# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  1 14:24:00 2020
#   Inital geometry file: a 131 line input string
#   Ligand name: [{2-[(carboxymethyl)(2,3-dihydroxybenzyl)amino]ethyl}(2-hydroxybenzyl)amino]acetic acid (non-preferred name)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)CN(CCN(CC(O)=O)Cc1cccc(O)c1O)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
 BHR  BHR  '[{2-[(carboxymethyl)(2,3-dihydroxybenzyl)amino]ethyl}(2-hydroxybenzyl)amino]acetic acid (non-preferred name)'  ligand  53  29  .  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_BHR
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
 BHR  C1    C  CR6   0  -0.003   3.0762  -0.8949   0.6705
 BHR  C2    C  CR16  0  -0.309   2.9623  -2.1423   0.0551
 BHR  C3    C  CR16  0  -0.264   4.0749  -2.8064  -0.4258
 BHR  C4    C  CR16  0  -0.384   5.3338  -2.2255  -0.3049
 BHR  C5    C  CR6   0   0.266   5.4645  -0.9840   0.2912
 BHR  O5    O  OH1   0  -0.649   6.6438  -0.3358   0.4446
 BHR  C6    C  CR6   0   0.263   4.3332  -0.3112   0.7779
 BHR  O6    O  OH1   0  -0.630   4.4498   0.9104   1.3444
 BHR  C7    C  CH2   0  -0.341   1.8348  -0.2035   1.1721
 BHR  N8    N  NT    0  -0.409   1.0970   0.4230   0.0844
 BHR  C9    C  CH2   0  -0.295  -0.2874   0.7471   0.3725
 BHR  C10   C  CH2   0  -0.286  -1.1866   0.3272  -0.7859
 BHR  N11   N  NT    0  -0.486  -2.5776   0.7145  -0.5560
 BHR  C12   C  CH2   0  -0.337  -3.5219  -0.1685  -1.2417
 BHR  C13   C  CR6   0  -0.047  -3.5258  -1.5575  -0.6595
 BHR  C14   C  CR16  0  -0.302  -3.6022  -2.6700  -1.4889
 BHR  C15   C  CR16  0  -0.275  -3.6778  -3.9576  -0.9761
 BHR  C16   C  CR16  0  -0.257  -3.6647  -4.1376   0.4007
 BHR  C17   C  CR16  0  -0.341  -3.5682  -3.0455   1.2494
 BHR  C18   C  CR6   0   0.325  -3.4988  -1.7538   0.7301
 BHR  O18   O  OH1   0  -0.652  -3.4083  -0.7233   1.5885
 BHR  C19   C  CH2   0  -0.447   1.8113   1.4139  -0.6623
 BHR  C20   C  C     0   0.540   2.1944   2.6791   0.0862
 BHR  O20   O  O     0  -0.444   1.8075   2.9933   1.1831
 BHR  C21   C  CH2   0  -0.412  -2.8125   2.1020  -0.8870
 BHR  O21   O  OH1   0  -0.598   3.0036   3.4379  -0.6469
 BHR  C22   C  C     0   0.534  -3.9686   2.6956  -0.1160
 BHR  O22   O  O     0  -0.431  -4.5064   2.1827   0.8313
 BHR  O23   O  OH1   0  -0.590  -4.2999   3.8846  -0.5995
 BHR  H2    H  HCR6  0   0.244   1.9798  -2.5894  -0.0376
 BHR  H3    H  HCR6  0   0.253   3.9746  -3.7757  -0.8955
 BHR  H4    H  HCR6  0   0.272   6.2134  -2.7396  -0.6762
 BHR  HO5   H  HOH1  0   0.482   7.3758  -0.8770   0.1300
 BHR  HO6   H  HOH1  0   0.473   5.3704   1.1973   1.3379
 BHR  H7    H  HCH2  0   0.251   1.1825  -0.9665   1.6016
 BHR  H7A   H  HCH2  0   0.228   2.0729   0.4897   1.9857
 BHR  H9    H  HCH2  0   0.237  -0.6039   0.1974   1.2608
 BHR  H9A   H  HCH2  0   0.222  -0.4310   1.8060   0.6179
 BHR  H10   H  HCH2  0   0.230  -0.8195   0.7299  -1.7409
 BHR  H10A  H  HCH2  0   0.254  -1.1350  -0.7589  -0.8737
 BHR  H12   H  HCH2  0   0.272  -4.5229   0.2610  -1.1388
 BHR  H12A  H  HCH2  0   0.248  -3.3181  -0.2180  -2.3205
 BHR  H14   H  HCR6  0   0.250  -3.6077  -2.5197  -2.5626
 BHR  H15   H  HCR6  0   0.249  -3.7420  -4.8066  -1.6432
