# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 17 23:12:55 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: (2S)-[6-bromo-4-(4-chlorophenyl)-2-methylquinolin-3-yl](methoxy)ethanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@H](C(O)=O)c1c(C)nc2ccc(Br)cc2c1c3ccc(Cl)cc3
#
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
 0L9  0L9  '(2S)-[6-bromo-4-(4-chlorophenyl)-2-methylquinolin-3-yl](methoxy)ethanoic acid'  ligand  39  25  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_0L9
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
 0L9  CL1  CL  CL     0  -0.128   1.1285  -5.4072   0.1775
 0L9  C19  C   CR6    0  -0.044   0.9727  -3.6810   0.1669
 0L9  C20  C   CR16   0  -0.203   1.3129  -2.9730  -0.9749
 0L9  C21  C   CR16   0  -0.264   1.1893  -1.5917  -0.9764
 0L9  C18  C   CR16   0  -0.201   0.5123  -3.0324   1.3019
 0L9  C17  C   CR16   0  -0.274   0.3859  -1.6517   1.2835
 0L9  C10  C   CR6    0  -0.062   0.7233  -0.9183   0.1490
 0L9  C9   C   CR6    0   0.164   0.5545   0.5559   0.1405
 0L9  C8   C   CR6    0   0.020   1.6218   1.4202   0.1956
 0L9  C11  C   CH1    0  -0.172   3.0411   0.9149   0.2513
 0L9  O13  O   O2     0  -0.487   3.6566   1.4490   1.3961
 0L9  C14  C   CH3    0  -0.406   4.7228   0.6749   1.8849
 0L9  C12  C   C      0   0.394   3.7817   1.1956  -1.0882
 0L9  O1   O   OC    -1  -0.581   3.1560   0.8466  -2.1069
 0L9  O2   O   O      0  -0.587   4.9119   1.7057  -1.0306
 0L9  C5   C   CR66   0   0.068  -0.7677   1.0826   0.0779
 0L9  C6   C   CR16   0  -0.307  -1.9213   0.2718  -0.0203
 0L9  C1   C   CR6    0  -0.115  -3.1565   0.8574  -0.0749
 0L9  BR   BR  BR     0  -0.042  -4.6975  -0.2264  -0.2089
 0L9  C2   C   CR16   0  -0.241  -3.3175   2.2553  -0.0399
 0L9  C3   C   CR16   0  -0.292  -2.2072   3.0491   0.0430
 0L9  C4   C   CR66   0   0.193  -0.9138   2.4854   0.1006
 0L9  N    N   N      0  -0.464   0.1455   3.3186   0.1689
 0L9  C7   C   CR6    0   0.211   1.3568   2.8290   0.2127
 0L9  C16  C   CH3    0  -0.734   2.4555   3.8480   0.3026
 0L9  H1   H   HCR6   0   0.281   1.6759  -3.4869  -1.8544
 0L9  H2   H   HCR6   0   0.272   1.4816  -1.0276  -1.8512
 0L9  H3   H   HCR6   0   0.282   0.2518  -3.5914   2.1902
 0L9  H4   H   HCR6   0   0.269   0.0212  -1.1449   2.1679
 0L9  H5   H   HCH1   0   0.239   3.0080  -0.1802   0.3415
 0L9  H6   H   HCH3   0   0.227   5.0813   1.1486   2.7988
 0L9  H7   H   HCH3   0   0.195   4.4025  -0.3451   2.1348
 0L9  H8   H   HCH3   0   0.210   5.5531   0.6093   1.1785
 0L9  H10  H   HCR6   0   0.280  -1.8207  -0.8039  -0.0579
 0L9  H11  H   HCR6   0   0.282  -4.3027   2.6994  -0.0827
 0L9  H12  H   HCR6   0   0.271  -2.3035   4.1268   0.0649
