S1

Supporting Information

Experimental and theoretical studies on hydrogen bond promoted fixation of

carbon dioxide and epoxides in cyclic carbonates

J Jin-Quan Wang, Jian Sun, Wei-Guo Cheng, Kun Dong, Xiang-Ping Zhang and Suo-Jiang

Zhang*

Beijing Key Laboratory of Ionic Liquids Clean Process, Key Laboratory of Green Process and

Engineering, State Key Laboratory of Multiphase Complex System, P.O. Box 353, Beijing, 100190,

China, Fax: (+86)-10-8262-7080, E-mail: sjzhang@home.ipe.ac.cn.

Supporting information

1. General information S2

2. Experiments details S2-S3

3. Supporting Table S4

4. Supporting Figures S5-S7

5. Characterization of catalysts and products S8-S11

6. Cartesian coordinates for the optimized geometries S12-S43

S2

1. General information

The Bu4NBr, epoxides and other organic and inorganic reagents were purchased from

J&KCHEMICA without further purification. GC-MS were measured on a Finnigan HP G1800 A. GC

analyses were performed on a Agilent GC-6890 equipped with a capillary column (DB-624, 30 m×0.32

μm) using a flame ionization detector. NMR spectra were recorded on a Bruker 300 or Varian 400

spectrometer in CDCl3. 1H and 13C NMR chemical shifts (δ) were given in ppm relative to TMS. 1H

and 13C positive chemical shifts (δ) in ppm were downfield from tetramethylsilane (CDCl3: δC = 77.0

ppm; residual CHCl3 in CDCl3: δH = 7.26 ppm).

The calculations were carried out by performing DFT by use of the B3PW91functional with the

6-311++G (d, p) basis set as implemented in Gaussian 09 program package. All geometries for the

isolated reactants, products, intermediates, and transition states involved in the cycloaddition reaction

have been fully optimized. Vibrational frequency calculations, from which the zero-point energies

(ZPEs) were derived, have been performed for each optimized structure at the same level to identify the

natures of all the stationary points (local minimum or first-order saddle point). The intrinsic reaction

coordinate (IRC) pathways have been traced in order to verify that each saddle point links two desired

minima.

2. Experiments details

Experiments details of fixation CO2 into cylic carbonate

The reaction of CO2 fixation with epoxides was conducted in a 25 mL stainless steel reactor

equipped with a magnetic stirrer and automatic temperature control system. Typically, in the reactor, an

appropriate volume of CO2 (1.0 MPa) was added to a mixture of PO (1mL, 14.3 mmol), Bu4NBr (46mg,

0.143 mmol), HBD (14.3 mmol) at room temperature. The temperature was then raised to 100 oC while

more CO2 was added from a reservoir tank to maintain a constant pressure (3 MPa). After the reaction

had proceeded for 30 min, the reactor was cooled to 0oC in an ice water bath, and the remaining CO2

was removed slowly. The products were analyzed by GC using biphenyl as the internal standard and

identified by GC-MS by comparing retention times and fragmentation patterns with authentic samples.

The products were purified by distillation or silica gel column chromatography for the substrates in

Table 2 and Table S1.

S3

Scheme S2. Synthesis of dual-functionalized poly (ionic liquids). AIBN: azobis(isobutyronitrile).

The tipical procedures to prepare monomer of PILs were similar to that reported.[9a] Thus,

2-bromoethanol (100 mmol) and 1-vinylimidazole (50 mmol) were added to a 50 mL three-necked

flask equipped with a magnetic stirrer. The mixture was heated at reflux for 20 h in an oil bath at 70 oC

under the protection of nitrogen. Then, the reaction mixture was cooled down to room temperature. The

top phase was poured out, and the residue was washed three times with ethyl acetate and then dried at

under vacuum.

PILs were prepared by radical copolymerization. In a typical experiment, ILs (30 mmol),

4-Vinylpyridine (30 mmol), and AIBN (3mmol) were dissolved in chloroform (200 mL) in a

three-necked flask under nitrogen protection. The mixture was maintained at 60 oC at reflux for 60 h

with stirring. The PIL formed was collected by filtration and washed washed four times with ethyl

acetate. Then, the solid was dried under vacuum. The MW of 1a was determined to be 245821, and

concentration of 4-Vinylpyridine (mol %) in the copolymer was 48%.

The experimental method for 1H NMR spectra of 1, 2-benzenediol with and without PO:

Without PO: 1, 2-benzenediol 2 μL, DCCl3 0.5 mL;

With PO: 1, 2-benzenediol 2μL, PO 20 μL, DCCl3 0.5 mL.

S4

3. Supporting Table

Table S1 Fixation CO2 with various epoxides.[a]

Entry Substrate Product Conv.[%] Yield [%][b]

1

99 94

2

96 93

3

95 92

4

90 88

5[c]

98 95

6[d]

96 94

[a] Reaction condition: PO (14.6 mmol), Catalyst 1a (0.2 mmol), 120 oC, 2.0 MPa, 4 h. [b] Isolated yields. [c] 8 h. [d] 18h.

S5

4. Supporting Figure

B

D TS2(406i)

TS1(299i)

CA

E

Figure S1 The proposed mechansim and the optimized geometries for the intermediates and transition

states for fixation of CO2 with ethylene oxide catalyzed by Bu4NBr promoted by H2O. Values in

parentheses denote the imaginary frequencies of transition states. Distances are in angstroms.

S6

-20

-10

0

10

20

30

40

50

60

Rea

ltiv

e E

nerg

y (k

cal m

ol-1

)

EO+CO2

0.00

IM-1.94

TS58.92

EC-12.77

2.877Å

1.774Å

2.292Å2.040Å

(342i)

Catalyst-free process

Figure S2 Potential energy surface profiles for the cycloaddition reaction without catalyst.

Figure S3 Optimized geometries for the intermediates and transition states for fixation of CO2 with

ethylene oxide catalyzed by Bu4NBr. Values in parentheses denote the imaginary frequencies of

transition states. Distances are in angstroms.

S7

-20

-10

0

10

20

30

Rel

ativ

e E

nerg

y [k

cal m

ol-1

]

0.00

F

28.20

TS3

11.26

G

H

-9.46

8.40

TS4

-20.32

I

CO2

Figure S4 The potential energy surface profiles of Bu4NBr-catalyzed process

0

5

10

15

20

Rel

ativ

Ene

rgy[

kcal

mol

-1]

J

K

TS5

0.00

20.45

2.87

1.034Å

1.503Å

1.919Å

2.525Å

1.621Å

1.782Å

Figure S5 The potential energy surface profiles of the rate-determining step catalyzed by Bu4NBr/1,

2-benzenediol

S8

5. Characterization of catalysts and products

5.1 NMR data for Catalysts and its intermediates in Table 2

4-methyl-1, 3-dioxolan-2-one:

1H NMR (CDCl3, TMS, 400 MHz):1.49 (d, J=6.0 Hz, 3H); 4.05 (t, J=8.8 Hz, 1H); 4.60 (t, J=8.0 Hz,

1H); 4.86-4.94 (m, 1H); 13C NMR (CDCl3, TMS, 100.4 MHz): 18.95, 70.46, 73.51, 154.95 (C=O).

