# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 23:22:03 2020
#   Inital geometry file: a 98 line input string
#   Ligand name: N-[6-(4-hydroxyphenyl)-1H-indazol-3-yl]butanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC(=O)Nc1n[nH]c2cc(ccc12)c3ccc(O)cc3
#
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
 OFI  OFI  N-[6-(4-hydroxyphenyl)-1H-indazol-3-yl]butanamide  ligand  39  22  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OFI
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
 OFI  C1    C  CR56  0  -0.158  -0.8134  -0.1145   0.2422
 OFI  C2    C  CR56  0   0.467  -0.0046  -1.2482   0.4136
 OFI  C3    C  CR5   0   0.447  -2.1405  -0.6137   0.3951
 OFI  C4    C  CR16  0  -0.296  -0.2207   1.1249  -0.0242
 OFI  C5    C  CR16  0  -0.367   1.3893  -1.1850   0.3406
 OFI  N6    N  NR15  0  -0.570  -0.8480  -2.2760   0.6430
 OFI  N7    N  N     0  -0.253  -2.1374  -1.8986   0.6349
 OFI  N8    N  NH1   0  -0.736  -3.2799   0.1696   0.3150
 OFI  C9    C  CR16  0  -0.327   1.1493   1.1896  -0.1041
 OFI  C10   C  CR6   0   0.084   1.9674   0.0440   0.0778
 OFI  C11   C  C     0   0.543  -4.5669  -0.2525   0.1541
 OFI  C12   C  CR6   0   0.065   3.4351   0.1669  -0.0168
 OFI  C13   C  CH2   0  -0.594  -5.5742   0.8766   0.1367
 OFI  O14   O  O     0  -0.455  -4.8713  -1.4232   0.0511
 OFI  C15   C  CR16  0  -0.297   4.0994   1.3014   0.4484
 OFI  C16   C  CR16  0  -0.296   4.2122  -0.8549  -0.5680
 OFI  C17   C  CH2   0  -0.421  -6.9485   0.4610  -0.3638
 OFI  C18   C  CR16  0  -0.369   5.4783   1.4138   0.3765
 OFI  C19   C  CR16  0  -0.323   5.5894  -0.7572  -0.6477
 OFI  C20   C  CH3   0  -0.664  -7.9291   1.6249  -0.3503
 OFI  C21   C  CR6   0   0.346   6.2356   0.3823  -0.1722
 OFI  O22   O  OH1   0  -0.629   7.5774   0.4325  -0.2679
 OFI  H4    H  HCR6  0   0.255  -0.8167   2.0154  -0.1810
 OFI  H5    H  HCR6  0   0.268   1.9939  -2.0671   0.5072
 OFI  HN8   H  HNH1  0   0.419  -3.1264   1.1650   0.3557
 OFI  H9    H  HCR6  0   0.255   1.6161   2.1372  -0.3384
 OFI  H13   H  HCH2  0   0.275  -5.6497   1.2696   1.1572
 OFI  H13A  H  HCH2  0   0.261  -5.1871   1.7033  -0.4671
 OFI  H15   H  HCR6  0   0.258   3.5391   2.1110   0.8987
 OFI  H16   H  HCR6  0   0.256   3.7327  -1.7410  -0.9645
 OFI  H17   H  HCH2  0   0.226  -6.8645   0.0632  -1.3777
 OFI  H17A  H  HCH2  0   0.227  -7.3356  -0.3511   0.2541
 OFI  H18   H  HCR6  0   0.273   5.9628   2.3044   0.7601
 OFI  H19   H  HCR6  0   0.266   6.1672  -1.5603  -1.0878
 OFI  H20   H  HCH3  0   0.220  -8.0719   2.0127   0.6598
 OFI  H20A  H  HCH3  0   0.220  -7.5790   2.4506  -0.9725
 OFI  H20B  H  HCH3  0   0.232  -8.9053   1.3198  -0.7276
