# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 17:13:42 2020
#   Inital geometry file: a 133 line input string
#   Ligand name: 3-(2-chlorophenyl)-N-[(1R)-1-(naphthalen-2-yl)ethyl]-5-(propan-2-yl)-1,2-oxazole-4-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)c1onc(c2ccccc2Cl)c1C(=O)N[C@H](C)c3ccc4ccccc4c3
#
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
 9O1  9O1  3-(2-chlorophenyl)-N-[(1R)-1-(naphthalen-2-yl)ethyl]-5-(propan-2-yl)-1,2-oxazole-4-carboxamide  ligand  53  30  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9O1
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
 9O1  C4    C   CR16  0  -0.293  -0.6927   1.7056  -1.0259
 9O1  C5    C   CR16  0  -0.228   0.4186   2.5184  -1.1864
 9O1  C6    C   CR16  0  -0.243   1.3160   2.6761  -0.1406
 9O1  C7    C   CR5   0   0.233  -2.0950   0.1563   0.3040
 9O1  C10   C   CR5   0   0.528  -3.4947  -1.5241   0.1771
 9O1  C13   C   CH3   0  -0.655  -5.1941  -3.0490   1.2001
 9O1  C20   C   CR6   0   0.149   2.3617  -1.3983  -0.2221
 9O1  C21   C   CH3   0  -0.649   1.6715  -3.8409  -0.0368
 9O1  C22   C   CR16  0  -0.299   2.8413  -1.2380   1.1005
 9O1  C24   C   CR16  0  -0.379   2.8014  -0.5426  -1.1960
 9O1  C26   C   CR66  0   0.099   4.1966   0.6438   0.4163
 9O1  C28   C   CR16  0  -0.261   5.5127   2.5494  -0.2755
 9O1  C12   C   CH1   0  -0.368  -4.2927  -2.7690  -0.0016
 9O1  C14   C   CH3   0  -0.650  -5.0944  -2.7010  -1.3053
 9O1  O9    O   O     0  -0.339  -4.1113  -0.4356   0.6300
 9O1  N8    N   N     0  -0.143  -3.2452   0.6154   0.6963
 9O1  C3    C   CR6   0   0.123  -0.9229   1.0434   0.1764
 9O1  C1    C   CR16  0  -0.177   1.1043   2.0280   1.0660
 9O1  C2    C   CR6   0  -0.109  -0.0097   1.2196   1.2102
 9O1  CL18  CL  CL    0  -0.111  -0.2445   0.3694   2.7044
 9O1  C11   C   CR5   0  -0.341  -2.1872  -1.2210  -0.0440
 9O1  O17   O   O     0  -0.477  -1.3358  -2.8025  -1.5846
 9O1  N16   N   NH1   0  -0.625   0.0534  -1.9695   0.0008
 9O1  C19   C   CH1   0  -0.176   1.3185  -2.4459  -0.5390
 9O1  C23   C   CR16  0  -0.293   3.7304  -0.2477   1.4098
 9O1  C27   C   CR16  0  -0.308   5.0975   1.6937   0.7088
 9O1  C29   C   CR16  0  -0.258   5.0482   2.3908  -1.5988
 9O1  C30   C   CR16  0  -0.310   4.1757   1.3834  -1.9086
 9O1  C25   C   CR66  0   0.153   3.7255   0.4877  -0.9111
 9O1  H1    H   HCR6  0   0.268  -1.3925   1.5741  -1.8410
 9O1  H2    H   HCR6  0   0.266   0.5845   3.0232  -2.1284
 9O1  H3    H   HCR6  0   0.269   2.1925   3.2984  -0.2610
 9O1  H4    H   HCH3  0   0.232  -5.9751  -2.2953   1.3050
 9O1  H5    H   HCH3  0   0.244  -5.6827  -4.0140   1.0685
 9O1  H6    H   HCH3  0   0.242  -4.6276  -3.0872   2.1305
 9O1  H7    H   HCH3  0   0.239   2.6197  -4.1676  -0.4639
 9O1  H8    H   HCH3  0   0.229   1.7561  -3.8769   1.0495
 9O1  H9    H   HCH3  0   0.244   0.9020  -4.5520  -0.3364
 9O1  H10   H   HCR6  0   0.254   2.5044  -1.9045   1.8855
