suppl_b.doc 116KB Jun 05 2011 09:30:47 PM

Table with details of the experimental structures used for the force field refinement
For the definition of structural parameters see Chart 1
I. Ethylenediamine
a) free ligand

1
2
3
4
5
6

CSD-REFCOD

r2

r1a

r1b

COHXOM

ETDIAM10
HIBFON
KUSGEK
KUSGEK10
TAVFIF

1.515
1.505
1.499
1.492
1.492
1.443

1.493
1.47
1.466
1.44
1.44
1.411


1.486
1.47
1.466
1.44
1.44
1.477

Average values
r1

average
stdev

1.45825
0.022895

r2

average
stdev


1.491
0.022884

50

I. Ethylenediamine
b) Coordinated to a 2+ charged metal ion

1
2
3
4
5
6
7
8
9
10
11

12
13
14
15
16
17
18
19

CSD-REFCOD

r1a

r1b

r2

AENCSE10
AENCSE10
AENCUS

AENNIC10
AENNIC10
AENNIN
BAYLIW10
BEMFAA
BEMFAA
BENKOU
BENKOU
BEPZOL
BEPZOL
BEZLIB
BIDWAM
BIDWAM
BIDWAM
BOWHOK
BOWHOK

1.447
1.481
1.483

1.479
1.493
1.464
1.48
1.513
1.493
1.471
1.465
1.469
1.465
1.491
1.458
1.5
1.481
1.479
1.481

1.477
1.405
1.483

1.483
1.473
1.494
1.477
1.53
1.465
1.477
1.48
1.49
1.476
1.502
1.465
1.466
1.424
1.487
1.473

1.481
1.455
1.513

1.517
1.48
1.463
1.482
1.444
1.599
1.497
1.508
1.5
1.52
1.49
1.501
1.489
1.515
1.497
1.512

51

20

21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40

41
42

BZHXZN01
CAXRAU
CEDHAU
CIBKON
CIBKON
CIBKON
CIHGEF
CIKSOE
CIKSOE
CIKSOE
CLEENI
CLEENI
COPDEN01
CUDKAN20
DODSCU
DUGMAT
DUGMAT

DUGMAT
DUPBAR10
DUPBAR10
DUPBAR10
EDCOPT
EDITCN

1.459
1.475
1.531
1.478
1.506
1.486
1.484
1.458
1.449
1.452
1.477
1.471
1.486
1.475
1.459
1.489
1.416
1.482
1.487
1.531
1.393
1.494
1.463

1.468
1.475
1.398
1.509
1.52
1.515
1.473
1.453
1.446
1.496
1.457
1.483
1.457
1.447
1.459
1.488
1.394
1.448
1.425
1.453
1.643
1.455
1.497

1.511
1.564
1.506
1.509
1.54
1.447
1.528
1.494
1.479
1.465
1.517
1.496
1.502
1.341
1.462
1.437
1.285
1.433
1.574
1.449
1.36
1.558
1.5

52

43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65

EDITCN01
EDITCN02
EDITCN02
ENCNIC01
ENCNIC01
ENCUCC10
ENCUCC10
ENCUCN01
ENCUID
ENIACH
ENIACH
ENIACH
ETCUCY10
ETCUCY10
FIDGII
FIDGII
FIDGII
FIDGOO
FIDGOO
FIDGOO
FIDGOO
GASRUN
GEDJOO

1.468
1.442
1.496
1.463
1.469
1.458
1.444
1.465
1.48
1.484
1.467
1.485
1.454
1.424
1.465
1.473
1.471
1.498
1.484
1.434
1.458
1.479
1.474

1.47
1.468
1.485
1.472
1.472
1.442
1.426
1.455
1.48
1.469
1.468
1.461
1.468
1.448
1.473
1.469
1.47
1.512
1.484
1.482
1.452
1.477
1.474

1.537
1.563
1.465
1.507
1.51
1.433
1.428
1.487
1.481
1.493
1.487
1.51
1.488
1.407
1.511
1.506
1.521
1.401
1.341
1.412
1.426
1.503
1.502

53

66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88

GEDJOO
GIFWOH
HEGBOK
JABTAH
JABTAH10
JIFMAM
JIRCIW
KENKUJ
KENKUJ
KEZDIC
LAHYIC
LAHYIC
LAHYIC
LIHCEK
LIHCEK
LIHCEK
NETDNI01
NETNIP02
PANPAV
PIMNII
PIMNII
POKZOE
SABDEE

1.475
1.487
1.488
1.47
1.47
1.52
1.418
1.446
1.495
1.494
1.41
1.411
1.473
1.46
1.485
1.472
1.471
1.465
1.492
1.467
1.45
1.485
1.457

1.469
1.476
1.485
1.478
1.478
1.501
1.418
1.464
1.476
1.452
1.471
1.452
1.47
1.481
1.476
1.482
1.473
1.465
1.487
1.459
1.462
1.472
1.482

1.499
1.523
1.513
1.482
1.482
1.506
1.427
1.533
1.503
1.474
1.419
1.444
1.483
1.505
1.518
1.492
1.505
1.486
1.506
1.507
1.507
1.503
1.495

54

89
90
91
92
93
94
95
96
97
98
99
100
101
102

SEVNUC
SUGSUI
TAENNI01
TEANIN
TEANIN01
TENCUS10
TENNIS10
VAPKAY
VAPKAY
VIYKOD
WESVOF
YASJAD
YORJOE
ZAMDUM

1.474
1.474
1.484
1.5
1.476
1.472
1.476
1.469
1.468
1.473
1.493
1.475
1.479
1.455

