0005 (10)	0.0017 (10)	−0.0002 (10)
O4	0.0149 (11)	0.0138 (12)	0.0135 (12)	0.0011 (9)	0.0044 (9)	0.0023 (9)
C4	0.0170 (18)	0.0160 (18)	0.0194 (19)	−0.0013 (14)	0.0060 (15)	−0.0088 (14)
C5	0.0166 (18)	0.0110 (17)	0.025 (2)	−0.0019 (14)	0.0050 (15)	−0.0037 (15)
C6	0.0166 (18)	0.0162 (18)	0.017 (2)	0.0029 (14)	0.0051 (15)	0.0022 (14)
C7	0.0129 (16)	0.0199 (18)	0.0147 (18)	0.0032 (14)	0.0052 (14)	0.0029 (14)
C8	0.0176 (17)	0.0154 (17)	0.0110 (17)	0.0003 (14)	0.0029 (14)	−0.0008 (14)
C9	0.0155 (17)	0.0174 (18)	0.0128 (18)	−0.0002 (14)	0.0058 (14)	0.0035 (14)

Geometric parameters (Å, º) top

Sn—C1	2.147 (3)	O3—C6	1.423 (4)
Sn—O1	2.228 (2)	O3—C5	1.424 (4)
Sn—O1W	2.243 (2)	O4—C9	1.434 (4)
Sn—Cl1	2.3800 (9)	O4—C7	1.450 (4)
Sn—Cl2	2.4208 (9)	C4—C5	1.496 (5)
Sn—Cl3	2.4329 (9)	C4—H4A	0.9900
O1—C3	1.263 (4)	C4—H4B	0.9900
O1W—H1W	0.84 (2)	C5—H5A	0.9900
O1W—H2W	0.84 (3)	C5—H5B	0.9900
N1—C3	1.309 (5)	C6—C7	1.500 (5)
N1—H1N	0.88 (3)	C6—H6A	0.9900
N1—H2N	0.88 (3)	C6—H6B	0.9900
C1—C2	1.522 (5)	C7—H7A	0.9900
C1—H1A	0.9900	C7—H7B	0.9900
C1—H1B	0.9900	C8—C9ⁱ	1.502 (5)
C2—C3	1.512 (5)	C8—H8A	0.9900
C2—H2A	0.9900	C8—H8B	0.9900
C2—H2B	0.9900	C9—C8ⁱ	1.502 (5)
O2—C8	1.429 (4)	C9—H9A	0.9900
O2—C4	1.435 (4)	C9—H9B	0.9900

C1—Sn—O1	80.00 (11)	C6—O3—C5	111.8 (3)
C1—Sn—O1W	86.63 (11)	C9—O4—C7	113.6 (2)
O1—Sn—O1W	87.14 (8)	O2—C4—C5	108.9 (3)
C1—Sn—Cl1	162.49 (10)	O2—C4—H4A	109.9
O1—Sn—Cl1	86.08 (6)	C5—C4—H4A	109.9
O1W—Sn—Cl1	82.09 (6)	O2—C4—H4B	109.9
C1—Sn—Cl2	98.92 (10)	C5—C4—H4B	109.9
O1—Sn—Cl2	88.03 (6)	H4A—C4—H4B	108.3
O1W—Sn—Cl2	171.91 (6)	O3—C5—C4	108.7 (3)
Cl1—Sn—Cl2	91.10 (3)	O3—C5—H5A	110.0
C1—Sn—Cl3	100.34 (10)	C4—C5—H5A	110.0
O1—Sn—Cl3	177.30 (6)	O3—C5—H5B	110.0
O1W—Sn—Cl3	90.20 (6)	C4—C5—H5B	110.0
Cl1—Sn—Cl3	93.07 (3)	H5A—C5—H5B	108.3
Cl2—Sn—Cl3	94.55 (3)	O3—C6—C7	107.4 (3)
C3—O1—Sn	112.2 (2)	O3—C6—H6A	110.2
Sn—O1W—H1W	115 (3)	C7—C6—H6A	110.2
Sn—O1W—H2W	123 (3)	O3—C6—H6B	110.2
H1W—O1W—H2W	106 (4)	C7—C6—H6B	110.2
C3—N1—H1N	120 (2)	H6A—C6—H6B	108.5
C3—N1—H2N	119 (2)	O4—C7—C6	113.4 (3)
H1N—N1—H2N	120.6 (19)	O4—C7—H7A	108.9
C2—C1—Sn	107.9 (2)	C6—C7—H7A	108.9
C2—C1—H1A	110.1	O4—C7—H7B	108.9
Sn—C1—H1A	110.1	C6—C7—H7B	108.9
C2—C1—H1B	110.1	H7A—C7—H7B	107.7
Sn—C1—H1B	110.1	O2—C8—C9ⁱ	108.6 (3)
H1A—C1—H1B	108.4	O2—C8—H8A	110.0
C3—C2—C1	113.6 (3)	C9ⁱ—C8—H8A	110.0
C3—C2—H2A	108.9	O2—C8—H8B	110.0
C1—C2—H2A	108.9	C9ⁱ—C8—H8B	110.0
C3—C2—H2B	108.9	H8A—C8—H8B	108.4
C1—C2—H2B	108.9	O4—C9—C8ⁱ	108.9 (3)
H2A—C2—H2B	107.7	O4—C9—H9A	109.9
O1—C3—N1	121.1 (3)	C8ⁱ—C9—H9A	109.9
O1—C3—C2	121.2 (3)	O4—C9—H9B	109.9
N1—C3—C2	117.7 (3)	C8ⁱ—C9—H9B	109.9
C8—O2—C4	112.2 (3)	H9A—C9—H9B	108.3