 OFI  HO22  H  HOH1  0   0.475   7.9107   1.2630   0.0890
 OFI  HN6   H  HNR5  0   0.416  -0.6197  -3.2442   0.7916

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
 OFI  C1   C2    aromatic  1.403  0.020  1.403
 OFI  C1   C4    aromatic  1.399  0.020  1.399
 OFI  C1   C3    aromatic  1.426  0.020  1.426
 OFI  C5   C2    aromatic  1.397  0.020  1.397
 OFI  C2   N6    aromatic  1.349  0.020  1.349
 OFI  N7   C3    aromatic  1.307  0.020  1.307
 OFI  C3   N8    single    1.385  0.020  1.385
 OFI  C9   C4    aromatic  1.374  0.020  1.374
 OFI  C4   H4    single    0.930  0.020  1.080
 OFI  C5   C10   aromatic  1.383  0.020  1.383
 OFI  C5   H5    single    0.930  0.020  1.080
 OFI  N6   N7    aromatic  1.344  0.020  1.344
 OFI  N8   C11   single    1.364  0.020  1.364
 OFI  N8   HN8   single    0.860  0.020  1.020
 OFI  C10  C9    aromatic  1.419  0.020  1.419
 OFI  C9   H9    single    0.930  0.020  1.080
 OFI  C12  C10   single    1.476  0.020  1.476
 OFI  O14  C11   double    1.214  0.020  1.214
 OFI  C11  C13   single    1.513  0.020  1.513
 OFI  C15  C12   aromatic  1.395  0.020  1.395
 OFI  C16  C12   aromatic  1.397  0.020  1.397
 OFI  C13  C17   single    1.521  0.020  1.521
 OFI  C13  H13   single    0.970  0.020  1.090
 OFI  C13  H13A  single    0.970  0.020  1.090
 OFI  C18  C15   aromatic  1.385  0.020  1.385
 OFI  C15  H15   single    0.930  0.020  1.080
 OFI  C19  C16   aromatic  1.383  0.020  1.383
 OFI  C16  H16   single    0.930  0.020  1.080
 OFI  C17  C20   single    1.522  0.020  1.522
 OFI  C17  H17   single    0.970  0.020  1.090
 OFI  C17  H17A  single    0.970  0.020  1.090
 OFI  C21  C18   aromatic  1.392  0.020  1.392
 OFI  C18  H18   single    0.930  0.020  1.080
 OFI  C21  C19   aromatic  1.394  0.020  1.394
 OFI  C19  H19   single    0.930  0.020  1.080
 OFI  C20  H20   single    0.970  0.020  1.090
 OFI  C20  H20A  single    0.970  0.020  1.090
 OFI  C20  H20B  single    0.970  0.020  1.090
 OFI  O22  C21   single    1.346  0.020  1.346
 OFI  O22  HO22  single    0.850  0.020  0.980
 OFI  N6   HN6   single    0.860  0.020  1.020

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
 OFI  C4    C1   C3    136.43  3.000
 OFI  C3    C1   C2    103.92  3.000
 OFI  C4    C1   C2    119.65  3.000
 OFI  N6    C2   C5    131.83  3.000
 OFI  N6    C2   C1    106.02  3.000
 OFI  C5    C2   C1    122.15  3.000
 OFI  N8    C3   N7    124.64  3.000
 OFI  N8    C3   C1    124.15  3.000
 OFI  N7    C3   C1    111.20  3.000
 OFI  H4    C4   C9    120.11  3.000
 OFI  H4    C4   C1    121.52  3.000
 OFI  C9    C4   C1    118.37  3.000
 OFI  H5    C5   C10   121.32  3.000
 OFI  H5    C5   C2    120.82  3.000