1.48
1.465
1.484
1.5
1.476
1.472
1.476
1.463
1.468
1.473
1.496
1.475
1.495
1.46

1.509
1.429
1.5
1.49
1.491
1.506
1.544
1.504
1.504
1.5
1.505
1.519
1.502
1.297

Average values
r1

average
stdev

1.472221
0.025593

r2

average
stdev

1.484814
0.050733

55

I. Ethylenediamine
c) coordinated to a 3+ charged metal ion

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19

CSD-REFCOD

r1a

r2

r1b

ASENCO
ASENCO
ASENCO
ASENCO
BAGSUX01
BAGSUX01
BAVGOU
BAVGOU
BAVGUA10
BAVGUA10
BEHZET
BEHZET
BEXHER
BMXCOE
BMXCOE
BOHGAG
BOHGAG
BORFAP
BUCSUN

1.47
1.489
1.48
1.464
1.482
1.479
1.503
1.518
1.498
1.488
1.471
1.488
1.478
1.477
1.491
1.51
1.494
1.507
1.484

1.504
1.471
1.505
1.494
1.509
1.506
1.5
1.486
1.483
1.516
1.435
1.447
1.496
1.464
1.499
1.516
1.52
1.518
1.504

1.477
1.502
1.463
1.489
1.484
1.491
1.499
1.464
1.496
1.483
1.498
1.473
1.53
1.484
1.493
1.502
1.5
1.483
1.491

56

20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
41
42
43

BUTDAV
BUTZIZ
BUTZIZ
CAJYER
CAJYER
CASDUV
CAZFEO
CAZFEO
CEHYAP01
CENCOS
CENCOS
CEWTUT
CEWTUT01
CIDLEG
CIDLIK
CIFPIQ
CLENCO
CLENCO
CNENCO
COCRCL
COCREN
COCREN
COCREN

1.481
1.485
1.485
1.48
1.514
1.469
1.487
1.459
1.487
1.484
1.479
1.517
1.489
1.484
1.477
1.476
1.482
1.471
1.475
1.412
1.486
1.488
1.508

1.506
1.501
1.504
1.529
1.491
1.521
1.507
1.544
1.519
1.507
1.533
1.513
1.448
1.482
1.456
1.502
1.493
1.486
1.497
1.506
1.507
1.489
1.573

1.481
1.481
1.494
1.448
1.496
1.498
1.478
1.493
1.488
1.475
1.496
1.51
1.501
1.496
1.464
1.487
1.497
1.488
1.484
1.502
1.525
1.483
1.503

57

44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66

COEMAL10
COENCH
COENCH
COENCL
COENCL
COENSI
COENSI
COENTC
COENTC
COENTC
COFYIF
CONAEN
CONAEN01
COTENC
CRENCL
CRENCL
CRENCL
CRENCL
CRENCL
CRENCL
CRENCL01
CRENCL01
CRENCL01

1.478
1.5
1.475
1.433
1.537
1.543
1.545
1.525
1.5
1.5
1.498
1.508
1.505
1.481
1.446
1.512
1.489
1.52
1.45
1.457
1.509
1.534
1.485

1.497
1.5
1.522
1.523
1.525
1.457
1.575
1.504
1.509
1.48
1.503
1.517
1.498
1.524
1.467
1.441
1.494
1.435
1.513
1.519
1.515
1.479
1.519

1.469
1.505
1.475
1.515
1.442
1.445
1.526
1.49
1.475
1.472
1.496
1.494
1.471
1.479
1.549
1.514
1.488
1.489
1.491
1.479
1.431
1.489
1.486

58

67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89

CRENCL01
CRENCL01
CRENCL01
CRENOX
CRENTC
CRENTC
CRENTC
CRENTC01
CRENTC01
CRHENC
CRTENC
CUNKIF
CUNKIF
CUSCOI
CUYZOL
CUYZOL
DAFHOH
DAFHOH
DEWLAS
DEWLAS
DISVIK
DISVIK
DISVUW

1.5
1.468
1.47
1.483
1.506
1.49
1.492
1.491
1.49
1.484
1.462
1.477
1.495
1.486
1.487
1.502
1.465
1.458
1.47
1.509
1.501
1.484
1.523

1.509
1.528
1.531
1.494
1.52
1.497
1.503
1.515
1.502
1.52
1.518
1.516
1.502
1.485
1.482
1.424
1.44
1.473
1.517
1.383
1.477
1.501
1.491

1.48
1.484
1.482
1.504
1.488
1.485
1.488
1.484
1.495
1.47
1.482
1.482
1.483
1.474
1.49
1.476
1.477
1.455
1.446
1.433
1.47
1.492
1.52

59

90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112

DISVUW
DOCZOK
DOCZOK
DOCZUQ
DOCZUQ
DOLTIH
DOLTIH
DOLTON
DOLTON
DSENCO
DSENCO
EDCHCO
EDCHCO
EDCHCO
EDCHCO
EDCRCN
EDCRCN
EDCRCN
EDCRCN
EDCRCN
EDCRCN
EINICI
EINIPC

1.449
1.488
1.481
1.479
1.491
1.486
1.497
1.485
1.493
1.461
1.488
1.462
1.47
1.437
1.421
1.486
1.496
1.473
1.487
1.494
1.5
1.486
1.472

1.486
1.503
1.499
1.495
1.496
1.515
1.513
1.521
1.512
1.506
1.472
1.397
1.434
1.375
1.337
1.489
1.49
1.505
1.518
1.498
1.515
1.452
1.495

1.459
1.486
1.486
1.485
1.489
1.492
1.488
1.494
1.49
1.489
1.509
1.462
1.497
1.405
1.433
1.5
1.495
1.461
1.497
1.502
1.494
1.495
1.449

