# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 16:16:50 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: 4-{4-[4-(3-aminopropoxy)phenyl]-1H-pyrazol-5-yl}-6-chlorobenzene-1,3-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NCCCOc1ccc(cc1)c2cn[nH]c2c3cc(Cl)c(O)cc3O
#
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
 KJ2  KJ2  4-{4-[4-(3-aminopropoxy)phenyl]-1H-pyrazol-5-yl}-6-chlorobenzene-1,3-diol  ligand  43  25  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_KJ2
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
 KJ2  C1    C   CR6   0   0.438   2.3975  -0.8057  -3.1073
 KJ2  C2    C   CR6   0  -0.192   1.8110   0.3468  -3.6315
 KJ2  C3    C   CR16  0  -0.476   1.6207  -1.6492  -2.3202
 KJ2  C4    C   CR6   0   0.373   0.2898  -1.3554  -2.0587
 KJ2  C5    C   CR6   0  -0.141  -0.2920  -0.1864  -2.5717
 KJ2  C6    C   CR16  0  -0.233   0.4896   0.6479  -3.3618
 KJ2  O7    O   OH1   0  -0.607  -0.4861  -2.1646  -1.3283
 KJ2  O8    O   OH1   0  -0.607   3.6713  -1.1485  -3.3218
 KJ2  CL9   CL  CL    0  -0.119   2.7683   1.4085  -4.6159
 KJ2  C10   C   CR5   0   0.451  -1.6923   0.1440  -2.3052
 KJ2  C11   C   CR5   0  -0.172  -2.4139   0.2911  -1.1300
 KJ2  N12   N   N     0  -0.258  -3.7841   0.6867  -2.8856
 KJ2  C13   C   CR15  0  -0.115  -3.7109   0.6264  -1.5703
 KJ2  N14   N   NR15  0  -0.491  -2.5615   0.3958  -3.3052
 KJ2  C15   C   CR6   0   0.060  -1.9538   0.1731   0.2526
 KJ2  C16   C   CR16  0  -0.312  -2.8067  -0.3138   1.2473
 KJ2  C17   C   CR16  0  -0.335  -2.3986  -0.4118   2.5639
 KJ2  C18   C   CR16  0  -0.369  -0.2432   0.4578   1.9544
 KJ2  C19   C   CR16  0  -0.313  -0.6727   0.5576   0.6378
 KJ2  C20   C   CR6   0   0.370  -1.1083  -0.0269   2.9327
 KJ2  O21   O   O2    0  -0.476  -0.7939  -0.1524   4.2369
 KJ2  C22   C   CH2   0  -0.174   0.4808   0.2867   4.6801
 KJ2  C23   C   CH2   0  -0.467   0.5418   0.1345   6.1856
 KJ2  C24   C   CH2   0  -0.278   1.8895   0.5848   6.7323
 KJ2  N25   N   NH2   0  -0.799   1.9265   0.4410   8.1800
 KJ2  H3    H   HCR6  0   0.290   2.0714  -2.5519  -1.9228
 KJ2  H6    H   HCR6  0   0.286   0.0626   1.5596  -3.7591
 KJ2  H7    H   HOH1  0   0.480   0.0190  -2.9192  -1.0045
 KJ2  H8    H   HOH1  0   0.472   4.1191  -0.5000  -3.8808
 KJ2  H13   H   HCR5  0   0.258  -4.5784   0.8433  -0.9638
 KJ2  H14   H   HNR5  0   0.418  -2.3694   0.3432  -4.2938
 KJ2  H16   H   HCR6  0   0.247  -3.8081  -0.6346   0.9872
 KJ2  H17   H   HCR6  0   0.259  -3.0776  -0.7923   3.3174
 KJ2  H18   H   HCR6  0   0.277   0.7626   0.7732   2.1952
 KJ2  H19   H   HCR6  0   0.251   0.0139   0.9591  -0.0969
 KJ2  H221  H   HCH2  0   0.220   0.6403   1.3341   4.3978
 KJ2  H222  H   HCH2  0   0.220   1.2736  -0.3045   4.2064
 KJ2  H231  H   HCH2  0   0.232   0.3706  -0.9088   6.4634
 KJ2  H232  H   HCH2  0   0.230  -0.2554   0.7284   6.6432
