# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 04:14:14 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: 1,4-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCNCCNc1ccc(NCCNCCO)c2C(=O)c3ccccc3C(=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
 AKE  AKE  1,4-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione  ligand  58  30  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_AKE
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
 AKE  O01  O  O     0  -0.464  -2.6792   2.2328  -0.0666
 AKE  C02  C  CR6   0   0.350  -1.4476   2.1776   0.0057
 AKE  C03  C  CR66  0  -0.013  -0.6902   3.4451   0.0654
 AKE  C04  C  CR16  0  -0.280  -1.3800   4.6575   0.0415
 AKE  C05  C  CR16  0  -0.238  -0.6887   5.8537   0.0909
 AKE  C06  C  CR16  0  -0.238   0.7017   5.8526   0.1650
 AKE  C07  C  CR16  0  -0.280   1.3922   4.6552   0.1898
 AKE  C08  C  CR66  0  -0.013   0.7016   3.4439   0.1409
 AKE  C09  C  CR6   0   0.350   1.4578   2.1747   0.1735
 AKE  O10  O  O     0  -0.464   2.6895   2.2270   0.2466
 AKE  C11  C  CR66  0  -0.174   0.7230   0.9242   0.1206
 AKE  C12  C  CR6   0   0.390   1.4354  -0.2949   0.1501
 AKE  N13  N  NH1   0  -0.701   2.7755  -0.3734   0.2376
 AKE  C14  C  CH2   0  -0.283   3.5383  -1.5958   0.1637
 AKE  C15  C  CH2   0  -0.292   5.0196  -1.2812   0.3015
 AKE  N16  N  NH1   0  -0.602   5.8008  -2.4877   0.1429
 AKE  C17  C  CH2   0  -0.289   7.2148  -2.2752   0.3837
 AKE  C18  C  CH2   0  -0.171   8.0134  -3.5433   0.1859
 AKE  O19  O  OH1   0  -0.675   7.9417  -3.9223  -1.1735
 AKE  C20  C  CR16  0  -0.328   0.6796  -1.5007   0.0891
 AKE  C21  C  CR16  0  -0.328  -0.6727  -1.4993   0.0085
 AKE  C22  C  CR6   0   0.391  -1.4272  -0.2918  -0.0270
 AKE  N23  N  NH1   0  -0.701  -2.7671  -0.3662  -0.1197
 AKE  C24  C  CH2   0  -0.283  -3.5331  -1.5885  -0.0866
 AKE  C25  C  CH2   0  -0.292  -5.0113  -1.2665  -0.2413
 AKE  N26  N  NH1   0  -0.602  -5.7982  -2.4730  -0.1164
 AKE  C27  C  CH2   0  -0.289  -7.2070  -2.2527  -0.3797
 AKE  C28  C  CH2   0  -0.171  -8.0133  -3.5199  -0.2098
 AKE  O29  O  OH1   0  -0.675  -7.9661  -3.9146   1.1463
 AKE  C30  C  CR66  0  -0.175  -0.7139   0.9257   0.0316
 AKE  H1   H  HCR6  0   0.265  -2.4595   4.6606  -0.0153
 AKE  H2   H  HCR6  0   0.269  -1.2303   6.7902   0.0714
 AKE  H3   H  HCR6  0   0.269   1.2437   6.7882   0.2039
 AKE  H4   H  HCR6  0   0.265   2.4718   4.6559   0.2464
 AKE  H5   H  HNH1  0   0.414   3.2639   0.5121   0.2417
 AKE  H6   H  HCH2  0   0.238   3.2511  -2.2896   0.9591
 AKE  H7   H  HCH2  0   0.233   3.3588  -2.1086  -0.7895
 AKE  H8   H  HCH2  0   0.203   5.2952  -0.4908  -0.4154
