Post on 21-Apr-2020
transcript
1
Supporting Information
Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative
dimerization of 2-aryl indoles and cross-addition of indoles
AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band Indresh
Kumar*a
aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
bDepartment of Chemistry, BITS Pilani, Hyderabad Campus, Secunderabad, India
§authors have contributed equally
Corresponding Email: indresh.kumar@pilani.bits-pilani.ac.in, indresh.chemistry@gmail.com
Table of Contents
1H,13C-NMRand HRMS data for the newly synthesized compounds…………….……...…......S2
Single Crystal X-ray and data for 2g…………………………………………………………...S40
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019
2
Figure S1: HRMS confirmation of in situ generated 2-phenyl indole-3-one
N
O
Calcd m/z = 208.0762Found m/z = 208.0757
3
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Oct02-2017.3.fidINDO1
1.01
1.03
1.02
1.05
1.04
8.21
1.46
1.04
1.02
1.07
2.02
0.97
6.70
6.72
6.78
6.80
6.81
6.91
6.91
6.92
6.93
6.93
6.94
6.95
6.99
7.01
7.13
7.14
7.15
7.16
7.17
7.18
7.19
7.23
7.24
7.24
7.25
7.27
7.27
7.31
7.33
7.39
7.41
7.42
7.44
7.44
7.44
7.46
7.46
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct02-2017.4.fidINDO1
72.0
9
110.
7211
2.08
112.
2711
9.19
120.
0012
0.44
121.
5812
2.36
125.
4012
7.25
127.
3912
7.55
127.
6912
8.26
129.
7413
3.26
135.
5513
7.09
137.
1414
0.38
159.
44
200.
34
NH
O
NH2a
NH
O
NH2a
4
NH
O
NH2a
5
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Jun28-2017.2.fidIND-03
0.98
7.62
2.07
1.10
2.14
3.09
0.98
5.20
6.78
6.78
6.80
6.81
6.82
6.83
6.84
6.84
6.86
6.86
6.87
6.88
6.88
6.90
6.90
6.91
6.92
6.92
6.94
6.94
7.03
7.05
7.06
7.07
7.14
7.15
7.16
7.16
7.17
7.18
7.18
7.31
7.33
7.34
7.36
7.36
8.16
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct02-2017.8.fidINDO3
71.3
9
110.
8811
2.49
112.
6511
4.52
114.
7311
4.95
115.
1611
9.63
120.
2112
0.46
121.
0712
2.61
125.
4112
7.13
128.
9012
8.98
131.
5713
1.66
135.
4813
5.85
135.
8713
6.01
137.
4515
9.26
161.
2016
1.40
163.
6516
3.87
200.
19
NH
O
NH
2bF
F
NH
O
NH
2bF
F
6
NH
O
NH
2bF
F
7
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Nov18-2017.1.fidInd09
0.87
2.05
1.97
5.38
2.08
1.15
1.32
1.03
2.19
1.01
5.21
6.86
6.87
6.88
6.89
6.90
6.94
6.95
7.02
7.03
7.05
7.07
7.10
7.10
7.10
7.12
7.12
7.12
7.15
7.16
7.17
7.19
7.19
7.20
7.21
7.21
7.21
7.32
7.34
7.36
7.37
7.37
7.38
7.39
7.39
7.45
7.46
7.50
7.51
7.52
7.53
7.54
7.54
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov18-2017.2.fidInd09
71.3
7
111.
0211
2.37
112.
6812
0.08
120.
4212
0.43
120.
9612
2.88
125.
4812
5.80
126.
9812
7.14
127.
7412
7.80
128.
4412
8.89
129.
4612
9.96
133.
6413
4.07
134.
5013
5.57
135.
9313
7.73
141.
9315
9.33
199.
