Acta Cryst. (2009). E65, m1268 [ doi:10.1107/S1600536809038938 ]
![[mu]](/logos/entities/mu_rmgif.gif)
2-methoxo-di-3-oxido-tetratin(IV)The title compound, [Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2], is a centrosymmetric dimer and displays a ladder type structural motif. There are four SnIV centres which can be divided into two sorts, viz. two endocyclic and two exocyclic. The endo- and exocyclic SnIV centres are linked by bidentate deprotonated methanol and 3-O atoms. Each exocyclic SnIV centre is also coordinated by a monodentate 2-[4-(2-hydroxybenzylideneamino)phenyl]acetate ligand. Parts of the butyl groups were found to be disordered over two sets of sites.
The reaction was carried out under a nitrogen atmosphere. (E)-2-(4-(benzylideneamino)phenyl)acetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Dibutyltin chloride (2 mmol) was then added to the reactor. After stirring for 6 h at 323 K, the yellow paste was obtained and then filtered. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of dichloromethane/methanol (1:1 V/V) solution over a period of six days (yield 86%. m.p.458 K). Anal. Calcd (%) for C64H98N2O10Sn4 (Mr = 1530.20): C, 50.23; H, 6.46; N, 1.83; O, 10.46; Sn, 31.03. Found (%): C, 50.19; H, 6.44; N, 1.85; O, 10.47; Sn, 31.05.
The atoms C18, C19, C20, C21, C22, C23, C29, C30 and C31 were found to be disordered over two sites, and the ratio of the occupancy factors refined to 0.70 (8):0.30 (8), 0.70 (8):0.30 (8), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3), 0.66 (3):0.34 (3) and 0.66 (3):0.34 (3) for atoms C18:c18', C19:c19', C20:c20', C21:C21', C22:C22', C23:C23', C29:C29', C30:C30' and C31:C31', respectively. H atoms were positioned geometrically, with C—H = 0.93, 0.96, 0.97 and 0.82 Å for aromatic, methyl, methylene and hydroxyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C, O) for the methyl and hydroxyl groups
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hg2567fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. [Symmetry code: -x + 1,-y + 1,-z] |
| [Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2] | Z = 1 |
| Mr = 1534.32 | F(000) = 780 |
| Triclinic, P1 | Dx = 1.451 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.6059 (14) Å | Cell parameters from 3867 reflections |
| b = 12.2128 (17) Å | θ = 2.2–25.7° |
| c = 14.522 (2) Å | µ = 1.46 mm−1 |
| α = 104.921 (2)° | T = 298 K |
| β = 104.271 (2)° | Block, colorless |
| γ = 91.991 (1)° | 0.40 × 0.39 × 0.19 mm |
| V = 1751.8 (4) Å3 |
| Siemens SMART CCD area-detector diffractometer | 6067 independent reflections |
| Radiation source: fine-focus sealed tube | 4114 reflections with I > 2σ(I) |
| graphite | Rint = 0.019 |
| φ and ω scans | θmax = 25.0°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→12 |
| Tmin = 0.593, Tmax = 0.769 | k = −14→13 |
| 9161 measured reflections | l = −17→17 |
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.140 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0706P)2 + 2.6157P] where P = (Fo2 + 2Fc2)/3 |
| 6067 reflections | (Δ/σ)max = 0.001 |
| 453 parameters | Δρmax = 1.31 e Å−3 |
| 0 restraints | Δρmin = −0.56 e Å−3 |
| [Sn4(C4H9)8(C15H12NO3)2(CH3O)2O2] | γ = 91.991 (1)° |
