# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 21:51:35 2022
#   Inital geometry file: a 118 line input string
#   Ligand name: 8-(2-chloranyl-4-methoxy-phenyl)-7-fluoranyl-1-piperidin-4-yl-imidazo[4,5-c]quinoline
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(c(Cl)c1)c2cc3c(cc2F)ncc4ncn(C5CCNCC5)c34
#
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
 80C  80C  "8-(2-chloranyl-4-methoxy-phenyl)-7-fluoranyl-1-piperidin-4-yl-imidazo[4,5-c]quinoline"
  ligand  49  29  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_80C
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
 80C  C1   C   CH3   0  -0.442   -1.8932  62.0789  35.6291
 80C  C3   C   CR6   0   0.381   -2.6388  64.1224  34.6828
 80C  C4   C   CR16  0  -0.320   -3.3159  64.7718  33.6480
 80C  C5   C   CR16  0  -0.291   -3.4190  66.1466  33.6511
 80C  C6   C   CR6   0   0.136   -2.8636  66.9298  34.6665
 80C  C7   C   CR6   0  -0.097   -2.2102  66.2566  35.6912
 80C  C11  C   CR16  0  -0.345   -4.2804  68.9581  34.6079
 80C  C12  C   CR66  0   0.117   -4.4786  70.3499  34.5284
 80C  C15  C   CR6   0   0.544   -1.9225  69.2631  34.5626
 80C  C18  C   CR16  0  -0.125   -4.5511  73.1501  34.3936
 80C  C19  C   CR56  0   0.022   -5.7549  72.4238  34.4141
 80C  C21  C   CR15  0   0.099   -7.7658  71.8003  34.4132
 80C  N22  N   NR5   0  -0.526   -7.0358  70.6505  34.4859
 80C  C23  C   CH1   0  -0.096   -7.5710  69.2897  34.4748
 80C  C24  C   CH2   0  -0.470   -9.0208  69.2225  34.9369
 80C  C27  C   CH2   0  -0.319   -7.9602  67.2141  33.1425
 80C  O2   O   O2    0  -0.461   -2.5709  62.7864  34.6081
 80C  CL8  CL  CL    0  -0.120   -1.5608  67.1443  37.0293
 80C  C9   C   CR16  0  -0.322   -2.0867  64.8743  35.7167
 80C  C10  C   CR6   0  -0.144   -3.0249  68.3958  34.6327
 80C  C13  C   CR66  0   0.162   -3.3374  71.2007  34.4885
 80C  C14  C   CR16  0  -0.465   -2.0547  70.6171  34.5027
 80C  N17  N   N     0  -0.445   -3.3908  72.5610  34.4266
 80C  N20  N   N     0  -0.450   -7.0416  72.8804  34.3737
 80C  C25  C   CH2   0  -0.319   -9.4691  67.7584  34.9375
 80C  N26  N   NH1   0  -0.569   -9.3120  67.0927  33.6578
 80C  C28  C   CH2   0  -0.455   -7.4377  68.6508  33.0950
 80C  C29  C   CR56  0   0.391   -5.7228  71.0340  34.4813
 80C  H1   H   HCH3  0   0.264   -1.9481  61.0267  35.3623
 80C  H2   H   HCH3  0   0.233   -0.8423  62.3710  35.6973
 80C  H3   H   HCH3  0   0.233   -2.3651  62.2196  36.6047
 80C  H4   H   HCR6  0   0.271   -3.7514  64.1923  32.8444
 80C  H5   H   HCR6  0   0.267   -3.9381  66.6399  32.8388
 80C  H6   H   HCR6  0   0.277   -5.1232  68.2855  34.6619
 80C  H7   H   HCR6  0   0.267   -4.5686  74.2347  34.3456
 80C  H8   H   HCR5  0   0.292   -8.8443  71.7865  34.3958
 80C  H9   H   HCH1  0   0.267   -6.9845  68.7218  35.2021
 80C  H10  H   HCH2  0   0.256   -9.1303  69.6479  35.9374
 80C  H11  H   HCH2  0   0.239   -9.6711  69.7852  34.2608
 80C  H12  H   HCH2  0   0.246   -7.9194  66.7724  32.1460
 80C  H13  H   HCH2  0   0.224   -7.2957  66.6174  33.7776
