# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 30 07:02:46 2020
#   Inital geometry file: a 153 line input string
#   Ligand name: 4-[[4-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methyl-phenyl]methoxy]-2,5-bis(fluoranyl)phenyl]methylamino]-3-oxidanylidene-butanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1c(COc2cc(F)c(CNCC(=O)CC(O)=O)cc2F)cccc1c3ccc4OCCOc4c3
#
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
 8HW  8HW  '4-[[4-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methyl-phenyl]methoxy]-2,5-bis(fluoranyl)phenyl]methylamino]-3-oxidanylidene-butanoic acid'  ligand  61  36  .  2022-07-23  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8HW
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
 8HW  F1   F  F     0  -0.306   -1.8747   3.4081  -1.3226
 8HW  C19  C  CR6   0   0.469   -2.2859   2.4740  -0.4544
 8HW  C20  C  CR16  0  -0.427   -3.6180   2.3696  -0.1358
 8HW  C21  C  CR6   0  -0.126   -4.0661   1.4070   0.7675
 8HW  C22  C  CH2   0  -0.316   -5.5232   1.2670   1.0988
 8HW  N    N  NH1   0  -0.581   -6.0810   0.0907   0.4571
 8HW  C23  C  CH2   0  -0.355   -7.4730  -0.0910   0.7636
 8HW  C24  C  C     0   0.384   -8.0896  -1.2328   0.0036
 8HW  O3   O  O     0  -0.374   -7.5507  -1.7695  -0.9317
 8HW  C25  C  CH2   0  -0.659   -9.4557  -1.6685   0.4931
 8HW  C26  C  C     0   0.543  -10.2145  -2.4090  -0.5742
 8HW  O4   O  O     0  -0.422  -10.4446  -3.5885  -0.5712
 8HW  O5   O  OH1   0  -0.572  -10.6035  -1.5864  -1.5418
 8HW  C2   C  CR6   0   0.272   -1.3290   1.6261   0.1036
 8HW  C1   C  CR16  0  -0.519   -1.7598   0.6574   1.0015
 8HW  C    C  CR6   0   0.568   -3.1077   0.5696   1.3053
 8HW  F    F  F     0  -0.304   -3.4854  -0.3702   2.1824
 8HW  O    O  O2    0  -0.465   -0.0607   1.8237  -0.2780
 8HW  C3   C  CH2   0  -0.200    0.9532   1.0439   0.3078
 8HW  C4   C  CR6   0   0.038    2.2915   1.4852  -0.2210
 8HW  C5   C  CR6   0   0.043    3.4221   0.7247   0.1116
 8HW  C6   C  CH3   0  -0.752    3.2634  -0.4757   1.0034
 8HW  C7   C  CR6   0   0.059    4.6738   1.1185  -0.3794
 8HW  C16  C  CR16  0  -0.283    4.7793   2.2744  -1.1528
 8HW  C17  C  CR16  0  -0.222    3.6607   3.0254  -1.4599
 8HW  C18  C  CR16  0  -0.303    2.4142   2.6275  -1.0010
 8HW  C8   C  CR6   0   0.026    5.9074   0.3415  -0.1148
 8HW  C9   C  CR16  0  -0.380    6.0144  -0.9850  -0.5197
 8HW  C10  C  CR6   0   0.337    7.1774  -1.7078  -0.3027
 8HW  C11  C  CR6   0   0.309    8.2646  -1.1024   0.3343
 8HW  C14  C  CR16  0  -0.332    8.1686   0.2249   0.7258
 8HW  C15  C  CR16  0  -0.290    7.0060   0.9419   0.4975
 8HW  O2   O  O2    0  -0.472    7.2271  -2.9954  -0.7281
 8HW  C13  C  CH2   0  -0.208    8.5329  -3.5327  -0.7904
 8HW  C12  C  CH2   0  -0.207    9.3034  -3.1770   0.4608
 8HW  O1   O  O2    0  -0.463    9.4150  -1.7743   0.5813
 8HW  H1   H  HCR6  0   0.268   -4.3236   3.0515  -0.5941
 8HW  H2   H  HCH2  0   0.243   -5.6571   1.1685   2.1791
 8HW  H3   H  HCH2  0   0.219   -6.0402   2.1945   0.8117
 8HW  H4   H  HNH1  0   0.345   -5.9590   0.1678  -0.5452
