# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 19 01:19:24 2020
#   Inital geometry file: a 78 line input string
#   Ligand name: 2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOCc1[nH]c2c3ccccc3nc(N)c2n1
#
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
 C09  C09  2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine  ligand  32  18  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C09
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
 C09  N    N  NH2   0  -0.830   1.6800   3.3091  -0.4754
 C09  C    C  CR6   0   0.369   1.6387   1.9754  -0.2634
 C09  C4   C  CR56  0  -0.019   0.3805   1.3319  -0.0728
 C09  N2   N  N     0  -0.461  -0.8802   1.8629  -0.0379
 C09  C5   C  CR5   0   0.390  -1.6644   0.8402   0.1661
 C09  C6   C  CH2   0  -0.207  -3.1423   0.8988   0.3425
 C09  O    O  O2    0  -0.493  -3.6923  -0.2927  -0.1443
 C09  C7   C  CH2   0  -0.143  -5.0808  -0.3998   0.1010
 C09  C8   C  CH3   0  -0.690  -5.5735  -1.7257  -0.4294
 C09  N3   N  NR15  0  -0.685  -0.9739  -0.3282   0.2617
 C09  C3   C  CR56  0   0.412   0.3450  -0.0341   0.1063
 C09  C2   C  CR66  0   0.053   1.5215  -0.8249   0.0985
 C09  C9   C  CR16  0  -0.320   1.5727  -2.2168   0.2679
 C09  C10  C  CR16  0  -0.271   2.7806  -2.8733   0.2449
 C09  C11  C  CR16  0  -0.261   3.9649  -2.1459   0.0522
 C09  C12  C  CR16  0  -0.305   3.9316  -0.7816  -0.1161
 C09  C1   C  CR66  0   0.167   2.7117  -0.0753  -0.0985
 C09  N1   N  N     0  -0.516   2.7480   1.2776  -0.2680
 C09  H1   H  HNH2  0   0.398   0.8771   3.8618  -0.2271
 C09  H2   H  HNH2  0   0.390   2.5717   3.7693  -0.4017
 C09  H4   H  HCH2  0   0.238  -3.3732   1.0347   1.4098
 C09  H5   H  HCH2  0   0.239  -3.5260   1.7840  -0.1795
 C09  H6   H  HCH2  0   0.206  -5.2807  -0.3216   1.1777
 C09  H7   H  HCH2  0   0.206  -5.6153   0.4271  -0.3842
 C09  H8   H  HCH3  0   0.231  -5.0757  -2.5611   0.0636
 C09  H9   H  HCH3  0   0.234  -6.6437  -1.8180  -0.2465
 C09  H10  H  HCH3  0   0.232  -5.4104  -1.8106  -1.5041
 C09  H12  H  HCR6  0   0.251   0.6569  -2.7759   0.4176
 C09  H13  H  HCR6  0   0.256   2.8184  -3.9466   0.3734
 C09  H14  H  HCR6  0   0.255   4.9148  -2.6648   0.0356
 C09  H15  H  HCR6  0   0.251   4.8461  -0.2218  -0.2677
 C09  H3   H  HNR5  0   0.421  -1.3846  -1.2380   0.4069

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
 C09  C11  C10  aromatic  1.403  0.020  1.403
 C09  C11  C12  aromatic  1.375  0.020  1.375
 C09  C10  C9   aromatic  1.375  0.020  1.375
 C09  C12  C1   aromatic  1.410  0.020  1.410
 C09  C9   C2   aromatic  1.403  0.020  1.403
 C09  C1   C2   aromatic  1.420  0.020  1.420
 C09  C1   N1   aromatic  1.364  0.020  1.364
 C09  C2   C3   aromatic  1.418  0.020  1.418
 C09  N1   C    aromatic  1.311  0.020  1.311
 C09  C3   N3   aromatic  1.360  0.020  1.360
 C09  C3   C4   aromatic  1.378  0.020  1.378
 C09  C    C4   aromatic  1.426  0.020  1.426
 C09  C    N    single    1.351  0.020  1.351
 C09  N3   C5   aromatic  1.361  0.020  1.361
