Impact of Ferrocene Substitution on the Electronic Properties of BODIPY Derivatives and Analogues

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Impact of Ferrocene Substitution on the Electronic Properties of BODIPY Derivatives and Analogues Kang Yuan, Goonay Yousefalizadeh, Felix Saraci, Tai Peng, Igor Kozin, Kevin G. Stamplecoskie, Suning Wang* Department of Chemistry, Queen s University, Kingston, Ontario K7L 3N6, Canada Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry, Beijing Institute of Technology, Beijing 100081, People s Republic of China Table of Contents S1. Transient Absorption Spectra S2. DFT and TD-DFT Data S3. 1 H, 13 C and 11 B NMR Spectra S1

S1. Transient Absorption Spectra Figure S1. Time-resolved transient absorption spectra of compound 1 in toluene under N 2. Figure S2. Transient absorption kinetics of for compound 1 measured at 530 nm. S2

Figure S3. Time-resolved transient absorption spectra of compound 3 in toluene under N 2. Figure S4. Transient absorption kinetics of for compound 3 measured at 530 nm. S3

Figure S5. Time-resolved transient absorption spectra of compound 4 in toluene under N 2. Figure S6. Transient absorption kinetics of for compound 4 measured at 505 nm. S4

Relative Reflectance 2.5 2 1.5 1 0.5 1 2 3 4 0 400 500 600 700 800 Wavelength / nm Figure S7. UV-Vis reflectance spectra of compounds 1-4 solids. S5

S2. DFT and TD-DFT data Table S1. Frontier molecular orbitals of compound 1 (isocontour = 0.03). LUMO+1 LUMO HOMO HOMO-1 HOMO-2 HOMO-3 HOMO-4 HOMO-5 HOMO-6 HOMO-7 Table S7. Frontier molecular orbitals of compound 2(isocontour = 0.03). LUMO+1 LUMO HOMO HOMO-1 HOMO-2 HOMO-3 HOMO-4 HOMO-5 HOMO-6 HOMO-7 S6

Table S3. Frontier molecular orbitals of compound 3 (isocontour = 0.03). LUMO+1 LUMO HOMO HOMO-1 HOMO-2 HOMO-3 HOMO-4 HOMO-5 HOMO-6 HOMO-7 S7

0.35 0.3 ε / 10 5 cm -1 M -1 0.25 0.2 0.15 0.1 0.05 0 300 400 500 600 700 λ / nm Figure S8. Predicted UV-Vis absorption spectra for compound 1. Table S4. TD-DFT calculated transitions for compound 1. λ Oscillator Major contributions (nm) Strength S 1 627 0.0003 H-1 LUMO (12%), HOMO LUMO (86%) S 2 624 0.0009 H-1 LUMO (86%), HOMO LUMO (12%) S 3 607 0.0002 H-2 LUMO (97%) S 4 595 0.0006 H-3 LUMO (94%) S 5 576 0.0004 H-3 L+6 (14%), H-2 L+5 (13%), H-1 L+3 (32%), H-1 L+4 (18%) S 6 576 0.0001 H-3 L+5 (12%), H-2 L+6 (14%), HOMO L+3 (21%), HOMO L+4 (29%) S 7 498 0.001 H-6 L+3 (25%), H-5 L+4 (20%), H-2 L+5 (14%) S 8 498 0.0001 H-6 L+4 (23%), H-5 L+3 (21%), H-2 L+6 (12%) S 9 490 0.0002 H-6 L+6 (21%), H-5 L+5 (23%), H-3 L+6 (10%), H-2 L+4 (10%) S 10 490 0 H-6 L+5 (22%), H-5 L+6 (22%) S 11 444 0.0005 H-5 LUMO (99%) S 12 431 0.0089 H-6 LUMO (95%) S 13 416 0.2987 H-4 LUMO (94%) S 14 392 0.0051 H-7 LUMO (98%) S 15 386 0.0244 H-8 LUMO (97%) S 16 371 0.0001 H-6 L+3 (12%), H-6 L+4 (10%), H-5 L+3 (15%) S 17 371 0.0001 H-6 L+3 (10%), H-6 L+4 (10%), H-5 L+4 (16%) S 18 365 0 H-6 L+6 (23%), H-5 L+5 (23%), H-2 L+4 (10%) S8

0.004 0.0035 ε / 10 5 cm -1 M -1 0.003 0.0025 0.002 0.0015 0.001 0.0005 0 300 400 500 600 700 λ / nm Figure S9. Predicted UV-Vis absorption spectra for compound 2. Table S5. TD-DFT calculated transitions for compound 2. λ Oscillator Major contributions (nm) Strength S 1 542 0.0005 H-2 LUMO (74%) S 2 540 0.0017 H-1 LUMO (46%) S 3 536 0 H-3 LUMO (67%) S 4 521 0 H-3 L+4 (25%), H-2 LUMO (15%), H-2 L+3 (28%) S 5 520 0.0001 H-3 LUMO (23%), H-3 L+3 (21%), H-2 L+4 (26%) S 6 509 0.0005 H-1 L+6 (22%), HOMO LUMO (28%) S 7 508 0.0009 H-1 LUMO (34%), HOMO L+6 (22%) S 8 464 0.0002 H-5 L+3 (31%), H-3 L+4 (21%), H-2 L+3 (13%) S 9 464 0.0002 H-4 L+3 (14%), H-4 L+5 (14%), H-4 L+7 (12%), H-1 L+6 (13%) S 10 462 0 H-5 L+4 (34%), H-3 L+3 (16%), H-2 L+4 (19%) S 11 461 0 H-4 L+6 (30%), H-4 L+7 (10%), HOMO L+6 (12%) S 12 438 0.001 H-2 L+1 (96%) S 13 436 0 H-3 L+1 (60%), HOMO L+1 (32%) S 14 431 0.0002 H-3 L+1 (23%), H-1 L+1 (10%), HOMO L+1 (63%) S 15 429 0.0003 H-3 L+1 (16%), H-1 L+1 (80%) S 16 401 0.0031 H-5 LUMO (45%), H-4 LUMO (52%) S 17 393 0.0034 H-5 LUMO (53%), H-4 LUMO (42%) S 18 360 0.0037 H-6 LUMO (97%) S 19 351 0 H-5 L+3 (21%), H-5 L+4 (12%), H-3 L+4 (24%), H-2 L+3 (17%) S9

0.3 ε / 10 5 cm -1 M -1 0.25 0.2 0.15 0.1 0.05 Figure S10. Predicted UV-Vis absorption spectra for compound 3. Table S6. TD-DFT calculated transitions for compound 3. λ Oscillator Major contributions (nm) Strength S 1 527 0.0001 H-2 L+3 (19%), H-2 L+4 (24%), H-1 L+6 (10%), HOMO L+6 (20%) S 2 527 0.0023 H-2 L+6 (24%), H-1 L+4 (12%), HOMO L+3 (17%), HOMO L+4 (15%) S 3 526 0.0001 H-3 L+3 (22%), H-3 L+4 (21%), H-1 L+5 (21%) S 4 526 0.0019 H-3 L+5 (25%), H-1 L+3 (19%), H-1 L+4 (12%), HOMO L+4 (10%) S 5 517 0.0004 HOMO LUMO (91%) S 6 505 0.0001 H-1 LUMO (95%) S 7 489 0.0002 H-2 LUMO (90%) S 8 486 0.0001 H-3 LUMO (90%), H-2 LUMO (10%) S 9 467 0.0008 H-7 L+3 (20%), H-7 L+4 (23%), H-2 L+6 (21%) S 10 466 0.0007 H-8 L+3 (22%), H-8 L+4 (20%), H-3 L+5 (21%) S 11 460 0 H-7 L+6 (31%), HOMO L+6 (14%) S 12 459 0 H-8 L+5 (30%), H-1 L+5 (15%) S 13 426 0.0841 H-5 LUMO (67%), H-4 LUMO (29%) S 14 407 0.2814 H-5 LUMO (30%), H-4 LUMO (66%) S 15 404 0 H-6 LUMO (92%) S 16 403 0.013 H-6 LUMO (93%) S 17 372 0.0303 H-9 LUMO (93%) 0 300 400 500 600 700 λ / nm S 18 367 0.001 H-8 LUMO (27%), H-7 LUMO (72%) S 19 366 0.0005 H-8 LUMO (68%), H-7 LUMO (25%) S 20 354 0.0008 H-7 L+3 (15%), H-7 L+4 (17%), H-2 L+6 (22%) S10

