# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 17:41:36 2020
#   Inital geometry file: a 127 line input string
#   Ligand name: 4-(2-chlorophenyl)-3-hydroxy-7,7-dimethyl-2-phenyl-2,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1(C)CC(=O)c2c(C1)nc3nn(c(O)c3c2c4ccccc4Cl)c5ccccc5
#
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
 O3Y  O3Y  4-(2-chlorophenyl)-3-hydroxy-7,7-dimethyl-2-phenyl-2,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one  ligand  50  30  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_O3Y
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
 O3Y  C2    C   CR56  0   0.403   0.6078  -1.5883  -0.3932
 O3Y  C3    C   CR56  0  -0.307   0.4374  -0.1778  -0.4187
 O3Y  C13   C   CR5   0   0.514   1.7434   0.3173  -0.3304
 O3Y  C15   C   CR6   0   0.337   3.9531  -0.7561  -0.1534
 O3Y  C16   C   CR16  0  -0.262   4.7339  -0.0097  -1.0252
 O3Y  C17   C   CR16  0  -0.230   6.1142  -0.0315  -0.8837
 O3Y  C18   C   CR16  0  -0.225   6.7054  -0.8007   0.1090
 O3Y  C19   C   CR16  0  -0.231   5.9129  -1.5529   0.9672
 O3Y  C20   C   CR16  0  -0.237   4.5325  -1.5314   0.8425
 O3Y  C23   C   CR6   0   0.060  -0.9447   1.8534  -0.4586
 O3Y  C24   C   CR6   0  -0.061  -1.2926   2.5470   0.6971
 O3Y  C25   C   CR16  0  -0.177  -1.2922   3.9304   0.7347
 O3Y  C26   C   CR16  0  -0.240  -0.9330   4.6450  -0.4002
 O3Y  C27   C   CR16  0  -0.211  -0.5708   3.9751  -1.5582
 O3Y  C28   C   CR16  0  -0.312  -0.5708   2.5865  -1.5823
 O3Y  C10   C   CR6   0   0.240  -1.6184  -1.9342  -0.5181
 O3Y  C4    C   CR6   0   0.303  -0.8425   0.3766  -0.4825
 O3Y  C5    C   CR6   0  -0.205  -1.8959  -0.5194  -0.5503
 O3Y  C6    C   C     0   0.341  -3.2915  -0.0376  -0.6356
 O3Y  C7    C   CH2   0  -0.523  -4.3968  -1.0629  -0.6387
 O3Y  C8    C   CT    0  -0.150  -4.0434  -2.3767   0.0537
 O3Y  C9    C   CH2   0  -0.470  -2.7619  -2.9020  -0.5907
 O3Y  N1    N   N     0  -0.422  -0.4237  -2.4544  -0.4379
 O3Y  N11   N   NR5   0  -0.437   2.5415  -0.7529  -0.2781
 O3Y  N12   N   N     0  -0.297   1.8745  -1.9373  -0.3036
 O3Y  O14   O   O     0  -0.358  -3.5467   1.1464  -0.7306
 O3Y  O30   O   OH1   0  -0.575   2.2448   1.5346  -0.2667
 O3Y  CL29  CL  CL    0  -0.100  -1.7343   1.6651   2.1180
 O3Y  H35   H   HCR6  0   0.254   4.2795   0.5690  -1.8179
 O3Y  H36   H   HCR6  0   0.243   6.7270   0.5474  -1.5613
 O3Y  H37   H   HCR6  0   0.237   7.7822  -0.8174   0.2127
 O3Y  H38   H   HCR6  0   0.238   6.3696  -2.1531   1.7428
 O3Y  H39   H   HCR6  0   0.259   3.9090  -2.1074   1.5127
 O3Y  H42   H   HCH3  0   0.225  -4.7677  -1.8019   2.0176
 O3Y  H40   H   HCH3  0   0.226  -3.5547  -3.0811   2.0498
 O3Y  H41   H   HCH3  0   0.234  -3.0702  -1.4116   1.7733
 O3Y  H43   H   HCH3  0   0.225  -6.1000  -3.0350   0.2849
