# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 15:25:10 2022
#   Inital geometry file: a 101 line input string
#   Ligand name: (5~{a}~{S},6~{R},9~{S},9~{a}~{S})-9-methyl-9-oxidanyl-1-oxidanylidene-6-propan-2-yl-3,5~{a},6,7,8,9~{a}-hexahydro-2-benzoxepine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@H]1CC[C@](C)(O)[C@@H]2[C@@H]1C=C(COC2=O)C(O)=O
#
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
 F4F  F4F  '(5~{a}~{S},6~{R},9~{S},9~{a}~{S})-9-methyl-9-oxidanyl-1-oxidanylidene-6-propan-2-yl-3,5~{a},6,7,8,9~{a}-hexahydro-2-benzoxepine-4-carboxylic acid'  ligand  41  20  .  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_F4F
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
 F4F  C11  C  CH1    0  -0.477  -14.9485  6.4756  -24.4365
 F4F  C12  C  CT     0   0.265  -13.6582  7.0559  -23.8131
 F4F  C13  C  CH3    0  -0.683  -12.8281  7.9389  -24.7402
 F4F  C15  C  CH2    0  -0.455  -12.8219  5.8586  -23.3549
 F4F  C16  C  CH2    0  -0.451  -12.5102  4.8900  -24.4878
 F4F  C17  C  CH1    0  -0.188  -13.7760  4.3592  -25.1609
 F4F  C18  C  CH1    0  -0.238  -13.4801  3.3288  -26.2710
 F4F  C19  C  CH3    0  -0.661  -12.6617  2.1527  -25.7421
 F4F  C20  C  CH3    0  -0.668  -12.8148  3.9252  -27.5088
 F4F  C02  C  C      0   0.599  -15.9695  7.5321  -24.8028
 F4F  C04  C  CH2    0  -0.286  -17.6339  5.7970  -24.7065
 F4F  C05  C  C      0  -0.166  -17.1790  5.0560  -25.9316
 F4F  C06  C  C      0   0.406  -18.2530  4.3788  -26.7912
 F4F  C09  C  C1     0  -0.180  -15.9017  5.0134  -26.3137
 F4F  C10  C  CH1    0  -0.266  -14.6730  5.5346  -25.6289
 F4F  O01  O  O      0  -0.422  -15.7184  8.6665  -25.1196
 F4F  O03  O  O2     0  -0.437  -17.2538  7.1786  -24.7587
 F4F  O07  O  O      0  -0.586  -17.8816  3.8349  -27.8480
 F4F  O08  O  OC    -1  -0.593  -19.4168  4.4246  -26.3444
 F4F  O14  O  OH1    0  -0.673  -13.9994  7.8684  -22.7027
 F4F  H1   H  HCH1   0   0.271  -15.3874  5.8567  -23.6438
 F4F  H2   H  HCH3   0   0.228  -11.8697  8.1618  -24.2674
 F4F  H3   H  HCH3   0   0.229  -12.6108  7.4511  -25.6889
 F4F  H4   H  HCH3   0   0.250  -13.3267  8.8785  -24.9592
 F4F  H5   H  HCH2   0   0.224  -13.3684  5.3191  -22.5708
 F4F  H6   H  HCH2   0   0.238  -11.8951  6.2191  -22.8999
 F4F  H7   H  HCH2   0   0.245  -11.9355  4.0564  -24.0808
 F4F  H8   H  HCH2   0   0.227  -11.8603  5.3730  -25.2228
 F4F  H9   H  HCH1   0   0.220  -14.3511  3.8234  -24.3919
 F4F  H10  H  HCH1   0   0.228  -14.4436  2.9141  -26.5838
 F4F  H11  H  HCH3   0   0.223  -13.0893  1.7476  -24.8225
 F4F  H12  H  HCH3   0   0.229  -12.6372  1.3466  -26.4771
 F4F  H13  H  HCH3   0   0.218  -11.6274  2.4310  -25.5341
 F4F  H14  H  HCH3   0   0.229  -13.4277  4.6939  -27.9815
 F4F  H15  H  HCH3   0   0.220  -11.8466  4.3707  -27.2735
 F4F  H16  H  HCH3   0   0.229  -12.6412  3.1490  -28.2558
