# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 16:57:00 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: 4-hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]-2H-chromen-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(=O)C[C@H](c1ccccc1)C2=C(O)c3ccccc3OC2=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
 RWF  RWF  4-hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]-2H-chromen-2-one  ligand  39  23  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_RWF
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
 RWF  C1    C  CR66  0  -0.054  -0.6489   0.5499   2.0719
 RWF  C2    C  CH1   0  -0.369   0.7309  -0.3143  -1.4237
 RWF  C3    C  CH2   0  -0.586   1.8447   0.7063  -1.6482
 RWF  C4    C  C     0   0.410   3.0860   0.4671  -0.8262
 RWF  C5    C  CH3   0  -0.772   4.0974   1.5796  -0.8590
 RWF  C6    C  CR6   0   0.180  -0.4669  -0.1346  -2.3412
 RWF  C7    C  CR16  0  -0.295  -1.3853  -1.1814  -2.4346
 RWF  C8    C  CR16  0  -0.243  -2.4993  -1.0876  -3.2537
 RWF  C9    C  CR16  0  -0.274  -2.7180   0.0629  -4.0030
 RWF  C10   C  CR16  0  -0.240  -1.8105   1.1080  -3.9226
 RWF  C11   C  CR6   0   0.526   0.4512  -1.6545   0.7050
 RWF  C12   C  CR16  0  -0.325  -0.6954   1.0099  -3.0970
 RWF  C13   C  CR6   0  -0.228   0.2922  -0.3937   0.0217
 RWF  C14   C  CR6   0   0.459  -0.2740   0.6560   0.6771
 RWF  C15   C  CR16  0  -0.322  -1.2047   1.5882   2.8286
 RWF  C16   C  CR16  0  -0.247  -1.5081   1.4015   4.1612
 RWF  C17   C  CR16  0  -0.254  -1.2602   0.1701   4.7665
 RWF  C18   C  CR16  0  -0.321  -0.7136  -0.8701   4.0406
 RWF  C19   C  CR66  0   0.354  -0.4137  -0.6714   2.6990
 RWF  O1    O  O     0  -0.466   0.1120  -1.7108   2.0229
 RWF  O2    O  OC    0  -0.441   0.8465  -2.6875   0.2187
 RWF  O3    O  O     0  -0.396   3.2592  -0.5440  -0.1841
 RWF  O4    O  OH1   0  -0.583  -0.4661   1.7859   0.0108
 RWF  H2    H  HCH1  0   0.285   1.1499  -1.2917  -1.6694
 RWF  H3C1  H  HCH2  0   0.274   1.5180   1.7348  -1.4816
 RWF  H3C2  H  HCH2  0   0.292   2.1617   0.6786  -2.6980
 RWF  H5C1  H  HCH3  0   0.260   5.0554   1.2627  -0.4521
 RWF  H5C2  H  HCH3  0   0.260   4.2347   1.9577  -1.8725
 RWF  H5C3  H  HCH3  0   0.269   3.7240   2.4156  -0.2621
 RWF  H7    H  HCR6  0   0.246  -1.2196  -2.0869  -1.8619
 RWF  H8    H  HCR6  0   0.253  -3.1945  -1.9150  -3.3121
 RWF  H9    H  HCR6  0   0.253  -3.5855   0.1397  -4.6457
 RWF  H10   H  HCR6  0   0.252  -1.9679   2.0089  -4.5021
 RWF  H12   H  HCR6  0   0.247  -0.0081   1.8438  -3.0546
 RWF  H15   H  HCR6  0   0.263  -1.4071   2.5584   2.3917
 RWF  H16   H  HCR6  0   0.273  -1.9360   2.2130   4.7329
 RWF  H17   H  HCR6  0   0.276  -1.4965   0.0230   5.8117
