# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 17:09:57 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: (2S)-tert-butoxy[4-(4-chlorophenyl)-2-methylquinolin-3-yl]ethanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1nc2ccccc2c(c3ccc(Cl)cc3)c1[C@H](OC(C)(C)C)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
 4BI  4BI  '(2S)-tert-butoxy[4-(4-chlorophenyl)-2-methylquinolin-3-yl]ethanoic acid'  ligand  49  27  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_4BI
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
 4BI  N1    N   N     0  -0.465  -3.1753  -1.3788   0.0760
 4BI  C2    C   CR66  0   0.196  -2.3111  -2.3737   0.3787
 4BI  C3    C   CR66  0   0.066  -0.9114  -2.1937   0.3336
 4BI  C4    C   CR6   0   0.181  -0.4251  -0.9012  -0.0185
 4BI  C5    C   CR6   0   0.017  -1.3238   0.0992  -0.3059
 4BI  C6    C   CR6   0   0.216  -2.7238  -0.2011  -0.2598
 4BI  C7    C   CR16  0  -0.333  -0.0732  -3.2949   0.6225
 4BI  C8    C   CR16  0  -0.251  -0.6109  -4.5082   0.9620
 4BI  C9    C   CR16  0  -0.262  -2.0073  -4.6784   1.0240
 4BI  C10   C   CR16  0  -0.294  -2.8420  -3.6332   0.7340
 4BI  C11   C   CH1   0  -0.186  -0.8620   1.5053  -0.6378
 4BI  C12   C   C     0   0.538  -1.1437   1.8870  -2.0917
 4BI  O13   O   OH1   0  -0.583  -0.9125   0.8708  -2.9107
 4BI  O14   O   O     0  -0.419  -1.4927   2.9782  -2.4513
 4BI  O15   O   O2    0  -0.485  -1.4555   2.4408   0.2028
 4BI  C16   C   CT    0   0.184  -0.6236   3.2825   1.0137
 4BI  C17   C   CH3   0  -0.754  -3.7699   0.8175  -0.6077
 4BI  C18   C   CR6   0  -0.062   1.0436  -0.6910  -0.0538
 4BI  C19   C   CR16  0  -0.278   1.7232  -0.5594  -1.2613
 4BI  C20   C   CR16  0  -0.195   3.0989  -0.3826  -1.2864
 4BI  C21   C   CR6   0  -0.044   3.7964  -0.3413  -0.0902
 4BI  C22   C   CR16  0  -0.197   3.1441  -0.4805   1.1250
 4BI  C23   C   CR16  0  -0.279   1.7703  -0.6610   1.1346
 4BI  CL    CL  CL    0  -0.123   5.5135  -0.1181  -0.1132
 4BI  C25   C   CH3   0  -0.672   0.3095   4.1352   0.1577
 4BI  C26   C   CH3   0  -0.659  -1.6115   4.1769   1.7506
 4BI  C27   C   CH3   0  -0.671   0.1727   2.4554   2.0191
 4BI  H7    H   HCR6  0   0.264   1.0013  -3.1840   0.5704
 4BI  H8    H   HCR6  0   0.264   0.0411  -5.3434   1.1810
 4BI  H9    H   HCR6  0   0.264  -2.4179  -5.6418   1.2961
 4BI  H10   H   HCR6  0   0.262  -3.9180  -3.7476   0.7666
 4BI  H11   H   HCH1  0   0.280   0.2341   1.5203  -0.5596
 4BI  H17   H   HCH3  0   0.266  -3.7595   1.6628   0.0773
 4BI  H17A  H   HCH3  0   0.249  -3.6401   1.2172  -1.6146
 4BI  H17B  H   HCH3  0   0.256  -4.7496   0.3476  -0.5673
 4BI  H19   H   HCR6  0   0.273   1.1813  -0.6036  -2.1963
 4BI  H20   H   HCR6  0   0.285   3.6166  -0.2807  -2.2303
 4BI  H22   H   HCR6  0   0.286   3.6956  -0.4493   2.0545
 4BI  H23   H   HCR6  0   0.277   1.2597  -0.7753   2.0825
 4BI  H25   H   HCH3  0   0.240  -0.2519   4.7553  -0.5408
 4BI  H25A  H   HCH3  0   0.237   0.8980   4.7923   0.7986
 4BI  H25B  H   HCH3  0   0.225   1.0195   3.5355  -0.4153
 4BI  H26   H   HCH3  0   0.234  -2.2888   3.5874   2.3710
 4BI  H26A  H   HCH3  0   0.226  -1.0793   4.8707   2.4021
 4BI  H26B  H   HCH3  0   0.234  -2.2088   4.7627   1.0507
