Acta Cryst. (2009). E65, m609-m610 [ doi:10.1107/S1600536809015475 ]
![[mu]](/logos/entities/mu_rmgif.gif)
3-oxido-bis(2-thiophene-3-acetato-![[kappa]](/logos/entities/kappa_rmgif.gif)
2O:O')(thiophene-3-acetato-O)tetratin(IV)In the centrosymmetric title compound, [Sn4(CH3)8(C6H5O2S)4O2], the central four-membered planar ring (Sn2O2) makes dihedral angles of 66.28 (12) and 77.43 (11)° with the heterocyclic rings of the bridging and monodentate ligands, respectively. One SnIV atom adopts a distorted SnO3C2 trigonal-bipyramidal geometry, with both C atoms in equatorial sites and the other a grossly distorted SnO4C2 octahedral or irregular arrangement. In the crystal, the molecules are connected into pillar-like polymeric units making R22(12) ring motifs due to intermolecular C-H
O interactions. C-H![[pi]](/logos/entities/pi_rmgif.gif)
interactions are also present. The O atoms of the chelating ligands and the S atom of the monodentate ligand are disordered over two sets of sites in a 0.65 (6):0.35 (6) ratio
The complex was synthesized by refluxing (CH3)2SnO (1.66 g, 0.01 mol) and 3-thiopheneacetic acid (1.42 g, 0.01 mol) under argon, in toluene for 4–6 h. Water formed during the reaction was continuously removed by the use of Dean-Stark apparatus. The reaction mixture was brought to room temperature and then boiled with anhydrous activated charcoal and filtered through alumina column. Toluene was removed completely from the filtrate under vacuum. The solid mass thus obtained was purified by repeated crystallization from chloroform-ethanol (8:2) mixture, to obtain colourless prisms of (I).
The H-atoms were positioned geometrically (C—H = 0.93–0.97Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./hb2953fig1thm.gif)
| Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are not shown for clarity. |
| [Sn4(CH3)8(C6H5O2S)4O2] | Z = 1 |
| Mr = 1191.79 | F(000) = 580 |
| Triclinic, P1 | Dx = 1.840 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.7330 (5) Å | Cell parameters from 3441 reflections |
| b = 9.7403 (5) Å | θ = 2.2–25.5° |
| c = 12.0432 (6) Å | µ = 2.54 mm−1 |
| α = 85.407 (2)° | T = 296 K |
| β = 85.259 (1)° | Prism, colourless |
| γ = 71.256 (2)° | 0.20 × 0.15 × 0.13 mm |
| V = 1075.74 (10) Å3 |
| Bruker Kappa APEXII CCD diffractometer | 4012 independent reflections |