S3. 1 H, 13 C and 11 B NMR spectra Figure S11. 1 H NMR spectrum of compound 1 in CDCl 3. Figure S12. 11 B NMR spectrum of compound 1 in CDCl 3. S11

Figure S13. 13 C{ 1 H} NMR spectrum of compound 1 in CDCl 3. S12

Figure S14. 1 H NMR spectrum of compound 2 in CDCl 3. Figure S15. 11 B NMR spectrum of compound 2 in CDCl 3. S13

Figure S16. 13 C{ 1 H} NMR spectrum of compound 2 in CDCl 3. S14

Figure S17. 1 H NMR spectrum of compound 3 in CDCl 3. Figure S18. 11 B NMR spectrum of compound 3 in CDCl 3. S15

Figure S19. 13 C{ 1 H} NMR spectrum of compound 3 in CDCl 3. S16

Table S7-1. Crystal data and structure refinement for compound 1. Identification code compound 1 Empirical formula C39 H37 B Fe2 N2 Formula weight 656.21 Temperature 180(2) K Wavelength 0.71073 Å Crystal system Triclinic Space group P-1 Unit cell dimensions a = 10.3803(19) Å = 79.180(10). b = 12.354(2) Å = 86.833(10). c = 13.522(3) Å = 70.461(7). Volume 1605.1(6) Å 3 Z 2 Density (calculated) 1.358 Mg/m 3 Absorption coefficient 0.934 mm -1 F(000) 684 Crystal size 0.068 x 0.067 x 0.048 mm 3 Theta range for data collection 2.576 to 27.465. Index ranges -13<=h<=13, -16<=k<=16, -17<=l<=17 Reflections collected 30862 Independent reflections 7339 [R(int) = 0.0663] Completeness to theta = 25.242 99.8 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.760 and 0.650 Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 7339 / 0 / 401 Goodness-of-fit on F 2 1.038 Final R indices [I>2sigma(I)] R1 = 0.0398, wr2 = 0.0768 R indices (all data) R1 = 0.0692, wr2 = 0.0848 Extinction coefficient n/a Largest diff. peak and hole 0.374 and -0.383 e.å -3 S17

Table S7-2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for compound 1. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) B(1) 7227(2) 6649(2) 7678(2) 17(1) Fe(1) 6212(1) 4172(1) 8154(1) 23(1) Fe(2) 8037(1) 8733(1) 8618(1) 24(1) N(1) 6086(2) 7232(1) 6827(1) 18(1) N(2) 8635(2) 6446(1) 7100(1) 17(1) C(1) 7256(2) 5351(2) 8241(2) 18(1) C(2) 6721(2) 4987(2) 9197(2) 23(1) C(3) 7269(2) 3747(2) 9478(2) 31(1) C(4) 8143(2) 3317(2) 8693(2) 32(1) C(5) 8117(2) 4291(2) 7936(2) 24(1) C(6) 6980(2) 7606(2) 8409(2) 17(1) C(7) 7343(2) 7455(2) 9447(2) 24(1) C(8) 6765(2) 8532(2) 9797(2) 32(1) C(9) 6036(2) 9379(2) 8984(2) 31(1) C(10) 6177(2) 8819(2) 8140(2) 23(1) C(11) 4688(2) 4875(2) 7093(2) 38(1) C(12) 4147(2) 4600(3) 8061(2) 44(1) C(13) 4740(3) 3400(3) 8419(2) 47(1) C(14) 5640(3) 2919(2) 7687(2) 45(1) C(15) 5629(3) 3821(3) 6862(2) 41(1) C(16) 9563(3) 8685(3) 7583(2) 47(1) C(17) 8699(3) 9853(3) 7593(2) 47(1) C(18) 8762(3) 10078(2) 8572(2) 44(1) C(19) 9650(3) 9059(3) 9150(2) 50(1) C(20) 10134(3) 8219(2) 8547(3) 49(1) C(21) 4725(2) 7609(2) 6971(2) 23(1) C(22) 4062(2) 8202(2) 6052(2) 28(1) C(23) 5026(2) 8224(2) 5317(2) 24(1) C(24) 6322(2) 7599(2) 5805(2) 18(1) C(25) 7647(2) 7361(2) 5437(2) 18(1) C(26) 8789(2) 6771(2) 6059(2) 20(1) S18

C(27) 10218(2) 6368(2) 5832(2) 28(1) C(28) 10869(2) 5833(2) 6739(2) 28(1) C(29) 9896(2) 5882(2) 7505(2) 21(1) C(30) 4722(2) 8851(2) 4245(2) 36(1) C(31) 10925(3) 6418(3) 4834(2) 51(1) C(32) 10195(2) 5378(2) 8594(2) 26(1) C(33) 4046(2) 7475(2) 7970(2) 31(1) C(34) 7871(2) 7766(2) 4347(2) 23(1) C(35) 8228(2) 8763(2) 4052(2) 32(1) C(36) 8446(3) 9148(2) 3043(2) 42(1) C(37) 8325(3) 8523(3) 2332(2) 45(1) C(38) 7967(3) 7533(3) 2617(2) 47(1) C(39) 7725(3) 7159(2) 3621(2) 37(1) Table S7-3. Bond lengths [Å] and angles [ ] for compound 1. B(1)-N(2) 1.585(3) B(1)-N(1) 1.586(3) B(1)-C(6) 1.629(3) B(1)-C(1) 1.632(3) Fe(1)-C(4) 2.030(2) Fe(1)-C(5) 2.033(2) Fe(1)-C(12) 2.034(2) Fe(1)-C(13) 2.040(2) Fe(1)-C(3) 2.040(2) Fe(1)-C(14) 2.043(2) Fe(1)-C(11) 2.045(2) Fe(1)-C(15) 2.046(2) Fe(1)-C(2) 2.063(2) Fe(1)-C(1) 2.108(2) Fe(2)-C(17) 2.029(3) Fe(2)-C(9) 2.030(2) Fe(2)-C(18) 2.030(2) Fe(2)-C(10) 2.033(2) Fe(2)-C(19) 2.044(3) S19 Fe(2)-C(8) 2.046(2) Fe(2)-C(16) 2.048(3) Fe(2)-C(20) 2.055(3) Fe(2)-C(7) 2.067(2) Fe(2)-C(6) 2.103(2) N(1)-C(21) 1.347(2) N(1)-C(24) 1.406(3) N(2)-C(29) 1.350(2) N(2)-C(26) 1.405(3) C(1)-C(2) 1.433(3) C(1)-C(5) 1.436(3) C(2)-C(3) 1.427(3) C(2)-H(2A) 1.0000 C(3)-C(4) 1.419(3) C(3)-H(3A) 1.0000 C(4)-C(5) 1.419(3) C(4)-H(4A) 1.0000 C(5)-H(5A) 1.0000 C(6)-C(7) 1.435(3)

