# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 03:19:33 2022
#   Inital geometry file: a 106 line input string
#   Ligand name: (1S)-1-[4-ethyl-6-(1,3-oxazol-5-yl)quinazolin-2-yl]-3-methylbutan-1-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1nc(nc2ccc(cc12)c3ocnc3)[C@@H](N)CC(C)C
#
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
 5OI  5OI  "(1S)-1-[4-ethyl-6-(1,3-oxazol-5-yl)quinazolin-2-yl]-3-methylbutan-1-amine"
  ligand  45  23  .  2022-09-15  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_5OI
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
 5OI  C13  C  CH3   0  -0.646   -5.8464  38.4062  -19.0277
 5OI  C18  C  CH1   0  -0.246   -6.5210  37.0417  -19.1333
 5OI  C17  C  CH1   0  -0.188   -7.7896  35.5260  -20.8163
 5OI  C16  C  CH2   0  -0.402   -7.0069  36.8176  -20.5660
 5OI  C15  C  CH2   0  -0.527  -12.1056  37.3401  -19.6388
 5OI  C11  C  CR6   0   0.345   -8.9758  35.4435  -19.8823
 5OI  C12  C  CH3   0  -0.655  -11.8660  38.2216  -20.8512
 5OI  C1   C  CR16  0  -0.307  -11.1667  33.5625  -16.2055
 5OI  C2   C  CR16  0  -0.291  -10.0928  33.5993  -17.0471
 5OI  C3   C  CR16  0  -0.380  -12.2275  35.3690  -17.3975
 5OI  C4   C  CR15  0  -0.231  -13.6412  33.6540  -14.3328
 5OI  C5   C  CR15  0   0.167  -15.3132  34.8859  -14.6819
 5OI  C6   C  CR66  0   0.051  -11.1280  35.4223  -18.2732
 5OI  C7   C  CR6   0   0.017  -12.2582  34.4516  -16.3706
 5OI  C8   C  CR66  0   0.245  -10.0485  34.5331  -18.1048
 5OI  C9   C  CR5   0   0.354  -13.3776  34.3745  -15.4525
 5OI  C10  C  CR6   0   0.291  -11.0180  36.3451  -19.3582
 5OI  C14  C  CH3   0  -0.655   -5.5730  35.9401  -18.6682
 5OI  N19  N  N     0  -0.407  -14.8847  33.9987  -13.8564
 5OI  N20  N  N     0  -0.440   -8.9740  34.5548  -18.9296
 5OI  N21  N  N     0  -0.440   -9.9642  36.3365  -20.1252
 5OI  N22  N  NH2   0  -0.777   -8.1618  35.4619  -22.2215
 5OI  O23  O  O     0  -0.400  -14.4593  35.1644  -15.6701
 5OI  H32  H  HCH3  0   0.224   -5.5243  38.6098  -18.0053
 5OI  H33  H  HCH3  0   0.213   -4.9631  38.4535  -19.6691
 5OI  H34  H  HCH3  0   0.223   -6.5198  39.2097  -19.3312
 5OI  H43  H  HCH1  0   0.219   -7.3901  37.0497  -18.4648
 5OI  H42  H  HCH1  0   0.246   -7.1473  34.6681  -20.6039
 5OI  H40  H  HCH2  0   0.226   -6.1440  36.8190  -21.2400
 5OI  H41  H  HCH2  0   0.221   -7.6365  37.6626  -20.8660
 5OI  H39  H  HCH2  0   0.264  -12.2448  37.9591  -18.7466
 5OI  H38  H  HCH2  0   0.262  -13.0471  36.7945  -19.7556
 5OI  H30  H  HCH3  0   0.234  -12.7091  38.8990  -20.9837
 5OI  H31  H  HCH3  0   0.227  -10.9662  38.8252  -20.7410
 5OI  H29  H  HCH3  0   0.227  -11.7624  37.6338  -21.7623
