# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 15:36:12 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  52  28  .  2021-08-07  2021-08-07  
;
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  -0.007  -2.6985  -0.9029   0.0692
 BHN  C2    C  CR16  0  -0.280  -2.7973  -0.8682   1.4527
 BHN  C3    C  CR16  0  -0.272  -3.4401  -1.8753   2.1652
 BHN  C4    C  CR16  0  -0.258  -3.9958  -2.9444   1.4811
 BHN  C5    C  CR16  0  -0.380  -3.9081  -3.0045   0.0963
 BHN  C6    C  CR6   0   0.325  -3.2640  -1.9919  -0.6057
 BHN  O6    O  OH1   0  -0.630  -3.1504  -2.0083  -1.9518
 BHN  C7    C  CH2   0  -0.328  -1.9981   0.1826  -0.7195
 BHN  N8    N  NT    0  -0.413  -1.5446   1.2891   0.0922
 BHN  C9    C  CH2   0  -0.287  -0.1267   1.5678   0.0529
 BHN  C10   C  CH2   0  -0.283   0.6285   0.5354   0.8834
 BHN  N11   N  NT    0  -0.481   2.0775   0.6657   0.7578
 BHN  C12   C  CH2   0  -0.342   2.7688  -0.5962   1.0261
 BHN  C13   C  CR6   0  -0.049   2.4735  -1.6360  -0.0222
 BHN  C14   C  CR16  0  -0.298   2.2303  -2.9557   0.3383
 BHN  C15   C  CR16  0  -0.273   2.0139  -3.9422  -0.6138
 BHN  C16   C  CR16  0  -0.255   2.0276  -3.5968  -1.9583
 BHN  C17   C  CR16  0  -0.339   2.2472  -2.2832  -2.3432
 BHN  C18   C  CR6   0   0.326   2.4713  -1.2973  -1.3844
 BHN  O18   O  OH1   0  -0.652   2.6868  -0.0370  -1.8005
 BHN  C19   C  CH2   0  -0.447  -2.4347   2.4018   0.1711
 BHN  C20   C  C     0   0.534  -2.5071   3.2656  -1.0769
 BHN  O20   O  O     0  -0.439  -1.8666   3.0859  -2.0814
 BHN  C21   C  CH2   0  -0.412   2.5942   1.7367   1.5789
 BHN  O21   O  OH1   0  -0.595  -3.3687   4.2641  -0.9223
 BHN  C22   C  C     0   0.535   3.8821   2.3149   1.0413
 BHN  O22   O  O     0  -0.431   4.3462   2.0871  -0.0459
 BHN  O23   O  OH1   0  -0.590   4.4314   3.1412   1.9206
 BHN  H2    H  HCR6  0   0.247  -2.3552  -0.0301   1.9759
 BHN  H3    H  HCR6  0   0.245  -3.5038  -1.8210   3.2440
 BHN  H4    H  HCR6  0   0.254  -4.5001  -3.7383   2.0167
 BHN  H5    H  HCR6  0   0.265  -4.3421  -3.8419  -0.4390
 BHN  HO6   H  HOH1  0   0.473  -3.5727  -2.7946  -2.3153
 BHN  H7    H  HCH2  0   0.247  -1.1400  -0.2561  -1.2397
 BHN  H7A   H  HCH2  0   0.247  -2.6580   0.5267  -1.5252
 BHN  H9    H  HCH2  0   0.214   0.2745   1.5717  -0.9686
 BHN  H9A   H  HCH2  0   0.236   0.0379   2.5712   0.4527
 BHN  H10   H  HCH2  0   0.230   0.3076   0.5940   1.9323
 BHN  H10A  H  HCH2  0   0.251   0.3480  -0.4601   0.5334
 BHN  H12   H  HCH2  0   0.271   3.8440  -0.3959   1.0409
 BHN  H12A  H  HCH2  0   0.248   2.5149  -0.9891   2.0204
 BHN  H14   H  HCR6  0   0.249   2.2142  -3.2138   1.3913
 BHN  H15   H  HCR6  0   0.247   1.8318  -4.9643  -0.3096
 BHN  H16   H  HCR6  0   0.252   1.8589  -4.3511  -2.7163
 BHN  H17   H  HCR6  0   0.254   2.2494  -2.0112  -3.3919
 BHN  HO18  H  HOH1  0   0.472   2.6047   0.5567  -1.0196
 BHN  H19   H  HCH2  0   0.288  -3.4464   2.0520   0.4027
