Poly[diaqua­(μ4-carboxyl­atomethyl­phospho­nato)(μ4-carb­oxy­methyl­phospho­nato)penta­deca­methyl­penta­tin(IV)]

Boye, M.S.; Diasse-Sarr, A.; Grosjean, A.; Guionneau, P.

doi:10.1107/S1600536813000676

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages m110-m111

doi:10.1107/S1600536813000676

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Poly[diaqua(μ₄-carboxylatomethylphosphonato)(μ₄-carboxymethylphosphonato)pentadecamethylpentatin(IV)]

Mouhamadou Sembene Boye,^a ^* Aminata Diasse-Sarr,^a Arnaud Grosjean ^b and Philippe Guionneau ^b

^aDepartement de Chimie, Faculte des Sciences et Techniques, Universite Cheikh Anta, Diop, Dakar, Senegal, and ^bCNRS, Univ. Bordeaux, ICMCB, UPR 9048, 87 avenue du Dr A. Schweitzer, F-33608 Pessac, France
^*Correspondence e-mail: mouhasboye@hotmail.com

(Received 29 November 2012; accepted 8 January 2013; online 19 January 2013)

The central Sn^IV atom of the pentanuclear title complex, {[Sn(CH₃)₃]₃O₂C(CH₂)PO₃[Sn(CH₃)₃(H₂O)]₂HO₂C(CH₂)PO₃}, is located on a twofold rotation axis; due to symmetry, the H atom of the carboxyl group of the anion is disordered with a site occupancy of 0.5. The central Sn^IV atom is bonded to three methyl groups (one of which is disordered about the twofold rotation axis) and is symmetrically trans coordinated by two phosphonate groups with Sn—O = 2.2665 (12) Å while the other SnMe₃ residues are asymmetrically trans coordinated with Sn—O = 2.1587 (12) and 2.3756 (13) Å for one residue and Sn—O = 2.1522 (12) and 2.4335 (12) Å for the other; the Sn–O distances involving two O atoms trans to carboxylate are longer than those trans to phosphonate groups. The Sn—C distances lie in a very narrow range [2.112 (2)–2.133 (3) Å]. The oxyanion behaves as a tetra-coordinating ligand. The bridging mode of the latter leads to the formation of layers parallel to (001) that are interconnected by O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For applications of tin-based materials, see: Dutrecq et al. (1992 ); Basu Baul et al. (2011 ). For related structures, see: Zhang et al. (2010 ).

Experimental

Crystal data

[Sn₅(CH₃)₁₅(C₂H₂O₅P)(C₂H₃O₅P)(H₂O)₂]
M_r = 1130.01
Monoclinic, C 2/c
a = 11.6939 (2) Å
b = 13.1689 (3) Å
c = 25.9575 (5) Å
β = 95.40 (1)°
V = 3979.61 (14) Å³
Z = 4
Mo Kα radiation
μ = 3.22 mm⁻¹
T = 150 K
0.32 × 0.15 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.426, T_max = 0.644
15302 measured reflections
7932 independent reflections
7236 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.054
S = 1.09
7932 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H1O⋯O5ⁱ	0.89	1.83	2.693 (2)	164
O6—H2O⋯O1ⁱ	0.85	1.88	2.706 (2)	161
C9—H9A⋯O4ⁱⁱ	0.99	2.51	3.227 (2)	129
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: COLLECT (Nonius, 2003 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: 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, 2012 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000676/pv2611sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000676/pv2611Isup2.hkl

checkCIF report

Comment top

Organotin(IV) compounds are involved in many applications in a large diversity of fields including agriculture, medicine and industry (Dutrecq et al., 1992; Basu Baul et al., 2011). Carboxylalkylphosphonate derivatives are interesting from the point of view of their structural tendency to form polymeric structures. The presence of carboxylate and phosphonate functions makes carboxylalkylphosphonate a polyfunctional ligand which can coordinate to the metal in all directions. The aim of combining organotin and carboxyalkylphosphonate is to exalte the biocidal activity in the resulting title complex. Only a few structures related to the title compound have been reported (Zhang et al., 2010).