 KJ2  H241  H   HCH2  0   0.195   2.0930   1.6094   6.3896
 KJ2  H242  H   HCH2  0   0.219   2.6772  -0.0420   6.3058
 KJ2  H251  H   HNH2  0   0.347   2.8487   0.6856   8.5172
 KJ2  H252  H   HNH2  0   0.339   1.2993   1.1187   8.5962

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
 KJ2  C1   C2    aromatic  1.395  0.020  1.395
 KJ2  C1   C3    aromatic  1.391  0.020  1.391
 KJ2  C1   O8    single    1.336  0.020  1.336
 KJ2  C2   C6    aromatic  1.382  0.020  1.382
 KJ2  C2   CL9   single    1.736  0.020  1.736
 KJ2  C3   C4    aromatic  1.388  0.020  1.388
 KJ2  C3   H3    single    0.930  0.020  1.080
 KJ2  C4   C5    aromatic  1.403  0.020  1.403
 KJ2  C4   O7    single    1.338  0.020  1.338
 KJ2  C5   C6    aromatic  1.390  0.020  1.390
 KJ2  C5   C10   single    1.463  0.020  1.463
 KJ2  C6   H6    single    0.930  0.020  1.080
 KJ2  O7   H7    single    0.850  0.020  0.980
 KJ2  O8   H8    single    0.850  0.020  0.980
 KJ2  C10  C11   aromatic  1.387  0.020  1.387
 KJ2  C10  N14   aromatic  1.349  0.020  1.349
 KJ2  C11  C13   aromatic  1.410  0.020  1.410
 KJ2  C11  C15   single    1.462  0.020  1.462
 KJ2  N12  C13   aromatic  1.319  0.020  1.319
 KJ2  N12  N14   aromatic  1.325  0.020  1.325
 KJ2  C13  H13   single    0.930  0.020  1.080
 KJ2  N14  H14   single    0.860  0.020  1.020
 KJ2  C15  C16   aromatic  1.398  0.020  1.398
 KJ2  C15  C19   aromatic  1.392  0.020  1.392
 KJ2  C16  C17   aromatic  1.382  0.020  1.382
 KJ2  C16  H16   single    0.930  0.020  1.080
 KJ2  C17  C20   aromatic  1.396  0.020  1.396
 KJ2  C17  H17   single    0.930  0.020  1.080
 KJ2  C18  C19   aromatic  1.388  0.020  1.388
 KJ2  C18  C20   aromatic  1.393  0.020  1.393
 KJ2  C18  H18   single    0.930  0.020  1.080
 KJ2  C19  H19   single    0.930  0.020  1.080
 KJ2  C20  O21   single    1.347  0.020  1.347
 KJ2  O21  C22   single    1.419  0.020  1.419
 KJ2  C22  C23   single    1.514  0.020  1.514
 KJ2  C22  H221  single    0.970  0.020  1.090
 KJ2  C22  H222  single    0.970  0.020  1.090
 KJ2  C23  C24   single    1.522  0.020  1.522
 KJ2  C23  H231  single    0.970  0.020  1.090
 KJ2  C23  H232  single    0.970  0.020  1.090
 KJ2  C24  N25   single    1.455  0.020  1.455
 KJ2  C24  H241  single    0.970  0.020  1.090
 KJ2  C24  H242  single    0.970  0.020  1.090
 KJ2  N25  H251  single    0.890  0.020  1.040
 KJ2  N25  H252  single    0.890  0.020  1.040

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
 KJ2  O8    C1   C3    117.88  3.000
 KJ2  O8    C1   C2    123.52  3.000
 KJ2  C3    C1   C2    118.60  3.000
 KJ2  CL9   C2   C6    120.32  3.000
 KJ2  CL9   C2   C1    119.11  3.000
 KJ2  C6    C2   C1    120.57  3.000
 KJ2  H3    C3   C4    120.38  3.000
 KJ2  H3    C3   C1    118.69  3.000
 KJ2  C4    C3   C1    120.92  3.000
 KJ2  O7    C4   C5    117.58  3.000
 KJ2  O7    C4   C3    122.07  3.000