90
NH
O
NH2c
Cl
Cl
NH
O
NH2c
Cl
Cl
8
NH
O
NH2c
Cl
Cl
9
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Nov22-2017/1Ind06
1.00
1.87
2.00
1.91
1.86
2.92
2.13
1.94
1.23
1.00
5.20
6.85
6.86
6.87
6.87
6.89
6.91
6.93
6.95
6.97
6.99
7.03
7.05
7.12
7.14
7.17
7.19
7.20
7.22
7.35
7.37
7.39
7.41
7.46
7.49
7.52
7.53
7.54
7.54
8.14
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov22-2017/3Ind06
71.4
0
110.
9211
2.52
119.
7812
0.35
120.
4912
1.07
122.
7812
5.46
127.
1112
7.84
128.
3912
8.65
131.
0613
1.22
132.
0213
3.68
134.
5913
5.55
135.
8113
7.54
138.
6815
9.25
199.
76
NH
O
NH
2dCl
Cl
NH
O
NH
2dCl
Cl
10
NH
O
NH
2dCl
Cl
11
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Oct02-2017.5.fidINDO2
1.00
2.10
2.01
2.22
1.10
2.07
1.40
2.26
1.07
1.06
1.10
1.00
1.01
5.25
6.90
6.91
6.92
6.93
6.96
6.97
7.00
7.02
7.04
7.06
7.10
7.12
7.17
7.19
7.20
7.21
7.26
7.27
7.27
7.33
7.35
7.35
7.36
7.38
7.43
7.45
7.47
7.49
7.53
7.53
7.55
7.56
7.57
7.70
7.71
7.71
8.27
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct02-2017.6.fidINDO2
71.3
1
111.
0411
2.35
112.
7112
0.13
120.
3812
0.43
120.
9312
1.82
122.
3412
2.87
125.
5012
6.29
126.
9312
8.18
129.
0912
9.73
129.
9813
0.72
131.
3113
2.79
134.
7513
5.57
135.
9213
7.76
142.
1115
9.34
199.
95
NH
O
NH2e
Br
Br
NH
O
NH2e
Br
Br
12
NH
O
NH2e
Br
Br
13
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec23-2017/1IND-15
0.98
0.98
0.99
2.03
6.86
1.25
1.98
2.12
0.98
5.13
6.57
6.59
7.04
7.04
7.12
7.13
7.15
7.18
7.20
7.21
7.22
7.23
7.23
7.23
7.24
7.25
7.29
7.29
7.30
7.31
7.33
7.33
7.33
7.41
7.42
7.43
7.43
7.48
7.50
7.51
8.15
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec23-2017/2IND-15
72.5
5
111.
2311
1.45
112.
1711
3.34
113.
7312
1.74
124.
0712
5.43
127.
0612
7.73
127.
9012
8.10
128.
5912
8.77
128.
9412
9.65
132.
6513
4.10
138.
1513
9.51
139.
7215
7.52
198.
61
NH
O
NH
Br
Br
2f
NH
O
NH
Br
Br
2f
14
NH
O
NH
Br
Br
2f
15
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
Nov15-2017.1.fidINDO8
3.20
3.11
1.00
0.97
1.04
8.05
1.06
1.02
2.95
1.02
0.96
2.27
2.33
5.17
6.67
6.69
6.76
6.78
6.80
6.91
6.92
6.95
6.99
7.01
7.02
7.04
7.11
7.13
7.15
7.27
7.29
7.35
7.37
7.39
7.41
7.41
7.43
7.45
7.45
8.10
6.66.76.86.97.07.17.27.37.47.5f1 (ppm)
0.97
1.04
8.05
1.06
1.02
2.95
1.02
6.67
6.69
6.76
6.78
6.80
6.91
6.92
6.95
6.99
7.01
7.02
7.04
7.11
7.13
7.15
7.27
7.29
7.35
7.37
7.39
7.41
7.41
7.43
7.45
7.45
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov15-2017.2.fidINDO8
21.0
221
.23
71.9
3
110.
6211
1.82
112.
1111
8.88
119.
7712
0.39
121.