3-dioxolan-2-one :

1H NMR (CDCl3, TMS, 400 MHz): 4.2 (t, J=10 Hz, 4H); 13C NMR (CDCl3, TMS, 100.4 MHz):

63.3, 155 (C=O).

4-butyl-1,3-dioxolan-2-one:

1H NMR (CDCl3, TMS, 400 MHz): 0.96 (t, J= 7.2 Hz, 3H); 1.33-1.38 (m, 2H); 1.29-1.31 (m, 2H); 1.53

(m, 2H); 4.16 (d, J=8.0 Hz, 2H); 4.19 (t, J=6.2 Hz, 1H); 13C NMR (CDCl3, TMS, 100.4 MHz): 14.00,

23.12, 26.19, 36.23, 68.04, 75.61, 155.07 (C=O).

4-chloromethyl-1,3-dioxolan-2-one :

1H NMR (CDCl3, TMS, 400 MHz): 1.490 (d, 2H, J=6.0 Hz); 4.05 (t, 1H, J=8.4 Hz); 4.60 (t, 1H, J=8.0

Hz); 4.86-4.94 (m, 1H); 13C NMR (CDCl3, TMS, 100.4 MHz): 18.95, 70.46, 73.51, 154.95 (C=O).

4-phenyl-1, 3-dioxolan-2-one:

S9

1H NMR (CDCl3, TMS, 400 MHz): 4.34 (t, 1H, J=8.4 Hz); 4.80 (t, 1H, J=8.4 Hz); 5.68 (t, 1H, J=8.0

Hz); 7.35-7.44 (m, 5H); 13C NMR (CDCl3, TMS, 100.4 MHz): 71.10, 77.92, 125.81, 129.12, 129.63,

135.70, 154.81 (C=O).

4-Phenoxymethyl-1,3-dioxolan-2-one:

1H NMR (CDCl3, 400 MHz): 4.15 [dd, 3J = 4.4 Hz, 2J=10.8 Hz, 1H, OCH2], 4.24 [dd, 3J = 3.6 Hz,

2J= 10.8 Hz, 1H, OCH2], 4.55 [dd, 3J= 8.4 Hz, 2J= 6 Hz, 1H, PhOCH2], 4.62 [t, 3J= 8.4 Hz, 1H,

PhOCH2], 5.03 [m, 1H, OCH], 6.91 [d, 3J= 8.0 Hz, 2H, C6H5], 7.02 [t, 3J = 7.4 Hz, 2H, C6H5], 7.31 [t,

3J= 8.0 Hz, 2H, C6H5]. 13C NMR (CDCl3, TMS, 100.4 MHz): 66.17, 68.84, 74.11, 114.57, 121.92,

129.62, 154.65, 157.71.

4, 5-tetramethylene-1, 3-dioxolan-2-one:

1H NMR (CDCl3, TMS, 400 MHz): 1.80-1.86 (m, 2H); 1.97-2.05 (m, 2H); 2.28 (d, 4H, J=4.8 Hz);

5.06-5.11 (m, 2H); 13C NMR (CDCl3, TMS, 100.4 MHz): 19.00, 26.61, 75.65, 155.27 (C=O).

5.2 NMR data for monomers of catalysts in Table 3

N

N

HO

Br

S10

1H NMR (CDCl3, TMS, 400 MHz): 3.72 (t, J=5.0 Hz, 2H); 4.25 (t, J=5.1 Hz, 2H); 5.36 (dd, J=2.2 Hz,

1H); 5.97 (dd, J=2.2 Hz, 1H); 7.34(dd, J=8.7 Hz, 1H); 7.91(s, 1H); 8.25(s, 1H); 9.60(s, 1H); 13C

NMR (CDCl3, TMS, 100.4 MHz): 59.56, 62.01, 109.26, 119.50, 124.12, 129.23, 136.02.

1H NMR (CDCl3, TMS, 400 MHz):0.88 (t, J=7.4 Hz, 3H); 1.27 (m, 2H); 1.80 (m, 2H); 4.23 (t, J=7.3

Hz, 2H); 5.42 (dd, J=8.8 Hz, 1H); 6.00 (dd, J=15.7 Hz, 1H); 7.35(dd, J=8.7 Hz, 1H); 8.02(s, 1H);

8.30(s, 1H); 9.75(s, 1H); 13C NMR (CDCl3, TMS, 100.4 MHz): 13.85, 19.32, 31.60, 49.41, 109.13,

119.71, 123.79, 129.39, 135.86.

N

NCl

1H NMR (CDCl3, TMS, 400 MHz):0.87 (t, J=7.4 Hz, 3H); 1.25 (m, 2H); 1.78 (m, 2H); 4.19 (t, J=7.3

Hz, 2H); 5.38 (dd, J=8.8 Hz, 1H); 5.97(dd, J=15.7 Hz, 1H); 7.31(dd, J=8.7 Hz, 1H); 7.96(s, 1H);

8.25(s, 1H); 9.81(s, 1H); 13C NMR (CDCl3, TMS, 100.4 MHz): 13.80, 19.26, 31.54, 49.37, 109.05,

119.65, 123.73, 129.34, 135.80.

5.3 Elementary analysis for catalysts in Table 3

Catalyst C [%] H [%] N [%] O [%]

1a 44.51 5.52 11.56 4.72

1b 61.85 7.42 12.56

1c 56.56 6.56 11.48

2a 38.26 5.02 12.74

2b 57.86 7.96 14.64

S11

5.4 Solid-state 13C NMR of catalyst 1a in Table 3.

ppm (t1)050100150200

0

50000

10000

16

4.2

68

15

1.8

61

15

1.0

57

15

0.5

47

14

6.3

81

13

7.5

63

12

7.5

30

12

6.6

00

61

.55

7

54

.74

7

41

.52

1

Figure S6 Solid-state 13C NMR of catalyst 1a

5.5 Thermogravimetric analysis of catalyst 1a in Table 3.

0.00 200.00 400.00 600.00Temp [C]

-2.00

0.00

2.00

4.00

6.00

mgTGA

300oC

Figure S7 Thermogravimetric analysis of catalyst 1a

S12

6. Cartesian coordinates for the optimized geometries of all species involved in the uncatalyzed and catalytic cycle (values in Angstrom).

