# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  2 10:35:01 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: 5-(4-hydroxyphenoxy)-6-(3-hydroxyphenyl)-7-methylnaphthalen-2-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc2cc(O)ccc2c(Oc3ccc(O)cc3)c1c4cccc(O)c4
#
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
 369  369  5-(4-hydroxyphenoxy)-6-(3-hydroxyphenyl)-7-methylnaphthalen-2-ol  ligand  45  27  .  2022-07-22  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_369
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
 369  C10  C  CR6   0   0.286  -0.8060  -0.3918  -0.3900
 369  C12  C  CR16  0  -0.283   1.5016   2.0972  -1.2859
 369  C13  C  CR16  0  -0.373   2.1926   3.1768  -0.7578
 369  C15  C  CR16  0  -0.332   0.6116   3.3046   1.0464
 369  C19  C  CR16  0  -0.280   2.1917  -0.3462   1.2975
 369  C21  C  CR16  0  -0.345   4.2485  -0.5400   0.0528
 369  C22  C  CR6   0   0.368   3.5621  -1.1762  -0.9780
 369  C23  C  CR16  0  -0.406   2.1919  -1.3933  -0.8682
 369  C1   C  CH3   0  -0.738   0.3923  -3.0923   1.9753
 369  C2   C  CR6   0   0.071  -0.5142  -2.2018   1.1777
 369  C3   C  CR16  0  -0.410  -1.8734  -2.3798   1.2145
 369  C4   C  CR66  0   0.150  -2.7520  -1.5726   0.4575
 369  C5   C  CR16  0  -0.473  -4.1520  -1.7560   0.5036
 369  C6   C  CR6   0   0.369  -4.9852  -0.9467  -0.2271
 369  O1   O  OH1   0  -0.629  -6.3257  -1.0676  -0.2275
 369  C7   C  CR16  0  -0.332  -4.4457   0.0824  -1.0342
 369  C8   C  CR16  0  -0.289  -3.0953   0.2720  -1.0979
 369  C9   C  CR66  0   0.003  -2.2116  -0.5489  -0.3580
 369  O2   O  O2    0  -0.522  -0.3047   0.5704  -1.2233
 369  C11  C  CR6   0   0.340   0.3663   1.6245  -0.6504
 369  C14  C  CR6   0   0.342   1.7569   3.7831   0.4163
 369  O3   O  OH1   0  -0.639   2.3978   4.8313   0.9813
 369  C16  C  CR16  0  -0.294  -0.0843   2.2323   0.5125
 369  C17  C  CR6   0  -0.045   0.0371  -1.1832   0.3516
 369  C18  C  CR6   0   0.041   1.5039  -0.9773   0.2664
 369  C20  C  CR16  0  -0.223   3.5569  -0.1305   1.1814
 369  H12  H  HCR6  0   0.261   1.8573   1.6132  -2.1860
 369  H13  H  HCR6  0   0.269   3.0828   3.5347  -1.2625
 369  H15  H  HCR6  0   0.264   0.2615   3.7776   1.9555
 369  H19  H  HCR6  0   0.240   1.6586  -0.0029   2.1743
 369  H21  H  HCR6  0   0.258   5.3143  -0.3689  -0.0349
 369  H23  H  HCR6  0   0.260   1.6537  -1.8828  -1.6730
 369  H1   H  HCH3  0   0.247   1.0905  -3.6259   1.3283
 369  H1A  H  HCH3  0   0.249   0.9937  -2.5245   2.6865
 369  H1B  H  HCH3  0   0.250  -0.1803  -3.8319   2.5328
 369  H3   H  HCR6  0   0.245  -2.2934  -3.1656   1.8321
 369  H5   H  HCR6  0   0.267  -4.5584  -2.5467   1.1255
 369  HO1  H  HOH1  0   0.476  -6.5980  -1.7951   0.3436
 369  H7   H  HCR6  0   0.269  -5.1158   0.7159  -1.6015
 369  H8   H  HCR6  0   0.259  -2.7021   1.0628  -1.7222
 369  HO3  H  HOH1  0   0.472   3.1640   5.0792   0.4526
 369  H16  H  HCR6  0   0.270  -0.9753   1.8753   1.0146
 369  H20  H  HCR6  0   0.251   4.0911   0.3698   1.9788
 369  HO4  H  HOH1  0   0.472   3.6975  -2.0123  -2.6919
 369  O4   O  OH1   0  -0.637   4.2697  -1.5615  -2.0613