| Mr = 1534.32 | V = 1751.8 (4) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 10.6059 (14) Å | Mo Kα radiation |
| b = 12.2128 (17) Å | µ = 1.46 mm−1 |
| c = 14.522 (2) Å | T = 298 K |
| α = 104.921 (2)° | 0.40 × 0.39 × 0.19 mm |
| β = 104.271 (2)° |
| Siemens SMART CCD area-detector diffractometer | 6067 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4114 reflections with I > 2σ(I) |
| Tmin = 0.593, Tmax = 0.769 | Rint = 0.019 |
| 9161 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.140 | Δρmax = 1.31 e Å−3 |
| S = 1.04 | Δρmin = −0.56 e Å−3 |
| 6067 reflections | Absolute structure: ? |
| 453 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Sn1 | 0.65357 (4) | 0.35975 (4) | 0.14820 (3) | 0.05024 (16) | |
| Sn2 | 0.52091 (4) | 0.59836 (4) | 0.10841 (3) | 0.04935 (16) | |
| N1 | 0.9801 (6) | 0.0426 (5) | −0.2942 (4) | 0.0634 (15) | |
| O1 | 0.6229 (5) | 0.2161 (4) | 0.0182 (3) | 0.0638 (13) | |
| O2 | 0.7256 (6) | 0.1199 (5) | 0.1181 (4) | 0.0823 (16) | |
| O3 | 1.0365 (6) | 0.1364 (5) | −0.4230 (5) | 0.0909 (18) | |
| H3 | 0.9947 | 0.1233 | −0.3857 | 0.136* | |
| O4 | 0.5571 (4) | 0.4355 (4) | 0.0470 (3) | 0.0547 (11) | |
| O5 | 0.6272 (5) | 0.5360 (4) | 0.2274 (3) | 0.0595 (12) | |
| C1 | 0.6645 (7) | 0.1245 (6) | 0.0363 (6) | 0.0583 (18) | |
| C2 | 0.6344 (7) | 0.0194 (6) | −0.0508 (5) | 0.0623 (18) | |
| H2A | 0.6435 | −0.0478 | −0.0268 | 0.075* | |
| H2B | 0.5444 | 0.0154 | −0.0888 | 0.075* | |
| C3 | 0.7237 (7) | 0.0198 (6) | −0.1167 (5) | 0.0560 (17) | |
| C4 | 0.6932 (8) | 0.0674 (7) | −0.1940 (6) | 0.070 (2) | |
| H4 | 0.6136 | 0.0975 | −0.2079 | 0.084* | |
| C5 | 0.7779 (8) | 0.0717 (7) | −0.2520 (6) | 0.068 (2) | |
| H5 | 0.7540 | 0.1037 | −0.3045 | 0.082* | |
| C6 | 0.8976 (7) | 0.0290 (6) | −0.2330 (5) | 0.0591 (18) | |
| C7 | 0.9282 (8) | −0.0209 (7) | −0.1563 (6) | 0.070 (2) | |
| H7 | 1.0071 | −0.0523 | −0.1432 | 0.084* | |
| C8 | 0.8430 (8) | −0.0247 (7) | −0.0990 (6) | 0.067 (2) | |
| H8 | 0.8661 | −0.0579 | −0.0471 | 0.081* | |
| C9 | 1.0880 (8) | 0.0011 (6) | −0.2867 (5) | 0.0654 (19) | |
| H9 | 1.1127 | −0.0415 | −0.2418 | 0.079* | |
| C10 | 1.1754 (7) | 0.0177 (6) | −0.3466 (5) | 0.0634 (19) | |
| C11 | 1.1448 (8) | 0.0835 (7) | −0.4122 (6) | 0.069 (2) | |
| C12 | 1.2303 (9) | 0.0984 (8) | −0.4689 (7) | 0.084 (2) | |
| H12 | 1.2097 | 0.1415 | −0.5138 | 0.101* | |
| C13 | 1.3438 (10) | 0.0486 (9) | −0.4572 (7) | 0.092 (3) | |
| H13 | 1.4007 | 0.0586 | −0.4946 | 0.110* | |
| C14 | 1.3772 (10) | −0.0163 (9) | −0.3913 (7) | 0.097 (3) | |
| H14 | 1.4558 | −0.0489 | −0.3842 | 0.117* | |
| C15 | 1.2924 (9) | −0.0321 (8) | −0.3362 (7) | 0.086 (3) | |
| H15 | 1.3134 | −0.0761 | −0.2921 | 0.103* | |
| C16 | 0.8584 (7) | 0.3962 (8) | 0.1767 (6) | 0.077 (2) | |
| H16A | 0.8793 | 0.3752 | 0.1135 | 0.092* | |
| H16B | 0.8781 | 0.4782 | 0.2025 | 0.092* | |
| C17 | 0.9505 (10) | 0.3444 (10) | 0.2443 (9) | 0.111 (3) | |
| H17A | 1.0393 | 0.3717 | 0.2486 | 0.133* | 0.70 (8) |
| H17B | 0.9397 | 0.2624 | 0.2161 | 0.133* | 0.70 (8) |
| H17C | 1.0235 | 0.4005 | 0.2841 | 0.133* | 0.30 (8) |
| H17D | 0.9854 | 0.2816 | 0.2056 | 0.133* | 0.30 (8) |
| C18 | 0.932 (5) | 0.370 (5) | 0.347 (4) | 0.108 (10) | 0.70 (8) |
| H18A | 0.8425 | 0.3452 | 0.3424 | 0.130* | 0.70 (8) |
