# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 03:22:19 2020
#   Inital geometry file: a 122 line input string
#   Ligand name: 6-[1-(2,2-difluoro-3-hydroxypropyl)-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl]-2H-1,4-benzoxazin-3(4H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1nn(CC(F)(F)CO)c(c2ccc(F)cc2)c1c3ccc4OCC(=O)Nc4c3
#
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
 HFN  HFN  6-[1-(2,2-difluoro-3-hydroxypropyl)-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl]-2H-1,4-benzoxazin-3(4H)-one  ligand  48  30  .  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_HFN
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
 HFN  N1   N  NR5   0  -0.364  -2.2019  -1.1206  -0.7247
 HFN  N3   N  NR16  0  -0.722   4.6452  -1.5709   0.7899
 HFN  C4   C  CR16  0  -0.402   2.3358  -1.2868   0.0871
 HFN  C5   C  CR6   0   0.032   1.3786  -0.6014  -0.6615
 HFN  C6   C  CR16  0  -0.326   1.7818   0.5157  -1.3942
 HFN  C7   C  CR16  0  -0.338   3.0993   0.9474  -1.3702
 HFN  C8   C  CR66  0   0.343   3.6582  -0.8734   0.0941
 HFN  C10  C  C     0  -0.310   6.0499   0.3682   0.5478
 HFN  C13  C  CR16  0  -0.249  -0.7363   1.8453   0.5879
 HFN  C15  C  CR6   0   0.526  -1.4598   3.9304  -0.3007
 HFN  C17  C  CR16  0  -0.273  -1.9167   1.9285  -1.5015
 HFN  C21  C  CH2   0  -0.256  -5.4507  -0.4986   1.1759
 HFN  F3   F  F     0  -0.342  -3.2017  -0.1204   1.6701
 HFN  F2   F  F     0  -0.341  -3.8139  -2.1852   1.3697
 HFN  O3   O  OH1   0  -0.668  -6.2819  -1.3134   0.3943
 HFN  C19  C  CH2   0  -0.409  -3.5982  -0.8255  -0.5430
 HFN  N2   N  N     0  -0.287  -1.8155  -2.3940  -0.8290
 HFN  C3   C  CR5   0   0.262  -0.4993  -2.3810  -0.8041
 HFN  C18  C  CH3   0  -0.756   0.2815  -3.6429  -0.9403
 HFN  C1   C  CR5   0  -0.222  -0.0137  -1.0561  -0.6760
 HFN  C2   C  CR5   0   0.475  -1.1518  -0.2730  -0.6243
 HFN  C12  C  CR6   0  -0.016  -1.2848   1.1831  -0.5080
 HFN  C16  C  CR16  0  -0.402  -2.0139   3.3085  -1.4025
 HFN  C14  C  CR16  0  -0.400  -0.8166   3.2238   0.6981
 HFN  C9   C  CR66  0   0.318   4.0409   0.2498  -0.6348
 HFN  O1   O  O     0  -0.475   5.3430   0.6251  -0.6503
 HFN  C11  C  CR6   0   0.481   5.8594  -1.0448   1.0627
 HFN  O2   O  O     0  -0.457   6.7150  -1.6218   1.7044
 HFN  H1   H  HNR6  0   0.416   4.4251  -2.4842   1.1639
 HFN  H2   H  HCR6  0   0.265   2.0530  -2.1511   0.6753
 HFN  H3   H  HCR6  0   0.253   1.0634   1.0568  -1.9953
 HFN  H4   H  HCR6  0   0.272   3.4029   1.8148  -1.9422
 HFN  H5   H  H     0   0.284   7.1048   0.5338   0.3407
 HFN  H6   H  H     0   0.269   5.7448   1.0635   1.3410
 HFN  H7   H  HCR6  0   0.265  -0.2407   1.2793   1.3653
 HFN  H8   H  HCR6  0   0.277  -2.3265   1.4335  -2.3728
 HFN  H9   H  HCH2  0   0.241  -5.6512  -0.5980   2.2508
 HFN  H10  H  HCH2  0   0.232  -5.5454   0.5631   0.9220
 HFN  H11  H  HOH1  0   0.471  -7.1709  -0.9480   0.4159
 HFN  H12  H  HCH2  0   0.288  -3.8143   0.1755  -0.9135
 HFN  H13  H  HCH2  0   0.306  -4.1789  -1.5260  -1.1395
 HFN  H14  H  HCH3  0   0.248   1.1079  -3.5232  -1.6412
 HFN  H15  H  HCH3  0   0.250   0.7078  -3.9608   0.0125
 HFN  H16  H  HCH3  0   0.256  -0.3561  -4.4490  -1.2999