 80C  H14  H   HCR6  0   0.301   -1.5722  64.4081  36.5453
 80C  H15  H   HCR6  0   0.282   -1.1847  71.2587  34.4490
 80C  H16  H   HCH2  0   0.248  -10.5148  67.6969  35.2424
 80C  H17  H   HCH2  0   0.225   -8.8914  67.2071  35.6868
 80C  H18  H   HNH1  0   0.343   -9.9603  67.4964  32.9915
 80C  H20  H   HCH2  0   0.250   -6.3994  68.6560  32.7536
 80C  H21  H   HCH2  0   0.241   -8.0147  69.2398  32.3751
 80C  F16  F   F     0  -0.298   -0.6967  68.7264  34.5300

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
 80C  C27  C28  single    1.530  0.020  1.530
 80C  C27  N26  single    1.452  0.020  1.452
 80C  C28  C23  single    1.526  0.020  1.526
 80C  N26  C25  single    1.451  0.020  1.451
 80C  C5   C4   aromatic  1.379  0.020  1.379
 80C  C5   C6   aromatic  1.397  0.020  1.397
 80C  C4   C3   aromatic  1.397  0.020  1.397
 80C  N20  C19  aromatic  1.366  0.020  1.366
 80C  N20  C21  aromatic  1.301  0.020  1.301
 80C  C18  N17  aromatic  1.302  0.020  1.302
 80C  C18  C19  aromatic  1.406  0.020  1.406
 80C  N17  C13  aromatic  1.363  0.020  1.363
 80C  C19  C29  aromatic  1.392  0.020  1.392
 80C  C21  N22  aromatic  1.364  0.020  1.364
 80C  C29  N22  aromatic  1.368  0.020  1.368
 80C  C29  C12  aromatic  1.421  0.020  1.421
 80C  C13  C14  aromatic  1.409  0.020  1.409
 80C  C13  C12  aromatic  1.424  0.020  1.424
 80C  N22  C23  single    1.462  0.020  1.462
 80C  C14  C15  aromatic  1.362  0.020  1.362
 80C  C12  C11  aromatic  1.408  0.020  1.408
 80C  C23  C24  single    1.523  0.020  1.523
 80C  C15  F16  single    1.339  0.020  1.339
 80C  C15  C10  aromatic  1.404  0.020  1.404
 80C  C11  C10  aromatic  1.376  0.020  1.376
 80C  C10  C6   single    1.475  0.020  1.475
 80C  C25  C24  single    1.531  0.020  1.531
 80C  C6   C7   aromatic  1.389  0.020  1.389
 80C  C1   O2   single    1.415  0.020  1.415
 80C  C3   O2   single    1.340  0.020  1.340
 80C  C3   C9   aromatic  1.392  0.020  1.392
 80C  C7   C9   aromatic  1.388  0.020  1.388
 80C  C7   CL8  single    1.732  0.020  1.732
 80C  C1   H1   single    0.970  0.020  1.090
 80C  C1   H2   single    0.970  0.020  1.090
 80C  C1   H3   single    0.970  0.020  1.090
 80C  C4   H4   single    0.930  0.020  1.080
 80C  C5   H5   single    0.930  0.020  1.080
 80C  C11  H6   single    0.930  0.020  1.080
 80C  C18  H7   single    0.930  0.020  1.080
 80C  C21  H8   single    0.930  0.020  1.080
 80C  C23  H9   single    0.970  0.020  1.090
 80C  C24  H10  single    0.970  0.020  1.090
 80C  C24  H11  single    0.970  0.020  1.090
 80C  C27  H12  single    0.970  0.020  1.090
 80C  C27  H13  single    0.970  0.020  1.090
 80C  C9   H14  single    0.930  0.020  1.080
 80C  C14  H15  single    0.930  0.020  1.080
 80C  C25  H16  single    0.970  0.020  1.090
 80C  C25  H17  single    0.970  0.020  1.090
 80C  N26  H18  single    0.890  0.020  1.040
 80C  C28  H20  single    0.970  0.020  1.090
 80C  C28  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
 80C  H3   C1   H2   108.97  3.000
 80C  H3   C1   H1   108.78  3.000