| Radiation source: fine-focus sealed tube | 3441 reflections with I > 2σ(I) |
| graphite | Rint = 0.025 |
| Detector resolution: 7.80 pixels mm-1 | θmax = 25.5°, θmin = 2.2° |
| ω scans | h = −11→11 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −11→11 |
| Tmin = 0.637, Tmax = 0.719 | l = −14→14 |
| 19310 measured reflections |
| 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) = 0.059 | w = 1/[σ2(Fo2) + (0.0219P)2 + 1.4193P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 4012 reflections | Δρmax = 0.84 e Å−3 |
| 250 parameters | Δρmin = −0.65 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00156 (19) |
| [Sn4(CH3)8(C6H5O2S)4O2] | γ = 71.256 (2)° |
| Mr = 1191.79 | V = 1075.74 (10) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 9.7330 (5) Å | Mo Kα radiation |
| b = 9.7403 (5) Å | µ = 2.54 mm−1 |
| c = 12.0432 (6) Å | T = 296 K |
| α = 85.407 (2)° | 0.20 × 0.15 × 0.13 mm |
| β = 85.259 (1)° |
| Bruker Kappa APEXII CCD diffractometer | 4012 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3441 reflections with I > 2σ(I) |
| Tmin = 0.637, Tmax = 0.719 | Rint = 0.025 |
| 19310 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
| wR(F2) = 0.059 | Δρmax = 0.84 e Å−3 |
| S = 1.03 | Δρmin = −0.65 e Å−3 |
| 4012 reflections | Absolute structure: ? |
| 250 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.18885 (2) | 0.25808 (2) | 0.45386 (2) | 0.0444 (1) | |
| Sn2 | 0.48666 (2) | −0.09190 (2) | 0.39587 (2) | 0.0446 (1) | |
| S1 | 0.27895 (18) | −0.25877 (16) | −0.05837 (11) | 0.0934 (5) | |
| S2A | 0.3409 (3) | 0.25077 (19) | 0.99888 (15) | 0.1310 (8) | 0.635 |
| O1A | 0.1177 (13) | 0.137 (3) | 0.333 (2) | 0.076 (4) | 0.65 (6) |
| O2A | 0.3179 (12) | −0.023 (3) | 0.2610 (14) | 0.065 (4) | 0.65 (6) |
| O3 | 0.3779 (2) | 0.0937 (2) | 0.47382 (18) | 0.0410 (7) | |
| O4 | 0.2813 (3) | 0.3298 (3) | 0.5913 (2) | 0.0584 (9) | |
| O5 | 0.0925 (4) | 0.5232 (4) | 0.5897 (3) | 0.1044 (16) | |
| C1 | 0.1856 (4) | 0.0434 (4) | 0.2645 (3) | 0.0497 (12) | |
| C2 | 0.0913 (4) | 0.0161 (4) | 0.1808 (3) | 0.0562 (12) | |
| C3 | 0.1613 (4) | −0.1092 (4) | 0.1087 (3) | 0.0532 (12) | |
| C4 | 0.1850 (5) | −0.2556 (5) | 0.1418 (4) | 0.0771 (19) | |
| C5 | 0.2468 (5) | −0.3522 (5) | 0.0595 (4) | 0.0719 (16) | |
| C6 | 0.2094 (6) | −0.0968 (5) | 0.0020 (4) | 0.0756 (19) | |
| C7 | 0.2415 (5) | 0.4034 (5) | 0.3342 (4) | 0.0789 (17) | |
