# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 05:59:39 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: (1R,2R,3R)-N-hydroxy-2-[4-(1,3-oxazol-5-yl)phenyl]-3-phenylcyclopropanecarboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: ONC(=O)[C@@H]1[C@@H]([C@H]1c2ccc(cc2)c3ocnc3)c4ccccc4
#
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
 KEE  KEE  (1R,2R,3R)-N-hydroxy-2-[4-(1,3-oxazol-5-yl)phenyl]-3-phenylcyclopropanecarboxamide  ligand  40  24  .  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_KEE
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
 KEE  C1   C  C     0   0.579   2.8166  -1.7794   0.2644
 KEE  C2   C  CH1   0  -0.408   1.6615  -1.1445  -0.4301
 KEE  C3   C  CH1   0  -0.388   0.8266  -0.1616   0.3485
 KEE  C4   C  CH1   0  -0.252   1.7181   0.3302  -0.7450
 KEE  C5   C  CR6   0   0.250  -0.6496  -0.1298   0.2259
 KEE  C6   C  CR16  0  -0.306  -1.4161   0.2681   1.3179
 KEE  C7   C  CR16  0  -0.279  -2.7990   0.3247   1.2492
 KEE  C8   C  CR6   0  -0.013  -3.4612  -0.0214   0.0717
 KEE  C9   C  CR16  0  -0.299  -2.6960  -0.4209  -1.0274
 KEE  C10  C  CR16  0  -0.336  -1.3175  -0.4730  -0.9504
 KEE  C11  C  CR6   0   0.128   2.9327   1.1498  -0.4801
 KEE  C12  C  CR16  0  -0.295   4.0405   1.0176  -1.3145
 KEE  C13  C  CR16  0  -0.242   5.1708   1.7983  -1.1213
 KEE  C14  C  CR16  0  -0.270   5.2073   2.7276  -0.0886
 KEE  C15  C  CR16  0  -0.241   4.1056   2.8690   0.7439
 KEE  C16  C  CR16  0  -0.309   2.9757   2.0852   0.5472
 KEE  C17  C  CR5   0   0.358  -4.9072   0.0215  -0.0360
 KEE  O18  O  O     0  -0.402  -5.6342   0.4420   1.0304
 KEE  C19  C  CR15  0   0.162  -6.9121   0.3776   0.6447
 KEE  N20  N  N     0  -0.410  -7.0722  -0.0421  -0.5593
 KEE  C21  C  CR15  0  -0.240  -5.7960  -0.2780  -1.0171
 KEE  O22  O  O     0  -0.464   3.3263  -1.3356   1.2760
 KEE  N23  N  NH1   0  -0.393   3.2204  -2.9165  -0.3425
 KEE  O24  O  OH1   0  -0.542   4.3905  -3.5000   0.0413
 KEE  H2   H  HCH1  0   0.291   1.1519  -1.7630  -1.1614
 KEE  H23  H  HNH1  0   0.415   2.9293  -3.1447  -1.2827
 KEE  H3   H  HCH1  0   0.276   1.1898   0.0198   1.3547
 KEE  H4   H  HCH1  0   0.297   1.2138   0.5836  -1.6738
 KEE  H6   H  HCR6  0   0.258  -0.9253   0.5433   2.2435
 KEE  H10  H  HCR6  0   0.257  -0.7656  -0.7883  -1.8276
 KEE  H7   H  HCR6  0   0.259  -3.3516   0.6408   2.1239
 KEE  H9   H  HCR6  0   0.255  -3.1783  -0.6978  -1.9563
 KEE  H12  H  HCR6  0   0.248   4.0200   0.2954  -2.1226
 KEE  H16  H  HCR6  0   0.245   2.1211   2.2074   1.2017
 KEE  H13  H  HCR6  0   0.254   6.0247   1.6805  -1.7762
 KEE  H14  H  HCR6  0   0.254   6.0885   3.3372   0.0651
 KEE  H15  H  HCR6  0   0.255   4.1235   3.5919   1.5493
 KEE  H21  H  HCR5  0   0.275  -5.6038  -0.6449  -2.0124