6112
2.10
125.
3312
7.10
127.
4812
8.32
128.
9312
9.52
130.
3113
5.45
136.
9313
7.00
137.
1313
7.46
137.
9915
9.14
200.
49
NH
O
NH
H3C
CH3
2g
NH
O
NH
H3C
CH3
2g
16
NH
O
NH
H3C
CH3
2g
17
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
Nov24-2017/2IND-10
2.99
3.02
0.99
0.97
2.00
2.95
1.08
6.39
1.16
2.10
0.99
3.56
3.67
5.20
6.64
6.64
6.64
6.69
6.70
6.71
6.71
6.74
6.78
6.79
6.80
6.81
6.82
6.83
6.92
6.94
6.95
7.05
7.07
7.08
7.09
7.10
7.11
7.13
7.15
7.17
7.31
7.33
7.42
7.42
7.44
7.45
7.47
7.47
8.101
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov25-2017/1ind-10
54.9
455
.17
71.9
8
110.
6711
1.70
112.
2111
2.88
113.
1911
4.71
114.
7711
9.21
119.
7412
0.05
120.
4212
1.50
121.
7512
2.38
125.
3812
7.35
128.
8312
9.19
134.
5713
5.41
136.
9913
7.12
141.
9015
8.68
159.
2115
9.38
200.
10
NH
O
NH
OCH3
H3CO
2h
NH
O
NH
OCH3
H3CO
2h
18
NH
O
NH
OCH3
H3CO
2h
19
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Jan15-2018/1IND17
3.03
3.07
1.02
2.10
3.07
1.17
1.17
1.14
2.06
1.10
1.07
4.22
1.00
3.73
3.77
5.18
6.64
6.66
6.71
6.71
6.72
6.73
6.73
6.74
6.76
6.78
6.80
6.90
6.90
6.92
6.92
6.94
6.94
6.97
6.99
7.01
7.03
7.11
7.11
7.13
7.13
7.13
7.15
7.15
7.29
7.31
7.38
7.39
7.41
7.43
7.43
7.44
7.45
7.45
8.07
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Jan15-2018/2IND17
55.2
455
.31
71.6
5
110.
6311
2.19
112.
2411
3.13
113.
6711
9.03
119.
8912
0.53
121.
5012
2.15
125.
4212
5.50
127.
5112
8.44
130.
9713
2.47
135.
4313
6.84
137.
03
159.
0815
9.17
159.
50
200.
67
NH
O
NH
2iH3CO
OCH3
NH
O
NH
2iH3CO
OCH3
20
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec16-2017/2IND13
3.09
3.17
2.96
3.23
1.12
1.91
1.98
1.00
1.00
2.05
1.98
1.99
1.11
2.16
2.16
2.21
2.30
2.31
4.94
6.65
6.68
6.93
6.95
7.11
7.16
7.24
7.25
7.28
7.35
7.37
7.85
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec27-2017/2IND 13
19.2
520
.35
21.3
1
71.7
5
111.
1711
2.12
113.
4011
8.86
121.
0012
1.56
122.
4412
5.02
125.
4912
6.31
128.
9312
9.01
130.
6013
1.11
131.
3213
1.99
132.
0313
4.57
134.
9113
9.78
148.
21
158.
56
199.
34
NH
O
NH
H3C
H3CCH3
CH3
Br
Br 2j
NH
O
NH
H3C
H3CCH3
CH3
Br
Br 2j
21
NH
O
NH
H3C
H3CCH3
CH3
Br
Br 2j
22
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Jul17-2019/1MEINDOLE
2.92
2.77
0.98
2.08
1.03
0.99
1.04
1.06
1.05
1.05
1.00
1.95
2.45
5.05
6.89
6.89
6.91
6.91
6.91
6.92
6.93
6.96
6.96
6.98
6.98
6.98
7.00
7.00
7.07
7.08
7.09
7.09
7.10
7.11
7.11
7.25
7.25
7.25
7.27
7.27
7.27
7.41
7.41
7.43
7.43
7.52
7.52
7.53
7.54
7.54
7.55
7.56
7.72
7.72
7.74
7.74
7.90
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Jul19-2019/2INDME
14.5
9
25.0
9
67.1
4
109.