| H18B | 0.9462 | 0.4521 | 0.3760 | 0.130* | 0.70 (8) |
| C19 | 1.026 (5) | 0.312 (4) | 0.413 (4) | 0.136 (11) | 0.70 (8) |
| H19A | 1.0285 | 0.2344 | 0.3777 | 0.203* | 0.70 (8) |
| H19B | 0.9956 | 0.3129 | 0.4707 | 0.203* | 0.70 (8) |
| H19C | 1.1120 | 0.3518 | 0.4337 | 0.203* | 0.70 (8) |
| C20 | 0.512 (3) | 0.289 (3) | 0.2016 (19) | 0.072 (7) | 0.66 (3) |
| H20A | 0.4270 | 0.3017 | 0.1650 | 0.087* | 0.66 (3) |
| H20B | 0.5168 | 0.2076 | 0.1863 | 0.087* | 0.66 (3) |
| C21 | 0.5211 (16) | 0.3327 (13) | 0.3105 (12) | 0.086 (6) | 0.66 (3) |
| H21A | 0.5249 | 0.4151 | 0.3279 | 0.103* | 0.66 (3) |
| H21B | 0.6021 | 0.3130 | 0.3477 | 0.103* | 0.66 (3) |
| C22 | 0.408 (3) | 0.286 (3) | 0.3417 (19) | 0.102 (8) | 0.66 (3) |
| H22A | 0.3282 | 0.3156 | 0.3129 | 0.122* | 0.66 (3) |
| H22B | 0.3954 | 0.2038 | 0.3163 | 0.122* | 0.66 (3) |
| C23 | 0.431 (4) | 0.318 (3) | 0.451 (2) | 0.145 (11) | 0.66 (3) |
| H23A | 0.5072 | 0.2855 | 0.4799 | 0.217* | 0.66 (3) |
| H23B | 0.3565 | 0.2892 | 0.4678 | 0.217* | 0.66 (3) |
| H23C | 0.4444 | 0.3993 | 0.4769 | 0.217* | 0.66 (3) |
| C18' | 0.914 (11) | 0.317 (9) | 0.329 (8) | 0.10 (2) | 0.30 (8) |
| H18C | 0.9037 | 0.2354 | 0.3180 | 0.116* | 0.30 (8) |
| H18D | 0.8304 | 0.3453 | 0.3337 | 0.116* | 0.30 (8) |
| C19' | 1.018 (10) | 0.371 (11) | 0.427 (8) | 0.13 (3) | 0.30 (8) |
| H19D | 0.9762 | 0.4141 | 0.4746 | 0.200* | 0.30 (8) |
| H19E | 1.0811 | 0.4212 | 0.4163 | 0.200* | 0.30 (8) |
| H19F | 1.0601 | 0.3124 | 0.4514 | 0.200* | 0.30 (8) |
| C20' | 0.552 (6) | 0.286 (7) | 0.238 (4) | 0.075 (13) | 0.34 (3) |
| H20C | 0.5450 | 0.2035 | 0.2138 | 0.090* | 0.34 (3) |
| H20D | 0.6054 | 0.3074 | 0.3055 | 0.090* | 0.34 (3) |
| C21' | 0.416 (3) | 0.322 (3) | 0.236 (2) | 0.096 (12) | 0.34 (3) |
| H21C | 0.3623 | 0.2996 | 0.1688 | 0.115* | 0.34 (3) |
| H21D | 0.4228 | 0.4046 | 0.2597 | 0.115* | 0.34 (3) |
| C22' | 0.347 (5) | 0.272 (6) | 0.300 (4) | 0.103 (14) | 0.34 (3) |
| H22C | 0.2535 | 0.2657 | 0.2723 | 0.123* | 0.34 (3) |
| H22D | 0.3719 | 0.1954 | 0.2976 | 0.123* | 0.34 (3) |
| C23' | 0.382 (7) | 0.343 (7) | 0.406 (5) | 0.14 (2) | 0.34 (3) |
| H23D | 0.4725 | 0.3400 | 0.4368 | 0.217* | 0.34 (3) |
| H23E | 0.3287 | 0.3134 | 0.4412 | 0.217* | 0.34 (3) |
| H23F | 0.3662 | 0.4204 | 0.4088 | 0.217* | 0.34 (3) |
| C24 | 0.3385 (7) | 0.6054 (7) | 0.1451 (6) | 0.069 (2) | |
| H24A | 0.2905 | 0.6593 | 0.1155 | 0.083* | |
| H24B | 0.2888 | 0.5311 | 0.1146 | 0.083* | |
| C25 | 0.3425 (8) | 0.6382 (8) | 0.2542 (6) | 0.077 (2) | |
| H25A | 0.3828 | 0.7159 | 0.2844 | 0.093* | |
| H25B | 0.3965 | 0.5891 | 0.2862 | 0.093* | |
| C26 | 0.2068 (9) | 0.6289 (9) | 0.2717 (8) | 0.102 (3) | |
| H26A | 0.1530 | 0.6781 | 0.2396 | 0.122* | |
| H26B | 0.1665 | 0.5513 | 0.2413 | 0.122* | |
| C27 | 0.2089 (13) | 0.6614 (12) | 0.3807 (9) | 0.144 (5) | |
| H27A | 0.2504 | 0.6060 | 0.4109 | 0.216* | |
| H27B | 0.1209 | 0.6634 | 0.3868 | 0.216* | |
| H27C | 0.2567 | 0.7351 | 0.4130 | 0.216* | |
| C28 | 0.6575 (8) | 0.7411 (7) | 0.1316 (6) | 0.078 (2) | |
| H28A | 0.6073 | 0.8061 | 0.1323 | 0.094* | 0.66 (3) |
| H28B | 0.7134 | 0.7541 | 0.1980 | 0.094* | 0.66 (3) |
| H28C | 0.6170 | 0.7986 | 0.1023 | 0.094* | 0.34 (3) |
| H28D | 0.6990 | 0.7753 | 0.2012 | 0.094* | 0.34 (3) |
