# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 08:41:31 2022
#   Inital geometry file: a 132 line input string
#   Ligand name: 3-[3-[2-[[(2~{S})-2-(3-chlorophenyl)-2-oxidanyl-ethyl]amino]ethylamino]phenyl]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@H](CNCCNc1cccc(c1)c2cccc(c2)C(O)=O)c3cccc(Cl)c3
#
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
 EI5  EI5  "3-[3-[2-[[(2~{S})-2-(3-chlorophenyl)-2-oxidanyl-ethyl]amino]ethylamino]phenyl]benzoic acid"  ligand  51  29  .  2022-08-10  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_EI5
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
 EI5  N1   N   NH1    0  -0.620  74.7127  84.4280  127.4601
 EI5  C7   C   CR6    0   0.107  76.1760  84.8483  133.8017
 EI5  C8   C   CR16   0  -0.424  75.8735  85.7246  132.7656
 EI5  C9   C   CR6    0   0.386  76.2346  85.4546  131.4380
 EI5  O1   O   OC    -1  -0.587  74.0987  83.6345  139.4132
 EI5  C1   C   C1     0  -0.320  75.8402  86.4718  135.6769
 EI5  C5   C   C1     0  -0.306  75.0062  85.7393  137.8133
 EI5  C4   C   C      0  -0.077  74.9303  84.4277  137.3510
 EI5  C3   C   C1     0  -0.362  75.3204  84.1606  136.0431
 EI5  C2   C   C      0   0.103  75.7751  85.1657  135.1892
 EI5  N    N   NH1    0  -0.679  75.9502  86.3754  130.4548
 EI5  C    C   C1     0  -0.228  75.4593  86.7528  136.9807
 EI5  O    O   O      0  -0.585  74.3652  82.1668  137.7546
 EI5  C10  C   CR16   0  -0.353  76.9067  84.2538  131.1703
 EI5  C11  C   CR16   0  -0.235  77.2060  83.3795  132.2040
 EI5  C12  C   CR16   0  -0.348  76.8520  83.6594  133.5135
 EI5  C13  C   CH2    0  -0.338  75.8673  85.9980  129.0630
 EI5  C14  C   CH2    0  -0.311  74.6599  85.1042  128.7432
 EI5  C15  C   CH2    0  -0.334  75.6992  83.3695  127.3563
 EI5  C16  C   CH1    0  -0.002  75.1452  82.0927  128.0066
 EI5  C17  C   C      0   0.097  76.0655  80.9357  127.7240
 EI5  C18  C   C1     0  -0.273  77.1019  80.6616  128.6107
 EI5  C19  C   C      0  -0.022  77.9950  79.6402  128.3304
 EI5  C20  C   C1     0  -0.229  77.8794  78.8730  127.1823
 EI5  C21  C   C1     0  -0.243  76.8399  79.1495  126.3050
 EI5  C22  C   C1     0  -0.296  75.9392  80.1712  126.5683
 EI5  O2   O   OH1    0  -0.674  73.8564  81.8403  127.5177
 EI5  CL   CL  CL     0  -0.133  79.2794  79.3113  129.4507
 EI5  H1   H   HNH1   0   0.364  74.8165  85.0913  126.7045
 EI5  H3   H   HCR6   0   0.248  75.3206  86.6332  132.9789
 EI5  H5   H   H      0   0.246  76.2083  87.2702  135.0440
 EI5  H6   H   H      0   0.240  74.7085  85.9651  138.8284
 EI5  H7   H   H      0   0.237  75.2464  83.1440  135.6786
 EI5  H8   H   HNH1   0   0.376  75.2965  87.0923  130.7294
 EI5  H9   H   H      0   0.246  75.5225  87.7692  137.3492
 EI5  H10  H   HCR6   0   0.261  77.2054  83.9931  130.1640
 EI5  H11  H   HCR6   0   0.249  77.7333  82.4614  131.9746
 EI5  H12  H   HCR6   0   0.241  77.1132  82.9710  134.3065
 EI5  H13  H   HCH2   0   0.237  76.7977  85.5110  128.7653
