# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 11:43:59 2020
#   Inital geometry file: a 119 line input string
#   Ligand name: 3-hydroxy-7,7-dimethyl-2-phenyl-4-(thiophen-2-yl)-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)c3c2c4sccc4)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
 O3V  O3V  3-hydroxy-7,7-dimethyl-2-phenyl-4-(thiophen-2-yl)-2,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one  ligand  47  28  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_O3V
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
 O3V  C2   C  CR56  0   0.415   0.5637   1.4542  -0.1078
 O3V  C3   C  CR56  0  -0.308   0.4089   0.0464  -0.2162
 O3V  C4   C  CR6   0   0.329  -0.8639  -0.5183  -0.3355
 O3V  C5   C  CR6   0  -0.218  -1.9296   0.3705  -0.3541
 O3V  C6   C  C     0   0.343  -3.3205  -0.1067  -0.5254
 O3V  C7   C  CH2   0  -0.536  -4.4349   0.9085  -0.4628
 O3V  C8   C  CT    0  -0.145  -4.1053   2.1795   0.3157
 O3V  C13  C  CR5   0   0.533   1.7184  -0.4414  -0.1340
 O3V  C17  C  CR16  0  -0.253   5.9663  -0.1428   1.0430
 O3V  C18  C  CR16  0  -0.248   6.6785   0.7371   0.2400
 O3V  C19  C  CR16  0  -0.254   6.0019   1.5785  -0.6341
 O3V  C20  C  CR16  0  -0.269   4.6189   1.5371  -0.7148
 O3V  C21  C  CH3   0  -0.639  -5.2282   3.1979   0.1410
 O3V  C22  C  CH3   0  -0.639  -3.9372   1.8742   1.8062
 O3V  C25  C  CR15  0  -0.255  -0.5085  -2.7805  -1.4269
 O3V  C26  C  CR15  0  -0.175  -0.6527  -4.1664  -1.1398
 O3V  C27  C  CR15  0  -0.454  -1.1716  -4.3890   0.0974
 O3V  C10  C  CR6   0   0.249  -1.6653   1.7838  -0.2328
 O3V  C15  C  CR6   0   0.336   3.9170   0.6502   0.0918
 O3V  C16  C  CR16  0  -0.280   4.5807  -0.1868   0.9790
 O3V  C24  C  CR5   0  -0.296  -0.9457  -1.9847  -0.4053
 O3V  C9   C  CH2   0  -0.484  -2.8145   2.7469  -0.2697
 O3V  N1   N  N     0  -0.464  -0.4771   2.3102  -0.1093
 O3V  N11  N  NR5   0  -0.432   2.5032   0.6314   0.0085
 O3V  N12  N  N     0  -0.339   1.8241   1.8100   0.0259
 O3V  O14  O  O     0  -0.397  -3.5674  -1.2746  -0.7504
 O3V  O23  O  OH1   0  -0.580   2.2310  -1.6525  -0.1949
 O3V  S28  S  S2    0   0.256  -1.5022  -2.9244   0.9212
 O3V  H29  H  HCH2  0   0.278  -4.6675   1.1725  -1.5028
 O3V  H30  H  HCH2  0   0.271  -5.3261   0.4148  -0.0666
 O3V  H35  H  HCR6  0   0.267   7.7584   0.7710   0.2986
 O3V  H36  H  HCR6  0   0.268   6.5527   2.2679  -1.2599
 O3V  H37  H  HCR6  0   0.276   4.0885   2.1865  -1.3982
 O3V  H39  H  HCH3  0   0.233  -6.1687   2.8191   0.5453
 O3V  H38  H  HCH3  0   0.233  -4.9908   4.1267   0.6640
