Towards the installation of transition metal ions on donor ligand decorated. tin sulfide clusters

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1 Towards the installation of transition metal ions on donor ligand decorated tin sulfide clusters Beatrix E. K. Barth, a Eliza Leusmann, a Klaus Harms a and Stefanie Dehnen a * Fachbereich Chemie, Wissenschaftliches Zentrum für Materialwissenschaften, Philipps-Universität Marburg, Hans-Meerwein-Straße, D Marburg, Germany, dehnen@chemie.uni-marburg.de SUPPLEMENTARY INFORMATION Contents: 1. Synthesis details 2. Single crystal X-ray crystallography 3. Electrospray ionization (ESI) mass spectrometry 4. Additional information on the formation processes of the title compounds 5. References for the Supporting Information

2 1. Synthesis details General: If not otherwise mentioned, all synthesis steps were performed with strict exclusion of air and external moisture. All solvents were dried and freshly distilled prior to use. Cl 3 SnCMe 2 CH 2 C(O)Me, [1] [(R 1 Sn) 4 S 6, A] (R 1 = CMe 2 CH 2 C(O)Me), [1] were prepared according to the reported methods. 2,2'-(Hydrazonomethylene)dipyridine (bispyridylhydrazone) was synthesized by a modified synthesis method (see below). Na 2 S 9H 2 O, mesityl oxide, N 2 H 4 H 2 O, di-2-pyridylketone were purchased from Aldrich and used without further purification. 1 H NMR, 13 C NMR and 119 Sn NMR measurements were carried out using a Bruker DRX 300 MHz and DRX 400 MHz spectrometer at 25ºC. The chemical shifts were quoted in ppm relative to the residual protons of deuterated solvents in 1 H-NMR and 13 C-NMR. Me 4 Sn was used as internal standard for 119 Sn-NMR measurements. EDX analyses were performed using the EDX device Voyager 4.0 of Noran Instruments coupled with the electron microscope CamScan CS 4DV. Data acquisition was performed with an acceleration voltage of 20 kv and 100 s accumulation time. Synthesis of bispyridylhydrazone: Di-2-pyridylketone (0.552 mg, 3.00 mmol) was dissolved in 20 ml of EtOH and 100 ml (109.2 g, 2.2 mol) of hydrazine-hydrate (80% in water) was added under air. The solution was heated to reflux for 3 h and afterwards stirred for 8 h. The solvent and remaining hydrazine was removed in vacuo. A light orange oil was received and used without further purification. Attempts to purify on silica gel/aluminumoxide, or by destillation led to decomposition. HRMS(ESI): m/z (calc.) [M Na] + = , m/z (exp.) = m/z; 1 H-NMR (300 MHz, CDCl 3, 25 C): = (m, 1H, py), (m, 1H, py), 8.03 (br, 2H, NH 2 ), 7.75 (d, 1H, py, J = 8.01 Hz), (m, 1H, py), (m, 1H, py), 7.33 (d, 1H, py, J = 8.07 Hz), (m, 1H, py), (m, 1H, py) ppm. 13 C-NMR (75 MHz, CDCl 3, 25 C): = (1C, py 2 CN), (2C, py),

