# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 04:44:21 2022
#   Inital geometry file: a 107 line input string
#   Ligand name: (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5ccccc5nc34)C2=O
#
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
 EHD  EHD  (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione  ligand  42  26  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_EHD
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
 EHD  O18   O  OC    0  -0.499   1.3343  -3.2588   0.3515
 EHD  C14   C  CR6   0   0.562   1.1511  -2.0567   0.1858
 EHD  C15   C  CR66  0  -0.240   2.1877  -1.0637   0.0551
 EHD  C19   C  C     0  -0.220   3.6070  -1.5152   0.1133
 EHD  O22   O  O     0  -0.421   4.4659  -0.7105  -0.7011
 EHD  C20   C  CR6   0   0.569   4.2288   0.5734  -0.9020
 EHD  O23   O  O     0  -0.426   4.9438   1.2031  -1.6359
 EHD  C16   C  CR66  0   0.280   1.9026   0.2603  -0.1082
 EHD  C17   C  CR16  0  -0.473   0.5687   0.7177  -0.1771
 EHD  C21   C  CR6   0  -0.011   3.0621   1.2229  -0.1542
 EHD  O24   O  OH1   0  -0.655   2.6530   2.3704  -0.8292
 EHD  C25   C  CH2   0  -0.449   3.4983   1.5348   1.2985
 EHD  C31   C  CH3   0  -0.689   4.6203   2.5571   1.4156
 EHD  N12   N  N     0  -0.636  -0.1209  -1.5396   0.1100
 EHD  C11   C  CH2   0  -0.298  -1.3129  -2.3813   0.2160
 EHD  C8    C  CR56  0   0.072  -2.4109  -1.3774   0.0926
 EHD  C7    C  CR16  0  -0.248  -3.7655  -1.5061   0.1183
 EHD  C6    C  CR66  0   0.103  -4.5397  -0.3311  -0.0249
 EHD  C5    C  CR66  0   0.202  -3.8713   0.9168  -0.1897
 EHD  N10   N  N     0  -0.448  -2.5219   1.0197  -0.2121
 EHD  C9    C  CR56  0   0.036  -1.8577  -0.0900  -0.0743
 EHD  C13   C  CR56  0   0.535  -0.4063  -0.2192  -0.0598
 EHD  C1    C  CR16  0  -0.314  -5.9523  -0.3565  -0.0073
 EHD  C2    C  CR16  0  -0.248  -6.6692   0.7999  -0.1474
 EHD  C3    C  CR16  0  -0.256  -6.0063   2.0349  -0.3127
 EHD  C4    C  CR16  0  -0.305  -4.6402   2.0944  -0.3334
 EHD  H191  H  H     0   0.286   3.7117  -2.5311  -0.2626
 EHD  H192  H  H     0   0.272   3.9881  -1.5073   1.1390
 EHD  H17   H  HCR6  0   0.278   0.3109   1.7571  -0.3075
 EHD  H24   H  HOH1  0   0.461   3.4164   2.9376  -0.9886
 EHD  H251  H  HCH2  0   0.253   3.7894   0.6130   1.8069
 EHD  H252  H  HCH2  0   0.266   2.6110   1.9021   1.8202
 EHD  H311  H  HCH3  0   0.254   4.8314   2.7421   2.4681
 EHD  H312  H  HCH3  0   0.237   5.5484   2.2182   0.9559
 EHD  H313  H  HCH3  0   0.230   4.3504   3.5171   0.9745
 EHD  H111  H  HCH2  0   0.300  -1.3259  -3.1252  -0.5826
 EHD  H112  H  HCH2  0   0.300  -1.3234  -2.9093   1.1711
 EHD  H7    H  HCR6  0   0.275  -4.2521  -2.4655   0.2468
 EHD  H1    H  HCR6  0   0.266  -6.4588  -1.3052   0.1212
 EHD  H2    H  HCR6  0   0.268  -7.7504   0.7725  -0.1321
 EHD  H3    H  HCR6  0   0.269  -6.5885   2.9400  -0.4246
 EHD  H4    H  HCR6  0   0.266  -4.1220   3.0361  -0.4614

