# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 23 05:53:11 2021
#   Inital geometry file: a 121 line input string
#   Ligand name: (3~{S},6~{S})-3-[(2,6-dimethyl-4-oxidanyl-phenyl)methyl]-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc(O)cc(C)c1C[C@@H]2NC(=O)[C@H](Cc3ccc(O)cc3)NC2=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
 OUC  OUC  (3~{S},6~{S})-3-[(2,6-dimethyl-4-oxidanyl-phenyl)methyl]-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione  ligand  48  26  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OUC
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
 OUC  C01  C  CH3   0  -0.755   -9.8125  14.4001   3.1104
 OUC  C02  C  CR6   0   0.101  -10.7596  15.4819   3.5534
 OUC  C03  C  CR16  0  -0.450  -12.0562  15.1217   3.8978
 OUC  C04  C  CR6   0   0.377  -12.9851  16.0869   4.2680
 OUC  C06  C  CR16  0  -0.400  -12.6106  17.4219   4.2762
 OUC  C07  C  CR6   0   0.064  -11.3126  17.8035   3.9451
 OUC  C08  C  CH3   0  -0.751  -10.9915  19.2724   3.9900
 OUC  C09  C  CR6   0   0.016  -10.3666  16.8312   3.5885
 OUC  C10  C  CH2   0  -0.541   -8.9329  17.1730   3.2699
 OUC  C11  C  CH1   0  -0.183   -8.0127  16.9684   4.4910
 OUC  C13  C  C     0   0.547   -7.4218  19.0022   5.8043
 OUC  C15  C  CH1   0  -0.189   -6.0159  18.9697   5.2424
 OUC  C16  C  CH2   0  -0.522   -5.7391  20.1952   4.3545
 OUC  C17  C  CR6   0   0.088   -6.5932  20.2600   3.1218
 OUC  C18  C  CR16  0  -0.278   -7.7470  21.0365   3.0877
 OUC  C19  C  CR16  0  -0.386   -8.5433  21.1032   1.9528
 OUC  C20  C  CR6   0   0.342   -8.2017  20.3730   0.8186
 OUC  C22  C  CR16  0  -0.324   -7.0491  19.5906   0.8335
 OUC  C23  C  CR16  0  -0.283   -6.2592  19.5462   1.9702
 OUC  C25  C  C     0   0.536   -6.5634  16.8352   4.0761
 OUC  N12  N  NH1   0  -0.633   -8.2239  17.9758   5.5036
 OUC  N24  N  NH1   0  -0.630   -5.7037  17.7360   4.5619
 OUC  O05  O  OH1   0  -0.637  -14.2529  15.7795   4.6131
 OUC  O14  O  O     0  -0.488   -7.7589  19.9200   6.5366
 OUC  O21  O  OH1   0  -0.632   -8.9374  20.3943  -0.3113
 OUC  O26  O  O     0  -0.484   -6.2227  15.9019   3.3651
 OUC  H1   H  HCH3  0   0.246   -8.8915  14.3740   3.6945
 OUC  H2   H  HCH3  0   0.255  -10.2777  13.4190   3.1908
 OUC  H3   H  HCH3  0   0.251   -9.5144  14.5384   2.0689
 OUC  H4   H  HCR6  0   0.259  -12.3446  14.0757   3.8724
 OUC  H5   H  HCR6  0   0.251  -13.3410  18.1772   4.5436
 OUC  H6   H  HCH3  0   0.241  -10.5686  19.5695   4.9516
 OUC  H7   H  HCH3  0   0.255  -10.2731  19.5693   3.2302
 OUC  H8   H  HCH3  0   0.252  -11.8924  19.8671   3.8439
 OUC  H9   H  HCH2  0   0.273   -8.5709  16.5363   2.4616
 OUC  H10  H  HCH2  0   0.273   -8.8210  18.1999   2.9202
 OUC  H11  H  HCH1  0   0.299   -8.2593  16.0029   4.9415
 OUC  H12  H  HCH1  0   0.306   -5.3546  19.0425   6.1107
 OUC  H13  H  HCH2  0   0.270   -4.6814  20.1682   4.0818
 OUC  H14  H  HCH2  0   0.268   -5.8750  21.0883   4.9655
 OUC  H15  H  HCR6  0   0.252   -8.0347  21.6104   3.9609
