Department of Chemistry, College of Science, Tianjin University, Tianjin , P. R. China.
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2019 Supporting Information for Synthesis, Catalysis, and DFT Study of A Ruthenium Carbene Complex Bearing A 1,2-Dicarbadodecaborane (12)-1,2- Dithiolate Ligand Tao Wang, a, b Botao Wu, *, b, c, d Weijie Guo, a, b Shutao Wu, a, b Huiqing Zhang, a, b Yanfeng Dang *, a, b Jianhui Wang, *, a, b a Department of Chemistry, College of Science, Tianjin University, Tianjin , P. R. China. b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) 30072, P. R. China. c School of Chemical Engineering and Technology, Tianjin University, Tianjin , P. R. China. d College of Chemistry and Molecular Engineering, Peking University, Beijing , China. Table of Contents Figure S1. X-ray crystal structure and CCDC: Figure S2. 1 H NMR spectrum of 7 in MeOD-d 4 (400 Hz)...3 Figure S3. 1 H{ 11 B} NMR spectrum of 7 in MeOD-d 4 (128 Hz)...4 Figure S4. 13 C{ 1 H} NMR spectrum of 7 in MeOD-d 4 (100 Hz)...4 Figure S5. 11 B NMR spectrum of 7 in MeOD-d 4 (128 Hz)...5 Figure S6. IR spectrum of 7 and 2588, 2561 cm -1 are the B-H stretches...5 Figure S7. 1 H NMR spectrum of 9 in CDCl 3 (400 Hz)...6 Figure S8. 13 C{ 1 H} NMR spectrum of 9 in CDCl 3 (100 Hz)...6 Figure S9. 11 B NMR spectrum of 9 in CD 3 CN (128 Hz)...7 Figure S B{ 1 H} NMR spectrum of 9 in acetone-d 6 (128 Hz)...7 Figure S11. 1 H{ 11 B} NMR spectrum of 9 in CDCl 3 (400 Hz)...8 Figure S12. IR spectrum of 9 and 2559, 2578, 2606 cm -1 are the B-H stretches...8 Figure S13. 1 H NMR spectrum of 12a in CDCl 3 (400 Hz)...9 Figure S C{ 1 H} NMR spectrum of 12a in CDCl 3 (100 Hz)...9 Figure S15. 1 H NMR spectrum of 12b in CDCl 3 (400 Hz)...10 Figure S C{ 1 H} NMR spectrum of 12b in CDCl 3 (100 Hz)...10 Figure S17. 1 H NMR spectrum of 14a in CDCl 3 (400 Hz)...11 Figure S C{ 1 H} NMR spectrum of 14a in CDCl 3 (100 Hz)...11 Figure S19. 1 H NMR spectrum of 14b in CDCl 3 (400 Hz)...12 Figure S C{ 1 H} NMR spectrum of 14b in CDCl 3 (100 Hz)...12 S1
2 Figure S21. 1 H NMR spectrum of 16 in CDCl 3 (400 Hz)...13 Figure S C{ 1 H} NMR spectrum of 16 in CDCl 3 (100 Hz)...13 Figure S23. 1 H NMR spectrum of 17 in CDCl 3 (400 Hz)...14 Figure S C{ 1 H} NMR spectrum of 17 in CDCl 3 (100 Hz)...14 Figure S25. 1 H NMR spectrum of 21 in CDCl 3 (400 Hz)...15 Figure S C{ 1 H} NMR spectrum of 21 in CDCl 3 (150 Hz)...15 Figure S27. 1 H NMR spectrum of 22 in CDCl 3 (400 Hz)...16 Figure S C{ 1 H} NMR spectrum of 22 in CDCl 3 (150 Hz)...16 Figure S29. 1 H NMR spectrum of 25 in CDCl 3 (400 Hz)...17 Figure S C{ 1 H} NMR spectrum of 25 in CDCl 3 (100 Hz)...17 Figure S31. 1 H NMR spectrum of 26 in CDCl 3 (400 Hz)...18 Figure S C NMR spectrum of 26 in CDCl 3 (100 Hz)...18 Figure S33. 1 H NMR spectrum of 27 in CDCl 3 (400 Hz)...19 Figure S C{ 1 H} NMR spectrum of 27 in CDCl 3 (150 Hz)...19 Figure S35. 