# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  9 17:36:17 2020
#   Inital geometry file: a 114 line input string
#   Ligand name: ethyl 4-{[(2S)-2-hydroxy-3-(propan-2-ylamino)propyl]oxy}-3-methyl-1-benzofuran-2-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1oc2cccc(OC[C@@H](O)CNC(C)C)c2c1C
#
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
 JSZ  JSZ  'ethyl 4-{[(2S)-2-hydroxy-3-(propan-2-ylamino)propyl]oxy}-3-methyl-1-benzofuran-2-carboxylate'  ligand  49  24  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_JSZ
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
 JSZ  C1    C  C     0   0.532   4.2569  -1.3996  -0.0379
 JSZ  N1    N  NH1   0  -0.596  -5.6964  -0.9865  -0.2483
 JSZ  O1    O  O     0  -0.447   4.1054  -2.5988  -0.0723
 JSZ  C2    C  CH2   0  -0.180   6.6122  -1.6124   0.0474
 JSZ  O2    O  O2    0  -0.459   5.4301  -0.7947   0.0200
 JSZ  C3    C  CH3   0  -0.689   7.8035  -0.6869   0.0878
 JSZ  O3    O  O     0  -0.457   3.4860   0.8861  -0.0156
 JSZ  C4    C  CR5   0   0.158   3.1537  -0.4389  -0.0560
 JSZ  C5    C  CR5   0   0.059   1.8048  -0.6242  -0.1009
 JSZ  O5    O  OH1   0  -0.652  -3.0466  -1.2769   0.9312
 JSZ  C6    C  CH3   0  -0.752   1.0295  -1.8932  -0.1640
 JSZ  C7    C  CR56  0  -0.053   1.2552   0.7028  -0.0874
 JSZ  C8    C  CR56  0   0.379   2.3375   1.5775  -0.0347
 JSZ  C9    C  CR16  0  -0.368   2.2186   2.9602  -0.0019
 JSZ  C10   C  CR16  0  -0.252   0.9258   3.4445  -0.0235
 JSZ  C11   C  CR16  0  -0.408  -0.1977   2.6052  -0.0746
 JSZ  C12   C  CR6   0   0.320  -0.0505   1.2261  -0.1088
 JSZ  C13   C  CH2   0  -0.187  -2.3829   0.8147  -0.1033
 JSZ  C14   C  CH1   0  -0.029  -3.3164  -0.3842  -0.1207
 JSZ  C15   C  CH2   0  -0.288  -4.7595   0.1097  -0.1272
 JSZ  C16   C  CH1   0  -0.067  -7.0926  -0.5682  -0.3160
 JSZ  C17   C  CH3   0  -0.670  -7.9408  -1.7499  -0.7638
 JSZ  C18   C  CH3   0  -0.659  -7.5728  -0.0535   1.0352
 JSZ  HN1   H  HNH1  0   0.339  -5.4786  -1.4886  -1.1019
 JSZ  H2    H  HCH2  0   0.239   6.5887  -2.2601   0.9259
 JSZ  H2A   H  HCH2  0   0.239   6.6394  -2.2476  -0.8400
 JSZ  H3    H  HCH3  0   0.238   7.8424  -0.0466  -0.7933
 JSZ  H3A   H  HCH3  0   0.238   7.7927  -0.0585   0.9781
 JSZ  H3B   H  HCH3  0   0.241   8.7167  -1.2808   0.1092
 JSZ  HO5   H  HOH1  0   0.443  -3.3978  -0.9045   1.7474
 JSZ  H6    H  HCH3  0   0.254   0.3002  -1.9397   0.6441
 JSZ  H6A   H  HCH3  0   0.252   0.4676  -1.9443  -1.0973
 JSZ  H6B   H  HCH3  0   0.257   1.6723  -2.7647  -0.1044
 JSZ  H9    H  HCR6  0   0.270   3.0779   3.6143   0.0390
 JSZ  H10   H  HCR6  0   0.269   0.7635   4.5139   0.0000
 JSZ  H11   H  HCR6  0   0.285  -1.1777   3.0613  -0.0896
 JSZ  H13   H  HCH2  0   0.227  -2.5357   1.4073   0.8078
 JSZ  H13A  H  HCH2  0   0.231  -2.5936   1.4638  -0.9602
 JSZ  H14   H  HCH1  0   0.232  -3.1323  -0.9461  -1.0440
 JSZ  H15   H  HCH2  0   0.203  -4.8746   0.8554  -0.9305
 JSZ  H15A  H  HCH2  0   0.226  -4.9468   0.6442   0.8099
