# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 21 08:56:41 2022
#   Inital geometry file: a 132 line input string
#   Ligand name: (4R)-N~4~-(6-chloro-2-methoxyacridin-9-yl)-N~1~,N~1~-diethylpentane-1,4-diamine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(CC)CCC[C@@H](C)Nc1c2ccc(Cl)cc2nc3ccc(OC)cc13
#
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
 QUN  QUN  (4R)-N~4~-(6-chloro-2-methoxyacridin-9-yl)-N~1~,N~1~-diethylpentane-1,4-diamine  ligand  58  28  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_QUN
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
 QUN  C1    C   CR6   0   0.404   3.1300  -0.4215   0.7244
 QUN  C2    C   CR16  0  -0.372   4.0450  -0.4109  -0.3636
 QUN  C3    C   CR16  0  -0.283   3.5932  -0.2291  -1.6351
 QUN  C4    C   CR66  0   0.141   2.2112  -0.0638  -1.9188
 QUN  C5    C   CR66  0   0.086   1.2908  -0.1435  -0.8329
 QUN  C6    C   CR16  0  -0.440   1.7881  -0.2891   0.4839
 QUN  N1    N   N     0  -0.494   1.8546   0.1855  -3.1799
 QUN  C7    C   CR66  0   0.155   0.5661   0.3677  -3.4384
 QUN  C8    C   CR66  0   0.063  -0.4605   0.2625  -2.4471
 QUN  C9    C   CR6   0   0.360  -0.0875  -0.0119  -1.1169
 QUN  C10   C   CR16  0  -0.256   0.2010   0.6590  -4.7856
 QUN  C11   C   CR6   0  -0.054  -1.1059   0.8130  -5.1166
 QUN  C12   C   CR16  0  -0.213  -2.1386   0.6773  -4.1563
 QUN  C13   C   CR16  0  -0.339  -1.8134   0.4062  -2.8639
 QUN  CL    CL  CL    0  -0.119  -1.5523   1.1720  -6.7499
 QUN  O     O   O2    0  -0.471   3.5153  -0.5433   2.0086
 QUN  C14   C   CH3   0  -0.440   4.8958  -0.5968   2.3132
 QUN  N2    N   NH1   0  -0.670  -1.0145  -0.1143  -0.0986
 QUN  C15   C   CH1   0  -0.132  -1.2528  -1.4194   0.5417
 QUN  C16   C   CH3   0  -0.655  -1.9572  -2.3842  -0.4068
 QUN  C17   C   CH2   0  -0.428  -2.0583  -1.2097   1.8184
 QUN  C18   C   CH2   0  -0.434  -1.3385  -0.4080   2.8936
 QUN  C19   C   CH2   0  -0.266  -2.1965  -0.2357   4.1403
 QUN  N3    N   NT    0  -0.414  -1.5266   0.5181   5.1880
 QUN  C20   C   CH2   0  -0.285  -1.5985   1.9510   4.9420
 QUN  C21   C   CH2   0  -0.284  -2.0071   0.1642   6.5153
 QUN  C22   C   CH3   0  -0.667  -0.5043   2.7345   5.6488
 QUN  C23   C   CH3   0  -0.663  -1.4597  -1.1654   7.0101
 QUN  H21   H   HCR6  0   0.288   5.1078  -0.5255  -0.1996
 QUN  H31   H   HCR6  0   0.268   4.2906  -0.1946  -2.4618
 QUN  H61   H   HCR6  0   0.275   1.1074  -0.2591   1.3229
 QUN  H101  H   HCR6  0   0.280   0.9891   0.7485  -5.5213
 QUN  H121  H   HCR6  0   0.283  -3.1730   0.7807  -4.4528
 QUN  H131  H   HCR6  0   0.254  -2.6227   0.2939  -2.1557
 QUN  H141  H   HCH3  0   0.263   4.9678  -0.6502   3.3966
 QUN  H142  H   HCH3  0   0.230   5.3776  -1.4813   1.8889
 QUN  H143  H   HCH3  0   0.230   5.4263   0.2955   1.9713
 QUN  HN21  H   HNH1  0   0.376  -1.8987   0.3158  -0.3348
 QUN  H151  H   HCH1  0   0.252  -0.2833  -1.8472   0.8061
