Supporting Information for the Article Entitled
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1 Supporting Information for the Article Entitled Catalytic Production of Isothiocyanates via a Mo(II) / Mo(IV) Cycle for the Soft Sulfur Oxidation of Isonitriles authored by Wesley S. Farrell, Peter Y. Zavalij, and Lawrence R. Sita* Department of Chemistry and Biochemistry University of Maryland, College Park, MD Crystallographic information for 1, 6, and 8. NMR spectral evidence demonstrating the (catalytic) activity of 1 3. Supporting spectra for thiosemicarbazides prepared via on-demand ITC synthesis. S1
2 NMR spectra Demonstrating the Generation of Compounds 1, 2, and 3. Figure S1. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the rapid conversion of 4 to 1 in the presence of excess methyl isocyanide. Labeled resonances are 4 (*), 1 (o), and methyl isocyanide (x). (Note: Reaction was nearly complete before the first NMR could be recorded). S2
3 Figure S2. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the conversion of 4 to 2 in the presence of excess tert-butyl isocyanide. Labeled resonances are 4 (*), 2 (o), and tert-butyl isocyanide (x). S3
4 Figure S3. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the conversion of 4 to 3 in the presence of excess 2,6-dimethylphenyl isocyanide. Labeled resonances are 4 (*), 3 (o), and 2,6-dimethylphenyl isocyanide (x). (Note: A second addition of 2,6-dimethylphenyl isocyanide was performed after recording the first NMR spectrum). S4
5 NMR Spectra Demonstrating the Generation Compounds 5, 6, and ppm Figure S4. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the immediate conversion of 1 to 5 upon the addition of excess sulfur. S5
6 Figure S5. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the immediate conversion of 2 (generated in situ) to 6 upon the addition of excess sulfur. Labeled resonance is tert-butyl isocyanide (x), which overlaps with broad doublet of compound 6. S6
7 ppm Figure S6. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the immediate conversion of 3 (generated in situ) to 7 upon the addition of excess sulfur. The unlabeled resonance at 2.1 ppm is excess 2,6-dimethylphenyl isocyanide (x). S7
8 NMR Spectra Demonstrating Catalytic Production of ITCs using Compounds 1, 2, and 3. Figure S7. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the generation of methyl isothiocyanate from S 8 and excess methyl isocyanide mediated by compound 1 after 0 h (bottom) and 3 d (top) at room temperature. Labeled resonances are methyl isocyanide (x) and methyl isothiocyanate (o). S8
9 Figure S8. Partial 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the generation of tert-butyl isothiocyanate from S 8 and excess tert-butyl isocyanide mediated by compound 2 after 0 h (bottom) and 4 d (top) at room temperature. Labeled resonances are tert-butyl isocyanide (x) and tert-butyl isothiocyanate (o). S9
10 Figure S9. 1 H NMR (400 MHz, benzene-d 6, 25 C) demonstrating the generation of 2,6-dimethylphenyl isothiocyanate from S 8 and excess 2,6-dimethylphenyl isocyanide mediated by compound 3 after 0 h (bottom) and 2 d (top) at 85 C. Labeled resonances are 2,6-dimethylphenyl isocyanide (x) and 2,6- dimethylphenyl isothiocyanate (o).. S10
11 Variable Temperature NMR Experiments Involving the Catalytic Formation of tert-butyl Isothiocyanate from tert-butyl Isocyanide and Sulfur Mediated by Compound 3. [SCNtBu] (M) y = x R² = time (m) Figure S10. Representative plot of concentration of tert-butyl isothiocyanate versus time at 50 C catalyzed by compound 2. k (1/s) y = x R² = T (K) Figure S11. Plot of initial rate constant (s -1 ) versus temperature (K) for the conversion of tert-butyl isocyanide to tert-butyl isothiocyanate catalyzed by 2. S11
