# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 24 18:10:00 2022
#   Inital geometry file: a 111 line input string
#   Ligand name: (1R)-3-amino-1-{4-fluoro-3-[(2-propylpentyl)oxy]phenyl}propan-1-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC(CCC)COc1cc(ccc1F)[C@H](O)CCN
#
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
 W9A  W9A  (1R)-3-amino-1-{4-fluoro-3-[(2-propylpentyl)oxy]phenyl}propan-1-ol  ligand  49  21  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_W9A
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
 W9A  C1   C  CH2   0  -0.453  -37.2917  131.6866   8.8056
 W9A  C2   C  CH1   0   0.011  -36.5700  132.9864   9.1590
 W9A  C4   C  CR16  0  -0.321  -37.6058  133.9782  11.2296
 W9A  C6   C  CR6   0   0.431  -39.3412  135.6082  11.0927
 W9A  C7   C  CR6   0   0.273  -39.2856  135.5984   9.6972
 W9A  C8   C  CH2   0  -0.204  -40.1339  136.4566   7.6473
 W9A  C9   C  CH1   0  -0.267  -41.1556  137.4844   7.1888
 W9A  C10  C  CH2   0  -0.405  -42.5805  137.1567   7.6464
 W9A  C11  C  CH2   0  -0.429  -43.1012  135.7845   7.2348
 W9A  C12  C  CH3   0  -0.657  -44.5601  135.5891   7.6275
 W9A  C14  C  CH2   0  -0.426  -41.4814  140.0191   6.8957
 W9A  F    F  F     0  -0.314  -40.2271  136.4295  11.6806
 W9A  C5   C  CR16  0  -0.392  -38.5201  134.8175  11.8588
 W9A  O1   O  O2    0  -0.469  -40.1335  136.4226   9.0665
 W9A  C13  C  CH2   0  -0.398  -40.7300  138.8974   7.6029
 W9A  C15  C  CH3   0  -0.658  -40.9760  141.3955   7.3053
 W9A  C16  C  CR16  0  -0.427  -38.3686  134.7530   9.0853
 W9A  C3   C  CR6   0   0.069  -37.5294  133.9375   9.8462
 W9A  O    O  OH1   0  -0.650  -36.0324  133.5517   7.9870
 W9A  C    C  CH2   0  -0.286  -36.4152  130.4733   8.5216
 W9A  N    N  NH2   0  -0.787  -35.5838  130.6150   7.3366
 W9A  H1   H  HCH2  0   0.228  -37.9715  131.8734   7.9660
 W9A  H2   H  HCH2  0   0.242  -37.9310  131.4233   9.6517
 W9A  H3   H  HCH1  0   0.212  -35.7720  132.7439   9.8775
 W9A  H4   H  HCR6  0   0.253  -36.9514  133.3583  11.8300
 W9A  H5   H  HCH2  0   0.237  -40.3653  135.4633   7.2473
 W9A  H6   H  HCH2  0   0.236  -39.1406  136.7346   7.2751
 W9A  H7   H  HCH1  0   0.228  -41.1307  137.4319   6.0921
 W9A  H8   H  HCH2  0   0.212  -42.6504  137.2606   8.7343
 W9A  H9   H  HCH2  0   0.224  -43.2576  137.9106   7.2352
 W9A  H10  H  HCH2  0   0.212  -42.9913  135.6624   6.1527
 W9A  H11  H  HCH2  0   0.217  -42.5029  134.9926   7.6932
 W9A  H12  H  HCH3  0   0.225  -44.9246  134.6020   7.3413
 W9A  H13  H  HCH3  0   0.216  -44.6915  135.6893   8.7066
 W9A  H14  H  HCH3  0   0.216  -45.2018  136.3313   7.1491
 W9A  H15  H  HCH2  0   0.217  -42.5511  139.9523   7.1084
