# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jun 10 06:37:41 2020
#   Inital geometry file: a 104 line input string
#   Ligand name: 3,6-diamino-5-cyano-4-(4-ethoxyphenyl)thieno[2,3-b]pyridine-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOc1ccc(cc1)c2c(C#N)c(N)nc3sc(C(N)=O)c(N)c23
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 ZZ5  ZZ5  3,6-diamino-5-cyano-4-(4-ethoxyphenyl)thieno[2,3-b]pyridine-2-carboxamide  ligand  40  25  .  2021-08-25  2021-08-25  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ZZ5
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 ZZ5  N19   N  NS    0  -0.243  -1.3895   4.0685   0.1761
 ZZ5  C14   C  CSP   0   0.003  -0.5460   3.2816   0.1416
 ZZ5  C6    C  CR6   0  -0.175   0.5348   2.3643   0.0984
 ZZ5  C13   C  CR6   0   0.511   1.8708   2.8625   0.2027
 ZZ5  N18   N  NH2   0  -0.830   2.1208   4.1697   0.2969
 ZZ5  N8    N  N     0  -0.482   2.9083   2.0332   0.2245
 ZZ5  C3    C  CR56  0  -0.010   2.6576   0.7445   0.1239
 ZZ5  S7    S  S2    0   0.193   3.9358  -0.4079   0.1302
 ZZ5  C9    C  CR5   0  -0.447   2.7967  -1.7331  -0.0724
 ZZ5  C15   C  C     0   0.531   3.2289  -3.1155  -0.2039
 ZZ5  N20   N  NH2   0  -0.835   4.5464  -3.3725  -0.0766
 ZZ5  O21   O  O     0  -0.514   2.4215  -4.0198  -0.4393
 ZZ5  C4    C  CR5   0   0.349   1.4852  -1.3002  -0.1390
 ZZ5  N10   N  NH2   0  -0.848   0.4167  -2.1065  -0.2841
 ZZ5  C1    C  CR56  0   0.027   1.3931   0.1399  -0.0031
 ZZ5  C2    C  CR6   0   0.313   0.2897   0.9988   0.0035
 ZZ5  C5    C  CR6   0  -0.141  -1.1090   0.5248  -0.0605
 ZZ5  C12   C  CR16  0  -0.228  -1.8788   0.7229  -1.2070
 ZZ5  C17   C  CR16  0  -0.337  -3.1912   0.2968  -1.2548
 ZZ5  C11   C  CR16  0  -0.238  -1.6889  -0.0998   1.0369
 ZZ5  C16   C  CR16  0  -0.372  -3.0096  -0.5228   1.0044
 ZZ5  C22   C  CR6   0   0.396  -3.7715  -0.3286  -0.1475
 ZZ5  O23   O  O2    0  -0.466  -5.0517  -0.7033  -0.2805
 ZZ5  C24   C  CH2   0  -0.193  -5.7078  -1.3367   0.8129
 ZZ5  C25   C  CH3   0  -0.681  -7.1227  -1.6501   0.3898
 ZZ5  H181  H  HNH2  0   0.420   1.3988   4.8679   0.2635
 ZZ5  H182  H  HNH2  0   0.412   3.0720   4.4869   0.3765
 ZZ5  H201  H  HNH2  0   0.406   5.2214  -2.6951   0.2342
 ZZ5  H202  H  HNH2  0   0.404   4.8592  -4.3289  -0.1106
 ZZ5  H101  H  HNH2  0   0.405   0.6034  -3.0666  -0.5264
 ZZ5  H102  H  HNH2  0   0.405  -0.4627  -1.7220  -0.5779
 ZZ5  H12   H  HCR6  0   0.268  -1.4446   1.2031  -2.0750
 ZZ5  H11   H  HCR6  0   0.269  -1.1086  -0.2595   1.9369
 ZZ5  H17   H  HCR6  0   0.270  -3.7795   0.4472  -2.1511
 ZZ5  H16   H  HCR6  0   0.287  -3.4213  -0.9992   1.8828
 ZZ5  H241  H  HCH2  0   0.229  -5.1789  -2.2543   1.0897
 ZZ5  H242  H  HCH2  0   0.229  -5.7064  -0.6761   1.6862
 ZZ5  H251  H  HCH3  0   0.236  -7.6692  -0.7452   0.1235
 ZZ5  H252  H  HCH3  0   0.236  -7.1435  -2.3325  -0.4598