12 1/T ln(k/t) y = x R² = Figure S12. Eyring plot for the conversion of tert-butyl isocyanide to tertbutyl isothiocyanate catalyzed by 2. S12
13 ppm Figure S13. Representative 1 H NMR (400 MHz, benzene-d 6, 50 C) spectra of the tert-butyl region during the catalytic generation of tert-butyl isothiocyanate from S 8 and tert-butyl isocyanide mediated by compound 2 (spectra recorded every 200 m). S13
14 Characterization of Thiosemicarbazides through On-Demand Generation of Isothiocyanates. 1-(p-tolylbenzoyl)-4-tert-butylthiosemicarbazide. Yield = 97%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 1.45 (9H, s), 2.36 (3H, s), 3.34 (1H, br), 7.30 (2H, d, J = 8.0 Hz), 7.79 (2H, d, J = 8.0 Hz), 9.11 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 20.9, 28.6, 52.6, 127.5, 128.8, 129.6, 141.8, 165.6, (br). ESI-MS m/z: (M+H). Figure S14. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4-tertbutylthiosemicarbazide. * denotes ethyl acetate solvent impurity. o denoted H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S14
15 Figure S C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4- tert-butylthiosemicarbazide. * denotes ethyl acetate solvent impurity. X denotes DMSO-d 6 solvent. 1-(p-methoxybenzoyl)-4-tert-butylthiosemicarbazide. Yield = 80%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 1.45 (9H, s), 3.82 (3H, s), 7.02 (2H, d, J = 8.8 Hz), 7.87 (2H, d, J = 8.8 Hz), 9.09 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 28.6, 52.6, 55.3, 113.6, 124.5, 129.4, 162.0, 165.2, (br). ESI-MS m/z: (M+H). S15
16 Figure S16. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-methoxybenzoyl)-4- tert-butylthiosemicarbazide. * denotes ethyl acetate solvent impurity. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S16
17 Figure S C( 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-(pmethoxybenzoyl)-4-tert-butylthiosemicarbazide. * denotes ethyl acetate solvent impurity. X denotes DMSO-d 6 solvent. 1-benzoyl-4-tert-butylthiosemicarbazide. Yield = 69%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 1.45 (9H, s), 7.49 (2H, t, J = 7.7 Hz), 7.58 (1H, t, J = 7.5 Hz), 7.89 (2H, d, J = 7.5 Hz), 9.14 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 28.6, 52.7, 127.5, 128.4, 131.8, 132.4, 165.7, ESI-MS m/z: (M+H). S17
18 Figure S18. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-benzoyl-4-tertbutylthiosemicarbazide. * denotes ethyl acetate solvent impurity. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. I denotes methyl substituted impurity present from using 1 as an isolated precatalyst in lieu of preparing 1 in situ. S18
19 Figure S C{ 1 H} NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-benzoyl-4- tert-butylthiosemicarbazide. X denotes DMSO-d 6 solvent. 1-(p-tolylbenzoyl)-4-methylthiosemicarbazide. Yield = 96%. %. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 2.36 (3H, s) (3H, d, J = 4.4 Hz), 7.29 (2H, d, J = 8.3 Hz), 7.81 (2H, d, J = 8.3 Hz), 8.02 (1H, br d), 9.29 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 20.8, 30.8, 127.6, 128.5, 129.6, 141.6, 165.8, ESI-MS m/z: (M+H). S19
20 Figure S20. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4- methylthiosemicarbazide. * denotes ethyl acetate solvent impurity. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S20
21 Figure S C( 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4- methylthiosemicarbazide. * denotes ethyl acetate solvent impurity. X denotes DMSO-d 6 solvent. 1-(p-methoxybenzoyl)-4-methylthiosemicarbazide. Yield = 82%. %. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 2.86 (3H, d, J = 4.4 Hz), 3.82 (3H, s), 7.02 (2H, d, J = 8.9 Hz), 7.89 (2H, d, J = 8.9 Hz), 8.02 (1H, br d, J = 4.4 Hz), 9.27 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 30.8, 55.3, 133.4, 124.6, 129.6, 162.0, 135.4, S21