 C09  C4   N2   aromatic  1.368  0.020  1.368
 C09  C5   N2   aromatic  1.305  0.020  1.305
 C09  C5   C6   single    1.489  0.020  1.489
 C09  C8   C7   single    1.511  0.020  1.511
 C09  C7   O    single    1.414  0.020  1.414
 C09  O    C6   single    1.400  0.020  1.400
 C09  N    H1   single    0.890  0.020  1.040
 C09  N    H2   single    0.890  0.020  1.040
 C09  C6   H4   single    0.970  0.020  1.090
 C09  C6   H5   single    0.970  0.020  1.090
 C09  C7   H6   single    0.970  0.020  1.090
 C09  C7   H7   single    0.970  0.020  1.090
 C09  C8   H8   single    0.970  0.020  1.090
 C09  C8   H9   single    0.970  0.020  1.090
 C09  C8   H10  single    0.970  0.020  1.090
 C09  C9   H12  single    0.930  0.020  1.080
 C09  C10  H13  single    0.930  0.020  1.080
 C09  C11  H14  single    0.930  0.020  1.080
 C09  C12  H15  single    0.930  0.020  1.080
 C09  N3   H3   single    0.860  0.020  1.020

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
 C09  H2   N    H1   115.98  3.000
 C09  H2   N    C    117.85  3.000
 C09  H1   N    C    118.64  3.000
 C09  N1   C    C4   120.47  3.000
 C09  C4   C    N    119.56  3.000
 C09  N1   C    N    119.95  3.000
 C09  C3   C4   N2   110.95  3.000
 C09  N2   C4   C    129.88  3.000
 C09  C3   C4   C    119.17  3.000
 C09  C5   N2   C4   104.69  3.000
 C09  N3   C5   C6   121.94  3.000
 C09  C6   C5   N2   125.74  3.000
 C09  N3   C5   N2   112.27  3.000
 C09  H5   C6   H4   106.77  3.000
 C09  H5   C6   O    112.58  3.000
 C09  H4   C6   O    111.10  3.000
 C09  H5   C6   C5   108.81  3.000
 C09  H4   C6   C5   109.15  3.000
 C09  O    C6   C5   108.38  3.000
 C09  C7   O    C6   112.96  3.000
 C09  H7   C7   H6   106.93  3.000
 C09  H7   C7   C8   110.31  3.000
 C09  H6   C7   C8   110.33  3.000
 C09  H7   C7   O    110.15  3.000
 C09  H6   C7   O    110.09  3.000
 C09  C8   C7   O    109.02  3.000
 C09  H10  C8   H9   107.81  3.000
 C09  H10  C8   H8   108.53  3.000
 C09  H9   C8   H8   107.92  3.000
 C09  H10  C8   C7   111.44  3.000
 C09  H9   C8   C7   109.62  3.000
 C09  H8   C8   C7   111.39  3.000
 C09  H3   N3   C3   127.32  3.000
 C09  H3   N3   C5   125.31  3.000
 C09  C3   N3   C5   107.36  3.000
 C09  C2   C3   N3   133.22  3.000
 C09  N3   C3   C4   104.72  3.000
 C09  C2   C3   C4   122.06  3.000
 C09  C1   C2   C9   120.65  3.000
 C09  C1   C2   C3   113.69  3.000
 C09  C9   C2   C3   125.66  3.000
 C09  H12  C9   C10  119.90  3.000
 C09  H12  C9   C2   119.86  3.000
 C09  C10  C9   C2   120.24  3.000
 C09  H13  C10  C11  120.08  3.000
 C09  H13  C10  C9   120.16  3.000
 C09  C11  C10  C9   119.76  3.000
 C09  H14  C11  C12  119.67  3.000
 C09  H14  C11  C10  119.62  3.000
 C09  C12  C11  C10  120.71  3.000
 C09  H15  C12  C1   118.26  3.000
 C09  H15  C12  C11  120.63  3.000
 C09  C1   C12  C11  121.10  3.000
 C09  N1   C1   C12  118.19  3.000
 C09  N1   C1   C2   124.26  3.000
 C09  C12  C1   C2   117.54  3.000
 C09  C1   N1   C    120.34  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
