C H Activation of Cp* Ligand Coordinated to Ruthenium. Center: Synthesis and Reactivity of a Thiolate-Bridged
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1 Supporting Information C H Activation of Cp* Ligand Coordinated to Ruthenium Center: Synthesis and Reactivity of a Thiolate-Bridged Diruthenium Complex Featuring Fulvene-like Cp* Ligand Xiaoxiao Ji, Dawei Yang,*, Peng Tong, Jianzhe Li, Baomin Wang, and Jingping Qu*,, State Key Laboratory of Fine Chemicals, Dalian University of Technology, 2 Linggong Road, Dalian , P. R. China Key Laboratory for Advanced Materials, East China University of Science and Technology, Shanghai , P. R. China * qujp@dlut.edu.cn yangdw@dlut.edu.cn S1
2 Contents: Table S1. Crystallographic data for 3[PF 6 ] and 4[PF 6 ]... S4 Table S2. Crystallographic data for 5[PF 6 ] and 6[PF 6 ]... S5 Table S3. Crystallographic data for 7[PF 6 ]... S6 Figure S1. ORTEP diagram of 3[PF 6 ]... S7 Table S4. Selected bond distances (Å) and bond angles ( ) for 3[PF 6 ]... S7 Figure S2. ORTEP diagram of 4[PF 6 ]... S8 Table S5. Selected bond distances (Å) and bond angles ( ) for 4[PF 6 ]... S8 Figure S3. ORTEP diagram of 5[PF 6 ]... S9 Table S6. Selected bond distances (Å) and bond angles ( ) for 5[PF 6 ]... S9 Figure S4. ORTEP diagram of 6[PF 6 ]... S10 Table S7. Selected bond distances (Å) and bond angles ( ) for 6[PF 6 ]... S10 Figure S5. ORTEP diagram of 7[PF 6 ]... S11 Table S8. Selected bond distances (Å) and bond angles ( ) for 7[PF 6 ]... S11 Figure S6. ESI-HRMS of 2[PF 6 ] in CH 2 Cl 2... S12 Figure S7. ESI-HRMS of 3[PF 6 ] in CH 2 Cl 2... S13 Figure S8. ESI-HRMS of 4[PF 6 ] in CH 2 Cl 2... S14 Figure S9. ESI-HRMS of 5[PF 6 ] in CH 2 Cl 2... S15 Figure S10. ESI-HRMS of 6[PF 6 ] in CH 2 Cl 2... S16 Figure S11. ESI-HRMS of 7[PF 6 ] in CH 2 Cl 2... S17 Figure S12. The 1 H NMR spectrum of 2[PF 6 ] in CD 2 Cl 2... S18 Figure S13. The 13 C NMR spectrum of 2[PF 6 ] in CD 2 Cl 2... S18 Figure S14. The 1 H NMR spectrum of 3[PF 6 ] in CD 2 Cl 2... S19 Figure S15. The 13 C NMR spectrum of 3[PF 6 ] in CD 2 Cl 2... S19 Figure S16. The 1 H NMR spectrum of 4[PF 6 ] in CD 2 Cl 2... S20 Figure S17. The 13 C NMR spectrum of 4[PF 6 ] in CD 2 Cl 2... S20 Figure S18. The 1 H NMR spectrum of 5[PF 6 ] in CD 2 Cl 2... S21 Figure S19. The 13 C NMR spectrum of 5[PF 6 ] in CD 2 Cl 2... S21 Figure S20. The 1 H NMR spectrum of 6[PF 6 ] in CD 2 Cl 2... S22 Figure S21. The 13 C NMR spectrum of 6[PF 6 ] in CD 2 Cl 2... S22 S2
