# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 05:49:59 2020
#   Inital geometry file: a 106 line input string
#   Ligand name: (4~{R})-4-(5-bromanyl-2-fluoranyl-phenyl)-5,6,7-trimethoxy-3,4-dihydro-1~{H}-quinolin-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc2NC(=O)C[C@@H](c3cc(Br)ccc3F)c2c(OC)c1OC
#
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
 EGH  EGH  (4~{R})-4-(5-bromanyl-2-fluoranyl-phenyl)-5,6,7-trimethoxy-3,4-dihydro-1~{H}-quinolin-2-one  ligand  42  25  .  2022-07-24  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_EGH
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
 EGH  C10  C   CR6   0   0.327  -3.1264   1.5176   0.1234
 EGH  C13  C   CH1   0  -0.384  -0.2334  -1.3243  -1.3186
 EGH  C15  C   C     0   0.502   0.5506   0.5344  -2.8589
 EGH  C17  C   CH2   0  -0.571   0.1942  -0.9230  -2.7352
 EGH  C20  C   CR6   0   0.536   1.8089  -2.5002  -0.4184
 EGH  C22  C   CR6   0  -0.030   0.9609  -1.4006  -0.3852
 EGH  C24  C   CR6   0  -0.112   2.3971  -0.4910   1.3273
 EGH  C02  C   CH3   0  -0.409  -3.7760  -0.0871   2.8036
 EGH  C03  C   CR6   0   0.185  -3.1900   0.1860   0.5607
 EGH  C04  C   CR6   0   0.289  -2.2619  -0.7323   0.0851
 EGH  O05  O   O2    0  -0.483  -2.2766  -2.0079   0.5475
 EGH  C06  C   CH3   0  -0.415  -3.2484  -2.8526  -0.0602
 EGH  C07  C   CR6   0  -0.076  -1.2801  -0.3625  -0.8332
 EGH  C08  C   CR6   0   0.400  -1.2336   0.9617  -1.2499
 EGH  C09  C   CR16  0  -0.505  -2.1514   1.9011  -0.7884
 EGH  O11  O   O2    0  -0.459  -4.0499   2.3433   0.6356
 EGH  C12  C   CH3   0  -0.442  -4.0475   3.6982   0.2280
 EGH  N14  N   NH1   0  -0.734  -0.2223   1.3704  -2.1192
 EGH  O16  O   O     0  -0.462   1.4272   0.9515  -3.5936
 EGH  C18  C   CR16  0  -0.229   3.2262  -1.5996   1.2758
 EGH  C19  C   CR16  0  -0.402   2.9213  -2.6205   0.3881
 EGH  F21  F   F     0  -0.309   1.5328  -3.4969  -1.2748
 EGH  C23  C   CR16  0  -0.254   1.2770  -0.3888   0.5153
 EGH  BR   BR  BR    0  -0.041   2.7919   0.9089   2.5317
 EGH  H1   H   HCH1  0   0.294  -0.6691  -2.3218  -1.3882
 EGH  H2   H   HCH2  0   0.283   1.0320  -1.5206  -3.0896
 EGH  H3   H   HCH2  0   0.300  -0.6405  -1.1099  -3.4200
 EGH  H4   H   HCH3  0   0.222  -2.9363  -0.7442   3.0408
 EGH  H5   H   HCH3  0   0.223  -3.5069   0.9381   3.0688
 EGH  H6   H   HCH3  0   0.238  -4.6354  -0.3885   3.3999
 EGH  H7   H   HCH3  0   0.243  -3.0916  -3.8535   0.3367
 EGH  H8   H   HCH3  0   0.233  -4.2658  -2.5349   0.1733
 EGH  H9   H   HCH3  0   0.221  -3.1266  -2.8833  -1.1465
 EGH  H10  H   HCR6  0   0.296  -2.0849   2.9206  -1.1444
 EGH  H11  H   HCH3  0   0.265  -4.8624   4.1801   0.7619
 EGH  H12  H   HCH3  0   0.232  -3.1119   4.2010   0.4852
