Acta Cryst. (2007). E63, m2917 [ doi:10.1107/S1600536807053731 ]
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2C,O]tin(IV)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.
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).
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.
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).
![[Figure 1]](./hb2617fig1thm.gif)
| 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. |
| [SnCl2(C5H9O2)2] | F000 = 776 |
| Mr = 391.83 | Dx = 1.685 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 3340 reflections |
| a = 20.251 (5) Å | θ = 2.2–27.0º |
| b = 9.321 (2) Å | µ = 2.00 mm−1 |
| c = 9.053 (2) Å | T = 295 (2) K |
| β = 115.304 (2)º | Block, colourless |
| V = 1544.9 (6) Å3 | 0.22 × 0.20 × 0.09 mm |
| Z = 4 |
| Bruker APEX CCD diffractometer | 1597 independent reflections |
| Radiation source: fine-focus sealed tube | 1454 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.024 |
| T = 295(2) K | θmax = 26.5º |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −24→25 |
| Tmin = 0.667, Tmax = 0.841 | k = −11→11 |
| 6017 measured reflections | l = −11→11 |
| 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)] = 0.024 | H-atom parameters constrained |
| wR(F2) = 0.063 | w = 1/[σ2(Fo2) + (0.0293P)2 + 0.6231P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 1597 reflections | Δρmax = 0.37 e Å−3 |
| 85 parameters | Δρmin = −0.29 e Å−3 |
| 2 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [SnCl2(C5H9O2)2] | V = 1544.9 (6) Å3 |
| Mr = 391.83 | Z = 4 |
| Monoclinic, C2/c | Mo Kα |
| a = 20.251 (5) Å | µ = 2.00 mm−1 |
| b = 9.321 (2) Å | T = 295 (2) K |
| c = 9.053 (2) Å | 0.22 × 0.20 × 0.09 mm |
| β = 115.304 (2)º |
| Bruker APEX CCD diffractometer | 1597 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1454 reflections with I > 2σ(I) |
| Tmin = 0.667, Tmax = 0.841 | Rint = 0.024 |
| 6017 measured reflections |
| R[F2 > 2σ(F2)] = 0.024 | 2 restraints |
| wR(F2) = 0.063 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.37 e Å−3 |
| 1597 reflections | Δρmin = −0.29 e Å−3 |
| 85 parameters |
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. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Sn1 | 0.0000 | 0.31014 (3) | 0.7500 | 0.06105 (12) | |
| Cl1 | 0.09960 (5) | 0.47778 (9) | 0.82861 (10) | 0.0824 (2) | |
| O1 | 0.09330 (14) | 0.1118 (3) | 0.7936 (2) | 0.0886 (7) | |
| O2 | 0.15884 (13) | 0.0386 (3) | 0.6668 (3) | 0.0882 (7) | |
