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SI 1
Supporting Information
2-Aroylindoles from o-bromochalcones via Cu (I)-catalyzed SNAr with azide and intramolecular nitrene C–H insertion Yogesh Goriya and Chepuri V. Ramana*
CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road,
Pune – 411 008 (India).
Email: [email protected]
Table of content ……………………………………………………………..……SI 2 General remarks ……………………………………………………….………….SI 5 General Procedure for Preparation of chalcone.…………………….…………… SI 5 General Scheme for Preparation of 4c–4e ………………………………….….…SI 6 General procedure for Cu (I)-catalyzed synthesis of 2-aroyl indole .......................SI 6
Electronic Supplementary Material (ESI) for ChemComm.This journal is © The Royal Society of Chemistry 2014
SI 2
S. No Compound Data Page No
1
Characterization data SI 6 1H NMR Spectrum SI 16 13C NMR Spectrum SI 17
DEPT Spectrum SI 18
2
Characterization data SI 6 1H NMR Spectrum SI 19 13C NMR Spectrum SI 20
DEPT Spectrum SI 21
Mass Spectrum (HRMS ) SI 22
3
Characterization data SI 7 1H NMR Spectrum SI 23 13C NMR Spectrum SI 24
DEPT Spectrum SI 25
4
Characterization data SI 7 1H NMR Spectrum SI 26 13C NMR Spectrum SI 27
DEPT Spectrum SI 28
Mass Spectrum (HRMS) SI 29
5
Characterization data SI 8 1H NMR Spectrum SI 30 13C NMR Spectrum SI 31
DEPT Spectrum SI 32
6
Characterization data SI 8 1H NMR Spectrum SI 33 13C NMR Spectrum SI 34
DEPT Spectrum SI 35
Mass Spectrum (HRMS) SI 36
7
Characterization data SI 8 1H NMR Spectrum SI 37 13C NMR Spectrum SI 38
DEPT Spectrum SI 39
Mass Spectrum (HRMS) SI 40
8
Characterization data SI 9 1H NMR Spectrum SI 41 13C NMR Spectrum SI 42
DEPT Spectrum SI 43
9
Characterization data SI 9 1H NMR Spectrum SI 44 13C NMR Spectrum SI 45
DEPT Spectrum SI 46
Mass Spectrum (HRMS) SI 47
10
Characterization data SI 9 1H NMR Spectrum SI 48 13C NMR Spectrum SI 49
DEPT Spectrum SI 50
11
Characterization data SI 10 1H NMR Spectrum SI 51 13C NMR Spectrum SI 52
DEPT Spectrum SI 53
Mass Spectrum (HRMS) SI 54
SI 3
S. No Compound Data Page No
12
Characterization data SI 10 1H NMR Spectrum SI 55 13C NMR Spectrum SI 56
DEPT Spectrum SI 57
13
Characterization data SI 10 1H NMR Spectrum SI 58 13C NMR Spectrum SI 59
DEPT Spectrum SI 60
Mass Spectrum (HRMS) SI 61
14
Characterization data SI 11 1H NMR Spectrum SI 62 13C NMR Spectrum SI 63
DEPT Spectrum SI 64
Mass Spectrum (HRMS) SI 65
15
Characterization data SI 11 1H NMR Spectrum SI 66 13C NMR Spectrum SI 67
DEPT Spectrum SI 68
Mass Spectrum (HRMS) SI 69
16
Characterization data SI 11 1H NMR Spectrum SI 70 13C NMR Spectrum SI 71
DEPT Spectrum SI 72
17
Characterization data SI 12 1H NMR Spectrum SI 73 13C NMR Spectrum SI 74
DEPT Spectrum SI 75
Mass Spectrum (HRMS) SI 76
18
Characterization data SI 12 1H NMR Spectrum SI 77 13C NMR Spectrum SI 78
DEPT Spectrum SI 79
Mass Spectrum (HRMS) SI 80
19
Characterization data SI 12 1H NMR Spectrum SI 81 13C NMR Spectrum SI 82
DEPT Spectrum SI 83
20
Characterization data SI 13 1H NMR Spectrum SI 84 13C NMR Spectrum SI 85
DEPT Spectrum SI 86
Mass Spectrum (HRMS) SI 87
21
Characterization data SI 13 1H NMR Spectrum SI 88 13C NMR Spectrum SI 89
DEPT Spectrum SI 90
SI 4
S. No Compound Data Page No
22
Characterization data SI 13 1H NMR Spectrum SI 91 13C NMR Spectrum SI 92
DEPT Spectrum SI 93
Mass Spectrum (HRMS) SI 94
23
Characterization data SI 14 1H NMR Spectrum SI 95 13C NMR Spectrum SI 96
DEPT Spectrum SI 97
24
Characterization data SI 14 1H NMR Spectrum SI 98 13C NMR Spectrum SI 99
DEPT Spectrum SI 100
Mass Spectrum (HRMS) SI 101
25
Characterization data SI 14 1H NMR Spectrum SI 102 13C NMR Spectrum SI 103
DEPT Spectrum SI 104
Mass Spectrum (HRMS) SI 105
26
Characterization data SI 15 1H NMR Spectrum SI 106 13C NMR Spectrum SI 107
DEPT Spectrum SI 108
27
Characterization data SI 15 1H NMR Spectrum SI 109 13C NMR Spectrum SI 110
DEPT Spectrum SI 111
SI 5
General Remarks
Reactions were carried out in anhydrous solvents under an atmosphere of argon in oven-dried
glassware. Commercial reagents and solvents were used without purification. Column
chromatography was carried out by using spectrochem silica gel (60–120, 100–200, 230–400
mesh). 1H and 13C NMR spectroscopy measurements were carried out on Bruker AC 200
MHz, Bruker DRX 400, DRX 500 MHz and JEOL 400 spectrometers, and TMS was used as
an internal standard. 1H and 13C NMR chemical shifts are reported in ppm downfield from
Chloroform-d (δ = 7.25) or TMS and coupling constants (J) are reported in Hertz (Hz). The
following abbreviations are used to designate signal multiplicity: s = singlet, d = doublet, t =
triplet, q = quartet, m = multiplet, b = broad. The Multiplicity of 13C NMR signals was
assigned with the help of DEPT spectra and the abbreviations used: s = singlet d = doublet t =
triplet q = quartet, represent C (quaternary), CH, CH2 and CH3 respectively. Mass
spectroscopy was carried out on PI QStar Pulsar (Hybrid Quadrupole-TOF LC/MS/MS) and
4800 plus MALDI TOF/TOF Applied Biosystem spectrometer or UPLC coupled Mass
Spectrometer (Waters). HRMS mass spectra were recorded on a Thermo Scientific Q-
Exactive, Accela 1250 pump.
General Procedure for Preparation of chalcone:
Compounds 1a–1t was prepared according to literature procedure.1 Aqueous NaOH (2.5 N, 1
mL) was added drop-wise to a mixture of 2-bromobenzaldehyde (2.7 mmol), acetophenone
(2.7 mmol) in ethanol (4 mL) at ambient temperature. After stirring overnight, the reaction
mixture was poured into brine solution (20 mL) and extracted with CH2Cl2 (20 mL). The
extract was washed with water (2 × 30 mL), dried over Na2SO4, and evaporated under
1 M. Shen, B. E. Leslie and T. G. Driver, Angew. Chem. Int. Ed., 2008, 47, 5056.
SI 6
reduced pressure. The crude was purified over silica gel (ethyl acetate and pet ether as eluent)
to give the product. Yields were not optimized.
General Scheme for Preparation of 4c–4e:2
General procedure for Cu(I)-catalyzed synthesis of 2-aroyl indole:
To a solution of o-bromochalcone (1.0 mmol) in NMP (1 mL), were added L-proline (0.2
mmol), K2CO3 (4.0 mmol), CuI (0.2 mmol), and NaN3 (1.2 mmol). The mixture was stirred at
110 C. After 15h the reaction mixture was cooled and diluted with 30 mL of water and
extracted with ethyl acetate (3 X 30 mL). Combined organic layer was dried (Na2SO4) and
evaporated under reduced pressure. The crude was purified over silica gel (ethyl acetate and
pet ether as eluent) provided 2-aroyl indole in moderate to good yields.
(1H-Indol-2-yl)(phenyl)methanone (2a)3:-
Light yellow solid; 76% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); 1H
NMR (200 MHz, CDCl3): 7.16 (s, 1H), 7.16 (dt, J = 1.0, 7.0 Hz, 1H),
7.37 (ddd, J = 1.0, 6.8, 8.4 Hz, 1H), 7.45–7.62 (m, 4H), 7.71 (d, J = 8.0
Hz, 1H), 7.96–8.01 (m, 2H), 9.27 (br s, 1H); 13C NMR (100 MHz, CDCl3): 112.2 (d), 112.9
(d), 121.0 (d), 123.2 (d), 126.5 (d), 127.7 (s), 128.5 (d, 2C), 129.2 (d, 2C), 132.4 (d), 134.3
(s), 137.5 (s), 138.0 (s), 187.2 (s) ppm.
(1H-Indol-2-yl)(2-methoxy-4-methylphenyl) methanone (2b):-
Brown solid; 59% Yield; Rf 0.2 (10% ethyl acetate/pet. ether); mp:
112–113 °C; 1H NMR (200 MHz, CDCl3): 2.43 (s, 3H), 3.82 (s, 3H),
2 M. Gallant, M. Belley, M.-C. Carriere, A. Chateauneuf, D. Denis, N. Lachance, S. Lamontagne, K. M. Metters, N. Sawyer, D. Slipetz, J. F. Truchon and M. Labelle, Bioorg. Med. Chem. Lett., 2003, 13, 3813 3 W.-C. Gao, S. Jiang, R.-L. Wang and C. Zhang, Chem. Commun., 2013, 49, 4890.
NH
O
SI 7
6.84 (s, 1H), 6.86 (d, J = 6.8 Hz, 1H), 6.93 (d, J = 1.8 Hz, 1H), 7.12 (ddd, J = 0.9, 6.9, 7.9
Hz, 1H), 7.29–7.37 (m, 1H), 7.42–7.48 (m, 2H), 7.64 (d, J = 8.0 Hz, 1H), 9.43 (s, 1H); 13C
NMR (50 MHz, CDCl3): 21.9 (q), 55.7 (q), 112.2 (d), 112.5 (d), 112.8 (d), 120.7 (d), 120.8
(d), 123.1 (d), 125.4 (s), 126.3 (d), 127.6 (s), 130.0 (d), 135.9 (s), 137.7 (s), 142.8 (s), 157.6
(s), 187.1 (s) ppm; HRMS (ESI+): calcd. for C17H15O2NNa = 288.0995, found 288.0995.
(5-Bromo-2-methoxyphenyl)(1H-Indol-2-yl)methanone (2c)4:
Brown solid; 67% Yield; Rf 0.5 (15% ethyl acetate/pet. ether); 1H
NMR (200 MHz, CDCl3): 3.80 (s, 3H), 6.91 (m, 2H), 7.14 (ddd, J =
1.1, 6.8, 8.0 Hz, 1H), 7.36 (ddd, J = 1.0, 6.8, 7.9 Hz, 1H), 7.44–7.48
(m, 1H), 7.55–7.60 (m, 2H), 7.66 (br d, J = 8.2 Hz, 1H), 9.37 (s, 1H); 13C NMR (125 MHz,
CDCl3): 56.0 (q), 112.7 (2C, s and d), 113.4 (d), 113.6 (d), 121.1 (d), 123.3 (d), 126.8 (d),
127.5 (s), 129.8 (s), 132.0 (d), 134.5 (d), 135.2 (s), 137.9 (s), 156.5 (s), 185.4 (s) ppm.
(1H-Indol-2-yl)(naphthalen-1-yl)methanone (2d):-
Yellow solid; 77% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); mp:
150–151 °C; 1H NMR (400 MHz, CDCl3): 6.97 (d, J = 1.0 Hz,
1H), 7.15 (t, J = 6.0 Hz, 1H), 7.38 (ddd, J = 0.8, 7.0, 8.0 Hz, 1H),
7.50–7.59 (m, 4H), 7.65 (d, J = 8.0 Hz, 1H), 7.88–7.95 (m, 2H), 8.04 (d, J = 8.3 Hz, 1H),
8.28–8.30 (m, 1H), 9.62 (s, 1H); 13C NMR (100 MHz, CDCl3): 112.3 (d), 113.7 (d), 121.1
(d), 123.3 (d), 124.3 (d), 125.5 (d), 126.5 (d), 126.8 (d), 127.3 (d), 127.6 (s), 127.8 (d), 128.4
(d), 130.8 (s), 131.5 (d), 133.8 (s), 135.6 (s), 136.0 (s), 137.9 (s), 188.8 (s) ppm; HRMS
(ESI+): calcd. for C19H13ONNa = 294.0889, found 294.0890.
4 Y. Miki, Y. Tsuzaki, C. Kai and H. Hachiken, Heterocycles, 2002, 57, 1635
NH
O
SI 8
Furan-2-yl(1H-Indol-2-yl)methanone (2e)3:
Brown solid; 76% Yield; Rf 0.5 (10% ethyl acetate/pet. ether); 1H NMR
(200 MHz, CDCl3): 6.63–6.64 (m, 1H), 7.71 (t, J = 7.6 Hz, 3H), 7.37
(t, J = 7.7 Hz, 1H), 7.45–7.47 (m, 2H), 7.72 (br d, J = 8.6 Hz, 2H), 7.76 (d, J = 1.0 Hz, 1H),
9.44 (s, 1H); 13C NMR (50 MHz, CDCl3): 111.5 (d), 112.1 (d), 112.5 (d), 118.6 (d), 121.0
(d), 123.3 (d), 126.5 (d), 128.0 (s), 133.4 (s), 137.2 (s), 146.5 (d), 152.7 (s), 172.6 (s) ppm.
(1H-Indol-2-yl)(1-methyl-1H-pyrrol-2-yl) methanone (2f):-
Brown solid; 49% Yield; Rf 0.2 (10% ethyl acetate/pet. ether); mp: 100–
101 °C; 1H NMR (500 MHz, CDCl3): 4.02 (s, 3H), 6.23 (dd, J = 2.7,
3.8 Hz, 1H), 6.94 (br s, 1H), 7.16 (t, J = 7.6 Hz, 1H), 7.20 (dd, J = 1.4, 3.9 Hz, 1H), 7.23 (s,
1H), 7.33 (t, J = 7.6 Hz, 1H), 7.45 (d, J = 8.3 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 9.37 (s, 1H);
13C NMR (125 MHz, CDCl3): 37.0 (q), 108.5 (d), 109.7 (d), 111.9 (d), 120.7 (d, 2C), 122.9
(d), 125.5 (d), 127.8 (s), 130.3 (s), 131.2 (d), 135.6 (s), 136.9 (s), 176.3 (s) ppm; HRMS
(ESI+): calcd. for C14H12ON2H+ = 225.1022, found 225.1021.
