# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 01:56:42 2020
#   Inital geometry file: a 92 line input string
#   Ligand name: 3-[(cyclopropylamino)methyl]-8-ethylquinolin-2(1H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1cccc2C=C(CNC3CC3)C(=O)Nc12
#
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
 5HL  5HL  3-[(cyclopropylamino)methyl]-8-ethylquinolin-2(1H)-one  ligand  36  18  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_5HL
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
 5HL  C4   C  CR16  0  -0.248   3.5720  -2.1402  -0.2648
 5HL  C5   C  CR16  0  -0.344   2.2369  -2.3677  -0.5075
 5HL  C6   C  CR66  0   0.047   1.3287  -1.3020  -0.4899
 5HL  N1   N  NR16  0  -0.760   0.8696   1.0152  -0.2191
 5HL  C7   C  CR16  0  -0.196  -0.0723  -1.4807  -0.7279
 5HL  C8   C  CR6   0  -0.128  -0.9513  -0.4576  -0.7063
 5HL  C9   C  CH2   0  -0.327  -2.4236  -0.6592  -0.8861
 5HL  C10  C  CH1   0  -0.092  -4.5153  -0.4898   0.2969
 5HL  C11  C  CH2   0  -0.504  -5.2504   0.1714   1.4176
 5HL  C12  C  CH2   0  -0.487  -5.1062   0.8702   0.0979
 5HL  C13  C  CR6   0   0.516  -0.4771   0.9012  -0.4526
 5HL  C14  C  CR66  0   0.335   1.7898  -0.0051  -0.2208
 5HL  O    O  O     0  -0.475  -1.1931   1.8939  -0.4568
 5HL  N    N  NH1   0  -0.584  -3.0926  -0.5630   0.3997
 5HL  C2   C  CR6   0   0.096   3.1515   0.2405   0.0323
 5HL  C1   C  CH2   0  -0.541   3.6623   1.6142   0.3718
 5HL  C    C  CH3   0  -0.652   3.4234   1.9857   1.8360
 5HL  C3   C  CR16  0  -0.329   4.0134  -0.8417   0.0012
 5HL  H1   H  HCR6  0   0.258   4.2800  -2.9574  -0.2791
 5HL  H2   H  HCR6  0   0.261   1.8737  -3.3665  -0.7153
 5HL  H3   H  HNR6  0   0.415   1.1960   1.9583  -0.0590
 5HL  H4   H  HCR6  0   0.268  -0.4274  -2.4860  -0.9297
 5HL  H5   H  HCH2  0   0.242  -2.8279   0.1187  -1.5365
 5HL  H6   H  HCH2  0   0.219  -2.6001  -1.6179  -1.3929
 5HL  H7   H  HCH1  0   0.227  -5.0312  -1.3130  -0.2011
 5HL  H8   H  HCH2  0   0.245  -6.2231  -0.2161   1.6917
 5HL  H9   H  HCH2  0   0.244  -4.6613   0.5384   2.2484
 5HL  H10  H  HCH2  0   0.246  -4.4086   1.6965   0.0413
 5HL  H11  H  HCH2  0   0.244  -5.9800   0.9664  -0.5336
 5HL  H12  H  HNH1  0   0.345  -2.8270  -1.3529   0.9752
 5HL  H14  H  HCH2  0   0.263   4.7334   1.6483   0.1659
 5HL  H15  H  HCH2  0   0.245   3.2175   2.3712  -0.2813
 5HL  H16  H  HCH3  0   0.238   3.8079   2.9836   2.0470
 5HL  H17  H  HCH3  0   0.224   2.3638   1.9796   2.0943
 5HL  H18  H  HCH3  0   0.232   3.9284   1.2840   2.4997
 5HL  H19  H  HCR6  0   0.257   5.0665  -0.6696   0.1893

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
 5HL  C4   C5   aromatic  1.376  0.020  1.376
 5HL  C4   C3   aromatic  1.397  0.020  1.397
 5HL  C5   C6   aromatic  1.400  0.020  1.400
 5HL  C3   C2   aromatic  1.384  0.020  1.384
 5HL  C6   C7   single    1.432  0.020  1.432
 5HL  C6   C14  aromatic  1.403  0.020  1.403
