# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr  5 00:24:49 2020
#   Inital geometry file: a 130 line input string
#   Ligand name: 1-cyclopentyl-6-[(1R)-1-(3-phenoxyazetidin-1-yl)ethyl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H](N1C[C@H](C1)Oc2ccccc2)C3=Nc4n(ncc4C(=O)N3)C5CCCC5
#
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
 0WF  0WF  1-cyclopentyl-6-[(1R)-1-(3-phenoxyazetidin-1-yl)ethyl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one  ligand  53  28  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_0WF
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
 0WF  C1   C  CH3   0  -0.664  -0.5755   3.5158   1.6872
 0WF  C2   C  CH1   0  -0.185  -0.0494   2.5777   0.6000
 0WF  C3   C  CR6   0   0.540  -1.2010   1.8172  -0.0080
 0WF  N1   N  NR16  0  -0.717  -1.9957   2.5312  -0.8523
 0WF  C4   C  CR6   0   0.515  -3.1518   2.0668  -1.4843
 0WF  O1   O  O     0  -0.458  -3.8059   2.7911  -2.2126
 0WF  C5   C  CR56  0  -0.346  -3.3917   0.6986  -1.1492
 0WF  C6   C  CR15  0  -0.071  -4.3458  -0.2831  -1.4772
 0WF  N2   N  N     0  -0.257  -4.0575  -1.4169  -0.8830
 0WF  N3   N  NR5   0  -0.386  -2.9394  -1.2114  -0.1696
 0WF  C7   C  CR56  0   0.597  -2.5039   0.0504  -0.2982
 0WF  N4   N  N     0  -0.446  -1.4123   0.5799   0.2964
 0WF  C8   C  CH1   0  -0.086  -2.3264  -2.2863   0.5835
 0WF  C9   C  CH2   0  -0.454  -3.2487  -2.8951   1.6670
 0WF  C10  C  CH2   0  -0.447  -3.1517  -4.4181   1.4852
 0WF  C11  C  CH2   0  -0.454  -1.8722  -4.6318   0.6749
 0WF  C12  C  CH2   0  -0.446  -1.8853  -3.4601  -0.2978
 0WF  N5   N  N     0  -0.414   0.9122   1.6644   1.1514
 0WF  C13  C  C     0  -0.297   1.6413   0.7744   0.2421
 0WF  C14  C  C     0  -0.030   2.8976   1.0161   1.0934
 0WF  C15  C  C     0  -0.302   2.1690   2.2381   1.6493
 0WF  O2   O  O2    0  -0.478   4.0981   1.3350   0.4418
 0WF  C16  C  CR6   0   0.380   4.7768   0.3515  -0.1891
 0WF  C17  C  CR16  0  -0.346   5.9739   0.7274  -0.8011
 0WF  C18  C  CR16  0  -0.241   6.7367  -0.2140  -1.4694
 0WF  C19  C  CR16  0  -0.280   6.3240  -1.5410  -1.5395
 0WF  C20  C  CR16  0  -0.243   5.1353  -1.9086  -0.9304
 0WF  C21  C  CR16  0  -0.370   4.3553  -0.9742  -0.2560
 0WF  H3   H  HCH3  0   0.243  -1.0876   2.9502   2.4654
 0WF  H4   H  HCH3  0   0.258   0.2484   4.0641   2.1435
 0WF  H2   H  HCH3  0   0.246  -1.2667   4.2511   1.2769
 0WF  H5   H  HCH1  0   0.245   0.3997   3.1934  -0.2011
 0WF  H1   H  HNR6  0   0.429  -1.7367   3.4902  -1.0493
 0WF  H6   H  HCR5  0   0.276  -5.2133  -0.1998  -2.1133
 0WF  H7   H  HCH1  0   0.277  -1.4511  -1.8406   1.0558
 0WF  H8   H  HCH2  0   0.244  -2.9011  -2.5919   2.6548
 0WF  H9   H  HCH2  0   0.247  -4.2730  -2.5367   1.5663
 0WF  H10  H  HCH2  0   0.237  -3.1484  -4.9542   2.4345
 0WF  H11  H  HCH2  0   0.227  -4.0085  -4.7826   0.9142
 0WF  H12  H  HCH2  0   0.225  -0.9949  -4.5717   1.3255
 0WF  H13  H  HCH2  0   0.239  -1.8396  -5.5994   0.1729
 0WF  H15  H  HCH2  0   0.237  -2.6308  -3.6332  -1.0777
 0WF  H14  H  HCH2  0   0.246  -0.9272  -3.2740  -0.7842
 0WF  H17  H  H     0   0.245   1.2471  -0.2401   0.1791
 0WF  H16  H  H     0   0.226   1.7612   1.1771  -0.7732