(1H-Indol-2-yl)(pyridin-2-yl)methanone (2g):-
Yellow solid; 57% Yield; Rf 0.2 (10% ethyl acetate/pet. ether); mp: 130–
131 °C; 1H NMR (400 MHz, CDCl3): 7.15 (t, J = 7.5 Hz, 1H), 7.36
(ddd, J = 0.5, 6.9, 7.9 Hz, 1H), 7.48–7.55 (m, 2H), 7.75 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 7.93
(dt, J = 1.5, 7.8 Hz, 1H), 8.28 (d, J = 8.0 Hz, 1H), 8.81 (d, J = 4.3 Hz, 1H), 10.84 (s, 1H); 13C
NMR (100 MHz, CDCl3): 112.4 (d), 113.3 (d), 120.8 (d), 123.3 (d), 124.2 (d), 126.3 (d),
126.7 (d), 127.4 (s), 135.0 (s), 137.4 (d), 137.7 (s), 148.5 (d), 155.0 (s), 181.2 (s) ppm;
HRMS (ESI+): calcd. for C14H10ON2Na = 245.0685, found 245.0688.
SI 9
Benzofuran-2-yl(1H-Indol-2-yl)methanone (2h)5:
Yellow solid; 78% Yield; Rf 0.4 (10% ethyl acetate/pet. ether); 1H
NMR (500 MHz, CDCl3): 7.20 (t, J = 7.5 Hz, 1H), 7.36 (t, J = 7.6 Hz,
1H), 7.40 (t, J = 7.6 Hz, 1H), 7.48 (d, J = 8.2 Hz, 1H), 7.53 (t, J = 7.8
Hz, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.77 (d, J = 7.9 Hz, 1H), 7.78 (s, 1H), 7.81 (d, J = 8.1 Hz,
1H), 7.88 (br s, 1H), 9.33 (s, 1H); 13C NMR (125 MHz, CDCl3): 112.1 (d), 112.3 (d), 112.4
(d), 114.3 (d), 121.2 (d), 123.2 (d), 123.6 (d), 124.0 (d), 126.9 (d), 127.1 (s), 128.0 (s), 128.2
(d), 133.7 (s), 137.5 (s), 152.9 (s), 155.9 (s), 174.0 (s) ppm.
Benzo[b]thiophen-3-yl(1H-Indol-2-yl)methanone (2i):-
Light brown solid; 69% Yield; Rf 0.4 (10% ethyl acetate/pet. ether);
mp: 187–188 °C; 1H NMR (500 MHz, CDCl3): 7.18 (t, J = 6.7 Hz,
1H), 7.25 (s, 1H), 7.38 (t, J = 6.6 Hz, 1H), 7.45–7.51 (m, 3H), 7.74 (d,
J = 7.3, 1H), 7.93 (d, J = 7.3 Hz, 1H), 8.36 (s, 1H), 8.50 (d, J = 7.3 Hz, 1H), 9.52 (s, 1H); 13C
NMR (125 MHz, CDCl3): 111.6 (d), 112.2 (d), 121.1 (d), 122.4 (d), 123.2 (d), 124.7 (d),
125.5 (d), 125.6 (d), 126.5 (d), 127.7 (s), 134.7 (s), 135.5 (2C, s and d), 137.2 (s), 137.6 (s),
140.0 (s), 181.2 (s) ppm; HRMS (ESI+): calcd. for C17H11ONSH+ = 278.0634, found
278.0634.
1-(1H-Indol-2-yl)pentan-1-one (2j)6:
Brown solid; 47% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); 1H NMR
(500 MHz, CDCl3): 0.96 (t, J = 7.4 Hz, 3H), 1.39–1.46 (m, 2H), 1.73–
1.79 (m, 2H), 2.94 (t, J = 7.6 Hz, 2H), 7.15 (t, J = 7.5 Hz, 1H), 7.20 (s, 1H), 7.34 (t, J = 7.6
Hz, 1H), 7.42 (d, J = 8.3 Hz, 1H), 7.70 (d, J = 8.1 Hz, 1H), 9.09 (s, 1H); 13C NMR (125
5 S. Mahboobi, A. Uecker, C. Cenac, A. Sellmer, E. Eichhorn, S. Elz, F.-D. Bohmer and S. Dove, Bioorg. Med. Chem., 2007, 15, 2187. 6 P. C. Too, S. H. Chua, S. H. Wong and S. Chiba, J. Org. Chem., 2011, 76, 6159.
NH O
S
NH
O
O
NH
C4H9
O
SI 10
MHz, CDCl3): 13.9 (q), 22.5 (t), 27.3 (t), 38.1 (t), 109.0 (d), 112.1 (d), 120.9 (d), 123.0 (d),
126.2 (d), 127.6 (s), 135.2 (s), 137.2 (s), 193.6 (s) ppm.
Cyclopropyl (1H-Indol-2-yl) methanone (2k):-
Brown solid; 46% Yield; Rf 0.5 (10% ethyl acetate/pet. ether); mp: 143–
145 °C; 1H NMR (200 MHz, CDCl3): 1.02–1.11 (m, 2H), 1.25–1.32 (m,
2H), 2.59–2.71 (m, 1H), 7.11–7.19 (m, 1H), 7.30–7.45 (m, 3H), 7.73 (dd, J = 0.5, 8.1 Hz,
1H), 9.24 (s, 1H); 13C NMR (125 MHz, CDCl3): 11.4 (t, 2C), 17.5 (d), 109.1 (d), 112.2 (d),
120.8 (d), 122.9 (d), 126.1 (d), 127.6 (s), 135.8 (s), 137.3 (s), 192.9 (s) ppm; HRMS (ESI+):
calcd. for C12H11ONH+ = 186.0913, found 186.0916.
(5-Methoxy-1H-Indol-2-yl)(phenyl)methanone (2l)7:-
Yellow solid; 74% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); 1H
NMR (200 MHz, CDCl3): 3.84 (s, 3H), 7.02–7.08 (m, 3H), 7.37–
7.41 (m, 1H), 7.49–7.63 (m, 3H), 7.69–8.01 (m, 2H), 9.52 (s, 1H);
13C NMR (100 MHz, CDCl3): 55.6 (q), 102.6 (d), 112.5 (d), 113.3 (d), 118.4 (d), 127.9 (s),
128.4 (d, 2C), 129.2 (d, 2C), 132.2 (d), 133.3 (s), 134.7 (s), 138.1 (s), 154.7 (s), 187.1 (s)
ppm.
(5-Chloro-1H-Indol-2-yl)(phenyl)methanone (2m):-
Light yellow solid; 74% Yield; Rf 0.3 (10% ethyl acetate/pet. ether);
mp: 198–200 °C; 1H NMR (400 MHz, CDCl3): 7.08–7.09 (m, 1H),
7.32 (dd, J = 1.9, 8.8 Hz, 1H), 7.42 (d, J = 8.8 Hz, 1H), 7.52–7.56 (m,
2H), 7.61–7.65 (m, 1H), 7.68 (br s, 1H), 7.97–7.99 (m, 2H), 9.47 (s, 1H); 13C NMR (100
MHz, CDCl3): 111.7 (d), 113.3 (d), 122.3 (d), 126.6 (s), 127.0 (d), 128.6 (d, 2C and s, 1C),
129.2 (d, 2C), 132.6 (d), 135.3 (s), 135.7 (s), 137.6 (s), 187.0 (s) ppm; HRMS (ESI+): calcd.
for C15H10ONClH+ = 256.0524, found 256.0522. 7 S. Mahboobi, S. Teller, H. Pongratz, H. Hufsky, A. Sellmer, A. Botzki, A. Uecker, T. Beckers, S. Baasner, C. Schachtele, F. Uberall, M. U. Kassack, S. Dove and F.-D. Bohmer, J. Med. Chem., 2002, 45, 1002.
SI 11
(6-Bromo-5-methoxy-1H-Indol-2-yl)(phenyl)methanone (2n):-
Yellow solid; 59% Yield; Rf 0.2 (10% ethyl acetate/pet. ether); mp:
177–178 °C; 1H NMR (200 MHz, CDCl3): 3.92 (s, 3H), 7.06 (s,
1H), 7.11 (s, 1H), 7.52 (d, J = 7.6 Hz, 1H), 7.54 (d, J = 7.7 Hz, 1H),
7.63 (t, J = 7.3 Hz, 1H), 7.71 (s, 1H), 7.96 (s, 1H), 7.98 (s, 1H), 9.42 (s, 1H); 13C NMR (125
MHz, CDCl3): 56.6 (q), 103.3 (d), 112.1 (d), 113.3 (s), 116.8 (d), 127.3 (s), 128.5 (d, 2C),
129.2 (d, 2C), 132.5 (d), 133.0 (s), 135.1 (s), 137.8 (s), 151.0 (s), 186.9 (s) ppm; HRMS
(ESI+): calcd. for C16H12O2NBrH+ = 330.0124, found 330.0132.
(5-Bromo-2-methoxyphenyl)(5-methoxy-1H-Indol-2-yl)methanone (2o):-
Yellow solid; 68% Yield; Rf 0.4 (15% ethyl acetate/pet. ether);
mp: 168–170 °C; 1H NMR (200 MHz, CDCl3): 3.80 (s, 3H),
3.82 (s, 3H), 6.84 (s, 1H), 6.91 (d, J = 8.7 Hz, 1H), 7.03–7.05
(m, 2H), 7.35 (d, J = 8.8 Hz, 1H), 7.56–7.59 (m, 2H), 9.20 (s, 1H); 13C NMR (125 MHz,
CDCl3): 55.6 (q), 56.1 (q), 102.8 (d), 112.3 (s), 113.0 (d), 113.2 (d), 113.4 (d), 118.9 (d),
127.9 (s), 129.9 (s), 132.1 (d), 133.4 (s), 134.4 (d), 135.6 (s), 154.8 (s), 156.5 (s), 185.0 (s)
ppm; HRMS (ESI+): calcd. for C17H14O3NBrH+ = 360.0230, found 360.0234.
(5-Methoxy-1H-Indol-2-yl)(naphthalen-1-yl)methanone (2p)7:-
Brown solid; 73% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); 1H
NMR (400 MHz, CDCl3): 3.82 (s, 3H), 6.87 (s, 1H), 7.01 (s,
1H), 7.06 (dd, J = 1.9, 8.9 Hz, 1H), 7.40 (d, J = 9.0 Hz, 1H),
7.52–7.57 (m, 3H), 7.87 (d, J = 7.1 Hz, 1H), 7.92–7.94 (m, 1H), 8.04 (d, J = 8.3 Hz, 1H),
8.27–8.28 (m, 1H), 9.54 (s, 1H); 13C NMR (100 MHz, CDCl3): 55.6 (q), 102.8 (d), 113.2
(d), 113.3 (d), 118.7 (d), 124.3 (d), 125.5 (d), 126.5 (d), 127.3 (d), 127.7 (d), 127.9 (s), 128.4
(d), 130.8 (s), 131.5 (d), 133.5 (s), 133.8 (s), 135.7 (s), 136.4 (s), 154.8 (s), 188.5 (s) ppm.
NH
O
MeO
Br
SI 12
(5-Methoxy-1H-Indol-2-yl)(2-methoxy-4-methylphenyl)methanone (2q):-
Grey solid; 64% Yield; Rf 0.3 (15% ethyl acetate/pet. ether); mp:
94–95 °C; 1H NMR (500 MHz, CDCl3): 2.43 (s, 3H), 3.82 (s,
6H), 6.83–6.85 (m, 3H), 7.01–7.03 (m, 2H), 7.34 (d, J = 9.7 Hz,
1H), 7.42 (d, J = 7.5 Hz, 1H), 9.17 (s, 1H); 13C NMR (125 MHz, CDCl3): 21.9 (q), 55.7 (q),
55.8 (q), 102.8 (d), 112.2 (d), 112.5 (d), 113.1 (d), 118.1 (d), 120.6 (d), 125.4 (s), 128.0 (s),
130.0 (d), 133.1 (s), 136.4 (s), 142.8 (s), 154.7 (s), 157.6 (s), 186.8 (s) ppm; HRMS (ESI+):
calcd. for C18H17O3NNa = 318.1101, found 318.1101.
Benzo[b]thiophen-3-yl(5-methoxy-1H-Indol-2-yl)methanone (2r):-
Light yellow solid; 52% Yield; Rf 0.3 (10% ethyl acetate/pet.
ether); mp: 198–199 °C; 1H NMR (500 MHz, CDCl3): 3.85 (s,
3H), 7.06 (dd, J = 2.4, 8.9 Hz, 1H), 7.10 (br d, J = 1.8 Hz, 1H),
7.15 (br d, J = 1.3 Hz, 1H), 7.39 (d, J = 8.9 Hz, 1H), 7.46 (br t, J = 7.5 Hz, 1H), 7.51(br t, J =
7.6 Hz, 1H), 7.93 (d, J = 7.9 Hz, 1H), 8.33 (s, 1H), 8.47 (d, J = 8.1 Hz, 1H), 9.27 (s, 1H); 13C
NMR (125 MHz, CDCl3): 55.7 (q), 102.8 (d), 111.1 (d), 113.1 (d), 118.3 (d), 122.4 (d),
124.7 (d), 125.5 (d), 125.6 (d), 128.0 (s), 133.0 (s), 134.7 (s), 135.2 (d), 135.9 (s), 137.3 (s),
140.0 (s), 154.9 (s), 180.0 (s) ppm; HRMS (ESI+): calcd. for C18H13O2NSH+ = 308.0740,
found 308.0741.
Phenyl(5,6,7-trimethoxy-1H-Indol-2-yl)methanone (2s)8:-
Light yellow solid; 72% Yield; Rf 0.3 (15% ethyl acetate/pet. ether);
1H NMR (500 MHz, CDCl3): 3.89 (s, 3H), 3.94 (s, 3H), 4.08 (s,
3H), 6.82 (s, 1H), 7.03 (d, J = 2.1 Hz, 1H), 7.50 (d, J = 7.5 Hz, 1H),
7.52 (d, J = 7.7 Hz, 1H), 7.58–7.61 (m, 1H), 7.94 (d, J = 7.4 Hz, 2H), 9.29 (s, 1H); 13C NMR
(125 MHz, CDCl3): 56.2 (q), 61.1 (q), 61.5 (q), 98.0 (d), 112.8 (d), 123.4 (s), 127.6 (s),
8 M. Arthuis, R. Pontikis, G. G. Chabot, L. Quentin, D. Scherman and J.-C. Florent, Eur. J. Med. Chem., 2011, 46, 95.
NH
O
MeO
OMe
NH
O
MeO
OMe
MeO
SI 13
128.4 (d, 2C), 129.1 (d, 2C), 132.1 (d), 134.2 (s), 138.2 (s), 138.9 (s), 141.6 (s), 150.4 (s),
186.4 (s) ppm.