 OFI  C10   C5   C2    117.84  3.000
 OFI  HN6   N6   N7    119.28  3.000
 OFI  HN6   N6   C2    128.06  3.000
 OFI  N7    N6   C2    112.64  3.000
 OFI  N6    N7   C3    106.23  3.000
 OFI  HN8   N8   C11   117.00  3.000
 OFI  HN8   N8   C3    115.52  3.000
 OFI  C11   N8   C3    127.45  3.000
 OFI  H9    C9   C10   119.07  3.000
 OFI  H9    C9   C4    118.95  3.000
 OFI  C10   C9   C4    121.96  3.000
 OFI  C12   C10  C9    119.85  3.000
 OFI  C12   C10  C5    120.11  3.000
 OFI  C9    C10  C5    120.03  3.000
 OFI  O14   C11  C13   123.48  3.000
 OFI  C13   C11  N8    113.49  3.000
 OFI  O14   C11  N8    123.03  3.000
 OFI  C16   C12  C15   117.50  3.000
 OFI  C16   C12  C10   121.17  3.000
 OFI  C15   C12  C10   121.33  3.000
 OFI  H13A  C13  H13   105.50  3.000
 OFI  H13A  C13  C17   110.16  3.000
 OFI  H13   C13  C17   110.01  3.000
 OFI  H13A  C13  C11   109.54  3.000
 OFI  H13   C13  C11   107.62  3.000
 OFI  C17   C13  C11   113.67  3.000
 OFI  H15   C15  C18   118.42  3.000
 OFI  H15   C15  C12   120.04  3.000
 OFI  C18   C15  C12   121.52  3.000
 OFI  H16   C16  C19   118.53  3.000
 OFI  H16   C16  C12   119.79  3.000
 OFI  C19   C16  C12   121.67  3.000
 OFI  H17A  C17  H17   106.37  3.000
 OFI  H17A  C17  C20   109.60  3.000
 OFI  H17   C17  C20   109.65  3.000
 OFI  H17A  C17  C13   109.73  3.000
 OFI  H17   C17  C13   109.60  3.000
 OFI  C20   C17  C13   111.74  3.000
 OFI  H18   C18  C21   120.33  3.000
 OFI  H18   C18  C15   119.55  3.000
 OFI  C21   C18  C15   120.11  3.000
 OFI  H19   C19  C21   119.85  3.000
 OFI  H19   C19  C16   120.16  3.000
 OFI  C21   C19  C16   119.99  3.000
 OFI  H20B  C20  H20A  107.56  3.000
 OFI  H20B  C20  H20   107.62  3.000
 OFI  H20A  C20  H20   107.50  3.000
 OFI  H20B  C20  C17   111.09  3.000
 OFI  H20A  C20  C17   111.52  3.000
 OFI  H20   C20  C17   111.36  3.000
 OFI  O22   C21  C19   117.93  3.000
 OFI  O22   C21  C18   122.86  3.000
 OFI  C19   C21  C18   119.21  3.000
 OFI  HO22  O22  C21   110.52  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
 OFI  CONST_01  C10  C5   C2   C1     0.00   0.0  0
 OFI  CONST_02  N7   N6   C2   C1     0.00   0.0  0
 OFI  CONST_03  C10  C9   C4   C1     0.00   0.0  0
 OFI  CONST_04  N6   N7   C3   C1     0.00   0.0  0
 OFI  CONST_05  C9   C4   C1   C2     0.00   0.0  0
 OFI  CONST_06  N7   C3   C1   C2     0.00   0.0  0
 OFI  CONST_07  C9   C10  C5   C2     0.00   0.0  0
 OFI  CONST_08  C12  C10  C5   C2   180.00   0.0  0
 OFI  CONST_09  C3   N7   N6   C2     0.00   0.0  0
 OFI  CONST_10  C5   C2   C1   C3   180.00   0.0  0
 OFI  CONST_11  N6   C2   C1   C3     0.00   0.0  0
 OFI  CONST_12  C9   C4   C1   C3   180.00   0.0  0