22 Figure S22. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-methoxybenzoyl)-4- methylthiosemicarbazide. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S22
23 Figure S C( 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-(pmethoxybenzoyl)-4-methylthiosemicarbazide. X denotes DMSO-d 6 solvent. 1-benzoyl-4-methylthiosemicarbazide. Yield = 76%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 2.87 (3H, d, J = 4.3 Hz), 7.49 (2H, t, J = 7.8 Hz), 7.58 (1H, t, J = 7.4 Hz), 7.92 (2H, d, J = 7.8 Hz), 8.05 (1H, br d, J = 4.3 Hz), 9.33 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 30.9, 127.7, 128.2, 131.7, 132.4, ESI-MS m/z: (M+H). S23
24 Figure S24. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4- methylthiosemicarbazide. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S24
25 Figure S C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-benzoyl-4- methylthiosemicarbazide. X denotes DMSO-d 6 solvent. (Note: C b cannot be seen due to the broadness of the signal). 1-(p-tolylbenzoyl)-4-(2,6-dimethylphenyl)thiosemicarbazide. Yield = 95%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 2.15 (6H, s), 2.36 (3H, s), 7.04 (3H, m), 7.29 (2H, d, J = 8.1 Hz), 7.86 (2H, d, J = 8.1), 9.39 (1H, br), 9.53 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 17.9, 20.9, 126.5, 127.3, 127.9, 128.5, 129.9, 136.5, 137.0, 141.5, 166.1, ESI-MS m/z: (M+H). S25
26 Figure S26. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4-(2,6- dimethylphenyl)thiosemicarbazide. * denotes ethyl acetate solvent impurity. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S26
27 Figure S C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-(p-tolylbenzoyl)-4- (2,6-dimethylphenyl)thiosemicarbazide. X denotes DMSO-d 6 solvent. * denotes ethyl acetate solvent impurity. 1-(p-methoxybenzoyl)-4-(2,6-dimethylphenyl)thiosemicarbazide. Yield = 91%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 2.16 (6H, s), 3.81 (3H, s), 7.05 (5H, m), 7.94 (2H, d, J = 8.6 Hz), 9.40 (1H, br), 9.51 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ):17.9, 55.4, 113.3, 124.9, 126.6, 127.3, 129.9, 136.5, 137.0, 161.9, 165.7, ESI-MS m/z: (M+H). S27
28 Figure S28. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-(p-methoxybenzoyl)-4- (2,6-dimethylphenyl)thiosemicarbazide. * denotes ethyl acetate solvent impurity. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S28
29 Figure S C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-(pmethoxybenzoyl)-4-(2,6-dimethylphenyl)thiosemicarbazide. * denotes ethyl acetate solvent impurity. X denotes DMSO-d 6 solvent. 1-benzoyl-4-(2,6-dimethylphenyl)thiosemicarbazide.Yield = 88%. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ): 2.17 (6H, s), 7.05 (3H, m), 7.49 (2H, t, J = 7.4 Hz), 7.57 (1H, t, J = 7.4 Hz), 7.97 (2H, d, J = 7.4 Hz), 9.42 (1H, br), 9.58 (1H, br), (1H, br). 13 C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ): 17.9, 126.6, 127.3, 127.9, 128.0, 131.6, 132.7, 136.5, 137.0, 166.1, ESI-MS m/z: (M+H). S29
30 Figure S30. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of 1-benzoyl-4-(2,6- dimethylphenyl)thiosemicarbazide. * denotes ethyl acetate solvent impurity. o denotes H 2 O solvent impurity. X denotes DMSO-d 6 solvent. S30
31 Figure S C{ 1 H} NMR (125 MHz, 25 C, DMSO-d 6 ) of 1-benzoyl -4-(2,6- dimethylphenyl)thiosemicarbazide. * denotes ethyl acetate solvent impurity. X denotes DMSO-d 6 solvent. Control Experiments For On-Demand Isothiocyanate Synthesis A representative procedure is given. A solution of S 8 (0.063 g, mmol), methyl isocyanide (15 μl, mmol) and p-tolylbenzhydrazide (0.038 g, mmol) in 5 ml THF was prepared and heated to 70 C for 16 h. Volatiles were removed in vacuo to furnish a yellow solid, and the crude reaction mixture was analyzed by 1 H NMR, revealing unreacted p-tolylbenzhydrazide as the only species present. S31
