# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 22:23:02 2020
#   Inital geometry file: a 120 line input string
#   Ligand name: 2-(2'-ethoxybiphenyl-4-yl)-4-hydroxy-1,6-naphthyridine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOc1ccccc1c2ccc(cc2)c3nc4ccncc4c(O)c3C#N
#
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
 4HN  4HN  2-(2'-ethoxybiphenyl-4-yl)-4-hydroxy-1,6-naphthyridine-3-carbonitrile  ligand  45  28  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_4HN
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
 4HN  C1    C  CSP   0   0.021   1.9519   1.8467  -1.8050
 4HN  C2    C  CR16  0  -0.273  -5.7079  -1.5317  -1.8143
 4HN  C3    C  CR16  0  -0.246  -6.5829  -0.9875  -0.8892
 4HN  C4    C  CR16  0  -0.283  -4.3431  -1.3435  -1.6437
 4HN  C5    C  CR16  0  -0.290  -1.5293  -1.5538  -0.5441
 4HN  C6    C  CR16  0  -0.271  -1.7890   0.8084  -0.2447
 4HN  C7    C  CR16  0  -0.266  -0.1545  -1.4184  -0.4602
 4HN  C8    C  CR16  0  -0.274  -0.4135   0.9501  -0.1796
 4HN  C9    C  CR16  0  -0.384  -6.1038  -0.2687   0.1988
 4HN  C10   C  CR16  0  -0.365   4.4975  -1.7993   1.5072
 4HN  C11   C  CR16  0  -0.065   5.8537  -1.7108   1.6575
 4HN  C12   C  CR16  0  -0.081   6.0188   0.1267   0.3258
 4HN  C13   C  CR6   0  -0.164   2.5944   0.9720  -0.8895
 4HN  C14   C  CR66  0  -0.109   4.6281   0.1414   0.0901
 4HN  C15   C  CR6   0   0.092  -2.3710  -0.4454  -0.4365
 4HN  C16   C  CR6   0   0.021   0.4204  -0.1610  -0.2904
 4HN  C17   C  CR6   0  -0.051  -3.8331  -0.6177  -0.5718
 4HN  C18   C  CR66  0   0.296   3.8342  -0.8527   0.7035
 4HN  C19   C  CR6   0   0.365  -4.7333  -0.0824   0.3676
 4HN  C20   C  CR6   0   0.481   3.9693   1.0796  -0.7449
 4HN  C21   C  CR6   0   0.244   1.8875  -0.0438  -0.1852
 4HN  C22   C  CH3   0  -0.679  -4.1696   1.8935   3.3763
 4HN  C23   C  CH2   0  -0.190  -5.0428   1.1952   2.3615
 4HN  N24   N  NS    0  -0.235   1.4605   2.5531  -2.5719
 4HN  N25   N  N     0  -0.398   6.6141  -0.7591   1.0777
 4HN  N26   N  N     0  -0.468   2.4939  -0.9262   0.5639
 4HN  O28   O  O2    0  -0.462  -4.1931   0.5743   1.4074
 4HN  H2    H  HCR6  0   0.254  -6.0779  -2.0897  -2.6635
 4HN  H3    H  HCR6  0   0.261  -7.6511  -1.1190  -1.0042
 4HN  H4    H  HCR6  0   0.256  -3.6532  -1.7551  -2.3705
 4HN  H9    H  HCR6  0   0.281  -6.8104   0.1335   0.9118
 4HN  H5    H  HCR6  0   0.260  -1.9556  -2.5395  -0.6834
 4HN  H7    H  HCR6  0   0.260   0.4779  -2.2929  -0.5373
 4HN  H6    H  HCR6  0   0.255  -2.4092   1.6894  -0.1571
 4HN  H8    H  HCR6  0   0.266   0.0014   1.9358  -0.0122
 4HN  H10   H  HCR6  0   0.285   3.9299  -2.5801   1.9940
 4HN  H11   H  HCR6  0   0.283   6.3820  -2.4291   2.2722
 4HN  H12   H  HCR6  0   0.271   6.6675   0.8740  -0.1210
 4HN  H27   H  HOH1  0   0.506   5.5364   2.0439  -1.2909
 4HN  H221  H  HCH3  0   0.237  -4.7997   2.4007   4.1063
 4HN  H222  H  HCH3  0   0.235  -3.5371   1.1866   3.9128
 4HN  H223  H  HCH3  0   0.234  -3.5323   2.6414   2.9039
 4HN  H231  H  HCH2  0   0.224  -5.6771   0.4481   2.8506
 4HN  H232  H  HCH2  0   0.225  -5.7034   1.9142   1.8658
 4HN  O27   O  OH1   0  -0.562   4.5783   2.0389  -1.4099