Naphthalen-1-yl(5,6,7-trimethoxy-1H-Indol-2-yl)methanone (2t):-
Yellow solid; 79% Yield; Rf 0.4 (20% ethyl acetate/pet. ether);
mp: 148–149 °C; 1H NMR (400 MHz, CDCl3): 3.85 (s, 3H),
3.95 (s, 3H), 4.10 (s, 3H), 6.75 (s, 1H), 6.82 (d, J = 2.2 Hz, 1H),
7.52–7.56 (m, 3H), 7.83 (br d, J = 7.1 Hz, 1H), 7.91–7.93 (m, 1H), 8.02 (d, J = 8.2 Hz, 1H),
8.23–8.26 (m, 1H), 9.41 (s, 1H); 13C NMR (100 MHz, CDCl3): 56.2 (q), 61.2 (q), 61.5 (q),
98.0 (d), 113.7 (d), 123.2 (s), 124.3 (d), 125.5 (d), 126.5 (d), 127.2 (d), 127.5 (d), 128.0 (s),
128.3 (d), 130.8 (s), 131.3 (d), 133.7 (s), 135.8 (s, 2C), 138.9 (s), 141.7 (s), 150.4 (s), 187.9
(s) ppm; HRMS (ESI+): calcd. for C22H19O4NH+ = 362.1387, found 362.1390.
Ethyl 1H-Indole-2-carboxylate (5a)9:
Brown solid; 57% Yield, Rf 0.4 (10% ethyl acetate/pet. ether); 1H NMR
(500 MHz, CDCl3): 1.42 (t, J = 7.1 Hz, 3H), 4.41 (q, J = 7.0 Hz, 2H),
7.15 (t, J = 7.5 Hz, 1H), 7.23 (s, 1H), 7.32 (t, J = 7.7 Hz, 1H), 7.42 (d, J = 8.3 Hz, 1H), 7.69
(d, J = 8.0 Hz, 1H), 9.0 (s, 1H); 13C NMR (125 MHz, CDCl3): 14.4 (q), 61.0 (t), 108.6 (d),
111.8 (d), 120.8 (d), 122.6 (d), 125.3 (d), 127.5 (s, 2C), 136.8 (s), 162.0 (s) ppm.
Ethyl 5-methoxy-1H-Indole-2-carboxylate (5b):-
Brown solid; 67% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); 1H
NMR (500 MHz, CDCl3): 1.41 (t, J = 7.1 Hz, 3H), 3.84 (s, 3H),
4.40 (q, J = 7.1 Hz, 2H), 6.99 (dd, J = 2.3, 9.0 Hz, 1H), 7.07 (d, J = 1.5 Hz, 1H), 7.14 (s, 1H),
7.31 (d, J = 9.0 Hz, 1H), 8.90 (s, 1H); 13C NMR (125 MHz, CDCl3): 14.4 (q), 55.7 (q), 61.0
(t), 102.5 (d), 108.2 (d), 112.7 (d), 116.9 (d), 127.8 (s), 127.9 (s), 132.1 (s), 154.7 (s), 161.9
(s) ppm; HRMS (ESI+): calcd. for C12H13O3NNa = 242.0788, found 242.0788.
9 Q. Cai, Z. Li, J. Wei, C. Ha, D. Pei and K. Ding, Chem. Commun., 2009, 7581.
NH
CO2Et
MeO
NH
O
MeO
MeO
OMe
SI 14
Ethyl 3-methyl-1H-Indole-2-carboxylate (5c)9:-
Light yellow solid; 74% Yield; Rf 0.3 (10% ethyl acetate/pet. ether); 1H
NMR (500 MHz, CDCl3): 1.43 (t, J = 7.1 Hz, 3H), 2.61 (s, 3H), 4.42 (q,
J = 7.1 Hz, 2H), 7.14 (t, J = 7.4 Hz, 1H), 7.32 (t, J = 7.5 Hz, 1H), 7.36 (d, J = 8.2 Hz, 1H),
7.66 (d, J = 8.1 Hz, 1H), 8.72 (s, 1H); 13C NMR (125 MHz, CDCl3): 9.9 (q), 14.5 (q), 60.7
(t), 111.6 (d), 119.9 (d), 120.2 (s), 120.8 (d), 123.4 (s), 125.5 (d), 128.5 (s), 135.8 (s), 162.7
(s) ppm.
Ethyl 3-butyl-1H-Indole-2-carboxylate (5d):-
Off white solid; 59% Yield; Rf 0.4 (15% ethyl acetate/pet. ether); mp: 71–
74 °C; 1H NMR (500 MHz, CDCl3): 0.94 (t, J = 7.3 Hz, 3H), 1.39–1.44
(m, 5H), 1.63–1.69 (m, 2H), 3.10 (t, J = 7.7 Hz, 2H), 4.41 (q, J = 7.1 Hz,
2H), 7.13 (t, J = 7.5 Hz, 1H), 7.31 (t, J = 7.6 Hz, 1H), 7.37 (d, J = 8.24 Hz, 1H), 7.68 (d, J =
8.24 Hz, 1H), 8.73 (s, 1H); 13C NMR (125 MHz, CDCl3): 14.0 (q), 14.4 (q), 22.8 (t), 24.5
(t), 33.2 (t), 60.6 (t), 111.7 (d), 119.8 (d), 120.9 (d), 123.0 (s), 125.4 (d and s), 128.1 (s),
135.9 (s), 162.5 (s) ppm; HRMS (ESI+): calcd. for C15H19O2NH+ = 246.1489, found
246.1491.
Ethyl 3-phenyl-1H-Indole-2-carboxylate (5e):-
Yellow solid; 61% Yield; Rf 0.4 (15% ethyl acetate/pet. ether); mp: 137–
139 °C; 1H NMR (200 MHz, CDCl3): 1.23 (t, J = 7.1 Hz, 3H), 4.29 (q, J
= 7.1 Hz, 2H), 7.11–7.18 (m, 1H), 7.32–7.49 (m, 5H), 7.52–7.58 (m, 2H), 7.63 (d, J = 8.3 Hz,
1H), 9.01 (s, 1H); 13C NMR (50 MHz, CDCl3): 14.0 (q), 60.9 (t), 111.7 (d), 120.9 (d), 121.8
(d), 122.8 (s), 124.3 (s), 125.8 (d), 127.2 (d), 127.7 (d, 2C), 127.9 (s), 130.6 (d, 2C), 133.5
(s), 135.7 (s), 162.0 (s) ppm; HRMS (ESI+): calcd. for C17H15O2NNa = 288.0995, found
288.0997.
NH
OEt
O
NH
OEt
O
C4H9
SI 15
3-Methyl-2-phenylquinoline (3u)10:-
Colorless oil; 29% Yield; Rf 0.4 (10% ethyl acetate/pet. ether); 1H NMR
(500 MHz, CDCl3): 2.46 (s, 3H), 7.41–7.53 (m, 4H), 7.58–7.60 (m, 2H),
7.63–7.68 (m, 1H), 7.77 (d, J = 8.2 Hz, 1H), 8.01 (s, 1H), 8.13 (d, J = 8.5 Hz, 1H); 13C NMR
(125 MHz, CDCl3): 20.6 (q), 126.4 (d), 126.7 (d), 127.6 (s), 128.2 (d), 128.3 (d, 2C), 128.7
(d), 128.8 (d, 2C), 129.2 (s), 129.3 (d), 136.7 (d), 140.8 (s), 146.6 (s), 160.5 (s) ppm.
(E)-3-(2-Aminophenyl)-2-methyl-1-phenylprop-2-en-1-one (7):-
Yellow Liquid; 42% Yield; Rf 0.2 (15% ethyl acetate/pet. ether); 1H NMR
(200 MHz, CDCl3): 2.16 (d, J = 1.4 Hz, 3H), 3.63 (s, 2H), 6.71 (dd, J =
0.9, 8.1 Hz, 1H), 6.81 (dt, J = 0.9, 7.6 Hz, 1H), 7.09–7.25 (m, 3H), 7.40–7.54 (m, 3H), 7.73–
7.77 (m, 2H); 13C NMR (100 MHz, CDCl3): 14.4 (q), 115.7 (d), 118.3 (d), 121.2 (s), 128.2
(d, 2C), 129.4 (d, 2C), 129.6 (d), 129.7 (d), 131.8 (d), 138.1 (s), 138.2 (d), 138.5 (s), 144.3
(s), 199.2 (s) ppm.
10 I. Hyodo, M. Tobisu and N. Chatani, Chem. Asian J., 2012, 7, 1357.
Acq
uisi
tion
Tim
e (s
ec)
7.91
67C
omm
ent
yoge
shD
ate
18/0
6/20
13 0
5:27
:24
File
Nam
eF
:\yog
esh\
Indo
le m
etho
\NM
R\y
m-9
36\H
NM
R B
.ES
PFr
eque
ncy
(MH
z)20
0.13
Nuc
leus
1HO
rigin
al P
oint
s C
ount
3276
8
Poin
ts C
ount
3276
8Sp
ectr
um O
ffset
(Hz)
1225
.148
4Sw
eep
Wid
th (H
z)41
39.0
7Te
mpe
ratu
re (d
egre
e C
)0.
000
HN
MR
B.E
SP
1.58
N HHO
2a
Chl
orof
orm
-d
5
SI
7.25
16I
018.00
7.977.96
97.567.52
46
7.167.16
2.02
1.05
3.94
1.00
1.95
0.769.27
8.0
7.667.62
7.59
7.47.34
7.137.12
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
34C
omm
ent
yoge
shD
ate
20 J
un 2
013
02:5
8:30
Dat
e St
amp
20 J
un 2
013
02:0
5:46
File
Nam
e\\a
gni\n
mr_
data
\JE
OL_
400\
2013
\Jun
e 20
13\W
ed4E
CX
400#
053_
CA
RB
ON
-3.jd
f
Freq
uenc
y (M
Hz)
100.
53Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s12
00O
rigin
EC
X 4
00
Orig
inal
Poi
nts
Cou
nt26
214
Ow
ner
delta
Poin
ts C
ount
2621
4Pu
lse
Sequ
ence
sing
le_p
ulse
_dec
Rec
eive
r Gai
n60
.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
040.
2900
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
124.
29Te
mpe
ratu
re (d
egre
e C
)19
.200
CN
MR
B.E
SP
CH
LOR
OF
OR
M-d
0077.31
77.076.69
N HO
2a
SI
129.21128.46
17I
132.36
126.52
123.21121.02
112.85112.18
187.23
137.96137.52
134.29
29.68
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
34C
omm
ent
yoge
shD
ate
20 J
un 2
013
02:5
8:30
Dat
e St
amp
20 J
un 2
013
02:3
7:03
File
Nam
e\\a
gni\n
mr_
data
\JE
OL_
400\
2013
\Jun
e 20
13\W
ed4E
CX
400#
053_
DE
PT
135-
3.jd
f
Freq
uenc
y (M
Hz)
100.
53Nu
cleu
s13
CN
umbe
r of T
rans
ient
s80
0O
rigin
EC
X 4
00
Orig
inal
Poi
nts
Cou
nt26
214
Ow
ner
delta
Poin
ts C
ount
2621
4Pu
lse
Sequ
ence
dept
.ex2
(se
lect
ion_
angl
e=13
5)
Rec
eive
r Gai
n60
.00
Solv
ent
CH
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OF
OR
M-d
Spec
trum
Offs
et (H
z)10
040.
0273
Spec
trum
Typ
eD
EP
T13
5Sw
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Wid
th (H
z)25
124.
29Te
mpe
ratu
re (d
egre
e C
)19
.100
DE
PT
B.E
SP
1128.46
129.21
N HO
2a
36
1
8
SI
132.3
126.52
123.21
121.02
112.85112.18
18I
150
145
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
55C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
7.91
67C
omm
ent
Yog
esh
Dat
e12
/07/
2013
22:
57:1
8
File
Nam
eF
:\yog
esh\
Indo
le m
etho
\NM
R\y
m-9
53\H
NM
R.E
SP
Freq
uenc
y (M
Hz)
200.
13Nu
cleu
s1H
Orig
inal
Poi
nts
Cou
nt32
768
Poin
ts C
ount
3276
8Sp
ectr
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ffset
(Hz)
1225
.401
1Sw
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Wid
th (H
z)41
39.0
7Te
mpe
ratu
re (d
egre
e C
)0.
000
HN
MR
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P
3.82
N HO
OM
e
2.43
O2b
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e
SI
Chl
orof
orm
-d
84
19I
667.62
87.467.44
7.42 .337.25
7.126.93
6.
3.46
3.01
1.97
0.95
1.05
1.14
1.99
1.00
0.869.43
7.67
7.48
7.
7 7.08
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
2.73
29C
omm
ent
yoge
shD
ate
25/0
7/20
13 0
7:52
:42
File
Nam
eF
:\yog
esh\
Indo
le m
etho
\NM
R\y
m-9
53\C
NM
R.E
SP
Freq
uenc
y (M
Hz)
50.3
2Nu
cleu
s13
CO
rigin
al P
oint
s C
ount
3276
8
Poin
ts C
ount
3276
8Sp
ectr
um O
ffset
(Hz)
5028
.808
1Sw
eep
Wid
th (H
z)11
990.
41Te
mpe
ratu
re (d
egre
e C
)0.
000
CN
MR
.ES
PC
hlor
ofor
m-d
77.00
N HO
OM
eO
2bO
Me
SI
29.96
126.2712120.77
120.677912.49
112.22
71
20I
.05
157.61
142.82
137.65135.92
12127.61
137
123.
112.711
55.
21.90
187.
125.
