N HCH3O

ドキュメント内 JOC SI 0326(proof) (Page 48-61)

N H CH 3 O

12c

12c

1 H NMR (CDCl 3 ) (13a)

13 C NMR (CDCl 3 ) (13a)

ab u n d an ce 0 1 .0 2 .0 3 .0 4 .0 5 .0 6 .0 7 .0 8 .0 9 .0 1 0 .0 1 1 .0 1 2 .0

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0

7 .8 7 5 7 7 .8 7 2 3 7 .8 6 3 1 7 .8 5 9 7 7 .2 6 9 9 7 .2 6 7 6 7 .2 6 3 0 7 .2 5 7 3 7 .2 4 4 7 7 .2 4 2 4 7 .2 2 8 7 7 .2 1 6 1 7 .1 4 2 8 7 .1 2 9 0 6 .9 8 4 7 6 .9 7 2 1 2 .9 1 3 5 2 .9 0 3 1 2 .8 9 2 8 2 .2 6 7 5 2 .1 8 0 5 2 .1 7 2 5 2 .1 5 9 9 1 .5 8 6 1 0 .0 0 5 7 0 .0 0 0 0

4 .5 2

4 .1 3 2 .0 0

1 .9 6 1 .8 6

0 .9 6 0 .8 6

Filename = 42JHTA12-139-38_Proton-1-5 Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA12-139-38 Solvent = CHLOROFORM-D Creation_Time = 7-AUG-2015 16:14:43 Revision_Time = 5-JAN-2016 13:01:14 Current_Time = 5-JAN-2016 13:01:19 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 13107 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 32 Total_Scans = 32 Relaxation_Delay = 5[s]

Recvr_Gain = 48 Temp_Get = 23.1[dC]

X_90_Width = 8[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以 以

以 以以以以 にににに 由由由由 由由由由 ::::: 42JHTA12-139-38_Proton-1-1.jdf

ab u n d an ce -0 .0 1 0 .0 1 0 .0 3 0 .0 5 0 .0 7 0 .0 9 0 .1 1 0 .1 3 0 .1 5 0 .1 7 0 .1 9 0 .2 1 0 .2 3 0 .2 5 0 .2 7 0 .2 9 0 .3 1

X : parts per Million : Carbon13

210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0

2 0 2 .0 6 5 6 1 7 0 .6 3 1 7 1 4 3 .3 5 3 1 1 4 0 .6 0 5 2 1 3 4 .3 1 4 6 1 3 2 .9 1 6 6 1 3 2 .3 5 1 7 1 2 9 .4 2 1 8 1 2 9 .0 1 9 7 1 2 8 .7 2 2 9 1 2 8 .6 9 4 2 1 2 7 .0 4 7 3 7 7 .2 1 0 6 7 7 .0 0 0 0 7 6 .7 8 9 4 4 7 .5 0 0 1 4 0 .1 9 4 6 2 2 .7 3 9 8 2 1 .3 6 1 0 -0 .0 1 9 4

Filename = 42JHTA12-139-38_Carbon-1-4 Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA12-139-38 Solvent = CHLOROFORM-D Creation_Time = 7-AUG-2015 16:20:25 Revision_Time = 5-JAN-2016 12:39:14 Current_Time = 5-JAN-2016 12:39:22 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.69206016[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.44496109[Hz]

X_Sweep = 47.34848485[kHz]

X_Sweep_Clipped = 37.87878788[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = FALSE Scans = 2000 Total_Scans = 2000 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 23[dC]

X_90_Width = 10.6[us]

X_Acq_Time = 0.69206016[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.53333333[us]

Irr_Atn_Dec = 22.054[dB]

Irr_Atn_Noe = 22.054[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.69206016[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以以

以 以以以 に以にに 由に由由 由由由由 :由:::: 42JHTA12-139-38_Carbon-1-1.jdf

13a

13a

1 H NMR (CDCl 3 ) (13b)

13 C NMR (CDCl 3 ) (13b)

a b u n d a n c e 0 1 .0 2 .0 3 .0 4 .0 5 .0 6 .0 7 .0 8 .0 9 .0 1 0 .0 1 1 .0 1 2 .0 1 3 .0 1 4 .0

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0

7 .2 6 3 0 7 .2 5 8 4 7 .2 4 5 8 7 .2 3 3 2 7 .1 8 0 6 6 .9 1 0 3 6 .8 9 7 7 4 .8 5 2 3 4 .8 4 0 9 4 .8 3 4 0 4 .8 3 0 6 4 .8 2 2 5 4 .8 1 9 1 4 .8 1 2 2 4 .8 0 0 8 3 .2 5 1 3 3 .2 4 5 6 3 .2 4 1 0 3 .2 3 4 1 3 .2 2 9 5 3 .2 1 9 2 2 .7 7 4 9 2 .7 5 4 3 2 .3 8 8 9 2 .2 2 4 0 1 .9 7 3 2 1 .8 3 2 4 1 .5 9 4 2 1 .2 5 4 0 0 .0 0 5 7 0 .0 0 0 0 -0 .0 0 5 7

3 .8 9

3 .7 9 2 .8 5

2 .1 3

1 .9 3 1 .9 0 1 .0 0 0 .9 7

0 .9 1 0 .9 0 0 .7 5

Filename = 42JHTA12-150-38_Proton-1-4 Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA12-150-38 Solvent = CHLOROFORM-D Creation_Time = 13-AUG-2015 10:25:20 Revision_Time = 5-JAN-2016 10:17:13 Current_Time = 5-JAN-2016 10:17:19 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 13107 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 64 Total_Scans = 64 Relaxation_Delay = 5[s]

Recvr_Gain = 48 Temp_Get = 22.6[dC]

X_90_Width = 8[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm

以 以 以

以 以 以 以 以に に に に由 由 由 由 由 由 由 由: : : :: 42JHTA12-150-38_Proton-1-1.jdf

a b u n d an c e 0 0 .0 2 0 .0 4 0 .0 6 0 .0 8 0 .1 0 .1 2 0 .1 4 0 .1 6 0 .1 8 0 .2 0 .2 2 0 .2 4 0 .2 6 0 .2 8