 0WF  H18  H  H     0   0.255   3.0543   0.2361   1.8450
 0WF  H19  H  H     0   0.226   2.4722   3.1522   1.1216
 0WF  H20  H  H     0   0.248   2.2131   2.4150   2.7250
 0WF  H21  H  HCR6  0   0.262   6.2969   1.7598  -0.7484
 0WF  H22  H  HCR6  0   0.258   7.6627   0.0923  -1.9385
 0WF  H23  H  HCR6  0   0.253   6.9224  -2.2743  -2.0632
 0WF  H24  H  HCR6  0   0.259   4.7978  -2.9362  -0.9747
 0WF  H25  H  HCR6  0   0.277   3.4320  -1.3001   0.2035

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
 0WF  C20  C19  aromatic  1.385  0.020  1.385
 0WF  C20  C21  aromatic  1.391  0.020  1.391
 0WF  C19  C18  aromatic  1.391  0.020  1.391
 0WF  C21  C16  aromatic  1.393  0.020  1.393
 0WF  C18  C17  aromatic  1.384  0.020  1.384
 0WF  C16  C17  aromatic  1.396  0.020  1.396
 0WF  C16  O2   single    1.351  0.020  1.351
 0WF  C14  O2   single    1.403  0.020  1.403
 0WF  C14  C15  single    1.527  0.020  1.527
 0WF  C14  C13  single    1.537  0.020  1.537
 0WF  C11  C10  single    1.529  0.020  1.529
 0WF  C11  C12  single    1.523  0.020  1.523
 0WF  C10  C9   single    1.537  0.020  1.537
 0WF  C15  N5   single    1.469  0.020  1.469
 0WF  C13  N5   single    1.467  0.020  1.467
 0WF  C12  C8   single    1.533  0.020  1.533
 0WF  N5   C2   single    1.436  0.020  1.436
 0WF  C9   C8   single    1.548  0.020  1.548
 0WF  C8   N3   single    1.449  0.020  1.449
 0WF  N4   C3   double    1.292  0.020  1.292
 0WF  N4   C7   single    1.351  0.020  1.351
 0WF  C2   C1   single    1.529  0.020  1.529
 0WF  C2   C3   single    1.508  0.020  1.508
 0WF  N3   C7   aromatic  1.341  0.020  1.341
 0WF  N3   N2   aromatic  1.342  0.020  1.342
 0WF  C3   N1   single    1.362  0.020  1.362
 0WF  C7   C5   aromatic  1.390  0.020  1.390
 0WF  N2   C6   aromatic  1.312  0.020  1.312
 0WF  N1   C4   single    1.397  0.020  1.397
 0WF  C5   C6   aromatic  1.408  0.020  1.408
 0WF  C5   C4   single    1.429  0.020  1.429
 0WF  C4   O1   double    1.218  0.020  1.218
 0WF  C1   H3   single    0.970  0.020  1.090
 0WF  C1   H4   single    0.970  0.020  1.090
 0WF  C1   H2   single    0.970  0.020  1.090
 0WF  C2   H5   single    0.970  0.020  1.090
 0WF  N1   H1   single    0.860  0.020  1.020
 0WF  C6   H6   single    0.930  0.020  1.080
 0WF  C8   H7   single    0.970  0.020  1.090
 0WF  C9   H8   single    0.970  0.020  1.090
 0WF  C9   H9   single    0.970  0.020  1.090
 0WF  C10  H10  single    0.970  0.020  1.090
 0WF  C10  H11  single    0.970  0.020  1.090
 0WF  C11  H12  single    0.970  0.020  1.090
 0WF  C11  H13  single    0.970  0.020  1.090
 0WF  C12  H15  single    0.970  0.020  1.090
 0WF  C12  H14  single    0.970  0.020  1.090
 0WF  C13  H17  single    0.970  0.020  1.090
 0WF  C13  H16  single    0.970  0.020  1.090
 0WF  C14  H18  single    0.970  0.020  1.090
 0WF  C15  H19  single    0.970  0.020  1.090
 0WF  C15  H20  single    0.970  0.020  1.090
 0WF  C17  H21  single    0.930  0.020  1.080
 0WF  C18  H22  single    0.930  0.020  1.080
 0WF  C19  H23  single    0.930  0.020  1.080
 0WF  C20  H24  single    0.930  0.020  1.080
 0WF  C21  H25  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
 0WF  H2   C1   H4   107.32  3.000
