# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 00:32:36 2022
#   Inital geometry file: a 122 line input string
#   Ligand name: (1~{S},6~{R})-6-[(1-methoxycarbonyl-3,4-dihydro-2~{H}-quinolin-6-yl)carbamoyl]cyclohex-3-ene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)N1CCCc2cc(NC(=O)[C@@H]3CC=CC[C@@H]3C(O)=O)ccc12
#
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
 EOO  EOO  '(1~{S},6~{R})-6-[(1-methoxycarbonyl-3,4-dihydro-2~{H}-quinolin-6-yl)carbamoyl]cyclohex-3-ene-1-carboxylic acid'  ligand  47  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_EOO
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
 EOO  C17   C  CH1    0  -0.406  19.1395  -1.8949   5.5391
 EOO  C20   C  C1     0  -0.236  19.1850   0.4195   6.5736
 EOO  C21   C  C1     0  -0.209  20.3049   0.7079   5.9182
 EOO  C22   C  CH2    0  -0.458  21.0999  -0.2923   5.1432
 EOO  C23   C  CH1    0  -0.377  20.6508  -1.7384   5.3770
 EOO  C24   C  C      0   0.441  21.2299  -2.7012   4.3165
 EOO  C16   C  C      0   0.575  18.3919  -1.6767   4.2404
 EOO  C01   C  CR6    0   0.301  14.3653  -2.7213   1.0976
 EOO  C02   C  CR6    0   0.112  14.5071  -3.7217   2.0614
 EOO  C03   C  CR16   0  -0.450  15.4968  -3.6113   3.0219
 EOO  C04   C  CR6    0   0.388  16.3587  -2.5125   3.0628
 EOO  C05   C  CR16   0  -0.343  16.2300  -1.5329   2.0770
 EOO  C06   C  CR16   0  -0.257  15.2537  -1.6543   1.0995
 EOO  C08   C  CH2    0  -0.268  13.1007  -4.2284  -0.4301
 EOO  C09   C  CH2    0  -0.493  13.7181  -5.3247   0.4280
 EOO  C10   C  CH2    0  -0.496  13.6547  -4.9416   1.9048
 EOO  C14   C  CH3    0  -0.412  11.8123   0.3130   0.0696
 EOO  C19   C  CH2    0  -0.452  18.5895  -0.9524   6.6230
 EOO  N07   N  NT     0  -0.614  13.3548  -2.8897   0.1233
 EOO  N15   N  NH1    0  -0.751  17.2972  -2.4783   4.0958
 EOO  O12   O  O2     0  -0.470  12.6380  -0.7869   0.4366
 EOO  O13   O  O      0  -0.504  11.7117  -2.0298  -1.1834
 EOO  O18   O  O      0  -0.464  18.6896  -0.8161   3.4313
 EOO  O25   O  O      0  -0.593  20.4492  -3.5456   3.8296
 EOO  O26   O  OC    -1  -0.605  22.4393  -2.5639   4.0461
 EOO  H171  H  HCH1   0   0.253  18.9450  -2.9164   5.8735
 EOO  H201  H  H      0   0.229  18.6675   1.2003   7.1213
 EOO  H211  H  H      0   0.225  20.6741   1.7289   5.9264
 EOO  H222  H  HCH2   0   0.225  22.1536  -0.1984   5.4180
 EOO  H221  H  HCH2   0   0.228  21.0568  -0.0302   4.0827
 EOO  H231  H  HCH1   0   0.237  21.0793  -2.0409   6.3425
 EOO  H031  H  HCR6   0   0.261  15.6082  -4.4049   3.7538
 EOO  H051  H  HCR6   0   0.275  16.8896  -0.6822   2.0490
 EOO  H061  H  HCR6   0   0.258  15.1990  -0.8940   0.3328
 EOO  H081  H  HCH2   0   0.244  12.0220  -4.3763  -0.4682
 EOO  H082  H  HCH2   0   0.249  13.4749  -4.2899  -1.4547
 EOO  H092  H  HCH2   0   0.258  13.1821  -6.2541   0.2313
 EOO  H091  H  HCH2   0   0.242  14.7608  -5.4951   0.1521