The asymmetry unit of the title complex, [(SnMe₃)₃O₂C(CH₂)PO₃(SnMe₃.H₂O)₂HO₂C(CH₂)PO₃]_n, contains one half of the trimethyltin(IV) (SnMe₃) lying on a 2-fold axis linked to a [(SnMe₃)2.H₂O](PO₃CH₂CO₂H_0.5) fragment leading to the pentanuclear complex (Fig. 1) that forms the repeat unit of the polymer; the hydroxyl H-atom is disordered with 0.5 occupancy factor. The geometry of all tin atoms (Sn1, Sn2 and Sn3) is trigonal bipyramidal. The Sn—O distances in the title complex involving two O atoms trans to carboxylate [Sn3—O5ⁱⁱ = 2.4335 (12) Å] are longer than those trans to phosphonate groups [Sn3—O3 = 2.1522 (12) Å] (Table 1). The longest P—O bond [P1—O3 = 1.5156 (12) Å] is linked to the strongest Sn—O bond while, on the contrary, the shortest C—O bond [C8—O5 = 1.257 (2) Å] is linked to the weakest one. The values of O—Sn—O angles are in the range [176.51 (5)–176.84 (6)°] indicating a significant deviation from linearity. The C—Sn—C angles [115.13 (11)–124.85 (9)°] indicate almost planar Sn—C₃ groups. The crystal structure obtained is three-dimensional since, within the packing, each pentacoordinated tin atom is bonded to two oxygen atoms in axial positions and three methyl groups in equatorial positions. The SnC₃ residues are asymmetrically trans coordinated. The oxoanion behaves as a tetradentate ligand involving three oxygen atoms of the phosphonate and one of the carboxylate oxygen atom. Resulting chains are interconnected by O—H ···O hydrogen bonds which generate crystal lattice rectangular (Fig. 2 & Table 1).

Related literature top

For applications of tin-based materials, see: Dutrecq et al. (1992); Basu Baul et al. (2011). For related structures, see: Zhang et al. (2010).

Experimental top

The title compound was synthesized by the reaction in ethanol (30 ml) of carboxymethylphosphonic acid (0.161 g, 1.13 mmol), KOH (0.229 g, 3.39 mmol) and trimethyltin(IV) chloride (0.675 g, 3.39 mmol) in a 1:3:3 ratio. The mixture was stirred around two hours at room temperature. Suitable crystals for X-ray diffraction were obtained after a slow evaporation of the solvent; m.p. 463–464 K.

Computing details top

Data collection: COLLECT (Nonius, 2003); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: 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, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the asymmetric unit of the title compound showing the numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H-atoms have been omitted for clarity. Symmetry code: ⁱ = -x + 1, y, -z + 1/2
	Fig. 2. A view of O—H···O hydrogen bonds in the crystal structure. H atoms non-participating in hydrogen bonding and carbon atoms of the Sn- methyl group have been omitted for clarity.

Poly[diaqua(µ₄-carboxylatomethylphosphonato)(µ₄- carboxymethylphosphonato)pentadecamethylpentatin(IV)] top

Crystal data top

[Sn₅(CH₃)₁₅(C₂H₂O₅P)(C₂H₃O₅P)(H₂O)₂]	F(000) = 2176
M_r = 1130.01	D_x = 1.886 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 34199 reflections
a = 11.6939 (2) Å	θ = 1.0–33.7°
b = 13.1689 (3) Å	µ = 3.22 mm⁻¹
c = 25.9575 (5) Å	T = 150 K
β = 95.40 (1)°	Prism, colorless
V = 3979.61 (14) Å³	0.32 × 0.15 × 0.15 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	7932 independent reflections
Radiation source: fine-focus sealed tube	7236 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans with κ ofset	θ_max = 33.8°, θ_min = 2.3°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −18→18
T_min = 0.426, T_max = 0.644	k = −20→20
15302 measured reflections	l = −40→40

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.0207P)² + 4.2723P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.005
7932 reflections	Δρ_max = 1.14 e Å⁻³
182 parameters	Δρ_min = −0.85 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00041 (3)

