# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 10:47:40 2022
#   Inital geometry file: a 110 line input string
#   Ligand name: 1-(5-bromopyridin-2-yl)-3-[(1S,2S)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(=O)c1ccc(F)c([C@@H]2C[C@@H]2NC(=O)Nc3ccc(Br)cn3)c1O
#
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
 BFU  BFU  1-(5-bromopyridin-2-yl)-3-[(1S,2S)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea  ligand  43  26  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_BFU
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
 BFU  BR    BR  BR    0  -0.033   1.9071   0.1211  -6.4910
 BFU  C2    C   CR6   0  -0.203   1.2277  -0.1685  -4.7610
 BFU  C3    C   CR16  0  -0.044  -0.0957   0.1165  -4.4741
 BFU  N4    N   N     0  -0.418  -0.6283  -0.0778  -3.2756
 BFU  C5    C   CR6   0   0.526   0.1381  -0.5435  -2.3032
 BFU  C6    C   CR16  0  -0.390   1.4883  -0.8588  -2.5009
 BFU  C7    C   CR16  0  -0.113   2.0374  -0.6741  -3.7510
 BFU  N8    N   NH1   0  -0.774  -0.4136  -0.7721  -1.0564
 BFU  C9    C   C     0   0.734  -1.5074  -0.1266  -0.5026
 BFU  O10   O   O     0  -0.496  -2.0531   0.8352  -1.0058
 BFU  N11   N   NH1   0  -0.690  -1.8983  -0.6866   0.6684
 BFU  C12   C   CH1   0  -0.063  -2.9088  -0.1050   1.4824
 BFU  C13   C   CH2   0  -0.509  -3.2533  -0.7877   2.7555
 BFU  C14   C   CH1   0  -0.271  -2.5603   0.5440   2.8054
 BFU  C15   C   CR6   0  -0.219  -1.1481   0.6379   3.2542
 BFU  C16   C   CR6   0   0.562  -0.2130   1.3469   2.5246
 BFU  F     F   F     0  -0.296  -0.6213   1.9670   1.4148
 BFU  C18   C   CR16  0  -0.422   1.1246   1.4680   2.8727
 BFU  C19   C   CR16  0  -0.291   1.5407   0.8619   4.0352
 BFU  C20   C   CR6   0  -0.171   0.6496   0.1571   4.8515
 BFU  C21   C   CR6   0   0.359  -0.7067   0.0617   4.4571
 BFU  O22   O   OH1   0  -0.607  -1.6035  -0.5619   5.2078
 BFU  C23   C   C     0   0.447   1.0895  -0.4676   6.1055
 BFU  O24   O   O     0  -0.464   0.2868  -1.0681   6.8166
 BFU  C25   C   CH2   0  -0.577   2.5352  -0.3688   6.5129
 BFU  C26   C   CH3   0  -0.659   2.8581  -1.0518   7.8298
 BFU  H3    H   HCR6  0   0.280  -0.7602   0.5042  -5.2384
 BFU  H6    H   HCR6  0   0.289   2.0953  -1.2348  -1.6876
 BFU  H7    H   HCR6  0   0.295   3.0784  -0.9110  -3.9252
 BFU  HN8   H   HNH1  0   0.415   0.1332  -1.3578  -0.4443
 BFU  H11   H   HNH1  0   0.403  -1.5194  -1.5781   0.9454
 BFU  H12   H   HCH1  0   0.280  -3.7168   0.3524   0.9255
 BFU  H131  H   HCH2  0   0.264  -2.6805  -1.6671   3.0239
 BFU  H132  H   HCH2  0   0.269  -4.2939  -0.8375   3.0464
 BFU  H14   H   HCH1  0   0.288  -3.1825   1.3927   3.0741
 BFU  H18   H   HCR6  0   0.283   1.8062   2.0326   2.2520
 BFU  H19   H   HCR6  0   0.281   2.5805   0.9488   4.3172
 BFU  H22   H   HOH1  0   0.479  -1.1259  -0.9131   5.9989
 BFU  H251  H   HCH2  0   0.276   2.8054   0.6904   6.5591
 BFU  H252  H   HCH2  0   0.277   3.1462  -0.7865   5.7072
