# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 07:51:30 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  51  29  .  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_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  -0.013   3.3162  -0.9044   0.7282
 BHR  C2    C  CR16   0  -0.323   3.3712  -2.2769   0.4705
 BHR  C3    C  CR16   0  -0.268   4.5750  -2.9102   0.2236
 BHR  C4    C  CR16   0  -0.364   5.7589  -2.1767   0.2216
 BHR  C5    C  CR6    0   0.284   5.7204  -0.8148   0.4597
 BHR  O5    O  OH1    0  -0.645   6.8655  -0.0965   0.4443
 BHR  C6    C  CR6    0   0.206   4.4970  -0.1627   0.7099
 BHR  O6    O  OH1    0  -0.708   4.5747   1.1573   0.9339
 BHR  C7    C  CH2    0  -0.347   1.9856  -0.2671   1.0242
 BHR  N8    N  NT     0  -0.411   1.1728  -0.0600  -0.1696
 BHR  C9    C  CH2    0  -0.273  -0.1590   0.3855   0.2037
 BHR  C10   C  CH2    0  -0.289  -1.1613   0.3744  -0.9435
 BHR  N11   N  NT     0  -0.420  -2.4632   0.8049  -0.4687
 BHR  C12   C  CH2    0  -0.381  -3.5688   0.1407  -1.1297
 BHR  C13   C  CR6    0  -0.009  -3.6714  -1.2955  -0.6992
 BHR  C14   C  CR16   0  -0.306  -3.6044  -2.3236  -1.6320
 BHR  C15   C  CR16   0  -0.285  -3.6848  -3.6606  -1.2653
 BHR  C16   C  CR16   0  -0.257  -3.8298  -3.9749   0.0788
 BHR  C17   C  CR16   0  -0.353  -3.8952  -2.9683   1.0299
 BHR  C18   C  CR6    0   0.323  -3.8204  -1.6211   0.6617
 BHR  O18   O  OH1    0  -0.676  -3.9101  -0.7184   1.6391
 BHR  C19   C  CH2    0  -0.437   1.8029   0.7615  -1.1963
 BHR  C20   C  C      0   0.445   1.9046   2.2539  -0.8379
 BHR  O20   O  O      0  -0.620   2.7919   2.5904   0.0082
 BHR  C21   C  CH2    0  -0.436  -2.6205   2.2363  -0.4118
 BHR  O21   O  OC    -1  -0.554   1.1089   3.0446  -1.3530
 BHR  C22   C  C      0   0.437  -3.6315   2.7054   0.6449
 BHR  O22   O  O      0  -0.603  -4.0961   1.8476   1.4386
 BHR  O23   O  OC    -1  -0.594  -3.9015   3.9156   0.6507
 BHR  H2    H  HCR6   0   0.238   2.4510  -2.8491   0.4789
 BHR  H3    H  HCR6   0   0.243   4.6042  -3.9756   0.0363
 BHR  H4    H  HCR6   0   0.252   6.7091  -2.6589   0.0257
 BHR  HO5   H  HOH1   0   0.463   6.6346   0.8337   0.5730
 BHR  HO6   H  HOH1   0   0.482   3.7773   1.6974   0.5370
 BHR  H7    H  HCH2   0   0.243   1.4247  -0.9485   1.6700
 BHR  H7A   H  HCH2   0   0.208   2.1192   0.6534   1.6103
 BHR  H9    H  HCH2   0   0.230  -0.5387  -0.3002   0.9661
 BHR  H9A   H  HCH2   0   0.192  -0.1440   1.3811   0.6791
 BHR  H10   H  HCH2   0   0.212  -0.8217   0.9923  -1.7856
 BHR  H10A  H  HCH2   0   0.230  -1.2375  -0.6498  -1.3157
 BHR  H12   H  HCH2   0   0.250  -4.4910   0.6651  -0.8657
 BHR  H12A  H  HCH2   0   0.223  -3.4993   0.1939  -2.2287
 BHR  H14   H  HCR6   0   0.243  -3.4807  -2.0624  -2.6773
 BHR  H15   H  HCR6   0   0.242  -3.6293  -4.4392  -2.0143
 BHR  H16   H  HCR6   0   0.246  -3.8927  -5.0091   0.3940
