# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 25 19:36:57 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: (2R)-2-{[4-(benzylamino)-8-(1-methylethyl)pyrazolo[1,5-a][1,3,5]triazin-2-yl]amino}butan-1-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@H](CO)Nc1nc(NCc2ccccc2)n3ncc(C(C)C)c3n1
#
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
 NNN  NNN  (2R)-2-{[4-(benzylamino)-8-(1-methylethyl)pyrazolo[1,5-a][1,3,5]triazin-2-yl]amino}butan-1-ol  ligand  52  26  .  2021-08-15  2021-08-15  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_NNN
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
 NNN  O1    O  OH1   0  -0.674   2.2860   4.9076   0.2022
 NNN  C15   C  CH2   0  -0.148   1.1305   4.4038   0.8337
 NNN  C12   C  CH1   0  -0.125   0.5346   3.2989  -0.0249
 NNN  C13   C  CH2   0  -0.413   0.0774   3.8014  -1.3969
 NNN  C14   C  CH3   0  -0.670  -0.6816   2.7513  -2.1938
 NNN  N2    N  NH1   0  -0.656   1.4755   2.2059  -0.1545
 NNN  C2    C  CR6   0   0.571   1.2619   0.9164   0.1528
 NNN  N1    N  N     0  -0.532   0.0619   0.6112   0.7018
 NNN  C6    C  CR6   0   0.792  -0.1682  -0.6329   1.0250
 NNN  N5    N  N     0  -0.443   0.7913  -1.5699   0.7966
 NNN  N7    N  N     0  -0.334   0.6980  -2.8854   1.0684
 NNN  C8    C  CR15  0  -0.048   1.8599  -3.3607   0.6612
 NNN  C9'   C  CR5   0  -0.179   2.7203  -2.3833   0.1246
 NNN  C9    C  CH1   0  -0.331   4.0997  -2.5539  -0.4326
 NNN  C10   C  CH3   0  -0.643   5.0766  -3.0527   0.6327
 NNN  C11   C  CH3   0  -0.643   4.1011  -3.4836  -1.6466
 NNN  C4    C  CR56  0   0.549   1.9915  -1.2093   0.2257
 NNN  N3    N  N     0  -0.524   2.2419   0.0646  -0.1057
 NNN  N6    N  NH1   0  -0.655  -1.3046  -1.0403   1.5785
 NNN  CA'   C  CH2   0  -0.385  -2.4309  -0.1711   1.8411
 NNN  C1'   C  CR6   0   0.123  -3.5152  -0.2832   0.7983
 NNN  C6'   C  CR16  0  -0.295  -3.2332  -0.0596  -0.5486
 NNN  C5'   C  CR16  0  -0.240  -4.2340  -0.1583  -1.5033
 NNN  C4'   C  CR16  0  -0.268  -5.5332  -0.4787  -1.1247
 NNN  C3'   C  CR16  0  -0.241  -5.8224  -0.7004   0.2136
 NNN  C2'   C  CR16  0  -0.311  -4.8158  -0.6052   1.1680
 NNN  HO1   H  HOH1  0   0.459   2.7023   5.5421   0.7920
 NNN  H15   H  HCH2  0   0.210   1.3594   3.9942   1.8254
 NNN  H15A  H  HCH2  0   0.200   0.3704   5.1837   0.9723
 NNN  H12   H  HCH1  0   0.265  -0.3343   2.9169   0.5131
 NNN  H13   H  HCH2  0   0.222  -0.5646   4.6733  -1.2433
 NNN  H13A  H  HCH2  0   0.223   0.9406   4.1526  -1.9683
 NNN  H14   H  HCH3  0   0.218  -1.5874   2.4404  -1.6706
 NNN  H14A  H  HCH3  0   0.233  -0.9791   3.1399  -3.1680
 NNN  H14B  H  HCH3  0   0.222  -0.0772   1.8600  -2.3652
 NNN  HN2   H  HNH1  0   0.384   2.3697   2.4108  -0.5723
