# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 10:48:53 2020
#   Inital geometry file: a 73 line input string
#   Ligand name: 6-chloro-9-hydroxy-1,3-dimethyl-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1nc(C)c2C(=O)c3cc(Cl)ccc3N(O)c12
#
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
 73Q  73Q  6-chloro-9-hydroxy-1,3-dimethyl-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one  ligand  28  18  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_73Q
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
 73Q  C1   C   CH3   0  -0.731   3.2671  -2.8464   0.1154
 73Q  C2   C   CR5   0   0.279   2.8775  -1.4128   0.0843
 73Q  N1   N   N     0  -0.286   3.7657  -0.4548   0.1050
 73Q  N2   N   NR5   0  -0.381   3.0928   0.7253   0.0634
 73Q  C3   C   CH3   0  -0.529   3.8473   1.9612   0.0920
 73Q  C4   C   CR56  0   0.740   1.7756   0.5080   0.0212
 73Q  N3   N   NR6   0  -0.356   0.7586   1.3973  -0.0394
 73Q  O1   O   O     0  -0.514   1.0153   2.7242   0.0748
 73Q  C5   C   CR66  0   0.387  -0.5475   0.9561  -0.0358
 73Q  C6   C   CR16  0  -0.324  -1.6045   1.8737  -0.0434
 73Q  C7   C   CR16  0  -0.205  -2.9059   1.4255  -0.0571
 73Q  C8   C   CR6   0  -0.046  -3.1741   0.0577  -0.0628
 73Q  CL   CL  CL    0  -0.125  -4.8183  -0.4861  -0.0863
 73Q  C9   C   CR16  0  -0.252  -2.1478  -0.8554  -0.0492
 73Q  C10  C   CR66  0  -0.139  -0.8186  -0.4255  -0.0329
 73Q  C11  C   CR6   0   0.398   0.2593  -1.4411  -0.0036
 73Q  O2   O   OC    0  -0.445   0.0234  -2.6446  -0.0031
 73Q  C12  C   CR56  0  -0.382   1.5678  -0.8681   0.0317
 73Q  H11  H   HCH3  0   0.251   2.8380  -3.3493   0.9821
 73Q  H12  H   HCH3  0   0.251   2.9047  -3.3690  -0.7698
 73Q  H13  H   HCH3  0   0.249   4.3496  -2.9481   0.1580
 73Q  H31  H   HCH3  0   0.259   3.6613   2.5610  -0.7958
 73Q  H32  H   HCH3  0   0.264   3.6202   2.5448   0.9804
 73Q  H33  H   HCH3  0   0.272   4.8969   1.6870   0.1103
 73Q  HO1  H   H     0   0.496   1.0382   3.0830  -0.8258
 73Q  H6   H   HCR6  0   0.291  -1.4192   2.9375  -0.0377
 73Q  H7   H   HCR6  0   0.293  -3.7151   2.1425  -0.0631
 73Q  H9   H   HCR6  0   0.286  -2.3492  -1.9183  -0.0490

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
 73Q  C1   C2   single    1.486  0.020  1.486
 73Q  C1   H11  single    0.970  0.020  1.090
 73Q  C1   H12  single    0.970  0.020  1.090
 73Q  C1   H13  single    0.970  0.020  1.090
 73Q  C2   N1   aromatic  1.307  0.020  1.307
 73Q  C2   C12  aromatic  1.419  0.020  1.419
 73Q  N1   N2   aromatic  1.359  0.020  1.359
 73Q  N2   C3   single    1.448  0.020  1.448
 73Q  N2   C4   aromatic  1.336  0.020  1.336
 73Q  C3   H31  single    0.970  0.020  1.090
 73Q  C3   H32  single    0.970  0.020  1.090
 73Q  C3   H33  single    0.970  0.020  1.090
 73Q  C4   N3   aromatic  1.352  0.020  1.352
 73Q  C4   C12  aromatic  1.392  0.020  1.392
