# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 11:56:51 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: N-(3-aminopropyl)-8-[(3-fluorophenyl)amino]-1,4,5,7-tetrahydropyrazolo[3,4-e]indazole-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NCCCNC(=O)c1n[nH]c2c1CCc3n[nH]c(Nc4cccc(F)c4)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
 1WS  1WS  N-(3-aminopropyl)-8-[(3-fluorophenyl)amino]-1,4,5,7-tetrahydropyrazolo[3,4-e]indazole-3-carboxamide  ligand  47  27  .  2021-08-03  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1WS
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
 1WS  O23   O  O     0  -0.493   4.1634  -1.7839  -0.6554
 1WS  C21   C  C     0   0.509   3.7365  -0.6971  -0.2815
 1WS  N22   N  NH1   0  -0.655   4.5040   0.3937  -0.1658
 1WS  C24   C  CH2   0  -0.237   5.9158   0.3932  -0.4832
 1WS  C25   C  CH2   0  -0.485   6.5354   1.7456  -0.1740
 1WS  C26   C  CH2   0  -0.271   8.0284   1.7584  -0.4639
 1WS  N27   N  NH2   0  -0.800   8.5989   3.0621  -0.1610
 1WS  C8    C  CR5   0   0.053   2.3115  -0.5177   0.0767
 1WS  C7    C  CR56  0  -0.119   1.3064  -1.5006   0.1203
 1WS  C4    C  C     0  -0.511   1.2486  -2.9628  -0.2047
 1WS  C3    C  C     0  -0.527   0.1286  -3.6723   0.5785
 1WS  N9    N  N     0  -0.285   1.8355   0.6767   0.4085
 1WS  N10   N  NR15  0  -0.521   0.5514   0.4865   0.6560
 1WS  C6    C  CR56  0   0.378   0.1790  -0.7967   0.4978
 1WS  C1    C  CR56  0  -0.141  -1.0923  -1.4438   0.6486
 1WS  C11   C  CR5   0   0.561  -2.4125  -1.0623   0.7553
 1WS  N12   N  NR15  0  -0.480  -3.1183  -2.2142   0.7881
 1WS  N5    N  N     0  -0.291  -2.3533  -3.3060   0.6896
 1WS  C2    C  CR56  0   0.223  -1.1211  -2.8544   0.6226
 1WS  N13   N  NH1   0  -0.806  -2.9738   0.1919   0.8571
 1WS  C14   C  CR6   0   0.397  -4.0226   0.6739   0.0977
 1WS  C19   C  CR16  0  -0.513  -4.6224   1.8761   0.4837
 1WS  C18   C  CR6   0   0.539  -5.6502   2.3854  -0.2802
 1WS  F20   F  F     0  -0.317  -6.2080   3.5446   0.1053
 1WS  C17   C  CR16  0  -0.439  -6.1322   1.7581  -1.4131
 1WS  C16   C  CR16  0  -0.230  -5.5269   0.5642  -1.7810
 1WS  C15   C  CR16  0  -0.355  -4.4839   0.0188  -1.0488
 1WS  H22   H  HNH1  0   0.404   4.0731   1.2540   0.1354
 1WS  H241  H  HCH2  0   0.231   6.4216  -0.3867   0.0926
 1WS  H242  H  HCH2  0   0.231   6.0634   0.1497  -1.5402
 1WS  H251  H  HCH2  0   0.233   6.0466   2.5265  -0.7635
 1WS  H252  H  HCH2  0   0.231   6.3686   1.9895   0.8805
 1WS  H261  H  HCH2  0   0.194   8.5031   0.9320   0.0848
 1WS  H262  H  HCH2  0   0.218   8.1881   1.5520  -1.5255
 1WS  H271  H  HNH2  0   0.339   8.5585   3.2184   0.8391
 1WS  H272  H  HNH2  0   0.348   9.5837   3.0597  -0.3935
 1WS  H41C  H  H     0   0.248   1.0754  -3.0834  -1.2789
 1WS  H42C  H  H     0   0.259   2.1986  -3.4483   0.0086
 1WS  H31C  H  H     0   0.263  -0.0643  -4.6568   0.1514
 1WS  H32C  H  H     0   0.259   0.4676  -3.8375   1.6065
 1WS  H10   H  HNR5  0   0.417  -0.0209   1.2679   0.9351
 1WS  H12   H  HNR5  0   0.425  -4.1190  -2.3105   0.8655
 1WS  H13   H  HNH1  0   0.415  -2.6434   0.7748   1.6097
 1WS  H19   H  HCR6  0   0.285  -4.2870   2.4055   1.3672
 1WS  H15   H  HCR6  0   0.274  -4.0283  -0.9035  -1.3823
