# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 01:09:04 2020
#   Inital geometry file: a 106 line input string
#   Ligand name: 1-{4-amino-2-[(ethylamino)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O
#
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
 9K3  9K3  1-{4-amino-2-[(ethylamino)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol  ligand  46  23  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_9K3
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
 9K3  N    N  N     0  -0.514   2.7914  -2.0907  -0.3004
 9K3  C    C  CR16  0  -0.267   4.5810   0.6250   1.3257
 9K3  O    O  OH1   0  -0.662  -1.6765   2.0505  -1.9092
 9K3  C1   C  CR16  0  -0.304   4.2884  -0.5659   0.7078
 9K3  C11  C  CH2   0  -0.270  -4.9348  -0.8724   0.7133
 9K3  C12  C  CH3   0  -0.676  -5.4920  -1.3029   2.0575
 9K3  C14  C  CT    0   0.202  -0.8782   2.6071  -0.8827
 9K3  C15  C  CH3   0  -0.687   0.5493   2.8047  -1.3835
 9K3  C16  C  CH3   0  -0.672  -1.4499   3.9412  -0.4046
 9K3  C2   C  CR66  0   0.159   2.9818  -0.8690   0.2730
 9K3  C3   C  CR66  0   0.081   1.9610   0.1057   0.4720
 9K3  C4   C  CR16  0  -0.323   2.2877   1.3106   1.1196
 9K3  C5   C  CR16  0  -0.263   3.5704   1.5704   1.5402
 9K3  C6   C  CR56  0   0.401   0.6750  -0.3002  -0.0027
 9K3  C7   C  CR6   0   0.370   1.5971  -2.4444  -0.6979
 9K3  C8   C  CR56  0  -0.030   0.4943  -1.5558  -0.5483
 9K3  C9   C  CR5   0   0.430  -1.4307  -0.6782  -0.5367
 9K3  N1   N  NH2   0  -0.831   1.4060  -3.6450  -1.2865
 9K3  N2   N  N     0  -0.458  -0.8108  -1.7770  -0.8668
 9K3  N3   N  NR5   0  -0.539  -0.5773   0.2642  -0.0191
 9K3  N4   N  NH1   0  -0.596  -3.4833  -0.9537   0.7046
 9K3  H1   H  HCR6  0   0.255   5.5924   0.8306   1.6518
 9K3  H2   H  HOH1  0   0.453  -1.5999   2.6073  -2.6915
 9K3  H3   H  HCR6  0   0.251   5.0602  -1.3077   0.5450
 9K3  H4   H  HCH2  0   0.236  -3.2097   0.4821  -0.8621
 9K3  H5   H  HCH2  0   0.262  -3.2891  -1.1983  -1.3486
 9K3  H6   H  HCH2  0   0.222  -5.3150  -1.5331  -0.0713
 9K3  H7   H  HCH2  0   0.195  -5.3003   0.1367   0.4680
 9K3  H8   H  HCH3  0   0.231  -6.5804  -1.2467   2.0591
 9K3  H9   H  HCH3  0   0.225  -5.2050  -2.3285   2.2908
 9K3  H10  H  HCH3  0   0.222  -5.1274  -0.6585   2.8600
 9K3  H11  H  HCH2  0   0.288  -0.3779   1.9870   1.1341
 9K3  H12  H  HCH2  0   0.285  -1.9982   1.6017   0.6577
 9K3  H13  H  HCH3  0   0.245   0.5476   3.4804  -2.2423
 9K3  H14  H  HCH3  0   0.229   1.1840   3.2583  -0.6233
 9K3  H15  H  HCH3  0   0.245   1.0087   1.8687  -1.7022
 9K3  H16  H  HCH3  0   0.240  -2.4877   3.8362  -0.0847
 9K3  H17  H  HCH3  0   0.231  -0.8742   4.3361   0.4335
 9K3  H18  H  HCH3  0   0.241  -1.4144   4.6819  -1.2049
 9K3  H19  H  HCR6  0   0.242   1.5300   2.0574   1.3012
 9K3  H20  H  HCR6  0   0.256   3.7947   2.5050   2.0367
 9K3  H21  H  HNH2  0   0.390   2.1306  -4.3370  -1.1955
 9K3  H22  H  HNH2  0   0.398   0.4672  -3.9949  -1.3743