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
 369  C10  C9   aromatic  1.415  0.020  1.415
 369  C10  O2   single    1.368  0.020  1.368
 369  C10  C17  aromatic  1.374  0.020  1.374
 369  C12  C13  aromatic  1.386  0.020  1.386
 369  C12  C11  aromatic  1.384  0.020  1.384
 369  C13  C14  aromatic  1.391  0.020  1.391
 369  C15  C14  aromatic  1.392  0.020  1.392
 369  C15  C16  aromatic  1.385  0.020  1.385
 369  C19  C18  aromatic  1.391  0.020  1.391
 369  C19  C20  aromatic  1.387  0.020  1.387
 369  C21  C22  aromatic  1.392  0.020  1.392
 369  C21  C20  aromatic  1.385  0.020  1.385
 369  C22  C23  aromatic  1.392  0.020  1.392
 369  C22  O4   single    1.350  0.020  1.350
 369  C23  C18  aromatic  1.391  0.020  1.391
 369  C1   C2   single    1.500  0.020  1.500
 369  C2   C3   aromatic  1.371  0.020  1.371
 369  C2   C17  aromatic  1.423  0.020  1.423
 369  C3   C4   aromatic  1.413  0.020  1.413
 369  C4   C5   aromatic  1.413  0.020  1.413
 369  C4   C9   aromatic  1.416  0.020  1.416
 369  C5   C6   aromatic  1.372  0.020  1.372
 369  C6   O1   single    1.346  0.020  1.346
 369  C6   C7   aromatic  1.415  0.020  1.415
 369  C7   C8   aromatic  1.365  0.020  1.365
 369  C8   C9   aromatic  1.415  0.020  1.415
 369  O2   C11  single    1.375  0.020  1.375
 369  C11  C16  aromatic  1.387  0.020  1.387
 369  C14  O3   single    1.352  0.020  1.352
 369  C17  C18  single    1.484  0.020  1.484
 369  C12  H12  single    0.930  0.020  1.080
 369  C13  H13  single    0.930  0.020  1.080
 369  C15  H15  single    0.930  0.020  1.080
 369  C19  H19  single    0.930  0.020  1.080
 369  C21  H21  single    0.930  0.020  1.080
 369  C23  H23  single    0.930  0.020  1.080
 369  C1   H1   single    0.970  0.020  1.090
 369  C1   H1A  single    0.970  0.020  1.090
 369  C1   H1B  single    0.970  0.020  1.090
 369  C3   H3   single    0.930  0.020  1.080
 369  C5   H5   single    0.930  0.020  1.080
 369  O1   HO1  single    0.850  0.020  0.980
 369  C7   H7   single    0.930  0.020  1.080
 369  C8   H8   single    0.930  0.020  1.080
 369  O3   HO3  single    0.850  0.020  0.980
 369  C16  H16  single    0.930  0.020  1.080
 369  C20  H20  single    0.930  0.020  1.080
 369  O4   HO4  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
 369  C17  C10  O2   120.60  3.000
 369  C17  C10  C9   122.25  3.000
 369  O2   C10  C9   117.13  3.000
 369  H12  C12  C11  119.91  3.000
 369  H12  C12  C13  120.09  3.000
 369  C11  C12  C13  119.99  3.000
 369  H13  C13  C14  120.40  3.000
 369  H13  C13  C12  119.28  3.000
 369  C14  C13  C12  120.32  3.000
 369  H15  C15  C16  119.94  3.000
 369  H15  C15  C14  119.73  3.000
 369  C16  C15  C14  120.33  3.000
 369  H19  C19  C20  120.23  3.000
 369  H19  C19  C18  120.07  3.000
 369  C20  C19  C18  119.69  3.000
 369  H21  C21  C20  120.70  3.000
 369  H21  C21  C22  119.82  3.000
 369  C20  C21  C22  119.48  3.000
 369  O4   C22  C23  122.33  3.000
 369  O4   C22  C21  117.78  3.000
 369  C23  C22  C21  119.89  3.000
 369  H23  C23  C18  119.65  3.000
 369  H23  C23  C22  120.02  3.000
 369  C18  C23  C22  120.32  3.000
 369  H1B  C1   H1A  108.04  3.000