 QUN  H161  H   HCH3  0   0.221  -2.9398  -2.0030  -0.6948
 QUN  H162  H   HCH3  0   0.237  -1.3775  -2.5461  -1.3165
 QUN  H163  H   HCH3  0   0.239  -2.1031  -3.3531   0.0724
 QUN  H171  H   HCH2  0   0.231  -2.3224  -2.1947   2.2151
 QUN  H172  H   HCH2  0   0.220  -3.0092  -0.7260   1.5636
 QUN  H181  H   HCH2  0   0.224  -1.0475   0.5652   2.4892
 QUN  H182  H   HCH2  0   0.214  -0.4134  -0.9188   3.1775
 QUN  H191  H   HCH2  0   0.226  -2.4416  -1.2300   4.5205
 QUN  H192  H   HCH2  0   0.193  -3.1611   0.2263   3.8674
 QUN  H201  H   HCH2  0   0.192  -2.5879   2.3570   5.2131
 QUN  H202  H   HCH2  0   0.227  -1.4923   2.1176   3.8683
 QUN  H211  H   HCH2  0   0.227  -1.6878   0.9391   7.2141
 QUN  H212  H   HCH2  0   0.191  -3.1090   0.1565   6.5590
 QUN  H221  H   HCH3  0   0.225  -0.5826   3.7949   5.4063
 QUN  H222  H   HCH3  0   0.223  -0.5604   2.6477   6.7346
 QUN  H223  H   HCH3  0   0.220   0.4804   2.3873   5.3349
 QUN  H231  H   HCH3  0   0.224  -1.8001  -1.3589   8.0278
 QUN  H232  H   HCH3  0   0.221  -1.7833  -2.0064   6.3958
 QUN  H233  H   HCH3  0   0.220  -0.3693  -1.1529   7.0140

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
 QUN  C1   C2    aromatic  1.422  0.020  1.422
 QUN  C1   C6    aromatic  1.370  0.020  1.370
 QUN  C1   O     single    1.346  0.020  1.346
 QUN  C2   C3    aromatic  1.362  0.020  1.362
 QUN  C2   H21   single    0.930  0.020  1.080
 QUN  C3   C4    aromatic  1.420  0.020  1.420
 QUN  C3   H31   single    0.930  0.020  1.080
 QUN  C4   C5    aromatic  1.426  0.020  1.426
 QUN  C4   N1    aromatic  1.334  0.020  1.334
 QUN  C5   C6    aromatic  1.415  0.020  1.415
 QUN  C5   C9    aromatic  1.413  0.020  1.413
 QUN  C6   H61   single    0.930  0.020  1.080
 QUN  N1   C7    aromatic  1.327  0.020  1.327
 QUN  C7   C8    aromatic  1.431  0.020  1.431
 QUN  C7   C10   aromatic  1.426  0.020  1.426
 QUN  C8   C9    aromatic  1.408  0.020  1.408
 QUN  C8   C13   aromatic  1.423  0.020  1.423
 QUN  C9   N2    single    1.381  0.020  1.381
 QUN  C10  C11   aromatic  1.357  0.020  1.357
 QUN  C10  H101  single    0.930  0.020  1.080
 QUN  C11  C12   aromatic  1.417  0.020  1.417
 QUN  C11  CL    single    1.731  0.020  1.731
 QUN  C12  C13   aromatic  1.360  0.020  1.360
 QUN  C12  H121  single    0.930  0.020  1.080
 QUN  C13  H131  single    0.930  0.020  1.080
 QUN  O    C14   single    1.415  0.020  1.415
 QUN  C14  H141  single    0.970  0.020  1.090
 QUN  C14  H142  single    0.970  0.020  1.090
 QUN  C14  H143  single    0.970  0.020  1.090
 QUN  N2   C15   single    1.473  0.020  1.473
 QUN  N2   HN21  single    0.890  0.020  1.040
 QUN  C15  C16   single    1.525  0.020  1.525
 QUN  C15  C17   single    1.524  0.020  1.524
 QUN  C15  H151  single    0.970  0.020  1.090
 QUN  C16  H161  single    0.970  0.020  1.090
 QUN  C16  H162  single    0.970  0.020  1.090
 QUN  C16  H163  single    0.970  0.020  1.090
 QUN  C17  C18   single    1.522  0.020  1.522
