fac-Aqua-(2-carboxy-ethyl-κC,O)trichlorido-tin(IV)-1,4,7,10,13-penta-oxacyclo-penta-deca-ne-water (1/1/2).

In the title compound, [Sn(C(3)H(5)O(2))Cl(3)(H(2)O)]·C(10)H(20)O(5)·2H(2)O, the Sn(IV) atom is octa-hedrally coordinated within a fac-CO(2)Cl(3) donor set, arising from the C,O-bidentate carboxy-ethyl ligand, a water mol-ecule and three chloride ligands. In the crystal, supra-molecular chains linked by O-H⋯O hydrogen bonds propagate along the c axis These chains are connected into layers in the ac plane via C-H⋯O inter-actions.

Related literature

For original industrial inter­est in functionally substituted alk­yl–tin compounds, see: Lanigen & Weinberg (1976 ▶). For studies concerning the coordination chemistry of functionally substituted alk­yl–tin compounds, see: Harrison et al. (1979 ▶); Howie et al. (1986 ▶); Balasubramanian et al. (1997 ▶); Tian et al. (2005 ▶); de Lima et al. (2009 ▶). For related structures of functionally substituted alk­yl–tin compounds, see: Buchanan et al. (1996 ▶); Howie & Wardell (2001 ▶, 2002 ▶). 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: Barnes & Weakley (1976 ▶); Cusack et al. (1984 ▶); Amini et al. (1984 ▶, 2002 ▶); Russo et al. (1984 ▶); Valle et al. (1984 ▶, 1985 ▶); Rivarola et al. (1986 ▶); Hough et al. (1986 ▶); Bott et al. (1987 ▶); Mitra et al. (1993 ▶); Yap et al. (1996 ▶); Wolff et al. (2009 ▶); Wardell et al. (2010 ▶). For a related tin compound with a 2-carboxy­ethyl ligand, see: Somphon et al. (2006 ▶). For the synthesis of MeO2CCH2CH2CO2SnCl3, see: Hutton & Oakes (1976 ▶).

Experimental

Crystal data

[Sn(C3H5O2)Cl3(H2O)]·C10H20O5·2H2O

M = 572.42

Monoclinic,

a = 7.2193 (2) Å

b = 29.6516 (13) Å

c = 10.3871 (5) Å

β = 91.857 (2)°

V = 2222.33 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.56 mm−1

T = 120 K

0.42 × 0.20 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.621, T max = 0.746

12758 measured reflections

3721 independent reflections

3241 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.088

S = 1.19

3721 reflections

265 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.74 e Å−3

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: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011633/hb5380sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011633/hb5380Isup2.hkl

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

[Sn(C3H5O2)Cl3(H2O)]·C10H20O5·2H2O	F(000) = 1160
Mr = 572.42	Dx = 1.711 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15234 reflections
a = 7.2193 (2) Å	θ = 2.9–27.5°
b = 29.6516 (13) Å	µ = 1.56 mm−1
c = 10.3871 (5) Å	T = 120 K
β = 91.857 (2)°	Blade, colourless
V = 2222.33 (16) Å3	0.42 × 0.20 × 0.07 mm
Z = 4

Nonius KappaCCD diffractometer	3721 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	3241 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.037
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.1°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −35→35
Tmin = 0.621, Tmax = 0.746	l = −12→12
12758 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1546P] where P = (Fo2 + 2Fc2)/3
3721 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.70 e Å−3
10 restraints	Δρmin = −0.74 e Å−3

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.