 EGH  H13  H   HCH3  0   0.232  -4.2204   3.8004  -0.8462
 EGH  H14  H   HNH1  0   0.409  -0.0754   2.3628  -2.2421
 EGH  H15  H   HCR6  0   0.290   4.0975  -1.6838   1.9103
 EGH  H16  H   HCR6  0   0.291   3.5464  -3.5014   0.3291
 EGH  H17  H   HCR6  0   0.286   0.6324   0.4771   0.5883
 EGH  O01  O   O2    0  -0.482  -4.1552  -0.1945   1.4371

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
 EGH  C12  O11  single    1.415  0.020  1.415
 EGH  C09  C08  aromatic  1.392  0.020  1.392
 EGH  C09  C10  aromatic  1.389  0.020  1.389
 EGH  N14  C08  single    1.395  0.020  1.395
 EGH  N14  C15  single    1.358  0.020  1.358
 EGH  O11  C10  single    1.340  0.020  1.340
 EGH  O16  C15  double    1.217  0.020  1.217
 EGH  C08  C07  aromatic  1.389  0.020  1.389
 EGH  C10  C03  aromatic  1.403  0.020  1.403
 EGH  C15  C17  single    1.505  0.020  1.505
 EGH  C03  O01  single    1.358  0.020  1.358
 EGH  C03  C04  aromatic  1.390  0.020  1.390
 EGH  C07  C04  aromatic  1.394  0.020  1.394
 EGH  C07  C13  single    1.502  0.020  1.502
 EGH  C02  O01  single    1.422  0.020  1.422
 EGH  C17  C13  single    1.533  0.020  1.533
 EGH  C04  O05  single    1.357  0.020  1.357
 EGH  C13  C22  single    1.518  0.020  1.518
 EGH  O05  C06  single    1.424  0.020  1.424
 EGH  C22  C23  aromatic  1.391  0.020  1.391
 EGH  C22  C20  aromatic  1.389  0.020  1.389
 EGH  C23  C24  aromatic  1.387  0.020  1.387
 EGH  F21  C20  single    1.343  0.020  1.343
 EGH  C20  C19  aromatic  1.379  0.020  1.379
 EGH  C24  BR   single    1.888  0.020  1.888
 EGH  C24  C18  aromatic  1.385  0.020  1.385
 EGH  C19  C18  aromatic  1.387  0.020  1.387
 EGH  C13  H1   single    0.970  0.020  1.090
 EGH  C17  H2   single    0.970  0.020  1.090
 EGH  C17  H3   single    0.970  0.020  1.090
 EGH  C02  H4   single    0.970  0.020  1.090
 EGH  C02  H5   single    0.970  0.020  1.090
 EGH  C02  H6   single    0.970  0.020  1.090
 EGH  C06  H7   single    0.970  0.020  1.090
 EGH  C06  H8   single    0.970  0.020  1.090
 EGH  C06  H9   single    0.970  0.020  1.090
 EGH  C09  H10  single    0.930  0.020  1.080
 EGH  C12  H11  single    0.970  0.020  1.090
 EGH  C12  H12  single    0.970  0.020  1.090
 EGH  C12  H13  single    0.970  0.020  1.090
 EGH  N14  H14  single    0.860  0.020  1.020
 EGH  C18  H15  single    0.930  0.020  1.080
 EGH  C19  H16  single    0.930  0.020  1.080
 EGH  C23  H17  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
 EGH  O11  C10  C09  124.36  3.000
 EGH  O11  C10  C03  115.74  3.000
 EGH  C09  C10  C03  119.90  3.000
 EGH  H1   C13  C07  109.14  3.000
 EGH  H1   C13  C22  107.92  3.000
 EGH  C07  C13  C22  112.45  3.000
 EGH  H1   C13  C17  106.97  3.000
 EGH  C22  C13  C17  111.22  3.000
