# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 06:38:21 2020
#   Inital geometry file: a 129 line input string
#   Ligand name: 2,2'-{ethane-1,2-diylbis[(2-hydroxybenzyl)imino]}diacetic acid (non-preferred name)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)CN(CCN(CC(O)=O)Cc1ccccc1O)Cc2ccccc2O
#
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
 BHN  BHN  '2,2'-{ethane-1,2-diylbis[(2-hydroxybenzyl)imino]}diacetic acid (non-preferred name)'  ligand  50  28  .  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_BHN
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
 BHN  C1    C  CR6    0  -0.023  -3.3438  -0.7262  -0.5528
 BHN  C2    C  CR16   0  -0.277  -2.9541  -1.7813   0.2624
 BHN  C3    C  CR16   0  -0.275  -3.7455  -2.9116   0.4301
 BHN  C4    C  CR16   0  -0.259  -4.9609  -2.9955  -0.2318
 BHN  C5    C  CR16   0  -0.382  -5.3722  -1.9585  -1.0576
 BHN  C6    C  CR6    0   0.312  -4.5689  -0.8337  -1.2216
 BHN  O6    O  OH1    0  -0.631  -4.9313   0.1874  -2.0318
 BHN  C7    C  CH2    0  -0.293  -2.4685   0.4975  -0.7378
 BHN  N8    N  NT     0  -0.418  -1.4720   0.6188   0.2984
 BHN  C9    C  CH2    0  -0.263  -0.1619   1.0644  -0.1292
 BHN  C10   C  CH2    0  -0.279   0.9195   0.6472   0.8632
 BHN  N11   N  NT     0  -0.413   2.2594   0.8384   0.3421
 BHN  C12   C  CH2    0  -0.389   3.2214  -0.0089   1.0244
 BHN  C13   C  CR6    0  -0.002   3.0866  -1.4416   0.5904
 BHN  C14   C  CR16   0  -0.301   2.7845  -2.4387   1.5100
 BHN  C15   C  CR16   0  -0.285   2.6420  -3.7691   1.1379
 BHN  C16   C  CR16   0  -0.257   2.7989  -4.1067  -0.1992
 BHN  C17   C  CR16   0  -0.354   3.0954  -3.1304  -1.1376
 BHN  C18   C  CR6    0   0.324   3.2475  -1.7915  -0.7627
 BHN  O18   O  OH1    0  -0.676   3.5592  -0.9233  -1.7258
 BHN  C19   C  CH2    0  -0.454  -1.9796   1.2153   1.5126
 BHN  C20   C  C      0   0.399  -2.3087   2.7267   1.5210
 BHN  O20   O  O      0  -0.597  -2.1946   3.3749   0.4638
 BHN  C21   C  CH2    0  -0.425   2.6797   2.2161   0.2943
 BHN  O21   O  OC    -1  -0.632  -2.6797   3.1708   2.6288
 BHN  C22   C  C      0   0.435   3.8232   2.4887  -0.6939
 BHN  O22   O  O      0  -0.603   4.1658   1.5652  -1.4759
 BHN  O23   O  OC    -1  -0.592   4.3135   3.6270  -0.6653
 BHN  H2    H  HCR6   0   0.251  -2.0056  -1.6952   0.7778
 BHN  H3    H  HCR6   0   0.242  -3.4152  -3.7159   1.0746
 BHN  H4    H  HCR6   0   0.252  -5.5961  -3.8639  -0.1122
 BHN  H5    H  HCR6   0   0.261  -6.3219  -2.0254  -1.5775
 BHN  HO6   H  HOH1   0   0.470  -5.8006   0.0181  -2.4106
 BHN  H7    H  HCH2   0   0.235  -1.9634   0.4139  -1.7057
 BHN  H7A   H  HCH2   0   0.221  -3.0943   1.3931  -0.8150
 BHN  H9    H  HCH2   0   0.218   0.0780   0.5684  -1.0730
 BHN  H9A   H  HCH2   0   0.197  -0.1271   2.1449  -0.3198
 BHN  H10   H  HCH2   0   0.187   0.7916   1.1583   1.8323
 BHN  H10A  H  HCH2   0   0.235   0.7762  -0.4186   1.0560
 BHN  H12   H  HCH2   0   0.251   4.2292   0.3473   0.7960
 BHN  H12A  H  HCH2   0   0.220   3.1254   0.0554   2.1210
