Correlating Electronic and Catalytic Properties of Frustrated

Lewis Pairs for Imine Hydrogenation

Éva Dorkó, Bianka Kótai, Tamás Földes, Ádám Gyömöre, Imre Pápai and Tibor Soós,

Hungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, Magyar

tudósok körútja 2A., H-1117, Budapest, Hungary

*Corresponding author: soos.tibor@ttk.mta.hu, papai.imre@ttk.mta.hu

Supporting Information

Table of Contents

1. General Methods. ................................................................................................................... 2 2. Experimental procedures ........................................................................................................ 3 

2.1 Synthesis of reagents ........................................................................................................ 3 2.2 Synthesis of triaryl-boranes ............................................................................................ 13 

2.2.1 Preparation of Grignard reagents: ........................................................................... 13 2.2.2 General method for the synthesis of boranes .......................................................... 13 

3. Determination of Lewis-acidity ........................................................................................... 36 3.1 Gutmann-Beckett method. ............................................................................................. 36 3.1.1. Et3P=O ........................................................................................................................ 36 3.1.2. Ph3P=O ....................................................................................................................... 37 

4. Reactivity ............................................................................................................................. 37 5. Theoretical Studies ............................................................................................................... 39 

5.1 Computational details ..................................................................................................... 39 5.2 Complete reference of Gaussian 09 ............................................................................... 40 5.3 Total energy data of the calculated structures ................................................................ 40 5.4 Cartesian coordinates of the reported structures ............................................................ 43 

- S2 -

1. General Methods. All air- and moisture-sensitive compounds were manipulated using standard Schlenk tech-

niques under an atmosphere of nitrogen or in nitrogen filled glovebox. All glass wares were

heated to 120oC overnight and either attached to the vacuum line or placed into the glovebox

while hot. All solvents were dried over the appropriate drying agents (CaH2,

Na/benzophenone) and freshly distilled prior to use. NMR solvents, BuLi, B(OMe)3, Mg turn-

ings, 2-chloropropane, N-clorosuccinimide, TCCA (trichloroisocyanuric acid), iPrMgCl*LiCl

complex and 1-bromo-2,6-difluorobenzene were purchased from Sigma-Aldrich Chemical

Company, pentafluorobromobenzene and 1-bromo-2,3,6-trifluorobenzene was purchased

from Fluorochem Ltd., 1-bromo-2,3,5,6-tetrafluorobenzene from Apollo Scientific Ltd.

Mesitylbromide, trimesitylphosphine and triethylphosphinoxide were purchased from Abcr

Chemical Gmbh and Co. Tris(pentafluorophenyl)borane was purchased from TCI Chemicals.

Trimethylborate was freshly distilled from sodium before use; other materials were used as

received.

1H, 19F, 11B, and 13C NMR spectra were recorded on a Varian Unity Inova 500 MHz or

Brucker Avance 400 MHz, or 250 MHz spectrometers at 303 K, unless indicated otherwise.

Chemical shifts referenced internally to residual solvent resonances (C6D6: 1H δ 7.15, 13C δ

128.62, CD2Cl2: 1H δ 5.32, 13C δ 53.84, C7D8:

1H δ 7.10, 13C δ 20.38, CDCl3: 1H δ 7.26, 13C δ

77.00, d8-THF: 1H δ 1.85, 3.76, 13C δ 25.62, 67.97, d6-DMSO: 1H δ 2.5, 13C δ 39.52). Other

nuclei were referenced to an external standard BF3*Et2O (11B), CFCl3 (19F), all at 0 ppm.

Chemical shifts are reported in ppm, and coupling constants are reported in Hz.

High resolution mass spectra were obtained on a Q-TOF Premier mass spectrometer (Waters

Corporation) in positive electrospray mode, or on a Waters GCT Premier mass spectrometer

in positive electron ionization (EI+) mode. Melting points were measured using an OptiMelt

MPA100 melting point apparatus and were uncorrected. Gas chromatography analyses were

performed on an Agilent HP-5 chromatograph (Series 6850, column: 30 m x 0.25 mm x 0.25

m, FID, Program: 80°C, 15°C min-1, 250°C, 5 min, Inj.: 250°C, Det.: 280°C). GC-MS

measurements were performed on a Shimadzu GC-MS-QP210ULTRA apparatus (column:

ZB-5MSi, 30 m x 0.25 mm x 0.25 m, EI+, Program: 80°C, 3 min, 15°C min-1, 250°C, 2 min,

Inj.: 250°C, Det.: 280°C). FT-IR spectra were recorded on a Varian 2000 (Scimitar Series)

FT-IR spectrophotometer in ATR mode and are reported in wavenumbers (cm-1).

- S3 -

2. Experimental procedures

2.1 Synthesis of reagents 2-bromo-4-chloro-1,3,5-trimethylbenzene1 (6b) was synthesized according to

published procedures.

2-bromo-4,6-dichloro-1,3,5-trimethylbenzene (6c). Trichloroisocyanuric acid (3.30 g, 10.0

mmol) was added in small portions to the mixture of 2-bromo-4-

chloromesitylene (1.20 g, 5.0 mmol), chloroform (10 ml) and perchloric acid

(70%, 0.40 ml) at room temperature, and stirred for 24 hours. The reaction was

followed by GC-FID. (In case off insufficient conversion, few more drops of perchloric acid

and calculated amount of trichloroisocyanuric acid was added.) The reaction mixture was hy-

drolyzed by pouring into ice/water, and was treated with 10% NaHCO3 solution until pH 7.

The solution was extracted with dichloromethane (3*10 ml). The combined organic layers

were dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was washed

with hexane to give the product as white crystals. Yield: 1.10 g (82%). M.p. 214-216°C. 1H

NMR (500 MHz, CDCl3) δ 2.47 (s, 3H), 2.56 (s, 6H). 13C NMR (126 MHz, CDCl3) δ 134.6,

133.5, 132.9, 125.6, 22.5, 19.2. IR (ATR): ν= 673, 711, 958, 1361, 1550 cm-1. HRMS (EI+)

m/z: [M+] calculated 265.9265, found: 265.9264.

1 Dorkó, É.; Varga, E.; Gáti, T.; Holczbauer, T.; Pápai, I.; Mehdi, H.; Soós, T.; Synlett, 2014, 25, 1525-1528.

Cl

Br

Cl

Br

Cl

- S4 -

General procedure of boronic acid synthesis

A solution of 1 equiv. (10 mmol) mesitylbromide and 5 ml THF was added

dropwise to 1.2 equiv. (12 mmol, 0.30g) activated Mg turnings in 10 ml THF.

After the reaction started, the mixture was refluxed for 3 hours. Then the reac-

tion mixture was cooled to -78°C, and treated with 2 equiv. (20 mmol, 2.0g) of

freshly distilled trimethylborate, and then the reaction mixture was allowed to warm up to

room temperature, and stirred overnight (12 hours). The reaction was quenched with 2 equiv.

(20 mmol, 20 ml) 1M HCl-solution at 0 °C, then the mixture was stirred at rt. for two hours.

The phases were separated and the aqueous phase was washed with 3x10 ml diethyl ether.

The combined organic layer was washed with brine three times, dried over anhydrous

Na2SO4, filtered off and evaporated to dryness. The resulted solid/oil was suspended in hex-

ane, filtered off, washed with hexane 3 times and dried.

(2,4,6-trimethylphenyl)boronic acid.2

White solid, yield: 85%, mp.: 201-202°C, 1H NMR (500 MHz, d6-DMSO) δ 8.00

(s, 2H), 6.74 (s, 2H), 2.24 (s, 6H), 2.21 (s, 3H). 13C NMR (126 MHz, d6-DMSO) δ

138.5, 136.1, 126.4, 21.8, 20.7. 11B NMR (160 MHz, d6-DMSO) δ 27.9 ppm. IR: νmax= 646,

828, 1016, 1094, 1335, 1602, 3279 cm-1.

2 Leermann, T., Leroux, F. R., Colobert, F., Org. Lett., 2011, 13, 4479–4481.

BHO OH

H/ClCl/H

BHO OH

- S5 -

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0ppm

3.19

6.81

2.00

1.79

2.21

2.24

2.50

6.74

8.00

BOH OH

proton, d6-DMSO

20.7

721

.87

39.3

539

.52

39.6

9

126.

36

136.

1013

8.46

(3-chloro-2,4,6-trimethylphenyl)boronic acid.3 White solid, yield: 91%. M.p.: 155-156 °C, 1H NMR (500 MHz, d6-DMSO) δ 8.19 (s, 2H), 6.94 (s, 2H), 2.30 (s, 3H), 2.28 (s,

3H), 2.22 (s, 3H). 13C NMR (126 MHz, d6-DMSO) δ 136.6, 135.7, 134.1, 130.6,

129.1, 21.3, 20.6, 20.20. 11B NMR (160 MHz, d6-DMSO) δ 32.8. IR (ATR): ν=

3 Similar compound: Furukawa, T. , Tobisu, M., Chatani, N., J. Am. Chem. Soc., 2015, 137, 12211–12214.

BHO OH

Cl

- S6 -

607, 815, 967, 1042, 1133, 1322, 1602, 3265 cm-1. HRMS (ESI-) m/z: [M-H]- calculated

197.0542, found: 197.0558.

(3,5-dichloro-2,4,6-trimethylphenyl)boronic acid. In this case, 1.2 equiv. (12 mmol, 5 ml,

2.54M) n-BuLi in hexanes was used at -78°C (4 hours) to activate the

bromobenzene, instead of Mg. Light yellow solid, yield: 72%. M.p.: 187-192°C. 1H NMR (500 MHz, d6-DMSO) δ 8.38 (s, 2H), 2.45 (s, 3H), 2.30 (s, 6H). 13C

NMR (126 MHz, d6-DMSO) δ 134.4, 132.1, 131.8, 20.7, 18.4. 11B NMR (160

BHO OH

ClCl

- S7 -

MHz, d6-DMSO) δ 25.5 ppm. IR (ATR): ν= 666, 802, 965, 1140, 1309, 3241 cm-1. HRMS

(ESI-) m/z: [M-H]- calculated 231.0153, found: 231.0163.

102030405060708090100110120130140150ppm

18.3

620

.72

39.3

539

.52

39.6

9

131.

8113

2.12

134.

42

BOH OH

ClCl

13C, d6-DMSO

General procedure of potassium aryltrifluoroborate salts synthesis

1 equiv. boronic acid (10 mmol) was dissolved in 15 ml methanol in a PE-

flask. The solution was treated with 4 equiv. (40 mmol, 3.12g) KHF2 in 10 ml

distilled water. The resulting suspension was stirred overnight. Next day, 200

ml acetone was added to the suspension, decanted from the solid residue and evaporated to

dryness. The gained white solid was dissolved in 200 ml acetone, and evaporated to dryness 3

BF3K

Cl/HH/Cl

- S8 -

times. The remaining dry solid was suspended in 20 ml hexane, filtered off, washed with hex-

ane 3*10 ml, and dried in vacuum exicator over phosphorus(V)-oxide overnight.

Potassium (2,4,6-trimethylphenyl)trifluoroborate (7a).4 White solid, yield: 89%, mp.:

above 300°C. 1H NMR (250 MHz, d6-DMSO) δ 6.50 (s, 2H), 2.26 (s, 6H), 2.10 (s,

3H). 13C NMR (126 MHz, d6-DMSO) δ 140.9, 132.5, 127.3, 23.2, 20.6. 19F NMR

(235 MHz, d6-DMSO) δ -129.3 (m, 3F). 11B NMR (160 MHz, d6-DMSO) δ 2.0 ppm.

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5ppm

3.05

6.05

2.00

2.11

2.26

2.27

2.50

2.51

2.51

3.39

6.50

B-

F FF

K+

proton, d6-DMSO

4 Darses, S.; Michaud, G.; Genet, J-P., Eur. J. Org. Chem., 1999, 1875 - 1883.

BF3K

- S9 -

-129

.26

Potassium (3-chloro-2,4,6-trimethylphenyl)trifluoroborate (7b). White solid, yield: 92%,

mp.: 295-296°C. 1H NMR (500 MHz, d6-DMSO) δ 6.68 (s, 1H), 2.38 (s, 3H), 2.27

(s, 3H), 2.20 (s, 3H). 13C NMR (126 MHz, d6-DMSO) δ 139.0, 138.4, 130.8,

129.6, 22.9, 20.4, 19.5. 19F NMR (235 MHz, d6-DMSO) δ -129.2 (m, 3F). 11B

NMR (160 MHz, d6-DMSO) δ 1.51 ppm. IR (ATR): ν= 633, 764, 854, 945, 1159, 1446, 1595

cm-1. HRMS (ESI-) m/z: [M-H]- calculated 231.0153, found: 231.0163. HRMS (ESI) m/z:

[M]- calculated 220.0440, found: 220.0432.

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5ppm

3.31

3.32

3.27

1.00

2.20

2.27

2.27

2.38

2.50

3.31

6.68

proton, d6-DMSO

B-

F FF

Cl

K+

BF3K

Cl

- S10 -

0102030405060708090100110120130140150ppm

19.5

420

.35

22.8

922

.91

39.3

539

.52

129.

6213

0.83

138.

4213

9.06

13C, d6-DMSO

B-

F FF

Cl

K+

Potassium (3,5-dichloro-2,4,6-trimethylphenyl)trifluoroborate (7c). White solid, yield:

91%. M.p.: above 300°C, 1H NMR (500 MHz, d6-DMSO) δ 2.40-2.41 (m, 9H), 13C NMR (126 MHz, d6-DMSO) δ 137.2, 129.1, 19.90, 18.8. 19F NMR (235

MHz, d6-DMSO) δ -128.4--128.7 (m, 3F). 11B NMR (160 MHz, d6-DMSO) δ

1.51. IR: νmax= 601, 704, 906, 1159, 1361, 1446 cm-1. HRMS (ESI) m/z: [M]- calculated

254.0050, found: 254.0046.

BF3K

ClCl

- S11 -

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0ppm

9.00

2.40

2.41

2.50

3.31

B-

F FF

ClCl

K+

proton, d6-DMSO

- S12 -

- S13 -

2.2 Synthesis of triaryl­boranes 

2.2.1 Preparation of Grignard reagents: (Perfluorophenyl)magnesium bromide (9d). 2.5 equiv. (25 mmol, 6.1g)

perfluorobromobenzene (8d) in 1m ml diethyl ether was added dropwise to 3

equiv. (30 mmol, 730 mg) activated magnesium turnings in 15 ml diethyl ether.

After the Grignard-reaction was started, the mixture was refluxed for 2 hours.

(2,3,5,6-tetrafluorophenyl)magnesium bromide (9c) was prepared from slow addition of

iPrMgCl (prepared from 2.25 equiv. (22.5 mmol, 550 mg) activated magnesium

turnings, 2.5 equiv. (25 mmol, 1.9g) 2-chloropropane in 15 ml Et2O), to a solution

of 2.25 equiv. (22.5 mmol, 5.1g) (2,3,5,6-tetrafluorophenyl)bromobenzene (8c) in

50 ml Et2O at 0°C. The solution was stirred for 2 hours at ambient temperature.

(2,3,6-trifluorophenyl)magnesium bromide (9b) was prepared from slow addition of

iPrMgCl (prepared from 2.25 equiv. (22.5 mmol, 550 mg) activated magnesium

turnings, 2.5 equiv. (25 mmol, 1.9g) 2-chloropropane in 15 ml THF), to a solution

of 2.25 equiv. (22.5 mmol, 4.7g) (2,3,6-trifluorophenyl)bromobenzene (8b) in 50

ml THF at 0°C. The solution was stirred for 2 hours at ambient temperature.