	x	y	z	Uiso*/Ueq
Sn	0.22564 (3)	0.175614 (7)	0.29201 (2)	0.01417 (11)
Cl1	0.34019 (12)	0.21445 (3)	0.10473 (9)	0.0209 (2)
Cl2	0.43021 (12)	0.21340 (3)	0.44366 (9)	0.0211 (2)
Cl3	0.42241 (11)	0.11255 (3)	0.26495 (9)	0.0186 (2)
O1	0.0296 (3)	0.13662 (7)	0.1555 (2)	0.0178 (5)
O2	−0.2328 (3)	0.14512 (9)	0.0433 (2)	0.0225 (6)
H1O	−0.195 (5)	0.1229 (8)	0.001 (3)	0.034*
O3	−0.2678 (3)	0.08134 (8)	0.6564 (2)	0.0199 (6)
O4	−0.0320 (3)	0.15697 (8)	0.6706 (2)	0.0187 (6)
O5	0.3096 (3)	0.12348 (8)	0.7855 (2)	0.0196 (6)
O6	0.1948 (3)	0.03774 (8)	0.8827 (2)	0.0198 (6)
O7	−0.0411 (3)	0.00568 (8)	0.6891 (2)	0.0194 (6)
O1W	0.1114 (3)	0.13208 (8)	0.4460 (2)	0.0204 (6)
H1W	0.168 (4)	0.1089 (7)	0.473 (3)	0.031*
H2W	0.056 (4)	0.1448 (10)	0.506 (2)	0.031*
O2W	−0.1475 (3)	0.07709 (8)	−0.0930 (2)	0.0183 (5)
H3W	−0.194 (4)	0.0799 (13)	−0.1676 (11)	0.027*
H4W	−0.0378 (18)	0.0677 (12)	−0.094 (3)	0.027*
O3W	0.2298 (3)	0.06380 (9)	0.5896 (2)	0.0228 (6)
H5W	0.137 (3)	0.0475 (10)	0.603 (3)	0.034*
H6W	0.256 (4)	0.0798 (11)	0.654 (2)	0.034*
C1	−0.0237 (5)	0.21467 (12)	0.3046 (4)	0.0225 (9)
H1A	−0.0752	0.2109	0.3911	0.027*
H1B	0.0051	0.2470	0.2924	0.027*
C2	−0.1649 (5)	0.19982 (13)	0.2036 (4)	0.0255 (9)
H2A	−0.1831	0.2245	0.1404	0.031*
H2B	−0.2845	0.1949	0.2454	0.031*
C3	−0.1152 (5)	0.15757 (12)	0.1323 (3)	0.0163 (8)
C4	−0.3106 (5)	0.12264 (12)	0.5911 (4)	0.0195 (8)
H4A	−0.4466	0.1262	0.5800	0.023*
H4B	−0.2561	0.1227	0.5048	0.023*
C5	−0.2309 (4)	0.16057 (12)	0.6714 (4)	0.0201 (8)
H5A	−0.2713	0.1900	0.6351	0.024*
H5B	−0.2740	0.1584	0.7607	0.024*
C6	0.0615 (5)	0.18000 (11)	0.7739 (4)	0.0198 (8)
H6A	0.0135	0.1697	0.8571	0.024*
H6B	0.0398	0.2129	0.7661	0.024*
C7	0.2661 (5)	0.17016 (12)	0.7691 (4)	0.0205 (8)
H7A	0.3118	0.1804	0.6851	0.025*
H7B	0.3322	0.1877	0.8374	0.025*
C8	0.3375 (5)	0.10950 (12)	0.9175 (4)	0.0197 (8)
H8A	0.2278	0.1173	0.9678	0.024*
H8B	0.4471	0.1249	0.9568	0.024*
C9	0.3668 (4)	0.05926 (12)	0.9177 (4)	0.0216 (8)
H9A	0.4623	0.0511	0.8554	0.026*
H9B	0.4101	0.0491	1.0044	0.026*
C10	0.2127 (5)	−0.00743 (12)	0.8347 (4)	0.0236 (9)
H10A	0.2632	−0.0275	0.9034	0.028*
H10B	0.2982	−0.0079	0.7620	0.028*
C11	0.0241 (5)	−0.02314 (12)	0.7904 (4)	0.0219 (8)
H11A	0.0305	−0.0546	0.7593	0.026*
H11B	−0.0617	−0.0221	0.8628	0.026*
C12	−0.2365 (4)	0.00224 (12)	0.6619 (4)	0.0201 (8)
H12A	−0.3045	0.0023	0.7431	0.024*
H12B	−0.2649	−0.0262	0.6153	0.024*
C13	−0.2938 (5)	0.04203 (12)	0.5804 (4)	0.0192 (8)
H13A	−0.2174	0.0437	0.5031	0.023*
H13B	−0.4255	0.0392	0.5520	0.023*