 EOO  H101  H  HCH2   0   0.250  12.6178  -4.7408   2.1945
 EOO  H102  H  HCH2   0   0.260  14.0147  -5.7512   2.5402
 EOO  H142  H  HCH3   0   0.247  12.0677   1.1150   0.7565
 EOO  H141  H  HCH3   0   0.234  12.0060   0.6415  -0.9515
 EOO  H143  H  HCH3   0   0.234  10.7537   0.0755   0.1741
 EOO  H191  H  HCH2   0   0.239  17.4986  -0.8914   6.5611
 EOO  H192  H  HCH2   0   0.248  18.7918  -1.3982   7.6029
 EOO  H151  H  HNH1   0   0.409  17.1840  -3.2013   4.7896
 EOO  C11   C  C      0   0.740  12.5114  -1.9006  -0.2800

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
 EOO  C14  O12   single    1.423  0.020  1.423
 EOO  O13  C11   double    1.213  0.020  1.213
 EOO  C11  O12   single    1.330  0.020  1.330
 EOO  C11  N07   single    1.361  0.020  1.361
 EOO  N07  C08   single    1.471  0.020  1.471
 EOO  N07  C01   single    1.414  0.020  1.414
 EOO  C08  C09   single    1.523  0.020  1.523
 EOO  C06  C01   aromatic  1.388  0.020  1.388
 EOO  C06  C05   aromatic  1.387  0.020  1.387
 EOO  C01  C02   aromatic  1.396  0.020  1.396
 EOO  C05  C04   aromatic  1.396  0.020  1.396
 EOO  C09  C10   single    1.527  0.020  1.527
 EOO  C02  C10   single    1.496  0.020  1.496
 EOO  C02  C03   aromatic  1.384  0.020  1.384
 EOO  C04  C03   aromatic  1.397  0.020  1.397
 EOO  C04  N15   single    1.396  0.020  1.396
 EOO  O25  C24   deloc     1.249  0.020  1.249
 EOO  O26  C24   deloc     1.247  0.020  1.247
 EOO  N15  C16   single    1.364  0.020  1.364
 EOO  C24  C23   single    1.545  0.020  1.545
 EOO  C16  O18   double    1.218  0.020  1.218
 EOO  C16  C17   single    1.514  0.020  1.514
 EOO  C23  C17   single    1.528  0.020  1.528
 EOO  C23  C22   single    1.532  0.020  1.532
 EOO  C17  C19   single    1.538  0.020  1.538
 EOO  C22  C21   single    1.494  0.020  1.494
 EOO  C19  C20   single    1.496  0.020  1.496
 EOO  C21  C20   double    1.329  0.020  1.329
 EOO  C17  H171  single    0.970  0.020  1.090
 EOO  C20  H201  single    0.930  0.020  1.080
 EOO  C21  H211  single    0.930  0.020  1.080
 EOO  C22  H222  single    0.970  0.020  1.090
 EOO  C22  H221  single    0.970  0.020  1.090
 EOO  C23  H231  single    0.970  0.020  1.090
 EOO  C03  H031  single    0.930  0.020  1.080
 EOO  C05  H051  single    0.930  0.020  1.080
 EOO  C06  H061  single    0.930  0.020  1.080
 EOO  C08  H081  single    0.970  0.020  1.090
 EOO  C08  H082  single    0.970  0.020  1.090
 EOO  C09  H092  single    0.970  0.020  1.090
 EOO  C09  H091  single    0.970  0.020  1.090
 EOO  C10  H101  single    0.970  0.020  1.090
 EOO  C10  H102  single    0.970  0.020  1.090
 EOO  C14  H142  single    0.970  0.020  1.090
 EOO  C14  H141  single    0.970  0.020  1.090
 EOO  C14  H143  single    0.970  0.020  1.090
 EOO  C19  H191  single    0.970  0.020  1.090
 EOO  C19  H192  single    0.970  0.020  1.090
