# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 14:39:29 2021
#   Inital geometry file: a 118 line input string
#   Ligand name: (3R,4R)-1-{3-[(E)-2-(4-chlorophenyl)ethenyl]-4-methoxy-5-methylphenyl}-3,4-dihydroxypyrrolidin-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1c(C)cc(cc1/C=C/c2ccc(Cl)cc2)N3C[C@@H](O)[C@@H](O)C3=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
 QSJ  QSJ  (3R,4R)-1-{3-[(E)-2-(4-chlorophenyl)ethenyl]-4-methoxy-5-methylphenyl}-3,4-dihydroxypyrrolidin-2-one  ligand  46  26  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_QSJ
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
 QSJ  C4    C   CR6   0   0.376  -36.8073  -12.8553  18.7586
 QSJ  C5    C   CR16  0  -0.388  -37.0747  -13.7981  17.7847
 QSJ  C6    C   CR6   0   0.074  -36.0968  -14.7190  17.4013
 QSJ  C7    C   CR6   0   0.270  -34.8432  -14.6532  18.0224
 QSJ  C10   C   C1    0  -0.302  -36.3501  -15.7244  16.3694
 QSJ  C11   C   C1    0  -0.290  -37.5612  -16.2028  16.0570
 QSJ  C12   C   CR6   0   0.175  -37.8553  -17.2037  15.0345
 QSJ  C13   C   CR16  0  -0.320  -39.1521  -17.7169  14.9536
 QSJ  C14   C   CR16  0  -0.198  -39.4950  -18.6813  14.0196
 QSJ  O8    O   O2    0  -0.481  -33.8619  -15.5229  17.6529
 QSJ  C15   C   CR6   0  -0.059  -38.5261  -19.1423  13.1438
 QSJ  C16   C   CR16  0  -0.184  -37.2294  -18.6476  13.1910
 QSJ  C17   C   CR16  0  -0.338  -36.9036  -17.6850  14.1291
 QSJ  C2    C   CR6   0   0.021  -34.5593  -13.7045  19.0076
 QSJ  C20   C   CH2   0  -0.309  -38.4388  -11.9322  20.4499
 QSJ  C21   C   CH1   0  -0.030  -39.0085  -10.5136  20.5592
 QSJ  C23   C   CH1   0  -0.054  -39.3731  -10.2385  19.1044
 QSJ  C25   C   C     0   0.481  -38.2414  -10.9259  18.3546
 QSJ  C3    C   CR16  0  -0.341  -35.5553  -12.8045  19.3606
 QSJ  N19   N   NT    0  -0.587  -37.7994  -11.9249  19.1400
 QSJ  O27   O   OH1   0  -0.663  -39.5388   -8.8994  18.7732
 QSJ  O28   O   OH1   0  -0.659  -38.0319   -9.5802  20.9338
 QSJ  CL18  CL  CL    0  -0.126  -38.9371  -20.3472  11.9695
 QSJ  H1    H   HCR6  0   0.263  -38.0475  -13.8097  17.3098
 QSJ  H2    H   HCH3  0   0.244  -33.0642  -17.3659  17.9509
 QSJ  H3    H   HCH3  0   0.226  -33.8371  -16.6802  19.3925
 QSJ  H4    H   HCH3  0   0.226  -34.8335  -17.3257  18.0714
 QSJ  H5    H   H     0   0.263  -35.4758  -16.1045  15.8530
 QSJ  H6    H   H     0   0.256  -38.4270  -15.8596  16.6153
 QSJ  H7    H   HCR6  0   0.265  -39.9108  -17.3588  15.6389
 QSJ  H8    H   HCR6  0   0.281  -40.5049  -19.0661  13.9786
 QSJ  H9    H   HCH3  0   0.250  -32.4170  -13.5021  18.9026
 QSJ  H10   H   HCH3  0   0.249  -33.1474  -12.8195  20.3538
 QSJ  H11   H   HCH3  0   0.246  -32.9681  -14.5599  20.1891
 QSJ  H12   H   HCR6  0   0.282  -36.4796  -19.0063  12.4991
 QSJ  H13   H   HCR6  0   0.263  -35.8899  -17.3064  14.1411
 QSJ  H14   H   HCH2  0   0.262  -39.2292  -12.6866  20.4962
 QSJ  H15   H   HCH2  0   0.273  -37.7164  -12.1503  21.2381
 QSJ  H16   H   HCH1  0   0.247  -39.8764  -10.4938  21.2264
 QSJ  H17   H   HCH1  0   0.259  -40.2863  -10.8118  18.8756
