# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  1 03:08:21 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: 1,4-dihydroxy-5,8-bis{[2-(2-hydroxyethoxy)ethyl]amino}anthracene-9,10-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCOCCNc1ccc(NCCOCCO)c2C(=O)c3c(O)ccc(O)c3C(=O)c12
#
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
 3OA  3OA  1,4-dihydroxy-5,8-bis{[2-(2-hydroxyethoxy)ethyl]amino}anthracene-9,10-dione  ligand  58  32  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_3OA
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
 3OA  OAC  O  OH1   0  -0.672   7.5078  -0.4251   1.5943
 3OA  CAK  C  CH2   0  -0.183   7.2375   0.0200   0.2852
 3OA  CAM  C  CH2   0  -0.160   6.7517  -1.1341  -0.5528
 3OA  O1   O  O2    0  -0.488   5.5091  -1.5845  -0.0707
 3OA  CAO  C  CH2   0  -0.167   4.9213  -2.5691  -0.8815
 3OA  CAQ  C  CH2   0  -0.317   3.5305  -2.8584  -0.3621
 3OA  NAU  N  NH1   0  -0.691   2.7497  -1.6435  -0.3692
 3OA  CAY  C  CR6   0   0.392   1.4274  -1.5644  -0.1543
 3OA  CAI  C  CR16  0  -0.325   0.6805  -2.7682   0.0115
 3OA  CAJ  C  CR16  0  -0.325  -0.6576  -2.7655   0.2105
 3OA  CBE  C  CR66  0  -0.151   0.7155  -0.3446  -0.0902
 3OA  CBA  C  CR6   0   0.435   1.4255   0.9033  -0.2259
 3OA  OAA  O  O     0  -0.551   2.6678   0.9420  -0.3926
 3OA  CBC  C  CR66  0  -0.191   0.6940   2.1647  -0.1691
 3OA  CAW  C  CR6   0   0.342   1.3867   3.3754  -0.2990
 3OA  OAE  O  OH1   0  -0.633   2.7063   3.4464  -0.4746
 3OA  CAG  C  CR16  0  -0.327   0.6671   4.5767  -0.2444
 3OA  CAH  C  CR16  0  -0.327  -0.6939   4.5783  -0.0672
 3OA  CAX  C  CR6   0   0.342  -1.4065   3.3786   0.0623
 3OA  OAF  O  OH1   0  -0.633  -2.7268   3.4522   0.2307
 3OA  CBD  C  CR66  0  -0.191  -0.7062   2.1663   0.0123
 3OA  CBB  C  CR6   0   0.435  -1.4301   0.9072   0.1533
 3OA  OAB  O  O     0  -0.552  -2.6739   0.9493   0.3077
 3OA  CBF  C  CR66  0  -0.151  -0.7109  -0.3422   0.1126
 3OA  CAZ  C  CR6   0   0.392  -1.4144  -1.5585   0.2701
 3OA  NAV  N  NH1   0  -0.691  -2.7380  -1.6286   0.4808
 3OA  CAR  C  CH2   0  -0.316  -3.5133  -2.8441   0.5644
 3OA  CAP  C  CH2   0  -0.167  -4.9132  -2.5172   1.0358
 3OA  O2   O  O2    0  -0.488  -5.4873  -1.6035   0.1371
 3OA  CAN  C  CH2   0  -0.160  -6.7303  -1.1022   0.5648
 3OA  CAL  C  CH2   0  -0.182  -7.1946  -0.0228  -0.3786
 3OA  OAD  O  OH1   0  -0.672  -7.4538  -0.5821  -1.6454
 3OA  H1   H  HOH1  0   0.456   7.8057   0.3294   2.1097
 3OA  H2   H  HCH2  0   0.200   6.4822   0.8166   0.2727
 3OA  H3   H  HCH2  0   0.203   8.1329   0.4231  -0.2046
 3OA  H4   H  HCH2  0   0.208   6.6660  -0.7890  -1.5920
 3OA  H5   H  HCH2  0   0.206   7.4922  -1.9463  -0.5454
