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

Transcription

1 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 , 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

2 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

3 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

4 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

5 Relative Reflectance Wavelength / nm Figure S7. UV-Vis reflectance spectra of compounds 1-4 solids. S5

6 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

7 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

8 ε / 10 5 cm -1 M 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 H-1 LUMO (12%), HOMO LUMO (86%) S H-1 LUMO (86%), HOMO LUMO (12%) S H-2 LUMO (97%) S H-3 LUMO (94%) S H-3 L+6 (14%), H-2 L+5 (13%), H-1 L+3 (32%), H-1 L+4 (18%) S H-3 L+5 (12%), H-2 L+6 (14%), HOMO L+3 (21%), HOMO L+4 (29%) S H-6 L+3 (25%), H-5 L+4 (20%), H-2 L+5 (14%) S H-6 L+4 (23%), H-5 L+3 (21%), H-2 L+6 (12%) S H-6 L+6 (21%), H-5 L+5 (23%), H-3 L+6 (10%), H-2 L+4 (10%) S H-6 L+5 (22%), H-5 L+6 (22%) S H-5 LUMO (99%) S H-6 LUMO (95%) S H-4 LUMO (94%) S H-7 LUMO (98%) S H-8 LUMO (97%) S H-6 L+3 (12%), H-6 L+4 (10%), H-5 L+3 (15%) S H-6 L+3 (10%), H-6 L+4 (10%), H-5 L+4 (16%) S H-6 L+6 (23%), H-5 L+5 (23%), H-2 L+4 (10%) S8

9 ε / 10 5 cm -1 M 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 H-2 LUMO (74%) S H-1 LUMO (46%) S H-3 LUMO (67%) S H-3 L+4 (25%), H-2 LUMO (15%), H-2 L+3 (28%) S H-3 LUMO (23%), H-3 L+3 (21%), H-2 L+4 (26%) S H-1 L+6 (22%), HOMO LUMO (28%) S H-1 LUMO (34%), HOMO L+6 (22%) S H-5 L+3 (31%), H-3 L+4 (21%), H-2 L+3 (13%) S H-4 L+3 (14%), H-4 L+5 (14%), H-4 L+7 (12%), H-1 L+6 (13%) S H-5 L+4 (34%), H-3 L+3 (16%), H-2 L+4 (19%) S H-4 L+6 (30%), H-4 L+7 (10%), HOMO L+6 (12%) S H-2 L+1 (96%) S H-3 L+1 (60%), HOMO L+1 (32%) S H-3 L+1 (23%), H-1 L+1 (10%), HOMO L+1 (63%) S H-3 L+1 (16%), H-1 L+1 (80%) S H-5 LUMO (45%), H-4 LUMO (52%) S H-5 LUMO (53%), H-4 LUMO (42%) S H-6 LUMO (97%) S H-5 L+3 (21%), H-5 L+4 (12%), H-3 L+4 (24%), H-2 L+3 (17%) S9

10 0.3 ε / 10 5 cm -1 M 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 H-2 L+3 (19%), H-2 L+4 (24%), H-1 L+6 (10%), HOMO L+6 (20%) S H-2 L+6 (24%), H-1 L+4 (12%), HOMO L+3 (17%), HOMO L+4 (15%) S H-3 L+3 (22%), H-3 L+4 (21%), H-1 L+5 (21%) S H-3 L+5 (25%), H-1 L+3 (19%), H-1 L+4 (12%), HOMO L+4 (10%) S HOMO LUMO (91%) S H-1 LUMO (95%) S H-2 LUMO (90%) S H-3 LUMO (90%), H-2 LUMO (10%) S H-7 L+3 (20%), H-7 L+4 (23%), H-2 L+6 (21%) S H-8 L+3 (22%), H-8 L+4 (20%), H-3 L+5 (21%) S H-7 L+6 (31%), HOMO L+6 (14%) S H-8 L+5 (30%), H-1 L+5 (15%) S H-5 LUMO (67%), H-4 LUMO (29%) S H-5 LUMO (30%), H-4 LUMO (66%) S H-6 LUMO (92%) S H-6 LUMO (93%) S H-9 LUMO (93%) λ / nm S H-8 LUMO (27%), H-7 LUMO (72%) S H-8 LUMO (68%), H-7 LUMO (25%) S H-7 L+3 (15%), H-7 L+4 (17%), H-2 L+6 (22%) S10