32 Figure S32. 1 H NMR (400 MHz, 25 C, DMSO-d 6 ) of a) crude reaction mixture obtained from heating of methyl isocyanide, S 8, and p-tolylbenzhydrazide in THF for 16 h, and b) pure p-tolylbenzhydrazide. X denotes DMSO-d 6 solvent. o denotes H 2 O solvent impurity. References 1. R. E. Schuster, J. E. Scott, J. Casanova, Org. Synth. 1966, 46, W. S. Farrell, P. Y. Zavalij, L. R. Sita, Angew. Chem. Int. Ed. 2015, 54, S32
33 Crystallographic Information Cp*Mo[N( i Pr)C(Ph)N( i Pr)](CNCH 3 ) 2 (1) Figure S33. Crystal structure of 1 with hydrogen atoms omitted for clarity, ellipsoids for the non-hydrogen atoms are shown at the 30% probability level. A red plate-like specimen of C 27 H 40 MoN 4, approximate dimensions 0.04 mm 0.17 mm 0.21 mm, was used for the X-ray crystallographic analysis. The X- ray intensity data were measured on a Bruker APEX-II CCD system equipped with a graphite monochromator and a MoKα sealed tube (λ = Å). Data collection temperature was 150 K. The total exposure time was hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a triclinic unit cell yielded a total of reflections to a maximum θ angle of (0.71 Å resolution), of which 7694 were independent (average redundancy 2.922, completeness = 99.3%, R int = 3.00%) and6680 (86.82%) were greater than 2σ(F 2 ). The final cell constants of a = (11) Å, b = (11) Å, c = (15) Å, α = (17), β = (18), γ = (17), V =1327.8(2) Å 3, are based upon the refinement of the XYZ-centroids of 8177 reflections above 20 σ(i) with < S33
34 2θ < Data were corrected for absorption effects using the multi-scan method (SADABS). The calculated minimum and maximum transmission coefficients (based on crystal size) are and The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P-1, with Z = 2 for the formula unit, C 27 H 40 MoN 4. The final anisotropic full-matrix least-squares refinement on F 2 with 331 variables converged at R 1 = 3.25%, for the observed data and wr 2 = 6.35% for all data. The goodness-of-fit was The largest peak in the final difference electron density synthesis was e - /Å 3 and the largest hole was e - /Å 3 with an RMS deviation of e - /Å 3. On the basis of the final model, the calculated density was 1.292g/cm 3 and F(000), 544 e -. APEX2 Version (Bruker AXS Inc.) SAINT Version 7.68A (Bruker AXS Inc., 2009) SADABS Version 2008/1 (G. M. Sheldrick, Bruker AXS Inc.) XPREP Version 2008/2 (G. M. Sheldrick, Bruker AXS Inc.) XS Version 2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, ) XL Version 2012/4 (G. M. Sheldrick, (2012) University of Gottingen, Germany) Platon (A. L. Spek, Acta Cryst. (1990). A46, C-34) Table S1. Sample and crystal data for 1. Identification code 2522 Chemical formula C 27 H 40 MoN 4 Formula weight Temperature 150(2) K Wavelength Å Crystal size mm Crystal habit red plate Crystal system triclinic Space group P-1 Unit cell dimensions a = (11) Å α = (17) b = (11) Å β = (18) c = (15) Å γ = (17) Volume (2) Å 3 Z 2 Density (calculated) Mg/cm 3 Absorption coefficient mm -1 F(000) 544 Table S2. Data collection and structure refinement for 1. S34
35 Diffractometer Bruker APEX-II CCD Radiation source sealed tube, MoKα Theta range for data collection 2.04 to Index ranges -14 h 14, -14 k 14, -19 l 19 Reflections collected Independent reflections 7694 [R(int) = ] Coverage of independent 99.3% reflections Absorption correction multi-scan Max. and min. transmission and Structure solution technique direct methods Structure solution program ShelXS-97 (Sheldrick, 2008) Refinement method Full-matrix least-squares on F 2 Refinement program ShelXL-2012 (Sheldrick, 2012) Function minimized Σ w(f 2 o - F 2 c ) 2 Data / restraints / parameters 7694 / 121 / 331 Goodness-of-fit on F Δ/σ max Final R indices 6680 data; I>2σ(I) R 1 = , wr 2 = all data R 1 = , wr 2 = Weighting scheme w=1/[σ 2 (F 2 o )+(0.0100P) P], P=(F 2 o +2F 2 c )/3 Largest diff. peak and hole and eå -3 R.M.S. deviation from mean eå -3 R int = Σ F o 2 - F o 2 (mean) / Σ[F o 2 ] R 1 = Σ F o - F c / Σ F o S35