 RWF  H18   H  HCR6  0   0.286  -0.5165  -1.8302   4.4988
 RWF  H4    H  HOH1  0   0.494  -0.8938   2.4700   0.5380

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
 RWF  C1   C14   aromatic  1.448  0.020  1.448
 RWF  C1   C15   aromatic  1.400  0.020  1.400
 RWF  C1   C19   aromatic  1.393  0.020  1.393
 RWF  C2   C3    single    1.527  0.020  1.527
 RWF  C2   C6    single    1.519  0.020  1.519
 RWF  C2   C13   single    1.513  0.020  1.513
 RWF  C2   H2    single    0.970  0.020  1.090
 RWF  C3   C4    single    1.508  0.020  1.508
 RWF  C3   H3C1  single    0.970  0.020  1.090
 RWF  C3   H3C2  single    0.970  0.020  1.090
 RWF  C4   C5    single    1.504  0.020  1.504
 RWF  C4   O3    double    1.210  0.020  1.210
 RWF  C5   H5C1  single    0.970  0.020  1.090
 RWF  C5   H5C2  single    0.970  0.020  1.090
 RWF  C5   H5C3  single    0.970  0.020  1.090
 RWF  C6   C7    aromatic  1.396  0.020  1.396
 RWF  C6   C12   aromatic  1.390  0.020  1.390
 RWF  C7   C8    aromatic  1.386  0.020  1.386
 RWF  C7   H7    single    0.930  0.020  1.080
 RWF  C8   C9    aromatic  1.390  0.020  1.390
 RWF  C8   H8    single    0.930  0.020  1.080
 RWF  C9   C10   aromatic  1.386  0.020  1.386
 RWF  C9   H9    single    0.930  0.020  1.080
 RWF  C10  C12   aromatic  1.391  0.020  1.391
 RWF  C10  H10   single    0.930  0.020  1.080
 RWF  C11  C13   aromatic  1.443  0.020  1.443
 RWF  C11  O1    aromatic  1.362  0.020  1.362
 RWF  C11  O2    double    1.208  0.020  1.208
 RWF  C12  H12   single    0.930  0.020  1.080
 RWF  C13  C14   aromatic  1.361  0.020  1.361
 RWF  C14  O4    single    1.326  0.020  1.326
 RWF  C15  C16   aromatic  1.379  0.020  1.379
 RWF  C15  H15   single    0.930  0.020  1.080
 RWF  C16  C17   aromatic  1.394  0.020  1.394
 RWF  C16  H16   single    0.930  0.020  1.080
 RWF  C17  C18   aromatic  1.381  0.020  1.381
 RWF  C17  H17   single    0.930  0.020  1.080
 RWF  C18  C19   aromatic  1.389  0.020  1.389
 RWF  C18  H18   single    0.930  0.020  1.080
 RWF  C19  O1    aromatic  1.347  0.020  1.347
 RWF  O4   H4    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
 RWF  C19   C1   C15   118.30  3.000
 RWF  C19   C1   C14   117.01  3.000
 RWF  C15   C1   C14   124.69  3.000
 RWF  H2    C2   C13   106.23  3.000
 RWF  H2    C2   C6    105.82  3.000
 RWF  C13   C2   C6    110.77  3.000
 RWF  H2    C2   C3    106.58  3.000
 RWF  C13   C2   C3    112.77  3.000
 RWF  C6    C2   C3    114.02  3.000
 RWF  H3C2  C3   H3C1  104.85  3.000
 RWF  H3C2  C3   C4    106.24  3.000
 RWF  H3C1  C3   C4    108.21  3.000
 RWF  H3C2  C3   C2    109.54  3.000
 RWF  H3C1  C3   C2    112.89  3.000