1 H NMR spectrum of 28 in CDCl 3 (400 Hz)...20 Figure S C{ 1 H} NMR spectrum of 28 in CDCl 3 (150 Hz)...20 Figure S37. 1 H NMR spectrum of 29 in CDCl 3 (400 Hz)...21 Figure S C{ 1 H} NMR spectrum of 29 in CDCl 3 (100 Hz)...21 Figure S39. 1 H NMR spectrum of 30 in CDCl 3 (400 Hz)...22 Figure S C{ 1 H} NMR spectrum of 30 in CDCl 3 (100 Hz)...22 Figure S41. 1 H NMR spectrum of 31 in CDCl 3 (400 Hz)...23 Figure S C{ 1 H} NMR spectrum of 31 in CDCl 3 (100 Hz)...23 Figure S43. 1 H NMR spectrum of 32 in CDCl 3 (400 Hz)...24 Figure S C{ 1 H} NMR spectrum of 32 in CDCl 3 (100 Hz)...24 Figure S45. 1 H NMR spectrum of 33 in CDCl 3 (400 Hz)...25 Figure S C{ 1 H} NMR spectrum of 33 in CDCl 3 (100 Hz)...25 Table S1. Crystal data and structure refinement for Ru-based complex...26 Table S2. Bond Lengths for Ru-based complex...26 Table S3. Bond Angles for Ru-based complex Table S4. Torsion Angles for Ru-based complex The date of DFT calculations...38 S2
3 = Mes H N N S Ru O S Mes = BH; = C Figure S1. X-ray crystal structure and CCDC: Figure S2. 1 H NMR spectrum of 7 in MeOD-d 4 (400 Hz) S3
4 Figure S3. 1 H{ 11 B} NMR spectrum of 7 in MeOD-d 4 (128 Hz) Figure S4. 13 C{ 1 H} NMR spectrum of 7 in MeOD-d 4 (100 Hz) S4
5 Figure S5. 11 B NMR spectrum of 7 in MeOD-d 4 (128 Hz) Figure S6. IR spectrum of 7 and 2588, 2561 cm -1 are the B-H stretches S5
6 Figure S7. 1 H NMR spectrum of 9 in CDCl 3 (400 Hz) Figure S8. 13 C{ 1 H} NMR spectrum of 9 in CDCl 3 (100 Hz) S6
7 Figure S9. 11 B NMR spectrum of 9 in CD 3 CN (128 Hz) Figure S B{ 1 H} NMR spectrum of 9 in acetone-d 6 (128 Hz) S7
8 Figure S11. 1 H{ 11 B} NMR spectrum of 9 in CDCl 3 (400 Hz) Figure S12. IR spectrum of 9 and 2559, 2578, 2606 cm -1 are the B-H stretches S8
9 Figure S13. 1 H NMR spectrum of 12a in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 12a in CDCl 3 (100 Hz) S9
10 Figure S15. 1 H NMR spectrum of 12b in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 12b in CDCl 3 (100 Hz) S10
11 Figure S17. 1 H NMR spectrum of 14a in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 14a in CDCl 3 (100 Hz) S11
12 Figure S19. 1 H NMR spectrum of 14b in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 14b in CDCl 3 (100 Hz) S12
13 Figure S21. 1 H NMR spectrum of 16 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 16 in CDCl 3 (100 Hz) S13
14 Figure S23. 1 H NMR spectrum of 17 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 17 in CDCl 3 (100 Hz) S14
15 Figure S25. 1 H NMR spectrum of 21 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 21 in CDCl 3 (150 Hz) S15
16 Figure S27. 1 H NMR spectrum of 22 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 22 in CDCl 3 (150 Hz) S16
17 Figure S29. 1 H NMR spectrum of 25 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 25 in CDCl 3 (100 Hz) S17