 ZZ5  H253  H  HCH3  0   0.239  -7.6485  -2.1270   1.2161

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 ZZ5  N19  C14   triple    1.154  0.020  1.154
 ZZ5  C14  C6    single    1.418  0.020  1.418
 ZZ5  C6   C13   aromatic  1.430  0.020  1.430
 ZZ5  C6   C2    aromatic  1.391  0.020  1.391
 ZZ5  C13  N18   single    1.334  0.020  1.334
 ZZ5  C13  N8    aromatic  1.328  0.020  1.328
 ZZ5  N8   C3    aromatic  1.317  0.020  1.317
 ZZ5  C3   S7    aromatic  1.721  0.020  1.721
 ZZ5  C3   C1    aromatic  1.407  0.020  1.407
 ZZ5  S7   C9    aromatic  1.759  0.020  1.759
 ZZ5  C9   C15   single    1.454  0.020  1.454
 ZZ5  C9   C4    aromatic  1.383  0.020  1.383
 ZZ5  C15  N20   single    1.348  0.020  1.348
 ZZ5  C15  O21   double    1.235  0.020  1.235
 ZZ5  C4   N10   single    1.346  0.020  1.346
 ZZ5  C4   C1    aromatic  1.449  0.020  1.449
 ZZ5  C1   C2    aromatic  1.398  0.020  1.398
 ZZ5  C2   C5    single    1.478  0.020  1.478
 ZZ5  C5   C12   aromatic  1.395  0.020  1.395
 ZZ5  C5   C11   aromatic  1.390  0.020  1.390
 ZZ5  C12  C17   aromatic  1.381  0.020  1.381
 ZZ5  C17  C22   aromatic  1.398  0.020  1.398
 ZZ5  C11  C16   aromatic  1.387  0.020  1.387
 ZZ5  C16  C22   aromatic  1.395  0.020  1.395
 ZZ5  C22  O23   single    1.341  0.020  1.341
 ZZ5  O23  C24   single    1.424  0.020  1.424
 ZZ5  C24  C25   single    1.510  0.020  1.510
 ZZ5  N18  H181  single    0.860  0.020  1.020
 ZZ5  N18  H182  single    0.860  0.020  1.020
 ZZ5  N20  H201  single    0.860  0.020  1.020
 ZZ5  N20  H202  single    0.860  0.020  1.020
 ZZ5  N10  H101  single    0.890  0.020  1.040
 ZZ5  N10  H102  single    0.890  0.020  1.040
 ZZ5  C12  H12   single    0.930  0.020  1.080
 ZZ5  C11  H11   single    0.930  0.020  1.080
 ZZ5  C17  H17   single    0.930  0.020  1.080
 ZZ5  C16  H16   single    0.930  0.020  1.080
 ZZ5  C24  H241  single    0.970  0.020  1.090
 ZZ5  C24  H242  single    0.970  0.020  1.090
 ZZ5  C25  H251  single    0.970  0.020  1.090
 ZZ5  C25  H252  single    0.970  0.020  1.090
 ZZ5  C25  H253  single    0.970  0.020  1.090

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 ZZ5  C6    C14  N19   180.00  3.000
 ZZ5  C2    C6   C13   120.79  3.000
 ZZ5  C2    C6   C14   120.19  3.000
 ZZ5  C13   C6   C14   118.98  3.000
 ZZ5  N8    C13  N18   117.66  3.000
 ZZ5  N8    C13  C6    120.89  3.000
 ZZ5  N18   C13  C6    121.44  3.000
 ZZ5  H182  N18  H181  117.58  3.000
 ZZ5  H182  N18  C13   119.45  3.000
 ZZ5  H181  N18  C13   122.94  3.000
 ZZ5  C3    N8   C13   117.46  3.000
 ZZ5  C1    C3   S7    112.33  3.000
 ZZ5  C1    C3   N8    126.76  3.000
 ZZ5  S7    C3   N8    120.91  3.000
 ZZ5  C9    S7   C3     91.32  3.000
 ZZ5  C4    C9   C15   125.11  3.000
 ZZ5  C4    C9   S7    112.57  3.000
 ZZ5  C15   C9   S7    122.28  3.000
 ZZ5  O21   C15  N20   121.15  3.000
 ZZ5  O21   C15  C9    121.27  3.000
