# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 19 13:50:26 2020
#   Inital geometry file: a 100 line input string
#   Ligand name: 2-chloranyl-4-[[5-chloranyl-4-[(4-fluorophenyl)amino]pyrimidin-2-yl]amino]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1ccc(Nc2ncc(Cl)c(Nc3ccc(F)cc3)n2)cc1Cl
#
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
 C1W  C1W  '2-chloranyl-4-[[5-chloranyl-4-[(4-fluorophenyl)amino]pyrimidin-2-yl]amino]benzoic acid'  ligand  36  26  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C1W
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
 C1W  C1   C   CR16   0  -0.330   6.3855  -1.7217  -0.0080
 C1W  C2   C   CR6    0   0.465   5.6304  -2.8786  -0.0012
 C1W  C3   C   CR16   0  -0.408   4.2534  -2.8353  -0.0409
 C1W  C7   C   CR6    0  -0.198   2.2385   2.6806  -0.1569
 C1W  C8   C   CR16   0   0.001   0.9230   3.0554  -0.1045
 C1W  C9   C   CR6    0   0.629   0.2750   0.9084   0.0379
 C1W  C10  C   C      0   0.382  -2.0536  -0.0003   0.2395
 C1W  C11  C   C1     0  -0.235  -2.8200   1.1657   0.2030
 C1W  C12  C   C1     0  -0.322  -4.1951   1.0723   0.3201
 C1W  C13  C   C      0  -0.071  -4.8904  -0.1289   0.4611
 C1W  C14  C   C      0  -0.045  -4.0959  -1.2761   0.4908
 C1W  C15  C   C1     0  -0.349  -2.7162  -1.2201   0.3902
 C1W  C16  C   C      0   0.393  -6.4152  -0.0803   0.5558
 C1W  F    F   F      0  -0.352   6.2527  -4.0690   0.0449
 C1W  C4   C   CR16   0  -0.242   3.6024  -1.6094  -0.0882
 C1W  C5   C   CR6    0   0.311   4.3395  -0.4245  -0.0936
 C1W  C    C   CR16   0  -0.364   5.7352  -0.5021  -0.0528
 C1W  N    N   NH1    0  -0.709   3.7996   0.8634  -0.1475
 C1W  C6   C   CR6    0   0.549   2.5215   1.2927  -0.1029
 C1W  N2   N   N      0  -0.524   1.5224   0.4352  -0.0066
 C1W  N1   N   N      0  -0.467  -0.0786   2.1832  -0.0076
 C1W  CL   CL  CL     0  -0.101  -4.7459  -2.8763   0.6906
 C1W  O1   O   OC    -1  -0.684  -6.9076   1.0548   0.7120
 C1W  O    O   O      0  -0.572  -7.0354  -1.1505   0.4584
 C1W  H1   H   HCR6   0   0.286   7.4661  -1.7644   0.0220
 C1W  H2   H   HCR6   0   0.273   3.6749  -3.7497  -0.0367
 C1W  H5   H   HCR6   0   0.296   0.6561   4.1057  -0.1417
 C1W  H7   H   H      0   0.274  -2.3522   2.1292   0.0873
 C1W  H8   H   H      0   0.248  -4.7742   1.9853   0.2978
 C1W  H9   H   H      0   0.259  -2.1418  -2.1377   0.4299
 C1W  H3   H   HCR6   0   0.299   2.5268  -1.5888  -0.1180
 C1W  H    H   HCR6   0   0.269   6.3282   0.4046  -0.0552
 C1W  H4   H   HNH1   0   0.404   4.4918   1.5948  -0.2063
 C1W  H6   H   HNH1   0   0.397  -0.2805  -0.9945   0.1659
 C1W  CL1  CL  CL     0  -0.041   3.4968   3.8560  -0.2808
 C1W  N3   N   NH1    0  -0.722  -0.6718  -0.0651   0.1397

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
 C1W  CL1  C7   single    1.726  0.020  1.726
 C1W  C8   C7   aromatic  1.369  0.020  1.369
 C1W  C8   N1   aromatic  1.332  0.020  1.332
 C1W  C7   C6   aromatic  1.417  0.020  1.417
 C1W  N1   C9   aromatic  1.324  0.020  1.324
 C1W  C9   N3   single    1.362  0.020  1.362
 C1W  C9   N2   aromatic  1.335  0.020  1.335
 C1W  C6   N2   aromatic  1.320  0.020  1.320
 C1W  C6   N    single    1.349  0.020  1.349
 C1W  N3   C10  single    1.387  0.020  1.387
 C1W  N    C5   single    1.397  0.020  1.397
 C1W  C10  C11  aromatic  1.396  0.020  1.396
 C1W  C10  C15  aromatic  1.396  0.020  1.396