 BHR  H16   H  HCR6  0   0.253  -3.7207  -5.1341   0.8205
 BHR  H17   H  HCR6  0   0.255  -3.5474  -3.1837   2.3236
 BHR  HO18  H  HOH1  0   0.473  -3.1657   0.0795   1.0704
 BHR  H19   H  HCH2  0   0.289   2.7186   0.9823  -1.0945
 BHR  H19A  H  HCH2  0   0.290   1.2155   1.7232  -1.5283
 BHR  H21   H  HCH2  0   0.301  -1.9334   2.6988  -0.6267
 BHR  H21A  H  HCH2  0   0.271  -2.9706   2.2567  -1.9632
 BHR  HO21  H  HOH1  0   0.478   3.2158   4.2541  -0.1700
 BHR  HO23  H  HOH1  0   0.485  -5.0128   4.2743  -0.0713

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
 BHR  C1   C2    aromatic  1.396  0.020  1.396
 BHR  C1   C6    aromatic  1.390  0.020  1.390
 BHR  C1   C7    single    1.507  0.020  1.507
 BHR  C2   C3    aromatic  1.382  0.020  1.382
 BHR  C3   C4    aromatic  1.392  0.020  1.392
 BHR  C4   C5    aromatic  1.383  0.020  1.383
 BHR  C5   O5    single    1.354  0.020  1.354
 BHR  C5   C6    aromatic  1.403  0.020  1.403
 BHR  C6   O6    single    1.352  0.020  1.352
 BHR  C7   N8    single    1.456  0.020  1.456
 BHR  N8   C9    single    1.451  0.020  1.451
 BHR  N8   C19   single    1.432  0.020  1.432
 BHR  C9   C10   single    1.525  0.020  1.525
 BHR  C10  N11   single    1.462  0.020  1.462
 BHR  N11  C12   single    1.463  0.020  1.463
 BHR  N11  C21   single    1.446  0.020  1.446
 BHR  C12  C13   single    1.506  0.020  1.506
 BHR  C13  C14   aromatic  1.390  0.020  1.390
 BHR  C13  C18   aromatic  1.404  0.020  1.404
 BHR  C14  C15   aromatic  1.388  0.020  1.388
 BHR  C15  C16   aromatic  1.389  0.020  1.389
 BHR  C16  C17   aromatic  1.387  0.020  1.387
 BHR  C17  C18   aromatic  1.394  0.020  1.394
 BHR  C18  O18   single    1.344  0.020  1.344
 BHR  C19  C20   single    1.519  0.020  1.519
 BHR  C20  O20   double    1.205  0.020  1.205
 BHR  C20  O21   single    1.330  0.020  1.330
 BHR  C21  C22   single    1.511  0.020  1.511
 BHR  C22  O22   double    1.204  0.020  1.204
 BHR  C22  O23   single    1.326  0.020  1.326
 BHR  C2   H2    single    0.930  0.020  1.080
 BHR  C3   H3    single    0.930  0.020  1.080
 BHR  C4   H4    single    0.930  0.020  1.080
 BHR  O5   HO5   single    0.850  0.020  0.980
 BHR  O6   HO6   single    0.850  0.020  0.980
 BHR  C7   H7    single    0.970  0.020  1.090
 BHR  C7   H7A   single    0.970  0.020  1.090
 BHR  C9   H9    single    0.970  0.020  1.090
 BHR  C9   H9A   single    0.970  0.020  1.090
 BHR  C10  H10   single    0.970  0.020  1.090
 BHR  C10  H10A  single    0.970  0.020  1.090
 BHR  C12  H12   single    0.970  0.020  1.090
 BHR  C12  H12A  single    0.970  0.020  1.090
 BHR  C14  H14   single    0.930  0.020  1.080
 BHR  C15  H15   single    0.930  0.020  1.080
 BHR  C16  H16   single    0.930  0.020  1.080
 BHR  C17  H17   single    0.930  0.020  1.080
 BHR  O18  HO18  single    0.850  0.020  0.980
 BHR  C19  H19   single    0.970  0.020  1.090
 BHR  C19  H19A  single    0.970  0.020  1.090
 BHR  C21  H21   single    0.970  0.020  1.090
 BHR  C21  H21A  single    0.970  0.020  1.090
 BHR  O21  HO21  single    0.850  0.020  0.980
 BHR  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
 BHR  C7    C1   C6   121.78  3.000
 BHR  C7    C1   C2   119.31  3.000