 80C  H2   C1   H1   108.82  3.000
 80C  H3   C1   O2   111.90  3.000
 80C  H2   C1   O2   111.84  3.000
 80C  H1   C1   O2   106.42  3.000
 80C  C9   C3   O2   124.04  3.000
 80C  C9   C3   C4   119.42  3.000
 80C  O2   C3   C4   116.54  3.000
 80C  H4   C4   C5   120.36  3.000
 80C  H4   C4   C3   119.76  3.000
 80C  C5   C4   C3   119.88  3.000
 80C  H5   C5   C6   118.70  3.000
 80C  H5   C5   C4   119.24  3.000
 80C  C6   C5   C4   122.06  3.000
 80C  C10  C6   C7   123.35  3.000
 80C  C7   C6   C5   116.82  3.000
 80C  C10  C6   C5   119.80  3.000
 80C  C9   C7   CL8  117.57  3.000
 80C  CL8  C7   C6   119.85  3.000
 80C  C9   C7   C6   122.55  3.000
 80C  H6   C11  C10  117.18  3.000
 80C  H6   C11  C12  120.58  3.000
 80C  C10  C11  C12  122.24  3.000
 80C  C29  C12  C13  114.41  3.000
 80C  C13  C12  C11  118.64  3.000
 80C  C29  C12  C11  126.95  3.000
 80C  F16  C15  C14  119.11  3.000
 80C  F16  C15  C10  118.19  3.000
 80C  C14  C15  C10  122.69  3.000
 80C  H7   C18  N17  117.88  3.000
 80C  H7   C18  C19  120.18  3.000
 80C  N17  C18  C19  121.94  3.000
 80C  C29  C19  N20  110.91  3.000
 80C  C29  C19  C18  119.78  3.000
 80C  N20  C19  C18  129.31  3.000
 80C  H8   C21  N20  124.52  3.000
 80C  H8   C21  N22  121.68  3.000
 80C  N20  C21  N22  113.80  3.000
 80C  C29  N22  C23  127.75  3.000
 80C  C23  N22  C21  126.03  3.000
 80C  C29  N22  C21  106.09  3.000
 80C  H9   C23  C28  109.70  3.000
 80C  H9   C23  C24  106.61  3.000
 80C  C28  C23  C24  109.80  3.000
 80C  H9   C23  N22  106.38  3.000
 80C  C24  C23  N22  112.78  3.000
 80C  C28  C23  N22  111.37  3.000
 80C  H11  C24  H10  107.82  3.000
 80C  H11  C24  C25  108.55  3.000
 80C  H10  C24  C25  110.03  3.000
 80C  H11  C24  C23  110.84  3.000
 80C  H10  C24  C23  110.85  3.000
 80C  C25  C24  C23  108.73  3.000
 80C  H13  C27  H12  106.64  3.000
 80C  H13  C27  C28  108.81  3.000
 80C  H12  C27  C28  109.83  3.000
 80C  H13  C27  N26  108.26  3.000
 80C  H12  C27  N26  108.98  3.000
 80C  C28  C27  N26  114.06  3.000
 80C  C3   O2   C1   118.85  3.000
 80C  H14  C9   C7   119.07  3.000
 80C  H14  C9   C3   121.67  3.000
 80C  C7   C9   C3   119.26  3.000
 80C  C15  C10  C11  117.58  3.000
 80C  C11  C10  C6   120.42  3.000
 80C  C15  C10  C6   121.94  3.000
 80C  N17  C13  C14  116.71  3.000
 80C  C14  C13  C12  118.80  3.000
 80C  N17  C13  C12  124.49  3.000
 80C  H15  C14  C13  119.06  3.000
 80C  H15  C14  C15  120.90  3.000
 80C  C13  C14  C15  120.04  3.000
 80C  C13  N17  C18  119.20  3.000
 80C  C21  N20  C19  104.24  3.000
 80C  H17  C25  H16  106.63  3.000
 80C  H17  C25  N26  108.38  3.000
 80C  H16  C25  N26  108.93  3.000
 80C  H17  C25  C24  109.10  3.000
 80C  H16  C25  C24  109.55  3.000
 80C  N26  C25  C24  113.99  3.000
 80C  H18  N26  C25  109.14  3.000
 80C  H18  N26  C27  109.20  3.000
 80C  C25  N26  C27  112.06  3.000
 80C  H21  C28  H20  107.02  3.000
 80C  H21  C28  C27  110.23  3.000
 80C  H20  C28  C27  109.80  3.000
 80C  H21  C28  C23  108.86  3.000
 80C  H20  C28  C23  111.30  3.000