(2,6-difluorophenyl)magnesium bromide (9a). 2.25 equiv. (22.5 mmol, 4.4g) (2,6-difluoro-

phenyl)bromobenzene (8a) was dissolved in abs. THF, cooled down to -78°C and

2.4 equiv. turbo Grignard (iPrMgCl*LiCl complex) solution was added dropwise

to the mixture, and the mixture was stirred for 5 hours at ambient temperature.

2.2.2 General method for the synthesis of boranes 2.25 equiv. Grignard reagent was cooled to 0°C and added dropwise to a suspension of 1

equiv. appropriate aryl-BF3K salt in 25 ml Et2O or THF at 0°C. The resulted mixture was al-

lowed to warm rt. and stirred overnight. Next day the solvent was evaporated and the solid

residue was dried in vacuo at 80°C for an hour. Then the residue was extracted with 50 ml

toluene and filtered off. The solid was washed 3*20 ml toluene and the mother liquor evapo-

rated to dryness. The residue was washed with 3*10 ml hexane at rt. and then dried in vacuo.

FF

F

MgBr

FF

FF

MgBr

FF

FF

MgBr

F

FF

MgBr

- S14 -

(2,4,6-trimethylphenyl)bis(pentafluorophenyl)borane (1d) and

(2,4,6-trimethylphenyl)bis(2,3,5,6-tetrafluorophenyl)borane

(1c) were synthesized according to published procedures. 5

(2,4,6-trimethylphenyl)bis(2,5,6-trifluorophenyl)borane (1b). White solid. Yield: 31%. 1H

NMR (400 MHz, C6D6) δ 6.68 (s, 2H), 6.48 (qd, J= 9.2, 5.2 Hz,

2H), 6.15 (dd, J= 2.8, 1.7 Hz, 2H), 2.14 (s, 6H), 2.11 (s, 3H). 13C

NMR (101 MHz, C6D6) δ 160.4 (ddd, J= 246, 8.9, 2.3 Hz),

152.6 (dt J= 252, 12 Hz), 147.8 (dd, J= 246, 14.9, 3.6 Hz),

141.4, 140.1, 138.6, 129.0, 122.1 (ddd, J= 19.6, 11.0, 2.0 Hz),

121.7, 112.0 (ddd, J= 27.5, 5.6, 4.1 Hz) 22.9, 21.8. 19F NMR

(377 MHz, C6D6) δ -104.46 – -105.28 (m, 2F), -124.34 (dd, J= 22.1, 8.9 Hz, 2F), -142.14 – -

143.21 (m, 2F). 11B NMR (128 MHz, C6D6) δ 70.3 ppm. IR: νmax= 821, 984, 1221, 1459,

1634 cm-1. HRMS (ESI-) m/z: [M+Br]- calculated 471.0354, found: 471.0364.

5 a) G. Erős, H. Mehdi, I. Pápai, T. A. Rokob, P. Király, G. Tárkányi, T. Soós, Angew. Chem. Int. Ed. 2010, 49, 6556-6563.; b) Erős, G.; Nagy, K.; Mehdi, H.; Pápai, I.; Nagy, P.; Király, P.; Tárkányi, G.; Soós, T.; Chem. Eur. J., 2012, 18, 574-585.

BF

F F

F

F F

B

F

FF F

F F

F

F

X

X

X=H, F

- S15 -

0102030405060708090100110120130140150160170ppm

21.8

422

.91

111.

8411

1.85

112.

1111

2.13

122.

0912

2.18

122.

2812

8.38

128.

6212

8.96

138.

5914

0.14

146.

6014

6.71

149.

0114

9.04

149.

1915

1.41

153.

9216

1.55

161.

5716

1.64

161.

66

apt, C6D6

140144148152156160

138.

5914

0.14

141.

42

146.

5614

6.60

146.

7114

6.75

149.

0114

9.04

151.

2815

1.41

153.

7915

3.92

154.

04

159.

1115

9.20

161.

5716

1.64

161.

66

B

F

F

F

F

F

F

(2,4,6-trimethylphenyl)bis(2,6-difluorophenyl)borane (1a). White solid. Yield: 46%. 1H

NMR (400 MHz, C6D6) δ 6.77 – 6.63 (m, 4H), 6.49 – 6.37 (m, 4H),

2.25 (s, 6H), 2.13 (s, 3H). 13C NMR (101 MHz, C6D6) δ 165.9 (dd,

J= 250, 12 Hz), 139.3, 138.4, 135.3 (t, J= 11 Hz), 135.0, 128.8,

112.1 (d, J= 26 Hz), 120.9, 22.9, 21.9. 19F NMR (377 MHz, C6D6) δ

-99.0 (t, J= 6.8 Hz).11B NMR (128 MHz, C6D6) δ 70.6 ppm. IR

BF

F F

F

- S16 -

(ATR): ν= 789, 984, 1218, 1439, 1614 cm-1. HRMS (ESI-) m/z: [M+Na]+ calculated

379.1257, found: 379.1260.

- S17 -

(3-chloro-2,4,6-trimethylphenyl)bis(perfluorophenyl)borane (2d). White solid. Yield:

86%. 1H NMR (400 MHz, C6D6) δ 6.63 (s, 2H), 2.23 (s, 3H),

2.20 (s, 3H), 1.88 (s, 3H). 13C NMR (101 MHz, C6D6) δ 149.0

(d, J= 247.0 Hz), 145.4 (d, J= 267.3 Hz), 142.2, 138.2 (d, J=

256.5 Hz), 138.6, 136.5, 135.5, 135.2, 133.6, 131.4, 114.9, 22.1,

22.0, 21.4. 19F NMR (377 MHz, C6D6) δ -129.0 (dt, J= 13.1, 6.3

Hz, 4F), -143.9 – -144.5 (m, 2F), -160.8 (dd, J= 21.1, 13.8 Hz,

4F). 11B NMR (128 MHz, C6D6) δ 68.6 ppm. IR (ATR): ν= 685,

809, 987, 1147, 1303, 1465, 1641 cm-1. HRMS (ESI-) m/z: [M+Br]- calculated 576.9588,

found: 576.9588.

B

F

FF F

F F

F

F

F

F

Cl

- S18 -

0102030405060708090100110120130140150ppm

apt, C6D6

134136138140142144146148150

B

F

F

F

F

F

FF

F

F

F

Cl

- S19 -

(3-chloro-2,4,6-trimethylphenyl)bis(2,3,5,6-tetrafluorophenyl)borane (2c). White solid.

Yield: 68%. 1H NMR (400 MHz, C6D6) δ 6.60 (s, 1H), 6.29 –

6.18 (m, 2H), 2.24 (s, 3H), 2.20 (s, 3H), 1.93 (s, 3H). 13C NMR

(101 MHz, C6D6) δ 148.2 (d, J= 246.5 Hz), 146.6 (d, J= 250.6

Hz), 142.5, 138.5, 135.7, 135.4, 133.5, 131.3, 121.3, 111.6 (t,

J= 22.7 Hz)., 22.0, 21.9, 21.4. 19F NMR (377 MHz, C6D6) δ -

129.4 – -130.3 (m, 4F), -137.4 – -138.2 (m, 4F). 11B NMR (128

MHz, C6D6) δ 69.1 ppm. IR (ATR): ν= 685, 912, 1179, 1257, 1361, 1465 cm-1. HRMS (ESI-)

m/z: [M+Br]- calculated 539.9813, found: 539.9825.

B

F

FF F

F F

F

F

Cl

- S20 -

- S21 -

-149-147-145-143-141-139-137-135-133-131-129-127-125-123-121ppm

4.06

4.00

-137

.91

-137

.90

-137

.88

-137

.88

-137

.87

-137

.84

-137

.82

-137

.81

-137

.80

-137

.78

-137

.78

-129

.94

-129

.92

-129

.90

-129

.88

-129

.86

-129

.84

-129

.82

B

F

F

F

F

F

FF

F

Cl

19F, C6D6

(3-chloro-2,4,6-trimethylphenyl)bis(2,5,6-trifluorophenyl)borane (2b). White solid. Yield:

40%. 1H NMR (400 MHz, C6D6) δ 6.63 (s, 1H), 6.46 (qd, J=

9.2, 5.2 Hz, 2H), 6.16 – 6.08 (m, 2H), 2.33 (s, 3H), 2.21 (s, 3H),

2.02 (s, 3H). 13C NMR (101 MHz, C6D6) δ 160.6 (dd, J=

249.8, 7.5 Hz), 157.9 (dt, J= 253.5, 11.9 Hz), 147.8 (ddd, J=

246.4, 14.9, 3.7 Hz), 143.2, 137.7, 135.7, 135.4, 133.4, 131.2,

122.7 (ddd, J= 19.5, 11.1, 2.2 Hz), 121.0, 112.1 (dt, J= 27.5,

5.6 Hz), 22.0, 21.9, 21.39. 19F NMR (377 MHz, C6D6) δ -103.7 – -104.5 (m, 2F), -123.7 (dd,

J= 22.0, 8.7 Hz, 2F), -142.32 (dddd, J= 22.1, 15.8, 9.4, 3.1 Hz, 2F). 11B NMR (128 MHz,

C6D6) δ 68.8 ppm. IR (ATR): ν= 607, 821, 1257, 1465, 1628 cm-1. HRMS (ESI-) m/z:

[M+Br]- calculated 504.9965, found: 504.9977.

B

F

FF F

F

FCl

- S22 -

2.73

2.98

2.75

1.91

1.96

1.00

2.02

2.21

2.22

2.33

6.11

6.12

6.12

6.12

6.13

6.14

6.14

6.45

6.46

6.47

6.48

6.63

6.63

7.15

- S23 -

-145-140-135-130-125-120-115-110-105ppm

0.98

1.04

1.00

-142

.38

-142

.36

-142

.35

-142

.34

-142

.33

-142

.33

-142

.32

-142

.31

-142

.30

-142

.29

-142

.28

-142

.28

-142

.26

-123

.74

-123

.72

-123

.69

-123

.66

-104

.18

-104

.16

-104

.14

-104

.12

-104

.10

B

F

F

F

F

FF

Cl

19F, C6D6

(3-chloro-2,4,6-trimethylphenyl)bis(2,6-difluorophenyl)borane (2a). White solid. Yield:

84%. 1H NMR (400 MHz, C6D6) δ 6.76 – 6.65 (m, 3H), 6.41 (t,

J= 7.9 Hz, 4H), 2.43 (s, 3H), 2.23 (s, 3H), 2.13 (s, 3H). 13C NMR

(101 MHz, C6D6) δ 166.2 (dd, J= 252.0, 11.1 Hz), 145.0, 137.0,

135.9 (t, J= 11.5 Hz), 135.7, 135.4, 134.7, 133.3, 131.0, 119.9,

112.1 (d, J= 5.3 Hz), 22.0, 21.8, 21.4. 19F NMR (377 MHz, C6D6)

δ -99.7 (t, J= 6.7 Hz, 4F), 11B NMR (128 MHz, C6D6) δ 68.2

ppm. IR (ATR): ν= 795, 984, 1224, 1439, 1608 cm-1. HRMS (ESI-) m/z: [M+Na]+ calculated

413.0867, found: 413.0863.

B

F

FF F

Cl

- S24 -

0102030405060708090100110120130140150160170ppm

21.3

921

.83

22.0

7

111.

9711

2.15

112.

19

119.

8712

8.62

131.

0613

5.40

135.

7413

5.80

135.

8913

5.98

137.

01

145.

05

165.

1216

5.21

167.

1316

7.21

13C, C6D6

B

F

F

F

F

Cl

- S25 -

(3,5-dichloro-2,4,6-trimethylphenyl)bis(perfluorophenyl)borane (3d). White solid. Yield:

65%. 1H NMR (400 MHz, C6D6) δ 2.43 (s, 3H), 2.11 (s, 6H). 13C

NMR (101 MHz, C6D6) δ 149.3 (d, J= 252.4 Hz), 145.6 (d, J=

258.9 Hz), 142.6, 138.2 (d, J= 257.0 Hz), 136.5, 134.7, 133.0,

114.4, 21.8, 19.4. 19F NMR (377 MHz, C6D6) δ -126.2 – -130.3

(m. 4F), -143.1 – -143.4 (m, 2F), -159.2 – -161.8 (m, 4F). 11B

NMR (128 MHz, C6D6) δ 66.0 ppm. IR (ATR): ν= 685, 965,

1147, 1309, 1459, 1641 cm-1. HRMS (ESI-) m/z: [M+Br]- calcu-

lated 610.9198, found: 610.9197.

B

F

FF F

F F

F

F

F

F

Cl

Cl

- S26 -

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0ppm

6.13

3.00

2.11

2.43

7.15

proton, C6D6

B

F

F

F

F

F

FF

F

F

F

Cl Cl

19.3

921

.80

114.

41

133.

0513

4.70

136.

4513

6.56

139.

9714

2.59

143.

9314

7.37

147.

6215

0.97

136.

4513

6.56

139.

97

142.

59

143.

93

147.

3714

7.62

150.

97

- S27 -

3.91

1.98

4.00

-160

.66

-160

.65

-160

.62

-160

.59

-160

.57

-160

.55

-160

.53

-160

.50

-160

.47

-160

.45

-143

.41

-143

.39

-143

.36

-143

.34

-143

.31

-143

.29

-143

.26

-143

.24

-143

.22

-128

.63

-128

.61

-128

.59

-128

.56

-128

.54

-128

.51

(3,6-dichloro-2,4,6-trimethylphenyl)bis(2,3,5,6-tetrafluorophenyl)borane (3c). White sol-

id. Yield: 62%. 1H NMR (400 MHz, C6D6) δ 6.29 – 6.17 (m,

2H), 2.40 (s, 3H), 2.14 (s, 6H). 13C NMR (101 MHz, C6D6) δ

148.5 (d, J= 251.0 Hz), 146.5 (d, J= 234.5 Hz), 142.9, 136.2,

134.6, 133.2, 121.1, 112.1 (t, J= 22.7 Hz), 21.7, 19.4. 19F NMR

(377 MHz, C6D6) δ -129.0 – -129.6 (m, 4F), -137.4 – -137.8 (m,

4F). 11B NMR (128 MHz, C6D6) δ 67.8 ppm. IR (ATR): ν= 692,

912, 1172, 1264, 1355, 1459 cm-1. HRMS (ESI-) m/z: [M+Br]- calculated 574.9386, found:

574.9419.

B

F

FF F

F F

F

F

Cl

Cl

- S28 -

- S29 -

1.00

1.00

-137

.63

-137

.62

-137

.60

-137

.60

-137

.59

-137

.56

-137

.54

-137

.53

-137

.52

-137

.50

-137

.50

-131

.55

-129

.41

-129

.39

-129

.38

-129

.35

-129

.33

-129

.32

-129

.30

-127

.30

(3-chloro-2,4,6-trimethylphenyl)bis(2,5,6-trifluorophenyl)borane (3b). White solid. Yield:

50%. 1H NMR (400 MHz, C6D6) δ 6.45 (qd, J= 9.2, 5.2 Hz,

2H), 6.14 – 6.04 (m, 2H), 2.40 (s, 3H), 2.23 (s, 6H). 13C NMR

(101 MHz, C6D6) δ 160.79 (ddd, J= 249.5, 6.2, 2.0 Hz), 153.1

(dt, J= 255.6, 12.8 Hz), 147.8 (ddd, J= 246.6, 14.8, 3.6 Hz),

144.1, 135.5, 134.5, 133.3, 123.2 (ddd, J = 19.5, 11.3, 2.2 Hz),

120.4, 112.2 (dt, J=27.5, 5.5 Hz), 21.6, 19.3. 19F NMR (377

MHz, C6D6) δ -103.01 – -104.34 (m, 2F), -123.20 (dd, J= 22.0, 9.0 Hz, 2F), -141.9 – -142.0

(m, 2F). 11B NMR (128 MHz, C6D6) δ 67.2 ppm. IR (ATR): ν= 821, 951, 1244, 1465, 1634

cm-1. HRMS (ESI-) m/z: [M+Br]- calculated 538.9575, found: 538.9593.