 JSZ  H16   H  HCH1  0   0.189  -7.2236   0.2429  -1.0533
 JSZ  H17   H  HCH3  0   0.220  -7.8847  -2.5653  -0.0396
 JSZ  H17A  H  HCH3  0   0.228  -8.9864  -1.4572  -0.8617
 JSZ  H17B  H  HCH3  0   0.228  -7.6136  -2.1338  -1.7326
 JSZ  H18   H  HCH3  0   0.226  -8.6257   0.2257   0.9825
 JSZ  H18A  H  HCH3  0   0.216  -7.4634  -0.8267   1.7983
 JSZ  H18B  H  HCH3  0   0.230  -7.0225   0.8277   1.3661
 JSZ  O4    O  O2    0  -0.454  -1.0507   0.3406  -0.1594

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
 JSZ  C1   O1    double    1.209  0.020  1.209
 JSZ  C1   O2    single    1.321  0.020  1.321
 JSZ  C1   C4    single    1.463  0.020  1.463
 JSZ  N1   C15   single    1.447  0.020  1.447
 JSZ  N1   C16   single    1.459  0.020  1.459
 JSZ  C2   O2    single    1.438  0.020  1.438
 JSZ  C2   C3    single    1.509  0.020  1.509
 JSZ  O3   C4    aromatic  1.367  0.020  1.367
 JSZ  O3   C8    aromatic  1.341  0.020  1.341
 JSZ  C4   C5    aromatic  1.362  0.020  1.362
 JSZ  O4   C12   single    1.337  0.020  1.337
 JSZ  O4   C13   single    1.415  0.020  1.415
 JSZ  C5   C6    single    1.488  0.020  1.488
 JSZ  C5   C7    aromatic  1.436  0.020  1.436
 JSZ  O5   C14   single    1.406  0.020  1.406
 JSZ  C7   C8    aromatic  1.393  0.020  1.393
 JSZ  C7   C12   aromatic  1.407  0.020  1.407
 JSZ  C8   C9    aromatic  1.388  0.020  1.388
 JSZ  C9   C10   aromatic  1.381  0.020  1.381
 JSZ  C10  C11   aromatic  1.403  0.020  1.403
 JSZ  C11  C12   aromatic  1.387  0.020  1.387
 JSZ  C13  C14   single    1.520  0.020  1.520
 JSZ  C14  C15   single    1.525  0.020  1.525
 JSZ  C16  C17   single    1.522  0.020  1.522
 JSZ  C16  C18   single    1.524  0.020  1.524
 JSZ  N1   HN1   single    0.890  0.020  1.040
 JSZ  C2   H2    single    0.970  0.020  1.090
 JSZ  C2   H2A   single    0.970  0.020  1.090
 JSZ  C3   H3    single    0.970  0.020  1.090
 JSZ  C3   H3A   single    0.970  0.020  1.090
 JSZ  C3   H3B   single    0.970  0.020  1.090
 JSZ  O5   HO5   single    0.850  0.020  0.980
 JSZ  C6   H6    single    0.970  0.020  1.090
 JSZ  C6   H6A   single    0.970  0.020  1.090
 JSZ  C6   H6B   single    0.970  0.020  1.090
 JSZ  C9   H9    single    0.930  0.020  1.080
 JSZ  C10  H10   single    0.930  0.020  1.080
 JSZ  C11  H11   single    0.930  0.020  1.080
 JSZ  C13  H13   single    0.970  0.020  1.090
 JSZ  C13  H13A  single    0.970  0.020  1.090
 JSZ  C14  H14   single    0.970  0.020  1.090
 JSZ  C15  H15   single    0.970  0.020  1.090
 JSZ  C15  H15A  single    0.970  0.020  1.090
 JSZ  C16  H16   single    0.970  0.020  1.090
 JSZ  C17  H17   single    0.970  0.020  1.090
 JSZ  C17  H17A  single    0.970  0.020  1.090
 JSZ  C17  H17B  single    0.970  0.020  1.090
 JSZ  C18  H18   single    0.970  0.020  1.090
 JSZ  C18  H18A  single    0.970  0.020  1.090
 JSZ  C18  H18B  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
 JSZ  C4    C1   O2    111.68  3.000