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
 EHD  O18  C14   double    1.227  0.020  1.227
 EHD  C14  C15   aromatic  1.441  0.020  1.441
 EHD  C14  N12   aromatic  1.375  0.020  1.375
 EHD  C15  C19   single    1.491  0.020  1.491
 EHD  C15  C16   aromatic  1.364  0.020  1.364
 EHD  C19  O22   single    1.431  0.020  1.431
 EHD  C19  H191  single    0.970  0.020  1.090
 EHD  C19  H192  single    0.970  0.020  1.090
 EHD  O22  C20   single    1.321  0.020  1.321
 EHD  C20  O23   double    1.203  0.020  1.203
 EHD  C20  C21   single    1.530  0.020  1.530
 EHD  C16  C17   aromatic  1.412  0.020  1.412
 EHD  C16  C21   single    1.508  0.020  1.508
 EHD  C17  C13   aromatic  1.357  0.020  1.357
 EHD  C17  H17   single    0.930  0.020  1.080
 EHD  C21  O24   single    1.393  0.020  1.393
 EHD  C21  C25   single    1.548  0.020  1.548
 EHD  O24  H24   single    0.850  0.020  0.980
 EHD  C25  C31   single    1.522  0.020  1.522
 EHD  C25  H251  single    0.970  0.020  1.090
 EHD  C25  H252  single    0.970  0.020  1.090
 EHD  C31  H311  single    0.970  0.020  1.090
 EHD  C31  H312  single    0.970  0.020  1.090
 EHD  C31  H313  single    0.970  0.020  1.090
 EHD  N12  C11   single    1.463  0.020  1.463
 EHD  N12  C13   aromatic  1.362  0.020  1.362
 EHD  C11  C8    single    1.493  0.020  1.493
 EHD  C11  H111  single    0.970  0.020  1.090
 EHD  C11  H112  single    0.970  0.020  1.090
 EHD  C8   C7    aromatic  1.361  0.020  1.361
 EHD  C8   C9    aromatic  1.411  0.020  1.411
 EHD  C7   C6    aromatic  1.414  0.020  1.414
 EHD  C7   H7    single    0.930  0.020  1.080
 EHD  C6   C5    aromatic  1.425  0.020  1.425
 EHD  C6   C1    aromatic  1.413  0.020  1.413
 EHD  C5   N10   aromatic  1.353  0.020  1.353
 EHD  C5   C4    aromatic  1.414  0.020  1.414
 EHD  N10  C9    aromatic  1.301  0.020  1.301
 EHD  C9   C13   aromatic  1.457  0.020  1.457
 EHD  C1   C2    aromatic  1.368  0.020  1.368
 EHD  C1   H1    single    0.930  0.020  1.080
 EHD  C2   C3    aromatic  1.411  0.020  1.411
 EHD  C2   H2    single    0.930  0.020  1.080
 EHD  C3   C4    aromatic  1.367  0.020  1.367
 EHD  C3   H3    single    0.930  0.020  1.080
 EHD  C4   H4    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
 EHD  N12   C14  C15   113.65  3.000
 EHD  N12   C14  O18   120.92  3.000
 EHD  C15   C14  O18   125.43  3.000
 EHD  C16   C15  C19   119.85  3.000
 EHD  C16   C15  C14   121.95  3.000
 EHD  C19   C15  C14   118.20  3.000
 EHD  H192  C19  H191  107.28  3.000
 EHD  H192  C19  O22   108.68  3.000
 EHD  H191  C19  O22   105.70  3.000
 EHD  H192  C19  C15   111.47  3.000
 EHD  H191  C19  C15   111.16  3.000
 EHD  O22   C19  C15   112.27  3.000
 EHD  C20   O22  C19   121.69  3.000
 EHD  C21   C20  O23   121.95  3.000
 EHD  C21   C20  O22   118.36  3.000
 EHD  O23   C20  O22   119.67  3.000
 EHD  C21   C16  C17   121.21  3.000
