# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 30 02:12:15 2020
#   Inital geometry file: a 117 line input string
#   Ligand name: (2~{S})-2-[(1-chloranyl-4-oxidanyl-isoquinolin-3-yl)carbonylamino]-3-(1~{H}-indol-3-yl)propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)c3nc(Cl)c4ccccc4c3O
#
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
 8NN  8NN  '(2~{S})-2-[(1-chloranyl-4-oxidanyl-isoquinolin-3-yl)carbonylamino]-3-(1~{H}-indol-3-yl)propanoic acid'  ligand  45  29  .  2022-11-17  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_8NN
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
 8NN  C24  C   CR15  0  -0.060  -3.5626   0.3098   1.6273
 8NN  C19  C   CH2   0  -0.543  -3.6418  -0.7199  -0.7063
 8NN  C20  C   CR5   0   0.004  -3.1606   0.2457   0.3231
 8NN  C21  C   CR56  0   0.006  -2.0652   1.1624   0.1992
 8NN  C16  C   C     0   0.549  -3.2086  -2.9576  -1.7965
 8NN  C10  C   CR6   0   0.352   1.4145  -0.5524   1.2372
 8NN  C01  C   CR16  0  -0.237   5.0334   1.4476   0.4289
 8NN  C02  C   CR16  0  -0.239   4.6380   1.2348   1.7598
 8NN  C03  C   CR16  0  -0.280   3.4633   0.5854   2.0386
 8NN  C04  C   CR66  0   0.103   2.6454   0.1255   0.9892
 8NN  C05  C   CR66  0   0.131   3.0417   0.3404  -0.3503
 8NN  C06  C   CR16  0  -0.308   4.2519   1.0098  -0.6095
 8NN  C07  C   CR6   0   0.052   2.1596  -0.1475  -1.3593
 8NN  N08  N   N     0  -0.411   1.0568  -0.7501  -1.1209
 8NN  C09  C   CR6   0  -0.073   0.6629  -0.9628   0.1537
 8NN  O13  O   O     0  -0.527  -1.0270  -1.8642   1.5252
 8NN  N14  N   NH1   0  -0.641  -1.4069  -1.7816  -0.7125
 8NN  C15  C   CH1   0  -0.204  -2.8202  -2.0370  -0.6578
 8NN  O17  O   OH1   0  -0.588  -4.4709  -3.3410  -1.6928
 8NN  O18  O   O     0  -0.428  -2.4753  -3.2832  -2.6940
 8NN  C22  C   CR56  0   0.361  -1.8516   1.7273   1.4756
 8NN  N23  N   NR15  0  -0.686  -2.7866   1.1960   2.3153
 8NN  C25  C   CR16  0  -0.302  -0.8291   2.6427   1.7212
 8NN  C26  C   CR16  0  -0.272  -0.0163   2.9901   0.6600
 8NN  C27  C   CR16  0  -0.258  -0.2230   2.4547  -0.6222
 8NN  C28  C   CR16  0  -0.359  -1.2370   1.5501  -0.8605
 8NN  H1   H   HCR5  0   0.279  -4.3475  -0.2356   2.1281
 8NN  H2   H   HCH2  0   0.270  -4.6933  -0.9607  -0.5443
 8NN  H3   H   HCH2  0   0.257  -3.5655  -0.2855  -1.7073
 8NN  H4   H   HOH1  0   0.483   0.1710  -1.2188   2.4535
 8NN  H5   H   HCR6  0   0.274   5.9622   1.9612   0.2205
 8NN  H6   H   HCR6  0   0.272   5.2655   1.5858   2.5681
 8NN  H7   H   HCR6  0   0.271   3.1638   0.4265   3.0650
 8NN  H8   H   HCR6  0   0.263   4.5686   1.1799  -1.6287
 8NN  H9   H   HNH1  0   0.407  -1.0119  -1.4741  -1.5907
 8NN  H10  H   HCH1  0   0.306  -3.0450  -2.5413   0.2838
 8NN  H11  H   HOH1  0   0.488  -4.7137  -3.9057  -2.4424
 8NN  H12  H   HNR5  0   0.406  -2.8935   1.4185   3.2904
 8NN  H13  H   HCR6  0   0.252  -0.6712   3.0584   2.7085
 8NN  H14  H   HCR6  0   0.241   0.7968   3.6866   0.8174
 8NN  H15  H   HCR6  0   0.236   0.4359   2.7470  -1.4298
 8NN  H16  H   HCR6  0   0.238  -1.3780   1.1386  -1.8528
 8NN  C12  C   C     0   0.636  -0.6603  -1.5782   0.3772
 8NN  CL1  CL  CL    0  -0.107   2.5724   0.0925  -3.0312