 BHN  H19A  H  HCH2  0   0.290  -2.1594   3.0493   1.0100
 BHN  H21   H  HCH2  0   0.304   1.8741   2.5596   1.6112
 BHN  H21A  H  HCH2  0   0.270   2.7414   1.4307   2.6242
 BHN  HO21  H  HOH1  0   0.480  -3.4006   4.8064  -1.7250
 BHN  HO23  H  HOH1  0   0.485   5.2398   3.5308   1.5547

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  1.387  0.020  1.387
 BHN  C1   C6    aromatic  1.400  0.020  1.400
 BHN  C1   C7    single    1.514  0.020  1.514
 BHN  C2   C3    aromatic  1.391  0.020  1.391
 BHN  C3   C4    aromatic  1.386  0.020  1.386
 BHN  C4   C5    aromatic  1.389  0.020  1.389
 BHN  C5   C6    aromatic  1.390  0.020  1.390
 BHN  C6   O6    single    1.351  0.020  1.351
 BHN  C7   N8    single    1.445  0.020  1.445
 BHN  N8   C9    single    1.446  0.020  1.446
 BHN  N8   C19   single    1.427  0.020  1.427
 BHN  C9   C10   single    1.525  0.020  1.525
 BHN  C10  N11   single    1.460  0.020  1.460
 BHN  N11  C12   single    1.464  0.020  1.464
 BHN  N11  C21   single    1.445  0.020  1.445
 BHN  C12  C13   single    1.506  0.020  1.506
 BHN  C13  C14   aromatic  1.390  0.020  1.390
 BHN  C13  C18   aromatic  1.404  0.020  1.404
 BHN  C14  C15   aromatic  1.388  0.020  1.388
 BHN  C15  C16   aromatic  1.388  0.020  1.388
 BHN  C16  C17   aromatic  1.386  0.020  1.386
 BHN  C17  C18   aromatic  1.393  0.020  1.393
 BHN  C18  O18   single    1.345  0.020  1.345
 BHN  C19  C20   single    1.519  0.020  1.519
 BHN  C20  O20   double    1.205  0.020  1.205
 BHN  C20  O21   single    1.328  0.020  1.328
 BHN  C21  C22   single    1.511  0.020  1.511
 BHN  C22  O22   double    1.204  0.020  1.204
 BHN  C22  O23   single    1.326  0.020  1.326
 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
 BHN  O21  HO21  single    0.850  0.020  0.980
 BHN  O23  HO23  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
 BHN  C7    C1   C6   119.56  3.000
 BHN  C7    C1   C2   122.32  3.000
 BHN  C6    C1   C2   118.12  3.000
 BHN  H2    C2   C3   120.11  3.000
 BHN  H2    C2   C1   118.18  3.000
 BHN  C3    C2   C1   121.70  3.000
 BHN  H3    C3   C4   120.49  3.000
 BHN  H3    C3   C2   120.10  3.000
 BHN  C4    C3   C2   119.41  3.000
 BHN  H4    C4   C5   119.41  3.000
 BHN  H4    C4   C3   120.57  3.000
 BHN  C5    C4   C3   120.02  3.000
 BHN  H5    C5   C6   119.90  3.000
 BHN  H5    C5   C4   120.02  3.000
 BHN  C6    C5   C4   120.07  3.000
 BHN  O6    C6   C5   122.22  3.000
 BHN  O6    C6   C1   117.11  3.000
 BHN  C5    C6   C1   120.67  3.000
 BHN  HO6   O6   C6   110.42  3.000
 BHN  H7A   C7   H7   104.38  3.000
 BHN  H7A   C7   N8   111.17  3.000
 BHN  H7    C7   N8   109.12  3.000
 BHN  H7A   C7   C1   109.23  3.000
 BHN  H7    C7   C1   108.83  3.000
 BHN  N8    C7   C1   113.68  3.000
 BHN  C19   N8   C9   117.58  3.000
 BHN  C19   N8   C7   115.61  3.000
 BHN  C9    N8   C7   116.11  3.000
 BHN  H9A   C9   H9   106.39  3.000
 BHN  H9A   C9   C10  110.35  3.000
 BHN  H9    C9   C10  109.16  3.000