60

113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135

EINIPC
ENCCUC10
ENCCUC10
ENCCUC10
ENCOAM10
ENCOCD
ENCOCD
ENCOCL01
ENCOCT
ENCOCT
ENCOCT
ENCOCT01
ENCOCT01
ENCOCT01
ENCOIH
ENCOIH
ENCOIH
ENCOPB01
ENCOPB01
ENCOPB01
ENCOPH
ENCOPH
ENCOPH

1.56
1.447
1.469
1.455
1.481
1.498
1.489
1.548
1.485
1.485
1.483
1.494
1.499
1.494
1.483
1.476
1.481
1.554
1.462
1.516
1.482
1.483
1.487

1.406
1.518
1.494
1.553
1.502
1.491
1.513
1.509
1.507
1.504
1.505
1.493
1.503
1.498
1.511
1.516
1.491
1.484
1.418
1.505
1.532
1.516
1.518

1.483
1.493
1.499
1.465
1.483
1.496
1.482
1.426
1.486
1.481
1.48
1.491
1.488
1.488
1.493
1.476
1.472
1.471
1.523
1.497
1.501
1.488
1.467

61

136
137
138
139
140
141
142
143
144
145
146
147
151
152
153
154
155
156
157
158
159
160
161

ENCOPH
ENCOPN
ENCOPN
ENCOSE
ENCOSE
ENCOSE
ENCOSE
ENCOSE01
ENCOSE01
ENCOSE01
ENCOSE01
ENCRBH10
ENCRBH10
ENCRBH10
ENCRBH10
ENCRBH10
ENCRBH10
ENCYCO
ENCYCO
ENCYSM
ENCYSM
ENDACR
ENDACR

1.488
1.485
1.486
1.497
1.519
1.476
1.459
1.514
1.498
1.48
1.478
1.454
1.42
1.438
1.453
1.526
1.464
1.477
1.487
1.439
1.492
1.5
1.49

1.518
1.501
1.502
1.519
1.478
1.424
1.38
1.414
1.414
1.547
1.565
1.464
1.524
1.388
1.456
1.542
1.452
1.503
1.513
1.333
1.518
1.504
1.455

1.475
1.495
1.483
1.526
1.473
1.507
1.491
1.475
1.587
1.517
1.478
1.5
1.552
1.449
1.558
1.54
1.495
1.484
1.485
1.49
1.493
1.491
1.494

62

162
163
164
165
166
167
168
169
170
171
172
173
174
175
176
177
178
179
180
181
182
183
184

ENDACR
ENGCOA
ENPCCO10
ENTCOF
ENTCOF
ENTXCO
ENTXCO
ENTZCO
ENZXCO
ENZXCO
ETDCOH02
ETDCOH03
ETDCOH11
FAGXUG
FAGYAN
FAGYAN
FEZXUD
FEZXUD
FIWDAQ
FOJBAH
FOJBAH
GAPHUA
GAPHUA

1.493
1.473
1.494
1.5
1.478
1.484
1.483
1.49
1.522
1.463
1.492
1.484
1.479
1.496
1.488
1.488
1.494
1.495
1.483
1.437
1.48
1.482
1.499

1.504
1.483
1.491
1.492
1.467
1.506
1.514
1.483
1.395
1.4
1.501
1.484
1.505
1.498
1.504
1.504
1.511
1.494
1.503
1.357
1.486
1.514
1.532

1.498
1.49
1.498
1.476
1.498
1.477
1.483
1.475
1.452
1.446
1.497
1.505
1.485
1.487
1.484
1.488
1.492
1.473
1.475
1.435
1.487
1.492
1.484

63

185
186
187
188
189
190
191
192
193
194
195
196
197
198
199
200
201
202
203
204
205
206
207

GAPHUA
GAPHUA
GAPHUA
GAPHUA
GAWGOA
GIHLIS
HANJIP
HANJIP
HCRENT
HCRENT
HXENCB
HXENCB
JAHDIF
JAHDIF
JAHDIF02
JATTAZ
JATTAZ
JATTAZ
JATTAZ
JATTAZ
JATTAZ
JOGPOK
KABXOA

1.49
1.504
1.481
1.476
1.485
1.481
1.478
1.491
1.496
1.483
1.487
1.496
1.497
1.501
1.492
1.481
1.523
1.478
1.491
1.49
1.476
1.513
1.481

1.524
1.491
1.525
1.526
1.473
1.511
1.484
1.503
1.502
1.499
1.505
1.511
1.506
1.502
1.517
1.514
1.495
1.501
1.499
1.496
1.485
1.482
1.509

1.49
1.499
1.494
1.487
1.482
1.478
1.506
1.488
1.476
1.486
1.485
1.49
1.497
1.501
1.492
1.514
1.469
1.485
1.504
1.493
1.477
1.503
1.453

64

208
209
210
211
212
213
214
215
216
217
218
219
220
221
222
223
224
225
226
227
228
229
230

KABXOA
KABXUG
KABXUG
KARFAK
KARFAK
KEGTAR
KEGTAR
KERFAO
KUMTIV
KUMTIV
PEVXAP
PEVXAP
PEVXAP
PEVXAP
PEVXAP
PEVXAP
PIBFEL
PIBFEL
PIBFEL
PIBFEL
PIBFIP
PIBFIP
PIBFIP

1.469
1.492
1.475
1.464
1.489
1.507
1.465
1.491
1.495
1.487
1.486
1.48
1.473
1.483
1.494
1.487
1.481
1.479
1.477
1.486
1.507
1.515
1.469

1.479
1.522
1.491
1.529
1.476
1.504
1.475
1.509
1.474
1.481
1.506
1.495
1.514
1.502
1.444
1.495
1.511
1.476
1.481
1.512
1.504
1.491
1.45

1.46
1.479
1.505
1.53
1.449
1.49
1.472
1.489
1.486
1.473
1.478
1.486
1.477
1.497
1.511
1.473
1.482
1.511
1.484
1.466
1.492
1.497
1.451

