Nickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings

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ickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings Braulio M. Puerta Lombardi, Rudy M. Braun, Chris Gendy, Chia Yun Chang, Tristram Chivers and Roland Roesler* Department of Chemistry, University of Calgary, 2500 University Drive W, Calgary, AB, T2 14 Canada Figure S1. 1 H MR spectrum for compound 1......S2 Figure S2. 13 C MR spectrum for compound 1..........S3 Figure S3. 31 P MR spectrum for compound 1........S4 Figure S4. HSQC MR spectrum for compound 1.............S5 Figure S5. 1 H MR spectrum for, -bispyrazolymethane...........s6 Figure S6. 13 C MR spectrum for, -bispyrazolymethane........s7 Figure S7. 1 H MR spectrum for compound 2...........S8 Figure S8. 13 C MR spectrum for compound 2..........S9 Figure S9. 31 P MR spectrum for compound 2.......S10 Figure S10. 1 H MR spectrum for compound 4.........S11 Figure S11. 13 C MR spectrum for compound 4........S12 Figure S12. 31 P MR spectrum for compound 4..............S13 Figure S13, S14, S15. HMBC MR spectrum for compound 4........S14 Figure S16. 1 H MR spectrum for compound 6.........S17 Figure S17. 13 C MR spectrum for compound 6............S18 Figure S18. 31 P MR spectrum for compound 6...... S19 Figure S19. 1 H MR spectrum for compound 7......S20 Figure S20. 13 C MR spectrum for compound 7........S21 Figure S21. 31 P MR spectrum for compound 7............S22 Figure S22. HMBC MR spectrum for compound 7...... S23 Figure S23. HSQC MR spectrum for compound 7.............. S24 Figure S24. 1 H MR spectrum for compound 8........S25 Figure S25. 13 C MR spectrum for compound 8............S26 Figure S26. 31 P MR spectrum for compound 8...... S27 Figure S27. HSQC MR spectrum for compound 8......... S28 Crystallographic data for compound 3........S29 Crystallographic data for compound 4......S35 Crystallographic data for compound 5....S41 Crystallographic data for compound 7.......S47 Crystallographic data for compound 9......S52

S2 Figure S1. 1 H MR (400 MHz, 298 K, CD2Cl2) for 1 ipr 2 P PiPr 2 CH(CH3)2 5 4 1 CH 4 CH 5 CH2 CH(CH3)2 CH2Cl2

S3 Figure S2. DEPTQ 13 C MR (101 MHz, 298 K, CD2Cl2) for 1 CH(CH3)2 ipr 2 P PiPr 2 CH(CH3)2 C 5 H 5 4 1 C 4 H 2C 2 P CH2 CD2Cl2

S4 Figure S3. 31 P MR (162 MHz, 298 K, toluene-d8) for 1 ipr 2 P PiPr 2 5 4 1

Figure S4. HSQC MR (400 MHz, 298 K, CD2Cl2) for 1 S5

Figure S5. 1 H MR (400 MHz, 298 K, CDCl3) for bis(pyrazolyl)methane S6 5 4 3 CH2 CH 3 CH 5 CH 4 CHCl3

S7 Figure S6. DEPTQ 13 C MR (101 MHz, 298 K, toluene-d8) for bis(pyrazolyl)methane 5 C 3 H C 4 H 4 3 C 5 H CH2

S8 Figure S7. 1 H MR (400 MHz, 298 K, CDCl3) for 2 ipr 2 P PiPr 2 4 3 2 CH3 CH 4 CH2 CH 3 CH CHCl3

S9 Figure S8. DEPTQ 13 C MR (101 MHz, 298 K, toluene-d8) for 2 ipr 2 P PiPr 2 4 3 2 C 5 H CH2 CH(CH3)2 C 3 H C 4 H CH(CH3)2

S10 Figure S9. 31 P MR (162 MHz, 298 K, toluene-d8) for 2 ipr 2 P PiPr 2 4 3 2

S11 Figure S10. 1 H MR (400 MHz, 298 K, toluene-d8) for 4 toluene-d7 Br ipr 2 P i PiPr 2 4 5 H 4 toluene-d7 CH(CH3)2 CH5 CH 4 2CH CH(CH3)2

S12 Figure S11. 13 C MR (101 MHz, 298 K, toluene-d8) for 4 toluene-d8 C 4 H Br ipr 2 P i PiPr 2 toluene-d8 2C 2 P C 5 H 4 5 H 4 CH(CH3)2 C 4 H CH(CH3)2 C 5 H 2C 2 P 2Ci

S13 Figure S12. 31 P MR (162 MHz, 298 K, toluene-d8) for 4 Br ipr 2 P i PiPr 2 H 4

S14 Figure S13. HMBC MR (400 MHz, 298 K, toluene-d8) for 4 Br ipr 2 P i PiPr 2 H 4

S15 Figure S14. HMBC MR (400 MHz, 298 K, toluene-d8) for 4 Br ipr 2 P i PiPr 2 H 4

S16 Figure S15. HMBC MR (400 MHz, 298 K, toluene-d8) for 4 Br ipr 2 P i PiPr 2 H 4

S17 Figure S16. 1 H MR (400 MHz, 298 K, CD2Cl2) for 6 CH 5 CH 4 CH(CH3)2 benzene Cl Cl Pt ipr 2 P H H PiPr 2 CHDCl2 4 5 6 CH(CH3)2 2CH2 2CH2 CH(CH3)2

S18 Figure S17. 13 C MR (101 MHz, 298 K, CD2Cl2) for 6 C 5 H Cl Cl Pt ipr 2 P H H PiPr 2 CHDCl2 4 5 6 CH(CH3)2 benzene C 4 H CH(CH3)2 CH2 2C 2 P

S19 Figure S18. 31 P MR (162 MHz, 162 K, CD2Cl2) for 6 Cl Cl Pt ipr 2 P H H PiPr 2 6

Figure S19. 1 H MR (400 MHz, 298 K, toluene-d8) for 7 S20 Cl ipr 2 P Pt PiPr 2 toluene-d7 H 4 5 7 CH(CH3)2 toluene-d7 CH 4 CH 5 PtCH CH(CH3)2

S21 Figure S20. 13 C MR (101 MHz, 298 K, CD2Cl2) for 7 Cl ipr 2 P Pt PiPr 2 HCPt CD2Cl2 CH(CH3)2 H 4 5 7 toluene C 4 H CH(CH3)2 C 5 H CH(CH3)2 toluene toluene 2C 2 P HCPt

