synthesis and conformational structure of hydrazo … · s1 supporting information synthesis and...

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Supporting Information

Synthesis and Conformational Structure of Hydrazo-Bridged Homo

Calix[2]pyridine[2]triazines

Dong-Dong Liang, Mei-Xiang Wang*

†The Key Laboratory of Bioorganic Phosphorous and Chemical Biology (Ministry of

Education), Department of Chemistry, Tsinghua University, Beijing 100084 China

E-mail: [email protected]

Table of Contents

Table of Contents .............................................................................................................................. 1

1. General Information ...................................................................................................................... 2

2. Synthesis ....................................................................................................................................... 2

3. Crystal Structures ........................................................................................................................ 10

4. NMR Titration .............................................................................................................................. 13

5. References ................................................................................................................................... 14

6. Copies of 1H and 13C Spectra ....................................................................................................... 14

Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2017

mailto:[email protected]

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1. General Information

Unless otherwise noted, all reactions were carried out in oven-dried glasswares.

Anhydrous solvents were purified and dried following standard procedures. All

commercially available reagents were used as received. Compounds 11, 2a2, 83 were

synthesized according to published procedures. TLC analysis was performed on pre-

coated, glass-backed silica gel plates and visualized with UV light. Unless otherwise

noted, flash column chromatography was performed on silica gel (200 - 300 mesh).

Melting points were uncorrected. The 1H NMR, 13C NMR spectra were recorded

on a 400 MHz NMR spectrometer. 1H and 13C NMR chemical shifts were reported

relative to the signals of residual of chloroform (7.26 ppm) DMSO (2.50ppm) and that

of internal standard of TMS (0.0 ppm), respectively. Abbreviations are used in the

description of NMR data as follows: chemical shift (, ppm), multiplicity (s = singlet,

d = doublet, t = triplet, q = quartet, dt = doublet of triplets, m = multiplet), coupling

constant (J, Hz). The electron spray ionization mass spectra (ESI-MS) were recorded

on a MASS spectrometer. Infrared spectra were recorded with KBr pellets in the 4000-

400 cm−1 region.

2. Synthesis

2.1 Synthesis of 1.

2,6-Bis-hydrazinopyridine 1 was synthesized according to literature.1 Hydrazine

hydrate (12.5 mL, 200 mmol, 20 equiv.) was added to a 25 mL oven-dried, argon-filled

pear flask equipped with a magnetic stirring bar. With rapid stirring, 2,6-

difluoropyridine (1.15g, 10 mmol, 1 equiv.) was added very slowly and cautiously. The

reaction mixture was then heated to 80 oC for 24 h. Upon cooling, a yellow solid formed.

Filtration of the resulting suspension, washing with isopropanol and diethyl ether, to

give 1 (1 g, 72% yield).

General procedure for the synthesis 2b-c:

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To an ice-bath cooled solution of cyanuric chloride 6 (4.05 g, 20 mmol) in THF (50

mL) was added, respectively, alcohol (22 mmol) and 2.9 mL of collidine. The reaction

mixture was stirred for another 12 hours and then hydrochloric acid salt of collidine

formed during the reaction was filtered off and filtrate was poured into ice-water

mixture and extracted with CH2Cl2 (3 x 50 mL). After drying (Na2SO4), the solvent was

removed and the residue was purified by column chromatography on a silica gel column

with a mixture of ethyl acetate and petroleum ether as the mobile phase to give pure

2b-c.

2.1 Synthesis of 2b.

2b was obtained from flash column chromatographed on a silica gel column

(petroleum ether and ethyl acetate = 50 / 1) (2.63g, 45% yield): colorless oil; 1H NMR

(400 MHz, CDCl3) δ 5.29-5.26 (m, 1H), 1.78-1.63 (m, 4H), 1.39-1.25 (m, 8H), 0.89

(t, J = 6.9Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 172.4, 171.1, 81.9, 33.2, 27.2, 22.5,

13.9; IR (KBr, cm-1) ν 2958, 2933, 2863, 1541, 1503. HRMS (APCI-ion trap) calcd.

for C12H20Cl2N3O: [M+H]+ 292.0978. Found: 292.0975.

