Post on 11-Jun-2020
transcript
S1
Supporting information
I2/DMSO mediated multicomponent reaction for the synthesis
of 2-arylbenzo[d]imidazo[2,1-b] thiazole derivatives
Asim Jana, Prabhas Bhaumick, Anoop Kumar Panday, Richa Mishra and Lokman H. Choudhury*
Department of Chemistry, Indian Institute of Technology Patna, Bihta, Patna-801106
Table of contents:
1. Copies of 1H and 13C NMR spectra of compounds..........................................S2-S39
2. Crystal structure description of 6o…………………………………………....S40-S48
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019
S2
Copies of 1H and 13C NMR spectra of compounds
1H and 13C NMR spectra of 4a
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.02
6.34
2.17
2.17
1.06
2.13
1.00
2.42
3.19
7.30
7.32
7.33
7.34
7.36
7.39
7.41
7.43
7.58
7.61
7.70
7.71
7.93
7.37.47.57.67.77.87.98.0f1 (ppm)
7.30
7.32
7.33
7.34
7.36
7.39
7.41
7.43
7.58
7.61
7.70
7.71
7.93
0102030405060708090100110120130140150160f1 (ppm)
21.38
28.04
76.30
115.02
122.01
125.05
126.85
128.30
128.79
129.05
129.51
131.13
131.56
136.15
145.12
153.03
162.11
122124126128130132f1 (ppm)
122.01
125.05
126.85
128.30
128.79
129.05
129.51
130.12
131.13
131.56
N
NS
N
NOH
O
O
N
NS
N
NOH
O
O
S3
1H and 13C NMR spectra of 4b
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
3.07
2.87
6.16
1.04
2.05
1.01
2.09
1.00
2.28
2.30
3.21
7.30
7.32
7.34
7.39
7.41
7.43
7.44
7.68
7.69
7.88
7.27.37.47.57.67.77.87.98.0f1 (ppm)
7.30
7.32
7.34
7.39
7.41
7.43
7.44
7.68
7.69
7.88
0102030405060708090100110120130140150160170f1 (ppm)
20.05
20.61
28.01
76.16
115.94
122.29
125.14
126.47
126.84
128.47
129.09
131.36
135.62
136.60
145.20
153.05
162.15
N
NS
N
NOH
O
O
N
NS
N
NOH
O
O
S4
1H and 13C NMR spectra of 4c
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.18
5.90
2.21
0.97
1.01
2.00
0.99
2.01
1.00
1.33
1.35
1.37
3.19
4.05
4.07
4.09
4.10
7.13
7.15
7.30
7.31
7.33
7.39
7.41
7.43
7.59
7.62
7.68
7.70
7.75
7.17.27.37.47.57.67.77.8f1 (ppm)
7.13
7.15
7.30
7.31
7.33
7.39
7.41
7.43
7.59
7.62
7.68
7.70
7.75
0102030405060708090100110120130140150160170f1 (ppm)
14.99
27.98
64.38
75.85
110.03
115.63
116.13
122.29
126.82
127.06
128.34
129.06
130.91
131.28
144.44
153.11
157.00
162.16
N
NS
N
NOH
O
O OC2H5
N
NS
N
NOH
O
O OC2H5
S5
1H and 13C NMR spectra of 4d
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
6.31
1.14
2.31
1.13
3.17
0.95
3.22
7.27
7.29
7.31
7.37
7.39
7.41
7.53
7.53
7.55
7.55
7.67
7.70
7.72
8.26
8.27
7.47.67.88.08.28.4f1 (ppm)
7.29
7.37
7.39
7.41
7.55
7.55
7.67
7.70
7.72
8.26
8.27
0102030405060708090100110120130140150160170180f1 (ppm)
28.35
77.44
116.10
120.29
124.87
126.73
127.77
128.06
129.00
129.84
131.42
132.14
132.60
140.97
146.16
152.63
161.91
N
NS
N
NOH
O
O Cl
N
NS
N
NOH
O
O Cl
S6
1H and 13C NMR spectra of 4e
N
NS
N
NOH
O
O NO2
N
NS
N
NOH
O
O NO2
S7
1H and 13C NMR spectra of 4f
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.00
6.02
2.31
0.96
2.98
2.01
1.04
1.33
1.35
1.37
3.20
4.05
4.06
4.08
4.10
7.07
7.07
7.09
7.09
7.53
7.55
7.61
7.63
7.68
7.68
7.07.17.27.37.47.57.67.77.8f1 (ppm)
7.07
7.07
7.09
7.09
7.53
7.55
7.61
7.63
7.68
7.68
0102030405060708090100110120130140150160f1 (ppm)
15.05
27.79
64.24
76.63
109.90
110.42
114.51
115.11
127.77
128.44
128.54
130.80
131.38
131.72
131.81
144.53
153.44
156.07
162.05
N
NS
N
NOH
O
O OC2H5
Br
N
NS
N
NOH
O
O OC2H5
Br
S8
1H and 13C NMR spectra of 4g
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.30
3.15
3.07
6.00
2.14
0.94
2.08
0.84
2.28
2.30
2.33
3.18
7.20
7.22
7.43
7.58
7.60
7.88
7.27.37.47.57.67.77.87.9f1 (ppm)
7.20
7.22
7.43
7.58
7.60
7.88
0102030405060708090100110120130140150160f1 (ppm)
20.06
20.63
21.27
27.93
75.77
116.03
122.33
125.13
126.47
126.77
127.88
129.67
131.36
135.72
136.66
138.09
144.80
153.18
162.26
120125130135140f1 (ppm)
122.33
125.13
126.47
126.77
127.88
129.67
131.36
135.72
136.66
137.26
138.09
N
NS
N
NOH
O
O
N
NS
N
NOH
O
O
S9
1H and 13C NMR spectra of 4h
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
5.60
3.00
2.00
1.92
1.00
1.06
0.79
3.24
3.76
6.94
6.96
7.66
7.68
7.82
7.84
8.27
8.28
8.30
8.30
9.11
9.11
7.07.58.08.59.0f1 (ppm)
6.94
6.96
7.66
7.68
7.82
7.84
8.27
8.28
8.30
8.30
9.11
9.11
0102030405060708090100110120130140150160170f1 (ppm)
28.49
55.55
78.25
114.40
118.37
121.57