 AKE  H9   H  HCH2  0   0.234   5.2070  -0.8745   1.2995
 AKE  H10  H  HNH1  0   0.343   5.6778  -2.8362  -0.8004
 AKE  H12  H  HCH2  0   0.197   7.6408  -1.4743  -0.2418
 AKE  H13  H  HCH2  0   0.227   7.3476  -1.9563   1.4213
 AKE  H14  H  HCH2  0   0.201   9.0484  -3.3562   0.4982
 AKE  H15  H  HCH2  0   0.196   7.6125  -4.3258   0.8423
 AKE  H16  H  HOH1  0   0.456   8.3837  -4.7696  -1.2736
 AKE  H17  H  HCR6  0   0.295   1.1912  -2.4533   0.1101
 AKE  H18  H  HCR6  0   0.295  -1.1852  -2.4506  -0.0325
 AKE  H19  H  HNH1  0   0.414  -3.2541   0.5200  -0.1037
 AKE  H20  H  HCH2  0   0.238  -3.2344  -2.2642  -0.8930
 AKE  H21  H  HCH2  0   0.233  -3.3710  -2.1242   0.8572
 AKE  H22  H  HCH2  0   0.203  -5.2952  -0.4888   0.4862
 AKE  H23  H  HCH2  0   0.235  -5.1824  -0.8406  -1.2342
 AKE  H24  H  HNH1  0   0.343  -5.6938  -2.8361   0.8236
 AKE  H26  H  HCH2  0   0.197  -7.6412  -1.4573   0.2475
 AKE  H27  H  HCH2  0   0.227  -7.3212  -1.9220  -1.4158
 AKE  H28  H  HCH2  0   0.201  -9.0423  -3.3258  -0.5373
 AKE  H29  H  HCH2  0   0.196  -7.6039  -4.2965  -0.8680
 AKE  H30  H  HOH1  0   0.456  -8.4163  -4.7595   1.2296

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
 AKE  O29  C28  single    1.413  0.020  1.413
 AKE  C28  C27  single    1.512  0.020  1.512
 AKE  C27  N26  single    1.450  0.020  1.450
 AKE  N26  C25  single    1.446  0.020  1.446
 AKE  C25  C24  single    1.521  0.020  1.521
 AKE  C24  N23  single    1.443  0.020  1.443
 AKE  N23  C22  single    1.345  0.020  1.345
 AKE  C21  C22  aromatic  1.424  0.020  1.424
 AKE  C21  C20  aromatic  1.355  0.020  1.355
 AKE  C22  C30  aromatic  1.412  0.020  1.412
 AKE  N16  C17  single    1.450  0.020  1.450
 AKE  N16  C15  single    1.446  0.020  1.446
 AKE  C20  C12  aromatic  1.424  0.020  1.424
 AKE  O01  C02  double    1.235  0.020  1.235
 AKE  C17  C18  single    1.512  0.020  1.512
 AKE  C30  C02  single    1.451  0.020  1.451
 AKE  C30  C11  aromatic  1.440  0.020  1.440
 AKE  C18  O19  single    1.413  0.020  1.413
 AKE  C02  C03  single    1.478  0.020  1.478
 AKE  C12  C11  aromatic  1.412  0.020  1.412
 AKE  C12  N13  single    1.345  0.020  1.345
 AKE  C14  C15  single    1.521  0.020  1.521
 AKE  C14  N13  single    1.443  0.020  1.443
 AKE  C11  C09  single    1.451  0.020  1.451
 AKE  C03  C04  aromatic  1.395  0.020  1.395
 AKE  C03  C08  aromatic  1.394  0.020  1.394
 AKE  C04  C05  aromatic  1.382  0.020  1.382
 AKE  C09  C08  single    1.478  0.020  1.478
 AKE  C09  O10  double    1.235  0.020  1.235
 AKE  C08  C07  aromatic  1.395  0.020  1.395
 AKE  C05  C06  aromatic  1.392  0.020  1.392
 AKE  C07  C06  aromatic  1.382  0.020  1.382