 KJ2  C5    C4   C3    120.34  3.000
 KJ2  C10   C5   C6    120.41  3.000
 KJ2  C10   C5   C4    121.23  3.000
 KJ2  C6    C5   C4    118.35  3.000
 KJ2  H6    C6   C5    119.51  3.000
 KJ2  H6    C6   C2    119.28  3.000
 KJ2  C5    C6   C2    121.20  3.000
 KJ2  H7    O7   C4    110.66  3.000
 KJ2  H8    O8   C1    111.24  3.000
 KJ2  N14   C10  C11   105.85  3.000
 KJ2  N14   C10  C5    121.59  3.000
 KJ2  C11   C10  C5    132.55  3.000
 KJ2  C15   C11  C13   127.15  3.000
 KJ2  C15   C11  C10   128.98  3.000
 KJ2  C13   C11  C10   103.84  3.000
 KJ2  N14   N12  C13   104.75  3.000
 KJ2  H13   C13  N12   120.41  3.000
 KJ2  H13   C13  C11   127.66  3.000
 KJ2  N12   C13  C11   111.92  3.000
 KJ2  H14   N14  N12   119.84  3.000
 KJ2  H14   N14  C10   126.47  3.000
 KJ2  N12   N14  C10   113.63  3.000
 KJ2  C19   C15  C16   117.45  3.000
 KJ2  C19   C15  C11   121.95  3.000
 KJ2  C16   C15  C11   120.60  3.000
 KJ2  H16   C16  C17   118.73  3.000
 KJ2  H16   C16  C15   119.77  3.000
 KJ2  C17   C16  C15   121.50  3.000
 KJ2  H17   C17  C20   119.49  3.000
 KJ2  H17   C17  C16   120.17  3.000
 KJ2  C20   C17  C16   120.34  3.000
 KJ2  H18   C18  C20   121.51  3.000
 KJ2  H18   C18  C19   118.55  3.000
 KJ2  C20   C18  C19   119.93  3.000
 KJ2  H19   C19  C18   118.29  3.000
 KJ2  H19   C19  C15   119.89  3.000
 KJ2  C18   C19  C15   121.82  3.000
 KJ2  O21   C20  C18   124.57  3.000
 KJ2  O21   C20  C17   116.47  3.000
 KJ2  C18   C20  C17   118.97  3.000
 KJ2  C22   O21  C20   118.88  3.000
 KJ2  H222  C22  H221  107.38  3.000
 KJ2  H222  C22  C23   110.25  3.000
 KJ2  H221  C22  C23   110.25  3.000
 KJ2  H222  C22  O21   110.34  3.000
 KJ2  H221  C22  O21   110.23  3.000
 KJ2  C23   C22  O21   108.39  3.000
 KJ2  H232  C23  H231  107.32  3.000
 KJ2  H232  C23  C24   109.52  3.000
 KJ2  H231  C23  C24   109.25  3.000
 KJ2  H232  C23  C22   109.37  3.000
 KJ2  H231  C23  C22   110.01  3.000
 KJ2  C24   C23  C22   111.28  3.000
 KJ2  H242  C24  H241  106.22  3.000
 KJ2  H242  C24  N25   108.25  3.000
 KJ2  H241  C24  N25   113.42  3.000
 KJ2  H242  C24  C23   109.15  3.000
 KJ2  H241  C24  C23   109.12  3.000
 KJ2  N25   C24  C23   110.51  3.000
 KJ2  H252  N25  H251  105.40  3.000
 KJ2  H252  N25  C24   109.08  3.000
 KJ2  H251  N25  C24   109.31  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
 KJ2  CONST_01  C5    C6   C2   C1     0.00   0.0  0
 KJ2  CONST_02  C5    C4   C3   C1     0.00   0.0  0
 KJ2  CONST_03  C4    C3   C1   C2     0.00   0.0  0
 KJ2  CONST_04  C4    C5   C6   C2     0.00   0.0  0
 KJ2  CONST_05  C10   C5   C6   C2   180.00   0.0  0
 KJ2  CONST_06  C6    C2   C1   C3     0.00   0.0  0
 KJ2  CONST_07  C6    C5   C4   C3     0.00   0.0  0
 KJ2  CONST_08  C10   C5   C4   C3   180.00   0.0  0
 KJ2  CONST_11  C13   C11  C10  C5   180.00   0.0  0
 KJ2  CONST_12  C15   C11  C10  C5     0.00   0.0  0
