# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 04:52:32 2021
#   Inital geometry file: a 87 line input string
#   Ligand name: 4-chloranyl-1-[[2-methoxy-4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(ccc1Cn2ncc3c(Cl)nc(N)nc23)C(F)(F)F
#
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
 FEU  FEU  4-chloranyl-1-[[2-methoxy-4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-6-amine  ligand  35  24  .  2022-03-18  2022-07-25
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FEU
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
 FEU  C13  C   CR6   0   0.026  77.9304  -107.4522  90.3676
 FEU  C15  C   CR16  0  -0.291  80.0949  -106.5821  91.0065
 FEU  C17  C   CR16  0  -0.422  78.5051  -105.1501  89.8856
 FEU  C24  C   CH3   0  -0.441  75.9527  -104.8822  88.7269
 FEU  C01  C   CR6   0   0.119  72.3505  -107.7031  91.4034
 FEU  N02  N   N     0  -0.456  71.8750  -107.8901  90.2119
 FEU  C03  C   CR6   0   0.568  72.7477  -108.2445  89.2274
 FEU  N04  N   N     0  -0.490  74.0555  -108.4189  89.3676
 FEU  C05  C   CR56  0   0.650  74.4902  -108.2078  90.6006
 FEU  C06  C   CR56  0  -0.107  73.6988  -107.8459  91.7033
 FEU  CL7  CL  CL    0  -0.082  71.2437  -107.2598  92.6496
 FEU  N08  N   NH2   0  -0.820  72.2086  -108.4098  88.0137
 FEU  N09  N   NR5   0  -0.378  75.7477  -108.3083  91.0619
 FEU  N10  N   N     0  -0.238  75.8172  -108.0272  92.3817
 FEU  C11  C   CR15  0  -0.102  74.6082  -107.7517  92.7850
 FEU  C12  C   CH2   0  -0.374  76.9498  -108.5898  90.3115
 FEU  C14  C   CR16  0  -0.283  79.1743  -107.6194  90.9497
 FEU  C16  C   CR6   0  -0.185  79.7499  -105.3508  90.4721
 FEU  C18  C   CR6   0   0.409  77.5966  -106.2019  89.8281
 FEU  C19  C   CT    0   1.050  80.7232  -104.2174  90.5772
 FEU  F20  F   F     0  -0.310  81.9716  -104.6028  90.2835
 FEU  F21  F   F     0  -0.303  80.4260  -103.2013  89.7615
 FEU  F22  F   F     0  -0.314  80.7610  -103.7172  91.8221
 FEU  O23  O   O2    0  -0.457  76.3807  -106.1138  89.2743
 FEU  H1   H   HCR6  0   0.271  81.0596  -106.7490  91.4663
 FEU  H2   H   HCR6  0   0.296  78.2466  -104.1851  89.4729
 FEU  H3   H   HCH3  0   0.264  74.9469  -105.0500  88.3510
 FEU  H4   H   HCH3  0   0.234  75.9212  -104.0911  89.4799
 FEU  H5   H   HCH3  0   0.234  76.5893  -104.5611  87.8989
 FEU  H6   H   HNH2  0   0.405  72.7696  -108.7655  87.2600
 FEU  H7   H   HNH2  0   0.406  71.2111  -108.3919  87.8976
 FEU  H8   H   HCR5  0   0.279  74.4105  -107.5008  93.8158
 FEU  H9   H   HCH2  0   0.287  76.6406  -108.7992  89.2872
 FEU  H10  H   HCH2  0   0.286  77.4107  -109.4968  90.7046
 FEU  H11  H   HCR6  0   0.268  79.4349  -108.5837  91.3675

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
 FEU  N08  C03  single    1.338  0.020  1.338
 FEU  C24  O23  single    1.414  0.020  1.414
 FEU  O23  C18  single    1.339  0.020  1.339
 FEU  C03  N04  aromatic  1.327  0.020  1.327
 FEU  C03  N02  aromatic  1.363  0.020  1.363
 FEU  N04  C05  aromatic  1.324  0.020  1.324
 FEU  C18  C17  aromatic  1.391  0.020  1.391
 FEU  C18  C13  aromatic  1.402  0.020  1.402
 FEU  C17  C16  aromatic  1.391  0.020  1.391
 FEU  F21  C19  single    1.336  0.020  1.336
 FEU  C12  C13  single    1.503  0.020  1.503
 FEU  C12  N09  single    1.445  0.020  1.445
 FEU  C13  C14  aromatic  1.384  0.020  1.384