 5OI  H24  H  HCR6  0   0.268  -11.1833  32.8381  -15.4013
 5OI  H25  H  HCR6  0   0.269   -9.2634  32.9168  -16.9161
 5OI  H26  H  HCR6  0   0.271  -13.0485  36.0589  -17.5379
 5OI  H27  H  HCR5  0   0.279  -13.0232  32.9203  -13.8407
 5OI  H28  H  HCR5  0   0.298  -16.2539  35.4153  -14.6700
 5OI  H37  H  HCH3  0   0.225   -5.1850  36.1553  -17.6712
 5OI  H35  H  HCH3  0   0.226   -6.0635  34.9674  -18.6236
 5OI  H36  H  HCH3  0   0.213   -4.7190  35.8546  -19.3445
 5OI  H44  H  HNH2  0   0.346   -8.6435  34.5914  -22.4122
 5OI  H1   H  HNH2  0   0.341   -8.8258  36.2003  -22.4258

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
 5OI  N22  C17  single    1.455  0.020  1.455
 5OI  C17  C16  single    1.531  0.020  1.531
 5OI  C17  C11  single    1.512  0.020  1.512
 5OI  C16  C18  single    1.529  0.020  1.529
 5OI  C12  C15  single    1.518  0.020  1.518
 5OI  N21  C11  aromatic  1.354  0.020  1.354
 5OI  N21  C10  aromatic  1.303  0.020  1.303
 5OI  C15  C10  single    1.500  0.020  1.500
 5OI  C11  N20  aromatic  1.303  0.020  1.303
 5OI  C10  C6   aromatic  1.429  0.020  1.429
 5OI  C18  C14  single    1.526  0.020  1.526
 5OI  C18  C13  single    1.526  0.020  1.526
 5OI  N20  C8   aromatic  1.355  0.020  1.355
 5OI  C6   C8   aromatic  1.409  0.020  1.409
 5OI  C6   C3   aromatic  1.407  0.020  1.407
 5OI  C8   C2   aromatic  1.412  0.020  1.412
 5OI  C3   C7   aromatic  1.377  0.020  1.377
 5OI  C2   C1   aromatic  1.365  0.020  1.365
 5OI  C7   C1   aromatic  1.417  0.020  1.417
 5OI  C7   C9   single    1.450  0.020  1.450
 5OI  O23  C9   aromatic  1.357  0.020  1.357
 5OI  O23  C5   aromatic  1.335  0.020  1.335
 5OI  C9   C4   aromatic  1.357  0.020  1.357
 5OI  C5   N19  aromatic  1.285  0.020  1.285
 5OI  C4   N19  aromatic  1.376  0.020  1.376
 5OI  C13  H32  single    0.970  0.020  1.090
 5OI  C13  H33  single    0.970  0.020  1.090
 5OI  C13  H34  single    0.970  0.020  1.090
 5OI  C18  H43  single    0.970  0.020  1.090
 5OI  C17  H42  single    0.970  0.020  1.090
 5OI  C16  H40  single    0.970  0.020  1.090
 5OI  C16  H41  single    0.970  0.020  1.090
 5OI  C15  H39  single    0.970  0.020  1.090
 5OI  C15  H38  single    0.970  0.020  1.090
 5OI  C12  H30  single    0.970  0.020  1.090
 5OI  C12  H31  single    0.970  0.020  1.090
 5OI  C12  H29  single    0.970  0.020  1.090
 5OI  C1   H24  single    0.930  0.020  1.080
 5OI  C2   H25  single    0.930  0.020  1.080
 5OI  C3   H26  single    0.930  0.020  1.080
 5OI  C4   H27  single    0.930  0.020  1.080
 5OI  C5   H28  single    0.930  0.020  1.080
 5OI  C14  H37  single    0.970  0.020  1.090
 5OI  C14  H35  single    0.970  0.020  1.090