 JSZ  C4    C1   O1    123.81  3.000
 JSZ  O2    C1   O1    124.51  3.000
 JSZ  HN1   N1   C16   107.96  3.000
 JSZ  HN1   N1   C15   107.85  3.000
 JSZ  C16   N1   C15   113.97  3.000
 JSZ  H2A   C2   H2    108.03  3.000
 JSZ  H2A   C2   C3    111.03  3.000
 JSZ  H2    C2   C3    111.06  3.000
 JSZ  H2A   C2   O2    109.63  3.000
 JSZ  H2    C2   O2    109.58  3.000
 JSZ  C3    C2   O2    107.50  3.000
 JSZ  C2    O2   C1    118.07  3.000
 JSZ  H3B   C3   H3A   107.85  3.000
 JSZ  H3B   C3   H3    107.83  3.000
 JSZ  H3A   C3   H3    108.78  3.000
 JSZ  H3B   C3   C2    109.14  3.000
 JSZ  H3A   C3   C2    111.57  3.000
 JSZ  H3    C3   C2    111.53  3.000
 JSZ  C8    O3   C4    106.94  3.000
 JSZ  C5    C4   O3    111.93  3.000
 JSZ  C5    C4   C1    131.13  3.000
 JSZ  O3    C4   C1    116.94  3.000
 JSZ  C7    C5   C6    126.06  3.000
 JSZ  C7    C5   C4    104.65  3.000
 JSZ  C6    C5   C4    129.28  3.000
 JSZ  HO5   O5   C14   108.57  3.000
 JSZ  H6B   C6   H6A   108.35  3.000
 JSZ  H6B   C6   H6    108.76  3.000
 JSZ  H6A   C6   H6    106.73  3.000
 JSZ  H6B   C6   C5    111.96  3.000
 JSZ  H6A   C6   C5    110.16  3.000
 JSZ  H6    C6   C5    110.71  3.000
 JSZ  C12   C7   C8    119.22  3.000
 JSZ  C12   C7   C5    134.33  3.000
 JSZ  C8    C7   C5    106.45  3.000
 JSZ  C9    C8   C7    124.05  3.000
 JSZ  C9    C8   O3    125.92  3.000
 JSZ  C7    C8   O3    110.02  3.000
 JSZ  H9    C9   C10   122.20  3.000
 JSZ  H9    C9   C8    122.39  3.000
 JSZ  C10   C9   C8    115.42  3.000
 JSZ  H10   C10  C11   118.15  3.000
 JSZ  H10   C10  C9    119.13  3.000
 JSZ  C11   C10  C9    122.72  3.000
 JSZ  H11   C11  C12   121.01  3.000
 JSZ  H11   C11  C10   118.30  3.000
 JSZ  C12   C11  C10   120.69  3.000
 JSZ  C11   C12  C7    117.90  3.000
 JSZ  C11   C12  O4    125.45  3.000
 JSZ  C7    C12  O4    116.65  3.000
 JSZ  H13A  C13  H13   107.61  3.000
 JSZ  H13A  C13  C14   109.90  3.000
 JSZ  H13   C13  C14   110.48  3.000
 JSZ  H13A  C13  O4    110.40  3.000
 JSZ  H13   C13  O4    110.17  3.000
 JSZ  C14   C13  O4    108.27  3.000
 JSZ  H14   C14  C15   108.74  3.000
 JSZ  H14   C14  C13   108.11  3.000
 JSZ  C15   C14  C13   109.02  3.000
 JSZ  H14   C14  O5    105.81  3.000
 JSZ  C15   C14  O5    112.98  3.000
 JSZ  C13   C14  O5    112.00  3.000
 JSZ  H15A  C15  H15   106.00  3.000
 JSZ  H15A  C15  C14   108.44  3.000
 JSZ  H15   C15  C14   108.73  3.000
 JSZ  H15A  C15  N1    109.31  3.000
 JSZ  H15   C15  N1    112.57  3.000
 JSZ  C14   C15  N1    111.57  3.000
 JSZ  H16   C16  C18   107.87  3.000
 JSZ  H16   C16  C17   107.94  3.000
 JSZ  C18   C16  C17   110.34  3.000
 JSZ  H16   C16  N1    110.80  3.000
 JSZ  C18   C16  N1    110.93  3.000
 JSZ  C17   C16  N1    108.92  3.000
 JSZ  H17B  C17  H17A  107.58  3.000
 JSZ  H17B  C17  H17   108.08  3.000
 JSZ  H17A  C17  H17   108.02  3.000
 JSZ  H17B  C17  C16   111.52  3.000
 JSZ  H17A  C17  C16   110.63  3.000
 JSZ  H17   C17  C16   110.86  3.000