18 Figure S31. 1 H NMR spectrum of 26 in CDCl 3 (400 Hz) Figure S C NMR spectrum of 26 in CDCl 3 (100 Hz) S18
19 Figure S33. 1 H NMR spectrum of 27 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 27 in CDCl 3 (150 Hz) S19
20 Figure S35. 1 H NMR spectrum of 28 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 28 in CDCl 3 (150 Hz) S20
21 Figure S37. 1 H NMR spectrum of 29 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 29 in CDCl 3 (100 Hz) S21
22 Figure S39. 1 H NMR spectrum of 30 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 30 in CDCl 3 (100 Hz) S22
23 Figure S41. 1 H NMR spectrum of 31 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 31 in CDCl 3 (100 Hz) S23
24 Figure S43. 1 H NMR spectrum of 32 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 32 in CDCl 3 (100 Hz) S24
25 Figure S45. 1 H NMR spectrum of 33 in CDCl 3 (400 Hz) Figure S C{ 1 H} NMR spectrum of 33 in CDCl 3 (100 Hz) S25
26 Table S1. Crystal data and structure refinement for Ru-based complex Identification code C 33 H 48 B 10 N 2 ORuS 2 Empirical formula C 34 H 51 B 10 Cl 2 N 2 ORuS 2 Formula weight Temperature/K 99.99(10) Crystal system monoclinic Space group P2 1 /n a/å (12) b/å (2) c/å (2) α/ 90 β/ (12) γ/ 90 Volume/Å (8) Z 4 ρ calc g/cm μ/mm F(000) Crystal size/mm Radiation CuKα (λ = ) 2Θ range for data collection/ to Index ranges -13 h 13, -25 k 25, -15 l 21 Reflections collected Independent reflections 7363 [R int = , R sigma = ] Data/restraints/parameters 7363/0/477 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.90 Table S2. Bond Lengths for Ru-based complex. Atom Atom Length/Å Atom Atom Length/Å Ru1 S (7) C25 C (4) Ru1 S (7) C26 C (5) Ru1 O (19) C27 C (4) Ru1 C (3) C29 C (4) Ru1 C (3) C29 C (4) S1 C (3) C33 C (4) S26
27 S2 C (3) C33 B (4) O1 C (3) C33 B (4) O1 C (3) C33 B (4) N1 C (4) C33 B (4) N1 C (4) C34 B (4) N1 C (4) C34 B (4) N2 C (4) C34 B (4) N2 C (4) C34 B (4) N2 C (3) B1 B (4) C1 C (4) B1 B (4) C1 C (5) B1 B (4) C2 C (4) B2 B (4) C2 C (4) B2 B (4) C3 C (5) B2 B (4) C4 C (4) B3 B (4) C4 C (4) B3 B (4) C5 C (4) B3 B (4) C6 C (4) B4 B (4) C10 C (4) B4 B (5) C13 C (4) B5 B (4) C13 C (4) B5 B (5) C14 C (4) B5 B (5) C14 C (4) B6 B (4) C15 C (5) B6 B (5) C16 C (5) B7 B (5) C16 C (4) B7 B (4) C17 C (4) B8 B (5) C18 C (4) B8 B (4) C22 C (4) B9 B (5) C23 C (4) Cl1 C (4) C23 C (4) Cl2 C (3) C24 C (4) Table S3. Bond Angles for Ru-based complex. Atom Atom Atom Angle/ Atom Atom Atom Angle/ S1 Ru1 S (2) C33 B1 B (2) S1 Ru1 O (5) C34 B1 C (15) O1 Ru1 S (5) C34 B1 B (16) C12 Ru1 S (8) C34 B1 B (2) S27