123.20
126.17
128.10
130.89
137.40
143.71
144.17
148.00
152.49
159.19
161.86
N
NS
N
NOH
O
O NO2
H3CO
N
NS
N
NOH
O
O NO2
H3CO
S10
1H and 13C NMR spectra of 4i
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
5.94
2.92
1.02
1.00
3.06
2.03
3.21
3.82
7.05
7.06
7.08
7.08
7.53
7.55
7.70
7.70
7.71
7.73
7.92
7.94
7.07.17.27.37.47.57.67.77.87.9f1 (ppm)
7.05
7.06
7.08
7.08
7.53
7.55
7.70
7.70
7.71
7.73
7.92
7.94
0102030405060708090100110120130140150160170f1 (ppm)
28.20
56.25
77.37
109.45
114.58
115.52
122.09
125.72
125.76
126.83
127.38
131.03
137.86
139.51
145.67
152.85
157.31
161.87
N
NS
N
NOH
O
O OCH3
F3C
N
NS
N
NOH
O
O OCH3
F3C
S11
1H and 13C NMR spectra of 4j
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.02
2.98
6.00
0.99
1.00
2.08
2.07
2.28
2.31
3.25
7.34
7.77
7.96
7.98
8.19
8.21
7.37.47.57.67.77.87.98.08.18.28.3f1 (ppm)
7.34
7.77
7.96
7.98
8.19
8.21
0102030405060708090100110120130140150160f1 (ppm)
19.92
20.47
28.40
78.45
115.38
122.32
124.24
124.99
126.66
126.88
131.47
134.63
135.86
140.00
140.97
146.00
147.13
152.57
161.64
N
NS
N
NOH
O
O
O2N
N
NS
N
NOH
O
O
O2N
S12
1H and 13C NMR spectra of 6a
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
5.89
3.16
1.04
1.05
2.12
1.04
1.00
2.09
3.17
3.81
7.07
7.08
7.09
7.10
7.21
7.23
7.25
7.33
7.34
7.36
7.50
7.53
7.68
7.68
7.73
7.74
7.17.27.37.47.57.67.7f1 (ppm)
7.07
7.08
7.09
7.10
7.21
7.23
7.25
7.33
7.34
7.36
7.50
7.53
7.68
7.68
7.73
7.74
0102030405060708090100110120130140150160170180f1 (ppm)
27.83
56.23
76.22
109.34
114.58
115.48
122.69
126.67
127.31
127.61
128.69
130.89
133.55
139.90
144.26
153.40
157.18
162.22
N
NS
NN
OH
O
O
OCH3
N
NS
NN
OH
O
O
OCH3
S13
1H and 13C NMR spectra of 6b
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.10
6.12
3.28
3.17
2.08
1.03
1.00
2.26
3.18
3.82
7.16
7.18
7.53
7.55
7.62
7.64
7.77
7.78
7.17.27.37.47.57.67.77.87.9f1 (ppm)
7.16
7.18
7.53
7.55
7.62
7.64
7.77
7.78
0102030405060708090100110120130140150160f1 (ppm)
21.25
27.94
56.31
75.41
109.45
115.46
116.35
122.26
126.65
127.01
127.53
129.66
130.99
136.92
138.17
144.07
153.18
157.89
162.34
N
NS
NN
OH
O
O
OCH3
N
NS
NN
OH
O
O
OCH3
S14
1H and 13C NMR spectra of 6c
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
6.00
2.97
2.94
2.14
1.18
1.01
3.23
3.16
3.74
3.80
6.89
6.91
7.06
7.06
7.08
7.09
7.47
7.50
7.64
7.66
6.97.07.17.27.37.47.57.67.7f1 (ppm)
6.89
6.91
7.06
7.06
7.08
7.09
7.47
7.50
7.64
7.66
0102030405060708090100110120130140150160170f1 (ppm)
27.75
55.49
56.21
76.07
109.30
114.12
114.47
115.31
121.91
127.75
127.98
130.77
140.05
143.70
153.52
157.02
158.72
162.32
N
NS
NN
OH
O
O
H3CO
OCH3
N
NS
NN
OH
O
O
H3CO
OCH3
S15
1H and 13C NMR spectra of 6d
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
6.00
2.89
3.04
0.98
1.02
3.12
1.00
0.93
3.18
3.72
3.82
6.86
6.88
7.13
7.13
7.15
7.16
7.27
7.29
7.31
7.33
7.35
7.60
7.62
7.75
7.76
6.97.07.17.27.37.47.57.67.77.8f1 (ppm)
6.86
6.88
7.13
7.13
7.15
7.16
7.27
7.29
7.31
7.33
7.35
7.60
7.62
7.75
7.76
0102030405060708090100110120130140150160f1 (ppm)
27.90
55.31
56.28
75.92
109.42
112.09
114.16
115.16
116.05
119.10
122.66
127.23
130.02
130.94
132.92
138.04
144.34
153.18
157.67
159.67
162.23
N
NS
NN
OH
O
O
H3CO
OCH3
N
NS
NN
OH
O
O
H3CO
OCH3
S16
1H and 13C NMR spectra of 6e
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
6.00
3.21
1.07
2.11
1.13
1.04
1.99
3.19
3.82
7.09
7.09
7.11
7.12
7.42
7.44
7.69
7.71
7.72
7.73
7.17.27.37.47.57.67.7f1 (ppm)
7.09
7.09
7.11
7.12
7.42
7.44
7.55
7.57
7.69
7.71
7.72
7.73
0102030405060708090100110120130140150160170f1 (ppm)
28.09
56.26
76.66
104.53
109.44
113.60
114.84
115.72
127.31
128.29
128.94
130.95
131.72
132.30
144.98
152.96
157.44
161.98
N
NS
NN
OH
O
O
Cl
OCH3
N
NS
NN
OH
O
O
Cl
OCH3
S17
1H and 13C NMR spectra of 6f
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
6.00
2.88
1.02
1.02
2.08
0.99
0.96
3.21
3.82
7.05
7.06
7.08
7.08
7.53
7.61
7.63
7.69
7.70
7.92
7.92
7.17.27.37.47.57.67.77.87.9f1 (ppm)
7.05
7.06
7.08
7.08
7.53
7.55
7.59
7.61
7.63
7.63
7.65
7.65
7.69
7.70
7.92
7.92
0102030405060708090100110120130140150160170f1 (ppm)
28.22
56.24
77.18
109.42
114.68
115.63
121.64
126.42
127.26
128.16
129.74
130.99
131.14
131.54
134.17
138.26
145.59
152.75
157.37
161.87
N
NS
NN
OH
O
O
Cl
Cl
OCH3
N
NS
NN
OH
O
O
Cl
Cl
OCH3
S18