 W9A  H16  H  HCH2  0   0.211  -41.3777  139.8960   5.8132
 W9A  H17  H  HCR6  0   0.276  -38.5874  134.8605  12.9385
 W9A  H18  H  HCH2  0   0.215  -39.6608  139.0176   7.3961
 W9A  H19  H  HCH2  0   0.214  -40.8453  139.0132   8.6855
 W9A  H20  H  HCH3  0   0.225  -41.5183  142.1904   6.7921
 W9A  H21  H  HCH3  0   0.216  -41.0944  141.5539   8.3787
 W9A  H22  H  HCH3  0   0.215  -39.9163  141.5131   7.0712
 W9A  H23  H  HCR6  0   0.282  -38.2942  134.7225   8.0063
 W9A  H24  H  HOH1  0   0.446  -35.5610  134.3549   8.2304
 W9A  H25  H  HCH2  0   0.200  -37.0831  129.6010   8.4774
 W9A  H26  H  HCH2  0   0.211  -35.7606  130.3064   9.3829
 W9A  H27  H  HNH2  0   0.341  -35.1251  129.7325   7.1484
 W9A  H28  H  HNH2  0   0.333  -36.1752  130.7916   6.5337

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
 W9A  C14  C15  single    1.522  0.020  1.522
 W9A  C14  C13  single    1.524  0.020  1.524
 W9A  C13  C9   single    1.533  0.020  1.533
 W9A  N    C    single    1.455  0.020  1.455
 W9A  C9   C8   single    1.520  0.020  1.520
 W9A  C9   C10  single    1.532  0.020  1.532
 W9A  C8   O1   single    1.420  0.020  1.420
 W9A  C11  C10  single    1.524  0.020  1.524
 W9A  C11  C12  single    1.523  0.020  1.523
 W9A  C    C1   single    1.524  0.020  1.524
 W9A  C1   C2   single    1.528  0.020  1.528
 W9A  O1   C7   single    1.340  0.020  1.340
 W9A  O    C2   single    1.408  0.020  1.408
 W9A  C16  C7   aromatic  1.389  0.020  1.389
 W9A  C16  C3   aromatic  1.396  0.020  1.396
 W9A  C2   C3   single    1.516  0.020  1.516
 W9A  C7   C6   aromatic  1.397  0.020  1.397
 W9A  C3   C4   aromatic  1.386  0.020  1.386
 W9A  C6   F    single    1.343  0.020  1.343
 W9A  C6   C5   aromatic  1.373  0.020  1.373
 W9A  C4   C5   aromatic  1.391  0.020  1.391
 W9A  C1   H1   single    0.970  0.020  1.090
 W9A  C1   H2   single    0.970  0.020  1.090
 W9A  C2   H3   single    0.970  0.020  1.090
 W9A  C4   H4   single    0.930  0.020  1.080
 W9A  C8   H5   single    0.970  0.020  1.090
 W9A  C8   H6   single    0.970  0.020  1.090
 W9A  C9   H7   single    0.970  0.020  1.090
 W9A  C10  H8   single    0.970  0.020  1.090
 W9A  C10  H9   single    0.970  0.020  1.090
 W9A  C11  H10  single    0.970  0.020  1.090
 W9A  C11  H11  single    0.970  0.020  1.090
 W9A  C12  H12  single    0.970  0.020  1.090
 W9A  C12  H13  single    0.970  0.020  1.090
 W9A  C12  H14  single    0.970  0.020  1.090
 W9A  C14  H15  single    0.970  0.020  1.090
 W9A  C14  H16  single    0.970  0.020  1.090
 W9A  C5   H17  single    0.930  0.020  1.080
 W9A  C13  H18  single    0.970  0.020  1.090
 W9A  C13  H19  single    0.970  0.020  1.090
 W9A  C15  H20  single    0.970  0.020  1.090