3 (1C, py), (1C, py), (2C, py), (1C, py), (1C, py), (2C, py) ppm. Synthesis of 2, 3a and 3b: Four eq. of bispyridylhydrazone (101 mg, mmol) and one eq. of A (136 mg, mmol) have been allowed to evacuate over 30 min and afterwards solved in a MeOH/1,4-dioxane mixture (8 ml/16 ml). The suspension was stirred for approximately 10 h until the solution of 3b becomes abruptly clear and red-brown. If the reaction is carried out in CH 2 Cl 2 (7 ml, stirred for 8 h), and crystallization is accomplished by layering with n-hexane, the crystal structure of the resulting modification 3a, which contains CH 2 Cl 2 instead of 1,4-dioxane/MeOH, suffers from heavy twinning problems. Crystals of 3a - 3b and 2 were obtained by layering each solution with n-hexane (or n-pentane) (1:1) within 2 days. Separation of the products was not possible. Yield (2 and 3): (54%, mmol); 1 H- NMR (400 MHz, CD 2 Cl 2, 25 C): = (ddd, 4H, py), (ddd, 4H, py), (m, 4H, py), (m, 8H, py), (m, 4H, py), (m, 8H, py), 2.61 (s, 8H, CH 2 ), 2.06 (s, 12H, C(NN)Me), 0.96 (s, 24H, CMe 2 ) ppm. 119 Sn-NMR (149 MHz, CD 2 Cl 2, 25 C): = 76; 82 ppm. HRMS(ESI): m/z (calc.) [M H] + = , m/z (exp.) = m/z, 2 [(RSn) 3 S 4 ] was found at m/z (calc.) [M] + = , m/z (exp.) = , [RSn 2 S 2 ] m/z (calc.) = , m/z (exp.) = ; EDX: Sn:S (calc.) 6:10, found 5.95:9.95. Synthesis of 4-6: One eq. of A ( mmol, 76 mg) and four eq. of bispyridylhydrazone (0.288 mmol, 57 mg) were dissolved in CH 2 Cl 2 (7 ml) and stirred for eight hours. After the solution was diluted with CHCl 3 (35 ml), it was layered with a methanolic (40 ml) solution of ZnX 2 (4: ZnCl mmol, 157 mg), (5: ZnBr mmol, 259 mg) (6: ZnI mmol, 368 mg). A thin layer of toluene between the reactive phases can lead to better crystallization. After one day brown and light yellow powder appears and after four days very small colorless single crystals were obtained. By stirring the methanolic solution with the 3

4 CHCl 3 /CH 2 Cl 2 phase for one hour and layering the filtrated mixture with n-hexane, the same product was received with lower crystallization tendency. Upon application of high vacuum, the single-crystals lose their crystal solvent and become amorphous. Yield: 29% (4, mmol), 41% (5, mmol), 23% (6, mmol); EDX (5, single crystals): Sn:Zn:S (calc.) 4:8:10, found 4.01:7.97: Single crystal X-ray crystallography General: Data of the X-ray structure analysis: T = 100 K, graphite monochromator, imaging plate detector Stoe IPDS2/2T. All structures were solves by direct methods in SHELXS97 refined by full-matrix least-squares refinement against F 2 in SHELXL97 [2] or SHELXL [5] Absorption correction were performed either using empirical, using indexed faces [5] or semi empirical, [6,7] using multi-scanned reflections. Where possible, H atoms were inserted assuming idealized geometry and refined riding on their parent atoms with Ueq = nueq (parent atom), where n = 1.5 for H atoms in methyl groups. Table S1 summarizes the crystallographic data of all crystalline compounds, including the data of compound 2 that should only be viewed as a structural model. Details on the refinement of the latter are provided below. Table S2 summarizes selected structural parameters. CCDC contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via Details on the refinement of compound 2: Crystals of compound 2 exhibited very poor scattering capability, resulting in a high R(int) value. For this, the structure shown below is only considered as a model to confirm its composition and topology. Restraints were needed to fix the carbon atoms of one of the pyridine rings. 4

5 Figure S1. Molecular structure of 2. H atoms are omitted for clarity. C atoms without labels are denoted as sticks. Figure S2. Arrangement of the molecules in the crystal structure of 2. H atoms are omitted for clarity. C and N atoms are denoted as sticks. Thermal ellipsoids are drawn at 50% probability. 5

6 Details on the refinement of compound 3a: Crystals of 3a were pseudo-merohedral twins. The structure has been refined using the twin matrix [ ]. The ratio of the twin components was 64/36. Disordered solvent (CH 2 Cl 2 ) and one disordered six-membered ring have been refined using restraints for distances and for the shape of the thermal displacement parameters. For further details see Table S1. Figure S3. Molecular structure of 3a with atom labeling scheme. H atoms are omitted for clarity. Thermal ellipsoids are drawn at 30% probability. 6