1H and 13C NMR spectra of 6g
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
5.93
3.14
1.00
3.07
3.10
3.18
3.81
7.06
7.07
7.09
7.09
7.52
7.54
7.64
7.66
7.69
7.17.27.37.47.57.67.7f1 (ppm)
7.06
7.07
7.09
7.09
7.51
7.52
7.53
7.54
7.54
7.64
7.66
7.68
7.69
0102030405060708090100110120130140150160170f1 (ppm)
27.92
56.22
76.64
109.34
114.42
115.38
120.21
122.47
127.59
128.49
130.89
131.58
133.50
139.68
144.75
153.24
157.09
162.03
N
NS
NN
OH
O
O
Br
OCH3
N
NS
NN
OH
O
O
Br
OCH3
S19
1H and 13C NMR spectra of 6h
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
6.00
3.25
1.04
1.00
2.04
3.09
3.16
3.80
7.03
7.03
7.05
7.05
7.44
7.52
7.54
7.63
7.64
7.66
7.07.17.27.37.47.57.6f1 (ppm)
7.03
7.03
7.05
7.05
7.44
7.46
7.52
7.54
7.63
7.64
7.66
0102030405060708090100110120130140150160170f1 (ppm)
27.82
56.19
76.61
92.51
109.29
114.20
115.20
122.91
127.74
128.60
130.86
134.56
137.28
140.34
144.56
153.40
156.90
162.06
N
NS
NN
OH
O
O
I
OCH3
N
NS
NN
OH
O
O
I
OCH3
S20
1H and 13C NMR spectra of 6i
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
6.00
3.14
1.05
0.98
0.98
2.15
2.11
3.23
3.81
7.03
7.04
7.05
7.06
7.51
7.66
7.66
7.95
7.97
8.17
8.20
7.17.37.57.77.98.1f1 (ppm)
7.03
7.04
7.05
7.06
7.51
7.54
7.66
7.66
7.95
7.97
8.17
8.20
0102030405060708090100110120130140150160170f1 (ppm)
28.33
56.23
77.96
109.43
114.44
115.50
124.23
126.79
127.28
131.13
139.07
139.81
141.15
145.90
146.43
152.71
152.74
157.29
161.73
N
NS
NN
OH
O
O
O2N
OCH3
N
NS
NN
OH
O
O
O2N
OCH3
S21
1H and 13C NMR spectra of 6j
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
6.00
3.09
1.12
1.15
2.23
1.08
1.11
0.95
3.22
3.82
7.04
7.04
7.06
7.07
7.52
7.67
7.67
8.04
8.12
8.14
8.58
8.58
8.58
7.07.27.47.67.88.08.28.48.6f1 (ppm)
7.04
7.06
7.07
7.52
7.54
7.64
7.66
7.67
7.67
8.04
8.05
8.06
8.07
8.12
8.14
8.58
8.58
0102030405060708090100110120130140150160f1 (ppm)
28.16
56.22
77.40
109.38
114.43
115.47
120.88
121.43
122.16
127.44
130.32
131.02
132.41
136.04
139.29
145.70
148.43
152.86
157.19
161.92
N
NS
N
NOH
O
O OCH3
NO2
N
NS
N
NOH
O
O OCH3
NO2
S22
1H and 13C NMR spectra of 6k
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
6.00
3.09
1.11
3.36
1.04
3.34
1.12
1.09
3.19
3.82
7.05
7.06
7.07
7.08
7.45
7.49
7.51
7.63
7.64
7.84
8.25
7.17.37.57.77.98.1f1 (ppm)
7.05
7.06
7.07
7.08
7.44
7.44
7.45
7.45
7.46
7.47
7.47
7.49
7.51
7.63
7.64
7.82
7.84
7.92
7.92
8.25
0102030405060708090100110120130140150160f1 (ppm)
27.83
56.21
76.69
109.29
114.28
115.31
124.96
125.24
126.51
127.81
127.86
128.37
130.85
132.25
133.45
140.90
144.48
153.50
156.94
162.29
122124126128130132134f1 (ppm)
123.22
124.96
125.24
125.97
126.51
127.81
127.86
128.37
130.85
132.25
133.45
N
NS
N
NOH
O
O OCH3
N
NS
N
NOH
O
O OCH3
S23
1H and 13C NMR spectra of 6l
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
6.00
3.24
2.25
1.03
1.08
1.09
3.16
1.07
2.09
1.03
3.22
3.78
3.81
7.09
7.11
7.28
7.30
7.32
7.35
7.37
7.39
7.52
7.55
7.57
7.72
7.74
7.82
7.84
7.89
7.17.27.37.47.57.67.77.87.9f1 (ppm)
7.09
7.11
7.28
7.30
7.32
7.35
7.37
7.39
7.52
7.55
7.57
7.72
7.74
7.82
7.84
7.89
0102030405060708090100110120130140150160f1 (ppm)
27.84
36.91
56.19
76.32
93.17
109.21
114.63
115.53
120.27
120.37
123.33
125.47
125.52
127.22
130.85
140.33
141.36
143.36
143.66
144.13
153.46
157.17
162.34
110115120125130135140145f1 (ppm)
109.21
114.63
115.53
120.27
120.37
123.33
125.47
125.52
127.08
127.22
127.59
130.85
141.36
143.36
143.66
144.13
N
NS
NN
OH
O
O
OCH3
N
NS
NN
OH
O
O
OCH3
S24
1H and 13C NMR spectra of 6m
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
6.02
4.31
1.00
4.25
0.97
1.00
3.23
7.44
7.44
7.46
7.47
7.48
7.49
7.49
7.50
7.52
7.54
7.55
7.72
7.74
7.84
7.85
7.86
7.86
7.88
7.88
7.89
7.91
8.07
8.09
8.24
7.47.57.67.77.87.98.08.18.2f1 (ppm)
7.46
7.47
7.48
7.49
7.49
7.50
7.52
7.54
7.72
7.74
7.84
7.85
7.86
7.86
7.88
7.88
7.89
8.07
8.09
8.24
0102030405060708090100110120130140150160f1 (ppm)
28.16
77.19
115.13
124.87
125.22
125.54
126.84
127.94
128.32
128.52
129.53
132.60
133.32
145.81
152.98
162.15
123125127129131133f1 (ppm)
121.96
124.87
125.22
125.54
125.87
126.58
126.84
127.60
127.94
128.32
128.52
129.53
130.37
132.60
133.32
N
NS
N
NOH
O
O
N
NS
N
NOH
O
O
S25
1H and 13C NMR spectra of 6n
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.00
5.97
1.00
2.06
