# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 07:53:51 2021
#   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  48  26  .  2022-03-18  2022-11-17
;
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  -0.423  19.8083  -1.9214   4.5976
 EOO  C20   C  C1    0  -0.234  19.6450  -2.7027   7.0016
 EOO  C21   C  C1    0  -0.210  19.5600  -1.4473   7.4267
 EOO  C22   C  CH2   0  -0.464  19.7820  -0.2512   6.5593
 EOO  C23   C  CH1   0  -0.387  20.3660  -0.6273   5.1883
 EOO  C24   C  C     0   0.580  20.2518   0.5070   4.2001
 EOO  C16   C  C     0   0.571  18.3510  -1.8031   4.1908
 EOO  C01   C  CR6   0   0.302  14.3958  -2.8618   1.0211
 EOO  C02   C  CR6   0   0.105  14.3876  -2.6129   2.3942
 EOO  C03   C  CR16  0  -0.398  15.5806  -2.4990   3.0942
 EOO  C04   C  CR6   0   0.381  16.8019  -2.6153   2.4342
 EOO  C05   C  CR16  0  -0.362  16.7999  -2.9089   1.0706
 EOO  C06   C  CR16  0  -0.259  15.6134  -3.0517   0.3754
 EOO  C08   C  CH2   0  -0.269  12.0205  -3.6285   1.0452
 EOO  C09   C  CH2   0  -0.493  12.2906  -3.8203   2.5295
 EOO  C10   C  CH2   0  -0.497  13.0561  -2.6197   3.0794
 EOO  C14   C  CH3   0  -0.413  13.6511  -1.0036  -2.5521
 EOO  C19   C  CH2   0  -0.455  19.9829  -3.0785   5.5940
 EOO  N07   N  NT    0  -0.614  13.1508  -2.9785   0.3632
 EOO  N15   N  NH1   0  -0.746  18.0421  -2.5143   3.0742
 EOO  O12   O  O2    0  -0.471  13.8447  -1.6175  -1.2814
 EOO  O13   O  O     0  -0.510  11.8299  -2.5875  -1.4371
 EOO  O18   O  O     0  -0.459  17.5298  -1.1734   4.8316
 EOO  O25   O  O     0  -0.436  19.7803   0.4091   3.0938
 EOO  O26   O  OH1   0  -0.593  20.7452   1.6417   4.6791
 EOO  H171  H  HCH1  0   0.281  20.3972  -2.1694   3.7109
 EOO  H201  H  H     0   0.242  19.4845  -3.5163   7.7005
 EOO  H211  H  H     0   0.241  19.3124  -1.2496   8.4641
 EOO  H222  H  HCH2  0   0.253  20.4691   0.4303   7.0662
 EOO  H221  H  HCH2  0   0.252  18.8414   0.2951   6.4567
 EOO  H231  H  HCH1  0   0.305  21.4399  -0.7978   5.3352
 EOO  H031  H  HCR6  0   0.265  15.5386  -2.3362   4.1605
 EOO  H051  H  HCR6  0   0.268  17.7383  -3.0437   0.5459
 EOO  H061  H  HCR6  0   0.264  15.6532  -3.3083  -0.6736
 EOO  H081  H  HCH2  0   0.243  11.1459  -2.9883   0.9307
 EOO  H082  H  HCH2  0   0.252  11.7938  -4.5842   0.5681
 EOO  H092  H  HCH2  0   0.260  11.3326  -3.9524   3.0340
 EOO  H091  H  HCH2  0   0.242  12.8719  -4.7274   2.7088
 EOO  H101  H  HCH2  0   0.251  12.4992  -1.6993   2.8738
 EOO  H102  H  HCH2  0   0.261  13.1800  -2.6858   4.1605
 EOO  H142  H  HCH3  0   0.249  14.5474  -0.4177  -2.7350
 EOO  H141  H  HCH3  0   0.236  13.5384  -1.7434  -3.3443
 EOO  H143  H  HCH3  0   0.236  12.7842  -0.3436  -2.5510
 EOO  H191  H  HCH2  0   0.254  19.3868  -3.9387   5.2781
 EOO  H192  H  HCH2  0   0.262  21.0216  -3.4218   5.5480
 EOO  H151  H  HNH1  0   0.411  18.8192  -2.9055   2.5644