28 C12 Ru1 S (8) C34 B1 B (2) C12 Ru1 O (9) B2 B1 B (2) C22 Ru1 S (9) B7 B1 B (18) C22 Ru1 S (8) B7 B1 B (18) C22 Ru1 O (10) C34 B2 B (16) C22 Ru1 C (11) C34 B2 B (16) C34 S1 Ru (9) C34 B2 B (2) C33 S2 Ru (9) C34 B2 B (2) C24 O1 Ru (16) B1 B2 B (2) C24 O1 C (2) B1 B2 B (18) C29 O1 Ru (16) B1 B2 B (2) C1 N1 C (2) B7 B2 B (2) C12 N1 C (2) B7 B2 B (18) C12 N1 C (2) B8 B2 B (17) C12 N2 C (2) C34 B3 B (16) C12 N2 C (2) C34 B3 B (17) C13 N2 C (2) C34 B3 B (2) C2 C1 N (3) C34 B3 B (2) C6 C1 N (3) B2 B3 B (2) C6 C1 C (3) B4 B3 B (2) C1 C2 C (3) B4 B3 B (2) C1 C2 C (3) B4 B3 B (18) C3 C2 C (3) B8 B3 B (17) C4 C3 C (3) B8 B3 B (18) C3 C4 C (3) C33 B4 C (15) C3 C4 C (3) C33 B4 B (2) C5 C4 C (3) C33 B4 B (16) C6 C5 C (3) C33 B4 B (2) C1 C6 C (3) C34 B4 B (16) C5 C6 C (3) C34 B4 B (2) C5 C6 C (3) C34 B4 B (2) N1 C10 C (2) B5 B4 B (2) N2 C11 C (2) B016 B4 B (18) N1 C12 Ru (2) B016 B4 B (19) N1 C12 N (2) C33 B5 B (17) N2 C12 Ru (19) C33 B5 B (16) C14 C13 N (2) C33 B5 B (2) C18 C13 N (3) C33 B5 B (2) C18 C13 C (3) B4 B5 B (2) C13 C14 C (3) B4 B5 B (2) S28
29 C15 C14 C (3) B4 B5 B (18) C15 C14 C (3) B9 B5 B (18) C16 C15 C (3) B016 B5 B (2) C15 C16 C (3) B016 B5 B (18) C15 C16 C (3) C33 B6 B (16) C17 C16 C (3) C33 B6 B (16) C16 C17 C (3) C33 B6 B (2) C13 C18 C (3) C33 B6 B (2) C17 C18 C (3) B1 B6 B (2) C17 C18 C (3) B1 B6 B (17) C23 C22 Ru (2) B1 B6 B (2) C24 C23 C (2) B7 B6 B (2) C28 C23 C (3) B9 B6 B (18) C28 C23 C (3) B9 B6 B (18) O1 C24 C (2) B1 B7 B (17) C25 C24 O (3) B1 B7 B (17) C25 C24 C (3) B1 B7 B (2) C24 C25 C (3) B1 B7 B (2) C27 C26 C (3) B2 B7 B (2) C28 C27 C (3) B2 B7 B (18) C27 C28 C (3) B2 B7 B (2) O1 C29 C (3) B6 B7 B (2) O1 C29 C (2) B6 B7 B (18) C31 C29 C (3) B9 B7 B (18) C34 C33 S (18) B2 B8 B (17) C34 C33 B (15) B2 B8 B (2) C34 C33 B (16) B2 B8 B (2) C34 C33 B (2) B3 B8 B (17) C34 C33 B (2) B3 B8 B (2) B1 C33 S (18) B3 B8 B (2) B4 C33 S (18) B3 B8 B (18) B4 C33 B (2) B7 B8 B (18) B5 C33 S (18) B7 B8 B (2) B5 C33 B (2) B016 B8 B (18) B5 C33 B (17) B5 B9 B (2) B5 C33 B (17) B5 B9 B (2) B6 C33 S (19) B5 B9 B (18) B6 C33 B (17) B6 B9 B (18) B6 C33 B (2) B6 B9 B (18) C33 C34 S (18) B6 B9 B (2) S29
30 C33 C34 B (16) B6 B9 B (2) C33 C34 B (2) B7 B9 B (18) C33 C34 B (2) B7 B9 B (2) C33 C34 B (16) B016 B9 B (18) B1 C34 S (18) B3 B016 B (17) B1 C34 B (2) B3 B016 B (2) B2 C34 S (18) B4 B016 B (17) B2 C34 B (17) B4 B016 B (18) B2 C34 B (2) B4 B016 B (2) B3 C34 S (18) B4 B016 B (2) B3 C34 B (2) B5 B016 B (2) B3 C34 B (17) B5 B016 B (2) B3 C34 B (17) B5 B016 B (18) B4 C34 S (18) B9 B016 B (18) C33 B1 B (2) Cl2 C32 Cl (19) C33 B1 B (16) Table S4. Torsion Angles for Ru-based complex. A B C D Angle/ A B C D Angle/ Ru1 S1 C34 C (19) B1 B7 B8 B2-37.1(2) Ru1 S1 C34 B (19) B1 B7 B8 B3 0.4(3) Ru1 S1 C34 B (19) B1 B7 B8 B (2) Ru1 S1 C34 B (17) B1 B7 B8 B (3) Ru1 S1 C34 B (19) B1 B7 B9 B5-0.6(3) Ru1 S2 C33 C (19) B1 B7 B9 B6 37.2(2) Ru1 S2 C33 B (19) B1 B7 B9 B (2) Ru1 S2 C33 B (19) B1 B7 B9 B (3) Ru1 S2 C33 B (19) B2 C34 B1 C (2) Ru1 S2 C33 B (18) B2 C34 B1 B (2) Ru1 O1 C24 C23-0.6(3) B2 C34 B1 B7 40.1(2) Ru1 O1 C24 C (2) B2 C34 B3 B (2) Ru1 O1 C29 C (2) B2 C34 B3 B8-39.4(2) Ru1 O1 C29 C (3) B2 C34 B3 B (2) Ru1 C22 C23 C24 1.3(4) B2 C34 B4 C (2) Ru1 C22 C23 C (2) B2 C34 B4 B3 37.1(2) S1 Ru1 C22 C (2) B2 C34 B4 B5-66.0(3) S1 C34 B1 C (2) B2 C34 B4 B (3) S1 C34 B1 B (2) B2 B1 B6 C (2) S1 C34 B1 B (19) B2 B1 B6 B5 62.8(3) S30