2.2 Synthesis of 2c.

2c was obtained from flash column chromatographed on a silica gel column

(petroleum ether and ethyl acetate = 5 / 1) (5.73 g, 75% yield): colorless oil; 1H NMR

(400 MHz, CDCl3) δ 4.57-4.49 (m, 3H), 13.78-3.35 (m, 12H), 1.74-1.38 (m, 6H); 13C

NMR (100 MHz, CDCl3) δ 172.3, 171.0, 98.7, 70.7, 70.5, 70.4, 69.3, 68.3, 66.5, 62.0,

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30.4, 25.3, 19.3; IR (KBr, cm-1) ν 2941, 2870, 1545, 1511. HRMS (ESI-ion trap)

calcd. for C14H21Cl2N3O5Na: [M+Na]+ 404.0750. Found: 404.0747.

General procedure for the synthesis 3a-c:

To a solution of 2,6-dihydrazinylpyridine 1 (2 mmol) in tetrahydrofuran (30 mL)

was added dropwise a mixture of substituted 2,4-dichloro-1,3,5-triazine 2a-c (4

mmol) and diisopropylethylamine (4.4 mmol) in tetrahydrofuran (20 mL) during 1 h.

The reaction mixture was stirred overnight. After removal of diisopropylethylamine

hydrochloride salt through filtration, the filtrate was extracted with ethyl acetate (3 x

50 mL). After drying (Na2SO4) and then removing the solvent, the residue was

chromatographed on a silica gel column with a mixture of petroleum ether and ethyl

acetate as the mobile phase to give pure linear trimer 3a-c.

2.3 Synthesis of 3a.

3a was obtained from flash column chromatographed on a silica gel column

(petroleum ether and ethyl acetate = 8 / 1) (753.6 mg, 74% yield): white solid, mp

105-107 oC; 1H NMR (400 MHz, C2D2Cl4, 120oC) δ 7.76 (br, 2H), 7.41 (t, J = 7.8Hz,

1H), 6.86 (br, 2H), 6.23 (d, J = 7.8Hz, 2H), 4.34 (t, J = 6.9Hz, 4H), 1.74-1.68 (m, 4H),

1.46-1.37 (m, 4H), 0.95 (t, J = 7.3Hz, 6H); 13C NMR (100 MHz, C2D2Cl4, 120oC) δ

171.6, 171.3, 169.1, 157.8, 140.5, 99.2, 68.9, 30.7, 19.0, 13.6; IR (KBr, cm–1) ν 3250,

2960, 1566. HRMS (ESI-ion trap) calcd. for C19H26Cl2N11O2: [M+H]+ 510.1642.

Found: 510.1640.

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(petroleum ether and ethyl acetate = 5 / 1). (885.0 mg, 68% yield): white solid, mp 128-

130 oC; 1H NMR (400 MHz, C2D2Cl4, 120oC): δ 7.66 (br, 2H), 7.42 (t, J = 7.8Hz, 1H),

6.70 (br, 2H), 6.23 (d, J = 7.8Hz, 2H), 5.15-5.09 (m, 2H), 1.74-1.58 (m, 8H), 1.33-1.28

(m, 16H), 0.90 (t, J = 6.8Hz, 12H); 13C NMR (100 MHz, C2D2Cl4, 120oC) δ 171.6,

171.4, 169.1, 158.0, 140.2, 90.1, 80.0, 33.6, 27.3, 22.5, 13.8; IR (KBr, cm–1) ν 3284,

2957, 2933, 2862, 1601, 1567, 1457. HRMS (ESI-ion trap) calcd. for C29H46Cl2N11O2:

[M+H]+ 650.3208. Found: 650.3204.


3c was obtained from flash column chromatographed on a silica gel column (petroleum

ether and ethyl acetate = 1 / 3). (498.4.0 mg, 30%): pale yellow oil; IR (KBr, cm–1) ν

3262, 2928, 1727, 1566. HRMS (ESI-ion trap) calcd. for C33H49Cl2N11O10Na: [M+Na]+

852.2933. Found: 852.2937.

It should be noted that the NMR spectra of these linear timer 3a-c are complicated

because of the rotation energy barrier of the N-N bond. 1H NMR of trimers show several

sets of signals at room temperature. The NMR spectra of 3a and 3b were then obtained

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in CDCl2CDCl2 at 120 oC. Since 3c was unstable at 120 oC. the attempts to obtain a

meaningful NMR spectrum of 3c failed.

