# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 30 08:47:40 2020
#   Inital geometry file: a 152 line input string
#   Ligand name: ~{N}-(3-imidazol-1-ylpropyl)-4-[[3-(3-methoxyphenyl)phenyl]methyl]oxane-4-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cccc(c1)c2cccc(CC3(CCOCC3)C(=O)NCCCn4ccnc4)c2
#
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
 F8N  F8N  ~{N}-(3-imidazol-1-ylpropyl)-4-[[3-(3-methoxyphenyl)phenyl]methyl]oxane-4-carboxamide  ligand  63  32  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_F8N
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
 F8N  C1   C  CT    0  -0.250   0.5148   2.1159  -0.3417
 F8N  N4   N  NR5   0  -0.399   6.6894  -1.7422   0.3549
 F8N  C5   C  CR15  0   0.095   7.0052  -2.7872  -0.4386
 F8N  C6   C  CR6   0   0.109  -3.0322  -0.8695  -0.7367
 F8N  C8   C  CH2   0  -0.505  -0.0073   1.3004  -1.5520
 F8N  C11  C  CR16  0  -0.389  -2.2319   0.2195  -1.0837
 F8N  C13  C  CR16  0  -0.415  -5.1999  -1.4147   0.3550
 F8N  C14  C  CR6   0   0.179  -0.8506   0.1059  -1.2031
 F8N  C23  C  CR16  0  -0.337  -5.2026   0.1117  -1.4999
 F8N  C24  C  CR16  0  -0.328  -2.4180  -2.1010  -0.5083
 F8N  C25  C  CR16  0  -0.227  -1.0437  -2.2322  -0.6351
 F8N  C2   C  C     0   0.612   1.2692   1.1637   0.5967
 F8N  N16  N  NH1   0  -0.648   2.4509   0.7078   0.1497
 F8N  C27  C  CH2   0  -0.242   3.2330  -0.2605   0.8875
 F8N  C19  C  CH2   0  -0.489   4.5621  -0.5041   0.1926
 F8N  C18  C  CH2   0  -0.296   5.4079  -1.4938   0.9810
 F8N  C10  C  CR15  0  -0.108   7.7863  -0.9284   0.3967
 F8N  C9   C  CR15  0  -0.218   8.7271  -1.5416  -0.3806
 F8N  N3   N  N     0  -0.457   8.2279  -2.7033  -0.8978
 F8N  C21  C  CH2   0  -0.448   1.4195   3.2408  -0.8722
 F8N  C30  C  CH2   0  -0.180   1.8090   4.2181   0.2236
 F8N  O15  O  O2    0  -0.482   0.6766   4.7925   0.8349
 F8N  C29  C  CH2   0  -0.183  -0.1613   3.8161   1.4178
 F8N  C20  C  CH2   0  -0.436  -0.6421   2.7866   0.4055
 F8N  C28  C  CR16  0  -0.318  -0.2645  -1.1391  -0.9836
 F8N  C7   C  CR6   0   0.107  -4.4986  -0.7209  -0.6242
 F8N  C26  C  CR16  0  -0.226  -6.5753   0.2329  -1.3807
 F8N  C31  C  CR16  0  -0.395  -7.2805  -0.4602  -0.4030
 F8N  C17  C  CR6   0   0.406  -6.5852  -1.2927   0.4702
 F8N  O22  O  O2    0  -0.473  -7.1592  -2.0077   1.4567
 F8N  C32  C  CH3   0  -0.437  -8.5596  -1.9201   1.6276
 F8N  H1   H  HCR5  0   0.279   6.3025  -3.5826  -0.6408
 F8N  H2   H  HCH2  0   0.260  -0.5798   1.9903  -2.1770
 F8N  H3   H  HCH2  0   0.256   0.8450   0.9776  -2.1565
 F8N  H4   H  HCR6  0   0.246  -2.6952   1.1842  -1.2565
 F8N  H5   H  HCR6  0   0.259  -4.6741  -2.0482   1.0598
 F8N  H6   H  HCR6  0   0.251  -4.6818   0.6429  -2.2857
 F8N  H7   H  HCR6  0   0.253  -3.0161  -2.9689  -0.2609
 F8N  H8   H  HCR6  0   0.255  -0.5795  -3.1967  -0.4742
 F8N  H9   H  HNH1  0   0.402   2.7687   0.9619  -0.7709
 F8N  H10  H  HCH2  0   0.242   3.4081   0.1083   1.9014
 F8N  H11  H  HCH2  0   0.235   2.6816  -1.2015   0.9829
 F8N  H12  H  HCH2  0   0.251   4.3927  -0.8947  -0.8148