7 Figure S4. Arrangement of the molecules in the crystal structure of 3a. H atoms and solvent molecules are omitted for clarity. C and N atoms are denoted as sticks. Thermal ellipsoids are drawn at 50% probability. Details on the refinement of compound 3b: Restraints were included for the refinement of the thermal displacement parameters of solvent molecules. For further details see Table S1. 7

8 Figure S5. Molecular structure of 3b with atom labeling scheme. H atoms are omitted for clarity. Thermal ellipsoids are drawn at 50% probability. 8

9 Figure S6. Arrangement of the molecules in the crystal structure of 3b. H atoms and solvent molecules are omitted for clarity. C and N atoms are denoted as sticks. Thermal ellipsoids are drawn at 50% probability. Details on the refinement of compound 4: Restraints for bond distances were included into the refinement of the heavily disordered solvent (superposition of CH 2 Cl 2 and CHCl 3 ). For further details see Table S1. 9

10 Figure S7. Molecular structure of 4 with atom labeling scheme of the inorganic core (left hand side) and the organic substituents (right hand side), H atoms are omitted for clarity. Thermal ellipsoids are drawn at 50% probability. 10

11 Figure S8. Arrangement of the molecules in the crystal structure of 4. H atoms and solvent molecules are omitted for clarity. C and N atoms are denoted as sticks. Thermal ellipsoids are drawn at 50% probability. 11

12 Details on the refinement of compound 5: Crystals of 5 were non-merohedral twins. Refinement was performed using detwinned data of the main domain. Disordered solvent (CH 2 Cl 2 ) has been refined using restraints. Large anisotropic thermal displacement parameters indicate additional disorder that has not been resolved. For further details see Table S1. Figure S9. Molecular structure of 5 with atom labeling scheme of the inorganic core (left hand side) and the organic substituents (right hand side), H atoms are omitted for clarity. Thermal ellipsoids are drawn at 50% probability. 12

13 Figure S10. Arrangement of the molecules in the crystal structure of 5. H atoms and solvent molecules are omitted for clarity. C and N atoms are denoted as sticks. Thermal ellipsoids are drawn at 50% probability. Details on the refinement of compound 6: Crystals of 6 were non-merohedral twins. For the refinement, detwinned data of the main twin component were used. Restraints were included for the refinement of disordered solvent water, CH 2 Cl 2, CHCl 3, MeOH. For further details see Table S1. 13

14 Figure S11. Molecular structure of 6 with atom labeling scheme of the inorganic core (left hand side) and the organic substituents (right hand side), H atoms are omitted for clarity. Thermal ellipsoids are drawn at 50% probability. Figure S12. Arrangement of the molecules in the crystal structure of 6. H atoms and solvent molecules are omitted for clarity. C and N atoms are denoted as sticks. Thermal ellipsoids are drawn at 50% probability. 14

15 Table S1: Crystallographic and refinement details of compounds 2, 3a, 3b, and 4-6 at 100(2) K (Mo K α -radiation, λ = Å). Compound 2 (only considered as a structural model) 3a = 3 5CH 2 Cl 2 3b = 3 1,4- dioxane 5MeOH 4 2CHCl 3 2CH 2 Cl 2 5 CHCl 3 CH 2 Cl CHCl MeOH 0.5H 2 O empirical formula C 51 H 58 N 12 S 5 Sn 3 C 73 H 84 Cl 10 N 16 S 10 Sn 6 C 77 H 104 N 16 O 7 S 10 Sn 6 C 72 H 82 Cl 18 N 16 S 10 Sn 4 Zn 8 C 70 H 79 B r8 Cl 5 N 16 S 10 Sn 4 Zn 8 C 70 H Cl 3.75 I 8 N 16 O 1.25 S 10 Sn 4 Zn 8 fw /g mol crystal color and shape needles,colorless plate, colorless block, colorless plate, colorless prism, colorless prism, colorless crystal size /mm x 0.16 x x 0.10 x x 0.13 x x 0.05 x x 0.10 x x 0.10 x 0.04 crystal system monclinic triclinic monclinic tetragonal triclinic triclinic space group C 2/c P C 2/m I 4 1 /a P P a /Å (3) (1) (1) (2) (1) (1) b /Å (2) (2) (1) (2) (1) (1) c /Å (3) (1) (1) (1) (1) (1) α /deg (1) (1) 85.02(1) β /deg (1) 71.42(1) 96.15(1) (1) 69.87(1) γ /deg (6) (1) 70.66(1) V /Å (2) (3) (6) (1) (6) (3) Z ρ calcd /g cm µ(mo K α ) /mm absorption correction type empirical semi-empirical from Empirical none empirical semi-empirical from equivalents equivalents min./max. transmission 0.29/ / / / / θrange /deg 2.54/ / / / / /51.00 no. of meas. reflns R(int) indep. reflns indep. reflns. (I >2σ(I)) no. of parameters R 1 (I > 2σ(I))/wR 2 (all data) / / / / / / S (all data) max. peak/hole/e - Å / / / / / / CCDC No. CCDC CCDC CCDC CCDC CCDC

