# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 08:19:41 2022
#   Inital geometry file: a 120 line input string
#   Ligand name: ~{N}-[6-(3-ethoxyphenyl)-1~{H}-indazol-3-yl]benzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOc1cccc(c1)c2ccc3c([nH]nc3NC(=O)c4ccccc4)c2
#
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
 466  466  "N-[6-(3-ethoxyphenyl)-1H-indazol-3-yl]benzamide"
  ligand  46  27  .  2022-08-08  2022-08-08
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_466
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
 466  O1   O  O     0  -0.452  86.5165   2.2930   8.3450
 466  C14  C  C     0   0.511  86.1577   1.1931   7.9655
 466  C18  C  CR6   0  -0.030  85.2749   1.0294   6.7719
 466  C17  C  CR16  0  -0.266  84.4544   2.1002   6.4204
 466  C16  C  CR16  0  -0.239  83.6297   2.0164   5.3103
 466  C19  C  CR16  0  -0.293  85.2735  -0.1175   5.9792
 466  C20  C  CR16  0  -0.237  84.4564  -0.1946   4.8608
 466  C15  C  CR16  0  -0.248  83.6289   0.8686   4.5277
 466  N3   N  NH1   0  -0.741  86.5156   0.0497   8.6040
 466  C5   C  CR5   0   0.403  87.4185   0.0071   9.6660
 466  C6   C  CR56  0  -0.110  87.4238   0.7595  10.8745
 466  C7   C  CR56  0   0.452  88.5209   0.2418  11.5826
 466  N2   N  NR15  0  -0.559  89.0474  -0.7305  10.8042
 466  N1   N  N     0  -0.238  88.3910  -0.8679   9.6520
 466  C1   C  CR16  0  -0.355  88.8830   0.7020  12.8513
 466  C4   C  CR16  0  -0.289  86.6429   1.7636  11.4625
 466  C3   C  CR16  0  -0.317  86.9883   2.2111  12.7139
 466  C2   C  CR6   0   0.069  88.1083   1.6963  13.4166
 466  C11  C  CR6   0   0.105  88.4358   2.2245  14.7581
 466  C10  C  CR16  0  -0.333  87.4223   2.5130  15.6770
 466  C9   C  CR16  0  -0.223  87.7502   2.9943  16.9315
 466  C12  C  CR16  0  -0.415  89.7595   2.4359  15.1245
 466  C13  C  CR6   0   0.414  90.0874   2.9243  16.3902
 466  C8   C  CR16  0  -0.394  89.0733   3.2052  17.3030
 466  O2   O  O2    0  -0.470  91.3991   3.0990  16.6311
 466  C21  C  CH2   0  -0.187  91.8089   3.6028  17.8945
 466  C22  C  CH3   0  -0.679  93.3143   3.7225  17.8848
 466  H11  H  HCR6  0   0.262  84.4553   2.9991   7.0222
 466  H10  H  HCR6  0   0.263  82.9879   2.8489   5.0535
 466  H12  H  HCR6  0   0.261  85.9287  -0.9511   6.1990
 466  H13  H  HCR6  0   0.265  84.4727  -1.0850   4.2465
 466  H9   H  HCR6  0   0.265  82.9897   0.8057   3.6566
 466  HN3  H  HNH1  0   0.419  86.2020  -0.8392   8.2461
 466  H4   H  HNR5  0   0.418  89.8381  -1.3220  11.0023
 466  H1   H  HCR6  0   0.269  89.7257   0.2745  13.3795
 466  H3   H  HCR6  0   0.255  85.7901   2.1824  10.9479
 466  H2   H  HCR6  0   0.254  86.4018   2.9985  13.1693
 466  H6   H  HCR6  0   0.250  86.3854   2.3393  15.4207
 466  H5   H  HCR6  0   0.258  86.9651   3.2079  17.6454
 466  H7   H  HCR6  0   0.256  90.5589   2.2422  14.4190
