# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 03:37:57 2020
#   Inital geometry file: a 144 line input string
#   Ligand name: 4-{7-methoxy-6-[3-(morpholin-4-yl)propoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc2c(Cc3c2[nH]nc3c4ccc(cc4)C#N)cc1OCCCN5CCOCC5
#
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
 3HK  3HK  4-{7-methoxy-6-[3-(morpholin-4-yl)propoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile  ligand  58  32  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_3HK
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
 3HK  N4   N  NS    0  -0.254   9.3239   4.2450   0.0041
 3HK  C21  C  CSP   0   0.053   8.5265   3.4126  -0.0015
 3HK  C18  C  CR6   0  -0.014   7.5413   2.3823  -0.0067
 3HK  C17  C  CR16  0  -0.226   7.9293   1.0452  -0.1133
 3HK  C16  C  CR16  0  -0.277   6.9717   0.0518  -0.1165
 3HK  C19  C  CR16  0  -0.215   6.1906   2.7117   0.0951
 3HK  C20  C  CR16  0  -0.346   5.2405   1.7080   0.0904
 3HK  C15  C  CR6   0   0.067   5.6128   0.3664  -0.0141
 3HK  C14  C  CR5   0   0.162   4.5960  -0.6816  -0.0136
 3HK  C12  C  CR55  0  -0.090   3.1952  -0.5699   0.0306
 3HK  C11  C  CH2   0  -0.568   2.0322   0.3715   0.0804
 3HK  N3   N  N     0  -0.283   4.9489  -1.9666  -0.0588
 3HK  N2   N  NR15  0  -0.524   3.8183  -2.6652  -0.0449
 3HK  C13  C  CR55  0   0.347   2.7430  -1.8678   0.0080
 3HK  C22  C  CR56  0   0.138   1.2977  -1.9261   0.0433
 3HK  C10  C  CR56  0   0.032   0.8673  -0.5989   0.0842
 3HK  C9   C  CR16  0  -0.455  -0.4891  -0.3116   0.1227
 3HK  C23  C  CR16  0  -0.456   0.3921  -2.9835   0.0425
 3HK  C24  C  CR6   0   0.305  -0.9629  -2.6971   0.0829
 3HK  O3   O  O2    0  -0.465  -1.9404  -3.6219   0.0863
 3HK  C25  C  CH3   0  -0.440  -1.5676  -4.9835   0.0472
 3HK  C8   C  CR6   0   0.324  -1.4073  -1.3539   0.1235
 3HK  O2   O  O2    0  -0.469  -2.7425  -1.1967   0.1607
 3HK  C7   C  CH2   0  -0.173  -3.2703   0.1192   0.1380
 3HK  C6   C  CH2   0  -0.483  -4.7813   0.0234   0.1716
 3HK  C5   C  CH2   0  -0.259  -5.4019   1.4087   0.0383
 3HK  N1   N  NT    0  -0.427  -6.8392   1.4142   0.2274
 3HK  C2   C  CH2   0  -0.310  -7.5501   0.7383  -0.8439
 3HK  C1   C  CH2   0  -0.186  -9.0448   0.7782  -0.5892
 3HK  C3   C  CH2   0  -0.302  -7.3401   2.7710   0.3622
 3HK  C4   C  CH2   0  -0.190  -8.8385   2.7612   0.5942
 3HK  O1   O  O2    0  -0.485  -9.5182   2.0991  -0.4490
 3HK  H21  H  HCR6  0   0.281   8.9770   0.7895  -0.1951
 3HK  H20  H  HCR6  0   0.266   7.2801  -0.9811  -0.2014
 3HK  H22  H  HCR6  0   0.282   5.8869   3.7461   0.1806
 3HK  H23  H  HCR6  0   0.278   4.1974   1.9809   0.1750
 3HK  H18  H  HCH2  0   0.277   2.0270   1.0035   0.9731
 3HK  H19  H  HCH2  0   0.278   1.9895   1.0446  -0.7807
 3HK  H2   H  HNR5  0   0.421   3.8582  -3.6716  -0.0716
 3HK  H17  H  HCR6  0   0.282  -0.8189   0.7189   0.1536
 3HK  H24  H  HCR6  0   0.281   0.7481  -4.0045   0.0093
