# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 21:32:44 2020
#   Inital geometry file: a 121 line input string
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]\1Nc2nc3c(cccc3c4[nH]c5[C@H](CNC(=O)c5c4)C\C=C\1)nc2C
#
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
 5QO  5QO  'None                     '  ligand  48  27  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_5QO
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
 5QO  C15  C  CH2   0  -0.256   4.2594   1.0982   0.6408
 5QO  N5   N  NH1   0  -0.660   4.9709  -0.1434   0.3756
 5QO  C16  C  C     0   0.465   4.3654  -1.3587   0.2972
 5QO  O1   O  O     0  -0.497   4.9897  -2.4128   0.3596
 5QO  C12  C  CR5   0  -0.159   2.9245  -1.2750   0.0929
 5QO  C13  C  CR15  0  -0.437   1.9061  -2.2622   0.1078
 5QO  C10  C  CR5   0   0.365   0.7155  -1.6066  -0.1389
 5QO  N4   N  NR15  0  -0.727   1.0153  -0.2807  -0.3263
 5QO  C11  C  CR5   0   0.408   2.3236  -0.0616  -0.1780
 5QO  C14  C  CH1   0  -0.341   3.0274   1.2463  -0.2515
 5QO  C17  C  CH2   0  -0.515   2.1442   2.4281   0.1750
 5QO  C21  C  C1    0  -0.217   1.1058   2.7634  -0.8556
 5QO  C20  C  C1    0  -0.221  -0.2095   2.9172  -0.7037
 5QO  C18  C  CH1   0  -0.134  -1.0105   2.8266   0.5708
 5QO  C19  C  CH3   0  -0.676  -1.1721   4.2093   1.1953
 5QO  N3   N  NH1   0  -0.690  -2.3355   2.2730   0.3336
 5QO  C2   C  CR6   0   0.492  -2.5666   0.9666   0.1173
 5QO  N2   N  N     0  -0.549  -1.5506   0.1534   0.0216
 5QO  C3   C  CR66  0   0.273  -1.7643  -1.1756  -0.1250
 5QO  C5   C  CR6   0  -0.017  -0.6636  -2.0783  -0.2003
 5QO  C6   C  CR16  0  -0.377  -0.9445  -3.4289  -0.3171
 5QO  C7   C  CR16  0  -0.247  -2.2577  -3.9119  -0.3644
 5QO  C8   C  CR16  0  -0.331  -3.3229  -3.0446  -0.3095
 5QO  C4   C  CR66  0   0.207  -3.0824  -1.6676  -0.1896
 5QO  N1   N  N     0  -0.409  -4.1377  -0.8022  -0.1342
 5QO  C1   C  CR6   0   0.163  -3.9261   0.4642   0.0089
 5QO  C9   C  CH3   0  -0.766  -5.0833   1.4061   0.0678
 5QO  H1   H  HCH2  0   0.232   3.9466   1.1485   1.6912
 5QO  H2   H  HCH2  0   0.263   4.9489   1.9230   0.4670
 5QO  H3   H  HNH1  0   0.394   5.9563  -0.1534   0.5904
 5QO  H4   H  HCR5  0   0.250   2.0291  -3.3160   0.3034
 5QO  H5   H  HNR5  0   0.446   0.2806   0.4122  -0.4270
 5QO  H6   H  HCH1  0   0.270   3.3658   1.4211  -1.2815
 5QO  H7   H  HCH2  0   0.252   1.7056   2.2298   1.1559
 5QO  H8   H  HCH2  0   0.270   2.7907   3.3036   0.2991
 5QO  H9   H  H     0   0.250   1.5020   2.9150  -1.8563
 5QO  H10  H  H     0   0.249  -0.7878   3.1938  -1.5808
 5QO  H11  H  HCH1  0   0.255  -0.4972   2.1821   1.2905
 5QO  H12  H  HCH3  0   0.236  -1.6618   4.8992   0.5058
 5QO  H13  H  HCH3  0   0.246  -1.7636   4.1563   2.1104
 5QO  H14  H  HCH3  0   0.250  -0.1963   4.6217   1.4451
 5QO  H15  H  HNH1  0   0.416  -3.1155   2.9080   0.3628
 5QO  H16  H  HCR6  0   0.255  -0.1269  -4.1359  -0.3809
 5QO  H17  H  HCR6  0   0.260  -2.4262  -4.9766  -0.4545
 5QO  H18  H  HCR6  0   0.261  -4.3448  -3.3987  -0.3561
 5QO  H19  H  HCH3  0   0.263  -5.1186   1.9304   1.0256
 5QO  H20  H  HCH3  0   0.262  -5.0170   2.1654  -0.7147
 5QO  H21  H  HCH3  0   0.273  -6.0167   0.8633  -0.0578