| C1 | −0.00940 (17) | 0.2465 (3) | 0.5166 (3) | 0.0689 (7) | |
| H1A | −0.0457 | 0.1711 | 0.4741 | 0.083* | |
| H1B | −0.0263 | 0.3275 | 0.4424 | 0.083* | |
| C2 | 0.06158 (18) | 0.1935 (3) | 0.5220 (3) | 0.0701 (8) | |
| H2A | 0.0516 | 0.1325 | 0.4280 | 0.084* | |
| H2B | 0.0899 | 0.2749 | 0.5146 | 0.084* | |
| C3 | 0.10580 (17) | 0.1111 (3) | 0.6745 (3) | 0.0659 (7) | |
| C4 | 0.2002 (5) | −0.0523 (10) | 0.8138 (9) | 0.094 (2) | 0.695 (12) |
| H4A | 0.2361 | 0.0047 | 0.9007 | 0.113* | 0.695 (12) |
| H4B | 0.1672 | −0.0953 | 0.8535 | 0.113* | 0.695 (12) |
| C5 | 0.2365 (5) | −0.1643 (9) | 0.7589 (11) | 0.127 (3) | 0.695 (12) |
| H5A | 0.2607 | −0.2311 | 0.8461 | 0.191* | 0.695 (12) |
| H5B | 0.2717 | −0.1204 | 0.7282 | 0.191* | 0.695 (12) |
| H5C | 0.2006 | −0.2140 | 0.6666 | 0.191* | 0.695 (12) |
| C4' | 0.2254 (11) | −0.0095 (19) | 0.801 (3) | 0.094 (2) | 0.305 (12) |
| H4C | 0.2312 | 0.0303 | 0.9048 | 0.113* | 0.305 (12) |
| H4D | 0.2684 | 0.0115 | 0.7831 | 0.113* | 0.305 (12) |
| C5' | 0.2082 (11) | −0.1677 (19) | 0.788 (3) | 0.127 (3) | 0.305 (12) |
| H5D | 0.2465 | −0.2178 | 0.8753 | 0.191* | 0.305 (12) |
| H5E | 0.2044 | −0.2032 | 0.6850 | 0.191* | 0.305 (12) |
| H5F | 0.1628 | −0.1827 | 0.7950 | 0.191* | 0.305 (12) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0721 (2) | 0.04839 (17) | 0.05327 (16) | 0.000 | 0.01786 (13) | 0.000 |
| Cl1 | 0.0798 (5) | 0.0725 (5) | 0.0833 (5) | −0.0154 (4) | 0.0236 (4) | −0.0075 (4) |
| O1 | 0.1139 (18) | 0.0912 (16) | 0.0615 (12) | 0.0366 (14) | 0.0382 (12) | 0.0192 (11) |
| O2 | 0.0941 (16) | 0.0971 (16) | 0.0656 (12) | 0.0289 (13) | 0.0266 (11) | 0.0012 (11) |
| C1 | 0.0797 (19) | 0.0659 (16) | 0.0494 (14) | 0.0011 (15) | 0.0164 (13) | 0.0037 (13) |
| C2 | 0.089 (2) | 0.0623 (17) | 0.0550 (15) | −0.0001 (14) | 0.0270 (15) | 0.0033 (12) |
| C3 | 0.0779 (19) | 0.0535 (15) | 0.0566 (15) | 0.0016 (13) | 0.0195 (14) | −0.0026 (12) |
| 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) |
| 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) |
| Sn1—C1i | 2.123 (3) | C2—H2A | 0.9700 |
| Sn1—C1 | 2.123 (3) | C2—H2B | 0.9700 |
| Sn1—Cl1 | 2.4062 (9) | C4—C5 | 1.479 (7) |
| Sn1—Cl1i | 2.4062 (9) | C4—H4A | 0.9700 |
| Sn1—O1i | 2.551 (2) | C4—H4B | 0.9700 |
| Sn1—O1 | 2.551 (2) | C5—H5A | 0.9600 |
| O1—C3 | 1.208 (3) | C5—H5B | 0.9600 |
| O2—C3 | 1.296 (4) | C5—H5C | 0.9600 |
| O2—C4' | 1.45 (2) | C4'—C5' | 1.508 (10) |