CO2

C 0.00000000 0.00000000 -0.00000300

O 0.00000000 0.00000000 -1.16079800

O 0.00000000 0.00000000 1.16080100

EO

C -0.66576500 -0.48434900 0.00000000

C 0.00000000 0.82328800 0.00000000

O 0.76245100 -0.38815800 0.00000000

H -1.10259200 -0.86414600 0.91977500

H -1.10259200 -0.86414600 -0.91977500

H 0.05008100 1.39996300 0.91977300

H 0.05008100 1.39996300 -0.91977300

IM

C 1.87874100 0.43118000 -0.60581100

C 1.97492800 -0.19200400 0.71813500

O 0.99101900 -0.63098500 -0.22830300

H 1.40849300 1.40566300 -0.70321900

H 2.60020100 0.17139600 -1.37541800

H 1.57919000 0.33178700 1.58410300

H 2.76662600 -0.90809500 0.91999200

C -1.77631400 0.11262000 0.03044300

O -2.18045900 -0.96347600 -0.12099000

O -1.41289000 1.20552100 0.18903500

TS

C 1.57818300 0.64277200 -0.34432300

C 1.47394400 -0.59109200 0.42283700

O 0.29759900 -0.94315500 -0.27365100

H 1.55490900 1.64111500 0.06503500

H 1.71401900 0.53230900 -1.41324900

H 1.33890600 -0.44994200 1.49832200

H 2.26966500 -1.31824900 0.22953700

C -1.07628100 0.13846300 0.02677400

O -2.07393400 -0.48069000 -0.06672000

S13

O -0.56523600 1.23058400 0.21394900

EC

C 1.30070600 -0.75534900 0.12228700

C 1.30069200 0.75536800 -0.12231700

O -0.07231700 1.11055200 0.10956900

H 1.92786400 -1.31444500 -0.57014700

H 1.56056900 -1.01459000 1.15169600

H 1.56040500 1.01483000 -1.15167800

H 1.92769300 1.31443900 0.57026100

C -0.85173900 0.00009100 -0.00000900

O -2.03981200 -0.00009800 0.00000200

O -0.07218200 -1.11056500 -0.10955900

A

C -1.69745600 1.28829400 -0.51974200

H -2.27684500 1.01317500 -1.40117400

H -0.73580100 1.69902000 -0.84897700

C -0.53099700 -0.82329100 -0.87812600

H -1.01814800 -0.61021900 -1.83045600

H 0.44499000 -0.33152300 -0.90507700

C -0.45700000 0.32548100 1.38478800

H 0.30286000 1.00517800 0.98462700

H -1.11420800 0.88047300 2.05500900

C -2.56642400 -0.77600900 0.64507300

H -2.98704400 -0.18533100 1.45995800

H -2.21920000 -1.71444700 1.07346000

N -1.33404900 -0.03436300 0.17480500

O 2.88832800 -2.22813700 0.47956300

H 3.46542700 -2.96724700 0.69292800

C 5.29901400 0.82615000 -0.14098500

C 5.07248500 0.35550400 -1.50811800

H 4.51152400 1.40764000 0.32771700

H 6.31338900 0.97285800 0.21910900

H 5.91966900 0.15453500 -2.15775000

H 4.12861600 0.61353100 -1.97792200

Br 1.80670100 2.11821000 -0.83213900

O 4.96094000 -0.55724100 -0.39171800

H 3.50152900 -1.53528000 0.16161800

S14

C -0.40893700 -2.33604800 -0.71244400

C 0.41464500 -2.91056800 -1.87696600

H -1.39466300 -2.81420100 -0.71135600

H 0.08844300 -2.59915800 0.22028100

C 0.54887700 -4.43299800 -1.79919700

H -0.04998400 -2.63068700 -2.83047300

H 1.40872100 -2.45682600 -1.85827300

H 1.14098100 -4.81743800 -2.63375100

H 1.04689700 -4.73331600 -0.87293400

H -0.42847700 -4.92623600 -1.83104800

C -3.63553200 -1.04523800 -0.41248400

C -4.73417900 -1.96325000 0.14399000

H -3.19393700 -1.51089100 -1.29853800

H -4.09111700 -0.10730000 -0.74246600

C -5.85171100 -2.23007000 -0.86803000

H -4.28871500 -2.91491200 0.45626000

H -5.16076300 -1.51361400 1.04854600

H -6.61684900 -2.88570100 -0.44525300

H -6.34198300 -1.30053000 -1.17239500

H -5.46289400 -2.71188700 -1.77012300

C -2.45707300 2.31930800 0.30828000

C -2.82182900 3.52442900 -0.57501100

H -1.84008300 2.67472400 1.13683100

H -3.37507200 1.90206000 0.73910700

C -3.54304400 4.62757000 0.20357500

H -1.90664800 3.92565500 -1.02140800

H -3.45331300 3.18965900 -1.40688300

H -3.79087900 5.46943400 -0.44770200

H -4.47626900 4.26216500 0.64458900

H -2.91737500 5.01040500 1.01515300

C 0.21439700 -0.81145500 2.14814900

C 0.89897700 -0.24025800 3.40183900

H 0.97771600 -1.29184400 1.53415600

H -0.50538200 -1.57778400 2.45810900

C 1.65647100 -1.31155100 4.19077300

H 1.59447000 0.54840800 3.09622800

H 0.15181100 0.23676400 4.04870100

H 2.14810200 -0.88051800 5.06701400

H 0.98247300 -2.09969100 4.54276500

S15

H 2.42360200 -1.77889600 3.56809500

TS1

C -0.72355000 1.50004400 -0.57888700

H -1.41421300 1.55662200 -1.42011500

H 0.28785000 1.34925800 -0.96287800

C -0.90404800 -0.92910000 -0.86219500

H -1.20768600 -0.50060700 -1.81768000

H 0.16722800 -1.12192200 -0.91060900

C -0.07081200 0.06257400 1.32353500

H 0.89989600 0.32174200 0.89529100

H -0.33346500 0.85278000 2.02739800

C -2.48096300 0.26105000 0.73520600

H -2.45495800 1.00241100 1.53387600

H -2.66792600 -0.70642600 1.19764400

N -1.07525900 0.20343700 0.16861200

O 1.57890300 -3.34389200 -0.19540300

H 1.77860700 -4.26134200 0.01073200

C 3.60528200 -0.54218400 -0.55118900

C 3.23833300 -1.07231600 -1.87172000

H 2.99207800 -0.82740100 0.28709700

H 4.65178900 -0.37110500 -0.35185200

H 3.83743400 -0.67803300 -2.70183300

H 2.17022700 -0.98826300 -2.12969400

Br 2.96961300 1.83980700 -0.29663200

O 3.64511800 -2.31123300 -1.39238400

H 2.41419700 -2.99935400 -0.66234100

C -3.59337200 0.60397500 -0.25456100

C -4.97194400 0.44508600 0.40531300

H -3.54262000 -0.03830900 -1.13879700