 BHR  C6    C1   C2   118.89  3.000
 BHR  H2    C2   C3   120.13  3.000
 BHR  H2    C2   C1   118.73  3.000
 BHR  C3    C2   C1   121.14  3.000
 BHR  H3    C3   C4   119.71  3.000
 BHR  H3    C3   C2   120.46  3.000
 BHR  C4    C3   C2   119.83  3.000
 BHR  H4    C4   C5   119.76  3.000
 BHR  H4    C4   C3   120.40  3.000
 BHR  C5    C4   C3   119.83  3.000
 BHR  C6    C5   O5   115.67  3.000
 BHR  C6    C5   C4   120.23  3.000
 BHR  O5    C5   C4   124.10  3.000
 BHR  HO5   O5   C5   110.84  3.000
 BHR  O6    C6   C5   120.61  3.000
 BHR  O6    C6   C1   119.33  3.000
 BHR  C5    C6   C1   120.06  3.000
 BHR  HO6   O6   C6   110.39  3.000
 BHR  H7A   C7   H7   106.26  3.000
 BHR  H7A   C7   N8   113.13  3.000
 BHR  H7    C7   N8   106.97  3.000
 BHR  H7A   C7   C1   111.01  3.000
 BHR  H7    C7   C1   107.60  3.000
 BHR  N8    C7   C1   111.48  3.000
 BHR  C19   N8   C9   115.16  3.000
 BHR  C19   N8   C7   115.76  3.000
 BHR  C9    N8   C7   115.56  3.000
 BHR  H9A   C9   H9   105.44  3.000
 BHR  H9A   C9   C10  111.02  3.000
 BHR  H9    C9   C10  107.97  3.000
 BHR  H9A   C9   N8   112.65  3.000
 BHR  H9    C9   N8   109.01  3.000
 BHR  C10   C9   N8   110.51  3.000
 BHR  H10A  C10  H10  106.20  3.000
 BHR  H10A  C10  N11  108.75  3.000
 BHR  H10   C10  N11  110.93  3.000
 BHR  H10A  C10  C9   107.90  3.000
 BHR  H10   C10  C9   111.22  3.000
 BHR  N11   C10  C9   111.62  3.000
 BHR  C21   N11  C12  111.52  3.000
 BHR  C21   N11  C10  111.89  3.000
 BHR  C12   N11  C10  112.36  3.000
 BHR  H12A  C12  H12  106.24  3.000
 BHR  H12A  C12  C13  109.77  3.000
 BHR  H12   C12  C13  108.86  3.000
 BHR  H12A  C12  N11  111.56  3.000
 BHR  H12   C12  N11  108.03  3.000
 BHR  C13   C12  N11  112.14  3.000
 BHR  C18   C13  C14  118.69  3.000
 BHR  C18   C13  C12  120.77  3.000
 BHR  C14   C13  C12  120.51  3.000
 BHR  H14   C14  C15  119.62  3.000
 BHR  H14   C14  C13  118.71  3.000
 BHR  C15   C14  C13  121.67  3.000
 BHR  H15   C15  C16  120.68  3.000
 BHR  H15   C15  C14  120.23  3.000
 BHR  C16   C15  C14  119.09  3.000
 BHR  H16   C16  C17  119.42  3.000
 BHR  H16   C16  C15  120.22  3.000
 BHR  C17   C16  C15  120.36  3.000
 BHR  H17   C17  C18  119.12  3.000
 BHR  H17   C17  C16  120.52  3.000
 BHR  C18   C17  C16  120.35  3.000
 BHR  O18   C18  C17  118.41  3.000
 BHR  O18   C18  C13  121.76  3.000
 BHR  C17   C18  C13  119.83  3.000
 BHR  HO18  O18  C18  107.77  3.000
 BHR  H19A  C19  H19  104.49  3.000
 BHR  H19A  C19  C20  106.94  3.000
 BHR  H19   C19  C20  108.31  3.000
 BHR  H19A  C19  N8   109.65  3.000
 BHR  H19   C19  N8   110.30  3.000
 BHR  C20   C19  N8   116.44  3.000
 BHR  O21   C20  O20  123.27  3.000
 BHR  O21   C20  C19  110.92  3.000
 BHR  O20   C20  C19  125.79  3.000
 BHR  H21A  C21  H21  105.77  3.000
 BHR  H21A  C21  C22  109.53  3.000
 BHR  H21   C21  C22  106.21  3.000
 BHR  H21A  C21  N11  112.51  3.000
 BHR  H21   C21  N11  109.79  3.000
 BHR  C22   C21  N11  112.62  3.000
 BHR  HO21  O21  C20  110.03  3.000
 BHR  O23   C22  O22  123.88  3.000
 BHR  O23   C22  C21  110.95  3.000
 BHR  O22   C22  C21  125.16  3.000
 BHR  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