B

F

FF F

F

FCl

Cl

- S30 -

19.3

721

.62

112.

0111

2.05

112.

1011

2.28

112.

3211

2.38

123.

1712

3.23

123.

2612

3.37

128.

3812

8.62

128.

8613

3.29

146.

5114

6.55

146.

6614

6.70

148.

9714

9.00

149.

1114

9.15

151.

8415

4.38

159.

5215

9.58

162.

0016

2.06

144.

1214

6.51

146.

5514

6.66

149.

0014

9.11

149.

15

151.

7315

1.84

151.

9715

4.25

154.

3815

4.50

159.

5215

9.58

162.

0016

2.06

- S31 -

0.98

1.06

1.00

-142

.03

-142

.03

-142

.02

-142

.01

-123

.24

-123

.21

-123

.18

-123

.16

-103

.67

-103

.67

-103

.65

-103

.63

-103

.62

(3,6-dichloro-2,4,6-trimethylphenyl)bis(2,6-difluorophenyl)borane (3a). White solid.

Yield: 66%. 1H NMR (500 MHz, C6D6) δ 6.76 – 6.63 (m, 2H),

6.39 (t, J= 7.9 Hz, 4H), 2.42 (s, 3H), 2.34 (s, 6H). 13C NMR (126

MHz, C6D6) δ 166.4 (d, J= 252.8 Hz), 145.7, 136.4 (t, J= 11.6

Hz), 134.9, 134.4, 133.4, 120.7, 112.2 (d, J= 27.5 Hz), 21.6, 19.4. 19F NMR (377 MHz, C6D6) δ -98.4 (t, J= 7.0 Hz, 4F). 11B NMR

(128 MHz, C6D6) δ 67.4 ppm. IR (ATR): ν= 789, 984, 1224,

1446, 1562, 1614 cm-1. HRMS (ESI-) m/z: [M+Na]+ calculated 447.0478, found: 447.0482.

B

F

FF F

Cl

Cl

- S32 -

- S33 -

(2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane (4c),

(2,3,6-trichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane (5c),

(2,3,6-trichlorophenyl)bis(2,3,6-trifluorophenyl)borane (5b), and

(2,6-dichlorophenyl)bis(2,3,6-trifluorophenyl)borane6 (4b) were

synthesized according to published procedures.

(2,6-dichlorophenyl)bis(2,6-difluorophenyl)borane (4a)6 were synthesized similar to pub-

lished procedures. The Grignard reagent, (2,6-difluoro)MgCl was pre-

pared from slow addition of iPrMgCl (prepared from 0.6 g, 23.0 mmol

activated magnesium turnings, 1.8g, 23.0 mmol 2-chloropropane, 10 ml

THF, stirred at 65°C for 1 hour), to a solution of 1-bromo-2,6-

difluorobenzene (5.0 g, 23.0 mmol) in THF (60 ml) at -20°C. The

cloudy solution was allowed to warm to 0°C, and stirred for 3 hours. After that the Grignard

reagent was added to the suspension of potassium (2,6-dichlorobenzene)trifluoroborate salt

(2.5g, 10.0 mmol in 10 ml THF) at 0°C and then it was allowed to warm to rt. and stirred

overnight. Next day, the solvent was evaporated, and the solid residue was extracted with 70

ml toluene. The mother liquor was evaporated to dryness. The remaining solid was washed

with hexane three times and dried under vacuum. The product was obtained as white solid. 6 Gyömöre, Á., Bakos, M., Földes, T., Pápai, I., Domján, A.. Soós, T., ACS Catal., 2015, 5 (9), 5366–5372.

BCl

Cl F

FF F

F H/F

H/F

FH/Cl

BF

F F

FCl Cl

- S34 -

Yield: 2.6g (69%). 1H NMR (400 MHz, CD2Cl2) δ 7.54 (tt, J= 8.3, 6.5 Hz, 2H), 7.28 (s, 3H),

6.90 (td, J= 8.3, 4.2 Hz, 4H). 13C NMR (101 MHz, CD2Cl2) δ 166.3 (dd, J= 253.5, 11.1 Hz),

143.4, 136.5 (t, J= 11.7 Hz), 135.0, 130.9, 127.2, 117.7, 111.7 (d, J= 26.3 Hz). 19F NMR (376

MHz, CD2Cl2) δ -98.5 (t, J= 7.0 Hz). 11B NMR (128 MHz, CD2Cl2) δ 63.5. IR (ATR): 767,

982, 1231, 1445, 1611 cm-1. HRMS (ESI-) m/z: [M+OH]- calculated 399.01434; found:

399.01495.

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5ppm

4.11

3.00

2.24

5.31

5.32

5.32

6.88

6.90

6.92

7.28

7.52

7.54

7.56

6.86.97.07.17.27.37.47.57.6

4.11

3.00

2.24

6.88

6.89

6.90

6.90

6.92

6.92

7.27

7.28

7.28

7.50

7.52

7.52

7.54

7.54

7.55

7.56

7.56

7.58

B

Cl

Cl

F F

F

F

proton, CD2Cl2

- S35 -

- S36 -

3. Determination of Lewis-acidity

3.1 Gutmann­Beckett method.7  An NMR tube was charged with borane (0.15 mmol) and Et3PO (6.7 mg, 0.05 mmol) or

Ph3PO (14.0 mg, 0.05 mmol) and dry CD2Cl2. A sealed capillary tube was also placed into the

NMR tube, filled with 1M solution of Mes3P, as an internal standard. The 31P{1H} NMR spec-

tra was recorded at 303K.

3.1.1. Et3P=O The internal standards (Mes3P) reference shift was = -35.88 ppm. The Et3P=O shift was =

51.5 ppm. The 31P{1H} NMR shifts of the Et3P=O-borane complexes, and their relation to

(Et3P=O)B(C6F5)3 adduct are summarized in Table S1.

Name 31P{1H} NMR shift of

adduct (ppm) (31P) =

(31P)adduct -51.5Lewis acidity relative

to B(C6F5)3 (%). Et3PO 51.50 0.0 0

1d 74.47 23.0 87 1c 73.63 22.1 84 1b 63.18 11.7 44 1a 55.43 3.9 15 2d 74.92 23.4 88 2c 74.36 22.9 86 2b 69.07 17.6 66 2a 57.74 6.2 24 3d 75.22 23.7 90 3c 74.77 23.3 88 3b 70.91 19.4 73 3a 53.40 1.9 7

B(C6F5)3 78.00 26.5 100 4c 75.22 23.7 90 4b 74.05 22.6 85 4a 72.17 20.7 78 5c 75.66 24.2 91 5b 74.20 22.7 86

Table S1. The 31P{1H} NMR shifts of the Et3P=O-borane complexes in CD2Cl2

7 Britovsek, G. J. P., Ugolotti, J., White, A. J. P., Organometallics 2005, 24, 1685-1691.

- S37 -

3.1.2. Ph3P=O The internal standards (Mes3P) reference shift was = -35.88 ppm. The Ph3P=O shift was =

28.05 ppm. The 31P{1H} NMR shifts of the Ph3P=O-borane complexes, and their relation to

(Ph3P=O)B(C6F5)3 adduct are summarized in Table S2.

Name 31P{1H} NMR shift

of adduct (ppm) (31P) =

(31P)adduct -51.5Lewis acidity relative

to B(C6F5)3 (%). Ph3PO 28,05 0.0 0

1d 42.00 14.0 76 1c 38.14 10.1 55 1b 29.98 1.9 10 1a 28.98 0.9 5 2d 44.38 16.3 89 2c 42.18 14.1 77 2b 30.27 2.2 12 2a 28.22 0.2 1 3d 45.36 17.3 94 3c 44.47 16.4 89 3b 32.75 4.7 25 3a 28.08 0.0 0

B(C6F5)3 46.49 18.4 100 4c 44.46 16.4 89 4b 42.64 14.6 79 4a 30.62 2.6 14 5c 44.92 16.9 91 5b 43.40 15.4 83

Table S2. The 31P{1H} NMR shifts of the Ph3P=O-borane complexes in CD2Cl2

4. Reactivity

In a glovebox, borane (0.05 mmol), DABCO (0.05 mmol, 6.0 mg), tert-butylbenzaldimine

(0.25 mmol, 40 mg) was dissolved in abs. toluene (1.0 ml), was added to a vial, and the vial

was placed in a high pressure reactor. The reactions took place under 10 bar H2 pressure at

room temperature. After the reaction time was over, the crude product was taken up in CDCl3

and 1H-NMR was taken. Conversions were calculated according to NMR integrals and GC-

MS, and can be seen in Table S3.

Name Conversion (%) in

0.5h 1h 2h 3h 4h 6h 24h blind - - - - - - 0

- S38 -

1d 24 32 64 81 87 99 - 1c 36 43 68 91 99 99 - 1b 7 10 20 70 87 99 - 1a 1 3 5 6 9 16 48 2d 20 35 48 80 99 - - 2c 24 42 60 88 99 - - 2b 9 15 26 40 80 99 - 2a 0 0 3 6 15 21 61

3d 5 12 23 33 43 65 99 3c 6 17 29 38 44 57 99 3b 2 8 11 17 27 50 99 3a 0 0 2 2 3 8 40 4c 53 68 99 - - - - 4b 37 56 75 94 99 - - 4a 8 20 32 47 56 80 99 5c 32 48 65 99 - - - 5b 22 33 57 90 99 - -

Table S3. Conversions due to the quantity of imine.

- S39 -

5. Theoretical Studies

5.1 Computational details  In our computational study, the geometries of boranes and borohydrides were optimized by

using density functional theory (DFT) at the B3LYP-D3/6-311G(d,p) level.8 Normal coordi-

nate analysis was carried out at the same level of theory for all optimized structures. The vi-

brational data were utilized to characterize the nature of the stationary points, and to estimate

various contributions to the Gibbs free energy. The thermochemical data were obtained within

the ideal gas – rigid rotor – harmonic oscillator approximation for T = 298.15K and c = 1

mol/dm3 conditions. For each located structure, additional single point energy calculations

were performed at the B3LYP-D3/6-311++G(3df,3pd) level to increase the accuracy of elec-

tronic structure predictions. The solvent effects were also taken into account at the B3LYP-

D3/6-311G(d,p) level by estimating the solvation free energies (solvent = toluene, chloro-

form, dichloromethane) by using the integral equation formalism variant of the polarizable

continuum model (IEFPCM)9. The atomic radii and non-electrostatic terms in the IEFPCM

calculations were those introduced by Truhlar and coworkers (SMD solvation model)10. All

DFT calculations were carried out with the Gaussian 09 package11. Several alternative ge-

ometries were tested for every borane and borohydride in order to identify their most stable

conformation. The energy values reported in the paper correspond to solution phase Gibbs

free energies of the most stable conformations that are based on LYP-D3/6-

311++G(3df,3pd) electronic energies and all additional terms obtained at the B3LYP-D3/6-

311G(d,p) level.

8 For the B3LYP-D3 functional, see: (a) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. (c) Becke, A. D. Phys. Rev. A 1988, 38, 3098. (d) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. (e) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623; (f) Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104. 9 Tomasi, J.; Mennucci, B.; Cancès, E. J. Mol. Struct. (Theochem) 1999, 464, 211. 10 Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378. 11 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.

- S40 -

Hydride affinity values presented in the paper were calculated as the Gibbs free energy of

hydride detachment defined by the following reaction:

[HB](sol) B(sol) + H(sol) Ghydr

Herein, B(sol) denotes the solvated borane species, [HB](sol) the solvated borohydride and

H(sol) the solvated hydride anion. Standard conditions (T = 298.15 K and c = 1 mol/dm3) and

several solvent models were used for free energy calculations.

5.2 Complete reference of Gaussian 09  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.;

Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.;

Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.;

Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.;

Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.;

Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant,

J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J.

B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.;

Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G.

A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J.

V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.

5.3 Total energy data of the calculated structures 

The energy data computed for the B3LYP-D3/6-311G(d,p) optimized geometries of the struc-

tures discussed in the manuscript and the Supporting Information are listed in Table S4.

structures Eo Eo′ Go Gstoluene Gs

chloroform GsDCM Go

vac Gotoluene Go

chloroform GoDCM

hidrid  ‐0.5099  ‐0.5342 ‐0.5199 ‐0.5958 ‐0.6283 ‐0.6440 ‐0.5442 ‐0.6271 ‐0.6596 ‐0.6753 

1a  ‐1235.0763  ‐1235.1826 ‐1234.8082 ‐1235.0943 ‐1235.0981 ‐1235.1002 ‐1234.9145 ‐1234.9294 ‐1234.9333 ‐1234.9354 

1a‐h  ‐1235.7424  ‐1235.8525 ‐1235.4632 ‐1235.7927 ‐1235.8099 ‐1235.8190 ‐1235.5733 ‐1235.6206 ‐1235.6378 ‐1235.6469 

1b  ‐1433.5880  ‐1433.7157 ‐1433.3389 ‐1433.6042 ‐1433.6083 ‐1433.6104 ‐1433.4666 ‐1433.4798 ‐1433.4839 ‐1433.4860 

1b‐h  ‐1434.2644  ‐1434.3959 ‐1434.0040 ‐1434.3109 ‐1434.3271 ‐1434.3355 ‐1434.1355 ‐1434.1789 ‐1434.1952 ‐1434.2036 

1c  ‐1632.0979  ‐1632.2471 ‐1631.8678 ‐1632.1119 ‐1632.1161 ‐1632.1182 ‐1632.0170 ‐1632.0279 ‐1632.0321 ‐1632.0342 

1c‐h  ‐1632.7845  ‐1632.9374 ‐1632.5427 ‐1632.8267 ‐1632.8418 ‐1632.8495 ‐1632.6957 ‐1632.7348 ‐1632.7500 ‐1632.7577 

1d  ‐1830.5958  ‐1830.7676 ‐1830.3842 ‐1830.6066 ‐1830.6105 ‐1830.6125 ‐1830.5561 ‐1830.5639 ‐1830.5678 ‐1830.5697 

1d‐h  ‐1831.2880  ‐1831.4631 ‐1831.0646 ‐1831.3255 ‐1831.3393 ‐1831.3460 ‐1831.2396 ‐1831.2741 ‐1831.2879 ‐1831.2946 

2a  ‐1694.7020  ‐1694.8139 ‐1694.4427 ‐1694.7211 ‐1694.7249 ‐1694.7269 ‐1694.5546 ‐1694.5707 ‐1694.5745 ‐1694.5765 

2a‐h  ‐1695.3743  ‐1695.4890 ‐1695.1045 ‐1695.4237 ‐1695.4400 ‐1695.4485 ‐1695.2192 ‐1695.2657 ‐1695.2820 ‐1695.2905 

2b  ‐1893.2132  ‐1893.3466 ‐1892.9729 ‐1893.2306 ‐1893.2347 ‐1893.2368 ‐1893.1063 ‐1893.1206 ‐1893.1247 ‐1893.1268 

2b‐h  ‐1893.8958  ‐1894.0320 ‐1893.6446 ‐1893.9417 ‐1893.9571 ‐1893.9649 ‐1893.7808 ‐1893.8236 ‐1893.8391 ‐1893.8469 

2c  ‐2091.7228  ‐2091.8777 ‐2091.5012 ‐2091.7380 ‐2091.7422 ‐2091.7442 ‐2091.6560 ‐2091.6682 ‐2091.6724 ‐2091.6744 

2c‐h  ‐2092.4154  ‐2092.5731 ‐2092.1828 ‐2092.4571 ‐2092.4715 ‐2092.4786 ‐2092.3405 ‐2092.3791 ‐2092.3935 ‐2092.4006 