 FEU  F20  C19  single    1.339  0.020  1.339
 FEU  N02  C01  aromatic  1.296  0.020  1.296
 FEU  C16  C19  single    1.498  0.020  1.498
 FEU  C16  C15  aromatic  1.386  0.020  1.386
 FEU  C05  N09  aromatic  1.343  0.020  1.343
 FEU  C05  C06  aromatic  1.405  0.020  1.405
 FEU  C19  F22  single    1.342  0.020  1.342
 FEU  N09  N10  aromatic  1.351  0.020  1.351
 FEU  C14  C15  aromatic  1.388  0.020  1.388
 FEU  C01  C06  aromatic  1.389  0.020  1.389
 FEU  C01  CL7  single    1.725  0.020  1.725
 FEU  C06  C11  aromatic  1.416  0.020  1.416
 FEU  N10  C11  aromatic  1.304  0.020  1.304
 FEU  C15  H1   single    0.930  0.020  1.080
 FEU  C17  H2   single    0.930  0.020  1.080
 FEU  C24  H3   single    0.970  0.020  1.090
 FEU  C24  H4   single    0.970  0.020  1.090
 FEU  C24  H5   single    0.970  0.020  1.090
 FEU  N08  H6   single    0.860  0.020  1.020
 FEU  N08  H7   single    0.860  0.020  1.020
 FEU  C11  H8   single    0.930  0.020  1.080
 FEU  C12  H9   single    0.970  0.020  1.090
 FEU  C12  H10  single    0.970  0.020  1.090
 FEU  C14  H11  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
 FEU  C18  C13  C14  118.93  3.000
 FEU  C14  C13  C12  120.72  3.000
 FEU  C18  C13  C12  120.35  3.000
 FEU  H1   C15  C16  121.54  3.000
 FEU  H1   C15  C14  119.58  3.000
 FEU  C16  C15  C14  118.88  3.000
 FEU  H2   C17  C18  120.20  3.000
 FEU  H2   C17  C16  120.27  3.000
 FEU  C18  C17  C16  119.53  3.000
 FEU  H5   C24  H4   109.04  3.000
 FEU  H5   C24  H3   108.81  3.000
 FEU  H4   C24  H3   108.88  3.000
 FEU  H5   C24  O23  111.89  3.000
 FEU  H4   C24  O23  111.87  3.000
 FEU  H3   C24  O23  106.23  3.000
 FEU  CL7  C01  C06  119.57  3.000
 FEU  CL7  C01  N02  117.76  3.000
 FEU  C06  C01  N02  122.67  3.000
 FEU  C03  N02  C01  117.82  3.000
 FEU  N08  C03  N04  118.46  3.000
 FEU  N04  C03  N02  126.10  3.000
 FEU  N08  C03  N02  115.43  3.000
 FEU  C05  N04  C03  113.63  3.000
 FEU  N09  C05  C06  106.09  3.000
 FEU  C06  C05  N04  125.95  3.000
 FEU  N09  C05  N04  127.96  3.000
 FEU  C11  C06  C05  104.77  3.000
 FEU  C11  C06  C01  141.41  3.000
 FEU  C05  C06  C01  113.82  3.000
 FEU  H7   N08  H6   118.31  3.000
 FEU  H7   N08  C03  120.18  3.000
 FEU  H6   N08  C03  119.94  3.000
 FEU  C12  N09  N10  120.34  3.000
 FEU  N10  N09  C05  111.59  3.000
 FEU  C12  N09  C05  127.96  3.000
 FEU  C11  N10  N09  107.37  3.000
 FEU  H8   C11  N10  120.97  3.000
 FEU  H8   C11  C06  128.85  3.000
 FEU  N10  C11  C06  110.18  3.000
 FEU  H10  C12  H9   107.38  3.000
 FEU  H10  C12  N09  109.05  3.000
 FEU  H9   C12  N09  106.83  3.000
 FEU  H10  C12  C13  109.89  3.000
 FEU  H9   C12  C13  111.44  3.000
 FEU  N09  C12  C13  112.08  3.000
 FEU  H11  C14  C15  119.34  3.000
 FEU  H11  C14  C13  119.11  3.000
 FEU  C15  C14  C13  121.55  3.000
 FEU  C19  C16  C17  120.14  3.000
 FEU  C19  C16  C15  118.92  3.000
 FEU  C17  C16  C15  120.91  3.000
 FEU  O23  C18  C17  124.08  3.000
 FEU  C17  C18  C13  120.20  3.000
 FEU  O23  C18  C13  115.72  3.000
 FEU  F22  C19  F21  106.79  3.000
 FEU  F22  C19  F20  106.52  3.000
 FEU  F21  C19  F20  106.99  3.000
 FEU  F22  C19  C16  111.43  3.000
 FEU  F20  C19  C16  111.89  3.000
 FEU  F21  C19  C16  112.84  3.000
 FEU  C18  O23  C24  119.49  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