 3OA  H6   H  HCH2  0   0.213   4.8614  -2.2296  -1.9251
 3OA  H7   H  HCH2  0   0.227   5.5040  -3.4993  -0.8756
 3OA  H8   H  HCH2  0   0.251   3.0859  -3.6141  -1.0135
 3OA  H9   H  HCH2  0   0.246   3.5867  -3.2915   0.6434
 3OA  H10  H  HNH1  0   0.419   3.2453  -0.7613  -0.3835
 3OA  H11  H  HCR6  0   0.297   1.1889  -3.7216  -0.0194
 3OA  H12  H  HCR6  0   0.297  -1.1571  -3.7170   0.3267
 3OA  H14  H  HOH1  0   0.480   3.0308   2.5109  -0.4914
 3OA  H15  H  HCR6  0   0.280   1.2013   5.5129  -0.3466
 3OA  H16  H  HCR6  0   0.280  -1.2334   5.5160  -0.0246
 3OA  H17  H  HOH1  0   0.480  -3.0451   2.5173   0.3045
 3OA  H19  H  HNH1  0   0.419  -3.2381  -0.7513   0.4144
 3OA  H20  H  HCH2  0   0.246  -3.5516  -3.3603  -0.4020
 3OA  H21  H  HCH2  0   0.251  -3.0759  -3.5399   1.2837
 3OA  H22  H  HCH2  0   0.227  -5.4947  -3.4463   1.0960
 3OA  H23  H  HCH2  0   0.213  -4.8705  -2.0935   2.0489
 3OA  H24  H  HCH2  0   0.206  -7.4790  -1.9051   0.6198
 3OA  H25  H  HCH2  0   0.208  -6.6522  -0.6683   1.5708
 3OA  H26  H  HCH2  0   0.202  -8.0917   0.4320   0.0606
 3OA  H27  H  HCH2  0   0.200  -6.4310   0.7643  -0.4282
 3OA  H28  H  HOH1  0   0.455  -7.7179   0.1284  -2.2363

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
 3OA  OAC  CAK  single    1.409  0.020  1.409
 3OA  OAD  CAL  single    1.409  0.020  1.409
 3OA  CAL  CAN  single    1.507  0.020  1.507
 3OA  CAK  CAM  single    1.507  0.020  1.507
 3OA  CAM  O1   single    1.407  0.020  1.407
 3OA  CAN  O2   single    1.407  0.020  1.407
 3OA  O1   CAO  single    1.404  0.020  1.404
 3OA  O2   CAP  single    1.404  0.020  1.404
 3OA  CAO  CAQ  single    1.513  0.020  1.513
 3OA  CAP  CAR  single    1.513  0.020  1.513
 3OA  CAI  CAJ  aromatic  1.353  0.020  1.353
 3OA  CAI  CAY  aromatic  1.426  0.020  1.426
 3OA  CAQ  NAU  single    1.444  0.020  1.444
 3OA  CAJ  CAZ  aromatic  1.426  0.020  1.426
 3OA  CAR  NAV  single    1.444  0.020  1.444
 3OA  CAY  NAU  single    1.342  0.020  1.342
 3OA  CAY  CBE  aromatic  1.414  0.020  1.414
 3OA  CAZ  NAV  single    1.342  0.020  1.342
 3OA  CAZ  CBF  aromatic  1.414  0.020  1.414
 3OA  CBE  CBF  aromatic  1.441  0.020  1.441
 3OA  CBE  CBA  single    1.442  0.020  1.442
 3OA  CBF  CBB  single    1.442  0.020  1.442
 3OA  OAA  CBA  double    1.254  0.020  1.254
 3OA  CBA  CBC  single    1.459  0.020  1.459
 3OA  CBB  OAB  double    1.254  0.020  1.254
 3OA  CBB  CBD  single    1.459  0.020  1.459
 3OA  CBC  CBD  aromatic  1.412  0.020  1.412
 3OA  CBC  CAW  aromatic  1.401  0.020  1.401
 3OA  CBD  CAX  aromatic  1.401  0.020  1.401
 3OA  OAE  CAW  single    1.333  0.020  1.333
 3OA  CAW  CAG  aromatic  1.401  0.020  1.401