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

12 Figure S C{ 1 H} NMR spectrum of compound 1 in CDCl 3. S12

13 Figure S14. 1 H NMR spectrum of compound 2 in CDCl 3. Figure S B NMR spectrum of compound 2 in CDCl 3. S13

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

15 Figure S17. 1 H NMR spectrum of compound 3 in CDCl 3. Figure S B NMR spectrum of compound 3 in CDCl 3. S15

16 Figure S C{ 1 H} NMR spectrum of compound 3 in CDCl 3. S16

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

18 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

19 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) C(3)-C(4) 1.419(3) C(3)-H(3A) C(4)-C(5) 1.419(3) C(4)-H(4A) C(5)-H(5A) C(6)-C(7) 1.435(3)

20 C(6)-C(10) 1.437(3) C(7)-C(8) 1.423(3) C(7)-H(7A) C(8)-C(9) 1.416(3) C(8)-H(8A) C(9)-C(10) 1.418(3) C(9)-H(9A) C(10)-H(10A) C(11)-C(15) 1.419(4) C(11)-C(12) 1.423(4) C(11)-H(11A) C(12)-C(13) 1.401(4) C(12)-H(12A) C(13)-C(14) 1.398(4) C(13)-H(13A) C(14)-C(15) 1.419(4) C(14)-H(14A) C(15)-H(15A) C(16)-C(20) 1.399(4) C(16)-C(17) 1.423(4) C(16)-H(16A) C(17)-C(18) 1.413(4) C(17)-H(17A) C(18)-C(19) 1.406(4) C(18)-H(18A) C(19)-C(20) 1.386(4) C(19)-H(19A) C(20)-H(20A) 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) 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) C(29)-C(32) 1.493(3) C(30)-H(30A) C(30)-H(30B) C(30)-H(30C) C(31)-H(31A) C(31)-H(31B) C(31)-H(31C) C(32)-H(32A) C(32)-H(32B) C(32)-H(32C) C(33)-H(33A) C(33)-H(33B) C(33)-H(33C) 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) C(36)-C(37) 1.376(4) C(36)-H(36A) C(37)-C(38) 1.376(4) C(37)-H(37A) C(38)-C(39) 1.387(3) C(38)-H(38A) C(39)-H(39A) N(2)-B(1)-N(1) (16) N(2)-B(1)-C(6) (16) N(1)-B(1)-C(6) (16) N(2)-B(1)-C(1) (16) N(1)-B(1)-C(1) (16) S20