 KJ2  CONST_13  N12   N14  C10  C5   180.00   0.0  0
 KJ2  CONST_16  N12   C13  C11  C10    0.00   0.0  0
 KJ2  CONST_19  C13   N12  N14  C10    0.00   0.0  0
 KJ2  CONST_20  N12   N14  C10  C11    0.00   0.0  0
 KJ2  CONST_21  N14   N12  C13  C11    0.00   0.0  0
 KJ2  CONST_22  C17   C16  C15  C11  180.00   0.0  0
 KJ2  CONST_23  C18   C19  C15  C11  180.00   0.0  0
 KJ2  CONST_24  C15   C11  C13  N12  180.00   0.0  0
 KJ2  CONST_25  N14   C10  C11  C13    0.00   0.0  0
 KJ2  CONST_28  C15   C11  C10  N14  180.00   0.0  0
 KJ2  CONST_29  C20   C17  C16  C15    0.00   0.0  0
 KJ2  CONST_30  C20   C18  C19  C15    0.00   0.0  0
 KJ2  CONST_31  C18   C19  C15  C16    0.00   0.0  0
 KJ2  CONST_32  C18   C20  C17  C16    0.00   0.0  0
 KJ2  CONST_33  C19   C15  C16  C17    0.00   0.0  0
 KJ2  CONST_34  C19   C18  C20  C17    0.00   0.0  0
 KJ2  CONST_35  O7    C4   C3   C1   180.00   0.0  0
 KJ2  CONST_36  CL9   C2   C1   C3   180.00   0.0  0
 KJ2  CONST_37  O8    C1   C3   C4   180.00   0.0  0
 KJ2  CONST_38  CL9   C2   C6   C5   180.00   0.0  0
 KJ2  CONST_39  O8    C1   C2   C6   180.00   0.0  0
 KJ2  CONST_40  O7    C4   C5   C6   180.00   0.0  0
 KJ2  CONST_41  C10   C5   C4   O7     0.00   0.0  0
 KJ2  CONST_42  O21   C20  C17  C16  180.00   0.0  0
 KJ2  CONST_43  O21   C20  C18  C19  180.00   0.0  0
 KJ2  CONST_44  H6    C6   C2   C1   180.00   0.0  0
 KJ2  CONST_45  H3    C3   C1   C2   180.00   0.0  0
 KJ2  CONST_46  H14   N14  C10  C5     0.00   0.0  0
 KJ2  CONST_47  H13   C13  C11  C10  180.00   0.0  0
 KJ2  CONST_48  H16   C16  C15  C11    0.00   0.0  0
 KJ2  CONST_49  H19   C19  C15  C11    0.00   0.0  0
 KJ2  CONST_50  H17   C17  C16  C15  180.00   0.0  0
 KJ2  CONST_51  H18   C18  C19  C15  180.00   0.0  0
 KJ2  Var_01    C23   C22  O21  C20  175.75  30.0  3
 KJ2  Var_02    C24   C23  C22  O21  179.82  30.0  3
 KJ2  Var_03    N25   C24  C23  C22  179.58  30.0  3
 KJ2  Var_04    H251  N25  C24  C23  176.23  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
 KJ2  plan-1  C5   0.020
 KJ2  plan-1  C10  0.020
 KJ2  plan-1  C11  0.020
 KJ2  plan-1  N12  0.020
 KJ2  plan-1  C13  0.020
 KJ2  plan-1  N14  0.020
 KJ2  plan-1  C15  0.020
 KJ2  plan-1  H13  0.020
 KJ2  plan-1  H14  0.020
 KJ2  plan-2  C1   0.020
 KJ2  plan-2  C2   0.020
 KJ2  plan-2  C3   0.020
 KJ2  plan-2  C4   0.020
 KJ2  plan-2  C5   0.020
 KJ2  plan-2  C6   0.020
 KJ2  plan-2  O7   0.020
 KJ2  plan-2  O8   0.020
 KJ2  plan-2  CL9  0.020
 KJ2  plan-2  C10  0.020
 KJ2  plan-2  H3   0.020
 KJ2  plan-2  H6   0.020
 KJ2  plan-3  C11  0.020
 KJ2  plan-3  C15  0.020
 KJ2  plan-3  C16  0.020
 KJ2  plan-3  C17  0.020
 KJ2  plan-3  C18  0.020
 KJ2  plan-3  C19  0.020
 KJ2  plan-3  C20  0.020
 KJ2  plan-3  O21  0.020
 KJ2  plan-3  H16  0.020
 KJ2  plan-3  H17  0.020
 KJ2  plan-3  H18  0.020
 KJ2  plan-3  H19  0.020