 4BI  H27   H   HCH3  0   0.233   0.9168   1.8179   1.5402
 4BI  H27A  H   HCH3  0   0.239   0.7128   3.1144   2.6997
 4BI  H27B  H   HCH3  0   0.236  -0.4852   1.8201   2.6134
 4BI  H221  H   HOH1  0   0.488  -1.0376   1.1466  -3.8318

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
 4BI  N1   C2    aromatic  1.352  0.020  1.352
 4BI  N1   C6    aromatic  1.305  0.020  1.305
 4BI  C2   C3    aromatic  1.412  0.020  1.412
 4BI  C2   C10   aromatic  1.412  0.020  1.412
 4BI  C3   C4    aromatic  1.425  0.020  1.425
 4BI  C3   C7    aromatic  1.414  0.020  1.414
 4BI  C4   C5    aromatic  1.375  0.020  1.375
 4BI  C4   C18   single    1.484  0.020  1.484
 4BI  C5   C6    aromatic  1.433  0.020  1.433
 4BI  C5   C11   single    1.517  0.020  1.517
 4BI  C6   C17   single    1.501  0.020  1.501
 4BI  C7   C8    aromatic  1.370  0.020  1.370
 4BI  C7   H7    single    0.930  0.020  1.080
 4BI  C8   C9    aromatic  1.408  0.020  1.408
 4BI  C8   H8    single    0.930  0.020  1.080
 4BI  C9   C10   aromatic  1.369  0.020  1.369
 4BI  C9   H9    single    0.930  0.020  1.080
 4BI  C10  H10   single    0.930  0.020  1.080
 4BI  C11  C12   single    1.529  0.020  1.529
 4BI  C11  O15   single    1.391  0.020  1.391
 4BI  C11  H11   single    0.970  0.020  1.090
 4BI  C12  O13   single    1.325  0.020  1.325
 4BI  C12  O14   double    1.201  0.020  1.201
 4BI  O15  C16   single    1.435  0.020  1.435
 4BI  C16  C25   single    1.527  0.020  1.527
 4BI  C16  C26   single    1.523  0.020  1.523
 4BI  C16  C27   single    1.526  0.020  1.526
 4BI  C17  H17   single    0.970  0.020  1.090
 4BI  C17  H17A  single    0.970  0.020  1.090
 4BI  C17  H17B  single    0.970  0.020  1.090
 4BI  C18  C19   aromatic  1.392  0.020  1.392
 4BI  C18  C23   aromatic  1.393  0.020  1.393
 4BI  C19  C20   aromatic  1.387  0.020  1.387
 4BI  C19  H19   single    0.930  0.020  1.080
 4BI  C20  C21   aromatic  1.385  0.020  1.385
 4BI  C20  H20   single    0.930  0.020  1.080
 4BI  C21  C22   aromatic  1.386  0.020  1.386
 4BI  C21  CL    single    1.732  0.020  1.732
 4BI  C22  C23   aromatic  1.386  0.020  1.386
 4BI  C22  H22   single    0.930  0.020  1.080
 4BI  C23  H23   single    0.930  0.020  1.080
 4BI  C25  H25   single    0.970  0.020  1.090
 4BI  C25  H25A  single    0.970  0.020  1.090
 4BI  C25  H25B  single    0.970  0.020  1.090
 4BI  C26  H26   single    0.970  0.020  1.090
 4BI  C26  H26A  single    0.970  0.020  1.090
 4BI  C26  H26B  single    0.970  0.020  1.090
 4BI  C27  H27   single    0.970  0.020  1.090
 4BI  C27  H27A  single    0.970  0.020  1.090
 4BI  C27  H27B  single    0.970  0.020  1.090
 4BI  O13  H221  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
 4BI  C6    N1   C2    120.03  3.000
 4BI  C10   C2   C3    119.64  3.000
 4BI  C10   C2   N1    118.18  3.000
 4BI  C3    C2   N1    122.18  3.000
 4BI  C7    C3   C4    123.68  3.000
 4BI  C7    C3   C2    118.81  3.000
 4BI  C4    C3   C2    117.51  3.000
 4BI  C18   C4   C5    122.60  3.000
 4BI  C18   C4   C3    118.17  3.000
 4BI  C5    C4   C3    119.23  3.000
 4BI  C11   C5   C6    119.92  3.000
 4BI  C11   C5   C4    121.41  3.000
 4BI  C6    C5   C4    118.65  3.000
 4BI  C17   C6   C5    122.10  3.000