 OUC  H16  H  HCR6  0   0.276   -9.4295  21.7283   1.9530
 OUC  H17  H  HCR6  0   0.262   -6.7694  19.0268  -0.0480
 OUC  H18  H  HCR6  0   0.250   -5.3557  18.9486   1.9499
 OUC  H19  H  HNH1  0   0.406   -9.1384  17.9860   5.9348
 OUC  H20  H  HNH1  0   0.405   -4.7335  17.6040   4.3095
 OUC  H21  H  HOH1  0   0.473  -14.3852  14.8255   4.5814
 OUC  H22  H  HOH1  0   0.474   -9.6987  20.9753  -0.2041

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
 OUC  O21  C20  single    1.348  0.020  1.348
 OUC  C22  C20  aromatic  1.393  0.020  1.393
 OUC  C22  C23  aromatic  1.385  0.020  1.385
 OUC  C20  C19  aromatic  1.391  0.020  1.391
 OUC  C23  C17  aromatic  1.395  0.020  1.395
 OUC  C19  C18  aromatic  1.388  0.020  1.388
 OUC  O26  C25  double    1.222  0.020  1.222
 OUC  C08  C07  single    1.504  0.020  1.504
 OUC  C17  C18  aromatic  1.391  0.020  1.391
 OUC  C17  C16  single    1.501  0.020  1.501
 OUC  C10  C09  single    1.508  0.020  1.508
 OUC  C10  C11  single    1.543  0.020  1.543
 OUC  C07  C06  aromatic  1.393  0.020  1.393
 OUC  C07  C09  aromatic  1.403  0.020  1.403
 OUC  C06  C04  aromatic  1.387  0.020  1.387
 OUC  C09  C02  aromatic  1.406  0.020  1.406
 OUC  C25  N24  single    1.337  0.020  1.337
 OUC  C25  C11  single    1.513  0.020  1.513
 OUC  C04  O05  single    1.349  0.020  1.349
 OUC  C04  C03  aromatic  1.390  0.020  1.390
 OUC  C02  C03  aromatic  1.389  0.020  1.389
 OUC  C02  C01  single    1.505  0.020  1.505
 OUC  N24  C15  single    1.443  0.020  1.443
 OUC  C16  C15  single    1.538  0.020  1.538
 OUC  C11  N12  single    1.444  0.020  1.444
 OUC  C15  C13  single    1.514  0.020  1.514
 OUC  N12  C13  single    1.337  0.020  1.337
 OUC  C13  O14  double    1.222  0.020  1.222
 OUC  C01  H1   single    0.970  0.020  1.090
 OUC  C01  H2   single    0.970  0.020  1.090
 OUC  C01  H3   single    0.970  0.020  1.090
 OUC  C03  H4   single    0.930  0.020  1.080
 OUC  C06  H5   single    0.930  0.020  1.080
 OUC  C08  H6   single    0.970  0.020  1.090
 OUC  C08  H7   single    0.970  0.020  1.090
 OUC  C08  H8   single    0.970  0.020  1.090
 OUC  C10  H9   single    0.970  0.020  1.090
 OUC  C10  H10  single    0.970  0.020  1.090
 OUC  C11  H11  single    0.970  0.020  1.090
 OUC  C15  H12  single    0.970  0.020  1.090
 OUC  C16  H13  single    0.970  0.020  1.090
 OUC  C16  H14  single    0.970  0.020  1.090
 OUC  C18  H15  single    0.930  0.020  1.080
 OUC  C19  H16  single    0.930  0.020  1.080
 OUC  C22  H17  single    0.930  0.020  1.080
 OUC  C23  H18  single    0.930  0.020  1.080
 OUC  N12  H19  single    0.860  0.020  1.020
 OUC  N24  H20  single    0.860  0.020  1.020
 OUC  O05  H21  single    0.850  0.020  0.980
 OUC  O21  H22  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
 OUC  H3   C01  H2   107.53  3.000
 OUC  H3   C01  H1   106.45  3.000
 OUC  H2   C01  H1   107.43  3.000
 OUC  H3   C01  C02  111.20  3.000
 OUC  H2   C01  C02  110.93  3.000
 OUC  H1   C01  C02  113.02  3.000
 OUC  C09  C02  C03  120.24  3.000