 AKE  C04  H1   single    0.930  0.020  1.080
 AKE  C05  H2   single    0.930  0.020  1.080
 AKE  C06  H3   single    0.930  0.020  1.080
 AKE  C07  H4   single    0.930  0.020  1.080
 AKE  N13  H5   single    0.860  0.020  1.020
 AKE  C14  H6   single    0.970  0.020  1.090
 AKE  C14  H7   single    0.970  0.020  1.090
 AKE  C15  H8   single    0.970  0.020  1.090
 AKE  C15  H9   single    0.970  0.020  1.090
 AKE  N16  H10  single    0.890  0.020  1.040
 AKE  C17  H12  single    0.970  0.020  1.090
 AKE  C17  H13  single    0.970  0.020  1.090
 AKE  C18  H14  single    0.970  0.020  1.090
 AKE  C18  H15  single    0.970  0.020  1.090
 AKE  O19  H16  single    0.850  0.020  0.980
 AKE  C20  H17  single    0.930  0.020  1.080
 AKE  C21  H18  single    0.930  0.020  1.080
 AKE  N23  H19  single    0.860  0.020  1.020
 AKE  C24  H20  single    0.970  0.020  1.090
 AKE  C24  H21  single    0.970  0.020  1.090
 AKE  C25  H22  single    0.970  0.020  1.090
 AKE  C25  H23  single    0.970  0.020  1.090
 AKE  N26  H24  single    0.890  0.020  1.040
 AKE  C27  H26  single    0.970  0.020  1.090
 AKE  C27  H27  single    0.970  0.020  1.090
 AKE  C28  H28  single    0.970  0.020  1.090
 AKE  C28  H29  single    0.970  0.020  1.090
 AKE  O29  H30  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
 AKE  C30  C02  C03  118.69  3.000
 AKE  C03  C02  O01  118.37  3.000
 AKE  C30  C02  O01  122.94  3.000
 AKE  C08  C03  C04  119.70  3.000
 AKE  C08  C03  C02  120.88  3.000
 AKE  C04  C03  C02  119.43  3.000
 AKE  H1   C04  C05  119.91  3.000
 AKE  H1   C04  C03  119.82  3.000
 AKE  C05  C04  C03  120.27  3.000
 AKE  H2   C05  C06  120.10  3.000
 AKE  H2   C05  C04  119.86  3.000
 AKE  C06  C05  C04  120.04  3.000
 AKE  H3   C06  C07  119.87  3.000
 AKE  H3   C06  C05  120.10  3.000
 AKE  C07  C06  C05  120.03  3.000
 AKE  H4   C07  C08  119.79  3.000
 AKE  H4   C07  C06  119.94  3.000
 AKE  C08  C07  C06  120.27  3.000
 AKE  C09  C08  C07  119.44  3.000
 AKE  C07  C08  C03  119.70  3.000
 AKE  C09  C08  C03  120.86  3.000
 AKE  C11  C09  O10  122.93  3.000
 AKE  O10  C09  C08  118.38  3.000
 AKE  C11  C09  C08  118.69  3.000
 AKE  C30  C11  C12  120.37  3.000
 AKE  C12  C11  C09  119.18  3.000
 AKE  C30  C11  C09  120.44  3.000
 AKE  C20  C12  N13  118.81  3.000
 AKE  N13  C12  C11  123.65  3.000
 AKE  C20  C12  C11  117.53  3.000
 AKE  H5   N13  C14  119.13  3.000
 AKE  H5   N13  C12  115.49  3.000
 AKE  C14  N13  C12  124.94  3.000
 AKE  H7   C14  H6   107.00  3.000
 AKE  H7   C14  C15  109.56  3.000
 AKE  H6   C14  C15  108.73  3.000
 AKE  H7   C14  N13  110.73  3.000
 AKE  H6   C14  N13  111.18  3.000