36 GOOF = S = {Σ[w(F o 2 - F c 2 ) 2 ] / (n - p)} 1/2 wr 2 = {Σ[w(F o 2 - F c 2 ) 2 ] / Σ[w(F o 2 ) 2 ]} 1/2 Cp*Mo[N( i Pr)C(Ph)N( i Pr)](CN t Bu)(η 2 -SCN t Bu) (6) Figure S34. Crystal structure of 6 with hydrogen atoms omitted for clarity, ellipsoids for the non-hydrogen atoms are shown at the 30% probability level. A orange prism-like specimen of C 33 H 52 MoN 4 S, approximate dimensions 0.09 mm &# mm &# mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured on a Bruker APEX-II CCD system equipped with a graphite monochromator and a MoKα sealed tube (λ = Å). Data collection temperature was 150 K. S36
37 The total exposure time was hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of reflections to a maximum θ angle of (0.71 Å resolution), of which9950 were independent (average redundancy 3.676, completeness = 99.6%, R int = 2.84%) and 8565 (86.08%) were greater than 2σ(F 2 ). The final cell constants of a = (11) Å, b = (5) Å, c = (13) Å, β = (2), V = (7) Å 3, are based upon the refinement of the XYZcentroids of 9913 reflections above 20 σ(i) with < 2θ < Data were corrected for absorption effects using the multi-scan method (SADABS). The calculated minimum and maximum transmission coefficients (based on crystal size) are and The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P2 1 /n, with Z = 4 for the formula unit, C 33 H 52 MoN 4 S. The final anisotropic full-matrix least-squares refinement on F 2 with 426 variables converged at R 1 = 3.77%, for the observed data and wr 2 = 7.48% for all data. The goodness-of-fit was The largest peak in the final difference electron density synthesis was e - /Å 3 and the largest hole was e - /Å 3 with an RMS deviation of e - /Å 3. On the basis of the final model, the calculated density was g/cm 3 and F(000), 1344 e -. APEX2 Version (Bruker AXS Inc.) SAINT Version 7.68A (Bruker AXS Inc., 2009) SADABS Version 2008/1 (G. M. Sheldrick, Bruker AXS Inc.) XPREP Version 2008/2 (G. M. Sheldrick, Bruker AXS Inc.) XS Version 2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, ) XL Version 2012/4 (G. M. Sheldrick, (2012) University of Gottingen, Germany) Platon (A. L. Spek, Acta Cryst. (1990). A46, C-34) Table S2. Sample and crystal data for 6. Identification code 2530 Chemical formula C 33 H 52 MoN 4 S Formula weight Temperature 150(2) K Wavelength Å Crystal size 0.09 &# &# mm Crystal habit orange prism Crystal system monoclinic Space group P2 1 /n Unit cell dimensions a = (11) Å α = 90 b = (5) Å β = (2) c = (13) Å γ = 90 Volume (7) Å 3 S37
38 Z 4 Density (calculated) Mg/cm 3 Absorption coefficient mm -1 F(000) 1344 Table S10. Data collection and structure refinement for 6. Diffractometer Bruker APEX-II CCD Radiation source sealed tube, MoKα Theta range for data collection 2.07 to Index ranges -12 ≤ h &# , -51 ≤ k &# , -15 ≤ l &# Reflections collected Independent reflections 9950 [R(int) = ] Coverage of independent 99.6% reflections Absorption correction multi-scan Max. and min. transmission and Structure solution direct methods technique Structure ShelXS-97 (Sheldrick, 2008) solution program Refinement method Full-matrix least-squares on F 2 Refinement program ShelXL-2012 (Sheldrick, 2012) Function minimized Σ w(f 2 o - F 2 c ) 2 Data / restraints / 9950 / 216 / 426 parameters Goodness-of-fit on F Δ/σ max Final R indices 8565 data; I>2σ(I) R 1 = , wr 2 = S38