 3HK  H25  H  HCH3  0   0.228  -0.9662  -5.2684   0.9149
 3HK  H27  H  HCH3  0   0.262  -2.4912  -5.5570   0.0585
 3HK  H26  H  HCH3  0   0.228  -1.0122  -5.2298  -0.8621
 3HK  H15  H  HCH2  0   0.225  -2.9058   0.6903   0.9998
 3HK  H16  H  HCH2  0   0.223  -2.9381   0.6408  -0.7675
 3HK  H13  H  HCH2  0   0.241  -5.1132  -0.6301  -0.6381
 3HK  H14  H  HCH2  0   0.237  -5.1053  -0.4282   1.1125
 3HK  H12  H  HCH2  0   0.233  -4.9680   2.0619   0.8012
 3HK  H11  H  HCH2  0   0.195  -5.1232   1.8435  -0.9373
 3HK  H6   H  HCH2  0   0.196  -7.3269   1.1920  -1.8258
 3HK  H5   H  HCH2  0   0.245  -7.2453  -0.3084  -0.8989
 3HK  H4   H  HCH2  0   0.236  -9.5775   0.3268  -1.4273
 3HK  H3   H  HCH2  0   0.200  -9.2738   0.1912   0.3120
 3HK  H7   H  HCH2  0   0.241  -6.8543   3.2538   1.2141
 3HK  H8   H  HCH2  0   0.195  -7.1147   3.3822  -0.5293
 3HK  H10  H  HCH2  0   0.200  -9.0558   2.2820   1.5596
 3HK  H9   H  HCH2  0   0.236  -9.2163   3.7841   0.6353

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
 3HK  C25  O3   single    1.412  0.020  1.412
 3HK  O3   C24  single    1.346  0.020  1.346
 3HK  C23  C24  aromatic  1.386  0.020  1.386
 3HK  C23  C22  aromatic  1.392  0.020  1.392
 3HK  C24  C8   aromatic  1.415  0.020  1.415
 3HK  N2   C13  aromatic  1.340  0.020  1.340
 3HK  N2   N3   aromatic  1.329  0.020  1.329
 3HK  C22  C13  aromatic  1.447  0.020  1.447
 3HK  C22  C10  aromatic  1.396  0.020  1.396
 3HK  C13  C12  aromatic  1.375  0.020  1.375
 3HK  N3   C14  aromatic  1.333  0.020  1.333
 3HK  C7   O2   single    1.418  0.020  1.418
 3HK  C7   C6   single    1.514  0.020  1.514
 3HK  C8   O2   single    1.345  0.020  1.345
 3HK  C8   C9   aromatic  1.389  0.020  1.389
 3HK  C5   C6   single    1.524  0.020  1.524
 3HK  C5   N1   single    1.450  0.020  1.450
 3HK  C14  C12  aromatic  1.406  0.020  1.406
 3HK  C14  C15  single    1.460  0.020  1.460
 3HK  C12  C11  single    1.497  0.020  1.497
 3HK  C10  C9   aromatic  1.387  0.020  1.387
 3HK  C10  C11  single    1.516  0.020  1.516
 3HK  C2   N1   single    1.453  0.020  1.453
 3HK  C2   C1   single    1.517  0.020  1.517
 3HK  C16  C15  aromatic  1.399  0.020  1.399
 3HK  C16  C17  aromatic  1.380  0.020  1.380
 3HK  C15  C20  aromatic  1.396  0.020  1.396
 3HK  N1   C3   single    1.453  0.020  1.453
 3HK  C17  C18  aromatic  1.396  0.020  1.396
 3HK  C20  C19  aromatic  1.382  0.020  1.382
 3HK  C1   O1   single    1.410  0.020  1.410
 3HK  C3   C4   single    1.516  0.020  1.516
 3HK  C18  C19  aromatic  1.394  0.020  1.394
 3HK  C18  C21  single    1.425  0.020  1.425
 3HK  C4   O1   single    1.410  0.020  1.410
 3HK  C21  N4   triple    1.153  0.020  1.153
 3HK  C17  H21  single    0.930  0.020  1.080
 3HK  C16  H20  single    0.930  0.020  1.080
 3HK  C19  H22  single    0.930  0.020  1.080
 3HK  C20  H23  single    0.930  0.020  1.080
 3HK  C11  H18  single    0.970  0.020  1.090
 3HK  C11  H19  single    0.970  0.020  1.090