 O3Y  H45   H   HCH3  0   0.216  -5.3446  -3.5736  -1.2162
 O3Y  H44   H   HCH3  0   0.225  -4.9169  -4.3432   0.3134
 O3Y  H46   H   HCR6  0   0.258  -1.5665   4.4481   1.6437
 O3Y  H47   H   HCR6  0   0.242  -0.9307   5.7260  -0.3693
 O3Y  H48   H   HCR6  0   0.239  -0.2832   4.5262  -2.4430
 O3Y  H49   H   HCR6  0   0.248  -0.2895   2.0615  -2.4868
 O3Y  H31   H   HCH2  0   0.263  -5.2895  -0.6078  -0.2021
 O3Y  H32   H   HCH2  0   0.253  -4.6347  -1.2591  -1.6925
 O3Y  H34   H   HCH2  0   0.247  -2.9584  -3.1197  -1.6479
 O3Y  H33   H   HCH2  0   0.261  -2.4511  -3.8425  -0.1321
 O3Y  H50   H   HOH1  0   0.482   1.5500   2.1980  -0.3859
 O3Y  C21   C   CH3   0  -0.627  -3.8431  -2.1518   1.5546
 O3Y  C22   C   CH3   0  -0.619  -5.1657  -3.3887  -0.1552

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
 O3Y  C26  C25   aromatic  1.388  0.020  1.388
 O3Y  C26  C27   aromatic  1.386  0.020  1.386
 O3Y  C25  C24   aromatic  1.384  0.020  1.384
 O3Y  C27  C28   aromatic  1.389  0.020  1.389
 O3Y  C24  CL29  single    1.730  0.020  1.730
 O3Y  C24  C23   aromatic  1.392  0.020  1.392
 O3Y  O30  C13   single    1.318  0.020  1.318
 O3Y  C17  C16   aromatic  1.388  0.020  1.388
 O3Y  C17  C18   aromatic  1.388  0.020  1.388
 O3Y  C28  C23   aromatic  1.393  0.020  1.393
 O3Y  C16  C15   aromatic  1.388  0.020  1.388
 O3Y  C18  C19   aromatic  1.389  0.020  1.389
 O3Y  C23  C4    single    1.481  0.020  1.481
 O3Y  C13  N11   aromatic  1.336  0.020  1.336
 O3Y  C13  C3    aromatic  1.399  0.020  1.399
 O3Y  C15  N11   single    1.417  0.020  1.417
 O3Y  C15  C20   aromatic  1.389  0.020  1.389
 O3Y  C19  C20   aromatic  1.386  0.020  1.386
 O3Y  N11  N12   aromatic  1.360  0.020  1.360
 O3Y  C4   C3    aromatic  1.396  0.020  1.396
 O3Y  C4   C5    aromatic  1.384  0.020  1.384
 O3Y  C3   C2    aromatic  1.421  0.020  1.421
 O3Y  O14  C6    double    1.215  0.020  1.215
 O3Y  C5   C6    single    1.479  0.020  1.479
 O3Y  C5   C10   aromatic  1.442  0.020  1.442
 O3Y  C6   C7    single    1.508  0.020  1.508
 O3Y  N12  C2    aromatic  1.317  0.020  1.317
 O3Y  C2   N1    aromatic  1.348  0.020  1.348
 O3Y  C10  N1    aromatic  1.305  0.020  1.305
 O3Y  C10  C9    single    1.500  0.020  1.500
 O3Y  C7   C8    single    1.527  0.020  1.527
 O3Y  C21  C8    single    1.531  0.020  1.531
 O3Y  C8   C9    single    1.528  0.020  1.528
 O3Y  C8   C22   single    1.526  0.020  1.526
 O3Y  C16  H35   single    0.930  0.020  1.080
 O3Y  C17  H36   single    0.930  0.020  1.080
 O3Y  C18  H37   single    0.930  0.020  1.080
 O3Y  C19  H38   single    0.930  0.020  1.080
 O3Y  C20  H39   single    0.930  0.020  1.080
 O3Y  C21  H42   single    0.970  0.020  1.090
 O3Y  C21  H40   single    0.970  0.020  1.090
 O3Y  C21  H41   single    0.970  0.020  1.090
 O3Y  C22  H43   single    0.970  0.020  1.090