X : parts per Million : Carbon13

210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0

2 0 4 .8 6 1 4 1 7 1 .0 0 5 1 1 4 0 .5 1 9 0 1 3 9 .0 9 2 4 1 3 5 .8 3 6 9 1 3 5 .3 2 9 5 1 3 2 .3 9 9 6 1 2 8 .3 8 7 8 1 2 8 .3 5 9 1 1 2 8 .3 3 9 9 1 2 6 .7 3 1 3 7 7 .2 1 0 6 7 7 .0 0 0 0 7 6 .7 8 9 4 4 4 .8 0 9 6 3 9 .6 7 7 6 2 1 .3 9 9 3 2 1 .3 1 3 2 1 7 .3 5 8 8 -0 .0 1 9 4

Filename = 42JHTA12-150-38_Carbon-1-3 Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA12-150-38 Solvent = CHLOROFORM-D Creation_Time = 13-AUG-2015 10:34:30 Revision_Time = 5-JAN-2016 12:38:11 Current_Time = 5-JAN-2016 12:38:30 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.69206016[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.44496109[Hz]

X_Sweep = 47.34848485[kHz]

X_Sweep_Clipped = 37.87878788[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = FALSE Scans = 3500 Total_Scans = 3500 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 23[dC]

X_90_Width = 10.6[us]

X_Acq_Time = 0.69206016[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.53333333[us]

Irr_Atn_Dec = 22.054[dB]

Irr_Atn_Noe = 22.054[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.69206016[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm

以 以 以

以以 以 以 以 に に に由 に 由 由由 由 由 由: 由 : :: 42JHTA12-150-38_Carbon-1-1.jdf :

13b

13b

1 H NMR (CDCl 3 ) (13c)

13 C NMR (CDCl 3 ) (13c)

a b u n d an c e 0 1 .0 2 .0 3 .0 4 .0 5 .0 6 .0 7 .0 8 .0 9 .0 1 0 .0 1 1 .0

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0

7 .9 7 1 9 7 .9 5 8 2 7 .2 6 5 3 7 .1 1 3 0 7 .1 0 0 4 6 .9 5 8 4 6 .9 4 5 8 6 .5 2 7 8 6 .5 1 5 2 4 .5 6 0 3 3 .3 3 9 5 2 .7 2 7 9 2 .7 1 7 6 2 .7 0 7 3 2 .3 5 8 0 2 .2 4 9 2 2 .2 3 5 5 2 .1 2 7 8 2 .0 4 5 4 1 .6 3 3 1 1 .2 5 9 7 0 .0 9 7 3 0 .0 0 5 7 0 .0 0 0 0 -0 .0 0 5 7

3 .3 6 3 .3 3

3 .3 0 2 .2 8

2 .2 5 1 .7 4

1 .0 8 1 .0 0 0 .9 6 0 .9 4

Filename = 42JHTA13-104-37_Proton-1-4 Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA13-104-37 Solvent = CHLOROFORM-D Creation_Time = 7-AUG-2015 14:01:41 Revision_Time = 5-JAN-2016 11:19:45 Current_Time = 5-JAN-2016 11:19:48 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 13107 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 32 Total_Scans = 32 Relaxation_Delay = 5[s]

Recvr_Gain = 40 Temp_Get = 22.9[dC]

X_90_Width = 8[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm

以 以 以

以以 以 以 以 に に に由 に 由 由由 由 由 由: 由 : :: 42JHTA13-104-37_Proton-1-1.jdf :

ab u n d an ce 0 0 .1 0 .2 0 .3 0 .4 0 .5 0 .6

X : parts per Million : Carbon13

210.0 200.0 190.0 180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0

2 0 7 .8 5 8 3 1 7 1 .5 9 8 7 1 4 0 .2 0 3 0 1 3 9 .5 9 9 8 1 3 7 .0 7 2 1 1 3 7 .0 1 4 6 1 3 2 .5 0 4 9 1 3 0 .6 7 6 1 1 3 0 .2 4 5 3 1 2 8 .5 5 0 6 1 2 8 .4 1 6 5 1 2 6 .4 7 2 8 7 7 .2 1 0 6 7 7 .0 0 0 0 7 6 .7 8 9 4 4 6 .6 7 6 7 4 1 .0 1 8 0 2 2 .3 4 7 2 2 1 .3 2 2 7 1 9 .4 9 3 9 -0 .0 2 9 0

Filename = 42JHTA13-104-37_Carbon-1-3 Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA13-104-37 Solvent = CHLOROFORM-D Creation_Time = 7-AUG-2015 14:07:23 Revision_Time = 5-JAN-2016 12:46:29 Current_Time = 5-JAN-2016 12:46:38 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.69206016[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.44496109[Hz]

X_Sweep = 47.34848485[kHz]

X_Sweep_Clipped = 37.87878788[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = FALSE Scans = 2000 Total_Scans = 2000 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 22.9[dC]

X_90_Width = 10.6[us]

X_Acq_Time = 0.69206016[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.53333333[us]

Irr_Atn_Dec = 22.054[dB]

Irr_Atn_Noe = 22.054[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.69206016[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以 以

以 以以以以 にににに 由由由由 由由由由 ::::: 42JHTA13-104-37_Carbon-1-1.jdf

13c

13c

1 H NMR (DMSO-d 6 ) (IIa)

13 C NMR (DMSO-d 6 ) (IIa)

ab u n d an ce 0 0 .1 0 .2 0 .3 0 .4 0 .5

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0

7 .5 8 5 5 7 .5 7 2 7 7 .0 1 5 9 7 .0 0 3 0 6 .9 7 1 4 6 .9 5 7 9 6 .6 2 4 4 6 .6 1 1 8 6 .5 4 5 2 6 .5 3 2 5 5 .5 5 4 2 5 .3 9 5 3 4 .9 1 7 3 4 .9 0 0 7 4 .6 6 9 1 4 .6 4 7 4 3 .3 7 8 1 3 .3 6 4 7 3 .3 5 2 9 3 .3 4 9 3 3 .3 2 2 3 3 .2 9 6 7 2 .6 4 4 9 2 .6 2 6 6 2 .4 9 0 0 2 .1 8 9 7 2 .0 9 8 7 1 .8 8 6 9 1 .7 2 0 3 1 .7 0 1 3 1 .6 1 7 6 1 .5 9 7 4 1 .5 0 9 4 1 .5 0 3 7 1 .4 8 6 1 1 .4 6 9 5