 3HK  N2   H2   single    0.860  0.020  1.020
 3HK  C9   H17  single    0.930  0.020  1.080
 3HK  C23  H24  single    0.930  0.020  1.080
 3HK  C25  H25  single    0.970  0.020  1.090
 3HK  C25  H27  single    0.970  0.020  1.090
 3HK  C25  H26  single    0.970  0.020  1.090
 3HK  C7   H15  single    0.970  0.020  1.090
 3HK  C7   H16  single    0.970  0.020  1.090
 3HK  C6   H13  single    0.970  0.020  1.090
 3HK  C6   H14  single    0.970  0.020  1.090
 3HK  C5   H12  single    0.970  0.020  1.090
 3HK  C5   H11  single    0.970  0.020  1.090
 3HK  C2   H6   single    0.970  0.020  1.090
 3HK  C2   H5   single    0.970  0.020  1.090
 3HK  C1   H4   single    0.970  0.020  1.090
 3HK  C1   H3   single    0.970  0.020  1.090
 3HK  C3   H7   single    0.970  0.020  1.090
 3HK  C3   H8   single    0.970  0.020  1.090
 3HK  C4   H10  single    0.970  0.020  1.090
 3HK  C4   H9   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
 3HK  C18  C21  N4   180.00  3.000
 3HK  C19  C18  C17  120.07  3.000
 3HK  C19  C18  C21  119.91  3.000
 3HK  C17  C18  C21  120.02  3.000
 3HK  H21  C17  C16  120.13  3.000
 3HK  H21  C17  C18  120.09  3.000
 3HK  C16  C17  C18  119.78  3.000
 3HK  H20  C16  C15  119.85  3.000
 3HK  H20  C16  C17  119.34  3.000
 3HK  C15  C16  C17  120.81  3.000
 3HK  H22  C19  C20  120.12  3.000
 3HK  H22  C19  C18  120.26  3.000
 3HK  C20  C19  C18  119.62  3.000
 3HK  H23  C20  C15  120.37  3.000
 3HK  H23  C20  C19  118.65  3.000
 3HK  C15  C20  C19  120.98  3.000
 3HK  C14  C15  C20  120.26  3.000
 3HK  C20  C15  C16  118.73  3.000
 3HK  C14  C15  C16  121.01  3.000
 3HK  N3   C14  C12  109.96  3.000
 3HK  C12  C14  C15  129.56  3.000
 3HK  N3   C14  C15  120.48  3.000
 3HK  C13  C12  C11  109.80  3.000
 3HK  C11  C12  C14  145.59  3.000
 3HK  C13  C12  C14  104.61  3.000
 3HK  H19  C11  H18  106.66  3.000
 3HK  H19  C11  C10  111.46  3.000
 3HK  H18  C11  C10  111.36  3.000
 3HK  H19  C11  C12  113.02  3.000
 3HK  H18  C11  C12  113.21  3.000
 3HK  C10  C11  C12  101.22  3.000
 3HK  N2   N3   C14  106.32  3.000
 3HK  H2   N2   C13  128.86  3.000
 3HK  H2   N2   N3   119.41  3.000
 3HK  C13  N2   N3   111.73  3.000
 3HK  C22  C13  N2   141.14  3.000
 3HK  C22  C13  C12  111.49  3.000
 3HK  N2   C13  C12  107.38  3.000
 3HK  C23  C22  C10  121.43  3.000
 3HK  C10  C22  C13  105.69  3.000
 3HK  C23  C22  C13  132.88  3.000
 3HK  C9   C10  C22  119.96  3.000
 3HK  C9   C10  C11  128.23  3.000
 3HK  C22  C10  C11  111.81  3.000
 3HK  H17  C9   C8   120.86  3.000
 3HK  H17  C9   C10  119.73  3.000
 3HK  C8   C9   C10  119.41  3.000
 3HK  H24  C23  C24  121.18  3.000
 3HK  H24  C23  C22  120.18  3.000
 3HK  C24  C23  C22  118.64  3.000
 3HK  C8   C24  O3   115.09  3.000
 3HK  C8   C24  C23  120.27  3.000
 3HK  O3   C24  C23  124.64  3.000
 3HK  C25  O3   C24  118.09  3.000
 3HK  H26  C25  H27  108.74  3.000
 3HK  H26  C25  H25  108.77  3.000
 3HK  H27  C25  H25  108.76  3.000