| C8 | 0.0351 (4) | 0.1981 (5) | 0.5611 (4) | 0.0822 (18) | |
| C9 | 0.3936 (5) | −0.2493 (5) | 0.4656 (5) | 0.089 (2) | |
| C10 | 0.6134 (5) | −0.0291 (5) | 0.2633 (3) | 0.0712 (16) | |
| C11 | 0.2064 (5) | 0.4535 (4) | 0.6276 (3) | 0.0628 (14) | |
| C12 | 0.2698 (6) | 0.5070 (5) | 0.7194 (4) | 0.0832 (19) | |
| C13 | 0.2700 (5) | 0.4165 (4) | 0.8259 (3) | 0.0607 (14) | |
| C14 | 0.1451 (6) | 0.4020 (6) | 0.8834 (4) | 0.0840 (19) | |
| C15 | 0.1689 (6) | 0.3121 (5) | 0.9827 (4) | 0.0761 (19) | |
| C16 | 0.3894 (5) | 0.3378 (6) | 0.8800 (4) | 0.0839 (19) | |
| S2B | 0.3409 (3) | 0.25077 (19) | 0.99888 (15) | 0.1310 (8) | 0.365 |
| O2B | 0.283 (5) | −0.0624 (18) | 0.299 (4) | 0.065 (7) | 0.35 (6) |
| O1B | 0.156 (5) | 0.168 (2) | 0.296 (3) | 0.062 (7) | 0.35 (6) |
| H2A | 0.00668 | 0.00014 | 0.22101 | 0.0672* | |
| H4 | 0.16091 | −0.28575 | 0.21394 | 0.0921* | |
| H5 | 0.26718 | −0.45241 | 0.06791 | 0.0864* | |
| H7A | 0.19235 | 0.40649 | 0.26765 | 0.1183* | |
| H7B | 0.34458 | 0.37212 | 0.31712 | 0.1183* | |
| H6A | 0.20504 | −0.00826 | −0.03533 | 0.0906* | |
| H2B | 0.05705 | 0.10329 | 0.13256 | 0.0672* | |
| H8B | 0.05988 | 0.09419 | 0.56672 | 0.1230* | |
| H8C | −0.05934 | 0.23970 | 0.53209 | 0.1230* | |
| H9A | 0.30262 | −0.20216 | 0.50480 | 0.1329* | |
| H9B | 0.45826 | −0.31449 | 0.51661 | 0.1329* | |
| H9C | 0.37745 | −0.30285 | 0.40721 | 0.1329* | |
| H10A | 0.67382 | 0.01893 | 0.29210 | 0.1063* | |
| H10B | 0.55061 | 0.03594 | 0.21106 | 0.1063* | |
| H10C | 0.67335 | −0.11358 | 0.22649 | 0.1063* | |
| H12A | 0.36857 | 0.50390 | 0.69644 | 0.0997* | |
| H12B | 0.21327 | 0.60710 | 0.73188 | 0.0997* | |
| H14 | 0.05271 | 0.44812 | 0.85838 | 0.1013* | |
| H15 | 0.09708 | 0.29176 | 1.03071 | 0.0912* | |
| H16A | 0.48440 | 0.33181 | 0.85601 | 0.1007* | |
| H7C | 0.21167 | 0.49849 | 0.36272 | 0.1183* | |
| H8A | 0.03409 | 0.23280 | 0.63361 | 0.1230* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0437 (1) | 0.0386 (1) | 0.0463 (2) | −0.0034 (1) | −0.0056 (1) | −0.0128 (1) |
| Sn2 | 0.0470 (1) | 0.0397 (1) | 0.0452 (2) | −0.0066 (1) | −0.0063 (1) | −0.0177 (1) |
| S1 | 0.1234 (11) | 0.0908 (9) | 0.0681 (8) | −0.0294 (8) | −0.0098 (7) | −0.0323 (7) |
| S2A | 0.206 (2) | 0.0932 (11) | 0.0868 (11) | −0.0321 (12) | −0.0320 (12) | −0.0049 (9) |
| O1A | 0.058 (4) | 0.088 (8) | 0.084 (8) | −0.016 (4) | −0.007 (4) | −0.050 (7) |