0.99
5.18
1.00
2.43
3.21
7.34
7.36
7.49
7.50
7.51
7.52
7.59
7.61
7.83
7.85
7.87
7.88
7.90
7.92
8.22
7.47.57.67.77.87.98.08.18.2f1 (ppm)
7.36
7.49
7.50
7.51
7.52
7.59
7.61
7.83
7.85
7.87
7.88
7.90
7.92
8.22
0102030405060708090100110120130140150160f1 (ppm)
21.36
28.06
76.27
114.97
124.80
124.98
125.69
126.95
127.97
128.42
128.51
129.53
132.68
133.26
145.32
153.12
162.28
122124126128130132134136138f1 (ppm)
120.85
122.46
124.80
124.98
125.69
126.74
126.95
127.97
128.42
128.51
128.67
129.53
131.20
132.68
133.26
136.02
138.91
N
NS
NN
OH
O
O
N
NS
NN
OH
O
O
S26
1H and 13C NMR spectra of 6o
0102030405060708090100110120130140150160f1 (ppm)
20.03
20.61
28.02
76.57
115.91
124.79
125.07
125.69
126.50
126.97
127.99
128.42
128.52
132.68
133.26
145.42
153.13
162.26
122124126128130132134136138f1 (ppm)
122.68
124.79
125.07
125.69
126.50
126.77
126.97
127.99
128.42
128.52
131.51
132.68
133.26
135.31
136.37
N
NS
NN
OH
O
O
N
NS
NN
OH
O
O
S27
1H and 13C NMR spectra of 6p
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
6.00
2.11
1.21
1.20
4.26
0.94
1.11
3.25
7.45
7.46
7.47
7.47
7.48
7.48
7.50
7.52
7.53
7.54
7.55
7.67
7.70
7.82
7.83
7.84
7.84
7.85
7.86
7.87
7.89
8.20
8.20
8.22
7.47.57.67.77.87.98.08.18.2f1 (ppm)
7.46
7.47
7.47
7.48
7.48
7.52
7.53
7.54
7.55
7.67
7.70
7.83
7.84
7.84
7.85
7.86
7.87
8.20
8.20
8.22
0102030405060708090100110120130140150160170f1 (ppm)
28.32
77.61
116.05
121.06
124.78
125.39
126.49
126.76
127.61
127.91
128.30
128.53
129.61
130.76
131.43
132.23
132.58
133.33
146.21
152.76
162.03
122124126128130132f1 (ppm)
121.06
124.78
125.39
126.49
126.76
127.61
127.91
128.30
128.53
129.61
130.76
131.43
132.23
132.58
133.33
N
NS
NN
OH
O
O
Cl
N
NS
NN
OH
O
O
Cl
S28
1H and 13C NMR spectra of 6q
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.28
6.44
2.36
1.01
3.11
0.99
3.16
1.04
1.00
1.34
1.35
1.37
3.18
4.04
4.06
4.08
4.10
7.01
7.01
7.03
7.04
7.43
7.45
7.58
7.59
7.80
7.82
8.26
7.07.27.47.67.88.08.2f1 (ppm)
7.01
7.03
7.04
7.42
7.43
7.45
7.47
7.58
7.59
7.78
7.80
7.82
7.83
7.95
7.96
7.98
8.26
0102030405060708090100110120130140150160f1 (ppm)
15.08
27.73
64.21
76.83
109.85
114.35
115.01
124.69
125.45
126.35
127.55
127.82
128.32
130.78
132.09
133.54
141.91
144.36
153.65
155.90
162.29
122124126128130132134136f1 (ppm)
123.50
124.69
125.45
125.66
126.35
127.55
127.82
127.99
128.32
130.78
132.09
133.46
133.54
N
NS
NN
OH
O
O
OEt
N
NS
NN
OH
O
O
OEt
S29
1H and 13C NMR spectra of 6r
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
6.00
1.95
5.39
2.01
0.86
3.27
7.47
7.47
7.48
7.48
7.48
7.49
7.50
7.86
7.89
8.28
8.29
8.31
8.31
9.08
9.09
7.57.67.77.87.98.08.18.28.3f1 (ppm)
7.47
7.48
7.48
7.48
7.49
7.83
7.86
7.87
7.87
7.89
7.90
7.90
7.92
7.92
8.28
8.29
8.31
8.31
0102030405060708090100110120130140150160f1 (ppm)
28.45
78.33
114.51
121.50
123.12
124.96
125.42
126.67
127.90
128.17
128.60
130.99
133.42
144.10
148.27
152.64
161.95
120122124126128130132f1 (ppm)
120.42
121.50
123.12
124.96
125.42
126.37
126.67
127.90
128.17
128.60
130.99
131.95
132.54
133.42
N
NS
NN
OH
O
O
NO2
N
NS
NN
OH
O
O
NO2
S30
1H and 13C NMR spectra of 6s
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
1.05
2.08
2.22
3.12
1.00
7.29
7.31
7.33
7.39
7.41
7.43
7.47
7.47
7.49
7.49
7.51
7.51
7.52
7.53
7.54
7.55
7.56
7.56
7.70
7.72
7.73
7.75
8.13
8.13
8.15
7.27.37.47.57.67.77.87.98.1f1 (ppm)
7.31
7.33
7.39
7.41
7.43
7.49
7.49
7.51
7.51
7.52
7.53
7.54
7.55
7.70
7.72
7.73
7.75
8.13
8.13
8.15
0102030405060708090100110120130140150160f1 (ppm)
28.18
76.84
115.29
125.36
126.25
126.84
127.85
128.30
129.06
129.54
133.18
139.37
145.75
152.86
162.05
126128130132134f1 (ppm)
125.36
126.25
126.84
127.85
128.30
129.06
129.54
131.77
133.18
N
NS
NN
OH
O
O
N
NS
NN
OH
O
O
S31
1H and 13C NMR spectra of 6t
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
3.01
3.02
6.03
2.07
1.05
3.08
1.00
2.29
2.43
3.19
7.18
7.20
7.35
7.37
7.57
7.59
7.61
7.93
7.17.27.37.47.57.67.77.87.98.0f1 (ppm)
7.18
7.20
7.35
7.37
7.57
7.59
7.61
7.93
0102030405060708090100110120130140150160170f1 (ppm)
21.27
21.40
27.94
75.86
115.10
125.05
126.76
128.84
129.49
129.62
131.11
136.20
137.84
144.70
153.18
162.23
N
NS
NN
OH
O
O
N
NS
NN
OH
O
O
S32
1H and 13C NMR spectra of 6u
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
6.00
3.21
1.07