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
 4HN  C1   C13   single    1.420  0.020  1.420
 4HN  C1   N24   triple    1.153  0.020  1.153
 4HN  C2   C3    aromatic  1.385  0.020  1.385
 4HN  C2   C4    aromatic  1.388  0.020  1.388
 4HN  C3   C9    aromatic  1.389  0.020  1.389
 4HN  C4   C17   aromatic  1.391  0.020  1.391
 4HN  C5   C7    aromatic  1.384  0.020  1.384
 4HN  C5   C15   aromatic  1.396  0.020  1.396
 4HN  C6   C8    aromatic  1.384  0.020  1.384
 4HN  C6   C15   aromatic  1.396  0.020  1.396
 4HN  C7   C16   aromatic  1.393  0.020  1.393
 4HN  C8   C16   aromatic  1.394  0.020  1.394
 4HN  C9   C19   aromatic  1.393  0.020  1.393
 4HN  C10  C11   aromatic  1.367  0.020  1.367
 4HN  C10  C18   aromatic  1.408  0.020  1.408
 4HN  C11  N25   aromatic  1.349  0.020  1.349
 4HN  C12  C14   aromatic  1.411  0.020  1.411
 4HN  C12  N25   aromatic  1.306  0.020  1.306
 4HN  C13  C20   aromatic  1.387  0.020  1.387
 4HN  C13  C21   aromatic  1.424  0.020  1.424
 4HN  C14  C18   aromatic  1.412  0.020  1.412
 4HN  C14  C20   aromatic  1.418  0.020  1.418
 4HN  C15  C17   single    1.478  0.020  1.478
 4HN  C16  C21   single    1.475  0.020  1.475
 4HN  C17  C19   aromatic  1.407  0.020  1.407
 4HN  C18  N26   aromatic  1.349  0.020  1.349
 4HN  C19  O28   single    1.343  0.020  1.343
 4HN  C20  O27   single    1.317  0.020  1.317
 4HN  C21  N26   aromatic  1.307  0.020  1.307
 4HN  C22  C23   single    1.510  0.020  1.510
 4HN  C23  O28   single    1.421  0.020  1.421
 4HN  C2   H2    single    0.930  0.020  1.080
 4HN  C3   H3    single    0.930  0.020  1.080
 4HN  C4   H4    single    0.930  0.020  1.080
 4HN  C9   H9    single    0.930  0.020  1.080
 4HN  C5   H5    single    0.930  0.020  1.080
 4HN  C7   H7    single    0.930  0.020  1.080
 4HN  C6   H6    single    0.930  0.020  1.080
 4HN  C8   H8    single    0.930  0.020  1.080
 4HN  C10  H10   single    0.930  0.020  1.080
 4HN  C11  H11   single    0.930  0.020  1.080
 4HN  C12  H12   single    0.930  0.020  1.080
 4HN  O27  H27   single    0.850  0.020  0.980
 4HN  C22  H221  single    0.970  0.020  1.090
 4HN  C22  H222  single    0.970  0.020  1.090
 4HN  C22  H223  single    0.970  0.020  1.090
 4HN  C23  H231  single    0.970  0.020  1.090
 4HN  C23  H232  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
 4HN  N24   C1   C13   180.00  3.000
 4HN  H2    C2   C4    120.19  3.000
 4HN  H2    C2   C3    120.74  3.000
 4HN  C4    C2   C3    119.07  3.000
 4HN  H3    C3   C9    119.11  3.000
 4HN  H3    C3   C2    120.32  3.000
 4HN  C9    C3   C2    120.57  3.000
 4HN  H4    C4   C17   118.79  3.000
 4HN  H4    C4   C2    119.48  3.000
 4HN  C17   C4   C2    121.72  3.000
 4HN  H5    C5   C15   119.69  3.000
 4HN  H5    C5   C7    119.20  3.000
 4HN  C15   C5   C7    121.10  3.000
 4HN  H6    C6   C15   120.27  3.000
 4HN  H6    C6   C8    118.87  3.000
 4HN  C15   C6   C8    120.85  3.000
 4HN  H7    C7   C16   119.80  3.000
 4HN  H7    C7   C5    119.81  3.000
 4HN  C16   C7   C5    120.38  3.000
 4HN  H8    C8   C16   120.59  3.000
 4HN  H8    C8   C6    118.78  3.000
 4HN  C16   C8   C6    120.61  3.000
 4HN  H9    C9   C19   120.87  3.000