H -3.48509000 1.63394600 -0.60580200

C -6.12232400 0.82857900 -0.52900400

H -5.09823000 -0.59208100 0.73671800

H -5.01456400 1.06324500 1.30982100

H -7.08807800 0.70473100 -0.03337300

H -6.04388600 1.87224600 -0.84749400

H -6.12827000 0.20544200 -1.42828600

C -0.76101500 2.79192500 0.23060400

C -0.48489500 3.99027600 -0.69278200

S16

H 0.01000100 2.77328700 1.00383900

H -1.73087800 2.93188700 0.72168100

C -0.46900600 5.31946700 0.06598200

H 0.48127000 3.83716500 -1.18303400

H -1.24374300 4.02739300 -1.48441700

H -0.27477000 6.15370300 -0.61253800

H -1.42589600 5.51039200 0.56311800

H 0.31434900 5.32481900 0.82884600

C -0.00423500 -1.27944600 2.04530500

C 0.93350900 -1.16209500 3.25968900

H 0.38596100 -2.05298600 1.37901500

H -0.99317400 -1.59357800 2.39766700

C 1.09338000 -2.49253400 3.99967600

H 1.91551900 -0.81126500 2.92522700

H 0.55311800 -0.39886500 3.94966700

H 1.76424100 -2.38625800 4.85584300

H 0.13172400 -2.85845900 4.37411500

H 1.51053400 -3.25770600 3.33979500

C -1.66054100 -2.23784300 -0.63977500

C -1.38286600 -3.19305500 -1.81271900

H -2.73890000 -2.06355400 -0.57391200

H -1.34492100 -2.72052400 0.28485600

C -2.12580200 -4.52319800 -1.66524400

H -1.67692900 -2.71225700 -2.75406200

H -0.30647500 -3.37645900 -1.85886500

H -1.91363900 -5.18356000 -2.50970600

H -1.81966400 -5.04504000 -0.75364800

H -3.21062500 -4.37926200 -1.62057100

B

C -0.90788700 1.41897600 0.33363700

H -0.67111600 1.69770900 -0.69233200

H -0.00330100 1.02736300 0.81040400

C -1.04501700 -0.85794400 -0.56967000

H -0.43780600 -0.30333200 -1.28368300

H -0.34415500 -1.27370200 0.15783500

C -2.05449800 -0.29751700 1.67115700

H -1.03368900 -0.37042300 2.07388900

H -2.60626500 0.49796400 2.17365200

S17

C -3.15831400 0.55196100 -0.40726300

H -3.69222400 1.17910900 0.30850500

H -3.72067200 -0.37523600 -0.50558700

N -1.83743400 0.19629800 0.23455600

O 0.95569400 -0.54251100 1.68290400

H 1.52640600 -0.78965500 2.41567700

C 4.39809300 -0.76801100 -0.27393000

C 3.35919900 0.33777400 -0.44339500

H 4.26344100 -1.31336100 0.65729800

H 4.39299200 -1.45455500 -1.11712600

H 3.58109600 0.90402500 -1.35523600

H 3.42797500 1.03298500 0.40570600

Br 6.25209300 -0.03025200 -0.19476100

O 2.08510700 -0.23701600 -0.54732000

H 1.69751000 -0.40092400 0.41309100

C -2.78839000 -1.62145700 1.86039000

C -3.02950100 -1.86790400 3.35866300

H -2.18609200 -2.44450900 1.46904100

H -3.75256300 -1.64033200 1.34018200

C -3.71732700 -3.20784700 3.63342900

H -2.06937700 -1.83215700 3.88402400

H -3.63790900 -1.05310200 3.76937400

H -3.87744000 -3.35633000 4.70438900

H -4.69338100 -3.26312400 3.14096300

H -3.11280800 -4.04413700 3.26988300

C -1.44314400 2.62463000 1.10074100

C -0.43221000 3.78036700 1.01784600

H -1.59580600 2.37613900 2.15444300

H -2.40678900 2.96953200 0.70772300

C -0.87583000 5.01248400 1.81041400

H 0.53704500 3.43172400 1.38844700

H -0.27836700 4.05509500 -0.03229100

H -0.14021100 5.81679200 1.73051100

H -1.83241700 5.40023900 1.44518900

H -0.99555000 4.77788600 2.87249000

C -3.07079800 1.25728700 -1.76046200

C -4.45741000 1.37514200 -2.41071000

H -2.40148500 0.71468000 -2.43410100

H -2.64806400 2.25865800 -1.64027800

S18

C -4.42060100 2.11656600 -3.74967800

H -4.87577000 0.37276800 -2.55903600

H -5.13882600 1.89283800 -1.72494100

H -5.41832700 2.18399400 -4.19025100

H -4.04082700 3.13548900 -3.62874300

H -3.77365900 1.60454100 -4.46822100

C -1.84043500 -1.93958900 -1.29919100

C -0.86793000 -2.96658800 -1.90418100

H -2.44392300 -1.51271700 -2.10764800

H -2.53131400 -2.45910100 -0.63204400

C -1.58457400 -4.05465500 -2.70767000

H -0.14464100 -2.44903700 -2.54309700

H -0.28245200 -3.42265900 -1.09950100

H -0.87076900 -4.77291500 -3.11894000

H -2.29184300 -4.61094700 -2.08421200

H -2.14483300 -3.62837500 -3.54615000

C

C 1.07413000 1.48359800 0.17956700

H 1.73492400 1.86196500 0.95931800

H 0.14473600 1.12242000 0.63716300

C 1.92060000 -0.70251300 0.86787700

H 2.16662200 -0.03875700 1.69597400

H 0.93374000 -1.11919300 1.06386900

C 0.75384300 -0.40735300 -1.36295100

H -0.20617400 -0.38403000 -0.83881100

H 0.72300400 0.29185400 -2.19941900

C 3.05520900 0.50884800 -1.05231000

H 2.80600900 1.04279100 -1.97022800

H 3.47910000 -0.45117200 -1.34177500

N 1.74365800 0.20941900 -0.36110100

O -0.79942500 -2.53354300 0.77854500

H -1.20235700 -1.60123000 0.82608500

H -1.29577800 -3.06827800 1.40371700

C -3.86499800 -0.55954400 0.41216900

C -2.69615900 0.39732300 0.17288300

H -3.65245600 -1.56094700 0.04364900

H -4.15091700 -0.58828000 1.46077600

H -3.00613200 1.40096600 0.51321000

S19

H -2.54329600 0.47854500 -0.92276300

Br -5.51542100 0.01319300 -0.56753000

O -1.56679000 -0.05486500 0.83929800

C -1.43186100 0.62594600 3.16153700

O -0.30067200 0.35652400 3.27809100

O -2.53854200 0.97071200 3.27830700

C 1.03693100 -1.81444400 -1.87937600

C 0.03686400 -2.15876600 -2.99549500

H 0.90564200 -2.53437300 -1.07028700

H 2.05405200 -1.90973100 -2.27626000