 F4F  H17  H  HCH2   0   0.273  -18.7192  5.8061  -24.6684
 F4F  H18  H  HCH2   0   0.238  -17.2842  5.3355  -23.7788
 F4F  H19  H  H      0   0.249  -15.7100  4.5197  -27.2596
 F4F  H20  H  HCH1   0   0.253  -14.1165  6.1060  -26.3821
 F4F  H22  H  HOH1   0   0.439  -14.3908  7.3084  -22.0226

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
 F4F  O07  C06  deloc   1.245  0.020  1.245
 F4F  C20  C18  single  1.527  0.020  1.527
 F4F  C06  O08  deloc   1.247  0.020  1.247
 F4F  C06  C05  single  1.533  0.020  1.533
 F4F  C09  C05  double  1.334  0.020  1.334
 F4F  C09  C10  single  1.500  0.020  1.500
 F4F  C18  C19  single  1.527  0.020  1.527
 F4F  C18  C17  single  1.543  0.020  1.543
 F4F  C05  C04  single  1.502  0.020  1.502
 F4F  C10  C17  single  1.551  0.020  1.551
 F4F  C10  C11  single  1.544  0.020  1.544
 F4F  C17  C16  single  1.529  0.020  1.529
 F4F  O01  C02  double  1.204  0.020  1.204
 F4F  C04  O03  single  1.434  0.020  1.434
 F4F  C02  O03  single  1.333  0.020  1.333
 F4F  C02  C11  single  1.514  0.020  1.514
 F4F  C16  C15  single  1.523  0.020  1.523
 F4F  C13  C12  single  1.526  0.020  1.526
 F4F  C11  C12  single  1.546  0.020  1.546
 F4F  C12  C15  single  1.531  0.020  1.531
 F4F  C12  O14  single  1.418  0.020  1.418
 F4F  C11  H1   single  0.970  0.020  1.090
 F4F  C13  H2   single  0.970  0.020  1.090
 F4F  C13  H3   single  0.970  0.020  1.090
 F4F  C13  H4   single  0.970  0.020  1.090
 F4F  C15  H5   single  0.970  0.020  1.090
 F4F  C15  H6   single  0.970  0.020  1.090
 F4F  C16  H7   single  0.970  0.020  1.090
 F4F  C16  H8   single  0.970  0.020  1.090
 F4F  C17  H9   single  0.970  0.020  1.090
 F4F  C18  H10  single  0.970  0.020  1.090
 F4F  C19  H11  single  0.970  0.020  1.090
 F4F  C19  H12  single  0.970  0.020  1.090
 F4F  C19  H13  single  0.970  0.020  1.090
 F4F  C20  H14  single  0.970  0.020  1.090
 F4F  C20  H15  single  0.970  0.020  1.090
 F4F  C20  H16  single  0.970  0.020  1.090
 F4F  C04  H17  single  0.970  0.020  1.090
 F4F  C04  H18  single  0.970  0.020  1.090
 F4F  C09  H19  single  0.930  0.020  1.080
 F4F  C10  H20  single  0.970  0.020  1.090
 F4F  O14  H22  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
 F4F  H1   C11  C10  106.59  3.000
 F4F  H1   C11  C02  107.37  3.000
 F4F  C10  C11  C02  111.02  3.000
 F4F  H1   C11  C12  104.73  3.000
 F4F  C02  C11  C12  113.48  3.000
 F4F  C10  C11  C12  113.04  3.000
 F4F  O14  C12  C15  110.20  3.000
 F4F  O14  C12  C13  105.97  3.000
 F4F  C15  C12  C13  109.71  3.000
 F4F  O14  C12  C11  109.28  3.000
 F4F  C15  C12  C11  106.45  3.000
 F4F  C13  C12  C11  115.23  3.000
 F4F  H4   C13  H3   107.67  3.000
 F4F  H4   C13  H2   108.28  3.000
 F4F  H3   C13  H2   107.08  3.000
 F4F  H4   C13  C12  111.93  3.000
 F4F  H3   C13  C12  112.26  3.000
 F4F  H2   C13  C12  109.43  3.000