	U11	U22	U33	U12	U13	U23
Sn	0.01453 (16)	0.01367 (15)	0.01420 (17)	0.00086 (9)	−0.00119 (11)	−0.00125 (10)
Cl1	0.0302 (5)	0.0175 (4)	0.0149 (5)	−0.0001 (4)	−0.0009 (4)	0.0030 (4)
Cl2	0.0254 (5)	0.0216 (5)	0.0161 (5)	−0.0061 (4)	−0.0053 (4)	0.0014 (4)
Cl3	0.0191 (4)	0.0172 (4)	0.0195 (5)	0.0051 (3)	0.0019 (4)	0.0019 (4)
O1	0.0169 (13)	0.0175 (12)	0.0188 (14)	0.0026 (10)	−0.0062 (10)	−0.0055 (11)
O2	0.0168 (13)	0.0307 (15)	0.0196 (15)	0.0026 (11)	−0.0035 (11)	−0.0100 (13)
O3	0.0264 (14)	0.0175 (13)	0.0155 (14)	0.0019 (10)	−0.0053 (11)	−0.0021 (11)
O4	0.0169 (13)	0.0208 (13)	0.0184 (15)	−0.0001 (10)	0.0010 (11)	−0.0043 (12)
O5	0.0248 (13)	0.0202 (13)	0.0138 (15)	−0.0001 (10)	0.0028 (11)	−0.0006 (11)
O6	0.0137 (12)	0.0207 (13)	0.0248 (15)	0.0007 (10)	−0.0010 (11)	−0.0024 (11)
O7	0.0178 (13)	0.0166 (12)	0.0240 (15)	−0.0002 (10)	0.0019 (11)	0.0037 (11)
O1W	0.0256 (14)	0.0191 (13)	0.0169 (14)	0.0009 (11)	0.0074 (11)	−0.0007 (12)
O2W	0.0178 (13)	0.0218 (13)	0.0149 (14)	0.0031 (11)	−0.0034 (10)	−0.0008 (12)
O3W	0.0274 (15)	0.0230 (14)	0.0183 (15)	−0.0063 (11)	0.0049 (12)	−0.0037 (12)
C1	0.0188 (19)	0.023 (2)	0.026 (2)	0.0051 (15)	−0.0010 (16)	−0.0038 (17)
C2	0.0254 (19)	0.026 (2)	0.025 (2)	0.0078 (17)	−0.0026 (17)	−0.0091 (18)
C3	0.0143 (18)	0.0206 (19)	0.014 (2)	−0.0030 (15)	0.0047 (15)	0.0044 (17)
C4	0.0179 (18)	0.024 (2)	0.017 (2)	0.0047 (15)	−0.0023 (15)	0.0053 (17)
C5	0.0195 (19)	0.0186 (18)	0.022 (2)	0.0033 (14)	0.0034 (16)	0.0022 (17)
C6	0.028 (2)	0.0159 (18)	0.015 (2)	−0.0033 (15)	0.0020 (16)	−0.0063 (15)
C7	0.025 (2)	0.0186 (19)	0.018 (2)	−0.0076 (15)	0.0036 (16)	0.0002 (16)
C8	0.0129 (18)	0.029 (2)	0.017 (2)	−0.0008 (15)	−0.0035 (15)	−0.0019 (17)
C9	0.0153 (18)	0.029 (2)	0.020 (2)	0.0014 (16)	−0.0012 (15)	0.0031 (18)
C10	0.027 (2)	0.0179 (19)	0.026 (2)	0.0065 (15)	0.0012 (17)	0.0086 (18)
C11	0.028 (2)	0.0155 (18)	0.023 (2)	−0.0010 (15)	0.0019 (16)	0.0061 (17)
C12	0.0172 (19)	0.0192 (19)	0.024 (2)	−0.0057 (14)	0.0019 (16)	−0.0086 (17)
C13	0.0199 (18)	0.0215 (19)	0.016 (2)	−0.0014 (15)	−0.0048 (15)	−0.0078 (16)