 4BI  C17   C6   N1    115.53  3.000
 4BI  C5    C6   N1    122.37  3.000
 4BI  H7    C7   C8    119.52  3.000
 4BI  H7    C7   C3    119.96  3.000
 4BI  C8    C7   C3    120.52  3.000
 4BI  H8    C8   C9    119.70  3.000
 4BI  H8    C8   C7    119.83  3.000
 4BI  C9    C8   C7    120.48  3.000
 4BI  H9    C9   C10   120.12  3.000
 4BI  H9    C9   C8    119.67  3.000
 4BI  C10   C9   C8    120.21  3.000
 4BI  H10   C10  C9    121.27  3.000
 4BI  H10   C10  C2    118.40  3.000
 4BI  C9    C10  C2    120.34  3.000
 4BI  H11   C11  O15   111.93  3.000
 4BI  H11   C11  C12   104.36  3.000
 4BI  O15   C11  C12   109.16  3.000
 4BI  H11   C11  C5    107.50  3.000
 4BI  O15   C11  C5    111.19  3.000
 4BI  C12   C11  C5    112.54  3.000
 4BI  O14   C12  O13   124.22  3.000
 4BI  O14   C12  C11   124.40  3.000
 4BI  O13   C12  C11   111.34  3.000
 4BI  H221  O13  C12   110.27  3.000
 4BI  C16   O15  C11   119.26  3.000
 4BI  C27   C16  C26   109.76  3.000
 4BI  C27   C16  C25   110.68  3.000
 4BI  C26   C16  C25   109.87  3.000
 4BI  C27   C16  O15   110.91  3.000
 4BI  C26   C16  O15   104.00  3.000
 4BI  C25   C16  O15   111.42  3.000
 4BI  H17B  C17  H17A  107.45  3.000
 4BI  H17B  C17  H17   108.72  3.000
 4BI  H17A  C17  H17   107.18  3.000
 4BI  H17B  C17  C6    109.03  3.000
 4BI  H17A  C17  C6    112.31  3.000
 4BI  H17   C17  C6    112.00  3.000
 4BI  C23   C18  C19   118.90  3.000
 4BI  C23   C18  C4    119.93  3.000
 4BI  C19   C18  C4    121.15  3.000
 4BI  H19   C19  C20   119.10  3.000
 4BI  H19   C19  C18   120.10  3.000
 4BI  C20   C19  C18   120.80  3.000
 4BI  H20   C20  C21   120.65  3.000
 4BI  H20   C20  C19   120.18  3.000
 4BI  C21   C20  C19   119.17  3.000
 4BI  CL    C21  C22   119.42  3.000
 4BI  CL    C21  C20   119.45  3.000
 4BI  C22   C21  C20   121.13  3.000
 4BI  H22   C22  C23   120.24  3.000
 4BI  H22   C22  C21   120.71  3.000
 4BI  C23   C22  C21   119.05  3.000
 4BI  H23   C23  C22   119.16  3.000
 4BI  H23   C23  C18   119.90  3.000
 4BI  C22   C23  C18   120.94  3.000
 4BI  H25B  C25  H25A  106.77  3.000
 4BI  H25B  C25  H25   108.13  3.000
 4BI  H25A  C25  H25   108.17  3.000
 4BI  H25B  C25  C16   112.64  3.000
 4BI  H25A  C25  C16   109.69  3.000
 4BI  H25   C25  C16   111.25  3.000
 4BI  H26B  C26  H26A  107.99  3.000
 4BI  H26B  C26  H26   108.37  3.000
 4BI  H26A  C26  H26   107.88  3.000
 4BI  H26B  C26  C16   111.11  3.000
 4BI  H26A  C26  C16   110.25  3.000
 4BI  H26   C26  C16   111.13  3.000
 4BI  H27B  C27  H27A  108.09  3.000
 4BI  H27B  C27  H27   108.08  3.000
 4BI  H27A  C27  H27   106.82  3.000
 4BI  H27B  C27  C16   111.09  3.000
 4BI  H27A  C27  C16   110.00  3.000
 4BI  H27   C27  C16   112.56  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
 4BI  CONST_01  C4    C3   C2   N1     0.00   0.0  0
 4BI  CONST_02  C7    C3   C2   N1   180.00   0.0  0
 4BI  CONST_03  C9    C10  C2   N1   180.00   0.0  0
 4BI  CONST_04  C4    C5   C6   N1     0.00   0.0  0
 4BI  CONST_05  C5    C6   N1   C2     0.00   0.0  0
 4BI  CONST_06  C5    C4   C3   C2     0.00   0.0  0
 4BI  CONST_07  C18   C4   C3   C2   180.00   0.0  0
 4BI  CONST_08  C8    C7   C3   C2     0.00   0.0  0
 4BI  CONST_09  C8    C9   C10  C2     0.00   0.0  0