| O2A | 0.054 (4) | 0.091 (10) | 0.051 (5) | −0.015 (4) | −0.010 (3) | −0.032 (5) |
| O3 | 0.0391 (11) | 0.0368 (12) | 0.0424 (12) | −0.0025 (9) | −0.0042 (9) | −0.0133 (9) |
| O4 | 0.0644 (16) | 0.0503 (14) | 0.0575 (16) | −0.0070 (12) | −0.0136 (12) | −0.0216 (12) |
| O5 | 0.099 (3) | 0.078 (2) | 0.108 (3) | 0.0243 (19) | −0.031 (2) | −0.036 (2) |
| C1 | 0.056 (2) | 0.051 (2) | 0.047 (2) | −0.0207 (18) | −0.0110 (17) | −0.0073 (17) |
| C2 | 0.063 (2) | 0.057 (2) | 0.052 (2) | −0.0193 (18) | −0.0162 (18) | −0.0092 (17) |
| C3 | 0.061 (2) | 0.057 (2) | 0.049 (2) | −0.0237 (18) | −0.0167 (17) | −0.0112 (17) |
| C4 | 0.103 (4) | 0.065 (3) | 0.073 (3) | −0.041 (3) | 0.002 (3) | −0.008 (2) |
| C5 | 0.095 (3) | 0.052 (2) | 0.077 (3) | −0.033 (2) | 0.002 (2) | −0.019 (2) |
| C6 | 0.116 (4) | 0.063 (3) | 0.052 (3) | −0.030 (3) | −0.016 (2) | −0.010 (2) |
| C7 | 0.099 (3) | 0.062 (3) | 0.059 (3) | −0.006 (2) | 0.000 (2) | 0.008 (2) |
| C8 | 0.051 (2) | 0.075 (3) | 0.117 (4) | −0.019 (2) | 0.014 (2) | −0.008 (3) |
| C9 | 0.066 (3) | 0.067 (3) | 0.143 (5) | −0.033 (2) | −0.002 (3) | −0.016 (3) |
| C10 | 0.088 (3) | 0.065 (3) | 0.047 (2) | −0.008 (2) | 0.007 (2) | −0.0032 (19) |
| C11 | 0.083 (3) | 0.049 (2) | 0.054 (2) | −0.013 (2) | −0.009 (2) | −0.0174 (18) |
| C12 | 0.137 (4) | 0.069 (3) | 0.058 (3) | −0.047 (3) | −0.012 (3) | −0.021 (2) |
| C13 | 0.077 (3) | 0.059 (2) | 0.052 (2) | −0.024 (2) | −0.005 (2) | −0.0255 (19) |
| C14 | 0.076 (3) | 0.085 (3) | 0.095 (4) | −0.028 (3) | 0.009 (3) | −0.032 (3) |
| C15 | 0.095 (4) | 0.067 (3) | 0.072 (3) | −0.037 (3) | 0.017 (3) | −0.013 (2) |
| C16 | 0.076 (3) | 0.098 (4) | 0.079 (3) | −0.022 (3) | −0.008 (2) | −0.032 (3) |
| S2B | 0.206 (2) | 0.0932 (11) | 0.0868 (11) | −0.0321 (12) | −0.0320 (12) | −0.0049 (9) |
| O2B | 0.075 (12) | 0.052 (7) | 0.076 (15) | −0.021 (5) | −0.033 (12) | −0.012 (7) |
| O1B | 0.076 (15) | 0.047 (7) | 0.062 (11) | −0.011 (6) | −0.025 (9) | −0.021 (6) |
| Sn1—O1A | 2.23 (2) | C3—C6 | 1.341 (6) |
| Sn1—O3 | 2.031 (2) | C4—C5 | 1.384 (7) |
| Sn1—O4 | 2.207 (3) | C11—C12 | 1.512 (7) |
| Sn1—C7 | 2.088 (5) | C12—C13 | 1.497 (6) |
| Sn1—C8 | 2.091 (4) | C13—C16 | 1.355 (7) |
| Sn1—O1B | 2.24 (4) | C13—C14 | 1.390 (8) |
| Sn2—O2A | 2.312 (17) | C14—C15 | 1.414 (7) |
| Sn2—O3 | 2.0366 (19) | C2—H2A | 0.9700 |