39 Weighting scheme Largest diff. peak and hole R.M.S. deviation from mean R all data 1 = , wr 2 = w=1/[σ 2 (F 2 o )+(0.0100P) P], P=(F 2 o +2F 2 c )/ and eå eå -3 R int = Σ F o 2 - F o 2 (mean) / Σ[F o 2 ] R 1 = Σ F o - F c / Σ F o GOOF = S = {Σ[w(F o 2 - F c 2 ) 2 ] / (n - p)} 1/2 wr 2 = {Σ[w(F o 2 - F c 2 ) 2 ] / Σ[w(F o 2 ) 2 ]} 1/2 Cp*Mo[N( i Pr)C(Ph)N( i Pr)](κ-(S,S)-S 2 CN t Bu) (8) Figure S35. Crystal structure of 8 with hydrogen atoms omitted for clarity, ellipsoids for the non-hydrogen atoms are shown at the 30% probability level. A orange prism-like specimen of C H MoN 3 O 0.38 S 2, approximate dimensions 0.14 mm &# mm &# mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured on a Bruker S39
40 APEX-II CCD system equipped with a graphite monochromator and a MoKα sealed tube (λ = Å). Data collection temperature was 150 K. The total exposure time was 4.04 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of reflections to a maximum θ angle of (0.71 Å resolution), of which 9155were independent (average redundancy 5.659, completeness = 100.0%, R int = 2.20%) and 8447 (92.27%) were greater than 2σ(F 2 ). The final cell constants of a = (9) Å, b = (19) Å, c = (18) Å, β = (14), V = (5) Å 3, are based upon the refinement of the XYZcentroids of 9946 reflections above 20 σ(i) with < 2θ < Data were corrected for absorption effects using the multi-scan method (SADABS). The calculated minimum and maximum transmission coefficients (based on crystal size) are and The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P2 1 /n, with Z = 4 for the formula unit, C H MoN 3 O 0.38 S 2. The final anisotropic fullmatrix least-squares refinement on F 2 with 319 variables converged at R 1 = 2.04%, for the observed data and wr 2 = 4.62% for all data. The goodnessof-fit was The largest peak in the final difference electron density synthesis was e - /Å 3 and the largest hole was e - /Å 3 with an RMS deviation of e - /Å 3. On the basis of the final model, the calculated density was g/cm 3 and F(000), 1287 e -. APEX2 Version (Bruker AXS Inc.) SAINT Version 7.68A (Bruker AXS Inc., 2009) SADABS Version 2008/1 (G. M. Sheldrick, Bruker AXS Inc.) XPREP Version 2008/2 (G. M. Sheldrick, Bruker AXS Inc.) XS Version 2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, ) XL Version 2012/4 (G. M. Sheldrick, (2012) University of Gottingen, Germany) Platon (A. L. Spek, Acta Cryst. (1990). A46, C-34) Table S3. Sample and crystal data for 8. Identification code 2480 Chemical formula C H MoN 3 O 0.38 S 2 Formula weight Temperature Wavelength Crystal size Crystal habit Crystal system 150(2) K Å 0.14 &# &# mm orange prism monoclinic Space group P2 1 /n S40
41 Unit cell dimensions a = (9) Å α = 90 b = (19) Å β = (14) c = (18) Å γ = 90 Volume (5) Å 3 Z 4 Density (calculated) Mg/cm 3 Absorption coefficient mm -1 F(000) 1287 Table S3. Data collection and structure refinement for 8. Diffractometer Radiation source Theta range for data collection Index ranges Reflections collected Bruker APEX-II CCD sealed tube, MoKα 2.14 to Independent reflections 9155 [R(int) = ] Coverage of independent reflections 100.0% Absorption correction Max. and min. transmission Structure solution technique Structure solution program -12 ≤ h &# , -26 ≤ k &# , -26 ≤ l &# multi-scan and direct methods ShelXS-97 (Sheldrick, 2008) Refinement method Full-matrix least-squares on F 2 Refinement program ShelXL-2012 (Sheldrick, 2012) Function minimized Σ w(f o 2 - F c 2 ) 2 Data / restraints / parameters Goodness-of-fit on F Δ/σ max / 0 / 319 Final R indices 8447 data; I>2σ(I) R 1 = , wr 2 = all data R 1 = , wr 2 = Weighting scheme w=1/[σ 2 (F o 2 )+(0.0100P) P], P=(F o 2 +2F c 2 )/3 Largest diff. peak and hole R.M.S. deviation from mean and eå eå -3 R int = Σ F o 2 - F o2 (mean) / Σ[F o2 ] R 1 = Σ F o - F c / Σ F o S41
42 GOOF = S = {Σ[w(F o 2 - F c 2 ) 2 ] / (n - p)} 1/2 wr 2 = {Σ[w(F o 2 - F c 2 ) 2 ] / Σ[w(F o 2 )2 ]} 1/2 S42
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