 ZZ5  N20   C15  C9    117.58  3.000
 ZZ5  H202  N20  H201  116.22  3.000
 ZZ5  H202  N20  C15   118.78  3.000
 ZZ5  H201  N20  C15   123.83  3.000
 ZZ5  C1    C4   N10   123.69  3.000
 ZZ5  C1    C4   C9    111.52  3.000
 ZZ5  N10   C4   C9    124.78  3.000
 ZZ5  H102  N10  H101  117.18  3.000
 ZZ5  H102  N10  C4    119.83  3.000
 ZZ5  H101  N10  C4    116.71  3.000
 ZZ5  C2    C1   C4    131.37  3.000
 ZZ5  C2    C1   C3    116.40  3.000
 ZZ5  C4    C1   C3    112.22  3.000
 ZZ5  C5    C2   C1    123.33  3.000
 ZZ5  C5    C2   C6    118.99  3.000
 ZZ5  C1    C2   C6    117.68  3.000
 ZZ5  C11   C5   C12   118.86  3.000
 ZZ5  C11   C5   C2    120.32  3.000
 ZZ5  C12   C5   C2    120.80  3.000
 ZZ5  H12   C12  C17   119.36  3.000
 ZZ5  H12   C12  C5    120.04  3.000
 ZZ5  C17   C12  C5    120.60  3.000
 ZZ5  H17   C17  C22   119.49  3.000
 ZZ5  H17   C17  C12   120.16  3.000
 ZZ5  C22   C17  C12   120.35  3.000
 ZZ5  H11   C11  C16   119.00  3.000
 ZZ5  H11   C11  C5    119.94  3.000
 ZZ5  C16   C11  C5    121.06  3.000
 ZZ5  H16   C16  C22   121.64  3.000
 ZZ5  H16   C16  C11   118.56  3.000
 ZZ5  C22   C16  C11   119.80  3.000
 ZZ5  O23   C22  C16   124.39  3.000
 ZZ5  O23   C22  C17   116.29  3.000
 ZZ5  C16   C22  C17   119.33  3.000
 ZZ5  C24   O23  C22   119.22  3.000
 ZZ5  H242  C24  H241  107.66  3.000
 ZZ5  H242  C24  C25   110.49  3.000
 ZZ5  H241  C24  C25   110.47  3.000
 ZZ5  H242  C24  O23   110.09  3.000
 ZZ5  H241  C24  O23   110.14  3.000
 ZZ5  C25   C24  O23   108.00  3.000
 ZZ5  H253  C25  H252  107.93  3.000
 ZZ5  H253  C25  H251  107.86  3.000
 ZZ5  H252  C25  H251  108.65  3.000
 ZZ5  H253  C25  C24   109.31  3.000
 ZZ5  H252  C25  C24   111.49  3.000
 ZZ5  H251  C25  C24   111.47  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 ZZ5  CONST_01  C3    N8   C13  C6      0.00   0.0  0
 ZZ5  CONST_02  C3    C1   C2   C6      0.00   0.0  0
 ZZ5  CONST_03  C4    C1   C2   C6    180.00   0.0  0
 ZZ5  CONST_06  C1    C2   C6   C13     0.00   0.0  0
 ZZ5  CONST_07  C5    C2   C6   C13   180.00   0.0  0
 ZZ5  CONST_08  S7    C3   N8   C13   180.00   0.0  0
 ZZ5  CONST_09  C1    C3   N8   C13     0.00   0.0  0
 ZZ5  CONST_10  C2    C6   C13  N8      0.00   0.0  0
 ZZ5  CONST_11  C9    S7   C3   N8    180.00   0.0  0
 ZZ5  CONST_12  C4    C1   C3   N8    180.00   0.0  0
 ZZ5  CONST_13  C2    C1   C3   N8      0.00   0.0  0
 ZZ5  CONST_14  C4    C9   S7   C3      0.00   0.0  0
 ZZ5  CONST_15  C9    C4   C1   C3      0.00   0.0  0
 ZZ5  CONST_16  C5    C2   C1   C3    180.00   0.0  0
 ZZ5  CONST_17  C4    C1   C3   S7      0.00   0.0  0
 ZZ5  CONST_18  C2    C1   C3   S7    180.00   0.0  0
 ZZ5  CONST_19  C1    C4   C9   S7      0.00   0.0  0
 ZZ5  CONST_20  C1    C3   S7   C9      0.00   0.0  0
 ZZ5  CONST_21  C2    C1   C4   C9    180.00   0.0  0
 ZZ5  CONST_22  C5    C2   C1   C4      0.00   0.0  0