 HFN  H17  H  HCR6  0   0.285  -2.5042   3.8862  -2.1746
 HFN  H18  H  HCR6  0   0.284  -0.3900   3.7382   1.5489
 HFN  F1   F  F     0  -0.312  -1.5472   5.2647  -0.1970
 HFN  C20  C  CT    0   0.727  -4.0174  -0.9155   0.9166

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
 HFN  F2   C20  single    1.363  0.020  1.363
 HFN  O3   C21  single    1.402  0.020  1.402
 HFN  C20  C19  single    1.521  0.020  1.521
 HFN  C20  C21  single    1.515  0.020  1.515
 HFN  C20  F3   single    1.366  0.020  1.366
 HFN  C19  N1   single    1.439  0.020  1.439
 HFN  N1   N2   aromatic  1.335  0.020  1.335
 HFN  N1   C2   aromatic  1.353  0.020  1.353
 HFN  C17  C16  aromatic  1.387  0.020  1.387
 HFN  C17  C12  aromatic  1.393  0.020  1.393
 HFN  C16  C15  aromatic  1.381  0.020  1.381
 HFN  N2   C3   aromatic  1.316  0.020  1.316
 HFN  F1   C15  single    1.341  0.020  1.341
 HFN  C15  C14  aromatic  1.382  0.020  1.382
 HFN  C12  C2   single    1.467  0.020  1.467
 HFN  C12  C13  aromatic  1.393  0.020  1.393
 HFN  C2   C1   aromatic  1.383  0.020  1.383
 HFN  C3   C1   aromatic  1.417  0.020  1.417
 HFN  C3   C18  single    1.490  0.020  1.490
 HFN  C13  C14  aromatic  1.385  0.020  1.385
 HFN  C1   C5   single    1.465  0.020  1.465
 HFN  C5   C6   aromatic  1.395  0.020  1.395
 HFN  C5   C4   aromatic  1.395  0.020  1.395
 HFN  C6   C7   aromatic  1.387  0.020  1.387
 HFN  C4   C8   aromatic  1.386  0.020  1.386
 HFN  C7   C9   aromatic  1.384  0.020  1.384
 HFN  C8   C9   aromatic  1.393  0.020  1.393
 HFN  C8   N3   single    1.395  0.020  1.395
 HFN  C9   O1   single    1.355  0.020  1.355
 HFN  N3   C11  single    1.351  0.020  1.351
 HFN  O1   C10  single    1.415  0.020  1.415
 HFN  C11  C10  single    1.516  0.020  1.516
 HFN  C11  O2   double    1.215  0.020  1.215
 HFN  N3   H1   single    0.860  0.020  1.020
 HFN  C4   H2   single    0.930  0.020  1.080
 HFN  C6   H3   single    0.930  0.020  1.080
 HFN  C7   H4   single    0.930  0.020  1.080
 HFN  C10  H5   single    0.970  0.020  1.090
 HFN  C10  H6   single    0.970  0.020  1.090
 HFN  C13  H7   single    0.930  0.020  1.080
 HFN  C17  H8   single    0.930  0.020  1.080
 HFN  C21  H9   single    0.970  0.020  1.090
 HFN  C21  H10  single    0.970  0.020  1.090
 HFN  O3   H11  single    0.850  0.020  0.980
 HFN  C19  H12  single    0.970  0.020  1.090
 HFN  C19  H13  single    0.970  0.020  1.090
 HFN  C18  H14  single    0.970  0.020  1.090
 HFN  C18  H15  single    0.970  0.020  1.090
 HFN  C18  H16  single    0.970  0.020  1.090
 HFN  C16  H17  single    0.930  0.020  1.080
 HFN  C14  H18  single    0.930  0.020  1.080

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
 HFN  C2   N1   N2   112.26  3.000
 HFN  C2   N1   C19  127.97  3.000
 HFN  N2   N1   C19  119.11  3.000
 HFN  H1   N3   C11  118.21  3.000
 HFN  H1   N3   C8   118.82  3.000
 HFN  C11  N3   C8   122.83  3.000
 HFN  H2   C4   C8   118.98  3.000
 HFN  H2   C4   C5   120.29  3.000
 HFN  C8   C4   C5   120.73  3.000
 HFN  C1   C5   C6   121.20  3.000
 HFN  C6   C5   C4   118.47  3.000
 HFN  C1   C5   C4   120.33  3.000
 HFN  H3   C6   C7   119.01  3.000
 HFN  H3   C6   C5   120.02  3.000