 BHN  H14   H  HCR6   0   0.241   2.6538  -2.1580   2.5494
 BHN  H15   H  HCR6   0   0.240   2.4089  -4.5242   1.8772
 BHN  H16   H  HCR6   0   0.245   2.6891  -5.1358  -0.5188
 BHN  H17   H  HCR6   0   0.243   3.2204  -3.3979  -2.1806
 BHN  HO18  H  HOH1   0   0.491   3.6243   0.0401  -1.4497
 BHN  H19   H  HCH2   0   0.235  -2.8904   0.6778   1.8012
 BHN  H19A  H  HCH2   0   0.232  -1.2795   1.0228   2.3312
 BHN  H21   H  HCH2   0   0.249   1.8377   2.8343  -0.0297
 BHN  H21A  H  HCH2   0   0.198   2.9667   2.6114   1.2840

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
 BHN  C1   C2    aromatic  1.389  0.020  1.389
 BHN  C1   C6    aromatic  1.400  0.020  1.400
 BHN  C1   C7    single    1.516  0.020  1.516
 BHN  C2   C3    aromatic  1.390  0.020  1.390
 BHN  C3   C4    aromatic  1.386  0.020  1.386
 BHN  C4   C5    aromatic  1.388  0.020  1.388
 BHN  C5   C6    aromatic  1.392  0.020  1.392
 BHN  C6   O6    single    1.353  0.020  1.353
 BHN  C7   N8    single    1.443  0.020  1.443
 BHN  N8   C9    single    1.448  0.020  1.448
 BHN  N8   C19   single    1.445  0.020  1.445
 BHN  C9   C10   single    1.526  0.020  1.526
 BHN  C10  N11   single    1.450  0.020  1.450
 BHN  N11  C12   single    1.452  0.020  1.452
 BHN  N11  C21   single    1.441  0.020  1.441
 BHN  C12  C13   single    1.503  0.020  1.503
 BHN  C13  C14   aromatic  1.390  0.020  1.390
 BHN  C13  C18   aromatic  1.407  0.020  1.407
 BHN  C14  C15   aromatic  1.389  0.020  1.389
 BHN  C15  C16   aromatic  1.388  0.020  1.388
 BHN  C16  C17   aromatic  1.386  0.020  1.386
 BHN  C17  C18   aromatic  1.399  0.020  1.399
 BHN  C18  O18   single    1.334  0.020  1.334
 BHN  C19  C20   single    1.547  0.020  1.547
 BHN  C20  O20   deloc     1.245  0.020  1.245
 BHN  C20  O21   deloc     1.250  0.020  1.250
 BHN  C21  C22   single    1.536  0.020  1.536
 BHN  C22  O22   deloc     1.258  0.020  1.258
 BHN  C22  O23   deloc     1.240  0.020  1.240
 BHN  C2   H2    single    0.930  0.020  1.080
 BHN  C3   H3    single    0.930  0.020  1.080
 BHN  C4   H4    single    0.930  0.020  1.080
 BHN  C5   H5    single    0.930  0.020  1.080
 BHN  O6   HO6   single    0.850  0.020  0.980
 BHN  C7   H7    single    0.970  0.020  1.090
 BHN  C7   H7A   single    0.970  0.020  1.090
 BHN  C9   H9    single    0.970  0.020  1.090
 BHN  C9   H9A   single    0.970  0.020  1.090
 BHN  C10  H10   single    0.970  0.020  1.090
 BHN  C10  H10A  single    0.970  0.020  1.090
 BHN  C12  H12   single    0.970  0.020  1.090
 BHN  C12  H12A  single    0.970  0.020  1.090
 BHN  C14  H14   single    0.930  0.020  1.080
 BHN  C15  H15   single    0.930  0.020  1.080
 BHN  C16  H16   single    0.930  0.020  1.080
 BHN  C17  H17   single    0.930  0.020  1.080
 BHN  O18  HO18  single    0.850  0.020  0.980
 BHN  C19  H19   single    0.970  0.020  1.090
 BHN  C19  H19A  single    0.970  0.020  1.090
 BHN  C21  H21   single    0.970  0.020  1.090
 BHN  C21  H21A  single    0.970  0.020  1.090

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