 O3Y  C22  H45   single    0.970  0.020  1.090
 O3Y  C22  H44   single    0.970  0.020  1.090
 O3Y  C25  H46   single    0.930  0.020  1.080
 O3Y  C26  H47   single    0.930  0.020  1.080
 O3Y  C27  H48   single    0.930  0.020  1.080
 O3Y  C28  H49   single    0.930  0.020  1.080
 O3Y  C7   H31   single    0.970  0.020  1.090
 O3Y  C7   H32   single    0.970  0.020  1.090
 O3Y  C9   H34   single    0.970  0.020  1.090
 O3Y  C9   H33   single    0.970  0.020  1.090
 O3Y  O30  H50   single    0.850  0.020  0.980

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
 O3Y  N12   C2   N1   124.62  3.000
 O3Y  N1    C2   C3   123.06  3.000
 O3Y  N12   C2   C3   112.31  3.000
 O3Y  C4    C3   C13  135.88  3.000
 O3Y  C4    C3   C2   120.32  3.000
 O3Y  C13   C3   C2   103.78  3.000
 O3Y  O30   C13  N11  120.71  3.000
 O3Y  N11   C13  C3   106.05  3.000
 O3Y  O30   C13  C3   133.21  3.000
 O3Y  N11   C15  C20  118.68  3.000
 O3Y  C20   C15  C16  121.06  3.000
 O3Y  N11   C15  C16  120.25  3.000
 O3Y  H35   C16  C17  120.07  3.000
 O3Y  H35   C16  C15  120.78  3.000
 O3Y  C17   C16  C15  119.14  3.000
 O3Y  H36   C17  C18  120.22  3.000
 O3Y  H36   C17  C16  119.42  3.000
 O3Y  C18   C17  C16  120.35  3.000
 O3Y  H37   C18  C19  120.01  3.000
 O3Y  H37   C18  C17  120.07  3.000
 O3Y  C19   C18  C17  119.92  3.000
 O3Y  H38   C19  C20  119.57  3.000
 O3Y  H38   C19  C18  120.16  3.000
 O3Y  C20   C19  C18  120.27  3.000
 O3Y  H39   C20  C19  120.67  3.000
 O3Y  H39   C20  C15  120.08  3.000
 O3Y  C19   C20  C15  119.25  3.000
 O3Y  C4    C23  C28  119.57  3.000
 O3Y  C4    C23  C24  121.85  3.000
 O3Y  C28   C23  C24  118.34  3.000
 O3Y  CL29  C24  C25  119.17  3.000
 O3Y  CL29  C24  C23  119.46  3.000
 O3Y  C25   C24  C23  121.37  3.000
 O3Y  H46   C25  C26  120.42  3.000
 O3Y  H46   C25  C24  120.09  3.000
 O3Y  C26   C25  C24  119.50  3.000
 O3Y  H47   C26  C27  120.43  3.000
 O3Y  H47   C26  C25  119.45  3.000
 O3Y  C27   C26  C25  120.12  3.000
 O3Y  H48   C27  C28  119.69  3.000
 O3Y  H48   C27  C26  120.45  3.000
 O3Y  C28   C27  C26  119.85  3.000
 O3Y  H49   C28  C27  119.95  3.000
 O3Y  H49   C28  C23  119.23  3.000
 O3Y  C27   C28  C23  120.82  3.000
 O3Y  N1    C10  C9   116.33  3.000
 O3Y  C9    C10  C5   119.03  3.000
 O3Y  N1    C10  C5   124.63  3.000
 O3Y  C5    C4   C23  126.42  3.000
 O3Y  C5    C4   C3   116.28  3.000
 O3Y  C23   C4   C3   117.30  3.000
 O3Y  C6    C5   C4   120.67  3.000
 O3Y  C6    C5   C10  120.16  3.000
 O3Y  C4    C5   C10  119.17  3.000
 O3Y  O14   C6   C7   120.57  3.000
 O3Y  C7    C6   C5   118.07  3.000
 O3Y  O14   C6   C5   121.34  3.000
 O3Y  H32   C7   H31  106.31  3.000
 O3Y  H32   C7   C8   109.37  3.000
 O3Y  H31   C7   C8   111.48  3.000
 O3Y  H32   C7   C6   106.40  3.000
 O3Y  H31   C7   C6   108.35  3.000