C 0.21224000 -3.58760300 -3.51603200

H -0.98044500 -2.03408300 -2.61122700

H 0.14875500 -1.44881400 -3.82441000

H -0.50770500 -3.80824200 -4.30825000

H 1.21564500 -3.74336100 -3.92585700

H 0.05981600 -4.31623400 -2.71496300

C 2.96377500 -1.81696000 0.78814600

C 2.89456200 -2.66762900 2.06741800

H 3.97549200 -1.40908100 0.68852200

H 2.79301100 -2.46493100 -0.07221100

C 3.93042800 -3.79456200 2.08000300

H 3.04202300 -2.02380800 2.94235700

H 1.88677600 -3.08360900 2.15672000

H 3.85815700 -4.38328600 2.99796700

H 3.78404800 -4.47710800 1.23720200

H 4.95077800 -3.40233900 2.01761700

C 4.07117200 1.31063200 -0.24046000

C 5.41328100 1.40256200 -0.98198800

H 4.23225400 0.85146900 0.73931400

H 3.69672200 2.32149800 -0.05657100

C 6.45169400 2.23396400 -0.22403400

H 5.80518000 0.39284600 -1.15097800

H 5.25092500 1.83799200 -1.97509800

H 7.39506200 2.28075300 -0.77336800

H 6.10432700 3.26024200 -0.07220600

H 6.66129000 1.80483900 0.76033900

C 0.77212600 2.58490600 -0.83276900

C 0.15725300 3.79603900 -0.11110400

H 0.06080500 2.23559600 -1.58510400

S20

H 1.67360800 2.91071100 -1.36448900

C -0.20692600 4.93252300 -1.06966100

H -0.73688500 3.47097900 0.43028300

H 0.85996100 4.16512400 0.64556400

H -0.63619400 5.77908100 -0.52817000

H 0.67222600 5.29589800 -1.61151800

H -0.94378300 4.60520100 -1.80886600

D

C -1.98359900 1.64532600 -0.35717100

H -2.34560300 1.74699100 -1.38031000

H -0.89242200 1.62386400 -0.37133400

C -1.69530700 -0.71958100 -0.89980400

H -1.73549400 -0.21180800 -1.86438200

H -0.65319800 -0.72906300 -0.58044000

C -1.85465800 0.03784800 1.51719800

H -0.80718500 0.34009400 1.45408300

H -2.40276900 0.75627100 2.12776300

C -3.90066700 0.06616600 0.09189300

H -4.27812400 0.67945000 0.91139400

H -4.09550200 -0.97263700 0.35076900

N -2.39575900 0.23340100 0.09129800

O 0.70284600 -2.77754200 0.67339400

H 1.24781600 -3.54698100 0.86026700

C 4.92101100 0.49032600 -0.87149200

C 4.38747200 1.04054800 0.44223900

H 4.45117300 -0.45463500 -1.12627900

H 4.82129400 1.20897700 -1.68150600

H 4.91883600 1.95301400 0.71795600

H 4.49215300 0.29846200 1.23423000

Br 6.86512600 0.11119300 -0.72663100

O 3.01927500 1.42159500 0.28572400

C 2.05452600 0.41082200 0.38661700

O 0.88555400 0.82621400 0.26646600

O 2.46293600 -0.75535300 0.57878600

H 1.34464200 -2.01653600 0.64928600

C -2.48278500 2.81224900 0.49025100

C -2.04793300 4.14179400 -0.14899200

H -2.06442500 2.76257600 1.49834500

S21

H -3.57443000 2.80464300 0.58969100

C -2.47400300 5.35901600 0.67575100

H -0.95960000 4.13940100 -0.26718000

H -2.46943100 4.21756000 -1.15856300

H -2.15346000 6.28808700 0.19799900

H -3.56170000 5.40296700 0.79169000

H -2.03233400 5.33200100 1.67624900

C -1.96151700 -1.35224600 2.13609700

C -1.52727700 -1.28585600 3.61038300

H -1.29525700 -2.04555800 1.61946700

H -2.98423300 -1.74388000 2.08906700

C -1.56094500 -2.65753800 4.28912400

H -0.51167600 -0.87976000 3.66298000

H -2.17265700 -0.58762200 4.15843500

H -1.24306900 -2.58830400 5.33272900

H -2.56944800 -3.08403800 4.27638900

H -0.89345800 -3.35857300 3.78113200

C -2.25461700 -2.13127600 -1.06061400

C -1.38469700 -2.91136000 -2.06050700

H -3.28569600 -2.10806100 -1.43021300

H -2.25746500 -2.66979600 -0.11336400

C -1.91295000 -4.32594100 -2.31188900

H -1.33675600 -2.36460700 -3.01050700

H -0.36802100 -2.96129600 -1.66225800

H -1.27692800 -4.86081500 -3.02187500

H -1.93472500 -4.90743200 -1.38528200

H -2.92849200 -4.31157800 -2.72185200

C -4.61674000 0.43013700 -1.20785100

C -6.10089500 0.03931900 -1.14119400

H -4.15089200 -0.07377700 -2.05989300

H -4.54132400 1.50483500 -1.39679600

C -6.87250800 0.42872300 -2.40478000

H -6.18431300 -1.04153200 -0.97905500

H -6.56381700 0.51631800 -0.26914700

H -7.92235500 0.13520900 -2.33008500

H -6.84107000 1.50945400 -2.57212300

H -6.45402500 -0.05761800 -3.29099200

TS2

S22

C -2.19122100 1.61160700 -0.43690400

H -2.67423500 1.63827100 -1.41340400

H -1.11194900 1.66273000 -0.58375300

C -1.80460300 -0.75680200 -0.90842800

H -1.98421600 -0.29980800 -1.88236100

H -0.73485500 -0.69562200 -0.71127900

C -1.73456500 0.11073500 1.47510100

H -0.72757300 0.48322900 1.28380400

H -2.26002700 0.81695600 2.11861500

C -3.92793700 -0.06129300 0.30523200

H -4.24843500 0.57164600 1.13375300

H -4.01652700 -1.09438400 0.63492500

N -2.44805900 0.20031800 0.11629000

O 0.97708900 -2.54798200 0.43758700

H 1.55698800 -3.30477900 0.56335300

C 4.46615600 -0.08724800 -0.14889800

C 4.31976300 1.38401100 -0.49054900

H 4.73188600 -0.39520500 0.84524200

H 4.52348200 -0.82375400 -0.92992000

H 4.72846800 1.59999400 -1.47350200

H 4.81576400 2.00701400 0.25011100

Br 7.00971600 0.06227400 -0.46282500

O 2.91388100 1.77414300 -0.51910400

C 2.06424200 0.79235100 -0.15828400

O 0.85405100 1.01321700 -0.13487000

O 2.63537800 -0.32817500 0.13632100

H 1.58082000 -1.77958600 0.35021400

C -1.66304900 -1.25171100 2.15988100