31 S1 C34 B1 B (18) B2 B1 B6 B7-37.7(2) S1 C34 B2 B (2) B2 B1 B6 B9-0.7(3) S1 C34 B2 B (2) B2 B1 B7 B (2) S1 C34 B2 B (19) B2 B1 B7 B8 37.1(2) S1 C34 B2 B (19) B2 B1 B7 B (2) S1 C34 B3 B (2) B2 B3 B4 C33 0.5(3) S1 C34 B3 B (2) B2 B3 B4 C (2) S1 C34 B3 B (18) B2 B3 B4 B5 62.0(3) S1 C34 B3 B (19) B2 B3 B4 B (2) S1 C34 B4 C (2) B2 B3 B8 B7-37.3(2) S1 C34 B4 B (2) B2 B3 B8 B (2) S1 C34 B4 B (19) B2 B3 B8 B (2) S1 C34 B4 B (19) B2 B3 B016 B (2) S2 Ru1 C22 C (2) B2 B3 B016 B5-63.5(3) S2 C33 C34 S1 1.9(3) B2 B3 B016 B8 37.5(2) S2 C33 C34 B (2) B2 B3 B016 B9-0.2(3) S2 C33 C34 B (19) B2 B7 B8 B3 37.5(2) S2 C33 C34 B (18) B2 B7 B8 B (2) S2 C33 C34 B (2) B2 B7 B8 B (2) S2 C33 B1 C (2) B2 B7 B9 B5 62.9(3) S2 C33 B1 B (19) B2 B7 B9 B (2) S2 C33 B1 B (2) B2 B7 B9 B8-37.5(2) S2 C33 B1 B (19) B2 B7 B9 B (3) S2 C33 B4 C (2) B2 B8 B9 B5-63.9(3) S2 C33 B4 B (19) B2 B8 B9 B6-0.2(3) S2 C33 B4 B (2) B2 B8 B9 B7 37.1(2) S2 C33 B4 B (18) B2 B8 B9 B (2) S2 C33 B5 B (2) B2 B8 B016 B3-37.6(2) S2 C33 B5 B (2) B2 B8 B016 B4-0.6(3) S2 C33 B5 B (2) B2 B8 B016 B5 62.7(3) S2 C33 B5 B (2) B2 B8 B016 B (2) S2 C33 B6 B (2) B3 C34 B1 C (2) S2 C33 B6 B (2) B3 C34 B1 B2-36.6(2) S2 C33 B6 B (19) B3 C34 B1 B6 66.2(3) S2 C33 B6 B (19) B3 C34 B1 B7 3.5(3) O1 Ru1 C22 C23-1.2(2) B3 C34 B2 B (2) O1 C24 C25 C (3) B3 C34 B2 B (2) N1 C1 C2 C (2) B3 C34 B2 B8 39.4(2) N1 C1 C2 C7 5.1(4) B3 C34 B4 C (2) N1 C1 C6 C (2) B3 C34 B4 B (2) S31
32 N1 C1 C6 C9-3.7(4) B3 C34 B4 B (2) N1 C10 C11 N2 15.2(3) B3 B2 B7 B (2) N2 C13 C14 C (2) B3 B2 B7 B6 63.5(3) N2 C13 C14 C19-2.8(4) B3 B2 B7 B8-37.5(2) N2 C13 C18 C (2) B3 B2 B7 B9 0.1(3) N2 C13 C18 C21 0.4(4) B3 B2 B8 B (2) C1 N1 C10 C (3) B3 B2 B8 B (2) C1 N1 C12 Ru1 6.3(5) B3 B2 B8 B (2) C1 N1 C12 N (3) B3 B4 B5 C (2) C1 C2 C3 C4 0.3(4) B3 B4 B5 B6-62.1(3) C2 C1 C6 C5 0.5(4) B3 B4 B5 B9 1.1(3) C2 C1 C6 C (3) B3 B4 B5 B (2) C2 C3 C4 C5-0.3(4) B3 B4 B016 B (2) C2 C3 C4 C (3) B3 B4 B016 B8-36.8(2) C3 C4 C5 C6 0.4(4) B3 B4 B016 B (2) C4 C5 C6 C1-0.5(4) B3 B8 B9 B5-0.4(3) C4 C5 C6 C (3) B3 B8 B9 B6 63.3(3) C6 C1 C2 C3-0.4(4) B3 B8 B9 B (2) C6 C1 C2 C (3) B3 B8 B9 B (2) C7 C2 C3 C (3) B3 B8 B016 B4 37.0(2) C8 C4 C5 C (3) B3 B8 B016 B (2) C10 N1 C1 C2 84.3(4) B3 B8 B016 B (2) C10 N1 C1 C6-91.1(3) B4 C33 C34 S (2) C10 N1 C12 Ru (2) B4 C33 C34 B (2) C10 N1 C12 N2 3.9(3) B4 C33 C34 B (2) C11 N2 C12 Ru (19) B4 C33 C34 B3 38.3(2) C11 N2 C12 N1 7.5(3) B4 C33 B1 C (2) C11 N2 C13 C (3) B4 C33 B1 B2 2.0(3) C11 N2 C13 C (3) B4 C33 B1 B (2) C12 Ru1 C22 C (2) B4 C33 B1 B7 64.7(3) C12 N1 C1 C2-94.4(4) B4 C33 B5 B (2) C12 N1 C1 C6 90.2(4) B4 C33 B5 B (2) C12 N1 C10 C (4) B4 C33 B5 B (2) C12 N2 C11 C (3) B4 C33 B6 B (2) C12 N2 C13 C (3) B4 C33 B6 B5 36.4(2) C12 N2 C13 C (4) B4 C33 B6 B7-65.7(3) C13 N2 C11 C (3) B4 C33 B6 B9-3.1(3) C13 N2 C12 Ru1-12.7(4) B4 C34 B1 C (2) C13 N2 C12 N (3) B4 C34 B1 B (2) C13 C14 C15 C16-0.9(4) B4 C34 B1 B6-2.0(3) S32