C(6)-C(10) 1.437(3) C(7)-C(8) 1.423(3) C(7)-H(7A) 1.0000 C(8)-C(9) 1.416(3) C(8)-H(8A) 1.0000 C(9)-C(10) 1.418(3) C(9)-H(9A) 1.0000 C(10)-H(10A) 1.0000 C(11)-C(15) 1.419(4) C(11)-C(12) 1.423(4) C(11)-H(11A) 1.0000 C(12)-C(13) 1.401(4) C(12)-H(12A) 1.0000 C(13)-C(14) 1.398(4) C(13)-H(13A) 1.0000 C(14)-C(15) 1.419(4) C(14)-H(14A) 1.0000 C(15)-H(15A) 1.0000 C(16)-C(20) 1.399(4) C(16)-C(17) 1.423(4) C(16)-H(16A) 1.0000 C(17)-C(18) 1.413(4) C(17)-H(17A) 1.0000 C(18)-C(19) 1.406(4) C(18)-H(18A) 1.0000 C(19)-C(20) 1.386(4) C(19)-H(19A) 1.0000 C(20)-H(20A) 1.0000 C(21)-C(22) 1.404(3) C(21)-C(33) 1.495(3) C(22)-C(23) 1.374(3) C(22)-H(22A) 0.9500 C(23)-C(24) 1.434(3) C(23)-C(30) 1.505(3) C(24)-C(25) 1.391(3) C(25)-C(26) 1.395(3) C(25)-C(34) 1.496(3) C(26)-C(27) 1.434(3) C(27)-C(28) 1.374(3) C(27)-C(31) 1.501(3) C(28)-C(29) 1.402(3) C(28)-H(28A) 0.9500 C(29)-C(32) 1.493(3) C(30)-H(30A) 0.9800 C(30)-H(30B) 0.9800 C(30)-H(30C) 0.9800 C(31)-H(31A) 0.9800 C(31)-H(31B) 0.9800 C(31)-H(31C) 0.9800 C(32)-H(32A) 0.9800 C(32)-H(32B) 0.9800 C(32)-H(32C) 0.9800 C(33)-H(33A) 0.9800 C(33)-H(33B) 0.9800 C(33)-H(33C) 0.9800 C(34)-C(35) 1.384(3) C(34)-C(39) 1.385(3) C(35)-C(36) 1.391(3) C(35)-H(35A) 0.9500 C(36)-C(37) 1.376(4) C(36)-H(36A) 0.9500 C(37)-C(38) 1.376(4) C(37)-H(37A) 0.9500 C(38)-C(39) 1.387(3) C(38)-H(38A) 0.9500 C(39)-H(39A) 0.9500 N(2)-B(1)-N(1) 105.12(16) N(2)-B(1)-C(6) 112.12(16) N(1)-B(1)-C(6) 105.35(16) N(2)-B(1)-C(1) 105.14(16) N(1)-B(1)-C(1) 113.39(16) S20

C(6)-B(1)-C(1) 115.38(17) C(4)-Fe(1)-C(5) 40.89(9) C(4)-Fe(1)-C(12) 158.36(11) C(5)-Fe(1)-C(12) 160.25(11) C(4)-Fe(1)-C(13) 120.77(11) C(5)-Fe(1)-C(13) 158.09(11) C(12)-Fe(1)-C(13) 40.23(12) C(4)-Fe(1)-C(3) 40.82(10) C(5)-Fe(1)-C(3) 68.40(9) C(12)-Fe(1)-C(3) 123.87(11) C(13)-Fe(1)-C(3) 105.35(11) C(4)-Fe(1)-C(14) 104.31(11) C(5)-Fe(1)-C(14) 122.97(11) C(12)-Fe(1)-C(14) 67.46(12) C(13)-Fe(1)-C(14) 40.03(11) C(3)-Fe(1)-C(14) 118.49(11) C(4)-Fe(1)-C(11) 156.72(11) C(5)-Fe(1)-C(11) 123.61(10) C(12)-Fe(1)-C(11) 40.83(10) C(13)-Fe(1)-C(11) 68.29(11) C(3)-Fe(1)-C(11) 162.31(11) C(14)-Fe(1)-C(11) 67.98(11) C(4)-Fe(1)-C(15) 119.37(11) C(5)-Fe(1)-C(15) 107.74(10) C(12)-Fe(1)-C(15) 68.28(11) C(13)-Fe(1)-C(15) 68.24(11) C(3)-Fe(1)-C(15) 154.17(11) C(14)-Fe(1)-C(15) 40.62(11) C(11)-Fe(1)-C(15) 40.61(11) C(4)-Fe(1)-C(2) 68.30(9) C(5)-Fe(1)-C(2) 67.59(9) C(12)-Fe(1)-C(2) 110.39(10) C(13)-Fe(1)-C(2) 122.19(10) C(3)-Fe(1)-C(2) 40.72(9) C(14)-Fe(1)-C(2) 155.44(10) C(11)-Fe(1)-C(2) 127.59(10) C(15)-Fe(1)-C(2) 163.46(10) C(4)-Fe(1)-C(1) 68.82(8) C(5)-Fe(1)-C(1) 40.53(8) C(12)-Fe(1)-C(1) 125.10(10) C(13)-Fe(1)-C(1) 158.70(11) C(3)-Fe(1)-C(1) 68.60(9) C(14)-Fe(1)-C(1) 161.00(10) C(11)-Fe(1)-C(1) 110.99(9) C(15)-Fe(1)-C(1) 126.08(10) C(2)-Fe(1)-C(1) 40.16(8) C(17)-Fe(2)-C(9) 114.20(11) C(17)-Fe(2)-C(18) 40.72(11) C(9)-Fe(2)-C(18) 104.73(11) C(17)-Fe(2)-C(10) 107.31(10) C(9)-Fe(2)-C(10) 40.86(9) C(18)-Fe(2)-C(10) 127.40(10) C(17)-Fe(2)-C(19) 67.92(12) C(9)-Fe(2)-C(19) 127.46(12) C(18)-Fe(2)-C(19) 40.39(11) C(10)-Fe(2)-C(19) 165.77(11) C(17)-Fe(2)-C(8) 147.16(12) C(9)-Fe(2)-C(8) 40.67(9) C(18)-Fe(2)-C(8) 114.59(11) C(10)-Fe(2)-C(8) 68.17(9) C(19)-Fe(2)-C(8) 108.07(11) C(17)-Fe(2)-C(16) 40.85(12) C(9)-Fe(2)-C(16) 149.35(12) C(18)-Fe(2)-C(16) 68.18(11) C(10)-Fe(2)-C(16) 118.64(11) C(19)-Fe(2)-C(16) 67.23(12) C(8)-Fe(2)-C(16) 169.86(12) C(17)-Fe(2)-C(20) 67.72(12) C(9)-Fe(2)-C(20) 166.38(12) C(18)-Fe(2)-C(20) 67.40(11) C(10)-Fe(2)-C(20) 152.72(11) C(19)-Fe(2)-C(20) 39.51(12) S21