 F8N  H13  H  HCH2  0   0.252   5.1025   0.4405   0.0898
 F8N  H14  H  HCH2  0   0.269   4.8914  -2.4495   1.0723
 F8N  H15  H  HCH2  0   0.268   5.5853  -1.1257   1.9924
 F8N  H16  H  HCR5  0   0.288   7.8031  -0.0157   0.9693
 F8N  H17  H  HCR5  0   0.249   9.7331  -1.2095  -0.5865
 F8N  H18  H  HCH2  0   0.241   2.3235   2.8615  -1.3554
 F8N  H19  H  HCH2  0   0.246   0.8723   3.7807  -1.6513
 F8N  H20  H  HCH2  0   0.199   2.4423   3.7167   0.9714
 F8N  H21  H  HCH2  0   0.241   2.3971   5.0366  -0.1951
 F8N  H22  H  HCH2  0   0.203   0.3554   3.3175   2.2475
 F8N  H23  H  HCH2  0   0.236  -1.0163   4.3466   1.8406
 F8N  H24  H  HCH2  0   0.235  -1.2800   3.2834  -0.3329
 F8N  H25  H  HCH2  0   0.249  -1.2673   2.0532   0.9152
 F8N  H26  H  HCR6  0   0.248   0.8066  -1.2581  -1.0964
 F8N  H27  H  HCR6  0   0.260  -7.1189   0.8717  -2.0647
 F8N  H28  H  HCR6  0   0.279  -8.3531  -0.3380  -0.3390
 F8N  H29  H  HCH3  0   0.259  -8.8089  -2.5639   2.4675
 F8N  H30  H  HCH3  0   0.229  -8.8815  -0.9012   1.8580
 F8N  H31  H  HCH3  0   0.228  -9.1021  -2.2692   0.7453
 F8N  O12  O  O     0  -0.487   0.8175   0.8041   1.6745

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
 F8N  C26  C31  aromatic  1.391  0.020  1.391
 F8N  C26  C23  aromatic  1.383  0.020  1.383
 F8N  C31  C17  aromatic  1.392  0.020  1.392
 F8N  O22  C17  single    1.347  0.020  1.347
 F8N  O22  C32  single    1.414  0.020  1.414
 F8N  C17  C13  aromatic  1.395  0.020  1.395
 F8N  C23  C7   aromatic  1.399  0.020  1.399
 F8N  C24  C25  aromatic  1.386  0.020  1.386
 F8N  C24  C6   aromatic  1.395  0.020  1.395
 F8N  C13  C7   aromatic  1.390  0.020  1.390
 F8N  C7   C6   single    1.478  0.020  1.478
 F8N  C25  C28  aromatic  1.387  0.020  1.387
 F8N  C6   C11  aromatic  1.395  0.020  1.395
 F8N  N3   C5   aromatic  1.309  0.020  1.309
 F8N  N3   C9   aromatic  1.366  0.020  1.366
 F8N  C29  O15  single    1.413  0.020  1.413
 F8N  C29  C20  single    1.522  0.020  1.522
 F8N  C28  C14  aromatic  1.393  0.020  1.393
 F8N  C5   N4   aromatic  1.350  0.020  1.350
 F8N  C9   C10  aromatic  1.366  0.020  1.366
 F8N  O15  C30  single    1.409  0.020  1.409
 F8N  C11  C14  aromatic  1.391  0.020  1.391
 F8N  C20  C1   single    1.532  0.020  1.532
 F8N  C14  C8   single    1.503  0.020  1.503
 F8N  N4   C10  aromatic  1.366  0.020  1.366
 F8N  N4   C18  single    1.448  0.020  1.448
 F8N  C30  C21  single    1.519  0.020  1.519
 F8N  C18  C19  single    1.522  0.020  1.522
 F8N  C19  C27  single    1.519  0.020  1.519
 F8N  C1   C8   single    1.550  0.020  1.550
 F8N  C1   C21  single    1.538  0.020  1.538
 F8N  C1   C2   single    1.535  0.020  1.535
 F8N  N16  C2   single    1.343  0.020  1.343
 F8N  N16  C27  single    1.447  0.020  1.447
 F8N  C2   O12  double    1.223  0.020  1.223
 F8N  C5   H1   single    0.930  0.020  1.080
 F8N  C8   H2   single    0.970  0.020  1.090
 F8N  C8   H3   single    0.970  0.020  1.090
 F8N  C11  H4   single    0.930  0.020  1.080
 F8N  C13  H5   single    0.930  0.020  1.080