Crystal data top

[Sn₅(CH₃)₁₅(C₂H₂O₅P)(C₂H₃O₅P)(H₂O)₂]	V = 3979.61 (14) Å³
M_r = 1130.01	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.6939 (2) Å	µ = 3.22 mm⁻¹
b = 13.1689 (3) Å	T = 150 K
c = 25.9575 (5) Å	0.32 × 0.15 × 0.15 mm
β = 95.40 (1)°

Data collection top

Nonius KappaCCD diffractometer	7932 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	7236 reflections with I > 2σ(I)
T_min = 0.426, T_max = 0.644	R_int = 0.020
15302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.09	Δρ_max = 1.14 e Å⁻³
7932 reflections	Δρ_min = −0.85 e Å⁻³
182 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	Occ. (<1)
Sn1	0.5000	0.755553 (11)	0.2500	0.01394 (4)
Sn3	0.657492 (10)	0.979143 (8)	0.093373 (4)	0.01521 (3)
Sn2	0.178461 (10)	0.935201 (8)	0.137009 (4)	0.01528 (3)
P1	0.43748 (3)	0.80781 (3)	0.118293 (15)	0.01189 (7)
O5	0.33357 (11)	0.57344 (9)	0.08457 (5)	0.0182 (2)
O4	0.24248 (11)	0.67603 (9)	0.02767 (5)	0.0180 (2)
O1	0.50422 (11)	0.75081 (9)	0.16291 (5)	0.0161 (2)
O3	0.49774 (11)	0.90382 (9)	0.10334 (5)	0.0186 (2)
C7	0.6528 (2)	0.94022 (17)	0.01376 (8)	0.0302 (4)
H7A	0.6136	0.9940	−0.0072	0.045*
H7B	0.6112	0.8761	0.0076	0.045*
H7C	0.7314	0.9326	0.0041	0.045*
O2	0.31351 (10)	0.82643 (9)	0.12850 (5)	0.0183 (2)
C9	0.43300 (13)	0.72417 (12)	0.06161 (6)	0.0139 (3)
H9A	0.4299	0.7663	0.0299	0.017*
H9B	0.5046	0.6836	0.0634	0.017*
C2	0.5000	0.9175 (2)	0.2500	0.0258 (5)
H2A	0.4976	0.9424	0.2143	0.039*	0.50
H2B	0.5699	0.9424	0.2698	0.039*	0.50
H2C	0.4325	0.9424	0.2658	0.039*	0.50
C8	0.33124 (13)	0.65301 (12)	0.05775 (6)	0.0135 (3)
C1	0.34603 (16)	0.66906 (15)	0.24300 (7)	0.0225 (3)
H1A	0.3063	0.6788	0.2084	0.034*
H1B	0.2962	0.6915	0.2691	0.034*
H1C	0.3645	0.5970	0.2482	0.034*
C4	0.28441 (19)	1.06554 (15)	0.13493 (10)	0.0303 (4)
H4A	0.2371	1.1245	0.1239	0.045*
H4B	0.3420	1.0543	0.1105	0.045*
H4C	0.3230	1.0781	0.1695	0.045*
C5	0.07938 (19)	0.89233 (17)	0.06770 (8)	0.0298 (4)
H5A	0.1051	0.8258	0.0564	0.045*
H5B	0.0891	0.9429	0.0408	0.045*
H5C	−0.0018	0.8885	0.0740	0.045*
C3	0.1385 (2)	0.86901 (18)	0.20725 (8)	0.0326 (5)