| C29 | 0.7475 (19) | 0.7479 (17) | 0.0664 (13) | 0.089 (6) | 0.66 (3) |
| H29A | 0.6982 | 0.7264 | −0.0025 | 0.106* | 0.66 (3) |
| H29B | 0.7889 | 0.8250 | 0.0830 | 0.106* | 0.66 (3) |
| C30 | 0.849 (2) | 0.6678 (15) | 0.0837 (13) | 0.090 (6) | 0.66 (3) |
| H30A | 0.8063 | 0.5910 | 0.0674 | 0.109* | 0.66 (3) |
| H30B | 0.8967 | 0.6893 | 0.1529 | 0.109* | 0.66 (3) |
| C31 | 0.943 (3) | 0.670 (3) | 0.021 (2) | 0.109 (8) | 0.66 (3) |
| H31A | 0.8973 | 0.6827 | −0.0410 | 0.163* | 0.66 (3) |
| H31B | 0.9799 | 0.5989 | 0.0082 | 0.163* | 0.66 (3) |
| H31C | 1.0121 | 0.7308 | 0.0548 | 0.163* | 0.66 (3) |
| C29' | 0.757 (4) | 0.682 (3) | 0.077 (3) | 0.082 (10) | 0.34 (3) |
| H29C | 0.7933 | 0.6256 | 0.1093 | 0.098* | 0.34 (3) |
| H29D | 0.7085 | 0.6412 | 0.0099 | 0.098* | 0.34 (3) |
| C30' | 0.868 (3) | 0.758 (3) | 0.071 (2) | 0.085 (12) | 0.34 (3) |
| H30C | 0.9201 | 0.7908 | 0.1390 | 0.102* | 0.34 (3) |
| H30D | 0.8295 | 0.8203 | 0.0489 | 0.102* | 0.34 (3) |
| C31' | 0.965 (5) | 0.718 (4) | 0.011 (4) | 0.096 (13) | 0.34 (3) |
| H31D | 1.0305 | 0.6814 | 0.0469 | 0.143* | 0.34 (3) |
| H31E | 1.0050 | 0.7821 | −0.0016 | 0.143* | 0.34 (3) |
| H31F | 0.9190 | 0.6647 | −0.0507 | 0.143* | 0.34 (3) |
| C32 | 0.6961 (9) | 0.6034 (8) | 0.3245 (6) | 0.097 (3) | |
| H32A | 0.7842 | 0.6253 | 0.3252 | 0.145* | |
| H32B | 0.6974 | 0.5596 | 0.3709 | 0.145* | |
| H32C | 0.6530 | 0.6704 | 0.3425 | 0.145* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.0542 (3) | 0.0548 (3) | 0.0449 (3) | 0.0153 (2) | 0.0181 (2) | 0.0133 (2) |
| Sn2 | 0.0521 (3) | 0.0467 (3) | 0.0438 (3) | 0.0123 (2) | 0.0129 (2) | 0.0019 (2) |
| N1 | 0.063 (4) | 0.068 (4) | 0.062 (4) | 0.012 (3) | 0.024 (3) | 0.015 (3) |
| O1 | 0.081 (3) | 0.058 (3) | 0.054 (3) | 0.025 (3) | 0.022 (3) | 0.010 (2) |
| O2 | 0.100 (4) | 0.078 (4) | 0.072 (4) | 0.024 (3) | 0.016 (3) | 0.029 (3) |
| O3 | 0.089 (4) | 0.106 (5) | 0.102 (4) | 0.032 (4) | 0.043 (4) | 0.052 (4) |
| O4 | 0.066 (3) | 0.048 (3) | 0.046 (2) | 0.023 (2) | 0.013 (2) | 0.005 (2) |
| O5 | 0.068 (3) | 0.057 (3) | 0.045 (2) | 0.014 (2) | 0.009 (2) | 0.005 (2) |
| C1 | 0.061 (4) | 0.058 (4) | 0.066 (5) | 0.020 (4) | 0.031 (4) | 0.021 (4) |
| C2 | 0.068 (5) | 0.050 (4) | 0.075 (5) | 0.010 (3) | 0.030 (4) | 0.016 (4) |
| C3 | 0.064 (4) | 0.047 (4) | 0.060 (4) | 0.009 (3) | 0.028 (4) | 0.010 (3) |
| C4 | 0.067 (5) | 0.074 (5) | 0.074 (5) | 0.022 (4) | 0.026 (4) | 0.020 (4) |
| C5 | 0.074 (5) | 0.076 (5) | 0.064 (5) | 0.022 (4) | 0.024 (4) | 0.028 (4) |
| C6 | 0.066 (5) | 0.059 (4) | 0.058 (4) | 0.015 (4) | 0.024 (4) | 0.018 (3) |
| C7 | 0.066 (5) | 0.080 (5) | 0.075 (5) | 0.028 (4) | 0.032 (4) | 0.025 (4) |
| C8 | 0.074 (5) | 0.074 (5) | 0.067 (5) | 0.024 (4) | 0.029 (4) | 0.029 (4) |
| C9 | 0.073 (5) | 0.066 (5) | 0.062 (5) | 0.016 (4) | 0.024 (4) | 0.018 (4) |
| C10 | 0.068 (5) | 0.065 (5) | 0.059 (4) | 0.008 (4) | 0.023 (4) | 0.014 (4) |
| C11 | 0.066 (5) | 0.074 (5) | 0.067 (5) | 0.007 (4) | 0.026 (4) | 0.014 (4) |
| C12 | 0.086 (6) | 0.090 (6) | 0.082 (6) | 0.004 (5) | 0.032 (5) | 0.025 (5) |
| C13 | 0.088 (7) | 0.111 (8) | 0.089 (6) | 0.012 (6) | 0.047 (6) | 0.026 (6) |
| C14 | 0.083 (6) | 0.122 (8) | 0.095 (7) | 0.026 (6) | 0.038 (6) | 0.028 (6) |