 0L9  H13  H   HCH3   0   0.256   2.7662   3.9823   1.3397
 0L9  H14  H   HCH3   0   0.252   3.3458   3.5732  -0.2581
 0L9  H15  H   HCH3   0   0.242   2.0878   4.8042  -0.0632

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
 0L9  C14  O13  single    1.405  0.020  1.405
 0L9  C16  C7   single    1.501  0.020  1.501
 0L9  O13  C11  single    1.405  0.020  1.405
 0L9  N    C7   aromatic  1.307  0.020  1.307
 0L9  N    C4   aromatic  1.350  0.020  1.350
 0L9  C3   C4   aromatic  1.412  0.020  1.412
 0L9  C3   C2   aromatic  1.367  0.020  1.367
 0L9  C7   C8   aromatic  1.434  0.020  1.434
 0L9  C4   C5   aromatic  1.411  0.020  1.411
 0L9  C2   C1   aromatic  1.408  0.020  1.408
 0L9  C17  C18  aromatic  1.387  0.020  1.387
 0L9  C17  C10  aromatic  1.392  0.020  1.392
 0L9  C8   C11  single    1.508  0.020  1.508
 0L9  C8   C9   aromatic  1.375  0.020  1.375
 0L9  C5   C9   aromatic  1.425  0.020  1.425
 0L9  C5   C6   aromatic  1.413  0.020  1.413
 0L9  C1   C6   aromatic  1.368  0.020  1.368
 0L9  C1   BR   single    1.889  0.020  1.889
 0L9  C18  C19  aromatic  1.386  0.020  1.386
 0L9  C11  C12  single    1.556  0.020  1.556
 0L9  C9   C10  single    1.484  0.020  1.484
 0L9  C10  C21  aromatic  1.392  0.020  1.392
 0L9  C19  CL1  single    1.733  0.020  1.733
 0L9  C19  C20  aromatic  1.386  0.020  1.386
 0L9  C12  O2   deloc     1.241  0.020  1.241
 0L9  C12  O1   deloc     1.246  0.020  1.246
 0L9  C21  C20  aromatic  1.387  0.020  1.387
 0L9  C20  H1   single    0.930  0.020  1.080
 0L9  C21  H2   single    0.930  0.020  1.080
 0L9  C18  H3   single    0.930  0.020  1.080
 0L9  C17  H4   single    0.930  0.020  1.080
 0L9  C11  H5   single    0.970  0.020  1.090
 0L9  C14  H6   single    0.970  0.020  1.090
 0L9  C14  H7   single    0.970  0.020  1.090
 0L9  C14  H8   single    0.970  0.020  1.090
 0L9  C6   H10  single    0.930  0.020  1.080
 0L9  C2   H11  single    0.930  0.020  1.080
 0L9  C3   H12  single    0.930  0.020  1.080
 0L9  C16  H13  single    0.970  0.020  1.090
 0L9  C16  H14  single    0.970  0.020  1.090
 0L9  C16  H15  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
 0L9  C18  C19  C20  121.14  3.000
 0L9  C20  C19  CL1  119.46  3.000
 0L9  C18  C19  CL1  119.40  3.000
 0L9  H1   C20  C21  120.16  3.000
 0L9  H1   C20  C19  120.64  3.000
 0L9  C21  C20  C19  119.20  3.000
 0L9  H2   C21  C10  119.49  3.000
 0L9  H2   C21  C20  119.77  3.000
 0L9  C10  C21  C20  120.72  3.000
 0L9  H3   C18  C17  120.24  3.000
 0L9  H3   C18  C19  120.72  3.000
 0L9  C17  C18  C19  119.04  3.000
 0L9  H4   C17  C10  120.05  3.000
 0L9  H4   C17  C18  119.08  3.000
 0L9  C10  C17  C18  120.88  3.000