 1WS  H17   H  HCR6  0   0.275  -6.9433   2.1856  -1.9865
 1WS  H16   H  HCR6  0   0.270  -5.8729   0.0459  -2.6656

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
 1WS  O23  C21   double    1.226  0.020  1.226
 1WS  C21  N22   single    1.339  0.020  1.339
 1WS  C21  C8    single    1.480  0.020  1.480
 1WS  N22  C24   single    1.447  0.020  1.447
 1WS  C24  C25   single    1.519  0.020  1.519
 1WS  C25  C26   single    1.521  0.020  1.521
 1WS  C26  N27   single    1.455  0.020  1.455
 1WS  C8   C7    aromatic  1.406  0.020  1.406
 1WS  C8   N9    aromatic  1.328  0.020  1.328
 1WS  C7   C4    single    1.499  0.020  1.499
 1WS  C7   C6    aromatic  1.382  0.020  1.382
 1WS  C4   C3    single    1.540  0.020  1.540
 1WS  C3   C2    single    1.494  0.020  1.494
 1WS  N9   N10   aromatic  1.322  0.020  1.322
 1WS  N10  C6    aromatic  1.346  0.020  1.346
 1WS  C6   C1    aromatic  1.434  0.020  1.434
 1WS  C1   C11   aromatic  1.378  0.020  1.378
 1WS  C1   C2    aromatic  1.411  0.020  1.411
 1WS  C11  N12   aromatic  1.351  0.020  1.351
 1WS  C11  N13   single    1.378  0.020  1.378
 1WS  N12  N5    aromatic  1.337  0.020  1.337
 1WS  N5   C2    aromatic  1.314  0.020  1.314
 1WS  N13  C14   single    1.382  0.020  1.382
 1WS  C14  C19   aromatic  1.398  0.020  1.398
 1WS  C14  C15   aromatic  1.399  0.020  1.399
 1WS  C19  C18   aromatic  1.378  0.020  1.378
 1WS  C18  F20   single    1.343  0.020  1.343
 1WS  C18  C17   aromatic  1.382  0.020  1.382
 1WS  C17  C16   aromatic  1.388  0.020  1.388
 1WS  C16  C15   aromatic  1.386  0.020  1.386
 1WS  N22  H22   single    0.860  0.020  1.020
 1WS  C24  H241  single    0.970  0.020  1.090
 1WS  C24  H242  single    0.970  0.020  1.090
 1WS  C25  H251  single    0.970  0.020  1.090
 1WS  C25  H252  single    0.970  0.020  1.090
 1WS  C26  H261  single    0.970  0.020  1.090
 1WS  C26  H262  single    0.970  0.020  1.090
 1WS  N27  H271  single    0.890  0.020  1.040
 1WS  N27  H272  single    0.890  0.020  1.040
 1WS  C4   H41C  single    0.970  0.020  1.090
 1WS  C4   H42C  single    0.970  0.020  1.090
 1WS  C3   H31C  single    0.970  0.020  1.090
 1WS  C3   H32C  single    0.970  0.020  1.090
 1WS  N10  H10   single    0.860  0.020  1.020
 1WS  N12  H12   single    0.860  0.020  1.020
 1WS  N13  H13   single    0.860  0.020  1.020
 1WS  C19  H19   single    0.930  0.020  1.080
 1WS  C15  H15   single    0.930  0.020  1.080
 1WS  C17  H17   single    0.930  0.020  1.080
 1WS  C16  H16   single    0.930  0.020  1.080

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
 1WS  C8    C21  N22   115.61  3.000
 1WS  C8    C21  O23   121.09  3.000
 1WS  N22   C21  O23   123.29  3.000
 1WS  H22   N22  C24   118.87  3.000
 1WS  H22   N22  C21   118.42  3.000
 1WS  C24   N22  C21   122.69  3.000
 1WS  H242  C24  H241  106.71  3.000
 1WS  H242  C24  C25   109.85  3.000
 1WS  H241  C24  C25   109.82  3.000
 1WS  H242  C24  N22   110.09  3.000
 1WS  H241  C24  N22   109.63  3.000
 1WS  C25   C24  N22   110.66  3.000
 1WS  H252  C25  H251  106.97  3.000
 1WS  H252  C25  C26   109.34  3.000
 1WS  H251  C25  C26   109.26  3.000
 1WS  H252  C25  C24   109.40  3.000
 1WS  H251  C25  C24   110.09  3.000