C -1.07852000 -1.07981700 3.57222900

H -1.00779500 -1.92083800 1.59954200

H -2.65103600 -1.71756400 2.24299100

C -0.93299000 -2.41399200 4.30860000

H -0.09789000 -0.59795000 3.49652000

H -1.71424500 -0.40381600 4.15754400

H -0.51216100 -2.26768100 5.30648900

H -1.90083100 -2.91206300 4.42577100

H -0.27074000 -3.09101700 3.76250200

C -2.66887400 2.78565900 0.41301400

C -2.41864700 4.10619700 -0.33529800

S23

H -2.12943000 2.81966400 1.36249500

H -3.73619900 2.70627500 0.64752200

C -2.82688200 5.33311500 0.48403900

H -1.35702700 4.17379400 -0.59441600

H -2.96908000 4.09833600 -1.28356000

H -2.64114900 6.25459100 -0.07280200

H -3.89096800 5.30780400 0.73943000

H -2.26007000 5.39104300 1.41778400

C -4.81699900 0.18063400 -0.91358300

C -6.24722600 -0.31519800 -0.64918200

H -4.41702600 -0.33234500 -1.79324200

H -4.85131000 1.24622300 -1.15779000

C -7.19041900 -0.05458400 -1.82641400

H -6.22316800 -1.38862400 -0.42881400

H -6.64144800 0.17321400 0.24982300

H -8.19671900 -0.42143400 -1.61120900

H -7.26676700 1.01455800 -2.04544700

H -6.84099600 -0.55638100 -2.73358200

C -2.28421000 -2.20593200 -0.94593700

C -1.48932700 -2.97716600 -2.01356800

H -3.35027600 -2.26321000 -1.18984100

H -2.14251900 -2.69927900 0.01552900

C -1.93732300 -4.43604200 -2.13229000

H -1.60211100 -2.47984200 -2.98473500

H -0.42871200 -2.93555000 -1.75200900

H -1.35833600 -4.96160000 -2.89563700

H -1.79809900 -4.96898400 -1.18695000

H -2.99454600 -4.51259700 -2.40688500

E

C -0.06993700 0.63860700 1.21522400

H 0.07056300 1.59168700 0.70866100

H 0.77614300 -0.01011600 0.97275200

C -0.86970900 -0.15644800 -0.94920700

H -0.33040300 0.75799500 -1.18829500

H -0.15293400 -0.98163600 -0.97121700

C -1.43215300 -1.41245100 1.18182100

H -0.42596300 -1.84236500 1.18282400

H -1.73855300 -1.21604200 2.20954100

S24

C -2.54083000 0.77639300 0.71950700

H -2.81619100 0.67789500 1.77053000

H -3.31271300 0.27638500 0.13668000

N -1.27314700 -0.03279400 0.53389900

O -0.06678100 2.96544500 -2.16093400

H 0.05370400 3.43384700 -2.99162000

C 4.20213800 -0.24708100 -1.68226200

C 4.63004300 -0.01139200 -0.22377600

H 3.66570900 -1.18891600 -1.79072700

H 5.01718600 -0.16032800 -2.40083000

H 5.69043700 0.21123500 -0.10482300

H 4.31254100 -0.83129400 0.41928600

Br 1.94080700 -2.37446600 0.18158100

O 3.88546400 1.17133200 0.16357800

C 3.09529800 1.56897100 -0.83816500

O 2.32222400 2.49341300 -0.75714300

O 3.26892500 0.83235100 -1.94176600

H 0.82613100 2.88891000 -1.77497100

C -1.98456400 -0.32806000 -1.97960000

C -1.36338400 -0.55744000 -3.36777600

H -2.60823500 0.57017800 -2.02366000

H -2.64212000 -1.16572500 -1.74219500

C -2.41999400 -0.69347400 -4.46724400

H -0.69308600 0.27652500 -3.59895400

H -0.74025500 -1.45762800 -3.33979400

H -1.95361200 -0.85548300 -5.44246500

H -3.08809400 -1.53915500 -4.27569400

H -3.03666300 0.20801400 -4.54008800

C -2.45321300 2.25185400 0.32980300

C -3.85179200 2.88569200 0.29996900

H -1.96997500 2.37954000 -0.64247300

H -1.83460000 2.79373500 1.05144700

C -3.81246400 4.38528100 -0.00683400

H -4.46499100 2.37480600 -0.45209600

H -4.35181400 2.72341200 1.26312100

H -4.82012500 4.80783800 -0.03632600

H -3.24497400 4.92955200 0.75385800

H -3.33753900 4.57759200 -0.97285000

C -0.16186400 0.84768000 2.72406600

S25

C 1.06297100 1.63839700 3.21431700

H -0.18763300 -0.11175400 3.24720700

H -1.07079300 1.39435300 3.00047700

C 1.05929900 1.84448300 4.73100200

H 1.97307600 1.10912600 2.91524100

H 1.09591900 2.60966600 2.70870500

H 1.93773900 2.41035800 5.05136100

H 0.17198300 2.39659500 5.05768000

H 1.07042900 0.88728600 5.26120600

C -2.39932000 -2.40287600 0.54184800

C -2.50568900 -3.65706400 1.42506400

H -2.03035100 -2.70495100 -0.44053100

H -3.39836000 -1.97434000 0.40605600

C -3.41441300 -4.72877800 0.81773600

H -1.50268300 -4.06845600 1.57792400

H -2.88263000 -3.37532800 2.41577200

H -3.47024600 -5.60819300 1.46427100

H -4.43382600 -4.35556600 0.67551700

H -3.03958900 -5.05747800 -0.15597800

F

C -1.62128400 1.10147000 -0.52052700

H -2.23115900 0.70276600 -1.33102300

H -0.76052900 1.62398800 -0.95443400

C -0.18505300 -0.83416600 -0.89808000

H -0.76868800 -0.74124000 -1.81482200

H 0.70231000 -0.20714300 -1.02150700

C -0.10771700 0.41945500 1.30713000

H 0.49682200 1.19577900 0.82555500

H -0.78777900 0.88498300 2.02121700

C -2.08067500 -1.01274700 0.78495800

H -2.51615600 -0.45812500 1.61728700

H -1.56485300 -1.87392700 1.20582400

N -1.01310000 -0.12061700 0.18875800

C 4.48491600 0.09360600 0.23025100

C 4.32235900 -0.46019500 -1.11405500

H 3.95466100 1.01232500 0.46316100

H 5.38955400 -0.11826900 0.79464400

H 5.10691300 -1.08072900 -1.53977900

S26

H 3.68118500 0.07833800 -1.80590500

Br 1.70956200 2.35948400 -1.15803200

O 3.63635900 -1.05221800 0.00898300

C 0.17042100 -2.30392000 -0.68327400

C 1.02999700 -2.80101200 -1.85766400

H -0.73042700 -2.92442100 -0.62221600

H 0.72848100 -2.45196800 0.24067700