 BHR  H17   H  HCR6   0   0.244  -4.0115  -3.2172   2.0783
 BHR  HO18  H  HOH1   0   0.490  -3.8272   0.2433   1.3627
 BHR  H19   H  HCH2   0   0.248   2.7950   0.3491  -1.3988
 BHR  H19A  H  HCH2   0   0.237   1.2348   0.6583  -2.1214
 BHR  H21   H  HCH2   0   0.252  -1.6553   2.6875  -0.1620
 BHR  H21A  H  HCH2   0   0.208  -2.8979   2.6738  -1.3855

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  1.398  0.020  1.398
 BHR  C1   C6    aromatic  1.395  0.020  1.395
 BHR  C1   C7    single    1.505  0.020  1.505
 BHR  C2   C3    aromatic  1.382  0.020  1.382
 BHR  C3   C4    aromatic  1.393  0.020  1.393
 BHR  C4   C5    aromatic  1.383  0.020  1.383
 BHR  C5   O5    single    1.352  0.020  1.352
 BHR  C5   C6    aromatic  1.409  0.020  1.409
 BHR  C6   O6    single    1.341  0.020  1.341
 BHR  C7   N8    single    1.459  0.020  1.459
 BHR  N8   C9    single    1.453  0.020  1.453
 BHR  N8   C19   single    1.458  0.020  1.458
 BHR  C9   C10   single    1.523  0.020  1.523
 BHR  C10  N11   single    1.451  0.020  1.451
 BHR  N11  C12   single    1.449  0.020  1.449
 BHR  N11  C21   single    1.441  0.020  1.441
 BHR  C12  C13   single    1.503  0.020  1.503
 BHR  C13  C14   aromatic  1.390  0.020  1.390
 BHR  C13  C18   aromatic  1.407  0.020  1.407
 BHR  C14  C15   aromatic  1.389  0.020  1.389
 BHR  C15  C16   aromatic  1.388  0.020  1.388
 BHR  C16  C17   aromatic  1.386  0.020  1.386
 BHR  C17  C18   aromatic  1.399  0.020  1.399
 BHR  C18  O18   single    1.334  0.020  1.334
 BHR  C19  C20   single    1.538  0.020  1.538
 BHR  C20  O20   deloc     1.271  0.020  1.271
 BHR  C20  O21   deloc     1.234  0.020  1.234
 BHR  C21  C22   single    1.536  0.020  1.536
 BHR  C22  O22   deloc     1.258  0.020  1.258
 BHR  C22  O23   deloc     1.240  0.020  1.240
 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

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   121.74  3.000
 BHR  C7    C1   C2   119.14  3.000
 BHR  C6    C1   C2   119.12  3.000
 BHR  H2    C2   C3   119.93  3.000
 BHR  H2    C2   C1   118.93  3.000
 BHR  C3    C2   C1   121.14  3.000
 BHR  H3    C3   C4   119.69  3.000
 BHR  H3    C3   C2   120.36  3.000
 BHR  C4    C3   C2   119.95  3.000
 BHR  H4    C4   C5   119.59  3.000
 BHR  H4    C4   C3   120.76  3.000
 BHR  C5    C4   C3   119.65  3.000
 BHR  C6    C5   O5   119.45  3.000
 BHR  C6    C5   C4   120.70  3.000
 BHR  O5    C5   C4   119.84  3.000
 BHR  HO5   O5   C5   107.90  3.000
 BHR  O6    C6   C5   115.78  3.000
 BHR  O6    C6   C1   124.77  3.000
 BHR  C5    C6   C1   119.44  3.000
 BHR  HO6   O6   C6   113.73  3.000
 BHR  H7A   C7   H7   105.62  3.000
 BHR  H7A   C7   N8   112.65  3.000
 BHR  H7    C7   N8   106.62  3.000
 BHR  H7A   C7   C1   110.61  3.000
 BHR  H7    C7   C1   107.80  3.000
 BHR  N8    C7   C1   113.06  3.000
 BHR  C19   N8   C9   113.84  3.000
 BHR  C19   N8   C7   114.54  3.000