 C09  CONST_01  C12  C1   N1   C     180.00   0.0  0
 C09  CONST_02  C2   C1   N1   C       0.00   0.0  0
 C09  CONST_03  C2   C3   C4   C       0.00   0.0  0
 C09  CONST_04  N3   C3   C4   C     180.00   0.0  0
 C09  CONST_05  C5   N2   C4   C     180.00   0.0  0
 C09  CONST_06  C9   C2   C3   C4    180.00   0.0  0
 C09  CONST_07  C1   C2   C3   C4      0.00   0.0  0
 C09  CONST_08  C5   N3   C3   C4      0.00   0.0  0
 C09  CONST_09  C1   N1   C    C4      0.00   0.0  0
 C09  CONST_10  N3   C5   N2   C4      0.00   0.0  0
 C09  CONST_11  C2   C3   C4   N2    180.00   0.0  0
 C09  CONST_12  N3   C3   C4   N2      0.00   0.0  0
 C09  CONST_13  N1   C    C4   N2    180.00   0.0  0
 C09  CONST_14  C3   N3   C5   N2      0.00   0.0  0
 C09  CONST_15  C2   C3   N3   C5    180.00   0.0  0
 C09  CONST_16  C3   C4   N2   C5      0.00   0.0  0
 C09  CONST_17  C9   C2   C3   N3      0.00   0.0  0
 C09  CONST_18  C1   C2   C3   N3    180.00   0.0  0
 C09  CONST_19  C10  C9   C2   C3    180.00   0.0  0
 C09  CONST_20  C12  C1   C2   C3    180.00   0.0  0
 C09  CONST_21  N1   C1   C2   C3      0.00   0.0  0
 C09  CONST_22  N1   C    C4   C3      0.00   0.0  0
 C09  CONST_23  C11  C10  C9   C2      0.00   0.0  0
 C09  CONST_24  C11  C12  C1   C2      0.00   0.0  0
 C09  CONST_25  C12  C11  C10  C9      0.00   0.0  0
 C09  CONST_26  C12  C1   C2   C9      0.00   0.0  0
 C09  CONST_27  N1   C1   C2   C9    180.00   0.0  0
 C09  CONST_28  C1   C12  C11  C10     0.00   0.0  0
 C09  CONST_29  C1   C2   C9   C10     0.00   0.0  0
 C09  CONST_30  N1   C1   C12  C11   180.00   0.0  0
 C09  CONST_31  C1   N1   C    N     180.00   0.0  0
 C09  CONST_32  C3   C4   C    N     180.00   0.0  0
 C09  CONST_33  N2   C4   C    N       0.00   0.0  0
 C09  CONST_34  C6   C5   N2   C4    180.00   0.0  0
 C09  CONST_35  C3   N3   C5   C6    180.00   0.0  0
 C09  CONST_36  H3   N3   C3   C4    180.00   0.0  0
 C09  CONST_37  H12  C9   C2   C3      0.00   0.0  0
 C09  CONST_38  H13  C10  C9   C2    180.00   0.0  0
 C09  CONST_39  H15  C12  C1   C2    180.00   0.0  0
 C09  CONST_40  H14  C11  C10  C9    180.00   0.0  0
 C09  CONST_42  H2   N    C    C4    180.00   0.0  0
 C09  Var_01    O    C6   C5   N2    149.66  30.0  2
 C09  Var_02    C8   C7   O    C6   -178.70  30.0  1
 C09  Var_03    H8   C8   C7   O      60.70  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
 C09  plan-1  N    0.020
 C09  plan-1  C    0.020
 C09  plan-1  C4   0.020
 C09  plan-1  N2   0.020
 C09  plan-1  C5   0.020
 C09  plan-1  C6   0.020
 C09  plan-1  N3   0.020
 C09  plan-1  C3   0.020
 C09  plan-1  C2   0.020
 C09  plan-1  C9   0.020
 C09  plan-1  C10  0.020
 C09  plan-1  C11  0.020
 C09  plan-1  C12  0.020
 C09  plan-1  C1   0.020
 C09  plan-1  N1   0.020
 C09  plan-1  H12  0.020
 C09  plan-1  H13  0.020
 C09  plan-1  H14  0.020
 C09  plan-1  H15  0.020
 C09  plan-1  H3   0.020
 C09  plan-2  N    0.020
 C09  plan-2  C    0.020
 C09  plan-2  H1   0.020
 C09  plan-2  H2   0.020