H3A	0.2046	0.8755	0.2332	0.049*
H3B	0.1204	0.7970	0.2016	0.049*
H3C	0.0721	0.9038	0.2195	0.049*
C6	0.59248 (18)	1.11584 (15)	0.12221 (9)	0.0284 (4)
H6A	0.5612	1.1025	0.1553	0.043*
H6B	0.5316	1.1424	0.0973	0.043*
H6C	0.6546	1.1658	0.1274	0.043*
O6	0.02501 (12)	1.04809 (10)	0.14945 (6)	0.0235 (3)
C10	0.76318 (18)	0.88614 (18)	0.14468 (9)	0.0339 (5)
H10A	0.8142	0.9290	0.1675	0.051*
H10B	0.8093	0.8413	0.1247	0.051*
H10C	0.7149	0.8451	0.1655	0.051*
H1O	−0.0374	1.0436	0.1273	0.050*
H2O	0.0350	1.1118	0.1539	0.050*
H1O4	0.2273	0.6343	0.0029	0.050*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01612 (7)	0.01318 (7)	0.01246 (7)	0.000	0.00108 (5)	0.000
Sn3	0.01622 (5)	0.01419 (5)	0.01498 (5)	−0.00358 (3)	0.00010 (4)	0.00139 (3)
Sn2	0.01507 (5)	0.01522 (5)	0.01564 (6)	0.00115 (3)	0.00182 (4)	−0.00054 (4)
P1	0.01177 (16)	0.01130 (16)	0.01267 (17)	−0.00176 (12)	0.00149 (13)	0.00042 (13)
O5	0.0157 (5)	0.0162 (5)	0.0220 (6)	−0.0029 (4)	−0.0018 (5)	0.0060 (4)
O4	0.0163 (5)	0.0181 (5)	0.0183 (5)	−0.0042 (4)	−0.0044 (4)	0.0046 (4)
O1	0.0189 (6)	0.0169 (5)	0.0123 (5)	0.0013 (4)	0.0005 (4)	0.0005 (4)
O3	0.0183 (6)	0.0140 (5)	0.0232 (6)	−0.0066 (4)	0.0010 (5)	0.0020 (4)
C7	0.0352 (11)	0.0341 (11)	0.0217 (9)	−0.0133 (8)	0.0055 (8)	−0.0054 (8)
O2	0.0134 (5)	0.0166 (5)	0.0258 (6)	0.0008 (4)	0.0063 (4)	−0.0011 (5)
C9	0.0130 (6)	0.0166 (7)	0.0123 (6)	−0.0039 (5)	0.0017 (5)	0.0001 (5)
C2	0.0419 (16)	0.0156 (10)	0.0194 (11)	0.000	0.0006 (11)	0.000
C8	0.0130 (6)	0.0135 (6)	0.0140 (6)	−0.0020 (5)	0.0013 (5)	0.0000 (5)
C1	0.0201 (8)	0.0262 (9)	0.0207 (8)	−0.0057 (6)	−0.0012 (6)	0.0045 (7)
C4	0.0254 (9)	0.0188 (8)	0.0481 (13)	−0.0023 (7)	0.0104 (9)	−0.0041 (8)
C5	0.0308 (10)	0.0330 (10)	0.0244 (9)	0.0088 (8)	−0.0042 (8)	−0.0088 (8)
C3	0.0387 (12)	0.0343 (11)	0.0269 (10)	0.0160 (9)	0.0150 (9)	0.0104 (8)
C6	0.0264 (9)	0.0196 (8)	0.0406 (11)	−0.0068 (7)	0.0110 (8)	−0.0071 (8)
O6	0.0195 (6)	0.0186 (6)	0.0308 (7)	0.0076 (5)	−0.0062 (5)	−0.0057 (5)
C10	0.0244 (9)	0.0344 (11)	0.0411 (12)	−0.0056 (8)	−0.0063 (9)	0.0204 (9)