 3HK  H26  C25  O3   111.97  3.000
 3HK  H27  C25  O3   106.50  3.000
 3HK  H25  C25  O3   111.99  3.000
 3HK  O2   C8   C24  115.05  3.000
 3HK  O2   C8   C9   124.65  3.000
 3HK  C24  C8   C9   120.30  3.000
 3HK  C7   O2   C8   118.53  3.000
 3HK  H16  C7   H15  107.49  3.000
 3HK  H16  C7   C6   110.53  3.000
 3HK  H15  C7   C6   110.32  3.000
 3HK  H16  C7   O2   109.99  3.000
 3HK  H15  C7   O2   110.31  3.000
 3HK  C6   C7   O2   108.20  3.000
 3HK  H14  C6   H13  107.52  3.000
 3HK  H14  C6   C5   109.29  3.000
 3HK  H13  C6   C5   110.81  3.000
 3HK  H14  C6   C7   109.94  3.000
 3HK  H13  C6   C7   108.94  3.000
 3HK  C5   C6   C7   110.30  3.000
 3HK  H11  C5   H12  106.32  3.000
 3HK  H11  C5   N1   111.35  3.000
 3HK  H12  C5   N1   107.45  3.000
 3HK  H11  C5   C6   109.43  3.000
 3HK  H12  C5   C6   108.68  3.000
 3HK  N1   C5   C6   113.31  3.000
 3HK  C3   N1   C2   109.53  3.000
 3HK  C3   N1   C5   110.95  3.000
 3HK  C2   N1   C5   112.78  3.000
 3HK  H5   C2   H6   107.02  3.000
 3HK  H5   C2   C1   107.99  3.000
 3HK  H6   C2   C1   109.73  3.000
 3HK  H5   C2   N1   110.29  3.000
 3HK  H6   C2   N1   111.45  3.000
 3HK  C1   C2   N1   110.25  3.000
 3HK  H3   C1   H4   107.88  3.000
 3HK  H3   C1   O1   110.41  3.000
 3HK  H4   C1   O1   107.46  3.000
 3HK  H3   C1   C2   109.20  3.000
 3HK  H4   C1   C2   109.95  3.000
 3HK  O1   C1   C2   111.85  3.000
 3HK  H8   C3   H7   107.10  3.000
 3HK  H8   C3   C4   109.20  3.000
 3HK  H7   C3   C4   108.83  3.000
 3HK  H8   C3   N1   111.82  3.000
 3HK  H7   C3   N1   109.36  3.000
 3HK  C4   C3   N1   110.42  3.000
 3HK  H9   C4   H10  107.88  3.000
 3HK  H9   C4   O1   107.52  3.000
 3HK  H10  C4   O1   110.47  3.000
 3HK  H9   C4   C3   109.99  3.000
 3HK  H10  C4   C3   109.42  3.000
 3HK  O1   C4   C3   111.47  3.000
 3HK  C4   O1   C1   110.58  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
 3HK  CONST_01  C15  C16  C17  C18     0.00   0.0  0
 3HK  CONST_02  C15  C20  C19  C18     0.00   0.0  0
 3HK  CONST_03  C14  C15  C16  C17   180.00   0.0  0
 3HK  CONST_04  C20  C15  C16  C17     0.00   0.0  0
 3HK  CONST_05  C20  C19  C18  C17     0.00   0.0  0
 3HK  CONST_06  N3   C14  C15  C16     0.00   0.0  0
 3HK  CONST_07  C12  C14  C15  C16   180.00   0.0  0
 3HK  CONST_08  C19  C20  C15  C16     0.00   0.0  0
 3HK  CONST_09  C19  C18  C17  C16     0.00   0.0  0
 3HK  CONST_10  C14  C15  C20  C19   180.00   0.0  0
 3HK  CONST_11  N3   C14  C15  C20   180.00   0.0  0
 3HK  CONST_12  C12  C14  C15  C20     0.00   0.0  0
 3HK  CONST_13  N2   N3   C14  C15   180.00   0.0  0
 3HK  CONST_14  C13  C12  C14  C15   180.00   0.0  0
 3HK  CONST_15  C13  N2   N3   C14     0.00   0.0  0
 3HK  CONST_16  N2   C13  C12  C14     0.00   0.0  0
 3HK  CONST_17  C22  C13  C12  C14   180.00   0.0  0
 3HK  CONST_18  N3   N2   C13  C12     0.00   0.0  0
 3HK  CONST_19  C23  C22  C13  C12   180.00   0.0  0