 EI5  H14  H   HCH2   0   0.255  75.8122  86.9140  128.4727
 EI5  H15  H   HCH2   0   0.243  73.7515  85.7103  128.7810
 EI5  H16  H   HCH2   0   0.236  74.5483  84.3504  129.5272
 EI5  H17  H   HCH2   0   0.226  76.6731  83.6056  127.8036
 EI5  H18  H   HCH2   0   0.252  75.8776  83.1769  126.2956
 EI5  H19  H   HCH1   0   0.218  75.1228  82.2427  129.0978
 EI5  H20  H   H      0   0.282  77.2040  81.2424  129.5202
 EI5  H21  H   H      0   0.276  78.5813  78.0762  126.9765
 EI5  H22  H   H      0   0.264  76.7363  78.5569  125.4055
 EI5  H23  H   H      0   0.254  75.1376  80.3692  125.8696
 EI5  H24  H   HOH1   0   0.440  73.4958  82.7207  127.3203
 EI5  C6   C   C      0   0.396  74.4185  83.3065  138.2550

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
 EI5  C21  C22  aromatic  1.387  0.020  1.387
 EI5  C21  C20  aromatic  1.388  0.020  1.388
 EI5  C22  C17  aromatic  1.391  0.020  1.391
 EI5  C20  C19  aromatic  1.386  0.020  1.386
 EI5  O2   C16  single    1.401  0.020  1.401
 EI5  C17  C16  single    1.505  0.020  1.505
 EI5  C17  C18  aromatic  1.391  0.020  1.391
 EI5  C19  C18  aromatic  1.385  0.020  1.385
 EI5  C19  CL   single    1.736  0.020  1.736
 EI5  C16  C15  single    1.536  0.020  1.536
 EI5  C15  N1   single    1.451  0.020  1.451
 EI5  N1   C14  single    1.451  0.020  1.451
 EI5  C14  C13  single    1.536  0.020  1.536
 EI5  C13  N    single    1.444  0.020  1.444
 EI5  N    C9   single    1.377  0.020  1.377
 EI5  C9   C10  aromatic  1.402  0.020  1.402
 EI5  C9   C8   aromatic  1.402  0.020  1.402
 EI5  C10  C11  aromatic  1.387  0.020  1.387
 EI5  C8   C7   aromatic  1.390  0.020  1.390
 EI5  C11  C12  aromatic  1.385  0.020  1.385
 EI5  C7   C12  aromatic  1.398  0.020  1.398
 EI5  C7   C2   single    1.479  0.020  1.479
 EI5  C1   C2   aromatic  1.396  0.020  1.396
 EI5  C1   C    aromatic  1.387  0.020  1.387
 EI5  C2   C3   aromatic  1.395  0.020  1.395
 EI5  C    C5   aromatic  1.388  0.020  1.388
 EI5  C3   C4   aromatic  1.391  0.020  1.391
 EI5  C5   C4   aromatic  1.393  0.020  1.393
 EI5  C4   C6   single    1.528  0.020  1.528
 EI5  C6   O    deloc     1.246  0.020  1.246
 EI5  C6   O1   deloc     1.246  0.020  1.246
 EI5  N1   H1   single    0.890  0.020  1.040
 EI5  C8   H3   single    0.930  0.020  1.080
 EI5  C1   H5   single    0.930  0.020  1.080
 EI5  C5   H6   single    0.930  0.020  1.080
 EI5  C3   H7   single    0.930  0.020  1.080
 EI5  N    H8   single    0.890  0.020  1.040
 EI5  C    H9   single    0.930  0.020  1.080
 EI5  C10  H10  single    0.930  0.020  1.080
 EI5  C11  H11  single    0.930  0.020  1.080
 EI5  C12  H12  single    0.930  0.020  1.080
 EI5  C13  H13  single    0.970  0.020  1.090
 EI5  C13  H14  single    0.970  0.020  1.090
 EI5  C14  H15  single    0.970  0.020  1.090
 EI5  C14  H16  single    0.970  0.020  1.090
 EI5  C15  H17  single    0.970  0.020  1.090
 EI5  C15  H18  single    0.970  0.020  1.090
 EI5  C16  H19  single    0.970  0.020  1.090