S22 Figure S21. 31 P MR (162 MHz, 298 K, CD2Cl2) for 7 Cl ipr 2 P Pt PiPr 2 H 7

S23 Figure S22. HMBC MR (400 MHz, 298 K, CD2Cl2) for 7 Cl ipr 2 P Pt PiPr 2 H 7

S24 Figure S23. HSQC MR (400 MHz, 298 K, CD2Cl2) for 7 Cl ipr 2 P Pt PiPr 2 H 7

S25 Figure S24. 1 H MR (400 MHz, 298 K, CD2Cl2) for 8 CH Cl Cl ipr 2 P Pt PiPr 2 Cl H 8 CDHCl2 CH(CH3)2 CH(CH3)2 PtCH CH(CH3)2 CH(CH3)2 THF-d6

S26 Figure S25. 13 C MR (101 MHz, 298 K, CD2Cl2) for 8 CD2Cl2 CH(CH3)2 Cl Cl ipr 2 P Pt PiPr 2 Cl H 8 CD2Cl2 THF-d8 THF-d8 HCPt CH(CH3)2 2CP C 4 H C 5 H CH(CH3)2

S27 Figure S26. 31 P MR (162 MHz, 298 K, CD2Cl2) for 8 Cl Cl ipr 2 P Pt PiPr 2 Cl H 8

Figure S27. HMQC MR (400 MHz, 298 K, CD2Cl2) for 8 S28

Figure S28. Solid state structure of 3 with thermal ellipsoids drawn at 50% probability level. All hydrogen atoms except those on the methylene bridge were omitted for clarity. S29

S30 Table S1: Crystal data and structure refinement for 3. Identification code 3 Chemical formula C 19H 34Br 2 4iP 2 Molecular weight 598.97 Temperature 293(2) Wavelength 0.71073 Crystal system ; space group monoclinic ; C 2/c Unit cell dimentions a = 36.559(7) Å ; α = 90 b = 9.0040(18) Å ; β = 96.61(3) c = 15.291(3) Å ; γ = 90 Volume 5000.0(18) ų Z, Calculated density 8, 1.591 g/cm³ Absorption coefficient 4.113 1/mm F(000) 2432 Theta range for data collection 2.819 to 25.000 Limiting indices -43 h 43 ; -10 k 10 ; -18 l 18 Reflexion collected / unique 15151 / 4355 [R(int) = 0.0453] Completness to theta max 98.7 % Refinement method Full-matrix least-square on F² Data / restraints / parameters 4355 / 237 / 261 Goodness of fit on F² 1.144 Final R indices [I>2sigma(I)] R1 = 0.0308 ; wr2 = 0.0742 Final R indices [all data] R1 = 0.0419 ; wr2 = 0.0903 Absolute structure parameter Largest diff peak and hole 0.362 and -0.538 e/å³

S31 Table S2: Atomic coordinates (x 10 4 ) and equivalent isotropic displacements parameters (Å 2 x 10 3 ) for 3. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. Label x y z U(eq) Br1 5888.4(2) 4582.5(4) 6303.9(3) 34.39(12) Br2 6424.4(2) 7663.1(5) 7865.9(2) 41.71(14) C1 6060.5(9) 5676(4) 4135(2) 25.8(8) C10 7162.9(1.3) 4269(6) 4962(3) 52.9(1.2) C11 5553.8(9) 7316(4) 4622(2) 24.2(7) C12 5409(1) 5897(5) 3460(2) 36.4(9) C13 5111.8(1.1) 6646(5) 3670(3) 40.7(1.0) C14 5984.5(1.0) 9910(4) 4916(2) 30.9(8) C15 6260.6(1.2) 10857(5) 5488(3) 45.8(1.1) C16 5675.5(1.2) 10851(5) 4439(3) 40.9(1.0) C17 5433.7(1.1) 8989(5) 6110(2) 32.5(8) C18 5249.3(1.2) 7686(5) 6528(3) 45.2(1.1) C19 5564.4(1.3) 10167(5) 6796(3) 46.0(1.1) C2 6646.2(9) 7142(4) 4585(2) 22.3(7) C3 6677.7(1.1) 8380(5) 3399(2) 33.8(9) C4 6368.9(1.0) 7553(4) 3249(2) 30.6(8) C5 7172.8(1.0) 7392(5) 6101(2) 30.8(8) C6 7114.3(1.1) 9050(5) 6241(3) 41.2(1.0) C7 7359.7(1.2) 6680(6) 6950(3) 46.0(1.1) C8 6843.4(1.0) 4456(4) 5522(2) 32.0(8) C9 6897.9(1.3) 3562(5) 6367(3) 46.4(1.1) 1 6345.2(8) 6754(3) 4008.6(1.8) 23.2(6) 2 6851.6(8) 8129(4) 4223.8(1.9) 30.0(7) 3 5696.6(8) 6325(3) 4065.3(1.8) 24.9(6) 4 5201.1(9) 7537(4) 4384(2) 34.7(8) i1 6224.2(2) 6840.8(5) 6444.2(3) 25.23(13) P1 6736.5(2) 6449.5(1.1) 5700.1(6) 23.2(2) P2 5814.2(2) 8319.3(1.0) 5516.9(6) 23.2(2)

S32 Table S3: Bond lengths (Ångstrom) and angles ( ) for 3. Br1 - i1 2.3722(7) Br2 - i1 2.3332(8) i1 - P1 2.3274(12) i1 - P2 2.3538(11) C1-1 1.452(4) C1-3 1.446(4) C2-1 1.373(4) C11-3 1.376(4) C2-2 1.325(5) C11-4 1.314(5) C4-1 1.378(5) C12-3 1.373(4) C3-2 1.364(5) C13-4 1.365(5) C3 - C4 1.350(5) C12 - C13 1.349(6) C2 - P1 1.810(3) C11 - P2 1.816(4) C5 - P1 1.848(4) C14 - P2 1.847(4) C8 - P1 1.864(4) C17 - P2 1.847(4) C5 - C6 1.526(6) C14 - C15 1.519(5) C5 - C7 1.535(5) C14 - C16 1.529(5) C8 - C9 1.516(5) C17 - C18 1.529(6) C8 - C10 1.535(6) C17 - C19 1.528(6) Br2 - i1 - Br1 117.38(3) P1 - i1 - P2 106.48(4) P1 - i1 - Br1 105.27(3) P2 - i1 - Br1 98.23(3) P1 - i1 - Br2 108.65(4) Br2 - i1 - P2 119.44(4) 3 - C1-1 112.8(3) C2-1 - C1 128.2(3) C11-3 - C1 128.9(3) C4-1 - C1 125.2(3) C12-3 - C1 124.3(3)

