# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  8 10:09:42 2020
#   Inital geometry file: a 119 line input string
#   Ligand name: N~2~-[(1R,2R)-2-aminocyclohexyl]-N~6~-(3-chlorophenyl)-9-ethyl-9H-purine-2,6-diamine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@@H]4CCCC[C@H]4N)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
 23D  23D  N~2~-[(1R,2R)-2-aminocyclohexyl]-N~6~-(3-chlorophenyl)-9-ethyl-9H-purine-2,6-diamine  ligand  51  27  .  2022-07-22  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_23D
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
 23D  CAS   C   CR16  0  -0.287  17.2067  31.8126   5.8964
 23D  CAQ   C   CR6   0  -0.032  17.6103  32.7804   4.9907
 23D  CL1   CL  CL    0  -0.121  18.7651  32.3327   3.7730
 23D  CAP   C   CR16  0  -0.245  17.1383  34.0804   5.0214
 23D  CAO   C   CR16  0  -0.249  16.2241  34.4109   6.0129
 23D  CAN   C   CR16  0  -0.353  15.8006  33.4724   6.9343
 23D  CAM   C   CR6   0   0.371  16.2867  32.1604   6.8879
 23D  N6    N   NH1   0  -0.775  15.8178  31.2864   7.8592
 23D  C6    C   CR6   0   0.531  16.0611  29.9682   8.0704
 23D  N1    N   N     0  -0.545  16.8523  29.2706   7.2734
 23D  C5    C   CR56  0  -0.066  15.4530  29.3249   9.1598
 23D  N7    N   N     0  -0.457  14.6012  29.7471  10.1491
 23D  C8    C   CR15  0   0.097  14.3939  28.6800  10.8617
 23D  N9    N   NR5   0  -0.500  15.0512  27.5724  10.3977
 23D  CAZ   C   CH2   0  -0.315  15.0738  26.2543  11.0023
 23D  CBA   C   CH3   0  -0.664  16.3408  26.0062  11.8018
 23D  C4    C   CR56  0   0.505  15.7463  27.9748   9.2985
 23D  N3    N   N     0  -0.516  16.5298  27.2471   8.5142
 23D  C2    C   CR6   0   0.594  17.0530  27.9632   7.5180
 23D  N2    N   NH1   0  -0.677  17.8895  27.3075   6.6794
 23D  CAG   C   CH1   0  -0.070  18.3601  27.8341   5.4156
 23D  CAF   C   CH2   0  -0.452  17.3164  27.7949   4.3026
 23D  CAE   C   CH2   0  -0.436  17.8155  28.5788   3.0787
 23D  CAD   C   CH2   0  -0.453  19.3457  28.5370   2.9588
 23D  CAC   C   CH2   0  -0.443  19.8793  27.2155   3.4920
 23D  CAA   C   CH1   0  -0.065  19.6285  27.0753   5.0009
 23D  NAB   N   NH2   0  -0.801  20.7581  27.6057   5.7512
 23D  HAS   H   HCR6  0   0.332  17.5922  30.8083   5.8401
 23D  HAP   H   HCR6  0   0.277  17.4701  34.8143   4.3009
 23D  HAO   H   HCR6  0   0.271  15.8364  35.4194   6.0657
 23D  HAN   H   HCR6  0   0.275  15.0880  33.7551   7.6999
 23D  HN6   H   HNH1  0   0.419  15.1822  31.6992   8.5263
 23D  H8    H   HCR5  0   0.288  13.7652  28.6257  11.7383
 23D  HAZ1  H   HCH2  0   0.262  14.9667  25.5141  10.2097
 23D  HAZ2  H   HCH2  0   0.265  14.1930  26.1744  11.6389