 369  H1B  C1   H1   107.93  3.000
 369  H1A  C1   H1   106.76  3.000
 369  H1B  C1   C2   110.95  3.000
 369  H1A  C1   C2   111.77  3.000
 369  H1   C1   C2   111.20  3.000
 369  C17  C2   C3   119.51  3.000
 369  C17  C2   C1   119.96  3.000
 369  C3   C2   C1   120.50  3.000
 369  H3   C3   C4   118.58  3.000
 369  H3   C3   C2   119.56  3.000
 369  C4   C3   C2   121.86  3.000
 369  C9   C4   C5   119.40  3.000
 369  C9   C4   C3   118.96  3.000
 369  C5   C4   C3   121.64  3.000
 369  H5   C5   C6   120.50  3.000
 369  H5   C5   C4   118.98  3.000
 369  C6   C5   C4   120.52  3.000
 369  C7   C6   O1   116.42  3.000
 369  C7   C6   C5   120.08  3.000
 369  O1   C6   C5   123.50  3.000
 369  HO1  O1   C6   110.42  3.000
 369  H7   C7   C8   120.44  3.000
 369  H7   C7   C6   119.25  3.000
 369  C8   C7   C6   120.32  3.000
 369  H8   C8   C9   119.94  3.000
 369  H8   C8   C7   119.21  3.000
 369  C9   C8   C7   120.85  3.000
 369  C8   C9   C4   118.83  3.000
 369  C8   C9   C10  122.97  3.000
 369  C4   C9   C10  118.20  3.000
 369  C11  O2   C10  117.66  3.000
 369  C16  C11  O2   121.79  3.000
 369  C16  C11  C12  120.10  3.000
 369  O2   C11  C12  118.09  3.000
 369  O3   C14  C15  117.86  3.000
 369  O3   C14  C13  122.82  3.000
 369  C15  C14  C13  119.32  3.000
 369  HO3  O3   C14  110.32  3.000
 369  H16  C16  C11  120.75  3.000
 369  H16  C16  C15  119.32  3.000
 369  C11  C16  C15  119.93  3.000
 369  C18  C17  C2   121.06  3.000
 369  C18  C17  C10  119.72  3.000
 369  C2   C17  C10  119.21  3.000
 369  C17  C18  C23  119.64  3.000
 369  C17  C18  C19  120.62  3.000
 369  C23  C18  C19  119.73  3.000
 369  H20  C20  C21  119.37  3.000
 369  H20  C20  C19  119.73  3.000
 369  C21  C20  C19  120.90  3.000
 369  HO4  O4   C22  110.33  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
 369  CONST_01  C3   C4   C9   C10    0.00   0.0  0
 369  CONST_02  C5   C4   C9   C10  180.00   0.0  0
 369  CONST_03  C7   C8   C9   C10  180.00   0.0  0
 369  CONST_04  C3   C2   C17  C10    0.00   0.0  0
 369  CONST_07  C15  C14  C13  C12    0.00   0.0  0
 369  CONST_08  C15  C16  C11  C12    0.00   0.0  0
 369  CONST_09  C16  C11  C12  C13    0.00   0.0  0
 369  CONST_10  C16  C15  C14  C13    0.00   0.0  0
 369  CONST_11  C22  C23  C18  C19    0.00   0.0  0
 369  CONST_13  C22  C21  C20  C19    0.00   0.0  0
 369  CONST_14  C18  C23  C22  C21    0.00   0.0  0
 369  CONST_15  C18  C19  C20  C21    0.00   0.0  0
 369  CONST_16  C17  C18  C23  C22  180.00   0.0  0
 369  CONST_17  C20  C21  C22  C23    0.00   0.0  0
 369  CONST_18  C20  C19  C18  C23    0.00   0.0  0
 369  CONST_20  C5   C4   C3   C2   180.00   0.0  0
 369  CONST_21  C9   C4   C3   C2     0.00   0.0  0
 369  CONST_22  C9   C10  C17  C2     0.00   0.0  0
 369  CONST_23  C18  C17  C2   C3   180.00   0.0  0
 369  CONST_24  C6   C5   C4   C3   180.00   0.0  0
 369  CONST_25  C8   C9   C4   C3   180.00   0.0  0
 369  CONST_26  C17  C2   C3   C4     0.00   0.0  0
 369  CONST_27  C7   C6   C5   C4     0.00   0.0  0
 369  CONST_28  C17  C10  C9   C4     0.00   0.0  0
 369  CONST_29  C7   C8   C9   C4     0.00   0.0  0