S33 2 - C2-1 110.7(3) 4 - C11-3 111.0(3) 1 - C2 - P1 124.3(3) 3 - C11 - P2 125.8(3) 2 - C2 - P1 125.0(3) 4 - C11 - P2 123.0(3) C2-1 - C4 106.5(3) C12-3 - C11 106.4(3) C2-2 - C3 105.7(3) C11-4 - C13 105.6(3) C3 - C4-1 106.1(3) C13 - C12-3 105.9(3) C4 - C3-2 111.0(3) C12 - C13-4 111.1(3) C2 - P1 - i1 109.80(11) C11 - P2 - i1 114.51(12) C5 - P1 - i1 118.71(13) C14 - P2 - i1 120.68(13) C8 - P1 - i1 114.28(13) C17 - P2 - i1 110.61(12) C2 - P1 - C5 102.22(17) C11 - P2 - C14 100.85(16) C2 - P1 - C8 102.28(16) C11 - P2 - C17 100.01(17) C5 - P1 - C8 107.65(18) C17 - P2 - C14 107.88(18) C6 - C5 - P1 111.5(3) C15 - C14 - P2 112.9(3) C7 - C5 - P1 111.8(3) C16 - C14 - P2 113.2(3) C10 - C8 - P1 111.9(3) C18 - C17 - P2 110.4(3) C9 - C8 - P1 113.4(3) C19 - C17 - P2 111.7(3) C6 - C5 - C7 110.3(3) C15 - C14 - C16 111.6(3) C9 - C8 - C10 112.5(3) C19 - C17 - C18 111.4(3)

S34 Table S4: Hydrogen coordinates (x 10 4 ) and isotropic displacements parameters (Å 2 x 10 3 ) for 3. Label x y z U(eq) H10A 7387.0 4610.0 5290.0 79.0 H10B 7114.0 4842.0 4432.0 79.0 H10C 7187.0 3240.0 4815.0 79.0 H12 5417.0 5227.0 3000.0 44.0 H13 4877.0 6567.0 3367.0 49.0 H14 6119.0 9484.0 4457.0 37.0 H15A 6420.0 11352.0 5123.0 69.0 H15B 6405.0 10236.0 5905.0 69.0 H15C 6132.0 11582.0 5796.0 69.0 H16A 5545.0 11350.0 4864.0 61.0 H16B 5508.0 10222.0 4078.0 61.0 H16C 5779.0 11573.0 4076.0 61.0 H17 5250.0 9450.0 5678.0 39.0 H18A 5414.0 7295.0 7008.0 68.0 H18B 5192.0 6924.0 6095.0 68.0 H18C 5027.0 8022.0 6743.0 68.0 H19A 5366.0 10419.0 7130.0 69.0 H19B 5641.0 11038.0 6504.0 69.0 H19C 5768.0 9785.0 7184.0 69.0 H1A 6064.0 4897.0 3698.0 31.0 H1B 6115.0 5225.0 4711.0 31.0 H3 6761.0 9034.0 2995.0 41.0 H4 6205.0 7527.0 2736.0 37.0 H5 7340.0 7285.0 5648.0 37.0 H6A 6945.0 9188.0 6670.0 62.0 H6B 7016.0 9497.0 5694.0 62.0 H6C 7345.0 9508.0 6446.0 62.0 H7A 7570.0 7261.0 7173.0 69.0 H7B 7437.0 5691.0 6825.0 69.0 H7C 7189.0 6641.0 7381.0 69.0 H8 6626.0 4039.0 5174.0 38.0 H9A 6906.0 2523.0 6228.0 70.0 H9B 6697.0 3747.0 6705.0 70.0 H9C 7125.0 3849.0 6703.0 70.0

Figure S29. Solid state structure of 4 with thermal ellipsoids drawn at 50% probability level. All hydrogen atoms except those on the methylene bridge were omitted for clarity. S35

S36 Table S5: Crystal data and structure refinement for 4. Identification code 4 Chemical formula C 19H 33Br 4iP 2 Molecular weight 518.05 Temperature 153(2) Wavelength 0.71073 Crystal system ; space group monoclinic ; P 21/c Unit cell dimentions a = 11.653(2) Å ; α = 90 b = 16.815(3) Å ; β = 113.29(3) c = 14.491(3) Å ; γ = 90 Volume 2608.1(11) ų Z, Calculated density 4, 1.319 g/cm³ Absorption coefficient 2.409 1/mm F(000) 1072 Theta range for data collection 2.422 to 24.999 Limiting indices -13 h 13 ; -19 k 19 ; -17 l 17 Reflexion collected / unique 8854 / 4532 [R(int) = 0.0278] Completness to theta max 98.8 % Refinement method Full-matrix least-square on F² Data / restraints / parameters 4532 / 243 / 252 Goodness of fit on F² 1.092 Final R indices [I>2sigma(I)] R1 = 0.0393 ; wr2 = 0.1154 Final R indices [all data] R1 = 0.0476 ; wr2 = 0.1215 Absolute structure parameter Largest diff peak and hole 0.458 and -0.473 e/å³

S37 Table S6: Atomic coordinates (x 10 4 ) and equivalent isotropic displacements parameters (Å 2 x 10 3 ) for 4. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. Label x y z U(eq) Br1 6838.2(4) 2138.0(2) 9871.9(3) 31.62(15) C1 6483(3) 3327(2) 7157(2) 20.1(7) C10 9648(4) 2480(3) 8659(3) 38.7(1.0) C11 4240(3) 3034(2) 6539(3) 22.5(7) C12 4632(3) 3974(2) 5660(3) 28.2(8) C13 3393(4) 3766(2) 5253(3) 32.4(9) C14 3634(3) 2463(3) 8184(3) 31.9(9) C15 3674(4) 3323(3) 8558(3) 44.7(1.1) C16 2303(4) 2211(3) 7514(4) 42.5(1.1) C17 4535(3) 1362(2) 7024(3) 27.6(8) C18 4741(4) 711(2) 7807(3) 37.5(9) C19 5417(4) 1256(2) 6501(3) 39.4(1.0) C2 8167(3) 4225(2) 8207(3) 22.6(7) C3 8491(3) 4974(2) 7143(3) 25.7(8) C4 7525(3) 4486(2) 6599(3) 25.2(7) C5 8412(3) 4221(2) 10254(3) 24.1(7) C6 7191(4) 4677(3) 10005(3) 34.7(9) C7 8806(4) 3785(3) 11259(3) 33.9(9) C8 9721(3) 3015(2) 9532(3) 25.9(8) C9 10883(3) 3548(3) 9862(3) 37.1(9) 1 7299(3) 4020.8(1.6) 7282(2) 19.8(6) 2 8903(3) 4814.6(1.8) 8151(2) 25.2(6) 3 5169(3) 3511.4(1.6) 6497(2) 20.5(6) 4 3144(3) 3172.7(1.9) 5790(2) 29.2(7) i1 6595.5(4) 2845.6(2) 8426.0(3) 18.26(15)