C(8)-Fe(2)-C(20) 130.95(12) C(16)-Fe(2)-C(20) 39.87(12) C(17)-Fe(2)-C(7) 169.81(11) C(9)-Fe(2)-C(7) 68.06(9) C(18)-Fe(2)-C(7) 149.41(11) C(10)-Fe(2)-C(7) 67.42(9) C(19)-Fe(2)-C(7) 119.31(11) C(8)-Fe(2)-C(7) 40.49(9) C(16)-Fe(2)-C(7) 132.90(10) C(20)-Fe(2)-C(7) 112.62(10) C(17)-Fe(2)-C(6) 130.20(10) C(9)-Fe(2)-C(6) 68.95(9) C(18)-Fe(2)-C(6) 166.96(10) C(10)-Fe(2)-C(6) 40.61(8) C(19)-Fe(2)-C(6) 152.34(10) C(8)-Fe(2)-C(6) 68.59(9) C(16)-Fe(2)-C(6) 111.07(9) C(20)-Fe(2)-C(6) 121.01(10) C(7)-Fe(2)-C(6) 40.23(8) C(21)-N(1)-C(24) 107.69(16) C(21)-N(1)-B(1) 126.22(17) C(24)-N(1)-B(1) 125.50(16) C(29)-N(2)-C(26) 107.67(17) C(29)-N(2)-B(1) 126.49(17) C(26)-N(2)-B(1) 125.76(16) C(2)-C(1)-C(5) 105.16(18) C(2)-C(1)-B(1) 130.13(18) C(5)-C(1)-B(1) 123.53(18) C(2)-C(1)-Fe(1) 68.21(11) C(5)-C(1)-Fe(1) 66.93(11) B(1)-C(1)-Fe(1) 138.09(14) C(3)-C(2)-C(1) 109.7(2) C(3)-C(2)-Fe(1) 68.80(13) C(1)-C(2)-Fe(1) 71.63(12) C(3)-C(2)-H(2A) 125.2 C(1)-C(2)-H(2A) 125.2 Fe(1)-C(2)-H(2A) 125.2 C(4)-C(3)-C(2) 107.6(2) C(4)-C(3)-Fe(1) 69.20(13) C(2)-C(3)-Fe(1) 70.48(12) C(4)-C(3)-H(3A) 126.2 C(2)-C(3)-H(3A) 126.2 Fe(1)-C(3)-H(3A) 126.2 C(5)-C(4)-C(3) 107.5(2) C(5)-C(4)-Fe(1) 69.67(12) C(3)-C(4)-Fe(1) 69.97(13) C(5)-C(4)-H(4A) 126.2 C(3)-C(4)-H(4A) 126.2 Fe(1)-C(4)-H(4A) 126.2 C(4)-C(5)-C(1) 110.0(2) C(4)-C(5)-Fe(1) 69.44(12) C(1)-C(5)-Fe(1) 72.54(12) C(4)-C(5)-H(5A) 125.0 C(1)-C(5)-H(5A) 125.0 Fe(1)-C(5)-H(5A) 125.0 C(7)-C(6)-C(10) 104.87(18) C(7)-C(6)-B(1) 130.36(18) C(10)-C(6)-B(1) 124.46(18) C(7)-C(6)-Fe(2) 68.55(12) C(10)-C(6)-Fe(2) 67.07(12) B(1)-C(6)-Fe(2) 133.00(14) C(8)-C(7)-C(6) 109.79(19) C(8)-C(7)-Fe(2) 68.93(13) C(6)-C(7)-Fe(2) 71.23(12) C(8)-C(7)-H(7A) 125.1 C(6)-C(7)-H(7A) 125.1 Fe(2)-C(7)-H(7A) 125.1 C(9)-C(8)-C(7) 107.7(2) C(9)-C(8)-Fe(2) 69.07(13) C(7)-C(8)-Fe(2) 70.58(13) C(9)-C(8)-H(8A) 126.1 C(7)-C(8)-H(8A) 126.1 S22

Fe(2)-C(8)-H(8A) 126.1 C(8)-C(9)-C(10) 107.5(2) C(8)-C(9)-Fe(2) 70.26(13) C(10)-C(9)-Fe(2) 69.68(12) C(8)-C(9)-H(9A) 126.2 C(10)-C(9)-H(9A) 126.2 Fe(2)-C(9)-H(9A) 126.2 C(9)-C(10)-C(6) 110.1(2) C(9)-C(10)-Fe(2) 69.46(13) C(6)-C(10)-Fe(2) 72.33(12) C(9)-C(10)-H(10A) 124.9 C(6)-C(10)-H(10A) 124.9 Fe(2)-C(10)-H(10A) 124.9 C(15)-C(11)-C(12) 107.4(2) C(15)-C(11)-Fe(1) 69.75(14) C(12)-C(11)-Fe(1) 69.19(14) C(15)-C(11)-H(11A) 126.3 C(12)-C(11)-H(11A) 126.3 Fe(1)-C(11)-H(11A) 126.3 C(13)-C(12)-C(11) 108.5(3) C(13)-C(12)-Fe(1) 70.11(15) C(11)-C(12)-Fe(1) 69.98(14) C(13)-C(12)-H(12A) 125.7 C(11)-C(12)-H(12A) 125.7 Fe(1)-C(12)-H(12A) 125.7 C(14)-C(13)-C(12) 108.0(3) C(14)-C(13)-Fe(1) 70.10(15) C(12)-C(13)-Fe(1) 69.65(14) C(14)-C(13)-H(13A) 126.0 C(12)-C(13)-H(13A) 126.0 Fe(1)-C(13)-H(13A) 126.0 C(13)-C(14)-C(15) 108.9(3) C(13)-C(14)-Fe(1) 69.86(15) C(15)-C(14)-Fe(1) 69.80(14) C(13)-C(14)-H(14A) 125.5 C(15)-C(14)-H(14A) 125.5 Fe(1)-C(14)-H(14A) 125.5 C(14)-C(15)-C(11) 107.2(2) C(14)-C(15)-Fe(1) 69.58(14) C(11)-C(15)-Fe(1) 69.64(14) C(14)-C(15)-H(15A) 126.4 C(11)-C(15)-H(15A) 126.4 Fe(1)-C(15)-H(15A) 126.4 C(20)-C(16)-C(17) 107.5(3) C(20)-C(16)-Fe(2) 70.35(16) C(17)-C(16)-Fe(2) 68.88(15) C(20)-C(16)-H(16A) 126.2 C(17)-C(16)-H(16A) 126.2 Fe(2)-C(16)-H(16A) 126.2 C(18)-C(17)-C(16) 107.4(3) C(18)-C(17)-Fe(2) 69.66(15) C(16)-C(17)-Fe(2) 70.26(15) C(18)-C(17)-H(17A) 126.3 C(16)-C(17)-H(17A) 126.3 Fe(2)-C(17)-H(17A) 126.3 C(19)-C(18)-C(17) 107.6(3) C(19)-C(18)-Fe(2) 70.33(15) C(17)-C(18)-Fe(2) 69.61(14) C(19)-C(18)-H(18A) 126.2 C(17)-C(18)-H(18A) 126.2 Fe(2)-C(18)-H(18A) 126.2 C(20)-C(19)-C(18) 108.6(3) C(20)-C(19)-Fe(2) 70.69(15) C(18)-C(19)-Fe(2) 69.28(15) C(20)-C(19)-H(19A) 125.7 C(18)-C(19)-H(19A) 125.7 Fe(2)-C(19)-H(19A) 125.7 C(19)-C(20)-C(16) 108.9(3) C(19)-C(20)-Fe(2) 69.80(16) C(16)-C(20)-Fe(2) 69.77(15) C(19)-C(20)-H(20A) 125.6 C(16)-C(20)-H(20A) 125.6 S23