65

231
232
233
234
235
236
237
238
239
240
241
242
243
244
245
246
247
248
249
250
251
252
253

PIBFIP
PIBFOV
PIBFOV
PIBFOV
PIFCOW
PIFCOW
PIFCOW
PIFCOW
SALRIG
SAYKUY
SAYKUY
SAYKUY
SAYLAF
SAYLAF
SOZFIW
TENCON
TENCON
TENCON
TENCRI
TENCRI
TENCRI
TZCECO
WESRER

1.499
1.484
1.489
1.479
1.477
1.497
1.455
1.471
1.494
1.516
1.492
1.482
1.459
1.445
1.49
1.464
1.474
1.496
1.494
1.49
1.491
1.494
1.477

1.449
1.513
1.483
1.498
1.623
1.638
1.62
1.584
1.499
1.501
1.502
1.494
1.508
1.505
1.501
1.494
1.525
1.457
1.506
1.504
1.502
1.495
1.521

1.479
1.496
1.497
1.474
1.469
1.477
1.495
1.492
1.489
1.496
1.489
1.495
1.485
1.504
1.491
1.463
1.475
1.479
1.501
1.499
1.489
1.5
1.488

66

254
255
256
257
258
259
260
261
262
263
264
265
266
267
268
269
270
271
272
273
274
275
276

WESRER
YIVHIU
YIVHIU
YIVHIU
YOPBAG
YOPBEK
YOPBOU
YOPCAH
YUXPOW
YUXPOW
YUXPOW
ZEKNIM
ZEKNIM
ZEKNOS
ZEKNOS
ZEKPEK
ZEKPOU
ZZZAZY10
ZZZAZY10
ZZZAZY10
ZZZAZY10
ZZZAZY10
ZZZAZY10

1.472
1.487
1.513
1.539
1.475
1.514
1.468
1.49
1.48
1.498
1.493
1.421
1.471
1.482
1.482
1.497
1.486
1.496
1.504
1.509
1.49
1.499
1.484

1.415
1.457
1.562
1.438
1.494
1.49
1.438
1.505
1.512
1.501
1.502
1.472
1.499
1.495
1.488
1.474
1.498
1.488
1.493
1.472
1.498
1.489
1.488

1.472
1.449
1.464
1.482
1.48
1.506
1.511
1.487
1.493
1.5
1.485
1.473
1.48
1.482
1.491
1.475
1.48
1.485
1.507
1.488
1.474
1.478
1.474

67

Average values
r1

average
stdev

1.486286
0.020482

r2

average
stdev

1.493949
0.037906

68

II. Diaminocyclohexane
a) free ligand

1
2
3
4
5
6

REFCOD

r1a

r1b

r2

r3a

r3b

PIWXEY
PIWXOI
PIWXUO
ZAVXAV
ZAVXEZ
ZAVXID

1.465
1.471
1.477
1.463
1.465
1.48

1.465
1.471
1.469
1.463
1.462
1.48

1.532
1.535
1.524
1.523
1.521
1.524

1.518
1.527
1.52
1.517
1.518
1.531

1.518
1.52
1.513
1.517
1.514
1.523

Average values
r1

average
stdev

1.46925
0.006339

r2

average
stdev

1.5265
0.005123

r3

average
stdev

1.519667
0.004939

69

II. Diaminocyclohexane
b) coordinated to a 2+ charged metal ion
NFRAG

CSD-REFCOD

r1a

r1b

r2a

r3a

r3b

1
2
3
4
5
6
7
8
9
10
11
12
13
14

AHDNIC
CUKXUB
FUYBOQ
JOBYUU
JOBYUU
JOBYUU
JOBZAB
JOBZAB
JOBZAB
SASNUV
SASNUV01
SENMED
VIDXEL
WIMMIO

1.465
1.494
1.495
1.49
1.483
1.475
1.492
1.498
1.499
1.488
1.495
1.506
1.488
1.488

1.465
1.494
1.479
1.484
1.494
1.486
1.49
1.49
1.484
1.488
1.495
1.491
1.492
1.492

1.539
1.497
1.525
1.535
1.544
1.524
1.538
1.525
1.521
1.507
1.513
1.518
1.519
1.507

1.51
1.491
1.529
1.53
1.523
1.536
1.519
1.512
1.528
1.528
1.519
1.515
1.529
1.527

1.51
1.491
1.526
1.523
1.528
1.537
1.526
1.52
1.543
1.528
1.519
1.526
1.523
1.511

70

Average values
r1

average
stdev

1.488571
0.008922

r2

average
stdev

1.522286
0.013095

r3

average
stdev

1.521679
0.011576

71

II. Diaminocyclohexane
c) coordinated to a 3+ charged metal ion

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19

CSD-REFCOD

r1a

r1b

r2a

r3a

r3b

ACHXCO
ACHXCO
ACHXCO
CHXNCO
CHXNCO
CHXNCO10
DOFFEJ
DOFFEJ
HDMPCO
HDMPCO
JESCIT
JESCIT
JESCIT
JESCOZ
JESCOZ
JESCOZ
KOHPEC
KUHJOM
TAHJAN

1.487
1.49
1.478
1.487
1.499
1.488
1.492
1.461
1.493
1.502
1.496
1.506
1.481
1.5
1.498
1.496
1.488
1.494
1.508

1.49
1.483
1.486
1.49
1.499
1.488
1.519
1.481
1.496
1.518
1.491
1.493
1.462
1.497
1.49
1.481
1.487
1.493
1.48

1.507
1.493
1.492
1.506
1.514
1.514
1.467
1.485
1.479
1.473
1.52
1.515
1.505
1.529
1.516
1.516
1.515
1.521
1.503