2.11
1.13
1.04
1.99
3.19
3.82
7.09
7.09
7.11
7.12
7.42
7.44
7.69
7.71
7.72
7.73
7.17.27.37.47.57.67.7f1 (ppm)
7.09
7.09
7.11
7.12
7.42
7.44
7.55
7.57
7.69
7.71
7.72
7.73
0102030405060708090100110120130140150160f1 (ppm)
28.09
56.26
76.66
104.55
109.44
114.84
115.72
127.31
128.29
128.94
130.95
131.72
132.32
138.57
144.98
152.96
157.44
161.98
N
NS
NN
OH
O
O
H3CO
Cl
N
NS
NN
OH
O
O
H3CO
Cl
S33
1H and 13C NMR spectra of 6v
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.00
5.76
2.96
2.29
2.01
0.99
3.06
0.99
1.33
1.35
1.37
3.19
3.72
4.04
4.06
4.07
4.09
6.92
6.94
7.13
7.14
7.15
7.16
7.57
7.59
7.61
7.73
7.73
6.97.07.17.27.37.47.57.67.7f1 (ppm)
6.92
6.94
7.13
7.14
7.15
7.16
7.57
7.59
7.61
7.73
7.73
0102030405060708090100110120130140150160f1 (ppm)
15.00
27.84
55.56
64.35
75.43
109.95
114.45
115.54
115.99
121.91
127.18
128.20
130.83
143.70
153.33
156.86
159.39
162.34
N
NS
NN
OH
O
O
OEt
MeO
N
NS
NN
OH
O
O
OEt
MeO
S34
1H and 13C NMR spectra of 6w
N
NS
NN
OH
O
O
NO2
N
NS
NN
OH
O
O
NO2
S35
1H and 13C NMR spectra of 6x
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
3.00
5.83
2.01
0.99
0.99
0.98
2.01
1.96
1.33
1.35
1.37
3.23
4.05
4.07
4.08
4.10
7.02
7.02
7.04
7.05
7.50
7.64
7.65
7.95
7.97
8.17
8.20
7.07.27.47.67.88.08.2f1 (ppm)
7.02
7.02
7.04
7.05
7.50
7.53
7.64
7.65
7.95
7.97
8.17
8.20
0102030405060708090100110120130140150160170f1 (ppm)
15.03
28.32
64.28
77.95
110.01
114.82
115.49
122.66
124.22
126.77
127.19
131.10
139.79
141.13
145.87
146.39
152.70
156.51
161.71
N
NS
NN
OH
O
O
OEt
O2N
N
NS
NN
OH
O
O
OEt
O2N
S36
1H and 13C NMR spectra of 6y
N
NS
N
NOH
O
O OCH3H
H
N
NS
N
NOH
O
O OCH3H
H
S37
1H and 13C NMR spectra of 6z
N
NS
N
NOH
O
O OCH3H
H
N
NS
N
NOH
O
O OCH3H
H
S38
1H and 13C NMR spectra of 6a&4e (competition experiment)
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
6.00
1.91
3.06
1.02
0.30
1.66
2.11
3.21
1.93
0.29
0.23
3.20
3.24
3.82
7.15
7.16
7.17
7.18
7.23
7.25
7.27
7.31
7.33
7.35
7.36
7.38
7.40
7.42
7.44
7.63
7.65
7.67
7.69
7.76
7.78
7.78
7.80
7.82
8.27
8.28
8.29
8.30
9.09
9.09
102030405060708090100110120130140150160170f1 (ppm)
28.04
28.41
56.30
75.79
78.13
109.49
114.41
115.44
116.29
119.96
121.51
122.13
123.12
126.72
126.85
127.02
127.59
128.60
128.81
129.15
130.68
130.96
144.10
144.52
152.63
153.03
157.89
161.89
162.19
N
NS
N
NOH
O
O NO2
N
NS
N
NOH
O
O NO2
S39
1H and 13C NMR spectra of7a
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
5.99
6.27
2.00
1.23
2.23
2.51
2.55
3.04
3.42
7.35
7.36
7.38
7.41
7.43
7.45
7.69
7.71
0102030405060708090100110120130140150160170180190200f1 (ppm)
28.09
104.39
127.89
128.10
131.24
138.93
151.97
161.31
165.04
196.11
ON
N
NN
O
O
O
O
O
O
H
7a
ON
N
NN
O
O
O
O
O
O
H
7a
S40
Crystal structure description of 6o.
A specimen of C27H22N4O3S, approximate dimensions 0.300 mm x 0.300 mm x 0.300 mm,
was used for the X-ray crystallographic analysis. The X-ray intensity data were measured.The
integration of the data using a monoclinic unit cell yielded a total of 35307 reflections to a
maximum θ angle of 25.00° (0.84 Å resolution), of which 4189 were independent (average
redundancy 8.429, completeness = 99.9%, Rint = 7.66%, Rsig = 5.23%) and 2724 (65.03%)
were greater than 2σ(F2). The final cell constants
of a = 11.638(4) Å, b = 14.774(6) Å, c = 14.105(5) Å, β = 101.385(10)°, volume
= 2377.5(15) Å3, are based upon the refinement of the XYZ-centroids of reflections above 20
σ(I). The calculated minimum and maximum transmission coefficients (based on crystal size)
are 0.9500 and 0.9500.
The structure was solved and refined using the Bruker SHELXTL Software Package, using the
space group P 1 21/n 1, with Z = 4 for the formula unit, C27H22N4O3S. The final anisotropic
full-matrix least-squares refinement on F2 with 322 variables converged at R1 = 5.42%, for the
observed data and wR2 = 14.64% for all data. The goodness-of-fit was 1.053. The largest peak
in the final difference electron density synthesis was 0.470 e-/Å3 and the largest hole was -
0.386 e-/Å3 with an RMS deviation of 0.055 e-/Å3. On the basis of the final model, the
calculated density was 1.348 g/cm3 and F(000), 1008 e-.
Figure S1. ORTEP view of 6owith 50% ellipsoidal probability (CCDC 1895624).
S41
Table S1. Sample and crystal information for 6o.