 73Q  N3   O1   single    1.356  0.020  1.356
 73Q  N3   C5   aromatic  1.379  0.020  1.379
 73Q  O1   HO1  single    0.850  0.020  0.980
 73Q  C5   C6   aromatic  1.400  0.020  1.400
 73Q  C5   C10  aromatic  1.408  0.020  1.408
 73Q  C6   C7   aromatic  1.376  0.020  1.376
 73Q  C6   H6   single    0.930  0.020  1.080
 73Q  C7   C8   aromatic  1.394  0.020  1.394
 73Q  C7   H7   single    0.930  0.020  1.080
 73Q  C8   CL   single    1.732  0.020  1.732
 73Q  C8   C9   aromatic  1.374  0.020  1.374
 73Q  C9   C10  aromatic  1.397  0.020  1.397
 73Q  C9   H9   single    0.930  0.020  1.080
 73Q  C10  C11  aromatic  1.481  0.020  1.481
 73Q  C11  O2   double    1.226  0.020  1.226
 73Q  C11  C12  aromatic  1.429  0.020  1.429

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
 73Q  H13  C1   H12  108.53  3.000
 73Q  H13  C1   H11  108.50  3.000
 73Q  H12  C1   H11  107.08  3.000
 73Q  H13  C1   C2   110.60  3.000
 73Q  H12  C1   C2   111.00  3.000
 73Q  H11  C1   C2   111.01  3.000
 73Q  C12  C2   N1   110.27  3.000
 73Q  C12  C2   C1   127.80  3.000
 73Q  N1   C2   C1   121.93  3.000
 73Q  N2   N1   C2   107.43  3.000
 73Q  C4   N2   C3   130.78  3.000
 73Q  C4   N2   N1   110.36  3.000
 73Q  C3   N2   N1   118.85  3.000
 73Q  H33  C3   H32  108.91  3.000
 73Q  H33  C3   H31  108.57  3.000
 73Q  H32  C3   H31  109.60  3.000
 73Q  H33  C3   N2   106.77  3.000
 73Q  H32  C3   N2   111.44  3.000
 73Q  H31  C3   N2   111.43  3.000
 73Q  C12  C4   N3   122.56  3.000
 73Q  C12  C4   N2   107.93  3.000
 73Q  N3   C4   N2   129.50  3.000
 73Q  C5   N3   O1   119.48  3.000
 73Q  C5   N3   C4   120.13  3.000
 73Q  O1   N3   C4   119.82  3.000
 73Q  HO1  O1   N3   106.76  3.000
 73Q  C10  C5   C6   119.86  3.000
 73Q  C10  C5   N3   119.77  3.000
 73Q  C6   C5   N3   120.37  3.000
 73Q  H6   C6   C7   118.89  3.000
 73Q  H6   C6   C5   121.08  3.000
 73Q  C7   C6   C5   120.03  3.000
 73Q  H7   C7   C8   120.45  3.000
 73Q  H7   C7   C6   119.45  3.000
 73Q  C8   C7   C6   120.10  3.000
 73Q  C9   C8   CL   120.04  3.000
 73Q  C9   C8   C7   120.56  3.000
 73Q  CL   C8   C7   119.40  3.000
 73Q  H9   C9   C10  118.65  3.000
 73Q  H9   C9   C8   120.93  3.000
 73Q  C10  C9   C8   120.42  3.000
 73Q  C11  C10  C9   118.79  3.000
 73Q  C11  C10  C5   122.19  3.000
 73Q  C9   C10  C5   119.02  3.000
 73Q  C12  C11  O2   124.73  3.000
 73Q  C12  C11  C10  113.07  3.000
 73Q  O2   C11  C10  122.20  3.000
 73Q  C11  C12  C4   122.22  3.000
 73Q  C11  C12  C2   133.79  3.000
 73Q  C4   C12  C2   104.00  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
 73Q  CONST_01  C4   N2   N1   C2    0.00   0.0  0
 73Q  CONST_02  N2   C4   C12  C2    0.00   0.0  0
 73Q  CONST_03  N3   C4   C12  C2  180.00   0.0  0
 73Q  CONST_04  C10  C11  C12  C2  180.00   0.0  0
 73Q  CONST_05  C4   C12  C2   N1    0.00   0.0  0