 QUN  C17  H171  single    0.970  0.020  1.090
 QUN  C17  H172  single    0.970  0.020  1.090
 QUN  C18  C19   single    1.523  0.020  1.523
 QUN  C18  H181  single    0.970  0.020  1.090
 QUN  C18  H182  single    0.970  0.020  1.090
 QUN  C19  N3    single    1.454  0.020  1.454
 QUN  C19  H191  single    0.970  0.020  1.090
 QUN  C19  H192  single    0.970  0.020  1.090
 QUN  N3   C20   single    1.456  0.020  1.456
 QUN  N3   C21   single    1.455  0.020  1.455
 QUN  C20  C22   single    1.520  0.020  1.520
 QUN  C20  H201  single    0.970  0.020  1.090
 QUN  C20  H202  single    0.970  0.020  1.090
 QUN  C21  C23   single    1.521  0.020  1.521
 QUN  C21  H211  single    0.970  0.020  1.090
 QUN  C21  H212  single    0.970  0.020  1.090
 QUN  C22  H221  single    0.970  0.020  1.090
 QUN  C22  H222  single    0.970  0.020  1.090
 QUN  C22  H223  single    0.970  0.020  1.090
 QUN  C23  H231  single    0.970  0.020  1.090
 QUN  C23  H232  single    0.970  0.020  1.090
 QUN  C23  H233  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
 QUN  O     C1   C6    117.17  3.000
 QUN  O     C1   C2    123.13  3.000
 QUN  C6    C1   C2    119.70  3.000
 QUN  H21   C2   C3    118.81  3.000
 QUN  H21   C2   C1    121.04  3.000
 QUN  C3    C2   C1    120.14  3.000
 QUN  H31   C3   C4    118.08  3.000
 QUN  H31   C3   C2    120.25  3.000
 QUN  C4    C3   C2    121.66  3.000
 QUN  N1    C4   C5    123.91  3.000
 QUN  N1    C4   C3    118.07  3.000
 QUN  C5    C4   C3    118.00  3.000
 QUN  C9    C5   C6    122.64  3.000
 QUN  C9    C5   C4    118.12  3.000
 QUN  C6    C5   C4    119.18  3.000
 QUN  H61   C6   C5    119.88  3.000
 QUN  H61   C6   C1    118.90  3.000
 QUN  C5    C6   C1    121.18  3.000
 QUN  C7    N1   C4    117.99  3.000
 QUN  C10   C7   C8    119.07  3.000
 QUN  C10   C7   N1    117.44  3.000
 QUN  C8    C7   N1    123.49  3.000
 QUN  C13   C8   C9    123.24  3.000
 QUN  C13   C8   C7    118.15  3.000
 QUN  C9    C8   C7    118.59  3.000
 QUN  N2    C9   C8    122.22  3.000
 QUN  N2    C9   C5    119.97  3.000
 QUN  C8    C9   C5    117.79  3.000
 QUN  H101  C10  C11   121.76  3.000
 QUN  H101  C10  C7    118.22  3.000
 QUN  C11   C10  C7    120.01  3.000
 QUN  CL    C11  C12   118.13  3.000
 QUN  CL    C11  C10   120.14  3.000
 QUN  C12   C11  C10   121.73  3.000
 QUN  H121  C12  C13   120.57  3.000
 QUN  H121  C12  C11   120.16  3.000
 QUN  C13   C12  C11   119.27  3.000
 QUN  H131  C13  C12   117.66  3.000
 QUN  H131  C13  C8    120.61  3.000
 QUN  C12   C13  C8    121.73  3.000
 QUN  C14   O    C1    119.22  3.000
 QUN  H143  C14  H142  108.98  3.000
 QUN  H143  C14  H141  108.65  3.000
 QUN  H142  C14  H141  108.54  3.000
 QUN  H143  C14  O     112.05  3.000
 QUN  H142  C14  O     112.16  3.000
 QUN  H141  C14  O     106.32  3.000
 QUN  HN21  N2   C15   109.68  3.000
 QUN  HN21  N2   C9    112.53  3.000
 QUN  C15   N2   C9    119.66  3.000