 23D  HBA1  H   HCH3  0   0.235  16.4487  26.7367  12.6032
 23D  HBA2  H   HCH3  0   0.242  16.3062  25.0135  12.2502
 23D  HBA3  H   HCH3  0   0.237  17.2243  26.0572  11.1663
 23D  HN2   H   HNH1  0   0.380  17.8929  26.3048   6.7879
 23D  HAG   H   HCH1  0   0.245  18.6457  28.8756   5.5844
 23D  HAF1  H   HCH2  0   0.239  16.3741  28.2131   4.6608
 23D  HAF2  H   HCH2  0   0.220  17.1141  26.7518   4.0397
 23D  HAE1  H   HCH2  0   0.221  17.4851  29.6181   3.1427
 23D  HAE2  H   HCH2  0   0.224  17.3605  28.1652   2.1760
 23D  HAD1  H   HCH2  0   0.217  19.7919  29.3591   3.5244
 23D  HAD2  H   HCH2  0   0.231  19.6457  28.6867   1.9198
 23D  HAC1  H   HCH2  0   0.233  20.9493  27.1104   3.2956
 23D  HAC2  H   HCH2  0   0.222  19.3938  26.3901   2.9634
 23D  HAA   H   HCH1  0   0.204  19.4556  26.0058   5.2086
 23D  HAB1  H   HNH2  0   0.340  20.5583  27.5448   6.7432
 23D  HAB2  H   HNH2  0   0.342  21.5671  27.0153   5.6006

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
 23D  CAS  CAQ   aromatic  1.386  0.020  1.386
 23D  CAS  CAM   aromatic  1.397  0.020  1.397
 23D  CAS  HAS   single    0.930  0.020  1.080
 23D  CAQ  CL1   single    1.737  0.020  1.737
 23D  CAQ  CAP   aromatic  1.383  0.020  1.383
 23D  CAP  CAO   aromatic  1.389  0.020  1.389
 23D  CAP  HAP   single    0.930  0.020  1.080
 23D  CAO  CAN   aromatic  1.382  0.020  1.382
 23D  CAO  HAO   single    0.930  0.020  1.080
 23D  CAN  CAM   aromatic  1.400  0.020  1.400
 23D  CAN  HAN   single    0.930  0.020  1.080
 23D  CAM  N6    single    1.388  0.020  1.388
 23D  N6   C6    single    1.357  0.020  1.357
 23D  N6   HN6   single    0.860  0.020  1.020
 23D  C6   N1    aromatic  1.322  0.020  1.322
 23D  C6   C5    aromatic  1.404  0.020  1.404
 23D  N1   C2    aromatic  1.345  0.020  1.345
 23D  C5   N7    aromatic  1.372  0.020  1.372
 23D  C5   C4    aromatic  1.389  0.020  1.389
 23D  N7   C8    aromatic  1.300  0.020  1.300
 23D  C8   N9    aromatic  1.369  0.020  1.369
 23D  C8   H8    single    0.930  0.020  1.080
 23D  N9   CAZ   single    1.450  0.020  1.450
 23D  N9   C4    aromatic  1.361  0.020  1.361
 23D  CAZ  CBA   single    1.519  0.020  1.519
 23D  CAZ  HAZ1  single    0.970  0.020  1.090
 23D  CAZ  HAZ2  single    0.970  0.020  1.090
 23D  CBA  HBA1  single    0.970  0.020  1.090
 23D  CBA  HBA2  single    0.970  0.020  1.090
 23D  CBA  HBA3  single    0.970  0.020  1.090
 23D  C4   N3    aromatic  1.326  0.020  1.326
 23D  N3   C2    aromatic  1.334  0.020  1.334
 23D  C2   N2    single    1.354  0.020  1.354
 23D  N2   CAG   single    1.448  0.020  1.448
 23D  N2   HN2   single    0.890  0.020  1.040
 23D  CAG  CAF   single    1.526  0.020  1.526
