# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 14:47:53 2020
#   Inital geometry file: a 124 line input string
#   Ligand name: 1-{(3S,3aS)-3-[3-fluoro-4-(trifluoromethoxy)phenyl]-8-methoxy-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl}-2-hydroxyethanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc2CC[C@H]3[C@H](N(N=C3c2c1)C(=O)CO)c4ccc(OC(F)(F)F)c(F)c4
#
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
 1HW  1HW  1-{(3S,3aS)-3-[3-fluoro-4-(trifluoromethoxy)phenyl]-8-methoxy-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl}-2-hydroxyethanone  ligand  49  31  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_1HW
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
 1HW  C1   C  CR16  0  -0.294  -4.0656  -2.5209   0.8544
 1HW  C2   C  CR6   0   0.053  -3.0845  -1.5781   1.1329
 1HW  C3   C  CR6   0   0.078  -3.1335  -0.3659   0.4276
 1HW  C4   C  CR16  0  -0.390  -4.1292  -0.1237  -0.5141
 1HW  C5   C  CR6   0   0.399  -5.1043  -1.0792  -0.7699
 1HW  C10  C  CR5   0   0.270  -2.0868   0.6096   0.6865
 1HW  C11  C  CR15  0  -0.129  -0.0134   1.4399   1.4207
 1HW  C6   C  CR16  0  -0.369  -5.0675  -2.2903  -0.0769
 1HW  C7   C  CH2   0  -0.517  -2.0170  -1.8539   2.1635
 1HW  C9   C  CR15  0  -0.376  -1.0969   0.4040   1.7934
 1HW  F31  F  F     0  -0.296   3.7803  -2.7465  -1.8251
 1HW  C28  C  CT    0   1.077   4.6614  -2.2899  -0.9342
 1HW  F29  F  F     0  -0.296   4.4165  -2.9242   0.2113
 1HW  F30  F  F     0  -0.273   5.8753  -2.6114  -1.3456
 1HW  C17  C  CR6   0   0.151   3.4615  -0.3983  -0.2915
 1HW  C16  C  CR6   0   0.529   3.4086  -0.0799   1.0560
 1HW  F26  F  F     0  -0.295   4.4591  -0.3545   1.8307
 1HW  C15  C  CR16  0  -0.467   2.2998   0.5347   1.5980
 1HW  C18  C  CR16  0  -0.281   2.3882  -0.0886  -1.1073
 1HW  C19  C  CR16  0  -0.314   1.2673   0.5235  -0.5686
 1HW  C14  C  CR6   0   0.171   1.2134   0.8353   0.7852
 1HW  C8   C  CH2   0  -0.447  -0.7329  -1.0658   1.9184
 1HW  N12  N  NR5   0  -0.369  -0.7647   2.2790   0.4883
 1HW  C20  C  C     0   0.507  -0.3224   3.4586  -0.0085
 1HW  O23  O  O     0  -0.464   0.7188   3.9513   0.3794
 1HW  C21  C  CH2   0  -0.258  -1.2144   4.0973  -1.0544
 1HW  O22  O  OH1   0  -0.659  -0.6227   5.3021  -1.4420
 1HW  N13  N  N     0  -0.248  -1.8950   1.6739   0.0104
 1HW  O24  O  O2    0  -0.474  -6.0305  -0.7582  -1.6931
 1HW  C25  C  CH3   0  -0.437  -7.0138  -1.7178  -2.0272
 1HW  H1   H  HCR6  0   0.259  -4.0513  -3.4712   1.3744
 1HW  H2   H  HCR6  0   0.261  -4.1466   0.8154  -1.0543
 1HW  H4   H  HCR5  0   0.300   0.2822   2.0175   2.2958
 1HW  H5   H  HCR6  0   0.283  -5.8037  -3.0627  -0.2529
 1HW  H6   H  HCH2  0   0.254  -2.4047  -1.6027   3.1569
 1HW  H7   H  HCH2  0   0.263  -1.7993  -2.9230   2.1848
 1HW  H8   H  HCR5  0   0.303  -1.5723   0.7180   2.7308
 1HW  H9   H  HCR6  0   0.290   2.2895   0.7787   2.6533
 1HW  H10  H  HCR6  0   0.293   2.4311  -0.3090  -2.1653
 1HW  H11  H  HCR6  0   0.266   0.4374   0.7507  -1.2246
 1HW  H12  H  HCH2  0   0.260  -0.0294  -1.2241   2.7371