6 .5 1 4 .4 4

1 .3 9 1 .3 9

1 .1 8 1 .1 5

1 .1 0 1 .1 0 1 .0 7

1 .0 6 1 .0 6

1 .0 1 1 .0 0

0 .9 8 0 .6 6

0 .6 3

0 .5 4 0 .4 0

0 .2 8

0 .2 8

Filename = 42JHTA12-142-31_scan64_Pro Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA12-142-31 Solvent = DMSO-D6 Creation_Time = 3-SEP-2014 16:05:20 Revision_Time = 5-JAN-2016 14:00:42 Current_Time = 5-JAN-2016 14:00:46 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 209715 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 64 Total_Scans = 64 Relaxation_Delay = 5[s]

Recvr_Gain = 40 Temp_Get = 22.3[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4.25[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 16 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以 以

以 以以以以 にににに 由由由由 由由由由 ::::: 42JHTA12-142-31_scan64_Proton-2-1.jdf

ab u n d an ce 0 0 .1 0 .2 0 .3 0 .4 0 .5

X : parts per Million : Carbon13

170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

1 6 8 .1 4 2 8 1 4 2 .6 5 4 8 1 4 0 .5 3 9 9 1 3 9 .3 1 8 1 1 3 3 .5 7 1 8 1 2 8 .7 6 9 1 1 2 8 .3 8 9 9 1 2 8 .0 7 8 1 1 2 8 .0 0 2 3 1 2 7 .8 6 7 5 1 2 7 .0 5 0 2 1 2 6 .6 6 2 6 1 2 5 .1 6 2 8 7 3 .1 5 0 4 6 9 .8 8 9 6 4 7 .6 0 3 4 4 6 .3 3 1 1 3 9 .9 7 8 1 3 9 .8 3 4 8 3 9 .7 0 0 0 3 9 .5 5 6 8 2 6 .1 1 7 6 2 2 .9 8 3 2 2 0 .9 6 9 5

Filename = HTA12-142-31_Carbon-1-3.jd Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA12-142-31 Solvent = DMSO-D6 Creation_Time = 6-SEP-2014 04:47:52 Revision_Time = 5-JAN-2016 14:02:42 Current_Time = 5-JAN-2016 14:02:52 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.786432[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.27156576[Hz]

X_Sweep = 41.66666667[kHz]

X_Sweep_Clipped = 33.33333333[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = FALSE Scans = 5000 Total_Scans = 5000 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 22.4[dC]

X_90_Width = 11.2[us]

X_Acq_Time = 0.786432[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.73333333[us]

Irr_Atn_Dec = 22.1[dB]

Irr_Atn_Noe = 22.1[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.786432[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以以

以 以以以 に以にに 由に由由 由由由由 :由:::: HTA12-142-31_Carbon-1-1.jdf

IIa

IIa

NOESY NMR (DMSO-d 6 ) (IIa)

COSY NMR (DMSO-d 6 ) (IIa)

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p er M il li o n : P ro to n 8 .0 7 .0 6 .0 5 .0 4 .0 3 .0 2 .0 1 .0

abundance 0 1.0 2.0 3.0 4.0 a b u n d a n ce 0 1 .0 2 .0

Filename = HTA12-142-31_NOESY-1-3.jdf Author = y-soyaku

Experiment = noesy.jxp Sample_Id = 42JHTA12-142-31 Solvent = DMSO-D6 Creation_Time = 5-SEP-2014 19:55:32 Revision_Time = 10-DEC-2015 10:17:48 Current_Time = 10-DEC-2015 10:19:20 Comment = phase sensitive noesy Data_Format = 2D COMPLEX COMPLEX Dim_Size = 819, 512 Dim_Title = Proton Proton Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.151552[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4.5[ppm]

X_Points = 1024 X_Prescans = 4 X_Resolution = 6.59839527[Hz]

X_Sweep = 6.75675676[kHz]

X_Sweep_Clipped = 5.40540541[kHz]

Y_Domain = 1H Y_Freq = 600.1723046[MHz]

Y_Offset = 4.5[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 21.10117761[Hz]

Y_Sweep = 5.40190147[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = TRUE Scans = 12 Total_Scans = 3072 Relaxation_Delay = 1.5[s]

Recvr_Gain = 46 Temp_Get = 22.7[dC]

Mix_Time = 0.7606[s]

X_Acq_Time = 0.151552[s]

X_Atn = 2.5[dB]

X_Pulse = 8.5[us]

Y_Acq_Time = 47.39072[ms]

Y_P1_Correction = 180 PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p e r M il li o n : P ro to n 8 .0 7 .0 6 .0 5 .0 4 .0 3 .0 2 .0 1 .0

abundance 0 0.1 0.2 0.3 0.4 ab u n d an c e 0 0 .1 0 .2

Filename = HTA12-142-31_COSY-1-3.jdf Author = y-soyaku

Experiment = cosy.jxp Sample_Id = 42JHTA12-142-31 Solvent = DMSO-D6 Creation_Time = 6-SEP-2014 00:07:41 Revision_Time = 30-JAN-2016 11:43:00 Current_Time = 30-JAN-2016 11:44:48 Comment = gradient absolute value co Data_Format = 2D REAL REAL Dim_Size = 1024, 1024 Dim_Title = Proton Proton Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.1895424[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4.5[ppm]

X_Points = 1280 X_Prescans = 4 X_Resolution = 5.2758644[Hz]

X_Sweep = 6.75310643[kHz]

X_Sweep_Clipped = 5.40248514[kHz]

Y_Domain = 1H Y_Freq = 600.1723046[MHz]

Y_Offset = 4.5[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 21.10345759[Hz]