2d  ‐2290.2207  ‐2290.3981 ‐2290.0173 ‐2290.2328 ‐2290.2368 ‐2290.2388 ‐2290.1948 ‐2290.2039 ‐2290.2079 ‐2290.2099 

2d‐h  ‐2290.9186  ‐2291.0985 ‐2290.7044 ‐2290.9557 ‐2290.9688 ‐2290.9750 ‐2290.8842 ‐2290.9183 ‐2290.9314 ‐2290.9375 

3a  ‐2154.3238  ‐2154.4417 ‐2154.0757 ‐2154.3437 ‐2154.3473 ‐2154.3491 ‐2154.1936 ‐2154.2104 ‐2154.2141 ‐2154.2159 

3a‐h  ‐2154.9990  ‐2155.1192 ‐2154.7410 ‐2155.0472 ‐2155.0625 ‐2155.0703 ‐2154.8613 ‐2154.9065 ‐2154.9218 ‐2154.9296 

3b  ‐2352.8347  ‐2352.9741 ‐2352.6054 ‐2352.8529 ‐2352.8569 ‐2352.8588 ‐2352.7448 ‐2352.7600 ‐2352.7640 ‐2352.7659 

3b‐h  ‐2353.5201  ‐2353.6618 ‐2353.2810 ‐2353.5648 ‐2353.5792 ‐2353.5863 ‐2353.4227 ‐2353.4644 ‐2353.4788 ‐2353.4860 

3c  ‐2551.3440  ‐2551.5049 ‐2551.1333 ‐2551.3599 ‐2551.3641 ‐2551.3659 ‐2551.2942 ‐2551.3071 ‐2551.3113 ‐2551.3131 

- S42 -

structures Eo Eo′ Go Gstoluene Gs

chloroform GsDCM Go

vac Gotoluene Go

chloroform GoDCM

3c‐h  ‐2552.0391  ‐2552.2024 ‐2551.8189 ‐2552.0799 ‐2552.0935 ‐2552.0999 ‐2551.9823 ‐2552.0201 ‐2552.0336 ‐2552.0401 

3d  ‐2749.8417  ‐2750.0253 ‐2749.6495 ‐2749.8545 ‐2749.8584 ‐2749.8602 ‐2749.8331 ‐2749.8428 ‐2749.8468 ‐2749.8486 

3d‐h  ‐2750.5420  ‐2750.7275 ‐2750.3403 ‐2750.5782 ‐2750.5905 ‐2750.5962 ‐2750.5258 ‐2750.5590 ‐2750.5713 ‐2750.5770 

4a  ‐2036.3347  ‐2036.4458 ‐2036.1634 ‐2036.3529 ‐2036.3565 ‐2036.3584 ‐2036.2745 ‐2036.2896 ‐2036.2933 ‐2036.2951 

4a‐h  ‐2037.0077  ‐2037.1224 ‐2036.8313 ‐2037.0586 ‐2037.0759 ‐2037.0850 ‐2036.9461 ‐2036.9940 ‐2037.0113 ‐2037.0204 

4b  ‐2234.8459  ‐2234.9785 ‐2234.6940 ‐2234.8623 ‐2234.8661 ‐2234.8679 ‐2234.8266 ‐2234.8399 ‐2234.8437 ‐2234.8455 

4b‐h  ‐2235.5296  ‐2235.6656 ‐2235.3708 ‐2235.5765 ‐2235.5928 ‐2235.6011 ‐2235.5068 ‐2235.5506 ‐2235.5669 ‐2235.5753 

4c  ‐2433.3553  ‐2433.5093 ‐2433.2217 ‐2433.3693 ‐2433.3731 ‐2433.3749 ‐2433.3757 ‐2433.3868 ‐2433.3906 ‐2433.3923 

4c‐h  ‐2434.0494  ‐2434.2069 ‐2433.9091 ‐2434.0922 ‐2434.1074 ‐2434.1149 ‐2434.0665 ‐2434.1063 ‐2434.1215 ‐2434.1290 

5b  ‐2694.4635  ‐2694.6030 ‐2694.3230 ‐2694.4805 ‐2694.4842 ‐2694.4859 ‐2694.4624 ‐2694.4763 ‐2694.4800 ‐2694.4817 

5b‐h  ‐2695.1526  ‐2695.2939 ‐2695.0026 ‐2695.1988 ‐2695.2142 ‐2695.2220 ‐2695.1440 ‐2695.1872 ‐2695.2026 ‐2695.2104 

5c  ‐2892.9726  ‐2893.1336 ‐2892.8510 ‐2892.9872 ‐2892.9909 ‐2892.9926 ‐2893.0119 ‐2893.0235 ‐2893.0273 ‐2893.0289 

5c‐h  ‐2893.6709  ‐2893.8346 ‐2893.5419 ‐2893.7128 ‐2893.7273 ‐2893.7343 ‐2893.7056 ‐2893.7445 ‐2893.7589 ‐2893.7660 

a Notation: Eo and Eo′ refer to electronic energies computed B3LYP-D3/6-311G(d,p) and B3LYP-D3/6-311++G(3df,3pd) level of DFT; Godenotes gas-phase Gibbs free energies and Gs

toluene, Gschloroform, Gs

DCM denote solvation corrected electronic energies obtained from B3LYP-D3/6-311G(d,p) calculations (T = 298.15 K). The last four columns are obtained as Go

i = Eo′ + (Go - Eo) + (Gsi - Eo) + ΔGconc where i refers to the applied solvation medium. In the case of vacuum Gs

vacuum = Eo. The value ΔGconc corresponds to concentration correction to the free energy when switching from p = 1 atm (ideal gas standard state) to c = 1mol/dm3 (standard concentration in solution phase, where ΔGconc = 0.00302 a.u.).

Table S4.The energy data (in atomic units) computed for B3LYP-D3/6-311G(d,p) optimized structures.

5.4 Cartesian coordinates of the reported structures  Cartesian coordinates of B3LYP-D3/6-311G(d,p) optimized geometries are given below in

standard XYZ format (units are in ångstroms). First line indicates total number of atoms, se-

cond line is molecule name (as defined in the paper).

43 1a B -0.2421500 -0.0001740 -0.0003720 C -1.0261840 1.3567350 0.0370440 C -1.0354010 -1.3515160 -0.0382050 C 1.3221820 -0.0044330 0.0004680 C -0.6451670 -2.4797060 0.6922650 C -1.3097000 -3.6953870 0.6576300 C -2.4277500 -3.8171670 -0.1626330 C -2.8702040 -2.7346480 -0.9194190 C -2.1754090 -1.5406690 -0.8279000 C -0.6321240 2.4796680 -0.6991670 C -1.2882930 3.6999050 -0.6652460 C -2.4012250 3.8319170 0.1604000 C -2.8469890 2.7549080 0.9231160 C -2.1606970 1.5560020 0.8319120 C 2.0349740 -0.3829810 -1.1541720 C 3.4294060 -0.3760650 -1.1369080 C 4.1466530 -0.0166010 0.0045050 C 3.4293240 0.3453450 1.1449770 C 2.0348620 0.3658660 1.1577510 F 0.4202780 -2.3790160 1.5168480 F -2.5986860 0.5267730 1.5936600 F 0.4283290 2.3686430 -1.5290750 C 1.2960840 0.7258950 2.4273350 C 5.6558980 0.0103470 -0.0044500 C 1.2966350 -0.7451000 -2.4233650 F -2.6107230 -0.5063240 -1.5840820 H -0.9488040 -4.5137700 1.2663450 H -3.7323830 -2.7991820 -1.5698330 H -3.7053210 2.8274090 1.5777720 H -0.9251760 4.5138100 -1.2786310 H -2.9588700 -4.7600920 -0.2113800 H -2.9257690 4.7785360 0.2087140 H 3.9696480 -0.6581850 -2.0363520 H 3.9691660 0.6150150 2.0484220 H 1.9862850 0.9985230 3.2280380 H 0.6157610 1.5681530 2.2701540 H 0.6958790 -0.1196710 2.7779530 H 6.0645200 -0.7309930 -0.6956500 H 6.0267590 0.9918820 -0.3202140

- S44 -

H 6.0650830 -0.1896620 0.9888800 H 0.7005400 0.1017510 -2.7778920 H 1.9869150 -1.0233640 -3.2220600 H 0.6124890 -1.5838760 -2.2641900 44 1a-hydride B 0.2712460 -0.0035610 0.6840240 C 1.2780630 -1.2564580 0.3367240 C 0.7951210 1.4562390 0.1299810 C -1.3048600 -0.2013500 0.2704470 C 1.7298920 1.7229600 -0.8688750 C 2.1310340 2.9878100 -1.2856580 C 1.5676370 4.1034150 -0.6751980 C 0.6216160 3.9212970 0.3307210 C 0.2760280 2.6256510 0.6921500 C 0.9466090 -2.4966050 -0.2100330 C 1.8276110 -3.5612230 -0.3891790 C 3.1520540 -3.4141780 0.0036900 C 3.5600720 -2.2069380 0.5671930 C 2.6243660 -1.1938350 0.7137740 C -2.3096230 -0.3588070 1.2544950 C -3.6571930 -0.4826940 0.8967160 C -4.0721630 -0.4596960 -0.4321650 C -3.0896630 -0.3061700 -1.4065110 C -1.7372720 -0.1780960 -1.0763930 F 2.3098170 0.6776000 -1.5301400 F 3.0807890 -0.0415120 1.2798160 F -0.3304320 -2.7304960 -0.6244150 C -0.7564820 -0.0081850 -2.2164640 C -5.5262630 -0.6388320 -0.8042670 C -1.9743800 -0.3917170 2.7314000 F -0.6510210 2.5139050 1.6855480 H 2.8680390 3.0709040 -2.0754040 H 0.1502890 4.7537840 0.8392120 H 4.5788120 -2.0342800 0.8929540 H 1.4540990 -4.4770810 -0.8314930 H 0.3704420 0.0968950 1.8877960 H 1.8591640 5.1023970 -0.9803350 H 3.8582480 -4.2268820 -0.1267260 H -4.4036110 -0.6020970 1.6801780 H -3.3818070 -0.2898490 -2.4554010 H -1.1670960 -0.4146110 -3.1459750 H -0.5317740 1.0507140 -2.3846800 H 0.1938700 -0.5009280 -2.0199670 H -6.1891420 -0.2632850 -0.0183040 H -5.7702090 -0.1088700 -1.7304950 H -5.7748700 -1.6963150 -0.9608030 H -1.2570790 -1.1837260 2.9613840 H -1.5138610 0.5482230 3.0439280

- S45 -

H -2.8753430 -0.5581910 3.3314240 43 1b B -0.2421500 -0.0001740 -0.0003720 C -1.0261840 1.3567350 0.0370440 C -1.0354010 -1.3515160 -0.0382050 C 1.3221820 -0.0044330 0.0004680 C -0.6451670 -2.4797060 0.6922650 C -1.3097000 -3.6953870 0.6576300 C -2.4277500 -3.8171670 -0.1626330 C -2.8702040 -2.7346480 -0.9194190 C -2.1754090 -1.5406690 -0.8279000 C -0.6321240 2.4796680 -0.6991670 C -1.2882930 3.6999050 -0.6652460 C -2.4012250 3.8319170 0.1604000 C -2.8469890 2.7549080 0.9231160 C -2.1606970 1.5560020 0.8319120 C 2.0349740 -0.3829810 -1.1541720 C 3.4294060 -0.3760650 -1.1369080 C 4.1466530 -0.0166010 0.0045050 C 3.4293240 0.3453450 1.1449770 C 2.0348620 0.3658660 1.1577510 F 0.4202780 -2.3790160 1.5168480 F -2.5986860 0.5267730 1.5936600 F 0.4283290 2.3686430 -1.5290750 C 1.2960840 0.7258950 2.4273350 C 5.6558980 0.0103470 -0.0044500 C 1.2966350 -0.7451000 -2.4233650 F -2.6107230 -0.5063240 -1.5840820 H -0.9488040 -4.5137700 1.2663450 H -3.7323830 -2.7991820 -1.5698330 H -3.7053210 2.8274090 1.5777720 H -0.9251760 4.5138100 -1.2786310 H -2.9588700 -4.7600920 -0.2113800 H -2.9257690 4.7785360 0.2087140 H 3.9696480 -0.6581850 -2.0363520 H 3.9691660 0.6150150 2.0484220 H 1.9862850 0.9985230 3.2280380 H 0.6157610 1.5681530 2.2701540 H 0.6958790 -0.1196710 2.7779530 H 6.0645200 -0.7309930 -0.6956500 H 6.0267590 0.9918820 -0.3202140 H 6.0650830 -0.1896620 0.9888800 H 0.7005400 0.1017510 -2.7778920 H 1.9869150 -1.0233640 -3.2220600 H 0.6124890 -1.5838760 -2.2641900 44 1b-hydride

- S46 -

B -0.0854510 -0.1880300 0.6802480 C -1.7125390 -0.2462110 0.4487120 C 0.7268470 -1.4539320 0.0076560 C 0.6621390 1.2140930 0.2769500 C 0.3053040 -2.3157040 -1.0061780 C 1.0454740 -3.3698220 -1.5223390 C 2.3175710 -3.6154560 -1.0107350 C 2.7871190 -2.7897170 -0.0054800 C 2.0063290 -1.7456170 0.4798860 C -2.5333700 0.7808570 -0.0099570 C -3.9242170 0.6790050 -0.0779780 C -4.5762640 -0.4694440 0.3207820 C -3.8038620 -1.5301030 0.7962420 C -2.4290400 -1.3833010 0.8463710 C 1.1942670 2.0721360 1.2684700 C 1.8703300 3.2462100 0.9175070 C 2.0489300 3.6253190 -0.4102570 C 1.5268030 2.7868780 -1.3912290 C 0.8492220 1.6075230 -1.0687210 F -0.9230870 -2.1241440 -1.5714080 F -1.7297220 -2.4492000 1.3263510 F -2.0130220 1.9570790 -0.4337590 C 0.3292070 0.7685630 -2.2160450 C 2.7432610 4.9184810 -0.7709650 C 1.0639000 1.7570520 2.7444340 F 2.5498100 -0.9950630 1.4679700 H 0.6223810 -3.9774190 -2.3125600 F 4.0238740 -3.0004330 0.5192720 H -4.2518960 -2.4594300 1.1251670 F -4.6419920 1.7346880 -0.5478120 H 0.0197460 -0.3843240 1.8706690 H 2.9418360 -4.4217460 -1.3743530 H -5.6556730 -0.5217810 0.2561560 H 2.2673950 3.8833240 1.7056320 H 1.6448830 3.0592790 -2.4386810 H 0.1852270 1.3811320 -3.1111110 H 1.0345450 -0.0308560 -2.4682270 H -0.6174000 0.2863690 -1.9793180 H 3.4876880 5.1957710 -0.0181210 H 3.2538870 4.8423770 -1.7360610 H 2.0307910 5.7497370 -0.8454140 H 0.0179270 1.6346760 3.0371010 H 1.5691790 0.8193490 2.9869890 H 1.4995300 2.5564990 3.3526210 43 1c B -0.1386450 0.0030990 0.0004840 C 0.6445060 -1.3565060 0.0906790 C 0.6883100 1.3363480 -0.0904790