 O3Y  C8    C7   C6   114.49  3.000
 O3Y  C9    C8   C7   107.39  3.000
 O3Y  C9    C8   C22  109.35  3.000
 O3Y  C7    C8   C22  109.78  3.000
 O3Y  C22   C8   C21  109.15  3.000
 O3Y  C9    C8   C21  110.75  3.000
 O3Y  C7    C8   C21  110.40  3.000
 O3Y  H33   C9   H34  106.55  3.000
 O3Y  H33   C9   C8   110.98  3.000
 O3Y  H34   C9   C8   108.94  3.000
 O3Y  H33   C9   C10  108.57  3.000
 O3Y  H34   C9   C10  108.13  3.000
 O3Y  C8    C9   C10  113.41  3.000
 O3Y  C10   N1   C2   116.52  3.000
 O3Y  N12   N11  C15  119.23  3.000
 O3Y  N12   N11  C13  113.83  3.000
 O3Y  C15   N11  C13  126.89  3.000
 O3Y  N11   N12  C2   104.02  3.000
 O3Y  H50   O30  C13  110.73  3.000
 O3Y  H41   C21  H40  107.41  3.000
 O3Y  H41   C21  H42  107.28  3.000
 O3Y  H40   C21  H42  107.71  3.000
 O3Y  H41   C21  C8   112.86  3.000
 O3Y  H40   C21  C8   110.75  3.000
 O3Y  H42   C21  C8   110.62  3.000
 O3Y  H44   C22  H45  107.84  3.000
 O3Y  H44   C22  H43  107.77  3.000
 O3Y  H45   C22  H43  107.85  3.000
 O3Y  H44   C22  C8   110.70  3.000
 O3Y  H45   C22  C8   111.47  3.000
 O3Y  H43   C22  C8   111.06  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
 O3Y  CONST_01  N11   C13  C3   C2     0.00   0.0  0
 O3Y  CONST_02  C23   C4   C3   C2   180.00   0.0  0
 O3Y  CONST_03  C5    C4   C3   C2     0.00   0.0  0
 O3Y  CONST_04  C13   N11  N12  C2     0.00   0.0  0
 O3Y  CONST_05  C15   N11  N12  C2   180.00   0.0  0
 O3Y  CONST_06  C5    C10  N1   C2     0.00   0.0  0
 O3Y  CONST_07  C15   N11  C13  C3   180.00   0.0  0
 O3Y  CONST_08  N12   N11  C13  C3     0.00   0.0  0
 O3Y  CONST_11  C10   C5   C4   C3     0.00   0.0  0
 O3Y  CONST_12  N11   N12  C2   C3     0.00   0.0  0
 O3Y  CONST_13  C10   N1   C2   C3     0.00   0.0  0
 O3Y  CONST_16  C23   C4   C3   C13    0.00   0.0  0
 O3Y  CONST_17  C5    C4   C3   C13  180.00   0.0  0
 O3Y  CONST_18  N12   C2   C3   C13    0.00   0.0  0
 O3Y  CONST_19  N1    C2   C3   C13  180.00   0.0  0
 O3Y  CONST_20  C18   C17  C16  C15    0.00   0.0  0
 O3Y  CONST_21  C18   C19  C20  C15    0.00   0.0  0
 O3Y  CONST_22  C19   C18  C17  C16    0.00   0.0  0
 O3Y  CONST_24  C19   C20  C15  C16    0.00   0.0  0
 O3Y  CONST_25  N11   C15  C16  C17  180.00   0.0  0
 O3Y  CONST_26  C20   C15  C16  C17    0.00   0.0  0
 O3Y  CONST_27  C20   C19  C18  C17    0.00   0.0  0
 O3Y  CONST_28  N11   C15  C20  C19  180.00   0.0  0
 O3Y  CONST_30  C26   C25  C24  C23    0.00   0.0  0
 O3Y  CONST_31  C26   C27  C28  C23    0.00   0.0  0
 O3Y  CONST_32  C10   C5   C4   C23  180.00   0.0  0
 O3Y  CONST_33  C27   C26  C25  C24    0.00   0.0  0
 O3Y  CONST_34  C27   C28  C23  C24    0.00   0.0  0
 O3Y  CONST_36  C28   C27  C26  C25    0.00   0.0  0
 O3Y  CONST_37  C28   C23  C24  C25    0.00   0.0  0
 O3Y  CONST_38  C4    C23  C24  C25  180.00   0.0  0