| C15 | 0.076 (6) | 0.106 (7) | 0.083 (6) | 0.025 (5) | 0.032 (5) | 0.029 (5) |
| C16 | 0.060 (5) | 0.094 (6) | 0.082 (6) | 0.018 (4) | 0.018 (4) | 0.034 (5) |
| C17 | 0.085 (7) | 0.126 (9) | 0.122 (9) | 0.008 (6) | 0.010 (6) | 0.049 (8) |
| C18 | 0.090 (19) | 0.13 (3) | 0.10 (2) | 0.00 (2) | 0.002 (15) | 0.04 (2) |
| C19 | 0.140 (19) | 0.13 (3) | 0.12 (2) | 0.03 (2) | −0.012 (17) | 0.05 (2) |
| C20 | 0.082 (19) | 0.077 (11) | 0.063 (17) | 0.006 (13) | 0.040 (13) | 0.011 (14) |
| C21 | 0.094 (12) | 0.100 (11) | 0.069 (11) | −0.005 (8) | 0.042 (9) | 0.015 (8) |
| C22 | 0.11 (2) | 0.111 (16) | 0.079 (19) | −0.015 (16) | 0.047 (14) | 0.008 (16) |
| C23 | 0.15 (3) | 0.16 (3) | 0.11 (2) | −0.009 (19) | 0.027 (19) | 0.036 (18) |
| C18' | 0.09 (4) | 0.11 (5) | 0.09 (4) | −0.01 (5) | 0.01 (3) | 0.04 (5) |
| C19' | 0.12 (4) | 0.13 (7) | 0.12 (4) | 0.01 (5) | 0.00 (3) | 0.02 (6) |
| C20' | 0.09 (4) | 0.08 (2) | 0.06 (3) | 0.00 (2) | 0.03 (2) | 0.02 (3) |
| C21' | 0.10 (3) | 0.10 (2) | 0.08 (2) | −0.001 (18) | 0.03 (2) | 0.017 (17) |
| C22' | 0.11 (4) | 0.11 (3) | 0.09 (3) | −0.01 (3) | 0.03 (2) | 0.02 (3) |
| C23' | 0.15 (6) | 0.16 (5) | 0.11 (5) | −0.01 (4) | 0.03 (4) | 0.04 (4) |
| C24 | 0.062 (5) | 0.073 (5) | 0.070 (5) | 0.017 (4) | 0.022 (4) | 0.010 (4) |
| C25 | 0.076 (5) | 0.088 (6) | 0.085 (6) | 0.027 (4) | 0.040 (5) | 0.030 (5) |
| C26 | 0.095 (7) | 0.112 (8) | 0.115 (8) | 0.017 (6) | 0.058 (6) | 0.031 (6) |
| C27 | 0.165 (12) | 0.182 (13) | 0.139 (11) | 0.055 (10) | 0.110 (10) | 0.065 (10) |
| C28 | 0.073 (5) | 0.072 (5) | 0.084 (6) | −0.001 (4) | 0.014 (5) | 0.020 (5) |
| C29 | 0.092 (14) | 0.075 (11) | 0.095 (11) | −0.019 (10) | 0.004 (9) | 0.040 (10) |
| C30 | 0.091 (13) | 0.073 (11) | 0.108 (12) | 0.007 (10) | 0.023 (11) | 0.029 (9) |
| C31 | 0.106 (16) | 0.098 (19) | 0.123 (17) | −0.022 (14) | 0.050 (13) | 0.014 (15) |
| C29' | 0.08 (2) | 0.07 (2) | 0.10 (2) | 0.00 (2) | 0.018 (19) | 0.033 (18) |
| C30' | 0.08 (2) | 0.08 (2) | 0.10 (2) | −0.002 (16) | 0.025 (16) | 0.031 (16) |
| C31' | 0.09 (3) | 0.10 (4) | 0.11 (3) | −0.01 (3) | 0.05 (2) | 0.03 (3) |
| C32 | 0.089 (6) | 0.096 (7) | 0.062 (5) | 0.011 (5) | −0.005 (4) | −0.030 (5) |
| Sn1—O4 | 2.022 (4) | C21—H21B | 0.9700 |
| Sn1—C20 | 2.10 (4) | C22—C23 | 1.49 (4) |
| Sn1—C16 | 2.117 (8) | C22—H22A | 0.9700 |
| Sn1—O1 | 2.169 (4) | C22—H22B | 0.9700 |
| Sn1—C20' | 2.21 (7) | C23—H23A | 0.9600 |
| Sn1—O5 | 2.227 (4) | C23—H23B | 0.9600 |
| Sn2—O4 | 2.051 (4) | C23—H23C | 0.9600 |
| Sn2—O4i | 2.127 (4) | C18'—C19' | 1.54 (16) |
| Sn2—C24 | 2.129 (7) | C18'—H18C | 0.9700 |
| Sn2—C28 | 2.129 (8) | C18'—H18D | 0.9700 |
| Sn2—O5 | 2.148 (5) | C19'—H19D | 0.9600 |
| N1—C9 | 1.260 (9) | C19'—H19E | 0.9600 |
| N1—C6 | 1.426 (9) | C19'—H19F | 0.9600 |
| O1—C1 | 1.281 (8) | C20'—C21' | 1.52 (8) |
| O2—C1 | 1.222 (8) | C20'—H20C | 0.9700 |
| O3—C11 | 1.333 (9) | C20'—H20D | 0.9700 |
| O3—H3 | 0.8200 | C21'—C22' | 1.53 (7) |
| O4—Sn2i | 2.127 (4) | C21'—H21C | 0.9700 |
| O5—C32 | 1.432 (8) | C21'—H21D | 0.9700 |
| C1—C2 | 1.512 (10) | C22'—C23' | 1.51 (7) |
| C2—C3 | 1.505 (9) | C22'—H22C | 0.9700 |
| C2—H2A | 0.9700 | C22'—H22D | 0.9700 |
| C2—H2B | 0.9700 | C23'—H23D | 0.9600 |
| C3—C4 | 1.368 (10) | C23'—H23E | 0.9600 |