| O2—C4 | 1.496 (8) | C4'—H4C | 0.9700 |
| C1—C2 | 1.501 (5) | C4'—H4D | 0.9700 |
| C1—H1A | 0.9700 | C5'—H5D | 0.9600 |
| C1—H1B | 0.9700 | C5'—H5E | 0.9600 |
| C2—C3 | 1.498 (4) | C5'—H5F | 0.9600 |
| C1i—Sn1—C1 | 147.58 (17) | H2A—C2—H2B | 107.8 |
| C1i—Sn1—Cl1 | 100.36 (9) | O1—C3—O2 | 123.1 (3) |
| C1—Sn1—Cl1 | 100.54 (9) | O1—C3—C2 | 123.3 (3) |
| C1i—Sn1—Cl1i | 100.54 (9) | O2—C3—C2 | 113.6 (3) |
| C1—Sn1—Cl1i | 100.36 (8) | C5—C4—O2 | 105.7 (6) |
| Cl1—Sn1—Cl1i | 99.01 (5) | C5—C4—H4A | 110.6 |
| C1i—Sn1—O1i | 72.36 (9) | O2—C4—H4A | 110.6 |
| C1—Sn1—O1i | 84.17 (10) | C5—C4—H4B | 110.6 |
| Cl1—Sn1—O1i | 171.24 (6) | O2—C4—H4B | 110.6 |
| Cl1i—Sn1—O1i | 87.31 (7) | H4A—C4—H4B | 108.7 |
| C1i—Sn1—O1 | 84.17 (10) | C4—C5—H5A | 109.5 |
| C1—Sn1—O1 | 72.36 (9) | C4—C5—H5B | 109.5 |
| Cl1—Sn1—O1 | 87.31 (7) | H5A—C5—H5B | 109.5 |
| Cl1i—Sn1—O1 | 171.24 (6) | C4—C5—H5C | 109.5 |
| O1i—Sn1—O1 | 87.10 (12) | H5A—C5—H5C | 109.5 |
| C3—O1—Sn1 | 106.85 (18) | H5B—C5—H5C | 109.5 |
| C3—O2—C4' | 127.8 (8) | O2—C4'—C5' | 97.8 (14) |
| C3—O2—C4 | 114.1 (3) | O2—C4'—H4C | 112.2 |
| C2—C1—Sn1 | 112.48 (19) | C5'—C4'—H4C | 112.2 |
| C2—C1—H1A | 109.1 | O2—C4'—H4D | 112.2 |
| Sn1—C1—H1A | 109.1 | C5'—C4'—H4D | 112.2 |
| C2—C1—H1B | 109.1 | H4C—C4'—H4D | 109.8 |
| Sn1—C1—H1B | 109.1 | C4'—C5'—H5D | 109.5 |
| H1A—C1—H1B | 107.8 | C4'—C5'—H5E | 109.5 |
| C3—C2—C1 | 112.7 (3) | H5D—C5'—H5E | 109.5 |
| C3—C2—H2A | 109.1 | C4'—C5'—H5F | 109.5 |
| C1—C2—H2A | 109.1 | H5D—C5'—H5F | 109.5 |
| C3—C2—H2B | 109.1 | H5E—C5'—H5F | 109.5 |
| C1—C2—H2B | 109.1 | ||
| C1i—Sn1—O1—C3 | −179.4 (2) | Sn1—O1—C3—C2 | −10.9 (4) |
| C1—Sn1—O1—C3 | 23.3 (2) | C4'—O2—C3—O1 | −23.8 (10) |
| Cl1—Sn1—O1—C3 | −78.7 (2) | C4—O2—C3—O1 | 4.0 (6) |
| O1i—Sn1—O1—C3 | 108.1 (2) | C4'—O2—C3—C2 | 156.3 (9) |
| C1i—Sn1—C1—C2 | −75.5 (2) | C4—O2—C3—C2 | −175.9 (5) |
| Cl1—Sn1—C1—C2 | 53.8 (2) | C1—C2—C3—O1 | −14.1 (4) |
| Cl1i—Sn1—C1—C2 | 155.14 (19) | C1—C2—C3—O2 | 165.9 (3) |
| O1i—Sn1—C1—C2 | −118.7 (2) | C3—O2—C4—C5 | 158.5 (8) |
| O1—Sn1—C1—C2 | −29.9 (2) | C4'—O2—C4—C5 | −75 (2) |
| Sn1—C1—C2—C3 | 36.4 (3) | C3—O2—C4'—C5' | 109.5 (14) |
| Sn1—O1—C3—O2 | 169.1 (2) | C4—O2—C4'—C5' | 41.5 (16) |
| Symmetry codes: (i) −x, y, −z+3/2. |
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Tian, L., Yu, Q., Shang, Z., Sun, Y. & Zhang, L. (2005). Appl. Organomet. Chem. 19, 677–682.
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).