 W9A  C15  H21  single    0.970  0.020  1.090
 W9A  C15  H22  single    0.970  0.020  1.090
 W9A  C16  H23  single    0.930  0.020  1.080
 W9A  O    H24  single    0.850  0.020  0.980
 W9A  C    H25  single    0.970  0.020  1.090
 W9A  C    H26  single    0.970  0.020  1.090
 W9A  N    H27  single    0.890  0.020  1.040
 W9A  N    H28  single    0.890  0.020  1.040

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
 W9A  H2   C1   H1   105.74  3.000
 W9A  H2   C1   C    106.80  3.000
 W9A  H1   C1   C    110.47  3.000
 W9A  H2   C1   C2   107.59  3.000
 W9A  H1   C1   C2   108.97  3.000
 W9A  C    C1   C2   116.67  3.000
 W9A  H3   C2   O    110.79  3.000
 W9A  H3   C2   C3   107.53  3.000
 W9A  O    C2   C3   111.54  3.000
 W9A  H3   C2   C1   107.81  3.000
 W9A  C3   C2   C1   109.86  3.000
 W9A  O    C2   C1   109.23  3.000
 W9A  H4   C4   C3   120.21  3.000
 W9A  H4   C4   C5   119.45  3.000
 W9A  C3   C4   C5   120.35  3.000
 W9A  C5   C6   F    120.14  3.000
 W9A  C5   C6   C7   121.97  3.000
 W9A  F    C6   C7   117.89  3.000
 W9A  C16  C7   O1   125.77  3.000
 W9A  C16  C7   C6   118.07  3.000
 W9A  O1   C7   C6   116.15  3.000
 W9A  H6   C8   H5   107.30  3.000
 W9A  H6   C8   O1   110.19  3.000
 W9A  H5   C8   O1   110.08  3.000
 W9A  H6   C8   C9   109.58  3.000
 W9A  H5   C8   C9   111.16  3.000
 W9A  O1   C8   C9   108.53  3.000
 W9A  H7   C9   C13  107.91  3.000
 W9A  H7   C9   C10  108.01  3.000
 W9A  C13  C9   C10  112.01  3.000
 W9A  H7   C9   C8   104.69  3.000
 W9A  C10  C9   C8   112.98  3.000
 W9A  C13  C9   C8   110.80  3.000
 W9A  H9   C10  H8   105.58  3.000
 W9A  H9   C10  C11  107.91  3.000
 W9A  H8   C10  C11  109.38  3.000
 W9A  H9   C10  C9   108.43  3.000
 W9A  H8   C10  C9   109.63  3.000
 W9A  C11  C10  C9   115.44  3.000
 W9A  H11  C11  H10  106.19  3.000
 W9A  H11  C11  C12  108.85  3.000
 W9A  H10  C11  C12  109.68  3.000
 W9A  H11  C11  C10  110.60  3.000
 W9A  H10  C11  C10  109.45  3.000
 W9A  C12  C11  C10  111.90  3.000
 W9A  H14  C12  H13  107.47  3.000
 W9A  H14  C12  H12  107.69  3.000
 W9A  H13  C12  H12  107.59  3.000
 W9A  H14  C12  C11  111.27  3.000
 W9A  H13  C12  C11  111.00  3.000
 W9A  H12  C12  C11  111.62  3.000
 W9A  H16  C14  H15  106.16  3.000
 W9A  H16  C14  C15  109.65  3.000
 W9A  H15  C14  C15  109.14  3.000
 W9A  H16  C14  C13  109.24  3.000
 W9A  H15  C14  C13  110.32  3.000
 W9A  C15  C14  C13  112.14  3.000
 W9A  H17  C5   C6   119.75  3.000
 W9A  H17  C5   C4   121.05  3.000
 W9A  C6   C5   C4   119.20  3.000
 W9A  C8   O1   C7   119.03  3.000
 W9A  H19  C13  H18  106.14  3.000
 W9A  H19  C13  C14  109.21  3.000
 W9A  H18  C13  C14  108.22  3.000
 W9A  H19  C13  C9   109.60  3.000