 4HN  H9    C9   C3    118.91  3.000
 4HN  C19   C9   C3    120.22  3.000
 4HN  H10   C10  C18   119.69  3.000
 4HN  H10   C10  C11   121.20  3.000
 4HN  C18   C10  C11   119.11  3.000
 4HN  H11   C11  N25   115.90  3.000
 4HN  H11   C11  C10   120.22  3.000
 4HN  N25   C11  C10   123.88  3.000
 4HN  H12   C12  N25   115.57  3.000
 4HN  H12   C12  C14   120.87  3.000
 4HN  N25   C12  C14   123.56  3.000
 4HN  C21   C13  C20   119.74  3.000
 4HN  C21   C13  C1    122.25  3.000
 4HN  C20   C13  C1    117.92  3.000
 4HN  C20   C14  C18   117.40  3.000
 4HN  C20   C14  C12   124.28  3.000
 4HN  C18   C14  C12   118.31  3.000
 4HN  C17   C15  C6    121.98  3.000
 4HN  C17   C15  C5    119.78  3.000
 4HN  C6    C15  C5    118.20  3.000
 4HN  C21   C16  C8    121.73  3.000
 4HN  C21   C16  C7    119.39  3.000
 4HN  C8    C16  C7    118.84  3.000
 4HN  C19   C17  C15   121.83  3.000
 4HN  C19   C17  C4    118.58  3.000
 4HN  C15   C17  C4    119.59  3.000
 4HN  N26   C18  C14   123.48  3.000
 4HN  N26   C18  C10   119.36  3.000
 4HN  C14   C18  C10   117.15  3.000
 4HN  O28   C19  C17   116.45  3.000
 4HN  O28   C19  C9    123.70  3.000
 4HN  C17   C19  C9    119.84  3.000
 4HN  O27   C20  C14   124.37  3.000
 4HN  O27   C20  C13   117.55  3.000
 4HN  C14   C20  C13   118.08  3.000
 4HN  N26   C21  C16   116.66  3.000
 4HN  N26   C21  C13   122.33  3.000
 4HN  C16   C21  C13   121.00  3.000
 4HN  H223  C22  H222  108.60  3.000
 4HN  H223  C22  H221  108.00  3.000
 4HN  H222  C22  H221  107.92  3.000
 4HN  H223  C22  C23   111.35  3.000
 4HN  H222  C22  C23   111.50  3.000
 4HN  H221  C22  C23   109.34  3.000
 4HN  H232  C23  H231  107.49  3.000
 4HN  H232  C23  O28   110.11  3.000
 4HN  H231  C23  O28   110.38  3.000
 4HN  H232  C23  C22   110.45  3.000
 4HN  H231  C23  C22   110.50  3.000
 4HN  O28   C23  C22   107.92  3.000
 4HN  C12   N25  C11   117.98  3.000
 4HN  C21   N26  C18   118.91  3.000
 4HN  C23   O28  C19   119.54  3.000
 4HN  H27   O27  C20   113.62  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
 4HN  CONST_01  C19   C9   C3   C2      0.00   0.0  0
 4HN  CONST_02  C15   C17  C4   C2    180.00   0.0  0
 4HN  CONST_03  C19   C17  C4   C2      0.00   0.0  0
 4HN  CONST_04  C17   C4   C2   C3      0.00   0.0  0
 4HN  CONST_05  C17   C19  C9   C3      0.00   0.0  0
 4HN  CONST_06  C9    C3   C2   C4      0.00   0.0  0
 4HN  CONST_09  C9    C19  C17  C4      0.00   0.0  0
 4HN  CONST_10  C8    C16  C7   C5      0.00   0.0  0
 4HN  CONST_11  C21   C16  C7   C5    180.00   0.0  0
 4HN  CONST_12  C8    C6   C15  C5      0.00   0.0  0
 4HN  CONST_14  C7    C16  C8   C6      0.00   0.0  0
 4HN  CONST_15  C21   C16  C8   C6    180.00   0.0  0
 4HN  CONST_16  C7    C5   C15  C6      0.00   0.0  0
 4HN  CONST_18  C17   C15  C5   C7    180.00   0.0  0
 4HN  CONST_21  C17   C15  C6   C8    180.00   0.0  0
 4HN  CONST_24  C15   C17  C19  C9    180.00   0.0  0
 4HN  CONST_25  C12   N25  C11  C10     0.00   0.0  0
 4HN  CONST_26  C12   C14  C18  C10     0.00   0.0  0
 4HN  CONST_27  C20   C14  C18  C10   180.00   0.0  0
 4HN  CONST_28  C21   N26  C18  C10   180.00   0.0  0
 4HN  CONST_29  C14   C18  C10  C11     0.00   0.0  0