| C3—C8 | 1.386 (10) | C23'—H23F | 0.9600 |
| C4—C5 | 1.382 (10) | C24—C25 | 1.520 (10) |
| C4—H4 | 0.9300 | C24—H24A | 0.9700 |
| C5—C6 | 1.380 (10) | C24—H24B | 0.9700 |
| C5—H5 | 0.9300 | C25—C26 | 1.527 (11) |
| C6—C7 | 1.379 (10) | C25—H25A | 0.9700 |
| C7—C8 | 1.379 (10) | C25—H25B | 0.9700 |
| C7—H7 | 0.9300 | C26—C27 | 1.523 (14) |
| C8—H8 | 0.9300 | C26—H26A | 0.9700 |
| C9—C10 | 1.460 (10) | C26—H26B | 0.9700 |
| C9—H9 | 0.9300 | C27—H27A | 0.9600 |
| C10—C11 | 1.385 (11) | C27—H27B | 0.9600 |
| C10—C15 | 1.393 (11) | C27—H27C | 0.9600 |
| C11—C12 | 1.403 (11) | C28—C29 | 1.514 (19) |
| C12—C13 | 1.360 (12) | C28—C29' | 1.56 (4) |
| C12—H12 | 0.9300 | C28—H28A | 0.9700 |
| C13—C14 | 1.383 (13) | C28—H28B | 0.9700 |
| C13—H13 | 0.9300 | C28—H28C | 0.9700 |
| C14—C15 | 1.382 (12) | C28—H28D | 0.9700 |
| C14—H14 | 0.9300 | C29—C30 | 1.50 (3) |
| C15—H15 | 0.9300 | C29—H29A | 0.9700 |
| C16—C17 | 1.485 (12) | C29—H29B | 0.9700 |
| C16—H16A | 0.9700 | C30—C31 | 1.52 (3) |
| C16—H16B | 0.9700 | C30—H30A | 0.9700 |
| C17—C18' | 1.49 (11) | C30—H30B | 0.9700 |
| C17—C18 | 1.50 (5) | C31—H31A | 0.9600 |
| C17—H17A | 0.9700 | C31—H31B | 0.9600 |
| C17—H17B | 0.9700 | C31—H31C | 0.9600 |
| C17—H17C | 0.9700 | C29'—C30' | 1.51 (6) |
| C17—H17D | 0.9700 | C29'—H29C | 0.9700 |
| C18—C19 | 1.54 (7) | C29'—H29D | 0.9700 |
| C18—H18A | 0.9700 | C30'—C31' | 1.52 (6) |
| C18—H18B | 0.9700 | C30'—H30C | 0.9700 |
| C19—H19A | 0.9600 | C30'—H30D | 0.9700 |
| C19—H19B | 0.9600 | C31'—H31D | 0.9600 |
| C19—H19C | 0.9600 | C31'—H31E | 0.9600 |
| C20—C21 | 1.51 (3) | C31'—H31F | 0.9600 |
| C20—H20A | 0.9700 | C32—H32A | 0.9600 |
| C20—H20B | 0.9700 | C32—H32B | 0.9600 |
| C21—C22 | 1.53 (3) | C32—H32C | 0.9600 |
| C21—H21A | 0.9700 | ||
| O4—Sn1—C20 | 107.0 (8) | C22—C21—H21A | 108.6 |
| O4—Sn1—C16 | 110.7 (3) | C20—C21—H21B | 108.6 |
| C20—Sn1—C16 | 141.6 (7) | C22—C21—H21B | 108.6 |
| O4—Sn1—O1 | 81.82 (17) | H21A—C21—H21B | 107.6 |
| C20—Sn1—O1 | 93.4 (10) | C23—C22—C21 | 112 (2) |
| C16—Sn1—O1 | 98.6 (3) | C23—C22—H22A | 109.2 |
| O4—Sn1—C20' | 121.8 (15) | C21—C22—H22A | 109.2 |
| C20—Sn1—C20' | 15.7 (15) | C23—C22—H22B | 109.2 |
| C16—Sn1—C20' | 126.1 (14) | C21—C22—H22B | 109.2 |
| O1—Sn1—C20' | 100.2 (19) | H22A—C22—H22B | 107.9 |
| O4—Sn1—O5 | 71.85 (16) | C17—C18'—C19' | 112 (8) |
| C20—Sn1—O5 | 91.6 (11) | C17—C18'—H18C | 109.3 |
| C16—Sn1—O5 | 93.4 (3) | C19'—C18'—H18C | 109.3 |
| O1—Sn1—O5 | 153.52 (18) | C17—C18'—H18D | 109.3 |
| C20'—Sn1—O5 | 92 (2) | C19'—C18'—H18D | 109.3 |
| O4—Sn2—O4i | 73.39 (19) | H18C—C18'—H18D | 108.0 |
| O4—Sn2—C24 | 113.0 (3) | C18'—C19'—H19D | 109.5 |
| O4i—Sn2—C24 | 96.7 (2) | C18'—C19'—H19E | 109.5 |
| O4—Sn2—C28 | 121.4 (3) | H19D—C19'—H19E | 109.5 |
| O4i—Sn2—C28 | 98.7 (3) | C18'—C19'—H19F | 109.5 |
| C24—Sn2—C28 | 125.6 (3) | H19D—C19'—H19F | 109.5 |
| O4—Sn2—O5 | 73.00 (17) | H19E—C19'—H19F | 109.5 |
| O4i—Sn2—O5 | 146.34 (17) | C21'—C20'—Sn1 | 115 (4) |
| C24—Sn2—O5 | 98.0 (3) | C21'—C20'—H20C | 108.6 |
| C28—Sn2—O5 | 97.1 (3) | Sn1—C20'—H20C | 108.6 |
| C9—N1—C6 | 121.4 (7) | C21'—C20'—H20D | 108.6 |
| C1—O1—Sn1 | 114.1 (4) | Sn1—C20'—H20D | 108.6 |
| C11—O3—H3 | 109.5 | H20C—C20'—H20D | 107.6 |