3 Figure S22. The 1 H NMR spectrum of 7[PF 6 ] in CD 2 Cl 2... S23 Figure S23. The 13 C NMR spectrum of 7[PF 6 ] in CD 2 Cl 2... S23 Figure S24. The IR (film) spectrum of 2[PF 6 ]... S24 Figure S25. The IR (film) spectrum of 3[PF 6 ]... S24 Figure S26. The IR (film) spectrum of 4[PF 6 ]... S25 Figure S27. The IR (film) spectrum of 5[PF 6 ]... S25 Figure S28. The IR (film) spectrum of 6[PF 6 ]... S26 Figure S29. The IR (film) spectrum of 7[PF 6 ]... S26 S3
4 Table S1. Crystallographic data for 3[PF 6 ] and 4[PF 6 ] Complex 3[PF 6 ] 4[PF 6 ] Formula C 26 H 34 ClF 6 PRu 2 S 2 C 26 H 33 F 6 I 2 PRu 2 S 2 Formula weight Crystal dimensions (mm 3 ) Crystal system Triclinic Monoclinic Space group P 1 P2(1)/n a (Å) (17) (4) b (Å) (3) 9.210(3) c (Å) (3) (9) α (º) (8) β (º) (9) (4) γ (º) (8) Volume (Å 3 ) (5) (17) Z 2 4 T (K) 301(2) 253(2) D calcd (g cm 3 ) μ (mm 1 ) F (000) No. of rflns. collected No. of indep. rflns. /R int 5438 / / No. of obsd. rflns. [I 0 > 2σ(I 0 )] Data / restraints / parameters 5438 / 0 / / 0 / 352 R 1 / wr 2 [I 0 > 2σ(I 0 )] / / R 1 / wr 2 (all data) / / GOF (on F 2 ) Largest diff. peak and hole (e Å 3 ) / / S4
5 Table S2. Crystallographic data for 5[PF 6 ] and 6[PF 6 ] Complex 5[PF 6 ] 6[PF 6 ] Formula C 26 H 33 F 6 PRu 2 S 4 C 27 H 33 F 6 OPRu 2 S 2 Formula weight Crystal dimensions (mm 3 ) Crystal system Monoclinic Triclinic Space group P2(1)/n P 1 a (Å) (8) (17) b (Å) (5) (17) c (Å) (15) (2) α (º) (4) β (º) (3) (4) γ (º) (4) Volume (Å 3 ) (3) (4) Z 4 2 T (K) 300(2) 298(2) D calcd (g cm 3 ) μ (mm 1 ) F (000) No. of rflns. collected No. of indep. rflns. /R int 5420 / / No. of obsd. rflns. [I 0 > 2σ(I 0 )] Data / restraints / parameters 5420 / 7 / / 14 / 352 R 1 / wr 2 [I 0 > 2σ(I 0 )] / / R 1 / wr 2 (all data) / / GOF (on F 2 ) Largest diff. peak and hole (e Å 3 ) / / S5
6 Table S3. Crystallographic data for 7[PF 6 ] Complex 7[PF 6 ] Formula C 31 H 42 F 6 NPRu 2 S 2 Formula weight Crystal dimensions (mm 3 ) Crystal system Space group Monoclinic P2(1)/n a (Å) (6) b (Å) (18) c (Å) (10) α (º) β (º) (10) γ (º) Volume (Å 3 ) (4) Z 4 T (K) 300(2) D calcd (g cm 3 ) μ (mm 1 ) F (000) 1696 No. of rflns. collected No. of indep. rflns. /R int / No. of obsd. rflns. [I 0 > 2σ(I 0 )] 5141 Data / restraints / parameters 5689 / 48 / 404 R 1 / wr 2 [I 0 > 2σ(I 0 )] / R 1 / wr 2 (all data) / GOF (on F 2 ) Largest diff. peak and hole (e Å 3 ) / S6
7 Figure S1. ORTEP diagram of 3[PF 6 ] Hydrogen atoms and counteranion PF 6 are omitted for clarity (thermal ellipsoids shown at 50% probability). Table S4. Selected bond distances (Å) and bond angles ( ) for 3[PF 6 ] Distances (Å) Ru1 Ru (8) Ru2 S (18) Ru1 S (17) Ru1 Cl (6) Ru1 S (18) Ru2 Cl (2) Ru2 S (17) Angles ( ) S1 Ru1 S (7) S1 Ru2 S (7) S1 Ru1 Ru (4) S1 Ru2 Ru (4) S2 Ru1 Ru (4) S2 Ru2 Ru (4) Ru1 Cl1 Ru (5) Torsion angles ( ) Ru2 Cl1Ru1 S (7) Cp*1 Cp* (27) Ru2 Cl1Ru1 S (6) S7