 NNN  H8    H  HCR5  0   0.264   2.0598  -4.4180   0.7662
 NNN  H9    H  HCH1  0   0.234   4.4390  -1.5672  -0.7632
 NNN  H10   H  HCH3  0   0.225   6.0845  -3.1483   0.2246
 NNN  H10A  H  HCH3  0   0.228   5.1204  -2.3694   1.4814
 NNN  H10B  H  HCH3  0   0.215   4.7792  -4.0335   1.0107
 NNN  H11   H  HCH3  0   0.228   3.4460  -3.1104  -2.4346
 NNN  H11A  H  HCH3  0   0.225   5.1055  -3.5793  -2.0636
 NNN  H11B  H  HCH3  0   0.215   3.7601  -4.4850  -1.3750
 NNN  HN6   H  HNH1  0   0.417  -1.4137  -2.0304   1.7411
 NNN  HA'   H  HCH2  0   0.279  -2.8312  -0.4229   2.8233
 NNN  HA'A  H  HCH2  0   0.280  -2.0601   0.8519   1.8956
 NNN  H6'   H  HCR6  0   0.255  -2.2265   0.1999  -0.8540
 NNN  H5'   H  HCR6  0   0.257  -4.0011   0.0169  -2.5458
 NNN  H4'   H  HCR6  0   0.257  -6.3132  -0.5554  -1.8709
 NNN  H3'   H  HCR6  0   0.257  -6.8296  -0.9536   0.5184
 NNN  H2'   H  HCR6  0   0.254  -5.0467  -0.7871   2.2111

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
 NNN  O1   C15   single    1.410  0.020  1.410
 NNN  O1   HO1   single    0.850  0.020  0.980
 NNN  C15  C12   single    1.521  0.020  1.521
 NNN  C15  H15   single    0.970  0.020  1.090
 NNN  C15  H15A  single    0.970  0.020  1.090
 NNN  N2   C12   single    1.448  0.020  1.448
 NNN  C12  C13   single    1.531  0.020  1.531
 NNN  C12  H12   single    0.970  0.020  1.090
 NNN  C13  C14   single    1.521  0.020  1.521
 NNN  C13  H13   single    0.970  0.020  1.090
 NNN  C13  H13A  single    0.970  0.020  1.090
 NNN  C14  H14   single    0.970  0.020  1.090
 NNN  C14  H14A  single    0.970  0.020  1.090
 NNN  C14  H14B  single    0.970  0.020  1.090
 NNN  C2   N2    single    1.343  0.020  1.343
 NNN  N2   HN2   single    0.860  0.020  1.020
 NNN  N1   C2    aromatic  1.355  0.020  1.355
 NNN  C2   N3    aromatic  1.324  0.020  1.324
 NNN  C6   N1    aromatic  1.306  0.020  1.306
 NNN  N6   C6    single    1.328  0.020  1.328
 NNN  C6   N5    aromatic  1.360  0.020  1.360
 NNN  N7   N5    aromatic  1.346  0.020  1.346
 NNN  N5   C4    aromatic  1.377  0.020  1.377
 NNN  N7   C8    aromatic  1.320  0.020  1.320
 NNN  C8   C9'   aromatic  1.408  0.020  1.408
 NNN  C8   H8    single    0.930  0.020  1.080
 NNN  C9'  C4    aromatic  1.386  0.020  1.386
 NNN  C9'  C9    single    1.497  0.020  1.497
 NNN  C11  C9    single    1.529  0.020  1.529
 NNN  C9   C10   single    1.529  0.020  1.529
 NNN  C9   H9    single    0.970  0.020  1.090
 NNN  C10  H10   single    0.970  0.020  1.090
 NNN  C10  H10A  single    0.970  0.020  1.090
 NNN  C10  H10B  single    0.970  0.020  1.090
 NNN  C11  H11   single    0.970  0.020  1.090
 NNN  C11  H11A  single    0.970  0.020  1.090