 80C  C27  C28  C23  109.59  3.000
 80C  N22  C29  C19  104.95  3.000
 80C  N22  C29  C12  134.87  3.000
 80C  C19  C29  C12  120.18  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
 80C  CONST_01  C6   C5   C4   C3      0.00   0.0  0
 80C  CONST_02  C6   C7   C9   C3      0.00   0.0  0
 80C  CONST_03  C10  C6   C5   C4    180.00   0.0  0
 80C  CONST_04  C7   C6   C5   C4      0.00   0.0  0
 80C  CONST_05  C7   C9   C3   C4      0.00   0.0  0
 80C  CONST_06  C9   C3   C4   C5      0.00   0.0  0
 80C  CONST_09  C9   C7   C6   C5      0.00   0.0  0
 80C  CONST_10  C14  C15  C10  C6    180.00   0.0  0
 80C  CONST_11  C12  C11  C10  C6    180.00   0.0  0
 80C  CONST_14  C19  C29  C12  C11   180.00   0.0  0
 80C  CONST_15  N22  C29  C12  C11     0.00   0.0  0
 80C  CONST_16  N17  C13  C12  C11   180.00   0.0  0
 80C  CONST_17  C14  C13  C12  C11     0.00   0.0  0
 80C  CONST_18  C14  C15  C10  C11     0.00   0.0  0
 80C  CONST_19  N20  C19  C29  C12   180.00   0.0  0
 80C  CONST_20  C18  C19  C29  C12     0.00   0.0  0
 80C  CONST_21  C21  N22  C29  C12   180.00   0.0  0
 80C  CONST_22  C18  N17  C13  C12     0.00   0.0  0
 80C  CONST_23  C15  C14  C13  C12     0.00   0.0  0
 80C  CONST_24  C15  C10  C11  C12     0.00   0.0  0
 80C  CONST_25  N17  C13  C14  C15   180.00   0.0  0
 80C  CONST_26  C14  C13  N17  C18   180.00   0.0  0
 80C  CONST_27  C21  N20  C19  C18   180.00   0.0  0
 80C  CONST_28  N22  C29  C19  C18   180.00   0.0  0
 80C  CONST_29  N22  C21  N20  C19     0.00   0.0  0
 80C  CONST_30  C13  N17  C18  C19     0.00   0.0  0
 80C  CONST_31  C21  N22  C29  C19     0.00   0.0  0
 80C  CONST_32  C13  C12  C29  C19     0.00   0.0  0
 80C  CONST_33  C29  C19  N20  C21     0.00   0.0  0
 80C  CONST_34  N20  C19  C29  N22     0.00   0.0  0
 80C  CONST_35  C13  C12  C29  N22   180.00   0.0  0
 80C  CONST_36  C10  C6   C7   C9    180.00   0.0  0
 80C  CONST_37  C13  C14  C15  C10     0.00   0.0  0
 80C  CONST_38  C29  C12  C11  C10   180.00   0.0  0
 80C  CONST_39  C13  C12  C11  C10     0.00   0.0  0
 80C  CONST_40  C29  C12  C13  C14   180.00   0.0  0
 80C  CONST_41  N20  C19  C18  N17   180.00   0.0  0
 80C  CONST_42  C29  C19  C18  N17     0.00   0.0  0
 80C  CONST_43  C29  C12  C13  N17     0.00   0.0  0
 80C  CONST_44  C29  N22  C21  N20     0.00   0.0  0
 80C  CONST_45  C23  N22  C29  C12     0.00   0.0  0
 80C  CONST_46  C23  N22  C29  C19   180.00   0.0  0
 80C  CONST_47  N20  C21  N22  C23   180.00   0.0  0
 80C  CONST_48  CL8  C7   C9   C3    180.00   0.0  0
 80C  CONST_49  O2   C3   C4   C5    180.00   0.0  0
 80C  CONST_50  CL8  C7   C6   C5    180.00   0.0  0
 80C  CONST_51  F16  C15  C10  C6      0.00   0.0  0
 80C  CONST_52  O2   C3   C9   C7    180.00   0.0  0
 80C  CONST_53  F16  C15  C10  C11   180.00   0.0  0
 80C  CONST_54  C10  C6   C7   CL8     0.00   0.0  0
 80C  CONST_55  F16  C15  C14  C13   180.00   0.0  0
 80C  CONST_56  H5   C5   C4   C3    180.00   0.0  0
 80C  CONST_57  H14  C9   C3   C4    180.00   0.0  0
 80C  CONST_58  H4   C4   C5   C6    180.00   0.0  0