33 C14 C13 C18 C17-4.2(4) B4 C34 B1 B7-64.7(3) C14 C13 C18 C (3) B4 C34 B2 B (2) C14 C15 C16 C17-1.1(4) B4 C34 B2 B3-36.8(2) C14 C15 C16 C (3) B4 C34 B2 B7 65.4(3) C15 C16 C17 C18 0.4(4) B4 C34 B2 B8 2.6(3) C16 C17 C18 C13 2.2(4) B4 C34 B3 B (2) C16 C17 C18 C (3) B4 C34 B3 B (2) C18 C13 C14 C15 3.5(4) B4 C34 B3 B (2) C18 C13 C14 C (3) B4 B3 B8 B (2) C19 C14 C15 C (3) B4 B3 B8 B7 64.3(3) C20 C16 C17 C (3) B4 B3 B8 B9 1.1(3) C22 C23 C24 O1-0.3(4) B4 B3 B8 B (2) C22 C23 C24 C (3) B4 B3 B016 B5 37.7(2) C22 C23 C28 C (3) B4 B3 B016 B (2) C23 C24 C25 C26 2.3(5) B4 B3 B016 B (2) C24 O1 C29 C (3) B4 B5 B6 C (2) C24 O1 C29 C (3) B4 B5 B6 B1-0.1(3) C24 C23 C28 C27 1.7(4) B4 B5 B6 B7 62.8(3) C24 C25 C26 C27-0.2(5) B4 B5 B6 B (2) C25 C26 C27 C28-1.1(5) B4 B5 B9 B (2) C26 C27 C28 C23 0.3(4) B4 B5 B9 B7-63.7(3) C28 C23 C24 O (2) B4 B5 B9 B8-0.4(3) C28 C23 C24 C25-3.1(4) B4 B5 B9 B (2) C29 O1 C24 C (2) B4 B5 B016 B3-37.8(2) C29 O1 C24 C (4) B4 B5 B016 B (2) C33 C34 B1 B (2) B4 B5 B016 B (2) C33 C34 B1 B (19) B5 C33 C34 S (19) C33 C34 B1 B7-98.4(2) B5 C33 C34 B (2) C33 C34 B2 B1 38.6(2) B5 C33 C34 B2 67.5(3) C33 C34 B2 B (2) B5 C33 C34 B3-0.2(3) C33 C34 B2 B7-1.3(3) B5 C33 C34 B4-38.5(2) C33 C34 B2 B8-64.1(3) B5 C33 B1 C (2) C33 C34 B3 B (2) B5 C33 B1 B2-65.8(3) C33 C34 B3 B4-38.1(2) B5 C33 B1 B6 36.9(2) C33 C34 B3 B8 64.0(2) B5 C33 B1 B7-3.2(3) C33 C34 B3 B (3) B5 C33 B4 C (2) C33 C34 B4 B (2) B5 C33 B4 B (2) C33 C34 B4 B5 35.8(2) B5 C33 B4 B (2) C33 C34 B4 B (2) B5 C33 B6 B (2) C33 B1 B2 C (18) B5 C33 B6 B (2) S33
34 C33 B1 B2 B3-1.6(3) B5 C33 B6 B9-39.5(2) C33 B1 B2 B7 99.1(2) B5 B4 B016 B (2) C33 B1 B2 B8 61.9(3) B5 B4 B016 B (2) C33 B1 B6 B5-33.8(2) B5 B4 B016 B9 37.1(2) C33 B1 B6 B (2) B5 B6 B7 B (2) C33 B1 B6 B9-97.3(2) B5 B6 B7 B2-63.5(3) C33 B1 B7 B2-98.8(2) B5 B6 B7 B8 0.0(3) C33 B1 B7 B (19) B5 B6 B7 B9 37.6(2) C33 B1 B7 B8-61.7(3) B5 B6 B9 B (2) C33 B1 B7 B9 2.2(3) B5 B6 B9 B (2) C33 B4 B5 B6 34.0(2) B5 B6 B9 B (2) C33 B4 B5 B9 97.2(2) B5 B9 B016 B (2) C33 B4 B5 B (2) B5 B9 B016 B4-37.1(2) C33 B4 B016 B3 98.3(2) B5 B9 B016 B (2) C33 B4 B016 B (19) B6 C33 C34 S (19) C33 B4 B016 B8 61.5(3) B6 C33 C34 B1 38.5(2) C33 B4 B016 B9-2.2(3) B6 C33 C34 B2-0.1(3) C33 B5 B6 B1 34.3(2) B6 C33 C34 B3-67.7(3) C33 B5 B6 B7 97.2(2) B6 C33 C34 B (2) C33 B5 B6 B (2) B6 C33 B1 C (2) C33 B5 B9 B6-38.9(2) B6 C33 B1 B (2) C33 B5 B9 B7-1.3(3) B6 C33 B1 B7-40.1(2) C33 B5 B9 B8 62.0(3) B6 C33 B4 C (2) C33 B5 B9 B (2) B6 C33 B4 B3 66.4(3) C33 B5 B016 B3 1.9(3) B6 C33 B4 B5-36.8(2) C33 B5 B016 B (19) B6 C33 B4 B (3) C33 B5 B016 B8-61.2(3) B6 C33 B5 B (2) C33 B5 B016 B9-98.8(2) B6 C33 B5 B9 39.4(2) C33 B6 B7 B (19) B6 C33 B5 B (2) C33 B6 B7 B2-2.2(3) B6 B1 B2 C (2) C33 B6 B7 B8 61.4(3) B6 B1 B2 B3-62.9(3) C33 B6 B7 B9 98.9(2) B6 B1 B2 B7 37.8(2) C33 B6 B9 B (19) B6 B1 B2 B8 0.5(3) C33 B6 B9 B7-99.1(2) B6 B1 B7 B (2) C33 B6 B9 B8-61.8(3) B6 B1 B7 B (2) C33 B6 B9 B (3) B6 B1 B7 B9-37.0(2) C34 C33 B1 B (19) B6 B5 B9 B7 37.6(2) C34 C33 B1 B (2) B6 B5 B9 B (2) C34 C33 B1 B7 98.5(2) B6 B5 B9 B (2) C34 C33 B4 B (19) B6 B5 B016 B3 63.4(3) S34