 23D  CAG  CAA   single    1.535  0.020  1.535
 23D  CAG  HAG   single    0.970  0.020  1.090
 23D  CAF  CAE   single    1.537  0.020  1.537
 23D  CAF  HAF1  single    0.970  0.020  1.090
 23D  CAF  HAF2  single    0.970  0.020  1.090
 23D  CAE  CAD   single    1.535  0.020  1.535
 23D  CAE  HAE1  single    0.970  0.020  1.090
 23D  CAE  HAE2  single    0.970  0.020  1.090
 23D  CAD  CAC   single    1.522  0.020  1.522
 23D  CAD  HAD1  single    0.970  0.020  1.090
 23D  CAD  HAD2  single    0.970  0.020  1.090
 23D  CAC  CAA   single    1.536  0.020  1.536
 23D  CAC  HAC1  single    0.970  0.020  1.090
 23D  CAC  HAC2  single    0.970  0.020  1.090
 23D  CAA  NAB   single    1.456  0.020  1.456
 23D  CAA  HAA   single    0.970  0.020  1.090
 23D  NAB  HAB1  single    0.890  0.020  1.040
 23D  NAB  HAB2  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
 23D  HAS   CAS  CAM   120.33  3.000
 23D  HAS   CAS  CAQ   120.85  3.000
 23D  CAM   CAS  CAQ   118.81  3.000
 23D  CAP   CAQ  CL1   118.99  3.000
 23D  CAP   CAQ  CAS   122.86  3.000
 23D  CL1   CAQ  CAS   118.16  3.000
 23D  HAP   CAP  CAO   121.10  3.000
 23D  HAP   CAP  CAQ   121.24  3.000
 23D  CAO   CAP  CAQ   117.66  3.000
 23D  HAO   CAO  CAN   119.40  3.000
 23D  HAO   CAO  CAP   119.52  3.000
 23D  CAN   CAO  CAP   121.08  3.000
 23D  HAN   CAN  CAM   119.76  3.000
 23D  HAN   CAN  CAO   119.71  3.000
 23D  CAM   CAN  CAO   120.53  3.000
 23D  N6    CAM  CAN   116.71  3.000
 23D  N6    CAM  CAS   124.22  3.000
 23D  CAN   CAM  CAS   119.06  3.000
 23D  HN6   N6   C6    114.03  3.000
 23D  HN6   N6   CAM   114.68  3.000
 23D  C6    N6   CAM   131.29  3.000
 23D  C5    C6   N1    119.03  3.000
 23D  C5    C6   N6    119.23  3.000
 23D  N1    C6   N6    121.74  3.000
 23D  C2    N1   C6    119.51  3.000
 23D  C4    C5   N7    111.00  3.000
 23D  C4    C5   C6    115.57  3.000
 23D  N7    C5   C6    133.43  3.000
 23D  C8    N7   C5    103.99  3.000
 23D  H8    C8   N9    120.92  3.000
 23D  H8    C8   N7    125.38  3.000
 23D  N9    C8   N7    113.69  3.000
 23D  C4    N9   CAZ   126.67  3.000
 23D  C4    N9   C8    106.24  3.000
 23D  CAZ   N9   C8    126.98  3.000
 23D  HAZ2  CAZ  HAZ1  107.19  3.000
 23D  HAZ2  CAZ  CBA   110.79  3.000
 23D  HAZ1  CAZ  CBA   110.73  3.000
 23D  HAZ2  CAZ  N9    107.31  3.000
 23D  HAZ1  CAZ  N9    108.21  3.000
 23D  CBA   CAZ  N9    112.40  3.000
 23D  HBA3  CBA  HBA2  107.97  3.000
 23D  HBA3  CBA  HBA1  108.50  3.000
 23D  HBA2  CBA  HBA1  108.13  3.000
 23D  HBA3  CBA  CAZ   111.21  3.000
 23D  HBA2  CBA  CAZ   109.82  3.000
 23D  HBA1  CBA  CAZ   111.11  3.000
 23D  N3    C4   N9    128.10  3.000
 23D  N3    C4   C5    126.82  3.000