 NNN  C11  H11B  single    0.970  0.020  1.090
 NNN  C4   N3    aromatic  1.340  0.020  1.340
 NNN  N6   CA'   single    1.447  0.020  1.447
 NNN  N6   HN6   single    0.860  0.020  1.020
 NNN  C1'  CA'   single    1.509  0.020  1.509
 NNN  CA'  HA'   single    0.970  0.020  1.090
 NNN  CA'  HA'A  single    0.970  0.020  1.090
 NNN  C6'  C1'   aromatic  1.394  0.020  1.394
 NNN  C1'  C2'   aromatic  1.390  0.020  1.390
 NNN  C5'  C6'   aromatic  1.387  0.020  1.387
 NNN  C6'  H6'   single    0.930  0.020  1.080
 NNN  C5'  C4'   aromatic  1.391  0.020  1.391
 NNN  C5'  H5'   single    0.930  0.020  1.080
 NNN  C4'  C3'   aromatic  1.387  0.020  1.387
 NNN  C4'  H4'   single    0.930  0.020  1.080
 NNN  C3'  C2'   aromatic  1.390  0.020  1.390
 NNN  C3'  H3'   single    0.930  0.020  1.080
 NNN  C2'  H2'   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
 NNN  HO1   O1   C15   108.43  3.000
 NNN  H15A  C15  H15   107.19  3.000
 NNN  H15A  C15  C12   108.42  3.000
 NNN  H15   C15  C12   108.71  3.000
 NNN  H15A  C15  O1    111.72  3.000
 NNN  H15   C15  O1    111.55  3.000
 NNN  C12   C15  O1    109.14  3.000
 NNN  H12   C12  N2    107.30  3.000
 NNN  H12   C12  C13   108.61  3.000
 NNN  N2    C12  C13   111.20  3.000
 NNN  H12   C12  C15   106.74  3.000
 NNN  C13   C12  C15   112.61  3.000
 NNN  N2    C12  C15   110.14  3.000
 NNN  H13A  C13  H13   106.31  3.000
 NNN  H13A  C13  C14   110.00  3.000
 NNN  H13   C13  C14   109.33  3.000
 NNN  H13A  C13  C12   109.76  3.000
 NNN  H13   C13  C12   108.13  3.000
 NNN  C14   C13  C12   113.07  3.000
 NNN  H14B  C14  H14A  107.58  3.000
 NNN  H14B  C14  H14   107.61  3.000
 NNN  H14A  C14  H14   107.66  3.000
 NNN  H14B  C14  C13   111.72  3.000
 NNN  H14A  C14  C13   111.00  3.000
 NNN  H14   C14  C13   111.08  3.000
 NNN  HN2   N2   C2    115.54  3.000
 NNN  HN2   N2   C12   117.39  3.000
 NNN  C2    N2   C12   126.94  3.000
 NNN  N3    C2   N1    126.16  3.000
 NNN  N3    C2   N2    117.09  3.000
 NNN  N1    C2   N2    116.75  3.000
 NNN  C6    N1   C2    118.10  3.000
 NNN  N6    C6   N5    117.53  3.000
 NNN  N5    C6   N1    119.37  3.000
 NNN  N6    C6   N1    123.11  3.000
 NNN  C4    N5   N7    113.57  3.000
 NNN  C4    N5   C6    120.26  3.000
 NNN  N7    N5   C6    126.17  3.000
 NNN  C8    N7   N5    103.21  3.000
 NNN  H8    C8   C9'   127.06  3.000
 NNN  H8    C8   N7    119.01  3.000
 NNN  C9'   C8   N7    113.92  3.000
 NNN  C4    C9'  C9    127.46  3.000
 NNN  C9    C9'  C8    128.72  3.000
 NNN  C4    C9'  C8    103.82  3.000
 NNN  H9    C9   C11   107.94  3.000
 NNN  H9    C9   C10   107.84  3.000
 NNN  C11   C9   C10   110.74  3.000
 NNN  H9    C9   C9'   107.18  3.000