 8HW  H6   H  HCH2  0   0.261   -7.5998  -0.2797   1.8355
 8HW  H7   H  HCH2  0   0.241   -8.1066   0.7903   0.5526
 8HW  H8   H  HCH2  0   0.314   -9.3091  -2.3225   1.3555
 8HW  H9   H  HCH2  0   0.291  -10.0275  -0.8061   0.8439
 8HW  H10  H  HOH1  0   0.457  -11.0701  -2.0870  -2.2239
 8HW  H11  H  HCR6  0   0.281   -1.0754  -0.0350   1.4713
 8HW  H12  H  HCH2  0   0.229    0.9286   1.1533   1.4008
 8HW  H13  H  HCH2  0   0.232    0.7923  -0.0188   0.0870
 8HW  H14  H  HCH3  0   0.241    2.8219  -1.3218   0.4717
 8HW  H15  H  HCH3  0   0.264    4.2124  -0.8142   1.4091
 8HW  H16  H  HCH3  0   0.235    2.6132  -0.2607   1.8525
 8HW  H17  H  HCR6  0   0.231    5.7493   2.5723  -1.5302
 8HW  H18  H  HCR6  0   0.235    3.7539   3.9162  -2.0663
 8HW  H19  H  HCR6  0   0.246    1.5434   3.2149  -1.2551
 8HW  H20  H  HCR6  0   0.246    5.1901  -1.4726  -1.0257
 8HW  H21  H  HCR6  0   0.250    9.0126   0.6901   1.2184
 8HW  H22  H  HCR6  0   0.234    6.9473   1.9728   0.8210
 8HW  H23  H  HCH2  0   0.234    8.4325  -4.6137  -0.8875
 8HW  H24  H  HCH2  0   0.228    9.0576  -3.1572  -1.6768
 8HW  H25  H  HCH2  0   0.227    8.8052  -3.5966   1.3425
 8HW  H26  H  HCH2  0   0.236   10.3160  -3.5776   0.4175

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
 8HW  C13  C12  single    1.512  0.020  1.512
 8HW  C13  O2   single    1.413  0.020  1.413
 8HW  C12  O1   single    1.412  0.020  1.412
 8HW  O2   C10  single    1.357  0.020  1.357
 8HW  O1   C11  single    1.355  0.020  1.355
 8HW  C10  C11  aromatic  1.398  0.020  1.398
 8HW  C10  C9   aromatic  1.386  0.020  1.386
 8HW  C11  C14  aromatic  1.387  0.020  1.387
 8HW  C9   C8   aromatic  1.391  0.020  1.391
 8HW  C14  C15  aromatic  1.385  0.020  1.385
 8HW  C8   C15  aromatic  1.394  0.020  1.394
 8HW  C8   C7   single    1.482  0.020  1.482
 8HW  C6   C5   single    1.504  0.020  1.504
 8HW  C7   C5   aromatic  1.401  0.020  1.401
 8HW  C7   C16  aromatic  1.395  0.020  1.395
 8HW  C5   C4   aromatic  1.403  0.020  1.403
 8HW  C16  C17  aromatic  1.382  0.020  1.382
 8HW  C4   C3   single    1.505  0.020  1.505
 8HW  C4   C18  aromatic  1.389  0.020  1.389
 8HW  C17  C18  aromatic  1.387  0.020  1.387
 8HW  C3   O    single    1.407  0.020  1.407
 8HW  F    C    single    1.340  0.020  1.340
 8HW  C1   C    aromatic  1.384  0.020  1.384
 8HW  C1   C2   aromatic  1.389  0.020  1.389
 8HW  O    C2   single    1.339  0.020  1.339
 8HW  C    C21  aromatic  1.382  0.020  1.382
 8HW  C2   C19  aromatic  1.395  0.020  1.395
 8HW  C21  C22  single    1.501  0.020  1.501
 8HW  C21  C20  aromatic  1.394  0.020  1.394
 8HW  C19  C20  aromatic  1.374  0.020  1.374
 8HW  C19  F1   single    1.340  0.020  1.340
 8HW  C22  N    single    1.451  0.020  1.451
 8HW  N    C23  single    1.437  0.020  1.437
 8HW  C23  C24  single    1.504  0.020  1.504
 8HW  O4   C26  double    1.202  0.020  1.202
 8HW  C24  O3   double    1.206  0.020  1.206
 8HW  C24  C25  single    1.515  0.020  1.515
 8HW  C26  O5   single    1.328  0.020  1.328
 8HW  C26  C25  single    1.504  0.020  1.504