 9O1  H11   H   HCR6  0   0.247   2.4324  -0.6422  -2.2109
 9O1  H12   H   HCR6  0   0.257   6.1993   3.3533  -0.0438
 9O1  H13   H   HCH1  0   0.269  -3.5718  -3.5838  -0.0933
 9O1  H14   H   HCH3  0   0.242  -4.4386  -2.5573  -2.1634
 9O1  H15   H   HCH3  0   0.243  -5.6401  -3.6339  -1.4490
 9O1  H16   H   HCH3  0   0.232  -5.8201  -1.8875  -1.2833
 9O1  H17   H   HCR6  0   0.282   1.8047   2.1419   1.8816
 9O1  H18   H   HNH1  0   0.395   0.0890  -1.4557   0.8672
 9O1  H19   H   HCH1  0   0.268   1.2026  -2.4933  -1.6233
 9O1  H20   H   HCR6  0   0.253   4.0822  -0.1333   2.4283
 9O1  H21   H   HCR6  0   0.253   5.4514   1.8146   1.7258
 9O1  H22   H   HCR6  0   0.257   5.3843   3.0735  -2.3684
 9O1  H23   H   HCR6  0   0.252   3.8137   1.2655  -2.9231
 9O1  C15   C   C     0   0.469  -1.1313  -2.0850  -0.6151

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
 9O1  C13  C12   single    1.528  0.020  1.528
 9O1  C14  C12   single    1.532  0.020  1.532
 9O1  C12  C10   single    1.490  0.020  1.490
 9O1  O9   C10   aromatic  1.330  0.020  1.330
 9O1  O9   N8    aromatic  1.363  0.020  1.363
 9O1  C10  C11   aromatic  1.360  0.020  1.360
 9O1  N8   C7    aromatic  1.299  0.020  1.299
 9O1  C11  C7    aromatic  1.424  0.020  1.424
 9O1  C11  C15   single    1.479  0.020  1.479
 9O1  C7   C3    single    1.475  0.020  1.475
 9O1  O17  C15   double    1.223  0.020  1.223
 9O1  C4   C3    aromatic  1.392  0.020  1.392
 9O1  C4   C5    aromatic  1.386  0.020  1.386
 9O1  C15  N16   single    1.340  0.020  1.340
 9O1  C3   C2    aromatic  1.391  0.020  1.391
 9O1  N16  C19   single    1.456  0.020  1.456
 9O1  C5   C6    aromatic  1.387  0.020  1.387
 9O1  C2   CL18  single    1.735  0.020  1.735
 9O1  C2   C1    aromatic  1.384  0.020  1.384
 9O1  C19  C21   single    1.524  0.020  1.524
 9O1  C19  C20   single    1.512  0.020  1.512
 9O1  C6   C1    aromatic  1.386  0.020  1.386
 9O1  C20  C24   aromatic  1.369  0.020  1.369
 9O1  C20  C22   aromatic  1.416  0.020  1.416
 9O1  C24  C25   aromatic  1.413  0.020  1.413
 9O1  C22  C23   aromatic  1.366  0.020  1.366
 9O1  C25  C30   aromatic  1.414  0.020  1.414
 9O1  C25  C26   aromatic  1.417  0.020  1.417
 9O1  C23  C26   aromatic  1.414  0.020  1.414
 9O1  C30  C29   aromatic  1.368  0.020  1.368
 9O1  C26  C27   aromatic  1.414  0.020  1.414
 9O1  C29  C28   aromatic  1.411  0.020  1.411
 9O1  C27  C28   aromatic  1.369  0.020  1.369
 9O1  C4   H1    single    0.930  0.020  1.080
 9O1  C5   H2    single    0.930  0.020  1.080
 9O1  C6   H3    single    0.930  0.020  1.080
 9O1  C13  H4    single    0.970  0.020  1.090
 9O1  C13  H5    single    0.970  0.020  1.090
 9O1  C13  H6    single    0.970  0.020  1.090
 9O1  C21  H7    single    0.970  0.020  1.090
 9O1  C21  H8    single    0.970  0.020  1.090
 9O1  C21  H9    single    0.970  0.020  1.090