 BFU  H261  H   HCH3  0   0.239   3.9187  -0.9353   8.0491
 BFU  H262  H   HCH3  0   0.232   2.2987  -0.6192   8.6582
 BFU  H263  H   HCH3  0   0.232   2.6422  -2.1189   7.7975

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
 BFU  BR   C2    single    1.881  0.020  1.881
 BFU  C2   C3    aromatic  1.384  0.020  1.384
 BFU  C2   C7    aromatic  1.390  0.020  1.390
 BFU  C3   N4    aromatic  1.326  0.020  1.326
 BFU  C3   H3    single    0.930  0.020  1.080
 BFU  N4   C5    aromatic  1.323  0.020  1.323
 BFU  C5   C6    aromatic  1.401  0.020  1.401
 BFU  C5   N8    single    1.382  0.020  1.382
 BFU  C6   C7    aromatic  1.378  0.020  1.378
 BFU  C6   H6    single    0.930  0.020  1.080
 BFU  C7   H7    single    0.930  0.020  1.080
 BFU  N8   C9    single    1.386  0.020  1.386
 BFU  N8   HN8   single    0.860  0.020  1.020
 BFU  C9   O10   double    1.215  0.020  1.215
 BFU  C9   N11   single    1.356  0.020  1.356
 BFU  N11  C12   single    1.422  0.020  1.422
 BFU  N11  H11   single    0.860  0.020  1.020
 BFU  C12  C13   single    1.485  0.020  1.485
 BFU  C12  C14   single    1.514  0.020  1.514
 BFU  C12  H12   single    0.970  0.020  1.090
 BFU  C13  C14   single    1.502  0.020  1.502
 BFU  C13  H131  single    0.970  0.020  1.090
 BFU  C13  H132  single    0.970  0.020  1.090
 BFU  C14  C15   single    1.485  0.020  1.485
 BFU  C14  H14   single    0.970  0.020  1.090
 BFU  C15  C16   aromatic  1.382  0.020  1.382
 BFU  C15  C21   aromatic  1.405  0.020  1.405
 BFU  C16  F     single    1.335  0.020  1.335
 BFU  C16  C18   aromatic  1.387  0.020  1.387
 BFU  C18  C19   aromatic  1.375  0.020  1.375
 BFU  C18  H18   single    0.930  0.020  1.080
 BFU  C19  C20   aromatic  1.399  0.020  1.399
 BFU  C19  H19   single    0.930  0.020  1.080
 BFU  C20  C21   aromatic  1.416  0.020  1.416
 BFU  C20  C23   single    1.468  0.020  1.468
 BFU  C21  O22   single    1.325  0.020  1.325
 BFU  O22  H22   single    0.850  0.020  0.980
 BFU  C23  O24   double    1.229  0.020  1.229
 BFU  C23  C25   single    1.505  0.020  1.505
 BFU  C25  C26   single    1.518  0.020  1.518
 BFU  C25  H251  single    0.970  0.020  1.090
 BFU  C25  H252  single    0.970  0.020  1.090
 BFU  C26  H261  single    0.970  0.020  1.090
 BFU  C26  H262  single    0.970  0.020  1.090
 BFU  C26  H263  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
 BFU  C7    C2   C3    118.78  3.000
 BFU  C7    C2   BR    120.93  3.000
 BFU  C3    C2   BR    120.29  3.000
 BFU  H3    C3   N4    116.32  3.000
 BFU  H3    C3   C2    120.89  3.000
 BFU  N4    C3   C2    122.78  3.000
 BFU  C5    N4   C3    118.91  3.000
 BFU  N8    C5   C6    118.35  3.000
 BFU  N8    C5   N4    119.34  3.000
 BFU  C6    C5   N4    122.28  3.000
 BFU  H6    C6   C7    120.32  3.000
 BFU  H6    C6   C5    120.85  3.000
 BFU  C7    C6   C5    118.82  3.000