8 Figure S2. ORTEP diagram of 4[PF 6 ] The PF 6 anion and hydrogen atoms except for the hydrogen atoms associated with C17 atom are omitted for clarity (thermal ellipsoids shown at 50% probability). Table S5. Selected bond distances (Å) and bond angles ( ) for 4[PF 6 ] Distances (Å) Ru1 Ru (1) C14 C (8) Ru1 S (2) C14 C (8) Ru1 S (2) C11 C (8) Ru2 S (2) C12 C (8) Ru2 S (2) C13 C (8) Ru1 I (2) C14 C (8) C11 C (8) C20 C (9) C12 C (8) C17 I (6) Angles ( ) I2 Ru1 Ru (2) S1 Ru2 Ru (4) S1 Ru1 Ru (3) S2 Ru2 Ru (3) S2 Ru1 Ru (3) C12 C17 I (4) Torsion angles ( ) S1 Ru1Ru2 S (7) C 5 Me 4 CH 2 I Cp* 80.40(19) S8
9 Figure S3. ORTEP diagram of 5[PF 6 ] The PF 6 anion and hydrogen atoms except for the hydrogen atoms associated with C17 atom are omitted for clarity (thermal ellipsoids shown at 50% probability). Table S6. Selected bond distances (Å) and bond angles ( ) for 5[PF 6 ] Distances (Å) Ru1 Ru (5) C14 C (10) Ru1 S (13) C14 C (10) Ru1 S (13) C11 C (9) Ru2 S (13) C12 C (9) Ru2 S (13) C13 C (10) Ru1 S (14) C14 C (10) C11 C (8) C20 C (9) C12 C (9) S4 C (7) S3 S (2) C11 C (9) Angles ( ) S1 Ru1 S (5) S1 Ru2 S (4) S1 Ru1 Ru (3) S4 S3 Ru (9) S2 Ru1 Ru (3) Torsion angles ( ) S1 Ru1Ru2 S (7) C 5 Me 4 CH 2 S 2 Cp* 73.76(24) S9
10 Figure S4. ORTEP diagram of 6[PF 6 ] The PF 6 anion and hydrogen atoms except for the hydrogen atoms associated with C20 atom are omitted for clarity (thermal ellipsoids shown at 50% probability). Table S7. Selected bond distances (Å) and bond angles ( ) for 6[PF 6 ] Distances (Å) Ru1 Ru (4) C14 C (5) Ru1 S (8) C14 C (5) Ru1 S (8) C11 C (5) Ru2 S (8) C12 C (5) Ru2 S (8) C13 C (5) Ru2 C (3) C14 C (5) C11 C (5) C20 C (5) C12 C (5) C15 C (5) C27 O (5) Ru1 C (4) Ru2 C (4) Angles ( ) S1 Ru1 S (3) S1 Ru2 S (3) S1 Ru1 Ru (2) C20 Ru2 Ru (10) S2 Ru1 Ru (2) Ru2 C20 C (22) Torsion angles ( ) S1 Ru1Ru2 S (4) C 5 Me 4 CH 2 Cp* 77.47(11) S10
11 Figure S5. ORTEP diagram of 7[PF 6 ] The PF 6 anion and hydrogen atoms except for the hydrogen atoms associated with C20 atom are omitted for clarity (thermal ellipsoids shown at 50% probability). Table S8. Selected bond distances (Å) and bond angles ( ) for 7[PF 6 ] Distances (Å) Ru1 Ru (4) C14 C (7) Ru1 S (10) C14 C (6) Ru1 S (11) C11 C (6) Ru2 S (9) C12 C (7) Ru2 S (11) C13 C (7) Ru2 C (4) C14 C (7) C11 C (7) C20 C (6) C12 C (7) C15 C (6) Ru1 C (5) C31 N (6) Angles ( ) S1 Ru1 S (4) S1 Ru2 S (4) S1 Ru1 Ru (2) C20 Ru2 Ru (12) S2 Ru1 Ru (3) Ru2 C31 N (5) Torsion angles ( ) S1 Ru1Ru2 S (5) C 5 Me 4 CH 2 Cp* 74.24(18) S11