16 Table S2: Selected structural parameters [Å, ] of compounds 3a, 3b and 4-6. Distances /Å and angles / 3a 3b 4 2CHCl 3 2CH 2 Cl 2 5 CHCl 3 CH 2 Cl CHCl MeOH 0.5H 2 O Sn1 S (3) 2.413(2) 2.469(4) 2.445(4) 2.446(3) Sn1 S (3) 2.499(2) 2.412(4) 2.439(4) 2.437(3) Sn1 S (3) 2.414(2) 2.398(4) 2.380(4) 2.387(3) Sn2 S (3) 2.396(2) 2.469(4) 2.423(4) 2.429(3) Sn2 S (2) 2.992(3) 2.412(4) - - Sn2 S (3) 2.379(3) (4) 2.462(3) Sn3 S (3) Sn3 S (2) Sn C 2.159(11)-2.208(11) 2.186(7) 2.167(16) 2.158(15)-2.224(15) 2.203(13)-2.234(16) Sn N 2.424(8)-2.450(9) 2.427(6) 2.72(1) - - N N 1.394(14)-1.397(12) 1.403(8) 1.411(16) 1.396(18)-1.430(15) 1.365(18)-1.393(15) Zn X (4) 2.336(3)-2.414(2) (18) (17) Zn a S (4) 2.286(4)-2.310(5) 2.291(3)-2.310(3) Zn b S (5) 2.313(4)-2.370(5) 2.312(3)-2.364(3) Zn1 N (13) 2.060(13) 2.087(12) Zn1 N (14) 2.069(14) 2.060(11) Sn c -S-Sn c 88.42(9) 83.95(8)-87.63(9) (6) (16) (16) (12) (12) Sn d -S-Sn c 84.56(7)-94.27(9) 96.59(7)-81.11(8) S-Sn-S 85.46(8) (9) 91.67(9) (9) 99.63(11) (14) 96.27(14) (14) 95.55(11) (11) Sn-S-Zn a (15) 94.08(14) (15) 94.02(12) (12) Sn-S-Zn b (17) (17) (16) (17) (12) (14) S-Zn a -X (2) (14) (13) (11) (12) S-Zn b -X (16) (17) (12) (12) (10) (9) N-Zn a -X (4)-108.3(3) 103.5(4)-113.8(4) 101.4(3)-113.4(3) S-Zn-S (15) (15) 98.96(15) (16) 99.53(12) (12) N-Zn-S (3)-117.4(3) 100.4(4)-122.0(4) 101.9(3)-122.1(3) Zn-S-Zn (18) (17) (16) (17) (13) (13) a = atoms coordinating to pyridine; b = atoms without coordination to pyridine; c = atoms bearing an organic moiety; d = atoms bearing no organic moiety 16