5111
0.43
111.
4911
2.45
119.
0811
9.50
119.
7612
1.27
125.
3212
7.45
132.
5913
4.90
137.
47
159.
55
204.
31
NH
OCH3
NH2k H3C
NH
OCH3
NH2k H3C
23
NH
OCH3
NH2k H3C
24
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec12-2017/2INDOLE 4F
0.92
5.10
3.21
1.08
2.96
1.00
0.95
5.36
6.91
6.93
6.94
6.95
6.96
6.98
7.00
7.02
7.03
7.05
7.05
7.15
7.17
7.18
7.19
7.20
7.20
7.22
7.23
7.24
7.40
7.42
7.51
7.52
7.54
7.54
7.56
7.56
7.58
7.71
7.73
8.20
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec12-2017/4INDOLE 4F
70.7
4
111.
7111
3.09
115.
1411
5.35
115.
5311
9.58
119.
9212
0.20
122.
7112
3.60
125.
4612
5.66
128.
5612
8.65
135.
3113
6.96
137.
65
160.
51
200.
35
NH
O
NH
F
4ab
NH
O
NH
F
4ab
25
NH
O
NH
F
4ab
26
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Dec16-2017/1INDOLE4CL
0.98
2.02
1.04
2.01
1.06
2.33
1.00
2.99
1.00
0.97
5.35
6.89
6.91
6.93
6.98
6.98
7.00
7.02
7.02
7.12
7.12
7.13
7.13
7.17
7.17
7.19
7.21
7.21
7.24
7.25
7.26
7.26
7.36
7.38
7.49
7.51
7.53
7.53
7.68
7.70
8.26
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec16-2017/3INDOLE4CL
70.7
8
111.
7411
3.11
115.
1511
9.45
119.
4611
9.95
120.
1712
2.68
123.
6512
5.34
125.
6012
8.29
128.
5213
3.66
136.
9013
7.70
138.
13
160.
54
200.
16
NH
O
NH
Cl
4ad
NH
O
NH
Cl
4ad
27
NH
O
NH
Cl
4ad
28
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Oct16-2017/1INDOLE3 Br
0.99
2.06
1.06
4.01
2.08
1.00
1.01
1.00
0.94
0.96
5.38
6.92
6.92
6.94
6.94
6.95
6.96
6.97
7.01
7.01
7.03
7.03
7.03
7.05
7.05
7.15
7.16
7.17
7.19
7.21
7.21
7.23
7.23
7.39
7.41
7.41
7.41
7.42
7.43
7.43
7.43
7.44
7.49
7.49
7.49
7.51
7.51
7.51
7.52
7.52
7.54
7.54
7.54
7.56
7.56
7.71
7.73
7.81
7.81
7.82
8.30
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct16-2017/2INDOLE3 Br
70.7
6
111.
8011
3.25
115.
0811
9.41
119.
4812
0.07
120.
2612
2.59
122.
7412
3.79
125.
3512
5.66
126.
0612
9.45
130.
0513
0.87
136.
9513
7.80
142.
01
160.
56
199.
92
NH
O
NH4ae
Br
NH
O
NH4ae
Br
29
NH
O
NH4ae
Br
30
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec07-2017/1INDOLE4CH3
3.05
0.94
2.15
1.09
3.11
2.21
1.13
2.07
1.08
1.02
0.98
2.31
5.39
6.86
6.86
6.88
6.89
6.91
6.96
6.96
6.98
7.00
7.00
7.09
7.10
7.11
7.11
7.14
7.14
7.16
7.16
7.17
7.18
7.18
7.19
7.33
7.35
7.42
7.44
7.47
7.47
7.49
7.49
7.49
7.51
7.51
7.68
7.69
8.29
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec08-2017/1INDOLE4CH3
31.6
3
71.2
4
111.