21 C(6)-B(1)-C(1) (17) C(4)-Fe(1)-C(5) 40.89(9) C(4)-Fe(1)-C(12) (11) C(5)-Fe(1)-C(12) (11) C(4)-Fe(1)-C(13) (11) C(5)-Fe(1)-C(13) (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) (11) C(13)-Fe(1)-C(3) (11) C(4)-Fe(1)-C(14) (11) C(5)-Fe(1)-C(14) (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) (11) C(4)-Fe(1)-C(11) (11) C(5)-Fe(1)-C(11) (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) (11) C(14)-Fe(1)-C(11) 67.98(11) C(4)-Fe(1)-C(15) (11) C(5)-Fe(1)-C(15) (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) (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) (10) C(13)-Fe(1)-C(2) (10) C(3)-Fe(1)-C(2) 40.72(9) C(14)-Fe(1)-C(2) (10) C(11)-Fe(1)-C(2) (10) C(15)-Fe(1)-C(2) (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) (10) C(13)-Fe(1)-C(1) (11) C(3)-Fe(1)-C(1) 68.60(9) C(14)-Fe(1)-C(1) (10) C(11)-Fe(1)-C(1) (9) C(15)-Fe(1)-C(1) (10) C(2)-Fe(1)-C(1) 40.16(8) C(17)-Fe(2)-C(9) (11) C(17)-Fe(2)-C(18) 40.72(11) C(9)-Fe(2)-C(18) (11) C(17)-Fe(2)-C(10) (10) C(9)-Fe(2)-C(10) 40.86(9) C(18)-Fe(2)-C(10) (10) C(17)-Fe(2)-C(19) 67.92(12) C(9)-Fe(2)-C(19) (12) C(18)-Fe(2)-C(19) 40.39(11) C(10)-Fe(2)-C(19) (11) C(17)-Fe(2)-C(8) (12) C(9)-Fe(2)-C(8) 40.67(9) C(18)-Fe(2)-C(8) (11) C(10)-Fe(2)-C(8) 68.17(9) C(19)-Fe(2)-C(8) (11) C(17)-Fe(2)-C(16) 40.85(12) C(9)-Fe(2)-C(16) (12) C(18)-Fe(2)-C(16) 68.18(11) C(10)-Fe(2)-C(16) (11) C(19)-Fe(2)-C(16) 67.23(12) C(8)-Fe(2)-C(16) (12) C(17)-Fe(2)-C(20) 67.72(12) C(9)-Fe(2)-C(20) (12) C(18)-Fe(2)-C(20) 67.40(11) C(10)-Fe(2)-C(20) (11) C(19)-Fe(2)-C(20) 39.51(12) S21

22 C(8)-Fe(2)-C(20) (12) C(16)-Fe(2)-C(20) 39.87(12) C(17)-Fe(2)-C(7) (11) C(9)-Fe(2)-C(7) 68.06(9) C(18)-Fe(2)-C(7) (11) C(10)-Fe(2)-C(7) 67.42(9) C(19)-Fe(2)-C(7) (11) C(8)-Fe(2)-C(7) 40.49(9) C(16)-Fe(2)-C(7) (10) C(20)-Fe(2)-C(7) (10) C(17)-Fe(2)-C(6) (10) C(9)-Fe(2)-C(6) 68.95(9) C(18)-Fe(2)-C(6) (10) C(10)-Fe(2)-C(6) 40.61(8) C(19)-Fe(2)-C(6) (10) C(8)-Fe(2)-C(6) 68.59(9) C(16)-Fe(2)-C(6) (9) C(20)-Fe(2)-C(6) (10) C(7)-Fe(2)-C(6) 40.23(8) C(21)-N(1)-C(24) (16) C(21)-N(1)-B(1) (17) C(24)-N(1)-B(1) (16) C(29)-N(2)-C(26) (17) C(29)-N(2)-B(1) (17) C(26)-N(2)-B(1) (16) C(2)-C(1)-C(5) (18) C(2)-C(1)-B(1) (18) C(5)-C(1)-B(1) (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) (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) C(1)-C(2)-H(2A) Fe(1)-C(2)-H(2A) 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) C(2)-C(3)-H(3A) Fe(1)-C(3)-H(3A) 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) C(3)-C(4)-H(4A) Fe(1)-C(4)-H(4A) 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) C(1)-C(5)-H(5A) Fe(1)-C(5)-H(5A) C(7)-C(6)-C(10) (18) C(7)-C(6)-B(1) (18) C(10)-C(6)-B(1) (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) (14) C(8)-C(7)-C(6) (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) C(6)-C(7)-H(7A) Fe(2)-C(7)-H(7A) 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) C(7)-C(8)-H(8A) S22