1.536
1.514
1.519
1.53
1.522
1.522
1.511
1.566
1.522
1.515
1.517
1.536
1.505
1.523
1.521
1.538
1.522
1.52
1.554

1.515
1.538
1.535
1.523
1.522
1.522
1.528
1.516
1.501
1.515
1.529
1.513
1.526
1.521
1.528
1.529
1.519
1.521
1.557

72

20
21
22
23
24
25
26
27
28
29
30
31
32
33

TAHJAN
TAHJAN
TAHJAN
TAHJAN
TAHJAN
TAHJAN
TAHJAN
TAHJAN
TAHJER
TAHJER
TAHJER
VIMWOD
VIMWOD
VIMWOD

1.472
1.491
1.51
1.51
1.514
1.555
1.549
1.507
1.505
1.483
1.57
1.487
1.471
1.491

1.478
1.563
1.478
1.534
1.566
1.51
1.513
1.482
1.56
1.438
1.44
1.468
1.494
1.466

1.566
1.567
1.565
1.548
1.531
1.495
1.593
1.557
1.526
1.447
1.501
1.513
1.507
1.501

73

1.526
1.522
1.483
1.536
1.525
1.597
1.521
1.504
1.524
1.532
1.542
1.525
1.509
1.518

1.571
1.547
1.498
1.483
1.528
1.516
1.562
1.502
1.465
1.515
1.502
1.512
1.521
1.535

Average values
r1

average
stdev

1.496561
0.025966

r2

average
stdev

1.514758
0.030415

r3

average
stdev

1.523818
0.019876

74

III. Methylamine
a) free ligand
No non-protonated structure available
b) coordinated to a 2+ charged metal
No structures available
c) coordinated to a 3+ charged metal ion

1
2
3
4
5
6
7
8
9
10

CSD-REFCOD

r1

CMACON10
CMACON10
CMACON10
CMACON10
CMACON10
MACRCC
MACRCC
MACRCC
MACRCC
MACRCC

1.479
1.466
1.488
1.483
1.476
1.449
1.461
1.457
1.488
1.472

75

Average values
r1

average
stdev

1.4719
0.012684

76

IV. Ethylamine
a) free ligand

1
2

REFCOD

r2

r1

YECVUX
YECVUX

1.482
1.48

1.461
1.462

Average values
r1

average
stdev

1.4615
0.0005

r2

average
stdev

1.481
0.001

b) coordinated to a 2+ charged metal ion
No structure available
c) coordinated to a 3+ charged metal ion
No structures available

77

V. Diammac
a) free ligand
No non-protonated structures available
b) coordinated to a 2+ charged metal ion

1
2
3
4
5
6
7
8
9

1
2
3
4
5

CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

r1h

DUMGIB
FANFEF
FEBZUH
FEBZUH10
KENPUO
PEHWOO
PEHXAB
PEHXEF
VISSUL

1.484
1.494
1.496
1.478
1.466
1.472
1.467
1.471
1.465

1.483
1.493
1.478
1.485
1.482
1.474
1.482
1.478
1.476

1.49
1.468
1.485
1.478
1.482
1.492
1.489
1.48
1.463

1.458
1.481
1.478
1.496
1.476
1.484
1.463
1.495
1.476

1.484
1.494
1.485
1.486
1.466
1.484
1.467
1.483
1.476

1.483
1.493
1.483
1.75
1.482
1.49
1.482
1.479
1.489

1.49
1.468
1.487
1.483
1.482
1.478
1.489
1.481
1.473

1.458
1.481
1.486
1.485
1.476
1.495
1.463
1.459
1.497

CSD-REFCOD

r2a

r2b

r3a

r3b

r3c

r3d

DUMGIB
FANFEF
FEBZUH
FEBZUH10
KENPUO

1.508
1.524
1.525
1.526
1.511

1.508
1.524
1.53
1.566
1.511

1.538
1.544
1.533
1.538
1.535

1.519
1.532
1.559
1.556
1.537

1.519
1.532
1.538
1.533
1.537

1.538
1.544
1.556
1.559
1.535

78

6
7
8
9

PEHWOO
PEHXAB
PEHXEF
VISSUL

1.506
1.495
1.516
1.501

1.518
1.495
1.52
1.501

1.551
1.532
1.537
1.526

Average values
r1

average
stdev

1.483958
0.033051

r2

average
stdev

1.515833
0.016046

r3

average
stdev

1.538306
0.009336

79

1.544
1.533
1.538
1.535

1.54
1.533
1.532
1.546

1.546
1.532
1.533
1.539

V. Diammac
c) coordinated to a 3+ charged metal ion
NFRAG

REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

r1h

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18

FEBZOB
FEBZOB10
HAFBEV
HAFBEV
HAFBEV
HAFBIZ
HAFBIZ
HAHLOR
JEVCAO
JEVCAO
KUWZIL
KUWZOR
KUWZUX
KUXBAG
SANLAU
SANLAU
SIZCEJ
ZUSCIZ

1.487
1.49
1.472
1.488
1.488
1.474
1.477
1.491
1.475
1.46
1.501
1.546
1.521
1.516
1.487
1.486
1.474
1.483

1.491
1.491
1.477
1.478
1.478
1.48
1.491
1.5
1.462
1.465
1.521
1.504
1.463
1.476
1.475
1.514
1.487
1.53

1.491
1.493
1.478
1.484
1.484
1.48
1.488
1.502
1.453
1.462
1.518
1.519
1.497
1.506
1.453
1.474
1.483
1.482

1.492
1.491
1.48
1.475
1.475
1.474
1.489
1.509
1.479
1.459
1.478
1.49
1.487
1.385
1.486
1.495
1.473
1.477

1.487
1.49
1.486
1.486
1.48
1.477
1.477
1.489
1.475
1.46
1.482
1.468
1.487
1.417
1.487
1.486
1.474
1.483