 3HK  CONST_20  C10  C22  C13  C12     0.00   0.0  0
 3HK  CONST_21  N2   N3   C14  C12     0.00   0.0  0
 3HK  CONST_22  C22  C13  N2   N3    180.00   0.0  0
 3HK  CONST_23  C13  C12  C14  N3      0.00   0.0  0
 3HK  CONST_24  C23  C22  C13  N2      0.00   0.0  0
 3HK  CONST_25  C10  C22  C13  N2    180.00   0.0  0
 3HK  CONST_26  C24  C23  C22  C13   180.00   0.0  0
 3HK  CONST_27  C9   C10  C22  C13   180.00   0.0  0
 3HK  CONST_28  C8   C24  C23  C22     0.00   0.0  0
 3HK  CONST_29  C8   C9   C10  C22     0.00   0.0  0
 3HK  CONST_30  C24  C23  C22  C10     0.00   0.0  0
 3HK  CONST_31  C24  C8   C9   C10     0.00   0.0  0
 3HK  CONST_32  C23  C24  C8   C9      0.00   0.0  0
 3HK  CONST_33  C23  C22  C10  C9      0.00   0.0  0
 3HK  CONST_34  C11  C12  C14  C15     0.00   0.0  0
 3HK  CONST_35  C16  C17  C18  C21   180.00   0.0  0
 3HK  CONST_36  C20  C19  C18  C21   180.00   0.0  0
 3HK  CONST_37  O3   C24  C23  C22   180.00   0.0  0
 3HK  CONST_38  O2   C8   C9   C10   180.00   0.0  0
 3HK  CONST_39  O3   C24  C8   C9    180.00   0.0  0
 3HK  CONST_40  O2   C8   C24  C23   180.00   0.0  0
 3HK  CONST_41  H20  C16  C17  C18   180.00   0.0  0
 3HK  CONST_42  H23  C20  C19  C18   180.00   0.0  0
 3HK  CONST_43  H22  C19  C18  C17   180.00   0.0  0
 3HK  CONST_44  H21  C17  C18  C19   180.00   0.0  0
 3HK  CONST_45  H2   N2   N3   C14   180.00   0.0  0
 3HK  CONST_46  H17  C9   C10  C11     0.00   0.0  0
 3HK  CONST_47  H24  C23  C22  C13     0.00   0.0  0
 3HK  Var_01    O1   C1   C2   N1     57.04  30.0  1
 3HK  Var_02    O1   C4   C3   N1    -57.49  30.0  1
 3HK  Var_03    C4   C3   N1   C2     56.28  30.0  1
 3HK  Var_04    C3   N1   C2   C1    -55.90  30.0  1
 3HK  Var_05    C3   C4   O1   C1     57.39  30.0  1
 3HK  Var_06    H18  C11  C12  C14   -61.36  30.0  1
 3HK  Var_07    C8   C24  O3   C25  -179.99  30.0  2
 3HK  Var_08    C2   N1   C5   C6    -68.35  30.0  3
 3HK  Var_09    C6   C7   O2   C8    179.34  30.0  2
 3HK  Var_10    N1   C5   C6   C7   -172.83  30.0  1
 3HK  Var_11    H25  C25  O3   C24    61.15  30.0  3
 3HK  Var_12    C5   C6   C7   O2   -175.56  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
 3HK  plan-1  N4   0.020
 3HK  plan-1  C21  0.020
 3HK  plan-1  C18  0.020
 3HK  plan-1  C17  0.020
 3HK  plan-1  C16  0.020
 3HK  plan-1  C19  0.020
 3HK  plan-1  C20  0.020
 3HK  plan-1  C15  0.020
 3HK  plan-1  C14  0.020
 3HK  plan-1  H21  0.020
 3HK  plan-1  H20  0.020
 3HK  plan-1  H22  0.020
 3HK  plan-1  H23  0.020
 3HK  plan-2  C15  0.020
 3HK  plan-2  C14  0.020
 3HK  plan-2  C12  0.020
 3HK  plan-2  C11  0.020
 3HK  plan-2  N3   0.020
 3HK  plan-2  N2   0.020
 3HK  plan-2  C13  0.020
 3HK  plan-2  C22  0.020
 3HK  plan-2  C10  0.020
 3HK  plan-2  C9   0.020
 3HK  plan-2  C23  0.020
 3HK  plan-2  C24  0.020
 3HK  plan-2  O3   0.020
 3HK  plan-2  C8   0.020
 3HK  plan-2  O2   0.020
 3HK  plan-2  H2   0.020
 3HK  plan-2  H17  0.020
 3HK  plan-2  H24  0.020