 466  H14  H  HCR6  0   0.278  89.2892   3.5839  18.2925
 466  H15  H  HCH2  0   0.223  91.3504   4.5802  18.0805
 466  H16  H  HCH2  0   0.223  91.4845   2.9291  18.6951
 466  H18  H  HCH3  0   0.236  93.6528   4.1061  18.8468
 466  H17  H  HCH3  0   0.234  93.7899   2.7551  17.7231
 466  H19  H  HCH3  0   0.234  93.6546   4.4110  17.1114

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
 466  C15  C20  aromatic  1.388  0.020  1.388
 466  C15  C16  aromatic  1.389  0.020  1.389
 466  C20  C19  aromatic  1.387  0.020  1.387
 466  C16  C17  aromatic  1.385  0.020  1.385
 466  C19  C18  aromatic  1.394  0.020  1.394
 466  C17  C18  aromatic  1.394  0.020  1.394
 466  C18  C14  single    1.494  0.020  1.494
 466  C14  N3   single    1.358  0.020  1.358
 466  C14  O1   double    1.218  0.020  1.218
 466  N3   C5   single    1.395  0.020  1.395
 466  C5   N1   aromatic  1.308  0.020  1.308
 466  C5   C6   aromatic  1.424  0.020  1.424
 466  N1   N2   aromatic  1.333  0.020  1.333
 466  C6   C4   aromatic  1.401  0.020  1.401
 466  C6   C7   aromatic  1.405  0.020  1.405
 466  N2   C7   aromatic  1.352  0.020  1.352
 466  C4   C3   aromatic  1.373  0.020  1.373
 466  C7   C1   aromatic  1.397  0.020  1.397
 466  C3   C2   aromatic  1.419  0.020  1.419
 466  C1   C2   aromatic  1.381  0.020  1.381
 466  C2   C11  single    1.478  0.020  1.478
 466  C11  C12  aromatic  1.390  0.020  1.390
 466  C11  C10  aromatic  1.398  0.020  1.398
 466  C12  C13  aromatic  1.396  0.020  1.396
 466  C10  C9   aromatic  1.383  0.020  1.383
 466  C13  O2   single    1.345  0.020  1.345
 466  C13  C8   aromatic  1.393  0.020  1.393
 466  C9   C8   aromatic  1.390  0.020  1.390
 466  O2   C21  single    1.421  0.020  1.421
 466  C21  C22  single    1.510  0.020  1.510
 466  C17  H11  single    0.930  0.020  1.080
 466  C16  H10  single    0.930  0.020  1.080
 466  C19  H12  single    0.930  0.020  1.080
 466  C20  H13  single    0.930  0.020  1.080
 466  C15  H9   single    0.930  0.020  1.080
 466  N3   HN3  single    0.860  0.020  1.020
 466  N2   H4   single    0.860  0.020  1.020
 466  C1   H1   single    0.930  0.020  1.080
 466  C4   H3   single    0.930  0.020  1.080
 466  C3   H2   single    0.930  0.020  1.080
 466  C10  H6   single    0.930  0.020  1.080
 466  C9   H5   single    0.930  0.020  1.080
 466  C12  H7   single    0.930  0.020  1.080
 466  C8   H14  single    0.930  0.020  1.080
 466  C21  H15  single    0.970  0.020  1.090
 466  C21  H16  single    0.970  0.020  1.090
 466  C22  H18  single    0.970  0.020  1.090
 466  C22  H17  single    0.970  0.020  1.090
 466  C22  H19  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
 466  N3   C14  C18  116.06  3.000
 466  N3   C14  O1   122.45  3.000
 466  C18  C14  O1   121.48  3.000
 466  C19  C18  C17  119.21  3.000
 466  C17  C18  C14  117.72  3.000