 NNN  C10   C9   C9'   111.50  3.000
 NNN  C11   C9   C9'   111.44  3.000
 NNN  H10B  C10  H10A  107.72  3.000
 NNN  H10B  C10  H10   107.58  3.000
 NNN  H10A  C10  H10   107.98  3.000
 NNN  H10B  C10  C9    111.10  3.000
 NNN  H10A  C10  C9    111.31  3.000
 NNN  H10   C10  C9    110.98  3.000
 NNN  H11B  C11  H11A  107.57  3.000
 NNN  H11B  C11  H11   107.81  3.000
 NNN  H11A  C11  H11   107.86  3.000
 NNN  H11B  C11  C9    111.09  3.000
 NNN  H11A  C11  C9    110.94  3.000
 NNN  H11   C11  C9    111.40  3.000
 NNN  N3    C4   C9'   133.56  3.000
 NNN  N3    C4   N5    120.96  3.000
 NNN  C9'   C4   N5    105.48  3.000
 NNN  C4    N3   C2    115.15  3.000
 NNN  HN6   N6   CA'   118.42  3.000
 NNN  HN6   N6   C6    117.43  3.000
 NNN  CA'   N6   C6    123.88  3.000
 NNN  HA'A  CA'  HA'   107.27  3.000
 NNN  HA'A  CA'  C1'   110.43  3.000
 NNN  HA'   CA'  C1'   109.98  3.000
 NNN  HA'A  CA'  N6    107.95  3.000
 NNN  HA'   CA'  N6    108.10  3.000
 NNN  C1'   CA'  N6    112.92  3.000
 NNN  C2'   C1'  C6'   118.91  3.000
 NNN  C2'   C1'  CA'   120.39  3.000
 NNN  C6'   C1'  CA'   120.70  3.000
 NNN  H6'   C6'  C5'   119.57  3.000
 NNN  H6'   C6'  C1'   119.91  3.000
 NNN  C5'   C6'  C1'   120.52  3.000
 NNN  H5'   C5'  C4'   120.03  3.000
 NNN  H5'   C5'  C6'   119.76  3.000
 NNN  C4'   C5'  C6'   120.21  3.000
 NNN  H4'   C4'  C3'   120.25  3.000
 NNN  H4'   C4'  C5'   120.13  3.000
 NNN  C3'   C4'  C5'   119.63  3.000
 NNN  H3'   C3'  C2'   119.76  3.000
 NNN  H3'   C3'  C4'   120.21  3.000
 NNN  C2'   C3'  C4'   120.03  3.000
 NNN  H2'   C2'  C3'   119.67  3.000
 NNN  H2'   C2'  C1'   119.62  3.000
 NNN  C3'   C2'  C1'   120.71  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
 NNN  CONST_01  N5   C6   N1   C2      0.00   0.0  0
 NNN  CONST_02  N5   C4   N3   C2      0.00   0.0  0
 NNN  CONST_03  C9'  C4   N3   C2    180.00   0.0  0
 NNN  CONST_04  C4   N3   C2   N1      0.00   0.0  0
 NNN  CONST_05  N7   N5   C6   N1    180.00   0.0  0
 NNN  CONST_06  C4   N5   C6   N1      0.00   0.0  0
 NNN  CONST_07  N3   C2   N1   C6      0.00   0.0  0
 NNN  CONST_08  C8   N7   N5   C6    180.00   0.0  0
 NNN  CONST_09  C9'  C4   N5   C6    180.00   0.0  0
 NNN  CONST_10  N3   C4   N5   C6      0.00   0.0  0
 NNN  CONST_11  C9'  C8   N7   N5      0.00   0.0  0
 NNN  CONST_12  C8   C9'  C4   N5      0.00   0.0  0
 NNN  CONST_13  C9'  C4   N5   N7      0.00   0.0  0
 NNN  CONST_14  N3   C4   N5   N7    180.00   0.0  0
 NNN  CONST_15  C4   C9'  C8   N7      0.00   0.0  0
 NNN  CONST_16  C4   N5   N7   C8      0.00   0.0  0
 NNN  CONST_17  N3   C4   C9'  C8    180.00   0.0  0
 NNN  CONST_18  C4'  C5'  C6'  C1'     0.00   0.0  0