17 Relative Abundance Electronic Supplementary Material (ESI) for Chemical Communications 3. Electrospray ionization (ESI) mass spectrometry ESI-MS measurements were performed on a Thermo Fischer Scientifics Finnigan LTQ-FT. Spectra recorded in the cation ESI (+) mode from the reaction solution of A with bispyridylhydrazone in CH 2 Cl 2 (Figures S13, Figure S14 and Figure S15) and of a THF solution containing re-dissolved crystals of 3a (Figure S16) are shown below. The fragment [RSn 2 S 2 ] + is found in the reaction solution ESI (+) mass spectrum with a relative abundance of 100%; it is not clear so far, whether it is generated under ESI-MS conditions or whether it already existed in the reaction solution. However it might play an important role later on in the formation process of 4-6. Barth_16_BB100etj_ #20-32 RT: AV: 13 NL: 6.18E2 F: FTMS + p ESI Full ms [ ] Figure S13. Overview ESI (+) mass spectrum of the reaction solution of A with bispyridylhydrazone in CH 2 Cl m/z 17

18 Relative Abundance Relative Abundance Electronic Supplementary Material (ESI) for Chemical Communications measured NL: 1.36E2 Barth_16_BB100etj_ #27 RT: 3.34 AV: 1 F: FTMS + p ESI Full ms [ ] NL: 1.64E3 c68 h 76 n 16 s 10 Sn 6 h 1: calculated C 68 H 77 N 16 S10 Sn 6 p (gss, s /p:40) Chrg 1 R: m/z measured NL: 8.01E2 Barth_16_BB100etj_ #68-69 RT: AV: 2 F: FTMS + p ESI Full ms [ ] calculated NL: 2.57E3 c51h 57 n 12 Sn 3 s 4: C 51H 57 N 12 Sn 3 S4 p (gss, s /p:40) Chrg 1 R: m/z Figure S14. ESI (+) mass spectra of the [M H] + peaks of 3 (top) and 1 (bottom) as measured and as simulated. 18

19 Relative Abundance Electronic Supplementary Material (ESI) for Chemical Communications measured NL: 7.37E2 Barth_16_ 44337#26 FTMS + p [ calculated NL: 3.80E3 c17 h 19 n 4 C 17 H 19 N p (gss, s / R: m/z Figure S15. ESI (+) mass spectra of the [M] + peaks of [RSn 2 S 2 ] + (bottom), as measured and as simulated. The peak at higher mass observed at m/z = could be taken as a hint for an alternative reaction pathway compared to that given in Scheme 2 (main text), which would start out from a ketazine derivative of A, followed by attack by an organotin-s(h) moiety. This pathway cannot be excluded for sure, but so far, we were not in the position to assign the according peak to a reasonable formula. For 4-6, several solvents were used to re-dissolve the crystals; additionally the reaction solutions themselves were investigated. However, only fragments of the ternary clusters were detected, exhibiting the isotopic patterns of zinc, tin and sulfur. None of them could be clearly assigned a formula due to the presence of (fragments) of the organic ligands 19

20 Relative Abundance Relative Abundance Electronic Supplementary Material (ESI) for Chemical Communications Barth_16_BB100h-b #19-25 RT: AV: 7 NL: 7.45E5 F: FTMS + c ESI Full ms [ ] m/z Figure S16. ESI (+) mass spectrum of a THF solution containing re-dissolved crystals of 3a NL: 3.12E2 Barth_16_BB100h-b#38-40 RT: AV: 3 F: FTMS + p ESI w SIM ms [ ] NL: 1.61E3 C 68 H 76 N 16 S10 Sn 6: C 68 H 76 N 16 S10 Sn 6 p (gss, s /p:40) Chrg 1 R: m/z Figure S17. ESI (+) mass spectra of the [M H] + peaks of re-dissolved crystals of 3a as measured and as simulations. 20