 C1W  C5   C    aromatic  1.398  0.020  1.398
 C1W  C5   C4   aromatic  1.395  0.020  1.395
 C1W  C11  C12  aromatic  1.383  0.020  1.383
 C1W  C    C1   aromatic  1.383  0.020  1.383
 C1W  C15  C14  aromatic  1.384  0.020  1.384
 C1W  C4   C3   aromatic  1.389  0.020  1.389
 C1W  C12  C13  aromatic  1.395  0.020  1.395
 C1W  C1   C2   aromatic  1.382  0.020  1.382
 C1W  C14  C13  aromatic  1.396  0.020  1.396
 C1W  C14  CL   single    1.739  0.020  1.739
 C1W  C13  C16  single    1.528  0.020  1.528
 C1W  C3   C2   aromatic  1.378  0.020  1.378
 C1W  C2   F    single    1.344  0.020  1.344
 C1W  C16  O    deloc     1.241  0.020  1.241
 C1W  C16  O1   deloc     1.247  0.020  1.247
 C1W  C1   H1   single    0.930  0.020  1.080
 C1W  C3   H2   single    0.930  0.020  1.080
 C1W  C8   H5   single    0.930  0.020  1.080
 C1W  C11  H7   single    0.930  0.020  1.080
 C1W  C12  H8   single    0.930  0.020  1.080
 C1W  C15  H9   single    0.930  0.020  1.080
 C1W  C4   H3   single    0.930  0.020  1.080
 C1W  C    H    single    0.930  0.020  1.080
 C1W  N    H4   single    0.860  0.020  1.020
 C1W  N3   H6   single    0.860  0.020  1.020

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
 C1W  H1   C1   C    120.36  3.000
 C1W  H1   C1   C2   120.85  3.000
 C1W  C    C1   C2   118.79  3.000
 C1W  F    C2   C3   119.43  3.000
 C1W  F    C2   C1   119.26  3.000
 C1W  C3   C2   C1   121.31  3.000
 C1W  H2   C3   C4   119.70  3.000
 C1W  H2   C3   C2   120.50  3.000
 C1W  C4   C3   C2   119.81  3.000
 C1W  CL1  C7   C6   121.59  3.000
 C1W  C6   C7   C8   117.29  3.000
 C1W  CL1  C7   C8   121.12  3.000
 C1W  H5   C8   N1   116.86  3.000
 C1W  H5   C8   C7   120.03  3.000
 C1W  N1   C8   C7   123.11  3.000
 C1W  N3   C9   N1   120.35  3.000
 C1W  N3   C9   N2   113.50  3.000
 C1W  N1   C9   N2   126.15  3.000
 C1W  N3   C10  C15  116.09  3.000
 C1W  C15  C10  C11  118.17  3.000
 C1W  N3   C10  C11  125.74  3.000
 C1W  H7   C11  C12  120.08  3.000
 C1W  H7   C11  C10  120.77  3.000
 C1W  C12  C11  C10  119.16  3.000
 C1W  H8   C12  C13  117.53  3.000
 C1W  H8   C12  C11  118.26  3.000
 C1W  C13  C12  C11  124.21  3.000
 C1W  C16  C13  C14  126.35  3.000
 C1W  C16  C13  C12  118.43  3.000
 C1W  C14  C13  C12  115.22  3.000
 C1W  CL   C14  C15  114.72  3.000
 C1W  CL   C14  C13  123.10  3.000
 C1W  C15  C14  C13  122.17  3.000
 C1W  H9   C15  C14  119.44  3.000
 C1W  H9   C15  C10  119.49  3.000
 C1W  C14  C15  C10  121.07  3.000
 C1W  O    C16  O1   126.69  3.000
 C1W  O1   C16  C13  115.50  3.000
 C1W  O    C16  C13  117.80  3.000
 C1W  H3   C4   C5   120.77  3.000
 C1W  H3   C4   C3   119.10  3.000
 C1W  C5   C4   C3   120.13  3.000
 C1W  N    C5   C    115.97  3.000
 C1W  C    C5   C4   118.68  3.000
 C1W  N    C5   C4   125.35  3.000
 C1W  H    C    C5   119.98  3.000
 C1W  H    C    C1   118.73  3.000
 C1W  C5   C    C1   121.28  3.000
 C1W  H4   N    C6   114.92  3.000
 C1W  H4   N    C5   113.91  3.000
 C1W  C6   N    C5   131.15  3.000
 C1W  N2   C6   N    120.85  3.000
 C1W  N    C6   C7   119.97  3.000
 C1W  N2   C6   C7   119.19  3.000
 C1W  C6   N2   C9   118.65  3.000
 C1W  C9   N1   C8   115.62  3.000
 C1W  H6   N3   C10  115.32  3.000
 C1W  H6   N3   C9   113.01  3.000
 C1W  C10  N3   C9   131.66  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
 C1W  CONST_01  C4   C5   C    C1     0.00   0.0  0