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
 5QO  C7   C6   aromatic  1.400  0.020  1.400
 5QO  C7   C8   aromatic  1.375  0.020  1.375
 5QO  C6   C5   single    1.384  0.020  1.384
 5QO  O1   C16  double    1.227  0.020  1.227
 5QO  C8   C4   aromatic  1.403  0.020  1.403
 5QO  C13  C12  aromatic  1.418  0.020  1.418
 5QO  C13  C10  aromatic  1.381  0.020  1.381
 5QO  C5   C10  aromatic  1.459  0.020  1.459
 5QO  C5   C3   aromatic  1.426  0.020  1.426
 5QO  C16  C12  single    1.458  0.020  1.458
 5QO  C16  N5   single    1.360  0.020  1.360
 5QO  C12  C11  aromatic  1.381  0.020  1.381
 5QO  C10  N4   aromatic  1.372  0.020  1.372
 5QO  C4   C3   single    1.408  0.020  1.408
 5QO  C4   N1   aromatic  1.366  0.020  1.366
 5QO  C3   N2   aromatic  1.354  0.020  1.354
 5QO  N5   C15  single    1.455  0.020  1.455
 5QO  N4   C11  aromatic  1.335  0.020  1.335
 5QO  C11  C14  single    1.487  0.020  1.487
 5QO  N1   C1   aromatic  1.292  0.020  1.292
 5QO  N2   C2   aromatic  1.305  0.020  1.305
 5QO  C15  C14  single    1.528  0.020  1.528
 5QO  C14  C17  single    1.536  0.020  1.536
 5QO  C1   C2   single    1.453  0.020  1.453
 5QO  C1   C9   single    1.493  0.020  1.493
 5QO  C2   N3   single    1.344  0.020  1.344
 5QO  C17  C21  single    1.501  0.020  1.501
 5QO  C21  C20  double    1.333  0.020  1.333
 5QO  N3   C18  single    1.455  0.020  1.455
 5QO  C20  C18  single    1.508  0.020  1.508
 5QO  C18  C19  single    1.526  0.020  1.526
 5QO  C15  H1   single    0.970  0.020  1.090
 5QO  C15  H2   single    0.970  0.020  1.090
 5QO  N5   H3   single    0.890  0.020  1.040
 5QO  C13  H4   single    0.930  0.020  1.080
 5QO  N4   H5   single    0.860  0.020  1.020
 5QO  C14  H6   single    0.970  0.020  1.090
 5QO  C17  H7   single    0.970  0.020  1.090
 5QO  C17  H8   single    0.970  0.020  1.090
 5QO  C21  H9   single    0.930  0.020  1.080
 5QO  C20  H10  single    0.930  0.020  1.080
 5QO  C18  H11  single    0.970  0.020  1.090
 5QO  C19  H12  single    0.970  0.020  1.090
 5QO  C19  H13  single    0.970  0.020  1.090
 5QO  C19  H14  single    0.970  0.020  1.090
 5QO  N3   H15  single    0.860  0.020  1.020
 5QO  C6   H16  single    0.930  0.020  1.080
 5QO  C7   H17  single    0.930  0.020  1.080
 5QO  C8   H18  single    0.930  0.020  1.080
 5QO  C9   H19  single    0.970  0.020  1.090
 5QO  C9   H20  single    0.970  0.020  1.090
 5QO  C9   H21  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
 5QO  H2   C15  H1   107.37  3.000
 5QO  H2   C15  C14  110.11  3.000
 5QO  H1   C15  C14  108.95  3.000
 5QO  H2   C15  N5   107.91  3.000
 5QO  H1   C15  N5   110.67  3.000
 5QO  C14  C15  N5   111.73  3.000
 5QO  H3   N5   C16  116.00  3.000
 5QO  H3   N5   C15  116.57  3.000
 5QO  C16  N5   C15  123.72  3.000
 5QO  C12  C16  O1   124.02  3.000
 5QO  C12  C16  N5   113.38  3.000
 5QO  O1   C16  N5   122.57  3.000
 5QO  C11  C12  C13  107.53  3.000
 5QO  C11  C12  C16  120.53  3.000
 5QO  C13  C12  C16  131.94  3.000
 5QO  H4   C13  C10  126.46  3.000
 5QO  H4   C13  C12  126.86  3.000
 5QO  C10  C13  C12  106.66  3.000
 5QO  C5   C10  N4   120.88  3.000
 5QO  N4   C10  C13  107.13  3.000