 RWF  C4    C3   C2    114.47  3.000
 RWF  O3    C4   C5    122.24  3.000
 RWF  O3    C4   C3    122.65  3.000
 RWF  C5    C4   C3    115.11  3.000
 RWF  H5C3  C5   H5C2  106.58  3.000
 RWF  H5C3  C5   H5C1  108.63  3.000
 RWF  H5C2  C5   H5C1  109.74  3.000
 RWF  H5C3  C5   C4    108.91  3.000
 RWF  H5C2  C5   C4    111.19  3.000
 RWF  H5C1  C5   C4    111.63  3.000
 RWF  C12   C6   C7    118.22  3.000
 RWF  C12   C6   C2    123.72  3.000
 RWF  C7    C6   C2    118.06  3.000
 RWF  H7    C7   C8    119.45  3.000
 RWF  H7    C7   C6    119.37  3.000
 RWF  C8    C7   C6    121.18  3.000
 RWF  H8    C8   C9    120.16  3.000
 RWF  H8    C8   C7    119.77  3.000
 RWF  C9    C8   C7    120.07  3.000
 RWF  H9    C9   C10   120.37  3.000
 RWF  H9    C9   C8    120.32  3.000
 RWF  C10   C9   C8    119.31  3.000
 RWF  H10   C10  C12   119.53  3.000
 RWF  H10   C10  C9    120.07  3.000
 RWF  C12   C10  C9    120.40  3.000
 RWF  O2    C11  O1    115.82  3.000
 RWF  O2    C11  C13   126.34  3.000
 RWF  O1    C11  C13   117.83  3.000
 RWF  H12   C12  C10   118.58  3.000
 RWF  H12   C12  C6    120.60  3.000
 RWF  C10   C12  C6    120.83  3.000
 RWF  C14   C13  C11   119.46  3.000
 RWF  C14   C13  C2    122.71  3.000
 RWF  C11   C13  C2    117.80  3.000
 RWF  O4    C14  C13   118.40  3.000
 RWF  O4    C14  C1    120.60  3.000
 RWF  C13   C14  C1    121.00  3.000
 RWF  H15   C15  C16   118.02  3.000
 RWF  H15   C15  C1    121.37  3.000
 RWF  C16   C15  C1    120.61  3.000
 RWF  H16   C16  C17   120.24  3.000
 RWF  H16   C16  C15   119.76  3.000
 RWF  C17   C16  C15   119.99  3.000
 RWF  H17   C17  C18   119.47  3.000
 RWF  H17   C17  C16   120.05  3.000
 RWF  C18   C17  C16   120.48  3.000
 RWF  H18   C18  C19   119.78  3.000
 RWF  H18   C18  C17   121.18  3.000
 RWF  C19   C18  C17   119.04  3.000
 RWF  O1    C19  C18   117.31  3.000
 RWF  O1    C19  C1    121.11  3.000
 RWF  C18   C19  C1    121.58  3.000
 RWF  C19   O1   C11   123.44  3.000
 RWF  H4    O4   C14   113.22  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
 RWF  CONST_01  C11   C13  C14  C1      0.00   0.0  0
 RWF  CONST_02  C17   C16  C15  C1      0.00   0.0  0
 RWF  CONST_03  C17   C18  C19  C1      0.00   0.0  0
 RWF  CONST_04  C11   O1   C19  C1      0.00   0.0  0
 RWF  CONST_05  C9    C8   C7   C6      0.00   0.0  0
 RWF  CONST_06  C9    C10  C12  C6      0.00   0.0  0
 RWF  CONST_07  C10   C12  C6   C7      0.00   0.0  0
 RWF  CONST_08  C10   C9   C8   C7      0.00   0.0  0
 RWF  CONST_09  C12   C6   C7   C8      0.00   0.0  0
 RWF  CONST_10  C12   C10  C9   C8      0.00   0.0  0
 RWF  CONST_11  C18   C19  O1   C11   180.00   0.0  0
 RWF  CONST_12  C19   O1   C11  C13     0.00   0.0  0