 3OA  OAF  CAX  single    1.333  0.020  1.333
 3OA  CAX  CAH  aromatic  1.401  0.020  1.401
 3OA  CAG  CAH  aromatic  1.372  0.020  1.372
 3OA  OAC  H1   single    0.850  0.020  0.980
 3OA  CAK  H2   single    0.970  0.020  1.090
 3OA  CAK  H3   single    0.970  0.020  1.090
 3OA  CAM  H4   single    0.970  0.020  1.090
 3OA  CAM  H5   single    0.970  0.020  1.090
 3OA  CAO  H6   single    0.970  0.020  1.090
 3OA  CAO  H7   single    0.970  0.020  1.090
 3OA  CAQ  H8   single    0.970  0.020  1.090
 3OA  CAQ  H9   single    0.970  0.020  1.090
 3OA  NAU  H10  single    0.860  0.020  1.020
 3OA  CAI  H11  single    0.930  0.020  1.080
 3OA  CAJ  H12  single    0.930  0.020  1.080
 3OA  OAE  H14  single    0.850  0.020  0.980
 3OA  CAG  H15  single    0.930  0.020  1.080
 3OA  CAH  H16  single    0.930  0.020  1.080
 3OA  OAF  H17  single    0.850  0.020  0.980
 3OA  NAV  H19  single    0.860  0.020  1.020
 3OA  CAR  H20  single    0.970  0.020  1.090
 3OA  CAR  H21  single    0.970  0.020  1.090
 3OA  CAP  H22  single    0.970  0.020  1.090
 3OA  CAP  H23  single    0.970  0.020  1.090
 3OA  CAN  H24  single    0.970  0.020  1.090
 3OA  CAN  H25  single    0.970  0.020  1.090
 3OA  CAL  H26  single    0.970  0.020  1.090
 3OA  CAL  H27  single    0.970  0.020  1.090
 3OA  OAD  H28  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
 3OA  H1   OAC  CAK  108.04  3.000
 3OA  H3   CAK  H2   106.84  3.000
 3OA  H3   CAK  CAM  107.23  3.000
 3OA  H2   CAK  CAM  109.13  3.000
 3OA  H3   CAK  OAC  111.97  3.000
 3OA  H2   CAK  OAC  111.83  3.000
 3OA  CAM  CAK  OAC  109.67  3.000
 3OA  H5   CAM  H4   106.92  3.000
 3OA  H5   CAM  O1   110.87  3.000
 3OA  H4   CAM  O1   110.85  3.000
 3OA  H5   CAM  CAK  110.18  3.000
 3OA  H4   CAM  CAK  108.10  3.000
 3OA  O1   CAM  CAK  109.84  3.000
 3OA  CAO  O1   CAM  113.34  3.000
 3OA  H7   CAO  H6   107.21  3.000
 3OA  H7   CAO  CAQ  108.91  3.000
 3OA  H6   CAO  CAQ  109.57  3.000
 3OA  H7   CAO  O1   111.64  3.000
 3OA  H6   CAO  O1   110.76  3.000
 3OA  CAQ  CAO  O1   108.70  3.000
 3OA  H9   CAQ  H8   107.13  3.000
 3OA  H9   CAQ  NAU  111.38  3.000
 3OA  H8   CAQ  NAU  111.04  3.000
 3OA  H9   CAQ  CAO  110.08  3.000
 3OA  H8   CAQ  CAO  107.57  3.000
 3OA  NAU  CAQ  CAO  109.55  3.000
 3OA  H10  NAU  CAY  115.68  3.000
 3OA  H10  NAU  CAQ  117.95  3.000
 3OA  CAY  NAU  CAQ  125.56  3.000
 3OA  CBE  CAY  CAI  117.34  3.000
 3OA  CBE  CAY  NAU  123.66  3.000
 3OA  CAI  CAY  NAU  119.00  3.000
 3OA  H11  CAI  CAJ  118.11  3.000
 3OA  H11  CAI  CAY  119.66  3.000
 3OA  CAJ  CAI  CAY  122.23  3.000
 3OA  H12  CAJ  CAZ  119.70  3.000
 3OA  H12  CAJ  CAI  118.11  3.000
 3OA  CAZ  CAJ  CAI  122.19  3.000