| Sn1—O4—Sn2 | 113.17 (19) | C20'—C21'—C22' | 114 (4) |
| Sn1—O4—Sn2i | 140.2 (2) | C20'—C21'—H21C | 108.7 |
| Sn2—O4—Sn2i | 106.61 (19) | C22'—C21'—H21C | 108.7 |
| C32—O5—Sn2 | 126.5 (5) | C20'—C21'—H21D | 108.7 |
| C32—O5—Sn1 | 128.9 (5) | C22'—C21'—H21D | 108.7 |
| Sn2—O5—Sn1 | 101.95 (17) | H21C—C21'—H21D | 107.6 |
| O2—C1—O1 | 123.5 (7) | C23'—C22'—C21' | 112 (5) |
| O2—C1—C2 | 120.5 (7) | C23'—C22'—H22C | 109.1 |
| O1—C1—C2 | 116.0 (7) | C21'—C22'—H22C | 109.1 |
| C3—C2—C1 | 111.9 (6) | C23'—C22'—H22D | 109.1 |
| C3—C2—H2A | 109.2 | C21'—C22'—H22D | 109.1 |
| C1—C2—H2A | 109.2 | H22C—C22'—H22D | 107.8 |
| C3—C2—H2B | 109.2 | C22'—C23'—H23D | 109.5 |
| C1—C2—H2B | 109.2 | C22'—C23'—H23E | 109.5 |
| H2A—C2—H2B | 107.9 | H23D—C23'—H23E | 109.5 |
| C4—C3—C8 | 117.3 (6) | C22'—C23'—H23F | 109.5 |
| C4—C3—C2 | 121.7 (7) | H23D—C23'—H23F | 109.5 |
| C8—C3—C2 | 120.9 (7) | H23E—C23'—H23F | 109.5 |
| C3—C4—C5 | 121.6 (7) | C25—C24—Sn2 | 117.3 (5) |
| C3—C4—H4 | 119.2 | C25—C24—H24A | 108.0 |
| C5—C4—H4 | 119.2 | Sn2—C24—H24A | 108.0 |
| C6—C5—C4 | 120.9 (7) | C25—C24—H24B | 108.0 |
| C6—C5—H5 | 119.6 | Sn2—C24—H24B | 108.0 |
| C4—C5—H5 | 119.6 | H24A—C24—H24B | 107.2 |
| C7—C6—C5 | 118.0 (7) | C24—C25—C26 | 112.7 (8) |
| C7—C6—N1 | 125.7 (7) | C24—C25—H25A | 109.1 |
| C5—C6—N1 | 116.4 (6) | C26—C25—H25A | 109.1 |
| C6—C7—C8 | 120.6 (7) | C24—C25—H25B | 109.1 |
| C6—C7—H7 | 119.7 | C26—C25—H25B | 109.1 |
| C8—C7—H7 | 119.7 | H25A—C25—H25B | 107.8 |
| C7—C8—C3 | 121.6 (7) | C27—C26—C25 | 113.5 (9) |
| C7—C8—H8 | 119.2 | C27—C26—H26A | 108.9 |
| C3—C8—H8 | 119.2 | C25—C26—H26A | 108.9 |
| N1—C9—C10 | 121.9 (7) | C27—C26—H26B | 108.9 |
| N1—C9—H9 | 119.0 | C25—C26—H26B | 108.9 |
| C10—C9—H9 | 119.0 | H26A—C26—H26B | 107.7 |
| C11—C10—C15 | 119.6 (7) | C26—C27—H27A | 109.5 |
| C11—C10—C9 | 121.2 (7) | C26—C27—H27B | 109.5 |
| C15—C10—C9 | 119.2 (7) | H27A—C27—H27B | 109.5 |
| O3—C11—C10 | 122.4 (7) | C26—C27—H27C | 109.5 |
| O3—C11—C12 | 117.5 (8) | H27A—C27—H27C | 109.5 |
| C10—C11—C12 | 120.1 (8) | H27B—C27—H27C | 109.5 |
| C13—C12—C11 | 118.9 (9) | C29—C28—C29' | 32.6 (11) |
| C13—C12—H12 | 120.6 | C29—C28—Sn2 | 124.4 (9) |
| C11—C12—H12 | 120.6 | C29'—C28—Sn2 | 100.1 (15) |
| C12—C13—C14 | 122.0 (9) | C29—C28—H28A | 106.2 |
| C12—C13—H13 | 119.0 | C29'—C28—H28A | 138.2 |
| C14—C13—H13 | 119.0 | Sn2—C28—H28A | 106.2 |
| C15—C14—C13 | 119.1 (9) | C29—C28—H28B | 106.2 |
| C15—C14—H14 | 120.4 | C29'—C28—H28B | 96.4 |
| C13—C14—H14 | 120.4 | Sn2—C28—H28B | 106.2 |
| C14—C15—C10 | 120.2 (9) | H28A—C28—H28B | 106.4 |
| C14—C15—H15 | 119.9 | C29—C28—H28C | 81.9 |
| C10—C15—H15 | 119.9 | C29'—C28—H28C | 112.1 |
| C17—C16—Sn1 | 120.8 (6) | Sn2—C28—H28C | 111.8 |
| C17—C16—H16A | 107.1 | H28A—C28—H28C | 27.4 |
| Sn1—C16—H16A | 107.1 | H28B—C28—H28C | 126.3 |
| C17—C16—H16B | 107.1 | C29—C28—H28D | 112.8 |
| Sn1—C16—H16B | 107.1 | C29'—C28—H28D | 111.2 |
| H16A—C16—H16B | 106.8 | Sn2—C28—H28D | 112.0 |
| C16—C17—C18' | 120 (5) | H28A—C28—H28D | 88.3 |
| C16—C17—C18 | 114 (2) | H28B—C28—H28D | 18.1 |
| C18'—C17—C18 | 24 (3) | H28C—C28—H28D | 109.4 |
| C16—C17—H17A | 108.8 | C30—C29—C28 | 107.6 (16) |
| C18'—C17—H17A | 121.9 | C30—C29—H29A | 110.2 |
| C18—C17—H17A | 108.8 | C28—C29—H29A | 110.2 |