Geometric parameters (Å, º) top

Sn1—C1	2.124 (2)	C9—C8	1.511 (2)
Sn1—C1ⁱ	2.124 (2)	C9—H9A	0.9900
Sn1—C2	2.133 (3)	C9—H9B	0.9900
Sn1—O1ⁱ	2.2665 (12)	C2—H2A	0.9800
Sn1—O1	2.2665 (12)	C2—H2B	0.9800
Sn3—C6	2.118 (2)	C2—H2C	0.9800
Sn3—C10	2.119 (2)	C1—H1A	0.9800
Sn3—C7	2.125 (2)	C1—H1B	0.9800
Sn3—O3	2.1522 (12)	C1—H1C	0.9800
Sn3—O5ⁱⁱ	2.4335 (12)	C4—H4A	0.9800
Sn2—C3	2.112 (2)	C4—H4B	0.9800
Sn2—C4	2.120 (2)	C4—H4C	0.9800
Sn2—C5	2.123 (2)	C5—H5A	0.9800
Sn2—O2	2.1587 (12)	C5—H5B	0.9800
Sn2—O6	2.3756 (13)	C5—H5C	0.9800
P1—O3	1.5156 (12)	C3—H3A	0.9800
P1—O2	1.5180 (13)	C3—H3B	0.9800
P1—O1	1.5310 (12)	C3—H3C	0.9800
P1—C9	1.8348 (16)	C6—H6A	0.9800
O5—C8	1.2571 (19)	C6—H6B	0.9800
O5—Sn3ⁱⁱⁱ	2.4335 (12)	C6—H6C	0.9800
O4—C8	1.2752 (19)	O6—H1O	0.8900
O4—H1O4	0.8500	O6—H2O	0.8500
C7—H7A	0.9800	C10—H10A	0.9800
C7—H7B	0.9800	C10—H10B	0.9800
C7—H7C	0.9800	C10—H10C	0.9800

C1—Sn1—C1ⁱ	115.13 (11)	P1—C9—H9B	109.0
C1—Sn1—C2	122.43 (6)	H9A—C9—H9B	107.8
C1ⁱ—Sn1—C2	122.43 (6)	Sn1—C2—H2A	109.5
C1—Sn1—O1ⁱ	88.44 (6)	Sn1—C2—H2B	109.5
C1ⁱ—Sn1—O1ⁱ	89.87 (6)	H2A—C2—H2B	109.5
C2—Sn1—O1ⁱ	91.58 (3)	Sn1—C2—H2C	109.5
C1—Sn1—O1	89.87 (6)	H2A—C2—H2C	109.5
C1ⁱ—Sn1—O1	88.44 (6)	H2B—C2—H2C	109.5
C2—Sn1—O1	91.58 (3)	O5—C8—O4	120.75 (14)
O1ⁱ—Sn1—O1	176.84 (6)	O5—C8—C9	120.30 (14)
C6—Sn3—C10	118.46 (10)	O4—C8—C9	118.94 (14)
C6—Sn3—C7	124.85 (9)	Sn1—C1—H1A	109.5
C10—Sn3—C7	115.59 (10)	Sn1—C1—H1B	109.5
C6—Sn3—O3	90.27 (6)	H1A—C1—H1B	109.5
C10—Sn3—O3	96.87 (7)	Sn1—C1—H1C	109.5
C7—Sn3—O3	93.58 (7)	H1A—C1—H1C	109.5
C6—Sn3—O5ⁱⁱ	86.24 (6)	H1B—C1—H1C	109.5
C10—Sn3—O5ⁱⁱ	84.57 (6)	Sn2—C4—H4A	109.5
C7—Sn3—O5ⁱⁱ	88.65 (7)	Sn2—C4—H4B	109.5
O3—Sn3—O5ⁱⁱ	176.51 (5)	H4A—C4—H4B	109.5
C3—Sn2—C4	122.21 (10)	Sn2—C4—H4C	109.5
C3—Sn2—C5	118.33 (10)	H4A—C4—H4C	109.5
C4—Sn2—C5	117.86 (10)	H4B—C4—H4C	109.5
C3—Sn2—O2	92.16 (7)	Sn2—C5—H5A	109.5
C4—Sn2—O2	95.72 (7)	Sn2—C5—H5B	109.5
C5—Sn2—O2	94.76 (7)	H5A—C5—H5B	109.5
C3—Sn2—O6	84.82 (7)	Sn2—C5—H5C	109.5
C4—Sn2—O6	86.99 (7)	H5A—C5—H5C	109.5
C5—Sn2—O6	85.56 (6)	H5B—C5—H5C	109.5
O2—Sn2—O6	176.72 (5)	Sn2—C3—H3A	109.5
O3—P1—O2	112.62 (7)	Sn2—C3—H3B	109.5
O3—P1—O1	112.74 (7)	H3A—C3—H3B	109.5
O2—P1—O1	111.98 (7)	Sn2—C3—H3C	109.5
O3—P1—C9	105.92 (7)	H3A—C3—H3C	109.5
O2—P1—C9	106.33 (7)	H3B—C3—H3C	109.5
O1—P1—C9	106.64 (7)	Sn3—C6—H6A	109.5
C8—O5—Sn3ⁱⁱⁱ	120.20 (10)	Sn3—C6—H6B	109.5
C8—O4—H1O4	114.10	H6A—C6—H6B	109.5
P1—O1—Sn1	133.13 (7)	Sn3—C6—H6C	109.5
P1—O3—Sn3	147.67 (8)	H6A—C6—H6C	109.5
Sn3—C7—H7A	109.5	H6B—C6—H6C	109.5
Sn3—C7—H7B	109.5	Sn2—O6—H1O	117.00
H7A—C7—H7B	109.5	Sn2—O6—H2O	123.00
Sn3—C7—H7C	109.5	H1O—O6—H2O	104.00
H7A—C7—H7C	109.5	Sn3—C10—H10A	109.5
H7B—C7—H7C	109.5	Sn3—C10—H10B	109.5
P1—O2—Sn2	147.66 (8)	H10A—C10—H10B	109.5
C8—C9—P1	112.86 (11)	Sn3—C10—H10C	109.5
C8—C9—H9A	109.0	H10A—C10—H10C	109.5
P1—C9—H9A	109.0	H10B—C10—H10C	109.5
C8—C9—H9B	109.0