 EOO  H3    H  HOH1  0   0.482  20.6501   2.3492   4.0233
 EOO  C11   C  C     0   0.744  12.8725  -2.4094  -0.8414

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    1.424  0.020  1.424
 EOO  O13  C11   double    1.214  0.020  1.214
 EOO  C11  O12   single    1.329  0.020  1.329
 EOO  C11  N07   single    1.361  0.020  1.361
 EOO  N07  C08   single    1.471  0.020  1.471
 EOO  N07  C01   single    1.413  0.020  1.413
 EOO  C08  C09   single    1.521  0.020  1.521
 EOO  C06  C01   aromatic  1.391  0.020  1.391
 EOO  C06  C05   aromatic  1.383  0.020  1.383
 EOO  C01  C02   aromatic  1.396  0.020  1.396
 EOO  C05  C04   aromatic  1.395  0.020  1.395
 EOO  C09  C10   single    1.526  0.020  1.526
 EOO  C02  C10   single    1.497  0.020  1.497
 EOO  C02  C03   aromatic  1.388  0.020  1.388
 EOO  C04  C03   aromatic  1.393  0.020  1.393
 EOO  C04  N15   single    1.399  0.020  1.399
 EOO  O25  C24   double    1.207  0.020  1.207
 EOO  O26  C24   single    1.327  0.020  1.327
 EOO  N15  C16   single    1.359  0.020  1.359
 EOO  C24  C23   single    1.509  0.020  1.509
 EOO  C16  O18   double    1.217  0.020  1.217
 EOO  C16  C17   single    1.518  0.020  1.518
 EOO  C23  C17   single    1.528  0.020  1.528
 EOO  C23  C22   single    1.537  0.020  1.537
 EOO  C17  C19   single    1.537  0.020  1.537
 EOO  C22  C21   single    1.494  0.020  1.494
 EOO  C19  C20   single    1.496  0.020  1.496
 EOO  C21  C20   double    1.328  0.020  1.328
 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
 EOO  O26  H3    single    0.850  0.020  0.980

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   107.09  3.000
 EOO  H171  C17  C16   108.52  3.000
 EOO  C19   C17  C16   109.97  3.000
 EOO  H171  C17  C23   108.01  3.000
 EOO  C19   C17  C23   110.21  3.000
 EOO  C16   C17  C23   112.84  3.000
 EOO  H201  C20  C19   116.84  3.000
 EOO  H201  C20  C21   119.56  3.000
 EOO  C19   C20  C21   123.58  3.000
 EOO  H211  C21  C22   116.31  3.000
 EOO  H211  C21  C20   119.53  3.000
 EOO  C22   C21  C20   124.15  3.000
 EOO  H221  C22  H222  105.85  3.000
 EOO  H221  C22  C23   111.45  3.000
 EOO  H222  C22  C23   109.12  3.000
 EOO  H221  C22  C21   109.08  3.000
 EOO  H222  C22  C21   108.88  3.000
 EOO  C23   C22  C21   112.24  3.000
 EOO  H231  C23  C24   106.17  3.000
 EOO  H231  C23  C22   106.89  3.000
 EOO  C24   C23  C22   111.81  3.000
 EOO  H231  C23  C17   106.11  3.000
 EOO  C22   C23  C17   114.42  3.000
 EOO  C24   C23  C17   110.85  3.000
 EOO  O26   C24  O25   123.07  3.000
 EOO  O26   C24  C23   112.24  3.000
 EOO  O25   C24  C23   124.69  3.000
 EOO  O18   C16  N15   123.36  3.000
 EOO  O18   C16  C17   123.16  3.000
 EOO  N15   C16  C17   113.42  3.000
 EOO  N07   C01  C06   122.95  3.000
 EOO  C06   C01  C02   119.08  3.000
 EOO  N07   C01  C02   117.88  3.000
 EOO  C10   C02  C03   122.27  3.000