Sn—C1	2.148 (3)	C2—C3	1.505 (5)
Sn—O1	2.284 (2)	C2—H2A	0.9900
Sn—O1w	2.234 (2)	C2—H2B	0.9900
Sn—Cl1	2.4287 (9)	C4—C5	1.504 (5)
Sn—Cl2	2.4014 (9)	C4—H4A	0.9900
Sn—Cl3	2.3706 (8)	C4—H4B	0.9900
O1—C3	1.233 (4)	C5—H5A	0.9900
O2—C3	1.289 (4)	C5—H5B	0.9900
O2—H1O	0.84 (3)	C6—C7	1.508 (5)
O3—C13	1.417 (4)	C6—H6A	0.9900
O3—C4	1.429 (4)	C6—H6B	0.9900
O4—C6	1.423 (4)	C7—H7A	0.9900
O4—C5	1.440 (4)	C7—H7B	0.9900
O5—C7	1.428 (4)	C8—C9	1.505 (5)
O5—C8	1.441 (4)	C8—H8A	0.9900
O6—C9	1.433 (4)	C8—H8B	0.9900
O6—C10	1.436 (4)	C9—H9A	0.9900
O7—C11	1.424 (4)	C9—H9B	0.9900
O7—C12	1.433 (4)	C10—C11	1.497 (5)
O1W—H1W	0.84 (2)	C10—H10A	0.9900
O1W—H2W	0.84 (3)	C10—H10B	0.9900
O2W—H3W	0.839 (16)	C11—H11A	0.9900
O2W—H4W	0.840 (17)	C11—H11B	0.9900
O3W—H5W	0.84 (2)	C12—C13	1.502 (5)
O3W—H6W	0.84 (3)	C12—H12A	0.9900
C1—C2	1.504 (5)	C12—H12B	0.9900
C1—H1A	0.9900	C13—H13A	0.9900
C1—H1B	0.9900	C13—H13B	0.9900
C1—Sn—O1W	86.48 (12)	O4—C5—H5B	110.2
C1—Sn—O1	78.88 (11)	C4—C5—H5B	110.2
O1W—Sn—O1	85.19 (9)	H5A—C5—H5B	108.5
C1—Sn—Cl3	159.90 (10)	O4—C6—C7	108.9 (3)
O1W—Sn—Cl3	82.27 (6)	O4—C6—H6A	109.9
O1—Sn—Cl3	83.61 (6)	C7—C6—H6A	109.9
C1—Sn—Cl2	101.97 (10)	O4—C6—H6B	109.9
O1W—Sn—Cl2	91.92 (7)	C7—C6—H6B	109.9
O1—Sn—Cl2	176.94 (6)	H6A—C6—H6B	108.3
Cl3—Sn—Cl2	95.03 (3)	O5—C7—C6	113.3 (3)
C1—Sn—Cl1	95.78 (11)	O5—C7—H7A	108.9
O1W—Sn—Cl1	172.17 (7)	C6—C7—H7A	108.9
O1—Sn—Cl1	87.89 (6)	O5—C7—H7B	108.9
Cl3—Sn—Cl1	93.33 (3)	C6—C7—H7B	108.9
Cl2—Sn—Cl1	94.94 (3)	H7A—C7—H7B	107.7
C3—O1—Sn	111.8 (2)	O5—C8—C9	107.5 (3)
C3—O2—H1O	112 (3)	O5—C8—H8A	110.2
C13—O3—C4	114.7 (3)	C9—C8—H8A	110.2
C6—O4—C5	114.1 (3)	O5—C8—H8B	110.2
C7—O5—C8	114.6 (3)	C9—C8—H8B	110.2
C9—O6—C10	114.6 (2)	H8A—C8—H8B	108.5
C11—O7—C12	113.7 (3)	O6—C9—C8	108.7 (3)
Sn—O1W—H1W	121 (2)	O6—C9—H9A	110.0
Sn—O1W—H2W	118 (2)	C8—C9—H9A	110.0
H1W—O1W—H2W	111 (3)	O6—C9—H9B	110.0
H3W—O2W—H4W	112 (3)	C8—C9—H9B	110.0
H5W—O3W—H6W	111 (3)	H9A—C9—H9B	108.3
C2—C1—Sn	110.5 (2)	O6—C10—C11	107.8 (3)
C2—C1—H1A	109.6	O6—C10—H10A	110.1
Sn—C1—H1A	109.6	C11—C10—H10A	110.1
C2—C1—H1B	109.6	O6—C10—H10B	110.1
Sn—C1—H1B	109.6	C11—C10—H10B	110.1
H1A—C1—H1B	108.1	H10A—C10—H10B	108.5
C1—C2—C3	114.8 (3)	O7—C11—C10	108.4 (3)
C1—C2—H2A	108.6	O7—C11—H11A	110.0
C3—C2—H2A	108.6	C10—C11—H11A	110.0
C1—C2—H2B	108.6	O7—C11—H11B	110.0
C3—C2—H2B	108.6	C10—C11—H11B	110.0