Chemical formula C27H22N4O3SFormula weight 482.54 g/molTemperature 298(2) KWavelength 0.71073 ÅCrystal size 0.300 x 0.300 x 0.300 mmCrystal system monoclinicSpace group P 1 21/n 1Unit cell dimensions a = 11.638(4) Å α = 90°
b = 14.774(6) Å β = 101.385(10)°c = 14.105(5) Å γ = 90°
Volume 2377.5(15) Å3
Z 4Density (calculated) 1.348 g/cm3
Absorption coefficient 0.174 mm-1
F(000) 1008
Table S2. Data collection and structure refinement for 6o.Theta range for data collection 2.53 to 25.00°Index ranges -13<=h<=13, -17<=k<=17, -16<=l<=16Reflections collected 35307Independent reflections 4189 [R(int) = 0.0766]Max. and min. transmission 0.9500 and 0.9500Structure solution technique direct methodsStructure solution program SHELXS-97 (Sheldrick 2008)Refinement method Full-matrix least-squares on F2
Refinement program SHELXL-2014 (Sheldrick 2014)Function minimized Σ w(Fo
2 - Fc2)2
Data / restraints / parameters 4189 / 0 / 322Goodness-of-fit on F2 1.053Δ/σmax 0.010Final R indices 2724 data; I>2σ(I) R1 = 0.0542, wR2 = 0.1230
all data R1 = 0.0998, wR2 = 0.1464
Weighting scheme w=1/[σ2(Fo2)+(0.0613P)2+1.6611P]
where P=(Fo2+2Fc
2)/3Extinction coefficient 0.0024(6)Largest diff. peak and hole 0.470 and -0.386 eÅ-3
R.M.S. deviation from mean 0.055 eÅ-3
S42
Table S3. Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for 6o.U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
x/a y/b z/c U(eq)S1 0.79191(6) 0.58897(6) 0.67106(6) 0.0393(3)O3 0.29216(18) 0.45779(15) 0.60164(17) 0.0450(6)O2 0.04719(18) 0.59847(16) 0.76763(18) 0.0566(7)N2 0.57178(19) 0.60111(16) 0.68066(17) 0.0304(6)O1 0.38399(19) 0.74586(16) 0.74446(18) 0.0558(7)N1 0.58721(19) 0.60245(16) 0.52741(18) 0.0319(6)N4 0.1706(2) 0.52982(17) 0.68330(19) 0.0369(7)N3 0.2174(2) 0.67091(18) 0.75892(19) 0.0406(7)C21 0.4559(2) 0.60759(19) 0.6264(2) 0.0291(7)C11 0.4671(2) 0.61115(19) 0.5315(2) 0.0302(7)C10 0.3813(2) 0.62733(19) 0.4421(2) 0.0311(7)C27 0.2762(2) 0.5276(2) 0.6489(2) 0.0312(7)C20 0.6295(2) 0.5977(2) 0.7785(2) 0.0322(7)C2 0.3327(2) 0.6388(2) 0.2659(2) 0.0340(7)C12 0.6465(2) 0.5972(2) 0.6187(2) 0.0306(7)C7 0.2157(2) 0.6631(2) 0.2700(2) 0.0336(7)C22 0.3509(2) 0.6027(2) 0.6698(2) 0.0309(7)C1 0.4128(2) 0.6215(2) 0.3529(2) 0.0351(8)C13 0.7511(2) 0.5902(2) 0.7848(2) 0.0343(8)C23 0.3230(3) 0.6774(2) 0.7244(2) 0.0380(8)C9 0.2640(2) 0.6536(2) 0.4449(2) 0.0382(8)C19 0.5823(3) 0.6014(2) 0.8611(2) 0.0393(8)C8 0.1858(3) 0.6707(2) 0.3616(2) 0.0401(8)C14 0.8243(3) 0.5847(2) 0.8744(2) 0.0429(8)C6 0.1361(3) 0.6787(2) 0.1827(2) 0.0441(9)C17 0.6561(3) 0.5965(2) 0.9505(2) 0.0451(9)C15 0.7783(3) 0.5870(2) 0.9579(2) 0.0457(9)C3 0.3655(3) 0.6328(2) 0.1744(2) 0.0484(9)C5 0.1694(3) 0.6715(2) 0.0955(3) 0.0529(10)C26 0.0866(3) 0.4549(2) 0.6580(3) 0.0548(10)C4 0.2860(3) 0.6483(3) 0.0915(3) 0.0552(10)C24 0.1844(3) 0.7471(3) 0.8152(3) 0.0616(11)C16 0.8590(3) 0.5787(3) 0.0551(3) 0.0754(13)C18 0.6052(3) 0.6033(3) 0.0407(3) 0.0778(14)C25 0.1392(2) 0.5998(2) 0.7382(2) 0.0389(8)
Table S4. Bond lengths (Å) for 6o.S1-C12 1.712(3) S1-C13 1.760(3)O3-C27 1.262(3) O3-H22 0.82O2-C25 1.223(3) N2-C12 1.350(3)
S43
N2-C20 1.412(4) N2-C21 1.416(3)O1-C23 1.237(4) N1-C12 1.338(4)N1-C11 1.417(3) N4-C25 1.384(4)N4-C27 1.407(3) N4-C26 1.473(4)N3-C25 1.382(4) N3-C23 1.412(4)N3-C24 1.471(4) C21-C11 1.371(4)C21-C22 1.473(4) C11-C10 1.466(4)C10-C1 1.380(4) C10-C9 1.427(4)C27-C22 1.405(4) C20-C19 1.384(4)C20-C13 1.405(4) C2-C1 1.411(4)C2-C3 1.418(4) C2-C7 1.421(4)C7-C6 1.406(4) C7-C8 1.407(4)C22-C23 1.418(4) C1-H1 0.93C13-C14 1.380(4) C9-C8 1.360(4)C9-H7 0.93 C19-C17 1.380(4)C19-H15 0.93 C8-H6 0.93C14-C15 1.387(4) C14-H8 0.93C6-C5 1.365(5) C6-H5 0.93C17-C15 1.413(4) C17-C18 1.509(5)C15-C16 1.507(5) C3-C4 1.360(5)C3-H2 0.93 C5-C4 1.410(5)C5-H4 0.93 C26-H20 0.96C26-H21 0.96 C26-H19 0.96C4-H3 0.93 C24-H18 0.96C24-H17 0.96 C24-H16 0.96C16-H9 0.96 C16-H11 0.96C16-H10 0.96 C18-H14 0.96C18-H13 0.96 C18-H12 0.96