 O3V  H40  H  HCH3  0   0.228  -5.3896   3.4392  -0.9114
 O3V  H41  H  HCH3  0   0.229  -3.1661   1.1268   2.0045
 O3V  H42  H  HCH3  0   0.234  -3.6632   2.7770   2.3554
 O3V  H43  H  HCH3  0   0.235  -4.8703   1.4976   2.2289
 O3V  H45  H  HCR5  0   0.287  -0.1304  -2.3882  -2.3615
 O3V  H46  H  HCR5  0   0.275  -0.3749  -4.9553  -1.8234
 O3V  H47  H  HCR5  0   0.303  -1.3685  -5.3358   0.5762
 O3V  H33  H  HCR6  0   0.280   4.0311  -0.8529   1.6297
 O3V  H32  H  HCH2  0   0.270  -2.9899   3.0261  -1.3163
 O3V  H31  H  HCH2  0   0.262  -2.5178   3.6609   0.2481
 O3V  H44  H  HOH1  0   0.507   1.5352  -2.3014  -0.3870
 O3V  H34  H  HCR6  0   0.269   6.4875  -0.7911   1.7347

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
 O3V  C26  C27  aromatic  1.360  0.020  1.360
 O3V  C26  C25  aromatic  1.423  0.020  1.423
 O3V  C27  S28  aromatic  1.713  0.020  1.713
 O3V  O14  C6   double    1.215  0.020  1.215
 O3V  C25  C24  aromatic  1.367  0.020  1.367
 O3V  C7   C6   single    1.509  0.020  1.509
 O3V  C7   C8   single    1.527  0.020  1.527
 O3V  C6   C5   single    1.480  0.020  1.480
 O3V  C24  S28  aromatic  1.718  0.020  1.718
 O3V  C24  C4   single    1.470  0.020  1.470
 O3V  C4   C5   aromatic  1.388  0.020  1.388
 O3V  C4   C3   aromatic  1.398  0.020  1.398
 O3V  C5   C10  aromatic  1.443  0.020  1.443
 O3V  C22  C8   single    1.531  0.020  1.531
 O3V  C8   C21  single    1.526  0.020  1.526
 O3V  C8   C9   single    1.527  0.020  1.527
 O3V  O23  C13  single    1.317  0.020  1.317
 O3V  C3   C13  aromatic  1.400  0.020  1.400
 O3V  C3   C2   aromatic  1.420  0.020  1.420
 O3V  C10  C9   single    1.500  0.020  1.500
 O3V  C10  N1   aromatic  1.306  0.020  1.306
 O3V  C13  N11  aromatic  1.337  0.020  1.337
 O3V  C2   N1   aromatic  1.348  0.020  1.348
 O3V  C2   N12  aromatic  1.316  0.020  1.316
 O3V  N11  N12  aromatic  1.360  0.020  1.360
 O3V  N11  C15  single    1.416  0.020  1.416
 O3V  C16  C15  aromatic  1.389  0.020  1.389
 O3V  C16  C17  aromatic  1.388  0.020  1.388
 O3V  C15  C20  aromatic  1.389  0.020  1.389
 O3V  C17  C18  aromatic  1.388  0.020  1.388
 O3V  C20  C19  aromatic  1.386  0.020  1.386
 O3V  C18  C19  aromatic  1.389  0.020  1.389
 O3V  C7   H29  single    0.970  0.020  1.090
 O3V  C7   H30  single    0.970  0.020  1.090
 O3V  C17  H34  single    0.930  0.020  1.080
 O3V  C18  H35  single    0.930  0.020  1.080
 O3V  C19  H36  single    0.930  0.020  1.080
 O3V  C20  H37  single    0.930  0.020  1.080
 O3V  C21  H39  single    0.970  0.020  1.090
 O3V  C21  H38  single    0.970  0.020  1.090