- S47 -

C -1.6948530 0.0276550 0.0010850 C 0.3536780 2.4565670 0.6724100 C 1.0780280 3.6395470 0.5913080 C 2.1544500 3.7466610 -0.2744600 C 2.5018720 2.6491970 -1.0468310 C 1.7862060 1.4646960 -0.9431580 C 0.2749130 -2.4638130 -0.6748360 C 0.9603410 -3.6698260 -0.5948420 C 2.0313820 -3.8133590 0.2723290 C 2.4130410 -2.7291150 1.0472230 C 1.7363750 -1.5218140 0.9446230 C -2.4010700 0.4360550 -1.1492420 C -3.7948160 0.4431660 -1.1326020 C -4.5168770 0.0757440 0.0035950 C -3.8057230 -0.3123320 1.1397020 C -2.4124310 -0.3542970 1.1533460 F -0.6668950 2.3975750 1.5449850 F 2.1312850 -0.5000260 1.7285520 F -0.7416980 -2.3698910 -1.5490870 C -1.6819120 -0.7473750 2.4181730 C -6.0256980 0.0681530 -0.0067200 C -1.6596070 0.8125190 -2.4127340 F 2.1488900 0.4294150 -1.7249090 F 0.7295890 4.6840300 1.3583940 F 3.5360400 2.7293510 -1.8986330 F 3.4427790 -2.8443040 1.9003800 F 0.5793890 -4.7010700 -1.3644250 H 2.7148860 4.6688940 -0.3446290 H 2.5614980 -4.7534090 0.3416540 H -4.3314120 0.7434430 -2.0279830 H -4.3502790 -0.5863170 2.0386420 H -2.3792130 -0.9873340 3.2226770 H -1.0450950 -1.6223080 2.2575580 H -1.0397350 0.0669160 2.7681250 H -6.4243390 0.8246170 -0.6869160 H -6.4062690 -0.9042300 -0.3383480 H -6.4331670 0.2568690 0.9892520 H -1.0389800 -0.0177940 -2.7639400 H -2.3498170 1.0722400 -3.2172130 H -0.9999450 1.6699730 -2.2500160 44 1c-hydride B -0.0648450 -0.0879300 0.7230950 C 1.3715260 -0.8245690 0.4003130 C -0.1510930 1.4665450 0.1812000 C -1.4186660 -0.8940780 0.2776000 C 0.6321660 2.0677670 -0.8007350 C 0.4815370 3.3938590 -1.1893790 C -0.4785130 4.2017370 -0.6054940

- S48 -

C -1.2768300 3.6338000 0.3750680 C -1.1097380 2.3079920 0.7498260 C 1.5557660 -2.0820600 -0.1731030 C 2.8083890 -2.6751410 -0.3128080 C 3.9561580 -2.0398420 0.1234190 C 3.8062320 -0.7899910 0.7046730 C 2.5522850 -0.2154800 0.8365000 C -2.2851000 -1.4559070 1.2450700 C -3.4645540 -2.1049540 0.8633180 C -3.8381570 -2.2303830 -0.4720960 C -2.9891460 -1.6817950 -1.4291160 C -1.8059270 -1.0266360 -1.0760930 F 1.5878690 1.3568590 -1.4523680 F 2.4999650 1.0046980 1.4221840 F 0.5086050 -2.8006300 -0.6415020 C -0.9617370 -0.4643870 -2.1994230 C -5.0936750 -2.9720070 -0.8693710 C -1.9815190 -1.3749490 2.7268870 F -1.9310100 1.8413270 1.7201280 F 1.2804910 3.9049380 -2.1591160 F -2.2290760 4.3905180 0.9758680 F 4.9038950 -0.1290070 1.1510220 F 2.9059790 -3.8996510 -0.8891050 H -0.0320710 0.0366950 1.9262920 H -0.6022420 5.2333570 -0.9032780 H 4.9293470 -2.4973080 0.0144210 H -4.1089270 -2.5258500 1.6327400 H -3.2508090 -1.7695720 -2.4820910 H -1.1631500 -0.9902910 -3.1371730 H -1.1786280 0.5973450 -2.3605350 H 0.1044030 -0.5386660 -1.9933250 H -5.8604510 -2.9047010 -0.0914800 H -5.5182270 -2.5719220 -1.7953040 H -4.8935330 -4.0375950 -1.0376720 H -1.0075680 -1.8121950 2.9612420 H -1.9474470 -0.3351320 3.0600710 H -2.7433370 -1.9031250 3.3090830 43 1d B 0.0011490 0.3086030 -0.0001540 C 1.3504170 -0.4931520 -0.0491880 C -1.3560330 -0.4796320 0.0492880 C 0.0093580 1.8672590 -0.0006350 C -2.4806990 -0.0475400 -0.6599290 C -3.6968010 -0.7162670 -0.6128040 C -3.8185390 -1.8507470 0.1817430 C -2.7259750 -2.3129990 0.9091850 C -1.5210080 -1.6330090 0.8216010 C 2.4788780 -0.0725590 0.6608710

- S49 -

C 3.6882490 -0.7534190 0.6142720 C 3.7991040 -1.8888420 -0.1805180 C 2.7024040 -2.3399240 -0.9087490 C 1.5042570 -1.6479110 -0.8217030 C -0.3771160 2.5821530 1.1512880 C -0.3577770 3.9758280 1.1340530 C 0.0193490 4.6903290 -0.0036690 C 0.3878380 3.9708110 -1.1409500 C 0.3989120 2.5768750 -1.1546420 F -2.4070820 1.0261910 -1.4595500 F 0.4739160 -2.1101390 -1.5511070 F 4.9548950 -2.5470270 -0.2436230 F 2.4154250 1.0015330 1.4609210 C 0.7606080 1.8382650 -2.4239350 C 0.0574880 6.1986860 0.0060120 C -0.7520730 1.8488340 2.4197520 F -0.4949680 -2.1057620 1.5503280 F -4.9808130 -2.4973500 0.2453560 F -4.7451450 -0.2867680 -1.3211110 F -2.8513910 -3.3989610 1.6777000 F 2.8173940 -3.4268780 -1.6774910 F 4.7404210 -0.3346340 1.3233600 H -0.6432520 4.5183730 2.0306760 H 0.6695000 4.5091770 -2.0412340 H 1.0570920 2.5273570 -3.2165260 H 1.5879480 1.1407650 -2.2629510 H -0.0916090 1.2577220 -2.7918600 H -0.6864390 6.6126360 0.6908250 H 1.0394110 6.5597450 0.3311520 H -0.1295010 6.6095920 -0.9888550 H 0.0914610 1.2571120 2.7898950 H -1.0410560 2.5421000 3.2114750 H -1.5882240 1.1623270 2.2570750 44 1d-hydride B 0.0445940 0.3079670 0.7565840 C -1.5333270 -0.0103770 0.4044340 C 1.0823130 -0.8776870 0.2652210 C 0.6178210 1.7647690 0.2806400 C 0.8574550 -1.8635480 -0.6896530 C 1.7933640 -2.8310380 -1.0420330 C 3.0329950 -2.8379870 -0.4219780 C 3.3116870 -1.8744570 0.5380980 C 2.3444750 -0.9299670 0.8573540 C -2.4400700 0.8434700 -0.2187550 C -3.7908120 0.5428090 -0.3901720 C -4.2935210 -0.6592320 0.0782300 C -3.4328570 -1.5450770 0.7131790 C -2.0971430 -1.2032990 0.8628430

- S50 -

C 0.9264320 2.7711370 1.2263020 C 1.4602940 3.9990610 0.8201500 C 1.7086010 4.2885740 -0.5190120 C 1.4042990 3.3039060 -1.4546310 C 0.8720120 2.0678400 -1.0770330 F -0.3185090 -1.9193480 -1.3628600 F -1.3212360 -2.1125190 1.4957920 F -5.5970380 -0.9662310 -0.0782330 F -2.0535990 2.0391310 -0.7160800 C 0.5830780 1.0710910 -2.1789430 C 2.2457000 5.6357330 -0.9439480 C 0.7013580 2.5642890 2.7099040 F 2.6867980 -0.0296500 1.8059120 F 3.9564620 -3.7649070 -0.7475170 F 1.5155890 -3.7577940 -1.9826950 F 4.5150460 -1.8761440 1.1488610 F -3.9114110 -2.7188390 1.1765990 F -4.6182020 1.4109770 -1.0095830 H 0.0715420 0.2217120 1.9626650 H 1.6870460 4.7515290 1.5728300 H 1.5807060 3.5033230 -2.5100090 H 0.4311620 1.5815960 -3.1342030 H 1.4169700 0.3718160 -2.3058060 H -0.3013960 0.4709490 -1.9734960 H 2.8728650 6.0795730 -0.1648110 H 2.8465630 5.5571230 -1.8551050 H 1.4332900 6.3435410 -1.1504040 H -0.3393500 2.3099020 2.9264630 H 1.3108160 1.7386050 3.0845480 H 0.9567860 3.4683460 3.2714710 43 2a B 0.6279510 -0.0204120 0.1187220 C 1.2669030 1.4076840 0.0099310 C 1.5197750 -1.2985010 -0.0166870 C -0.9162180 -0.1576140 0.3644510 C 1.0673980 -2.4770890 -0.6268390 C 1.8223960 -3.6340230 -0.7367670 C 3.1057530 -3.6434820 -0.1985480 C 3.6186140 -2.5090350 0.4259300 C 2.8247590 -1.3770020 0.4894100 C 0.8951400 2.4770510 0.8323620 C 1.4224440 3.7547770 0.7325500 C 2.3687770 4.0070410 -0.2562140 C 2.7783890 2.9910650 -1.1168140 C 2.2288920 1.7317190 -0.9538320 C -1.4052380 -0.5446990 1.6252180 C -2.7801260 -0.6277570 1.8254390 C -3.7019010 -0.3541910 0.8128900

- S51 -

C -3.1826730 0.0121050 -0.4302990 C -1.8112480 0.1186900 -0.6830700 F -0.1633900 -2.4913360 -1.1787160 F 2.6192970 0.7636250 -1.8169660 F -0.0042330 2.2544430 1.8164760 C -1.3085210 0.4631220 -2.0642280 C -5.1827630 -0.4600810 1.0639320 C -0.4525000 -0.8233950 2.7648800 F 3.3397590 -0.2947470 1.1144800 H 1.4001890 -4.4951180 -1.2374610 H 4.6102880 -2.4864560 0.8578030 H 3.5046700 3.1566070 -1.9013890 H 1.0893970 4.5198230 1.4212120 H 3.7110990 -4.5392640 -0.2672400 H 2.7890310 5.0002510 -0.3579840 H -3.1564520 -0.9140600 2.8027470 Cl -4.3188000 0.3484140 -1.7511710 H -1.6570840 -0.2732860 -2.7929410 H -1.6740500 1.4401160 -2.3914650 H -0.2184760 0.4772410 -2.1097410 H -5.3801740 -0.7600720 2.0941670 H -5.6830290 0.4947330 0.8791490 H -5.6445100 -1.1920240 0.3951720 H 0.1053200 0.0796520 3.0306130 H -0.9840170 -1.1610580 3.6565390 H 0.2764260 -1.5942400 2.4974830 44 2a-hydride B 0.7231600 0.0250540 0.8118050 C 1.6854440 -1.2168740 0.3366940 C 1.0928480 1.4833720 0.1372420 C -0.9003480 -0.2093610 0.6848510 C 1.8501270 1.7514520 -1.0018550 C 2.1275880 3.0151380 -1.5115740 C 1.6203850 4.1289700 -0.8514740 C 0.8516500 3.9463440 0.2953250 C 0.6208190 2.6520900 0.7416340 C 1.2915510 -2.4829480 -0.0966680 C 2.1518510 -3.5364980 -0.3969770 C 3.5212320 -3.3485750 -0.2558830 C 3.9939120 -2.1138000 0.1837620 C 3.0750240 -1.1136090 0.4636680 C -1.7121280 -0.3012190 1.8378450 C -3.1007120 -0.4014960 1.7279800 C -3.7610180 -0.4080630 0.5018280 C -2.9455020 -0.3311460 -0.6252420 C -1.5501600 -0.2492710 -0.5743470 F 2.3693220 0.7069900 -1.7141730 F 3.5942140 0.0672380 0.9011020

- S52 -

F -0.0344500 -2.7554830 -0.2581830 C -0.7691580 -0.2309940 -1.8665000 C -5.2631590 -0.4986660 0.4233800 C -1.1238580 -0.2877040 3.2329240 F -0.1331870 2.5402410 1.8724460 H 2.7293210 3.0982610 -2.4085100 H 0.4309370 4.7773160 0.8484790 H 5.0500040 -1.9103820 0.3135480 H 1.7285620 -4.4756820 -0.7322690 Cl -3.7648960 -0.3357720 -2.2267000 H 1.0168960 0.1668830 1.9779750 H 1.8180450 5.1269340 -1.2267080 H 4.2128250 -4.1517690 -0.4852140 H -3.7010980 -0.4697240 2.6322490 H -1.1019920 -1.0368160 -2.5255210 H -0.9192420 0.7110560 -2.4048890 H 0.2934330 -0.3554540 -1.6963000 H -5.6950180 -0.5555550 1.4254650 H -5.6909280 0.3702880 -0.0870620 H -5.5831540 -1.3809530 -0.1403330 H -0.3716050 -1.0702070 3.3571440 H -0.6253670 0.6632780 3.4317300 H -1.9056040 -0.4383360 3.9846810 43 2b B 0.5312350 0.0159410 0.1092850 C 1.4873330 -1.2233800 0.1635050 C 1.1136350 1.4388390 -0.2093960 C -1.0034210 -0.1524920 0.3745870 C 0.6983720 2.5845760 0.4719360 C 1.1963870 3.8479180 0.1709950 C 2.1192720 4.0112130 -0.8468300 C 2.5534900 2.8985040 -1.5647230 C 2.0541840 1.6554740 -1.2236960 C 1.0874980 -2.4848460 -0.2902520 C 1.9222830 -3.5952470 -0.2231200 C 3.1896120 -3.4854830 0.3212510 C 3.6297860 -2.2513210 0.7949220 C 2.7833690 -1.1623890 0.6951840 C -1.9058760 -0.0597910 -0.6989420 C -3.2722690 -0.1883930 -0.4300230 C -3.7782920 -0.4010910 0.8540510 C -2.8490240 -0.4937040 1.8921720 C -1.4782520 -0.3829400 1.6787750 F -0.1807470 2.4862510 1.4838830 F 3.2288970 0.0203820 1.1754650 F -0.1219820 -2.6516210 -0.8463620 C -0.5179640 -0.4615540 2.8432750 C -5.2539220 -0.5330580 1.1216420

- S53 -

C -1.4140730 0.1121240 -2.1158000 F 2.4696840 0.5888510 -1.9483120 F 0.7715270 4.9080730 0.8808090 H 3.2660080 2.9860160 -2.3737440 H 4.6112080 -2.1273620 1.2322800 F 1.4848800 -4.7762240 -0.6939570 H 2.4869680 5.0056040 -1.0646840 H 3.8173630 -4.3661730 0.3653230 Cl -4.4165140 -0.0857420 -1.7802290 H -3.2159760 -0.6573360 2.9006260 H -1.0377210 -0.6943180 3.7743280 H 0.2426580 -1.2317490 2.6839310 H 0.0016410 0.4914820 2.9816880 H -5.7925710 0.3653210 0.8074810 H -5.6820400 -1.3691750 0.5615650 H -5.4420220 -0.6955080 2.1838740 H -1.7283600 -0.7319960 -2.7350300 H -1.8203530 1.0178050 -2.5737760 H -0.3253270 0.1661330 -2.1672150 44 2b-hydride B 0.6061930 0.2258310 0.8012280 C 1.8366650 -0.8001840 0.4447850 C 0.6624390 1.6650860 -0.0028750 C -0.9194530 -0.3752970 0.6910500 C 1.3671080 1.9883680 -1.1636540 C 1.3686940 3.2301820 -1.7824070 C 0.6184650 4.2627510 -1.2255910 C -0.0999920 3.9991670 -0.0737110 C -0.0699090 2.7365560 0.5089380 C 1.7296620 -2.1508800 0.1244310 C 2.8336400 -2.9832480 -0.0674830 C 4.1200720 -2.5015250 0.0618750 C 4.2874260 -1.1559930 0.3919010 C 3.1637710 -0.3695230 0.5734810 C -1.7144880 -0.5449120 1.8468930 C -3.0439940 -0.9590780 1.7433290 C -3.6599890 -1.2171200 0.5213050 C -2.8580100 -1.0603670 -0.6071000 C -1.5161880 -0.6676950 -0.5606310 F 2.1165480 1.0238500 -1.7760580 F 3.3879450 0.9321000 0.9050690 F 0.5188720 -2.7391260 -0.0268800 C -0.7308460 -0.5921830 -1.8480610 C -5.1033600 -1.6435450 0.4484080 C -1.1737590 -0.2829570 3.2366670 F -0.8007950 2.5775900 1.6387600 H 1.9512280 3.3714680 -2.6841090 F -0.8417400 4.9826290 0.5005900