 F8N  C23  H6   single    0.930  0.020  1.080
 F8N  C24  H7   single    0.930  0.020  1.080
 F8N  C25  H8   single    0.930  0.020  1.080
 F8N  N16  H9   single    0.860  0.020  1.020
 F8N  C27  H10  single    0.970  0.020  1.090
 F8N  C27  H11  single    0.970  0.020  1.090
 F8N  C19  H12  single    0.970  0.020  1.090
 F8N  C19  H13  single    0.970  0.020  1.090
 F8N  C18  H14  single    0.970  0.020  1.090
 F8N  C18  H15  single    0.970  0.020  1.090
 F8N  C10  H16  single    0.930  0.020  1.080
 F8N  C9   H17  single    0.930  0.020  1.080
 F8N  C21  H18  single    0.970  0.020  1.090
 F8N  C21  H19  single    0.970  0.020  1.090
 F8N  C30  H20  single    0.970  0.020  1.090
 F8N  C30  H21  single    0.970  0.020  1.090
 F8N  C29  H22  single    0.970  0.020  1.090
 F8N  C29  H23  single    0.970  0.020  1.090
 F8N  C20  H24  single    0.970  0.020  1.090
 F8N  C20  H25  single    0.970  0.020  1.090
 F8N  C28  H26  single    0.930  0.020  1.080
 F8N  C26  H27  single    0.930  0.020  1.080
 F8N  C31  H28  single    0.930  0.020  1.080
 F8N  C32  H29  single    0.970  0.020  1.090
 F8N  C32  H30  single    0.970  0.020  1.090
 F8N  C32  H31  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
 F8N  C20  C1   C21  106.99  3.000
 F8N  C21  C1   C2   112.05  3.000
 F8N  C20  C1   C2   110.16  3.000
 F8N  C2   C1   C8   108.45  3.000
 F8N  C21  C1   C8   108.28  3.000
 F8N  C20  C1   C8   110.91  3.000
 F8N  C10  N4   C18  126.52  3.000
 F8N  C18  N4   C5   126.46  3.000
 F8N  C10  N4   C5   106.94  3.000
 F8N  H1   C5   N3   126.10  3.000
 F8N  H1   C5   N4   121.86  3.000
 F8N  N3   C5   N4   112.04  3.000
 F8N  C7   C6   C24  120.87  3.000
 F8N  C7   C6   C11  120.63  3.000
 F8N  C24  C6   C11  118.50  3.000
 F8N  H3   C8   H2   106.17  3.000
 F8N  H3   C8   C14  109.33  3.000
 F8N  H2   C8   C14  109.90  3.000
 F8N  H3   C8   C1   108.93  3.000
 F8N  H2   C8   C1   106.91  3.000
 F8N  C14  C8   C1   115.20  3.000
 F8N  H4   C11  C14  118.90  3.000
 F8N  H4   C11  C6   119.28  3.000
 F8N  C14  C11  C6   121.81  3.000
 F8N  H5   C13  C17  118.62  3.000
 F8N  H5   C13  C7   120.34  3.000
 F8N  C17  C13  C7   121.03  3.000
 F8N  C28  C14  C11  118.49  3.000
 F8N  C11  C14  C8   120.80  3.000
 F8N  C28  C14  C8   120.70  3.000
 F8N  H6   C23  C26  119.82  3.000
 F8N  H6   C23  C7   120.31  3.000
 F8N  C26  C23  C7   119.85  3.000
 F8N  H7   C24  C25  119.52  3.000
 F8N  H7   C24  C6   120.12  3.000
 F8N  C25  C24  C6   120.33  3.000
 F8N  H8   C25  C28  119.91  3.000
 F8N  H8   C25  C24  119.73  3.000
 F8N  C28  C25  C24  120.36  3.000
 F8N  N16  C2   O12  121.24  3.000
 F8N  O12  C2   C1   122.67  3.000
 F8N  N16  C2   C1   116.07  3.000
 F8N  H9   N16  C27  117.69  3.000
 F8N  H9   N16  C2   119.78  3.000
 F8N  C27  N16  C2   122.20  3.000
 F8N  H11  C27  H10  106.85  3.000
 F8N  H11  C27  C19  110.03  3.000
 F8N  H10  C27  C19  109.77  3.000
 F8N  H11  C27  N16  110.33  3.000
 F8N  H10  C27  N16  109.50  3.000
 F8N  C19  C27  N16  110.29  3.000
 F8N  H13  C19  H12  107.37  3.000
