fac-(2-Amido-ethyl-κC,O)aqua-tri-chlorido-tin(IV) 1,4,7,10,13,16-hexa-oxacyclo-octa-decane (2/1).

The asymmetric unit of the title compound, [Sn(C(3)H(6)NO)Cl(3)(H(2)O)](2)·C(12)H(24)O(6), comprises a six-coordinate tin complex and a 18-crown-6 mol-ecule, 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 mol-ecule. The resulting CCl(3)O(2) donor set defines a distorted octa-hedral geometry. The tin-bound aqua ligand forms O-H⋯O hydrogen bonds to the centrosymmetric 18-crown-6 mol-ecule, resulting in a tri-mol-ecular aggregate. These assemble into a supra-molecular 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 = 894.64

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.090

S = 1.12

3555 reflections

184 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −1.31 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

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

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

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

[Sn(C3H6NO)Cl3(H2O)]2·C12H24O6	F(000) = 888
Mr = 894.64	Dx = 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

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	Rint = 0.062
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −13→13
Tmin = 0.638, Tmax = 0.746	l = −20→20
19526 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)] = 0.030	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(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
3555 reflections	(Δ/σ)max = 0.002
184 parameters	Δρmax = 0.81 e Å−3
6 restraints	Δρmin = −1.31 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	0.78251 (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*

	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)

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)

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)

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) ; (ii) .