 0WF  H2   C1   H3   108.73  3.000
 0WF  H4   C1   H3   108.51  3.000
 0WF  H2   C1   C2   111.38  3.000
 0WF  H4   C1   C2   110.25  3.000
 0WF  H3   C1   C2   110.54  3.000
 0WF  H5   C2   N5   111.12  3.000
 0WF  H5   C2   C3   107.39  3.000
 0WF  N5   C2   C3   110.21  3.000
 0WF  H5   C2   C1   108.25  3.000
 0WF  C3   C2   C1   109.46  3.000
 0WF  N5   C2   C1   110.33  3.000
 0WF  N4   C3   N1   123.57  3.000
 0WF  N1   C3   C2   115.55  3.000
 0WF  N4   C3   C2   120.86  3.000
 0WF  H1   N1   C4   116.00  3.000
 0WF  H1   N1   C3   117.90  3.000
 0WF  C4   N1   C3   126.10  3.000
 0WF  C5   C4   O1   128.29  3.000
 0WF  O1   C4   N1   121.16  3.000
 0WF  C5   C4   N1   110.55  3.000
 0WF  C7   C5   C6   104.49  3.000
 0WF  C6   C5   C4   136.63  3.000
 0WF  C7   C5   C4   118.87  3.000
 0WF  H6   C6   N2   120.69  3.000
 0WF  H6   C6   C5   128.93  3.000
 0WF  N2   C6   C5   110.38  3.000
 0WF  N3   N2   C6   106.94  3.000
 0WF  C8   N3   C7   127.64  3.000
 0WF  C7   N3   N2   111.33  3.000
 0WF  C8   N3   N2   121.01  3.000
 0WF  N4   C7   N3   126.08  3.000
 0WF  N3   C7   C5   106.86  3.000
 0WF  N4   C7   C5   127.05  3.000
 0WF  C7   N4   C3   113.82  3.000
 0WF  H7   C8   C12  109.34  3.000
 0WF  H7   C8   C9   109.64  3.000
 0WF  C12  C8   C9   105.83  3.000
 0WF  H7   C8   N3   105.17  3.000
 0WF  C9   C8   N3   113.81  3.000
 0WF  C12  C8   N3   113.02  3.000
 0WF  H9   C9   H8   106.98  3.000
 0WF  H9   C9   C10  111.97  3.000
 0WF  H8   C9   C10  111.27  3.000
 0WF  H9   C9   C8   111.47  3.000
 0WF  H8   C9   C8   109.57  3.000
 0WF  C10  C9   C8   105.63  3.000
 0WF  H11  C10  H10  107.07  3.000
 0WF  H11  C10  C11  109.43  3.000
 0WF  H10  C10  C11  112.96  3.000
 0WF  H11  C10  C9   110.06  3.000
 0WF  H10  C10  C9   112.61  3.000
 0WF  C11  C10  C9   104.71  3.000
 0WF  H13  C11  H12  107.37  3.000
 0WF  H13  C11  C12  112.88  3.000
 0WF  H12  C11  C12  110.15  3.000
 0WF  H13  C11  C10  113.13  3.000
 0WF  H12  C11  C10  110.38  3.000
 0WF  C12  C11  C10  102.93  3.000
 0WF  H14  C12  H15  107.95  3.000
 0WF  H14  C12  C11  114.12  3.000
 0WF  H15  C12  C11  109.87  3.000
 0WF  H14  C12  C8   112.25  3.000
 0WF  H15  C12  C8   109.60  3.000
 0WF  C11  C12  C8   102.97  3.000
 0WF  C15  N5   C13   91.25  3.000
 0WF  C13  N5   C2   118.73  3.000
 0WF  C15  N5   C2   117.05  3.000
 0WF  H16  C13  H17  109.10  3.000
 0WF  H16  C13  C14  111.41  3.000
 0WF  H17  C13  C14  118.29  3.000
 0WF  H16  C13  N5   113.88  3.000
 0WF  H17  C13  N5   114.89  3.000
 0WF  C14  C13  N5    88.14  3.000
 0WF  H18  C14  O2   111.01  3.000
 0WF  H18  C14  C15  112.86  3.000
 0WF  O2   C14  C15  113.30  3.000
 0WF  H18  C14  C13  112.66  3.000
 0WF  C15  C14  C13   86.42  3.000
 0WF  O2   C14  C13  118.56  3.000
 0WF  H20  C15  H19  109.12  3.000
 0WF  H20  C15  C14  117.99  3.000
 0WF  H19  C15  C14  111.06  3.000
 0WF  H20  C15  N5   115.61  3.000
 0WF  H19  C15  N5   113.49  3.000
 0WF  C14  C15  N5    88.42  3.000
 0WF  C16  O2   C14  118.77  3.000
 0WF  C21  C16  C17  119.66  3.000
 0WF  C17  C16  O2   116.07  3.000
 0WF  C21  C16  O2   124.28  3.000
 0WF  H21  C17  C18  120.50  3.000
