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The mol­ecule of the title compound, [SnCl2(C5H9O2)2], has crystallographic twofold symmetry with the Sn atom lying on the rotation axis. The Sn atom is in a distorted SnC2Cl2O2 octa­hedral geometry with two five-membered chelate rings formed by intra­molecular Sn—O inter­actions [2.551 (2) Å]. The pendant ethyl group is disordered over two positions in a 0.695 (12):0.305 (12) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053731/hb2617sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053731/hb2617Isup2.hkl
Contains datablock I

CCDC reference: 672599

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.024
  • wR factor = 0.063
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Dichlorobis(3-alkoxy-3-oxopropyltins(IV), Cl2Sn(CH2CH2CO2R), known as estertins, have received much attention because of their coordination chemistry and application in PVC stabilizers (Tian et al., 2005). The structures of several estertin compounds, such as dichlorobis(3-methoxy-3-oxopropyltin (Harrison et al., 1979; Ng, 1993), dihalobis(3-methoxy-3-oxopropyl)tin (Balasubramanian et al., 1997) and diiodobis(3-ethoxy-3-oxopropyltin (Howie & Wardell, 2002), have been reported. We report herein the crystal structure of the title compound (Fig. 1).

The coordination geometry about the tin atom in (I) is a distorted octahedron (Fig. 1). The organic groups, EtOCOCH2CH2, act as C4,O-chelating ligands, with the O atoms trans to the cis-chloride ions. The two carbon atoms of the ligands occupy trans positions. The chelate bite angles [72.36 (9)°] are slightly smaller than those [73.3 (2) and 74.0 (2)°] found in dichlorobis(3-methoxy-3-oxopropyltin (Harrison et al., 1979). The Sn—O and Sn—Cl distances are similar to those [2.528 (2) and 2.4054 (9) Å, respectively] in dichlorobis(3-methoxy-3-oxopropyltin (Ng, 1993).

Related literature top

For related structures, see: Balasubramanian et al. (1997); Harrison et al. (1979); Howie & Wardell (2002); Ng (1993). For background, see: Tian et al. (2005).

Experimental top

The title compound was synthesized by the transesterification of (MeOCOCH2CH2)2SnCl2 (1.32 g, 5 mmol) with ethanol (30 ml) according to the reported procedure (Tian et al., 2005). Colourless blocks of (I) were obtained from a solution of chloroform by slow evaporation at room temperature (yield 81%, m.p. 343–344 K).