| Sn2—C9 | 2.106 (5) | C2—H2B | 0.9700 |
| Sn2—C10 | 2.109 (4) | C4—H4 | 0.9300 |
| Sn2—O3i | 2.127 (2) | C5—H5 | 0.9300 |
| Sn2—O4i | 2.670 (3) | C6—H6A | 0.9300 |
| Sn2—O2B | 2.31 (5) | C7—H7A | 0.9600 |
| Sn2—Sn2i | 3.2694 (4) | C7—H7B | 0.9600 |
| S1—C5 | 1.686 (5) | C7—H7C | 0.9600 |
| S1—C6 | 1.701 (5) | C8—H8A | 0.9600 |
| S2A—C15 | 1.609 (7) | C8—H8B | 0.9600 |
| S2A—C16 | 1.715 (5) | C8—H8C | 0.9600 |
| S2B—C16 | 1.715 (5) | C9—H9A | 0.9600 |
| S2B—C15 | 1.609 (7) | C9—H9B | 0.9600 |
| O1A—C1 | 1.26 (3) | C9—H9C | 0.9600 |
| O1B—C1 | 1.24 (2) | C10—H10A | 0.9600 |
| O2A—C1 | 1.240 (19) | C10—H10B | 0.9600 |
| O2B—C1 | 1.23 (3) | C10—H10C | 0.9600 |
| O4—C11 | 1.281 (5) | C12—H12A | 0.9700 |
| O5—C11 | 1.204 (6) | C12—H12B | 0.9700 |
| C1—C2 | 1.511 (5) | C14—H14 | 0.9300 |
| C2—C3 | 1.498 (5) | C15—H15 | 0.9300 |
| C3—C4 | 1.399 (6) | C16—H16A | 0.9300 |
| O1A—Sn1—O3 | 91.9 (6) | C3—C4—C5 | 115.2 (4) |
| O1A—Sn1—O4 | 167.3 (7) | S1—C5—C4 | 109.0 (3) |
| O1A—Sn1—C7 | 95.5 (6) | S1—C6—C3 | 113.4 (3) |
| O1A—Sn1—C8 | 82.7 (5) | O4—C11—C12 | 116.3 (4) |
| O3—Sn1—O4 | 77.69 (9) | O4—C11—O5 | 121.5 (4) |
| O3—Sn1—C7 | 104.94 (15) | O5—C11—C12 | 122.2 (4) |
| O3—Sn1—C8 | 104.92 (14) | C11—C12—C13 | 111.4 (4) |
| O1B—Sn1—O3 | 90.8 (9) | C12—C13—C14 | 124.0 (5) |
| O4—Sn1—C7 | 94.25 (15) | C12—C13—C16 | 125.7 (5) |
| O4—Sn1—C8 | 92.93 (15) | C14—C13—C16 | 110.4 (4) |
| O1B—Sn1—O4 | 164.9 (12) | C13—C14—C15 | 115.1 (5) |
| C7—Sn1—C8 | 150.12 (18) | S2A—C15—C14 | 108.6 (4) |
| O1B—Sn1—C7 | 79.1 (9) | S2B—C15—C14 | 108.6 (4) |
| O1B—Sn1—C8 | 99.6 (11) | S2A—C16—C13 | 110.5 (4) |
| O2A—Sn2—O3 | 89.1 (6) | S2B—C16—C13 | 110.5 (4) |
| O2A—Sn2—C9 | 90.5 (6) | C1—C2—H2A | 108.00 |
| O2A—Sn2—C10 | 80.5 (4) | C1—C2—H2B | 108.00 |
| Sn2i—Sn2—O2A | 128.1 (6) | C3—C2—H2A | 108.00 |
| O2A—Sn2—O3i | 164.4 (7) | C3—C2—H2B | 108.00 |
| O2A—Sn2—O4i | 128.2 (6) | H2A—C2—H2B | 107.00 |
| O3—Sn2—C9 | 105.78 (15) | C3—C4—H4 | 122.00 |
| O3—Sn2—C10 | 105.39 (14) | C5—C4—H4 | 122.00 |
| O2B—Sn2—O3 | 89.1 (7) | S1—C5—H5 | 126.00 |
| Sn2i—Sn2—O3 | 39.25 (6) | C4—C5—H5 | 125.00 |
| O3—Sn2—O3i | 76.53 (8) | S1—C6—H6A | 123.00 |
| O3—Sn2—O4i | 142.67 (8) | C3—C6—H6A | 123.00 |
| C9—Sn2—C10 | 147.33 (19) | Sn1—C7—H7A | 109.00 |
| O2B—Sn2—C9 | 73.5 (9) | Sn1—C7—H7B | 110.00 |
| Sn2i—Sn2—C9 | 105.84 (16) | Sn1—C7—H7C | 109.00 |