 5HL  C    C1   single    1.529  0.020  1.529
 5HL  C2   C14  aromatic  1.407  0.020  1.407
 5HL  C2   C1   single    1.504  0.020  1.504
 5HL  C7   C8   double    1.349  0.020  1.349
 5HL  C14  N1   single    1.374  0.020  1.374
 5HL  C8   C9   single    1.497  0.020  1.497
 5HL  C8   C13  single    1.461  0.020  1.461
 5HL  N1   C13  single    1.371  0.020  1.371
 5HL  C9   N    single    1.453  0.020  1.453
 5HL  C13  O    double    1.224  0.020  1.224
 5HL  N    C10  single    1.428  0.020  1.428
 5HL  C11  C10  single    1.494  0.020  1.494
 5HL  C11  C12  single    1.500  0.020  1.500
 5HL  C10  C12  single    1.496  0.020  1.496
 5HL  C4   H1   single    0.930  0.020  1.080
 5HL  C5   H2   single    0.930  0.020  1.080
 5HL  N1   H3   single    0.860  0.020  1.020
 5HL  C7   H4   single    0.930  0.020  1.080
 5HL  C9   H5   single    0.970  0.020  1.090
 5HL  C9   H6   single    0.970  0.020  1.090
 5HL  C10  H7   single    0.970  0.020  1.090
 5HL  C11  H8   single    0.970  0.020  1.090
 5HL  C11  H9   single    0.970  0.020  1.090
 5HL  C12  H10  single    0.970  0.020  1.090
 5HL  C12  H11  single    0.970  0.020  1.090
 5HL  N    H12  single    0.890  0.020  1.040
 5HL  C1   H14  single    0.970  0.020  1.090
 5HL  C1   H15  single    0.970  0.020  1.090
 5HL  C    H16  single    0.970  0.020  1.090
 5HL  C    H17  single    0.970  0.020  1.090
 5HL  C    H18  single    0.970  0.020  1.090
 5HL  C3   H19  single    0.930  0.020  1.080

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
 5HL  H1   C4   C3   119.87  3.000
 5HL  H1   C4   C5   120.53  3.000
 5HL  C3   C4   C5   119.60  3.000
 5HL  H2   C5   C6   119.14  3.000
 5HL  H2   C5   C4   120.78  3.000
 5HL  C6   C5   C4   120.08  3.000
 5HL  C14  C6   C7   117.96  3.000
 5HL  C14  C6   C5   119.54  3.000
 5HL  C7   C6   C5   122.50  3.000
 5HL  H3   N1   C14  118.47  3.000
 5HL  H3   N1   C13  114.94  3.000
 5HL  C14  N1   C13  126.56  3.000
 5HL  H4   C7   C8   119.49  3.000
 5HL  H4   C7   C6   117.82  3.000
 5HL  C8   C7   C6   122.69  3.000
 5HL  C13  C8   C9   117.73  3.000
 5HL  C13  C8   C7   119.77  3.000
 5HL  C9   C8   C7   122.47  3.000
 5HL  H6   C9   H5   106.70  3.000
 5HL  H6   C9   N    113.09  3.000
 5HL  H5   C9   N    108.04  3.000
 5HL  H6   C9   C8   109.33  3.000
 5HL  H5   C9   C8   109.87  3.000
 5HL  N    C9   C8   109.74  3.000
 5HL  H7   C10  N    117.71  3.000
 5HL  H7   C10  C12  115.98  3.000
 5HL  N    C10  C12  116.72  3.000
 5HL  H7   C10  C11  116.31  3.000
 5HL  C12  C10  C11   60.22  3.000
 5HL  N    C10  C11  117.30  3.000
 5HL  H9   C11  H8   114.58  3.000
 5HL  H9   C11  C12  117.70  3.000
 5HL  H8   C11  C12  118.43  3.000
 5HL  H9   C11  C10  117.24  3.000
 5HL  H8   C11  C10  118.27  3.000
 5HL  C12  C11  C10   59.94  3.000
 5HL  H11  C12  H10  114.95  3.000
 5HL  H11  C12  C11  118.49  3.000