 466  C19  C18  C14  123.03  3.000
 466  H11  C17  C16  119.77  3.000
 466  H11  C17  C18  119.84  3.000
 466  C16  C17  C18  120.39  3.000
 466  H10  C16  C15  120.10  3.000
 466  H10  C16  C17  119.79  3.000
 466  C15  C16  C17  120.11  3.000
 466  H12  C19  C20  118.51  3.000
 466  H12  C19  C18  121.15  3.000
 466  C20  C19  C18  120.31  3.000
 466  H13  C20  C15  120.22  3.000
 466  H13  C20  C19  119.64  3.000
 466  C15  C20  C19  120.14  3.000
 466  H9   C15  C20  120.05  3.000
 466  H9   C15  C16  120.12  3.000
 466  C20  C15  C16  119.83  3.000
 466  HN3  N3   C5   116.41  3.000
 466  HN3  N3   C14  119.58  3.000
 466  C5   N3   C14  123.68  3.000
 466  N1   C5   C6   111.09  3.000
 466  C6   C5   N3   129.25  3.000
 466  N1   C5   N3   119.57  3.000
 466  C4   C6   C7   119.20  3.000
 466  C7   C6   C5   103.65  3.000
 466  C4   C6   C5   137.12  3.000
 466  C1   C7   N2   131.19  3.000
 466  C1   C7   C6   122.60  3.000
 466  N2   C7   C6   106.20  3.000
 466  H4   N2   N1   119.73  3.000
 466  H4   N2   C7   127.94  3.000
 466  N1   N2   C7   112.33  3.000
 466  N2   N1   C5   106.72  3.000
 466  H1   C1   C2   121.41  3.000
 466  H1   C1   C7   120.97  3.000
 466  C2   C1   C7   117.60  3.000
 466  H3   C4   C3   120.42  3.000
 466  H3   C4   C6   121.18  3.000
 466  C3   C4   C6   118.41  3.000
 466  H2   C3   C2   118.90  3.000
 466  H2   C3   C4   118.96  3.000
 466  C2   C3   C4   122.12  3.000
 466  C11  C2   C3   119.64  3.000
 466  C11  C2   C1   120.28  3.000
 466  C3   C2   C1   120.08  3.000
 466  C12  C11  C10  119.06  3.000
 466  C10  C11  C2   120.63  3.000
 466  C12  C11  C2   120.31  3.000
 466  H6   C10  C9   119.85  3.000
 466  H6   C10  C11  120.39  3.000
 466  C9   C10  C11  119.74  3.000
 466  H5   C9   C8   118.95  3.000
 466  H5   C9   C10  119.67  3.000
 466  C8   C9   C10  121.38  3.000
 466  H7   C12  C13  118.66  3.000
 466  H7   C12  C11  120.25  3.000
 466  C13  C12  C11  121.07  3.000
 466  O2   C13  C8   124.50  3.000
 466  C8   C13  C12  119.59  3.000
 466  O2   C13  C12  115.91  3.000
 466  H14  C8   C13  121.67  3.000
 466  H14  C8   C9   119.18  3.000
 466  C13  C8   C9   119.15  3.000
 466  C21  O2   C13  119.12  3.000
 466  H16  C21  H15  107.50  3.000
 466  H16  C21  C22  110.40  3.000
 466  H15  C21  C22  110.34  3.000
 466  H16  C21  O2   110.27  3.000
 466  H15  C21  O2   110.28  3.000
 466  C22  C21  O2   108.05  3.000
 466  H19  C22  H17  108.61  3.000
 466  H19  C22  H18  107.89  3.000
 466  H17  C22  H18  107.93  3.000
 466  H19  C22  C21  111.46  3.000
 466  H17  C22  C21  111.44  3.000
 466  H18  C22  C21  109.38  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
 466  CONST_01  C15  C20  C19  C18     0.00   0.0  0
 466  CONST_02  C15  C16  C17  C18     0.00   0.0  0
 466  CONST_03  C20  C15  C16  C17     0.00   0.0  0
 466  CONST_04  C20  C19  C18  C17     0.00   0.0  0