 O3Y  CONST_39  C4    C23  C28  C27  180.00   0.0  0
 O3Y  CONST_41  N12   C2   N1   C10  180.00   0.0  0
 O3Y  CONST_42  N11   C13  C3   C4   180.00   0.0  0
 O3Y  CONST_43  N12   C2   C3   C4   180.00   0.0  0
 O3Y  CONST_44  N1    C2   C3   C4     0.00   0.0  0
 O3Y  CONST_45  N1    C10  C5   C4     0.00   0.0  0
 O3Y  CONST_46  N11   N12  C2   N1   180.00   0.0  0
 O3Y  CONST_47  C6    C5   C4   C23    0.00   0.0  0
 O3Y  CONST_48  O30   C13  C3   C2   180.00   0.0  0
 O3Y  CONST_49  O30   C13  N11  C15    0.00   0.0  0
 O3Y  CONST_50  CL29  C24  C25  C26  180.00   0.0  0
 O3Y  CONST_51  CL29  C24  C23  C28  180.00   0.0  0
 O3Y  CONST_52  CL29  C24  C23  C4     0.00   0.0  0
 O3Y  CONST_53  O30   C13  C3   C4     0.00   0.0  0
 O3Y  CONST_54  O30   C13  N11  N12  180.00   0.0  0
 O3Y  CONST_55  H36   C17  C16  C15  180.00   0.0  0
 O3Y  CONST_56  H38   C19  C20  C15  180.00   0.0  0
 O3Y  CONST_57  H37   C18  C17  C16  180.00   0.0  0
 O3Y  CONST_58  H39   C20  C15  C16  180.00   0.0  0
 O3Y  CONST_59  H35   C16  C17  C18  180.00   0.0  0
 O3Y  CONST_60  H46   C25  C24  C23  180.00   0.0  0
 O3Y  CONST_61  H48   C27  C28  C23  180.00   0.0  0
 O3Y  CONST_62  H47   C26  C25  C24  180.00   0.0  0
 O3Y  CONST_63  H49   C28  C23  C24  180.00   0.0  0
 O3Y  Var_01    C7    C6   C5   C10    2.07  30.0  1
 O3Y  Var_02    C7    C8   C9   C10   57.11  30.0  1
 O3Y  Var_03    C8    C7   C6   C5    26.27  30.0  1
 O3Y  Var_04    C8    C9   C10  C5   -31.77  30.0  1
 O3Y  Var_05    C9    C8   C7   C6   -54.50  30.0  1
 O3Y  Var_06    H42   C21  C8   C7    62.70  30.0  3
 O3Y  Var_07    H43   C22  C8   C7   -61.74  30.0  3

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
 O3Y  plan-1  C15   0.020
 O3Y  plan-1  C16   0.020
 O3Y  plan-1  C17   0.020
 O3Y  plan-1  C18   0.020
 O3Y  plan-1  C19   0.020
 O3Y  plan-1  C20   0.020
 O3Y  plan-1  N11   0.020
 O3Y  plan-1  H35   0.020
 O3Y  plan-1  H36   0.020
 O3Y  plan-1  H37   0.020
 O3Y  plan-1  H38   0.020
 O3Y  plan-1  H39   0.020
 O3Y  plan-2  C23   0.020
 O3Y  plan-2  C24   0.020
 O3Y  plan-2  C25   0.020
 O3Y  plan-2  C26   0.020
 O3Y  plan-2  C27   0.020
 O3Y  plan-2  C28   0.020
 O3Y  plan-2  C4    0.020
 O3Y  plan-2  CL29  0.020
 O3Y  plan-2  H46   0.020
 O3Y  plan-2  H47   0.020
 O3Y  plan-2  H48   0.020
 O3Y  plan-2  H49   0.020
 O3Y  plan-3  C2    0.020
 O3Y  plan-3  C3    0.020
 O3Y  plan-3  C13   0.020
 O3Y  plan-3  C15   0.020
 O3Y  plan-3  C23   0.020
 O3Y  plan-3  C10   0.020
 O3Y  plan-3  C4    0.020
 O3Y  plan-3  C5    0.020
 O3Y  plan-3  C6    0.020
 O3Y  plan-3  C9    0.020
 O3Y  plan-3  N1    0.020
 O3Y  plan-3  N11   0.020
 O3Y  plan-3  N12   0.020
 O3Y  plan-3  O30   0.020
 O3Y  plan-4  C5    0.020
 O3Y  plan-4  C6    0.020
 O3Y  plan-4  C7    0.020
 O3Y  plan-4  O14   0.020