C1—Sn—O1—C3	12.0 (2)	Sn—O1—C3—C2	−1.3 (4)
O1W—Sn—O1—C3	99.0 (2)	C1—C2—C3—O1	−15.9 (5)
Cl1—Sn—O1—C3	−178.7 (2)	C1—C2—C3—N1	165.8 (3)
Cl2—Sn—O1—C3	−87.5 (2)	C8—O2—C4—C5	165.3 (3)
O1—Sn—C1—C2	−18.7 (2)	C6—O3—C5—C4	−175.7 (3)
O1W—Sn—C1—C2	−106.4 (2)	O2—C4—C5—O3	57.7 (4)
Cl1—Sn—C1—C2	−56.6 (4)	C5—O3—C6—C7	173.4 (3)
Cl2—Sn—C1—C2	67.6 (2)	C9—O4—C7—C6	−75.0 (4)
Cl3—Sn—C1—C2	164.0 (2)	O3—C6—C7—O4	−65.3 (3)
Sn—C1—C2—C3	24.0 (4)	C4—O2—C8—C9ⁱ	177.2 (3)
Sn—O1—C3—N1	177.0 (3)	C7—O4—C9—C8ⁱ	−169.7 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O4	0.84 (2)	1.96 (2)	2.784 (3)	166 (3)
O1w—H2w···O2	0.84 (3)	2.01 (3)	2.839 (3)	169 (4)
N1—H1n···O3ⁱⁱ	0.88 (3)	2.51 (3)	3.061 (4)	121 (2)
N1—H2n···Cl1ⁱⁱⁱ	0.88 (3)	2.68 (3)	3.516 (3)	161 (3)

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

Experimental details

Crystal data
Chemical formula	[Sn(C₃H₆NO)Cl₃(H₂O)]₂·C₁₂H₂₄O₆
M_r	894.64
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	10.1260 (2), 10.0893 (3), 15.8229 (4)
β (°)	105.814 (2)
V (Å³)	1555.35 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.17
Crystal size (mm)	0.20 × 0.18 × 0.02

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.638, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	19526, 3555, 2981
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.090, 1.12
No. of reflections	3555
No. of parameters	184
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −1.31

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O4	0.84 (2)	1.96 (2)	2.784 (3)	166 (3)
O1w—H2w···O2	0.84 (3)	2.01 (3)	2.839 (3)	169 (4)
N1—H1n···O3ⁱ	0.88 (3)	2.51 (3)	3.061 (4)	121 (2)
N1—H2n···Cl1ⁱⁱ	0.88 (3)	2.68 (3)	3.516 (3)	161 (3)

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

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

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