 1HW  H13  H  HCH2  0   0.244  -0.2499  -1.4191   1.0046
 1HW  H14  H  HCH2  0   0.238  -1.3307   3.3942  -1.8890
 1HW  H15  H  HCH2  0   0.239  -2.2168   4.2345  -0.6295
 1HW  H16  H  HOH1  0   0.462  -1.1817   5.6942  -2.1187
 1HW  H18  H  HCH3  0   0.260  -7.6281  -1.2716  -2.8053
 1HW  H19  H  HCH3  0   0.229  -6.5706  -2.6393  -2.4140
 1HW  H20  H  HCH3  0   0.229  -7.6524  -1.9642  -1.1748
 1HW  O27  O  O2    0  -0.514   4.6177  -0.9537  -0.8061

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
 1HW  C1   C6   aromatic  1.387  0.020  1.387
 1HW  C1   C2   aromatic  1.389  0.020  1.389
 1HW  C6   C5   aromatic  1.396  0.020  1.396
 1HW  C7   C2   single    1.509  0.020  1.509
 1HW  C7   C8   single    1.526  0.020  1.526
 1HW  C2   C3   aromatic  1.403  0.020  1.403
 1HW  C5   O24  single    1.347  0.020  1.347
 1HW  C5   C4   aromatic  1.389  0.020  1.389
 1HW  O24  C25  single    1.414  0.020  1.414
 1HW  C3   C4   aromatic  1.392  0.020  1.392
 1HW  C3   C10  single    1.454  0.020  1.454
 1HW  C8   C9   single    1.519  0.020  1.519
 1HW  C9   C10  single    1.499  0.020  1.499
 1HW  C9   C11  single    1.545  0.020  1.545
 1HW  C10  N13  double    1.275  0.020  1.275
 1HW  N13  N12  single    1.368  0.020  1.368
 1HW  C11  N12  single    1.462  0.020  1.462
 1HW  C11  C14  single    1.508  0.020  1.508
 1HW  N12  C20  single    1.354  0.020  1.354
 1HW  C15  C14  aromatic  1.390  0.020  1.390
 1HW  C15  C16  aromatic  1.379  0.020  1.379
 1HW  C14  C19  aromatic  1.390  0.020  1.390
 1HW  F26  C16  single    1.334  0.020  1.334
 1HW  C16  C17  aromatic  1.386  0.020  1.386
 1HW  C19  C18  aromatic  1.386  0.020  1.386
 1HW  C20  C21  single    1.516  0.020  1.516
 1HW  C20  O23  double    1.215  0.020  1.215
 1HW  C17  C18  aromatic  1.383  0.020  1.383
 1HW  C17  O27  single    1.382  0.020  1.382
 1HW  C21  O22  single    1.397  0.020  1.397
 1HW  O27  C28  single    1.343  0.020  1.343
 1HW  F31  C28  single    1.334  0.020  1.334
 1HW  C28  F29  single    1.332  0.020  1.332
 1HW  C28  F30  single    1.321  0.020  1.321
 1HW  C1   H1   single    0.930  0.020  1.080
 1HW  C4   H2   single    0.930  0.020  1.080
 1HW  C11  H4   single    0.970  0.020  1.090
 1HW  C6   H5   single    0.930  0.020  1.080
 1HW  C7   H6   single    0.970  0.020  1.090
 1HW  C7   H7   single    0.970  0.020  1.090
 1HW  C9   H8   single    0.970  0.020  1.090
 1HW  C15  H9   single    0.930  0.020  1.080
 1HW  C18  H10  single    0.930  0.020  1.080
 1HW  C19  H11  single    0.930  0.020  1.080
 1HW  C8   H12  single    0.970  0.020  1.090
 1HW  C8   H13  single    0.970  0.020  1.090
 1HW  C21  H14  single    0.970  0.020  1.090
 1HW  C21  H15  single    0.970  0.020  1.090
 1HW  O22  H16  single    0.850  0.020  0.980
 1HW  C25  H18  single    0.970  0.020  1.090
 1HW  C25  H19  single    0.970  0.020  1.090
 1HW  C25  H20  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
 1HW  H1   C1   C6   118.52  3.000
 1HW  H1   C1   C2   119.33  3.000
 1HW  C6   C1   C2   122.14  3.000