 OFI  CONST_13  C5   C2   C1   C4     0.00   0.0  0
 OFI  CONST_14  N6   C2   C1   C4   180.00   0.0  0
 OFI  CONST_15  N7   C3   C1   C4   180.00   0.0  0
 OFI  CONST_16  C5   C10  C9   C4     0.00   0.0  0
 OFI  CONST_17  C12  C10  C9   C4   180.00   0.0  0
 OFI  CONST_18  N7   N6   C2   C5   180.00   0.0  0
 OFI  CONST_21  C10  C5   C2   N6   180.00   0.0  0
 OFI  CONST_24  C18  C15  C12  C10  180.00   0.0  0
 OFI  CONST_25  C19  C16  C12  C10  180.00   0.0  0
 OFI  CONST_26  C21  C18  C15  C12    0.00   0.0  0
 OFI  CONST_27  C21  C19  C16  C12    0.00   0.0  0
 OFI  CONST_28  C19  C16  C12  C15    0.00   0.0  0
 OFI  CONST_29  C19  C21  C18  C15    0.00   0.0  0
 OFI  CONST_30  C18  C15  C12  C16    0.00   0.0  0
 OFI  CONST_31  C18  C21  C19  C16    0.00   0.0  0
 OFI  CONST_32  N8   C3   C1   C2   180.00   0.0  0
 OFI  CONST_33  N8   C3   C1   C4     0.00   0.0  0
 OFI  CONST_34  N8   C3   N7   N6   180.00   0.0  0
 OFI  CONST_35  O22  C21  C18  C15  180.00   0.0  0
 OFI  CONST_36  O22  C21  C19  C16  180.00   0.0  0
 OFI  CONST_37  H5   C5   C2   C1   180.00   0.0  0
 OFI  CONST_38  HN6  N6   C2   C1   180.00   0.0  0
 OFI  CONST_39  H9   C9   C4   C1   180.00   0.0  0
 OFI  CONST_40  H4   C4   C1   C2   180.00   0.0  0
 OFI  CONST_41  H15  C15  C12  C10    0.00   0.0  0
 OFI  CONST_42  H16  C16  C12  C10    0.00   0.0  0
 OFI  CONST_43  H18  C18  C15  C12  180.00   0.0  0
 OFI  CONST_44  H19  C19  C16  C12  180.00   0.0  0
 OFI  CONST_47  HN8  N8   C3   C1     0.00   0.0  0
 OFI  CONST_48  O14  C11  N8   C3     0.00   0.0  0
 OFI  CONST_49  C13  C11  N8   C3   180.00   0.0  0
 OFI  Var_01    C17  C13  C11  N8   166.35  30.0  3
 OFI  Var_02    C20  C17  C13  C11  179.45  30.0  3
 OFI  Var_03    H20  C20  C17  C13  -61.07  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
 OFI  plan-1  C10  0.020
 OFI  plan-1  C12  0.020
 OFI  plan-1  C15  0.020
 OFI  plan-1  C16  0.020
 OFI  plan-1  C18  0.020
 OFI  plan-1  C19  0.020
 OFI  plan-1  C21  0.020
 OFI  plan-1  O22  0.020
 OFI  plan-1  H15  0.020
 OFI  plan-1  H16  0.020
 OFI  plan-1  H18  0.020
 OFI  plan-1  H19  0.020
 OFI  plan-2  C1   0.020
 OFI  plan-2  C2   0.020
 OFI  plan-2  C3   0.020
 OFI  plan-2  C4   0.020
 OFI  plan-2  C5   0.020
 OFI  plan-2  N6   0.020
 OFI  plan-2  N7   0.020
 OFI  plan-2  N8   0.020
 OFI  plan-2  C9   0.020
 OFI  plan-2  C10  0.020
 OFI  plan-2  C12  0.020
 OFI  plan-2  H4   0.020
 OFI  plan-2  H5   0.020
 OFI  plan-2  H9   0.020
 OFI  plan-2  HN6  0.020
 OFI  plan-3  C3   0.020
 OFI  plan-3  N8   0.020
 OFI  plan-3  C11  0.020
 OFI  plan-3  C13  0.020
 OFI  plan-3  O14  0.020
 OFI  plan-3  HN8  0.020