 9K3  H23  H  HNH1  0   0.344  -3.1238  -0.3618   1.4461
 9K3  C10  C  CH2   0  -0.390  -2.9169  -0.5310  -0.5687
 9K3  C13  C  CH2   0  -0.347  -0.9693   1.6248   0.2969

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
 9K3  C    C5   aromatic  1.401  0.020  1.401
 9K3  C    C1   aromatic  1.373  0.020  1.373
 9K3  C5   C4   aromatic  1.375  0.020  1.375
 9K3  C1   C2   aromatic  1.410  0.020  1.410
 9K3  C4   C3   aromatic  1.406  0.020  1.406
 9K3  C2   N    aromatic  1.363  0.020  1.363
 9K3  C2   C3   aromatic  1.425  0.020  1.425
 9K3  N    C7   aromatic  1.308  0.020  1.308
 9K3  C3   C6   aromatic  1.430  0.020  1.430
 9K3  C7   N1   single    1.351  0.020  1.351
 9K3  C7   C8   aromatic  1.424  0.020  1.424
 9K3  C6   C8   aromatic  1.381  0.020  1.381
 9K3  C6   N3   aromatic  1.374  0.020  1.374
 9K3  C12  C11  single    1.517  0.020  1.517
 9K3  C8   N2   aromatic  1.361  0.020  1.361
 9K3  C13  N3   single    1.451  0.020  1.451
 9K3  C13  C14  single    1.538  0.020  1.538
 9K3  N3   C9   aromatic  1.373  0.020  1.373
 9K3  C11  N4   single    1.454  0.020  1.454
 9K3  O    C14  single    1.414  0.020  1.414
 9K3  N2   C9   aromatic  1.304  0.020  1.304
 9K3  C14  C16  single    1.528  0.020  1.528
 9K3  C14  C15  single    1.526  0.020  1.526
 9K3  C9   C10  single    1.494  0.020  1.494
 9K3  N4   C10  single    1.456  0.020  1.456
 9K3  C    H1   single    0.930  0.020  1.080
 9K3  O    H2   single    0.850  0.020  0.980
 9K3  C1   H3   single    0.930  0.020  1.080
 9K3  C10  H4   single    0.970  0.020  1.090
 9K3  C10  H5   single    0.970  0.020  1.090
 9K3  C11  H6   single    0.970  0.020  1.090
 9K3  C11  H7   single    0.970  0.020  1.090
 9K3  C12  H8   single    0.970  0.020  1.090
 9K3  C12  H9   single    0.970  0.020  1.090
 9K3  C12  H10  single    0.970  0.020  1.090
 9K3  C13  H11  single    0.970  0.020  1.090
 9K3  C13  H12  single    0.970  0.020  1.090
 9K3  C15  H13  single    0.970  0.020  1.090
 9K3  C15  H14  single    0.970  0.020  1.090
 9K3  C15  H15  single    0.970  0.020  1.090
 9K3  C16  H16  single    0.970  0.020  1.090
 9K3  C16  H17  single    0.970  0.020  1.090
 9K3  C16  H18  single    0.970  0.020  1.090
 9K3  C4   H19  single    0.930  0.020  1.080
 9K3  C5   H20  single    0.930  0.020  1.080
 9K3  N1   H21  single    0.890  0.020  1.040
 9K3  N1   H22  single    0.890  0.020  1.040
 9K3  N4   H23  single    0.890  0.020  1.040

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
 9K3  C7   N    C2   119.87  3.000
 9K3  H1   C    C5   119.99  3.000
 9K3  H1   C    C1   119.97  3.000
 9K3  C5   C    C1   120.04  3.000
 9K3  H2   O    C14  108.48  3.000
 9K3  H3   C1   C2   117.83  3.000
 9K3  H3   C1   C    120.66  3.000
 9K3  C2   C1   C    121.51  3.000
 9K3  H7   C11  H6   106.17  3.000
 9K3  H7   C11  N4   112.42  3.000
 9K3  H6   C11  N4   108.00  3.000
 9K3  H7   C11  C12  109.60  3.000