 AKE  C15  C14  N13  109.58  3.000
 AKE  H9   C15  H8   106.50  3.000
 AKE  H9   C15  N16  108.53  3.000
 AKE  H8   C15  N16  113.07  3.000
 AKE  H9   C15  C14  109.06  3.000
 AKE  H8   C15  C14  109.45  3.000
 AKE  N16  C15  C14  110.10  3.000
 AKE  H10  N16  C17  108.87  3.000
 AKE  H10  N16  C15  108.88  3.000
 AKE  C17  N16  C15  112.73  3.000
 AKE  H13  C17  H12  106.24  3.000
 AKE  H13  C17  C18  107.74  3.000
 AKE  H12  C17  C18  109.34  3.000
 AKE  H13  C17  N16  108.59  3.000
 AKE  H12  C17  N16  112.91  3.000
 AKE  C18  C17  N16  111.75  3.000
 AKE  H15  C18  H14  107.22  3.000
 AKE  H15  C18  O19  111.45  3.000
 AKE  H14  C18  O19  111.55  3.000
 AKE  H15  C18  C17  109.08  3.000
 AKE  H14  C18  C17  108.55  3.000
 AKE  O19  C18  C17  108.91  3.000
 AKE  H16  O19  C18  108.27  3.000
 AKE  H17  C20  C21  118.31  3.000
 AKE  H17  C20  C12  119.59  3.000
 AKE  C21  C20  C12  122.10  3.000
 AKE  H18  C21  C22  119.59  3.000
 AKE  H18  C21  C20  118.33  3.000
 AKE  C22  C21  C20  122.09  3.000
 AKE  C30  C22  N23  123.62  3.000
 AKE  C30  C22  C21  117.53  3.000
 AKE  N23  C22  C21  118.85  3.000
 AKE  H19  N23  C24  119.10  3.000
 AKE  H19  N23  C22  115.47  3.000
 AKE  C24  N23  C22  125.04  3.000
 AKE  H21  C24  H20  106.99  3.000
 AKE  H21  C24  C25  109.54  3.000
 AKE  H20  C24  C25  108.74  3.000
 AKE  H21  C24  N23  110.79  3.000
 AKE  H20  C24  N23  111.19  3.000
 AKE  C25  C24  N23  109.53  3.000
 AKE  H23  C25  H22  106.51  3.000
 AKE  H23  C25  N26  108.55  3.000
 AKE  H22  C25  N26  113.05  3.000
 AKE  H23  C25  C24  109.08  3.000
 AKE  H22  C25  C24  109.43  3.000
 AKE  N26  C25  C24  110.10  3.000
 AKE  H24  N26  C27  108.85  3.000
 AKE  H24  N26  C25  108.85  3.000
 AKE  C27  N26  C25  112.72  3.000
 AKE  H27  C27  H26  106.25  3.000
 AKE  H27  C27  C28  107.72  3.000
 AKE  H26  C27  C28  109.33  3.000
 AKE  H27  C27  N26  108.63  3.000
 AKE  H26  C27  N26  112.90  3.000
 AKE  C28  C27  N26  111.74  3.000
 AKE  H29  C28  H28  107.23  3.000
 AKE  H29  C28  O29  111.44  3.000
 AKE  H28  C28  O29  111.55  3.000
 AKE  H29  C28  C27  109.08  3.000
 AKE  H28  C28  C27  108.56  3.000
 AKE  O29  C28  C27  108.92  3.000
 AKE  H30  O29  C28  108.25  3.000
 AKE  C22  C30  C11  120.38  3.000
 AKE  C11  C30  C02  120.44  3.000
 AKE  C22  C30  C02  119.18  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
 AKE  CONST_01  C06  C05  C04  C03     0.00   0.0  0
 AKE  CONST_02  C06  C07  C08  C03     0.00   0.0  0
 AKE  CONST_03  C07  C08  C03  C04     0.00   0.0  0
 AKE  CONST_04  C07  C06  C05  C04     0.00   0.0  0
 AKE  CONST_05  C08  C03  C04  C05     0.00   0.0  0
 AKE  CONST_06  C08  C07  C06  C05     0.00   0.0  0