 5OI  C14  H36  single    0.970  0.020  1.090
 5OI  N22  H44  single    0.890  0.020  1.040
 5OI  N22  H1   single    0.890  0.020  1.040

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
 5OI  H34  C13  H33  107.68  3.000
 5OI  H34  C13  H32  107.78  3.000
 5OI  H33  C13  H32  107.66  3.000
 5OI  H34  C13  C18  111.49  3.000
 5OI  H33  C13  C18  110.83  3.000
 5OI  H32  C13  C18  111.23  3.000
 5OI  H43  C18  C14  108.17  3.000
 5OI  H43  C18  C16  108.68  3.000
 5OI  C14  C18  C16  112.15  3.000
 5OI  H43  C18  C13  107.57  3.000
 5OI  C14  C18  C13  110.48  3.000
 5OI  C16  C18  C13  109.65  3.000
 5OI  H42  C17  N22  107.67  3.000
 5OI  H42  C17  C11  107.35  3.000
 5OI  N22  C17  C11  113.17  3.000
 5OI  H42  C17  C16  109.28  3.000
 5OI  C11  C17  C16  110.25  3.000
 5OI  N22  C17  C16  109.02  3.000
 5OI  H41  C16  H40  106.46  3.000
 5OI  H41  C16  C17  108.19  3.000
 5OI  H40  C16  C17  107.66  3.000
 5OI  H41  C16  C18  109.03  3.000
 5OI  H40  C16  C18  109.03  3.000
 5OI  C17  C16  C18  116.06  3.000
 5OI  H38  C15  H39  105.04  3.000
 5OI  H38  C15  C10  108.23  3.000
 5OI  H39  C15  C10  108.34  3.000
 5OI  H38  C15  C12  109.88  3.000
 5OI  H39  C15  C12  110.04  3.000
 5OI  C10  C15  C12  114.83  3.000
 5OI  N21  C11  N20  125.59  3.000
 5OI  N20  C11  C17  119.20  3.000
 5OI  N21  C11  C17  115.21  3.000
 5OI  H29  C12  H31  107.76  3.000
 5OI  H29  C12  H30  107.90  3.000
 5OI  H31  C12  H30  107.88  3.000
 5OI  H29  C12  C15  111.70  3.000
 5OI  H31  C12  C15  111.80  3.000
 5OI  H30  C12  C15  109.64  3.000
 5OI  H24  C1   C7   119.64  3.000
 5OI  H24  C1   C2   119.22  3.000
 5OI  C7   C1   C2   121.14  3.000
 5OI  H25  C2   C8   118.94  3.000
 5OI  H25  C2   C1   120.76  3.000
 5OI  C8   C2   C1   120.30  3.000
 5OI  H26  C3   C7   120.31  3.000
 5OI  H26  C3   C6   119.24  3.000
 5OI  C7   C3   C6   120.45  3.000
 5OI  H27  C4   N19  122.05  3.000
 5OI  H27  C4   C9   128.79  3.000
 5OI  N19  C4   C9   109.16  3.000
 5OI  H28  C5   O23  117.58  3.000
 5OI  H28  C5   N19  128.46  3.000
 5OI  O23  C5   N19  113.96  3.000
 5OI  C10  C6   C8   116.08  3.000
 5OI  C8   C6   C3   120.04  3.000
 5OI  C10  C6   C3   123.88  3.000
 5OI  C9   C7   C3   121.65  3.000
 5OI  C9   C7   C1   119.17  3.000
 5OI  C3   C7   C1   119.18  3.000
 5OI  N20  C8   C6   121.66  3.000
 5OI  C6   C8   C2   118.89  3.000
 5OI  N20  C8   C2   119.44  3.000
 5OI  O23  C9   C7   118.88  3.000
 5OI  O23  C9   C4   106.64  3.000
 5OI  C7   C9   C4   134.48  3.000
 5OI  N21  C10  C6   120.32  3.000
 5OI  C6   C10  C15  120.97  3.000
 5OI  N21  C10  C15  118.71  3.000
 5OI  H36  C14  H35  107.88  3.000
 5OI  H36  C14  H37  107.63  3.000