 ZZ5  CONST_25  C17   C12  C5   C2    180.00   0.0  0
 ZZ5  CONST_26  C16   C11  C5   C2    180.00   0.0  0
 ZZ5  CONST_27  C22   C17  C12  C5      0.00   0.0  0
 ZZ5  CONST_28  C22   C16  C11  C5      0.00   0.0  0
 ZZ5  CONST_29  C16   C11  C5   C12     0.00   0.0  0
 ZZ5  CONST_30  C16   C22  C17  C12     0.00   0.0  0
 ZZ5  CONST_31  C11   C5   C12  C17     0.00   0.0  0
 ZZ5  CONST_32  C11   C16  C22  C17     0.00   0.0  0
 ZZ5  CONST_33  N8    C13  C6   C14   180.00   0.0  0
 ZZ5  CONST_34  C1    C2   C6   C14   180.00   0.0  0
 ZZ5  CONST_35  C5    C2   C6   C14     0.00   0.0  0
 ZZ5  CONST_36  C2    C6   C13  N18   180.00   0.0  0
 ZZ5  CONST_37  C3    N8   C13  N18   180.00   0.0  0
 ZZ5  CONST_38  C15   C9   S7   C3    180.00   0.0  0
 ZZ5  CONST_39  N10   C4   C1   C3    180.00   0.0  0
 ZZ5  CONST_40  N10   C4   C9   S7    180.00   0.0  0
 ZZ5  CONST_41  C1    C4   C9   C15   180.00   0.0  0
 ZZ5  CONST_42  C2    C1   C4   N10     0.00   0.0  0
 ZZ5  CONST_43  O23   C22  C17  C12   180.00   0.0  0
 ZZ5  CONST_44  O23   C22  C16  C11   180.00   0.0  0
 ZZ5  CONST_45  H12   C12  C5   C2      0.00   0.0  0
 ZZ5  CONST_46  H11   C11  C5   C2      0.00   0.0  0
 ZZ5  CONST_47  H17   C17  C12  C5    180.00   0.0  0
 ZZ5  CONST_48  H16   C16  C11  C5    180.00   0.0  0
 ZZ5  CONST_49  H181  N18  C13  C6      0.00   0.0  0
 ZZ5  CONST_50  H182  N18  C13  C6    180.00   0.0  0
 ZZ5  CONST_51  H101  N10  C4   C9      0.00   0.0  0
 ZZ5  CONST_53  H201  N20  C15  C9      0.00   0.0  0
 ZZ5  CONST_54  H202  N20  C15  C9    180.00   0.0  0
 ZZ5  Var_01    N20   C15  C9   S7      4.33  30.0  2
 ZZ5  Var_02    C25   C24  O23  C22  -179.85  30.0  3
 ZZ5  Var_03    H251  C25  C24  O23   -60.28  30.0  3

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 ZZ5  plan-1  C2    0.020
 ZZ5  plan-1  C5    0.020
 ZZ5  plan-1  C12   0.020
 ZZ5  plan-1  C17   0.020
 ZZ5  plan-1  C11   0.020
 ZZ5  plan-1  C16   0.020
 ZZ5  plan-1  C22   0.020
 ZZ5  plan-1  O23   0.020
 ZZ5  plan-1  H12   0.020
 ZZ5  plan-1  H11   0.020
 ZZ5  plan-1  H17   0.020
 ZZ5  plan-1  H16   0.020
 ZZ5  plan-2  N19   0.020
 ZZ5  plan-2  C14   0.020
 ZZ5  plan-2  C6    0.020
 ZZ5  plan-2  C13   0.020
 ZZ5  plan-2  N18   0.020
 ZZ5  plan-2  N8    0.020
 ZZ5  plan-2  C3    0.020
 ZZ5  plan-2  S7    0.020
 ZZ5  plan-2  C9    0.020
 ZZ5  plan-2  C15   0.020
 ZZ5  plan-2  C4    0.020
 ZZ5  plan-2  N10   0.020
 ZZ5  plan-2  C1    0.020
 ZZ5  plan-2  C2    0.020
 ZZ5  plan-2  C5    0.020
 ZZ5  plan-3  C9    0.020
 ZZ5  plan-3  C15   0.020
 ZZ5  plan-3  N20   0.020
 ZZ5  plan-3  O21   0.020
 ZZ5  plan-3  H201  0.020
 ZZ5  plan-3  H202  0.020
 ZZ5  plan-4  C13   0.020
 ZZ5  plan-4  N18   0.020
 ZZ5  plan-4  H181  0.020
 ZZ5  plan-4  H182  0.020
 ZZ5  plan-5  C4    0.020
 ZZ5  plan-5  N10   0.020
 ZZ5  plan-5  H101  0.020
 ZZ5  plan-5  H102  0.020