S38 Table S7: Bond lengths (Ångstrom) and angles ( ) for 4. Br1 - i1 2.3275(7) C1 - i1 1.965(3) i1 - P1 2.1710(11) i1 - P2 2.1802(12) C1-1 1.471(4) C1-3 1.483(4) C2-1 1.366(4) C11-3 1.368(4) C2-2 1.334(5) C11-4 1.330(5) C4-1 1.366(4) C12-3 1.366(4) C3-2 1.373(5) C13-4 1.365(5) C3 - C4 1.364(5) C12 - C13 1.372(5) C2 - P1 1.788(4) C11 - P2 1.791(4) C5 - P1 1.838(4) C14 - P2 1.830(4) C8 - P1 1.835(4) C17 - P2 1.835(4) C5 - C6 1.529(5) C14 - C15 1.539(6) C5 - C7 1.530(5) C14 - C16 1.529(5) C8 - C9 1.535(5) C17 - C18 1.526(5) C8 - C10 1.527(6) C17 - C19 1.509(6) P1 - i1 - P2 168.25(4) C1 - i1 - Br1 172.81(10) P1 - i1 - Br1 93.06(4) P2 - i1 - Br1 93.17(4) C1 - i1 - P1 88.30(10) C1 - i1 - P2 86.75(10) 1 - C1-3 111.4(3) 1 - C1 - i1 114.2(2) 3 - C1 - i1 111.1(2) 2 - C2-1 111.8(3) 4 - C11-3 112.5(3)

S39 C2-1 - C1 120.8(3) C11-3 - C1 118.8(3) C4-1 - C1 131.7(3) C12-3 - C1 133.3(3) C2-1 - C4 106.7(3) C12-3 - C11 106.3(3) C2-2 - C3 104.3(3) C11-4 - C13 103.9(3) C4 - C3-2 111.0(3) 4 - C13 - C12 111.5(3) C3 - C4-1 106.1(3) 3 - C12 - C13 105.7(3) 1 - C2 - P1 114.5(2) 3 - C11 - P2 114.2(2) 2 - C2 - P1 132.8(3) 4 - C11 - P2 133.3(3) C2 - P1 - i1 100.25(12) C11 - P2 - i1 98.98(12) C5 - P1 - i1 122.80(12) C17 - P2 - i1 121.15(12) C8 - P1 - i1 113.80(13) C14 - P2 - i1 115.12(13) C2 - P1 - C5 104.40(17) C11 - P2 - C14 106.71(18) C2 - P1 - C8 105.88(16) C11 - P2 - C17 105.48(17) C8 - P1 - C5 107.68(17) C14 - P2 - C17 107.65(18) C6 - C5 - P1 109.0(2) C15 - C14 - P2 109.2(3) C7 - C5 - P1 113.5(3) C16 - C14 - P2 113.5(3) C9 - C8 - P1 114.0(3) C18 - C17 - P2 112.0(3) C10 - C8 - P1 109.6(3) C19 - C17 - P2 109.4(3) C6 - C5 - C7 110.8(3) C16 - C14 - C15 111.5(3) C10 - C8 - C9 111.5(3) C19 - C17 - C18 110.5(3)

S40 Table S8: Hydrogen coordinates (x 10 4 ) and isotropic displacements parameters (Å 2 x 10 3 ) for 4. Label x y z U(eq) H1 6765.0 2921.0 6808.0 24.0 H10A 9558.0 2802.0 8088.0 58.0 H10B 8941.0 2131.0 8489.0 58.0 H10C 10398.0 2170.0 8852.0 58.0 H12 5025.0 4352.0 5418.0 34.0 H13 2798.0 4000.0 4683.0 39.0 H14 3921.0 2115.0 8775.0 38.0 H15A 3386.0 3678.0 7994.0 67.0 H15B 4516.0 3458.0 8992.0 67.0 H15C 3144.0 3369.0 8922.0 67.0 H16A 1763.0 2303.0 7860.0 64.0 H16B 2294.0 1656.0 7357.0 64.0 H16C 2017.0 2515.0 6904.0 64.0 H17 3678.0 1317.0 6520.0 33.0 H18A 4627.0 200.0 7488.0 56.0 H18B 4152.0 774.0 8113.0 56.0 H18C 5575.0 749.0 8312.0 56.0 H19A 6262.0 1247.0 6991.0 59.0 H19B 5314.0 1690.0 6044.0 59.0 H19C 5235.0 764.0 6135.0 59.0 H3 8826.0 5364.0 6866.0 31.0 H4 7105.0 4472.0 5904.0 30.0 H5 9064.0 4610.0 10318.0 29.0 H6A 6526.0 4309.0 9915.0 52.0 H6B 7003.0 4976.0 9397.0 52.0 H6C 7277.0 5034.0 10545.0 52.0 H7A 8940.0 4164.0 11787.0 51.0 H7B 9566.0 3497.0 11388.0 51.0 H7C 8161.0 3419.0 11233.0 51.0 H8 9810.0 2668.0 10100.0 31.0 H9A 11618.0 3222.0 10062.0 56.0 H9B 10919.0 3872.0 10418.0 56.0 H9C 10839.0 3882.0 9312.0 56.0

Figure S30. Solid state structure of 5 with thermal ellipsoids drawn at 50% probability level. All hydrogen atoms except those on the methylene bridge were omitted for clarity. S41