 OUC  C03  C02  C01  118.30  3.000
 OUC  C09  C02  C01  121.44  3.000
 OUC  H4   C03  C04  119.86  3.000
 OUC  H4   C03  C02  119.49  3.000
 OUC  C04  C03  C02  120.65  3.000
 OUC  O05  C04  C06  118.14  3.000
 OUC  O05  C04  C03  122.54  3.000
 OUC  C06  C04  C03  119.32  3.000
 OUC  H5   C06  C07  119.71  3.000
 OUC  H5   C06  C04  119.35  3.000
 OUC  C07  C06  C04  120.93  3.000
 OUC  C09  C07  C08  122.72  3.000
 OUC  C09  C07  C06  119.94  3.000
 OUC  C08  C07  C06  117.34  3.000
 OUC  H8   C08  H7   107.68  3.000
 OUC  H8   C08  H6   106.85  3.000
 OUC  H7   C08  H6   106.58  3.000
 OUC  H8   C08  C07  110.65  3.000
 OUC  H7   C08  C07  112.77  3.000
 OUC  H6   C08  C07  112.00  3.000
 OUC  C10  C09  C07  122.53  3.000
 OUC  C07  C09  C02  118.89  3.000
 OUC  C10  C09  C02  118.56  3.000
 OUC  H10  C10  H9   106.15  3.000
 OUC  H10  C10  C11  108.51  3.000
 OUC  H9   C10  C11  108.13  3.000
 OUC  H10  C10  C09  112.26  3.000
 OUC  H9   C10  C09  109.86  3.000
 OUC  C11  C10  C09  111.70  3.000
 OUC  H11  C11  N12  107.10  3.000
 OUC  H11  C11  C25  104.54  3.000
 OUC  N12  C11  C25  113.19  3.000
 OUC  H11  C11  C10  107.98  3.000
 OUC  N12  C11  C10  112.05  3.000
 OUC  C25  C11  C10  111.46  3.000
 OUC  O14  C13  N12  123.10  3.000
 OUC  O14  C13  C15  119.65  3.000
 OUC  N12  C13  C15  117.20  3.000
 OUC  H12  C15  N24  107.48  3.000
 OUC  H12  C15  C16  107.24  3.000
 OUC  N24  C15  C16  111.71  3.000
 OUC  H12  C15  C13  105.38  3.000
 OUC  C16  C15  C13  111.35  3.000
 OUC  N24  C15  C13  113.21  3.000
 OUC  H14  C16  H13  106.30  3.000
 OUC  H14  C16  C17  110.72  3.000
 OUC  H13  C16  C17  110.30  3.000
 OUC  H14  C16  C15  107.85  3.000
 OUC  H13  C16  C15  107.37  3.000
 OUC  C17  C16  C15  113.95  3.000
 OUC  C23  C17  C18  117.63  3.000
 OUC  C18  C17  C16  121.07  3.000
 OUC  C23  C17  C16  121.30  3.000
 OUC  H15  C18  C19  118.75  3.000
 OUC  H15  C18  C17  119.73  3.000
 OUC  C19  C18  C17  121.51  3.000
 OUC  H16  C19  C20  120.22  3.000
 OUC  H16  C19  C18  119.75  3.000
 OUC  C20  C19  C18  120.03  3.000
 OUC  O21  C20  C22  117.98  3.000
 OUC  C22  C20  C19  119.28  3.000
 OUC  O21  C20  C19  122.74  3.000
 OUC  H17  C22  C23  120.27  3.000
 OUC  H17  C22  C20  119.82  3.000
 OUC  C23  C22  C20  119.91  3.000
 OUC  H18  C23  C22  118.55  3.000
 OUC  H18  C23  C17  119.81  3.000
 OUC  C22  C23  C17  121.63  3.000
 OUC  O26  C25  N24  123.16  3.000
 OUC  N24  C25  C11  117.19  3.000
 OUC  O26  C25  C11  119.59  3.000
 OUC  H19  N12  C13  116.04  3.000
 OUC  H19  N12  C11  116.00  3.000
 OUC  C13  N12  C11  127.27  3.000
 OUC  H20  N24  C25  116.01  3.000
 OUC  H20  N24  C15  115.90  3.000
 OUC  C25  N24  C15  127.47  3.000
 OUC  H21  O05  C04  110.24  3.000
 OUC  H22  O21  C20  110.32  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
 OUC  CONST_01  C06  C07  C09  C02     0.00   0.0  0
 OUC  CONST_02  C06  C04  C03  C02     0.00   0.0  0
 OUC  CONST_03  C07  C06  C04  C03     0.00   0.0  0
 OUC  CONST_04  C07  C09  C02  C03     0.00   0.0  0