7011
2.87
115.
5011
9.54
119.
5911
9.82
119.
9712
2.45
123.
8312
5.62
125.
6812
6.72
129.
2213
6.52
136.
9813
7.46
137.
54
160.
58
200.
96
CH3
NH
O
NH4ag
CH3
NH
O
NH4ag
31
CH3
NH
O
NH4ag
32
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
Oct14-2017/1INDOLE2OH
1.29
0.96
6.47
1.11
1.18
2.43
1.06
1.02
1.01
0.98
2.08
5.42
6.90
6.91
6.93
6.94
6.95
6.96
6.96
6.98
6.98
6.99
7.01
7.08
7.10
7.12
7.13
7.14
7.16
7.16
7.24
7.25
7.26
7.26
7.27
7.29
7.56
7.56
7.58
7.58
7.59
7.60
7.60
7.70
7.70
7.72
7.72
7.75
7.77
8.39.
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct14-2017/2INDOLE2OH
71.6
2
111.
8711
3.44
113.
7811
8.81
119.
0812
0.15
120.
2512
0.70
122.
5812
4.06
124.
5712
4.96
125.
6912
8.18
129.
9613
6.89
138.
71
156.
08
160.
12
171.
36
204.
04
NH
O
NH
HO
4ak
NH
O
NH
HO
4ak
33
NH
O
NH
HO
4ak
34
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec01-2017/1INDOLE8
3.00
0.92
0.99
1.01
0.99
0.96
1.00
4.53
1.04
2.00
1.02
0.99
3.63
5.39
6.57
6.58
6.83
6.84
6.86
6.86
6.90
6.92
6.94
6.95
6.97
7.11
7.12
7.26
7.28
7.29
7.30
7.31
7.32
7.34
7.51
7.52
7.53
7.55
7.55
7.61
7.61
7.63
7.63
7.71
7.73
8.14
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec01-2017/4INDOLE8
55.5
9
71.2
7
101.
8611
2.27
112.
3111
2.88
115.
4711
9.64
119.
7712
4.46
125.
5112
6.04
126.
8412
7.72
128.
4013
1.99
137.
5213
9.35
154.
02
160.
54
200.
71
NH
O
NH4ba
OCH3
NH
O
NH4ba
OCH3
35
NH
O
NH4ba
OCH3
36
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Dec01-2017/2INDOLE9
2.94
1.04
1.02
1.04
4.04
1.03
1.41
3.10
1.01
1.00
3.65
5.37
6.55
6.55
6.84
6.85
6.86
6.87
6.91
6.93
6.95
6.97
6.98
7.00
7.03
7.09
7.09
7.26
7.28
7.52
7.52
7.54
7.55
7.57
7.58
7.59
7.60
7.71
7.73
8.19
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec01-2017/3INDOLE9 55
.66
70.7
9
101.
77
112.
3711
2.43
113.
1011
5.12
115.
2811
5.33
119.
7011
9.93
124.
4112
5.58
125.
9112
8.65
128.
7313
2.05
135.
1613
7.70
154.
13
160.
5916
1.30
163.
74
200.
64
NH
O
NH4bb
OCH3
F
NH
O
NH4bb
OCH3
F
37
NH
O
NH4bb
OCH3
F
38
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec21-2017/1INDOLEDM
3.00
3.03
0.99
0.96
1.94
1.04
1.00
0.95
2.18
1.12
0.91
1.12
1.00
1.00
3.62
3.74
5.32
6.58
6.59
6.80
6.81
6.82
6.82
6.83
6.84
6.87
6.89
6.91
6.92
6.94
7.11
7.11
7.17
7.18
7.18
7.19
7.19
7.21
7.23
7.24
7.25
7.27
7.48
7.48
7.50
7.50
7.52
7.52
7.68
7.70
8.01
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec23-2017/3INDOLEEDM
55.2
455
.65
71.1
4
101.