 HFN  C7   C6   C5   120.98  3.000
 HFN  H4   C7   C9   119.60  3.000
 HFN  H4   C7   C6   120.45  3.000
 HFN  C9   C7   C6   119.93  3.000
 HFN  C9   C8   C4   120.02  3.000
 HFN  C9   C8   N3   118.04  3.000
 HFN  C4   C8   N3   121.93  3.000
 HFN  H6   C10  H5   108.10  3.000
 HFN  H6   C10  C11  108.06  3.000
 HFN  H5   C10  C11  109.18  3.000
 HFN  H6   C10  O1   110.97  3.000
 HFN  H5   C10  O1   107.20  3.000
 HFN  C11  C10  O1   113.21  3.000
 HFN  H7   C13  C14  119.34  3.000
 HFN  H7   C13  C12  119.80  3.000
 HFN  C14  C13  C12  120.85  3.000
 HFN  C14  C15  F1   118.88  3.000
 HFN  C14  C15  C16  122.21  3.000
 HFN  F1   C15  C16  118.91  3.000
 HFN  H8   C17  C16  119.07  3.000
 HFN  H8   C17  C12  120.05  3.000
 HFN  C16  C17  C12  120.87  3.000
 HFN  H10  C21  H9   107.39  3.000
 HFN  H10  C21  O3   112.50  3.000
 HFN  H9   C21  O3   112.64  3.000
 HFN  H10  C21  C20  107.98  3.000
 HFN  H9   C21  C20  108.38  3.000
 HFN  O3   C21  C20  107.79  3.000
 HFN  H11  O3   C21  108.35  3.000
 HFN  H13  C19  H12  107.42  3.000
 HFN  H13  C19  C20  109.92  3.000
 HFN  H12  C19  C20  109.04  3.000
 HFN  H13  C19  N1   108.46  3.000
 HFN  H12  C19  N1   109.77  3.000
 HFN  C20  C19  N1   112.12  3.000
 HFN  C3   N2   N1   106.17  3.000
 HFN  C1   C3   C18  128.35  3.000
 HFN  C18  C3   N2   120.92  3.000
 HFN  C1   C3   N2   110.70  3.000
 HFN  H16  C18  H15  107.55  3.000
 HFN  H16  C18  H14  108.23  3.000
 HFN  H15  C18  H14  107.30  3.000
 HFN  H16  C18  C3   110.50  3.000
 HFN  H15  C18  C3   111.81  3.000
 HFN  H14  C18  C3   111.28  3.000
 HFN  C2   C1   C3   104.53  3.000
 HFN  C3   C1   C5   128.10  3.000
 HFN  C2   C1   C5   127.32  3.000
 HFN  C12  C2   C1   129.79  3.000
 HFN  C1   C2   N1   106.33  3.000
 HFN  C12  C2   N1   123.88  3.000
 HFN  C2   C12  C17  121.04  3.000
 HFN  C2   C12  C13  119.90  3.000
 HFN  C17  C12  C13  119.02  3.000
 HFN  H17  C16  C17  120.81  3.000
 HFN  H17  C16  C15  120.71  3.000
 HFN  C17  C16  C15  118.48  3.000
 HFN  H18  C14  C15  120.58  3.000
 HFN  H18  C14  C13  120.86  3.000
 HFN  C15  C14  C13  118.57  3.000
 HFN  O1   C9   C8   119.56  3.000
 HFN  O1   C9   C7   120.55  3.000
 HFN  C8   C9   C7   119.86  3.000
 HFN  C9   O1   C10  114.84  3.000
 HFN  O2   C11  C10  122.24  3.000
 HFN  O2   C11  N3   123.68  3.000
 HFN  C10  C11  N3   114.03  3.000
 HFN  C19  C20  F2   109.44  3.000
 HFN  C19  C20  F3   109.28  3.000
 HFN  F2   C20  F3   105.64  3.000
 HFN  F3   C20  C21  108.08  3.000
 HFN  C19  C20  C21  114.12  3.000
 HFN  F2   C20  C21  109.92  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
 HFN  CONST_01  C1   C3   N2   N1      0.00   0.0  0
 HFN  CONST_04  C3   C1   C2   N1      0.00   0.0  0
 HFN  CONST_05  C5   C1   C2   N1    180.00   0.0  0
 HFN  CONST_08  C7   C6   C5   C4      0.00   0.0  0
 HFN  CONST_09  C7   C9   C8   C4      0.00   0.0  0
 HFN  CONST_10  C12  C2   C1   C5      0.00   0.0  0
 HFN  CONST_11  N2   C3   C1   C5    180.00   0.0  0
 HFN  CONST_12  C9   C7   C6   C5      0.00   0.0  0
 HFN  CONST_13  C9   C8   C4   C5      0.00   0.0  0
 HFN  CONST_16  C8   C4   C5   C6      0.00   0.0  0