 OUC  CONST_05  C09  C07  C06  C04     0.00   0.0  0
 OUC  CONST_06  C09  C02  C03  C04     0.00   0.0  0
 OUC  CONST_07  C20  C22  C23  C17     0.00   0.0  0
 OUC  CONST_08  C20  C19  C18  C17     0.00   0.0  0
 OUC  CONST_09  C22  C20  C19  C18     0.00   0.0  0
 OUC  CONST_10  C22  C23  C17  C18     0.00   0.0  0
 OUC  CONST_11  C23  C22  C20  C19     0.00   0.0  0
 OUC  CONST_12  C23  C17  C18  C19     0.00   0.0  0
 OUC  CONST_13  C15  N24  C25  C11     0.00   0.0  0
 OUC  CONST_14  C15  C13  N12  C11     0.00   0.0  0
 OUC  CONST_15  C07  C09  C02  C01   180.00   0.0  0
 OUC  CONST_16  C04  C03  C02  C01   180.00   0.0  0
 OUC  CONST_17  C08  C07  C09  C02   180.00   0.0  0
 OUC  CONST_18  O05  C04  C03  C02   180.00   0.0  0
 OUC  CONST_19  C10  C09  C02  C03   180.00   0.0  0
 OUC  CONST_20  C08  C07  C06  C04   180.00   0.0  0
 OUC  CONST_21  C10  C09  C07  C06   180.00   0.0  0
 OUC  CONST_22  O05  C04  C06  C07   180.00   0.0  0
 OUC  CONST_23  C22  C23  C17  C16   180.00   0.0  0
 OUC  CONST_24  C19  C18  C17  C16   180.00   0.0  0
 OUC  CONST_25  O21  C20  C19  C18   180.00   0.0  0
 OUC  CONST_26  O21  C20  C22  C23   180.00   0.0  0
 OUC  CONST_27  O14  C13  N12  C11   180.00   0.0  0
 OUC  CONST_28  O26  C25  N24  C15   180.00   0.0  0
 OUC  CONST_29  H5   C06  C04  C03   180.00   0.0  0
 OUC  CONST_30  H4   C03  C04  C06   180.00   0.0  0
 OUC  CONST_31  H17  C22  C23  C17   180.00   0.0  0
 OUC  CONST_32  H16  C19  C18  C17   180.00   0.0  0
 OUC  CONST_33  H18  C23  C17  C18   180.00   0.0  0
 OUC  CONST_34  H15  C18  C19  C20   180.00   0.0  0
 OUC  CONST_35  H20  N24  C25  C11   180.00   0.0  0
 OUC  CONST_36  H19  N12  C13  C15   180.00   0.0  0
 OUC  Var_01    C11  C10  C09  C02   -81.72  30.0  3
 OUC  Var_02    C23  C17  C16  C15   -82.72  30.0  2
 OUC  Var_03    H1   C01  C02  C03  -124.90  30.0  2
 OUC  Var_04    H6   C08  C07  C06    93.77  30.0  2

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
 OUC  chir_01  C11  C10  C25  N12  negativ
 OUC  chir_02  C15  N24  C16  C13  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
 OUC  plan-1  C01  0.020
 OUC  plan-1  C02  0.020
 OUC  plan-1  C03  0.020
 OUC  plan-1  C04  0.020
 OUC  plan-1  C06  0.020
 OUC  plan-1  C07  0.020
 OUC  plan-1  C08  0.020
 OUC  plan-1  C09  0.020
 OUC  plan-1  C10  0.020
 OUC  plan-1  O05  0.020
 OUC  plan-1  H4   0.020
 OUC  plan-1  H5   0.020
 OUC  plan-2  C16  0.020
 OUC  plan-2  C17  0.020
 OUC  plan-2  C18  0.020
 OUC  plan-2  C19  0.020
 OUC  plan-2  C20  0.020
 OUC  plan-2  C22  0.020
 OUC  plan-2  C23  0.020
 OUC  plan-2  O21  0.020
 OUC  plan-2  H15  0.020
 OUC  plan-2  H16  0.020
 OUC  plan-2  H17  0.020
 OUC  plan-2  H18  0.020
 OUC  plan-3  C11  0.020
 OUC  plan-3  C13  0.020
 OUC  plan-3  C15  0.020
 OUC  plan-3  N12  0.020
 OUC  plan-3  O14  0.020
 OUC  plan-3  H19  0.020
 OUC  plan-4  C11  0.020
 OUC  plan-4  C15  0.020
 OUC  plan-4  C25  0.020
 OUC  plan-4  N24  0.020
 OUC  plan-4  O26  0.020
 OUC  plan-4  H20  0.020