 8NN  O11  O   OH1   0  -0.613   1.0472  -0.7512   2.4909

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
 8NN  C26  C27  aromatic  1.405  0.020  1.405
 8NN  C26  C25  aromatic  1.381  0.020  1.381
 8NN  C27  C28  aromatic  1.380  0.020  1.380
 8NN  C25  C22  aromatic  1.394  0.020  1.394
 8NN  C28  C21  aromatic  1.400  0.020  1.400
 8NN  O11  C10  single    1.321  0.020  1.321
 8NN  C03  C02  aromatic  1.371  0.020  1.371
 8NN  C03  C04  aromatic  1.408  0.020  1.408
 8NN  C22  C21  aromatic  1.412  0.020  1.412
 8NN  C22  N23  aromatic  1.364  0.020  1.364
 8NN  C21  C20  aromatic  1.434  0.020  1.434
 8NN  C02  C01  aromatic  1.405  0.020  1.405
 8NN  N23  C24  aromatic  1.364  0.020  1.364
 8NN  C20  C19  single    1.491  0.020  1.491
 8NN  C20  C24  aromatic  1.366  0.020  1.366
 8NN  C19  C15  single    1.553  0.020  1.553
 8NN  C10  C04  aromatic  1.427  0.020  1.427
 8NN  C10  C09  aromatic  1.381  0.020  1.381
 8NN  O13  C12  double    1.239  0.020  1.239
 8NN  C04  C05  aromatic  1.413  0.020  1.413
 8NN  C01  C06  aromatic  1.371  0.020  1.371
 8NN  C12  C09  single    1.476  0.020  1.476
 8NN  C12  N14  single    1.336  0.020  1.336
 8NN  C09  N08  aromatic  1.351  0.020  1.351
 8NN  C05  C06  aromatic  1.407  0.020  1.407
 8NN  C05  C07  aromatic  1.426  0.020  1.426
 8NN  C15  N14  single    1.437  0.020  1.437
 8NN  C15  C16  single    1.515  0.020  1.515
 8NN  N08  C07  aromatic  1.279  0.020  1.279
 8NN  C07  CL1  single    1.739  0.020  1.739
 8NN  C16  O18  double    1.204  0.020  1.204
 8NN  C16  O17  single    1.323  0.020  1.323
 8NN  C24  H1   single    0.930  0.020  1.080
 8NN  C19  H2   single    0.970  0.020  1.090
 8NN  C19  H3   single    0.970  0.020  1.090
 8NN  O11  H4   single    0.850  0.020  0.980
 8NN  C01  H5   single    0.930  0.020  1.080
 8NN  C02  H6   single    0.930  0.020  1.080
 8NN  C03  H7   single    0.930  0.020  1.080
 8NN  C06  H8   single    0.930  0.020  1.080
 8NN  N14  H9   single    0.860  0.020  1.020
 8NN  C15  H10  single    0.970  0.020  1.090
 8NN  O17  H11  single    0.850  0.020  0.980
 8NN  N23  H12  single    0.860  0.020  1.020
 8NN  C25  H13  single    0.930  0.020  1.080
 8NN  C26  H14  single    0.930  0.020  1.080
 8NN  C27  H15  single    0.930  0.020  1.080
 8NN  C28  H16  single    0.930  0.020  1.080

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
 8NN  H1   C24  N23  120.53  3.000
 8NN  H1   C24  C20  129.30  3.000
 8NN  N23  C24  C20  110.15  3.000
 8NN  H3   C19  H2   106.91  3.000
 8NN  H3   C19  C15  109.17  3.000
 8NN  H2   C19  C15  108.54  3.000
 8NN  H3   C19  C20  110.61  3.000
 8NN  H2   C19  C20  110.58  3.000
 8NN  C15  C19  C20  110.91  3.000
 8NN  C21  C20  C19  126.94  3.000
 8NN  C19  C20  C24  126.47  3.000
 8NN  C21  C20  C24  106.10  3.000
 8NN  C28  C21  C22  118.95  3.000
 8NN  C22  C21  C20  107.05  3.000
 8NN  C28  C21  C20  133.99  3.000
 8NN  O18  C16  O17  124.13  3.000
 8NN  O17  C16  C15  111.21  3.000
 8NN  O18  C16  C15  124.65  3.000
 8NN  C09  C10  C04  118.31  3.000
 8NN  C09  C10  O11  123.26  3.000
 8NN  C04  C10  O11  118.43  3.000
 8NN  H5   C01  C06  119.68  3.000
 8NN  H5   C01  C02  119.75  3.000