 466  CONST_05  C19  C20  C15  C16     0.00   0.0  0
 466  CONST_06  C19  C18  C17  C16     0.00   0.0  0
 466  CONST_07  C7   N2   N1   C5      0.00   0.0  0
 466  CONST_08  C3   C4   C6   C5    180.00   0.0  0
 466  CONST_09  N2   C7   C6   C5      0.00   0.0  0
 466  CONST_10  C1   C7   C6   C5    180.00   0.0  0
 466  CONST_11  N2   N1   C5   C6      0.00   0.0  0
 466  CONST_12  C2   C3   C4   C6      0.00   0.0  0
 466  CONST_13  N1   N2   C7   C6      0.00   0.0  0
 466  CONST_14  C2   C1   C7   C6      0.00   0.0  0
 466  CONST_15  N1   C5   C6   C7      0.00   0.0  0
 466  CONST_16  C3   C4   C6   C7      0.00   0.0  0
 466  CONST_17  C3   C2   C1   C7      0.00   0.0  0
 466  CONST_18  C11  C2   C1   C7    180.00   0.0  0
 466  CONST_19  C4   C6   C7   N2    180.00   0.0  0
 466  CONST_20  C2   C1   C7   N2    180.00   0.0  0
 466  CONST_21  C4   C6   C5   N1    180.00   0.0  0
 466  CONST_22  C1   C7   N2   N1    180.00   0.0  0
 466  CONST_23  C4   C6   C7   C1      0.00   0.0  0
 466  CONST_24  C4   C3   C2   C1      0.00   0.0  0
 466  CONST_27  C11  C2   C3   C4    180.00   0.0  0
 466  CONST_30  C13  C12  C11  C2    180.00   0.0  0
 466  CONST_31  C9   C10  C11  C2    180.00   0.0  0
 466  CONST_32  C8   C13  C12  C11     0.00   0.0  0
 466  CONST_33  C8   C9   C10  C11     0.00   0.0  0
 466  CONST_34  C13  C12  C11  C10     0.00   0.0  0
 466  CONST_35  C13  C8   C9   C10     0.00   0.0  0
 466  CONST_36  C12  C11  C10  C9      0.00   0.0  0
 466  CONST_37  C12  C13  C8   C9      0.00   0.0  0
 466  CONST_38  C20  C19  C18  C14   180.00   0.0  0
 466  CONST_39  C16  C17  C18  C14   180.00   0.0  0
 466  CONST_40  N2   N1   C5   N3    180.00   0.0  0
 466  CONST_41  C4   C6   C5   N3      0.00   0.0  0
 466  CONST_42  C7   C6   C5   N3    180.00   0.0  0
 466  CONST_43  O2   C13  C12  C11   180.00   0.0  0
 466  CONST_44  O2   C13  C8   C9    180.00   0.0  0
 466  CONST_45  H13  C20  C19  C18   180.00   0.0  0
 466  CONST_46  H10  C16  C17  C18   180.00   0.0  0
 466  CONST_47  H9   C15  C16  C17   180.00   0.0  0
 466  CONST_48  H12  C19  C18  C17   180.00   0.0  0
 466  CONST_49  H13  C20  C15  C16   180.00   0.0  0
 466  CONST_50  H9   C15  C20  C19   180.00   0.0  0
 466  CONST_51  H11  C17  C18  C19   180.00   0.0  0
 466  CONST_52  H10  C16  C15  C20   180.00   0.0  0
 466  CONST_53  H12  C19  C20  C15   180.00   0.0  0
 466  CONST_54  H11  C17  C16  C15   180.00   0.0  0
 466  CONST_55  H4   N2   N1   C5    180.00   0.0  0
 466  CONST_56  H3   C4   C6   C5      0.00   0.0  0
 466  CONST_57  H2   C3   C4   C6    180.00   0.0  0
 466  CONST_58  H4   N2   C7   C6    180.00   0.0  0
 466  CONST_59  H1   C1   C7   C6    180.00   0.0  0
 466  CONST_60  H3   C4   C6   C7    180.00   0.0  0
 466  CONST_61  H1   C1   C7   N2      0.00   0.0  0
