# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr  5 15:44:57 2020
#   Inital geometry file: a 120 line input string
#   Ligand name: 5-[4-bromo-2-(2-chloro-6-fluorophenyl)-1H-imidazol-5-yl]-2-{[4-(trifluoromethyl)phenyl]ethynyl}pyridine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Fc1cccc(Cl)c1c2[nH]c(c(Br)n2)c3ccc(nc3)C#Cc4ccc(cc4)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
 4U9  4U9  5-[4-bromo-2-(2-chloro-6-fluorophenyl)-1H-imidazol-5-yl]-2-{[4-(trifluoromethyl)phenyl]ethynyl}pyridine  ligand  43  32  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_4U9
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
 4U9  C7   C   CSP   0   0.130   -2.9450   0.0454   0.1255
 4U9  C6   C   CR6   0   0.043   -1.5259  -0.0877   0.1206
 4U9  C1   C   CR5   0   0.447    4.7241   0.3992  -0.0920
 4U9  N1   N   NR15  0  -0.644    3.4447   0.7556   0.1371
 4U9  C5   C   CR16  0  -0.109    0.4916   0.8252  -0.4142
 4U9  C4   C   CR6   0  -0.029    1.1982  -0.2936   0.0400
 4U9  C3   C   CR5   0  -0.114    3.5391  -1.3194  -0.4252
 4U9  C2   C   CR5   0   0.361    2.6471  -0.3365  -0.0632
 4U9  C23  C   CR6   0  -0.063    6.9640   1.0818   0.8266
 4U9  C22  C   CR16  0  -0.218    8.0296   1.9653   0.8812
 4U9  C21  C   CR16  0  -0.245    7.9942   3.1229   0.1181
 4U9  C20  C   CR16  0  -0.397    6.9072   3.4051  -0.6940
 4U9  C19  C   CR6   0   0.544    5.8660   2.5022  -0.7245
 4U9  F4   F   F     0  -0.295    4.8179   2.7526  -1.5171
 4U9  C18  C   CR6   0  -0.134    5.8519   1.3270   0.0187
 4U9  N2   N   N     0  -0.398    4.8053  -0.8629  -0.4450
 4U9  C17  C   CR16  0  -0.206    0.4546  -1.3437   0.5738
 4U9  C16  C   CR16  0  -0.306   -0.9228  -1.2456   0.6103
 4U9  N3   N   N     0  -0.403   -0.8217   0.9331  -0.3750
 4U9  C8   C   CSP   0   0.161   -4.1473   0.1458   0.1230
 4U9  C9   C   CR6   0  -0.108   -5.5636   0.2624   0.1130
 4U9  C15  C   CR16  0  -0.282   -6.3598  -0.7609   0.6363
 4U9  C14  C   CR16  0  -0.260   -7.7369  -0.6484   0.6203
 4U9  C12  C   CR6   0  -0.197   -8.3375   0.4851   0.0803
 4U9  C13  C   CT    0   1.053   -9.8294   0.6047   0.1120
 4U9  F3   F   F     0  -0.313  -10.2656   0.9580   1.3302
 4U9  F2   F   F     0  -0.302  -10.2881   1.5201  -0.7458
 4U9  F1   F   F     0  -0.309  -10.4301  -0.5531  -0.1882
 4U9  C11  C   CR16  0  -0.271   -7.5537   1.5083  -0.4384
 4U9  C10  C   CR16  0  -0.273   -6.1742   1.3980  -0.4236
 4U9  H1   H   HNR5  0   0.436    3.1347   1.6482   0.4938
 4U9  H2   H   HCR6  0   0.271    1.0237   1.6668  -0.8452
 4U9  H3   H   HCR6  0   0.291    8.8771   1.7538   1.5178
 4U9  H4   H   HCR6  0   0.288    8.8247   3.8138   0.1594
 4U9  H5   H   HCR6  0   0.294    6.8697   4.3021  -1.2973
 4U9  H7   H   HCR6  0   0.276    0.9400  -2.2221   0.9755
