# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 08:55:55 2020
#   Inital geometry file: a 139 line input string
#   Ligand name: 4'-[3-({4-[(cyclopropylamino)methyl]phenyl}amino)-1H-pyrazol-5-yl]biphenyl-2,4-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(c(O)c1)c2ccc(cc2)c3[nH]nc(Nc4ccc(CNC5CC5)cc4)c3
#
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
 TC0  TC0  4'-[3-({4-[(cyclopropylamino)methyl]phenyl}amino)-1H-pyrazol-5-yl]biphenyl-2,4-diol  ligand  55  31  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_TC0
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
 TC0  C1    C  CH2   0  -0.504  -11.0118   1.0591   1.3489
 TC0  C2    C  CH2   0  -0.488  -11.0432  -0.0149   0.3011
 TC0  C3    C  CH1   0  -0.091  -10.0798   1.1235   0.1827
 TC0  N1    N  NH1   0  -0.587   -8.6986   0.8365   0.4149
 TC0  C4    C  CH2   0  -0.331   -8.0183   0.3510  -0.7766
 TC0  C5    C  CR6   0   0.072   -6.5782   0.0402  -0.4836
 TC0  C6    C  CR16  0  -0.278   -6.2275  -1.0463   0.3188
 TC0  C7    C  CR16  0  -0.356   -4.9081  -1.3299   0.6060
 TC0  C10   C  CR16  0  -0.300   -5.5487   0.8348  -0.9666
 TC0  C9    C  CR16  0  -0.323   -4.2121   0.5732  -0.6854
 TC0  C8    C  CR6   0   0.347   -3.8704  -0.5251   0.1076
 TC0  N2    N  NH1   0  -0.797   -2.5776  -0.8835   0.4342
 TC0  C11   C  CR5   0   0.507   -1.3834  -0.2969   0.0915
 TC0  C12   C  CR15  0  -0.614   -0.1162  -0.8329   0.4078
 TC0  N4    N  N     0  -0.327   -1.2735   0.8468  -0.5607
 TC0  N3    N  NR15  0  -0.517    0.0451   1.0544  -0.6619
 TC0  C13   C  CR5   0   0.463    0.7837   0.0788  -0.1049
 TC0  C14   C  CR6   0   0.061    2.2427   0.0832  -0.0921
 TC0  C19   C  CR16  0  -0.287    2.9726   1.2621  -0.2392
 TC0  C18   C  CR16  0  -0.291    4.3575   1.2398  -0.2231
 TC0  C15   C  CR16  0  -0.304    2.9422  -1.1130   0.0736
 TC0  C16   C  CR16  0  -0.275    4.3250  -1.1307   0.0955
 TC0  C17   C  CR6   0   0.095    5.0615   0.0467  -0.0555
 TC0  C20   C  CR6   0  -0.065    6.5377   0.0510  -0.0849
 TC0  C21   C  CR16  0  -0.275    7.2161   0.7186  -1.1014
 TC0  C22   C  CR16  0  -0.403    8.5984   0.7646  -1.1728
 TC0  C23   C  CR6   0   0.362    9.3461   0.1270  -0.1870
 TC0  O2    O  OH1   0  -0.629   10.6914   0.1231  -0.1805
 TC0  C24   C  CR16  0  -0.471    8.7005  -0.5409   0.8486
 TC0  C25   C  CR6   0   0.347    7.3125  -0.5776   0.9024
 TC0  O1    O  OH1   0  -0.623    6.6708  -1.1921   1.9128
 TC0  H11C  H  HCH2  0   0.246  -11.8316   1.7645   1.3904
 TC0  H12C  H  HCH2  0   0.244  -10.5848   0.8062   2.3112
 TC0  H21C  H  HCH2  0   0.245  -10.6321  -0.9815   0.5649
 TC0  H22C  H  HCH2  0   0.245  -11.8852  -0.0519  -0.3779
 TC0  H3    H  HCH1  0   0.228  -10.3142   1.8666  -0.5822
 TC0  H1    H  HNH1  0   0.344   -8.2290   1.6702   0.7485
 TC0  H41C  H  HCH2  0   0.232   -8.5365  -0.5548  -1.1045
 TC0  H42C  H  HCH2  0   0.208   -8.0719   1.0603  -1.6166
 TC0  H6    H  HCR6  0   0.244   -7.0027  -1.6885   0.7208