2.4 Synthesis of 4a.

Both solutions of a mixture of 2,6-dihydrazinylpyridine 1 (2 mmol) and DIPEA

(2.4 equiv) in acetonitrile (100 mL) and of the trimer 3a-c (2 mmol) in acetonitrile (100

mL) were added dropwise at the same time and the same rate to a refluxing acetonitrile

(200 mL). After addition of two reactants, the resulting mixture was stirred for another

8 h until the starting materials were consumed. Pale yellow precipitate formed during

the reaction was collected, and the solid mixture of crude products contained the desired

all hydrazo-bridged calix[2]pyridine[2]triazine 4a and its lager ring homolog

calix[4]pyridine[4]triazine, as supported by HRMS and 1H NMR spectra, in the ratio

of 4 to1 (Figure S1-2). Recrystallization of the crude products twice from a mixture of

DMSO and acetonitrile gave pure 4a. The lager ring homolog

calix[4]pyridine[4]triazine was not obtained in pure form.

4a (484 mg, 42% yield): white solid, mp >300 oC; 1H NMR (400 MHz, DMSO,

60oC) δ 8.98 (s, 4H), 8.65 (br, 4H), 6.98 (t, J = 8.0Hz, 2H), 5.48 (d, J = 7.8Hz, 4H),

4.25 (t, J = 6.4Hz, 4H), 1.71-1.64 (m, 4H), 1.48-1.38 (m, 4H), 0.95 (t, J = 7.8Hz, 6H);

13C NMR (100 MHz, DMSO, 60oC) δ 170.1, 169.1, 158.5, 138.5, 94.3, 65.6, 30.3,

18.4, 13.3; IR (KBr, cm–1) ν 3229, 2960, 1589, 1419. HRMS (ESI-ion trap) calcd. for

C24H33N16O2: [M+H]+ 577.2967. Found: 577.2968. Elemental analysis calcd. (%) for

C24H32N16O2: C, 49.99; H, 5.59; N, 38.87. Found: C, 49.84; H, 5.67; N, 38.82.

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Figure S1. 1H NMR spectra of crude product and 4a

a)

b)

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200 400 600 800 1000 1200 1400 1600 1800 2000

m/z

1[c].D1

81 mV[sum= 7419 mV] Prof iles 1-92 Smooth Gauss 5 -Baseline 15

Data: TPT-DHP0001.D1[c] 20 Nov 2013 16:39 Cal: zcb-20130604 20 Nov 2013 16:38

Shimadzu Biotech Axima Perf ormance 2.9.3.20110624: Mode Ref lectron_HiRes, Power: 65, Blanked, P.Ext. @ 1150 (bin 62)

598.7523

597.7343

578.7950

1174.7060614.6658

1172.6836612.6699

4a

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c)

Figure S2. a) MALDI-TOF HRMS of the crude product; b) Partial expansion of the

spectrum. c) Partial expansion of the spectrum.


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535 540 545 550 555 560 565 570 575 580 585 590 595 600 605 610 615 620 625 630 635 640

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598.7523

576.7709

597.7343577.7745

578.7950

600.7769614.6658

612.6699579.7894539.8250

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1125 1130 1135 1140 1145 1150 1155 1160 1165 1170 1175 1180 1185 1190 1195 1200 1205 1210

m/z

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1174.7060

1173.6944

1172.6836

1176.7283

1152.72891177.7497

1170.6422 1190.69441154.7477

1178.75221151.7013 1194.6425

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(CHCl3 / methanol = 20 / 1) (501 mg, 35% yield): white solid, mp 200-202 oC; 1H

NMR (400 MHz, DMSO, 60oC) δ 8.89 (s, 4H), 8.27 (br, 4H), 6.99 (t, J = 7.8Hz, 2H),

5.51 (d, J = 7.8Hz, 4H), 5.13-5.07 (m, 2H), 1.64-1.58 (m, 8H), 1.37-1.30 (m, 16H),

0.92-0.88 (m, 12H); 13C NMR (100 MHz, DMSO, 60oC) δ 170.1, 169.0, 158.6, 138.4,

94.4, 75.0, 32.9, 26.6, 21.9, 13.5; IR (KBr, cm–1) ν 3286, 2955, 2869, 1571, 1414.

HRMS (ESI-ion trap) calcd. for C34H53N16O2: [M+H]+ 717.4532. Found: 717.4529.

Elemental analysis calcd. (%) for C34H52N16O2: C, 56.96; H, 7.31; N, 31.26. Found:

C, 56.59; H, 7.15; N, 31.05.