Y_Sweep = 5.40248514[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 20 Total_Scans = 5120 Relaxation_Delay = 1.5[s]

Recvr_Gain = 44 Temp_Get = 22.6[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 0.1895424[s]

X_Atn = 2.5[dB]

X_Pulse = 8.5[us]

Y_Acq_Time = 47.3856[ms]

Irr_Mode = Off PROCESSING PARAMETERS ----sinbell_auto

fft( 1, TRUE, TRUE ) ppm

[transpose]

sinbell_auto zerofill( 4 ) fft( 1, TRUE, TRUE ) ppm

abs

symmetrize( Cosy, 24 ) [transpose]

IIa

HMQC NMR (DMSO-d 6 ) (IIa)

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p e r M il li o n : C ar b o n 1 3 1 7 0 .0 1 6 0 .0 1 5 0 .0 1 4 0 .0 1 3 0 .0 1 2 0 .0 1 1 0 .0 1 0 0 .0 9 0 .0 8 0 .0 7 0 .0 6 0 .0 5 0 .0 4 0 .0 3 0 .0 2 0 .0 1 0 .0

abundance

0 0.1 0.2 0.3

ab u n d a n ce 0 0 .1

Filename = HTA12-142-31_HMQC-1-3.j Author = y-soyaku Experiment = hmqc.jxp Sample_Id = 42JHTA12-142-31 Solvent = DMSO-D6 Creation_Time = 6-SEP-2014 02:36:51 Revision_Time = 30-JAN-2016 12:54:13 Current_Time = 30-JAN-2016 12:55:55 Comment = gradient enhanced HMQC Data_Format = 2D REAL REAL Dim_Size = 819, 512 Dim_Title = Proton Carbon13 Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz X_Acq_Duration = 0.151552[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4.5[ppm]

X_Points = 1024 X_Prescans = 4 X_Resolution = 6.59839527[Hz]

X_Sweep = 6.75675676[kHz]

X_Sweep_Clipped = 5.40540541[kHz]

Y_Domain = 13C Y_Freq = 150.91343039[MHz]

Y_Offset = 95[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 112.24856322[Hz]

Y_Sweep = 28.73563218[kHz]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 18 Total_Scans = 4608 Relaxation_Delay = 1.5[s]

Recvr_Gain = 90 Temp_Get = 22.9[dC]

X_Acq_Time = 0.151552[s]

X_Atn = 2.5[dB]

X_Gamma = 42576375 X_Pulse = 8.5[us]

Y_Acq_Time = 8.9088[ms]

Y_Atn = 12[dB]

Y_Gamma = 10705836.9 Y_Pulse = 11.2[us]

Irr_Atn_Dec = 31.8[dB]

PROCESSING PARAMETERS ----sinbell4( -60, 160 ) zerofill( 1 ) fft( 1, TRUE, TRUE ) ppm

[transpose]

sinbell4( -60, 160 ) zerofill( 2 ) fft( 1, TRUE, TRUE ) ppm

abs [transpose]

IIa

1 H NMR (DMSO-d 6 ) ( IIb )

13 C NMR (DMSO-d 6 ) (IIb)

ab u n d an ce 0 0 .1 0 .2 0 .3 0 .4 0 .5 0 .6 0 .7 0 .8 0 .9 1 .0 1 .1 1 .2 1 .3 1 .4

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0

7 .4 5 9 2 7 .4 4 6 4 7 .4 2 1 3 7 .3 3 9 5 7 .3 2 6 0 7 .1 6 1 2 7 .0 4 8 5 7 .0 3 5 0 6 .9 5 3 9 6 .9 4 0 8 6 .9 0 3 5 6 .8 9 1 0 5 .5 4 9 5 5 .5 4 2 0 5 .3 8 5 3 4 .9 8 2 0 4 .9 6 4 2 4 .6 3 1 6 4 .6 2 5 4 4 .6 1 8 3 4 .6 0 9 7 4 .6 0 3 4 3 .3 6 7 7 3 .3 4 0 6 3 .3 1 7 0 3 .3 1 2 8 3 .2 8 4 4 3 .2 5 7 3 3 .2 5 2 9 2 .4 9 2 9 2 .4 9 1 6 2 .4 9 0 0 2 .1 9 4 9 1 .9 5 3 8 1 .7 6 5 0 1 .4 8 7 5 1 .4 7 5 0 1 .4 7 0 2 1 .4 5 3 4

4 .0 2 2 .9 1

2 .1 4 2 .0 1

1 .3 7 1 .2 9 1 .2 4 1 .0 9

1 .0 4

1 .0 4 1 .0 1

1 .0 0 0 .9 9

0 .9 9 0 .8 9 0 .6 7

0 .6 7 0 .4 7

0 .3 9 0 .3 4

0 .3 3 0 .2 1 0 .1 7 0 .1 2 3 8 .0 8 m

Filename = 42JHTA12-151-30_Proton-1-1 Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA12-151-30 Solvent = DMSO-D6 Creation_Time = 20-OCT-2014 19:00:16 Revision_Time = 5-JAN-2016 13:34:16 Current_Time = 5-JAN-2016 13:34:27 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 209715 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 16 Total_Scans = 16 Relaxation_Delay = 5[s]

Recvr_Gain = 46 Temp_Get = 22.8[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4.25[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 16 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以以

以 以以以 に以ににに 由由由由 由由由由 ::::: 42JHTA12-151-30_Proton-1-1.jdf

ab u n d an ce -0 .0 1 0 .0 1 0 .0 3 0 .0 5 0 .0 7 0 .0 9 0 .1 1 0 .1 3 0 .1 5 0 .1 7 0 .1 9 0 .2 1 0 .2 3 0 .2 5 0 .2 7