 466  CONST_62  H4   N2   C7   C1      0.00   0.0  0
 466  CONST_63  H2   C3   C2   C1    180.00   0.0  0
 466  CONST_64  H1   C1   C2   C3    180.00   0.0  0
 466  CONST_65  H3   C4   C3   C2    180.00   0.0  0
 466  CONST_66  H7   C12  C11  C2      0.00   0.0  0
 466  CONST_67  H6   C10  C11  C2      0.00   0.0  0
 466  CONST_68  H2   C3   C2   C11     0.00   0.0  0
 466  CONST_69  H1   C1   C2   C11     0.00   0.0  0
 466  CONST_70  H5   C9   C10  C11   180.00   0.0  0
 466  CONST_71  H7   C12  C11  C10   180.00   0.0  0
 466  CONST_72  H14  C8   C9   C10   180.00   0.0  0
 466  CONST_73  H6   C10  C11  C12   180.00   0.0  0
 466  CONST_74  H14  C8   C13  C12   180.00   0.0  0
 466  CONST_75  H5   C9   C8   C13   180.00   0.0  0
 466  CONST_76  H7   C12  C13  C8    180.00   0.0  0
 466  CONST_77  H6   C10  C9   C8    180.00   0.0  0
 466  CONST_78  C5   N3   C14  C18   180.00   0.0  0
 466  CONST_83  C5   N3   C14  O1      0.00   0.0  0
 466  CONST_84  HN3  N3   C14  C18     0.00   0.0  0
 466  CONST_85  HN3  N3   C14  O1    180.00   0.0  0
 466  Var_01    C19  C18  C14  O1    152.80  30.0  2
 466  Var_02    C17  C18  C14  O1    -24.89  30.0  2
 466  Var_03    N3   C14  C18  C17   154.26  30.0  2
 466  Var_04    N3   C14  C18  C19   -28.04  30.0  2
 466  Var_05    C21  O2   C13  C12   179.53  30.0  2
 466  Var_06    C21  O2   C13  C8      0.02  30.0  2
 466  Var_07    C22  C21  O2   C13  -178.98  30.0  3
 466  Var_08    H15  C21  O2   C13   -58.30  30.0  3
 466  Var_09    H16  C21  O2   C13    60.27  30.0  3
 466  Var_10    H18  C22  C21  O2   -179.89  30.0  3
 466  Var_11    H17  C22  C21  O2    -60.62  30.0  3
 466  Var_12    H19  C22  C21  O2     60.89  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
 466  plan-1  C14  0.020
 466  plan-1  C18  0.020
 466  plan-1  C17  0.020
 466  plan-1  C16  0.020
 466  plan-1  C19  0.020
 466  plan-1  C20  0.020
 466  plan-1  C15  0.020
 466  plan-1  H11  0.020
 466  plan-1  H10  0.020
 466  plan-1  H12  0.020
 466  plan-1  H13  0.020
 466  plan-1  H9   0.020
 466  plan-2  C2   0.020
 466  plan-2  C11  0.020
 466  plan-2  C10  0.020
 466  plan-2  C9   0.020
 466  plan-2  C12  0.020
 466  plan-2  C13  0.020
 466  plan-2  C8   0.020
 466  plan-2  O2   0.020
 466  plan-2  H6   0.020
 466  plan-2  H5   0.020
 466  plan-2  H7   0.020
 466  plan-2  H14  0.020
 466  plan-3  N3   0.020
 466  plan-3  C5   0.020
 466  plan-3  C6   0.020
 466  plan-3  C7   0.020
 466  plan-3  N2   0.020
 466  plan-3  N1   0.020
 466  plan-3  C1   0.020
 466  plan-3  C4   0.020
 466  plan-3  C3   0.020
 466  plan-3  C2   0.020
 466  plan-3  C11  0.020
 466  plan-3  H4   0.020
 466  plan-3  H1   0.020
 466  plan-3  H3   0.020
 466  plan-3  H2   0.020
 466  plan-4  O1   0.020
 466  plan-4  C14  0.020
 466  plan-4  C18  0.020
 466  plan-4  N3   0.020
 466  plan-4  C5   0.020
 466  plan-4  HN3  0.020