 AKE  CONST_07  C21  C22  C30  C11     0.00   0.0  0
 AKE  CONST_08  C21  C20  C12  C11     0.00   0.0  0
 AKE  CONST_09  C22  C21  C20  C12     0.00   0.0  0
 AKE  CONST_10  C22  C30  C11  C12     0.00   0.0  0
 AKE  CONST_11  C30  C22  C21  C20     0.00   0.0  0
 AKE  CONST_12  C30  C11  C12  C20     0.00   0.0  0
 AKE  CONST_13  N23  C22  C30  C02     0.00   0.0  0
 AKE  CONST_14  N13  C12  C11  C09     0.00   0.0  0
 AKE  CONST_15  N23  C22  C30  C11   180.00   0.0  0
 AKE  CONST_16  C21  C20  C12  N13   180.00   0.0  0
 AKE  CONST_17  C30  C11  C12  N13   180.00   0.0  0
 AKE  CONST_18  N23  C22  C21  C20   180.00   0.0  0
 AKE  CONST_19  H1   C04  C03  C02     0.00   0.0  0
 AKE  CONST_20  H2   C05  C04  C03   180.00   0.0  0
 AKE  CONST_21  H4   C07  C08  C03   180.00   0.0  0
 AKE  CONST_22  H3   C06  C05  C04   180.00   0.0  0
 AKE  CONST_23  H17  C20  C12  C11   180.00   0.0  0
 AKE  CONST_24  H18  C21  C20  C12   180.00   0.0  0
 AKE  CONST_25  C14  N13  C12  C11   180.00   0.0  0
 AKE  CONST_26  C20  C12  N13  C14     0.00   0.0  0
 AKE  CONST_27  C24  N23  C22  C21     0.00   0.0  0
 AKE  CONST_28  C30  C22  N23  C24   180.00   0.0  0
 AKE  CONST_29  H5   N13  C12  C11     0.00   0.0  0
 AKE  CONST_30  H19  N23  C22  C21   180.00   0.0  0
 AKE  Var_01    C15  C14  N13  C12   179.95  30.0  1
 AKE  Var_02    C25  C24  N23  C22  -179.08  30.0  1
 AKE  Var_03    N16  C15  C14  N13  -176.33  30.0  3
 AKE  Var_04    C17  N16  C15  C14  -174.76  30.0  1
 AKE  Var_05    C18  C17  N16  C15  -178.90  30.0  3
 AKE  Var_06    O19  C18  C17  N16    65.19  30.0  3
 AKE  Var_07    N26  C25  C24  N23  -176.02  30.0  1
 AKE  Var_08    C27  N26  C25  C24  -174.55  30.0  1
 AKE  Var_09    C28  C27  N26  C25  -178.59  30.0  1
 AKE  Var_10    O29  C28  C27  N26    65.15  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
 AKE  plan-1  O01  0.020
 AKE  plan-1  C02  0.020
 AKE  plan-1  C03  0.020
 AKE  plan-1  C04  0.020
 AKE  plan-1  C05  0.020
 AKE  plan-1  C06  0.020
 AKE  plan-1  C07  0.020
 AKE  plan-1  C08  0.020
 AKE  plan-1  C09  0.020
 AKE  plan-1  O10  0.020
 AKE  plan-1  C11  0.020
 AKE  plan-1  C12  0.020
 AKE  plan-1  N13  0.020
 AKE  plan-1  C20  0.020
 AKE  plan-1  C21  0.020
 AKE  plan-1  C22  0.020
 AKE  plan-1  N23  0.020
 AKE  plan-1  C30  0.020
 AKE  plan-1  H1   0.020
 AKE  plan-1  H2   0.020
 AKE  plan-1  H3   0.020
 AKE  plan-1  H4   0.020
 AKE  plan-1  H17  0.020
 AKE  plan-1  H18  0.020
 AKE  plan-2  C12  0.020
 AKE  plan-2  N13  0.020
 AKE  plan-2  C14  0.020
 AKE  plan-2  H5   0.020
 AKE  plan-3  C22  0.020
 AKE  plan-3  N23  0.020
 AKE  plan-3  C24  0.020
 AKE  plan-3  H19  0.020