X : parts per Million : Carbon13

170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

1 6 7 .3 2 5 5 1 4 3 .7 5 0 1 1 3 9 .8 0 6 8 1 3 8 .9 9 8 0 1 3 3 .3 6 9 5 1 3 3 .3 3 5 8 1 2 9 .1 2 2 9 1 2 8 .9 1 2 3 1 2 8 .1 5 4 0 1 2 7 .7 4 9 5 1 2 7 .6 8 2 1 1 2 7 .5 6 4 2 1 2 6 .5 1 0 9 1 2 2 .8 0 3 6 7 3 .1 6 7 3 6 9 .9 9 9 2 4 5 .8 9 3 0 3 9 .8 3 4 8 3 9 .7 0 0 0 3 9 .5 5 6 8 2 6 .0 5 0 2 2 0 .9 5 2 6 1 7 .6 6 6 6 1 7 .4 5 5 9

Filename = 42JHTA12-151-30_Carbon-1-1 Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA12-151-30 Solvent = DMSO-D6 Creation_Time = 21-OCT-2014 03:19:52 Revision_Time = 5-JAN-2016 14:05:23 Current_Time = 5-JAN-2016 14:05:38 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.786432[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.27156576[Hz]

X_Sweep = 41.66666667[kHz]

X_Sweep_Clipped = 33.33333333[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = FALSE Scans = 6000 Total_Scans = 6000 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 22.9[dC]

X_90_Width = 11.2[us]

X_Acq_Time = 0.786432[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.73333333[us]

Irr_Atn_Dec = 22.1[dB]

Irr_Atn_Noe = 22.1[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.786432[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以 以

以 以以以以 にににに 由由由由 由由由由 ::::: 42JHTA12-151-30_Carbon-1-1.jdf

IIb

IIb

NOESY NMR (DMSO-d 6 ) (IIb)

COSY NMR (DMSO-d 6 ) (IIb)

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0

Y : p ar ts p er M il li o n : P ro to n 7 .0 6 .0 5 .0 4 .0 3 .0 2 .0

abundance 0 0.1 0.2 0.3 0.4 ab u n d an ce 0 0 .1 0 .2

Filename = 42JHTA12-151-30_NOESY-1-3.

Author = y-soyaku Experiment = noesy.jxp Sample_Id = 42JHTA12-151-30 Solvent = DMSO-D6 Creation_Time = 20-OCT-2014 19:09:30 Revision_Time = 10-DEC-2015 10:31:29 Current_Time = 10-DEC-2015 10:32:47 Comment = phase sensitive noesy Data_Format = 2D COMPLEX COMPLEX Dim_Size = 819, 512 Dim_Title = Proton Proton Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.17055744[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4[ppm]

X_Points = 1024 X_Prescans = 4 X_Resolution = 5.8631274[Hz]

X_Sweep = 6.00384246[kHz]

X_Sweep_Clipped = 4.80307397[kHz]

Y_Domain = 1H Y_Freq = 600.1723046[MHz]

Y_Offset = 4[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 18.75660232[Hz]

Y_Sweep = 4.80169019[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 8 Total_Scans = 2048 Relaxation_Delay = 1.5[s]

Recvr_Gain = 46 Temp_Get = 22.7[dC]

Mix_Time = 1.08087[s]

X_Acq_Time = 0.17055744[s]

X_Atn = 2.5[dB]

X_Pulse = 8.5[us]

Y_Acq_Time = 53.31456[ms]

Y_P1_Correction = 180.0 PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 16 )

fft( 1, TRUE, TRUE ) machinephase ppm

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p e r M il li o n : P ro to n 7 .0 6 .0 5 .0 4 .0 3 .0 2 .0 1 .0

abundance 0 0.1 0.2 0.3 0.4 ab u n d a n ce 0 0 .1 0 .2 0 .3 0 .4

Filename = 42JHTA12-151-30_COSY-1-3.j Author = y-soyaku

Experiment = cosy.jxp Sample_Id = 42JHTA12-151-30 Solvent = DMSO-D6 Creation_Time = 20-OCT-2014 22:21:49 Revision_Time = 30-JAN-2016 13:19:25 Current_Time = 30-JAN-2016 13:21:23 Comment = gradient absolute value co Data_Format = 2D REAL REAL Dim_Size = 1024, 1024 Dim_Title = Proton Proton Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.2131968[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4[ppm]

X_Points = 1280 X_Prescans = 4 X_Resolution = 4.69050192[Hz]

X_Sweep = 6.00384246[kHz]

X_Sweep_Clipped = 4.80307397[kHz]

Y_Domain = 1H Y_Freq = 600.1723046[MHz]

Y_Offset = 4[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 18.75660232[Hz]

Y_Sweep = 4.80169019[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 20 Total_Scans = 5120 Relaxation_Delay = 1.5[s]

Recvr_Gain = 52 Temp_Get = 22.7[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 0.2131968[s]

X_Atn = 2.5[dB]

X_Pulse = 8.5[us]

Y_Acq_Time = 53.31456[ms]

Irr_Mode = Off PROCESSING PARAMETERS ----sinbell_auto

fft( 1, TRUE, TRUE ) ppm

[transpose]

sinbell_auto zerofill( 4 ) fft( 1, TRUE, TRUE ) ppm

abs

symmetrize( Cosy, 24 ) [transpose]

IIb

HMQC NMR (DMSO-d 6 ) (IIb)

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p e r M il li o n : C ar b o n 1 3 1 7 0 .0 1 6 0 .0 1 5 0 .0 1 4 0 .0 1 3 0 .0 1 2 0 .0 1 1 0 .0 1 0 0 .0 9 0 .0 8 0 .0 7 0 .0 6 0 .0 5 0 .0 4 0 .0 3 0 .0 2 0 .0 1 0 .0

abundance

0 0.1

a b u n d an c e 0 0 .1 0 .2 0 .3 0 .4

Filename = 42JHTA12-151-30_HMQC-1-Author = y-soyaku Experiment = hmqc.jxp Sample_Id = 42JHTA12-151-30 Solvent = DMSO-D6 Creation_Time = 21-OCT-2014 00:53:18 Revision_Time = 30-JAN-2016 13:22:34 Current_Time = 30-JAN-2016 13:23:42 Comment = gradient enhanced HMQC Data_Format = 2D REAL REAL Dim_Size = 819, 512 Dim_Title = Proton Carbon13 Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz X_Acq_Duration = 0.17055744[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4[ppm]

X_Points = 1024 X_Prescans = 4 X_Resolution = 5.8631274[Hz]