 4BI  CONST_10  C6    N1   C2   C3     0.00   0.0  0
 4BI  CONST_11  C9    C10  C2   C3     0.00   0.0  0
 4BI  CONST_12  C6    C5   C4   C3     0.00   0.0  0
 4BI  CONST_15  C9    C8   C7   C3     0.00   0.0  0
 4BI  CONST_16  C10   C2   C3   C4   180.00   0.0  0
 4BI  CONST_17  C8    C7   C3   C4   180.00   0.0  0
 4BI  CONST_18  C20   C19  C18  C4   180.00   0.0  0
 4BI  CONST_19  C22   C23  C18  C4   180.00   0.0  0
 4BI  CONST_20  C7    C3   C4   C5   180.00   0.0  0
 4BI  CONST_23  C10   C2   N1   C6   180.00   0.0  0
 4BI  CONST_24  C18   C4   C5   C6   180.00   0.0  0
 4BI  CONST_25  C10   C2   C3   C7     0.00   0.0  0
 4BI  CONST_26  C18   C4   C3   C7     0.00   0.0  0
 4BI  CONST_27  C10   C9   C8   C7     0.00   0.0  0
 4BI  CONST_28  C21   C20  C19  C18    0.00   0.0  0
 4BI  CONST_29  C21   C22  C23  C18    0.00   0.0  0
 4BI  CONST_30  C22   C23  C18  C19    0.00   0.0  0
 4BI  CONST_31  C22   C21  C20  C19    0.00   0.0  0
 4BI  CONST_32  C23   C18  C19  C20    0.00   0.0  0
 4BI  CONST_33  C23   C22  C21  C20    0.00   0.0  0
 4BI  CONST_34  C11   C5   C6   N1   180.00   0.0  0
 4BI  CONST_35  C17   C6   N1   C2   180.00   0.0  0
 4BI  CONST_36  C11   C5   C4   C3   180.00   0.0  0
 4BI  CONST_37  C17   C6   C5   C4   180.00   0.0  0
 4BI  CONST_38  C18   C4   C5   C11    0.00   0.0  0
 4BI  CONST_39  CL    C21  C20  C19  180.00   0.0  0
 4BI  CONST_40  CL    C21  C22  C23  180.00   0.0  0
 4BI  CONST_41  H10   C10  C2   N1     0.00   0.0  0
 4BI  CONST_42  H7    C7   C3   C2   180.00   0.0  0
 4BI  CONST_43  H9    C9   C10  C2   180.00   0.0  0
 4BI  CONST_44  H8    C8   C7   C3   180.00   0.0  0
 4BI  CONST_45  H19   C19  C18  C4     0.00   0.0  0
 4BI  CONST_46  H23   C23  C18  C4     0.00   0.0  0
 4BI  CONST_47  H20   C20  C19  C18  180.00   0.0  0
 4BI  CONST_48  H22   C22  C23  C18  180.00   0.0  0
 4BI  CONST_49  H221  O13  C12  C11  180.00   0.0  0
 4BI  Var_01    H17   C17  C6   N1   117.08  30.0  2
 4BI  Var_02    C25   C16  O15  C11   60.28  30.0  3
 4BI  Var_03    H25   C25  C16  O15   58.02  30.0  3
 4BI  Var_04    H26   C26  C16  O15   60.72  30.0  3
 4BI  Var_05    H27   C27  C16  O15   67.33  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
 4BI  chir_01  C11  C5  C12  O15  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
 4BI  plan-1  C4    0.020
 4BI  plan-1  C18   0.020
 4BI  plan-1  C19   0.020
 4BI  plan-1  C20   0.020
 4BI  plan-1  C21   0.020
 4BI  plan-1  C22   0.020
 4BI  plan-1  C23   0.020
 4BI  plan-1  CL    0.020
 4BI  plan-1  H19   0.020
 4BI  plan-1  H20   0.020
 4BI  plan-1  H22   0.020
 4BI  plan-1  H23   0.020
 4BI  plan-2  N1    0.020
 4BI  plan-2  C2    0.020
 4BI  plan-2  C3    0.020
 4BI  plan-2  C4    0.020
 4BI  plan-2  C5    0.020
 4BI  plan-2  C6    0.020
 4BI  plan-2  C7    0.020
 4BI  plan-2  C8    0.020
 4BI  plan-2  C9    0.020
 4BI  plan-2  C10   0.020
 4BI  plan-2  C11   0.020
 4BI  plan-2  C17   0.020
 4BI  plan-2  C18   0.020
 4BI  plan-2  H7    0.020
 4BI  plan-2  H8    0.020
 4BI  plan-2  H9    0.020
 4BI  plan-2  H10   0.020
 4BI  plan-3  C11   0.020
 4BI  plan-3  C12   0.020
 4BI  plan-3  O13   0.020
 4BI  plan-3  O14   0.020
 4BI  plan-3  H221  0.020