 F8N  H13  C19  C18  109.62  3.000
 F8N  H12  C19  C18  109.33  3.000
 F8N  H13  C19  C27  109.69  3.000
 F8N  H12  C19  C27  110.07  3.000
 F8N  C18  C19  C27  110.70  3.000
 F8N  H15  C18  H14  107.18  3.000
 F8N  H15  C18  C19  110.57  3.000
 F8N  H14  C18  C19  110.50  3.000
 F8N  H15  C18  N4   108.35  3.000
 F8N  H14  C18  N4   107.76  3.000
 F8N  C19  C18  N4   112.30  3.000
 F8N  H16  C10  C9   132.22  3.000
 F8N  H16  C10  N4   122.22  3.000
 F8N  C9   C10  N4   105.55  3.000
 F8N  H17  C9   N3   122.01  3.000
 F8N  H17  C9   C10  127.77  3.000
 F8N  N3   C9   C10  110.21  3.000
 F8N  C9   N3   C5   105.25  3.000
 F8N  H19  C21  H18  105.66  3.000
 F8N  H19  C21  C30  108.92  3.000
 F8N  H18  C21  C30  109.27  3.000
 F8N  H19  C21  C1   108.20  3.000
 F8N  H18  C21  C1   112.66  3.000
 F8N  C30  C21  C1   111.88  3.000
 F8N  H21  C30  H20  106.99  3.000
 F8N  H21  C30  O15  107.08  3.000
 F8N  H20  C30  O15  110.68  3.000
 F8N  H21  C30  C21  110.12  3.000
 F8N  H20  C30  C21  110.15  3.000
 F8N  O15  C30  C21  111.66  3.000
 F8N  C29  O15  C30  111.96  3.000
 F8N  H23  C29  H22  107.27  3.000
 F8N  H23  C29  C20  109.82  3.000
 F8N  H22  C29  C20  110.14  3.000
 F8N  H23  C29  O15  106.77  3.000
 F8N  H22  C29  O15  110.29  3.000
 F8N  C20  C29  O15  112.37  3.000
 F8N  H25  C20  H24  106.64  3.000
 F8N  H25  C20  C29  108.98  3.000
 F8N  H24  C20  C29  109.01  3.000
 F8N  H25  C20  C1   111.50  3.000
 F8N  H24  C20  C1   108.04  3.000
 F8N  C29  C20  C1   112.46  3.000
 F8N  H26  C28  C25  119.67  3.000
 F8N  H26  C28  C14  119.83  3.000
 F8N  C25  C28  C14  120.49  3.000
 F8N  C23  C7   C13  118.97  3.000
 F8N  C13  C7   C6   120.26  3.000
 F8N  C23  C7   C6   120.77  3.000
 F8N  H27  C26  C31  118.93  3.000
 F8N  H27  C26  C23  119.71  3.000
 F8N  C31  C26  C23  121.35  3.000
 F8N  H28  C31  C17  121.72  3.000
 F8N  H28  C31  C26  119.23  3.000
 F8N  C17  C31  C26  119.05  3.000
 F8N  O22  C17  C31  124.33  3.000
 F8N  O22  C17  C13  115.92  3.000
 F8N  C31  C17  C13  119.75  3.000
 F8N  C32  O22  C17  118.55  3.000
 F8N  H31  C32  H30  108.77  3.000
 F8N  H31  C32  H29  108.70  3.000
 F8N  H30  C32  H29  108.76  3.000
 F8N  H31  C32  O22  111.98  3.000
 F8N  H30  C32  O22  112.03  3.000
 F8N  H29  C32  O22  106.49  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
 F8N  CONST_01  C9   N3   C5   N4      0.00   0.0  0
 F8N  CONST_02  N3   C9   C10  N4      0.00   0.0  0
 F8N  CONST_03  C10  C9   N3   C5      0.00   0.0  0
 F8N  CONST_04  C9   C10  N4   C5      0.00   0.0  0
 F8N  CONST_05  C28  C25  C24  C6      0.00   0.0  0
 F8N  CONST_06  C26  C23  C7   C6    180.00   0.0  0
 F8N  CONST_07  C17  C13  C7   C6    180.00   0.0  0
 F8N  CONST_08  C28  C14  C11  C6      0.00   0.0  0
 F8N  CONST_09  C25  C24  C6   C11     0.00   0.0  0
 F8N  CONST_12  C25  C28  C14  C11     0.00   0.0  0
 F8N  CONST_13  C26  C31  C17  C13     0.00   0.0  0
 F8N  CONST_14  C26  C23  C7   C13     0.00   0.0  0
 F8N  CONST_16  C24  C25  C28  C14     0.00   0.0  0
 F8N  CONST_17  C24  C6   C11  C14     0.00   0.0  0