 EGH  C07  C13  C17  108.98  3.000
 EGH  O16  C15  N14  121.85  3.000
 EGH  O16  C15  C17  123.49  3.000
 EGH  N14  C15  C17  114.62  3.000
 EGH  H3   C17  H2   106.81  3.000
 EGH  H3   C17  C15  107.10  3.000
 EGH  H2   C17  C15  108.82  3.000
 EGH  H3   C17  C13  108.68  3.000
 EGH  H2   C17  C13  111.83  3.000
 EGH  C15  C17  C13  113.29  3.000
 EGH  F21  C20  C19  118.30  3.000
 EGH  C19  C20  C22  123.19  3.000
 EGH  F21  C20  C22  118.51  3.000
 EGH  C23  C22  C20  116.92  3.000
 EGH  C20  C22  C13  120.36  3.000
 EGH  C23  C22  C13  122.71  3.000
 EGH  BR   C24  C23  119.18  3.000
 EGH  BR   C24  C18  119.46  3.000
 EGH  C23  C24  C18  121.36  3.000
 EGH  H6   C02  H5   108.75  3.000
 EGH  H6   C02  H4   108.75  3.000
 EGH  H5   C02  H4   108.81  3.000
 EGH  H6   C02  O01  107.15  3.000
 EGH  H5   C02  O01  111.70  3.000
 EGH  H4   C02  O01  111.60  3.000
 EGH  C04  C03  O01  120.69  3.000
 EGH  C04  C03  C10  119.36  3.000
 EGH  O01  C03  C10  119.95  3.000
 EGH  C07  C04  O05  118.78  3.000
 EGH  O05  C04  C03  119.82  3.000
 EGH  C07  C04  C03  121.36  3.000
 EGH  C06  O05  C04  114.81  3.000
 EGH  H9   C06  H8   108.94  3.000
 EGH  H9   C06  H7   108.70  3.000
 EGH  H8   C06  H7   108.92  3.000
 EGH  H9   C06  O05  111.38  3.000
 EGH  H8   C06  O05  111.86  3.000
 EGH  H7   C06  O05  106.96  3.000
 EGH  C08  C07  C04  118.30  3.000
 EGH  C04  C07  C13  122.25  3.000
 EGH  C08  C07  C13  119.35  3.000
 EGH  N14  C08  C09  119.14  3.000
 EGH  N14  C08  C07  119.38  3.000
 EGH  C09  C08  C07  121.46  3.000
 EGH  H10  C09  C08  119.10  3.000
 EGH  H10  C09  C10  121.29  3.000
 EGH  C08  C09  C10  119.61  3.000
 EGH  C12  O11  C10  118.60  3.000
 EGH  H13  C12  H12  108.89  3.000
 EGH  H13  C12  H11  108.83  3.000
 EGH  H12  C12  H11  108.80  3.000
 EGH  H13  C12  O11  111.86  3.000
 EGH  H12  C12  O11  111.97  3.000
 EGH  H11  C12  O11  106.37  3.000
 EGH  H14  N14  C08  117.96  3.000
 EGH  H14  N14  C15  117.10  3.000
 EGH  C08  N14  C15  124.88  3.000
 EGH  H15  C18  C19  119.70  3.000
 EGH  H15  C18  C24  121.53  3.000
 EGH  C19  C18  C24  118.77  3.000
 EGH  H16  C19  C18  120.49  3.000
 EGH  H16  C19  C20  120.34  3.000
 EGH  C18  C19  C20  119.17  3.000
 EGH  H17  C23  C24  120.03  3.000
 EGH  H17  C23  C22  119.38  3.000
 EGH  C24  C23  C22  120.59  3.000
 EGH  C03  O01  C02  114.17  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
 EGH  CONST_01  C07  C08  C09  C10     0.00   0.0  0
 EGH  CONST_02  C07  C04  C03  C10     0.00   0.0  0
 EGH  CONST_03  C24  C23  C22  C20     0.00   0.0  0
 EGH  CONST_04  C24  C18  C19  C20     0.00   0.0  0
 EGH  CONST_05  C18  C24  C23  C22     0.00   0.0  0
 EGH  CONST_06  C18  C19  C20  C22     0.00   0.0  0