Fe(2)-C(20)-H(20A) 125.6 N(1)-C(21)-C(22) 109.26(19) N(1)-C(21)-C(33) 124.79(19) C(22)-C(21)-C(33) 125.85(19) C(23)-C(22)-C(21) 109.15(18) C(23)-C(22)-H(22A) 125.4 C(21)-C(22)-H(22A) 125.4 C(22)-C(23)-C(24) 105.70(19) C(22)-C(23)-C(30) 125.1(2) C(24)-C(23)-C(30) 129.2(2) C(25)-C(24)-N(1) 120.74(17) C(25)-C(24)-C(23) 131.1(2) N(1)-C(24)-C(23) 108.18(18) C(24)-C(25)-C(26) 121.94(19) C(24)-C(25)-C(34) 119.67(18) C(26)-C(25)-C(34) 118.38(18) C(25)-C(26)-N(2) 120.55(18) C(25)-C(26)-C(27) 131.2(2) N(2)-C(26)-C(27) 108.27(18) C(28)-C(27)-C(26) 105.53(19) C(28)-C(27)-C(31) 124.5(2) C(26)-C(27)-C(31) 129.9(2) C(27)-C(28)-C(29) 109.43(19) C(27)-C(28)-H(28A) 125.3 C(29)-C(28)-H(28A) 125.3 N(2)-C(29)-C(28) 109.09(19) N(2)-C(29)-C(32) 125.20(19) C(28)-C(29)-C(32) 125.70(19) C(23)-C(30)-H(30A) 109.5 C(23)-C(30)-H(30B) 109.5 H(30A)-C(30)-H(30B) 109.5 C(23)-C(30)-H(30C) 109.5 H(30A)-C(30)-H(30C) 109.5 H(30B)-C(30)-H(30C) 109.5 C(27)-C(31)-H(31A) 109.5 C(27)-C(31)-H(31B) 109.5 H(31A)-C(31)-H(31B) 109.5 C(27)-C(31)-H(31C) 109.5 H(31A)-C(31)-H(31C) 109.5 H(31B)-C(31)-H(31C) 109.5 C(29)-C(32)-H(32A) 109.5 C(29)-C(32)-H(32B) 109.5 H(32A)-C(32)-H(32B) 109.5 C(29)-C(32)-H(32C) 109.5 H(32A)-C(32)-H(32C) 109.5 H(32B)-C(32)-H(32C) 109.5 C(21)-C(33)-H(33A) 109.5 C(21)-C(33)-H(33B) 109.5 H(33A)-C(33)-H(33B) 109.5 C(21)-C(33)-H(33C) 109.5 H(33A)-C(33)-H(33C) 109.5 H(33B)-C(33)-H(33C) 109.5 C(35)-C(34)-C(39) 119.0(2) C(35)-C(34)-C(25) 120.0(2) C(39)-C(34)-C(25) 121.0(2) C(34)-C(35)-C(36) 120.7(2) C(34)-C(35)-H(35A) 119.7 C(36)-C(35)-H(35A) 119.7 C(37)-C(36)-C(35) 119.7(2) C(37)-C(36)-H(36A) 120.2 C(35)-C(36)-H(36A) 120.2 C(36)-C(37)-C(38) 120.1(2) C(36)-C(37)-H(37A) 120.0 C(38)-C(37)-H(37A) 120.0 C(37)-C(38)-C(39) 120.3(3) C(37)-C(38)-H(38A) 119.8 C(39)-C(38)-H(38A) 119.8 C(34)-C(39)-C(38) 120.2(2) C(34)-C(39)-H(39A) 119.9 C(38)-C(39)-H(39A) 119.9 S24

Table S7-4. Anisotropic displacement parameters (Å 2 x 10 3 ) for compound 1. The anisotropic displacement factor exponent takes the form: -2 2 [ h 2 a* 2 U 11 +... + 2 h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 B(1) 12(1) 21(1) 16(1) 1(1) 0(1) -6(1) Fe(1) 22(1) 27(1) 24(1) -3(1) 0(1) -14(1) Fe(2) 25(1) 23(1) 26(1) -4(1) -1(1) -11(1) N(1) 14(1) 21(1) 16(1) 0(1) -2(1) -5(1) N(2) 13(1) 19(1) 15(1) 1(1) -1(1) -3(1) C(1) 14(1) 21(1) 18(1) -2(1) -3(1) -7(1) C(2) 22(1) 29(1) 19(1) -1(1) -2(1) -12(1) C(3) 36(1) 33(1) 26(1) 11(1) -9(1) -20(1) C(4) 25(1) 18(1) 50(2) 1(1) -7(1) -7(1) C(5) 19(1) 23(1) 30(1) -3(1) 1(1) -8(1) C(6) 14(1) 20(1) 17(1) 0(1) 2(1) -8(1) C(7) 29(1) 27(1) 16(1) 1(1) 0(1) -12(1) C(8) 41(1) 37(1) 22(1) -11(1) 7(1) -17(1) C(9) 29(1) 27(1) 37(1) -13(1) 9(1) -8(1) C(10) 19(1) 22(1) 25(1) -1(1) 0(1) -5(1) C(11) 34(1) 45(2) 41(2) 1(1) -17(1) -21(1) C(12) 24(1) 70(2) 45(2) -18(2) 1(1) -23(1) C(13) 50(2) 66(2) 45(2) -4(2) 0(1) -47(2) C(14) 54(2) 41(2) 52(2) -12(1) -12(1) -28(1) C(15) 43(2) 63(2) 31(2) -19(1) 2(1) -30(1) C(16) 46(2) 62(2) 56(2) -28(2) 24(1) -42(2) C(17) 45(2) 51(2) 49(2) 19(1) -9(1) -34(1) C(18) 48(2) 31(2) 65(2) -14(1) 4(1) -25(1) C(19) 50(2) 57(2) 54(2) -3(2) -17(1) -35(2) C(20) 26(1) 37(2) 85(2) -5(2) -2(1) -17(1) C(21) 16(1) 23(1) 27(1) -1(1) -1(1) -5(1) C(22) 16(1) 29(1) 34(1) 1(1) -9(1) -3(1) C(23) 25(1) 23(1) 23(1) -1(1) -9(1) -6(1) C(24) 21(1) 18(1) 16(1) -2(1) -2(1) -7(1) C(25) 24(1) 17(1) 15(1) -2(1) 1(1) -7(1) S25