 5OI  H35  C14  H37  107.37  3.000
 5OI  H36  C14  C18  110.69  3.000
 5OI  H35  C14  C18  112.15  3.000
 5OI  H37  C14  C18  110.92  3.000
 5OI  C5   N19  C4   104.59  3.000
 5OI  C8   N20  C11  117.06  3.000
 5OI  C10  N21  C11  119.28  3.000
 5OI  H1   N22  H44  106.05  3.000
 5OI  H1   N22  C17  109.27  3.000
 5OI  H44  N22  C17  109.96  3.000
 5OI  C9   O23  C5   105.64  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
 5OI  CONST_01  C6   C10  N21  C11     0.00   0.0  0
 5OI  CONST_02  C6   C8   N20  C11     0.00   0.0  0
 5OI  CONST_03  C2   C8   N20  C11   180.00   0.0  0
 5OI  CONST_04  N20  C8   C2   C1    180.00   0.0  0
 5OI  CONST_05  C6   C8   C2   C1      0.00   0.0  0
 5OI  CONST_06  C6   C3   C7   C1      0.00   0.0  0
 5OI  CONST_07  O23  C9   C7   C1    180.00   0.0  0
 5OI  CONST_08  C4   C9   C7   C1      0.00   0.0  0
 5OI  CONST_09  C10  C6   C8   C2    180.00   0.0  0
 5OI  CONST_10  C3   C6   C8   C2      0.00   0.0  0
 5OI  CONST_11  C3   C7   C1   C2      0.00   0.0  0
 5OI  CONST_12  C9   C7   C1   C2    180.00   0.0  0
 5OI  CONST_13  N21  C10  C6   C3    180.00   0.0  0
 5OI  CONST_14  N20  C8   C6   C3    180.00   0.0  0
 5OI  CONST_15  O23  C9   C7   C3      0.00   0.0  0
 5OI  CONST_16  C4   C9   C7   C3    180.00   0.0  0
 5OI  CONST_17  C5   O23  C9   C4      0.00   0.0  0
 5OI  CONST_18  O23  C5   N19  C4      0.00   0.0  0
 5OI  CONST_19  C7   C9   O23  C5    180.00   0.0  0
 5OI  CONST_20  C9   C4   N19  C5      0.00   0.0  0
 5OI  CONST_21  C9   C7   C3   C6    180.00   0.0  0
 5OI  CONST_22  C10  C6   C3   C7    180.00   0.0  0
 5OI  CONST_23  C8   C6   C3   C7      0.00   0.0  0
 5OI  CONST_24  C8   C2   C1   C7      0.00   0.0  0
 5OI  CONST_25  N19  C4   C9   C7    180.00   0.0  0
 5OI  CONST_26  N21  C11  N20  C8      0.00   0.0  0
 5OI  CONST_27  N21  C10  C6   C8      0.00   0.0  0
 5OI  CONST_28  N19  C5   O23  C9      0.00   0.0  0
 5OI  CONST_29  N20  C11  N21  C10     0.00   0.0  0
 5OI  CONST_30  N20  C8   C6   C10     0.00   0.0  0
 5OI  CONST_31  O23  C9   C4   N19     0.00   0.0  0
 5OI  CONST_32  C10  N21  C11  C17   180.00   0.0  0
 5OI  CONST_33  C8   N20  C11  C17   180.00   0.0  0
 5OI  CONST_34  C11  N21  C10  C15   180.00   0.0  0
 5OI  CONST_35  C8   C6   C10  C15   180.00   0.0  0
 5OI  CONST_36  C3   C6   C10  C15     0.00   0.0  0
 5OI  CONST_37  H26  C3   C7   C1    180.00   0.0  0
 5OI  CONST_38  H24  C1   C7   C3    180.00   0.0  0
 5OI  CONST_39  H28  C5   N19  C4    180.00   0.0  0
 5OI  CONST_40  H27  C4   N19  C5    180.00   0.0  0
 5OI  CONST_41  H25  C2   C8   C6    180.00   0.0  0
 5OI  CONST_42  H25  C2   C1   C7    180.00   0.0  0