S42 Table S9: Crystal data and structure refinement for 5. Identification code 5 Chemical formula C 19H 34Br 4iP 2 Molecular weight 519.06 Temperature 153(2) Wavelength 0.71073 Crystal system ; space group monoclinic; P 21/c Unit cell dimentions a = 14.9160(2) Å ; α = 90.0000 b = 9.4370(4) Å ; β = 110.7410(10) c = 22.5270(6) Å ; γ = 90.0000 Volume 2965.44(15) ų Z, Calculated density 4, 1.163 g/cm³ Absorption coefficient 2.119 1/mm F(000) 1076 Theta range for data collection 2.365 to 25.000 Limiting indices -17 h 17 ; -11 k 11 ; -26 l 26 Reflexion collected / unique 18242 / 5163 [R(int) = 0.0514] Completness to theta max 98.9 % Refinement method Full-matrix least-square on F² Data / restraints / parameters 5163 / 0 / 252 Goodness of fit on F² 1.075 Final R indices [I>2sigma(I)] R1 = 0.0411 ; wr2 = 0.1099 Final R indices [all data] R1 = 0.0494 ; wr2 = 0.1152 Largest diff peak and hole 0.505 and -0.453 e/å³

S43 Table S10: Atomic coordinates (x 10 4 ) and equivalent isotropic displacements parameters (Å 2 x 10 3 ) for 5. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. Label x y z U(eq) Br1 1104.8(3) 3128.4(4) 2766.6(2) 35.55(13) C1 1462(2) 8646(4) 2529.4(1.5) 27.9(7) C10 707(3) 3594(4) 865.8(1.9) 46.4(1.0) C11 3212(2) 7899(3) 3103.1(1.6) 28.3(7) C12 2942(3) 10138(4) 2796.7(1.9) 38.8(9) C13 3890(3) 9900(4) 3089(2) 41.4(9) C14 4190(3) 5248(4) 3391.9(1.9) 37.7(9) C15 4207(3) 3787(4) 3678(2) 51.9(1.1) C16 4479(4) 5202(5) 2809(2) 61.2(1.3) C17 2827(3) 6033(4) 3985.1(1.6) 35.9(8) C18 1888(3) 6749(4) 3937.4(1.9) 44.9(1.0) C19 3663(3) 6637(5) 4537.4(1.9) 55.1(1.2) C2 1032(2) 7869(3) 1377.6(1.6) 27.1(7) C3 398(3) 9813(4) 919.4(1.7) 36.2(8) C4 682(3) 10074(4) 1547.1(1.8) 34.1(8) C5 2439(3) 6109(4) 1175.1(1.7) 35.8(8) C6 3115(3) 7349(5) 1457(2) 46.3(1.0) C7 2083(3) 6166(5) 454.9(1.9) 49.8(1.1) C8 443(3) 5142(3) 931.7(1.6) 32.2(8) C9-406(3) 5237(4) 1158.2(1.9) 44.8(1.0) 1 1085.4(1.9) 8844(3) 1848.1(1.3) 25.3(6) 2 619(2) 8432(3) 812.8(1.4) 33.5(7) 3 2495.2(1.9) 8871(3) 2799.0(1.3) 28.2(6) 4 4064(2) 8509(3) 3278.4(1.5) 38.4(7) i1 1788.2(3) 5041.4(4) 2456.9(2) 26.58(14)

S44 Table S11: Bond lengths (Ångstrom) and angles ( ) for 5. Br1 - i1 2.2997(5) i1 - P1 2.2242(9) i1 - P2 2.2088(10) C1-1 1.448(4) C1-3 1.458(4) C2-1 1.384(4) C11-3 1.391(4) C2-2 1.314(4) C11-4 1.322(4) C4-1 1.371(4) C12-3 1.370(4) C3-2 1.386(4) C13-4 1.376(5) C3 - C4 1.347(5) C12 - C13 1.351(6) C2 - P1 1.815(3) C11 - P2 1.810(3) C5 - P1 1.853(4) C14 - P2 1.843(4) C8 - P1 1.849(3) C17 - P2 1.842(4) C5 - C6 1.528(5) C14 - C15 1.518(5) C5 - C7 1.519(5) C14 - C16 1.522(6) C8 - C10 1.534(5) C17 - C18 1.524(5) C8 - C9 1.525(6) C17 - C19 1.526(5) P1 - i1 - Br1 131.57(3) P2 - i1 - Br1 115.55(3) P2 - i1 - P1 112.87(4) 1 - C1-3 112.3(3) C4-1 - C1 124.8(3) C11-3 - C1 128.6(3) C4-1 - C2 106.7(3) C12-3 - C1 124.7(3) C2-1 - C1 128.4(3) C12-3 - C11 106.7(3) 2 - C2-1 110.7(3) 4 - C11-3 110.5(3)

S45 C2-2 - C3 105.7(3) C11-4 - C13 105.5(3) C4 - C3-2 110.4(3) C12 - C13-4 111.1(3) C3 - C4-1 106.5(3) C13 - C12-3 106.2(3) 1 - C2 - P1 125.1(2) 3 - C11 - P2 124.1(2) 2 - C2 - P1 124.2(2) 4 - C11 - P2 125.4(3) C2 - P1 - i1 120.68(11) C11 - P2 - i1 116.42(11) C5 - P1 - i1 118.21(12) C14 - P2 - i1 116.92(13) C8 - P1 - i1 108.38(12) C17 - P2 - i1 112.23(12) C2 - P1 - C5 101.32(16) C11 - P2 - C14 102.70(16) C2 - P1 - C8 99.13(15) C11 - P2 - C17 103.18(16) C8 - P1 - C5 106.87(17) C17 - P2 - C14 103.67(17) C10 - C8 - P1 109.8(3) C15 - C14 - P2 109.5(3) C6 - C5 - P1 109.9(2) C16 - C14 - P2 111.8(3) C7 - C5 - P1 114.4(3) C18 - C17 - P2 111.1(3) C9 - C8 - P1 108.4(2) C19 - C17 - P2 114.9(3) C7 - C5 - C6 110.2(3) C15 - C14 - C16 111.9(3) C9 - C8 - C10 111.1(3) C18 - C17 - C19 110.9(3)