 EHD  C21   C16  C15   117.56  3.000
 EHD  C17   C16  C15   121.18  3.000
 EHD  H17   C17  C13   120.25  3.000
 EHD  H17   C17  C16   122.95  3.000
 EHD  C13   C17  C16   116.80  3.000
 EHD  C25   C21  O24   111.81  3.000
 EHD  C25   C21  C16   108.46  3.000
 EHD  O24   C21  C16   108.36  3.000
 EHD  C25   C21  C20   109.22  3.000
 EHD  O24   C21  C20   109.68  3.000
 EHD  C16   C21  C20   109.28  3.000
 EHD  H24   O24  C21   109.40  3.000
 EHD  H252  C25  H251  106.13  3.000
 EHD  H252  C25  C31   109.63  3.000
 EHD  H251  C25  C31   109.54  3.000
 EHD  H252  C25  C21   106.67  3.000
 EHD  H251  C25  C21   109.98  3.000
 EHD  C31   C25  C21   114.52  3.000
 EHD  H313  C31  H312  108.30  3.000
 EHD  H313  C31  H311  106.81  3.000
 EHD  H312  C31  H311  107.18  3.000
 EHD  H313  C31  C25   112.19  3.000
 EHD  H312  C31  C25   112.73  3.000
 EHD  H311  C31  C25   109.34  3.000
 EHD  C13   N12  C11   113.34  3.000
 EHD  C13   N12  C14   124.43  3.000
 EHD  C11   N12  C14   122.23  3.000
 EHD  H112  C11  H111  108.09  3.000
 EHD  H112  C11  C8    112.99  3.000
 EHD  H111  C11  C8    112.90  3.000
 EHD  H112  C11  N12   110.46  3.000
 EHD  H111  C11  N12   110.42  3.000
 EHD  C8    C11  N12   101.91  3.000
 EHD  C9    C8   C7    118.60  3.000
 EHD  C9    C8   C11   109.56  3.000
 EHD  C7    C8   C11   131.83  3.000
 EHD  H7    C7   C6    120.12  3.000
 EHD  H7    C7   C8    122.21  3.000
 EHD  C6    C7   C8    117.66  3.000
 EHD  C1    C6   C5    119.08  3.000
 EHD  C1    C6   C7    122.07  3.000
 EHD  C5    C6   C7    118.84  3.000
 EHD  C4    C5   N10   118.50  3.000
 EHD  C4    C5   C6    119.08  3.000
 EHD  N10   C5   C6    122.42  3.000
 EHD  C9    N10  C5    116.26  3.000
 EHD  C13   C9   N10   125.83  3.000
 EHD  C13   C9   C8    107.97  3.000
 EHD  N10   C9   C8    126.20  3.000
 EHD  C9    C13  N12   107.22  3.000
 EHD  C9    C13  C17   130.80  3.000
 EHD  N12   C13  C17   121.98  3.000
 EHD  H1    C1   C2    120.51  3.000
 EHD  H1    C1   C6    119.00  3.000
 EHD  C2    C1   C6    120.50  3.000
 EHD  H2    C2   C3    119.56  3.000
 EHD  H2    C2   C1    120.07  3.000
 EHD  C3    C2   C1    120.38  3.000
 EHD  H3    C3   C4    119.97  3.000
 EHD  H3    C3   C2    119.43  3.000
 EHD  C4    C3   C2    120.60  3.000
 EHD  H4    C4   C3    121.19  3.000
 EHD  H4    C4   C5    118.44  3.000
 EHD  C3    C4   C5    120.37  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
 EHD  CONST_01  C17   C16  C15  C14    0.00   0.0  0
 EHD  CONST_02  C17   C13  N12  C14    0.00   0.0  0
 EHD  CONST_03  C9    C13  N12  C14  180.00   0.0  0
 EHD  CONST_04  C13   N12  C14  C15    0.00   0.0  0
 EHD  CONST_05  C13   C17  C16  C15    0.00   0.0  0
 EHD  CONST_06  N12   C14  C15  C16    0.00   0.0  0
 EHD  CONST_07  N12   C13  C17  C16    0.00   0.0  0
 EHD  CONST_08  C9    C13  C17  C16  180.00   0.0  0
 EHD  CONST_09  C8    C9   C13  C17  180.00   0.0  0