1.491
1.491
1.478
1.478
1.478
1.491
1.491
1.498
1.462
1.465
1.515
1.506
1.494
1.478
1.475
1.514
1.487
1.53

1.491
1.493
1.478
1.478
1.477
1.488
1.488
1.503
1.453
1.462
1.497
1.465
1.502
1.486
1.453
1.474
1.483
1.482

1.492
1.491
1.485
1.485
1.472
1.489
1.489
1.493
1.479
1.459
1.51
1.481
1.514
1.524
1.486
1.495
1.473
1.477

80

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18

CSD-REFCOD

r2a

r2b

r3a

r3b

r3c

r3d

FEBZOB
FEBZOB10
HAFBEV
HAFBEV
HAFBEV
HAFBIZ
HAFBIZ
HAHLOR
JEVCAO
JEVCAO
KUWZIL
KUWZOR
KUWZUX
KUXBAG
SANLAU
SANLAU
SIZCEJ
ZUSCIZ

1.503
1.503
1.517
1.519
1.519
1.496
1.488
1.501
1.323
1.339
1.526
1.5
1.504
1.599
1.387
1.435
1.473
1.498

1.503
1.503
1.515
1.515
1.517
1.488
1.488
1.507
1.323
1.339
1.513
1.55
1.513
1.521
1.387
1.435
1.473
1.498

1.533
1.532
1.547
1.557
1.557
1.53
1.525
1.531
1.509
1.523
1.521
1.556
1.525
1.568
1.507
1.525
1.528
1.524

1.533
1.534
1.539
1.539
1.547
1.531
1.531
1.535
1.526
1.532
1.542
1.54
1.52
1.523
1.56
1.525
1.524
1.52

1.533
1.534
1.549
1.54
1.54
1.53
1.531
1.521
1.526
1.532
1.529
1.584
1.55
1.575
1.56
1.525
1.524
1.52

1.533
1.532
1.548
1.548
1.549
1.525
1.525
1.538
1.509
1.523
1.551
1.581
1.502
1.565
1.507
1.525
1.528
1.524