O3—P1—O1—Sn1	91.91 (11)	O1—P1—O2—Sn2	121.26 (15)
O2—P1—O1—Sn1	−36.34 (12)	C9—P1—O2—Sn2	−122.63 (15)
C9—P1—O1—Sn1	−152.26 (9)	C3—Sn2—O2—P1	−130.11 (17)
C1—Sn1—O1—P1	76.70 (11)	C4—Sn2—O2—P1	−7.43 (17)
C1ⁱ—Sn1—O1—P1	−168.15 (11)	C5—Sn2—O2—P1	111.23 (16)
C2—Sn1—O1—P1	−45.74 (10)	O3—P1—C9—C8	−151.17 (11)
O2—P1—O3—Sn3	164.46 (14)	O2—P1—C9—C8	−31.14 (13)
O1—P1—O3—Sn3	36.55 (17)	O1—P1—C9—C8	88.51 (12)
C9—P1—O3—Sn3	−79.71 (16)	Sn3ⁱⁱⁱ—O5—C8—O4	−12.4 (2)
C6—Sn3—O3—P1	−142.37 (16)	Sn3ⁱⁱⁱ—O5—C8—C9	166.22 (11)
C10—Sn3—O3—P1	−23.64 (17)	P1—C9—C8—O5	−80.06 (17)
C7—Sn3—O3—P1	92.69 (16)	P1—C9—C8—O4	98.60 (16)
O3—P1—O2—Sn2	−7.05 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1O···O5^iv	0.89	1.83	2.693 (2)	164
O6—H2O···O1^iv	0.85	1.88	2.706 (2)	161
C9—H9A···O4^v	0.99	2.51	3.227 (2)	129

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

Experimental details

Crystal data
Chemical formula	[Sn₅(CH₃)₁₅(C₂H₂O₅P)(C₂H₃O₅P)(H₂O)₂]
M_r	1130.01
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	11.6939 (2), 13.1689 (3), 25.9575 (5)
β (°)	95.40 (1)
V (Å³)	3979.61 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.22
Crystal size (mm)	0.32 × 0.15 × 0.15

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.426, 0.644
No. of measured, independent and observed [I > 2σ(I)] reflections	15302, 7932, 7236
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.782

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.054, 1.09
No. of reflections	7932
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.85

Computer programs: COLLECT (Nonius, 2003), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1O···O5ⁱ	0.89	1.83	2.693 (2)	164
O6—H2O···O1ⁱ	0.85	1.88	2.706 (2)	161
C9—H9A···O4ⁱⁱ	0.99	2.51	3.227 (2)	129

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

References

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