X_Sweep = 6.00384246[kHz]

X_Sweep_Clipped = 4.80307397[kHz]

Y_Domain = 13C Y_Freq = 150.91343039[MHz]

Y_Offset = 90[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 106.14809783[Hz]

Y_Sweep = 27.17391304[kHz]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 20 Total_Scans = 5120 Relaxation_Delay = 1.5[s]

Recvr_Gain = 92 Temp_Get = 22.8[dC]

X_Acq_Time = 0.17055744[s]

X_Atn = 2.5[dB]

X_Gamma = 42576375 X_Pulse = 8.5[us]

Y_Acq_Time = 9.4208[ms]

Y_Atn = 12[dB]

Y_Gamma = 10705836.9 Y_Pulse = 11.2[us]

Irr_Atn_Dec = 31.8[dB]

PROCESSING PARAMETERS ----sinbell4( -60, 160 ) zerofill( 1 ) fft( 1, TRUE, TRUE ) ppm

[transpose]

sinbell4( -60, 160 ) zerofill( 2 ) fft( 1, TRUE, TRUE ) ppm

abs [transpose]

IIb

1 H NMR (DMSO-d 6 ) ( IIc )

13 C NMR (DMSO-d 6 ) (IIc)

ab u n d an ce 0 0 .1 0 .2 0 .3 0 .4 0 .5 0 .6 0 .7

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

7 .3 1 7 3 7 .3 0 3 9 6 .9 3 0 6 6 .9 2 1 5 6 .9 0 8 3 6 .7 8 3 2 6 .3 8 1 2 6 .3 6 8 4 5 .2 7 6 0 5 .2 6 6 9 5 .2 0 2 5 5 .2 0 1 1 4 .7 9 5 1 4 .7 7 3 1 3 .3 4 5 6 3 .3 4 2 5 3 .3 1 5 8 2 .6 3 5 7 2 .4 9 6 0 2 .4 9 3 0 2 .4 9 0 0 2 .4 8 6 9 2 .4 8 3 9 2 .3 6 3 1 2 .1 8 4 4 1 .5 8 0 8 1 .5 6 2 9 1 .2 2 4 0

3 .3 7

3 .1 7 3 .1 7

2 .0 8 2 .0 1

1 .9 9

1 .1 6 1 .0 3

1 .0 0

0 .9 8 0 .9 1

Filename = HTA13-3-32_Proton-1-8.jdf Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA13-3-32 Solvent = DMSO-D6 Creation_Time = 3-DEC-2014 18:56:08 Revision_Time = 5-JAN-2016 13:45:50 Current_Time = 5-JAN-2016 13:45:55 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 209715 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 16 Total_Scans = 16 Relaxation_Delay = 5[s]

Recvr_Gain = 42 Temp_Get = 22.6[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4.25[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 16 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以 以

以 以以以以 にににに 由由由由 由由由由 ::::: HTA13-3-32_Proton-1-1.jdf

ab u n d an ce -0 .0 1 0 .0 1 0 .0 3 0 .0 5 0 .0 7 0 .0 9 0 .1 1 0 .1 3 0 .1 5 0 .1 7 0 .1 9 0 .2 1 0 .2 3 0 .2 5

X : parts per Million : Carbon13

170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

1 6 8 .0 5 9 2 1 4 3 .5 6 2 7 1 3 8 .4 1 0 6 1 3 6 .1 6 4 6 1 3 4 .3 1 3 1 1 2 9 .0 5 6 3 1 2 8 .7 8 2 6 1 2 7 .9 2 1 3 1 2 7 .4 6 2 4 1 2 7 .1 1 6 3 6 6 .1 4 4 6 4 7 .6 7 7 7 3 9 .9 7 3 7 3 9 .8 3 6 9 3 9 .7 0 0 0 3 9 .5 5 5 1 3 9 .4 1 8 2 2 2 .7 3 0 3 2 0 .9 7 5 4 2 0 .1 7 0 4

Filename = HTA13-3-32_Carbon-1-3.jdf Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA13-3-32 Solvent = DMSO-D6 Creation_Time = 4-DEC-2014 03:18:07 Revision_Time = 5-JAN-2016 14:06:54 Current_Time = 5-JAN-2016 14:07:06 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.82313216[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.21487174[Hz]

X_Sweep = 39.8089172[kHz]

X_Sweep_Clipped = 31.84713376[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = TRUE Scans = 6000 Total_Scans = 6000 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 22.7[dC]

X_90_Width = 11.2[us]

X_Acq_Time = 0.82313216[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.73333333[us]

Irr_Atn_Dec = 22.1[dB]

Irr_Atn_Noe = 22.1[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.82313216[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以以

以 以以以 に以にに 由に由由 由由由由 :由:::: HTA13-3-32_Carbon-1-1.jdf

IIc

IIc

NOESY NMR (DMSO-d 6 ) ( IIc )

COSY NMR (DMSO-d 6 ) (IIc)

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0

Y : p ar ts p er M il li o n : P ro to n 7 .0 6 .0 5 .0 4 .0 3 .0 2 .0

abundance 0 0.2 0.4 0.6 a b u n d a n ce 0 0 .1 0 .2 0 .3

Filename = HTA13-3-32_NOESY-1-3.jdf Author = y-soyaku Experiment = noesy.jxp Sample_Id = 42JHTA13-3-32 Solvent = DMSO-D6 Creation_Time = 3-DEC-2014 19:11:15 Revision_Time = 10-DEC-2015 10:39:09 Current_Time = 10-DEC-2015 10:40:33 Comment = phase sensitive noesy Data_Format = 2D COMPLEX COMPLEX Dim_Size = 819, 512 Dim_Title = Proton Proton Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.17055744[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4[ppm]

X_Points = 1024 X_Prescans = 4 X_Resolution = 5.8631274[Hz]

X_Sweep = 6.00384246[kHz]

X_Sweep_Clipped = 4.80307397[kHz]

Y_Domain = 1H Y_Freq = 600.1723046[MHz]

Y_Offset = 4[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 18.75660232[Hz]