81

Average values
r1

average
stdev

1.484722
0.019117

r2

average
stdev

1.478278
0.064339

r3

average
stdev

1.534931
0.016535

82

VI. Sar
a) free ligand

1
2

1
2

1
2

CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

r1h

r1i

LEJPOF
LEJPUL

1.499
1.475

1.462
1.455

1.444
1.442

1.46
1.46

1.421
1.467

1.419
1.448

1.498
1.445

1.489
1.452

1.459
1.464

CSD-REFCOD

r1j

r1k

r1l

r2a

r2b

r2c

r3a

r3b

r3c

LEJPOF
LEJPUL

1.473
1.458

1.474
1.453

1.466
1.449

1.535
1.514

1.535
1.503

1.502
1.513

1.554
1.53

1.543
1.536

1.52
1.528

CSD-REFCOD

r3d

r3e

r3f

LEJPOF
LEJPUL

1.491
1.53

1.53
1.524

1.577
1.513

83

Average values
r1

average
stdev

1.459667
0.019271

r2

average
stdev

1.517
0.013503

r3

average
stdev

1.531333
0.020246

VI. Sar
b) coordinated to a 2+ charged metal ion

1
2

1
2

1
2

CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

r1h

LAFXIZ
LEJRAT

1.486
1.493

1.483
1.465

1.467
1.459

1.471
1.481

1.478
1.493

1.475
1.465

1.462
1.459

1.488
1.481

CSD-REFCOD

r1j

r1l

r1k

r1l

r2a

r2b

r3a

r3b

LAFXIZ
LEJRAT

1.48
1.454

1.445
1.476

1.477
1.454

1.474
1.476

1.505
1.475

1.451
1.487

1.496
1.514

1.516
1.503

CSD-REFCOD

r3c

r3d

r3e

r3f

LAFXIZ
LEJRAT

1.514
1.518

1.512
1.518

1.501
1.514

1.528
1.503

84

Average values
r1

average
stdev

1.472583
0.012446

r2

average
stdev

1.4795
0.019615

r3

average
stdev

1.511417
0.008616

VI. Sar
c) coordinated to a 3+ charged metal ion

1
2
3
4
5
6
7
8

CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

HAFBUL
VOBCEU
YOZSAH
YUMDIT
YUMFIV
YUMGIW
YUMHIX
YUMHIX

1.516
1.484
1.515
1.515
1.496
1.496
1.607
1.499

1.432
1.495
1.494
1.474
1.488
1.478
1.498
1.581

1.432
1.504
1.481
1.466
1.489
1.472
1.66
1.507

1.516
1.48
1.503
1.492
1.486
1.502
1.444
1.501

1.503
1.48
1.492
1.495
1.495
1.479
1.432
1.504

1.443
1.505
1.495
1.488
1.486
1.505
1.538
1.583

1.472
1.513
1.49
1.495
1.501
1.491
1.46
1.552

85

1
2
3
4
5
6
7
8

1
2
3
4
5
6
7
8

CSD-REFCOD

r1h

r1i

r1j

r1k

r1l

r2a

r2b

HAFBUL
VOBCEU
YOZSAH
YUMDIT
YUMFIV
YUMGIW
YUMHIX
YUMHIX

1.505
1.49
1.504
1.516
1.506
1.519
1.464
1.437

1.503
1.492
1.506
1.492
1.496
1.498
1.666
1.541

1.443
1.497
1.483
1.505
1.491
1.494
1.458
1.468

1.472
1.508
1.487
1.509
1.497
1.502
1.54
1.49

1.505
1.483
1.499
1.517
1.505
1.531
1.477
1.46

1.485
1.496
1.495
1.499
1.494
1.489
1.484
1.466

1.548
1.489
1.494
1.493
1.489
1.496
1.416
1.455

CSD-REFCOD

r3a

r3b

r3c

r3d

r3e

r3f

HAFBUL
VOBCEU
YOZSAH
YUMDIT
YUMFIV
YUMGIW
YUMHIX
YUMHIX

1.56
1.543
1.497
1.528
1.547
1.551
1.499
1.6

1.527
1.553
1.496
1.498
1.514
1.501
1.487
1.559

1.535
1.548
1.509
1.528
1.531
1.501
1.437
1.51

1.527
1.544
1.522
1.513
1.515
1.541
1.573
1.485

1.535
1.544
1.504
1.508
1.529
1.508
1.487
1.537

1.56
1.537
1.514
1.523
1.525
1.509
1.559
1.576

86

Average values
r1

average
stdev

1.4985
0.037238

r2

average
stdev

1.48675
0.025927

r3

average
stdev

1.525708
0.028239

87

VII. Cyclam
a) free ligand
No non-protonated structures available
b) coordinated to a 2+ charged metal ion

1
2
3
4

1
2
3
4

CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

DOHXON
FAGVUE
HAFSUC
ZIQXOM

1.466
1.473
1.477
1.48

1.488
1.49
1.462
1.482

1.459
1.482
1.486
1.489

1.479
1.492
1.471
1.475

1.466
1.48
1.477
1.48

1.488
1.478
1.462
1.482

1.459
1.488
1.486
1.489

CSD-REFCOD

r1h

r2a

r2b

r3a

r3b

r3c

r3d

DOHXON
FAGVUE
HAFSUC
ZIQXOM

1.479
1.487
1.471
1.475

1.467
1.516
1.49
1.503

1.467
1.503
1.49
1.503

1.485
1.495
1.511
1.521

1.525
1.538
1.5
1.526

1.525
1.506
1.5
1.526

1.485
1.504
1.511
1.521

88

Average values
r1

average
stdev

1.478063
0.009384

r2

average
stdev

1.492375
0.016568

r3

average
stdev

1.511188
0.015195

VII. Cyclam
c) coordinated to a 3+ charged metal ion

1
2
3
4
5
6
7
8
9
10

CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r1g

r1h

AZMTCO
BINPET
BINPET
COANEC
CUSBUN
DOHBEH
FEBZOB
FEBZOB10
FUMWUF
HAHLOR

1.461
1.48
1.486
1.494
1.499
1.492
1.492
1.491
1.439
1.509

1.493
1.479
1.485
1.486
1.487
1.494
1.491
1.493
1.453
1.502

1.496
1.477
1.474
1.489
1.483
1.492
1.491
1.491
1.521
1.5

1.437
1.484
1.477
1.493
1.482
1.497
1.487
1.49
1.459
1.491

1.461
1.48
1.486
1.494
1.499
1.492
1.492
1.491
1.5
1.493

1.493
1.479
1.485
1.486
1.487
1.494
1.491
1.493
1.52
1.503

1.496
1.477
1.474
1.489
1.483
1.495
1.491
1.491
1.485
1.498

1.437
1.484
1.477
1.493
1.482
1.491
1.487
1.49
1.499
1.489

89

11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33

HENYAA
HENYAA
JOFYIM
JOFYOS
JOMNEE
KEFYAV
KUGMAA
LALTEX
PACHAC
PACJOS
PASFOE
PASGAR
SANLAU
SANLAU
TZCECO
VEFVEH
VIZYOS
VIZYUY
VIZZAF
VIZZAF
WAMWOW
WESLAH
ZUSCIZ

1.479
1.491
1.478
1.471
1.483
1.487
1.482
1.484
1.484
1.501
1.496
1.49
1.486
1.495
1.493
1.473
1.484
1.475
1.487
1.482
1.515
1.469
1.477

1.34
1.481
1.482
1.493
1.481
1.488
1.495
1.567
1.481
1.491
1.476
1.492
1.453
1.474
1.485
1.482
1.489
1.502
1.483
1.502
1.487
1.476
1.482

1.474
1.486
1.496
1.485
1.499
1.493
1.493
1.439
1.482
1.481
1.49
1.472
1.475
1.514
1.495
1.482
1.485
1.502
1.488
1.473
1.509
1.471
1.53

90

1.42
1.468
1.473
1.485
1.488
1.487
1.486
1.485
1.514
1.486
1.5
1.485
1.487
1.486
1.509
1.473
1.484
1.475
1.486
1.5
1.517
1.499
1.483

1.352
1.38
1.483
1.471
1.493
1.472
1.482
1.484
1.481
1.495
1.479
1.484
1.486
1.495
1.501
1.473
1.484
1.475
1.487
1.482
1.515
1.498
1.477

1.527
1.543
1.481
1.493
1.491
1.483
1.495
1.567
1.475
1.493
1.479
1.488
1.453
1.474
1.497
1.482
1.489
1.502
1.483
1.502
1.487
1.478
1.482

1.504
1.528
1.483
1.485
1.493
1.497
1.493
1.439
1.455
1.486
1.466
1.48
1.475
1.514
1.495
1.482
1.485
1.502
1.488
1.473
1.509
1.488
1.53

1.35
1.412
1.49
1.485
1.491
1.489
1.486
1.485
1.482
1.507
1.495
1.478
1.487
1.486
1.501
1.473
1.484
1.475
1.486
1.5
1.517
1.476
1.483

34

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20

ZUZSOC

1.489

1.475

1.479

1.476

1.494

1.473

CSD-REFCOD

r2a

r2b

r3a

r3b

r3c

r3d

AZMTCO
BINPET
BINPET
COANEC
CUSBUN
DOHBEH
FEBZOB
FEBZOB10
FUMWUF
HAHLOR
HENYAA
HENYAA
JOFYIM
JOFYOS
JOMNEE
KEFYAV
KUGMAA
LALTEX
PACHAC
PACJOS