Table S5. Bond angles (°) for 6o.C12-S1-C13 88.32(14) C27-O3-H22 109.5C12-N2-C20 112.9(2) C12-N2-C21 108.6(2)C20-N2-C21 138.6(2) C12-N1-C11 106.9(2)C25-N4-C27 123.7(3) C25-N4-C26 117.5(2)C27-N4-C26 118.8(3) C25-N3-C23 124.0(3)C25-N3-C24 117.7(2) C23-N3-C24 118.2(3)C11-C21-N2 105.5(2) C11-C21-C22 130.9(3)N2-C21-C22 123.5(3) C21-C11-N1 108.7(2)C21-C11-C10 131.8(2) N1-C11-C10 119.3(2)C1-C10-C9 118.1(3) C1-C10-C11 121.0(3)C9-C10-C11 120.9(3) O3-C27-C22 127.3(3)
S44
O3-C27-N4 115.5(3) C22-C27-N4 117.2(3)C19-C20-C13 120.9(3) C19-C20-N2 129.1(3)C13-C20-N2 110.1(2) C1-C2-C3 122.0(3)C1-C2-C7 118.9(3) C3-C2-C7 119.1(3)N1-C12-N2 110.2(2) N1-C12-S1 134.2(2)N2-C12-S1 115.6(2) C6-C7-C8 123.5(3)C6-C7-C2 118.4(3) C8-C7-C2 118.1(3)C27-C22-C23 121.9(3) C27-C22-C21 118.8(3)C23-C22-C21 119.0(3) C10-C1-C2 122.2(3)C10-C1-H1 118.9 C2-C1-H1 118.9C14-C13-C20 119.6(3) C14-C13-S1 127.2(2)C20-C13-S1 113.2(2) O1-C23-N3 118.4(3)O1-C23-C22 125.3(3) N3-C23-C22 116.3(3)C8-C9-C10 120.5(3) C8-C9-H7 119.8C10-C9-H7 119.8 C17-C19-C20 119.2(3)C17-C19-H15 120.4 C20-C19-H15 120.4C9-C8-C7 122.2(3) C9-C8-H6 118.9C7-C8-H6 118.9 C13-C14-C15 120.3(3)C13-C14-H8 119.8 C15-C14-H8 119.8C5-C6-C7 121.5(3) C5-C6-H5 119.3C7-C6-H5 119.3 C19-C17-C15 120.5(3)C19-C17-C18 119.3(3) C15-C17-C18 120.2(3)C14-C15-C17 119.5(3) C14-C15-C16 119.7(3)C17-C15-C16 120.8(3) C4-C3-C2 120.7(3)C4-C3-H2 119.6 C2-C3-H2 119.6C6-C5-C4 120.1(3) C6-C5-H4 120.0C4-C5-H4 120.0 N4-C26-H20 109.5N4-C26-H21 109.5 H20-C26-H21 109.5N4-C26-H19 109.5 H20-C26-H19 109.5H21-C26-H19 109.5 C3-C4-C5 120.2(3)C3-C4-H3 119.9 C5-C4-H3 119.9N3-C24-H18 109.5 N3-C24-H17 109.5H18-C24-H17 109.5 N3-C24-H16 109.5H18-C24-H16 109.5 H17-C24-H16 109.5C15-C16-H9 109.5 C15-C16-H11 109.5H9-C16-H11 109.5 C15-C16-H10 109.5H9-C16-H10 109.5 H11-C16-H10 109.5C17-C18-H14 109.5 C17-C18-H13 109.5H14-C18-H13 109.5 C17-C18-H12 109.5H14-C18-H12 109.5 H13-C18-H12 109.5O2-C25-N3 121.7(3) O2-C25-N4 121.5(3)N3-C25-N4 116.8(2)
Table S6. Torsion angles (°) for 6o.
S45
C12-N2-C21-C11 -2.5(3) C20-N2-C21-C11 177.5(3)C12-N2-C21-C22 172.8(3) C20-N2-C21-C22 -7.2(5)N2-C21-C11-N1 2.8(3) C22-C21-C11-N1 -172.0(3)N2-C21-C11-C10 -172.8(3) C22-C21-C11-C10 12.4(6)C12-N1-C11-C21 -2.2(3) C12-N1-C11-C10 174.1(3)C21-C11-C10-C1 -175.5(3) N1-C11-C10-C1 9.3(4)C21-C11-C10-C9 7.4(5) N1-C11-C10-C9 -167.9(3)C25-N4-C27-O3 178.5(3) C26-N4-C27-O3 -3.0(4)C25-N4-C27-C22 -2.0(4) C26-N4-C27-C22 176.4(3)C12-N2-C20-C19 178.9(3) C21-N2-C20-C19 -1.1(6)C12-N2-C20-C13 -0.5(4) C21-N2-C20-C13 179.5(3)C11-N1-C12-N2 0.6(3) C11-N1-C12-S1 -178.0(3)C20-N2-C12-N1 -178.8(2) C21-N2-C12-N1 1.2(3)C20-N2-C12-S1 0.1(3) C21-N2-C12-S1 -179.9(2)C13-S1-C12-N1 178.8(3) C13-S1-C12-N2 0.3(2)C1-C2-C7-C6 -178.9(3) C3-C2-C7-C6 1.1(4)C1-C2-C7-C8 1.3(4) C3-C2-C7-C8 -178.6(3)O3-C27-C22-C23 -179.8(3) N4-C27-C22-C23 0.9(4)O3-C27-C22-C21 5.9(5) N4-C27-C22-C21 -173.5(3)C11-C21-C22-C27 61.6(4) N2-C21-C22-C27 -112.4(3)C11-C21-C22-C23 -113.0(4) N2-C21-C22-C23 73.1(4)C9-C10-C1-C2 -1.2(4) C11-C10-C1-C2 -178.4(3)C3-C2-C1-C10 179.9(3) C7-C2-C1-C10 0.0(5)C19-C20-C13-C14 1.3(5) N2-C20-C13-C14 -179.2(3)C19-C20-C13-S1 -178.7(2) N2-C20-C13-S1 0.8(3)C12-S1-C13-C14 179.3(3) C12-S1-C13-C20 -0.6(2)C25-N3-C23-O1 177.2(3) C24-N3-C23-O1 1.4(5)C25-N3-C23-C22 -3.7(4) C24-N3-C23-C22 -179.5(3)C27-C22-C23-O1 -179.2(3) C21-C22-C23-O1 -4.8(5)C27-C22-C23-N3 1.8(4) C21-C22-C23-N3 176.1(3)C1-C10-C9-C8 1.2(4) C11-C10-C9-C8 178.4(3)C13-C20-C19-C17 -0.9(5) N2-C20-C19-C17 179.8(3)C10-C9-C8-C7 0.2(5) C6-C7-C8-C9 178.8(3)C2-C7-C8-C9 -1.4(5) C20-C13-C14-C15 -0.3(5)S1-C13-C14-C15 179.7(3) C8-C7-C6-C5 179.3(3)C2-C7-C6-C5 -0.4(5) C20-C19-C17-C15 -0.5(5)C20-C19-C17-C18 178.2(3) C13-C14-C15-C17 -1.0(5)C13-C14-C15-C16 178.6(3) C19-C17-C15-C14 1.5(5)C18-C17-C15-C14 -177.3(3) C19-C17-C15-C16 -178.1(3)C18-C17-C15-C16 3.1(6) C1-C2-C3-C4 178.8(3)C7-C2-C3-C4 -1.2(5) C7-C6-C5-C4 -0.3(5)C2-C3-C4-C5 0.5(6) C6-C5-C4-C3 0.2(6)C23-N3-C25-O2 -177.9(3) C24-N3-C25-O2 -2.0(5)C23-N3-C25-N4 2.7(4) C24-N3-C25-N4 178.5(3)C27-N4-C25-O2 -179.1(3) C26-N4-C25-O2 2.4(5)
S46
C27-N4-C25-N3 0.4(4) C26-N4-C25-N3 -178.1(3)
Table S7. Anisotropic atomic displacement parameters (Å2) for 6o.