C 1.41709600 -4.27508400 -1.71501100

H 0.48657100 -2.65228900 -2.79853700

H 1.93333900 -2.18828900 -1.91654600

H 2.02054000 -4.60575500 -2.56416100

H 2.00447100 -4.44033700 -0.80719300

H 0.53298500 -4.91935400 -1.66559300

C -3.17973400 -1.47285600 -0.17103600

C -4.08813700 -2.51580100 0.49786000

H -2.74607300 -1.90435000 -1.07800600

H -3.79005500 -0.62223400 -0.48731400

C -5.22478700 -2.98115000 -0.41591400

H -3.48633700 -3.37973700 0.80303800

H -4.50871900 -2.09481600 1.41879700

H -5.85413300 -3.72062200 0.08508800

H -5.86530700 -2.14444400 -0.71028400

H -4.83626200 -3.44022300 -1.32988400

C -2.44292600 2.05940300 0.33535500

C -3.03481400 3.16542900 -0.55448400

H -1.81359600 2.52964700 1.09459100

H -3.25807700 1.54455200 0.85768200

C -3.83372100 4.19887400 0.24345900

H -2.21861800 3.66193600 -1.08886000

H -3.67850400 2.71394400 -1.31912900

H -4.24241200 4.97051900 -0.41370700

H -4.67221300 3.73549800 0.77358600

H -3.20284700 4.69690000 0.98541100

C 0.80359900 -0.56640500 2.03024900

C 1.46894700 0.14232000 3.22241000

H 1.58798100 -0.91767400 1.35686200

H 0.25462000 -1.43878000 2.40244100

C 2.44204100 -0.76871400 3.97543600

H 2.00007200 1.02778200 2.85795300

S27

H 0.69737100 0.50585400 3.91248100

H 2.91132900 -0.23960100 4.80896300

H 1.93012700 -1.64570400 4.38493300

H 3.23639900 -1.12570000 3.31427700

TS3

C -0.11720800 1.45652900 -0.53967900

H -0.77721900 1.74395300 -1.35757100

H 0.76712400 0.97690700 -0.96270600

C -1.10520400 -0.77695500 -0.80158100

H -1.32841100 -0.26100400 -1.73571700

H -0.16189200 -1.30857400 -0.94610000

C 0.08502000 -0.10092400 1.35854400

H 1.08966600 -0.09519300 0.93105400

H 0.04878700 0.70059100 2.09655800

C -2.14569700 0.86050400 0.83425300

H -1.85984800 1.57535300 1.60592600

H -2.60904000 0.01092400 1.33440300

N -0.85301100 0.34658900 0.22813600

C 2.55286500 -1.72072500 -0.98626500

C 1.92151700 -1.61026200 -2.31324700

H 1.91297000 -1.65111000 -0.12723900

H 3.39881300 -2.38622700 -0.88419600

H 2.63759300 -1.70691400 -3.14355200

H 1.33783100 -0.68502000 -2.47850900

Br 3.65766700 0.37044100 -0.27337200

O 1.20347100 -2.74681000 -2.00748400

C -2.21150200 -1.79425300 -0.52278500

C -2.27807700 -2.78381500 -1.70212500

H -3.18730800 -1.31248700 -0.40340100

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S38

C -3.94731300 -3.93231600 -0.18723900

H -3.09525700 -2.50143900 -1.55980300

H -4.52255300 -1.92371400 -0.71544000

C -4.86613000 -4.62037100 -1.20033800

H -3.02448000 -4.51340400 -0.07653500

H -4.42785800 -3.92965800 0.79833900

H -5.09589400 -5.64317800 -0.89191300

H -5.81406300 -4.08409600 -1.30484500

H -4.40040400 -4.66814400 -2.18920600

C -4.36661900 0.78794300 0.76576000

C -5.43390400 1.71448700 0.16004900

H -3.94048800 1.28319700 1.64130600

H -4.84752700 -0.13409600 1.11301800

C -6.53267300 2.08143500 1.16081000

H -4.94600700 2.62486600 -0.20229700

H -5.88296300 1.23195200 -0.71656400

H -7.27671000 2.73773300 0.70249000

H -7.05516900 1.19170600 1.52721000

H -6.11824300 2.60594300 2.02677500

C -0.20682000 -0.54485600 1.87521100

C 0.20461400 0.10560200 3.20788900

H 0.61582400 -0.43123100 1.16830700

H -0.35666300 -1.61774100 2.03953800

C 1.46849800 -0.51988200 3.80327400

H 0.36593500 1.17641600 3.04483000

H -0.61919900 0.02290700 3.92836300

H 1.74350100 -0.02861600 4.74047400

H 1.32184100 -1.58391800 4.01589800

H 2.31247400 -0.43237500 3.11518000

C -0.26314000 -1.67549500 -1.24246000

C 0.55196500 -1.50108200 -2.53608100

H -0.81679900 -2.61868200 -1.30745200

H 0.43229100 -1.75830100 -0.40789400

C 1.45106100 -2.70538100 -2.82588500

H -0.12787700 -1.33831000 -3.38178900

H 1.16473200 -0.59991200 -2.44612500

H 2.03133700 -2.54982500 -3.73912200

H 2.15307000 -2.87179800 -2.00538500

H 0.86201100 -3.61939300 -2.95915400

S39

C 6.37376300 -1.80554900 0.54264400

C 6.36268400 -0.48267900 0.11370900

C 5.15162300 0.17051500 -0.11582100

C 3.93456500 -0.48639100 0.07938600

C 3.95229100 -1.82479300 0.51042000

C 5.16277600 -2.47106400 0.73761700

H 7.30857900 -2.32212700 0.72436600

H 7.29367000 0.04925700 -0.04444800

H 5.13285300 1.20106000 -0.45084900

H 5.15589300 -3.50586900 1.07049700

O 2.72486700 0.09724700 -0.12689800

H 2.83479800 1.03671000 -0.39295700

O 2.73689900 -2.45075200 0.68900000

H 2.89802200 -3.34056100 1.01960900

TS5

C 3.11426600 -0.03733100 -0.36834500

H 3.49887600 0.52822300 -1.21652500

H 2.72081200 -0.99016500 -0.73266400

C 0.91627900 0.77272100 -1.06698100

H 1.55087600 0.85949800 -1.94962500

H 0.46608400 -0.21969300 -1.09279200

C 1.29163400 -0.06144400 1.30053800

H 1.25248500 -1.09435500 0.94486600

H 2.04511900 -0.01208500 2.08694300

C 2.26085400 2.12663000 0.61112600

H 2.83373700 1.98680700 1.52859100

H 1.32962500 2.61984300 0.88237200

N 1.88555800 0.73824600 0.13091000

C -0.78165000 -3.24979600 -0.44028900

C -1.30940600 -2.90341600 -1.76139300

H -0.69815700 -2.46725800 0.29355600

H -0.91941800 -4.25667600 -0.08027900