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
2.73
29C
omm
ent
yoge
shD
ate
25/0
7/20
13 0
7:14
:56
File
Nam
eF
:\yog
esh\
Indo
le m
etho
\NM
R\y
m-9
53\D
EP
T.E
SP
Freq
uenc
y (M
Hz)
50.3
2N
ucle
us13
CO
rigin
al P
oint
s C
ount
3276
8
Pi
tC
t32
768
St
Off
t(H
)50
2720
90S
Wid
th(H
)11
990
41T
t(d
C)
000
0Po
ints
Cou
nt32
768
Spec
trum
Offs
et (H
z)50
27.2
090
Swee
p W
idth
(Hz)
1199
0.41
Tem
pera
ture
(deg
ree
C)
0.00
0
DE
PT
.ES
P
129.96
6.26
123.10120.74
120.62
2.82112.42
112.21
55.68
N HO
OM
e
126
112
21.90
2b
SI 21I
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
N HO
OM
e2b
SI 22I
Acq
uisi
tion
Tim
e (s
ec)
3.95
84C
omm
ent
yoge
shD
ate
07 A
ug 2
013
15:2
6:00
Dat
e St
amp
07 A
ug 2
013
15:2
6:00
File
Nam
e\\a
gni\n
mr_
data
\AV
200\
AU
G_1
3#A
V20
0\da
ta\A
dmin
istr
ator
\nm
r\W
ed2a
v2#0
32\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
200.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
8O
rigin
av20
0
Orig
inal
Poin
tsC
ount
1638
4O
wne
rA
dmin
istr
ator
Poin
tsC
ount
3276
8Pu
lse
Sequ
ence
zg30
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
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49.4
0SW
(cyc
lical
) (H
z)41
39.0
7So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)12
25.6
606
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)41
38.9
5Te
mpe
ratu
re (d
egre
e C
)27
.000
Wed
2av2
#032
.001
.001
.1r.
esp
3.80
Wed
2av2
#032
.001
.001
.1r.
esp
7.60
CH
LOR
OF
OR
M-d
8
64
7
7.56
7.44
66
7.25
4
6.936.93
89
1.98
1.08
1.09
1.07
1.90
1.007.68
7.6
77.55
7.48
7.407.397.367.36
7.327.32
7.187.17
7.17.107.10
6.8
SI
CH
LOR
OF
OR
M-d
7.607.
77.
67.
57.
47.
37.
27.
17.
06.
96.
8C
hem
ical
Shi
ft (p
pm)
23I
6.896.936.93
7.14
7.25.367.44
7.567.6468
3.13
1.98
1.08
1.09
1.07
1.90
1.00
0.92
3.82
7.107
7
7.
9.37
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e14
Aug
201
3 10
:49:
04D
ate
Stam
p14
Aug
201
3 10
:49:
04
File
Nam
eH
:\New
fol
der\
Wed
3av5
00#0
01 y
m-9
67\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CNu
mbe
r of T
rans
ient
s63
5
Oi
isp
ect
Oi
ilP
it
Ct
3276
8O
nmr
Pi
tC
t32
768
Pl
Szg
pg30
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
3125
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
979.
3203
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05Te
mpe
ratu
re (d
egre
e C
)22
.500
Wed
3av5
00#0
01.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
7.00 77
7
SI
56.04
112.273.413.59
1.0723.32
126.84
132.0434.47
24I
5
1111
1212
127.51.83
13135.1837.93
56.48
36
1129
113
15
185.3
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
14 A
ug 2
013
10:2
7:44
Dat
e St
amp
14 A
ug 2
013
10:2
7:44
File
Nam
eH
:\New
fol
der\
Wed
3av5
00#0
01 y
m-9
67\2
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CNu
mbe
r of T
rans
ient
s10
00
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90So
lven
tC
HLO
RO
FO
RM
-dSp
ectr
um O
ffset
(Hz)
1256
8.33
20
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00Te
mpe
ratu
re (d
egre
e C
)22
.000
Wed
3av5
00#0
01.0
02.0
01.1
r.es
p
56.04 5
27113.41
06
112.2
113.60
121.0
123.32
126.84
132.04
134.47
SI 25I
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
Che
mic
al S
hift
(ppm
)
Acq
uisi
tion
Tim
e (s
ec)
1.99
23C
omm
ent
Yog
esh
1HD
ate
31 J
ul 2
013
21:4
5:44
Dat
e St
amp
31 J
ul 2
013
21:4
5:44
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
July
_13_
400\
Wed
5av4
00#0
19\1
\PD
AT
A\1
\1r
F(M
H)
400
13N
l1H
Nb
fTi
t64
Oi
isp
ect
Oi
ilP
it
Ct
1638
4Fr
eque
ncy
(MH
z)40
0.13
Nuc
leus
1HN
umbe
r of T
rans
ient
s64
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30R
ecei
ver G
ain
456.
00SW
(cyc
lical
) (H
z)82
23.6
8
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)24
56.8
567
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)82
23.4
3
Tem
pera
ture
(deg
ree
C)
23.1
00
Wed
5av4
00#0
19.0
01.H
NM
R.1
r.es
p
7.55
CH
LOR
OF
OR
M-d
7.56
7.25
6.97
N HO
2d
58.03
7.88
.64
7.54 7.50
77.15
SI
8.30288.05
87.93
7.667.
7.38
26I
9.62
8.
7.13
100
104
106
414
102
203
104
100
096
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
1.00
1.04
1.06
4.14
1.02
2.03
1.04
1.00
0.96
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
13C
Dat
e01
Aug
201
3 08
:55:
36
Dat
e St
amp
01 A
ug 2
013
08:5
5:36
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
July
_13_
400\
Wed
5av4
00#0
19\3
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
100
61N
ucle
us13
CN
umbe
rofT
rans
ient
s10
855
Orig
insp
ect
Orig
inal
Poin
tsC
ount
1638
4Fr
eque
ncy
(MH
z)10
0.61
Nuc
leus
13C
Num
ber o
f Tra
nsie
nts
1085
5O
rigin
spec
tO
rigin
al P
oint
s C
ount
1638
4
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
2050
.00
SW(c
yclic
al) (
Hz)
2525
2.53
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)95
53.9
619
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
251.
75
Tem
pera
ture
(deg
ree
C)
23.3
00
Wed
5av4
00#0
19.0
03.C
NM
R.1
r.es
pC
HLO
RO
FO
RM
-d
Wed
5av4
00#0
1900
3C
NM
R1r
esp
Wed
5av4
00#0
19.0
03.C
NM
R.1
r.es
p
21.07
123.32
24.30
125.48
26.53126.77
127.32
127.81
128.36
31.54
N HO
2d
1
1
1
1
121
1127.58
1
1
130.77
1
133.79
135.61135.96
137.94
SI
131.54128.36127.81127.32126.77
125.48124.30123.32
121.07113.74
112.29
136
134
132
130
128
126
124
122
Che
mic
al S
hift
(ppm
)
27I
76
7.9435.96
133.791
0.77
1
188.7
1313
1
130
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
DE
PT
Dat
e01
Aug
201
3 00
:44:
56
Dat
e St
amp
01 A
ug 2
013
00:4
4:56
File
Nam
e\\a
gni\n
mr
data
\AV
400\
July
1340
0\W
ed5a
v400
#019
\2\P
DA
TA
\1\1
rp
gg
_y_
_
Freq
uenc
y (M
Hz)
100.
61N
ucle
us13
CNu
mbe
r of T
rans
ient
s40
00O
rigin
spec
tO
rigin
al P
oint
s C
ount
1638
4
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n16
384.
00SW
(cyc
lical
) (H
z)25
252.
53
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
056.
6826
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
251.
75
Tem
pera
ture
(deg
ree
C)
23.2
00
Wed
5av4
00#0
19.0
02.D
EP
T.1
r.es
p
3
29
131.55
126.77126.53
125.49123.34
121.08
113.74112.2
N HO
2d
Wed
5av4
00#0
19.0
02.D
EP
T.1
r.es
p
121.08
123.34
124.30
125.49
126.53126.77
127.33
127.82
128.37
131.55
SI 28I
131
130
129
128
127
126
125
124
123
122
121
131
130
129
128
127
126
125
124
123
122
121
Che
mic
al S
hift
(ppm
)
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
NN HO
2d
SI 29I
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
08 A
ug 2
013
23:0
9:20
Dat
e St
amp
08 A
ug 2
013
23:0
9:20
File
Nam
eH
:\New
fol
der\
Thu
2av5
00#0
26\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt20
031
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n25
6.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
19.7
769
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0Te
mpe
ratu
re (d
egre
e C
)21
.900
Thu
2av5
00#0
26.0
01.0
01.1
r.es
p
7.49
7.737.74
Thu
2av5
00#0
26.0
01.0
01.1
r.es
p
.49
SI
6.656.66
6.66
7.187.27
7.387.47
7.777.78
7.787.77
7.747.74
7.73
7.497.
7.47
7.407.38
37
7.27
7.207.18
17
30I
7.17
9.46
780
775
770
765
760
755
750
745
740
735
730
725
720
715
710
1.11
1.16
2.08
1.98
1.03
7
7.3
7
7.
1.00
1.11
1.16
2.08
1.98
1.03
1.06
7.80
7.75
7.70
7.65
7.60
7.55
7.50
7.45
7.40
7.35
7.30
7.25
7.20
7.15
7.10
Che
mic
al S
hift
(ppm
)
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e09
Aug
201
3 09
:40:
48D
ate
Stam
p09
Aug
201
3 09
:40:
48
File
Nam
eH
:\New
fol
der\
Thu
2av5
00#0
26\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s94
71
Oi
isp
ect
Oi
ilP
it
Ct
3276
8O
nmr
Pi
tC
t32
768
Pl
Szg
pg30
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
3125
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
981.
2275
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05Te
mpe
ratu
re (d
egre
e C
)22
.400
Thu
2av5
00#0
26.0
03.0
01.1
r.es
p
77.00
SI
608.45
.5683
.48
31I
111.4112.112
118.120.98123.33
126.4799
4
146.
127.9
133.44
137.24
152.72
172.57
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
09 A
ug 2
013
01:3
0:08
Dat
e St
amp
09 A
ug 2
013
01:3
0:08
File
Nam
eH
:\New
fol
der\
Thu
2av5
00#0
26\2
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s32
00
Oi
isp
ect
Oi
ilP
it
Ct
3276
8O
nmr
Pi
tC
t32
768
Pl
Sde
pt13
5O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8O
wne
rnm
rPo
ints
Cou
nt32
768
Puls
e Se
quen
cede
pt13
5
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90So
lven
tC
HLO
RO
FO
RM
-dSp
ectr
um O
ffset
(Hz)
1257
0.55
76
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00Te
mpe
ratu
re (d
egre
e C
)22
.100
Thu
2av5
00#0
26.0
02.0
01.1
r.es
p
112.08
120.99123.34
126.48
111.46112.46
118.56
49
SI
146.
32I
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
yoge
sh 1
HD
ate
19 S
ep 2
013
12:4
4:16
Dat
e St
amp
19 S
ep 2
013
12:4
4:16
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Thu
3av5
00#0
02\1
\PD
AT
A\1
\1r
F(M
H)
500
13N
l1H
Nb
fTi
t64
Oi
isp
ect
Oi
ilP
it
Ct
2003
1Fr
eque
ncy
(MH
z)50
0.13
Nuc
leus
1HNu
mbe
r of T
rans
ient
s64
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt20
031
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n28
7.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
19.7
769
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
23.0
00
Thu
3av5
00#0
02.0
01.0
01.1
r.es
p
4.04
Thu
3av5
00#0
02.0
01.0
01.1
r.es
p
N H
2fO
N
CH
LOR
OF
OR
M-d
7.757.73
7.477.46
7.367.34
.33
7.27
7.25
7.227.22
7.197.17
7.16
6.96
SI
7.75
7.70
7.65
7.60
7.55
7.50
7.45
7.40
7.35
7.30
7.25
7.20
7.15
7.10
7.05
7.00
6.95
6.90
6.85
Che
mic
alS
hift
(ppm
)
1.00
1.04
1.00
0.97
1.05
1.05
1.02
7
7
7
33I
CH
LOR
OF
OR
M-d
46.255
6.967.177.22
7.25.347.46
477.73.75
Che
mic
al S
hift
(ppm
)
315
098
100
104
100
097
105
105
102
103
6.246
6.25
7.1677
7
7.47
7.
9.39
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.15
0.98
1.00
1.04
1.00
0.97
1.05
1.05
1.02
1.03
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e19
Sep
201
3 13
:39:
44
Dat
e St
amp
19 S
ep 2
013
13:3
9:44
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Thu
3av5
00#0
02\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s11
75O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
981.
2275
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
23.9
00
Thu
3av5
00#0
02.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
77.00
N H
2fO
N
0.71
SI
37.04
108.49109.67
111.91
120122.85
125.50
131.21
34I
127.830.33
35.59136.89
6.31
130
13
176
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
19 S
ep 2
013
12:5
0:40
Dat
e St
amp
19 S
ep 2
013
12:5
0:40
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Thu
3av5
00#0
02\2
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76N
ucle
us13
CNu
mbe
rofT
rans
ient
s60
0O
rigin
spec
tO
rigin
alPo
ints
Cou
nt32
768
Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CNu
mbe
r of T
rans
ient
s60
0O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
570.
3867
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
23.3
00
Thu
3av5
00#0
02.0
02.0
01.1
r.es
p
120.71
37.04
08.49109.67
111.91
122.85
125.50
N H
2fO
N
10
1
131.21
SI 35I
150
145
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
5550
4540
3530
2520
15C
hem
ical
Shi
ft (p
pm)
N H
2fO
N
SI 36I
Acq
uisi
tion
Tim
e (s
ec)
1.99
23C
omm
ent
Yog
esh
1HD
ate
01 A
ug 2
013
21:4
5:44
Dat
e St
amp
01 A
ug 2
013
21:4
5:44
File
Nam
eE
:\New
fol
der\
Thu
1av4
00#0
10\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
400.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64
Orig
insp
ect
Orig
inal
Poin
tsC
ount
1638
4O
wne
rA
dmin
istr
ator
Poin
tsC
ount
3276
8Pu
lse
Sequ
ence
zg30
Thu
1av4
00#0
10.0
01.H
NM
R.1
r.es
pC
HLO
RO
FO
RM
-d
7.25
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
n64
5.00
SW(c
yclic
al) (
Hz)
8223
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Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)24
64.8
591
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)82
23.4
3Te
mpe
ratu
re (d
egre
e C
)23
.700
7
Thu
1av4
00#0
10.0
01.H
NM
R.1
r.es
pC
HLO
RO
FO
RM
-d
7.25
SI
7.14
367.48
7.747.76
7.84
.27
14
6
.48
7476
7.84
7
37I
M01
(m)
7.13
7.3
7.507.54
7
7.93 7.95
8.8.29
8.808.81
1.00
1.00
2.05
1.01
0.98
1.02
1.00
1.00
7.137.1
7.16
7.347.36
7.387.
7.507.52
7.547.55
7.77.7
7.917.937.93
7.957.95
8.278.29
8.808.81
1.00
1.00
2.05
1.01
0.98
1.02
1.00
1.00
0.90
10.84
8.5
8.0
7.5
Che
mic
al S
hift
(ppm
)
1.00
1.00
2.05
1.01
0.98
1.02
1.00
1.00
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
Che
mic
al S
hift
(ppm
)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
13C
Dat
e01
Aug
201
3 23
:47:
20D
ate
Stam
p01
Aug
201
3 23
:47:
20
File
Nam
eE
:\New
fol
der\
Thu
1av4
00#0
10\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
100.