 F4F  H6   C15  H5   106.66  3.000
 F4F  H6   C15  C16  110.23  3.000
 F4F  H5   C15  C16  108.71  3.000
 F4F  H6   C15  C12  109.26  3.000
 F4F  H5   C15  C12  109.05  3.000
 F4F  C16  C15  C12  112.75  3.000
 F4F  H8   C16  H7   105.97  3.000
 F4F  H8   C16  C17  110.46  3.000
 F4F  H7   C16  C17  109.57  3.000
 F4F  H8   C16  C15  109.92  3.000
 F4F  H7   C16  C15  108.43  3.000
 F4F  C17  C16  C15  112.27  3.000
 F4F  H9   C17  C10  106.13  3.000
 F4F  H9   C17  C18  106.15  3.000
 F4F  C10  C17  C18  113.57  3.000
 F4F  H9   C17  C16  107.11  3.000
 F4F  C10  C17  C16  110.40  3.000
 F4F  C18  C17  C16  112.94  3.000
 F4F  H10  C18  C20  107.45  3.000
 F4F  H10  C18  C19  106.19  3.000
 F4F  C20  C18  C19  110.37  3.000
 F4F  H10  C18  C17  106.84  3.000
 F4F  C19  C18  C17  111.58  3.000
 F4F  C20  C18  C17  113.95  3.000
 F4F  H13  C19  H12  107.19  3.000
 F4F  H13  C19  H11  107.78  3.000
 F4F  H12  C19  H11  107.58  3.000
 F4F  H13  C19  C18  112.18  3.000
 F4F  H12  C19  C18  110.34  3.000
 F4F  H11  C19  C18  111.56  3.000
 F4F  H16  C20  H15  107.27  3.000
 F4F  H16  C20  H14  107.10  3.000
 F4F  H15  C20  H14  107.71  3.000
 F4F  H16  C20  C18  110.28  3.000
 F4F  H15  C20  C18  111.80  3.000
 F4F  H14  C20  C18  112.44  3.000
 F4F  O03  C02  O01  117.35  3.000
 F4F  O03  C02  C11  117.17  3.000
 F4F  O01  C02  C11  125.47  3.000
 F4F  H18  C04  H17  107.06  3.000
 F4F  H18  C04  O03  110.66  3.000
 F4F  H17  C04  O03  104.96  3.000
 F4F  H18  C04  C05  112.76  3.000
 F4F  H17  C04  C05  109.59  3.000
 F4F  O03  C04  C05  111.42  3.000
 F4F  C09  C05  C06  119.73  3.000
 F4F  C09  C05  C04  122.64  3.000
 F4F  C06  C05  C04  117.58  3.000
 F4F  O08  C06  O07  126.74  3.000
 F4F  O08  C06  C05  115.88  3.000
 F4F  O07  C06  C05  117.38  3.000
 F4F  H19  C09  C10  114.31  3.000
 F4F  H19  C09  C05  115.71  3.000
 F4F  C10  C09  C05  129.97  3.000
 F4F  H20  C10  C09  106.44  3.000
 F4F  H20  C10  C17  107.97  3.000
 F4F  C09  C10  C17  110.38  3.000
 F4F  H20  C10  C11  107.66  3.000
 F4F  C17  C10  C11  109.40  3.000
 F4F  C09  C10  C11  114.73  3.000
 F4F  C04  O03  C02  120.81  3.000
 F4F  H22  O14  C12  108.51  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
 F4F  Var_01  C17  C16  C15  C12  -57.45  30.0  1
 F4F  Var_02  H14  C20  C18  C17  -60.06  30.0  3
 F4F  Var_03  H11  C19  C18  C17   48.92  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
 F4F  chir_01  C11  C10  C02  C12  positiv
 F4F  chir_02  C12  C13  C11  C15  negativ
 F4F  chir_03  C17  C16  C10  C18  negativ
 F4F  chir_04  C10  C09  C17  C11  positiv

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
 F4F  plan-1  C05  0.020
 F4F  plan-1  C06  0.020
 F4F  plan-1  O07  0.020
 F4F  plan-1  O08  0.020
 F4F  plan-2  C11  0.020
 F4F  plan-2  C02  0.020
 F4F  plan-2  O01  0.020
 F4F  plan-2  O03  0.020