1.455
1.509
1.514
1.498
1.503
1.498
1.503
1.503
1.482
1.501
1.461
1.448
1.499
1.511
1.504
1.504
1.512
1.517
1.486
1.496

1.455
1.509
1.514
1.498
1.503
1.502
1.503
1.503
1.499
1.507
1.399
1.458
1.494
1.511
1.502
1.509
1.512
1.517
1.341
1.493

1.509
1.517
1.515
1.509
1.52
1.527
1.533
1.532
1.527
1.538
1.358
1.49
1.507
1.518
1.507
1.515
1.523
1.472
1.488
1.524

1.539
1.514
1.506
1.509
1.509
1.518
1.533
1.534
1.497
1.521
1.508
1.499
1.518
1.531
1.505
1.507
1.52
1.628
1.523
1.509

1.509
1.517
1.515
1.509
1.52
1.513
1.533
1.532
1.548
1.531
1.487
1.506
1.531
1.518
1.524
1.534
1.523
1.472
1.513
1.535

1.539
1.514
1.506
1.509
1.509
1.509
1.533
1.534
1.511
1.535
1.471
1.503
1.519
1.531
1.531
1.533
1.52
1.628
1.516
1.523

91

1.479

1.48

21
22
23
24
25
26
27
28
29
30
31
32
33
34

PASFOE
PASGAR
SANLAU
SANLAU
TZCECO
VEFVEH
VIZYOS
VIZYUY
VIZZAF
VIZZAF
WAMWOW
WESLAH
ZUSCIZ
ZUZSOC

1.505
1.492
1.387
1.435
1.488
1.524
1.507
1.484
1.509
1.501
1.571
1.501
1.498
1.517

1.512
1.487
1.387
1.435
1.487
1.524
1.507
1.484
1.509
1.501
1.571
1.492
1.498
1.521

1.517
1.524
1.507
1.525
1.513
1.556
1.511
1.524
1.51
1.491
1.559
1.523
1.524
1.529

Average values
r1

average
stdev

1.485162
0.023217

r2

average
stdev

1.492162
0.036658

r3

average
stdev

1.517978
0.025711

92

1.491
1.506
1.56
1.525
1.506
1.556
1.517
1.524
1.516
1.51
1.532
1.49
1.52
1.487

1.495
1.516
1.507
1.525
1.502
1.556
1.511
1.524
1.51
1.491
1.559
1.509
1.524
1.513

1.496
1.504
1.56
1.525
1.505
1.556
1.517
1.524
1.516
1.51
1.532
1.485
1.52
1.499

VIII. Tacn
a) free ligand
CSD-REFCOD

r1a

r1b

r1c

r1d

r1e

r1f

r2a

ZOJFIN

1.465

1.461

1.454

1.457

1.469

1.458

1.52

CSD-REFCOD

r2b

r2c

ZOJFIN

1.527

1.517

1

1
Average values
r1

average

1.460667

stdev

0.005055

r2

average

1.521333

stdev

0.00419

b) coordinated to a 2+ charged metal ion

1
2
3
4
5
6
7

CSD-REFCOD

r1a

r1b

r1c

r2a

r2b

r2c

BAZNCU
CLAZCU
DORTIN
DORTIN
DUSJAC
DUSJAC
DUSJAC01

1.474
1.484
1.463
1.506
1.48
1.47
1.489

1.482
1.478
1.512
1.497
1.475
1.467
1.481

1.493
1.473
1.497
1.483
1.469
1.483
1.466

1.51
1.521
1.503
1.495
1.524
1.484
1.519

1.52
1.5
1.492
1.507
1.52
1.497
1.517

1.514
1.517
1.539
1.515
1.511
1.491
1.51

93

8
9
10
11
12
13
14

DUSJAC01
FECLII
JEMBAE
JUXXIJ
JUXXIJ
KURPES
VUFJIP

1.482
1.46
1.482
1.458
1.425
1.489
1.373

r1

average
stdev

1.476476
0.030012

r2

average
stdev

1.50831
0.02976

1.472
1.471
1.478
1.446
1.454
1.477
1.51

1.49
1.468
1.48
1.457
1.441
1.478
1.599

1.509
1.535
1.517
1.51
1.557
1.507
1.454

1.525
1.555
1.514
1.494
1.496
1.518
1.427

1.525
1.525
1.521
1.564
1.48
1.517
1.393

VIII. Tacn
c) coordinated to a 3+ charged metal ion

1
2
3
4
5
6

CSD-REFCOD

r1a

r1b

r1c

r2a

r2b

r2c

AMGZCO
DEGZIY
FOPLUR
KUYZAF
KUYZIN
KUZDAK

1.488
1.486
1.43
1.43
1.434
1.516

1.513
1.487
1.493
1.46
1.451
1.506

1.506
1.462
1.482
1.469
1.462
1.516

1.5
1.405
1.426
1.388
1.369
1.496

1.505
1.443
1.445
1.474
1.369
1.511

1.483
1.463
1.426
1.486
1.459
1.51

94

7
8
9
10
11
12

VAVGII
WEZCIN
WEZCIN
ZETXEB
ZEZTON
ZEZTON

1.468
1.484
1.483
1.503
1.468
1.47

r1

average
stdev

1.479694
0.02349

r2

average
stdev

1.465278
0.046752

1.456
1.475
1.486
1.479
1.49
1.452

1.508
1.503
1.494
1.514
1.464
1.481

95

1.461
1.526
1.511
1.487
1.502
1.384

1.4
1.522
1.503
1.475
1.494
1.434

1.429
1.528
1.511
1.505
1.504
1.416

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