61Nu
cleu
s13
CN
umbe
r of T
rans
ient
s10
86
Orig
insp
ect
Orig
inal
Poin
tsC
ount
1638
4O
wne
rro
otPo
ints
Cou
nt32
768
Puls
eSe
quen
cezg
pg30
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)25
252.
53So
lven
tC
HLO
RO
FO
RM
-dSp
ectr
um O
ffset
(Hz)
9554
.733
4
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
251.
75Te
mpe
ratu
re (d
egre
e C
)23
.600
Thu
1av4
00#0
10.0
03.C
NM
R.1
r.es
pC
HLO
RO
FO
RM
-d
SI
7.36
2126.33
23.32120.80
12.36
38I
7
148.45
65137
.43126.72124.22
12
113.3111
181.19
154.97
137.
135.01
127
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
DE
PT
Dat
e01
Aug
201
3 21
:52:
08D
ate
Stam
p01
Aug
201
3 21
:52:
08
File
Nam
eE
:\New
fol
der\
Thu
1av4
00#0
10\2
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
100.
61Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s26
85
Orig
insp
ect
Orig
inal
Poin
tsC
ount
1638
4O
wne
rro
otPo
ints
Cou
nt32
768
Puls
eSe
quen
cede
pt13
5O
rigin
spec
tO
rigin
al P
oint
s C
ount
1638
4O
wne
rro
otPo
ints
Cou
nt32
768
Puls
e Se
quen
cede
pt13
5
Rec
eive
r Gai
n16
384.
00SW
(cyc
lical
) (H
z)25
252.
53So
lven
tC
HLO
RO
FO
RM
-dSp
ectr
um O
ffset
(Hz)
1005
6.79
00
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
251.
75Te
mpe
ratu
re (d
egre
e C
)23
.800
Thu
1av4
00#0
10.0
02.D
EP
T.1
r.es
p
6
112.36
148.44
137.36
126.72126.34
2123.32
120.80
124.22
SI
113.32
39I
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
Che
mic
al S
hift
(ppm
)
SI 40I
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Ana
nd 1
HD
ate
03 S
ep 2
013
09:1
7:20
Dat
e St
amp
03 S
ep 2
013
09:1
7:20
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Tue
1av5
00#0
01\1
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
500
13Nu
cleu
s1H
Num
bero
fTra
nsie
nts
64O
rigin
spec
tO
rigin
alPo
ints
Cou
nt20
031
Tue
1av5
00#0
01.0
01.0
01.1
r.es
pC
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RO
FO
RM
-d
5
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
19.7
769
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
22.4
00
7.25T
ue1a
v500
#001
.001
.001
.1r.
esp
CH
LOR
OF
OR
M-d
5
SI
7.78
7.78
7.25
41I
3
7.88
7.777.68 547.487.47
7.357.19 8
108
216
229
110
319
100
7.88
7.827.80
7.777.76
7.707.68
7.547.52
7.517.48
7.47
7.417.39
7.377.35
7.34
7.217.19
7.18
1.08
2.16
2.29
1.10
3.19
1.00
1.029.33
7.5
7.1
7.9
7.8
7.7
7.6
7.5
7.4
7.3
7.2
Che
mic
al S
hift
(ppm
)
1.08
2.16
2.29
1.10
3.19
1.00
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e03
Sep
201
3 10
:23:
28
Dat
e St
amp
03 S
ep 2
013
10:2
3:28
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Tue
1av5
00#0
01\3
\PD
AT
A\1
\1r
F(M
H)
125
76N
l13
CN
bfT
it
808
Oi
isp
ect
Oi
ilP
it
Ct
3276
8Fr
eque
ncy
(MH
z)12
5.76
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
808
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
983.
1357
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
23.0
00
Tue
1av5
00#0
01.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
Tue
1av5
00#0
01.0
03.0
01.1
r.es
p
2
SI
128.15
127.06126.88
124.02123.55
123.20
121.20
114.26
112.42
42I
112.10112.28
112.42114.26
121.20123.20
123.55124.02
126.88128.15
126
124
122
120
118
116
114
112
Che
mic
al S
hift
(ppm
)
133.68
137.46
152.87
155.90
173.98
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
03 S
ep 2
013
09:5
1:28
Dat
e St
amp
03 S
ep 2
013
09:5
1:28
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Tue
1av5
00#0
01\2
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76N
ucle
us13
CNu
mbe
rofT
rans
ient
s80
0O
rigin
spec
tO
rigin
alPo
ints
Cou
nt32
768
Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CNu
mbe
r of T
rans
ient
s80
0O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
572.
0234
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
22.5
00
Tue
1av5
00#0
01.0
02.0
01.1
r.es
p
10
121.19
123.55
112.112.27
112.43114.26
123.19124.01
126.88
8.15 128
SI 43I
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
55C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
YO
GE
SH
1H
Dat
e15
Aug
201
3 15
:13:
36D
ate
Stam
p15
Aug
201
3 15
:13:
36
File
Nam
eE
:\New
fol
der\
Thu
3av5
00#0
03 y
m-9
60\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt20
031
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n36
2.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)21
75.4
456
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0Te
mpe
ratu
re (d
egre
e C
)22
.400
Thu
3av5
00#0
03 y
m-9
60.0
01.0
01.1
r.es
p
7.1843.44
7.47.
8.29
SI
7.11
7.39
7.667.67
7.867.87
8.428.44
44I
7.33
9.45
1.11
1.72
4.35
1.00
0.97
1.02
1.00
0.90
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e15
Aug
201
3 17
:00:
16D
ate
Stam
p15
Aug
201
3 17
:00:
16
File
Nam
eE
:\New
fol
der\
Thu
3av5
00#0
03 y
m-9
60\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s13
42
Oi
isp
ect
Oi
ilP
it
Ct
3276
8O
nmr
Pi
tC
t32
768
Pl
Szg
pg30
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
3125
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
980.
2744
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05Te
mpe
ratu
re (d
egre
e C
)23
.200
Thu
3av5
00#0
03 y
m-9
60.0
03.0
01.1
r.es
p
Thu
3av5
00#0
03ym
960
003
001
1res
pT
hu3a
v500
#003
ym
-960
.003
.001
.1r.
esp
01
5924
135.48
66
65
126.45
125.59125.52
124.71
123.16
122.42
121.10
SI
140
138
136
134
132
130
128
126
124
122
140.0
137.5137.2
134.6
127.6
45I
111.59112.19121.10122.42123.16124.71125.52
126.45
135.48
140
138
136
134
132
130
128
126
124
122
Che
mic
al S
hift
(ppm
)
127.65
134.66
137.59140.01
181.21
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
15 A
ug 2
013
15:3
9:12
Dat
e St
amp
15 A
ug 2
013
15:3
9:12
File
Nam
eE
:\New
fold
er\T
hu3a
v500
#003
ym-9
60\2
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76Nu
cleu
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le N
ame
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ew f
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#003
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960\
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rFr
eque
ncy
(MH
z)12
5.76
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
800
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
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ence
dept
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Rec
eive
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n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90So
lven
tC
HLO
RO
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RM
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ectr
um O
ffset
(Hz)
1256
8.74
02
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00Te
mpe
ratu
re (d
egre
e C
)22
.700
Thu
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00#0
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m-9
60.0
02.0
01.1
r.es
p
112.18
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111.59
121.09
123.15124.70
125125 126.45
35.49 13
SI 46I
160
155
150
145
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
Che
mic
al S
hift
(ppm
)
SI 47I
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uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
10 S
ep 2
013
09:5
7:52
Dat
e St
amp
10 S
ep 2
013
09:5
7:52
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Tue
2av5
00#0
01\1
\PD
AT
A\1
\1r
F(M
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500
13N
l1H
Nb
fTi
t64
Oi
isp
ect
Oi
ilP
it
Ct
2003
1
Tue
2av5
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01.0
01.0
01.1
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0.96
Freq
uenc
y (M
Hz)
500.
13N
ucle
us1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
19.7
769
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
23.2
00
CH
LOR
OF
OR
M-d
7.25
N H
2j
C4H
9
O
2.94
0.9794
SI
41
7.20
.952.92
1.76
1.431.42
00.9
48I
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7.717.69
7.427.4
7.33
7.14 7.13
2.
91.781.75 1.731.59 1.45
1.40
3.10
2.15
2.06
1.99
1.04
1.04
0.97
0.99
1.00
1.04
9.0
1.79
1
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e10
Sep
201
3 10
:46:
56
Dat
e St
amp
10 S
ep 2
013
10:4
6:56
File
Nam
e\\a
gni\n
mr
data
\AV
500\
Sep
1350
0\T
ue2a
v500
#001
\3\P
DA
TA
\1\1
rp
pg
__
p__
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s52
2O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
982.
1826
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
24.1
00
Tue
2av5
00#0
01.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
77.00
N H
2j
C4H
9
O
SI 49I
13.88
22.52
27.26
38.09
109.02
112.11
120.89123.01126.19
127.58
135.22137.15
193.62
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
10 S
ep 2
013
10:2
1:20
Dat
e St
amp
10 S
ep 2
013
10:2
1:20
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Tue
2av5
00#0
01\2
\PD
AT
A\1
\1r
F(M
H)
125
76N
l13
CN
bfT
it
1000
Oi
isp
ect
Oi
ilP
it
Ct
3276
8Fr
eque
ncy
(MH
z)12
5.76
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
1000
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
570.
6299
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
23.5
00
Tue
2av5
00#0
01.0
02.0
01.1
r.es
p
12.10
13.88
109.03
1
120.88123.00
126.19
N H
2j
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9
O
SI 50I
22
27
38.09
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
2.52
7.26
Acq
uisi
tion
Tim
e (s
ec)
3.95
84C
omm
ent
Yog
esh
Dat
e26
Aug
201
3 23
:17:
28
Dat
e St
amp
26 A
ug 2
013
23:1
7:28
File
Nam
e\\a
gni\n
mr_
data
\AV
200\
AU
G_1
3#A
V20
0\da
ta\A
dmin
istr
ator
\nm
r\M
on5a
v2#0
81\1
\PD
AT
A\1
\1r
F(M
H)
200
13N
l1H
Nb
fTi
t8
Oi
ia
200
Mon
5av2
#081
.001
.001
.1r.
esp
CH
LOR
OF
OR
M-d
5
Freq
uenc
y (M
Hz)
200.
13N
ucle
us1H
Num
ber o
f Tra
nsie
nts
8O
rigin
av20
0
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
n11
49.4
0SW
(cyc
lical
) (H
z)41
39.0
7So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)12
29.5
370
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)41
38.9
5Te
mpe
ratu
re (d
egre
e C
)27
.000
7.257.34
.28
SI
7.40
301.
1.267
1.06
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7.757.71
7.45
7.157.12
7.11
2.692.67
2.652.63
2.61
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1.25 1.111.071.04 1.02
2.06
2.24
1.00
1.11
2.98
1.00
0.94
9.24
7
2.712
2.59
1
1
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e14
Aug
201
3 20
:46:
24D
ate
Stam
p14
Aug
201
3 20
:46:
24
File
Nam
eH
:\New
fold
er\W
ed3a
v500
#016
ym-9
62\3
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76N
ucle
us13
CN
umbe
rofT
rans
ient
s20
43Fi
le N
ame
H:\N
ew f
olde
r\W
ed3a
v500
#016
ym
-962
\3\P
DA
TA
\1\1
rFr
eque
ncy
(MH
z)12
5.76
Nuc
leus
13C
Num
ber o
f Tra
nsie
nts
2043
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
3125
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Solv
ent
CH
LOR
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OR
M-d
Spec
trum
Offs
et (H
z)11
980.
2744
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05Te
mpe
ratu
re (d
egre
e C
)22
.800
Wed
3av5
00#0
16.0
03.0
01.1
r.es
p
77.00
SI
11.43
52I
17.52
109.12
112.22
120.78122.94
126.11127.63
135.81137.27
192.91
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
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168
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ical
Shi
ft (p
pm)
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uisi
tion
Tim
e (s
ec)
1.10
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ent
DE
PT
;D
ate
14 A
ug 2
013
19:0
4:00
Dat
e St
amp
14 A
ug 2
013
19:0
4:00
File
Nam
eH
:\New
fold
er\W
ed3a
v500
#016
ym-9
62\2
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76N
ucle
us13
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umbe
rofT
rans
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s12
00Fi
le N
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H:\N
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Num
ber o
f Tra
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nts
1200
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90So
lven
tC
HLO
RO
FO
RM
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ectr
um O
ffset
(Hz)
1256
9.51
56
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00Te
mpe
ratu
re (d
egre
e C
)22
.400
Wed
3av5
00#0
16.0
02.0
01.1
r.es
p
7.52
109.12112.22
120.78.94
126.11
17
1
1221
SI 53I
11
220
210
200
190
180
170
160
150
140
130
120
110
100
9080
7060
5040
3020
100
-10
-20
Che
mic
al S
hift
(ppm
)
.43
SI 54I
Acq
uisi
tion
Tim
e (s
ec)
7.91
67C
omm
ent
yoge
shD
ate
25/0
6/20
13 1
5:30
:18
File
Nam
eF
:\yog
esh\
Indo
le m
etho
\NM
R\y
m-9
42\H
NM
R B
.ES
PFr
eque
ncy
(MH
z)20
0.13
Nucl
eus
1HO
rigin
al P
oint
s C
ount
3276
8
Poin
tsC
ont
3276
8Sp
ectr
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ffset
(H)
1225
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See
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idth
(H)
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re(d
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ts C
ount
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8Sp
ectr
um O
ffset
(Hz)
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SI 55I
04.257.37
417.527.56
7.5962
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8.018.01
311
298
100
310
197
094
1.71
7.027.07
7.4
7.6
9.52
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.11
2.98
1.00
3.10
1.97
0.94
Acq
uisi
tion
Tim
e (s
ec)
1.04
34C
omm
ent
yoge
shD
ate
19 S
ep 2
013
07:5
6:04
Dat
e St
amp
19 S
ep 2
013
07:2
8:11
File
Nam
e\\a
gni\n
mr_
data
\JE
OL_
400\
2013
\Sep
201
3 Li
quid
\Wed
3EC
X40
0#02
7_C
AR
BO
N-3
.jdf
Freq
uenc
y(M
Hz)
100
53Nu
cleu
s13
CNu
mbe
rofT
rans
ient
s10
1O
rigin
EC
X40
0Fr
eque
ncy
(MH
z)10
0.53
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
101
Orig
inE
CX
400
Orig
inal
Poi
nts
Cou
nt26
214
Ow
ner
delta
Poin
ts C
ount
2621
4Pu
lse
Sequ
ence
sing
le_p
ulse
_dec
Rec
eive
r Gai
n60
.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
036.