| O3i—Sn2—C9 | 99.16 (16) | H7A—C7—H7B | 109.00 |
| O4i—Sn2—C9 | 78.01 (15) | H7A—C7—H7C | 109.00 |
| O2B—Sn2—C10 | 97.5 (12) | H7B—C7—H7C | 109.00 |
| Sn2i—Sn2—C10 | 104.38 (12) | Sn1—C8—H8A | 109.00 |
| O3i—Sn2—C10 | 97.34 (14) | Sn1—C8—H8B | 109.00 |
| O4i—Sn2—C10 | 83.18 (14) | Sn1—C8—H8C | 109.00 |
| Sn2i—Sn2—O2B | 127.4 (8) | H8A—C8—H8B | 110.00 |
| O2B—Sn2—O3i | 161.6 (11) | H8A—C8—H8C | 109.00 |
| O2B—Sn2—O4i | 126.4 (5) | H8B—C8—H8C | 109.00 |
| Sn2i—Sn2—O3i | 37.29 (5) | Sn2—C9—H9A | 109.00 |
| Sn2i—Sn2—O4i | 103.52 (6) | Sn2—C9—H9B | 109.00 |
| O3i—Sn2—O4i | 66.28 (8) | Sn2—C9—H9C | 109.00 |
| C5—S1—C6 | 92.5 (2) | H9A—C9—H9B | 109.00 |
| C15—S2A—C16 | 95.4 (3) | H9A—C9—H9C | 109.00 |
| C15—S2B—C16 | 95.4 (3) | H9B—C9—H9C | 110.00 |
| Sn1—O1A—C1 | 133.2 (11) | Sn2—C10—H10A | 109.00 |
| Sn1—O1B—C1 | 134 (2) | Sn2—C10—H10B | 109.00 |
| Sn2—O2A—C1 | 132.8 (12) | Sn2—C10—H10C | 109.00 |
| Sn2—O2B—C1 | 134 (2) | H10A—C10—H10B | 109.00 |
| Sn2—O3—Sn2i | 103.47 (9) | H10A—C10—H10C | 110.00 |
| Sn1—O3—Sn2i | 120.70 (10) | H10B—C10—H10C | 110.00 |
| Sn1—O3—Sn2 | 135.83 (11) | C11—C12—H12A | 109.00 |
| Sn2i—O4—C11 | 149.5 (3) | C11—C12—H12B | 109.00 |
| Sn1—O4—Sn2i | 95.14 (9) | C13—C12—H12A | 109.00 |
| Sn1—O4—C11 | 115.4 (3) | C13—C12—H12B | 109.00 |
| O1A—C1—O2A | 125.9 (13) | H12A—C12—H12B | 108.00 |
| O1A—C1—C2 | 114.1 (9) | C13—C14—H14 | 122.00 |
| O2A—C1—C2 | 120.0 (10) | C15—C14—H14 | 122.00 |
| O1B—C1—O2B | 125 (3) | S2A—C15—H15 | 126.00 |
| O1B—C1—C2 | 118 (2) | C14—C15—H15 | 126.00 |
| O2B—C1—C2 | 116.6 (18) | S2B—C15—H15 | 126.00 |
| C1—C2—C3 | 116.3 (3) | S2A—C16—H16A | 125.00 |
| C2—C3—C4 | 125.4 (4) | C13—C16—H16A | 125.00 |
| C2—C3—C6 | 124.6 (4) | S2B—C16—H16A | 125.00 |
| C4—C3—C6 | 110.0 (4) | ||
| O3—Sn1—O1A—C1 | −29 (2) | C10—Sn2—Sn2i—O2Ai | −90.9 (6) |
| C7—Sn1—O1A—C1 | 76 (2) | C10—Sn2—Sn2i—O3i | −83.16 (16) |
| C8—Sn1—O1A—C1 | −134 (2) | C10—Sn2—Sn2i—C9i | 12.55 (19) |
| O1A—Sn1—O3—Sn2 | 11.1 (6) | C10—Sn2—Sn2i—C10i | 180.0 (2) |
| O1A—Sn1—O3—Sn2i | −168.5 (6) | O3i—Sn2—Sn2i—O3 | 180.00 (14) |
| O4—Sn1—O3—Sn2 | −176.29 (17) | O3i—Sn2—Sn2i—O4 | 176.85 (11) |
| O4—Sn1—O3—Sn2i | 4.13 (11) | O4i—Sn2—Sn2i—O3 | −176.85 (11) |
| C7—Sn1—O3—Sn2 | −85.1 (2) | O4i—Sn2—Sn2i—O4 | 180.00 (8) |
| C7—Sn1—O3—Sn2i | 95.29 (17) | O3—Sn2—O3i—Sn1i | −179.70 (13) |
| C8—Sn1—O3—Sn2 | 94.0 (2) | O3—Sn2—O3i—Sn2i | 0.00 (10) |