 TC0  H10   H  HCR6  0   0.243   -5.7861   1.6920  -1.5870
 TC0  H7    H  HCR6  0   0.258   -4.6672  -2.1893   1.2223
 TC0  H9    H  HCR6  0   0.277   -3.4468   1.2216  -1.0814
 TC0  H2    H  HNH1  0   0.407   -2.4863  -1.7278   0.9746
 TC0  H12   H  HCR5  0   0.273    0.1002  -1.7400   0.9487
 TC0  HA    H  HNR5  0   0.416    0.3735   1.8514  -1.1822
 TC0  H19   H  HCR6  0   0.250    2.4678   2.2143  -0.3457
 TC0  H15   H  HCR6  0   0.256    2.3990  -2.0447   0.1713
 TC0  H18   H  HCR6  0   0.258    4.9005   2.1713  -0.3241
 TC0  H16   H  HCR6  0   0.253    4.8339  -2.0788   0.2051
 TC0  H21   H  HCR6  0   0.260    6.6402   1.2065  -1.8783
 TC0  H22   H  HCR6  0   0.270    9.0846   1.2842  -1.9897
 TC0  HB    H  HOH1  0   0.476   11.0327   0.6062  -0.9413
 TC0  H24   H  HCR6  0   0.276    9.2889  -1.0228   1.6222
 TC0  HC    H  HOH1  0   0.477    7.3050  -1.5773   2.5278

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
 TC0  C1   C2    single    1.501  0.020  1.501
 TC0  C1   C3    single    1.494  0.020  1.494
 TC0  C2   C3    single    1.496  0.020  1.496
 TC0  C3   N1    single    1.430  0.020  1.430
 TC0  N1   C4    single    1.455  0.020  1.455
 TC0  C4   C5    single    1.502  0.020  1.502
 TC0  C5   C6    aromatic  1.395  0.020  1.395
 TC0  C5   C10   aromatic  1.387  0.020  1.387
 TC0  C6   C7    aromatic  1.380  0.020  1.380
 TC0  C7   C8    aromatic  1.405  0.020  1.405
 TC0  C10  C9    aromatic  1.391  0.020  1.391
 TC0  C9   C8    aromatic  1.397  0.020  1.397
 TC0  C8   N2    single    1.381  0.020  1.381
 TC0  N2   C11   single    1.374  0.020  1.374
 TC0  C11  C12   aromatic  1.412  0.020  1.412
 TC0  C11  N4    aromatic  1.321  0.020  1.321
 TC0  C12  C13   aromatic  1.380  0.020  1.380
 TC0  N4   N3    aromatic  1.339  0.020  1.339
 TC0  N3   C13   aromatic  1.344  0.020  1.344
 TC0  C13  C14   single    1.459  0.020  1.459
 TC0  C14  C19   aromatic  1.394  0.020  1.394
 TC0  C14  C15   aromatic  1.396  0.020  1.396
 TC0  C19  C18   aromatic  1.385  0.020  1.385
 TC0  C18  C17   aromatic  1.395  0.020  1.395
 TC0  C15  C16   aromatic  1.383  0.020  1.383
 TC0  C16  C17   aromatic  1.397  0.020  1.397
 TC0  C17  C20   single    1.476  0.020  1.476
 TC0  C20  C21   aromatic  1.393  0.020  1.393
 TC0  C20  C25   aromatic  1.404  0.020  1.404
 TC0  C21  C22   aromatic  1.385  0.020  1.385
 TC0  C22  C23   aromatic  1.392  0.020  1.392
 TC0  C23  O2    single    1.345  0.020  1.345
 TC0  C23  C24   aromatic  1.391  0.020  1.391
 TC0  C24  C25   aromatic  1.390  0.020  1.390
 TC0  C25  O1    single    1.345  0.020  1.345
 TC0  C1   H11C  single    0.970  0.020  1.090
 TC0  C1   H12C  single    0.970  0.020  1.090
 TC0  C2   H21C  single    0.970  0.020  1.090
 TC0  C2   H22C  single    0.970  0.020  1.090
 TC0  C3   H3    single    0.970  0.020  1.090
 TC0  N1   H1    single    0.890  0.020  1.040
 TC0  C4   H41C  single    0.970  0.020  1.090
 TC0  C4   H42C  single    0.970  0.020  1.090
 TC0  C6   H6    single    0.930  0.020  1.080