C(26) 20(1) 21(1) 19(1) -2(1) 4(1) -7(1) C(27) 20(1) 34(1) 26(1) -3(1) 6(1) -6(1) C(28) 14(1) 33(1) 31(1) 0(1) 3(1) -4(1) C(29) 16(1) 21(1) 23(1) 0(1) -1(1) -5(1) C(30) 34(1) 39(2) 28(1) 3(1) -13(1) -6(1) C(31) 27(1) 77(2) 32(2) 2(2) 14(1) -1(1) C(32) 16(1) 31(1) 24(1) 3(1) -5(1) -4(1) C(33) 16(1) 42(2) 31(1) 0(1) 3(1) -8(1) C(34) 23(1) 25(1) 17(1) -1(1) 1(1) -5(1) C(35) 38(1) 37(1) 26(1) -4(1) 1(1) -19(1) C(36) 47(2) 48(2) 31(2) 11(1) 2(1) -25(1) C(37) 45(2) 66(2) 20(1) 7(1) 5(1) -20(2) C(38) 66(2) 59(2) 20(1) -13(1) 4(1) -21(2) C(39) 56(2) 36(1) 23(1) -6(1) 5(1) -20(1) Table S7-5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for compound 1. x y z U(eq) H(2A) 6053 5520 9601 27 H(3A) 7079 3268 10116 38 H(4A) 8687 2482 8680 38 H(5A) 8630 4246 7289 29 H(7A) 7935 6710 9857 29 H(8A) 6852 8666 10493 38 H(9A) 5505 10215 9004 37 H(10A) 5773 9210 7458 28 H(11A) 4449 5664 6656 46 H(12A) 3460 5168 8426 53 H(13A) 4549 2964 9080 57 H(14A) 6211 2078 7741 54 H(15A) 6176 3731 6232 49 H(16A) 9733 8274 6994 57 H(17A) 8162 10416 7010 56 S26

H(18A) 8274 10829 8809 53 H(19A) 9889 8958 9876 60 H(20A) 10772 7407 8768 58 H(22A) 3101 8534 5953 34 H(28A) 11830 5485 6833 33 H(30A) 3742 9287 4167 54 H(30B) 4986 8281 3792 54 H(30C) 5240 9394 4077 54 H(31A) 11899 5965 4929 77 H(31B) 10820 7232 4542 77 H(31C) 10518 6089 4378 77 H(32A) 9598 5917 9005 38 H(32B) 11152 5259 8739 38 H(32C) 10032 4628 8753 38 H(33A) 4564 6731 8386 47 H(33B) 3113 7488 7870 47 H(33C) 4017 8119 8308 47 H(35A) 8324 9188 4544 39 H(36A) 8678 9838 2845 51 H(37A) 8489 8775 1643 55 H(38A) 7885 7104 2124 57 H(39A) 7458 6485 3811 44 S27

Table S8-1. Crystal data and structure refinement for compound 2. Identification code compound 2 Empirical formula C31 H26 B Fe2 N Formula weight 535.04 Temperature 180(2) K Wavelength 0.71073 Å Crystal system Monoclinic Space group P21/c Unit cell dimensions a = 15.621(14) Å = 90. b = 9.497(5) Å = 95.76(4). c = 15.952(15) Å = 90. Volume 2355(3) Å 3 Z 4 Density (calculated) 1.509 Mg/m 3 Absorption coefficient 1.253 mm -1 F(000) 1104 Crystal size 0.207 x 0.178 x 0.154 mm 3 Theta range for data collection 2.499 to 28.918. Index ranges -21<=h<=21, -12<=k<=10, -20<=l<=20 Reflections collected 47288 Independent reflections 5860 [R(int) = 0.1014] Completeness to theta = 25.242 99.9 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.746 and 0.508 Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 5860 / 0 / 316 Goodness-of-fit on F 2 1.075 Final R indices [I>2sigma(I)] R1 = 0.0453, wr2 = 0.1006 R indices (all data) R1 = 0.0708, wr2 = 0.1104 Extinction coefficient n/a Largest diff. peak and hole 0.442 and -0.616 e.å -3 S28

Table S8-2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for compound 2. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) Fe(2) 7364(1) 2475(1) 5627(1) 18(1) Fe(1) 6003(1) 7629(1) 6935(1) 17(1) N(1) 8590(1) 5248(2) 7234(1) 18(1) C(1) 8706(2) 4738(3) 8038(2) 25(1) C(2) 9497(2) 4429(3) 8417(2) 33(1) C(3) 10183(2) 4653(3) 7964(2) 42(1) C(4) 10076(2) 5220(3) 7148(2) 36(1) C(5) 9259(1) 5518(2) 6790(2) 21(1) C(6) 8978(1) 6145(2) 5956(2) 20(1) C(7) 9485(2) 6564(3) 5330(2) 26(1) C(8) 9103(2) 7150(3) 4580(2) 27(1) C(9) 8238(2) 7306(3) 4465(2) 25(1) C(10) 7740(2) 6866(3) 5094(2) 21(1) C(11) 8096(1) 6269(2) 5856(1) 15(1) C(12) 7168(1) 6630(2) 7215(1) 16(1) C(13) 6566(1) 6200(2) 7790(1) 20(1) C(14) 6280(2) 7401(3) 8224(2) 24(1) C(15) 6692(2) 8598(3) 7926(2) 24(1) C(16) 7234(1) 8131(2) 7312(2) 20(1) C(17) 5511(2) 7220(3) 5698(2) 24(1) C(18) 4974(2) 6690(3) 6291(2) 29(1) C(19) 4726(2) 7839(3) 6783(2) 30(1) C(20) 5112(2) 9082(3) 6499(2) 28(1) C(21) 5600(2) 8690(3) 5824(2) 25(1) C(22) 7211(1) 4118(2) 6484(1) 17(1) C(23) 7355(2) 2793(2) 6921(2) 21(1) C(24) 6723(2) 1803(3) 6612(2) 26(1) C(25) 6174(2) 2488(2) 5981(2) 25(1) C(26) 6471(1) 3892(2) 5902(2) 21(1) C(27) 8194(2) 3088(3) 4790(2) 34(1) C(28) 8540(2) 1999(3) 5333(2) 38(1) S29

C(29) 8017(2) 812(3) 5215(2) 40(1) C(30) 7341(2) 1155(3) 4604(2) 41(1) C(31) 7448(2) 2559(3) 4337(2) 38(1) B(1) 7694(2) 5592(3) 6666(2) 16(1) Table S8-33. Bond lengths [Å] and angles [ ] for compound 2. Fe(2)-C(28) 1.994(3) Fe(2)-C(25) 1.996(3) Fe(2)-C(26) 2.018(3) Fe(2)-C(29) 2.026(3) Fe(2)-C(27) 2.037(3) Fe(2)-C(24) 2.048(3) Fe(2)-C(30) 2.056(3) Fe(2)-C(31) 2.077(3) Fe(2)-C(23) 2.087(3) Fe(2)-C(22) 2.104(2) Fe(1)-C(19) 1.995(3) Fe(1)-C(16) 2.014(3) Fe(1)-C(18) 2.024(3) Fe(1)-C(20) 2.032(3) Fe(1)-C(15) 2.041(3) Fe(1)-C(13) 2.058(2) Fe(1)-C(12) 2.062(3) Fe(1)-C(14) 2.070(3) Fe(1)-C(21) 2.080(3) Fe(1)-C(17) 2.080(3) N(1)-C(5) 1.345(3) N(1)-C(1) 1.365(3) N(1)-B(1) 1.622(3) C(1)-C(2) 1.352(4) C(2)-C(3) 1.368(4) C(3)-C(4) 1.404(4) C(4)-C(5) 1.375(3) C(5)-C(6) 1.482(3) C(6)-C(11) 1.376(3) S30 C(6)-C(7) 1.393(3) C(7)-C(8) 1.399(4) C(8)-C(9) 1.353(4) C(9)-C(10) 1.394(4) C(10)-C(11) 1.404(3) C(11)-B(1) 1.626(4) C(12)-C(16) 1.436(3) C(12)-C(13) 1.437(3) C(12)-B(1) 1.599(3) C(13)-C(14) 1.430(3) C(14)-C(15) 1.412(4) C(15)-C(16) 1.428(3) C(17)-C(21) 1.416(3) C(17)-C(18) 1.418(4) C(18)-C(19) 1.421(4) C(19)-C(20) 1.420(4) C(20)-C(21) 1.429(4) C(22)-C(26) 1.425(3) C(22)-C(23) 1.446(3) C(22)-B(1) 1.603(3) C(23)-C(24) 1.415(3) C(24)-C(25) 1.415(4) C(25)-C(26) 1.421(3) C(27)-C(31) 1.401(4) C(27)-C(28) 1.420(4) C(28)-C(29) 1.394(4) C(29)-C(30) 1.401(4) C(30)-C(31) 1.415(4)