35 C34 C33 B4 B (2) B6 B5 B016 B (2) C34 C33 B4 B (2) B6 B5 B016 B8 0.3(3) C34 C33 B5 B4 38.6(2) B6 B5 B016 B9-37.2(2) C34 C33 B5 B (2) B6 B7 B8 B (2) C34 C33 B5 B9-63.7(3) B6 B7 B8 B3-63.3(3) C34 C33 B5 B (3) B6 B7 B8 B9 37.4(2) C34 C33 B6 B1-38.2(2) B6 B7 B8 B (3) C34 C33 B6 B (2) B6 B7 B9 B5-37.7(2) C34 C33 B6 B7 1.4(3) B6 B7 B9 B (2) C34 C33 B6 B9 64.0(3) B6 B7 B9 B (2) C34 B1 B2 B (19) B6 B9 B016 B3-63.1(3) C34 B1 B2 B (2) B6 B9 B016 B4 0.4(3) C34 B1 B2 B8 97.0(2) B6 B9 B016 B5 37.5(2) C34 B1 B6 C (18) B6 B9 B016 B (2) C34 B1 B6 B5 1.2(3) B7 B1 B2 C (2) C34 B1 B6 B7-99.3(2) B7 B1 B2 B (2) C34 B1 B6 B9-62.2(3) B7 B1 B2 B8-37.3(2) C34 B1 B7 B (19) B7 B1 B6 C (2) C34 B1 B7 B6 98.6(2) B7 B1 B6 B (2) C34 B1 B7 B8-2.3(3) B7 B1 B6 B9 37.1(2) C34 B1 B7 B9 61.5(3) B7 B2 B3 C (2) C34 B2 B3 B4 34.6(2) B7 B2 B3 B4-62.6(3) C34 B2 B3 B (2) B7 B2 B3 B8 37.7(2) C34 B2 B3 B (2) B7 B2 B3 B (3) C34 B2 B7 B (19) B7 B2 B8 B (2) C34 B2 B7 B6 2.2(3) B7 B2 B8 B9-37.2(2) C34 B2 B7 B8-98.8(2) B7 B2 B8 B (2) C34 B2 B7 B9-61.2(3) B7 B6 B9 B (2) C34 B2 B8 B3-38.7(2) B7 B6 B9 B8 37.3(2) C34 B2 B8 B7 99.3(2) B7 B6 B9 B (2) C34 B2 B8 B9 62.1(3) B7 B8 B9 B (2) C34 B2 B8 B (3) B7 B8 B9 B6-37.3(2) C34 B3 B4 C (18) B7 B8 B9 B (2) C34 B3 B4 B5 96.2(2) B7 B8 B016 B (2) C34 B3 B4 B (2) B7 B8 B016 B4-63.6(3) C34 B3 B8 B (19) B7 B8 B016 B5-0.3(3) C34 B3 B8 B7 1.6(3) B7 B8 B016 B9 37.2(2) C34 B3 B8 B9-61.5(3) B7 B9 B016 B3 0.3(3) C34 B3 B8 B (2) B7 B9 B016 B4 63.8(3) C34 B3 B016 B4-39.7(2) B7 B9 B016 B (2) S35
36 C34 B3 B016 B5-2.0(3) B7 B9 B016 B8-37.2(2) C34 B3 B016 B8 99.0(2) B8 B2 B3 C (2) C34 B3 B016 B9 61.3(3) B8 B2 B3 B (2) C34 B4 B5 C (19) B8 B2 B3 B (2) C34 B4 B5 B6-1.1(3) B8 B2 B7 B (2) C34 B4 B5 B9 62.2(3) B8 B2 B7 B (2) C34 B4 B5 B (2) B8 B2 B7 B9 37.6(2) C34 B4 B016 B (19) B8 B3 B4 C (3) C34 B4 B016 B5-98.6(2) B8 B3 B4 C (2) C34 B4 B016 B8 2.1(3) B8 B3 B4 B5-1.4(3) C34 B4 B016 B9-61.5(3) B8 B3 B4 B (2) B1 C33 C34 S (2) B8 B3 B016 B (2) B1 C33 C34 B2-38.6(2) B8 B3 B016 B (2) B1 C33 C34 B (2) B8 B3 B016 B9-37.7(2) B1 C33 C34 B (2) B8 B7 B9 B (2) B1 C33 B4 C (2) B8 B7 B9 B (2) B1 C33 B4 B3-1.6(3) B8 B7 B9 B (2) B1 C33 B4 B (2) B8 B9 B016 B3 37.5(2) B1 C33 B4 B (3) B8 B9 B016 B (2) B1 C33 B5 B (2) B8 B9 B016 B (2) B1 C33 B5 B6-36.5(2) B9 B5 B6 C (2) B1 C33 B5 B9 2.8(3) B9 B5 B6 B (2) B1 C33 B5 B (3) B9 B5 B6 B7-37.7(2) B1 C33 B6 B (2) B9 B5 B016 B (2) B1 C33 B6 B7 39.6(2) B9 B5 B016 B (2) B1 C33 B6 B (2) B9 B5 B016 B8 37.5(2) B1 C34 B2 B (2) B9 B6 B7 B (2) B1 C34 B2 B7-39.9(2) B9 B6 B7 B (2) B1 C34 B2 B (2) B9 B6 B7 B8-37.5(2) B1 C34 B3 B2 36.2(2) B9 B7 B8 B (2) B1 C34 B3 B (2) B9 B7 B8 B (2) B1 C34 B3 B8-3.3(3) B9 B7 B8 B (2) B1 C34 B3 B (3) B9 B8 B016 B (2) B1 C34 B4 C (2) B9 B8 B016 B (2) B1 C34 B4 B (2) B9 B8 B016 B5-37.5(2) B1 C34 B4 B5 2.0(3) B016 B3 B4 C (2) B1 C34 B4 B (3) B016 B3 B4 C (2) B1 B2 B3 C (2) B016 B3 B4 B5-38.3(2) B1 B2 B3 B4 0.7(3) B016 B3 B8 B (2) B1 B2 B3 B (2) B016 B3 B8 B (2) S36