 HFN  CONST_17  C8   C9   C7   C6      0.00   0.0  0
 HFN  CONST_18  C1   C5   C6   C7    180.00   0.0  0
 HFN  CONST_19  C1   C5   C4   C8    180.00   0.0  0
 HFN  CONST_20  C16  C17  C12  C13     0.00   0.0  0
 HFN  CONST_22  C16  C15  C14  C13     0.00   0.0  0
 HFN  CONST_23  C12  C17  C16  C15     0.00   0.0  0
 HFN  CONST_24  C12  C13  C14  C15     0.00   0.0  0
 HFN  CONST_25  C14  C15  C16  C17     0.00   0.0  0
 HFN  CONST_27  C14  C13  C12  C17     0.00   0.0  0
 HFN  CONST_28  C12  C2   N1   N2    180.00   0.0  0
 HFN  CONST_29  C1   C2   N1   N2      0.00   0.0  0
 HFN  CONST_30  C2   C1   C3   N2      0.00   0.0  0
 HFN  CONST_31  C2   N1   N2   C3      0.00   0.0  0
 HFN  CONST_32  C12  C2   C1   C3    180.00   0.0  0
 HFN  CONST_33  C16  C17  C12  C2    180.00   0.0  0
 HFN  CONST_34  C14  C13  C12  C2    180.00   0.0  0
 HFN  CONST_35  C10  C11  N3   C8      0.00   0.0  0
 HFN  CONST_36  C18  C3   N2   N1    180.00   0.0  0
 HFN  CONST_37  C18  C3   C1   C5      0.00   0.0  0
 HFN  CONST_38  F1   C15  C14  C13   180.00   0.0  0
 HFN  CONST_39  F1   C15  C16  C17   180.00   0.0  0
 HFN  CONST_40  C3   N2   N1   C19   180.00   0.0  0
 HFN  CONST_41  C12  C2   N1   C19     0.00   0.0  0
 HFN  CONST_42  C1   C2   N1   C19   180.00   0.0  0
 HFN  CONST_43  C2   C1   C3   C18   180.00   0.0  0
 HFN  CONST_44  O2   C11  N3   C8    180.00   0.0  0
 HFN  CONST_45  H2   C4   C8   N3      0.00   0.0  0
 HFN  CONST_46  H3   C6   C5   C4    180.00   0.0  0
 HFN  CONST_47  H4   C7   C6   C5    180.00   0.0  0
 HFN  CONST_48  H8   C17  C12  C13   180.00   0.0  0
 HFN  CONST_49  H7   C13  C14  C15   180.00   0.0  0
 HFN  CONST_50  H17  C16  C17  C12   180.00   0.0  0
 HFN  CONST_51  H18  C14  C13  C12   180.00   0.0  0
 HFN  CONST_52  H1   N3   C11  C10   180.00   0.0  0
 HFN  Var_01    O1   C10  C11  N3    -32.25  30.0  1
 HFN  Var_02    C11  N3   C8   C4   -164.80  30.0  1
 HFN  Var_03    C11  C10  O1   C9     48.89  30.0  1
 HFN  Var_04    N2   N1   C19  C20    83.98  30.0  2
 HFN  Var_05    H14  C18  C3   N2    134.50  30.0  2
 HFN  Var_06    F2   C20  C19  N1    -61.32  30.0  2
 HFN  Var_07    O3   C21  C20  F3    179.68  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
 HFN  plan-1  N1   0.020
 HFN  plan-1  C5   0.020
 HFN  plan-1  C19  0.020
 HFN  plan-1  N2   0.020
 HFN  plan-1  C3   0.020
 HFN  plan-1  C18  0.020
 HFN  plan-1  C1   0.020
 HFN  plan-1  C2   0.020
 HFN  plan-1  C12  0.020
 HFN  plan-2  C13  0.020
 HFN  plan-2  C15  0.020
 HFN  plan-2  C17  0.020
 HFN  plan-2  C2   0.020
 HFN  plan-2  C12  0.020
 HFN  plan-2  C16  0.020
 HFN  plan-2  C14  0.020
 HFN  plan-2  H7   0.020
 HFN  plan-2  H8   0.020
 HFN  plan-2  H17  0.020
 HFN  plan-2  H18  0.020
 HFN  plan-2  F1   0.020
 HFN  plan-3  N3   0.020
 HFN  plan-3  C4   0.020
 HFN  plan-3  C5   0.020
 HFN  plan-3  C6   0.020
 HFN  plan-3  C7   0.020
 HFN  plan-3  C8   0.020
 HFN  plan-3  C1   0.020
 HFN  plan-3  C9   0.020
 HFN  plan-3  O1   0.020
 HFN  plan-3  H2   0.020
 HFN  plan-3  H3   0.020
 HFN  plan-3  H4   0.020
 HFN  plan-4  N3   0.020
 HFN  plan-4  C8   0.020
 HFN  plan-4  C10  0.020
 HFN  plan-4  C11  0.020
 HFN  plan-4  O2   0.020
 HFN  plan-4  H1   0.020