 EOO  N15  H151  single    0.860  0.020  1.020

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
 EOO  H171  C17  C19   107.08  3.000
 EOO  H171  C17  C16   108.03  3.000
 EOO  C19   C17  C16   109.85  3.000
 EOO  H171  C17  C23   107.71  3.000
 EOO  C19   C17  C23   111.45  3.000
 EOO  C16   C17  C23   112.49  3.000
 EOO  H201  C20  C19   116.95  3.000
 EOO  H201  C20  C21   119.64  3.000
 EOO  C19   C20  C21   123.40  3.000
 EOO  H211  C21  C22   116.90  3.000
 EOO  H211  C21  C20   119.13  3.000
 EOO  C22   C21  C20   123.96  3.000
 EOO  H221  C22  H222  105.15  3.000
 EOO  H221  C22  C23   111.27  3.000
 EOO  H222  C22  C23   108.98  3.000
 EOO  H221  C22  C21   108.76  3.000
 EOO  H222  C22  C21   108.96  3.000
 EOO  C23   C22  C21   113.37  3.000
 EOO  H231  C23  C24   106.59  3.000
 EOO  H231  C23  C22   106.24  3.000
 EOO  C24   C23  C22   111.93  3.000
 EOO  H231  C23  C17   105.32  3.000
 EOO  C22   C23  C17   113.75  3.000
 EOO  C24   C23  C17   112.32  3.000
 EOO  O26   C24  O25   126.60  3.000
 EOO  O26   C24  C23   116.35  3.000
 EOO  O25   C24  C23   117.04  3.000
 EOO  O18   C16  N15   122.73  3.000
 EOO  O18   C16  C17   123.42  3.000
 EOO  N15   C16  C17   113.72  3.000
 EOO  N07   C01  C06   123.35  3.000
 EOO  C06   C01  C02   118.99  3.000
 EOO  N07   C01  C02   117.58  3.000
 EOO  C10   C02  C03   123.03  3.000
 EOO  C03   C02  C01   119.65  3.000
 EOO  C10   C02  C01   117.00  3.000
 EOO  H031  C03  C04   119.47  3.000
 EOO  H031  C03  C02   118.90  3.000
 EOO  C04   C03  C02   121.62  3.000
 EOO  N15   C04  C05   124.57  3.000
 EOO  N15   C04  C03   117.11  3.000
 EOO  C05   C04  C03   118.32  3.000
 EOO  H051  C05  C06   118.82  3.000
 EOO  H051  C05  C04   121.08  3.000
 EOO  C06   C05  C04   120.09  3.000
 EOO  H061  C06  C05   118.29  3.000
 EOO  H061  C06  C01   120.47  3.000
 EOO  C05   C06  C01   121.24  3.000
 EOO  H082  C08  H081  107.38  3.000
 EOO  H082  C08  N07   110.18  3.000
 EOO  H081  C08  N07   107.93  3.000
 EOO  H082  C08  C09   110.42  3.000
 EOO  H081  C08  C09   108.87  3.000
 EOO  N07   C08  C09   111.91  3.000
 EOO  H091  C09  H092  106.90  3.000
 EOO  H091  C09  C10   108.86  3.000
 EOO  H092  C09  C10   111.58  3.000
 EOO  H091  C09  C08   110.92  3.000
 EOO  H092  C09  C08   108.21  3.000
 EOO  C10   C09  C08   110.33  3.000
 EOO  H102  C10  H101  107.13  3.000
 EOO  H102  C10  C09   111.32  3.000
 EOO  H101  C10  C09   109.95  3.000
 EOO  H102  C10  C02   110.87  3.000
 EOO  H101  C10  C02   111.23  3.000
 EOO  C09   C10  C02   106.38  3.000
 EOO  H143  C14  H141  109.15  3.000
 EOO  H143  C14  H142  109.18  3.000
 EOO  H141  C14  H142  109.14  3.000
 EOO  H143  C14  O12   111.74  3.000
 EOO  H141  C14  O12   111.80  3.000
 EOO  H142  C14  O12   105.73  3.000
 EOO  H192  C19  H191  104.92  3.000
 EOO  H192  C19  C20   109.22  3.000
 EOO  H191  C19  C20   110.11  3.000