 KEE  H19  H  HCR5  0   0.298  -7.6651   0.6749   1.3581
 KEE  H24  H  HOH1  0   0.479   4.1440  -4.2545   0.5912

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
 KEE  C1   C2   single    1.490  0.020  1.490
 KEE  C1   O22  double    1.217  0.020  1.217
 KEE  C1   N23  single    1.351  0.020  1.351
 KEE  C2   C3   single    1.506  0.020  1.506
 KEE  C2   C4   single    1.509  0.020  1.509
 KEE  C3   C4   single    1.494  0.020  1.494
 KEE  C3   C5   single    1.482  0.020  1.482
 KEE  C4   C11  single    1.489  0.020  1.489
 KEE  C5   C6   aromatic  1.392  0.020  1.392
 KEE  C5   C10  aromatic  1.396  0.020  1.396
 KEE  C6   C7   aromatic  1.386  0.020  1.386
 KEE  C7   C8   aromatic  1.395  0.020  1.395
 KEE  C8   C9   aromatic  1.398  0.020  1.398
 KEE  C8   C17  single    1.451  0.020  1.451
 KEE  C9   C10  aromatic  1.382  0.020  1.382
 KEE  C11  C12  aromatic  1.393  0.020  1.393
 KEE  C11  C16  aromatic  1.390  0.020  1.390
 KEE  C12  C13  aromatic  1.387  0.020  1.387
 KEE  C13  C14  aromatic  1.390  0.020  1.390
 KEE  C14  C15  aromatic  1.388  0.020  1.388
 KEE  C15  C16  aromatic  1.389  0.020  1.389
 KEE  C17  O18  aromatic  1.357  0.020  1.357
 KEE  C17  C21  aromatic  1.357  0.020  1.357
 KEE  O18  C19  aromatic  1.336  0.020  1.336
 KEE  C19  N20  aromatic  1.285  0.020  1.285
 KEE  N20  C21  aromatic  1.376  0.020  1.376
 KEE  N23  O24  single    1.363  0.020  1.363
 KEE  C2   H2   single    0.970  0.020  1.090
 KEE  N23  H23  single    0.890  0.020  1.040
 KEE  C3   H3   single    0.970  0.020  1.090
 KEE  C4   H4   single    0.970  0.020  1.090
 KEE  C6   H6   single    0.930  0.020  1.080
 KEE  C10  H10  single    0.930  0.020  1.080
 KEE  C7   H7   single    0.930  0.020  1.080
 KEE  C9   H9   single    0.930  0.020  1.080
 KEE  C12  H12  single    0.930  0.020  1.080
 KEE  C16  H16  single    0.930  0.020  1.080
 KEE  C13  H13  single    0.930  0.020  1.080
 KEE  C14  H14  single    0.930  0.020  1.080
 KEE  C15  H15  single    0.930  0.020  1.080
 KEE  C21  H21  single    0.930  0.020  1.080
 KEE  C19  H19  single    0.930  0.020  1.080
 KEE  O24  H24  single    0.850  0.020  0.980

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
 KEE  N23  C1   O22  123.74  3.000
 KEE  N23  C1   C2   112.40  3.000
 KEE  O22  C1   C2   123.85  3.000
 KEE  H2   C2   C4   115.73  3.000
 KEE  H2   C2   C3   117.39  3.000
 KEE  C4   C2   C3    59.40  3.000
 KEE  H2   C2   C1   115.81  3.000
 KEE  C4   C2   C1   118.99  3.000
 KEE  C3   C2   C1   117.83  3.000
 KEE  H3   C3   C5   113.99  3.000
 KEE  H3   C3   C4   115.08  3.000
 KEE  C5   C3   C4   121.80  3.000
 KEE  H3   C3   C2   113.76  3.000
 KEE  C5   C3   C2   121.57  3.000
 KEE  C4   C3   C2    60.38  3.000
 KEE  H4   C4   C11  113.72  3.000
 KEE  H4   C4   C3   115.17  3.000