 TC0  C10  H10   single    0.930  0.020  1.080
 TC0  C7   H7    single    0.930  0.020  1.080
 TC0  C9   H9    single    0.930  0.020  1.080
 TC0  N2   H2    single    0.860  0.020  1.020
 TC0  C12  H12   single    0.930  0.020  1.080
 TC0  N3   HA    single    0.860  0.020  1.020
 TC0  C19  H19   single    0.930  0.020  1.080
 TC0  C15  H15   single    0.930  0.020  1.080
 TC0  C18  H18   single    0.930  0.020  1.080
 TC0  C16  H16   single    0.930  0.020  1.080
 TC0  C21  H21   single    0.930  0.020  1.080
 TC0  C22  H22   single    0.930  0.020  1.080
 TC0  O2   HB    single    0.850  0.020  0.980
 TC0  C24  H24   single    0.930  0.020  1.080
 TC0  O1   HC    single    0.850  0.020  0.980

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
 TC0  H12C  C1   H11C  114.64  3.000
 TC0  H12C  C1   C3    117.24  3.000
 TC0  H11C  C1   C3    118.31  3.000
 TC0  H12C  C1   C2    117.49  3.000
 TC0  H11C  C1   C2    118.51  3.000
 TC0  C3    C1   C2     59.93  3.000
 TC0  H22C  C2   H21C  114.68  3.000
 TC0  H22C  C2   C3    118.52  3.000
 TC0  H21C  C2   C3    117.00  3.000
 TC0  H22C  C2   C1    118.60  3.000
 TC0  H21C  C2   C1    117.43  3.000
 TC0  C3    C2   C1     59.82  3.000
 TC0  H3    C3   N1    117.25  3.000
 TC0  H3    C3   C2    115.78  3.000
 TC0  N1    C3   C2    117.17  3.000
 TC0  H3    C3   C1    116.24  3.000
 TC0  N1    C3   C1    117.85  3.000
 TC0  C2    C3   C1     60.25  3.000
 TC0  H1    N1   C4    109.11  3.000
 TC0  H1    N1   C3    109.63  3.000
 TC0  C4    N1   C3    112.68  3.000
 TC0  H42C  C4   H41C  106.37  3.000
 TC0  H42C  C4   C5    109.20  3.000
 TC0  H41C  C4   C5    109.96  3.000
 TC0  H42C  C4   N1    112.77  3.000
 TC0  H41C  C4   N1    107.47  3.000
 TC0  C5    C4   N1    110.94  3.000
 TC0  C10   C5   C6    117.37  3.000
 TC0  C10   C5   C4    121.67  3.000
 TC0  C6    C5   C4    120.94  3.000
 TC0  H6    C6   C7    119.01  3.000
 TC0  H6    C6   C5    119.66  3.000
 TC0  C7    C6   C5    121.33  3.000
 TC0  H7    C7   C8    119.44  3.000
 TC0  H7    C7   C6    119.57  3.000
 TC0  C8    C7   C6    120.99  3.000
 TC0  H10   C10  C9    118.34  3.000
 TC0  H10   C10  C5    119.31  3.000
 TC0  C9    C10  C5    122.35  3.000
 TC0  H9    C9   C8    120.50  3.000
 TC0  H9    C9   C10   119.65  3.000
 TC0  C8    C9   C10   119.85  3.000
 TC0  N2    C8   C9    124.56  3.000
 TC0  N2    C8   C7    117.33  3.000
 TC0  C9    C8   C7    118.11  3.000
 TC0  H2    N2   C11   114.40  3.000
 TC0  H2    N2   C8    115.45  3.000
 TC0  C11   N2   C8    130.09  3.000
 TC0  N4    C11  C12   111.39  3.000
 TC0  N4    C11  N2    124.40  3.000
 TC0  C12   C11  N2    124.21  3.000
 TC0  H12   C12  C13   127.70  3.000
 TC0  H12   C12  C11   127.74  3.000
 TC0  C13   C12  C11   104.55  3.000
 TC0  N3    N4   C11   104.68  3.000
 TC0  HA    N3   C13   127.54  3.000
 TC0  HA    N3   N4    118.89  3.000
 TC0  C13   N3   N4    113.41  3.000
 TC0  C14   C13  N3    123.42  3.000
 TC0  C14   C13  C12   130.61  3.000