 5OI  CONST_43  H27  C4   C9   C7      0.00   0.0  0
 5OI  CONST_44  H26  C3   C6   C8    180.00   0.0  0
 5OI  CONST_45  H24  C1   C2   C8    180.00   0.0  0
 5OI  CONST_46  H26  C3   C7   C9      0.00   0.0  0
 5OI  CONST_47  H24  C1   C7   C9      0.00   0.0  0
 5OI  CONST_48  H28  C5   O23  C9    180.00   0.0  0
 5OI  CONST_49  H26  C3   C6   C10     0.00   0.0  0
 5OI  CONST_50  H25  C2   C8   N20     0.00   0.0  0
 5OI  CONST_51  H27  C4   C9   O23   180.00   0.0  0
 5OI  Var_01    N21  C10  C15  C12     1.95  30.0  2
 5OI  Var_02    C6   C10  C15  C12  -178.06  30.0  2
 5OI  Var_03    H39  C15  C10  C6     58.49  30.0  2
 5OI  Var_04    H38  C15  C10  C6    -54.91  30.0  2
 5OI  Var_05    H39  C15  C10  N21  -121.50  30.0  2
 5OI  Var_06    H38  C15  C10  N21   125.11  30.0  2
 5OI  Var_07    H30  C12  C15  C10   179.23  30.0  3
 5OI  Var_08    H31  C12  C15  C10   -61.18  30.0  3
 5OI  Var_09    H29  C12  C15  C10    59.68  30.0  3
 5OI  Var_10    C17  C16  C18  C13  -176.18  30.0  1
 5OI  Var_11    C14  C18  C16  C17    60.69  30.0  3
 5OI  Var_12    H40  C16  C18  C13    62.09  30.0  1
 5OI  Var_13    H41  C16  C18  C13   -53.76  30.0  1
 5OI  Var_14    H37  C14  C18  C13    53.41  30.0  3
 5OI  Var_15    H35  C14  C18  C13   173.45  30.0  3
 5OI  Var_16    H36  C14  C18  C13   -66.00  30.0  3
 5OI  Var_17    H43  C18  C16  C17   -58.85  30.0  3
 5OI  Var_18    H37  C14  C18  C16   176.07  30.0  3
 5OI  Var_19    H35  C14  C18  C16   -63.88  30.0  3
 5OI  Var_20    H36  C14  C18  C16    56.66  30.0  3
 5OI  Var_21    H32  C13  C18  C16   177.76  30.0  3
 5OI  Var_22    H33  C13  C18  C16   -62.51  30.0  3
 5OI  Var_23    H34  C13  C18  C16    57.43  30.0  3
 5OI  Var_24    H40  C16  C18  C14   -61.04  30.0  1
 5OI  Var_25    H41  C16  C18  C14  -176.89  30.0  1
 5OI  Var_26    H32  C13  C18  C14   -58.13  30.0  3
 5OI  Var_27    H33  C13  C18  C14    61.60  30.0  3
 5OI  Var_28    H34  C13  C18  C14  -178.46  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
 5OI  chir_01  C17  N22  C16  C11  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
 5OI  plan-1  C4   0.020
 5OI  plan-1  C5   0.020
 5OI  plan-1  C7   0.020
 5OI  plan-1  C9   0.020
 5OI  plan-1  N19  0.020
 5OI  plan-1  O23  0.020
 5OI  plan-1  H27  0.020
 5OI  plan-1  H28  0.020
 5OI  plan-2  C17  0.020
 5OI  plan-2  C15  0.020
 5OI  plan-2  C11  0.020
 5OI  plan-2  C1   0.020
 5OI  plan-2  C2   0.020
 5OI  plan-2  C3   0.020
 5OI  plan-2  C6   0.020
 5OI  plan-2  C7   0.020
 5OI  plan-2  C8   0.020
 5OI  plan-2  C9   0.020
 5OI  plan-2  C10  0.020
 5OI  plan-2  N20  0.020
 5OI  plan-2  N21  0.020
 5OI  plan-2  H24  0.020
 5OI  plan-2  H25  0.020
 5OI  plan-2  H26  0.020