- S54 -

H 5.2695600 -0.7154950 0.5093150 F 2.6295110 -4.2890170 -0.3856180 H 0.8371340 0.5309770 1.9492170 H 0.5797670 5.2515710 -1.6644630 H 4.9586680 -3.1682160 -0.0937550 H -3.6338870 -1.0801140 2.6487300 Cl -3.6195390 -1.3849890 -2.2019680 H -0.8574670 -1.5106350 -2.4266440 H -1.0785950 0.2357010 -2.4752810 H 0.3284060 -0.4551740 -1.6671610 H -5.5338620 -1.7074400 1.4505000 H -5.6997900 -0.9376720 -0.1384330 H -5.2087990 -2.6199460 -0.0351950 H -0.2691910 -0.8643430 3.4301120 H -0.9048380 0.7686790 3.3557030 H -1.9179230 -0.5415640 3.9966910 43 2c B 0.2332440 -0.0337270 0.1490800 C 0.8180240 1.4156170 -0.0221800 C 1.2017310 -1.2662200 0.0945930 C -1.2998980 -0.2346420 0.3786040 C 0.8272600 -2.4650030 -0.5214960 C 1.6758300 -3.5648170 -0.5604310 C 2.9253380 -3.5109270 0.0349260 C 3.3175290 -2.3370460 0.6589660 C 2.4735720 -1.2358280 0.6756930 C 0.4067120 2.4789920 0.7841950 C 0.9140490 3.7623940 0.6207250 C 1.8378650 4.0320080 -0.3754310 C 2.2535680 2.9958420 -1.1971880 C 1.7588450 1.7134190 -1.0107140 C -1.7829880 -0.6121750 1.6454280 C -3.1550120 -0.7469660 1.8342360 C -4.0766060 -0.5382400 0.8060370 C -3.5622780 -0.1807810 -0.4423160 C -2.1942420 -0.0211440 -0.6847770 F -0.3630720 -2.5706080 -1.1320050 F 2.1751250 0.7427640 -1.8481220 F -0.4721860 2.2722730 1.7799710 C -1.6928820 0.3094380 -2.0697030 C -5.5536970 -0.7013450 1.0459630 C -0.8316200 -0.8206440 2.8012930 F 2.8973600 -0.1257150 1.3070390 F 1.2774970 -4.6861910 -1.1793670 F 4.5200530 -2.2616500 1.2492370 F 3.1392600 3.2310630 -2.1771250 F 0.5017200 4.7451070 1.4355650 Cl -4.6961560 0.0732660 -1.7796950

- S55 -

H 3.5838570 -4.3685260 0.0115010 H 2.2270070 5.0319980 -0.5100060 H -3.5292590 -1.0232470 2.8149500 H -2.0063890 -0.4569560 -2.7830660 H -2.0931530 1.2630580 -2.4238150 H -0.6035700 0.3629230 -2.1096630 H -5.7493920 -0.9844460 2.0810760 H -6.0913790 0.2266130 0.8323670 H -5.9759000 -1.4681760 0.3904670 H -0.3047250 0.1073950 3.0432830 H -1.3601180 -1.1448610 3.6993070 H -0.0769600 -1.5776630 2.5677270 44 2c-hydride B 0.3335610 0.0165250 0.8915790 C 1.5087720 -1.0430470 0.4491330 C 0.4950870 1.5241870 0.2398390 C -1.2214230 -0.4735970 0.7019950 C 1.2491650 1.8961870 -0.8703230 C 1.3212500 3.2023150 -1.3407000 C 0.6321620 4.2239000 -0.7113430 C -0.1277070 3.8891320 0.3982860 C -0.1865410 2.5788730 0.8514580 C 1.3223460 -2.3418190 -0.0217490 C 2.3777710 -3.2137020 -0.2776590 C 3.6897170 -2.8322970 -0.0657740 C 3.9084890 -1.5488690 0.4110340 C 2.8461490 -0.6950320 0.6607730 C -2.0415710 -0.7160680 1.8267270 C -3.3918990 -1.0337280 1.6676490 C -4.0038660 -1.1202180 0.4197810 C -3.1777370 -0.8934420 -0.6790340 C -1.8151470 -0.5927040 -0.5789440 F 1.9524070 0.9683880 -1.5700960 F 3.1504870 0.5371040 1.1326720 F 0.0821250 -2.8276850 -0.2648300 C -1.0070530 -0.4305420 -1.8440880 C -5.4691890 -1.4458720 0.2891840 C -1.5069430 -0.6377730 3.2410760 F -0.9482110 2.3481680 1.9475230 F 2.0743320 3.4815400 -2.4325810 F -0.8167860 4.8590110 1.0485420 F 5.1788740 -1.1316990 0.6376330 F 2.1152450 -4.4603130 -0.7421530 Cl -3.9328930 -0.9959530 -2.3045950 H 0.5629950 0.1921090 2.0655950 H 0.6824280 5.2415420 -1.0719770 H 4.5109270 -3.5062050 -0.2650320 H -4.0014000 -1.2145810 2.5496170

- S56 -

H -1.1853980 -1.2693010 -2.5212630 H -1.2888900 0.4821830 -2.3799920 H 0.0562960 -0.3875870 -1.6415750 H -5.9177720 -1.5915870 1.2745540 H -6.0125010 -0.6446560 -0.2217670 H -5.6261700 -2.3553320 -0.2993470 H -0.6397100 -1.2879400 3.3782220 H -1.1814320 0.3776750 3.4767100 H -2.2752580 -0.9336800 3.9621560 43 2d B 0.0596260 -0.0439890 0.1701650 C 0.3147910 1.5006720 0.0413430 C 1.2633950 -1.0443430 0.0933650 C -1.3980900 -0.5726240 0.3778740 C 1.1312780 -2.3090980 -0.4929920 C 2.1775880 -3.2201210 -0.5505630 C 3.4049440 -2.8833700 0.0091020 C 3.5800730 -1.6399530 0.6089880 C 2.5209260 -0.7461420 0.6311490 C -0.3762830 2.4336910 0.8197040 C -0.1824380 3.8031530 0.6951240 C 0.7151180 4.2795960 -0.2536270 C 1.4165710 3.3871400 -1.0588380 C 1.2145620 2.0265100 -0.8903180 C -1.8055640 -1.0569250 1.6345460 C -3.1174950 -1.4897470 1.8011520 C -4.0480190 -1.4773660 0.7599600 C -3.6066780 -1.0042010 -0.4778490 C -2.3028660 -0.5485120 -0.6975370 F -0.0223320 -2.6766500 -1.0652200 F 1.8959440 1.1986490 -1.7027620 F 0.9038230 5.5898900 -0.3929520 F -1.2364060 2.0253050 1.7645020 C -1.8661930 -0.1034710 -2.0723350 C -5.4571450 -1.9609030 0.9753490 C -0.8495140 -1.0574290 2.8051010 F 2.7340850 0.4361100 1.2320820 F 4.4140100 -3.7497700 -0.0296470 F 2.0202300 -4.4099310 -1.1365390 F 4.7589930 -1.3256950 1.1528930 F 2.2680850 3.8496930 -1.9782830 F -0.8437110 4.6633410 1.4742560 Cl -4.7490320 -0.9907240 -1.8313610 H -3.4361570 -1.8499600 2.7742110 H -1.9875480 -0.9148830 -2.7945420 H -2.4642380 0.7385180 -2.4305600 H -0.8162620 0.1947640 -2.0912940 H -5.6014090 -2.2889950 2.0055760

- S57 -

H -6.1812030 -1.1707570 0.7581170 H -5.6921200 -2.7955680 0.3089810 H -0.5631650 -0.0352680 3.0717380 H -1.2985810 -1.5156930 3.6877630 H 0.0678520 -1.6077280 2.5751640 44 2d-hydride B 0.1593570 -0.0172590 0.9459610 C 1.6522780 -0.5257210 0.4796500 C -0.2687410 1.4629850 0.3491550 C -1.0851060 -1.0595120 0.7101350 C 0.2893410 2.1440690 -0.7276210 C -0.1339120 3.3976030 -1.1584160 C -1.1704220 4.0328750 -0.4929130 C -1.7643590 3.3987700 0.5899890 C -1.3067790 2.1476050 0.9823900 C 1.9791510 -1.7731850 -0.0457030 C 3.2843870 -2.1742560 -0.3265590 C 4.3380280 -1.3121890 -0.0729850 C 4.0677290 -0.0582590 0.4594350 C 2.7536760 0.2973010 0.7242650 C -1.7489360 -1.6469900 1.8103170 C -2.8724560 -2.4526870 1.6154720 C -3.4026760 -2.7144560 0.3547040 C -2.7271830 -2.1403830 -0.7203030 C -1.5858510 -1.3426900 -0.5845220 F 1.2991910 1.5931570 -1.4468880 F 2.5665560 1.5293650 1.2488960 F 5.6065570 -1.6829890 -0.3366810 F 1.0249940 -2.6883350 -0.3272830 C -0.9019030 -0.8276700 -1.8284980 C -4.6290800 -3.5733070 0.1860920 C -1.2867040 -1.4294440 3.2355630 F -1.9286270 1.5992190 2.0506020 F -1.5975470 5.2472050 -0.8913630 F 0.4472600 4.0018740 -2.2146460 F -2.7712130 4.0107440 1.2464750 F 5.0863470 0.7888060 0.7139560 F 3.5356530 -3.3954690 -0.8416640 Cl -3.3823470 -2.4555890 -2.3606450 H 0.3019370 0.1870100 2.1285420 H -3.3659150 -2.8919020 2.4788650 H -0.7427010 -1.6403230 -2.5412840 H -1.5136250 -0.0723910 -2.3334910 H 0.0627360 -0.3871260 -1.6067450 H -4.9881050 -3.9222830 1.1569410 H -5.4383520 -3.0219900 -0.3029450 H -4.4224460 -4.4470440 -0.4399100 H -0.2357520 -1.6997830 3.3621040

- S58 -

H -1.3788050 -0.3782950 3.5174140 H -1.8812950 -2.0295000 3.9311580 43 3a B 0.8922320 0.0006060 -0.0000650 C 1.6645110 -1.3574840 -0.0972610 C 1.6642650 1.3590520 0.0930050 C -0.6815250 0.0000730 0.0020500 C 1.2230240 2.4398690 0.8683650 C 1.8734620 3.6613550 0.9404100 C 3.0277480 3.8452400 0.1852670 C 3.5178790 2.8176110 -0.6172160 C 2.8353430 1.6142770 -0.6333220 C 1.2226350 -2.4364910 -0.8745690 C 1.8733820 -3.6575830 -0.9503920 C 3.0287330 -3.8428130 -0.1971990 C 3.5195670 -2.8168930 0.6070770 C 2.8365790 -1.6138940 0.6268680 C -1.3740000 0.3288540 -1.1726200 C -2.7680770 0.3154090 -1.1344020 C -3.5146020 -0.0026380 0.0081910 C -2.7691640 -0.3198360 1.1502410 C -1.3709960 -0.3287930 1.1769780 F 0.1178790 2.2856200 1.6277010 F 3.3163550 -0.6405660 1.4352620 F 0.1163870 -2.2806090 -1.6322170 C -0.6191220 -0.6387050 2.4482860 C -5.0201290 0.0072270 -0.0325000 C -0.6324480 0.6419250 -2.4486000 F 3.3145870 0.6395660 -1.4402680 H 1.4716420 4.4370300 1.5785850 H 4.4067150 2.9319470 -1.2232390 H 4.4092350 -2.9323710 1.2116580 H 1.4710250 -4.4319310 -1.5898380 H 3.5482670 4.7945790 0.2208790 H 3.5495300 -4.7918850 -0.2357200 Cl -3.6484680 0.7159150 -2.6188530 Cl -3.6161230 -0.7274170 2.6549100 H -0.8705750 0.0814810 3.2306020 H -0.8678950 -1.6332190 2.8274470 H 0.4614600 -0.5965680 2.2993810 H -5.3867870 0.9965010 -0.3184240 H -5.3848770 -0.6962750 -0.7855190 H -5.4527170 -0.2583230 0.9277750 H 0.4493230 0.6062180 -2.3076760 H -0.8863330 -0.0800750 -3.2285540 H -0.8903880 1.6347260 -2.8262420 44

- S59 -

3a-hydride B -0.9122610 -0.0557030 -0.7515140 C -1.9209620 -1.2733180 -0.3201040 C -1.4012920 1.4533080 -0.3068490 C 0.6712600 -0.2266500 -0.3190340 C -2.3627830 1.8201640 0.6327470 C -2.7362830 3.1235720 0.9410170 C -2.1151960 4.1730500 0.2726840 C -1.1408140 3.8898710 -0.6812580 C -0.8255040 2.5618780 -0.9342740 C -1.5882460 -2.4709570 0.3125110 C -2.4698910 -3.5171380 0.5726010 C -3.7954670 -3.3936590 0.1749840 C -4.2039740 -2.2301060 -0.4736730 C -3.2673230 -1.2326770 -0.6983000 C 1.6675130 -0.4373320 -1.3046150 C 3.0109150 -0.4136690 -0.9190210 C 3.4578780 -0.2121880 0.3921220 C 2.4397110 -0.0554450 1.3344080 C 1.0757900 -0.0721740 1.0253630 F -3.0018910 0.8432410 1.3429280 F -3.7184450 -0.1235380 -1.3462970 F -0.3067000 -2.6742620 0.7321310 C 0.0663900 0.0478480 2.1419380 C 4.9285050 -0.1798840 0.7234030 C 1.2772580 -0.6745940 -2.7459980 F 0.1293020 2.3462650 -1.8830490 H -3.4982860 3.2870080 1.6933500 H -0.6250300 4.6680320 -1.2305470 H -5.2237590 -2.0800890 -0.8067230 H -2.0974370 -4.4000510 1.0777830 H -1.0059210 -0.0297220 -1.9559170 H -2.3839180 5.1999260 0.4939790 H -4.5031710 -4.1924130 0.3672670 Cl 4.2995860 -0.6267380 -2.1567410 Cl 2.9071590 0.1967430 3.0513910 H 0.2995070 -0.6590400 2.9418680 H 0.0777020 1.0511160 2.5803040 H -0.9395700 -0.1582550 1.7982000 H 5.4323860 0.6133250 0.1636550 H 5.0955160 -0.0131740 1.7841740 H 5.4093450 -1.1206140 0.4399360 H 0.4560080 -1.3885840 -2.8017360 H 0.9195490 0.2565360 -3.1929240 H 2.1084310 -1.0503220 -3.3394810 44 3b B -0.7301360 -0.0417240 -0.6544010 C -1.8251750 -1.2039090 -0.2809280