 TC0  N3    C13  C12   105.97  3.000
 TC0  C15   C14  C19   118.34  3.000
 TC0  C15   C14  C13   119.98  3.000
 TC0  C19   C14  C13   121.68  3.000
 TC0  H19   C19  C18   118.77  3.000
 TC0  H19   C19  C14   120.64  3.000
 TC0  C18   C19  C14   120.57  3.000
 TC0  H18   C18  C17   119.58  3.000
 TC0  H18   C18  C19   119.10  3.000
 TC0  C17   C18  C19   121.31  3.000
 TC0  H15   C15  C16   119.28  3.000
 TC0  H15   C15  C14   119.78  3.000
 TC0  C16   C15  C14   120.93  3.000
 TC0  H16   C16  C17   120.11  3.000
 TC0  H16   C16  C15   118.90  3.000
 TC0  C17   C16  C15   120.97  3.000
 TC0  C20   C17  C16   122.12  3.000
 TC0  C20   C17  C18   119.97  3.000
 TC0  C16   C17  C18   117.88  3.000
 TC0  C25   C20  C21   117.33  3.000
 TC0  C25   C20  C17   122.45  3.000
 TC0  C21   C20  C17   120.20  3.000
 TC0  H21   C21  C22   118.60  3.000
 TC0  H21   C21  C20   118.71  3.000
 TC0  C22   C21  C20   122.68  3.000
 TC0  H22   C22  C23   120.84  3.000
 TC0  H22   C22  C21   120.18  3.000
 TC0  C23   C22  C21   118.97  3.000
 TC0  C24   C23  O2    117.33  3.000
 TC0  C24   C23  C22   119.86  3.000
 TC0  O2    C23  C22   122.82  3.000
 TC0  HB    O2   C23   110.42  3.000
 TC0  H24   C24  C25   120.16  3.000
 TC0  H24   C24  C23   119.50  3.000
 TC0  C25   C24  C23   120.34  3.000
 TC0  O1    C25  C24   121.17  3.000
 TC0  O1    C25  C20   118.00  3.000
 TC0  C24   C25  C20   120.82  3.000
 TC0  HC    O1   C25   110.36  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
 TC0  CONST_01  C8   C7   C6   C5      0.00   0.0  0
 TC0  CONST_02  C8   C9   C10  C5      0.00   0.0  0
 TC0  CONST_03  C9   C10  C5   C6      0.00   0.0  0
 TC0  CONST_04  C9   C8   C7   C6      0.00   0.0  0
 TC0  CONST_05  C10  C5   C6   C7      0.00   0.0  0
 TC0  CONST_06  C10  C9   C8   C7      0.00   0.0  0
 TC0  CONST_07  N3   C13  C12  C11     0.00   0.0  0
 TC0  CONST_08  C14  C13  C12  C11   180.00   0.0  0
 TC0  CONST_09  C13  N3   N4   C11     0.00   0.0  0
 TC0  CONST_10  N3   N4   C11  C12     0.00   0.0  0
 TC0  CONST_11  N4   N3   C13  C12     0.00   0.0  0
 TC0  CONST_14  C13  C12  C11  N4      0.00   0.0  0
 TC0  CONST_15  C14  C13  N3   N4    180.00   0.0  0
 TC0  CONST_18  C18  C19  C14  C13   180.00   0.0  0
 TC0  CONST_19  C16  C15  C14  C13   180.00   0.0  0
 TC0  CONST_20  C17  C18  C19  C14     0.00   0.0  0
 TC0  CONST_21  C17  C16  C15  C14     0.00   0.0  0
 TC0  CONST_22  C16  C15  C14  C19     0.00   0.0  0
 TC0  CONST_23  C16  C17  C18  C19     0.00   0.0  0
 TC0  CONST_24  C20  C17  C18  C19   180.00   0.0  0
 TC0  CONST_25  C15  C14  C19  C18     0.00   0.0  0
 TC0  CONST_26  C15  C16  C17  C18     0.00   0.0  0
 TC0  CONST_29  C20  C17  C16  C15   180.00   0.0  0
 TC0  CONST_32  C22  C21  C20  C17   180.00   0.0  0
 TC0  CONST_33  C24  C25  C20  C17   180.00   0.0  0
 TC0  CONST_34  C23  C22  C21  C20     0.00   0.0  0
 TC0  CONST_35  C23  C24  C25  C20     0.00   0.0  0
 TC0  CONST_36  C24  C25  C20  C21     0.00   0.0  0