12 % % % Figure S6. ESI-HRMS of 2[PF 6 ] in CH 2 Cl 2 (a) The signal at an m/z = corresponds to [2] +. (b) Calculated isotopic distribution for [2] + (upper) and the amplifying experimental diagram for [2] + (bottom). (a) JXX (0.296) AM (Cen,2, 80.00, Ht,5000.0,0.00,1.00); Sm (SG, 2x3.00); Cm (30:31) (b) m/z m/z S12
13 Figure S7. ESI-HRMS of 3[PF 6 ] in CH 2 Cl 2 (a) The signal at an m/z = corresponds to [3] +. (b) Calculated isotopic distribution for [3] + (bottom) and the amplifying experimental diagram for [3] + (upper). (a) (b) S13
14 Figure S8. ESI-HRMS of 4[PF 6 ] in CH 2 Cl 2 (a) The signal at an m/z = corresponds to [4] +. (b) Calculated isotopic distribution for [4] + (bottom) and the amplifying experimental diagram for [4] + (upper). (a) (b) S14
15 Figure S9. ESI-HRMS of 5[PF 6 ] in CH 2 Cl 2 (a) The signal at an m/z = corresponds to [5] +. (b) Calculated isotopic distribution for [5] + (bottom) and the amplifying experimental diagram for [5] + (upper). (a) (b) S15
16 % % % Figure S10. ESI-HRMS of 6[PF 6 ] in CH 2 Cl 2 (a) The signal at an m/z = corresponds to [6] +. (b) Calculated isotopic distribution for [6] + (upper) and the amplifying experimental diagram for [6] + (bottom). (a) JXX (0.247) AM (Cen,2, 80.00, Ht,5000.0,0.00,1.00); Sm (SG, 2x3.00); Cm (22:32) e (b) m/z m/z S16
17 % % % Figure S11. ESI-HRMS of 7[PF 6 ] in CH 2 Cl 2 (a) The signal at an m/z = corresponds to [7] +. (b) Calculated isotopic distribution for [7] + (upper) and the amplifying experimental diagram for [7] + (bottom). (a) JXX (0.682) AM (Cen,2, 80.00, Ht,5000.0,0.00,1.00); Sm (SG, 2x3.00); Cm (56:73) (b) m/z m/z S17
18 Figure S12. The 1 H NMR spectrum of 2[PF 6 ] in CD 2 Cl 2 Figure S13. The 13 C NMR spectrum of 2[PF 6 ] in CD 2 Cl 2 S18
19 Figure S14. The 1 H NMR spectrum of 3[PF 6 ] in CD 2 Cl 2 Figure S15. The 13 C NMR spectrum of 3[PF 6 ] in CD 2 Cl 2 S19
20 Figure S16. The 1 H NMR spectrum of 4[PF 6 ] in CD 2 Cl 2 Figure S17. The 13 C NMR spectrum of 4[PF 6 ] in CD 2 Cl 2 S20
21 Figure S18. The 1 H NMR spectrum of 5[PF 6 ] in CD 2 Cl 2 Figure S19. The 13 C NMR spectrum of 5[PF 6 ] in CD 2 Cl 2 S21
22 Figure S20. The 1 H NMR spectrum of 6[PF 6 ] in CD 2 Cl 2 Figure S21. The 13 C NMR spectrum of 6[PF 6 ] in CD 2 Cl 2 S22
23 Figure S22. The 1 H NMR spectrum of 7[PF 6 ] in CD 2 Cl 2 Figure S23. The 13 C NMR spectrum of 7[PF 6 ] in CD 2 Cl 2 S23
24 Figure S24. The IR (film) spectrum of 2[PF 6 ] Figure S25. The IR (film) spectrum of 3[PF 6 ] S24
25 Figure S26. The IR (film) spectrum of 4[PF 6 ] Figure S27. The IR (film) spectrum of 5[PF 6 ] S25
26 Figure S28. The IR (film) spectrum of 6[PF 6 ] Figure S29. The IR (film) spectrum of 7[PF 6 ] S26
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