 1HW  C7   C2   C3   121.72  3.000
 1HW  C3   C2   C1   117.45  3.000
 1HW  C7   C2   C1   120.83  3.000
 1HW  C10  C3   C4   121.25  3.000
 1HW  C10  C3   C2   117.70  3.000
 1HW  C4   C3   C2   121.02  3.000
 1HW  H2   C4   C5   119.55  3.000
 1HW  H2   C4   C3   119.98  3.000
 1HW  C5   C4   C3   120.48  3.000
 1HW  O24  C5   C6   124.42  3.000
 1HW  O24  C5   C4   116.44  3.000
 1HW  C6   C5   C4   119.14  3.000
 1HW  N13  C10  C9   113.99  3.000
 1HW  N13  C10  C3   125.01  3.000
 1HW  C9   C10  C3   120.98  3.000
 1HW  H4   C11  N12  110.33  3.000
 1HW  H4   C11  C14  109.29  3.000
 1HW  N12  C11  C14  112.30  3.000
 1HW  H4   C11  C9   110.61  3.000
 1HW  C14  C11  C9   113.79  3.000
 1HW  N12  C11  C9   100.27  3.000
 1HW  H5   C6   C5   121.40  3.000
 1HW  H5   C6   C1   118.83  3.000
 1HW  C5   C6   C1   119.77  3.000
 1HW  H7   C7   H6   106.11  3.000
 1HW  H7   C7   C8   109.95  3.000
 1HW  H6   C7   C8   108.96  3.000
 1HW  H7   C7   C2   109.48  3.000
 1HW  H6   C7   C2   109.08  3.000
 1HW  C8   C7   C2   113.02  3.000
 1HW  H8   C9   C8   108.09  3.000
 1HW  H8   C9   C11  108.55  3.000
 1HW  C8   C9   C11  120.04  3.000
 1HW  H8   C9   C10  107.79  3.000
 1HW  C11  C9   C10  101.13  3.000
 1HW  C8   C9   C10  110.59  3.000
 1HW  O27  C28  F30  107.56  3.000
 1HW  F30  C28  F29  108.71  3.000
 1HW  O27  C28  F29  112.69  3.000
 1HW  F30  C28  F31  108.40  3.000
 1HW  F29  C28  F31  106.86  3.000
 1HW  O27  C28  F31  112.51  3.000
 1HW  C18  C17  C16  119.50  3.000
 1HW  C18  C17  O27  121.30  3.000
 1HW  C16  C17  O27  119.10  3.000
 1HW  C15  C16  F26  119.79  3.000
 1HW  F26  C16  C17  119.17  3.000
 1HW  C15  C16  C17  121.03  3.000
 1HW  H9   C15  C14  120.91  3.000
 1HW  H9   C15  C16  119.41  3.000
 1HW  C14  C15  C16  119.68  3.000
 1HW  H10  C18  C19  120.15  3.000
 1HW  H10  C18  C17  120.03  3.000
 1HW  C19  C18  C17  119.81  3.000
 1HW  H11  C19  C14  120.90  3.000
 1HW  H11  C19  C18  118.51  3.000
 1HW  C14  C19  C18  120.59  3.000
 1HW  C19  C14  C15  119.39  3.000
 1HW  C19  C14  C11  122.12  3.000
 1HW  C15  C14  C11  118.44  3.000
 1HW  H13  C8   H12  107.20  3.000
 1HW  H13  C8   C9   110.48  3.000
 1HW  H12  C8   C9   110.89  3.000
 1HW  H13  C8   C7   109.83  3.000
 1HW  H12  C8   C7   110.31  3.000
 1HW  C9   C8   C7   108.13  3.000
 1HW  N13  N12  C20  121.79  3.000
 1HW  C20  N12  C11  124.48  3.000
 1HW  N13  N12  C11  113.17  3.000
 1HW  C21  C20  O23  123.61  3.000
 1HW  O23  C20  N12  121.05  3.000
 1HW  C21  C20  N12  115.34  3.000
 1HW  H15  C21  H14  106.13  3.000
 1HW  H15  C21  O22  112.73  3.000
 1HW  H14  C21  O22  112.73  3.000
 1HW  H15  C21  C20  108.85  3.000
 1HW  H14  C21  C20  108.49  3.000
 1HW  O22  C21  C20  107.79  3.000
 1HW  H16  O22  C21  107.50  3.000
 1HW  N12  N13  C10  107.94  3.000
 1HW  C25  O24  C5   118.59  3.000
 1HW  H20  C25  H19  108.82  3.000
 1HW  H20  C25  H18  108.69  3.000
 1HW  H19  C25  H18  108.77  3.000
 1HW  H20  C25  O24  112.02  3.000
 1HW  H19  C25  O24  111.95  3.000
