Bis(2-carboethoxy­ethyl)­di­iodo­tin at 120 K

In the structure of the title compound, [Sn(C₁₀H₁₈O₄)I₂], Sn lies on a crystallographic twofold axis and the mol­ecule therefore has C₂ molecular symmetry. As is usual for an ester-tin compound of this kind, the carbonyl O atom of the carboethoxy moiety bonds to Sn, creating a five-membered chelate ring and, due to the molecular symmetry, renders Sn six-coordinate.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.038
• wR factor = 0.077
• Data-to-parameter ratio = 24.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      6.341
          Tmax scaled      0.900 Tmin scaled      0.717

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

Bis(2-carboethoxyethyl)diiodotin

Crystal data

[Sn(C10H18O4)I2]	F(000) = 1064
Mr = 574.73	Dx = 2.293 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.9399 (10) Å	Cell parameters from 2840 reflections
b = 9.1673 (5) Å	θ = 2.9–27.5°
c = 9.6144 (5) Å	µ = 5.24 mm^−1
β = 115.559 (3)°	T = 120 K
V = 1664.99 (15) Å^3	Prism, colourless
Z = 4	0.05 × 0.02 × 0.02 mm

Data collection

Enraf-Nonius KappaCCD area-detector diffractometer	1898 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode	1390 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
φ and ω scans to fill the Ewald sphere	h = −27→22
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −10→11
Tmin = 0.113, Tmax = 0.142	l = −12→10
5078 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 0.89	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2)]
1898 reflections	(Δ/σ)max < 0.001
79 parameters	Δρmax = 1.51 e Å^−3
0 restraints	Δρmin = −1.17 e Å^−3

Special details

Experimental. Lattice absent reflections not present in input intensity data so that completeness of data is in fact twice that computed by SHELXL i.e. 93.4%.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Assymmetric unit consists of Sn in 4 e s pecial positions and representative I and a complete alkyl ester group in the general (8f) positions.

Anisotropic displacement parameters refined for all non-H atoms. H atoms in calculated positions and refined with a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.0000	0.20062 (6)	0.7500	0.01956 (17)
I1	−0.11478 (2)	0.00964 (4)	0.64925 (5)	0.02590 (15)
C1	−0.0047 (3)	0.2568 (6)	0.5308 (6)	0.0238 (13)
H1A	−0.0159	0.1685	0.4651	0.029*
H1B	−0.0431	0.3285	0.4798	0.029*
C2	0.0652 (3)	0.3213 (6)	0.5458 (6)	0.0249 (13)
H2A	0.0978	0.2410	0.5510	0.030*
H2B	0.0564	0.3802	0.4530	0.030*
C3	0.0999 (3)	0.4158 (6)	0.6870 (6)	0.0225 (13)
O1	0.0838 (2)	0.4114 (4)	0.7953 (4)	0.0259 (9)
O2	0.1490 (2)	0.5013 (4)	0.6825 (4)	0.0223 (10)
C4	0.1854 (3)	0.5996 (6)	0.8135 (6)	0.0280 (14)
H4A	0.2146	0.5427	0.9071	0.034*
H4B	0.1505	0.6572	0.8343	0.034*
C5	0.2312 (3)	0.6983 (6)	0.7727 (7)	0.0339 (15)
H5A	0.2644	0.6400	0.7488	0.051*
H5B	0.2577	0.7630	0.8599	0.051*
H5C	0.2016	0.7570	0.6826	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0238 (3)	0.0163 (3)	0.0198 (3)	0.000	0.0105 (2)	0.000
I1	0.0264 (3)	0.0228 (2)	0.0295 (2)	−0.00501 (16)	0.0131 (2)	−0.00468 (17)
C1	0.032 (4)	0.021 (3)	0.017 (3)	0.003 (3)	0.010 (3)	−0.001 (3)
C2	0.031 (4)	0.024 (3)	0.022 (3)	−0.002 (3)	0.014 (3)	−0.002 (3)
C3	0.023 (3)	0.017 (3)	0.027 (3)	0.002 (3)	0.011 (3)	0.003 (3)
O1	0.030 (2)	0.030 (2)	0.024 (2)	−0.0114 (18)	0.017 (2)	−0.0028 (19)
O2	0.027 (2)	0.020 (2)	0.020 (2)	−0.0027 (17)	0.010 (2)	−0.0026 (17)
C4	0.032 (4)	0.022 (3)	0.030 (3)	−0.004 (3)	0.014 (3)	−0.003 (3)
C5	0.031 (4)	0.030 (4)	0.044 (4)	−0.007 (3)	0.020 (3)	−0.004 (3)