 EHD  CONST_10  N10   C9   C13  C17    0.00   0.0  0
 EHD  CONST_11  C8    C9   C13  N12    0.00   0.0  0
 EHD  CONST_12  N10   C9   C13  N12  180.00   0.0  0
 EHD  CONST_13  C5    C6   C7   C8     0.00   0.0  0
 EHD  CONST_14  C1    C6   C7   C8   180.00   0.0  0
 EHD  CONST_15  C5    N10  C9   C8     0.00   0.0  0
 EHD  CONST_16  N10   C9   C8   C7     0.00   0.0  0
 EHD  CONST_17  C13   C9   C8   C7   180.00   0.0  0
 EHD  CONST_18  N10   C5   C6   C7     0.00   0.0  0
 EHD  CONST_19  C4    C5   C6   C7   180.00   0.0  0
 EHD  CONST_20  C2    C1   C6   C7   180.00   0.0  0
 EHD  CONST_21  C9    C8   C7   C6     0.00   0.0  0
 EHD  CONST_22  C9    N10  C5   C6     0.00   0.0  0
 EHD  CONST_23  C3    C4   C5   C6     0.00   0.0  0
 EHD  CONST_24  C3    C2   C1   C6     0.00   0.0  0
 EHD  CONST_25  C2    C1   C6   C5     0.00   0.0  0
 EHD  CONST_26  C13   C9   N10  C5   180.00   0.0  0
 EHD  CONST_27  C2    C3   C4   C5     0.00   0.0  0
 EHD  CONST_28  C1    C6   C5   N10  180.00   0.0  0
 EHD  CONST_29  C3    C4   C5   N10  180.00   0.0  0
 EHD  CONST_30  C4    C5   N10  C9   180.00   0.0  0
 EHD  CONST_31  C4    C5   C6   C1     0.00   0.0  0
 EHD  CONST_32  C4    C3   C2   C1     0.00   0.0  0
 EHD  CONST_33  C11   N12  C14  C15  180.00   0.0  0
 EHD  CONST_34  C19   C15  C14  O18    0.00   0.0  0
 EHD  CONST_35  C16   C15  C14  O18  180.00   0.0  0
 EHD  CONST_36  C11   N12  C14  O18    0.00   0.0  0
 EHD  CONST_37  C13   N12  C14  O18  180.00   0.0  0
 EHD  CONST_38  H17   C17  C16  C15  180.00   0.0  0
 EHD  CONST_39  H7    C7   C8   C11    0.00   0.0  0
 EHD  CONST_40  H1    C1   C6   C7     0.00   0.0  0
 EHD  CONST_41  H4    C4   C5   C6   180.00   0.0  0
 EHD  CONST_42  H2    C2   C1   C6   180.00   0.0  0
 EHD  CONST_43  H3    C3   C4   C5   180.00   0.0  0
 EHD  Var_01    O22   C19  C15  C14  147.97  30.0  1
 EHD  Var_02    C21   C20  O22  C19    4.60  30.0  1
 EHD  Var_03    H111  C11  N12  C14  -60.45  30.0  1
 EHD  Var_04    H311  C31  C25  C21  177.73  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
 EHD  chir_01  C21  C16  C20  C25  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
 EHD  plan-1  O18  0.020
 EHD  plan-1  C14  0.020
 EHD  plan-1  C15  0.020
 EHD  plan-1  C19  0.020
 EHD  plan-1  C16  0.020
 EHD  plan-1  C17  0.020
 EHD  plan-1  C21  0.020
 EHD  plan-1  N12  0.020
 EHD  plan-1  C11  0.020
 EHD  plan-1  C8   0.020
 EHD  plan-1  C7   0.020
 EHD  plan-1  C6   0.020
 EHD  plan-1  C5   0.020
 EHD  plan-1  N10  0.020
 EHD  plan-1  C9   0.020
 EHD  plan-1  C13  0.020
 EHD  plan-1  C1   0.020
 EHD  plan-1  C2   0.020
 EHD  plan-1  C3   0.020
 EHD  plan-1  C4   0.020
 EHD  plan-1  H17  0.020
 EHD  plan-1  H7   0.020
 EHD  plan-1  H1   0.020
 EHD  plan-1  H2   0.020
 EHD  plan-1  H3   0.020
 EHD  plan-1  H4   0.020
 EHD  plan-2  O22  0.020
 EHD  plan-2  C20  0.020
 EHD  plan-2  O23  0.020
 EHD  plan-2  C21  0.020