 0L9  C9   C10  C17  120.02  3.000
 0L9  C9   C10  C21  120.94  3.000
 0L9  C17  C10  C21  119.02  3.000
 0L9  C5   C9   C8   119.34  3.000
 0L9  C5   C9   C10  118.24  3.000
 0L9  C8   C9   C10  122.42  3.000
 0L9  C7   C8   C11  120.20  3.000
 0L9  C11  C8   C9   121.45  3.000
 0L9  C7   C8   C9   118.35  3.000
 0L9  H5   C11  C12  105.35  3.000
 0L9  H5   C11  O13  108.96  3.000
 0L9  C12  C11  O13  115.10  3.000
 0L9  H5   C11  C8   107.97  3.000
 0L9  C12  C11  C8   110.85  3.000
 0L9  O13  C11  C8   108.36  3.000
 0L9  C14  O13  C11  113.97  3.000
 0L9  H8   C14  H7   108.25  3.000
 0L9  H8   C14  H6   108.56  3.000
 0L9  H7   C14  H6   107.99  3.000
 0L9  H8   C14  O13  112.64  3.000
 0L9  H7   C14  O13  111.69  3.000
 0L9  H6   C14  O13  107.56  3.000
 0L9  O2   C12  O1   127.63  3.000
 0L9  O1   C12  C11  114.48  3.000
 0L9  O2   C12  C11  117.88  3.000
 0L9  C4   C5   C6   119.15  3.000
 0L9  C6   C5   C9   123.26  3.000
 0L9  C4   C5   C9   117.59  3.000
 0L9  H10  C6   C1   120.57  3.000
 0L9  H10  C6   C5   119.82  3.000
 0L9  C1   C6   C5   119.61  3.000
 0L9  C2   C1   BR   118.58  3.000
 0L9  BR   C1   C6   119.59  3.000
 0L9  C2   C1   C6   121.82  3.000
 0L9  H11  C2   C3   120.24  3.000
 0L9  H11  C2   C1   120.73  3.000
 0L9  C3   C2   C1   119.03  3.000
 0L9  H12  C3   C4   118.58  3.000
 0L9  H12  C3   C2   120.47  3.000
 0L9  C4   C3   C2   120.96  3.000
 0L9  N    C4   C3   118.33  3.000
 0L9  C3   C4   C5   119.42  3.000
 0L9  N    C4   C5   122.25  3.000
 0L9  C7   N    C4   119.85  3.000
 0L9  C16  C7   N    115.21  3.000
 0L9  N    C7   C8   122.62  3.000
 0L9  C16  C7   C8   122.17  3.000
 0L9  H15  C16  H14  109.00  3.000
 0L9  H15  C16  H13  107.92  3.000
 0L9  H14  C16  H13  106.75  3.000
 0L9  H15  C16  C7   109.21  3.000
 0L9  H14  C16  C7   113.38  3.000
 0L9  H13  C16  C7   110.42  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
 0L9  CONST_01  C10  C17  C18  C19     0.00   0.0  0
 0L9  CONST_02  C10  C21  C20  C19     0.00   0.0  0
 0L9  CONST_03  C17  C18  C19  C20     0.00   0.0  0
 0L9  CONST_04  C17  C10  C21  C20     0.00   0.0  0
 0L9  CONST_05  C9   C10  C21  C20   180.00   0.0  0
 0L9  CONST_06  C18  C17  C10  C21     0.00   0.0  0
 0L9  CONST_09  C18  C19  C20  C21     0.00   0.0  0
 0L9  CONST_10  C9   C10  C17  C18   180.00   0.0  0
 0L9  CONST_13  C7   C8   C9   C10   180.00   0.0  0
 0L9  CONST_14  C4   C5   C9   C10   180.00   0.0  0
 0L9  CONST_15  C6   C5   C9   C10     0.00   0.0  0
 0L9  CONST_16  N    C7   C8   C9      0.00   0.0  0
 0L9  CONST_17  N    C4   C5   C9      0.00   0.0  0
 0L9  CONST_18  C3   C4   C5   C9    180.00   0.0  0
 0L9  CONST_19  C1   C6   C5   C9    180.00   0.0  0