| C16—C17—H17B | 108.8 | C30—C29—H29B | 110.2 |
| C18'—C17—H17B | 84.6 | C28—C29—H29B | 110.2 |
| C18—C17—H17B | 108.8 | H29A—C29—H29B | 108.5 |
| H17A—C17—H17B | 107.7 | C29—C30—C31 | 110.5 (18) |
| C16—C17—H17C | 109.4 | C29—C30—H30A | 109.5 |
| C18'—C17—H17C | 95.7 | C31—C30—H30A | 109.5 |
| C18—C17—H17C | 75.9 | C29—C30—H30B | 109.5 |
| H17A—C17—H17C | 36.6 | C31—C30—H30B | 109.5 |
| H17B—C17—H17C | 135.0 | H30A—C30—H30B | 108.1 |
| C16—C17—H17D | 109.4 | C30'—C29'—C28 | 117 (3) |
| C18'—C17—H17D | 112.8 | C30'—C29'—H29C | 108.1 |
| C18—C17—H17D | 132.5 | C28—C29'—H29C | 108.1 |
| H17A—C17—H17D | 73.7 | C30'—C29'—H29D | 108.1 |
| H17B—C17—H17D | 36.0 | C28—C29'—H29D | 108.1 |
| H17C—C17—H17D | 107.6 | H29C—C29'—H29D | 107.3 |
| C17—C18—C19 | 112 (4) | C29'—C30'—C31' | 124 (3) |
| C17—C18—H17C | 36.7 | C29'—C30'—H30C | 106.3 |
| C19—C18—H17C | 100.4 | C31'—C30'—H30C | 106.3 |
| C17—C18—H18A | 109.1 | C29'—C30'—H30D | 106.3 |
| C19—C18—H18A | 109.1 | C31'—C30'—H30D | 106.3 |
| H17C—C18—H18A | 143.1 | H30C—C30'—H30D | 106.4 |
| C17—C18—H18B | 109.1 | C30'—C31'—H31D | 109.5 |
| C19—C18—H18B | 109.1 | C30'—C31'—H31E | 109.5 |
| H17C—C18—H18B | 81.9 | H31D—C31'—H31E | 109.5 |
| H18A—C18—H18B | 107.8 | C30'—C31'—H31F | 109.5 |
| C21—C20—Sn1 | 118 (2) | H31D—C31'—H31F | 109.5 |
| C21—C20—H20A | 107.9 | H31E—C31'—H31F | 109.5 |
| Sn1—C20—H20A | 107.9 | O5—C32—H32A | 109.5 |
| C21—C20—H20B | 107.9 | O5—C32—H32B | 109.5 |
| Sn1—C20—H20B | 107.9 | H32A—C32—H32B | 109.5 |
| H20A—C20—H20B | 107.2 | O5—C32—H32C | 109.5 |
| C20—C21—C22 | 114.6 (19) | H32A—C32—H32C | 109.5 |
| C20—C21—H21A | 108.6 | H32B—C32—H32C | 109.5 |
| Symmetry codes: (i) −x+1, −y+1, −z. |
We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the `Students Technology Cultural Innovation Fund' of Liaocheng University (SRT08045HX2).
Berceanc, V., Crainic, C., Haiduc, I., Mahon, M. F., Molloy, K. C., Venter, M. M. & Wilson, P. J. (2002). J. Chem. Soc. Dalton Trans. pp. 1036–1045.
Garcia-Zarracino, R. & Hopfl, H. (2005). J. Am. Chem. Soc. 127, 3120–3130.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Wu, X., Kang, W., Zhu, D., Zhu, C. & Liu, S. (2009). J. Organomet. Chem. 694, 2981–2986.
Recently, a large number of organotin compounds with different structural features have been reported in the literature (Berceanc et al., 2002; Garcia-Zarracino & Hopfl et al., 2005). In continuation of our study of organotin compounds, we present here the synthesis and crystal structure of the title compound (I).
The title compound (Fig. 1) is a centrosymmetric dimer, with three linearly fused four-membered Sn—O—Sn—O rings, resulting in a ladder type structural motif. There are two tri-coordinate O atoms in (I), and each of them links two endocyclic tin atoms and one exocyclic tin atom (Sn(1)—O(4) = 2.022 (4) Å; Sn(2)—O(4) = 2.051 (4) Å; Sn(1)—O(4 A) = 2.127 (4) Å)(Table. 1). The additional links between the endo- and exocyclic Sn are provided by bidentate deprotonated methanol. Each exocyclic Sn atom is also coordinated by monodentate carboxylato ligand. Part of butyl groups were found to be disordered over two sites. The crystal structure of a similiar compound has been reported recently (Wu et al., 2009).