23 Fe(2)-C(8)-H(8A) 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) C(10)-C(9)-H(9A) Fe(2)-C(9)-H(9A) 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) C(6)-C(10)-H(10A) Fe(2)-C(10)-H(10A) 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) C(12)-C(11)-H(11A) Fe(1)-C(11)-H(11A) 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) C(11)-C(12)-H(12A) Fe(1)-C(12)-H(12A) 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) C(12)-C(13)-H(13A) Fe(1)-C(13)-H(13A) 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) C(15)-C(14)-H(14A) Fe(1)-C(14)-H(14A) 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) C(11)-C(15)-H(15A) Fe(1)-C(15)-H(15A) 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) C(17)-C(16)-H(16A) Fe(2)-C(16)-H(16A) 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) C(16)-C(17)-H(17A) Fe(2)-C(17)-H(17A) 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) C(17)-C(18)-H(18A) Fe(2)-C(18)-H(18A) 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) C(18)-C(19)-H(19A) Fe(2)-C(19)-H(19A) 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) C(16)-C(20)-H(20A) S23

24 Fe(2)-C(20)-H(20A) N(1)-C(21)-C(22) (19) N(1)-C(21)-C(33) (19) C(22)-C(21)-C(33) (19) C(23)-C(22)-C(21) (18) C(23)-C(22)-H(22A) C(21)-C(22)-H(22A) C(22)-C(23)-C(24) (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) (17) C(25)-C(24)-C(23) 131.1(2) N(1)-C(24)-C(23) (18) C(24)-C(25)-C(26) (19) C(24)-C(25)-C(34) (18) C(26)-C(25)-C(34) (18) C(25)-C(26)-N(2) (18) C(25)-C(26)-C(27) 131.2(2) N(2)-C(26)-C(27) (18) C(28)-C(27)-C(26) (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) (19) C(27)-C(28)-H(28A) C(29)-C(28)-H(28A) N(2)-C(29)-C(28) (19) N(2)-C(29)-C(32) (19) C(28)-C(29)-C(32) (19) C(23)-C(30)-H(30A) C(23)-C(30)-H(30B) H(30A)-C(30)-H(30B) C(23)-C(30)-H(30C) H(30A)-C(30)-H(30C) H(30B)-C(30)-H(30C) C(27)-C(31)-H(31A) C(27)-C(31)-H(31B) H(31A)-C(31)-H(31B) C(27)-C(31)-H(31C) H(31A)-C(31)-H(31C) H(31B)-C(31)-H(31C) C(29)-C(32)-H(32A) C(29)-C(32)-H(32B) H(32A)-C(32)-H(32B) C(29)-C(32)-H(32C) H(32A)-C(32)-H(32C) H(32B)-C(32)-H(32C) C(21)-C(33)-H(33A) C(21)-C(33)-H(33B) H(33A)-C(33)-H(33B) C(21)-C(33)-H(33C) H(33A)-C(33)-H(33C) H(33B)-C(33)-H(33C) 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) C(36)-C(35)-H(35A) C(37)-C(36)-C(35) 119.7(2) C(37)-C(36)-H(36A) C(35)-C(36)-H(36A) C(36)-C(37)-C(38) 120.1(2) C(36)-C(37)-H(37A) C(38)-C(37)-H(37A) C(37)-C(38)-C(39) 120.3(3) C(37)-C(38)-H(38A) C(39)-C(38)-H(38A) C(34)-C(39)-C(38) 120.2(2) C(34)-C(39)-H(39A) C(38)-C(39)-H(39A) S24

25 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 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

26 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) H(3A) H(4A) H(5A) H(7A) H(8A) H(9A) H(10A) H(11A) H(12A) H(13A) H(14A) H(15A) H(16A) H(17A) S26

27 H(18A) H(19A) H(20A) H(22A) H(28A) H(30A) H(30B) H(30C) H(31A) H(31B) H(31C) H(32A) H(32B) H(32C) H(33A) H(33B) H(33C) H(35A) H(36A) H(37A) H(38A) H(39A) S27

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

29 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

30 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)