 BFU  H7    C7   C6    120.02  3.000
 BFU  H7    C7   C2    121.55  3.000
 BFU  C6    C7   C2    118.42  3.000
 BFU  HN8   N8   C9    117.13  3.000
 BFU  HN8   N8   C5    115.28  3.000
 BFU  C9    N8   C5    126.76  3.000
 BFU  N11   C9   O10   123.73  3.000
 BFU  N11   C9   N8    112.36  3.000
 BFU  O10   C9   N8    123.91  3.000
 BFU  H11   N11  C12   118.15  3.000
 BFU  H11   N11  C9    119.64  3.000
 BFU  C12   N11  C9    122.03  3.000
 BFU  H12   C12  C14   116.11  3.000
 BFU  H12   C12  C13   117.52  3.000
 BFU  C14   C12  C13    60.10  3.000
 BFU  H12   C12  N11   114.12  3.000
 BFU  C14   C12  N11   120.79  3.000
 BFU  C13   C12  N11   117.87  3.000
 BFU  H132  C13  H131  113.87  3.000
 BFU  H132  C13  C14   118.41  3.000
 BFU  H131  C13  C14   117.87  3.000
 BFU  H132  C13  C12   118.35  3.000
 BFU  H131  C13  C12   117.58  3.000
 BFU  C14   C13  C12    60.91  3.000
 BFU  H14   C14  C15   114.88  3.000
 BFU  H14   C14  C13   115.89  3.000
 BFU  C15   C14  C13   120.32  3.000
 BFU  H14   C14  C12   114.79  3.000
 BFU  C15   C14  C12   120.67  3.000
 BFU  C13   C14  C12    58.99  3.000
 BFU  C21   C15  C16   116.74  3.000
 BFU  C21   C15  C14   122.12  3.000
 BFU  C16   C15  C14   121.10  3.000
 BFU  C18   C16  F     117.57  3.000
 BFU  C18   C16  C15   124.38  3.000
 BFU  F     C16  C15   118.05  3.000
 BFU  H18   C18  C19   121.65  3.000
 BFU  H18   C18  C16   120.62  3.000
 BFU  C19   C18  C16   117.72  3.000
 BFU  H19   C19  C20   120.07  3.000
 BFU  H19   C19  C18   118.43  3.000
 BFU  C20   C19  C18   121.50  3.000
 BFU  C23   C20  C21   119.75  3.000
 BFU  C23   C20  C19   121.45  3.000
 BFU  C21   C20  C19   118.79  3.000
 BFU  O22   C21  C20   121.48  3.000
 BFU  O22   C21  C15   117.73  3.000
 BFU  C20   C21  C15   120.79  3.000
 BFU  H22   O22  C21   107.07  3.000
 BFU  C25   C23  O24   120.18  3.000
 BFU  C25   C23  C20   119.40  3.000
 BFU  O24   C23  C20   120.42  3.000
 BFU  H252  C25  H251  105.24  3.000
 BFU  H252  C25  C26   110.38  3.000
 BFU  H251  C25  C26   110.27  3.000
 BFU  H252  C25  C23   108.18  3.000
 BFU  H251  C25  C23   108.19  3.000
 BFU  C26   C25  C23   114.17  3.000
 BFU  H263  C26  H262  108.05  3.000
 BFU  H263  C26  H261  107.68  3.000
 BFU  H262  C26  H261  107.72  3.000
 BFU  H263  C26  C25   111.90  3.000
 BFU  H262  C26  C25   111.83  3.000
 BFU  H261  C26  C25   109.49  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
 BFU  CONST_01  C5    N4   C3   C2      0.00   0.0  0
 BFU  CONST_02  C5    C6   C7   C2      0.00   0.0  0
 BFU  CONST_03  C6    C7   C2   C3      0.00   0.0  0
 BFU  CONST_04  C6    C5   N4   C3      0.00   0.0  0
 BFU  CONST_05  C7    C2   C3   N4      0.00   0.0  0
 BFU  CONST_06  C7    C6   C5   N4      0.00   0.0  0
 BFU  CONST_07  C19   C18  C16  C15     0.00   0.0  0
 BFU  CONST_08  C19   C20  C21  C15     0.00   0.0  0
 BFU  CONST_09  C20   C21  C15  C16     0.00   0.0  0