37 B1 B2 B3 B (3) B016 B3 B8 B9 37.6(2) B1 B2 B7 B6-37.6(2) B016 B4 B5 C (2) B1 B2 B7 B (2) B016 B4 B5 B (2) B1 B2 B7 B (2) B016 B4 B5 B9-37.2(2) B1 B2 B8 B (2) B016 B5 B6 C (2) B1 B2 B8 B7 37.0(2) B016 B5 B6 B1-63.1(3) B1 B2 B8 B9-0.2(3) B016 B5 B6 B7-0.2(3) B1 B2 B8 B (3) B016 B5 B6 B9 37.4(2) B1 B6 B7 B2 37.5(2) B016 B5 B9 B (2) B1 B6 B7 B (2) B016 B5 B9 B (2) B1 B6 B7 B (2) B016 B5 B9 B8-37.4(2) B1 B6 B9 B (2) B016 B8 B9 B5 37.3(2) B1 B6 B9 B7-36.8(2) B016 B8 B9 B (2) B1 B6 B9 B8 0.5(3) B016 B8 B9 B (2) B1 B6 B9 B (3) S37
38 The date of DFT calculations Activated_Complex 9 E(M06)= Hartree Ru S S N N C C C C C C C C C C C C C C C C C C C C C C C C S38
39 B B B B B B B B B B H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S39
40 H C H H H Activated_Complex 9-propene E(M06)= Hartree Ru S S N N C C C C C C C C C C C C C C C C C C C S40
41 C C C C C B B B B B B B B B B H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S41
42 H H H H H H C H H C H C H H H C H H H Activated_Complex 9-propene-[2+2]_TS E(M06)= Hartree Ru S S N N C C C C C C S42
43 C C C C C C C C C C C C C C C C C C B B B B B B B B B B H H H H H H H H H H H H H H H H S43
44 H H H H H H H H H H H H H H H H H H H C H H C H C H H H C H H H H H S44
45 Activated_Complex 9-propene-[2+2] E(M06)= Hartree Ru S S N N C C C C C C C C C C C C C C C C C C C C C C C C B S45
46 B B B B B B B B B H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S46
47 C H H C C H H H H C H H H Activated_Complex 9_S-shift_TS E(M06)= Hartree Ru S S C N N C C C C C C C C S47
48 H H C H H H C H H H C C C C C C H H C H H H C H H H C H C C H H C H H H C H H H H C B B S48
49 B B B H B H B B H C B B H H H H H H H H H C H H H C H H H Activated_Complex 9_S-shift E(M06)= Hartree S49
50 Ru S S N N C C C C C C C C C C C C C C C C C C C C C C C C B B B B B B B B B B H H H H H S50
51 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C H H C H C H H H C H H H S51
52 Activated_Complex 9_[2+2]_ringopen_TS E(M06)= Hartree Ru S S N N C C C C C C C C C C C C C C C C C C C C C C C C B B S52
53 B B B B B B B B H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C S53
54 H H C C H H H H H H C H H H Activated_Complex 9_[2+2]_ringopen E(M06)= Hartree Ru S S N N C C C C C C C C C C S54
55 C C C C C C C C C C C C C C B B B B B B B B B B H H H H H H H H H H H H H H H H H H H H S55
56 H H H H H H H H H H H H H H H C H H C C H H H H H H C H H H S56
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