 BHR  C9    N8   C7   110.11  3.000
 BHR  H9A   C9   H9   105.67  3.000
 BHR  H9A   C9   C10  109.88  3.000
 BHR  H9    C9   C10  106.98  3.000
 BHR  H9A   C9   N8   112.02  3.000
 BHR  H9    C9   N8   107.76  3.000
 BHR  C10   C9   N8   114.04  3.000
 BHR  H10A  C10  H10  106.73  3.000
 BHR  H10A  C10  N11  109.09  3.000
 BHR  H10   C10  N11  111.18  3.000
 BHR  H10A  C10  C9   108.02  3.000
 BHR  H10   C10  C9   111.71  3.000
 BHR  N11   C10  C9   109.98  3.000
 BHR  C21   N11  C12  112.95  3.000
 BHR  C21   N11  C10  113.92  3.000
 BHR  C12   N11  C10  113.53  3.000
 BHR  H12A  C12  H12  105.71  3.000
 BHR  H12A  C12  C13  109.63  3.000
 BHR  H12   C12  C13  109.37  3.000
 BHR  H12A  C12  N11  112.61  3.000
 BHR  H12   C12  N11  108.27  3.000
 BHR  C13   C12  N11  111.06  3.000
 BHR  C18   C13  C14  118.88  3.000
 BHR  C18   C13  C12  120.36  3.000
 BHR  C14   C13  C12  120.76  3.000
 BHR  H14   C14  C15  119.54  3.000
 BHR  H14   C14  C13  118.31  3.000
 BHR  C15   C14  C13  122.15  3.000
 BHR  H15   C15  C16  120.86  3.000
 BHR  H15   C15  C14  120.47  3.000
 BHR  C16   C15  C14  118.67  3.000
 BHR  H16   C16  C17  119.41  3.000
 BHR  H16   C16  C15  120.27  3.000
 BHR  C17   C16  C15  120.33  3.000
 BHR  H17   C17  C18  118.79  3.000
 BHR  H17   C17  C16  120.13  3.000
 BHR  C18   C17  C16  121.08  3.000
 BHR  O18   C18  C17  117.10  3.000
 BHR  O18   C18  C13  124.01  3.000
 BHR  C17   C18  C13  118.89  3.000
 BHR  HO18  O18  C18  116.17  3.000
 BHR  H19A  C19  H19  106.25  3.000
 BHR  H19A  C19  C20  108.90  3.000
 BHR  H19   C19  C20  110.44  3.000
 BHR  H19A  C19  N8   108.60  3.000
 BHR  H19   C19  N8   108.06  3.000
 BHR  C20   C19  N8   114.28  3.000
 BHR  O21   C20  O20  123.92  3.000
 BHR  O21   C20  C19  118.80  3.000
 BHR  O20   C20  C19  117.26  3.000
 BHR  H21A  C21  H21  105.06  3.000
 BHR  H21A  C21  C22  108.70  3.000
 BHR  H21   C21  C22  107.32  3.000
 BHR  H21A  C21  N11  112.74  3.000
 BHR  H21   C21  N11  108.80  3.000
 BHR  C22   C21  N11  113.73  3.000
 BHR  O23   C22  O22  125.62  3.000
 BHR  O23   C22  C21  116.40  3.000
 BHR  O22   C22  C21  117.97  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  Var_01    N8   C7   C1   C2    -77.03  30.0  2
 BHR  Var_02    C14  C13  C12  N11  -121.97  30.0  2
 BHR  Var_03    C9   N8   C7   C1    172.28  30.0  3
 BHR  Var_04    C13  C12  N11  C10    71.46  30.0  3
 BHR  Var_05    C10  C9   N8   C7   -168.91  30.0  3
 BHR  Var_06    C20  C19  N8   C7    -71.68  30.0  3
 BHR  Var_07    N11  C10  C9   N8    178.75  30.0  3
 BHR  Var_08    O20  C20  C19  N8     75.26  30.0  3
 BHR  Var_09    C12  N11  C10  C9   -145.76  30.0  3
 BHR  Var_10    C22  C21  N11  C10  -152.63  30.0  3
 BHR  Var_11    O22  C22  C21  N11     7.83  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-4  C21  0.020
 BHR  plan-4  C22  0.020
 BHR  plan-4  O22  0.020
 BHR  plan-4  O23  0.020