 8HW  C20  H1   single    0.930  0.020  1.080
 8HW  C22  H2   single    0.970  0.020  1.090
 8HW  C22  H3   single    0.970  0.020  1.090
 8HW  N    H4   single    0.890  0.020  1.040
 8HW  C23  H6   single    0.970  0.020  1.090
 8HW  C23  H7   single    0.970  0.020  1.090
 8HW  C25  H8   single    0.970  0.020  1.090
 8HW  C25  H9   single    0.970  0.020  1.090
 8HW  O5   H10  single    0.850  0.020  0.980
 8HW  C1   H11  single    0.930  0.020  1.080
 8HW  C3   H12  single    0.970  0.020  1.090
 8HW  C3   H13  single    0.970  0.020  1.090
 8HW  C6   H14  single    0.970  0.020  1.090
 8HW  C6   H15  single    0.970  0.020  1.090
 8HW  C6   H16  single    0.970  0.020  1.090
 8HW  C16  H17  single    0.930  0.020  1.080
 8HW  C17  H18  single    0.930  0.020  1.080
 8HW  C18  H19  single    0.930  0.020  1.080
 8HW  C9   H20  single    0.930  0.020  1.080
 8HW  C14  H21  single    0.930  0.020  1.080
 8HW  C15  H22  single    0.930  0.020  1.080
 8HW  C13  H23  single    0.970  0.020  1.090
 8HW  C13  H24  single    0.970  0.020  1.090
 8HW  C12  H25  single    0.970  0.020  1.090
 8HW  C12  H26  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
 8HW  C2   C19  C20  121.75  3.000
 8HW  C20  C19  F1   120.06  3.000
 8HW  C2   C19  F1   118.19  3.000
 8HW  H1   C20  C21  119.97  3.000
 8HW  H1   C20  C19  119.06  3.000
 8HW  C21  C20  C19  120.97  3.000
 8HW  C    C21  C22  122.07  3.000
 8HW  C22  C21  C20  121.30  3.000
 8HW  C    C21  C20  116.60  3.000
 8HW  H3   C22  H2   106.05  3.000
 8HW  H3   C22  N    112.79  3.000
 8HW  H2   C22  N    108.47  3.000
 8HW  H3   C22  C21  108.66  3.000
 8HW  H2   C22  C21  110.21  3.000
 8HW  N    C22  C21  110.55  3.000
 8HW  H4   N    C23  109.72  3.000
 8HW  H4   N    C22  109.24  3.000
 8HW  C23  N    C22  112.36  3.000
 8HW  H7   C23  H6   104.93  3.000
 8HW  H7   C23  C24  105.89  3.000
 8HW  H6   C23  C24  108.43  3.000
 8HW  H7   C23  N    114.43  3.000
 8HW  H6   C23  N    110.03  3.000
 8HW  C24  C23  N    112.67  3.000
 8HW  C25  C24  O3   121.72  3.000
 8HW  C25  C24  C23  115.13  3.000
 8HW  O3   C24  C23  123.15  3.000
 8HW  H9   C25  H8   106.82  3.000
 8HW  H9   C25  C26  110.63  3.000
 8HW  H8   C25  C26  109.46  3.000
 8HW  H9   C25  C24  110.41  3.000
 8HW  H8   C25  C24  107.83  3.000
 8HW  C26  C25  C24  111.53  3.000
 8HW  O5   C26  O4   123.62  3.000
 8HW  O5   C26  C25  111.08  3.000
 8HW  O4   C26  C25  125.30  3.000
 8HW  H10  O5   C26  109.56  3.000
 8HW  O    C2   C1   125.50  3.000
 8HW  O    C2   C19  116.49  3.000
 8HW  C1   C2   C19  118.01  3.000
 8HW  H11  C1   C    118.71  3.000
 8HW  H11  C1   C2   122.08  3.000
 8HW  C    C1   C2   119.20  3.000
 8HW  F    C    C1   117.55  3.000
 8HW  C1   C    C21  123.47  3.000
 8HW  F    C    C21  118.97  3.000
 8HW  C3   O    C2   118.83  3.000
 8HW  H13  C3   H12  107.05  3.000
 8HW  H13  C3   C4   110.10  3.000
 8HW  H12  C3   C4   109.89  3.000
 8HW  H13  C3   O    110.32  3.000
 8HW  H12  C3   O    110.06  3.000
 8HW  C4   C3   O    109.39  3.000
 8HW  C18  C4   C5   120.52  3.000