H -1.26286500 -3.70365100 -2.50633300

H -0.93580100 -1.96687800 -2.19617500

Br 1.73368200 -3.46314400 -0.48367900

O -2.53259600 -2.80602700 -1.08800600

C 3.05087200 2.98774700 -0.37287400

C 3.19668400 4.42248300 0.15741600

S40

H 2.55605600 3.01509500 -1.34820800

H 4.04734800 2.56710900 -0.53502800

C 4.01943700 5.31594600 -0.77448500

H 2.20153800 4.85902600 0.30020800

H 3.66582400 4.39775800 1.14807300

H 4.10603100 6.32801500 -0.37212500

H 5.03206300 4.92413900 -0.90872000

H 3.55717800 5.39025500 -1.76329300

C 4.22817500 -0.30090200 0.63977000

C 5.40172300 -1.00450700 -0.06291700

H 3.87065200 -0.94963900 1.44249800

H 4.58820500 0.62705600 1.09850400

C 6.54148000 -1.34683400 0.89969200

H 5.03113800 -1.91982000 -0.53493800

H 5.78089100 -0.36548900 -0.86961800

H 7.36101400 -1.84292700 0.37413500

H 6.94743700 -0.44886300 1.37672000

H 6.19941700 -2.02114800 1.68990100

C -0.05778700 0.37824300 1.86069400

C -0.37343600 -0.45179700 3.11802600

H -0.86250200 0.23282900 1.13738300

H -0.05094500 1.43849100 2.13467200

C -1.71731600 -0.07591500 3.74756700

H -0.37864300 -1.51542200 2.85553000

H 0.42836300 -0.32262300 3.85604300

H -1.91875000 -0.68913700 4.62968900

H -1.72764700 0.97289400 4.06096400

H -2.53679300 -0.21998800 3.04007700

C -0.15133700 1.86399100 -1.11444300

C -0.98014500 1.71005300 -2.40232400

H 0.31232900 2.85586300 -1.11668300

H -0.83026700 1.81455400 -0.26366600

C -1.99449200 2.84325400 -2.57534300

H -0.31135500 1.67751200 -3.27180300

H -1.50965900 0.75400500 -2.36681300

H -2.58125400 2.70448600 -3.48669800

H -2.68608200 2.87104700 -1.73047800

H -1.49775800 3.81719300 -2.64447100

C -6.70979200 0.80464600 0.39110300

S41

C -6.45846100 -0.46325600 -0.12477400

C -5.14796700 -0.89166900 -0.33070900

C -4.06004400 -0.06390100 -0.02594500

C -4.32585400 1.21648600 0.49617800

C -5.63465100 1.64023100 0.69854300

H -7.72457200 1.14736200 0.55442600

H -7.28059400 -1.12636800 -0.36900000

H -4.94131000 -1.87835800 -0.73024300

H -5.81423600 2.63450100 1.10084300

O -2.77871100 -0.44025000 -0.20982800

H -2.72974900 -1.41074600 -0.56541800

O -3.23962300 2.02321600 0.79021000

H -3.56944400 2.83458600 1.19000200

K

C 1.48263900 0.46866300 1.57367000

H 0.78431600 -0.35365400 1.41513500

H 0.88097000 1.37800600 1.52632300

C 1.39784300 0.65676500 -0.86886600

H 0.50946800 0.07322900 -0.60126900

H 1.12409600 1.71409300 -0.86469800

C 3.29146900 1.71141500 0.44761400

H 2.63533200 2.54629700 0.70158700

H 3.92411700 1.51610300 1.31350000

C 3.20701900 -0.76424900 0.21016300

H 3.96662100 -0.70016700 0.99160600

H 3.72193700 -0.71312000 -0.74774000

N 2.37544900 0.50373100 0.31921800

C -3.94603800 1.61865000 0.76621600

C -2.53355400 2.09401900 0.44354000

H -4.08325800 0.56239600 0.54576500

H -4.21394300 1.82940900 1.79878100

H -2.46416600 3.17320000 0.60819700

H -2.31664800 1.89837700 -0.61478800

Br -5.28712700 2.57883100 -0.34757600

O -1.60201200 1.46002100 1.29308500

C 2.42733400 -2.07287500 0.32475800

C 3.31327100 -3.26390700 -0.06961400

H 1.53244600 -2.05438400 -0.30187000

S42

H 2.07828100 -2.21208100 1.35155100

C 2.60285200 -4.60657500 0.12494400

H 3.61583500 -3.15881500 -1.11880700

H 4.24008200 -3.25233800 0.51867600

H 3.23778400 -5.43800600 -0.19221900

H 2.34278300 -4.76701200 1.17523600

H 1.67500600 -4.64681400 -0.45117900

C 2.19187700 0.35248100 2.91936300

C 1.14657100 0.20408100 4.03929700

H 2.80790100 1.23241700 3.13209900

H 2.85739300 -0.51735300 2.94364100

C 1.78172100 0.12152400 5.42928900

H 0.45077600 1.04817900 3.99651600

H 0.54476300 -0.69055900 3.85093300

H 1.01713300 0.01581900 6.20287900

H 2.45530100 -0.73762600 5.51069500

H 2.36138200 1.02170300 5.65787200

C 4.16885300 2.08979800 -0.74342800

C 5.12010600 3.23468200 -0.35962000

H 3.55217600 2.41054900 -1.58587400

H 4.76166500 1.23539000 -1.08279400

C 5.99902200 3.68785300 -1.52844900

H 4.53515300 4.08555500 0.00867200

H 5.75624300 2.91554000 0.47433000

H 6.66741700 4.49749800 -1.22585800

H 6.61922800 2.86679400 -1.90047400

H 5.39300400 4.05237100 -2.36306500

C 1.87999100 0.21972200 -2.25121900

C 0.81186000 0.58270500 -3.29652000

H 2.01575500 -0.86433600 -2.27018900

H 2.83092200 0.67596000 -2.53670800

C 1.19947500 0.13674500 -4.70879000

H -0.13246100 0.11383500 -3.00689200

H 0.64511000 1.66669600 -3.28903600

H 0.42305800 0.40200400 -5.43078400

H 2.13270300 0.60603200 -5.03729000

H 1.33852500 -0.94773400 -4.75644700

C -3.24780500 -4.27800000 -0.45095400

C -3.52328100 -3.48769200 0.66188000

S43

C -2.75580600 -2.35605000 0.93440800

C -1.67767200 -1.94949300 0.11143900

C -1.42275900 -2.78631100 -1.01447800

C -2.18430900 -3.91370300 -1.28416300

H -3.83855200 -5.15845600 -0.67390500

H -4.34067900 -3.75156400 1.32548300

H -2.96880600 -1.74765100 1.80796800

H -1.95070700 -4.51748400 -2.15991100

O -0.94987200 -0.88968800 0.35042500

H -1.45654700 0.51806500 0.97532000

O -0.35798400 -2.41924300 -1.83892300

H -0.35272800 -3.02177000 -2.58992000