 8NN  C06  C01  C02  120.58  3.000
 8NN  H6   C02  C03  119.91  3.000
 8NN  H6   C02  C01  119.71  3.000
 8NN  C03  C02  C01  120.38  3.000
 8NN  H7   C03  C04  119.92  3.000
 8NN  H7   C03  C02  120.01  3.000
 8NN  C04  C03  C02  120.06  3.000
 8NN  C05  C04  C03  119.60  3.000
 8NN  C05  C04  C10  118.61  3.000
 8NN  C03  C04  C10  121.79  3.000
 8NN  C07  C05  C06  124.35  3.000
 8NN  C07  C05  C04  116.43  3.000
 8NN  C06  C05  C04  119.22  3.000
 8NN  H8   C06  C05  120.04  3.000
 8NN  H8   C06  C01  119.79  3.000
 8NN  C05  C06  C01  120.17  3.000
 8NN  CL1  C07  N08  116.68  3.000
 8NN  CL1  C07  C05  119.09  3.000
 8NN  N08  C07  C05  124.23  3.000
 8NN  C09  N08  C07  120.10  3.000
 8NN  N08  C09  C10  122.33  3.000
 8NN  N08  C09  C12  118.02  3.000
 8NN  C10  C09  C12  119.53  3.000
 8NN  H9   N14  C15  118.12  3.000
 8NN  H9   N14  C12  116.35  3.000
 8NN  C15  N14  C12  123.05  3.000
 8NN  H10  C15  N14  108.51  3.000
 8NN  H10  C15  C16  108.35  3.000
 8NN  N14  C15  C16  109.36  3.000
 8NN  H10  C15  C19  108.05  3.000
 8NN  C16  C15  C19  110.87  3.000
 8NN  N14  C15  C19  111.61  3.000
 8NN  H11  O17  C16  110.31  3.000
 8NN  C25  C22  N23  130.53  3.000
 8NN  N23  C22  C21  107.27  3.000
 8NN  C25  C22  C21  122.20  3.000
 8NN  H12  N23  C22  125.69  3.000
 8NN  H12  N23  C24  124.90  3.000
 8NN  C22  N23  C24  109.41  3.000
 8NN  H13  C25  C26  121.22  3.000
 8NN  H13  C25  C22  121.30  3.000
 8NN  C26  C25  C22  117.48  3.000
 8NN  H14  C26  C27  119.25  3.000
 8NN  H14  C26  C25  119.49  3.000
 8NN  C27  C26  C25  121.26  3.000
 8NN  H15  C27  C28  119.71  3.000
 8NN  H15  C27  C26  119.24  3.000
 8NN  C28  C27  C26  121.05  3.000
 8NN  H16  C28  C27  120.20  3.000
 8NN  H16  C28  C21  120.74  3.000
 8NN  C27  C28  C21  119.06  3.000
 8NN  N14  C12  O13  123.73  3.000
 8NN  N14  C12  C09  116.15  3.000
 8NN  O13  C12  C09  120.12  3.000
 8NN  H4   O11  C10  106.27  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
 8NN  CONST_01  C25  C22  N23  C24  180.00   0.0  0
 8NN  CONST_02  C21  C22  N23  C24    0.00   0.0  0
 8NN  CONST_03  C28  C21  C20  C24  180.00   0.0  0
 8NN  CONST_04  C22  C21  C20  C24    0.00   0.0  0
 8NN  CONST_05  C27  C28  C21  C20  180.00   0.0  0
 8NN  CONST_06  C25  C22  C21  C20  180.00   0.0  0
 8NN  CONST_07  N23  C22  C21  C20    0.00   0.0  0
 8NN  CONST_08  C22  N23  C24  C20    0.00   0.0  0
 8NN  CONST_09  C26  C27  C28  C21    0.00   0.0  0
 8NN  CONST_10  C26  C25  C22  C21    0.00   0.0  0
 8NN  CONST_11  N23  C24  C20  C21    0.00   0.0  0
 8NN  CONST_12  C02  C03  C04  C10  180.00   0.0  0
 8NN  CONST_13  C06  C05  C04  C10  180.00   0.0  0
 8NN  CONST_14  C07  C05  C04  C10    0.00   0.0  0
 8NN  CONST_15  C07  N08  C09  C10    0.00   0.0  0
 8NN  CONST_16  C04  C03  C02  C01    0.00   0.0  0
 8NN  CONST_17  C04  C05  C06  C01    0.00   0.0  0
 8NN  CONST_18  C07  C05  C06  C01  180.00   0.0  0
 8NN  CONST_19  C05  C04  C03  C02    0.00   0.0  0
 8NN  CONST_20  C05  C06  C01  C02    0.00   0.0  0
 8NN  CONST_21  C06  C01  C02  C03    0.00   0.0  0
 8NN  CONST_22  C09  C10  C04  C03  180.00   0.0  0
 8NN  CONST_23  C06  C05  C04  C03    0.00   0.0  0