 4HN  CONST_30  N26   C18  C10  C11   180.00   0.0  0
 4HN  CONST_31  C14   C12  N25  C11     0.00   0.0  0
 4HN  CONST_32  N26   C18  C14  C12   180.00   0.0  0
 4HN  CONST_33  C13   C20  C14  C12   180.00   0.0  0
 4HN  CONST_34  C18   C14  C20  C13     0.00   0.0  0
 4HN  CONST_35  C18   N26  C21  C13     0.00   0.0  0
 4HN  CONST_36  C21   N26  C18  C14     0.00   0.0  0
 4HN  CONST_37  C21   C13  C20  C14     0.00   0.0  0
 4HN  CONST_38  C16   C7   C5   C15     0.00   0.0  0
 4HN  CONST_39  C16   C8   C6   C15     0.00   0.0  0
 4HN  CONST_40  C20   C13  C21  C16   180.00   0.0  0
 4HN  CONST_41  C18   N26  C21  C16   180.00   0.0  0
 4HN  CONST_42  N25   C11  C10  C18     0.00   0.0  0
 4HN  CONST_43  N25   C12  C14  C18     0.00   0.0  0
 4HN  CONST_44  N26   C21  C13  C20     0.00   0.0  0
 4HN  CONST_45  N25   C12  C14  C20   180.00   0.0  0
 4HN  CONST_46  N26   C18  C14  C20     0.00   0.0  0
 4HN  CONST_47  C14   C20  C13  C1    180.00   0.0  0
 4HN  CONST_48  C16   C21  C13  C1      0.00   0.0  0
 4HN  CONST_49  N26   C21  C13  C1    180.00   0.0  0
 4HN  CONST_50  O28   C19  C9   C3    180.00   0.0  0
 4HN  CONST_51  O28   C19  C17  C4    180.00   0.0  0
 4HN  CONST_52  O27   C20  C14  C12     0.00   0.0  0
 4HN  CONST_53  O28   C19  C17  C15     0.00   0.0  0
 4HN  CONST_54  O27   C20  C14  C18   180.00   0.0  0
 4HN  CONST_55  O27   C20  C13  C21   180.00   0.0  0
 4HN  CONST_56  H9    C9   C3   C2    180.00   0.0  0
 4HN  CONST_57  H4    C4   C2   C3    180.00   0.0  0
 4HN  CONST_58  H3    C3   C2   C4    180.00   0.0  0
 4HN  CONST_59  H6    C6   C15  C5    180.00   0.0  0
 4HN  CONST_60  H5    C5   C15  C6    180.00   0.0  0
 4HN  CONST_61  H8    C8   C16  C7    180.00   0.0  0
 4HN  CONST_62  H7    C7   C16  C8    180.00   0.0  0
 4HN  CONST_63  H2    C2   C3   C9    180.00   0.0  0
 4HN  CONST_64  H12   C12  N25  C11   180.00   0.0  0
 4HN  CONST_65  H11   C11  N25  C12   180.00   0.0  0
 4HN  CONST_66  H10   C10  C18  C14   180.00   0.0  0
 4HN  Var_01    C22   C23  O28  C19  -177.91  30.0  1
 4HN  Var_02    H221  C22  C23  O28   178.54  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
 4HN  plan-1  C2   0.020
 4HN  plan-1  C3   0.020
 4HN  plan-1  C4   0.020
 4HN  plan-1  C9   0.020
 4HN  plan-1  C15  0.020
 4HN  plan-1  C17  0.020
 4HN  plan-1  C19  0.020
 4HN  plan-1  O28  0.020
 4HN  plan-1  H2   0.020
 4HN  plan-1  H3   0.020
 4HN  plan-1  H4   0.020
 4HN  plan-1  H9   0.020
 4HN  plan-2  C5   0.020
 4HN  plan-2  C6   0.020
 4HN  plan-2  C7   0.020
 4HN  plan-2  C8   0.020
 4HN  plan-2  C15  0.020
 4HN  plan-2  C16  0.020
 4HN  plan-2  C17  0.020
 4HN  plan-2  C21  0.020
 4HN  plan-2  H5   0.020
 4HN  plan-2  H7   0.020
 4HN  plan-2  H6   0.020
 4HN  plan-2  H8   0.020
 4HN  plan-3  C1   0.020
 4HN  plan-3  C10  0.020
 4HN  plan-3  C11  0.020
 4HN  plan-3  C12  0.020
 4HN  plan-3  C13  0.020
 4HN  plan-3  C14  0.020
 4HN  plan-3  C16  0.020
 4HN  plan-3  C18  0.020
 4HN  plan-3  C20  0.020
 4HN  plan-3  C21  0.020
 4HN  plan-3  N24  0.020
 4HN  plan-3  N25  0.020
 4HN  plan-3  N26  0.020
 4HN  plan-3  H10  0.020
 4HN  plan-3  H11  0.020
 4HN  plan-3  H12  0.020
 4HN  plan-3  O27  0.020