 FEU  CONST_01  C16  C17  C18  C13     0.00   0.0  0
 FEU  CONST_02  C16  C15  C14  C13     0.00   0.0  0
 FEU  CONST_03  C18  C17  C16  C15     0.00   0.0  0
 FEU  CONST_04  C18  C13  C14  C15     0.00   0.0  0
 FEU  CONST_05  C14  C13  C18  C17     0.00   0.0  0
 FEU  CONST_06  C14  C15  C16  C17     0.00   0.0  0
 FEU  CONST_07  N04  C03  N02  C01     0.00   0.0  0
 FEU  CONST_08  N04  C05  C06  C01     0.00   0.0  0
 FEU  CONST_09  N09  C05  C06  C01   180.00   0.0  0
 FEU  CONST_10  N10  C11  C06  C01   180.00   0.0  0
 FEU  CONST_11  C05  N04  C03  N02     0.00   0.0  0
 FEU  CONST_12  C05  C06  C01  N02     0.00   0.0  0
 FEU  CONST_13  C11  C06  C01  N02   180.00   0.0  0
 FEU  CONST_14  N09  C05  N04  C03   180.00   0.0  0
 FEU  CONST_15  C06  C05  N04  C03     0.00   0.0  0
 FEU  CONST_16  C06  C01  N02  C03     0.00   0.0  0
 FEU  CONST_17  N10  N09  C05  N04   180.00   0.0  0
 FEU  CONST_18  C11  C06  C05  N04   180.00   0.0  0
 FEU  CONST_19  C11  N10  N09  C05     0.00   0.0  0
 FEU  CONST_20  N10  C11  C06  C05     0.00   0.0  0
 FEU  CONST_21  N10  N09  C05  C06     0.00   0.0  0
 FEU  CONST_22  N09  N10  C11  C06     0.00   0.0  0
 FEU  CONST_23  C11  C06  C05  N09     0.00   0.0  0
 FEU  CONST_24  C12  C13  C14  C15   180.00   0.0  0
 FEU  CONST_25  C12  C13  C18  C17   180.00   0.0  0
 FEU  CONST_26  N08  C03  N02  C01   180.00   0.0  0
 FEU  CONST_27  CL7  C01  N02  C03   180.00   0.0  0
 FEU  CONST_28  C12  N09  C05  N04     0.00   0.0  0
 FEU  CONST_29  N08  C03  N04  C05   180.00   0.0  0
 FEU  CONST_30  CL7  C01  C06  C05   180.00   0.0  0
 FEU  CONST_31  C12  N09  C05  C06   180.00   0.0  0
 FEU  CONST_32  C11  C06  C01  CL7     0.00   0.0  0
 FEU  CONST_33  C12  N09  N10  C11   180.00   0.0  0
 FEU  CONST_34  O23  C18  C13  C14   180.00   0.0  0
 FEU  CONST_35  C19  C16  C15  C14   180.00   0.0  0
 FEU  CONST_36  O23  C18  C17  C16   180.00   0.0  0
 FEU  CONST_37  C19  C16  C17  C18   180.00   0.0  0
 FEU  CONST_38  H2   C17  C18  C13   180.00   0.0  0
 FEU  CONST_39  H1   C15  C14  C13   180.00   0.0  0
 FEU  CONST_40  H8   C11  C06  C01     0.00   0.0  0
 FEU  CONST_41  H11  C14  C15  C16   180.00   0.0  0
 FEU  CONST_42  H6   N08  C03  N02   180.00   0.0  0
 FEU  CONST_43  H7   N08  C03  N02     0.00   0.0  0
 FEU  Var_01    C05  N09  C12  C13   117.36  30.0  2
 FEU  Var_02    C18  C13  C12  N09   -63.09  30.0  2
 FEU  Var_03    F21  C19  C16  C15   164.81  30.0  2
 FEU  Var_04    H3   C24  O23  C18  -179.44  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
 FEU  plan-1  C13  0.020
 FEU  plan-1  C15  0.020
 FEU  plan-1  C17  0.020
 FEU  plan-1  C12  0.020
 FEU  plan-1  C14  0.020
 FEU  plan-1  C16  0.020
 FEU  plan-1  C18  0.020
 FEU  plan-1  C19  0.020
 FEU  plan-1  O23  0.020
 FEU  plan-1  H1   0.020
 FEU  plan-1  H2   0.020
 FEU  plan-1  H11  0.020
 FEU  plan-2  C01  0.020
 FEU  plan-2  N02  0.020
 FEU  plan-2  C03  0.020
 FEU  plan-2  N04  0.020
 FEU  plan-2  C05  0.020
 FEU  plan-2  C06  0.020
 FEU  plan-2  CL7  0.020
 FEU  plan-2  N08  0.020
 FEU  plan-2  N09  0.020
 FEU  plan-2  N10  0.020
 FEU  plan-2  C11  0.020
 FEU  plan-2  C12  0.020
 FEU  plan-2  H8   0.020
 FEU  plan-3  C03  0.020
 FEU  plan-3  N08  0.020
 FEU  plan-3  H6   0.020
 FEU  plan-3  H7   0.020