Refinement top

The ethyl group (C4 and C5) is disordered over two positions with site occupancy factors of 0.695 (12) and 0.305 (12). The C—C distances of the ethyl group were restrained to 1.53 (1) Å. H atoms were placed at calculated positions and were included in the refinement in the riding-model approximation, with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene H atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (H atoms omitted for clarity). For the ethyl group (C4 and C5), the minor disordered component has been omitted for clarity.
Dichloridobis[2-(ethoxycarbonyl)ethyl-κ2C,O]tin(IV) top
Crystal data top
[SnCl2(C5H9O2)2]F(000) = 776
Mr = 391.83Dx = 1.685 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3340 reflections
a = 20.251 (5) Åθ = 2.2–27.0°
b = 9.321 (2) ŵ = 2.00 mm1
c = 9.053 (2) ÅT = 295 K
β = 115.304 (2)°Block, colourless
V = 1544.9 (6) Å30.22 × 0.20 × 0.09 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
1597 independent reflections
Radiation source: fine-focus sealed tube1454 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 2425
Tmin = 0.667, Tmax = 0.841k = 1111
6017 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0293P)2 + 0.6231P]
where P = (Fo2 + 2Fc2)/3
1597 reflections(Δ/σ)max < 0.001
85 parametersΔρmax = 0.37 e Å3
2 restraintsΔρmin = 0.30 e Å3
Crystal data top
[SnCl2(C5H9O2)2]V = 1544.9 (6) Å3
Mr = 391.83Z = 4
Monoclinic, C2/cMo Kα radiation
a = 20.251 (5) ŵ = 2.00 mm1
b = 9.321 (2) ÅT = 295 K
c = 9.053 (2) Å0.22 × 0.20 × 0.09 mm
β = 115.304 (2)°
Data collection top
Bruker APEX CCD
diffractometer
1597 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1454 reflections with I > 2σ(I)
Tmin = 0.667, Tmax = 0.841Rint = 0.024
6017 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0242 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.07Δρmax = 0.37 e Å3
1597 reflectionsΔρmin = 0.30 e Å3
85 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.00000.31014 (3)0.75000.06105 (12)
Cl10.09960 (5)0.47778 (9)0.82861 (10)0.0824 (2)
O10.09330 (14)0.1118 (3)0.7936 (2)0.0886 (7)
O20.15884 (13)0.0386 (3)0.6668 (3)0.0882 (7)
C10.00940 (17)0.2465 (3)0.5166 (3)0.0689 (7)
H1A0.04570.17110.47410.083*
H1B0.02630.32750.44240.083*
C20.06158 (18)0.1935 (3)0.5220 (3)0.0701 (8)
H2A0.05160.13250.42800.084*
H2B0.08990.27490.51460.084*
C30.10580 (17)0.1111 (3)0.6745 (3)0.0659 (7)
C40.2002 (5)0.0523 (10)0.8138 (9)0.094 (2)0.695 (12)
H4A0.23610.00470.90070.113*0.695 (12)
H4B0.16720.09530.85350.113*0.695 (12)
C50.2365 (5)0.1643 (9)0.7589 (11)0.127 (3)0.695 (12)
H5A0.26070.23110.84610.191*0.695 (12)
H5B0.27170.12040.72820.191*0.695 (12)
H5C0.20060.21400.66660.191*0.695 (12)
C4'0.2254 (11)0.0095 (19)0.801 (3)0.094 (2)0.305 (12)
H4C0.23120.03030.90480.113*0.305 (12)
H4D0.26840.01150.78310.113*0.305 (12)
C5'0.2082 (11)0.1677 (19)0.788 (3)0.127 (3)0.305 (12)
H5D0.24650.21780.87530.191*0.305 (12)
H5E0.20440.20320.68500.191*0.305 (12)
H5F0.16280.18270.79500.191*0.305 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0721 (2)0.04839 (17)0.05327 (16)0.0000.01786 (13)0.000
Cl10.0798 (5)0.0725 (5)0.0833 (5)0.0154 (4)0.0236 (4)0.0075 (4)
O10.1139 (18)0.0912 (16)0.0615 (12)0.0366 (14)0.0382 (12)0.0192 (11)