- S60 -

C -1.0879710 1.4613330 -0.0799030 C 0.8438460 -0.3720970 -0.2931420 C -1.9917560 1.8220450 0.9202420 C -2.2522880 3.1200800 1.3349670 C -1.5747510 4.1720770 0.7241450 C -0.6656130 3.8725060 -0.2742070 C -0.4394200 2.5542970 -0.6555500 C -1.5732970 -2.4664720 0.2608630 C -2.5317820 -3.4506970 0.4699780 C -3.8534530 -3.1967480 0.1169690 C -4.1565390 -1.9639960 -0.4333560 C -3.1643700 -1.0111830 -0.6251670 C 1.7857520 -0.5936000 -1.3281860 C 3.1382310 -0.7076610 -0.9932030 C 3.6417450 -0.6360220 0.3109930 C 2.6717610 -0.4640900 1.3002140 C 1.3019820 -0.3476270 1.0423160 F -2.6807380 0.8416760 1.5764930 F -3.5491870 0.1627410 -1.1778590 F -0.3045700 -2.7974280 0.6320670 C 0.3423010 -0.2280190 2.2018340 C 5.1197730 -0.7463050 0.5876000 C 1.3313210 -0.6963520 -2.7667220 F 0.4620840 2.3576300 -1.6470940 H -2.9746410 3.2891300 2.1235270 F 0.0123020 4.8729840 -0.8941360 F -5.4357040 -1.6802150 -0.7942700 H -2.2298450 -4.3960070 0.9031010 H -0.8581560 0.0862240 -1.8482950 H -1.7354000 5.2046210 1.0067000 H -4.6407540 -3.9259660 0.2596120 Cl 4.3620720 -0.9381450 -2.2894350 Cl 3.2126280 -0.3737750 3.0103470 H 0.5433620 -1.0054590 2.9426530 H 0.4482420 0.7375510 2.7070780 H -0.6876500 -0.3308990 1.8836230 H 5.6691040 0.0406650 0.0631590 H 5.3346380 -0.6680390 1.6499120 H 5.5106680 -1.7008670 0.2237330 H 0.4451730 -1.3261140 -2.8392360 H 1.0515410 0.2915120 -3.1421150 H 2.1050350 -1.1069380 -3.4123120 43 3b-hydride B 0.6738500 -0.0169600 -0.1396030 C 1.3469550 1.3979530 -0.1823550 C 1.5497430 -1.3158740 -0.1789190 C -0.8906910 -0.1329800 -0.0547430 C 1.1591770 -2.4789480 -0.8576100

- S61 -

C 1.9070950 -3.6439660 -0.8827950 C 3.1089870 -3.6854570 -0.1819510 C 3.5335090 -2.5646450 0.5116760 C 2.7689490 -1.4059240 0.5004790 C 0.8599020 2.4800280 0.5574250 C 1.4419860 3.7417520 0.4971570 C 2.5272230 3.9726570 -0.3293710 C 3.0391800 2.9295280 -1.0982600 C 2.4502560 1.6830950 -0.9988570 C -1.4956900 -0.4294750 1.1754180 C -2.8870800 -0.5202400 1.2130820 C -3.7110700 -0.3368220 0.0943440 C -3.0504150 -0.0462530 -1.1058170 C -1.6602260 0.0628760 -1.2096040 F 0.0088210 -2.4663900 -1.5627080 F 2.9492090 0.6910370 -1.7728120 F -0.1796940 2.3165820 1.3908230 C -0.9979550 0.3375940 -2.5375210 C -5.2075080 -0.4521130 0.2182150 C -0.6696710 -0.5980320 2.4265060 F 3.2175490 -0.3547330 1.2110060 H 1.5456860 -4.4959970 -1.4424870 F 4.6865680 -2.5880610 1.2028580 H 3.8800510 3.0723930 -1.7632930 F 0.9382310 4.7337880 1.2513250 H 3.7235920 -4.5762380 -0.1623310 H 2.9585800 4.9648620 -0.3608040 Cl -3.6581010 -0.8800210 2.7655490 Cl -3.9988850 0.1927170 -2.5845770 H -1.2340430 -0.4501120 -3.2569950 H -1.3384500 1.2837450 -2.9659120 H 0.0892430 0.3817680 -2.4467900 H -5.4835620 -1.4427560 0.5885900 H -5.5856660 0.2743080 0.9422540 H -5.7066010 -0.2858780 -0.7320180 H 0.3982630 -0.4931770 2.2251380 H -0.9384010 0.1557910 3.1704870 H -0.8312760 -1.5782660 2.8822130 43 3c B -0.4875240 -0.0004410 0.0012090 C -1.2723020 -1.3590180 -0.0360950 C -1.2723680 1.3582460 0.0346370 C 1.0806280 -0.0003600 0.0026090 C -0.8434780 2.4808450 -0.6803810 C -1.5307140 3.6877920 -0.6319970 C -2.6621590 3.8226020 0.1552720 C -3.1010090 2.7289570 0.8851420 C -2.4223030 1.5213800 0.8135280

- S62 -

C -0.8449000 -2.4829050 0.6779270 C -1.5320010 -3.6897900 0.6259750 C -2.6617120 -3.8233280 -0.1639930 C -3.0989800 -2.7284900 -0.8929990 C -2.4204990 -1.5209880 -0.8178940 C 1.7689520 0.2326960 1.2010380 C 3.1670910 0.2258170 1.1730940 C 3.9106290 0.0016750 0.0074890 C 3.1648290 -0.2232020 -1.1578820 C 1.7706230 -0.2334500 -1.1962000 F 0.2371940 2.4077660 -1.4735880 F -2.8726490 -0.4945920 -1.5633720 F 0.2340420 -2.4112990 1.4734490 C 1.0274440 -0.4413260 -2.4924950 C 5.4158380 -0.0048450 -0.0345800 C 1.0167280 0.4379970 2.4930900 F -2.8759730 0.4959730 1.5594650 F -1.0892450 4.7284620 -1.3534420 F -4.1872720 2.8353230 1.6647170 F -4.1834720 -2.8336090 -1.6752100 F -1.0920440 -4.7316860 1.3465510 Cl 4.0128530 0.5107910 2.7033770 Cl 4.0422850 -0.5028590 -2.6684370 H -3.1927210 4.7639280 0.2005800 H -3.1921350 -4.7645990 -0.2120410 H 1.2861000 0.3368120 -3.2145550 H 1.2782190 -1.4035590 -2.9462220 H -0.0548770 -0.4077680 -2.3512030 H 5.8494550 0.1816380 0.9435470 H 5.7816100 -0.9676150 -0.4005850 H 5.7793830 0.7576290 -0.7283750 H -0.0645230 0.3998990 2.3441290 H 1.2727000 -0.3391520 3.2170920 H 1.2598160 1.4012430 2.9487340 44 3c-hydride B -0.5221310 -0.0412820 -0.7814940 C -1.6429580 -1.1810010 -0.4122500 C -0.9009020 1.4865850 -0.2901730 C 1.0301400 -0.3578490 -0.3343060 C -1.8558230 1.8697810 0.6476200 C -2.1101990 3.1961040 0.9772730 C -1.4102640 4.2253840 0.3729470 C -0.4517370 3.8790870 -0.5664130 C -0.2133750 2.5489180 -0.8820090 C -1.4070080 -2.4064600 0.2082360 C -2.4010100 -3.3633800 0.3970320 C -3.6955030 -3.1452800 -0.0368310 C -3.9610050 -1.9381750 -0.6653870

- S63 -

C -2.9591980 -0.9980180 -0.8457690 C 2.0155320 -0.6351870 -1.3118220 C 3.3589960 -0.7179360 -0.9205390 C 3.7998970 -0.5701160 0.3988510 C 2.7835640 -0.3538520 1.3325310 C 1.4277580 -0.2582530 1.0177690 F -2.5837580 0.9356610 1.3123140 F -3.3021650 0.1505230 -1.4742680 F -0.1768750 -2.7290330 0.6743080 C 0.4238860 -0.0807920 2.1310720 C 5.2434050 -0.6400640 0.8289330 C 1.6178720 -0.8313570 -2.7581660 F 0.7337430 2.3031450 -1.8175130 F -3.0531380 3.4872170 1.9058620 F 0.2550530 4.8556630 -1.1851710 F -5.2157450 -1.6822170 -1.1098190 F -2.0949310 -4.5292860 1.0166060 Cl 4.6140350 -1.0020000 -2.1767190 Cl 3.2805430 -0.1748020 3.0443450 H -0.5977360 0.0391300 -1.9831610 H -1.6015220 5.2588140 0.6252170 H -4.4697640 -3.8850920 0.1095930 H 0.6030610 -0.8119000 2.9227630 H 0.5040980 0.9130390 2.5835750 H -0.5933220 -0.2118570 1.7828160 H 5.9075640 -0.8087240 -0.0139300 H 5.5404260 0.2882240 1.3251710 H 5.3896190 -1.4461200 1.5537400 H 0.7081890 -1.4264710 -2.8227180 H 1.4021220 0.1343440 -3.2240880 H 2.3980360 -1.3252200 -3.3336160 43 3d B -0.2953520 -0.0007420 0.0010340 C -1.0761470 -1.3603760 -0.0077360 C -1.0739280 1.3603530 0.0062490 C 1.2736640 -0.0014860 0.0024510 C -0.6106640 2.4846900 -0.6864560 C -1.2754300 3.7036060 -0.6651920 C -2.4361200 3.8331350 0.0890710 C -2.9266940 2.7453090 0.8052270 C -2.2499820 1.5376350 0.7435910 C -0.6141310 -2.4876180 0.6813700 C -1.2809730 -3.7053430 0.6572280 C -2.4425980 -3.8308000 -0.0962840 C -2.9320280 -2.7401360 -0.8088640 C -2.2532560 -1.5337440 -0.7445610 C 1.9622840 0.2446670 1.1980760 C 3.3604620 0.2373260 1.1707880

- S64 -

C 4.1041660 -0.0001360 0.0078820 C 3.3585390 -0.2380480 -1.1550480 C 1.9642750 -0.2482070 -1.1932230 F 0.4925060 2.4103380 -1.4433580 F -2.7496640 -0.5140470 -1.4662830 F -3.0864210 -4.9942050 -0.1378200 F 0.4898040 -2.4175630 1.4373200 C 1.2216130 -0.4685810 -2.4877570 C 5.6093260 -0.0073860 -0.0338400 C 1.2101610 0.4623220 2.4881920 F -2.7471000 0.5204290 1.4684590 F -3.0780030 4.9977460 0.1278840 F -0.8150440 4.7476140 -1.3587910 F -4.0341370 2.8784110 1.5396040 F -4.0403810 -2.8693330 -1.5425630 F -0.8216520 -4.7521240 1.3473120 Cl 4.2055370 0.5385680 2.6977910 Cl 4.2357320 -0.5342270 -2.6620560 H 1.4778780 0.3042650 -3.2164800 H 1.4748570 -1.4333590 -2.9346140 H 0.1391960 -0.4378000 -2.3452650 H 6.0429390 0.1898530 0.9421520 H 5.9748920 -0.9742240 -0.3891310 H 5.9730400 0.7472720 -0.7360250 H 0.1288490 0.4261180 2.3379650 H 1.4641730 -0.3091330 3.2191000 H 1.4549720 1.4284300 2.9367770 44 3d-hydride B -0.3296640 -0.0585630 -0.8115040 C -1.6088590 -1.0116550 -0.4226740 C -0.4878920 1.5210860 -0.3586810 C 1.1541140 -0.5886320 -0.3382830 C -1.3834690 2.0635810 0.5563560 C -1.4584520 3.4196850 0.8585620 C -0.6033550 4.3072670 0.2244550 C 0.3119760 3.8195620 -0.6988010 C 0.3483490 2.4576050 -0.9681590 C -1.5607030 -2.2382880 0.2340650 C -2.6785060 -3.0432690 0.4472470 C -3.9181230 -2.6326820 -0.0139580 C -4.0200960 -1.4194430 -0.6826460 C -2.8807430 -0.6521890 -0.8732460 C 2.0922330 -1.0402120 -1.2968140 C 3.4079090 -1.3036490 -0.8909590 C 3.8591670 -1.1789080 0.4272990 C 2.8808740 -0.7877760 1.3447130 C 1.5551530 -0.5056270 1.0138500 F -2.2443450 1.2664990 1.2372860

- S65 -

F -3.0514630 0.5131000 -1.5362140 F -5.0096870 -3.3973830 0.1815590 F -0.3981460 -2.7266760 0.7221710 C 0.5819150 -0.1502430 2.1118250 C 5.2750170 -1.4441260 0.8727410 C 1.6769780 -1.2285880 -2.7393150 F 1.2565440 2.0577800 -1.8854720 F -0.6572720 5.6244920 0.5008440 F -2.3468430 3.8817440 1.7612140 F 1.1448560 4.6763220 -1.3229620 F -5.2218860 -1.0112810 -1.1379900 F -2.5681950 -4.2196780 1.0969360 Cl 4.6128190 -1.8043280 -2.1266120 Cl 3.3893850 -0.6289810 3.0540490 H -0.3830460 0.0028700 -2.0150460 H 0.6493830 -0.8743490 2.9269660 H 0.8024810 0.8348610 2.5359090 H -0.4418110 -0.1442220 1.7579000 H 5.9109940 -1.7371730 0.0423530 H 5.7024780 -0.5525680 1.3402230 H 5.2983120 -2.2372690 1.6255230 H 0.6822380 -1.6679800 -2.7925580 H 1.6278220 -0.2619140 -3.2490600 H 2.3689800 -1.8684600 -3.2829590 34 4a B 0.0000000 0.0000000 -0.1495370 C 1.3068190 0.4080540 -0.8948860 C -1.3068190 -0.4080540 -0.8948860 C 0.0000000 0.0000000 1.4300420 C -0.0166240 -1.1820260 2.1721780 C -0.0122000 -1.2077670 3.5608510 C 0.0000000 0.0000000 4.2521340 C 0.0122000 1.2077670 3.5608510 C 0.0166240 1.1820260 2.1721780 Cl 0.0000000 -2.7186720 1.2997650 H -0.0151690 -2.1539900 4.0854390 H 0.0000000 0.0000000 5.3356010 H 0.0151690 2.1539900 4.0854390 Cl 0.0000000 2.7186720 1.2997650 C -2.5863770 -0.1581470 -0.3777210 C -3.7641370 -0.5470420 -0.9950940 C -3.6849610 -1.2482530 -2.1941450 C -2.4467380 -1.5417980 -2.7602660 C -1.3047000 -1.1124530 -2.1081150 F -2.6975680 0.5290870 0.7776380 H -4.7099240 -0.2982500 -0.5326420 H -4.5928070 -1.5685060 -2.6909940 H -2.3514270 -2.0920270 -3.6867890