Y_Sweep = 4.80169019[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 8 Total_Scans = 2048 Relaxation_Delay = 1.5[s]

Recvr_Gain = 46 Temp_Get = 22.5[dC]

Mix_Time = 1.03366[s]

X_Acq_Time = 0.17055744[s]

X_Atn = 2.5[dB]

X_Pulse = 8.5[us]

Y_Acq_Time = 53.31456[ms]

Y_P1_Correction = 180.0 PROCESSING PARAMETERS ----sexp( 5.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) ppm

machinephase [transpose]

sexp( 5.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 2 )

fft( 1, TRUE, TRUE ) ppm

machinephase [transpose]

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p e r M il li o n : P ro to n 7 .0 6 .0 5 .0 4 .0 3 .0 2 .0 1 .0

abundance 0 0.1 0.2 0.3 0.4 ab u n d an c e 0 0 .1 0 .2 0 .3 0 .4

Filename = HTA13-3-32_COSY-1-3.jdf Author = y-soyaku Experiment = cosy.jxp Sample_Id = 42JHTA13-3-32 Solvent = DMSO-D6 Creation_Time = 3-DEC-2014 22:20:13 Revision_Time = 30-JAN-2016 13:00:22 Current_Time = 30-JAN-2016 13:01:33 Comment = gradient absolute value co Data_Format = 2D REAL REAL Dim_Size = 1024, 1024 Dim_Title = Proton Proton Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.2131968[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4[ppm]

X_Points = 1280 X_Prescans = 4 X_Resolution = 4.69050192[Hz]

X_Sweep = 6.00384246[kHz]

X_Sweep_Clipped = 4.80307397[kHz]

Y_Domain = 1H Y_Freq = 600.1723046[MHz]

Y_Offset = 4[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 18.75660232[Hz]

Y_Sweep = 4.80169019[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 20 Total_Scans = 5120 Relaxation_Delay = 1.5[s]

Recvr_Gain = 50 Temp_Get = 22.5[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 0.2131968[s]

X_Atn = 2.5[dB]

X_Pulse = 8.5[us]

Y_Acq_Time = 53.31456[ms]

Irr_Mode = Off PROCESSING PARAMETERS ----sinbell_auto

fft( 1, TRUE, TRUE ) ppm

[transpose]

sinbell_auto zerofill( 4 ) fft( 1, TRUE, TRUE ) ppm

abs

symmetrize( Cosy, 24 ) [transpose]

IIc

HMQC NMR (DMSO-d 6 ) (IIc)

X : parts per Million : Proton

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Y : p ar ts p e r M il li o n : C ar b o n 1 3 1 7 0 .0 1 6 0 .0 1 5 0 .0 1 4 0 .0 1 3 0 .0 1 2 0 .0 1 1 0 .0 1 0 0 .0 9 0 .0 8 0 .0 7 0 .0 6 0 .0 5 0 .0 4 0 .0 3 0 .0 2 0 .0 1 0 .0

abundance

0 0.1 0.2 0.3

ab u n d an c e 0 0 .1 0 .2 0 .3 0 .4

Filename = HTA13-3-32_HMQC-1-3.jdf Author = y-soyaku Experiment = hmqc.jxp Sample_Id = 42JHTA13-3-32 Solvent = DMSO-D6 Creation_Time = 4-DEC-2014 00:51:40 Revision_Time = 30-JAN-2016 13:02:29 Current_Time = 30-JAN-2016 13:05:28 Comment = gradient enhanced HMQC Data_Format = 2D REAL REAL Dim_Size = 819, 512 Dim_Title = Proton Carbon13 Dim_Units = [ppm] [ppm]

Dimensions = X Y Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz X_Acq_Duration = 0.17055744[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 4[ppm]

X_Points = 1024 X_Prescans = 4 X_Resolution = 5.8631274[Hz]

X_Sweep = 6.00384246[kHz]

X_Sweep_Clipped = 4.80307397[kHz]

Y_Domain = 13C Y_Freq = 150.91343039[MHz]

Y_Offset = 95[ppm]

Y_Points = 256 Y_Prescans = 0 Y_Resolution = 112.24856322[Hz]

Y_Sweep = 28.73563218[kHz]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = TRUE Scans = 20 Total_Scans = 5120 Relaxation_Delay = 1.5[s]

Recvr_Gain = 92 Temp_Get = 22.7[dC]

X_Acq_Time = 0.17055744[s]

X_Atn = 2.5[dB]

X_Gamma = 42576375 X_Pulse = 8.5[us]

Y_Acq_Time = 8.9088[ms]

Y_Atn = 12[dB]

Y_Gamma = 10705836.9 Y_Pulse = 11.2[us]

Irr_Atn_Dec = 31.8[dB]

PROCESSING PARAMETERS ----sinbell4( -60, 160 ) zerofill( 1 ) fft( 1, TRUE, TRUE ) ppm

[transpose]

sinbell4( -60, 160 ) zerofill( 2 ) fft( 1, TRUE, TRUE ) ppm

abs [transpose]

IIc

1 H NMR (DMSO-d 6 ) (IIIa)

13 C NMR (DMSO-d 6 ) (IIIa)

ab u n d an ce 0 0 .0 1 0 .0 2 0 .0 3 0 .0 4 0 .0 5 0 .0 6 0 .0 7 0 .0 8 0 .0 9 0 .1 0 .1 1 0 .1 2 0 .1 3 0 .1 4 0 .1 5 0 .1 6 0 .1 7 0 .1 8 0 .1 9 0 .2

X : parts per Million : Proton

8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0

7 .4 9 0 1 7 .4 7 7 7 7 .0 0 6 3 6 .9 8 0 6 6 .9 6 8 8 6 .7 6 8 7 6 .6 0 7 9 6 .5 9 5 3 6 .5 2 4 3 6 .5 2 1 7 4 .8 8 1 1 4 .8 7 9 7 4 .8 6 1 0 4 .8 5 9 8 3 .9 8 5 0 3 .9 6 5 3 3 .9 4 6 5 3 .9 4 5 5 3 .5 7 3 7 3 .5 6 6 5 3 .3 2 0 6 3 .2 8 8 9 3 .0 2 2 6 2 .5 9 4 4 2 .3 4 1 5 2 .1 8 5 4 2 .0 9 5 9 1 .7 9 2 5 1 .6 6 7 9 1 .5 6 6 2 1 .2 7 6 4 1 .1 0 7 4 1 .1 0 6 0 1 .0 9 1 8 1 .0 9 0 7