S46 Table S12: Hydrogen coordinates (x 10 4 ) and isotropic displacements parameters (Å 2 x 10 3 ) for 5. Label x y z U(eq) H10A 829.0 3111.0 1262.0 70.0 H10B 1271.0 3564.0 755.0 70.0 H10C 187.0 3140.0 540.0 70.0 H12 2651.0 10992.0 2628.0 47.0 H13 4363.0 10585.0 3153.0 50.0 H14 4656.0 5840.0 3712.0 45.0 H15A 3744.0 3190.0 3377.0 78.0 H15B 4053.0 3864.0 4056.0 78.0 H15C 4834.0 3381.0 3781.0 78.0 H16A 5098.0 4767.0 2917.0 92.0 H16B 4505.0 6150.0 2660.0 92.0 H16C 4016.0 4662.0 2480.0 92.0 H17 2766.0 5036.0 4087.0 43.0 H18A 1762.0 6587.0 4322.0 67.0 H18B 1374.0 6361.0 3584.0 67.0 H18C 1935.0 7749.0 3876.0 67.0 H19A 3739.0 7624.0 4463.0 83.0 H19B 4240.0 6136.0 4573.0 83.0 H19C 3535.0 6531.0 4924.0 83.0 H1A 1317.0 7692.0 2628.0 34.0 H1B 1148.0 9303.0 2724.0 34.0 H3 97.0 10467.0 603.0 43.0 H4 618.0 10921.0 1739.0 41.0 H5 2813.0 5236.0 1306.0 43.0 H6A 3684.0 7248.0 1355.0 69.0 H6B 3284.0 7357.0 1909.0 69.0 H6C 2801.0 8223.0 1283.0 69.0 H7A 1706.0 7006.0 310.0 75.0 H7B 1698.0 5346.0 284.0 75.0 H7C 2622.0 6182.0 316.0 75.0 H8 276.0 5614.0 519.0 39.0 H9A -953.0 4781.0 856.0 67.0 H9B -553.0 6215.0 1199.0 67.0 H9C -245.0 4776.0 1562.0 67.0

Figure S31. Solid state structure of 7 with thermal ellipsoids drawn at 50% probability level. All hydrogen atoms except those on the methylene bridge were omitted for clarity. S47

S48 Table S13: Crystal data and structure refinement for 7. Identification code 7 Chemical formula C 19H 33Cl 4P 2Pt Molecular weight 609.97 Temperature 173(2) Wavelength 1.54178 Crystal system ; space group monoclinic ; P 21/c Unit cell dimentions a = 11.9159(2) Å ; α = 90 b = 16.2190(3) Å ; β = 113.1680(10) c = 14.7281(4) Å ; γ = 90 Volume 2616.86(10) ų Z, Calculated density 4, 1.548 g/cm³ Absorption coefficient 12.201 1/mm F(000) 1200 Theta range for data collection 4.035 to 67.497 Limiting indices -14 h 14; -19 k 19; -17 l 17 Reflexion collected / unique 33297 / 4718 [R(int) = 0.0286] Completness to theta max 100.0 % Refinement method Full-matrix least-square on F² Data / restraints / parameters 4718 / 0 / 252 Goodness of fit on F² 1.177 Final R indices [I>2sigma(I)] R1 = 0.0190 ; wr2 = 0.0493 Final R indices [all data] R1 = 0.0191 ; wr2 = 0.0494 Largest diff peak and hole 0.545 and -0.633 e/å³

S49 Table S14: Atomic coordinates (x 10 4 ) and equivalent isotropic displacements parameters (Å 2 x 10 3 ) for 7. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. Label x y z U(eq) C1 3414(2) 6738.5(1.5) 7895.0(1.7) 14.8(5) C10 4648(3) 8855(2) 8627(2) 34.1(7) C11 1745(2) 5812.7(1.6) 6812.0(1.8) 16.9(5) C12 2385(2) 5515.4(1.6) 8384.6(1.9) 20.3(5) C13 1452(3) 5007.0(1.7) 7835(2) 22.5(5) C14 1466(2) 5871.0(1.7) 4763.5(1.9) 19.8(5) C15 1074(3) 6367(2) 3806(2) 30.1(6) C16 2676(3) 5422.3(1.9) 4984(2) 29.6(6) C17 131(2) 7044.2(1.8) 5519(2) 22.1(5) C18 190(3) 7577(2) 6393(3) 36.6(7) C19-973(2) 6467(2) 5189(2) 30.5(6) C2 5647(2) 6992.8(1.6) 8494.4(1.9) 18.3(5) C3 6429(3) 6216.9(1.8) 9747(2) 26.6(6) C4 5212(3) 6035.9(1.7) 9349.8(1.9) 22.5(5) C5 6324(3) 7589(2) 6902(2) 28.6(6) C6 6243(3) 6706(2) 6520(3) 42.4(8) C7 7638(3) 7820(2) 7571(3) 39.4(8) C8 5498(2) 8746.6(1.7) 8082(2) 23.1(6) C9 5288(3) 9415.4(1.9) 7308(2) 34.6(7) Cl1 3251.6(7) 7941.1(5) 5150.8(5) 30.79(15) 1 4705.4(1.9) 6528.2(1.3) 8528.5(1.5) 15.7(4) 2 6705(2) 6820.5(1.5) 9215.8(1.7) 24.8(5) 3 2601.0(1.9) 6019.3(1.3) 7724.1(1.5) 15.6(4) 4 1044(2) 5195.0(1.4) 6848.7(1.7) 23.4(5) P1 5247.0(6) 7724.0(4) 7501.4(5) 16.85(14) P2 1600.5(5) 6515.8(4) 5822.7(4) 14.28(12) Pt1 3324.9(2) 7270.6(2) 6594.3(2) 13.27(5)