 KEE  C11  C4   C3   122.53  3.000
 KEE  H4   C4   C2   112.88  3.000
 KEE  C11  C4   C2   122.10  3.000
 KEE  C3   C4   C2    60.21  3.000
 KEE  C10  C5   C6   117.90  3.000
 KEE  C10  C5   C3   122.77  3.000
 KEE  C6   C5   C3   119.33  3.000
 KEE  H6   C6   C7   118.96  3.000
 KEE  H6   C6   C5   119.57  3.000
 KEE  C7   C6   C5   121.48  3.000
 KEE  H7   C7   C8   120.84  3.000
 KEE  H7   C7   C6   118.79  3.000
 KEE  C8   C7   C6   120.37  3.000
 KEE  C17  C8   C9   119.73  3.000
 KEE  C17  C8   C7   121.92  3.000
 KEE  C9   C8   C7   118.36  3.000
 KEE  H9   C9   C10  118.86  3.000
 KEE  H9   C9   C8   120.26  3.000
 KEE  C10  C9   C8   120.88  3.000
 KEE  H10  C10  C9   118.30  3.000
 KEE  H10  C10  C5   120.69  3.000
 KEE  C9   C10  C5   121.01  3.000
 KEE  C16  C11  C12  118.81  3.000
 KEE  C16  C11  C4   121.82  3.000
 KEE  C12  C11  C4   119.33  3.000
 KEE  H12  C12  C13  119.62  3.000
 KEE  H12  C12  C11  119.65  3.000
 KEE  C13  C12  C11  120.73  3.000
 KEE  H13  C13  C14  120.11  3.000
 KEE  H13  C13  C12  119.81  3.000
 KEE  C14  C13  C12  120.08  3.000
 KEE  H14  C14  C15  120.23  3.000
 KEE  H14  C14  C13  120.23  3.000
 KEE  C15  C14  C13  119.54  3.000
 KEE  H15  C15  C16  119.71  3.000
 KEE  H15  C15  C14  120.08  3.000
 KEE  C16  C15  C14  120.21  3.000
 KEE  H16  C16  C15  119.50  3.000
 KEE  H16  C16  C11  119.86  3.000
 KEE  C15  C16  C11  120.63  3.000
 KEE  C21  C17  O18  106.59  3.000
 KEE  C21  C17  C8   134.42  3.000
 KEE  O18  C17  C8   118.99  3.000
 KEE  C19  O18  C17  105.69  3.000
 KEE  H19  C19  N20  128.50  3.000
 KEE  H19  C19  O18  117.59  3.000
 KEE  N20  C19  O18  113.91  3.000
 KEE  C21  N20  C19  104.60  3.000
 KEE  H21  C21  N20  122.06  3.000
 KEE  H21  C21  C17  128.73  3.000
 KEE  N20  C21  C17  109.21  3.000
 KEE  H23  N23  O24  114.38  3.000
 KEE  H23  N23  C1   121.47  3.000
 KEE  O24  N23  C1   119.38  3.000
 KEE  H24  O24  N23  106.01  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
 KEE  CONST_01  C8   C7   C6   C5      0.00   0.0  0
 KEE  CONST_02  C8   C9   C10  C5      0.00   0.0  0
 KEE  CONST_03  C9   C10  C5   C6      0.00   0.0  0
 KEE  CONST_04  C9   C8   C7   C6      0.00   0.0  0
 KEE  CONST_05  C17  C8   C7   C6    180.00   0.0  0
 KEE  CONST_06  C10  C5   C6   C7      0.00   0.0  0
 KEE  CONST_07  C10  C9   C8   C7      0.00   0.0  0
 KEE  CONST_08  O18  C17  C8   C7      0.00   0.0  0
 KEE  CONST_09  C21  C17  C8   C7    180.00   0.0  0
 KEE  CONST_10  C19  O18  C17  C8    180.00   0.0  0
 KEE  CONST_11  N20  C21  C17  C8    180.00   0.0  0
 KEE  CONST_12  O18  C17  C8   C9    180.00   0.0  0
 KEE  CONST_13  C21  C17  C8   C9      0.00   0.0  0
 KEE  CONST_14  C17  C8   C9   C10   180.00   0.0  0
 KEE  CONST_15  C14  C13  C12  C11     0.00   0.0  0