 9O1  C22  H10   single    0.930  0.020  1.080
 9O1  C24  H11   single    0.930  0.020  1.080
 9O1  C28  H12   single    0.930  0.020  1.080
 9O1  C12  H13   single    0.970  0.020  1.090
 9O1  C14  H14   single    0.970  0.020  1.090
 9O1  C14  H15   single    0.970  0.020  1.090
 9O1  C14  H16   single    0.970  0.020  1.090
 9O1  C1   H17   single    0.930  0.020  1.080
 9O1  N16  H18   single    0.860  0.020  1.020
 9O1  C19  H19   single    0.970  0.020  1.090
 9O1  C23  H20   single    0.930  0.020  1.080
 9O1  C27  H21   single    0.930  0.020  1.080
 9O1  C29  H22   single    0.930  0.020  1.080
 9O1  C30  H23   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
 9O1  H1    C4   C3   119.06  3.000
 9O1  H1    C4   C5   120.16  3.000
 9O1  C3    C4   C5   120.77  3.000
 9O1  H2    C5   C6   120.29  3.000
 9O1  H2    C5   C4   119.83  3.000
 9O1  C6    C5   C4   119.87  3.000
 9O1  H3    C6   C1   119.32  3.000
 9O1  H3    C6   C5   120.38  3.000
 9O1  C1    C6   C5   120.29  3.000
 9O1  C11   C7   C3   127.74  3.000
 9O1  C3    C7   N8   121.13  3.000
 9O1  C11   C7   N8   111.00  3.000
 9O1  C11   C10  O9   108.58  3.000
 9O1  C11   C10  C12  132.98  3.000
 9O1  O9    C10  C12  118.45  3.000
 9O1  H6    C13  H5   107.76  3.000
 9O1  H6    C13  H4   108.32  3.000
 9O1  H5    C13  H4   107.62  3.000
 9O1  H6    C13  C12  111.79  3.000
 9O1  H5    C13  C12  109.38  3.000
 9O1  H4    C13  C12  111.81  3.000
 9O1  C19   C20  C24  120.37  3.000
 9O1  C24   C20  C22  119.01  3.000
 9O1  C19   C20  C22  120.52  3.000
 9O1  H9    C21  H8   107.89  3.000
 9O1  H9    C21  H7   108.11  3.000
 9O1  H8    C21  H7   108.24  3.000
 9O1  H9    C21  C19  110.07  3.000
 9O1  H8    C21  C19  112.12  3.000
 9O1  H7    C21  C19  110.29  3.000
 9O1  H10   C22  C23  118.96  3.000
 9O1  H10   C22  C20  120.11  3.000
 9O1  C23   C22  C20  120.92  3.000
 9O1  H11   C24  C25  118.56  3.000
 9O1  H11   C24  C20  119.94  3.000
 9O1  C25   C24  C20  121.49  3.000
 9O1  C25   C26  C27  119.16  3.000
 9O1  C27   C26  C23  122.20  3.000
 9O1  C25   C26  C23  118.63  3.000
 9O1  H12   C28  C29  119.54  3.000
 9O1  H12   C28  C27  120.19  3.000
 9O1  C29   C28  C27  120.27  3.000
 9O1  H13   C12  C14  107.89  3.000
 9O1  H13   C12  C13  108.59  3.000
 9O1  C14   C12  C13  111.63  3.000
 9O1  H13   C12  C10  106.26  3.000
 9O1  C14   C12  C10  110.21  3.000
 9O1  C13   C12  C10  112.01  3.000
 9O1  H16   C14  H15  107.93  3.000
 9O1  H16   C14  H14  108.55  3.000
 9O1  H15   C14  H14  108.07  3.000
 9O1  H16   C14  C12  111.36  3.000
 9O1  H15   C14  C12  109.64  3.000
 9O1  H14   C14  C12  111.17  3.000
 9O1  N8    O9   C10  110.66  3.000
 9O1  O9    N8   C7   105.98  3.000
 9O1  C2    C3   C7   122.25  3.000
 9O1  C2    C3   C4   118.25  3.000
 9O1  C7    C3   C4   119.48  3.000
 9O1  H17   C1   C2   120.30  3.000
 9O1  H17   C1   C6   120.57  3.000