 0L9  CONST_20  C4   N    C7   C8      0.00   0.0  0
 0L9  CONST_21  C4   C5   C9   C8      0.00   0.0  0
 0L9  CONST_22  C6   C5   C9   C8    180.00   0.0  0
 0L9  CONST_23  C7   N    C4   C5      0.00   0.0  0
 0L9  CONST_24  C2   C3   C4   C5      0.00   0.0  0
 0L9  CONST_25  C7   C8   C9   C5      0.00   0.0  0
 0L9  CONST_26  C2   C1   C6   C5      0.00   0.0  0
 0L9  CONST_27  N    C4   C5   C6    180.00   0.0  0
 0L9  CONST_28  C3   C4   C5   C6      0.00   0.0  0
 0L9  CONST_29  C3   C2   C1   C6      0.00   0.0  0
 0L9  CONST_30  C4   C3   C2   C1      0.00   0.0  0
 0L9  CONST_31  C4   C5   C6   C1      0.00   0.0  0
 0L9  CONST_32  N    C4   C3   C2    180.00   0.0  0
 0L9  CONST_33  C7   N    C4   C3    180.00   0.0  0
 0L9  CONST_34  C17  C18  C19  CL1   180.00   0.0  0
 0L9  CONST_35  C21  C20  C19  CL1   180.00   0.0  0
 0L9  CONST_36  C11  C8   C9   C10     0.00   0.0  0
 0L9  CONST_37  C16  C7   C8   C9    180.00   0.0  0
 0L9  CONST_38  N    C7   C8   C11   180.00   0.0  0
 0L9  CONST_39  C5   C9   C8   C11   180.00   0.0  0
 0L9  CONST_40  BR   C1   C6   C5    180.00   0.0  0
 0L9  CONST_41  C3   C2   C1   BR    180.00   0.0  0
 0L9  CONST_42  C16  C7   N    C4    180.00   0.0  0
 0L9  CONST_43  H4   C17  C18  C19   180.00   0.0  0
 0L9  CONST_44  H2   C21  C20  C19   180.00   0.0  0
 0L9  CONST_45  H3   C18  C19  C20   180.00   0.0  0
 0L9  CONST_46  H1   C20  C19  C18   180.00   0.0  0
 0L9  CONST_47  H10  C6   C5   C9      0.00   0.0  0
 0L9  CONST_48  H12  C3   C4   C5    180.00   0.0  0
 0L9  CONST_49  H11  C2   C1   C6    180.00   0.0  0
 0L9  Var_01    H13  C16  C7   C8    -82.31  30.0  2
 0L9  Var_02    H6   C14  O13  C11  -176.68  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
 0L9  chir_01  C11  O13  C8  C12  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
 0L9  plan-1  CL1  0.020
 0L9  plan-1  C19  0.020
 0L9  plan-1  C20  0.020
 0L9  plan-1  C21  0.020
 0L9  plan-1  C18  0.020
 0L9  plan-1  C17  0.020
 0L9  plan-1  C10  0.020
 0L9  plan-1  C9   0.020
 0L9  plan-1  H1   0.020
 0L9  plan-1  H2   0.020
 0L9  plan-1  H3   0.020
 0L9  plan-1  H4   0.020
 0L9  plan-2  C10  0.020
 0L9  plan-2  C9   0.020
 0L9  plan-2  C8   0.020
 0L9  plan-2  C11  0.020
 0L9  plan-2  C5   0.020
 0L9  plan-2  C6   0.020
 0L9  plan-2  C1   0.020
 0L9  plan-2  BR   0.020
 0L9  plan-2  C2   0.020
 0L9  plan-2  C3   0.020
 0L9  plan-2  C4   0.020
 0L9  plan-2  N    0.020
 0L9  plan-2  C7   0.020
 0L9  plan-2  C16  0.020
 0L9  plan-2  H10  0.020
 0L9  plan-2  H11  0.020
 0L9  plan-2  H12  0.020
 0L9  plan-3  C11  0.020
 0L9  plan-3  C12  0.020
 0L9  plan-3  O1   0.020
 0L9  plan-3  O2   0.020