| C8—Sn1—O3—Sn2i | −85.63 (17) | C9—Sn2—O3i—Sn1i | 76.14 (17) |
| O3—Sn1—O4—C11 | 178.3 (3) | C9—Sn2—O3i—Sn2i | −104.16 (16) |
| O3—Sn1—O4—Sn2i | −2.84 (8) | C10—Sn2—O3i—Sn1i | −75.56 (16) |
| C7—Sn1—O4—C11 | 73.9 (3) | C10—Sn2—O3i—Sn2i | 104.14 (15) |
| C7—Sn1—O4—Sn2i | −107.23 (15) | O2A—Sn2—O4i—Sn1i | 170.4 (6) |
| C8—Sn1—O4—C11 | −77.1 (3) | O2A—Sn2—O4i—C11i | −7.7 (8) |
| C8—Sn1—O4—Sn2i | 101.80 (14) | O3—Sn2—O4i—Sn1i | −8.27 (18) |
| O3—Sn2—O2A—C1 | −35 (2) | O3—Sn2—O4i—C11i | 173.7 (5) |
| C9—Sn2—O2A—C1 | 71 (2) | C9—Sn2—O4i—Sn1i | −108.63 (18) |
| C10—Sn2—O2A—C1 | −140 (2) | C9—Sn2—O4i—C11i | 73.3 (5) |
| Sn2i—Sn2—O2A—C1 | −39 (2) | C10—Sn2—O4i—Sn1i | 98.23 (15) |
| O4i—Sn2—O2A—C1 | 146.3 (19) | C10—Sn2—O4i—C11i | −79.9 (5) |
| O2A—Sn2—O3—Sn1 | 6.5 (5) | C6—S1—C5—C4 | −0.7 (4) |
| O2A—Sn2—O3—Sn2i | −173.9 (5) | C5—S1—C6—C3 | −0.3 (5) |
| C9—Sn2—O3—Sn1 | −83.8 (2) | C16—S2A—C15—C14 | 0.2 (4) |
| C9—Sn2—O3—Sn2i | 95.88 (17) | C15—S2A—C16—C13 | 0.0 (4) |
| C10—Sn2—O3—Sn1 | 86.34 (19) | Sn1—O1A—C1—O2A | 13 (3) |
| C10—Sn2—O3—Sn2i | −94.03 (15) | Sn1—O1A—C1—C2 | −166.7 (15) |
| Sn2i—Sn2—O3—Sn1 | −179.6 (2) | Sn2—O2A—C1—O1A | 29 (3) |
| O3i—Sn2—O3—Sn1 | −179.63 (17) | Sn2—O2A—C1—C2 | −152.2 (14) |
| O3i—Sn2—O3—Sn2i | 0.00 (8) | Sn1—O4—C11—O5 | 1.2 (5) |
| O4i—Sn2—O3—Sn1 | −174.57 (12) | Sn1—O4—C11—C12 | −178.2 (3) |
| O4i—Sn2—O3—Sn2i | 5.06 (18) | Sn2i—O4—C11—O5 | −176.6 (3) |
| O2A—Sn2—Sn2i—O3 | 7.8 (6) | Sn2i—O4—C11—C12 | 4.0 (7) |
| O2A—Sn2—Sn2i—O4 | 4.6 (6) | O1A—C1—C2—C3 | −171.2 (13) |
| O2A—Sn2—Sn2i—O2Ai | −180.0 (8) | O2A—C1—C2—C3 | 9.5 (13) |
| O2A—Sn2—Sn2i—O3i | −172.2 (6) | C1—C2—C3—C4 | 78.1 (5) |
| O2A—Sn2—Sn2i—C9i | −76.5 (6) | C1—C2—C3—C6 | −102.5 (5) |
| O2A—Sn2—Sn2i—C10i | 90.9 (6) | C2—C3—C4—C5 | 177.7 (4) |
| O3—Sn2—Sn2i—O4 | −3.15 (11) | C6—C3—C4—C5 | −1.7 (6) |
| O3—Sn2—Sn2i—O2Ai | 172.2 (6) | C2—C3—C6—S1 | −178.3 (3) |
| O3—Sn2—Sn2i—O3i | −180.00 (14) | C4—C3—C6—S1 | 1.2 (6) |
| O3—Sn2—Sn2i—C9i | −84.29 (17) | C3—C4—C5—S1 | 1.5 (6) |
| O3—Sn2—Sn2i—C10i | 83.16 (16) | O4—C11—C12—C13 | −68.4 (5) |
| C9—Sn2—Sn2i—O3 | −95.71 (17) | O5—C11—C12—C13 | 112.2 (5) |
| C9—Sn2—Sn2i—O4 | −98.86 (15) | C11—C12—C13—C14 | −61.4 (6) |
| C9—Sn2—Sn2i—O2Ai | 76.5 (6) | C11—C12—C13—C16 | 118.7 (5) |
| C9—Sn2—Sn2i—O3i | 84.29 (17) | C12—C13—C14—C15 | −179.6 (4) |
| C9—Sn2—Sn2i—C9i | −180.0 (2) | C16—C13—C14—C15 | 0.3 (6) |