1 2 .4 6

1 0 .3 6 9 .3 2 8 .3 5 7 .2 2

4 .9 2 1 .3 7

1 .1 9

1 .1 6

1 .1 5 1 .1 4 1 .1 0

1 .0 6

1 .0 6

1 .0 0 0 .9 8

0 .9 3 0 .9 0 0 .8 7

Filename = 42JHTA12-146-36_Proton-1-5 Author = y-soyaku

Experiment = proton.jxp Sample_Id = 42JHTA12-146-36 Solvent = DMSO-D6 Creation_Time = 16-SEP-2014 19:38:31 Revision_Time = 5-JAN-2016 13:40:43 Current_Time = 5-JAN-2016 13:40:47 Comment = single_pulse Data_Format = 1D COMPLEX Dim_Size = 209715 Dim_Title = Proton Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 1.4548992[s]

X_Domain = 1H X_Freq = 600.1723046[MHz]

X_Offset = 5[ppm]

X_Points = 16384 X_Prescans = 1 X_Resolution = 0.68733284[Hz]

X_Sweep = 11.26126126[kHz]

X_Sweep_Clipped = 9.00900901[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = Proton Tri_Freq = 600.1723046[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE Scans = 8 Total_Scans = 8 Relaxation_Delay = 5[s]

Recvr_Gain = 36 Temp_Get = 21.9[dC]

X_90_Width = 8.5[us]

X_Acq_Time = 1.4548992[s]

X_Angle = 45[deg]

X_Atn = 2.5[dB]

X_Pulse = 4.25[us]

Irr_Mode = Off Tri_Mode = Off Dante_Presat = FALSE Initial_Wait = 1[s]

Repetition_Time = 6.4548992[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 0.2[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 16 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以 以

以 以以以以 にににに 由由由由 由由由由 ::::: 42JHTA12-146-36_Proton-1-1.jdf

ab u n d an ce -0 .0 1 0 0 .0 1 0 .0 2 0 .0 3 0 .0 4 0 .0 5 0 .0 6 0 .0 7 0 .0 8 0 .0 9 0 .1 0 .1 1 0 .1 2 0 .1 3 0 .1 4 0 .1 5 0 .1 6 0 .1 7 0 .1 8 0 .1 9 0 .2 0 .2 1 0 .2 2

X : parts per Million : Carbon13

170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

1 6 8 .9 1 8 0 1 6 8 .7 4 1 0 1 3 9 .7 8 1 6 1 3 9 .4 0 2 4 1 3 3 .6 2 2 3 1 3 2 .2 6 5 8 1 3 0 .3 1 9 4 1 2 8 .7 9 4 3 1 2 8 .4 4 0 4 1 2 8 .2 4 6 7 1 2 8 .0 4 4 4 1 2 7 .9 8 5 5 1 2 7 .8 5 0 6 1 2 7 .3 0 3 0 1 2 7 .0 9 2 3 1 2 6 .3 7 6 1 1 2 6 .0 0 5 4 7 1 .7 3 4 9 6 4 .8 6 7 8 3 9 .9 7 8 1 3 9 .8 3 4 8 3 9 .7 0 0 0 3 9 .5 5 6 8 3 9 .4 2 1 9 3 9 .2 7 8 7 2 9 .3 1 9 4 2 8 .2 8 3 1 2 3 .9 6 9 0 2 3 .2 9 5 0 2 0 .9 4 4 2

Filename = HTA12-146-36_Carbon-1-8.jd Author = y-soyaku

Experiment = carbon.jxp Sample_Id = 42JHTA12-146-36 Solvent = DMSO-D6 Creation_Time = 17-SEP-2014 03:55:26 Revision_Time = 5-JAN-2016 14:08:41 Current_Time = 5-JAN-2016 14:09:17 Comment = single pulse decoupled gat Data_Format = 1D COMPLEX Dim_Size = 26214 Dim_Title = Carbon13 Dim_Units = [ppm]

Dimensions = X Site = JNM-ECA600 Spectrometer = DELTA2_NMR Field_Strength = 14.09636928[T] (600[MHz]) X_Acq_Duration = 0.786432[s]

X_Domain = 13C X_Freq = 150.91343039[MHz]

X_Offset = 100[ppm]

X_Points = 32768 X_Prescans = 4 X_Resolution = 1.27156576[Hz]

X_Sweep = 41.66666667[kHz]

X_Sweep_Clipped = 33.33333333[kHz]

Irr_Domain = Proton Irr_Freq = 600.1723046[MHz]

Irr_Offset = 5[ppm]

Clipped = FALSE Scans = 6000 Total_Scans = 6000 Relaxation_Delay = 2[s]

Recvr_Gain = 58 Temp_Get = 22.2[dC]

X_90_Width = 11.2[us]

X_Acq_Time = 0.786432[s]

X_Angle = 30[deg]

X_Atn = 12[dB]

X_Pulse = 3.73333333[us]

Irr_Atn_Dec = 22.1[dB]

Irr_Atn_Noe = 22.1[dB]

Irr_Noise = WALTZ Irr_Pwidth = 76[us]

Decoupling = TRUE Initial_Wait = 1[s]

Noe = TRUE Noe_Time = 2[s]

Repetition_Time = 2.786432[s]

PROCESSING PARAMETERS ----dc_balance( 0, FALSE ) sexp( 2.0[Hz], 0.0[s] ) trapezoid( 0[%], 0[%], 80[%], 100[%] ) zerofill( 1 )

fft( 1, TRUE, TRUE ) machinephase ppm 以 以以

以 以以以 に以にに 由に由由 由由由由 :由:::: HTA12-146-36_Carbon-1-1.jdf

ドキュメント内 JOC SI 0326(proof) (Page 48-61)