4c was obtained from recrystallization from a mixture of DMSO and DCM (574

mg, 32% yield): white solid, mp 259-260 oC; 1H NMR (400 MHz, DMSO, 100oC) δ

8.79 (br, 4H), 7.63 (br, 4H), 7.00 (br, 2H), 5.62 (br, 4H), 4.58-4.61 (m, 2H), 4.37 (s,

4H), 3.80-3.40 (m, 24H), 1.80-1.45 (m, 12H); 13C NMR (100 MHz, DMSO, 100oC) δ

169.9, 168.9, 158.3, 138.2, 97.9, 94.4, 69.6, 69.5, 69.5, 68.3, 65.7, 65.1, 61.0, 29.9,

24.6, 18.7; IR (KBr, cm–1) ν 3290, 2942, 1575, 1416, 1334. HRMS (ESI-ion trap)

calcd. for C38H56N16O10Na: [M+Na]+ 919.4258. Found: 919.4267. Elemental analysis

calcd. (%) for C38H56N16O10: C, 50.88; H, 6.29; N, 24.99. Found: C, 50.66; H, 6.29;

N, 24.80.

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2.7 Synthesis of 5.

An oven-dried Schlenk tube was charged with 4a (1 mmol, 577mg ) and NaH (12

mmol, 288mg). Under the protection of argon, the tube was cooled to 0o C in an ice-

bath. DMSO (5.0 mL, deoxygenated prior to use) was added. The Schlenk tube was

sealed and the reaction mixture was stirred at room temperature for 1 h. MeI (12 mmol,

1.7g) was added dropwise and the reaction mixture was stirred overnight. The reaction

was quenched by adding a dilute hydrochloric acid (1 N). The resulting suspension was

extracted with ethyl acetate (3 x 50 mL) and then dried with anhydrous Na2SO4. After

removal of solvent, the residue was chromatographed on a silica gel column with a

mixture of petroleum ether and ethyl acetate (5:1) as the mobile phase to give pure

linear trimer 5.

5 (586 mg, 85% yield): white solid, mp 257-258 oC; 1H NMR (400 MHz, CDCl3)

δ 6.84 (t, J = 8.0Hz, 2H), 5.38 (d, J = 8.0Hz, 4H), 4.36 (t, J = 6.8Hz, 4H), 3.32 (s, 12H),

3.29 (s, 12H), 1.82-1.64 (m, 4H), 1.53-1.47 (m, 4H), 0.99 (t, J = 7.2Hz, 6H); 13C NMR

(100 MHz, CDCl3) δ 171.3, 167.9, 156.9, 138.6, 94.2, 67.0, 34.6, 34.4, 31.1, 19.4, 14.0;

IR (KBr, cm–1) ν 2954, 1932, 2870, 1592, 1561, 1538. HRMS (ESI-ion trap) calcd. for

C32H49N16O2: [M+H]+ 689.4219. Found: 689.4216. Elemental analysis calcd. (%) for

C32H48N16O2: C, 55.80; H, 7.02; N, 32.53. Found: C, 55.82; H, 7.07; N, 32.32.

3. Crystal Structures

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Compound 4a 5 5.[(Co(ClO4)2(H2O)3]2

empirical formula C22H10Cl4F8N6O6 C34 H52 Cl4 N16 O2 C36 H60 Co2 N16 O24

Mr 1387.69 858.71 1312.62

crystal size [mm3] 0.530.380.19 0.51 x 0.37 x 0.22 0.10 x 0.08 x 0.04

crystal system triclinic triclinic monoclinic

space group P-1 P-1 P 21/c

a [Å] 13.180(3) 9.8942(18) 11.9766(4)

b [Å] 19.895(4) 11.644(2) 19.3355(5)

c [Å] 20.590(4) 20.487(4) 12.7804(4)

[deg] 108.27(3) 87.078(8) 90

[deg] 107.63(3) 78.302(9) 114.734(4)

γ [deg] 90.48(3) 68.651(6) 90

V [Å3] 4854(2) 2151.9(8) 2688.08(17)

d [g/cm3] 0.949 1.325 1.622

Z 2 2 12

T [K] 173.1500 173.1500 173.00(10)

R factor [I>2σ(I)] 0.1520 0.1118 0.0672

R factor

(all data) 0.1775 0.1208 0.073

quality of fit 1.136 1.120 1.048

(a) (b)

(c) (d)