 80C  CONST_59  H6   C11  C10  C6      0.00   0.0  0
 80C  CONST_60  H14  C9   C7   C6    180.00   0.0  0
 80C  CONST_61  H5   C5   C6   C7    180.00   0.0  0
 80C  CONST_62  H15  C14  C13  C12   180.00   0.0  0
 80C  CONST_63  H6   C11  C10  C15   180.00   0.0  0
 80C  CONST_64  H8   C21  N20  C19   180.00   0.0  0
 80C  CONST_65  H8   C21  N22  C23     0.00   0.0  0
 80C  CONST_66  H4   C4   C3   C9    180.00   0.0  0
 80C  CONST_67  H15  C14  C15  C10   180.00   0.0  0
 80C  CONST_68  H5   C5   C6   C10     0.00   0.0  0
 80C  CONST_69  H7   C18  N17  C13   180.00   0.0  0
 80C  CONST_70  H6   C11  C12  C13   180.00   0.0  0
 80C  CONST_71  H15  C14  C13  N17     0.00   0.0  0
 80C  CONST_72  H7   C18  C19  N20     0.00   0.0  0
 80C  CONST_73  H7   C18  C19  C29   180.00   0.0  0
 80C  CONST_74  H8   C21  N22  C29   180.00   0.0  0
 80C  CONST_75  H6   C11  C12  C29     0.00   0.0  0
 80C  Var_01    N26  C27  C28  C23    54.15  30.0  1
 80C  Var_02    N26  C25  C24  C23   -56.24  30.0  1
 80C  Var_03    C27  N26  C25  C24    53.35  30.0  1
 80C  Var_04    C28  C27  N26  C25   -52.12  30.0  1
 80C  Var_05    H12  C27  C28  C23   176.81  30.0  1
 80C  Var_06    H13  C27  C28  C23   -66.81  30.0  1
 80C  Var_07    H16  C25  C24  C23  -178.57  30.0  1
 80C  Var_08    H17  C25  C24  C23    65.05  30.0  1
 80C  Var_09    H18  N26  C25  C24   -67.73  30.0  1
 80C  Var_10    H16  C25  N26  C27   176.03  30.0  1
 80C  Var_11    H17  C25  N26  C27   -68.34  30.0  1
 80C  Var_12    H12  C27  N26  C25  -175.24  30.0  1
 80C  Var_13    H13  C27  N26  C25    69.15  30.0  1
 80C  Var_14    H20  C28  C27  N26   176.70  30.0  1
 80C  Var_15    H21  C28  C27  N26   -65.64  30.0  1
 80C  Var_16    H10  C24  C25  N26  -177.81  30.0  1
 80C  Var_17    H11  C24  C25  N26    64.42  30.0  1
 80C  Var_18    H18  N26  C27  C28    68.92  30.0  1
 80C  Var_19    C4   C3   O2   C1    179.84  30.0  2
 80C  Var_20    C9   C3   O2   C1     -0.42  30.0  2
 80C  Var_21    H1   C1   O2   C3   -179.18  30.0  3
 80C  Var_22    H2   C1   O2   C3    -60.47  30.0  3
 80C  Var_23    H3   C1   O2   C3     62.11  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
 80C  chir_01  C23  C28  N22  C24  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
 80C  plan-1  C3   0.020
 80C  plan-1  C4   0.020
 80C  plan-1  C5   0.020
 80C  plan-1  C6   0.020
 80C  plan-1  C7   0.020
 80C  plan-1  O2   0.020
 80C  plan-1  CL8  0.020
 80C  plan-1  C9   0.020
 80C  plan-1  C10  0.020
 80C  plan-1  H4   0.020
 80C  plan-1  H5   0.020
 80C  plan-1  H14  0.020
 80C  plan-2  C6   0.020
 80C  plan-2  C11  0.020
 80C  plan-2  C12  0.020
 80C  plan-2  C15  0.020
 80C  plan-2  C18  0.020
 80C  plan-2  C19  0.020
 80C  plan-2  C21  0.020
 80C  plan-2  N22  0.020
 80C  plan-2  C23  0.020
 80C  plan-2  C10  0.020
 80C  plan-2  C13  0.020
 80C  plan-2  C14  0.020
 80C  plan-2  N17  0.020
 80C  plan-2  N20  0.020
 80C  plan-2  C29  0.020
 80C  plan-2  H6   0.020
 80C  plan-2  H7   0.020
 80C  plan-2  H8   0.020
 80C  plan-2  H15  0.020
 80C  plan-2  F16  0.020