 8HW  C18  C4   C3   121.14  3.000
 8HW  C5   C4   C3   118.33  3.000
 8HW  C7   C5   C6   121.77  3.000
 8HW  C7   C5   C4   118.99  3.000
 8HW  C6   C5   C4   119.23  3.000
 8HW  H16  C6   H15  106.95  3.000
 8HW  H16  C6   H14  106.90  3.000
 8HW  H15  C6   H14  107.07  3.000
 8HW  H16  C6   C5   111.54  3.000
 8HW  H15  C6   C5   112.21  3.000
 8HW  H14  C6   C5   111.85  3.000
 8HW  C8   C7   C16  118.08  3.000
 8HW  C16  C7   C5   119.66  3.000
 8HW  C8   C7   C5   122.26  3.000
 8HW  H17  C16  C17  119.88  3.000
 8HW  H17  C16  C7   119.28  3.000
 8HW  C17  C16  C7   120.82  3.000
 8HW  H18  C17  C18  119.96  3.000
 8HW  H18  C17  C16  120.16  3.000
 8HW  C18  C17  C16  119.88  3.000
 8HW  H19  C18  C17  119.38  3.000
 8HW  H19  C18  C4   120.53  3.000
 8HW  C17  C18  C4   120.10  3.000
 8HW  C15  C8   C9   118.56  3.000
 8HW  C15  C8   C7   120.59  3.000
 8HW  C9   C8   C7   120.81  3.000
 8HW  H20  C9   C10  118.48  3.000
 8HW  H20  C9   C8   120.45  3.000
 8HW  C10  C9   C8   121.07  3.000
 8HW  O2   C10  C11  121.68  3.000
 8HW  C11  C10  C9   119.87  3.000
 8HW  O2   C10  C9   118.45  3.000
 8HW  O1   C11  C14  118.81  3.000
 8HW  C14  C11  C10  119.28  3.000
 8HW  O1   C11  C10  121.91  3.000
 8HW  H21  C14  C15  120.48  3.000
 8HW  H21  C14  C11  119.06  3.000
 8HW  C15  C14  C11  120.46  3.000
 8HW  H22  C15  C14  119.31  3.000
 8HW  H22  C15  C8   119.93  3.000
 8HW  C14  C15  C8   120.74  3.000
 8HW  C13  O2   C10  114.10  3.000
 8HW  H24  C13  H23  108.16  3.000
 8HW  H24  C13  C12  110.16  3.000
 8HW  H23  C13  C12  110.74  3.000
 8HW  H24  C13  O2   110.34  3.000
 8HW  H23  C13  O2   107.20  3.000
 8HW  C12  C13  O2   110.18  3.000
 8HW  H26  C12  H25  108.27  3.000
 8HW  H26  C12  O1   107.16  3.000
 8HW  H25  C12  O1   110.33  3.000
 8HW  H26  C12  C13  110.74  3.000
 8HW  H25  C12  C13  110.12  3.000
 8HW  O1   C12  C13  110.16  3.000
 8HW  C12  O1   C11  114.20  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
 8HW  CONST_01  C    C1   C2   C19     0.00   0.0  0
 8HW  CONST_02  C    C21  C20  C19     0.00   0.0  0
 8HW  CONST_03  C1   C    C21  C20     0.00   0.0  0
 8HW  CONST_04  C1   C2   C19  C20     0.00   0.0  0
 8HW  CONST_05  C2   C1   C    C21     0.00   0.0  0
 8HW  CONST_06  C2   C19  C20  C21     0.00   0.0  0
 8HW  CONST_07  C8   C7   C5   C4    180.00   0.0  0
 8HW  CONST_08  C16  C7   C5   C4      0.00   0.0  0
 8HW  CONST_09  C16  C17  C18  C4      0.00   0.0  0
 8HW  CONST_12  C17  C16  C7   C5      0.00   0.0  0
 8HW  CONST_13  C17  C18  C4   C5      0.00   0.0  0
 8HW  CONST_14  C10  C9   C8   C7    180.00   0.0  0
 8HW  CONST_15  C14  C15  C8   C7    180.00   0.0  0
 8HW  CONST_16  C18  C4   C5   C7      0.00   0.0  0
 8HW  CONST_17  C18  C17  C16  C7      0.00   0.0  0
 8HW  CONST_20  C8   C7   C16  C17   180.00   0.0  0
 8HW  CONST_21  C11  C10  C9   C8      0.00   0.0  0
 8HW  CONST_22  C11  C14  C15  C8      0.00   0.0  0
 8HW  CONST_23  C14  C11  C10  C9      0.00   0.0  0
 8HW  CONST_24  C14  C15  C8   C9      0.00   0.0  0