 W9A  H18  C13  C9   108.73  3.000
 W9A  C14  C13  C9   114.59  3.000
 W9A  H22  C15  H21  107.49  3.000
 W9A  H22  C15  H20  107.66  3.000
 W9A  H21  C15  H20  107.64  3.000
 W9A  H22  C15  C14  111.22  3.000
 W9A  H21  C15  C14  111.08  3.000
 W9A  H20  C15  C14  111.55  3.000
 W9A  H23  C16  C3   119.06  3.000
 W9A  H23  C16  C7   120.12  3.000
 W9A  C3   C16  C7   120.82  3.000
 W9A  C16  C3   C4   119.59  3.000
 W9A  C4   C3   C2   120.39  3.000
 W9A  C16  C3   C2   120.00  3.000
 W9A  H24  O    C2   108.15  3.000
 W9A  H26  C    H25  105.90  3.000
 W9A  H26  C    N    108.30  3.000
 W9A  H25  C    N    113.06  3.000
 W9A  H26  C    C1   108.59  3.000
 W9A  H25  C    C1   106.85  3.000
 W9A  N    C    C1   113.78  3.000
 W9A  H28  N    H27  105.62  3.000
 W9A  H28  N    C    109.21  3.000
 W9A  H27  N    C    109.00  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
 W9A  CONST_01  C7   C16  C3   C4      0.00   0.0  0
 W9A  CONST_02  C7   C6   C5   C4      0.00   0.0  0
 W9A  CONST_03  C3   C16  C7   C6      0.00   0.0  0
 W9A  CONST_04  C3   C4   C5   C6      0.00   0.0  0
 W9A  CONST_05  C16  C7   C6   C5      0.00   0.0  0
 W9A  CONST_06  C16  C3   C4   C5      0.00   0.0  0
 W9A  CONST_07  C7   C16  C3   C2    180.00   0.0  0
 W9A  CONST_08  C5   C4   C3   C2    180.00   0.0  0
 W9A  CONST_09  F    C6   C5   C4    180.00   0.0  0
 W9A  CONST_10  C16  C7   C6   F     180.00   0.0  0
 W9A  CONST_11  O1   C7   C6   C5    180.00   0.0  0
 W9A  CONST_12  C3   C16  C7   O1    180.00   0.0  0
 W9A  CONST_13  H23  C16  C3   C4    180.00   0.0  0
 W9A  CONST_14  H4   C4   C5   C6    180.00   0.0  0
 W9A  CONST_15  H17  C5   C6   C7    180.00   0.0  0
 W9A  Var_01    C16  C7   O1   C8      0.57  30.0  2
 W9A  Var_02    C9   C8   O1   C7   -178.80  30.0  2
 W9A  Var_03    N    C    C1   C2    -65.02  30.0  1
 W9A  Var_04    C14  C13  C9   C8    165.03  30.0  1
 W9A  Var_05    C11  C10  C9   C8    -55.96  30.0  3
 W9A  Var_06    C15  C14  C13  C9   -177.64  30.0  1
 W9A  Var_07    C12  C11  C10  C9   -175.17  30.0  1
 W9A  Var_08    O1   C8   C9   C10   -60.66  30.0  3
 W9A  Var_09    H27  N    C    C1   -172.79  30.0  3
 W9A  Var_10    H12  C12  C11  C10  -179.34  30.0  3
 W9A  Var_11    H20  C15  C14  C13   179.87  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
 W9A  chir_01  C2  C1  O  C3  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
 W9A  plan-1  C2   0.020
 W9A  plan-1  C4   0.020
 W9A  plan-1  C6   0.020
 W9A  plan-1  C7   0.020
 W9A  plan-1  F    0.020
 W9A  plan-1  C5   0.020
 W9A  plan-1  O1   0.020
 W9A  plan-1  C16  0.020
 W9A  plan-1  C3   0.020
 W9A  plan-1  H4   0.020
 W9A  plan-1  H17  0.020
 W9A  plan-1  H23  0.020