31 C(28)-Fe(2)-C(25) (12) C(28)-Fe(2)-C(26) (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) (11) C(26)-Fe(2)-C(29) (11) C(28)-Fe(2)-C(27) 41.23(12) C(25)-Fe(2)-C(27) (12) C(26)-Fe(2)-C(27) (11) C(29)-Fe(2)-C(27) 68.60(12) C(28)-Fe(2)-C(24) (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) (12) C(27)-Fe(2)-C(24) (11) C(28)-Fe(2)-C(30) 67.50(12) C(25)-Fe(2)-C(30) (12) C(26)-Fe(2)-C(30) (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) (12) C(28)-Fe(2)-C(31) 67.89(13) C(25)-Fe(2)-C(31) (12) C(26)-Fe(2)-C(31) (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) (12) C(30)-Fe(2)-C(31) 40.05(12) C(28)-Fe(2)-C(23) (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) (11) C(27)-Fe(2)-C(23) (11) C(24)-Fe(2)-C(23) 40.00(10) C(30)-Fe(2)-C(23) (12) C(31)-Fe(2)-C(23) (11) C(28)-Fe(2)-C(22) (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) (11) C(27)-Fe(2)-C(22) (11) C(24)-Fe(2)-C(22) 68.69(10) C(30)-Fe(2)-C(22) (12) C(31)-Fe(2)-C(22) (11) C(23)-Fe(2)-C(22) 40.37(9) C(19)-Fe(1)-C(16) (11) C(19)-Fe(1)-C(18) 41.40(12) C(16)-Fe(1)-C(18) (11) C(19)-Fe(1)-C(20) 41.30(11) C(16)-Fe(1)-C(20) (11) C(18)-Fe(1)-C(20) 69.18(11) C(19)-Fe(1)-C(15) (11) C(16)-Fe(1)-C(15) 41.24(10) C(18)-Fe(1)-C(15) (11) C(20)-Fe(1)-C(15) (11) C(19)-Fe(1)-C(13) (11) C(16)-Fe(1)-C(13) 68.05(10) C(18)-Fe(1)-C(13) (11) C(20)-Fe(1)-C(13) (10) C(15)-Fe(1)-C(13) 68.08(11) C(19)-Fe(1)-C(12) (10) C(16)-Fe(1)-C(12) 41.24(10) C(18)-Fe(1)-C(12) (11) C(20)-Fe(1)-C(12) (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) (11) C(16)-Fe(1)-C(14) 68.29(10) C(18)-Fe(1)-C(14) (11) C(20)-Fe(1)-C(14) (10) C(15)-Fe(1)-C(14) 40.18(10) C(13)-Fe(1)-C(14) 40.54(9) S31

32 C(12)-Fe(1)-C(14) 69.20(10) C(19)-Fe(1)-C(21) 68.60(11) C(16)-Fe(1)-C(21) (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) (11) C(13)-Fe(1)-C(21) (10) C(12)-Fe(1)-C(21) (10) C(14)-Fe(1)-C(21) (10) C(19)-Fe(1)-C(17) 68.55(11) C(16)-Fe(1)-C(17) (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) (10) C(13)-Fe(1)-C(17) (10) C(12)-Fe(1)-C(17) (10) C(14)-Fe(1)-C(17) (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) (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) (19) C(10)-C(11)-B(1) 134.2(2) C(16)-C(12)-C(13) (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) (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

33 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) (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) (19) C(12)-B(1)-N(1) (18) C(22)-B(1)-N(1) (18) C(12)-B(1)-C(11) (19) C(22)-B(1)-C(11) (19) N(1)-B(1)-C(11) 98.24(18) S33

34 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 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

35 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) H(2) H(3) H(4) H(7) H(8) H(9) H(10) H(13) H(14) H(15) H(16) H(17) H(18) H(19) H(20) H(21) H(23) H(24) H(25) H(26) H(27) H(28) H(29) S35

36 H(30) H(31) S36