 EOO  C03   C02  C01   120.39  3.000
 EOO  C10   C02  C01   117.04  3.000
 EOO  H031  C03  C04   120.98  3.000
 EOO  H031  C03  C02   118.50  3.000
 EOO  C04   C03  C02   120.52  3.000
 EOO  N15   C04  C05   117.62  3.000
 EOO  N15   C04  C03   123.67  3.000
 EOO  C05   C04  C03   118.65  3.000
 EOO  H051  C05  C06   119.14  3.000
 EOO  H051  C05  C04   119.89  3.000
 EOO  C06   C05  C04   120.97  3.000
 EOO  H061  C06  C05   118.75  3.000
 EOO  H061  C06  C01   121.00  3.000
 EOO  C05   C06  C01   120.24  3.000
 EOO  H082  C08  H081  107.56  3.000
 EOO  H082  C08  N07   110.09  3.000
 EOO  H081  C08  N07   107.95  3.000
 EOO  H082  C08  C09   110.66  3.000
 EOO  H081  C08  C09   108.61  3.000
 EOO  N07   C08  C09   111.82  3.000
 EOO  H091  C09  H092  106.91  3.000
 EOO  H091  C09  C10   109.10  3.000
 EOO  H092  C09  C10   111.66  3.000
 EOO  H091  C09  C08   111.08  3.000
 EOO  H092  C09  C08   108.10  3.000
 EOO  C10   C09  C08   109.97  3.000
 EOO  H102  C10  H101  107.15  3.000
 EOO  H102  C10  C09   111.50  3.000
 EOO  H101  C10  C09   109.78  3.000
 EOO  H102  C10  C02   110.67  3.000
 EOO  H101  C10  C02   111.25  3.000
 EOO  C09   C10  C02   106.54  3.000
 EOO  H143  C14  H141  109.24  3.000
 EOO  H143  C14  H142  109.27  3.000
 EOO  H141  C14  H142  109.22  3.000
 EOO  H143  C14  O12   111.61  3.000
 EOO  H141  C14  O12   111.71  3.000
 EOO  H142  C14  O12   105.70  3.000
 EOO  H192  C19  H191  104.97  3.000
 EOO  H192  C19  C20   109.43  3.000
 EOO  H191  C19  C20   110.28  3.000
 EOO  H192  C19  C17   108.45  3.000
 EOO  H191  C19  C17   110.07  3.000
 EOO  C20   C19  C17   113.29  3.000
 EOO  C11   N07  C08   115.97  3.000
 EOO  C08   N07  C01   119.84  3.000
 EOO  C11   N07  C01   123.90  3.000
 EOO  H151  N15  C04   115.07  3.000
 EOO  H151  N15  C16   116.31  3.000
 EOO  C04   N15  C16   127.94  3.000
 EOO  C14   O12  C11   116.92  3.000
 EOO  H3    O26  C24   110.09  3.000
 EOO  O13   C11  O12   123.59  3.000
 EOO  O12   C11  N07   113.11  3.000
 EOO  O13   C11  N07   123.27  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_16  O18   C16  N15  C04     0.00   0.0  0
 EOO  CONST_17  H3    O26  C24  C23   180.00   0.0  0
 EOO  Var_01    C21   C20  C19  C17   -17.41  30.0  1
 EOO  Var_02    C23   C22  C21  C20   -10.33  30.0  1
 EOO  Var_03    C19   C20  C21  C22     0.33  30.0  1
 EOO  Var_04    C09   C08  N07  C01    12.77  30.0  1
 EOO  Var_05    C09   C10  C02  C01    43.32  30.0  1
 EOO  Var_06    C08   N07  C01  C02   -36.74  30.0  1
 EOO  Var_07    C08   C09  C10  C02   -64.61  30.0  1
 EOO  Var_08    N07   C08  C09  C10    37.46  30.0  1
 EOO  Var_09    O13   C11  N07  C01   175.07  30.0  2
 EOO  Var_10    N07   C11  O12  C14   178.57  30.0  1
 EOO  Var_11    H142  C14  O12  C11  -179.24  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-3  H3    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