 BHR  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 BHR  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 BHR  CONST_03  C5    C6   C1   C2      0.00   0.0  0
 BHR  CONST_04  C5    C4   C3   C2      0.00   0.0  0
 BHR  CONST_05  C6    C1   C2   C3      0.00   0.0  0
 BHR  CONST_06  C6    C5   C4   C3      0.00   0.0  0
 BHR  CONST_07  C16   C15  C14  C13     0.00   0.0  0
 BHR  CONST_08  C16   C17  C18  C13     0.00   0.0  0
 BHR  CONST_09  C17   C18  C13  C14     0.00   0.0  0
 BHR  CONST_10  C17   C16  C15  C14     0.00   0.0  0
 BHR  CONST_11  C18   C13  C14  C15     0.00   0.0  0
 BHR  CONST_12  C18   C17  C16  C15     0.00   0.0  0
 BHR  CONST_13  O5    C5   C6   C1    180.00   0.0  0
 BHR  CONST_14  O6    C6   C1   C2    180.00   0.0  0
 BHR  CONST_15  C7    C1   C2   C3    180.00   0.0  0
 BHR  CONST_16  O5    C5   C4   C3    180.00   0.0  0
 BHR  CONST_17  O6    C6   C5   C4    180.00   0.0  0
 BHR  CONST_18  C7    C1   C6   C5    180.00   0.0  0
 BHR  CONST_19  C15   C14  C13  C12   180.00   0.0  0
 BHR  CONST_20  C17   C18  C13  C12   180.00   0.0  0
 BHR  CONST_21  O18   C18  C13  C14   180.00   0.0  0
 BHR  CONST_22  O18   C18  C17  C16   180.00   0.0  0
 BHR  CONST_23  H3    C3   C2   C1    180.00   0.0  0
 BHR  CONST_24  H4    C4   C3   C2    180.00   0.0  0
 BHR  CONST_25  H2    C2   C3   C4    180.00   0.0  0
 BHR  CONST_26  H15   C15  C14  C13   180.00   0.0  0
 BHR  CONST_27  H17   C17  C18  C13   180.00   0.0  0
 BHR  CONST_28  H16   C16  C15  C14   180.00   0.0  0
 BHR  CONST_29  H14   C14  C15  C16   180.00   0.0  0
 BHR  CONST_30  HO21  O21  C20  C19   180.00   0.0  0
 BHR  CONST_31  HO23  O23  C22  C21   180.00   0.0  0
 BHR  Var_01    N8    C7   C1   C2    -78.23  30.0  2
 BHR  Var_02    C14   C13  C12  N11  -139.49  30.0  2
 BHR  Var_03    C9    N8   C7   C1    161.64  30.0  3
 BHR  Var_04    C13   C12  N11  C10    67.74  30.0  3
 BHR  Var_05    C10   C9   N8   C7   -134.90  30.0  3
 BHR  Var_06    C20   C19  N8   C7    -65.77  30.0  3
 BHR  Var_07    N11   C10  C9   N8   -176.61  30.0  3
 BHR  Var_08    O20   C20  C19  N8    -10.15  30.0  3
 BHR  Var_09    C12   N11  C10  C9   -152.44  30.0  3
 BHR  Var_10    C22   C21  N11  C10  -153.84  30.0  3
 BHR  Var_11    O22   C22  C21  N11    12.13  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
 BHR  plan-1  C1    0.020
 BHR  plan-1  C2    0.020
 BHR  plan-1  C3    0.020
 BHR  plan-1  C4    0.020
 BHR  plan-1  C5    0.020
 BHR  plan-1  O5    0.020
 BHR  plan-1  C6    0.020
 BHR  plan-1  O6    0.020
 BHR  plan-1  C7    0.020
 BHR  plan-1  H2    0.020
 BHR  plan-1  H3    0.020
 BHR  plan-1  H4    0.020
 BHR  plan-2  C12   0.020
 BHR  plan-2  C13   0.020
 BHR  plan-2  C14   0.020
 BHR  plan-2  C15   0.020
 BHR  plan-2  C16   0.020
 BHR  plan-2  C17   0.020
 BHR  plan-2  C18   0.020
 BHR  plan-2  O18   0.020
 BHR  plan-2  H14   0.020
 BHR  plan-2  H15   0.020
 BHR  plan-2  H16   0.020
 BHR  plan-2  H17   0.020
 BHR  plan-3  C19   0.020
 BHR  plan-3  C20   0.020
 BHR  plan-3  O20   0.020
 BHR  plan-3  O21   0.020
 BHR  plan-3  HO21  0.020
 BHR  plan-4  C21   0.020
 BHR  plan-4  C22   0.020
 BHR  plan-4  O22   0.020
 BHR  plan-4  O23   0.020
 BHR  plan-4  HO23  0.020