 369  CONST_30  C8   C9   C4   C5     0.00   0.0  0
 369  CONST_31  C8   C7   C6   C5     0.00   0.0  0
 369  CONST_32  C9   C4   C5   C6     0.00   0.0  0
 369  CONST_33  C9   C8   C7   C6     0.00   0.0  0
 369  CONST_34  C17  C10  C9   C8   180.00   0.0  0
 369  CONST_35  C18  C17  C10  C9   180.00   0.0  0
 369  CONST_36  C14  C13  C12  C11    0.00   0.0  0
 369  CONST_37  C14  C15  C16  C11    0.00   0.0  0
 369  CONST_38  C20  C19  C18  C17  180.00   0.0  0
 369  CONST_39  C1   C2   C17  C10  180.00   0.0  0
 369  CONST_40  O3   C14  C13  C12  180.00   0.0  0
 369  CONST_41  O2   C11  C12  C13  180.00   0.0  0
 369  CONST_42  O2   C11  C16  C15  180.00   0.0  0
 369  CONST_43  C4   C3   C2   C1   180.00   0.0  0
 369  CONST_44  C18  C17  C2   C1     0.00   0.0  0
 369  CONST_45  O2   C10  C17  C2   180.00   0.0  0
 369  CONST_46  O1   C6   C5   C4   180.00   0.0  0
 369  CONST_47  O2   C10  C9   C4   180.00   0.0  0
 369  CONST_48  C8   C7   C6   O1   180.00   0.0  0
 369  CONST_49  O2   C10  C9   C8     0.00   0.0  0
 369  CONST_50  C18  C17  C10  O2     0.00   0.0  0
 369  CONST_51  C16  C15  C14  O3   180.00   0.0  0
 369  CONST_52  O4   C22  C23  C18  180.00   0.0  0
 369  CONST_53  O4   C22  C21  C20  180.00   0.0  0
 369  CONST_54  H8   C8   C9   C10    0.00   0.0  0
 369  CONST_55  H16  C16  C11  C12  180.00   0.0  0
 369  CONST_56  H15  C15  C14  C13  180.00   0.0  0
 369  CONST_57  H13  C13  C14  C15  180.00   0.0  0
 369  CONST_58  H23  C23  C18  C19  180.00   0.0  0
 369  CONST_59  H21  C21  C20  C19  180.00   0.0  0
 369  CONST_60  H19  C19  C20  C21  180.00   0.0  0
 369  CONST_61  H20  C20  C21  C22  180.00   0.0  0
 369  CONST_62  H5   C5   C4   C3     0.00   0.0  0
 369  CONST_63  H3   C3   C4   C5     0.00   0.0  0
 369  CONST_64  H7   C7   C6   C5   180.00   0.0  0
 369  CONST_65  H12  C12  C13  C14  180.00   0.0  0
 369  Var_01    C12  C11  O2   C10  140.37  30.0  2
 369  Var_02    C17  C10  O2   C11  -65.25  30.0  2
 369  Var_03    H1   C1   C2   C3   120.11  30.0  2

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
 369  plan-1  C12  0.020
 369  plan-1  C13  0.020
 369  plan-1  C15  0.020
 369  plan-1  O2   0.020
 369  plan-1  C11  0.020
 369  plan-1  C14  0.020
 369  plan-1  O3   0.020
 369  plan-1  C16  0.020
 369  plan-1  H12  0.020
 369  plan-1  H13  0.020
 369  plan-1  H15  0.020
 369  plan-1  H16  0.020
 369  plan-2  C19  0.020
 369  plan-2  C21  0.020
 369  plan-2  C22  0.020
 369  plan-2  C23  0.020
 369  plan-2  C17  0.020
 369  plan-2  C18  0.020
 369  plan-2  C20  0.020
 369  plan-2  H19  0.020
 369  plan-2  H21  0.020
 369  plan-2  H23  0.020
 369  plan-2  H20  0.020
 369  plan-2  O4   0.020
 369  plan-3  C10  0.020
 369  plan-3  C1   0.020
 369  plan-3  C2   0.020
 369  plan-3  C3   0.020
 369  plan-3  C4   0.020
 369  plan-3  C5   0.020
 369  plan-3  C6   0.020
 369  plan-3  O1   0.020
 369  plan-3  C7   0.020
 369  plan-3  C8   0.020
 369  plan-3  C9   0.020
 369  plan-3  O2   0.020
 369  plan-3  C17  0.020
 369  plan-3  C18  0.020
 369  plan-3  H3   0.020
 369  plan-3  H5   0.020
 369  plan-3  H7   0.020
 369  plan-3  H8   0.020