S50 Table S15: Bond lengths (Ångstrom) for 7. C1 - Pt1 2.065(2) Cl1 - Pt1 2.3587(6) P1 - Pt1 2.2724(6) P2 - Pt1 2.2748(6) C1-1 1.492(3) C1-3 1.473(3) C2 - P1 1.796(3) C11 - P2 1.804(3) C5 - P1 1.835(3) C14 - P2 1.832(3) C8 - P1 1.836(3) C17 - P2 1.840(3) C2-1 1.369(3) C11-3 1.371(3) C2-2 1.320(3) C11-4 1.319(3) C4-1 1.375(3) C12-3 1.370(3) C3-2 1.372(4) C13-4 1.373(3) C3 - C4 1.365(4) C12 - C13 1.365(4) C5 - C6 1.528(5) C14 - C15 1.529(4) C5 - C7 1.533(4) C14 - C16 1.532(4) C8 - C10 1.530(4) C17 - C18 1.528(4) C8 - C9 1.522(4) C17 - C19 1.529(4) P1 - Pt1 - P2 166.23(2) C1 - Pt1 - Cl1 177.16(7) P1 - Pt1 - Cl1 92.98(2) P2 - Pt1 - Cl1 95.28(2) C1 - Pt1 - P1 85.29(7) C1 - Pt1 - P2 86.85(7) 3 - C1-1 111.90(19) 1 - C1 - Pt1 109.85(15) 3 - C1 - Pt1 112.46(15) 1 - C2 - P1 115.75(18) 3 - C11 - P2 115.76(18) 2 - C2 - P1 131.2(2) 4 - C11 - P2 130.7(2) 2 - C2-1 113.0(2) 4 - C11-3 112.6(2) C2-1 - C1 120.7(2) C11-3 - C1 123.1(2) C4-1 - C1 132.2(2) C12-3 - C1 130.2(2) C2-1 - C4 105.6(2) C12-3 - C11 105.9(2) C2-2 - C3 104.1(2) C11-4 - C13 104.2(2) C3 - C4-1 106.1(2) C13 - C12-3 106.0(2) C4 - C3-2 111.2(2) C12 - C13-4 111.1(2) C2 - P1 - Pt1 98.54(9) C11 - P2 - Pt1 99.00(8) C5 - P1 - Pt1 114.38(10) C17 - P2 - Pt1 117.20(9) C8 - P1 - Pt1 120.53(9) C14 - P2 - Pt1 119.46(9) C2 - P1 - C5 107.53(14) C11 - P2 - C14 105.98(12) C2 - P1 - C8 105.95(12) C11 - P2 - C17 105.64(12) C5 - P1 - C8 108.37(14) C14 - P2 - C17 107.64(12) C6 - C5 - P1 109.5(2) C15 - C14 - P2 112.2(2) C7 - C5 - P1 113.1(2) C16 - C14 - P2 109.33(18) C9 - C8 - P1 110.2(2) C19 - C17 - P2 114.2(2) C10 - C8 - P1 109.14(19) C18 - C17 - P2 109.5(2) C6 - C5 - C7 111.5(3) C15 - C14 - C16 111.5(2) C9 - C8 - C10 111.4(3) C18 - C17 - C19 111.3(3)

S51 Table S16: Hydrogen coordinates (x 10 4 ) and isotropic displacements parameters (Å 2 x 10 3 ) for 7. Label x y z U(eq) H1 3136.0 7161.0 8256.0 18.0 H10A 4810.0 9387.0 8969.0 51.0 H10B 4793.0 8410.0 9111.0 51.0 H10C 3797.0 8836.0 8152.0 51.0 H12 2801.0 5519.0 9083.0 24.0 H13 1128.0 4579.0 8101.0 27.0 H14 825.0 5445.0 4679.0 24.0 H15A 1676.0 6802.0 3879.0 45.0 H15B 275.0 6618.0 3664.0 45.0 H15C 1022.0 6001.0 3262.0 45.0 H16A 2582.0 5036.0 4447.0 44.0 H16B 2908.0 5118.0 5606.0 44.0 H16C 3312.0 5826.0 5040.0 44.0 H17 17.0 7425.0 4956.0 27.0 H18A -577.0 7882.0 6217.0 55.0 H18B 869.0 7967.0 6558.0 55.0 H18C 315.0 7223.0 6965.0 55.0 H19A -910.0 6099.0 5734.0 46.0 H19B -992.0 6139.0 4624.0 46.0 H19C -1723.0 6794.0 4996.0 46.0 H3 7009.0 5959.0 10318.0 32.0 H4 4799.0 5648.0 9592.0 27.0 H5 6061.0 7965.0 6316.0 34.0 H6A 6793.0 6641.0 6175.0 64.0 H6B 5403.0 6589.0 6063.0 64.0 H6C 6481.0 6321.0 7077.0 64.0 H7A 7915.0 7474.0 8164.0 59.0 H7B 7669.0 8401.0 7762.0 59.0 H7C 8171.0 7733.0 7215.0 59.0 H8 6362.0 8781.0 8573.0 28.0 H9A 4473.0 9350.0 6783.0 52.0 H9B 5905.0 9368.0 7025.0 52.0 H9C 5352.0 9958.0 7616.0 52.0

Figure S32. Solid state structure of 9 with thermal ellipsoids drawn at 50% probability level. All hydrogen atoms except those on the methylene bridge were omitted for clarity. S52

S53 Table S17: Crystal data and structure refinement for 9. Identification code 9 Chemical formula C 19H 34Br 2Co 4P 2 Molecular weight 599.19 Temperature 293(2) Wavelength 0.71073 Crystal system ; space group triclinic ; P -1 Unit cell dimentions a = 8.6470(17) Å ; α = 68.96(3) b = 12.380(3) Å ; β = 76.06(3) c = 13.300(3) Å ; γ = 78.83(3) Volume 1280.6(5) ų Z, Calculated density 2, 1.554 g/cm³ Absorption coefficient 3.927 1/mm F(000) 606 Theta range for data collection 1.775 to 24.997 Limiting indices -10 h 10 ; -14 k 14 ; -15 l 15 Reflexion collected / unique 8244 / 4447 [R(int) = 0.0238] Completness to theta max 98.4 % Refinement method Full-matrix least-square on F² Data / restraints / parameters 4447 / 6 / 261 Goodness of fit on F² 1.171 Final R indices [I>2sigma(I)] R1 = 0.0337 ; wr2 = 0.0880 Final R indices [all data] R1 = 0.0402 ; wr2 = 0.1019 Largest diff peak and hole 0.613 and -0.709 e/å³