 0WF  H21  C17  C16  119.42  3.000
 0WF  C18  C17  C16  120.08  3.000
 0WF  H22  C18  C19  120.12  3.000
 0WF  H22  C18  C17  119.24  3.000
 0WF  C19  C18  C17  120.64  3.000
 0WF  H23  C19  C20  120.51  3.000
 0WF  H23  C19  C18  120.45  3.000
 0WF  C20  C19  C18  119.04  3.000
 0WF  H24  C20  C21  118.85  3.000
 0WF  H24  C20  C19  120.09  3.000
 0WF  C21  C20  C19  121.05  3.000
 0WF  H25  C21  C20  118.82  3.000
 0WF  H25  C21  C16  121.65  3.000
 0WF  C20  C21  C16  119.53  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
 0WF  CONST_01  N2   N3   C7   C5     0.00   0.0  0
 0WF  CONST_02  N3   N2   C6   C5     0.00   0.0  0
 0WF  CONST_03  C7   N3   N2   C6     0.00   0.0  0
 0WF  CONST_04  N3   C7   C5   C6     0.00   0.0  0
 0WF  CONST_05  C7   C5   C6   N2     0.00   0.0  0
 0WF  CONST_06  C19  C20  C21  C16    0.00   0.0  0
 0WF  CONST_07  C19  C18  C17  C16    0.00   0.0  0
 0WF  CONST_08  C20  C19  C18  C17    0.00   0.0  0
 0WF  CONST_09  C20  C21  C16  C17    0.00   0.0  0
 0WF  CONST_10  C21  C20  C19  C18    0.00   0.0  0
 0WF  CONST_11  C21  C16  C17  C18    0.00   0.0  0
 0WF  CONST_12  C8   N3   C7   C5   180.00   0.0  0
 0WF  CONST_13  C8   N3   N2   C6   180.00   0.0  0
 0WF  CONST_14  C8   N3   C7   N4     0.00   0.0  0
 0WF  CONST_15  C5   C4   N1   C3     0.00   0.0  0
 0WF  CONST_16  C7   N4   C3   N1     0.00   0.0  0
 0WF  CONST_17  N4   C3   N1   C4     0.00   0.0  0
 0WF  CONST_18  C20  C21  C16  O2   180.00   0.0  0
 0WF  CONST_19  C18  C17  C16  O2   180.00   0.0  0
 0WF  CONST_20  C7   N4   C3   C2   180.00   0.0  0
 0WF  CONST_21  C4   N1   C3   C2   180.00   0.0  0
 0WF  CONST_22  O1   C4   N1   C3   180.00   0.0  0
 0WF  CONST_23  H6   C6   C5   C4     0.00   0.0  0
 0WF  CONST_24  H24  C20  C21  C16  180.00   0.0  0
 0WF  CONST_25  H22  C18  C17  C16  180.00   0.0  0
 0WF  CONST_26  H23  C19  C18  C17  180.00   0.0  0
 0WF  CONST_27  H25  C21  C16  C17  180.00   0.0  0
 0WF  CONST_28  H21  C17  C18  C19  180.00   0.0  0
 0WF  CONST_29  H1   N1   C4   C5   180.00   0.0  0
 0WF  Var_01    C10  C11  C12  C8    42.29  30.0  1
 0WF  Var_02    C11  C10  C9   C8    18.59  30.0  1
 0WF  Var_03    C12  C11  C10  C9   -37.87  30.0  1
 0WF  Var_04    C14  C15  N5   C13  -18.49  30.0  1
 0WF  Var_05    C21  C16  O2   C14    0.92  30.0  2

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
 0WF  chir_01  C2   N5  C1   C3   positiv
 0WF  chir_02  C8   N3  C12  C9   positiv
 0WF  chir_03  C14  O2  C15  C13  negativ

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
 0WF  plan-1  O2   0.020
 0WF  plan-1  C16  0.020
 0WF  plan-1  C17  0.020
 0WF  plan-1  C18  0.020
 0WF  plan-1  C19  0.020
 0WF  plan-1  C20  0.020
 0WF  plan-1  C21  0.020
 0WF  plan-1  H21  0.020
 0WF  plan-1  H22  0.020
 0WF  plan-1  H23  0.020
 0WF  plan-1  H24  0.020
 0WF  plan-1  H25  0.020
 0WF  plan-2  C2   0.020
 0WF  plan-2  C3   0.020
 0WF  plan-2  N1   0.020
 0WF  plan-2  C4   0.020
 0WF  plan-2  O1   0.020
 0WF  plan-2  C5   0.020
 0WF  plan-2  C6   0.020
 0WF  plan-2  N2   0.020
 0WF  plan-2  N3   0.020
 0WF  plan-2  C7   0.020
 0WF  plan-2  N4   0.020
 0WF  plan-2  C8   0.020
 0WF  plan-2  H1   0.020
 0WF  plan-2  H6   0.020