 O3V  C21  H40  single    0.970  0.020  1.090
 O3V  C22  H41  single    0.970  0.020  1.090
 O3V  C22  H42  single    0.970  0.020  1.090
 O3V  C22  H43  single    0.970  0.020  1.090
 O3V  C25  H45  single    0.930  0.020  1.080
 O3V  C26  H46  single    0.930  0.020  1.080
 O3V  C27  H47  single    0.930  0.020  1.080
 O3V  C16  H33  single    0.930  0.020  1.080
 O3V  C9   H32  single    0.970  0.020  1.090
 O3V  C9   H31  single    0.970  0.020  1.090
 O3V  O23  H44  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
 O3V  N12  C2   N1   124.60  3.000
 O3V  N12  C2   C3   112.33  3.000
 O3V  N1   C2   C3   123.05  3.000
 O3V  C13  C3   C4   135.74  3.000
 O3V  C13  C3   C2   103.83  3.000
 O3V  C4   C3   C2   120.41  3.000
 O3V  C24  C4   C5   126.54  3.000
 O3V  C5   C4   C3   116.22  3.000
 O3V  C24  C4   C3   117.23  3.000
 O3V  C10  C5   C6   119.83  3.000
 O3V  C10  C5   C4   119.05  3.000
 O3V  C6   C5   C4   121.10  3.000
 O3V  O14  C6   C7   120.30  3.000
 O3V  C7   C6   C5   118.18  3.000
 O3V  O14  C6   C5   121.49  3.000
 O3V  H30  C7   H29  106.21  3.000
 O3V  H30  C7   C8   111.54  3.000
 O3V  H29  C7   C8   109.19  3.000
 O3V  H30  C7   C6   108.26  3.000
 O3V  H29  C7   C6   106.20  3.000
 O3V  C8   C7   C6   114.96  3.000
 O3V  C9   C8   C22  110.77  3.000
 O3V  C9   C8   C21  109.28  3.000
 O3V  C22  C8   C21  108.99  3.000
 O3V  C9   C8   C7   107.24  3.000
 O3V  C21  C8   C7   109.78  3.000
 O3V  C22  C8   C7   110.75  3.000
 O3V  O23  C13  N11  120.97  3.000
 O3V  N11  C13  C3   106.01  3.000
 O3V  O23  C13  C3   133.01  3.000
 O3V  H34  C17  C16  119.45  3.000
 O3V  H34  C17  C18  120.17  3.000
 O3V  C16  C17  C18  120.38  3.000
 O3V  H35  C18  C19  120.08  3.000
 O3V  H35  C18  C17  120.04  3.000
 O3V  C19  C18  C17  119.88  3.000
 O3V  H36  C19  C20  119.56  3.000
 O3V  H36  C19  C18  120.14  3.000
 O3V  C20  C19  C18  120.30  3.000
 O3V  H37  C20  C15  120.16  3.000
 O3V  H37  C20  C19  120.54  3.000
 O3V  C15  C20  C19  119.30  3.000
 O3V  H40  C21  H38  107.80  3.000
 O3V  H40  C21  H39  107.84  3.000
 O3V  H38  C21  H39  107.76  3.000
 O3V  H40  C21  C8   111.52  3.000
 O3V  H38  C21  C8   110.66  3.000
 O3V  H39  C21  C8   111.10  3.000
 O3V  H43  C22  H42  107.77  3.000
 O3V  H43  C22  H41  107.29  3.000
 O3V  H42  C22  H41  107.31  3.000
 O3V  H43  C22  C8   110.61  3.000
 O3V  H42  C22  C8   110.64  3.000
 O3V  H41  C22  C8   113.01  3.000
 O3V  H45  C25  C24  123.12  3.000
 O3V  H45  C25  C26  124.26  3.000
 O3V  C24  C25  C26  112.58  3.000