 EI5  C18  H20  single    0.930  0.020  1.080
 EI5  C20  H21  single    0.930  0.020  1.080
 EI5  C21  H22  single    0.930  0.020  1.080
 EI5  C22  H23  single    0.930  0.020  1.080
 EI5  O2   H24  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
 EI5  H1   N1   C15  110.82  3.000
 EI5  H1   N1   C14  111.04  3.000
 EI5  C15  N1   C14  115.34  3.000
 EI5  C12  C7   C2   120.48  3.000
 EI5  C2   C7   C8   120.33  3.000
 EI5  C12  C7   C8   119.19  3.000
 EI5  H3   C8   C9   118.60  3.000
 EI5  H3   C8   C7   119.49  3.000
 EI5  C9   C8   C7   121.89  3.000
 EI5  C10  C9   N    122.38  3.000
 EI5  C10  C9   C8   117.99  3.000
 EI5  N    C9   C8   119.62  3.000
 EI5  H5   C1   C    119.55  3.000
 EI5  H5   C1   C2   120.09  3.000
 EI5  C    C1   C2   120.35  3.000
 EI5  H6   C5   C    120.03  3.000
 EI5  H6   C5   C4   119.54  3.000
 EI5  C    C5   C4   120.43  3.000
 EI5  C3   C4   C6   120.61  3.000
 EI5  C6   C4   C5   120.85  3.000
 EI5  C3   C4   C5   118.54  3.000
 EI5  H7   C3   C2   119.52  3.000
 EI5  H7   C3   C4   118.54  3.000
 EI5  C2   C3   C4   121.92  3.000
 EI5  C3   C2   C1   118.39  3.000
 EI5  C3   C2   C7   120.54  3.000
 EI5  C1   C2   C7   121.07  3.000
 EI5  H8   N    C13  114.27  3.000
 EI5  H8   N    C9   114.51  3.000
 EI5  C13  N    C9   121.69  3.000
 EI5  H9   C    C5   120.02  3.000
 EI5  H9   C    C1   119.60  3.000
 EI5  C5   C    C1   120.37  3.000
 EI5  H10  C10  C11  118.82  3.000
 EI5  H10  C10  C9   121.10  3.000
 EI5  C11  C10  C9   120.08  3.000
 EI5  H11  C11  C12  119.72  3.000
 EI5  H11  C11  C10  118.79  3.000
 EI5  C12  C11  C10  121.48  3.000
 EI5  H12  C12  C11  120.18  3.000
 EI5  H12  C12  C7   120.44  3.000
 EI5  C11  C12  C7   119.37  3.000
 EI5  H14  C13  H13  105.67  3.000
 EI5  H14  C13  C14  109.64  3.000
 EI5  H13  C13  C14  110.71  3.000
 EI5  H14  C13  N    107.75  3.000
 EI5  H13  C13  N    109.30  3.000
 EI5  C14  C13  N    113.44  3.000
 EI5  H16  C14  H15  105.83  3.000
 EI5  H16  C14  C13  109.40  3.000
 EI5  H15  C14  C13  108.88  3.000
 EI5  H16  C14  N1   108.45  3.000
 EI5  H15  C14  N1   108.62  3.000
 EI5  C13  C14  N1   115.25  3.000
 EI5  H18  C15  H17  106.78  3.000
 EI5  H18  C15  C16  108.86  3.000
 EI5  H17  C15  C16  109.05  3.000
 EI5  H18  C15  N1   108.00  3.000
 EI5  H17  C15  N1   114.67  3.000
 EI5  C16  C15  N1   109.33  3.000
 EI5  H19  C16  O2   110.57  3.000
 EI5  H19  C16  C17  107.65  3.000
 EI5  O2   C16  C17  111.00  3.000
 EI5  H19  C16  C15  108.27  3.000
 EI5  C17  C16  C15  109.81  3.000
 EI5  O2   C16  C15  109.49  3.000
 EI5  C22  C17  C18  119.25  3.000
 EI5  C18  C17  C16  119.16  3.000
 EI5  C22  C17  C16  121.52  3.000
 EI5  H20  C18  C19  120.27  3.000
 EI5  H20  C18  C17  119.95  3.000
 EI5  C19  C18  C17  119.77  3.000
 EI5  CL   C19  C20  119.44  3.000
 EI5  CL   C19  C18  119.09  3.000
 EI5  C20  C19  C18  121.47  3.000
 EI5  H21  C20  C21  120.83  3.000
 EI5  H21  C20  C19  120.76  3.000
 EI5  C21  C20  C19  118.41  3.000