4561
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
124.
29Te
mpe
ratu
re (d
egre
e C
)22
.500
Wed
3EC
X40
0#02
7_C
AR
BO
N-3
.esp
128.38129.22
CH
LOR
OF
OR
M-d
77.00
1
SI
55.60
102.64
112.48113.30
118.40
132.23
56I
127.93
134.73138.10
154.74
187.13
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
34C
omm
ent
yoge
shD
ate
19 S
ep 2
013
07:5
6:04
Dat
e St
amp
19 S
ep 2
013
07:3
0:24
File
Nam
e\\a
gni\n
mr
data
\JE
OL
400\
2013
\Sep
201
3 Li
quid
\Wed
3EC
X40
0#02
7D
EP
T13
5-3.
jdf
pp
g_
_p
q_
j
Freq
uenc
y (M
Hz)
100.
53N
ucle
us13
CNu
mbe
r of T
rans
ient
s47
Orig
inE
CX
400
Orig
inal
Poi
nts
Cou
nt26
214
Ow
ner
delta
Poin
ts C
ount
2621
4Pu
lse
Sequ
ence
dept
.ex2
(se
lect
ion_
angl
e=13
5)
Rec
eive
r Gai
n60
.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
036.
0127
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
124.
29Te
mpe
ratu
re (d
egre
e C
)22
.600
Wed
3EC
X40
0#02
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EP
T13
5-3.
esp
3829.22
128.31
SI
55.60
102.63
112.47113.29
118.39
132.23
57I
1
176
168
160
152
144
136
128
120
112
104
9688
8072
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0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
2.04
47C
omm
ent
Yog
esh
1HD
ate
19 S
ep 2
013
17:2
9:44
Dat
e St
amp
19 S
ep 2
013
17:2
9:44
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Sep
_13_
400\
Thu
3av4
00#0
03\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
400.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
1638
4
Ow
ner
Adm
inis
trat
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ints
Cou
nt32
768
Puls
e Se
quen
cezg
30R
ecei
ver G
ain
724.
00SW
(cyc
lical
) (H
z)80
12.8
2
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
57.9
458
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)80
12.5
8
Tem
pera
ture
(deg
ree
C)
25.1
00
Thu
3av4
00#0
03.0
01.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
5 7.25
7.54
7.977.99
7.09
37.40
7.68
7.97
Thu
3av4
00#0
03.0
01.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
4
.25
SI
7.33
7.63
7.68
7.6361
7.567.5
7.52
7.437.40
7.337.33
310
7.
7.097.09
7.08
58I
9.47
1.01
1.01
1.01
2.02
1.02
0.99
7.65
7.6
7
7.7.3
1.01
1.01
1.01
2.02
1.02
0.99
2.03
0.96
7.7
7.6
7.5
7.4
7.3
7.2
7.1
Che
mic
al S
hift
(ppm
)
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
13C
Dat
e19
Sep
201
3 19
:48:
24
Dat
e St
amp
19 S
ep 2
013
19:4
8:24
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Sep
_13_
400\
Thu
3av4
00#0
03\3
\PD
AT
A\1
\1r
Freq
enc
(MH
)10
061
Ncl
es
13C
Nm
bero
fTra
nsie
nts
2063
Orig
insp
ect
Orig
inal
Poin
tsC
ont
1638
4Fr
eque
ncy
(MH
z)10
0.61
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
2063
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
2050
.00
SW(c
yclic
al) (
Hz)
2525
2.53
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)96
34.8
799
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
251.
75
Tem
pera
ture
(deg
ree
C)
24.8
00
Thu
3av4
00#0
03.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
0 77.00
128.56129.20
SI
8
59I
111.74113.31
122.28
3126.96
132.623
126.63
135.33135.71137.64
187.04
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
DE
PT
Dat
e19
Sep
201
3 18
:16:
40
Dat
e St
amp
19 S
ep 2
013
18:1
6:40
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Sep
_13_
400\
Thu
3av4
00#0
03\2
\PD
AT
A\1
\1r
Freq
enc
(MH
)10
061
Ncl
es
13C
Nm
bero
fTra
nsie
nts
1000
Orig
insp
ect
Orig
inal
Poin
tsC
ont
1638
4Fr
eque
ncy
(MH
z)10
0.61
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
1000
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n16
384.
00SW
(cyc
lical
) (H
z)25
252.
53
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)76
08.4
902
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
251.
75
Tem
pera
ture
(deg
ree
C)
24.7
00
Thu
3av4
00#0
03.0
02.0
01.1
r.es
p
129.20128.55
SI
111.74113.31
122.26
126.95
132.62
60I
160
155
150
145
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
5550
4540
3530
Che
mic
al S
hift
(ppm
)
SI 61I
Acq
uisi
tion
Tim
e (s
ec)
3.95
84C
omm
ent
yoge
shD
ate
07 A
ug 2
013
15:2
6:00
Dat
e St
amp
07 A
ug 2
013
15:2
6:00
File
Nam
e\\a
gni\n
mr_
data
\AV
200\
AU
G_1
3#A
V20
0\da
ta\A
dmin
istr
ator
\nm
r\W
ed2a
v2#0
32\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
200.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
8O
rigin
av20
0
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
n11
49.4
0SW
(cyc
lical
) (H
z)41
39.0
7So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)12
25.6
606
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)41
38.9
5Te
mpe
ratu
re (d
egre
e C
)27
.000
Wed
2av2
#032
.001
.001
.1r.
esp
3.80
Wed
2av2
#032
.001
.001
.1r.
esp
CH
LOR
OF
OR
M-d
7.60
9393
SI
CH
LOR
OF
OR
M-d
7.60
7.68
7.64
7.567.55
7.48
7.447.407.397.367.36
7.327.32
7.25
7.187.17
7.147.107.10
6.6.9
6.89
62I
6.896.936.93
7.14
7.257.367.44
7.567.6468
7.7
7.6
7.5
7.4
7.3
7.2
7.1
7.0
6.9
6.8
Che
mic
al S
hift
(ppm
)
1.98
1.08
1.09
1.07
1.90
1.00
3.13
1.98
1.08
1.09
1.07
1.90
1.00
0.92
3.82
7.107
7
7.6
9.37
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e14
Aug
201
3 10
:49:
04D
ate
Stam
p14
Aug
201
3 10
:49:
04
File
Nam
eH
:\New
fol
der\
Wed
3av5
00#0
01 y
m-9
67\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s63
5
Oi
isp
ect
Oi
ilP
it
Ct
3276
8O
nmr
Pi
tC
t32
768
Pl
Szg
pg30
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
Hz)
3125
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
979.
3203
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05Te
mpe
ratu
re (d
egre
e C
)22
.500
Wed
3av5
00#0
01.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
.00 77.
SI
112.27
63I
56.04
113.41113.59
121.07123.32
126.8451
132.04134.47
183
48
127.5129.83
135.137.93
156.4
185.36
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
14 A
ug 2
013
10:2
7:44
Dat
e St
amp
14 A
ug 2
013
10:2
7:44
File
Nam
eH
:\New
fold
er\W
ed3a
v500
#001
ym-9
67\2
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76Nu
cleu
s13
CNu
mbe
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rans
ient
s10
00Fi
le N
ame
H:\N
ew f
olde
r\W
ed3a
v500
#001
ym
-967
\2\P
DA
TA
\1\1
rFr
eque
ncy
(MH
z)12
5.76
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
1000
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90So
lven
tC
HLO
RO
FO
RM
-dSp
ectr
um O
ffset
(Hz)
1256
8.33
20
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00Te
mpe
ratu
re (d
egre
e C
)22
.000
Wed
3av5
00#0
01.0
02.0
01.1
r.es
p
04 56.0
13.41112.27
11113.60
121.06123.32
126.84
132.04
134.47
SI 64I
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
Che
mic
al S
hift
(ppm
)
SI 65I
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
19 A
ug 2
013
17:2
5:52
Dat
e St
amp
19 A
ug 2
013
17:2
5:52
File
Nam
e\\a
gni\n
mr
data
\AV
500\
Aug
1350
0\M
on4a
v500
#013
\1\P
DA
TA
\1\1
r
Mon
4av5
00#0
13.0
01.0
01.1
r.es
p
3.820
pg
g_
_g_
_
Freq
uenc
y (M
Hz)
500.
13N
ucle
us1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n32
2.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
19.7
769
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
22.2
00
MeO
3.80
N HO
2o
MeO
OM
e
Br
SI
CH
LOR
OF
OR
M-d
66I
7.597.59
.58
7.347.25
57.037.03
6.91
6.84
616
100
104
201
107
194
1039.20
7 7.56
7
7.0
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
6.16
1.00
1.04
2.01
1.07
1.94
1.03
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e19
Aug
201
3 20
:08:
00
Dat
e St
amp
19 A
ug 2
013
20:0
8:00
File
Nam
e\\a
gni\n
mr
data
\AV
500\
Aug
1350
0\M
on4a
v500
#013
\3\P
DA
TA
\1\1
rp
gg
__
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Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CNu
mbe
r of T
rans
ient
s21
02O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
982.
1816
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
22.8
00
Mon
4av5
00#0
13.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
77.00
N HO
MeO
OM
e
Br
O2o
OM
e
SI 67I
55.6356.08
102.75
113.00113.20
113.42
118.87
132.06134.41
112.26
127.87129.90
135.60
154.83156.50
185.04
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
19 A
ug 2
013
18:1
9:12
Dt
St19
A20
1318
1912
Fil
N\\
i\d
t\A
V50
0\A
1350
0\M
450
0#01
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PD
AT
A\1
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ate
Stam
p19
Aug
201
3 18
:19:
12Fi
le N
ame
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i\nm
r_da
ta\A
V_5
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ug_1
3_50
0\M
on4a
v500
#013
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DA
TA
\1\1
r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s12
00O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
571.
2676
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
22.5
00
Mon
4av5
00#0
13.0
02.0
01.1
r.es
p
6356.08
55.65
73
113.21.42
N HO
MeO
OM
e
Br
102.
113.00
113
118.87
32.06
134.42
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e
SI
13
68I
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
16C
hem
ical
Shi
ft (p
pm)
N H
MeO
Br
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OM
e
SI 69I
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
yoge
sh 1
HD
ate
16 A
ug 2
013
13:2
9:04
Dat
e St
amp
16 A
ug 2
013
13:2
9:04
File
Nam
eH
:\New
fol
der\
Fri3
av50
0#01
0\1\
PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64
Oi
isp
ect
Oi
ilP
it
Ct
2003
1O
nmr
Pi
tC
t32
768
Pl
Szg
30O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1O
wne
rnm
rPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
n32
2.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
09.7
742
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0Te
mpe
ratu
re (d
egre
e C
)22
.400
Fri3
av50
0#01
0.00
1.00
1.1r
.esp
3.82
SI 70I
CH
LOR
OF
OR
M-d
6.877.01
067.25
7.397.417.54
7.547.56 57
7.867.88
92
8.038.04
8
301
099
099
095
101
304
102
100
102
100
105
7.0
7.5
7.
8.28
9.54
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.01
0.99
0.99
0.95
1.01
3.04
1.02
1.00
1.02
1.00
1.05
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e16
Aug
201
3 15
:00:
48D
ate
Stam
p16
Aug
201
3 15
:00:
48
File
Nam
eH
:\New
fol
der\
Fri3
av50
0#01
0\3\
PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s11
72
Orig
insp
ect
Orig
inal
Poin
tsC
ount
3276
8O
wne
rnm
rPo
ints
Cou
nt32
768
Puls
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pg30
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
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Poin
ts C
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3276
8Pu
lse
Sequ
ence
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30
Rec
eive
r Gai
n57
5.00
SW(c
yclic
al) (
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3125
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Solv
ent
CH
LOR
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OR
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Spec
trum
Offs
et (H
z)11
981.
2275
Spec
trum
Typ
eS
TA
ND
AR
DSw
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Wid
th (H
z)31
249.
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mpe
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re (d
egre
e C
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0.00
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SI
55.63
102.75
113.18
118.73124.28
125.52126.50127.29
127.74128.35131.46
71I
130.78
133.78136.37
154.83
8.52 188
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
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ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
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omm
ent
DE
PT
;D
ate
16 A
ug 2
013
13:4
4:00
Dat
e St
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16 A
ug 2
013
13:4
4:00
File
Nam
eH
:\New
fol
der\
Fri3
av50
0#01
0\2\
PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
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mbe
r of T
rans
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s70
0
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um O
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1257
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Spec
trum
Typ
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EP
T13
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Wid
th (H
z)29
761.
00Te
mpe
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re (d
egre
e C
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6
102.75
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118.73
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127.28128.35
131.46
11
12
SI 72I
155
150
145
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
5550
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ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
17 A
ug 2
013
15:0
2:56
Dat
e St
amp
17 A
ug 2
013
15:0
2:56
File
Nam
eE
:\New
fol
der\
Sat
3av5
00#0
14\1
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
500.
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cleu
s1H
Num
ber o
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9
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Solv
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Spec
trum
Offs
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Spec
trum
Typ
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Wid
th (H
z)99
99.7
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re (d
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73I
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hem
ical
Shi
ft (p
pm)
3.14
6.38
3.06
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0.98
Acq
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tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e17
Aug
201
3 15
:43:
28D
ate
Stam
p17
Aug
201
3 15
:43:
28
File
Nam
eE
:\New
fol
der\
Sat
3av5
00#0
14\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s95
9
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n57
5.00
SW(c
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al) (
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3125
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Solv
ent
CH
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Spec
trum
Offs
et (H
z)11
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Spec
trum
Typ
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TA
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Wid
th (H
z)31
249.