 EOO  H192  C19  C17   108.36  3.000
 EOO  H191  C19  C17   110.53  3.000
 EOO  C20   C19  C17   113.34  3.000
 EOO  C11   N07  C08   116.29  3.000
 EOO  C08   N07  C01   119.42  3.000
 EOO  C11   N07  C01   124.10  3.000
 EOO  H151  N15  C04   114.58  3.000
 EOO  H151  N15  C16   116.00  3.000
 EOO  C04   N15  C16   129.21  3.000
 EOO  C14   O12  C11   116.92  3.000
 EOO  O13   C11  O12   123.57  3.000
 EOO  O12   C11  N07   112.94  3.000
 EOO  O13   C11  N07   123.48  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
 EOO  CONST_01  C04   C05  C06  C01     0.00   0.0  0
 EOO  CONST_02  C04   C03  C02  C01     0.00   0.0  0
 EOO  CONST_03  C05   C06  C01  C02     0.00   0.0  0
 EOO  CONST_04  C05   C04  C03  C02     0.00   0.0  0
 EOO  CONST_05  C06   C01  C02  C03     0.00   0.0  0
 EOO  CONST_06  C06   C05  C04  C03     0.00   0.0  0
 EOO  CONST_07  N15   C04  C03  C02   180.00   0.0  0
 EOO  CONST_08  N15   C04  C05  C06   180.00   0.0  0
 EOO  CONST_09  H051  C05  C06  C01   180.00   0.0  0
 EOO  CONST_10  H031  C03  C02  C01   180.00   0.0  0
 EOO  CONST_11  H061  C06  C01  C02   180.00   0.0  0
 EOO  CONST_12  C04   N15  C16  C17   180.00   0.0  0
 EOO  CONST_13  C05   C04  N15  C16     0.00   0.0  0
 EOO  CONST_14  C03   C04  N15  C16   180.00   0.0  0
 EOO  CONST_15  H151  N15  C04  C03     0.00   0.0  0
 EOO  CONST_16  O18   C16  N15  C04     0.00   0.0  0
 EOO  Var_01    C21   C20  C19  C17   -16.77  30.0  1
 EOO  Var_02    C23   C22  C21  C20   -10.50  30.0  1
 EOO  Var_03    C19   C20  C21  C22     0.52  30.0  1
 EOO  Var_04    C09   C08  N07  C01    16.30  30.0  1
 EOO  Var_05    C09   C10  C02  C01    44.31  30.0  1
 EOO  Var_06    C08   N07  C01  C02   -38.74  30.0  1
 EOO  Var_07    C08   C09  C10  C02   -63.96  30.0  1
 EOO  Var_08    N07   C08  C09  C10    34.75  30.0  1
 EOO  Var_09    O13   C11  N07  C01   174.56  30.0  2
 EOO  Var_10    N07   C11  O12  C14   178.83  30.0  1
 EOO  Var_11    H142  C14  O12  C11  -179.49  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
 EOO  chir_01  C17  C16  C23  C19  negativ
 EOO  chir_02  C23  C22  C17  C24  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
 EOO  plan-1  C17   0.020
 EOO  plan-1  C16   0.020
 EOO  plan-1  C04   0.020
 EOO  plan-1  N15   0.020
 EOO  plan-1  O18   0.020
 EOO  plan-1  H151  0.020
 EOO  plan-2  C01   0.020
 EOO  plan-2  C02   0.020
 EOO  plan-2  C03   0.020
 EOO  plan-2  C04   0.020
 EOO  plan-2  C05   0.020
 EOO  plan-2  C06   0.020
 EOO  plan-2  C10   0.020
 EOO  plan-2  N07   0.020
 EOO  plan-2  N15   0.020
 EOO  plan-2  H031  0.020
 EOO  plan-2  H051  0.020
 EOO  plan-2  H061  0.020
 EOO  plan-3  C23   0.020
 EOO  plan-3  C24   0.020
 EOO  plan-3  O25   0.020
 EOO  plan-3  O26   0.020
 EOO  plan-4  N07   0.020
 EOO  plan-4  O12   0.020
 EOO  plan-4  O13   0.020
 EOO  plan-4  C11   0.020