S54 Table S18: Atomic coordinates (x 10 4 ) and equivalent isotropic displacements parameters (Å 2 x 10 3 ) for 9. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. Label x y z U(eq) Br1 4385.0(5) 4258.4(3) 6964.1(4) 40.95(14) Br2 2808.3(5) 6801.4(3) 8298.3(3) 35.43(13) C1 7518(4) 6209(3) 4948(3) 24.9(7) C10 8110(6) 3338(4) 8200(4) 49.3(1.1) C11 6232(4) 8261(3) 4027(3) 26.7(7) C12 4841(5) 8906(3) 4369(3) 33.8(9) C13 4194(5) 8235(3) 5416(3) 31.3(8) C14 8807(6) 9628(4) 2993(4) 48.3(1.1) C15 10542(9) 9537(8) 2341(7) 104(3) C16 8884(6) 9414(4) 4178(4) 50.7(1.2) C17 6458(6) 9602(4) 1815(3) 44.7(1.0) C18 5237(7) 8991(5) 1647(4) 58.5(1.3) C19 7513(9) 10198(6) 734(4) 76.7(1.8) C2 9060(4) 6078(3) 6418(3) 26.7(7) C3 10627(5) 6239(3) 6327(3) 33.6(8) C4 11309(4) 6473(3) 5224(3) 33.5(8) C5 7660(5) 6837(4) 8231(3) 38.4(9) C6 7096(6) 8043(4) 7505(4) 50.5(1.2) C7 6705(6) 6579(5) 9407(4) 52.9(1.2) C8 8176(5) 4330(4) 8590(3) 36.4(9) C9 9833(5) 4254(4) 8852(4) 48.0(1.1) Co1 4904.7(6) 5944.1(4) 7196.2(4) 24.81(14) 1 8896(3) 6240(2) 5369(2) 23.9(6) 2 10274(4) 6479(3) 4635(3) 30.1(7) 3 6345(3) 7248(2) 4873(2) 22.8(6) 4 5111(3) 7222(2) 5729(2) 24.7(6) P1 7495.1(1.1) 5740.7(8) 7632.3(8) 26.1(2) P2 7752.0(1.2) 8563.1(8) 2775.7(8) 29.9(2)

S55 Table S19: Bond lengths (Ångstrom) and angles ( ) for 9. Br1 - Co1 Co1 - P1 C1-1 C2-1 C2 - C3 1-2 C4-2 C3 - C4 C2 - P1 C5 - P1 C8 - P1 C5 - C6 C5 - C7 C8 - C9 C8 - C10 2.3547(7) 2.3916(11) 1.446(4) 1.375(5) 1.378(5) 1.352(4) 1.322(5) 1.388(6) 1.815(4) 1.845(4) 1.840(4) 1.519(6) 1.533(6) 1.532(6) 1.509(6) Br2 - Co1 Co1-4 C1-3 C11-3 C11 - C12 3-4 C13-4 C12 - C13 C11 - P2 C14 - P2 C17 - P2 C14 - C15 C14 - C16 C17 - C18 C17 - C19 2.3775(10) 2.017(3) 1.465(4) 1.356(5) 1.384(5) 1.356(4) 1.331(5) 1.385(5) 1.824(4) 1.877(4) 1.868(5) 1.547(8) 1.517(6) 1.511(7) 1.521(7) Br1 - Co1 - Br2 Br1 - Co1 - P1 4 - Co1 - Br1 1 - C1-3 2-1 - C1 2-1 - C2 1 - C2 - C3 C2-1 - C1 C4-2 - 1 C2 - C3 - C4 2 - C4 - C3 C3 - C2 - P1 1 - C2 - P1 C6 - C5 - P1 C7 - C5 - P1 C9 - C8 - P1 C10 - C8 - P1 C2 - P1 - C5 C2 - P1 - C8 C8 - P1 - C5 C2 - P1 - Co1 C5 - P1 - Co1 C8 - P1 - Co1 C10 - C8 - C9 C6 - C5 - C7 115.98(3) 112.77(4) 108.47(9) 113.2(3) 117.0(3) 112.3(3) 105.2(3) 130.7(3) 104.5(3) 105.7(3) 112.2(3) 129.0(3) 125.8(3) 109.4(3) 111.4(3) 114.8(3) 111.2(3) 100.72(18) 107.58(18) 105.2(2) 112.41(12) 112.40(14) 117.07(14) 110.4(4) 111.0(4) 4 - Co1 - P1 Br2 - Co1 - P1 4 - Co1 - Br2 4-3 - C1 4-3 - C11 3 - C11 - C12 C11-3 - C1 C13-4 - 3 C11 - C12 - C13 4 - C13 - C12 C12 - C11 - P2 3 - C11 - P2 C15 - C14 - P2 C16 - C14 - P2 C18 - C17 - P2 C19 - C17 - P2 C11 - P2 - C14 C11 - P2 - C17 C17 - P2 - C14 C13-4 - Co1 3-4 - Co1 C16 - C14 - C15 C18 - C17 - C19 101.68(9) 113.89(4) 102.27(9) 118.3(3) 112.0(3) 105.4(3) 129.6(3) 105.6(3) 106.6(3) 110.5(3) 132.7(3) 121.9(3) 106.5(3) 115.0(3) 111.3(3) 109.2(4) 99.93(18) 98.21(19) 99.6(2) 129.1(2) 125.1(2) 108.4(5) 111.4(4)

S56 Table S20: Hydrogen coordinates (x 10 4 ) and isotropic displacements parameters (Å 2 x 10 3 ) for 9. Label x y z U(eq) H10A 8804.0 3435.0 7499.0 74.0 H10B 7030.0 3335.0 8134.0 74.0 H10C 8454.0 2613.0 8719.0 74.0 H12 4423.0 9646.0 3972.0 41.0 H13 3252.0 8460.0 5841.0 38.0 H14 8277.0 10417.0 2688.0 58.0 H15A 11148.0 10040.0 2459.0 155.0 H15B 10520.0 9767.0 1574.0 155.0 H15C 11036.0 8747.0 2586.0 155.0 H16A 9451.0 8658.0 4472.0 76.0 H16B 7815.0 9450.0 4598.0 76.0 H16C 9434.0 9998.0 4214.0 76.0 H17 5881.0 10199.0 2138.0 54.0 H18A 4593.0 9543.0 1148.0 88.0 H18B 4560.0 8652.0 2338.0 88.0 H18C 5781.0 8389.0 1348.0 88.0 H19A 8068.0 9628.0 397.0 115.0 H19B 8280.0 10573.0 867.0 115.0 H19C 6858.0 10770.0 256.0 115.0 H1A 6998.0 5527.0 5421.0 30.0 H1B 7880.0 6132.0 4225.0 30.0 H3 11125.0 6199.0 6888.0 40.0 H4 12372.0 6610.0 4934.0 40.0 H5 8792.0 6813.0 8250.0 46.0 H6A 6000.0 8073.0 7452.0 76.0 H6B 7755.0 8203.0 6787.0 76.0 H6C 7178.0 8614.0 7817.0 76.0 H7A 6848.0 7146.0 9705.0 79.0 H7B 7082.0 5814.0 9849.0 79.0 H7C 5587.0 6616.0 9403.0 79.0 H8 7407.0 4220.0 9283.0 44.0 H9A 9987.0 3577.0 9478.0 72.0 H9B 9902.0 4940.0 9010.0 72.0 H9C 10648.0 4198.0 8233.0 72.0

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