91
112.
2211
2.32
112.
8411
2.88
112.
9311
5.51
119.
3411
9.66
119.
8212
4.46
125.
5312
6.07
129.
3713
1.97
137.
4914
1.02
154.
0915
9.63
160.
48
200.
41
NH
O
NH4bh
OCH3
H3CO
NH
O
NH4bh
OCH3
H3CO
39
NH
O
NH4bh
OCH3
H3CO
40
Crystal structure data for (2g):
Crystal structure of 2-(p-tolyl)-2-(2-(p-tolyl)-1H-indol-3-yl)indolin-3-one(2g):
(CCDC No.1832862)
Single crystals of2-(p-tolyl)-2-(2-(p-tolyl)-1H-indol-3-yl)indolin-3-
oneC61H49Cl3N4O2was selected on aXtaLAB Pro: Kappa dual
offset/far diffractometer. The crystal was kept at 93(2) K during data
collection. Using Olex2,[1] the structure was solved with the ShelXT[2]
structure solution program using Intrinsic Phasing and refined with theShelXL[3] refinement
package using Least Squares minimization.
Crystal Data for C61H49Cl3N4O2 (M =976.39 g/mol): triclinic, space group P-1 (no. 2), a =
13.13930(10) Å, b = 14.65600(10) Å, c = 15.47680(10) Å, α = 110.2300(10)°, β = 91.2620(10)°,
γ = 108.1490(10)°, V = 2629.10(4) Å3, Z = 2, T = 93(2) K, μ(CuKα) = 1.943 mm-1, Dcalc =
1.233 g/cm3, 28497 reflections measured (7.156° ≤ 2Θ ≤ 149.04°), 10338 unique (Rint = 0.0246,
Rsigma = 0.0226) which were used in all calculations. The final R1 was 0.0623 (I >2σ(I)) and wR2
was 0.1867 (all data).
TableS1:Crystal structure data of (2g): (CCDC No.1832862)
Table 1 Crystal data and structure refinement for exp_255-IND8a.
Identification code CCDC No.1832862
Empirical formula C61H49Cl3N4O2
Formula weight 976.39
Temperature/K 93(2)
Crystal system triclinic
NH
O
NH
H3C
CH3
2g
41
Space group P-1
a/Å 13.13930(10)
b/Å 14.65600(10)
c/Å 15.47680(10)
α/° 110.2300(10)
β/° 91.2620(10)
γ/° 108.1490(10)
Volume/Å3 2629.10(4)
Z 2
ρcalcg/cm3 1.233
μ/mm-1 1.943
F(000) 1020.0
Crystal size/mm3 0.2 × 0.2 × 0.1
Radiation CuKα (λ = 1.54184)
2Θ range for data collection/° 7.156 to 149.04
Index ranges -15 ≤ h ≤ 16, -18 ≤ k ≤ 18, -19 ≤ l ≤ 13
Reflections collected 28497
Independent reflections 10338 [Rint = 0.0246, Rsigma = 0.0226]
Data/restraints/parameters 10338/0/635
Goodness-of-fit on F2 1.069
Final R indexes [I>=2σ (I)] R1 = 0.0623, wR2 = 0.1847
42
Final R indexes [all data] R1 = 0.0645, wR2 = 0.1867
Largest diff. peak/hole / e Å-3 0.49/-0.84
FigureS2 Single crystal X-ray of 2g(CCDC No.1832862). The thermal ellipsoids are drawn at
the 50% probability level. The compound was crystalized with CHCl3.
References:
1. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. &Puschmann, H. (2009), J.
Appl. Cryst. 42, 339-341.
2. Sheldrick, G.M. (2015). ActaCryst. A71, 3-8.
3. Sheldrick, G.M. (2015). ActaCryst. C71, 3-8.
NH
O
NH
H3C
CH3
2g