Geometric parameters (Å, º)

Sn1—C1	2.131 (5)	C3—O1	1.226 (6)
Sn1—O1	2.518 (4)	C3—O2	1.309 (6)
Sn1—I1	2.7877 (5)	O2—C4	1.467 (6)
C1—C2	1.526 (8)	C4—C5	1.489 (8)
C1—H1A	0.9900	C4—H4A	0.9900
C1—H1B	0.9900	C4—H4B	0.9900
C2—C3	1.506 (7)	C5—H5A	0.9800
C2—H2A	0.9900	C5—H5B	0.9800
C2—H2B	0.9900	C5—H5C	0.9800
C1—Sn1—C1^i	152.0 (3)	C1—C2—H2B	109.2
C1—Sn1—O1	73.55 (17)	H2A—C2—H2B	107.9
C1—Sn1—O1^i	84.99 (17)	O1—C3—O2	123.8 (5)
O1—Sn1—O1^i	79.80 (18)	O1—C3—C2	123.0 (5)
C1—Sn1—I1^i	99.21 (15)	O2—C3—C2	113.3 (5)
O1—Sn1—I1^i	89.42 (9)	C3—O1—Sn1	107.8 (4)
C1—Sn1—I1	98.24 (15)	C3—O2—C4	117.7 (4)
O1—Sn1—I1	166.87 (9)	O2—C4—C5	107.6 (4)
I1—Sn1—I1^i	102.19 (2)	O2—C4—H4A	110.2
C2—C1—Sn1	111.5 (3)	C5—C4—H4A	110.2
C2—C1—H1A	109.3	O2—C4—H4B	110.2
Sn1—C1—H1A	109.3	C5—C4—H4B	110.2
C2—C1—H1B	109.3	H4A—C4—H4B	108.5
Sn1—C1—H1B	109.3	C4—C5—H5A	109.5
H1A—C1—H1B	108.0	C4—C5—H5B	109.5
C3—C2—C1	112.2 (4)	H5A—C5—H5B	109.5
C3—C2—H2A	109.2	C4—C5—H5C	109.5
C1—C2—H2A	109.2	H5A—C5—H5C	109.5
C3—C2—H2B	109.2	H5B—C5—H5C	109.5
C1^i—Sn1—C1—C2	70.7 (4)	C2—C3—O1—Sn1	7.7 (6)
O1—Sn1—C1—C2	29.3 (4)	C1—Sn1—O1—C3	−21.5 (4)
O1^i—Sn1—C1—C2	110.1 (4)	C1^i—Sn1—O1—C3	176.6 (4)
I1^i—Sn1—C1—C2	−57.3 (4)	O1^i—Sn1—O1—C3	−109.2 (4)
I1—Sn1—C1—C2	−161.2 (4)	I1^i—Sn1—O1—C3	78.3 (4)
Sn1—C1—C2—C3	−36.8 (6)	I1—Sn1—O1—C3	−74.0 (6)
C1—C2—C3—O1	17.3 (8)	O1—C3—O2—C4	−1.5 (8)
C1—C2—C3—O2	−163.3 (5)	C2—C3—O2—C4	179.1 (4)
O2—C3—O1—Sn1	−171.7 (4)	C3—O2—C4—C5	−172.6 (5)

Symmetry code: (i) −x, y, −z+3/2.