 QSJ  H18   H   HCR6  0   0.263  -35.3553  -12.0459  20.1085
 QSJ  H19   H   HOH1  0   0.451  -38.9800   -8.6976  18.0136
 QSJ  H20   H   HOH1  0   0.458  -37.7552   -9.7761  21.8344
 QSJ  C1    C   CH3   0  -0.714  -33.2028  -13.6439  19.6450
 QSJ  C9    C   CH3   0  -0.412  -33.9127  -16.7854  18.3072
 QSJ  O26   O   O     0  -0.472  -37.8353  -10.6169  17.2502

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
 QSJ  CL18  C15  single    1.732  0.020  1.732
 QSJ  C15   C16  aromatic  1.389  0.020  1.389
 QSJ  C15   C14  aromatic  1.385  0.020  1.385
 QSJ  C16   C17  aromatic  1.383  0.020  1.383
 QSJ  C14   C13  aromatic  1.386  0.020  1.386
 QSJ  C17   C12  aromatic  1.399  0.020  1.399
 QSJ  C13   C12  aromatic  1.397  0.020  1.397
 QSJ  C12   C11  single    1.461  0.020  1.461
 QSJ  C11   C10  double    1.339  0.020  1.339
 QSJ  C10   C6   single    1.463  0.020  1.463
 QSJ  C6    C5   aromatic  1.397  0.020  1.397
 QSJ  C6    C7   aromatic  1.401  0.020  1.401
 QSJ  O26   C25  double    1.217  0.020  1.217
 QSJ  O8    C7   single    1.362  0.020  1.362
 QSJ  O8    C9   single    1.423  0.020  1.423
 QSJ  C5    C4   aromatic  1.382  0.020  1.382
 QSJ  C7    C2   aromatic  1.397  0.020  1.397
 QSJ  O27   C23  single    1.389  0.020  1.389
 QSJ  C25   N19  single    1.345  0.020  1.345
 QSJ  C25   C23  single    1.522  0.020  1.522
 QSJ  C4    N19  single    1.413  0.020  1.413
 QSJ  C4    C3   aromatic  1.390  0.020  1.390
 QSJ  C2    C3   aromatic  1.388  0.020  1.388
 QSJ  C2    C1   single    1.500  0.020  1.500
 QSJ  N19   C20  single    1.458  0.020  1.458
 QSJ  C23   C21  single    1.525  0.020  1.525
 QSJ  O28   C21  single    1.402  0.020  1.402
 QSJ  C21   C20  single    1.533  0.020  1.533
 QSJ  C5    H1   single    0.930  0.020  1.080
 QSJ  C9    H2   single    0.970  0.020  1.090
 QSJ  C9    H3   single    0.970  0.020  1.090
 QSJ  C9    H4   single    0.970  0.020  1.090
 QSJ  C10   H5   single    0.930  0.020  1.080
 QSJ  C11   H6   single    0.930  0.020  1.080
 QSJ  C13   H7   single    0.930  0.020  1.080
 QSJ  C14   H8   single    0.930  0.020  1.080
 QSJ  C1    H9   single    0.970  0.020  1.090
 QSJ  C1    H10  single    0.970  0.020  1.090
 QSJ  C1    H11  single    0.970  0.020  1.090
 QSJ  C16   H12  single    0.930  0.020  1.080
 QSJ  C17   H13  single    0.930  0.020  1.080
 QSJ  C20   H14  single    0.970  0.020  1.090
 QSJ  C20   H15  single    0.970  0.020  1.090
 QSJ  C21   H16  single    0.970  0.020  1.090
 QSJ  C23   H17  single    0.970  0.020  1.090
 QSJ  C3    H18  single    0.930  0.020  1.080
 QSJ  O27   H19  single    0.850  0.020  0.980
 QSJ  O28   H20  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
 QSJ  N19   C4   C3   119.44  3.000
 QSJ  C3    C4   C5   120.30  3.000
 QSJ  N19   C4   C5   120.26  3.000
 QSJ  H1    C5   C6   120.10  3.000
 QSJ  H1    C5   C4   119.37  3.000
 QSJ  C6    C5   C4   120.52  3.000
 QSJ  C10   C6   C7   120.01  3.000
 QSJ  C7    C6   C5   118.29  3.000
 QSJ  C10   C6   C5   121.70  3.000