 QUN  H151  C15  C17   108.68  3.000
 QUN  H151  C15  C16   108.22  3.000
 QUN  C17   C15  C16   111.34  3.000
 QUN  H151  C15  N2    107.97  3.000
 QUN  C17   C15  N2    109.13  3.000
 QUN  C16   C15  N2    111.39  3.000
 QUN  H163  C16  H162  107.79  3.000
 QUN  H163  C16  H161  107.78  3.000
 QUN  H162  C16  H161  108.05  3.000
 QUN  H163  C16  C15   110.52  3.000
 QUN  H162  C16  C15   111.54  3.000
 QUN  H161  C16  C15   111.01  3.000
 QUN  H172  C17  H171  105.78  3.000
 QUN  H172  C17  C18   109.99  3.000
 QUN  H171  C17  C18   109.40  3.000
 QUN  H172  C17  C15   108.92  3.000
 QUN  H171  C17  C15   107.90  3.000
 QUN  C18   C17  C15   114.47  3.000
 QUN  H182  C18  H181  106.65  3.000
 QUN  H182  C18  C19   108.46  3.000
 QUN  H181  C18  C19   110.61  3.000
 QUN  H182  C18  C17   109.70  3.000
 QUN  H181  C18  C17   109.47  3.000
 QUN  C19   C18  C17   111.80  3.000
 QUN  H192  C19  H191  105.72  3.000
 QUN  H192  C19  N3    111.33  3.000
 QUN  H191  C19  N3    108.93  3.000
 QUN  H192  C19  C18   109.71  3.000
 QUN  H191  C19  C18   107.96  3.000
 QUN  N3    C19  C18   112.88  3.000
 QUN  C21   N3   C20   112.16  3.000
 QUN  C21   N3   C19   112.27  3.000
 QUN  C20   N3   C19   111.45  3.000
 QUN  H202  C20  H201  105.83  3.000
 QUN  H202  C20  C22   107.98  3.000
 QUN  H201  C20  C22   109.97  3.000
 QUN  H202  C20  N3    108.16  3.000
 QUN  H201  C20  N3    111.41  3.000
 QUN  C22   C20  N3    113.16  3.000
 QUN  H212  C21  H211  105.78  3.000
 QUN  H212  C21  C23   109.92  3.000
 QUN  H211  C21  C23   107.89  3.000
 QUN  H212  C21  N3    111.58  3.000
 QUN  H211  C21  N3    108.35  3.000
 QUN  C23   C21  N3    112.99  3.000
 QUN  H223  C22  H222  107.92  3.000
 QUN  H223  C22  H221  108.08  3.000
 QUN  H222  C22  H221  107.17  3.000
 QUN  H223  C22  C20   110.61  3.000
 QUN  H222  C22  C20   112.63  3.000
 QUN  H221  C22  C20   110.25  3.000
 QUN  H233  C23  H232  107.91  3.000
 QUN  H233  C23  H231  108.11  3.000
 QUN  H232  C23  H231  107.22  3.000
 QUN  H233  C23  C21   110.56  3.000
 QUN  H232  C23  C21   112.60  3.000
 QUN  H231  C23  C21   110.27  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
 QUN  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 QUN  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 QUN  CONST_03  C9    C5   C6   C1    180.00   0.0  0
 QUN  CONST_04  C5    C6   C1   C2      0.00   0.0  0
 QUN  CONST_05  C5    C4   C3   C2      0.00   0.0  0
 QUN  CONST_06  N1    C4   C3   C2    180.00   0.0  0
 QUN  CONST_07  C6    C1   C2   C3      0.00   0.0  0
 QUN  CONST_08  C6    C5   C4   C3      0.00   0.0  0
 QUN  CONST_09  C9    C5   C4   C3    180.00   0.0  0
 QUN  CONST_10  C7    N1   C4   C3    180.00   0.0  0
 QUN  CONST_11  C8    C9   C5   C4      0.00   0.0  0
 QUN  CONST_12  C8    C7   N1   C4      0.00   0.0  0
 QUN  CONST_13  C10   C7   N1   C4    180.00   0.0  0
 QUN  CONST_14  C7    N1   C4   C5      0.00   0.0  0