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mpe
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re (d
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655
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4
74I
21.94
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112112.4
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3527.95
129.97
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6
2.79
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136.36
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1
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186.7
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168
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ical
Shi
ft (p
pm)
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tion
Tim
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ec)
1.10
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ent
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ate
17 A
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013
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Dat
e St
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17 A
ug 2
013
15:0
2:56
File
Nam
eE
:\New
fol
der\
Sat
3av5
00#0
14\2
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
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umbe
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rans
ient
s60
0
Orig
insp
ect
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inal
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nts
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nt32
768
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Poin
ts C
ount
3276
8Pu
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Sequ
ence
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(cyc
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lven
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Spec
trum
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Wid
th (H
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mpe
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re (d
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pm)
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Tim
e (s
ec)
2.00
31C
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esh
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ate
02 A
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Dat
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Sequ
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Rec
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Solv
ent
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Spec
trum
Offs
et (H
z)22
09.7
742
Spec
trum
Typ
eS
TA
ND
AR
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Wid
th (H
z)99
99.7
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re (d
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hem
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Shi
ft (p
pm)
3.19
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Acq
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tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e02
Aug
201
3 14
:52:
16D
ate
Stam
p02
Aug
201
3 14
:52:
16
File
Nam
eH
:\New
fol
der\
Fri1
av50
0#00
7\3\
PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s12
23q
y(
)O
rigin
spec
tO
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3276
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wne
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rPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
pg30
Rec
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r Gai
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5.00
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CH
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Spec
trum
Offs
et (H
z)11
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1357
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trum
Typ
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TA
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13
14
180.96
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184
176
168
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120
112
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168
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ft (p
pm)
Acq
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tion
Tim
e (s
ec)
1.10
10C
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ent
DE
PT
;D
ate
02 A
ug 2
013
14:3
5:12
Dat
e St
amp
02 A
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013
14:3
5:12
File
Nam
eH
:\New
fol
der\
Fri1
av50
0#00
7\2\
PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
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mbe
r of T
rans
ient
s80
0
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insp
ect
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inal
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tsC
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3276
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ner
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ont
3276
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lse
Seq
ence
dept
135
Orig
insp
ect
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inal
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nts
Cou
nt32
768
Ow
ner
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ts C
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3276
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Sequ
ence
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(cyc
lical
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z)29
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lven
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um O
ffset
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1257
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Spec
trum
Typ
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EP
T13
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Wid
th (H
z)29
761.
00Te
mpe
ratu
re (d
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)22
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125.5158
N HO
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S
111
1
12
125.
135.24
SI 79I
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
16C
hem
ical
Shi
ft (p
pm)
N HO
2
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S
2r
SI 80I
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uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
08 S
ep 2
013
12:0
5:52
Dat
e St
amp
08 S
ep 2
013
12:0
5:52
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Sun
2av5
00#0
01\1
\PD
AT
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\1r
Freq
uenc
y(M
Hz)
500
13Nu
cleu
s1H
Num
bero
fTra
nsie
nts
64O
rigin
spec
tO
rigin
alPo
ints
Cou
nt20
031
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
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Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n36
2.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
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Spec
trum
Offs
et (H
z)22
09.7
742
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
24.8
00
Sun
2av5
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01.0
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01.1
r.es
p
3.893.944.08
SI
CH
LOR
OF
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82
81I
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6.87.037.03
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7.947.95
313
319
304
100
098
202
105
200
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1
7
7 7.61
9.29
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
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3.5
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ical
Shi
ft (p
pm)
3.13
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3.04
1.00
0.98
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2.00
0.97
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e08
Sep
201
3 13
:50:
24
Dat
e St
amp
08 S
ep 2
013
13:5
0:24
File
Nam
e\\a
gni\n
mr
data
\AV
500\
Sep
1350
0\S
un2a
v500
#001
\3\P
DA
TA
\1\1
rp
pg
__
p__
Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CN
umbe
r of T
rans
ient
s18
62O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
982.
1826
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
25.7
00
Sun
2av5
00#0
01.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
77.00
SI
128.39129.11
82I
56.2461.1461.45
98.04
112.79
132.14
123.38
127.57
134.24
138.18138.94141.56
150.38
186.44
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
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0C
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ical
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ft (p
pm)
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uisi
tion
Tim
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ec)
1.10
10C
omm
ent
DE
PT
;D
ate
08 S
ep 2
013
12:1
2:16
Dat
e St
amp
08 S
ep 2
013
12:1
2:16
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Sun
2av5
00#0
01\2
\PD
AT
A\1
\1r
Freq
enc
(MH
)12
576
Ncl
es
13C
Nm
bero
fTra
nsie
nts
183
Orig
insp
ect
Orig
inal
Poin
tsC
ont
3276
8Fr
eque
ncy
(MH
z)12
5.76
Nuc
leus
13C
Num
ber o
f Tra
nsie
nts
183
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
572.
5947
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
25.1
00
Sun
2av5
00#0
01.0
02.0
01.1
r.es
p
128.4029.12
4
12
56.24
98.04
81
SI
61.1561.46
112.
132.15
83I
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
Che
mic
al S
hift
(ppm
)
Acq
uisi
tion
Tim
e (s
ec)
1.99
23C
omm
ent
Yog
esh
1HD
ate
15 A
ug 2
013
17:3
1:52
Dat
e St
amp
15 A
ug 2
013
17:3
1:52
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Aug
_13_
400\
Thu
3av4
00#0
04\1
\PD
AT
A\1
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400
13N
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Nb
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t64
Oi
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Oi
ilP
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1638
4Fr
eque
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0.13
Nucl
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1HNu
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s64
Orig
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Orig
inal
Poi
nts
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nt16
384
Ow
ner
Adm
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Cou
nt32
768
Puls
e Se
quen
cezg
30R
ecei
ver G
ain
256.
00SW
(cyc
lical
) (H
z)82
23.6
8
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)24
56.8
564
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)82
23.4
3
Tem
pera
ture
(deg
ree
C)
22.2
00
Thu
3av4
00#0
04.0
01.0
01.1
r.es
p
3.853.95
4.10
SI
CH
LOR
OF
OR
M-d
5
84I
6.756.82
7.25
7.527.54
7.567.82.848.0003
305
307
311
095
098
315
101
106
106
100
095
7
78
8.8.23
8.26
9.41
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.05
3.07
3.11
0.95
0.98
3.15
1.01
1.06
1.06
1.00
0.95
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
13C
Dat
e15
Aug
201
3 21
:20:
08
Dat
e St
amp
15 A
ug 2
013
21:2
0:08
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Aug
_13_
400\
Thu
3av4
00#0
04\3
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
100
61N
ucle
us13
CN
umbe
rofT
rans
ient
s40
00O
rigin
spec
tO
rigin
alPo
ints
Cou
nt16
384
Freq
uenc
y (M
Hz)
100.
61N
ucle
us13
CN
umbe
r of T
rans
ient
s40
00O
rigin
spec
tO
rigin
al P
oint
s C
ount
1638
4
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
2050
.00
SW(c
yclic
al) (
Hz)
2525
2.53
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)95
53.9
619
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
251.
75
Tem
pera
ture
(deg
ree
C)
22.3
00
Thu
3av4
00#0
04.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
77.00
SI
56.1861.1861.46
98.03
113.70
124.27125.51126.47127.23127.49
128.31131.31
135.83
85I
123.23
130.76
133.74
38.9341.74
150.38
87.93
114
18
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
DE
PT
Dat
e15
Aug
201
3 18
:18:
48
Dat
e St
amp
15 A
ug 2
013
18:1
8:48
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Aug
_13_
400\
Thu
3av4
00#0
04\2
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
100.
61N
ucle
us13
CN
umbe
r of T
rans
ient
s10
00O
rigin
spec
tO
rigin
al P
oint
s C
ount
1638
4
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n16
384.
00SW
(cyc
lical
) (H
z)25
252.
53
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
055.
5107
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
251.
75
Tem
pera
ture
(deg
ree
C)
22.3
00
Thu
3av4
00#0
04.0
02.0
01.1
r.es
p
56.18
61.1761.46
2
6
98.02
113.70
124.27125.50
126.46127.49
128.30131.31
SI 86I
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
Che
mic
al S
hift
(ppm
)
SI 87I
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
yoge
sh 1
HD
ate
30 A
ug 2
013
11:1
2:32
Dat
e St
amp
30 A
ug 2
013
11:1
2:32
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Aug
_13_
500\
Fri5
av50
0#00
4\1\
PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
500
13N
ucle
us1H
Num
bero
fTra
nsie
nts
64O
rigin
spec
tO
rigin
alPo
ints
Cou
nt20
031
Fri5
av50
0#00
4.00
1.00
1.1r
.esp
1.41
Freq
uenc
y (M
Hz)
500.
13N
ucle
us1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n32
2.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
19.7
769
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
22.1
00
CH
LOR
OF
OR
M-d
1.40.43
0
SI
11
4.404.42
7.23
7.41
88I
4.394.43
7.137.15
7.327
7.43
7.687.69
8.99
3.16
2.04
1.01
1.02
1.05
1.06
1.00
1.018
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e30
Aug
201
3 12
:14:
24
Dat
e St
amp
30 A
ug 2
013
12:1
4:24
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Aug
_13_
500\
Fri5
av50
0#00
4\3\
PD
AT
A\1
\1r
pg
g_
_g_
_
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s67
4O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
981.
2275
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
22.9
00
Fri5
av50
0#00
4.00
3.00
1.1r
.esp
CH
LOR
OF
OR
M-d
8
2
SI
14.38
61.03
108.62
111.84
120.76122.58
125.3248
89I
127.4
6.77
03
13
162.0
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
30 A
ug 2
013
11:3
3:52
Dat
e St
amp
30 A
ug 2
013
11:3
3:52
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Aug
_13_
500\
Fri5
av50
0#00
4\2\
PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
125
76Nu
cleu
s13
CN
umbe
rofT
rans
ient
s60
0O
rigin
spec
tO
rigin
alPo
ints
Cou
nt32
768
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CN
umbe
r of T
rans
ient
s60
0O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
569.
9307
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
22.4
00
Fri5
av50
0#00
4.00
2.00
1.1r
.esp
111.83
8
108.62
120.76122.58125.31
14.38
SI 90I
61
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
.02
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
yoge
sh 1
HD
ate
14 S
ep 2
013
13:2
2:40
Dat
e St
amp
14 S
ep 2
013
13:2
2:40
File
Nam
e\\a
gni\n
mr
data
\AV
500\
Sep
1350
0\S
at2a
v500
#008
\1\P
DA
TA
\1\1
rp
pg
__
p__
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n28
7.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
09.7
742
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
22.1
00
Sat
2av5
00#0
08.0
01.0
01.1
r.es
p
3.84
SI
1.40
91I
CH
LOR
OF
OR
M-d
1.391.42
4.394.40
7.067.077.14
7.3031
0.06
4.37
4.42
6.986.99
7.00
77.3
8.90
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.38
3.35
2.24
1.07
1.08
1.00
1.08
1.07
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e14
Sep
201
3 13
:58:
56
Dat
e St
amp
14 S
ep 2
013
13:5
8:56
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Sat
2av5
00#0
08\3
\PD
AT
A\1
\1r
F(M
H)
125
76N
l13
CN
bfT
it
223
Oi
isp
ect
Oi
ilP
it
Ct
3276
8Fr
eque
ncy
(MH
z)12
5.76
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
223
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
981.
2275
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
23.0
00
Sat
2av5
00#0
08.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
3
SI
14.38
55.65
60.95
102.50
108.18
112.7
116.93
92I
127.81
132.14
154.65
161.93
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
Che
mic
al S
hift
(ppm
)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
14 S
ep 2
013
13:4
8:16
Dat
e St
amp
14 S
ep 2
013
13:4
8:16
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Sep
_13_
500\
Sat
2av5
00#0
08\2
\PD
AT
A\1
\1r
F(M
H)
125
76N
l13
CN
bfT
it
600
Oi
isp
ect
Oi
ilP
it
Ct
3276
8Fr
eque
ncy
(MH
z)12
5.76
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
600
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt32
768
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
569.
0225
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
22.5
00
Sat
2av5
00#0
08.0
02.0
01.1
r.es
p
55.64
102.48
108.16
112.73
116.92
14.38
SI 93I
60
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
0.93
SI 94I
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
28 A
ug 2
013
16:0
4:48
Dat
e St
amp
28 A
ug 2
013
16:0
4:48
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Aug
_13_
500\
Wed
5av5
00#0
16\1
\PD
AT
A\1
\1r
pg
g_
_g_
_
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
64O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n25
6.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
09.4
690
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
22.2
00
Wed
5av5
00#0
16.0
01.0
01.1
r.es
p
1.43
2.61
41
SI
CH
LOR
OF
OR
M-d
1.41.44
4.414.42
7.35
95I
4.39
4.44
.127.147.25
7.317.37
7.657.67
7.
8.72
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.24
3.08
2.08
1.01
1.04
0.99
1.00
0.96
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e28
Aug
201
3 18
:17:
04
Dat
e St
amp
28 A
ug 2
013
18:1
7:04
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Aug
_13_
500\
Wed
5av5
00#0
16\3
\PD
AT
A\1
\1r
pg
g_
_g_
_
Freq
uenc
y (M
Hz)
125.
76N
ucle
us13
CNu
mbe
r of T
rans
ient
s15
25O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)11
981.
2275
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
23.0
00
Wed
5av5
00#0
16.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-d
77.00
4.45
76
SI
9.92
14
60.67
111.59
119.8120.7
125.54
96I
0
28.54
5.80
2.66
123.40
12
135
162
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.10
10C
omm
ent
DE
PT
;D
ate
28 A
ug 2
013
16:5
8:08
Dat
e St
amp
28 A
ug 2
013
16:5
8:08
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Aug
_13_
500\
Wed
5av5
00#0
16\2
\PD
AT
A\1
\1r
pg
g_
_g_
_
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s12
00O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)29
761.
90
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
570.
3564
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)29
761.
00
Tem
pera
ture
(deg
ree
C)
22.5
00
Wed
5av5
00#0
16.0
02.0
01.1
r.es
p
60.67
SI 97I
9.92
14.466
111
1112
125.5
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
1.59
9.8720.75
53
Acq
uisi
tion
Tim
e (s
ec)
2.00
31C
omm
ent
Yog
esh
1HD
ate
03 O
ct 2
013
11:2
1:04
Dat
e St
amp
03 O
ct 2
013
11:2
1:04
File
Nam
e\\a
gni\n
mr
data
\AV
500\
Oct
1350
0\T
hu1a
v500
#001
\1\P
DA
TA
\1\1
rp
g_
__
_
Freq
uenc
y (M
Hz)
500.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
37O
rigin
spec
tO
rigin
al P
oint
s C
ount
2003
1
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zg30
Rec
eive
r Gai
n20
3.00
SW(c
yclic
al) (
Hz)
1000
0.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)22
09.7
744
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)99
99.7
0
Tem
pera
ture
(deg
ree
C)
22.7
00
Thu
1av5
00#0
01.0
01.0
01.1
r.es
p
1.42
C4H
9
94
N HOO
Et
5d
0.9
1.41.44
SI
0.920.95
1
3.10
4.404.42
98I
CH
LOR
OF
OR
M-d
1.39
1.631.641.66
1.67
3.083.11
39
43
7.12.25
7.317.36
7.37
7.677.69
0.07
1.69
4.3
4.
7.117.