 8HW  CONST_25  C15  C14  C11  C10     0.00   0.0  0
 8HW  CONST_26  C15  C8   C9   C10     0.00   0.0  0
 8HW  CONST_27  C1   C2   C19  F1    180.00   0.0  0
 8HW  CONST_28  C21  C20  C19  F1    180.00   0.0  0
 8HW  CONST_29  C22  C21  C20  C19   180.00   0.0  0
 8HW  CONST_30  F    C    C21  C20   180.00   0.0  0
 8HW  CONST_31  O    C2   C19  C20   180.00   0.0  0
 8HW  CONST_32  C1   C    C21  C22   180.00   0.0  0
 8HW  CONST_33  F    C    C1   C2    180.00   0.0  0
 8HW  CONST_34  O    C2   C1   C     180.00   0.0  0
 8HW  CONST_35  C7   C5   C4   C3    180.00   0.0  0
 8HW  CONST_36  C17  C18  C4   C3    180.00   0.0  0
 8HW  CONST_37  C8   C7   C5   C6      0.00   0.0  0
 8HW  CONST_38  C16  C7   C5   C6    180.00   0.0  0
 8HW  CONST_39  C18  C4   C5   C6    180.00   0.0  0
 8HW  CONST_40  H11  C1   C2   C19   180.00   0.0  0
 8HW  CONST_41  H1   C20  C19  C2    180.00   0.0  0
 8HW  CONST_42  H18  C17  C18  C4    180.00   0.0  0
 8HW  CONST_43  H17  C16  C7   C5    180.00   0.0  0
 8HW  CONST_44  H19  C18  C4   C5    180.00   0.0  0
 8HW  CONST_45  H20  C9   C8   C7      0.00   0.0  0
 8HW  CONST_46  H22  C15  C8   C7      0.00   0.0  0
 8HW  CONST_47  H21  C14  C15  C8    180.00   0.0  0
 8HW  CONST_48  H10  O5   C26  C25   180.00   0.0  0
 8HW  Var_01    C12  C13  O2   C10    45.09  30.0  1
 8HW  Var_02    C13  C12  O1   C11    44.75  30.0  1
 8HW  Var_03    O1   C12  C13  O2    -61.00  30.0  1
 8HW  Var_04    N    C22  C21  C20   105.53  30.0  2
 8HW  Var_05    C4   C3   O    C2   -177.23  30.0  1
 8HW  Var_06    C5   C4   C3   O    -172.21  30.0  1
 8HW  Var_07    H14  C6   C5   C4     75.48  30.0  2
 8HW  Var_08    C23  N    C22  C21   179.21  30.0  3
 8HW  Var_09    C24  C23  N    C22   174.72  30.0  3
 8HW  Var_10    O3   C24  C23  N     -12.91  30.0  3
 8HW  Var_11    C26  C25  C24  C23   158.43  30.0  3
 8HW  Var_12    O4   C26  C25  C24   108.71  30.0  2

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
 8HW  plan-1  F1   0.020
 8HW  plan-1  C19  0.020
 8HW  plan-1  C20  0.020
 8HW  plan-1  C21  0.020
 8HW  plan-1  C22  0.020
 8HW  plan-1  C2   0.020
 8HW  plan-1  C1   0.020
 8HW  plan-1  C    0.020
 8HW  plan-1  F    0.020
 8HW  plan-1  O    0.020
 8HW  plan-1  H1   0.020
 8HW  plan-1  H11  0.020
 8HW  plan-2  C3   0.020
 8HW  plan-2  C4   0.020
 8HW  plan-2  C5   0.020
 8HW  plan-2  C6   0.020
 8HW  plan-2  C7   0.020
 8HW  plan-2  C16  0.020
 8HW  plan-2  C17  0.020
 8HW  plan-2  C18  0.020
 8HW  plan-2  C8   0.020
 8HW  plan-2  H17  0.020
 8HW  plan-2  H18  0.020
 8HW  plan-2  H19  0.020
 8HW  plan-3  C7   0.020
 8HW  plan-3  C8   0.020
 8HW  plan-3  C9   0.020
 8HW  plan-3  C10  0.020
 8HW  plan-3  C11  0.020
 8HW  plan-3  C14  0.020
 8HW  plan-3  C15  0.020
 8HW  plan-3  O2   0.020
 8HW  plan-3  O1   0.020
 8HW  plan-3  H20  0.020
 8HW  plan-3  H21  0.020
 8HW  plan-3  H22  0.020
 8HW  plan-4  C23  0.020
 8HW  plan-4  C24  0.020
 8HW  plan-4  O3   0.020
 8HW  plan-4  C25  0.020
 8HW  plan-5  C25  0.020
 8HW  plan-5  C26  0.020
 8HW  plan-5  O4   0.020
 8HW  plan-5  O5   0.020
 8HW  plan-5  H10  0.020