 5QO  C5   C10  C13  131.98  3.000
 5QO  H5   N4   C11  127.48  3.000
 5QO  H5   N4   C10  121.00  3.000
 5QO  C11  N4   C10  110.95  3.000
 5QO  C14  C11  N4   127.07  3.000
 5QO  C14  C11  C12  125.21  3.000
 5QO  N4   C11  C12  107.70  3.000
 5QO  H6   C14  C17  108.37  3.000
 5QO  H6   C14  C11  109.40  3.000
 5QO  C17  C14  C11  113.01  3.000
 5QO  H6   C14  C15  108.34  3.000
 5QO  C17  C14  C15  112.08  3.000
 5QO  C11  C14  C15  105.51  3.000
 5QO  H8   C17  H7   106.28  3.000
 5QO  H8   C17  C21  107.91  3.000
 5QO  H7   C17  C21  112.28  3.000
 5QO  H8   C17  C14  107.89  3.000
 5QO  H7   C17  C14  109.91  3.000
 5QO  C21  C17  C14  112.28  3.000
 5QO  H9   C21  C20  116.65  3.000
 5QO  H9   C21  C17  114.28  3.000
 5QO  C20  C21  C17  129.07  3.000
 5QO  H10  C20  C18  114.51  3.000
 5QO  H10  C20  C21  117.56  3.000
 5QO  C18  C20  C21  127.84  3.000
 5QO  H11  C18  N3   108.08  3.000
 5QO  H11  C18  C19  108.32  3.000
 5QO  N3   C18  C19  108.36  3.000
 5QO  H11  C18  C20  110.01  3.000
 5QO  C19  C18  C20  110.35  3.000
 5QO  N3   C18  C20  111.63  3.000
 5QO  H14  C19  H13  108.18  3.000
 5QO  H14  C19  H12  107.92  3.000
 5QO  H13  C19  H12  108.50  3.000
 5QO  H14  C19  C18  110.02  3.000
 5QO  H13  C19  C18  110.90  3.000
 5QO  H12  C19  C18  111.21  3.000
 5QO  H15  N3   C2   119.00  3.000
 5QO  H15  N3   C18  117.45  3.000
 5QO  C2   N3   C18  123.53  3.000
 5QO  C1   C2   N2   120.49  3.000
 5QO  C1   C2   N3   120.58  3.000
 5QO  N2   C2   N3   118.92  3.000
 5QO  C3   N2   C2   119.79  3.000
 5QO  C4   C3   C5   119.93  3.000
 5QO  C4   C3   N2   119.71  3.000
 5QO  C5   C3   N2   120.36  3.000
 5QO  C6   C5   C3   117.74  3.000
 5QO  C3   C5   C10  121.53  3.000
 5QO  C6   C5   C10  120.72  3.000
 5QO  H16  C6   C7   118.75  3.000
 5QO  H16  C6   C5   119.26  3.000
 5QO  C7   C6   C5   121.99  3.000
 5QO  H17  C7   C8   120.24  3.000
 5QO  H17  C7   C6   119.24  3.000
 5QO  C8   C7   C6   120.52  3.000
 5QO  H18  C8   C4   119.11  3.000
 5QO  H18  C8   C7   121.56  3.000
 5QO  C4   C8   C7   119.33  3.000
 5QO  N1   C4   C8   119.54  3.000
 5QO  N1   C4   C3   119.99  3.000
 5QO  C8   C4   C3   120.48  3.000
 5QO  C1   N1   C4   119.94  3.000
 5QO  C9   C1   N1   119.72  3.000
 5QO  C9   C1   C2   120.26  3.000
 5QO  N1   C1   C2   120.02  3.000
 5QO  H21  C9   H20  108.44  3.000
 5QO  H21  C9   H19  108.26  3.000
 5QO  H20  C9   H19  107.24  3.000
 5QO  H21  C9   C1   110.23  3.000
 5QO  H20  C9   C1   111.30  3.000
 5QO  H19  C9   C1   111.25  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
 5QO  CONST_01  C5   C10  C13  C12   180.00   0.0  0
 5QO  CONST_02  N4   C10  C13  C12     0.00   0.0  0
 5QO  CONST_03  C10  N4   C11  C12     0.00   0.0  0
 5QO  CONST_04  N4   C11  C12  C13     0.00   0.0  0
 5QO  CONST_07  C11  N4   C10  C13     0.00   0.0  0
 5QO  CONST_08  C11  C12  C13  C10     0.00   0.0  0
 5QO  CONST_09  C7   C6   C5   C10   180.00   0.0  0
 5QO  CONST_10  C4   C3   C5   C10   180.00   0.0  0
 5QO  CONST_11  N2   C3   C5   C10     0.00   0.0  0
 5QO  CONST_12  C6   C5   C10  N4    180.00   0.0  0
 5QO  CONST_14  C5   C10  N4   C11   180.00   0.0  0