 O3V  H46  C26  C27  123.66  3.000
 O3V  H46  C26  C25  123.90  3.000
 O3V  C27  C26  C25  112.44  3.000
 O3V  H47  C27  S28  120.11  3.000
 O3V  H47  C27  C26  128.09  3.000
 O3V  S28  C27  C26  111.79  3.000
 O3V  N1   C10  C9   116.16  3.000
 O3V  N1   C10  C5   124.72  3.000
 O3V  C9   C10  C5   119.12  3.000
 O3V  N11  C15  C16  120.45  3.000
 O3V  C16  C15  C20  120.95  3.000
 O3V  N11  C15  C20  118.59  3.000
 O3V  H33  C16  C15  120.85  3.000
 O3V  H33  C16  C17  119.95  3.000
 O3V  C15  C16  C17  119.19  3.000
 O3V  S28  C24  C25  111.23  3.000
 O3V  S28  C24  C4   121.79  3.000
 O3V  C25  C24  C4   126.76  3.000
 O3V  H31  C9   H32  106.43  3.000
 O3V  H31  C9   C10  108.52  3.000
 O3V  H32  C9   C10  108.02  3.000
 O3V  H31  C9   C8   111.04  3.000
 O3V  H32  C9   C8   108.98  3.000
 O3V  C10  C9   C8   113.56  3.000
 O3V  C10  N1   C2   116.55  3.000
 O3V  N12  N11  C15  119.09  3.000
 O3V  C15  N11  C13  127.08  3.000
 O3V  N12  N11  C13  113.80  3.000
 O3V  N11  N12  C2   104.04  3.000
 O3V  H44  O23  C13  110.18  3.000
 O3V  C24  S28  C27   91.94  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
 O3V  CONST_01  C24  C4   C3   C2   180.00   0.0  0
 O3V  CONST_02  C5   C4   C3   C2     0.00   0.0  0
 O3V  CONST_03  N11  C13  C3   C2     0.00   0.0  0
 O3V  CONST_04  C5   C10  N1   C2     0.00   0.0  0
 O3V  CONST_05  C13  N11  N12  C2     0.00   0.0  0
 O3V  CONST_06  C15  N11  N12  C2   180.00   0.0  0
 O3V  CONST_09  C10  C5   C4   C3     0.00   0.0  0
 O3V  CONST_10  N12  N11  C13  C3     0.00   0.0  0
 O3V  CONST_11  C15  N11  C13  C3   180.00   0.0  0
 O3V  CONST_12  C10  N1   C2   C3     0.00   0.0  0
 O3V  CONST_13  N11  N12  C2   C3     0.00   0.0  0
 O3V  CONST_14  C26  C25  C24  C4   180.00   0.0  0
 O3V  CONST_15  C27  S28  C24  C4   180.00   0.0  0
 O3V  CONST_16  N1   C10  C5   C4     0.00   0.0  0
 O3V  CONST_17  N11  C13  C3   C4   180.00   0.0  0
 O3V  CONST_18  N1   C2   C3   C4     0.00   0.0  0
 O3V  CONST_19  N12  C2   C3   C4   180.00   0.0  0
 O3V  CONST_22  C13  C3   C4   C5   180.00   0.0  0
 O3V  CONST_23  C24  C4   C3   C13    0.00   0.0  0
 O3V  CONST_24  N1   C2   C3   C13  180.00   0.0  0
 O3V  CONST_25  N12  C2   C3   C13    0.00   0.0  0
 O3V  CONST_28  N11  C15  C16  C17  180.00   0.0  0
 O3V  CONST_29  C20  C15  C16  C17    0.00   0.0  0
 O3V  CONST_30  C20  C19  C18  C17    0.00   0.0  0
 O3V  CONST_31  C15  C16  C17  C18    0.00   0.0  0
 O3V  CONST_32  C15  C20  C19  C18    0.00   0.0  0
 O3V  CONST_33  N11  C15  C20  C19  180.00   0.0  0
 O3V  CONST_34  C16  C15  C20  C19    0.00   0.0  0