 QUN  CONST_15  C7    C8   C9   C5      0.00   0.0  0
 QUN  CONST_16  C13   C8   C9   C5    180.00   0.0  0
 QUN  CONST_17  N1    C4   C5   C6    180.00   0.0  0
 QUN  CONST_18  C8    C9   C5   C6    180.00   0.0  0
 QUN  CONST_19  C9    C5   C4   N1      0.00   0.0  0
 QUN  CONST_20  C9    C8   C7   N1      0.00   0.0  0
 QUN  CONST_21  C13   C8   C7   N1    180.00   0.0  0
 QUN  CONST_22  C11   C10  C7   N1    180.00   0.0  0
 QUN  CONST_23  C12   C13  C8   C7      0.00   0.0  0
 QUN  CONST_24  C12   C11  C10  C7      0.00   0.0  0
 QUN  CONST_25  C11   C10  C7   C8      0.00   0.0  0
 QUN  CONST_26  C11   C12  C13  C8      0.00   0.0  0
 QUN  CONST_27  C10   C7   C8   C9    180.00   0.0  0
 QUN  CONST_28  C12   C13  C8   C9    180.00   0.0  0
 QUN  CONST_29  C13   C8   C7   C10     0.00   0.0  0
 QUN  CONST_30  C13   C12  C11  C10     0.00   0.0  0
 QUN  CONST_31  O     C1   C2   C3    180.00   0.0  0
 QUN  CONST_32  N2    C9   C5   C4    180.00   0.0  0
 QUN  CONST_33  O     C1   C6   C5    180.00   0.0  0
 QUN  CONST_34  N2    C9   C5   C6      0.00   0.0  0
 QUN  CONST_35  N2    C9   C8   C7    180.00   0.0  0
 QUN  CONST_36  CL    C11  C10  C7    180.00   0.0  0
 QUN  CONST_37  N2    C9   C8   C13     0.00   0.0  0
 QUN  CONST_38  CL    C11  C12  C13   180.00   0.0  0
 QUN  CONST_39  H31   C3   C2   C1    180.00   0.0  0
 QUN  CONST_40  H61   C6   C1   C2    180.00   0.0  0
 QUN  CONST_41  H21   C2   C3   C4    180.00   0.0  0
 QUN  CONST_42  H101  C10  C7   N1      0.00   0.0  0
 QUN  CONST_43  H131  C13  C8   C7    180.00   0.0  0
 QUN  CONST_44  H121  C12  C13  C8    180.00   0.0  0
 QUN  Var_01    H141  C14  O    C1    177.57  30.0  3
 QUN  Var_02    C19   C18  C17  C15  -179.98  30.0  3
 QUN  Var_03    N3    C19  C18  C17   179.52  30.0  3
 QUN  Var_04    C20   N3   C19  C18    80.51  30.0  3
 QUN  Var_05    C22   C20  N3   C19  -157.38  30.0  3
 QUN  Var_06    C23   C21  N3   C19    76.35  30.0  3
 QUN  Var_07    H221  C22  C20  N3    178.13  30.0  3
 QUN  Var_08    H231  C23  C21  N3    176.71  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
 QUN  chir_01  C15  N2  C16  C17  positiv

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
 QUN  plan-1  C1    0.020
 QUN  plan-1  C2    0.020
 QUN  plan-1  C3    0.020
 QUN  plan-1  C4    0.020
 QUN  plan-1  C5    0.020
 QUN  plan-1  C6    0.020
 QUN  plan-1  N1    0.020
 QUN  plan-1  C7    0.020
 QUN  plan-1  C8    0.020
 QUN  plan-1  C9    0.020
 QUN  plan-1  C10   0.020
 QUN  plan-1  C11   0.020
 QUN  plan-1  C12   0.020
 QUN  plan-1  C13   0.020
 QUN  plan-1  CL    0.020
 QUN  plan-1  O     0.020
 QUN  plan-1  N2    0.020
 QUN  plan-1  H21   0.020
 QUN  plan-1  H31   0.020
 QUN  plan-1  H61   0.020
 QUN  plan-1  H101  0.020
 QUN  plan-1  H121  0.020
 QUN  plan-1  H131  0.020
 QUN  plan-2  C9    0.020
 QUN  plan-2  N2    0.020
 QUN  plan-2  C15   0.020
 QUN  plan-2  HN21  0.020