 5QO  CONST_15  C5   C3   N2   C2    180.00   0.0  0
 5QO  CONST_16  C4   C3   N2   C2      0.00   0.0  0
 5QO  CONST_17  C4   N1   C1   C2      0.00   0.0  0
 5QO  CONST_18  C6   C5   C3   N2    180.00   0.0  0
 5QO  CONST_19  C8   C4   C3   N2    180.00   0.0  0
 5QO  CONST_20  N1   C4   C3   N2      0.00   0.0  0
 5QO  CONST_21  N1   C1   C2   N2      0.00   0.0  0
 5QO  CONST_22  C7   C6   C5   C3      0.00   0.0  0
 5QO  CONST_23  C7   C8   C4   C3      0.00   0.0  0
 5QO  CONST_24  C1   N1   C4   C3      0.00   0.0  0
 5QO  CONST_25  C1   C2   N2   C3      0.00   0.0  0
 5QO  CONST_26  C8   C7   C6   C5      0.00   0.0  0
 5QO  CONST_27  C8   C4   C3   C5      0.00   0.0  0
 5QO  CONST_28  N1   C4   C3   C5    180.00   0.0  0
 5QO  CONST_29  C4   C8   C7   C6      0.00   0.0  0
 5QO  CONST_30  C4   C3   C5   C6      0.00   0.0  0
 5QO  CONST_31  N1   C4   C8   C7    180.00   0.0  0
 5QO  CONST_32  C1   N1   C4   C8    180.00   0.0  0
 5QO  CONST_33  N2   C2   N3   C18     0.00   0.0  0
 5QO  CONST_34  C1   C2   N3   C18   180.00   0.0  0
 5QO  CONST_36  C18  C20  C21  C17     0.00   0.0  0
 5QO  CONST_37  C9   C1   C2   N3      0.00   0.0  0
 5QO  CONST_38  C9   C1   C2   N2    180.00   0.0  0
 5QO  CONST_39  C9   C1   N1   C4    180.00   0.0  0
 5QO  CONST_41  H4   C13  C12  C16     0.00   0.0  0
 5QO  CONST_42  H5   N4   C11  C12   180.00   0.0  0
 5QO  CONST_43  H16  C6   C5   C10     0.00   0.0  0
 5QO  CONST_44  H18  C8   C4   C3    180.00   0.0  0
 5QO  CONST_45  H17  C7   C6   C5    180.00   0.0  0
 5QO  CONST_46  H15  N3   C2   N2    180.00   0.0  0
 5QO  CONST_47  H3   N5   C16  C12   180.00   0.0  0
 5QO  CONST_48  H10  C20  C21  C17   180.00   0.0  0
 5QO  CONST_49  H9   C21  C20  C18   180.00   0.0  0
 5QO  Var_01    C13  C12  C16  N5   -171.75  30.0  2
 5QO  Var_02    C14  C15  N5   C16   -48.54  30.0  1
 5QO  Var_03    C20  C21  C17  C14   128.68  30.0  1
 5QO  Var_04    H19  C9   C1   C2    -61.54  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
 5QO  chir_01  C14  C11  C15  C17  positiv
 5QO  chir_02  C18  N3   C20  C19  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
 5QO  plan-1  C10  0.020
 5QO  plan-1  N3   0.020
 5QO  plan-1  C2   0.020
 5QO  plan-1  N2   0.020
 5QO  plan-1  C3   0.020
 5QO  plan-1  C5   0.020
 5QO  plan-1  C6   0.020
 5QO  plan-1  C7   0.020
 5QO  plan-1  C8   0.020
 5QO  plan-1  C4   0.020
 5QO  plan-1  N1   0.020
 5QO  plan-1  C1   0.020
 5QO  plan-1  C9   0.020
 5QO  plan-1  H16  0.020
 5QO  plan-1  H17  0.020
 5QO  plan-1  H18  0.020
 5QO  plan-2  C16  0.020
 5QO  plan-2  C12  0.020
 5QO  plan-2  C13  0.020
 5QO  plan-2  C10  0.020
 5QO  plan-2  N4   0.020
 5QO  plan-2  C11  0.020
 5QO  plan-2  C14  0.020
 5QO  plan-2  C5   0.020
 5QO  plan-2  H4   0.020
 5QO  plan-2  H5   0.020
 5QO  plan-3  C18  0.020
 5QO  plan-3  N3   0.020
 5QO  plan-3  C2   0.020
 5QO  plan-3  H15  0.020
 5QO  plan-4  C15  0.020
 5QO  plan-4  N5   0.020
 5QO  plan-4  C16  0.020
 5QO  plan-4  O1   0.020
 5QO  plan-4  C12  0.020
 5QO  plan-4  H3   0.020
 5QO  plan-5  C17  0.020
 5QO  plan-5  C21  0.020
 5QO  plan-5  C20  0.020
 5QO  plan-5  C18  0.020
 5QO  plan-5  H9   0.020
 5QO  plan-5  H10  0.020