 BHN  C7    C1   C6   120.60  3.000
 BHN  C7    C1   C2   121.52  3.000
 BHN  C6    C1   C2   117.88  3.000
 BHN  H2    C2   C3   120.40  3.000
 BHN  H2    C2   C1   117.69  3.000
 BHN  C3    C2   C1   121.92  3.000
 BHN  H3    C3   C4   120.46  3.000
 BHN  H3    C3   C2   120.15  3.000
 BHN  C4    C3   C2   119.39  3.000
 BHN  H4    C4   C5   119.41  3.000
 BHN  H4    C4   C3   120.68  3.000
 BHN  C5    C4   C3   119.91  3.000
 BHN  H5    C5   C6   119.91  3.000
 BHN  H5    C5   C4   119.91  3.000
 BHN  C6    C5   C4   120.19  3.000
 BHN  O6    C6   C5   121.73  3.000
 BHN  O6    C6   C1   117.55  3.000
 BHN  C5    C6   C1   120.72  3.000
 BHN  HO6   O6   C6   110.16  3.000
 BHN  H7A   C7   H7   105.29  3.000
 BHN  H7A   C7   N8   112.12  3.000
 BHN  H7    C7   N8   108.83  3.000
 BHN  H7A   C7   C1   109.80  3.000
 BHN  H7    C7   C1   108.22  3.000
 BHN  N8    C7   C1   112.28  3.000
 BHN  C19   N8   C9   116.03  3.000
 BHN  C19   N8   C7   113.30  3.000
 BHN  C9    N8   C7   116.01  3.000
 BHN  H9A   C9   H9   106.85  3.000
 BHN  H9A   C9   C10  111.07  3.000
 BHN  H9    C9   C10  106.38  3.000
 BHN  H9A   C9   N8   112.51  3.000
 BHN  H9    C9   N8   108.29  3.000
 BHN  C10   C9   N8   111.40  3.000
 BHN  H10A  C10  H10  106.36  3.000
 BHN  H10A  C10  N11  108.25  3.000
 BHN  H10   C10  N11  111.20  3.000
 BHN  H10A  C10  C9   106.78  3.000
 BHN  H10   C10  C9   111.26  3.000
 BHN  N11   C10  C9   112.64  3.000
 BHN  C21   N11  C12  112.34  3.000
 BHN  C21   N11  C10  114.04  3.000
 BHN  C12   N11  C10  111.48  3.000
 BHN  H12A  C12  H12  105.61  3.000
 BHN  H12A  C12  C13  109.57  3.000
 BHN  H12   C12  C13  109.45  3.000
 BHN  H12A  C12  N11  112.06  3.000
 BHN  H12   C12  N11  108.81  3.000
 BHN  C13   C12  N11  111.16  3.000
 BHN  C18   C13  C14  118.87  3.000
 BHN  C18   C13  C12  120.30  3.000
 BHN  C14   C13  C12  120.82  3.000
 BHN  H14   C14  C15  119.49  3.000
 BHN  H14   C14  C13  118.34  3.000
 BHN  C15   C14  C13  122.17  3.000
 BHN  H15   C15  C16  120.85  3.000
 BHN  H15   C15  C14  120.50  3.000
 BHN  C16   C15  C14  118.65  3.000
 BHN  H16   C16  C17  119.41  3.000
 BHN  H16   C16  C15  120.26  3.000
 BHN  C17   C16  C15  120.33  3.000
 BHN  H17   C17  C18  118.79  3.000
 BHN  H17   C17  C16  120.14  3.000
 BHN  C18   C17  C16  121.07  3.000
 BHN  O18   C18  C17  117.07  3.000
 BHN  O18   C18  C13  124.01  3.000
 BHN  C17   C18  C13  118.91  3.000
 BHN  HO18  O18  C18  116.18  3.000
 BHN  H19A  C19  H19  104.38  3.000
 BHN  H19A  C19  C20  107.70  3.000
 BHN  H19   C19  C20  107.51  3.000
 BHN  H19A  C19  N8   109.34  3.000
 BHN  H19   C19  N8   108.10  3.000
 BHN  C20   C19  N8   118.86  3.000
 BHN  O21   C20  O20  126.50  3.000
 BHN  O21   C20  C19  114.52  3.000
 BHN  O20   C20  C19  118.98  3.000
 BHN  H21A  C21  H21  105.27  3.000
 BHN  H21A  C21  C22  108.65  3.000
 BHN  H21   C21  C22  106.40  3.000
 BHN  H21A  C21  N11  112.86  3.000
 BHN  H21   C21  N11  109.00  3.000
 BHN  C22   C21  N11  114.09  3.000
 BHN  O23   C22  O22  125.51  3.000
 BHN  O23   C22  C21  116.27  3.000