 C1W  CONST_02  C4   C3   C2   C1     0.00   0.0  0
 C1W  CONST_03  C5   C    C1   C2     0.00   0.0  0
 C1W  CONST_04  C5   C4   C3   C2     0.00   0.0  0
 C1W  CONST_05  C    C5   C4   C3     0.00   0.0  0
 C1W  CONST_06  C    C1   C2   C3     0.00   0.0  0
 C1W  CONST_07  C9   N1   C8   C7     0.00   0.0  0
 C1W  CONST_08  C9   N2   C6   C7     0.00   0.0  0
 C1W  CONST_09  N2   C6   C7   C8     0.00   0.0  0
 C1W  CONST_10  N2   C9   N1   C8     0.00   0.0  0
 C1W  CONST_11  C13  C12  C11  C10    0.00   0.0  0
 C1W  CONST_12  C13  C14  C15  C10    0.00   0.0  0
 C1W  CONST_13  C14  C15  C10  C11    0.00   0.0  0
 C1W  CONST_14  C14  C13  C12  C11    0.00   0.0  0
 C1W  CONST_15  C15  C10  C11  C12    0.00   0.0  0
 C1W  CONST_16  C15  C14  C13  C12    0.00   0.0  0
 C1W  CONST_17  N1   C8   C7   C6     0.00   0.0  0
 C1W  CONST_18  N1   C9   N2   C6     0.00   0.0  0
 C1W  CONST_19  N    C5   C    C1   180.00   0.0  0
 C1W  CONST_20  N    C5   C4   C3   180.00   0.0  0
 C1W  CONST_21  N    C6   C7   C8   180.00   0.0  0
 C1W  CONST_22  N3   C9   N1   C8   180.00   0.0  0
 C1W  CONST_23  N    C6   N2   C9   180.00   0.0  0
 C1W  CONST_24  CL   C14  C15  C10  180.00   0.0  0
 C1W  CONST_25  C16  C13  C12  C11  180.00   0.0  0
 C1W  CONST_26  N3   C10  C11  C12  180.00   0.0  0
 C1W  CONST_27  CL   C14  C13  C12  180.00   0.0  0
 C1W  CONST_28  N3   C10  C15  C14  180.00   0.0  0
 C1W  CONST_29  C16  C13  C14  C15  180.00   0.0  0
 C1W  CONST_30  C    C1   C2   F    180.00   0.0  0
 C1W  CONST_31  C4   C3   C2   F    180.00   0.0  0
 C1W  CONST_32  N3   C9   N2   C6   180.00   0.0  0
 C1W  CONST_33  CL1  C7   C6   N2   180.00   0.0  0
 C1W  CONST_34  CL1  C7   C8   N1   180.00   0.0  0
 C1W  CONST_35  H2   C3   C2   C1   180.00   0.0  0
 C1W  CONST_36  H    C    C1   C2   180.00   0.0  0
 C1W  CONST_37  H3   C4   C3   C2   180.00   0.0  0
 C1W  CONST_38  H1   C1   C2   C3   180.00   0.0  0
 C1W  CONST_39  H5   C8   N1   C9   180.00   0.0  0
 C1W  CONST_40  H8   C12  C11  C10  180.00   0.0  0
 C1W  CONST_41  H9   C15  C10  C11  180.00   0.0  0
 C1W  CONST_42  H7   C11  C12  C13  180.00   0.0  0
 C1W  Var_01    C5   N    C6   C7   179.02  30.0  2
 C1W  Var_02    C11  C10  N3   C9     2.76  30.0  2
 C1W  Var_03    N1   C9   N3   C10   -1.48  30.0  2
 C1W  Var_04    C6   N    C5   C4     5.75  30.0  3
 C1W  Var_05    O    C16  C13  C12  168.34  30.0  2

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
 C1W  plan-1  C7   0.020
 C1W  plan-1  C8   0.020
 C1W  plan-1  C9   0.020
 C1W  plan-1  N    0.020
 C1W  plan-1  C6   0.020
 C1W  plan-1  N2   0.020
 C1W  plan-1  N1   0.020
 C1W  plan-1  H5   0.020
 C1W  plan-1  CL1  0.020
 C1W  plan-1  N3   0.020
 C1W  plan-2  C10  0.020
 C1W  plan-2  C11  0.020
 C1W  plan-2  C12  0.020
 C1W  plan-2  C13  0.020
 C1W  plan-2  C14  0.020
 C1W  plan-2  C15  0.020
 C1W  plan-2  C16  0.020
 C1W  plan-2  CL   0.020
 C1W  plan-2  H7   0.020
 C1W  plan-2  H8   0.020
 C1W  plan-2  H9   0.020
 C1W  plan-2  N3   0.020
 C1W  plan-3  C1   0.020
 C1W  plan-3  C2   0.020
 C1W  plan-3  C3   0.020
 C1W  plan-3  F    0.020
 C1W  plan-3  C4   0.020
 C1W  plan-3  C5   0.020
 C1W  plan-3  C    0.020
 C1W  plan-3  N    0.020
 C1W  plan-3  H1   0.020
 C1W  plan-3  H2   0.020
 C1W  plan-3  H3   0.020
 C1W  plan-3  H    0.020
 C1W  plan-4  C13  0.020
 C1W  plan-4  C16  0.020
 C1W  plan-4  O1   0.020
 C1W  plan-4  O    0.020