 RWF  CONST_13  C15   C1   C14  C13   180.00   0.0  0
 RWF  CONST_14  C19   C1   C14  C13     0.00   0.0  0
 RWF  CONST_15  C16   C15  C1   C14   180.00   0.0  0
 RWF  CONST_16  C18   C19  C1   C14   180.00   0.0  0
 RWF  CONST_17  O1    C19  C1   C14     0.00   0.0  0
 RWF  CONST_18  O1    C11  C13  C14     0.00   0.0  0
 RWF  CONST_19  C18   C19  C1   C15     0.00   0.0  0
 RWF  CONST_20  O1    C19  C1   C15   180.00   0.0  0
 RWF  CONST_21  C18   C17  C16  C15     0.00   0.0  0
 RWF  CONST_22  C19   C1   C15  C16     0.00   0.0  0
 RWF  CONST_23  C19   C18  C17  C16     0.00   0.0  0
 RWF  CONST_24  O1    C19  C18  C17   180.00   0.0  0
 RWF  CONST_25  C2    C13  C14  C1    180.00   0.0  0
 RWF  CONST_26  C8    C7   C6   C2    180.00   0.0  0
 RWF  CONST_27  C10   C12  C6   C2    180.00   0.0  0
 RWF  CONST_28  O1    C11  C13  C2    180.00   0.0  0
 RWF  CONST_29  O4    C14  C13  C11   180.00   0.0  0
 RWF  CONST_30  O2    C11  C13  C14   180.00   0.0  0
 RWF  CONST_31  O4    C14  C1   C15     0.00   0.0  0
 RWF  CONST_32  O4    C14  C1   C19   180.00   0.0  0
 RWF  CONST_33  O2    C11  O1   C19   180.00   0.0  0
 RWF  CONST_34  H16   C16  C15  C1    180.00   0.0  0
 RWF  CONST_35  H18   C18  C19  C1    180.00   0.0  0
 RWF  CONST_36  H8    C8   C7   C6    180.00   0.0  0
 RWF  CONST_37  H10   C10  C12  C6    180.00   0.0  0
 RWF  CONST_38  H12   C12  C6   C7    180.00   0.0  0
 RWF  CONST_39  H9    C9   C8   C7    180.00   0.0  0
 RWF  CONST_40  H7    C7   C8   C9    180.00   0.0  0
 RWF  CONST_41  H15   C15  C1   C14     0.00   0.0  0
 RWF  CONST_42  H17   C17  C16  C15   180.00   0.0  0
 RWF  Var_01    C5    C4   C3   C2   -170.24  30.0  3
 RWF  Var_02    H5C1  C5   C4   C3   -166.51  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
 RWF  chir_01  C2  C3  C6  C13  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
 RWF  plan-1  C2   0.020
 RWF  plan-1  C6   0.020
 RWF  plan-1  C7   0.020
 RWF  plan-1  C8   0.020
 RWF  plan-1  C9   0.020
 RWF  plan-1  C10  0.020
 RWF  plan-1  C12  0.020
 RWF  plan-1  H7   0.020
 RWF  plan-1  H8   0.020
 RWF  plan-1  H9   0.020
 RWF  plan-1  H10  0.020
 RWF  plan-1  H12  0.020
 RWF  plan-2  C1   0.020
 RWF  plan-2  C14  0.020
 RWF  plan-2  C15  0.020
 RWF  plan-2  C16  0.020
 RWF  plan-2  C17  0.020
 RWF  plan-2  C18  0.020
 RWF  plan-2  C19  0.020
 RWF  plan-2  O1   0.020
 RWF  plan-2  H15  0.020
 RWF  plan-2  H16  0.020
 RWF  plan-2  H17  0.020
 RWF  plan-2  H18  0.020
 RWF  plan-3  C3   0.020
 RWF  plan-3  C4   0.020
 RWF  plan-3  C5   0.020
 RWF  plan-3  O3   0.020
 RWF  plan-4  C11  0.020
 RWF  plan-4  C13  0.020
 RWF  plan-4  O1   0.020
 RWF  plan-4  O2   0.020