Figure S6 X-ray molecular structure of 4a. (a) top view; (b) side views; (c) side views with partial

atom labeling and (d) 4a.3DMSO in side views. Alkyl substituents were omitted for clarity in (b), (c)

structures. Selected bond lengths (Å): N4-C3 1.386(9), N5-C4 1.371(7), N7-C8 1.390(8), N8-C9

1.358(7), N12-C11 1.332(8), N13-C12 1.386(7), N15-C16 1.370(7), N16-C1 1.359(8); Selected bond

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angles(o): N5-N4-C3 123.6(5), N4-N5-C4 120.7(5), N8-N7-C8 121.8(5), C9-N8-N7 123.1(5), C11-

N12-N13 122.9(5), C12-N13-N12 119.7(4), C16-N15-N16 122.0(5), C1-N16-N15 121.0(5).

(a) (b)

(c)

Figure S7 X-ray molecular structure of 5. (a) top view; (b) side views; (c) side views with partial

atom labeling. Alkyl substituents were omitted for clarity in side-view structures. Selected bond

lengths (Å): N4-C6 1.359(4), N4-C8 1.448(5), N5-C9 1.463(5), N5-C10 1.394(4), N7-C11 1.387(4),

N7-C15 1.441(5), N8-C16 1.459(4), N8-C17 1.366(4), N12-C19 1.361(4), N12-C24 1.461(5), N13-

C25 1.449(5), N13-C26 1.389(4), N15-C7 1.358(4), N15-C32 1.460(4), N00K-C30 1.385(4), N00K-

C31 1.449(5); Selected bond angles: N5-N4-C8 115.7(3), C6-N4-N5 120.1(3), C6-N4-C8 123.9(3),

N4-N5-C9 115.8(3), N4-N5-C10 117.8(3), C10-N5-C9 122.6(3), N8-N7-C11 118.6(3), N8-N7-C15

116.4(3), C11-N7-C15 124.3(3), N7-N8-C16 115.4(3), C17-N8-N7 119.7(3), C17-N8-C16 124.5(3),

N13-N12-C24 116.4(3), C19-N12-N13 120.5(3), C19-N12-C24 123.1(3), N12-N13-C25 117.7(3),

N12-N13-C26 117.2(3), C26-N13-C25 122.0(3), N00K-N15-C32 115.9(3), C7-N15-N00K 119.7(3),

C7-N15-C32 124.4(3), N15-N00K-C31 117.0(3), C30-N00K-N15 117.7(3), C30-N00K-C31 124.1(3).

(a) (b)

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(c)

Figure S8 X-ray molecular structure of 5.[(Co(ClO4)2(H2O)3]2. (a) top view; (b) side views; (c)

side views with partial atom labeling. Alkyl substituents and free perchlorate groups were

omitted for clarity. Selected bond lengths (Å): Co1-O2 2.121(3), Co1-O3 2.084(3), Co1-O4

2.038(3), Co1-N1 2.255(3), Co1-N2 2.191(3), Co1-N5 2.061(3).

4. NMR Titration

Stacked 1H NMR spectra of 4a in d6-DMSO with the increase of concentration (6, 8, 20, 40,

60, 80 mM) at 333K (Figure S9).

Figure S9 Stacked 1H NMR spectra of 4a in d6-DMSO at 60 oC

Stacked 1H NMR spectra of 4b in Cl2CDCDCl2 with the increase of concentration (6, 8, 20, 40,

60, 80 mM) at 333K (Figure S10).

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Figure S10 Stacked 1H NMR spectra of 4b in CDCl2CDCl2 at 60 oC

5. References

[1] Brien, K. A.; Garner, C. M.; Klausmeyer, K. K.; Feazell, R. P. J. Chem.

Crystallogr. 2005, 35, 875-883.

[2] Naseer, M. M.; Wang, D.-X.; Zhao, L.; Huang, Z.-T.; Wang, M.-X. J. Org.

Chem. 2011, 76, 1804-1813.

[3] Richard, A.; Bourel-Bonnet, L. Chem. Eur. J. 2005, 11, 7315-7321.