 NNN  CONST_19  C4'  C3'  C2'  C1'     0.00   0.0  0
 NNN  CONST_20  C3'  C2'  C1'  C6'     0.00   0.0  0
 NNN  CONST_21  C3'  C4'  C5'  C6'     0.00   0.0  0
 NNN  CONST_22  C2'  C1'  C6'  C5'     0.00   0.0  0
 NNN  CONST_23  C2'  C3'  C4'  C5'     0.00   0.0  0
 NNN  CONST_24  C6   N1   C2   N2    180.00   0.0  0
 NNN  CONST_25  C4   N3   C2   N2    180.00   0.0  0
 NNN  CONST_26  N6   C6   N1   C2    180.00   0.0  0
 NNN  CONST_27  C9   C9'  C4   N5    180.00   0.0  0
 NNN  CONST_28  N6   C6   N5   N7      0.00   0.0  0
 NNN  CONST_29  C9   C9'  C8   N7    180.00   0.0  0
 NNN  CONST_30  N3   C4   C9'  C9      0.00   0.0  0
 NNN  CONST_31  N6   C6   N5   C4    180.00   0.0  0
 NNN  CONST_32  C5'  C6'  C1'  CA'   180.00   0.0  0
 NNN  CONST_33  C3'  C2'  C1'  CA'   180.00   0.0  0
 NNN  CONST_34  H8   C8   N7   N5    180.00   0.0  0
 NNN  CONST_35  H5'  C5'  C6'  C1'   180.00   0.0  0
 NNN  CONST_36  H3'  C3'  C2'  C1'   180.00   0.0  0
 NNN  CONST_37  H2'  C2'  C1'  C6'   180.00   0.0  0
 NNN  CONST_38  H4'  C4'  C5'  C6'   180.00   0.0  0
 NNN  CONST_39  H6'  C6'  C5'  C4'   180.00   0.0  0
 NNN  CONST_40  N1   C2   N2   C12     0.00   0.0  0
 NNN  CONST_41  N3   C2   N2   C12   180.00   0.0  0
 NNN  CONST_42  CA'  N6   C6   N1      0.00   0.0  0
 NNN  CONST_43  CA'  N6   C6   N5    180.00   0.0  0
 NNN  CONST_44  HN2  N2   C2   N1    180.00   0.0  0
 NNN  CONST_45  HN6  N6   C6   N1    180.00   0.0  0
 NNN  Var_01    C1'  CA'  N6   C6     99.99  30.0  3
 NNN  Var_02    C11  C9   C9'  C8     61.41  30.0  2
 NNN  Var_03    C6'  C1'  CA'  N6    -56.65  30.0  2
 NNN  Var_04    H11  C11  C9   C9'    58.18  30.0  3
 NNN  Var_05    H10  C10  C9   C9'  -178.47  30.0  3
 NNN  Var_06    H14  C14  C13  C12    61.00  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
 NNN  chir_01  C12  C15  N2  C13  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
 NNN  plan-1  CA'  0.020
 NNN  plan-1  C1'  0.020
 NNN  plan-1  C6'  0.020
 NNN  plan-1  C5'  0.020
 NNN  plan-1  C4'  0.020
 NNN  plan-1  C3'  0.020
 NNN  plan-1  C2'  0.020
 NNN  plan-1  H6'  0.020
 NNN  plan-1  H5'  0.020
 NNN  plan-1  H4'  0.020
 NNN  plan-1  H3'  0.020
 NNN  plan-1  H2'  0.020
 NNN  plan-2  N2   0.020
 NNN  plan-2  C2   0.020
 NNN  plan-2  N1   0.020
 NNN  plan-2  C6   0.020
 NNN  plan-2  N5   0.020
 NNN  plan-2  N7   0.020
 NNN  plan-2  C8   0.020
 NNN  plan-2  C9'  0.020
 NNN  plan-2  C9   0.020
 NNN  plan-2  C4   0.020
 NNN  plan-2  N3   0.020
 NNN  plan-2  N6   0.020
 NNN  plan-2  H8   0.020
 NNN  plan-3  C12  0.020
 NNN  plan-3  N2   0.020
 NNN  plan-3  C2   0.020
 NNN  plan-3  HN2  0.020
 NNN  plan-4  C6   0.020
 NNN  plan-4  N6   0.020
 NNN  plan-4  CA'  0.020
 NNN  plan-4  HN6  0.020