 23D  N9    C4   C5    105.08  3.000
 23D  C2    N3   C4    112.27  3.000
 23D  N2    C2   N3    116.43  3.000
 23D  N2    C2   N1    116.76  3.000
 23D  N3    C2   N1    126.80  3.000
 23D  HN2   N2   CAG   117.03  3.000
 23D  HN2   N2   C2    114.64  3.000
 23D  CAG   N2   C2    124.43  3.000
 23D  HAG   CAG  CAA   107.27  3.000
 23D  HAG   CAG  CAF   108.41  3.000
 23D  CAA   CAG  CAF   110.82  3.000
 23D  HAG   CAG  N2    107.26  3.000
 23D  CAA   CAG  N2    108.94  3.000
 23D  CAF   CAG  N2    113.88  3.000
 23D  HAF2  CAF  HAF1  106.53  3.000
 23D  HAF2  CAF  CAE   110.78  3.000
 23D  HAF1  CAF  CAE   110.26  3.000
 23D  HAF2  CAF  CAG   109.03  3.000
 23D  HAF1  CAF  CAG   109.96  3.000
 23D  CAE   CAF  CAG   110.21  3.000
 23D  HAE2  CAE  HAE1  106.42  3.000
 23D  HAE2  CAE  CAD   109.90  3.000
 23D  HAE1  CAE  CAD   109.38  3.000
 23D  HAE2  CAE  CAF   109.26  3.000
 23D  HAE1  CAE  CAF   109.90  3.000
 23D  CAD   CAE  CAF   111.84  3.000
 23D  HAD2  CAD  HAD1  106.09  3.000
 23D  HAD2  CAD  CAC   110.86  3.000
 23D  HAD1  CAD  CAC   109.19  3.000
 23D  HAD2  CAD  CAE   110.15  3.000
 23D  HAD1  CAD  CAE   110.24  3.000
 23D  CAC   CAD  CAE   110.23  3.000
 23D  HAC2  CAC  HAC1  105.97  3.000
 23D  HAC2  CAC  CAA   109.48  3.000
 23D  HAC1  CAC  CAA   109.12  3.000
 23D  HAC2  CAC  CAD   109.29  3.000
 23D  HAC1  CAC  CAD   111.34  3.000
 23D  CAA   CAC  CAD   111.48  3.000
 23D  HAA   CAA  NAB   112.19  3.000
 23D  HAA   CAA  CAC   107.40  3.000
 23D  NAB   CAA  CAC   110.26  3.000
 23D  HAA   CAA  CAG   107.39  3.000
 23D  NAB   CAA  CAG   108.77  3.000
 23D  CAC   CAA  CAG   110.80  3.000
 23D  HAB2  NAB  HAB1  105.54  3.000
 23D  HAB2  NAB  CAA   109.32  3.000
 23D  HAB1  NAB  CAA   109.24  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
 23D  CONST_01  CAO   CAP  CAQ  CAS    0.00   0.0  0
 23D  CONST_02  CAO   CAN  CAM  CAS    0.00   0.0  0
 23D  CONST_03  CAN   CAM  CAS  CAQ    0.00   0.0  0
 23D  CONST_04  CAN   CAO  CAP  CAQ    0.00   0.0  0
 23D  CONST_05  CAM   CAS  CAQ  CAP    0.00   0.0  0
 23D  CONST_06  CAM   CAN  CAO  CAP    0.00   0.0  0
 23D  CONST_07  N3    C2   N1   C6     0.00   0.0  0
 23D  CONST_08  C8    N7   C5   C6   180.00   0.0  0
 23D  CONST_09  N9    C4   C5   C6   180.00   0.0  0
 23D  CONST_10  N3    C4   C5   C6     0.00   0.0  0
 23D  CONST_11  N7    C5   C6   N1   180.00   0.0  0
 23D  CONST_12  C4    C5   C6   N1     0.00   0.0  0
 23D  CONST_13  C4    N3   C2   N1     0.00   0.0  0
 23D  CONST_14  C2    N1   C6   C5     0.00   0.0  0
 23D  CONST_15  N9    C8   N7   C5     0.00   0.0  0
 23D  CONST_16  C8    N9   C4   C5     0.00   0.0  0
 23D  CONST_17  C2    N3   C4   C5     0.00   0.0  0