6. Copies of 1H and 13C Spectra

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0

Filename = 2b-H-6.jdf

Author = delta

Experiment = single_pulse.ex2

Sample_Id = S#174290

Solvent = CHLOROFORM-D

Creation_Time = 7-FEB-2017 04:42:57

Revision_Time = 16-FEB-2017 00:07:26

Current_Time = 16-FEB-2017 00:12:29

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Dim_Title = 1H

Dim_Units = [ppm]

Dimensions = X

Site = ECX 400

Spectrometer = JNM-ECX400

Field_Strength = 9.389766[T] (400[MHz])

X_Acq_Duration = 2.18365952[s]

X_Domain = 1H

X_Freq = 399.78219838[MHz]

X_Offset = 5[ppm]

X_Points = 16384

X_Prescans = 1

X_Resolution = 0.45794685[Hz]

X_Sweep = 7.5030012[kHz]

Irr_Domain = 1H

Irr_Freq = 399.78219838[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = 1H

Tri_Freq = 399.78219838[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE

Scans = 8

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Relaxation_Delay = 5[s]

Recvr_Gain = 34

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X_Angle = 45[deg]

X_Atn = 3.4[dB]

X_Pulse = 6[us]

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Tri_Mode = Off

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---- PROCESSING PARAMETERS ----

dc_balance : 0 : FALSE

sexp : 0.2[Hz] : 0.0[s]

trapezoid3 : 0[%] : 80[%] : 100[%]

zerofill : 1

fft : 1 : TRUE : TRUE

machinephase

ppm

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.0

X : parts per Million : 13C

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

17

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30

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85

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1.9

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7

7.4

75

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60

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36

3

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72

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80

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2.5

36

1

3.9

27

Filename = 2b-C-3.jdf

Author = delta

Experiment = single_pulse_dec






Comment = single pulse decoupled gat


Dim_Size = 26214

Dim_Title = 13C

Dim_Units = [ppm]

Dimensions = X

Site = ECX 400




X_Domain = 13C

X_Freq = 100.52530333[MHz]

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X_Points = 32768

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X_Sweep = 31.40703518[kHz]

Irr_Domain = 1H

Irr_Freq = 399.78219838[MHz]

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Incomplete_Copy = TRUE

Scans = 1

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Recvr_Gain = 50

Temp_Get = 19[dC]

X_90_Width = 9[us]

X_Acq_Time = 1.04333312[s]

X_Angle = 30[deg]

X_Atn = 8.823[dB]

X_Pulse = 3[us]

Irr_Atn_Dec = 23.03[dB]

Irr_Atn_Noe = 23.03[dB]

Irr_Noise = WALTZ

Decoupling = TRUE

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X_Freq = 399.78219838[MHz]

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Recvr_Gain = 20

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Initial_Wait = 1[s]


dc_balance( 0, FALSE )

sexp( 0.2[Hz], 0.0[s] )

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X_Freq = 100.52530333[MHz]

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sexp( 2.0[Hz], 0.0[s] )

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X_Sweep = 7.5030012[kHz]

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Irr_Freq = 399.78219838[MHz]

Irr_Offset = 5[ppm]

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Tri_Freq = 399.78219838[MHz]

Tri_Offset = 5[ppm]

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Recvr_Gain = 34

Temp_Get = 120[dC]

X_90_Width = 12[us]

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X_Angle = 45[deg]

X_Atn = 9[dB]

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zerofill : 1


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X_Domain = 13C

X_Freq = 100.52530333[MHz]

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X_90_Width = 9[us]

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Dimensions = X

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X_Domain = 1H

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trapezoid3 : 0[%] : 80[%] : 100[%]

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X_Domain = 13C

X_Freq = 100.52530333[MHz]

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Solvent = DMSO-D6






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Dim_Units = [ppm]

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X_Domain = 1H

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Temp_Get = 60[dC]

X_90_Width = 12[us]

X_Acq_Time = 2.18365952[s]

X_Angle = 45[deg]

X_Atn = 3.4[dB]

X_Pulse = 6[us]

Irr_Mode = Off

Tri_Mode = Off


Initial_Wait = 1[s]



sexp : 0.2[Hz] : 0.0[s]

trapezoid3 : 0[%] : 80[%] : 100[%]

zerofill : 1


machinephase

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X_Domain = 13C

X_Freq = 100.52530333[MHz]

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X_Points = 32768

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X_Sweep = 31.40703518[kHz]

Irr_Domain = 1H

Irr_Freq = 399.78219838[MHz]

Irr_Offset = 5[ppm]

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Scans = 501

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Recvr_Gain = 54

Temp_Get = 60[dC]

X_90_Width = 9[us]

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X_Angle = 30[deg]