| C9—Sn2—Sn2i—C10i | −12.55 (19) | C12—C13—C16—S2A | 179.8 (4) |
| C10—Sn2—Sn2i—O3 | 96.85 (16) | C14—C13—C16—S2A | −0.2 (5) |
| C10—Sn2—Sn2i—O4 | 93.70 (15) | C13—C14—C15—S2A | −0.4 (6) |
| Symmetry codes: (i) −x+1, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C8—H8C···O5ii | 0.96 | 2.58 | 3.103 (6) | 115 |
| C5—H5···CgCiii | 0.93 | 2.83 | 3.513 (5) | 131 |
| C10—H10C···CgCi | 0.96 | 2.80 | 3.697 (5) | 156 |
| Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x, y−1, z−1; (i) −x+1, −y, −z+1. |
| Sn1—O1A | 2.23 (2) | Sn2—O3 | 2.0366 (19) |
| Sn1—O3 | 2.031 (2) | Sn2—C9 | 2.106 (5) |
| Sn1—O4 | 2.207 (3) | Sn2—C10 | 2.109 (4) |
| Sn1—C7 | 2.088 (5) | Sn2—O3i | 2.127 (2) |
| Sn1—C8 | 2.091 (4) | Sn2—O4i | 2.670 (3) |
| Sn2—O2A | 2.312 (17) |
| Symmetry codes: (i) −x+1, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C8—H8C···O5ii | 0.96 | 2.58 | 3.103 (6) | 115 |
| C5—H5···CgCiii | 0.93 | 2.83 | 3.513 (5) | 131 |
| C10—H10C···CgCi | 0.96 | 2.80 | 3.697 (5) | 156 |
| Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x, y−1, z−1; (i) −x+1, −y, −z+1. |
The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer and for technical support, respectively.
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In continuation to our interest with the tin chemistry in various forms (Danish et al., 1995, 1996), (Tahir et al., 1997a, 1997b), we report here the title compound (I), (Fig. 1).
The crystal structure of bis(dicyclohexylammonium 3-thienylacetate) (Ng et al., 2001) has been reported which shows disorder in the 3-thienylacetate unit. In our present complex the ligand is also in disorder. The O-atoms of chelating carboxylate are disordered over two sites with occupancy ratio of 0.65:0.35, whereas in other ligands the disorder is present at the S-atoms. In the title molecule symmetry related central four membered ring A (Sn2/O3/Sn2i/O3i; i = -x + 1, -y, -z + 1) is of course planar. The five membered rings B (C3—C5/S1/C6) and C (C13—C15/S2A/C16) are also planar. The dihedral angles between A/B, A/C and B/C are 66.28 (12)°, 77.43 (11)° and 71.23 (18)°, respectively. Due to intermolecular H-bonding, the stannoxanes are connected in pillar like polymeric form making R22(12) ring motifs (Bernstein et al., 1995), (Fig. 2). The molecules are also stabilized due to C–H···π interactions (Table 1).