 23D  CONST_18  N9    C4   C5   N7     0.00   0.0  0
 23D  CONST_19  N3    C4   C5   N7   180.00   0.0  0
 23D  CONST_20  C4    N9   C8   N7     0.00   0.0  0
 23D  CONST_21  C4    C5   N7   C8     0.00   0.0  0
 23D  CONST_22  N3    C4   N9   C8   180.00   0.0  0
 23D  CONST_23  C2    N3   C4   N9   180.00   0.0  0
 23D  CONST_24  N6    CAM  CAS  CAQ  180.00   0.0  0
 23D  CONST_25  CAM   CAS  CAQ  CL1  180.00   0.0  0
 23D  CONST_26  CAO   CAP  CAQ  CL1  180.00   0.0  0
 23D  CONST_27  N6    CAM  CAN  CAO  180.00   0.0  0
 23D  CONST_28  C2    N1   C6   N6   180.00   0.0  0
 23D  CONST_29  N7    C5   C6   N6     0.00   0.0  0
 23D  CONST_30  C4    C5   C6   N6   180.00   0.0  0
 23D  CONST_31  N2    C2   N1   C6   180.00   0.0  0
 23D  CONST_32  CAZ   N9   C4   C5   180.00   0.0  0
 23D  CONST_33  CAZ   N9   C8   N7   180.00   0.0  0
 23D  CONST_34  N3    C4   N9   CAZ    0.00   0.0  0
 23D  CONST_35  N2    C2   N3   C4   180.00   0.0  0
 23D  CONST_36  CAG   N2   C2   N1     0.00   0.0  0
 23D  CONST_37  CAG   N2   C2   N3   180.00   0.0  0
 23D  CONST_38  HAP   CAP  CAQ  CAS  180.00   0.0  0
 23D  CONST_39  HAN   CAN  CAM  CAS  180.00   0.0  0
 23D  CONST_40  HAO   CAO  CAP  CAQ  180.00   0.0  0
 23D  CONST_41  HAS   CAS  CAQ  CAP  180.00   0.0  0
 23D  CONST_42  H8    C8   N7   C5   180.00   0.0  0
 23D  CONST_43  HN2   N2   C2   N1   180.00   0.0  0
 23D  Var_01    CAD   CAE  CAF  CAG   30.26  30.0  1
 23D  Var_02    CAC   CAD  CAE  CAF   32.23  30.0  1
 23D  Var_03    CAA   CAC  CAD  CAE  -65.39  30.0  1
 23D  Var_04    C6    N6   CAM  CAS   -2.38  30.0  2
 23D  Var_05    N1    C6   N6   CAM   -1.06  30.0  2
 23D  Var_06    CBA   CAZ  N9   C8   -99.76  30.0  2
 23D  Var_07    HBA1  CBA  CAZ  N9    59.45  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
 23D  chir_01  CAG  N2   CAF  CAA  positiv
 23D  chir_02  CAA  NAB  CAC  CAG  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
 23D  plan-1  CAS  0.020
 23D  plan-1  CAQ  0.020
 23D  plan-1  CL1  0.020
 23D  plan-1  CAP  0.020
 23D  plan-1  CAO  0.020
 23D  plan-1  CAN  0.020
 23D  plan-1  CAM  0.020
 23D  plan-1  N6   0.020
 23D  plan-1  HAS  0.020
 23D  plan-1  HAP  0.020
 23D  plan-1  HAO  0.020
 23D  plan-1  HAN  0.020
 23D  plan-2  N6   0.020
 23D  plan-2  C6   0.020
 23D  plan-2  N1   0.020
 23D  plan-2  C5   0.020
 23D  plan-2  N7   0.020
 23D  plan-2  C8   0.020
 23D  plan-2  N9   0.020
 23D  plan-2  CAZ  0.020
 23D  plan-2  C4   0.020
 23D  plan-2  N3   0.020
 23D  plan-2  C2   0.020
 23D  plan-2  N2   0.020
 23D  plan-2  H8   0.020
 23D  plan-3  C2   0.020
 23D  plan-3  N2   0.020
 23D  plan-3  CAG  0.020
 23D  plan-3  HN2  0.020