 5HL  H10  C12  C11  117.60  3.000
 5HL  H11  C12  C10  118.50  3.000
 5HL  H10  C12  C10  116.50  3.000
 5HL  C11  C12  C10   59.84  3.000
 5HL  O    C13  C8   124.31  3.000
 5HL  O    C13  N1   120.50  3.000
 5HL  C8   C13  N1   115.18  3.000
 5HL  C2   C14  N1   121.23  3.000
 5HL  N1   C14  C6   117.82  3.000
 5HL  C2   C14  C6   120.94  3.000
 5HL  H12  N    C10  110.01  3.000
 5HL  H12  N    C9   109.30  3.000
 5HL  C10  N    C9   113.48  3.000
 5HL  C3   C2   C1   120.51  3.000
 5HL  C1   C2   C14  121.92  3.000
 5HL  C3   C2   C14  117.54  3.000
 5HL  H15  C1   H14  105.35  3.000
 5HL  H15  C1   C    109.87  3.000
 5HL  H14  C1   C    109.05  3.000
 5HL  H15  C1   C2   111.04  3.000
 5HL  H14  C1   C2   108.62  3.000
 5HL  C    C1   C2   112.63  3.000
 5HL  H18  C    H17  107.60  3.000
 5HL  H18  C    H16  107.94  3.000
 5HL  H17  C    H16  107.58  3.000
 5HL  H18  C    C1   110.75  3.000
 5HL  H17  C    C1   112.16  3.000
 5HL  H16  C    C1   110.65  3.000
 5HL  H19  C3   C2   118.51  3.000
 5HL  H19  C3   C4   119.19  3.000
 5HL  C2   C3   C4   122.30  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
 5HL  CONST_01  C14  C6   C5   C4      0.00   0.0  0
 5HL  CONST_02  C14  C2   C3   C4      0.00   0.0  0
 5HL  CONST_03  C2   C3   C4   C5      0.00   0.0  0
 5HL  CONST_04  C2   C14  C6   C5      0.00   0.0  0
 5HL  CONST_05  C3   C4   C5   C6      0.00   0.0  0
 5HL  CONST_06  C3   C2   C14  C6      0.00   0.0  0
 5HL  CONST_07  C14  N1   C13  C8      0.00   0.0  0
 5HL  CONST_08  C1   C2   C3   C4    180.00   0.0  0
 5HL  CONST_09  C1   C2   C14  C6    180.00   0.0  0
 5HL  CONST_10  C1   C2   C14  N1      0.00   0.0  0
 5HL  CONST_11  O    C13  N1   C14   180.00   0.0  0
 5HL  CONST_12  H19  C3   C4   C5    180.00   0.0  0
 5HL  CONST_13  H1   C4   C5   C6    180.00   0.0  0
 5HL  CONST_14  H2   C5   C6   C7      0.00   0.0  0
 5HL  CONST_15  H3   N1   C13  C8    180.00   0.0  0
 5HL  Var_01    N    C10  C12  C11  -107.67  30.0  1
 5HL  Var_02    H10  C12  C11  C10  -106.17  30.0  1
 5HL  Var_03    N    C9   C8   C7    103.34  30.0  3
 5HL  Var_04    C10  N    C9   C8    168.82  30.0  3
 5HL  Var_05    C11  C10  N    C9   -154.70  30.0  3
 5HL  Var_06    C    C1   C2   C14    79.71  30.0  2
 5HL  Var_07    H16  C    C1   C2    179.82  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
 5HL  chir_01  C10  N  C11  C12  both

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
 5HL  plan-1  C4   0.020
 5HL  plan-1  C5   0.020
 5HL  plan-1  C6   0.020
 5HL  plan-1  N1   0.020
 5HL  plan-1  C7   0.020
 5HL  plan-1  C8   0.020
 5HL  plan-1  C9   0.020
 5HL  plan-1  C13  0.020
 5HL  plan-1  C14  0.020
 5HL  plan-1  O    0.020
 5HL  plan-1  C2   0.020
 5HL  plan-1  C1   0.020
 5HL  plan-1  C3   0.020
 5HL  plan-1  H1   0.020
 5HL  plan-1  H2   0.020
 5HL  plan-1  H3   0.020
 5HL  plan-1  H4   0.020
 5HL  plan-1  H19  0.020