The anisotropic atomic displacement factor exponent takes the form: -2π2[ h2 a*2 U11 + ... + 2 h k a* b* U12 ]
U11 U22 U33 U23 U13 U12
S1 0.0221(4) 0.0568(6) 0.0418(5) -0.0005(4) 0.0130(3) 0.0020(4)O3 0.0342(13) 0.0469(14) 0.0619(16) -0.0080(12) 0.0290(12) -0.0039(11)O2 0.0341(13) 0.0697(17) 0.0757(18) -0.0060(14) 0.0343(13) 0.0010(12)N2 0.0224(12) 0.0376(15) 0.0339(15) -0.0015(12) 0.0119(11) 0.0003(11)O1 0.0456(14) 0.0513(15) 0.0784(18) -0.0237(13) 0.0311(13) -0.0135(12)N1 0.0212(12) 0.0394(15) 0.0370(16) -0.0012(12) 0.0103(11) -0.0013(11)N4 0.0249(13) 0.0416(16) 0.0488(17) -0.0017(13) 0.0183(12) -0.0020(12)N3 0.0318(14) 0.0461(17) 0.0499(17) -0.0103(14) 0.0226(13) 0.0019(13)C21 0.0213(14) 0.0330(18) 0.0348(18) -0.0041(13) 0.0099(13) -0.0013(12)C11 0.0214(14) 0.0335(19) 0.0388(19) -0.0039(14) 0.0134(13) -0.0026(12)C10 0.0260(15) 0.0305(17) 0.0390(19) -0.0025(14) 0.0116(14) -0.0014(13)C27 0.0246(15) 0.0386(19) 0.0343(18) 0.0015(15) 0.0150(13) 0.0035(14)C20 0.0279(15) 0.0365(18) 0.0343(18) -0.0049(14) 0.0114(14) -0.0015(14)C2 0.0305(16) 0.0356(18) 0.0373(19) 0.0002(15) 0.0102(15) 0.0004(14)C12 0.0224(15) 0.0355(18) 0.0374(19) -0.0035(14) 0.0142(14) 0.0010(13)C7 0.0303(16) 0.0305(18) 0.0407(19) 0.0015(15) 0.0085(15) -0.0015(13)C22 0.0218(15) 0.0379(19) 0.0359(18) -0.0032(14) 0.0129(13) -0.0009(13)C1 0.0260(16) 0.0391(19) 0.043(2) 0.0009(15) 0.0133(15) 0.0014(14)C13 0.0243(15) 0.0405(19) 0.041(2) -0.0008(15) 0.0122(14) 0.0010(14)C23 0.0283(16) 0.046(2) 0.043(2) -0.0010(16) 0.0144(15) -0.0009(15)C9 0.0312(17) 0.046(2) 0.040(2) -0.0040(16) 0.0150(15) 0.0027(15)C19 0.0274(16) 0.053(2) 0.041(2) -0.0033(16) 0.0143(15) -0.0007(15)C8 0.0249(16) 0.045(2) 0.053(2) -0.0008(17) 0.0126(16) 0.0045(14)C14 0.0267(16) 0.056(2) 0.047(2) -0.0012(17) 0.0080(16) 0.0006(15)C6 0.0331(18) 0.046(2) 0.052(2) 0.0023(17) 0.0056(17) 0.0017(15)C17 0.0381(18) 0.064(2) 0.036(2) -0.0040(17) 0.0136(16) -0.0034(17)C15 0.0397(19) 0.061(2) 0.036(2) -0.0037(17) 0.0075(16) -0.0027(17)C3 0.0388(19) 0.063(2) 0.046(2) 0.0011(18) 0.0147(18) 0.0065(17)C5 0.048(2) 0.061(2) 0.046(2) 0.0046(19) -0.0010(18) 0.0004(18)C26 0.0359(19) 0.051(2) 0.083(3) -0.004(2) 0.0257(19) -0.0113(17)C4 0.051(2) 0.076(3) 0.040(2) 0.0017(19) 0.0124(18) 0.009(2)C24 0.059(2) 0.058(2) 0.079(3) -0.022(2) 0.040(2) 0.003(2)C16 0.049(2) 0.128(4) 0.045(2) -0.006(2) -0.0012(19) 0.000(2)C18 0.055(2) 0.139(4) 0.045(2) -0.007(3) 0.023(2) -0.002(3)C25 0.0234(16) 0.052(2) 0.044(2) 0.0033(17) 0.0154(15) 0.0054(15)
Table S8. Hydrogen atomic coordinates and isotropic atomic displacement
S47
parameters (Å2) for 6o.x/a y/b z/c U(eq)
H22 0.3548 0.4620 0.5837 0.067H1 0.4894 0.6055 0.3502 0.042H7 0.2410 0.6592 0.5041 0.046H15 0.5018 0.6072 0.8565 0.047H6 0.1099 0.6879 0.3653 0.048H8 0.9048 0.5794 0.8788 0.051H5 0.0592 0.6943 0.1844 0.053H2 0.4423 0.6180 0.1711 0.058H4 0.1152 0.6819 0.0386 0.063H20 0.1157 0.4021 0.6948 0.082H21 0.0770 0.4418 0.5903 0.082H19 0.0124 0.4719 0.6726 0.082H3 0.3085 0.6437 0.0320 0.066H18 0.1106 0.7344 0.8330 0.092H17 0.1778 0.8012 0.7768 0.092H16 0.2434 0.7554 0.8726 0.092H9 0.9377 0.5688 1.0463 0.113H11 0.8347 0.5286 1.0898 0.113H10 0.8560 0.6334 1.0912 0.113H14 0.5217 0.6102 1.0230 0.117H13 0.6382 0.6548 1.0780 0.117H12 0.6233 0.5493 1.0785 0.117