 EI5  H22  C21  C22  119.93  3.000
 EI5  H22  C21  C20  119.20  3.000
 EI5  C22  C21  C20  120.87  3.000
 EI5  H23  C22  C21  119.56  3.000
 EI5  H23  C22  C17  120.21  3.000
 EI5  C21  C22  C17  120.22  3.000
 EI5  H24  O2   C16  104.42  3.000
 EI5  O    C6   C4   116.61  3.000
 EI5  O    C6   O1   127.11  3.000
 EI5  C4   C6   O1   116.28  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
 EI5  CONST_01  C10  C9   C8   C7      0.00   0.0  0
 EI5  CONST_02  C10  C11  C12  C7      0.00   0.0  0
 EI5  CONST_03  C    C1   C2   C7    180.00   0.0  0
 EI5  CONST_04  C4   C3   C2   C7    180.00   0.0  0
 EI5  CONST_05  C11  C10  C9   C8      0.00   0.0  0
 EI5  CONST_06  C11  C12  C7   C8      0.00   0.0  0
 EI5  CONST_09  C12  C11  C10  C9      0.00   0.0  0
 EI5  CONST_10  C12  C7   C8   C9      0.00   0.0  0
 EI5  CONST_11  C2   C7   C8   C9    180.00   0.0  0
 EI5  CONST_13  C4   C3   C2   C1      0.00   0.0  0
 EI5  CONST_14  C4   C5   C    C1      0.00   0.0  0
 EI5  CONST_15  C2   C1   C    C5      0.00   0.0  0
 EI5  CONST_16  C2   C3   C4   C5      0.00   0.0  0
 EI5  CONST_18  C    C1   C2   C3      0.00   0.0  0
 EI5  CONST_19  C    C5   C4   C3      0.00   0.0  0
 EI5  CONST_20  C11  C12  C7   C2    180.00   0.0  0
 EI5  CONST_21  C20  C21  C22  C17     0.00   0.0  0
 EI5  CONST_22  C20  C19  C18  C17     0.00   0.0  0
 EI5  CONST_23  C21  C22  C17  C18     0.00   0.0  0
 EI5  CONST_24  C21  C20  C19  C18     0.00   0.0  0
 EI5  CONST_25  C22  C21  C20  C19     0.00   0.0  0
 EI5  CONST_26  C22  C17  C18  C19     0.00   0.0  0
 EI5  CONST_27  N    C9   C8   C7    180.00   0.0  0
 EI5  CONST_28  C2   C3   C4   C6    180.00   0.0  0
 EI5  CONST_29  C    C5   C4   C6    180.00   0.0  0
 EI5  CONST_30  C11  C10  C9   N     180.00   0.0  0
 EI5  CONST_31  C21  C22  C17  C16   180.00   0.0  0
 EI5  CONST_32  C19  C18  C17  C16   180.00   0.0  0
 EI5  CONST_33  CL   C19  C18  C17   180.00   0.0  0
 EI5  CONST_34  CL   C19  C20  C21   180.00   0.0  0
 EI5  CONST_35  H11  C11  C12  C7    180.00   0.0  0
 EI5  CONST_36  H5   C1   C2   C7      0.00   0.0  0
 EI5  CONST_37  H7   C3   C2   C7      0.00   0.0  0
 EI5  CONST_38  H10  C10  C9   C8    180.00   0.0  0
 EI5  CONST_39  H12  C12  C7   C8    180.00   0.0  0
 EI5  CONST_40  H11  C11  C10  C9    180.00   0.0  0
 EI5  CONST_41  H7   C3   C2   C1    180.00   0.0  0
 EI5  CONST_42  H6   C5   C    C1    180.00   0.0  0
 EI5  CONST_43  H5   C1   C    C5    180.00   0.0  0
 EI5  CONST_44  H7   C3   C4   C5    180.00   0.0  0
 EI5  CONST_45  H9   C    C5   C4    180.00   0.0  0
 EI5  CONST_46  H5   C1   C2   C3    180.00   0.0  0
 EI5  CONST_47  H6   C5   C4   C3    180.00   0.0  0
 EI5  CONST_48  H3   C8   C7   C2      0.00   0.0  0
 EI5  CONST_49  H12  C12  C7   C2      0.00   0.0  0
 EI5  CONST_50  H9   C    C1   C2    180.00   0.0  0
 EI5  CONST_51  H3   C8   C9   C10   180.00   0.0  0
 EI5  CONST_52  H12  C12  C11  C10   180.00   0.0  0