 QSJ  C2    C7   O8   118.58  3.000
 QSJ  C2    C7   C6   121.78  3.000
 QSJ  O8    C7   C6   119.63  3.000
 QSJ  H5    C10  C11  119.54  3.000
 QSJ  H5    C10  C6   115.93  3.000
 QSJ  C11   C10  C6   124.52  3.000
 QSJ  H6    C11  C12  114.58  3.000
 QSJ  H6    C11  C10  119.23  3.000
 QSJ  C12   C11  C10  126.17  3.000
 QSJ  C17   C12  C13  117.88  3.000
 QSJ  C13   C12  C11  118.63  3.000
 QSJ  C17   C12  C11  123.49  3.000
 QSJ  H7    C13  C14  118.89  3.000
 QSJ  H7    C13  C12  119.48  3.000
 QSJ  C14   C13  C12  121.63  3.000
 QSJ  H8    C14  C15  120.72  3.000
 QSJ  H8    C14  C13  120.29  3.000
 QSJ  C15   C14  C13  118.99  3.000
 QSJ  C9    O8   C7   114.59  3.000
 QSJ  CL18  C15  C16  119.50  3.000
 QSJ  C16   C15  C14  120.88  3.000
 QSJ  CL18  C15  C14  119.62  3.000
 QSJ  H12   C16  C17  120.10  3.000
 QSJ  H12   C16  C15  120.50  3.000
 QSJ  C17   C16  C15  119.41  3.000
 QSJ  H13   C17  C16  118.15  3.000
 QSJ  H13   C17  C12  120.64  3.000
 QSJ  C16   C17  C12  121.21  3.000
 QSJ  C3    C2   C1   120.98  3.000
 QSJ  C1    C2   C7   120.73  3.000
 QSJ  C3    C2   C7   118.29  3.000
 QSJ  H15   C20  H14  108.06  3.000
 QSJ  H15   C20  N19  111.08  3.000
 QSJ  H14   C20  N19  111.01  3.000
 QSJ  H15   C20  C21  112.30  3.000
 QSJ  H14   C20  C21  111.52  3.000
 QSJ  N19   C20  C21  102.86  3.000
 QSJ  H16   C21  O28  112.17  3.000
 QSJ  H16   C21  C23  112.87  3.000
 QSJ  O28   C21  C23  107.54  3.000
 QSJ  H16   C21  C20  110.78  3.000
 QSJ  O28   C21  C20  112.11  3.000
 QSJ  C23   C21  C20  100.82  3.000
 QSJ  H17   C23  O27  110.67  3.000
 QSJ  H17   C23  C25  106.20  3.000
 QSJ  O27   C23  C25  114.00  3.000
 QSJ  H17   C23  C21  107.59  3.000
 QSJ  C25   C23  C21  102.17  3.000
 QSJ  O27   C23  C21  115.45  3.000
 QSJ  O26   C25  N19  127.51  3.000
 QSJ  N19   C25  C23  106.99  3.000
 QSJ  O26   C25  C23  125.51  3.000
 QSJ  H18   C3   C2   119.79  3.000
 QSJ  H18   C3   C4   119.38  3.000
 QSJ  C2    C3   C4   120.83  3.000
 QSJ  C25   N19  C20  112.59  3.000
 QSJ  C20   N19  C4   123.19  3.000
 QSJ  C25   N19  C4   124.21  3.000
 QSJ  H19   O27  C23  108.68  3.000
 QSJ  H20   O28  C21  108.35  3.000
 QSJ  H11   C1   H10  107.47  3.000
 QSJ  H11   C1   H9   107.08  3.000
 QSJ  H10   C1   H9   107.95  3.000
 QSJ  H11   C1   C2   111.87  3.000
 QSJ  H10   C1   C2   110.69  3.000
 QSJ  H9    C1   C2   111.57  3.000
 QSJ  H4    C9   H3   108.66  3.000
 QSJ  H4    C9   H2   108.82  3.000
 QSJ  H3    C9   H2   108.82  3.000
 QSJ  H4    C9   O8   111.68  3.000
 QSJ  H3    C9   O8   111.63  3.000
 QSJ  H2    C9   O8   107.16  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
 QSJ  CONST_01  C7    C6   C5   C4      0.00   0.0  0
 QSJ  CONST_02  C7    C2   C3   C4      0.00   0.0  0
 QSJ  CONST_03  C2    C7   C6   C5      0.00   0.0  0
 QSJ  CONST_04  C2    C3   C4   C5      0.00   0.0  0
 QSJ  CONST_05  C3    C4   C5   C6      0.00   0.0  0
 QSJ  CONST_06  C3    C2   C7   C6      0.00   0.0  0
 QSJ  CONST_07  C15   C16  C17  C12     0.00   0.0  0
 QSJ  CONST_08  C15   C14  C13  C12     0.00   0.0  0