 BHN  O22   C22  C21  118.20  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
 BHN  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 BHN  CONST_02  C4   C5   C6   C1      0.00   0.0  0
 BHN  CONST_03  C5   C6   C1   C2      0.00   0.0  0
 BHN  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 BHN  CONST_05  C6   C1   C2   C3      0.00   0.0  0
 BHN  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 BHN  CONST_07  C16  C15  C14  C13     0.00   0.0  0
 BHN  CONST_08  C16  C17  C18  C13     0.00   0.0  0
 BHN  CONST_09  C17  C18  C13  C14     0.00   0.0  0
 BHN  CONST_10  C17  C16  C15  C14     0.00   0.0  0
 BHN  CONST_11  C18  C13  C14  C15     0.00   0.0  0
 BHN  CONST_12  C18  C17  C16  C15     0.00   0.0  0
 BHN  CONST_13  O6   C6   C1   C2    180.00   0.0  0
 BHN  CONST_14  C7   C1   C2   C3    180.00   0.0  0
 BHN  CONST_15  O6   C6   C5   C4    180.00   0.0  0
 BHN  CONST_16  C7   C1   C6   C5    180.00   0.0  0
 BHN  CONST_17  C15  C14  C13  C12   180.00   0.0  0
 BHN  CONST_18  C17  C18  C13  C12   180.00   0.0  0
 BHN  CONST_19  O18  C18  C13  C14   180.00   0.0  0
 BHN  CONST_20  O18  C18  C17  C16   180.00   0.0  0
 BHN  CONST_21  H3   C3   C2   C1    180.00   0.0  0
 BHN  CONST_22  H5   C5   C6   C1    180.00   0.0  0
 BHN  CONST_23  H4   C4   C3   C2    180.00   0.0  0
 BHN  CONST_24  H2   C2   C3   C4    180.00   0.0  0
 BHN  CONST_25  H15  C15  C14  C13   180.00   0.0  0
 BHN  CONST_26  H17  C17  C18  C13   180.00   0.0  0
 BHN  CONST_27  H16  C16  C15  C14   180.00   0.0  0
 BHN  CONST_28  H14  C14  C15  C16   180.00   0.0  0
 BHN  Var_01    N8   C7   C1   C2    -18.16  30.0  2
 BHN  Var_02    C14  C13  C12  N11  -120.02  30.0  2
 BHN  Var_03    C9   N8   C7   C1    140.37  30.0  3
 BHN  Var_04    C13  C12  N11  C10    74.15  30.0  3
 BHN  Var_05    C10  C9   N8   C7   -157.60  30.0  3
 BHN  Var_06    C20  C19  N8   C7    -71.75  30.0  3
 BHN  Var_07    N11  C10  C9   N8    168.43  30.0  3
 BHN  Var_08    O20  C20  C19  N8      3.73  30.0  3
 BHN  Var_09    C12  N11  C10  C9   -157.53  30.0  3
 BHN  Var_10    C22  C21  N11  C10  -158.60  30.0  3
 BHN  Var_11    O22  C22  C21  N11     8.92  30.0  3

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
 BHN  plan-1  C1   0.020
 BHN  plan-1  C2   0.020
 BHN  plan-1  C3   0.020
 BHN  plan-1  C4   0.020
 BHN  plan-1  C5   0.020
 BHN  plan-1  C6   0.020
 BHN  plan-1  O6   0.020
 BHN  plan-1  C7   0.020
 BHN  plan-1  H2   0.020
 BHN  plan-1  H3   0.020
 BHN  plan-1  H4   0.020
 BHN  plan-1  H5   0.020
 BHN  plan-2  C12  0.020
 BHN  plan-2  C13  0.020
 BHN  plan-2  C14  0.020
 BHN  plan-2  C15  0.020
 BHN  plan-2  C16  0.020
 BHN  plan-2  C17  0.020
 BHN  plan-2  C18  0.020
 BHN  plan-2  O18  0.020
 BHN  plan-2  H14  0.020
 BHN  plan-2  H15  0.020
 BHN  plan-2  H16  0.020
 BHN  plan-2  H17  0.020
 BHN  plan-3  C19  0.020
 BHN  plan-3  C20  0.020
 BHN  plan-3  O20  0.020
 BHN  plan-3  O21  0.020
 BHN  plan-4  C21  0.020
 BHN  plan-4  C22  0.020
 BHN  plan-4  O22  0.020
 BHN  plan-4  O23  0.020