 9O1  C2    C1   C6   119.13  3.000
 9O1  CL18  C2   C1   119.00  3.000
 9O1  C1    C2   C3   121.68  3.000
 9O1  CL18  C2   C3   119.29  3.000
 9O1  C15   C11  C10  128.23  3.000
 9O1  C15   C11  C7   127.83  3.000
 9O1  C10   C11  C7   103.77  3.000
 9O1  H18   N16  C19  117.06  3.000
 9O1  H18   N16  C15  118.04  3.000
 9O1  C19   N16  C15  124.73  3.000
 9O1  H19   C19  N16  106.88  3.000
 9O1  H19   C19  C21  108.19  3.000
 9O1  N16   C19  C21  112.25  3.000
 9O1  H19   C19  C20  108.15  3.000
 9O1  C21   C19  C20  113.91  3.000
 9O1  N16   C19  C20  107.17  3.000
 9O1  H20   C23  C26  119.13  3.000
 9O1  H20   C23  C22  120.04  3.000
 9O1  C26   C23  C22  120.83  3.000
 9O1  H21   C27  C28  120.40  3.000
 9O1  H21   C27  C26  119.02  3.000
 9O1  C28   C27  C26  120.58  3.000
 9O1  H22   C29  C30  120.10  3.000
 9O1  H22   C29  C28  119.58  3.000
 9O1  C30   C29  C28  120.32  3.000
 9O1  H23   C30  C25  119.02  3.000
 9O1  H23   C30  C29  120.34  3.000
 9O1  C25   C30  C29  120.64  3.000
 9O1  C30   C25  C26  119.02  3.000
 9O1  C26   C25  C24  119.11  3.000
 9O1  C30   C25  C24  121.86  3.000
 9O1  N16   C15  O17  124.23  3.000
 9O1  N16   C15  C11  113.79  3.000
 9O1  O17   C15  C11  121.95  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
 9O1  CONST_03  C1    C2   C3   C4      0.00   0.0  0
 9O1  CONST_04  C1    C6   C5   C4      0.00   0.0  0
 9O1  CONST_05  C7    C3   C4   C5    180.00   0.0  0
 9O1  CONST_06  C2    C3   C4   C5      0.00   0.0  0
 9O1  CONST_07  C2    C1   C6   C5      0.00   0.0  0
 9O1  CONST_08  C3    C4   C5   C6      0.00   0.0  0
 9O1  CONST_09  C3    C2   C1   C6      0.00   0.0  0
 9O1  CONST_10  C10   O9   N8   C7      0.00   0.0  0
 9O1  CONST_11  O9    C10  C11  C7      0.00   0.0  0
 9O1  CONST_12  C1    C2   C3   C7    180.00   0.0  0
 9O1  CONST_13  N8    C7   C11  C10     0.00   0.0  0
 9O1  CONST_14  C3    C7   C11  C10   180.00   0.0  0
 9O1  CONST_15  C30   C25  C24  C20   180.00   0.0  0
 9O1  CONST_16  C26   C25  C24  C20     0.00   0.0  0
 9O1  CONST_17  C26   C23  C22  C20     0.00   0.0  0
 9O1  CONST_18  C25   C24  C20  C22     0.00   0.0  0
 9O1  CONST_19  C25   C26  C23  C22     0.00   0.0  0
 9O1  CONST_20  C27   C26  C23  C22   180.00   0.0  0
 9O1  CONST_21  C23   C22  C20  C24     0.00   0.0  0
 9O1  CONST_22  C29   C30  C25  C24   180.00   0.0  0
 9O1  CONST_23  C23   C26  C25  C24     0.00   0.0  0
 9O1  CONST_24  C27   C26  C25  C24   180.00   0.0  0
 9O1  CONST_25  C29   C30  C25  C26     0.00   0.0  0
 9O1  CONST_26  C29   C28  C27  C26     0.00   0.0  0
 9O1  CONST_27  C25   C30  C29  C28     0.00   0.0  0
 9O1  CONST_28  C25   C26  C27  C28     0.00   0.0  0
 9O1  CONST_29  C23   C26  C27  C28   180.00   0.0  0
 9O1  CONST_30  C11   C7   N8   O9      0.00   0.0  0
 9O1  CONST_31  C3    C7   N8   O9    180.00   0.0  0
 9O1  CONST_32  C11   C10  O9   N8      0.00   0.0  0