 3OA  CBF  CBE  CBA  119.95  3.000
 3OA  CBA  CBE  CAY  119.63  3.000
 3OA  CBF  CBE  CAY  120.42  3.000
 3OA  CBC  CBA  OAA  118.37  3.000
 3OA  CBC  CBA  CBE  119.83  3.000
 3OA  OAA  CBA  CBE  121.80  3.000
 3OA  CBD  CBC  CAW  120.09  3.000
 3OA  CAW  CBC  CBA  119.71  3.000
 3OA  CBD  CBC  CBA  120.21  3.000
 3OA  CAG  CAW  OAE  117.89  3.000
 3OA  CAG  CAW  CBC  118.90  3.000
 3OA  OAE  CAW  CBC  123.21  3.000
 3OA  H14  OAE  CAW  106.04  3.000
 3OA  H15  CAG  CAH  120.03  3.000
 3OA  H15  CAG  CAW  118.96  3.000
 3OA  CAH  CAG  CAW  121.01  3.000
 3OA  H16  CAH  CAX  118.97  3.000
 3OA  H16  CAH  CAG  120.02  3.000
 3OA  CAX  CAH  CAG  121.01  3.000
 3OA  CBD  CAX  OAF  123.19  3.000
 3OA  OAF  CAX  CAH  117.91  3.000
 3OA  CBD  CAX  CAH  118.90  3.000
 3OA  H17  OAF  CAX  106.00  3.000
 3OA  CBB  CBD  CAX  119.69  3.000
 3OA  CAX  CBD  CBC  120.09  3.000
 3OA  CBB  CBD  CBC  120.23  3.000
 3OA  CBF  CBB  OAB  121.81  3.000
 3OA  OAB  CBB  CBD  118.36  3.000
 3OA  CBF  CBB  CBD  119.83  3.000
 3OA  CAZ  CBF  CBB  119.61  3.000
 3OA  CBB  CBF  CBE  119.94  3.000
 3OA  CAZ  CBF  CBE  120.46  3.000
 3OA  NAV  CAZ  CBF  123.58  3.000
 3OA  CBF  CAZ  CAJ  117.36  3.000
 3OA  NAV  CAZ  CAJ  119.06  3.000
 3OA  H19  NAV  CAR  117.92  3.000
 3OA  H19  NAV  CAZ  115.58  3.000
 3OA  CAR  NAV  CAZ  125.63  3.000
 3OA  H21  CAR  H20  107.13  3.000
 3OA  H21  CAR  CAP  107.63  3.000
 3OA  H20  CAR  CAP  110.12  3.000
 3OA  H21  CAR  NAV  111.06  3.000
 3OA  H20  CAR  NAV  111.35  3.000
 3OA  CAP  CAR  NAV  109.45  3.000
 3OA  H23  CAP  H22  107.24  3.000
 3OA  H23  CAP  O2   110.79  3.000
 3OA  H22  CAP  O2   111.67  3.000
 3OA  H23  CAP  CAR  109.55  3.000
 3OA  H22  CAP  CAR  108.93  3.000
 3OA  O2   CAP  CAR  108.63  3.000
 3OA  CAN  O2   CAP  113.48  3.000
 3OA  H25  CAN  H24  106.92  3.000
 3OA  H25  CAN  CAL  108.20  3.000
 3OA  H24  CAN  CAL  110.16  3.000
 3OA  H25  CAN  O2   110.88  3.000
 3OA  H24  CAN  O2   110.90  3.000
 3OA  CAL  CAN  O2   109.71  3.000
 3OA  H27  CAL  H26  106.83  3.000
 3OA  H27  CAL  OAD  111.83  3.000
 3OA  H26  CAL  OAD  111.96  3.000
 3OA  H27  CAL  CAN  109.12  3.000
 3OA  H26  CAL  CAN  107.35  3.000
 3OA  OAD  CAL  CAN  109.59  3.000
 3OA  H28  OAD  CAL  108.05  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
 3OA  CONST_01  CAZ  CAJ  CAI  CAY     0.00   0.0  0
 3OA  CONST_02  CAZ  CBF  CBE  CAY     0.00   0.0  0
 3OA  CONST_03  CBF  CAZ  CAJ  CAI     0.00   0.0  0
 3OA  CONST_04  CBF  CBE  CAY  CAI     0.00   0.0  0
 3OA  CONST_05  CBE  CAY  CAI  CAJ     0.00   0.0  0
 3OA  CONST_06  CBE  CBF  CAZ  CAJ     0.00   0.0  0
 3OA  CONST_07  CAH  CAX  CBD  CBC     0.00   0.0  0
 3OA  CONST_08  CAH  CAG  CAW  CBC     0.00   0.0  0