H2A—C2—H2B	107.5	H11A—C11—H11B	108.4
O1—C3—O2	122.1 (3)	O7—C12—C13	107.9 (3)
O1—C3—C2	122.5 (3)	O7—C12—H12A	110.1
O2—C3—C2	115.4 (3)	C13—C12—H12A	110.1
O3—C4—C5	107.7 (3)	O7—C12—H12B	110.1
O3—C4—H4A	110.2	C13—C12—H12B	110.1
C5—C4—H4A	110.2	H12A—C12—H12B	108.4
O3—C4—H4B	110.2	O3—C13—C12	107.7 (3)
C5—C4—H4B	110.2	O3—C13—H13A	110.2
H4A—C4—H4B	108.5	C12—C13—H13A	110.2
O4—C5—C4	107.8 (3)	O3—C13—H13B	110.2
O4—C5—H5A	110.2	C12—C13—H13B	110.2
C4—C5—H5A	110.2	H13A—C13—H13B	108.5
C1—Sn—O1—C3	10.9 (2)	C13—O3—C4—C5	−165.7 (3)
O1W—Sn—O1—C3	98.2 (2)	C6—O4—C5—C4	−159.8 (3)
Cl3—Sn—O1—C3	−179.1 (2)	O3—C4—C5—O4	67.1 (3)
Cl2—Sn—O1—C3	117.3 (11)	C5—O4—C6—C7	174.9 (3)
Cl1—Sn—O1—C3	−85.5 (2)	C8—O5—C7—C6	−87.7 (4)
O1W—Sn—C1—C2	−95.8 (3)	O4—C6—C7—O5	−62.2 (4)
O1—Sn—C1—C2	−10.0 (3)	C7—O5—C8—C9	175.7 (3)
Cl3—Sn—C1—C2	−39.8 (5)	C10—O6—C9—C8	158.9 (3)
Cl2—Sn—C1—C2	173.0 (2)	O5—C8—C9—O6	−70.4 (3)
Cl1—Sn—C1—C2	76.7 (3)	C9—O6—C10—C11	−174.4 (3)
Sn—C1—C2—C3	9.1 (4)	C12—O7—C11—C10	−164.0 (3)
Sn—O1—C3—O2	169.4 (3)	O6—C10—C11—O7	61.5 (4)
Sn—O1—C3—C2	−9.3 (4)	C11—O7—C12—C13	165.3 (3)
C1—C2—C3—O1	0.5 (5)	C4—O3—C13—C12	178.0 (3)
C1—C2—C3—O2	−178.3 (3)	O7—C12—C13—O3	−65.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1o···O2w	0.84 (3)	1.71 (3)	2.551 (3)	172 (4)
O1w—H1w···O3w	0.84 (2)	1.85 (3)	2.640 (3)	156 (3)
O1w—H2w···O4	0.84 (3)	1.88 (2)	2.686 (3)	161 (3)
O2w—H3w···O3i	0.839 (16)	1.888 (14)	2.720 (3)	172 (3)
O2w—H4w···O6i	0.840 (17)	1.92 (2)	2.752 (3)	169 (3)
O3w—H5w···O7	0.84 (2)	2.02 (3)	2.827 (3)	162 (3)
O3w—H6w···O5	0.84 (3)	1.91 (3)	2.744 (3)	172 (3)
C8—H8b···O2ii	0.99	2.52	3.491 (4)	165
C12—H12b···O3wiii	0.99	2.42	3.266 (5)	143

Table 1

Selected bond lengths (Å)

Sn—C1	2.148 (3)
Sn—O1	2.284 (2)
Sn—O1w	2.234 (2)
Sn—Cl1	2.4287 (9)
Sn—Cl2	2.4014 (9)
Sn—Cl3	2.3706 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1o⋯O2w	0.84 (3)	1.71 (3)	2.551 (3)	172 (4)
O1w—H1w⋯O3w	0.84 (2)	1.85 (3)	2.640 (3)	156 (3)
O1w—H2w⋯O4	0.84 (3)	1.88 (2)	2.686 (3)	161 (3)
O2w—H3w⋯O3i	0.84 (2)	1.89 (1)	2.720 (3)	172 (3)
O2w—H4w⋯O6i	0.84 (2)	1.92 (2)	2.752 (3)	169 (3)
O3w—H5w⋯O7	0.84 (2)	2.02 (3)	2.827 (3)	162 (3)
O3w—H6w⋯O5	0.84 (3)	1.91 (3)	2.744 (3)	172 (3)
C8—H8b⋯O2ii	0.99	2.52	3.491 (4)	165
C12—H12b⋯O3wiii	0.99	2.42	3.266 (5)	143

Symmetry codes: (i) ; (ii) ; (iii) .