- S66 -

F -0.1190530 -1.4289250 -2.6696740 C 2.5863770 0.1581470 -0.3777210 C 3.7641370 0.5470420 -0.9950940 C 3.6849610 1.2482530 -2.1941450 C 2.4467380 1.5417980 -2.7602660 C 1.3047000 1.1124530 -2.1081150 F 2.6975680 -0.5290870 0.7776380 H 4.7099240 0.2982500 -0.5326420 H 4.5928070 1.5685060 -2.6909940 H 2.3514270 2.0920270 -3.6867890 F 0.1190530 1.4289250 -2.6696740 35 4a-hydride B -0.0435110 0.1138610 0.6050440 C -1.5921440 -0.3706440 0.4134710 C 1.0805110 -0.9836880 0.1192130 C 0.2670340 1.6109210 0.0324810 C 0.9545960 -1.9325230 -0.9100140 C 1.9030690 -2.9036950 -1.2211250 C 3.0904630 -2.9489120 -0.5029520 C 3.3139980 -2.0074310 0.4932640 C 2.3273050 -1.0645830 0.7672080 C -2.5894330 0.2464950 -0.3394040 C -3.9158270 -0.1664960 -0.4033930 C -4.3069760 -1.2857780 0.3241090 C -3.3640200 -1.9601000 1.0957470 C -2.0602100 -1.4843440 1.1136780 C 0.9705360 1.9311880 -1.1261060 C 1.2591840 3.2213410 -1.5583140 C 0.8115680 4.2971380 -0.7990560 C 0.0870940 4.0558040 0.3655830 C -0.1595130 2.7398740 0.7333730 Cl -0.4626300 -1.9200400 -1.9880480 Cl 2.7651670 0.1249590 2.0213200 H 1.8182020 3.3547150 -2.4766040 H -0.2915860 4.8578240 0.9876810 F -0.8886140 2.5614530 1.8690600 H -4.6076780 0.3883700 -1.0256170 H -3.6130060 -2.8404570 1.6758500 F -1.1748870 -2.1852710 1.8750270 F -2.2720260 1.3264320 -1.1068270 F 1.4182530 0.9249390 -1.9280200 H 0.0817340 0.1847940 1.8050060 H 1.7115760 -3.6015400 -2.0264410 H 3.8410080 -3.6986790 -0.7289720 H 4.2400960 -1.9958450 1.0539180 H -5.3342780 -1.6314140 0.2879630 H 1.0204010 5.3139290 -1.1133690

- S67 -

34 4b B -0.0460290 -0.0623930 0.1035630 C 0.7562550 1.2763160 0.1239160 C 0.7472100 -1.4203160 -0.0130770 C -1.6036220 -0.1097810 0.1923010 C 0.7270800 -2.1915620 -1.1763540 C 1.4227690 -3.3864630 -1.3063370 C 2.1691930 -3.8465000 -0.2255250 C 2.2192110 -3.1179700 0.9593030 C 1.5148060 -1.9237830 1.0384340 C 0.3617510 2.3888000 0.8832540 C 1.0876810 3.5618270 0.9683670 C 2.2762220 3.6682180 0.2493360 C 2.7062590 2.6013450 -0.5188820 C 1.9629830 1.4274960 -0.5694700 C -2.2939580 -1.1616420 0.8134590 C -3.6742870 -1.2495130 0.8714790 C -4.4353630 -0.2548390 0.2647270 C -3.8001660 0.7996590 -0.3692400 C -2.4140870 0.8689620 -0.3948560 Cl -0.1914380 -1.5918290 -2.5609840 Cl 1.5542850 -1.0167020 2.5538440 H -4.1330010 -2.0854270 1.3818460 F -4.5198850 1.7656600 -0.9673780 F -1.8569390 1.9058110 -1.0403430 H 0.7219980 4.3710470 1.5856600 F 3.8479500 2.6870810 -1.2241080 F 2.4303750 0.4341360 -1.3403930 F -0.7760120 2.3095530 1.6050890 F -1.5869890 -2.1368020 1.4200600 H 1.3819040 -3.9392650 -2.2354130 H 2.7159900 -4.7782130 -0.3073210 H 2.7907300 -3.4676170 1.8087480 H 2.8753740 4.5693370 0.2745790 H -5.5173890 -0.2833520 0.2740950 35 4b-hydride B 0.0763540 0.1590450 -0.6098820 C -1.3946750 -0.5481280 -0.5659470 C 0.1213210 1.7270460 -0.1172480 C 1.2603070 -0.7122670 0.1046970 C -0.7467550 2.3773560 0.7768640 C -0.6959720 3.7335290 1.0917680 C 0.2887900 4.5289400 0.5224190 C 1.2145970 3.9488730 -0.3349890 C 1.1125430 2.5910170 -0.6221930 C -1.7532000 -1.6828600 0.1538550 C -3.0159770 -2.2671640 0.0742590

- S68 -

C -3.9963180 -1.7340690 -0.7394910 C -3.6899980 -0.5939410 -1.4824730 C -2.4214980 -0.0500500 -1.3749550 C 1.7017850 -0.5537150 1.4186290 C 2.7370250 -1.2688860 2.0012340 C 3.3971310 -2.2344630 1.2436260 C 2.9878890 -2.4391890 -0.0604400 C 1.9444720 -1.6951750 -0.6043540 Cl -1.9991970 1.4715090 1.6605270 Cl 2.3888930 1.9605530 -1.6944130 H 3.0058140 -1.0715410 3.0313250 F 3.6078320 -3.3784340 -0.8240320 F 1.6060220 -1.9743010 -1.8840140 F -3.2828890 -3.3747520 0.8161450 H -4.4172270 -0.1256520 -2.1337650 F -2.1765870 1.0695910 -2.1086460 F -0.8785270 -2.2693960 1.0060250 F 1.0777380 0.3569890 2.2142060 H 0.3361000 0.1916350 -1.7881850 H -1.4154310 4.1490160 1.7858430 H 0.3433480 5.5867130 0.7558150 H 2.0095920 4.5344610 -0.7788750 H -4.9694860 -2.2065890 -0.7807160 H 4.2096100 -2.8267410 1.6453080 34 4c B 0.0000000 0.0000000 0.1721240 C 0.0308630 1.3683100 -0.5821960 C 0.0000000 0.0000000 1.7465850 C -0.0308630 -1.3683100 -0.5821960 C -0.7027120 -2.4807860 -0.0611770 C -0.6971830 -3.7109370 -0.7068250 C 0.0000000 -3.8805660 -1.8909720 C 0.6826440 -2.7983000 -2.4240270 C 0.6579660 -1.5677570 -1.7849760 F -1.4039230 -2.3791710 1.0778620 F -1.3714790 -4.7405020 -0.1728340 H 0.0110460 -4.8392200 -2.3915310 F 1.3715600 -2.9388350 -3.5666500 F 1.3495410 -0.5598130 -2.3412680 C 1.1073840 -0.4187110 2.4863830 C 1.1325350 -0.4223000 3.8747090 C 0.0000000 0.0000000 4.5649180 C -1.1325350 0.4223000 3.8747090 C -1.1073840 0.4187110 2.4863830 Cl 2.5556710 -0.9210080 1.6095780 H 2.0211440 -0.7456910 4.4002400 H 0.0000000 0.0000000 5.6482750 H -2.0211440 0.7456910 4.4002400

- S69 -

Cl -2.5556710 0.9210080 1.6095780 C -0.6579660 1.5677570 -1.7849760 C -0.6826440 2.7983000 -2.4240270 C 0.0000000 3.8805660 -1.8909720 C 0.6971830 3.7109370 -0.7068250 C 0.7027120 2.4807860 -0.0611770 F -1.3495410 0.5598130 -2.3412680 F -1.3715600 2.9388350 -3.5666500 H -0.0110460 4.8392200 -2.3915310 F 1.3714790 4.7405020 -0.1728340 F 1.4039230 2.3791710 1.0778620 35 4c-hydride B 0.0091620 0.2282030 0.6440540 C 1.3653030 -0.6289930 0.3303110 C 0.0360790 1.7866410 0.1311430 C -1.3684220 -0.5363950 0.2072430 C 0.7561460 2.3203450 -0.9509860 C 0.8060020 3.6716450 -1.2842430 C 0.0784000 4.5844400 -0.5330490 C -0.7014990 4.1260910 0.5206780 C -0.7079800 2.7662090 0.8157390 C 1.4542670 -1.7911120 -0.4315900 C 2.6406970 -2.4979370 -0.5907960 C 3.8126450 -2.0710780 0.0092300 C 3.7548360 -0.9157040 0.7723690 C 2.5616530 -0.2254730 0.9249840 C -2.1158620 -0.2564550 -0.9331130 C -3.3070620 -0.9076090 -1.2311590 C -3.8081710 -1.8916830 -0.3965990 C -3.0774190 -2.2008380 0.7390650 C -1.8909850 -1.5388020 1.0231200 Cl 1.6449060 1.2564520 -2.0675600 Cl -1.7922570 2.2967940 2.1489220 F -3.9872550 -0.5826290 -2.3584090 F -3.5309970 -3.1646070 1.5791140 F -1.2322820 -1.9149830 2.1432330 F 2.6554680 -3.6200130 -1.3522010 F 4.8809440 -0.4601530 1.3753090 F 2.5914130 0.8984760 1.6774200 F 0.3737800 -2.2730700 -1.0916050 F -1.6920840 0.6710930 -1.8226140 H -0.0106970 0.2863530 1.8491400 H 1.3981510 3.9930890 -2.1314550 H 0.1053540 5.6407610 -0.7769890 H -1.3017600 4.8074920 1.1098590 H 4.7374710 -2.6166500 -0.1146060 H -4.7319940 -2.4040390 -0.6256930

- S70 -

34 5b B -0.3452330 0.0246700 0.2274320 C -1.0119070 1.4167900 0.0042310 C 1.2153690 -0.0377790 0.4673750 C -1.1531740 -1.3102850 0.2316030 C 2.0759260 -0.5112060 -0.5264200 C 3.4565290 -0.5749980 -0.3246610 C 3.9902750 -0.1616410 0.8936840 C 3.1586850 0.3128130 1.8989550 C 1.7906940 0.3705300 1.6680240 C -2.3040940 1.7232610 0.4602100 C -2.8924570 2.9673270 0.3325550 C -2.1798110 3.9847910 -0.2979680 C -0.9034440 3.7333620 -0.7683000 C -0.3314450 2.4764730 -0.6084710 C -0.7970680 -2.4106740 1.0260560 C -1.4719920 -3.6191710 1.0160650 C -2.5558940 -3.7744320 0.1571820 C -2.9399450 -2.7206810 -0.6550420 C -2.2537340 -1.5150910 -0.6091750 Cl 1.3619180 -0.9816080 -2.0588940 Cl 0.7316390 0.9458110 2.9550000 H -1.1447890 -4.4164550 1.6694260 F -3.9793700 -2.8557350 -1.4972170 F -2.6602300 -0.5379260 -1.4347980 H -3.8892110 3.1272420 0.7204890 F -0.2016450 4.7010790 -1.3829300 F 0.9062930 2.2965590 -1.0930290 F -3.0125540 0.7648850 1.0927880 F 0.2435310 -2.2912290 1.8759210 Cl 4.5431450 -1.1593050 -1.5630240 H 5.0601250 -0.2135390 1.0461980 H 3.5674370 0.6310590 2.8486240 H -2.6008310 4.9729980 -0.4314700 H -3.1098010 -4.7029410 0.1051470 35 5b-hydride B -0.3458630 0.0397680 0.9469070 C -0.9612240 -1.4088680 0.4744560 C 1.2676170 0.0466730 0.6123900 C -1.1639250 1.3606640 0.4425210 C 1.7728770 -0.1372730 -0.6925400 C 3.1387260 -0.2302450 -0.9717050 C 4.0710440 -0.1254250 0.0525970 C 3.6252410 0.0870530 1.3457500 C 2.2578400 0.1726990 1.5966520 C -1.9125970 -1.6522170 -0.5115730 C -2.3959790 -2.9246920 -0.8083680

- S71 -

C -1.9361880 -4.0362200 -0.1297260 C -0.9746020 -3.8521770 0.8626680 C -0.5274540 -2.5676670 1.1280090 C -0.6179640 2.5094230 -0.1221050 C -1.3726480 3.6382300 -0.4416820 C -2.7296280 3.6802840 -0.1947760 C -3.3262430 2.5633290 0.3906650 C -2.5378280 1.4670880 0.6916770 Cl 0.6438880 -0.2057110 -2.0395990 Cl 1.8417090 0.4893240 3.2951150 F -0.7527850 4.7108230 -1.0000010 H -4.3848540 2.5338090 0.6154660 F -3.1678580 0.4142200 1.2815250 F -3.3273730 -3.0684420 -1.7875320 H -0.5720010 -4.6828760 1.4284140 F 0.4108580 -2.4461250 2.1062520 F -2.4107100 -0.6399000 -1.2582890 F 0.7080680 2.5934070 -0.3886050 H -0.4781830 0.0443380 2.1447620 Cl 3.7566240 -0.4750490 -2.6087370 H 5.1274730 -0.2005220 -0.1690780 H 4.3331650 0.1872840 2.1581950 H -2.3257660 -5.0140450 -0.3828640 H -3.2924730 4.5678150 -0.4542750 34 5c B 0.1833920 0.0105170 0.1351930 C 1.3623610 -0.9993220 -0.0364280 C -1.2581840 -0.5519990 0.4422630 C 0.3788190 1.5566920 0.0241840 C -2.2579930 -0.5349400 -0.5335160 C -3.5388290 -1.0261270 -0.2712970 C -3.8289840 -1.5399630 0.9907240 C -2.8548330 -1.5678110 1.9794750 C -1.5881970 -1.0792210 1.6882490 C 2.6603820 -0.7033700 0.3989220 C 3.6956490 -1.6214220 0.3052380 C 3.4764080 -2.8739730 -0.2462430 C 2.2047510 -3.1928820 -0.6914500 C 1.1670820 -2.2763410 -0.5774770 C -0.3827060 2.4540200 0.7826910 C -0.2406930 3.8299980 0.6539240 C 0.6553080 4.3620220 -0.2576640 C 1.4135730 3.4966150 -1.0306100 C 1.2813550 2.1239910 -0.8839370 Cl -1.8302670 0.0853540 -2.1180730 Cl -0.3571890 -1.0839270 2.9498460 F -0.9826550 4.6448880 1.4182400 F 2.2825600 3.9870200 -1.9269120

- S72 -

F 2.0303020 1.3353330 -1.6715940 F 4.9166250 -1.2914840 0.7517470 F 1.9667370 -4.3961920 -1.2336250 F -0.0398580 -2.6442440 -1.0327850 F 2.9301720 0.4875560 0.9570900 F -1.2633240 2.0017020 1.6882470 Cl -4.7948570 -1.0176090 -1.4854540 H -4.8228770 -1.9178610 1.1905020 H -3.0774030 -1.9608560 2.9624050 H 4.2840090 -3.5887380 -0.3275980 H 0.7619900 5.4329400 -0.3646510 35 5c-hydride B 0.1043500 -0.0514760 -0.5567620 C 1.5471850 -0.7932510 -0.3561950 C -1.1742580 -0.8370750 0.1147850 C 0.1209230 1.5379700 -0.1807770 C -1.1457490 -1.6760350 1.2380930 C -2.2374100 -2.4014450 1.7044760 C -3.4583950 -2.2863960 1.0623060 C -3.5685360 -1.4241850 -0.0203880 C -2.4533280 -0.7108560 -0.4725290 C 2.6712830 -0.2636350 0.2721080 C 3.8870900 -0.9350710 0.3300580 C 4.0398400 -2.1866080 -0.2410810 C 2.9365880 -2.7404480 -0.8707750 C 1.7324030 -2.0543300 -0.9241690 C -0.4194830 2.1007340 0.9714540 C -0.4136830 3.4693970 1.2147110 C 0.1500350 4.3504500 0.3084040 C 0.7070520 3.8165210 -0.8424970 C 0.6903300 2.4478590 -1.0706140 Cl 0.3160930 -1.8282560 2.2349550 Cl -2.6883520 0.4196200 -1.8051250 F -0.9606700 3.9505600 2.3576900 F 1.2755890 4.6457380 -1.7522950 F 1.2713030 2.0070820 -2.2098860 F 4.9396520 -0.3614000 0.9630820 F 3.0412310 -3.9663110 -1.4399820 F 0.6999690 -2.6668490 -1.5483220 F 2.6156720 0.9366670 0.8971570 F -0.9717250 1.3166350 1.9268980 H -0.0693240 -0.1108110 -1.7486590 H -2.1331240 -3.0397000 2.5721930 H -4.3235910 -2.8396040 1.4027340 Cl -5.1577210 -1.2793520 -0.7777450 H 4.9829950 -2.7125990 -0.1955200 H 0.1604270 5.4152200 0.4943150