 3OA  CONST_09  CAX  CBD  CBC  CAW     0.00   0.0  0
 3OA  CONST_10  CAX  CAH  CAG  CAW     0.00   0.0  0
 3OA  CONST_11  CBD  CBC  CAW  CAG     0.00   0.0  0
 3OA  CONST_12  CBD  CAX  CAH  CAG     0.00   0.0  0
 3OA  CONST_13  CAJ  CAI  CAY  NAU   180.00   0.0  0
 3OA  CONST_14  CBF  CBE  CAY  NAU   180.00   0.0  0
 3OA  CONST_15  CBA  CBE  CAY  NAU     0.00   0.0  0
 3OA  CONST_16  NAV  CAZ  CAJ  CAI   180.00   0.0  0
 3OA  CONST_17  NAV  CAZ  CBF  CBE   180.00   0.0  0
 3OA  CONST_18  OAE  CAW  CBC  CBA     0.00   0.0  0
 3OA  CONST_19  OAF  CAX  CBD  CBC   180.00   0.0  0
 3OA  CONST_20  CBD  CBC  CAW  OAE   180.00   0.0  0
 3OA  CONST_21  CAH  CAG  CAW  OAE   180.00   0.0  0
 3OA  CONST_22  OAF  CAX  CAH  CAG   180.00   0.0  0
 3OA  CONST_23  CBB  CBD  CAX  OAF     0.00   0.0  0
 3OA  CONST_24  NAV  CAZ  CBF  CBB     0.00   0.0  0
 3OA  CONST_25  H12  CAJ  CAI  CAY   180.00   0.0  0
 3OA  CONST_26  H11  CAI  CAY  CBE   180.00   0.0  0
 3OA  CONST_27  H15  CAG  CAW  CBC   180.00   0.0  0
 3OA  CONST_28  H16  CAH  CAG  CAW   180.00   0.0  0
 3OA  CONST_29  CAI  CAY  NAU  CAQ     0.00   0.0  0
 3OA  CONST_30  CBE  CAY  NAU  CAQ   180.00   0.0  0
 3OA  CONST_31  CAR  NAV  CAZ  CAJ     0.00   0.0  0
 3OA  CONST_32  CAR  NAV  CAZ  CBF   180.00   0.0  0
 3OA  CONST_33  H10  NAU  CAY  CAI   180.00   0.0  0
 3OA  CONST_34  H19  NAV  CAZ  CAJ   180.00   0.0  0
 3OA  Var_01    CAY  NAU  CAQ  CAO   170.08  30.0  3
 3OA  Var_02    CAP  CAR  NAV  CAZ   170.64  30.0  1
 3OA  Var_03    O1   CAM  CAK  OAC    65.71  30.0  3
 3OA  Var_04    CAQ  CAO  O1   CAM  -173.45  30.0  3
 3OA  Var_05    NAU  CAQ  CAO  O1     58.38  30.0  3
 3OA  Var_06    O2   CAP  CAR  NAV    58.14  30.0  2
 3OA  Var_07    CAL  CAN  O2   CAP   173.74  30.0  2
 3OA  Var_08    OAD  CAL  CAN  O2     65.67  30.0  2

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
 3OA  plan-1  NAU  0.020
 3OA  plan-1  CAY  0.020
 3OA  plan-1  CAI  0.020
 3OA  plan-1  CAJ  0.020
 3OA  plan-1  CBE  0.020
 3OA  plan-1  CBA  0.020
 3OA  plan-1  OAA  0.020
 3OA  plan-1  CBC  0.020
 3OA  plan-1  CAW  0.020
 3OA  plan-1  OAE  0.020
 3OA  plan-1  CAG  0.020
 3OA  plan-1  CAH  0.020
 3OA  plan-1  CAX  0.020
 3OA  plan-1  OAF  0.020
 3OA  plan-1  CBD  0.020
 3OA  plan-1  CBB  0.020
 3OA  plan-1  OAB  0.020
 3OA  plan-1  CBF  0.020
 3OA  plan-1  CAZ  0.020
 3OA  plan-1  NAV  0.020
 3OA  plan-1  H11  0.020
 3OA  plan-1  H12  0.020
 3OA  plan-1  H15  0.020
 3OA  plan-1  H16  0.020
 3OA  plan-2  CAQ  0.020
 3OA  plan-2  NAU  0.020
 3OA  plan-2  CAY  0.020
 3OA  plan-2  H10  0.020
 3OA  plan-3  CAZ  0.020
 3OA  plan-3  NAV  0.020
 3OA  plan-3  CAR  0.020
 3OA  plan-3  H19  0.020