 9K3  H6   C11  C12  109.66  3.000
 9K3  N4   C11  C12  110.86  3.000
 9K3  H10  C12  H9   108.06  3.000
 9K3  H10  C12  H8   107.58  3.000
 9K3  H9   C12  H8   108.12  3.000
 9K3  H10  C12  C11  111.16  3.000
 9K3  H9   C12  C11  111.08  3.000
 9K3  H8   C12  C11  110.70  3.000
 9K3  C16  C14  C15  109.86  3.000
 9K3  C15  C14  C13  112.95  3.000
 9K3  C16  C14  C13  107.19  3.000
 9K3  C15  C14  O    109.93  3.000
 9K3  C16  C14  O    111.07  3.000
 9K3  C13  C14  O    105.77  3.000
 9K3  H15  C15  H14  108.42  3.000
 9K3  H15  C15  H13  107.57  3.000
 9K3  H14  C15  H13  106.97  3.000
 9K3  H15  C15  C14  112.27  3.000
 9K3  H14  C15  C14  111.72  3.000
 9K3  H13  C15  C14  109.67  3.000
 9K3  H18  C16  H17  107.49  3.000
 9K3  H18  C16  H16  108.14  3.000
 9K3  H17  C16  H16  108.15  3.000
 9K3  H18  C16  C14  110.55  3.000
 9K3  H17  C16  C14  111.04  3.000
 9K3  H16  C16  C14  111.33  3.000
 9K3  C3   C2   C1   118.27  3.000
 9K3  C3   C2   N    124.86  3.000
 9K3  C1   C2   N    116.86  3.000
 9K3  C6   C3   C4   127.24  3.000
 9K3  C6   C3   C2   113.81  3.000
 9K3  C4   C3   C2   118.93  3.000
 9K3  H19  C4   C5   118.22  3.000
 9K3  H19  C4   C3   120.48  3.000
 9K3  C5   C4   C3   121.31  3.000
 9K3  H20  C5   C4   119.82  3.000
 9K3  H20  C5   C    120.26  3.000
 9K3  C4   C5   C    119.93  3.000
 9K3  N3   C6   C8   104.45  3.000
 9K3  N3   C6   C3   135.02  3.000
 9K3  C8   C6   C3   120.47  3.000
 9K3  N1   C7   C8   119.40  3.000
 9K3  C8   C7   N    120.44  3.000
 9K3  N1   C7   N    120.14  3.000
 9K3  N2   C8   C7   128.05  3.000
 9K3  N2   C8   C6   111.45  3.000
 9K3  C7   C8   C6   120.50  3.000
 9K3  N3   C9   N2   112.24  3.000
 9K3  N2   C9   C10  123.40  3.000
 9K3  N3   C9   C10  123.98  3.000
 9K3  H22  N1   H21  116.16  3.000
 9K3  H22  N1   C7   118.64  3.000
 9K3  H21  N1   C7   118.04  3.000
 9K3  C9   N2   C8   105.04  3.000
 9K3  C9   N3   C6   106.80  3.000
 9K3  C9   N3   C13  123.92  3.000
 9K3  C6   N3   C13  128.98  3.000
 9K3  H23  N4   C11  108.47  3.000
 9K3  H23  N4   C10  109.38  3.000
 9K3  C11  N4   C10  112.17  3.000
 9K3  H5   C10  H4   106.43  3.000
 9K3  H5   C10  N4   108.33  3.000
 9K3  H4   C10  N4   113.51  3.000
 9K3  H5   C10  C9   107.12  3.000
 9K3  H4   C10  C9   111.29  3.000
 9K3  N4   C10  C9   109.86  3.000
 9K3  H12  C13  H11  105.40  3.000
 9K3  H12  C13  N3   107.89  3.000
 9K3  H11  C13  N3   109.47  3.000
 9K3  H12  C13  C14  108.85  3.000
 9K3  H11  C13  C14  110.22  3.000
 9K3  N3   C13  C14  114.58  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
 9K3  CONST_01  C    C1   C2   N     180.00   0.0  0
 9K3  CONST_02  C4   C3   C2   N     180.00   0.0  0
 9K3  CONST_03  C6   C3   C2   N       0.00   0.0  0
 9K3  CONST_04  C6   C8   C7   N       0.00   0.0  0
 9K3  CONST_05  N2   C8   C7   N     180.00   0.0  0
 9K3  CONST_06  C3   C4   C5   C       0.00   0.0  0
 9K3  CONST_07  C3   C2   C1   C       0.00   0.0  0