O20.0941 (16)0.0971 (16)0.0656 (12)0.0289 (13)0.0266 (11)0.0012 (11)
C10.0797 (19)0.0659 (16)0.0494 (14)0.0011 (15)0.0164 (13)0.0037 (13)
C20.089 (2)0.0623 (17)0.0550 (15)0.0001 (14)0.0270 (15)0.0033 (12)
C30.0779 (19)0.0535 (15)0.0566 (15)0.0016 (13)0.0195 (14)0.0026 (12)
C40.096 (6)0.113 (6)0.074 (3)0.038 (4)0.037 (3)0.022 (3)
C50.106 (7)0.154 (5)0.127 (5)0.064 (5)0.056 (4)0.036 (4)
C4'0.096 (6)0.113 (6)0.074 (3)0.038 (4)0.037 (3)0.022 (3)
C5'0.106 (7)0.154 (5)0.127 (5)0.064 (5)0.056 (4)0.036 (4)
Geometric parameters (Å, º) top
Sn1—C1i2.123 (3)C2—H2A0.9700
Sn1—C12.123 (3)C2—H2B0.9700
Sn1—Cl12.4062 (9)C4—C51.479 (7)
Sn1—Cl1i2.4062 (9)C4—H4A0.9700
Sn1—O1i2.551 (2)C4—H4B0.9700
Sn1—O12.551 (2)C5—H5A0.9600
O1—C31.208 (3)C5—H5B0.9600
O2—C31.296 (4)C5—H5C0.9600
O2—C4'1.45 (2)C4'—C5'1.508 (10)
O2—C41.496 (8)C4'—H4C0.9700
C1—C21.501 (5)C4'—H4D0.9700
C1—H1A0.9700C5'—H5D0.9600
C1—H1B0.9700C5'—H5E0.9600
C2—C31.498 (4)C5'—H5F0.9600
C1i—Sn1—C1147.58 (17)H2A—C2—H2B107.8
C1i—Sn1—Cl1100.36 (9)O1—C3—O2123.1 (3)
C1—Sn1—Cl1100.54 (9)O1—C3—C2123.3 (3)
C1i—Sn1—Cl1i100.54 (9)O2—C3—C2113.6 (3)
C1—Sn1—Cl1i100.36 (8)C5—C4—O2105.7 (6)
Cl1—Sn1—Cl1i99.01 (5)C5—C4—H4A110.6
C1i—Sn1—O1i72.36 (9)O2—C4—H4A110.6
C1—Sn1—O1i84.17 (10)C5—C4—H4B110.6
Cl1—Sn1—O1i171.24 (6)O2—C4—H4B110.6
Cl1i—Sn1—O1i87.31 (7)H4A—C4—H4B108.7
C1i—Sn1—O184.17 (10)C4—C5—H5A109.5
C1—Sn1—O172.36 (9)C4—C5—H5B109.5
Cl1—Sn1—O187.31 (7)H5A—C5—H5B109.5
Cl1i—Sn1—O1171.24 (6)C4—C5—H5C109.5
O1i—Sn1—O187.10 (12)H5A—C5—H5C109.5
C3—O1—Sn1106.85 (18)H5B—C5—H5C109.5
C3—O2—C4'127.8 (8)O2—C4'—C5'97.8 (14)
C3—O2—C4114.1 (3)O2—C4'—H4C112.2
C2—C1—Sn1112.48 (19)C5'—C4'—H4C112.2
C2—C1—H1A109.1O2—C4'—H4D112.2
Sn1—C1—H1A109.1C5'—C4'—H4D112.2
C2—C1—H1B109.1H4C—C4'—H4D109.8
Sn1—C1—H1B109.1C4'—C5'—H5D109.5
H1A—C1—H1B107.8C4'—C5'—H5E109.5
C3—C2—C1112.7 (3)H5D—C5'—H5E109.5
C3—C2—H2A109.1C4'—C5'—H5F109.5
C1—C2—H2A109.1H5D—C5'—H5F109.5
C3—C2—H2B109.1H5E—C5'—H5F109.5
C1—C2—H2B109.1
C1i—Sn1—O1—C3179.4 (2)Sn1—O1—C3—C210.9 (4)
C1—Sn1—O1—C323.3 (2)C4'—O2—C3—O123.8 (10)
Cl1—Sn1—O1—C378.7 (2)C4—O2—C3—O14.0 (6)
O1i—Sn1—O1—C3108.1 (2)C4'—O2—C3—C2156.3 (9)
C1i—Sn1—C1—C275.5 (2)C4—O2—C3—C2175.9 (5)
Cl1—Sn1—C1—C253.8 (2)C1—C2—C3—O114.1 (4)
Cl1i—Sn1—C1—C2155.14 (19)C1—C2—C3—O2165.9 (3)
O1i—Sn1—C1—C2118.7 (2)C3—O2—C4—C5158.5 (8)
O1—Sn1—C1—C229.9 (2)C4'—O2—C4—C575 (2)
Sn1—C1—C2—C336.4 (3)C3—O2—C4'—C5'109.5 (14)
Sn1—O1—C3—O2169.1 (2)C4—O2—C4'—C5'41.5 (16)
Symmetry code: (i) x, y, z+3/2.

Experimental details

Crystal data
Chemical formula[SnCl2(C5H9O2)2]
Mr391.83
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)20.251 (5), 9.321 (2), 9.053 (2)
β (°) 115.304 (2)
V3)1544.9 (6)
Z4
Radiation typeMo Kα
µ (mm1)2.00
Crystal size (mm)0.22 × 0.20 × 0.09
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.667, 0.841
No. of measured, independent and
observed [I > 2σ(I)] reflections
6017, 1597, 1454
Rint0.024
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.063, 1.07
No. of reflections1597
No. of parameters85
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.30

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top
Sn1—C12.123 (3)Sn1—O12.551 (2)
Sn1—Cl12.4062 (9)
 

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