 QSJ  CONST_09  C16   C15  C14  C13     0.00   0.0  0
 QSJ  CONST_10  C16   C17  C12  C13     0.00   0.0  0
 QSJ  CONST_11  C17   C16  C15  C14     0.00   0.0  0
 QSJ  CONST_12  C17   C12  C13  C14     0.00   0.0  0
 QSJ  CONST_13  N19   C4   C5   C6    180.00   0.0  0
 QSJ  CONST_14  N19   C4   C3   C2    180.00   0.0  0
 QSJ  CONST_15  C23   C25  N19  C4    180.00   0.0  0
 QSJ  CONST_16  C23   C25  N19  C20     0.00   0.0  0
 QSJ  CONST_17  C10   C6   C5   C4    180.00   0.0  0
 QSJ  CONST_18  C1    C2   C3   C4    180.00   0.0  0
 QSJ  CONST_19  O8    C7   C6   C5    180.00   0.0  0
 QSJ  CONST_20  C1    C2   C7   C6    180.00   0.0  0
 QSJ  CONST_21  C2    C7   C6   C10   180.00   0.0  0
 QSJ  CONST_22  C16   C17  C12  C11   180.00   0.0  0
 QSJ  CONST_23  C14   C13  C12  C11   180.00   0.0  0
 QSJ  CONST_24  CL18  C15  C14  C13   180.00   0.0  0
 QSJ  CONST_25  C3    C2   C7   O8    180.00   0.0  0
 QSJ  CONST_26  CL18  C15  C16  C17   180.00   0.0  0
 QSJ  CONST_27  O26   C25  N19  C4      0.00   0.0  0
 QSJ  CONST_28  O26   C25  N19  C20   180.00   0.0  0
 QSJ  CONST_29  H18   C3   C4   C5    180.00   0.0  0
 QSJ  CONST_30  H1    C5   C6   C7    180.00   0.0  0
 QSJ  CONST_31  H12   C16  C17  C12   180.00   0.0  0
 QSJ  CONST_32  H8    C14  C13  C12   180.00   0.0  0
 QSJ  CONST_33  H13   C17  C12  C13   180.00   0.0  0
 QSJ  CONST_34  H7    C13  C14  C15   180.00   0.0  0
 QSJ  CONST_35  C12   C11  C10  C6    180.00   0.0  0
 QSJ  CONST_36  H6    C11  C10  C6      0.00   0.0  0
 QSJ  CONST_37  H5    C10  C11  C12     0.00   0.0  0
 QSJ  Var_01    C21   C20  N19  C4    160.31  30.0  1
 QSJ  Var_02    C25   N19  C4   C5    -69.37  30.0  2
 QSJ  Var_03    C11   C10  C6   C5    -25.75  30.0  3
 QSJ  Var_04    C2    C7   O8   C9     96.22  30.0  2
 QSJ  Var_05    C17   C12  C11  C10    -7.80  30.0  3
 QSJ  Var_06    H9    C1   C2   C7     57.18  30.0  2
 QSJ  Var_07    H2    C9   O8   C7   -178.14  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
 QSJ  chir_01  C21  C23  O28  C20  positiv
 QSJ  chir_02  C23  O27  C21  C25  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
 QSJ  plan-1  C4    0.020
 QSJ  plan-1  C5    0.020
 QSJ  plan-1  C6    0.020
 QSJ  plan-1  C7    0.020
 QSJ  plan-1  C10   0.020
 QSJ  plan-1  O8    0.020
 QSJ  plan-1  C2    0.020
 QSJ  plan-1  C3    0.020
 QSJ  plan-1  N19   0.020
 QSJ  plan-1  H1    0.020
 QSJ  plan-1  H18   0.020
 QSJ  plan-1  C1    0.020
 QSJ  plan-2  C11   0.020
 QSJ  plan-2  C12   0.020
 QSJ  plan-2  C13   0.020
 QSJ  plan-2  C14   0.020
 QSJ  plan-2  C15   0.020
 QSJ  plan-2  C16   0.020
 QSJ  plan-2  C17   0.020
 QSJ  plan-2  CL18  0.020
 QSJ  plan-2  H7    0.020
 QSJ  plan-2  H8    0.020
 QSJ  plan-2  H12   0.020
 QSJ  plan-2  H13   0.020
 QSJ  plan-3  C4    0.020
 QSJ  plan-3  C20   0.020
 QSJ  plan-3  C23   0.020
 QSJ  plan-3  C25   0.020
 QSJ  plan-3  N19   0.020
 QSJ  plan-3  O26   0.020
 QSJ  plan-4  C6    0.020
 QSJ  plan-4  C10   0.020
 QSJ  plan-4  C11   0.020
 QSJ  plan-4  C12   0.020
 QSJ  plan-4  H5    0.020
 QSJ  plan-4  H6    0.020