 BFU  CONST_10  C20   C19  C18  C16     0.00   0.0  0
 BFU  CONST_11  C21   C15  C16  C18     0.00   0.0  0
 BFU  CONST_12  C21   C20  C19  C18     0.00   0.0  0
 BFU  CONST_13  C18   C16  C15  C14   180.00   0.0  0
 BFU  CONST_14  C20   C21  C15  C14   180.00   0.0  0
 BFU  CONST_15  N4    C3   C2   BR    180.00   0.0  0
 BFU  CONST_16  C6    C7   C2   BR    180.00   0.0  0
 BFU  CONST_17  N8    C5   N4   C3    180.00   0.0  0
 BFU  CONST_18  N8    C5   C6   C7    180.00   0.0  0
 BFU  CONST_19  F     C16  C15  C14     0.00   0.0  0
 BFU  CONST_20  O22   C21  C15  C14     0.00   0.0  0
 BFU  CONST_21  C23   C20  C21  C15   180.00   0.0  0
 BFU  CONST_22  O22   C21  C15  C16   180.00   0.0  0
 BFU  CONST_23  C21   C15  C16  F     180.00   0.0  0
 BFU  CONST_24  C19   C18  C16  F     180.00   0.0  0
 BFU  CONST_25  C23   C20  C19  C18   180.00   0.0  0
 BFU  CONST_26  O22   C21  C20  C19   180.00   0.0  0
 BFU  CONST_27  H6    C6   C7   C2    180.00   0.0  0
 BFU  CONST_28  H7    C7   C2   C3    180.00   0.0  0
 BFU  CONST_29  H3    C3   N4   C5    180.00   0.0  0
 BFU  CONST_30  H18   C18  C16  C15   180.00   0.0  0
 BFU  CONST_31  H19   C19  C18  C16   180.00   0.0  0
 BFU  CONST_35  O10   C9   N8   C5      0.00   0.0  0
 BFU  CONST_36  C12   N11  C9   O10     0.00   0.0  0
 BFU  CONST_37  N11   C9   N8   C5    180.00   0.0  0
 BFU  CONST_38  C12   N11  C9   N8    180.00   0.0  0
 BFU  CONST_39  H11   N11  C9   O10   180.00   0.0  0
 BFU  Var_01    C15   C14  C13  C12  -109.75  30.0  1
 BFU  Var_02    C16   C15  C14  C12    61.71  30.0  2
 BFU  Var_03    C14   C13  C12  N11   111.33  30.0  1
 BFU  Var_04    C13   C12  N11  C9   -179.26  30.0  3
 BFU  Var_05    O24   C23  C20  C19   179.08  30.0  2
 BFU  Var_06    C26   C25  C23  C20   179.82  30.0  3
 BFU  Var_07    H261  C26  C25  C23   179.92  30.0  3

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
 BFU  chir_01  C12  N11  C13  C14  both
 BFU  chir_02  C14  C12  C13  C15  both

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
 BFU  plan-1  BR   0.020
 BFU  plan-1  C2   0.020
 BFU  plan-1  C3   0.020
 BFU  plan-1  N4   0.020
 BFU  plan-1  C5   0.020
 BFU  plan-1  C6   0.020
 BFU  plan-1  C7   0.020
 BFU  plan-1  N8   0.020
 BFU  plan-1  H3   0.020
 BFU  plan-1  H6   0.020
 BFU  plan-1  H7   0.020
 BFU  plan-2  C14  0.020
 BFU  plan-2  C15  0.020
 BFU  plan-2  C16  0.020
 BFU  plan-2  F    0.020
 BFU  plan-2  C18  0.020
 BFU  plan-2  C19  0.020
 BFU  plan-2  C20  0.020
 BFU  plan-2  C21  0.020
 BFU  plan-2  O22  0.020
 BFU  plan-2  C23  0.020
 BFU  plan-2  H18  0.020
 BFU  plan-2  H19  0.020
 BFU  plan-3  C5   0.020
 BFU  plan-3  N8   0.020
 BFU  plan-3  C9   0.020
 BFU  plan-3  O10  0.020
 BFU  plan-3  N11  0.020
 BFU  plan-3  C12  0.020
 BFU  plan-3  HN8  0.020
 BFU  plan-3  H11  0.020
 BFU  plan-4  C20  0.020
 BFU  plan-4  C23  0.020
 BFU  plan-4  O24  0.020
 BFU  plan-4  C25  0.020