21 4. Additional information on the formation processes of the title compounds We assume that after addition of an HS group at 1 +, an intermediate is formed (Scheme 1), which provokes an intramolecular, nucleophilic attack to form a (protonated) diazo group in 2 (see Scheme S1), while the excess electron density is pushed onto the bispyridine unit, where the negative charge is delocalized over the two aromatic rings and its connecting carbon atom C24; this is additionally confirmed by a trigonal planar arrangement of the two pyridinecarbon atoms, the adjacent aza-nitrogen atom N6 and C24 (see Figure S1). Thus, the extended aromatic system promoted the formation of compound 2. Scheme S1. Addition of HS ions to 1 + for the generation of 2. The formation of 2 provides a so far unprecedented hint toward the extension of the defectheterocubane moiety leading to the µ-s-bridged [Sn 6 S 10 ] skeleton, such as observed in 3. The cation 1 + generally suggests an attack of HS ions to be the starting point for re-arrangements, such as for the generation of the [(R 4 Sn) 2 (µ-s)s 2 ] unit present in 4-6. The formation of SnS during the reaction of A with bispyridylhydrazone, comes along with the release of R 6 (R 6 = Me 2 CCHC(NNpy 2 )Me), probably as a result of a β-h-elimination in the reaction solution (Scheme 2). This agrees with the occurrence of two observable signals in the 1 H-NMR spectrum of the reaction solution in CD 2 Cl 2 arising at 2.08 ( 4 J = 1.0, d, 3H, trans-me) and 1.87 ppm ( 4 J = 1.0, d, 3H, cis-me), both coupling with the vinyl hydrogen to give a multiplet at 6.11 ppm (m, 1H), as shown in Figure S18. 21

22 Figure S18. 1 H NMR detail of reaction solution of 1, 2 and 3 in CD 2 Cl 2. Monitoring of the reaction solution by means of time-dependent 119 Sn-NMR measurements over a period of 16 hours in CH 2 Cl 2 (Scheme 3) helped to gain some information on the equilibrium of the precursors. The development of the spectra indicated that A (44.6 ppm), its conformers ( ppm) [1] and its adamantane-type isomer ( ppm) in solution, are consumed within the first 6 h. Two signals at 14.7 and 15.1 ppm, which cannot be detected after 6.5 h, point toward the interim formation of a mixed valence species [{(RSn IV ) 2 -(µ-s) 2 } 3 Sn III 2S 6 ] (Sn III : 12.3 ppm, Sn IV : 15.2 ppm). [1] Further weak signals appear after 1.5 h at 57.1 ppm, 62.1 ppm, 76.5 ppm and 81.6 ppm, but vanish again after 6.5 h. In contrast to the defect-heterocubane species 1 +, no signals are detected in CD 2 Cl 2 that can be assigned to the product 3, indicating low abundance of 3 in the solution equilibrium. However signals at 62.0 ppm, at 76.4 ppm and 81.6 ppm can clearly be seen as product 22

23 signals of a defect-heterocubane species [(RSn) 3 S 4 ] in solution, which is in good accordance with already known hydrazine functionalized Sn/S cages. [3] Vanishing of signals of both the double-decker complex A and its adamantane-type isomer during the first two hours confirms the equilibrium between the starting conformers, but it also indicates that the intermediate products are primarily formed from A (44.6 ppm), which is consumed much faster. Furthermore, the inorganic core of 1 +, 2 and 3 contain a RSnS 2 SnR unit, which also supports the assumption. 23

24 * * * * * * * ** Scheme S3. Time-dependent 119 Sn-NMR measurement upon a reaction of A (0.071 g, mmol, 1 eq.) with bispyridylhydrazone (0.053 g, mmol, 4 eqs.), recorded at 300 K with rotation over a period of 16 h in CD 2 Cl 2. 24

25 6. References for the Supporting Information [1] Z. Hassanzadeh Fard, C. Müller, T. Harmening, R. Pöttgen and S. Dehnen Angew. Chem. Int. Ed. 2009, 48, [2] Sheldrick, G. M. SHELXTL, version 5.1; Bruker AXS Inc.: Madison, WI, 1997 [3] Z. Hassanzadeh Fard, L. Xiong, C. Müller, M. Hołyńska and S. Dehnen Chem. Eur. J. 2009, 15, [4] G. M. Sheldrick, Acta Crystallogr. 2008, A64, [5] G. M. Sheldrick, SHELXL-2013, University of Göttingen, Germany, [6] X-AREA version 1.56, Stoe & Cie GmbH, Darmstadt, Germany, [7] XPREP version 2013/1, Bruker-AXS, Karlsruhe, Germany,

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