 1WS  C26   C25  C24   111.65  3.000
 1WS  H262  C26  H261  106.24  3.000
 1WS  H262  C26  N27   108.31  3.000
 1WS  H261  C26  N27   113.59  3.000
 1WS  H262  C26  C25   109.08  3.000
 1WS  H261  C26  C25   108.80  3.000
 1WS  N27   C26  C25   110.65  3.000
 1WS  H272  N27  H271  105.43  3.000
 1WS  H272  N27  C26   109.37  3.000
 1WS  H271  N27  C26   109.16  3.000
 1WS  N9    C8   C7    111.38  3.000
 1WS  N9    C8   C21   120.97  3.000
 1WS  C7    C8   C21   127.65  3.000
 1WS  C6    C7   C4    121.65  3.000
 1WS  C6    C7   C8    103.63  3.000
 1WS  C4    C7   C8    134.62  3.000
 1WS  H42C  C4   H41C  106.34  3.000
 1WS  H42C  C4   C3    109.25  3.000
 1WS  H41C  C4   C3    109.46  3.000
 1WS  H42C  C4   C7    111.05  3.000
 1WS  H41C  C4   C7    109.04  3.000
 1WS  C3    C4   C7    111.55  3.000
 1WS  H32C  C3   H31C  106.63  3.000
 1WS  H32C  C3   C2    108.28  3.000
 1WS  H31C  C3   C2    110.97  3.000
 1WS  H32C  C3   C4    108.78  3.000
 1WS  H31C  C3   C4    110.21  3.000
 1WS  C2    C3   C4    111.79  3.000
 1WS  N10   N9   C8    105.41  3.000
 1WS  H10   N10  C6    127.93  3.000
 1WS  H10   N10  N9    119.47  3.000
 1WS  C6    N10  N9    112.59  3.000
 1WS  C1    C6   N10   131.54  3.000
 1WS  C1    C6   C7    121.47  3.000
 1WS  N10   C6   C7    106.98  3.000
 1WS  C2    C1   C11   104.99  3.000
 1WS  C2    C1   C6    117.84  3.000
 1WS  C11   C1   C6    137.07  3.000
 1WS  N13   C11  N12   124.15  3.000
 1WS  N13   C11  C1    130.38  3.000
 1WS  N12   C11  C1    105.44  3.000
 1WS  H12   N12  N5    119.71  3.000
 1WS  H12   N12  C11   126.99  3.000
 1WS  N5    N12  C11   113.30  3.000
 1WS  C2    N5   N12   105.05  3.000
 1WS  N5    C2   C1    111.21  3.000
 1WS  N5    C2   C3    126.70  3.000
 1WS  C1    C2   C3    122.05  3.000
 1WS  H13   N13  C14   117.24  3.000
 1WS  H13   N13  C11   116.63  3.000
 1WS  C14   N13  C11   125.88  3.000
 1WS  C15   C14  C19   119.19  3.000
 1WS  C15   C14  N13   122.52  3.000
 1WS  C19   C14  N13   118.29  3.000
 1WS  H19   C19  C18   120.16  3.000
 1WS  H19   C19  C14   120.84  3.000
 1WS  C18   C19  C14   118.99  3.000
 1WS  C17   C18  F20   118.84  3.000
 1WS  C17   C18  C19   123.15  3.000
 1WS  F20   C18  C19   118.01  3.000
 1WS  H17   C17  C16   121.78  3.000
 1WS  H17   C17  C18   121.12  3.000
 1WS  C16   C17  C18   117.10  3.000
 1WS  H16   C16  C15   118.95  3.000
 1WS  H16   C16  C17   119.28  3.000
 1WS  C15   C16  C17   121.77  3.000
 1WS  H15   C15  C16   119.32  3.000
 1WS  H15   C15  C14   120.88  3.000
 1WS  C16   C15  C14   119.79  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
 1WS  CONST_01  N10   C6   C7   C8      0.00   0.0  0
 1WS  CONST_02  C1    C6   C7   C8    180.00   0.0  0
 1WS  CONST_03  C6    N10  N9   C8      0.00   0.0  0
 1WS  CONST_04  N10   N9   C8   C7      0.00   0.0  0
 1WS  CONST_05  N9    N10  C6   C7      0.00   0.0  0
 1WS  CONST_06  C11   C1   C6   C7    180.00   0.0  0
 1WS  CONST_07  C2    C1   C6   C7      0.00   0.0  0
 1WS  CONST_08  C6    C7   C8   N9      0.00   0.0  0
 1WS  CONST_09  C1    C6   N10  N9    180.00   0.0  0
 1WS  CONST_10  C11   C1   C6   N10     0.00   0.0  0
 1WS  CONST_11  C2    C1   C6   N10   180.00   0.0  0