 JSZ  H18B  C18  H18A  108.04  3.000
 JSZ  H18B  C18  H18   107.16  3.000
 JSZ  H18A  C18  H18   108.17  3.000
 JSZ  H18B  C18  C16   112.52  3.000
 JSZ  H18A  C18  C16   110.43  3.000
 JSZ  H18   C18  C16   110.36  3.000
 JSZ  C13   O4   C12   118.74  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
 JSZ  CONST_01  C7   C5   C4   O3      0.00   0.0  0
 JSZ  CONST_02  C5   C7   C8   O3      0.00   0.0  0
 JSZ  CONST_03  C12  C7   C8   O3    180.00   0.0  0
 JSZ  CONST_04  C10  C9   C8   O3    180.00   0.0  0
 JSZ  CONST_05  C7   C8   O3   C4      0.00   0.0  0
 JSZ  CONST_06  C9   C8   O3   C4    180.00   0.0  0
 JSZ  CONST_07  C8   C7   C5   C4      0.00   0.0  0
 JSZ  CONST_08  C12  C7   C5   C4    180.00   0.0  0
 JSZ  CONST_09  C8   O3   C4   C5      0.00   0.0  0
 JSZ  CONST_10  C9   C8   C7   C5    180.00   0.0  0
 JSZ  CONST_11  C11  C12  C7   C5    180.00   0.0  0
 JSZ  CONST_12  C10  C9   C8   C7      0.00   0.0  0
 JSZ  CONST_13  C10  C11  C12  C7      0.00   0.0  0
 JSZ  CONST_14  C11  C12  C7   C8      0.00   0.0  0
 JSZ  CONST_15  C11  C10  C9   C8      0.00   0.0  0
 JSZ  CONST_16  C12  C7   C8   C9      0.00   0.0  0
 JSZ  CONST_17  C12  C11  C10  C9      0.00   0.0  0
 JSZ  CONST_18  C8   O3   C4   C1    180.00   0.0  0
 JSZ  CONST_19  C7   C5   C4   C1    180.00   0.0  0
 JSZ  CONST_20  C6   C5   C4   O3    180.00   0.0  0
 JSZ  CONST_21  C5   C7   C12  O4      0.00   0.0  0
 JSZ  CONST_22  C8   C7   C12  O4    180.00   0.0  0
 JSZ  CONST_23  C10  C11  C12  O4    180.00   0.0  0
 JSZ  CONST_24  C8   C7   C5   C6    180.00   0.0  0
 JSZ  CONST_25  C12  C7   C5   C6      0.00   0.0  0
 JSZ  CONST_26  H9   C9   C8   O3      0.00   0.0  0
 JSZ  CONST_27  H11  C11  C12  C7    180.00   0.0  0
 JSZ  CONST_28  H10  C10  C9   C8    180.00   0.0  0
 JSZ  Var_01    O3   C4   C1   O1   -179.82  30.0  2
 JSZ  Var_02    H6   C6   C5   C4    125.48  30.0  2
 JSZ  Var_03    C4   C1   O2   C2    179.87  30.0  1
 JSZ  Var_04    C14  C13  O4   C12  -177.71  30.0  3
 JSZ  Var_05    C3   C2   O2   C1    179.00  30.0  1
 JSZ  Var_06    C16  N1   C15  C14  -177.58  30.0  1
 JSZ  Var_07    C17  C16  N1   C15   166.89  30.0  3
 JSZ  Var_08    H17  C17  C16  N1     62.40  30.0  3
 JSZ  Var_09    H18  C18  C16  N1   -178.14  30.0  3
 JSZ  Var_10    H3   C3   C2   O2    -60.97  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
 JSZ  chir_01  C14  O5  C13  C15  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
 JSZ  plan-1  C1   0.020
 JSZ  plan-1  O3   0.020
 JSZ  plan-1  C4   0.020
 JSZ  plan-1  C5   0.020
 JSZ  plan-1  C6   0.020
 JSZ  plan-1  C7   0.020
 JSZ  plan-1  C8   0.020
 JSZ  plan-1  C9   0.020
 JSZ  plan-1  C10  0.020
 JSZ  plan-1  C11  0.020
 JSZ  plan-1  C12  0.020
 JSZ  plan-1  H9   0.020
 JSZ  plan-1  H10  0.020
 JSZ  plan-1  H11  0.020
 JSZ  plan-1  O4   0.020
 JSZ  plan-2  C1   0.020
 JSZ  plan-2  O1   0.020
 JSZ  plan-2  O2   0.020
 JSZ  plan-2  C4   0.020