C(28)-Fe(2)-C(25) 167.03(12) C(28)-Fe(2)-C(26) 151.17(12) C(25)-Fe(2)-C(26) 41.47(9) C(28)-Fe(2)-C(29) 40.57(12) C(25)-Fe(2)-C(29) 127.62(11) C(26)-Fe(2)-C(29) 166.48(11) C(28)-Fe(2)-C(27) 41.23(12) C(25)-Fe(2)-C(27) 148.83(12) C(26)-Fe(2)-C(27) 116.83(11) C(29)-Fe(2)-C(27) 68.60(12) C(28)-Fe(2)-C(24) 130.00(12) C(25)-Fe(2)-C(24) 40.94(11) C(26)-Fe(2)-C(24) 68.88(11) C(29)-Fe(2)-C(24) 107.88(12) C(27)-Fe(2)-C(24) 169.75(11) C(28)-Fe(2)-C(30) 67.50(12) C(25)-Fe(2)-C(30) 106.61(12) C(26)-Fe(2)-C(30) 128.47(12) C(29)-Fe(2)-C(30) 40.14(12) C(27)-Fe(2)-C(30) 67.37(12) C(24)-Fe(2)-C(30) 116.64(12) C(28)-Fe(2)-C(31) 67.89(13) C(25)-Fe(2)-C(31) 115.68(12) C(26)-Fe(2)-C(31) 107.67(11) C(29)-Fe(2)-C(31) 67.91(12) C(27)-Fe(2)-C(31) 39.81(12) C(24)-Fe(2)-C(31) 148.98(12) C(30)-Fe(2)-C(31) 40.05(12) C(28)-Fe(2)-C(23) 111.29(12) C(25)-Fe(2)-C(23) 67.74(11) C(26)-Fe(2)-C(23) 67.41(10) C(29)-Fe(2)-C(23) 119.16(11) C(27)-Fe(2)-C(23) 132.41(11) C(24)-Fe(2)-C(23) 40.00(10) C(30)-Fe(2)-C(23) 150.67(12) C(31)-Fe(2)-C(23) 169.01(11) C(28)-Fe(2)-C(22) 119.25(11) C(25)-Fe(2)-C(22) 69.04(10) C(26)-Fe(2)-C(22) 40.38(9) C(29)-Fe(2)-C(22) 152.02(11) C(27)-Fe(2)-C(22) 109.58(11) C(24)-Fe(2)-C(22) 68.69(10) C(30)-Fe(2)-C(22) 166.97(12) C(31)-Fe(2)-C(22) 129.63(11) C(23)-Fe(2)-C(22) 40.37(9) C(19)-Fe(1)-C(16) 157.77(11) C(19)-Fe(1)-C(18) 41.40(12) C(16)-Fe(1)-C(18) 160.23(11) C(19)-Fe(1)-C(20) 41.30(11) C(16)-Fe(1)-C(20) 122.80(11) C(18)-Fe(1)-C(20) 69.18(11) C(19)-Fe(1)-C(15) 119.49(11) C(16)-Fe(1)-C(15) 41.24(10) C(18)-Fe(1)-C(15) 157.18(11) C(20)-Fe(1)-C(15) 104.40(11) C(19)-Fe(1)-C(13) 120.16(11) C(16)-Fe(1)-C(13) 68.05(10) C(18)-Fe(1)-C(13) 108.09(11) C(20)-Fe(1)-C(13) 155.12(10) C(15)-Fe(1)-C(13) 68.08(11) C(19)-Fe(1)-C(12) 157.35(10) C(16)-Fe(1)-C(12) 41.24(10) C(18)-Fe(1)-C(12) 123.09(11) C(20)-Fe(1)-C(12) 161.06(10) C(15)-Fe(1)-C(12) 69.73(10) C(13)-Fe(1)-C(12) 40.84(9) C(19)-Fe(1)-C(14) 103.74(11) C(16)-Fe(1)-C(14) 68.29(10) C(18)-Fe(1)-C(14) 122.27(11) C(20)-Fe(1)-C(14) 118.58(10) C(15)-Fe(1)-C(14) 40.18(10) C(13)-Fe(1)-C(14) 40.54(9) S31

C(12)-Fe(1)-C(14) 69.20(10) C(19)-Fe(1)-C(21) 68.60(11) C(16)-Fe(1)-C(21) 109.71(10) C(18)-Fe(1)-C(21) 67.98(11) C(20)-Fe(1)-C(21) 40.66(10) C(15)-Fe(1)-C(21) 122.15(11) C(13)-Fe(1)-C(21) 163.06(10) C(12)-Fe(1)-C(21) 126.32(10) C(14)-Fe(1)-C(21) 155.77(10) C(19)-Fe(1)-C(17) 68.55(11) C(16)-Fe(1)-C(17) 125.29(10) C(18)-Fe(1)-C(17) 40.39(10) C(20)-Fe(1)-C(17) 68.13(11) C(15)-Fe(1)-C(17) 159.17(10) C(13)-Fe(1)-C(17) 126.72(10) C(12)-Fe(1)-C(17) 110.71(10) C(14)-Fe(1)-C(17) 160.58(10) C(21)-Fe(1)-C(17) 39.79(10) C(5)-N(1)-C(1) 121.7(2) C(5)-N(1)-B(1) 109.84(19) C(1)-N(1)-B(1) 128.5(2) C(2)-C(1)-N(1) 121.8(2) C(1)-C(2)-C(3) 117.3(3) C(2)-C(3)-C(4) 121.5(3) C(5)-C(4)-C(3) 118.9(3) N(1)-C(5)-C(4) 118.7(2) N(1)-C(5)-C(6) 112.0(2) C(4)-C(5)-C(6) 129.3(2) C(11)-C(6)-C(7) 121.8(2) C(11)-C(6)-C(5) 110.0(2) C(7)-C(6)-C(5) 128.3(2) C(6)-C(7)-C(8) 120.2(2) C(9)-C(8)-C(7) 119.6(2) C(8)-C(9)-C(10) 119.5(2) C(9)-C(10)-C(11) 122.9(2) C(6)-C(11)-C(10) 116.1(2) C(6)-C(11)-B(1) 109.61(19) C(10)-C(11)-B(1) 134.2(2) C(16)-C(12)-C(13) 104.95(19) C(16)-C(12)-B(1) 129.5(2) C(13)-C(12)-B(1) 125.4(2) C(16)-C(12)-Fe(1) 67.60(12) C(13)-C(12)-Fe(1) 69.42(13) B(1)-C(12)-Fe(1) 130.99(15) C(14)-C(13)-C(12) 109.8(2) C(14)-C(13)-Fe(1) 70.18(15) C(12)-C(13)-Fe(1) 69.74(13) C(15)-C(14)-C(13) 107.7(2) C(15)-C(14)-Fe(1) 68.82(14) C(13)-C(14)-Fe(1) 69.28(14) C(14)-C(15)-C(16) 107.6(2) C(14)-C(15)-Fe(1) 71.00(15) C(16)-C(15)-Fe(1) 68.37(14) C(15)-C(16)-C(12) 109.9(2) C(15)-C(16)-Fe(1) 70.39(14) C(12)-C(16)-Fe(1) 71.16(12) C(21)-C(17)-C(18) 108.2(2) C(21)-C(17)-Fe(1) 70.10(14) C(18)-C(17)-Fe(1) 67.69(15) C(17)-C(18)-C(19) 107.9(2) C(17)-C(18)-Fe(1) 71.92(15) C(19)-C(18)-Fe(1) 68.18(15) C(20)-C(19)-C(18) 108.3(2) C(20)-C(19)-Fe(1) 70.77(15) C(18)-C(19)-Fe(1) 70.42(15) C(19)-C(20)-C(21) 107.4(2) C(19)-C(20)-Fe(1) 67.93(15) C(21)-C(20)-Fe(1) 71.47(14) C(17)-C(21)-C(20) 108.1(2) C(17)-C(21)-Fe(1) 70.11(14) C(20)-C(21)-Fe(1) 67.87(15) C(26)-C(22)-C(23) 105.1(2) S32