 8NN  CONST_24  C07  C05  C04  C03  180.00   0.0  0
 8NN  CONST_25  N08  C09  C10  C04    0.00   0.0  0
 8NN  CONST_26  N08  C07  C05  C04    0.00   0.0  0
 8NN  CONST_27  C09  C10  C04  C05    0.00   0.0  0
 8NN  CONST_28  C09  N08  C07  C05    0.00   0.0  0
 8NN  CONST_29  N08  C07  C05  C06  180.00   0.0  0
 8NN  CONST_30  C27  C26  C25  C22    0.00   0.0  0
 8NN  CONST_31  C27  C28  C21  C22    0.00   0.0  0
 8NN  CONST_32  C26  C25  C22  N23  180.00   0.0  0
 8NN  CONST_33  C28  C21  C22  N23  180.00   0.0  0
 8NN  CONST_34  C28  C27  C26  C25    0.00   0.0  0
 8NN  CONST_35  C28  C21  C22  C25    0.00   0.0  0
 8NN  CONST_36  C28  C21  C20  C19    0.00   0.0  0
 8NN  CONST_37  C22  C21  C20  C19  180.00   0.0  0
 8NN  CONST_38  N23  C24  C20  C19  180.00   0.0  0
 8NN  CONST_39  C03  C04  C10  O11    0.00   0.0  0
 8NN  CONST_40  C05  C04  C10  O11  180.00   0.0  0
 8NN  CONST_41  N08  C09  C10  O11  180.00   0.0  0
 8NN  CONST_42  C04  C10  C09  C12  180.00   0.0  0
 8NN  CONST_43  C07  N08  C09  C12  180.00   0.0  0
 8NN  CONST_44  CL1  C07  C05  C04  180.00   0.0  0
 8NN  CONST_45  CL1  C07  C05  C06    0.00   0.0  0
 8NN  CONST_46  CL1  C07  N08  C09  180.00   0.0  0
 8NN  CONST_47  H16  C28  C21  C20    0.00   0.0  0
 8NN  CONST_48  H12  N23  C24  C20  180.00   0.0  0
 8NN  CONST_49  H15  C27  C28  C21  180.00   0.0  0
 8NN  CONST_50  H13  C25  C22  C21  180.00   0.0  0
 8NN  CONST_51  H1   C24  C20  C21  180.00   0.0  0
 8NN  CONST_52  H7   C03  C04  C10    0.00   0.0  0
 8NN  CONST_53  H8   C06  C01  C02  180.00   0.0  0
 8NN  CONST_54  H5   C01  C02  C03  180.00   0.0  0
 8NN  CONST_55  H6   C02  C03  C04  180.00   0.0  0
 8NN  CONST_56  H14  C26  C25  C22  180.00   0.0  0
 8NN  CONST_58  H9   N14  C12  C09    0.00   0.0  0
 8NN  CONST_60  H11  O17  C16  C15  180.00   0.0  0
 8NN  Var_01    C15  C19  C20  C24  -86.45  30.0  2
 8NN  Var_02    O13  C12  C09  C10   -8.24  30.0  2

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
 8NN  chir_01  C15  C19  N14  C16  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
 8NN  plan-1  C24  0.020
 8NN  plan-1  C19  0.020
 8NN  plan-1  C20  0.020
 8NN  plan-1  C21  0.020
 8NN  plan-1  C22  0.020
 8NN  plan-1  N23  0.020
 8NN  plan-1  C25  0.020
 8NN  plan-1  C26  0.020
 8NN  plan-1  C27  0.020
 8NN  plan-1  C28  0.020
 8NN  plan-1  H1   0.020
 8NN  plan-1  H12  0.020
 8NN  plan-1  H13  0.020
 8NN  plan-1  H14  0.020
 8NN  plan-1  H15  0.020
 8NN  plan-1  H16  0.020
 8NN  plan-2  C10  0.020
 8NN  plan-2  C01  0.020
 8NN  plan-2  C02  0.020
 8NN  plan-2  C03  0.020
 8NN  plan-2  C04  0.020
 8NN  plan-2  C05  0.020
 8NN  plan-2  C06  0.020
 8NN  plan-2  C07  0.020
 8NN  plan-2  N08  0.020
 8NN  plan-2  C09  0.020
 8NN  plan-2  H5   0.020
 8NN  plan-2  H6   0.020
 8NN  plan-2  H7   0.020
 8NN  plan-2  H8   0.020
 8NN  plan-2  C12  0.020
 8NN  plan-2  CL1  0.020
 8NN  plan-2  O11  0.020
 8NN  plan-3  C09  0.020
 8NN  plan-3  O13  0.020
 8NN  plan-3  N14  0.020
 8NN  plan-3  C15  0.020
 8NN  plan-3  H9   0.020
 8NN  plan-3  C12  0.020
 8NN  plan-4  C16  0.020
 8NN  plan-4  C15  0.020
 8NN  plan-4  O17  0.020
 8NN  plan-4  O18  0.020
 8NN  plan-4  H11  0.020