 TC0  CONST_37  C24  C23  C22  C21     0.00   0.0  0
 TC0  CONST_38  C25  C20  C21  C22     0.00   0.0  0
 TC0  CONST_39  C25  C24  C23  C22     0.00   0.0  0
 TC0  CONST_40  C7   C6   C5   C4    180.00   0.0  0
 TC0  CONST_41  C9   C10  C5   C4    180.00   0.0  0
 TC0  CONST_42  N2   C8   C7   C6    180.00   0.0  0
 TC0  CONST_43  N2   C8   C9   C10   180.00   0.0  0
 TC0  CONST_44  C13  C12  C11  N2    180.00   0.0  0
 TC0  CONST_45  N3   N4   C11  N2    180.00   0.0  0
 TC0  CONST_46  O1   C25  C20  C17     0.00   0.0  0
 TC0  CONST_47  O1   C25  C20  C21   180.00   0.0  0
 TC0  CONST_48  O2   C23  C22  C21   180.00   0.0  0
 TC0  CONST_49  O1   C25  C24  C23   180.00   0.0  0
 TC0  CONST_50  C25  C24  C23  O2    180.00   0.0  0
 TC0  CONST_51  H7   C7   C6   C5    180.00   0.0  0
 TC0  CONST_52  H9   C9   C10  C5    180.00   0.0  0
 TC0  CONST_53  H10  C10  C5   C6    180.00   0.0  0
 TC0  CONST_54  H6   C6   C5   C10   180.00   0.0  0
 TC0  CONST_55  HA   N3   N4   C11   180.00   0.0  0
 TC0  CONST_56  H12  C12  C11  N4    180.00   0.0  0
 TC0  CONST_57  H19  C19  C14  C13     0.00   0.0  0
 TC0  CONST_58  H15  C15  C14  C13     0.00   0.0  0
 TC0  CONST_59  H18  C18  C19  C14   180.00   0.0  0
 TC0  CONST_60  H16  C16  C15  C14   180.00   0.0  0
 TC0  CONST_61  H21  C21  C20  C17     0.00   0.0  0
 TC0  CONST_62  H22  C22  C21  C20   180.00   0.0  0
 TC0  CONST_63  H24  C24  C25  C20   180.00   0.0  0
 TC0  Var_01    N1   C3   C2   C1    108.15  30.0  1
 TC0  Var_02    C11  N2   C8   C7    179.75  30.0  2
 TC0  Var_03    C12  C11  N2   C8   -174.64  30.0  2
 TC0  Var_04    C4   N1   C3   C1    154.44  30.0  3
 TC0  Var_05    C5   C4   N1   C3   -179.04  30.0  3
 TC0  Var_06    C6   C5   C4   N1     69.75  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 TC0  chir_01  C3  C1  C2  N1  both

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
 TC0  plan-1  N2   0.020
 TC0  plan-1  C11  0.020
 TC0  plan-1  C12  0.020
 TC0  plan-1  N4   0.020
 TC0  plan-1  N3   0.020
 TC0  plan-1  C13  0.020
 TC0  plan-1  C14  0.020
 TC0  plan-1  H12  0.020
 TC0  plan-1  HA   0.020
 TC0  plan-2  C4   0.020
 TC0  plan-2  C5   0.020
 TC0  plan-2  C6   0.020
 TC0  plan-2  C7   0.020
 TC0  plan-2  C10  0.020
 TC0  plan-2  C9   0.020
 TC0  plan-2  C8   0.020
 TC0  plan-2  N2   0.020
 TC0  plan-2  H6   0.020
 TC0  plan-2  H10  0.020
 TC0  plan-2  H7   0.020
 TC0  plan-2  H9   0.020
 TC0  plan-3  C13  0.020
 TC0  plan-3  C14  0.020
 TC0  plan-3  C19  0.020
 TC0  plan-3  C18  0.020
 TC0  plan-3  C15  0.020
 TC0  plan-3  C16  0.020
 TC0  plan-3  C17  0.020
 TC0  plan-3  C20  0.020
 TC0  plan-3  H19  0.020
 TC0  plan-3  H15  0.020
 TC0  plan-3  H18  0.020
 TC0  plan-3  H16  0.020
 TC0  plan-4  C17  0.020
 TC0  plan-4  C20  0.020
 TC0  plan-4  C21  0.020
 TC0  plan-4  C22  0.020
 TC0  plan-4  C23  0.020
 TC0  plan-4  O2   0.020
 TC0  plan-4  C24  0.020
 TC0  plan-4  C25  0.020
 TC0  plan-4  O1   0.020
 TC0  plan-4  H21  0.020
 TC0  plan-4  H22  0.020
 TC0  plan-4  H24  0.020