 EI5  CONST_53  H10  C10  C11  C12   180.00   0.0  0
 EI5  CONST_54  H3   C8   C7   C12   180.00   0.0  0
 EI5  CONST_55  H22  C21  C22  C17   180.00   0.0  0
 EI5  CONST_56  H23  C22  C17  C18   180.00   0.0  0
 EI5  CONST_57  H21  C20  C19  C18   180.00   0.0  0
 EI5  CONST_58  H22  C21  C20  C19   180.00   0.0  0
 EI5  CONST_59  H23  C22  C21  C20   180.00   0.0  0
 EI5  CONST_60  H20  C18  C19  C20   180.00   0.0  0
 EI5  CONST_61  H21  C20  C21  C22   180.00   0.0  0
 EI5  CONST_62  H20  C18  C17  C22   180.00   0.0  0
 EI5  CONST_65  H8   N    C9   C8      0.00   0.0  0
 EI5  CONST_66  H8   N    C9   C10   180.00   0.0  0
 EI5  Var_01    C3   C4   C6   O1    179.58  30.0  2
 EI5  Var_02    C5   C4   C6   O1     -0.95  30.0  2
 EI5  Var_03    O    C6   C4   C5    178.98  30.0  2
 EI5  Var_04    O    C6   C4   C3     -0.49  30.0  2
 EI5  Var_05    C14  C13  N    C9     68.43  30.0  1
 EI5  Var_06    H13  C13  N    C9    -55.64  30.0  1
 EI5  Var_07    H14  C13  N    C9   -170.01  30.0  1
 EI5  Var_08    N    C13  C14  N1   -165.08  30.0  3
 EI5  Var_09    C15  N1   C14  C13    70.15  30.0  2
 EI5  Var_10    C16  C15  N1   C14    80.43  30.0  1
 EI5  Var_11    H13  C13  C14  N1    -41.78  30.0  3
 EI5  Var_12    H14  C13  C14  N1     74.42  30.0  3
 EI5  Var_13    H15  C14  C13  N      72.62  30.0  1
 EI5  Var_14    H16  C14  C13  N     -42.59  30.0  1
 EI5  Var_15    H1   N1   C14  C13   -56.97  30.0  2
 EI5  Var_16    H17  C15  N1   C14   -42.36  30.0  1
 EI5  Var_17    H18  C15  N1   C14  -161.26  30.0  1
 EI5  Var_18    H8   N    C13  C14   -75.98  30.0  3
 EI5  Var_19    H15  C14  N1   C15  -167.42  30.0  3
 EI5  Var_20    H16  C14  N1   C15   -52.85  30.0  3
 EI5  Var_21    H1   N1   C15  C16  -152.34  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 EI5  chir_01  C16  O2  C17  C15  negativ

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
 EI5  plan-1  C7   0.020
 EI5  plan-1  C8   0.020
 EI5  plan-1  C9   0.020
 EI5  plan-1  C2   0.020
 EI5  plan-1  N    0.020
 EI5  plan-1  C10  0.020
 EI5  plan-1  C11  0.020
 EI5  plan-1  C12  0.020
 EI5  plan-1  H3   0.020
 EI5  plan-1  H10  0.020
 EI5  plan-1  H11  0.020
 EI5  plan-1  H12  0.020
 EI5  plan-2  C7   0.020
 EI5  plan-2  C1   0.020
 EI5  plan-2  C5   0.020
 EI5  plan-2  C4   0.020
 EI5  plan-2  C3   0.020
 EI5  plan-2  C2   0.020
 EI5  plan-2  C    0.020
 EI5  plan-2  H5   0.020
 EI5  plan-2  H6   0.020
 EI5  plan-2  H7   0.020
 EI5  plan-2  H9   0.020
 EI5  plan-2  C6   0.020
 EI5  plan-3  C16  0.020
 EI5  plan-3  C17  0.020
 EI5  plan-3  C18  0.020
 EI5  plan-3  C19  0.020
 EI5  plan-3  C20  0.020
 EI5  plan-3  C21  0.020
 EI5  plan-3  C22  0.020
 EI5  plan-3  CL   0.020
 EI5  plan-3  H20  0.020
 EI5  plan-3  H21  0.020
 EI5  plan-3  H22  0.020
 EI5  plan-3  H23  0.020
 EI5  plan-4  C9   0.020
 EI5  plan-4  N    0.020
 EI5  plan-4  C13  0.020
 EI5  plan-4  H8   0.020
 EI5  plan-5  O1   0.020
 EI5  plan-5  C4   0.020
 EI5  plan-5  O    0.020
 EI5  plan-5  C6   0.020