 9O1  CONST_35  C30   C25  C26  C23   180.00   0.0  0
 9O1  CONST_36  C30   C25  C26  C27     0.00   0.0  0
 9O1  CONST_37  C30   C29  C28  C27     0.00   0.0  0
 9O1  CONST_38  CL18  C2   C3   C4    180.00   0.0  0
 9O1  CONST_39  CL18  C2   C1   C6    180.00   0.0  0
 9O1  CONST_40  C12   C10  C11  C7    180.00   0.0  0
 9O1  CONST_41  CL18  C2   C3   C7      0.00   0.0  0
 9O1  CONST_42  O9    C10  C11  C15   180.00   0.0  0
 9O1  CONST_43  N8    C7   C11  C15   180.00   0.0  0
 9O1  CONST_44  C3    C7   C11  C15     0.00   0.0  0
 9O1  CONST_45  N8    O9   C10  C12   180.00   0.0  0
 9O1  CONST_46  C25   C24  C20  C19   180.00   0.0  0
 9O1  CONST_47  C23   C22  C20  C19   180.00   0.0  0
 9O1  CONST_48  H3    C6   C5   C4    180.00   0.0  0
 9O1  CONST_49  H17   C1   C6   C5    180.00   0.0  0
 9O1  CONST_50  H1    C4   C5   C6    180.00   0.0  0
 9O1  CONST_51  H20   C23  C22  C20   180.00   0.0  0
 9O1  CONST_52  H11   C24  C20  C22   180.00   0.0  0
 9O1  CONST_53  H10   C22  C20  C24   180.00   0.0  0
 9O1  CONST_54  H23   C30  C25  C24     0.00   0.0  0
 9O1  CONST_55  H12   C28  C27  C26   180.00   0.0  0
 9O1  CONST_56  H2    C5   C4   C3    180.00   0.0  0
 9O1  CONST_57  H21   C27  C26  C23     0.00   0.0  0
 9O1  CONST_58  H22   C29  C28  C27   180.00   0.0  0
 9O1  CONST_60  H18   N16  C15  C11     0.00   0.0  0
 9O1  CONST_61  C19   N16  C15  O17     0.00   0.0  0
 9O1  Var_01    O17   C15  C11  C7   -131.88  30.0  2
 9O1  Var_02    O9    C10  C12  C13   -45.66  30.0  2
 9O1  Var_03    H4    C13  C12  C10    66.39  30.0  3
 9O1  Var_04    H14   C14  C12  C10    58.06  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
 9O1  chir_01  C19  N16  C21  C20  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
 9O1  plan-1  C7    0.020
 9O1  plan-1  C10   0.020
 9O1  plan-1  C12   0.020
 9O1  plan-1  O9    0.020
 9O1  plan-1  N8    0.020
 9O1  plan-1  C3    0.020
 9O1  plan-1  C11   0.020
 9O1  plan-1  C15   0.020
 9O1  plan-2  C4    0.020
 9O1  plan-2  C5    0.020
 9O1  plan-2  C6    0.020
 9O1  plan-2  C7    0.020
 9O1  plan-2  C3    0.020
 9O1  plan-2  C1    0.020
 9O1  plan-2  C2    0.020
 9O1  plan-2  CL18  0.020
 9O1  plan-2  H1    0.020
 9O1  plan-2  H2    0.020
 9O1  plan-2  H3    0.020
 9O1  plan-2  H17   0.020
 9O1  plan-3  C20   0.020
 9O1  plan-3  C22   0.020
 9O1  plan-3  C24   0.020
 9O1  plan-3  C26   0.020
 9O1  plan-3  C28   0.020
 9O1  plan-3  C19   0.020
 9O1  plan-3  C23   0.020
 9O1  plan-3  C27   0.020
 9O1  plan-3  C29   0.020
 9O1  plan-3  C30   0.020
 9O1  plan-3  C25   0.020
 9O1  plan-3  H10   0.020
 9O1  plan-3  H11   0.020
 9O1  plan-3  H12   0.020
 9O1  plan-3  H20   0.020
 9O1  plan-3  H21   0.020
 9O1  plan-3  H22   0.020
 9O1  plan-3  H23   0.020
 9O1  plan-4  C11   0.020
 9O1  plan-4  O17   0.020
 9O1  plan-4  N16   0.020
 9O1  plan-4  C19   0.020
 9O1  plan-4  H18   0.020
 9O1  plan-4  C15   0.020