 BHN  H9A   C9   N8   108.36  3.000
 BHN  H9    C9   N8   112.61  3.000
 BHN  C10   C9   N8   109.90  3.000
 BHN  H10A  C10  H10  106.24  3.000
 BHN  H10A  C10  N11  107.98  3.000
 BHN  H10   C10  N11  111.55  3.000
 BHN  H10A  C10  C9   108.39  3.000
 BHN  H10   C10  C9   109.82  3.000
 BHN  N11   C10  C9   112.59  3.000
 BHN  C21   N11  C12  111.46  3.000
 BHN  C21   N11  C10  111.84  3.000
 BHN  C12   N11  C10  112.09  3.000
 BHN  H12A  C12  H12  106.28  3.000
 BHN  H12A  C12  C13  109.74  3.000
 BHN  H12   C12  C13  109.19  3.000
 BHN  H12A  C12  N11  111.41  3.000
 BHN  H12   C12  N11  108.00  3.000
 BHN  C13   C12  N11  112.02  3.000
 BHN  C18   C13  C14  118.73  3.000
 BHN  C18   C13  C12  120.62  3.000
 BHN  C14   C13  C12  120.63  3.000
 BHN  H14   C14  C15  119.65  3.000
 BHN  H14   C14  C13  118.72  3.000
 BHN  C15   C14  C13  121.62  3.000
 BHN  H15   C15  C16  120.60  3.000
 BHN  H15   C15  C14  120.32  3.000
 BHN  C16   C15  C14  119.08  3.000
 BHN  H16   C16  C17  119.37  3.000
 BHN  H16   C16  C15  120.22  3.000
 BHN  C17   C16  C15  120.41  3.000
 BHN  H17   C17  C18  119.22  3.000
 BHN  H17   C17  C16  120.46  3.000
 BHN  C18   C17  C16  120.32  3.000
 BHN  O18   C18  C17  118.43  3.000
 BHN  O18   C18  C13  121.75  3.000
 BHN  C17   C18  C13  119.83  3.000
 BHN  HO18  O18  C18  107.85  3.000
 BHN  H19A  C19  H19  105.02  3.000
 BHN  H19A  C19  C20  107.77  3.000
 BHN  H19   C19  C20  108.14  3.000
 BHN  H19A  C19  N8   110.28  3.000
 BHN  H19   C19  N8   109.80  3.000
 BHN  C20   C19  N8   115.31  3.000
 BHN  O21   C20  O20  123.65  3.000
 BHN  O21   C20  C19  111.27  3.000
 BHN  O20   C20  C19  125.08  3.000
 BHN  H21A  C21  H21  105.63  3.000
 BHN  H21A  C21  C22  109.32  3.000
 BHN  H21   C21  C22  106.49  3.000
 BHN  H21A  C21  N11  112.46  3.000
 BHN  H21   C21  N11  109.81  3.000
 BHN  C22   C21  N11  112.72  3.000
 BHN  HO21  O21  C20  110.22  3.000
 BHN  O23   C22  O22  123.86  3.000
 BHN  O23   C22  C21  110.84  3.000
 BHN  O22   C22  C21  125.28  3.000
 BHN  HO23  O23  C22  110.23  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  CONST_29  HO21  O21  C20  C19   180.00   0.0  0
 BHN  CONST_30  HO23  O23  C22  C21   180.00   0.0  0
 BHN  Var_01    N8    C7   C1   C2     -4.53  30.0  2
 BHN  Var_02    C14   C13  C12  N11  -137.98  30.0  2
 BHN  Var_03    C9    N8   C7   C1    121.49  30.0  3
 BHN  Var_04    C13   C12  N11  C10    66.88  30.0  3
 BHN  Var_05    C10   C9   N8   C7    -75.82  30.0  3
 BHN  Var_06    C20   C19  N8   C7    -73.92  30.0  3
 BHN  Var_07    N11   C10  C9   N8    173.23  30.0  3
 BHN  Var_08    O20   C20  C19  N8     -1.22  30.0  3
 BHN  Var_09    C12   N11  C10  C9   -154.62  30.0  3
 BHN  Var_10    C22   C21  N11  C10  -153.62  30.0  3
 BHN  Var_11    O22   C22  C21  N11    11.17  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-3  HO21  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
 BHN  plan-4  HO23  0.020