 O3V  CONST_35  C16  C17  C18  C19    0.00   0.0  0
 O3V  CONST_37  S28  C27  C26  C25    0.00   0.0  0
 O3V  CONST_38  C27  S28  C24  C25    0.00   0.0  0
 O3V  CONST_39  C24  S28  C27  C26    0.00   0.0  0
 O3V  CONST_40  S28  C24  C25  C26    0.00   0.0  0
 O3V  CONST_41  C24  C25  C26  C27    0.00   0.0  0
 O3V  CONST_42  C24  C4   C5   C10  180.00   0.0  0
 O3V  CONST_43  N12  C2   N1   C10  180.00   0.0  0
 O3V  CONST_45  N11  N12  C2   N1   180.00   0.0  0
 O3V  CONST_46  C24  C4   C5   C6     0.00   0.0  0
 O3V  CONST_47  O23  C13  C3   C2   180.00   0.0  0
 O3V  CONST_48  O23  C13  C3   C4     0.00   0.0  0
 O3V  CONST_49  O23  C13  N11  C15    0.00   0.0  0
 O3V  CONST_50  O23  C13  N11  N12  180.00   0.0  0
 O3V  CONST_51  H45  C25  C24  C4     0.00   0.0  0
 O3V  CONST_52  H36  C19  C18  C17  180.00   0.0  0
 O3V  CONST_53  H33  C16  C17  C18  180.00   0.0  0
 O3V  CONST_54  H37  C20  C19  C18  180.00   0.0  0
 O3V  CONST_55  H34  C17  C18  C19  180.00   0.0  0
 O3V  CONST_56  H35  C18  C19  C20  180.00   0.0  0
 O3V  CONST_57  H47  C27  C26  C25  180.00   0.0  0
 O3V  CONST_58  H46  C26  C25  C24  180.00   0.0  0
 O3V  Var_01    C7   C6   C5   C4   176.82  30.0  1
 O3V  Var_02    C8   C7   C6   C5   -24.10  30.0  1
 O3V  Var_03    C8   C9   C10  C5    31.73  30.0  1
 O3V  Var_04    C9   C8   C7   C6    53.48  30.0  1
 O3V  Var_05    C10  C9   C8   C7   -57.13  30.0  1
 O3V  Var_06    H41  C22  C8   C7    57.44  30.0  3
 O3V  Var_07    H39  C21  C8   C7    62.31  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
 O3V  plan-1  C4   0.020
 O3V  plan-1  C25  0.020
 O3V  plan-1  C26  0.020
 O3V  plan-1  C27  0.020
 O3V  plan-1  C24  0.020
 O3V  plan-1  S28  0.020
 O3V  plan-1  H45  0.020
 O3V  plan-1  H46  0.020
 O3V  plan-1  H47  0.020
 O3V  plan-2  C17  0.020
 O3V  plan-2  C18  0.020
 O3V  plan-2  C19  0.020
 O3V  plan-2  C20  0.020
 O3V  plan-2  C15  0.020
 O3V  plan-2  C16  0.020
 O3V  plan-2  N11  0.020
 O3V  plan-2  H35  0.020
 O3V  plan-2  H36  0.020
 O3V  plan-2  H37  0.020
 O3V  plan-2  H33  0.020
 O3V  plan-2  H34  0.020
 O3V  plan-3  C2   0.020
 O3V  plan-3  C3   0.020
 O3V  plan-3  C4   0.020
 O3V  plan-3  C5   0.020
 O3V  plan-3  C6   0.020
 O3V  plan-3  C13  0.020
 O3V  plan-3  C10  0.020
 O3V  plan-3  C15  0.020
 O3V  plan-3  C24  0.020
 O3V  plan-3  C9   0.020
 O3V  plan-3  N1   0.020
 O3V  plan-3  N11  0.020
 O3V  plan-3  N12  0.020
 O3V  plan-3  O23  0.020
 O3V  plan-4  C5   0.020
 O3V  plan-4  C6   0.020
 O3V  plan-4  C7   0.020
 O3V  plan-4  O14  0.020