 KEE  CONST_16  C14  C15  C16  C11     0.00   0.0  0
 KEE  CONST_17  C15  C16  C11  C12     0.00   0.0  0
 KEE  CONST_18  C15  C14  C13  C12     0.00   0.0  0
 KEE  CONST_19  C16  C11  C12  C13     0.00   0.0  0
 KEE  CONST_20  C16  C15  C14  C13     0.00   0.0  0
 KEE  CONST_21  N20  C19  O18  C17     0.00   0.0  0
 KEE  CONST_22  C19  N20  C21  C17     0.00   0.0  0
 KEE  CONST_23  N20  C21  C17  O18     0.00   0.0  0
 KEE  CONST_24  C21  N20  C19  O18     0.00   0.0  0
 KEE  CONST_25  C21  C17  O18  C19     0.00   0.0  0
 KEE  CONST_26  C7   C6   C5   C3    180.00   0.0  0
 KEE  CONST_27  C9   C10  C5   C3    180.00   0.0  0
 KEE  CONST_28  C13  C12  C11  C4    180.00   0.0  0
 KEE  CONST_29  C15  C16  C11  C4    180.00   0.0  0
 KEE  CONST_30  H6   C6   C5   C3      0.00   0.0  0
 KEE  CONST_31  H10  C10  C5   C3      0.00   0.0  0
 KEE  CONST_32  H12  C12  C11  C4      0.00   0.0  0
 KEE  CONST_33  H16  C16  C11  C4      0.00   0.0  0
 KEE  CONST_34  H7   C7   C6   C5    180.00   0.0  0
 KEE  CONST_35  H9   C9   C10  C5    180.00   0.0  0
 KEE  CONST_36  H21  C21  C17  C8      0.00   0.0  0
 KEE  CONST_37  H13  C13  C12  C11   180.00   0.0  0
 KEE  CONST_38  H15  C15  C16  C11   180.00   0.0  0
 KEE  CONST_39  H14  C14  C13  C12   180.00   0.0  0
 KEE  CONST_40  H19  C19  O18  C17   180.00   0.0  0
 KEE  CONST_41  O24  N23  C1   C2    180.00   0.0  0
 KEE  CONST_43  O24  N23  C1   O22     0.00   0.0  0
 KEE  Var_01    C11  C4   C3   C2   -111.17  30.0  1
 KEE  Var_02    C6   C5   C3   C2    149.58  30.0  2
 KEE  Var_03    C12  C11  C4   C2     74.43  30.0  2
 KEE  Var_04    O22  C1   C2   C3    -18.74  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
 KEE  chir_01  C2  C1  C3  C4   both
 KEE  chir_02  C3  C5  C4  C2   both
 KEE  chir_03  C4  C2  C3  C11  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
 KEE  plan-1  C8   0.020
 KEE  plan-1  C17  0.020
 KEE  plan-1  O18  0.020
 KEE  plan-1  C19  0.020
 KEE  plan-1  N20  0.020
 KEE  plan-1  C21  0.020
 KEE  plan-1  H21  0.020
 KEE  plan-1  H19  0.020
 KEE  plan-2  C3   0.020
 KEE  plan-2  C5   0.020
 KEE  plan-2  C6   0.020
 KEE  plan-2  C7   0.020
 KEE  plan-2  C8   0.020
 KEE  plan-2  C9   0.020
 KEE  plan-2  C10  0.020
 KEE  plan-2  C17  0.020
 KEE  plan-2  H6   0.020
 KEE  plan-2  H10  0.020
 KEE  plan-2  H7   0.020
 KEE  plan-2  H9   0.020
 KEE  plan-3  C4   0.020
 KEE  plan-3  C11  0.020
 KEE  plan-3  C12  0.020
 KEE  plan-3  C13  0.020
 KEE  plan-3  C14  0.020
 KEE  plan-3  C15  0.020
 KEE  plan-3  C16  0.020
 KEE  plan-3  H12  0.020
 KEE  plan-3  H16  0.020
 KEE  plan-3  H13  0.020
 KEE  plan-3  H14  0.020
 KEE  plan-3  H15  0.020
 KEE  plan-4  C1   0.020
 KEE  plan-4  C2   0.020
 KEE  plan-4  O22  0.020
 KEE  plan-4  N23  0.020
 KEE  plan-4  O24  0.020
 KEE  plan-4  H23  0.020