C(26)-C(22)-B(1) 125.9(2) C(23)-C(22)-B(1) 128.7(2) C(26)-C(22)-Fe(2) 66.56(13) C(23)-C(22)-Fe(2) 69.21(14) B(1)-C(22)-Fe(2) 133.12(16) C(24)-C(23)-C(22) 109.9(2) C(24)-C(23)-Fe(2) 68.49(14) C(22)-C(23)-Fe(2) 70.42(14) C(23)-C(24)-C(25) 107.1(2) C(23)-C(24)-Fe(2) 71.51(15) C(25)-C(24)-Fe(2) 67.57(16) C(24)-C(25)-C(26) 108.3(2) C(24)-C(25)-Fe(2) 71.48(16) C(26)-C(25)-Fe(2) 70.07(14) C(25)-C(26)-C(22) 109.6(2) C(25)-C(26)-Fe(2) 68.46(14) C(22)-C(26)-Fe(2) 73.06(14) C(31)-C(27)-C(28) 107.4(3) C(31)-C(27)-Fe(2) 71.63(18) C(28)-C(27)-Fe(2) 67.75(16) C(29)-C(28)-C(27) 108.9(3) C(29)-C(28)-Fe(2) 70.96(17) C(27)-C(28)-Fe(2) 71.02(16) C(28)-C(29)-C(30) 107.2(3) C(28)-C(29)-Fe(2) 68.47(17) C(30)-C(29)-Fe(2) 71.06(17) C(29)-C(30)-C(31) 109.0(3) C(29)-C(30)-Fe(2) 68.80(16) C(31)-C(30)-Fe(2) 70.80(17) C(27)-C(31)-C(30) 107.4(3) C(27)-C(31)-Fe(2) 68.56(17) C(30)-C(31)-Fe(2) 69.16(16) C(12)-B(1)-C(22) 112.30(19) C(12)-B(1)-N(1) 106.27(18) C(22)-B(1)-N(1) 106.83(18) C(12)-B(1)-C(11) 116.88(19) C(22)-B(1)-C(11) 114.43(19) N(1)-B(1)-C(11) 98.24(18) S33

Table S-84. Anisotropic displacement parameters (Å 2 x 10 3 ) for compound 2. The anisotropic displacement factor exponent takes the form: -2 2 [ h 2 a* 2 U 11 +... + 2 h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 Fe(2) 16(1) 18(1) 19(1) -3(1) 3(1) 0(1) Fe(1) 13(1) 19(1) 20(1) 1(1) 2(1) 1(1) N(1) 18(1) 18(1) 19(1) -1(1) 2(1) 1(1) C(1) 28(1) 26(1) 21(1) 1(1) 1(1) 2(1) C(2) 34(2) 38(2) 25(1) 4(1) -4(1) 8(1) C(3) 25(1) 57(2) 40(2) 5(2) -10(1) 11(1) C(4) 17(1) 52(2) 37(2) 4(1) 0(1) 3(1) C(5) 16(1) 23(1) 25(1) -3(1) 4(1) -1(1) C(6) 17(1) 21(1) 21(1) -2(1) 2(1) -3(1) C(7) 16(1) 32(1) 31(1) 0(1) 7(1) -4(1) C(8) 27(1) 31(1) 25(1) 3(1) 14(1) -10(1) C(9) 31(1) 25(1) 20(1) 3(1) 1(1) -4(1) C(10) 17(1) 23(1) 23(1) -1(1) 1(1) -1(1) C(11) 13(1) 14(1) 20(1) -3(1) 3(1) -2(1) C(12) 14(1) 18(1) 16(1) 0(1) -3(1) -1(1) C(13) 16(1) 23(1) 19(1) 3(1) 0(1) -1(1) C(14) 18(1) 33(1) 20(1) -1(1) 4(1) 3(1) C(15) 23(1) 23(1) 24(1) -6(1) 1(1) 2(1) C(16) 17(1) 18(1) 25(1) -1(1) 0(1) -1(1) C(17) 18(1) 30(1) 25(1) -2(1) -4(1) 4(1) C(18) 18(1) 31(1) 36(2) 4(1) -4(1) -3(1) C(19) 17(1) 42(2) 32(2) 7(1) 4(1) 0(1) C(20) 19(1) 27(1) 36(2) 2(1) 2(1) 8(1) C(21) 21(1) 25(1) 28(1) 5(1) -2(1) 3(1) C(22) 17(1) 17(1) 18(1) -2(1) 4(1) 1(1) C(23) 26(1) 20(1) 18(1) 0(1) 4(1) -1(1) C(24) 32(1) 18(1) 29(1) -1(1) 11(1) -3(1) C(25) 20(1) 22(1) 35(2) -7(1) 8(1) -3(1) C(26) 16(1) 19(1) 29(1) -3(1) 2(1) 2(1) C(27) 36(2) 27(1) 42(2) -6(1) 23(1) -4(1) S34

C(28) 24(1) 49(2) 40(2) -12(1) 10(1) 5(1) C(29) 53(2) 25(1) 45(2) -5(1) 25(2) 10(1) C(30) 45(2) 48(2) 33(2) -23(1) 16(1) -18(1) C(31) 37(2) 54(2) 25(2) 2(1) 11(1) 4(1) B(1) 12(1) 18(1) 18(1) 1(1) 0(1) -1(1) Table S8-5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for compound 2. x y z U(eq) H(1) 8218 4597 8339 30 H(2) 9573 4070 8976 40 H(3) 10745 4420 8208 50 H(4) 10560 5395 6847 43 H(7) 10092 6450 5414 31 H(8) 9448 7438 4153 33 H(9) 7973 7712 3960 30 H(10) 7133 6975 5003 25 H(13) 6363 5212 7861 24 H(14) 5853 7398 8651 28 H(15) 6620 9592 8113 28 H(16) 7605 8756 6996 24 H(17) 5797 6648 5281 29 H(18) 4796 5686 6348 35 H(19) 4333 7787 7240 36 H(20) 5050 10054 6726 33 H(21) 5960 9336 5511 30 H(23) 7848 2589 7354 26 H(24) 6672 809 6808 31 H(25) 5653 2067 5659 30 H(26) 6199 4612 5502 25 H(27) 8440 4052 4738 41 H(28) 9081 2064 5723 45 H(29) 8112-117 5505 48 S35

H(30) 6855 517 4399 49 H(31) 7055 3086 3914 45 S36

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