X_Atn = 8.823[dB]

X_Pulse = 3[us]



Irr_Noise = WALTZ

Decoupling = TRUE

Initial_Wait = 1[s]

Noe = TRUE

Noe_Time = 2[s]



sexp : 2.0[Hz] : 0.0[s]

trapezoid3 : 0[%] : 80[%] : 100[%]

zerofill : 1


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Solvent = DMSO-D6

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Dim_Units = [ppm]

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X_Domain = 1H

X_Freq = 399.78219838[MHz]

X_Offset = 5[ppm]

X_Points = 16384

X_Prescans = 1


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Irr_Freq = 399.78219838[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = 1H

Tri_Freq = 399.78219838[MHz]

Tri_Offset = 5[ppm]

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X_Angle = 45[deg]

X_Atn = 3.4[dB]

X_Pulse = 6[us]

Irr_Mode = Off

Tri_Mode = Off


Initial_Wait = 1[s]



sexp( 0.2[Hz], 0.0[s] )

trapezoid3( 0[%], 80[%], 100[%] )

zerofill( 1 )


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Filename = 4c-C-3.jdf

Author = delta



Solvent = DMSO-D6


Revision_Time = 17-MAR-2016 08:25:44




Dim_Size = 26214

Dim_Title = 13C

Dim_Units = [ppm]

Dimensions = X

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X_Domain = 13C

X_Freq = 100.52530333[MHz]

X_Offset = 100[ppm]

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Recvr_Gain = 52

Temp_Get = 90[dC]

X_90_Width = 11[us]

X_Acq_Time = 1.04333312[s]

X_Angle = 30[deg]

X_Atn = 7.8[dB]

X_Pulse = 3.66666667[us]



Irr_Noise = WALTZ

Decoupling = TRUE

Initial_Wait = 1[s]

Noe = TRUE

Noe_Time = 2[s]



sexp : 2.0[Hz] : 0.0[s]

trapezoid3 : 0[%] : 80[%] : 100[%]

zerofill : 1


machinephase

ppm

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Author = delta









Dim_Size = 13107

Dim_Title = 1H

Dim_Units = [ppm]

Dimensions = X

Site = ECX 400




X_Domain = 1H

X_Freq = 399.78219838[MHz]

X_Offset = 5[ppm]

X_Points = 16384

X_Prescans = 1


X_Sweep = 7.5030012[kHz]

Irr_Domain = 1H

Irr_Freq = 399.78219838[MHz]

Irr_Offset = 5[ppm]

Tri_Domain = 1H

Tri_Freq = 399.78219838[MHz]

Tri_Offset = 5[ppm]

Clipped = FALSE

Scans = 8

Total_Scans = 8


Recvr_Gain = 60

Temp_Get = 20.4[dC]

X_90_Width = 11[us]

X_Acq_Time = 2.18365952[s]

X_Angle = 45[deg]

X_Atn = 3.4[dB]

X_Pulse = 5.5[us]

Irr_Mode = Off

Tri_Mode = Off


Initial_Wait = 1[s]



sexp : 0.2[Hz] : 0.0[s]

trapezoid3 : 0[%] : 80[%] : 100[%]

zerofill : 1


machinephase

ppm

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Filename = 5-C-9.jdf

Author = delta


Sample_Id = S#90517







Dim_Size = 26214

Dim_Title = 13C

Dim_Units = [ppm]

Dimensions = X

Site = ECX 400




X_Domain = 13C

X_Freq = 100.52530333[MHz]

X_Offset = 100[ppm]

X_Points = 32768

X_Prescans = 42


X_Sweep = 31.40703518[kHz]

Irr_Domain = 1H

Irr_Freq = 399.78219838[MHz]

Irr_Offset = 5[ppm]

Clipped = TRUE

Scans = 6844

Total_Scans = 6844


Recvr_Gain = 58

Temp_Get = 19.9[dC]

X_90_Width = 9.25[us]

X_Acq_Time = 1.04333312[s]

X_Angle = 30[deg]

X_Atn = 7.8[dB]

X_Pulse = 3.08333333[us]



Irr_Noise = WALTZ

Decoupling = TRUE

Initial_Wait = 1[s]

Noe = TRUE

Noe_Time = 2[s]



sexp( 2.0, 0.0[s] )

trapezoid3( 0[%], 80[%], 100[%] )

zerofill( 1 )


ppm

machinephase

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