 73Q  CONST_06  C11  C12  C2   N1  180.00   0.0  0
 73Q  CONST_07  N3   C4   N2   N1  180.00   0.0  0
 73Q  CONST_08  C12  C4   N2   N1    0.00   0.0  0
 73Q  CONST_09  C12  C2   N1   N2    0.00   0.0  0
 73Q  CONST_10  C5   N3   C4   N2  180.00   0.0  0
 73Q  CONST_11  C11  C12  C4   N2  180.00   0.0  0
 73Q  CONST_12  C6   C5   N3   C4  180.00   0.0  0
 73Q  CONST_13  C10  C5   N3   C4    0.00   0.0  0
 73Q  CONST_14  C10  C11  C12  C4    0.00   0.0  0
 73Q  CONST_15  C11  C12  C4   N3    0.00   0.0  0
 73Q  CONST_16  C7   C6   C5   N3  180.00   0.0  0
 73Q  CONST_17  C9   C10  C5   N3  180.00   0.0  0
 73Q  CONST_18  C11  C10  C5   N3    0.00   0.0  0
 73Q  CONST_19  C12  C4   N3   C5    0.00   0.0  0
 73Q  CONST_20  C8   C7   C6   C5    0.00   0.0  0
 73Q  CONST_21  C8   C9   C10  C5    0.00   0.0  0
 73Q  CONST_22  C12  C11  C10  C5    0.00   0.0  0
 73Q  CONST_23  C9   C10  C5   C6    0.00   0.0  0
 73Q  CONST_24  C11  C10  C5   C6  180.00   0.0  0
 73Q  CONST_25  C9   C8   C7   C6    0.00   0.0  0
 73Q  CONST_26  C10  C5   C6   C7    0.00   0.0  0
 73Q  CONST_27  C10  C9   C8   C7    0.00   0.0  0
 73Q  CONST_28  C11  C10  C9   C8  180.00   0.0  0
 73Q  CONST_29  C12  C11  C10  C9  180.00   0.0  0
 73Q  CONST_30  N2   N1   C2   C1  180.00   0.0  0
 73Q  CONST_31  C4   C12  C2   C1  180.00   0.0  0
 73Q  CONST_32  C11  C12  C2   C1    0.00   0.0  0
 73Q  CONST_33  C3   N2   N1   C2  180.00   0.0  0
 73Q  CONST_34  O2   C11  C12  C2    0.00   0.0  0
 73Q  CONST_35  O1   N3   C4   N2    0.00   0.0  0
 73Q  CONST_36  N3   C4   N2   C3    0.00   0.0  0
 73Q  CONST_37  C12  C4   N2   C3  180.00   0.0  0
 73Q  CONST_38  O2   C11  C12  C4  180.00   0.0  0
 73Q  CONST_39  C12  C4   N3   O1  180.00   0.0  0
 73Q  CONST_40  C6   C5   N3   O1    0.00   0.0  0
 73Q  CONST_41  C10  C5   N3   O1  180.00   0.0  0
 73Q  CONST_42  O2   C11  C10  C5  180.00   0.0  0
 73Q  CONST_43  CL   C8   C7   C6  180.00   0.0  0
 73Q  CONST_44  C10  C9   C8   CL  180.00   0.0  0
 73Q  CONST_45  O2   C11  C10  C9    0.00   0.0  0
 73Q  CONST_46  H6   C6   C5   N3    0.00   0.0  0
 73Q  CONST_47  H7   C7   C6   C5  180.00   0.0  0
 73Q  CONST_48  H9   C9   C10  C5  180.00   0.0  0
 73Q  Var_01    H11  C1   C2   N1  120.62  30.0  2
 73Q  Var_02    H31  C3   N2   N1  120.37  30.0  2

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
 73Q  plan-1  C1   0.020
 73Q  plan-1  C2   0.020
 73Q  plan-1  N1   0.020
 73Q  plan-1  N2   0.020
 73Q  plan-1  C3   0.020
 73Q  plan-1  C4   0.020
 73Q  plan-1  N3   0.020
 73Q  plan-1  O1   0.020
 73Q  plan-1  C5   0.020
 73Q  plan-1  C6   0.020
 73Q  plan-1  C7   0.020
 73Q  plan-1  C8   0.020
 73Q  plan-1  CL   0.020
 73Q  plan-1  C9   0.020
 73Q  plan-1  C10  0.020
 73Q  plan-1  C11  0.020
 73Q  plan-1  O2   0.020
 73Q  plan-1  C12  0.020
 73Q  plan-1  H6   0.020
 73Q  plan-1  H7   0.020
 73Q  plan-1  H9   0.020