 1WS  CONST_12  N12   C11  C1   C6    180.00   0.0  0
 1WS  CONST_13  N5    C2   C1   C6    180.00   0.0  0
 1WS  CONST_14  N5    N12  C11  C1      0.00   0.0  0
 1WS  CONST_15  N12   N5   C2   C1      0.00   0.0  0
 1WS  CONST_16  N5    C2   C1   C11     0.00   0.0  0
 1WS  CONST_17  C2    N5   N12  C11     0.00   0.0  0
 1WS  CONST_18  C2    C1   C11  N12     0.00   0.0  0
 1WS  CONST_19  C17   C18  C19  C14     0.00   0.0  0
 1WS  CONST_20  C17   C16  C15  C14     0.00   0.0  0
 1WS  CONST_21  C16   C15  C14  C19     0.00   0.0  0
 1WS  CONST_22  C16   C17  C18  C19     0.00   0.0  0
 1WS  CONST_23  C15   C14  C19  C18     0.00   0.0  0
 1WS  CONST_24  C15   C16  C17  C18     0.00   0.0  0
 1WS  CONST_25  C4    C7   C8   C21     0.00   0.0  0
 1WS  CONST_26  C6    C7   C8   C21   180.00   0.0  0
 1WS  CONST_27  N10   N9   C8   C21   180.00   0.0  0
 1WS  CONST_28  N13   C11  C1   C6      0.00   0.0  0
 1WS  CONST_29  N13   C11  N12  N5    180.00   0.0  0
 1WS  CONST_30  N13   C11  C1   C2    180.00   0.0  0
 1WS  CONST_31  C18   C19  C14  N13   180.00   0.0  0
 1WS  CONST_32  C16   C15  C14  N13   180.00   0.0  0
 1WS  CONST_33  F20   C18  C19  C14   180.00   0.0  0
 1WS  CONST_34  C16   C17  C18  F20   180.00   0.0  0
 1WS  CONST_35  H10   N10  N9   C8    180.00   0.0  0
 1WS  CONST_36  H12   N12  C11  C1    180.00   0.0  0
 1WS  CONST_37  H16   C16  C15  C14   180.00   0.0  0
 1WS  CONST_38  H15   C15  C14  C19   180.00   0.0  0
 1WS  CONST_39  H17   C17  C18  C19   180.00   0.0  0
 1WS  CONST_40  H19   C19  C18  C17   180.00   0.0  0
 1WS  CONST_41  C8    C21  N22  C24   180.00   0.0  0
 1WS  CONST_42  H22   N22  C21  C8      0.00   0.0  0
 1WS  CONST_43  C24   N22  C21  O23     0.00   0.0  0
 1WS  Var_01    C3    C4   C7   C8    154.92  30.0  1
 1WS  Var_02    C2    C3   C4   C7     41.75  30.0  1
 1WS  Var_03    C1    C2   C3   C4    -32.61  30.0  1
 1WS  Var_04    C14   N13  C11  C1    130.56  30.0  2
 1WS  Var_05    C19   C14  N13  C11   168.97  30.0  2
 1WS  Var_06    C7    C8   C21  O23     3.77  30.0  2
 1WS  Var_07    C25   C24  N22  C21  -176.52  30.0  3
 1WS  Var_08    C26   C25  C24  N22   178.44  30.0  3
 1WS  Var_09    N27   C26  C25  C24   179.98  30.0  3
 1WS  Var_10    H271  N27  C26  C25    67.25  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
 1WS  plan-1  N13  0.020
 1WS  plan-1  C14  0.020
 1WS  plan-1  C19  0.020
 1WS  plan-1  C18  0.020
 1WS  plan-1  F20  0.020
 1WS  plan-1  C17  0.020
 1WS  plan-1  C16  0.020
 1WS  plan-1  C15  0.020
 1WS  plan-1  H19  0.020
 1WS  plan-1  H15  0.020
 1WS  plan-1  H17  0.020
 1WS  plan-1  H16  0.020
 1WS  plan-2  C21  0.020
 1WS  plan-2  C8   0.020
 1WS  plan-2  C7   0.020
 1WS  plan-2  C4   0.020
 1WS  plan-2  N9   0.020
 1WS  plan-2  N10  0.020
 1WS  plan-2  C6   0.020
 1WS  plan-2  C1   0.020
 1WS  plan-2  H10  0.020
 1WS  plan-3  C3   0.020
 1WS  plan-3  C6   0.020
 1WS  plan-3  C1   0.020
 1WS  plan-3  C11  0.020
 1WS  plan-3  N12  0.020
 1WS  plan-3  N5   0.020
 1WS  plan-3  C2   0.020
 1WS  plan-3  N13  0.020
 1WS  plan-3  H12  0.020
 1WS  plan-4  O23  0.020
 1WS  plan-4  C21  0.020
 1WS  plan-4  N22  0.020
 1WS  plan-4  C24  0.020
 1WS  plan-4  C8   0.020
 1WS  plan-4  H22  0.020