8.73
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.05
5.21
2.66
2.01
2.00
0.97
0.96
0.96
1.00
0.94
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
13C
Dat
e03
Oct
201
3 11
:50:
56
Dt
St03
Ot2
013
1150
56Fi
lN
\\i\
dt
\AV
500\
Ot
1350
0\T
h1
500#
001\
3\P
DA
TA
\1\1
Dat
e St
amp
03 O
ct 2
013
11:5
0:56
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Oct
_13_
500\
Thu
1av5
00#0
01\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s51
2O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30R
ecei
ver G
ain
575.
00SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
570.
5986
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
23.6
00
Thu
1av5
00#0
01.0
03.0
01.1
r.es
pC
HLO
RO
FO
RM
-dC
4H
9
77.00
N HOO
Et
5d
SI
14.024.40
22.83.48
33.22
1.65
9.8392
125.44
99I
1
24.
3
60.64
11
119120.
7
6
123.04
128.07
135.86
162.54
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
86C
omm
ent
DE
PT
;D
ate
03 O
ct 2
013
11:2
3:12
Dat
e St
amp
03 O
ct 2
013
11:2
3:12
File
Nam
e\\a
gni\n
mr_
data
\AV
_500
\Oct
_13_
500\
Thu
1av5
00#0
01\2
\PD
AT
A\1
\1r
pg
__
__
Freq
uenc
y (M
Hz)
125.
76Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s30
0O
rigin
spec
tO
rigin
al P
oint
s C
ount
3276
8
Ow
ner
nmr
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)31
250.
00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)12
570.
6387
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)31
249.
05
Tem
pera
ture
(deg
ree
C)
22.9
00
Thu
1av5
00#0
01.0
02.0
01.1
r.es
p
14.02
65
9.8320.92
C4H
9
111.6
11912
125.44
N HOO
Et
5d
SI 100
22.832
33
6
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
24.49
3.22
60.65
NOO
Et
C4H
9
HO
5d
SI 101
Acq
uisi
tion
Tim
e (s
ec)
3.95
84C
omm
ent
Yog
esh
Dat
e13
Sep
201
3 15
:04:
40
Dat
e St
amp
13 S
ep 2
013
15:0
4:40
File
Nam
e\\a
gni\n
mr_
data
\AV
200\
SE
PT
_13#
AV
200\
data
\Adm
inis
trat
or\n
mr\
Fri2
av2#
031\
1\P
DA
TA
\1\1
r
Freq
uenc
y(M
Hz)
200
13Nu
cleu
s1H
Num
bero
fTra
nsie
nts
8O
rigin
av20
0Fr
eque
ncy
(MH
z)20
0.13
Nucl
eus
1HNu
mbe
r of T
rans
ient
s8
Orig
inav
200
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
n11
49.4
0SW
(cyc
lical
) (H
z)41
39.0
7So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)12
25.5
343
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)41
38.9
5Te
mpe
ratu
re (d
egre
e C
)27
.000
Fri2
av2#
031.
001.
001.
1r.e
sp
1.23
Ph
N HOO
Et
Ph
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CH
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OR
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7.25
SI
1.191
4.274.30
7.407.457.54
102
4.23
4.34
117.14
7.36
7.577.61
7.65
01
3.49
2.00
1.05
5.09
2.01
0.99
0.98
7.
9.
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.68
32C
omm
ent
yoge
shD
ate
14 S
ep 2
013
21:3
9:20
Dat
e St
amp
14 S
ep 2
013
21:3
9:20
File
Nam
e\\a
gni\n
mr_
data
\AV
200\
SE
PT
_13#
AV
200\
data
\Adm
inis
trat
or\n
mr\
Sat
2av2
#051
\2\P
DA
TA
\1\1
r
F(M
H)
5032
Nl
13C
Nb
fTi
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00O
ii
av20
0Fr
eque
ncy
(MH
z)50
.32
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
1600
Orig
inav
200
Orig
inal
Poi
nts
Cou
nt81
92O
wne
rA
dmin
istr
ator
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
30
Rec
eive
r Gai
n81
2.70
SW(c
yclic
al) (
Hz)
1199
0.41
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)50
29.8
706
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)11
990.
04Te
mpe
ratu
re (d
egre
e C
)27
.000
Sat
2av2
#051
.002
.001
.1r.
esp
CH
LOR
OF
OR
M-d
Sat
2av2
#051
.002
.001
.1r.
esp
64
73
77.00
130.
94127.7
127.18
125.78
79
121.75
120.85
N HOO
Et
Ph
5e
131
130
129
128
127
126
125
124
123
122
121
Che
mic
al S
hift
(ppm
)
127.
124.25
122.7
SI
127.73
130.64
103
14.03
60.87
111.68
120.85121.75125.78127.18
122.79
127.94
133.51135.70
162.04
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.68
32C
omm
ent
yoge
shD
ate
14 S
ep 2
013
20:2
4:40
Dat
e St
amp
14 S
ep 2
013
20:2
4:40
File
Nam
e\\a
gni\n
mr_
data
\AV
200\
SE
PT
_13#
AV
200\
data
\Adm
inis
trat
or\n
mr\
Sat
2av2
#051
\1\P
DA
TA
\1\1
r
F(M
H)
5032
Nl
13C
Nb
fTi
t80
0O
ii
av20
0Fr
eque
ncy
(MH
z)50
.32
Nucl
eus
13C
Num
ber o
f Tra
nsie
nts
800
Orig
inav
200
Orig
inal
Poi
nts
Cou
nt81
92O
wne
rA
dmin
istr
ator
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
dept
135
Rec
eive
r Gai
n16
384.
00SW
(cyc
lical
) (H
z)11
990.
41So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)50
29.1
680
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)11
990.
04Te
mpe
ratu
re (d
egre
e C
)27
.000
Sat
2av2
#051
.001
.001
.1r.
esp
127.73
130.63
Ph
3
N HOO
Et
Ph
5e
14.03
111.68
120.83121.73
125.77127.18
SI 104
60
150
145
140
135
130
125
120
115
110
105
100
9590
8580
7570
6560
5550
4540
3530
2520
1510
Che
mic
al S
hift
(ppm
)
0.89
NOO
Et
Ph
H 5e
SI 105
Acq
uisi
tion
Tim
e (s
ec)
2.04
47C
omm
ent
Yog
esh
1HD
ate
18 F
eb 2
014
15:5
8:00
Dat
e St
amp
18 F
eb 2
014
15:5
8:00
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Feb
_14_
400\
Tue
4av4
00#0
07\1
\PD
AT
A\1
\1r
Freq
uenc
y(M
Hz)
400
13Nu
cleu
s1H
Num
bero
fTra
nsie
nts
32O
rigin
spec
tFr
eque
ncy
(MH
z)40
0.13
Nucl
eus
1HNu
mbe
r of T
rans
ient
s32
Orig
insp
ect
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30
Rec
eive
r Gai
n28
7.00
SW(c
yclic
al) (
Hz)
8012
.82
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)27
87.6
018
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)80
12.5
8Te
mpe
ratu
re (d
egre
e C
)22
.200
Tue
4av4
00#0
07.0
01.0
01.1
r.es
p
2.46
Tue
4av4
00#0
07.0
01.0
01.1
r.es
p
7.49
7.5860
8.01
SI
CH
LOR
OF
OR
M-d 7.25
7.417.427.43
7.457.45
7.47
7.507.51
7.537.53
7.67.60 7.63
7.647.66
7.66
7.68
7.767.78
8.11
8.14
I 106
8.1
8.0
7.9
7.8
7.7
7.6
7.5
7.4
7.3
Che
mic
al S
hift
(ppm
)
4.14
1.99
1.05
1.04
1.01
1.00
CH
LOR
OF
OR
M-d
18.01
6
7.607.607.587.49
7.47 53
8.148.1
7.787.76
7.667
7.457.43
7.41
7.25
0.00
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.14
4.14
1.99
1.05
1.04
1.01
1.00
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
13C
Dat
e18
Feb
201
4 16
:49:
12
Dat
e St
amp
18 F
eb 2
014
16:4
9:12
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Feb
_14_
400\
Tue
4av4
00#0
07\3
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
100.
61Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s10
46O
rigin
spec
t
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
root
Poin
ts C
ount
3276
8Pu
lse
Sequ
ence
zgpg
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)25
252.
53So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)96
32.5
684
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
251.
75Te
mpe
ratu
re (d
egre
e C
)22
.700
Tue
4av4
00#0
07.0
03.0
01.1
r.es
p
128.82128.28
CH
LOR
OF
OR
M-d
77.00
SI
8.1639
I 107
136.72
129.25
128126.
20.60
Tue
4av4
00#0
07.0
03.0
01.1
r.es
p
9
6
128.28
2
128.82
126.39
126.67
127.57
128.16
128.72
129.19129.25
160.51
146.58
140.82
129.
012
8.5
128.
012
7.5
127.
012
6.5
Che
mic
al S
hift
(ppm
)
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
0.64
88C
omm
ent
DE
PT
Dat
e18
Feb
201
4 16
:21:
28
Dat
e St
amp
18 F
eb 2
014
16:2
1:28
File
Nam
e\\a
gni\n
mr_
data
\AV
400\
Feb
_14_
400\
Tue
4av4
00#0
07\2
\PD
AT
A\1
\1r
Freq
uenc
y (M
Hz)
100.
61N
ucle
us13
CNu
mbe
r of T
rans
ient
s78
2O
rigin
spec
t
Orig
inal
Poin
tsC
ount
1638
4O
wne
rro
otPo
ints
Cou
nt32
768
Puls
eSe
quen
cede
pt13
5O
rigin
al P
oint
s C
ount
1638
4O
wne
rro
otPo
ints
Cou
nt32
768
Puls
e Se
quen
cede
pt13
5
Rec
eive
r Gai
n20
50.0
0SW
(cyc
lical
) (H
z)25
252.
53So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)10
056.
9004
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
251.
75Te
mpe
ratu
re (d
egre
e C
)22
.600
Tue
4av4
00#0
07.0
02.0
01.1
r.es
p
128.82128.28
SI
73
126.39
I 108
136.7
129.25
20.60
Tue
4av4
00#0
07.0
02.0
01.1
r.es
p
128.28
128.82
126.39
126.68
128.16
128.73
129.25
129.
012
8.5
128.
012
7.5
127.
012
6.5
126.
0C
hem
ical
Shi
ft (p
pm)
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
3.95
84C
omm
ent
Yog
esh
Dat
e12
Mar
201
4 17
:23:
20
Dat
e St
amp
12 M
ar 2
014
17:2
3:20
File
Nam
eK
:\Wed
3av2
#041
\1\P
DA
TA
\1\1
r
Freq
uenc
y (M
Hz)
200.
13Nu
cleu
s1H
Num
ber o
f Tra
nsie
nts
8O
rigin
av20
0
Orig
inal
Poi
nts
Cou
nt16
384
Ow
ner
Adm
inis
trat
orPo
ints
Cou
nt32
768
Puls
e Se
quen
cezg
30R
ecei
ver G
ain
724.
10SW
(cyc
lical
) (H
z)41
39.0
7So
lven
tC
HLO
RO
FO
RM
-d
Spec
trum
Offs
et (H
z)12
25.6
606
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)41
38.9
5
Tem
pera
ture
(deg
ree
C)
27.0
00
Wed
3av2
#041
.001
.001
.1r.
esp
2.162.16
OO
Ph
NH
2 7
SII 109
CH
LOR
OF
OR
M-d
1
69.696.73
6.736.81.82
7.097.217.25
7.447.48
7.507.547.73
7.747.77 7.77
-0.0
3.63
6.66
66.
6.85
7
7.41
7
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0C
hem
ical
Shi
ft (p
pm)
3.04
2.01
1.00
1.03
3.27
3.39
2.07
Acq
uisi
tion
Tim
e (s
ec)
1.04
34C
omm
ent
yoge
sh g
oria
Dat
e16
Mar
201
4 01
:25:
29
Dat
e St
amp
16 M
ar 2
014
00:3
6:06
File
Nam
eK
:\Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_CA
RB
ON
-3.jd
f
Freq
uenc
y (M
Hz)
100.
53Nu
cleu
s13
CNu
mbe
r of T
rans
ient
s60
0O
rigin
EC
X 4
00
Orig
inal
Poi
nts
Cou
nt26
214
Ow
ner
delta
Poin
ts C
ount
2621
4Pu
lse
Sequ
ence
sing
le_p
ulse
_dec
Rec
eive
r Gai
n60
.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
039.
3311
Spec
trum
Typ
eS
TA
ND
AR
DSw
eep
Wid
th (H
z)25
124.
29Te
mpe
ratu
re (d
egre
e C
)22
.900
Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_CA
RB
ON
-3.e
sp
77.00
O
Ph
Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_CA
RB
ON
-3.e
sp
129.43
128.22
NH
2 7
SI
128.22129.43
138.47138.24
138.11
131.77
129.74129.60
I 110
14.44
25
77
138
137
136
135
134
133
132
131
130
129
128
Che
mic
al S
hift
(ppm
)
1
115.72118.25
121.19
131.7
138.11138.24
8.47
144.34
15
138
199.
E:\Y
oges
h\2-
Aro
yl In
dole
\Indo
le m
etho
\NM
R\P
ropi
onat
e B
\Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_CA
RB
ON
-3.e
sp
200
192
184
176
168
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
Acq
uisi
tion
Tim
e (s
ec)
1.04
34C
omm
ent
yoge
sh g
oria
Dat
e16
Mar
201
4 01
:25:
29
Dat
e St
amp
16 M
ar 2
014
00:4
8:10
File
Nam
eK
:\Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_DE
PT
135-
3.jd
f
Freq
uenc
y (M
Hz)
100.
53Nu
cleu
s13
CN
umbe
r of T
rans
ient
s30
0O
rigin
EC
X 4
00
Orig
inal
Poi
nts
Cou
nt26
214
Ow
ner
delta
Poin
ts C
ount
2621
4Pu
lse
Sequ
ence
dept
.ex2
(se
lect
ion_
angl
e=13
5)
Rec
eive
r Gai
n60
.00
Solv
ent
CH
LOR
OF
OR
M-d
Spec
trum
Offs
et (H
z)10
038.
3789
Spec
trum
Typ
eD
EP
T13
5Sw
eep
Wid
th (H
z)25
124.
29Te
mpe
ratu
re (d
egre
e C
)22
.800
Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_DE
PT
135-
3.es
p
128.21129.42
OO
Ph
NH
2 7
SI
115.72
5
9.73
I 111
118.2
129131.76
138.23
14.43
E:\Y
oges
h\2-
Aro
yl In
dole
\Indo
le m
etho
\NM
R\P
ropi
onat
e B
\Fri3
EC
X40
0#04
3_M
AR
_14_
2014
_DE
PT
135-
3.es
p
160
152
144
136
128
120
112
104
9688
8072
6456
4840
3224
168
0C
hem
ical
Shi
ft (p
pm)