 1HW  H18  C25  O24  106.47  3.000
 1HW  C17  O27  C28  117.55  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
 1HW  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 1HW  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 1HW  CONST_03  C5   C6   C1   C2      0.00   0.0  0
 1HW  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 1HW  CONST_05  C6   C1   C2   C3      0.00   0.0  0
 1HW  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 1HW  CONST_07  C14  C15  C16  C17     0.00   0.0  0
 1HW  CONST_08  C14  C19  C18  C17     0.00   0.0  0
 1HW  CONST_09  C19  C14  C15  C16     0.00   0.0  0
 1HW  CONST_10  C19  C18  C17  C16     0.00   0.0  0
 1HW  CONST_11  C18  C19  C14  C15     0.00   0.0  0
 1HW  CONST_12  C18  C17  C16  C15     0.00   0.0  0
 1HW  CONST_13  C16  C15  C14  C11   180.00   0.0  0
 1HW  CONST_14  C18  C19  C14  C11   180.00   0.0  0
 1HW  CONST_15  O24  C5   C6   C1    180.00   0.0  0
 1HW  CONST_16  O24  C5   C4   C3    180.00   0.0  0
 1HW  CONST_17  C15  C16  C17  O27   180.00   0.0  0
 1HW  CONST_18  C19  C18  C17  O27   180.00   0.0  0
 1HW  CONST_19  C14  C15  C16  F26   180.00   0.0  0
 1HW  CONST_20  C18  C17  C16  F26   180.00   0.0  0
 1HW  CONST_21  H5   C6   C1   C2    180.00   0.0  0
 1HW  CONST_22  H2   C4   C3   C2    180.00   0.0  0
 1HW  CONST_23  H1   C1   C2   C3    180.00   0.0  0
 1HW  CONST_24  H9   C15  C14  C11     0.00   0.0  0
 1HW  CONST_25  H11  C19  C14  C11     0.00   0.0  0
 1HW  CONST_26  H10  C18  C17  C16   180.00   0.0  0
 1HW  CONST_27  C21  C20  N12  C11   180.00   0.0  0
 1HW  CONST_28  O23  C20  N12  C11     0.00   0.0  0
 1HW  CONST_29  N13  N12  C20  O23   180.00   0.0  0
 1HW  CONST_30  N13  N12  C20  C21     0.00   0.0  0
 1HW  Var_01    C8   C7   C2   C1    154.30  30.0  1
 1HW  Var_02    C9   C8   C7   C2     53.19  30.0  1
 1HW  Var_03    C9   C10  C3   C2     -7.84  30.0  1
 1HW  Var_04    C11  N12  N13  C10    10.18  30.0  1
 1HW  Var_05    C16  C17  O27  C28    97.24  30.0  2
 1HW  Var_06    O22  C21  C20  N12   179.26  30.0  3
 1HW  Var_07    H18  C25  O24  C5   -178.03  30.0  3

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
 1HW  chir_01  C11  C9  N12  C14  positiv
 1HW  chir_02  C9   C8  C10  C11  positiv

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
 1HW  plan-1  C11  0.020
 1HW  plan-1  C17  0.020
 1HW  plan-1  C16  0.020
 1HW  plan-1  F26  0.020
 1HW  plan-1  C15  0.020
 1HW  plan-1  C18  0.020
 1HW  plan-1  C19  0.020
 1HW  plan-1  C14  0.020
 1HW  plan-1  H9   0.020
 1HW  plan-1  H10  0.020
 1HW  plan-1  H11  0.020
 1HW  plan-1  O27  0.020
 1HW  plan-2  C1   0.020
 1HW  plan-2  C2   0.020
 1HW  plan-2  C3   0.020
 1HW  plan-2  C4   0.020
 1HW  plan-2  C5   0.020
 1HW  plan-2  C10  0.020
 1HW  plan-2  C6   0.020
 1HW  plan-2  C7   0.020
 1HW  plan-2  O24  0.020
 1HW  plan-2  H1   0.020
 1HW  plan-2  H2   0.020
 1HW  plan-2  H5   0.020
 1HW  plan-3  C11  0.020
 1HW  plan-3  N12  0.020
 1HW  plan-3  C20  0.020
 1HW  plan-3  O23  0.020
 1HW  plan-3  C21  0.020
 1HW  plan-3  N13  0.020