 9K3  CONST_08  C4   C5   C    C1      0.00   0.0  0
 9K3  CONST_09  C7   N    C2   C1    180.00   0.0  0
 9K3  CONST_10  C4   C3   C2   C1      0.00   0.0  0
 9K3  CONST_11  C6   C3   C2   C1    180.00   0.0  0
 9K3  CONST_12  C5   C    C1   C2      0.00   0.0  0
 9K3  CONST_13  C8   C7   N    C2      0.00   0.0  0
 9K3  CONST_14  C5   C4   C3   C2      0.00   0.0  0
 9K3  CONST_15  C8   C6   C3   C2      0.00   0.0  0
 9K3  CONST_16  N3   C6   C3   C2    180.00   0.0  0
 9K3  CONST_17  C7   N    C2   C3      0.00   0.0  0
 9K3  CONST_18  C7   C8   C6   C3      0.00   0.0  0
 9K3  CONST_19  N2   C8   C6   C3    180.00   0.0  0
 9K3  CONST_20  C9   N3   C6   C3    180.00   0.0  0
 9K3  CONST_21  C8   C6   C3   C4    180.00   0.0  0
 9K3  CONST_22  N3   C6   C3   C4      0.00   0.0  0
 9K3  CONST_23  C6   C3   C4   C5    180.00   0.0  0
 9K3  CONST_24  C9   N2   C8   C6      0.00   0.0  0
 9K3  CONST_25  N2   C9   N3   C6      0.00   0.0  0
 9K3  CONST_26  N3   C6   C8   C7    180.00   0.0  0
 9K3  CONST_27  C9   N2   C8   C7    180.00   0.0  0
 9K3  CONST_28  C9   N3   C6   C8      0.00   0.0  0
 9K3  CONST_29  N3   C9   N2   C8      0.00   0.0  0
 9K3  CONST_30  N3   C6   C8   N2      0.00   0.0  0
 9K3  CONST_31  C6   N3   C9   C10   180.00   0.0  0
 9K3  CONST_32  C8   N2   C9   C10   180.00   0.0  0
 9K3  CONST_33  C3   C6   N3   C13     0.00   0.0  0
 9K3  CONST_34  C8   C6   N3   C13   180.00   0.0  0
 9K3  CONST_35  N2   C9   N3   C13   180.00   0.0  0
 9K3  CONST_36  N1   C7   N    C2    180.00   0.0  0
 9K3  CONST_37  N1   C7   C8   C6    180.00   0.0  0
 9K3  CONST_38  N2   C8   C7   N1      0.00   0.0  0
 9K3  CONST_39  H3   C1   C2   N       0.00   0.0  0
 9K3  CONST_40  H19  C4   C5   C     180.00   0.0  0
 9K3  CONST_41  H20  C5   C    C1    180.00   0.0  0
 9K3  CONST_42  H1   C    C1   C2    180.00   0.0  0
 9K3  Var_01    C6   N3   C13  C14    86.43  30.0  2
 9K3  Var_02    N4   C10  C9   N2     88.15  30.0  2
 9K3  Var_03    N3   C13  C14  O      56.13  30.0  2
 9K3  Var_04    C9   C10  N4   C11  -178.11  30.0  3
 9K3  Var_05    C12  C11  N4   C10  -179.31  30.0  1
 9K3  Var_06    H16  C16  C14  O      55.48  30.0  3
 9K3  Var_07    H13  C15  C14  O      60.00  30.0  3
 9K3  Var_08    H8   C12  C11  N4   -179.66  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
 9K3  plan-1  N    0.020
 9K3  plan-1  C    0.020
 9K3  plan-1  C1   0.020
 9K3  plan-1  C2   0.020
 9K3  plan-1  C3   0.020
 9K3  plan-1  C4   0.020
 9K3  plan-1  C5   0.020
 9K3  plan-1  C6   0.020
 9K3  plan-1  C7   0.020
 9K3  plan-1  C8   0.020
 9K3  plan-1  C9   0.020
 9K3  plan-1  N1   0.020
 9K3  plan-1  N2   0.020
 9K3  plan-1  N3   0.020
 9K3  plan-1  H1   0.020
 9K3  plan-1  H3   0.020
 9K3  plan-1  H19  0.020
 9K3  plan-1  H20  0.020
 9K3  plan-1  C10  0.020
 9K3  plan-1  C13  0.020
 9K3  plan-2  C7   0.020
 9K3  plan-2  N1   0.020
 9K3  plan-2  H21  0.020
 9K3  plan-2  H22  0.020