 F8N  CONST_18  C7   C6   C11  C14   180.00   0.0  0
 F8N  CONST_19  C17  C31  C26  C23     0.00   0.0  0
 F8N  CONST_20  C17  C13  C7   C23     0.00   0.0  0
 F8N  CONST_22  C7   C6   C24  C25   180.00   0.0  0
 F8N  CONST_23  N3   C5   N4   C10     0.00   0.0  0
 F8N  CONST_24  C31  C26  C23  C7      0.00   0.0  0
 F8N  CONST_25  C31  C17  C13  C7      0.00   0.0  0
 F8N  CONST_26  C8   C14  C11  C6    180.00   0.0  0
 F8N  CONST_27  C25  C28  C14  C8    180.00   0.0  0
 F8N  CONST_28  N3   C5   N4   C18   180.00   0.0  0
 F8N  CONST_29  C9   C10  N4   C18   180.00   0.0  0
 F8N  CONST_30  O22  C17  C13  C7    180.00   0.0  0
 F8N  CONST_31  O22  C17  C31  C26   180.00   0.0  0
 F8N  CONST_32  H17  C9   C10  N4    180.00   0.0  0
 F8N  CONST_33  H16  C10  N4   C5    180.00   0.0  0
 F8N  CONST_34  H8   C25  C24  C6    180.00   0.0  0
 F8N  CONST_35  H6   C23  C7   C6      0.00   0.0  0
 F8N  CONST_36  H5   C13  C7   C6      0.00   0.0  0
 F8N  CONST_37  H7   C24  C6   C11   180.00   0.0  0
 F8N  CONST_38  H26  C28  C14  C11   180.00   0.0  0
 F8N  CONST_39  H28  C31  C17  C13   180.00   0.0  0
 F8N  CONST_40  H4   C11  C6   C24   180.00   0.0  0
 F8N  CONST_41  H1   C5   N4   C10   180.00   0.0  0
 F8N  CONST_42  H27  C26  C23  C7    180.00   0.0  0
 F8N  CONST_43  C27  N16  C2   C1    180.00   0.0  0
 F8N  CONST_44  H9   N16  C2   C1      0.00   0.0  0
 F8N  CONST_45  C27  N16  C2   O12     0.00   0.0  0
 F8N  Var_01    O15  C29  C20  C1     54.85  30.0  1
 F8N  Var_02    O15  C30  C21  C1    -57.63  30.0  1
 F8N  Var_03    C20  C29  O15  C30   -58.14  30.0  1
 F8N  Var_04    C28  C14  C8   C1    -89.12  30.0  1
 F8N  Var_05    C19  C18  N4   C5    -97.99  30.0  2
 F8N  Var_06    C27  C19  C18  N4   -179.47  30.0  3
 F8N  Var_07    H29  C32  O22  C17  -179.84  30.0  3
 F8N  Var_08    C19  C27  N16  C2   -175.66  30.0  3
 F8N  Var_09    C18  C19  C27  N16   178.49  30.0  1

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 F8N  chir_01  C1  C20  C21  C2  negativ

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
 F8N  plan-1  N4   0.020
 F8N  plan-1  C5   0.020
 F8N  plan-1  C18  0.020
 F8N  plan-1  C10  0.020
 F8N  plan-1  C9   0.020
 F8N  plan-1  N3   0.020
 F8N  plan-1  H1   0.020
 F8N  plan-1  H16  0.020
 F8N  plan-1  H17  0.020
 F8N  plan-2  C6   0.020
 F8N  plan-2  C8   0.020
 F8N  plan-2  C11  0.020
 F8N  plan-2  C14  0.020
 F8N  plan-2  C24  0.020
 F8N  plan-2  C25  0.020
 F8N  plan-2  C28  0.020
 F8N  plan-2  C7   0.020
 F8N  plan-2  H4   0.020
 F8N  plan-2  H7   0.020
 F8N  plan-2  H8   0.020
 F8N  plan-2  H26  0.020
 F8N  plan-3  C6   0.020
 F8N  plan-3  C13  0.020
 F8N  plan-3  C23  0.020
 F8N  plan-3  C7   0.020
 F8N  plan-3  C26  0.020
 F8N  plan-3  C31  0.020
 F8N  plan-3  C17  0.020
 F8N  plan-3  O22  0.020
 F8N  plan-3  H5   0.020
 F8N  plan-3  H6   0.020
 F8N  plan-3  H27  0.020
 F8N  plan-3  H28  0.020
 F8N  plan-4  C1   0.020
 F8N  plan-4  C2   0.020
 F8N  plan-4  N16  0.020
 F8N  plan-4  C27  0.020
 F8N  plan-4  H9   0.020
 F8N  plan-4  O12  0.020