 EGH  CONST_07  C08  C09  C10  C03     0.00   0.0  0
 EGH  CONST_08  C08  C07  C04  C03     0.00   0.0  0
 EGH  CONST_09  C09  C10  C03  C04     0.00   0.0  0
 EGH  CONST_10  C09  C08  C07  C04     0.00   0.0  0
 EGH  CONST_11  C23  C22  C20  C19     0.00   0.0  0
 EGH  CONST_12  C23  C24  C18  C19     0.00   0.0  0
 EGH  CONST_13  C24  C23  C22  C13   180.00   0.0  0
 EGH  CONST_14  C19  C20  C22  C13   180.00   0.0  0
 EGH  CONST_15  C08  N14  C15  C17     0.00   0.0  0
 EGH  CONST_16  O05  C04  C03  C10   180.00   0.0  0
 EGH  CONST_17  O05  C04  C07  C13     0.00   0.0  0
 EGH  CONST_18  F21  C20  C22  C13     0.00   0.0  0
 EGH  CONST_19  BR   C24  C23  C22   180.00   0.0  0
 EGH  CONST_20  C09  C10  C03  O01   180.00   0.0  0
 EGH  CONST_21  C07  C04  C03  O01   180.00   0.0  0
 EGH  CONST_22  O11  C10  C03  C04   180.00   0.0  0
 EGH  CONST_23  C08  C07  C04  O05   180.00   0.0  0
 EGH  CONST_24  O11  C10  C09  C08   180.00   0.0  0
 EGH  CONST_25  F21  C20  C19  C18   180.00   0.0  0
 EGH  CONST_26  BR   C24  C18  C19   180.00   0.0  0
 EGH  CONST_27  C23  C22  C20  F21   180.00   0.0  0
 EGH  CONST_28  O16  C15  N14  C08   180.00   0.0  0
 EGH  CONST_29  H17  C23  C22  C13     0.00   0.0  0
 EGH  CONST_30  H15  C18  C19  C20   180.00   0.0  0
 EGH  CONST_31  H16  C19  C20  C22   180.00   0.0  0
 EGH  CONST_32  H10  C09  C10  C03   180.00   0.0  0
 EGH  CONST_33  H14  N14  C15  C17   180.00   0.0  0
 EGH  Var_01    N14  C15  C17  C13   -37.14  30.0  1
 EGH  Var_02    C09  C08  N14  C15  -165.27  30.0  1
 EGH  Var_03    C04  C03  O01  C02    89.40  30.0  2
 EGH  Var_04    C07  C04  O05  C06  -101.22  30.0  2
 EGH  Var_05    H11  C12  O11  C10  -179.67  30.0  3
 EGH  Var_06    H4   C02  O01  C03   -62.75  30.0  3
 EGH  Var_07    H7   C06  O05  C04   175.14  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
 EGH  chir_01  C13  C07  C17  C22  negativ

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
 EGH  plan-1  C13  0.020
 EGH  plan-1  C20  0.020
 EGH  plan-1  C22  0.020
 EGH  plan-1  C24  0.020
 EGH  plan-1  C18  0.020
 EGH  plan-1  C19  0.020
 EGH  plan-1  F21  0.020
 EGH  plan-1  C23  0.020
 EGH  plan-1  BR   0.020
 EGH  plan-1  H15  0.020
 EGH  plan-1  H16  0.020
 EGH  plan-1  H17  0.020
 EGH  plan-2  C10  0.020
 EGH  plan-2  C13  0.020
 EGH  plan-2  C03  0.020
 EGH  plan-2  C04  0.020
 EGH  plan-2  O05  0.020
 EGH  plan-2  C07  0.020
 EGH  plan-2  C08  0.020
 EGH  plan-2  C09  0.020
 EGH  plan-2  O11  0.020
 EGH  plan-2  N14  0.020
 EGH  plan-2  H10  0.020
 EGH  plan-2  O01  0.020
 EGH  plan-3  C15  0.020
 EGH  plan-3  C17  0.020
 EGH  plan-3  C08  0.020
 EGH  plan-3  N14  0.020
 EGH  plan-3  O16  0.020
 EGH  plan-3  H14  0.020