 4U9  H8   H   HCR6  0   0.287   -1.5239  -2.0455   1.0190
 4U9  H9   H   HCR6  0   0.276   -5.8967  -1.6439   1.0542
 4U9  H10  H   HCR6  0   0.283   -8.3313  -1.4541   1.0303
 4U9  H11  H   HCR6  0   0.281   -8.0008   2.3976  -0.8601
 4U9  H12  H   HCR6  0   0.276   -5.5683   2.1954  -0.8309
 4U9  BR1  BR  BR    0  -0.025    3.1443  -3.0653  -0.9346
 4U9  CL1  CL  CL    0  -0.099    7.0140  -0.3331   1.8120

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
 4U9  F1   C13  single    1.338  0.020  1.338
 4U9  F2   C13  single    1.336  0.020  1.336
 4U9  F3   C13  single    1.341  0.020  1.341
 4U9  C13  C12  single    1.497  0.020  1.497
 4U9  C12  C14  aromatic  1.392  0.020  1.392
 4U9  C12  C11  aromatic  1.389  0.020  1.389
 4U9  C14  C15  aromatic  1.382  0.020  1.382
 4U9  C11  C10  aromatic  1.384  0.020  1.384
 4U9  C15  C9   aromatic  1.398  0.020  1.398
 4U9  C10  C9   aromatic  1.397  0.020  1.397
 4U9  C9   C8   single    1.421  0.020  1.421
 4U9  C8   C7   triple    1.206  0.020  1.206
 4U9  C7   C6   single    1.425  0.020  1.425
 4U9  C6   N3   aromatic  1.335  0.020  1.335
 4U9  C6   C16  aromatic  1.394  0.020  1.394
 4U9  N3   C5   aromatic  1.318  0.020  1.318
 4U9  C16  C17  aromatic  1.381  0.020  1.381
 4U9  C5   C4   aromatic  1.399  0.020  1.399
 4U9  C17  C4   aromatic  1.393  0.020  1.393
 4U9  C4   C2   single    1.453  0.020  1.453
 4U9  C2   N1   aromatic  1.367  0.020  1.367
 4U9  C2   C3   aromatic  1.376  0.020  1.376
 4U9  N1   C1   aromatic  1.348  0.020  1.348
 4U9  F4   C19  single    1.338  0.020  1.338
 4U9  C3   BR1  single    1.861  0.020  1.861
 4U9  C3   N2   aromatic  1.346  0.020  1.346
 4U9  C1   C18  single    1.465  0.020  1.465
 4U9  C1   N2   aromatic  1.313  0.020  1.313
 4U9  C19  C18  aromatic  1.391  0.020  1.391
 4U9  C19  C20  aromatic  1.378  0.020  1.378
 4U9  C18  C23  aromatic  1.396  0.020  1.396
 4U9  C20  C21  aromatic  1.386  0.020  1.386
 4U9  C23  CL1  single    1.725  0.020  1.725
 4U9  C23  C22  aromatic  1.385  0.020  1.385
 4U9  C21  C22  aromatic  1.387  0.020  1.387
 4U9  N1   H1   single    0.860  0.020  1.020
 4U9  C5   H2   single    0.930  0.020  1.080
 4U9  C22  H3   single    0.930  0.020  1.080
 4U9  C21  H4   single    0.930  0.020  1.080
 4U9  C20  H5   single    0.930  0.020  1.080
 4U9  C17  H7   single    0.930  0.020  1.080
 4U9  C16  H8   single    0.930  0.020  1.080
 4U9  C15  H9   single    0.930  0.020  1.080
 4U9  C14  H10  single    0.930  0.020  1.080
 4U9  C11  H11  single    0.930  0.020  1.080
 4U9  C10  H12  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
 4U9  C8   C7   C6   180.00  3.000
 4U9  N3   C6   C16  122.48  3.000
 4U9  C16  C6   C7   120.46  3.000
 4U9  N3   C6   C7   117.06  3.000
 4U9  N2   C1   C18  125.56  3.000
 4U9  N2   C1   N1   111.01  3.000
 4U9  C18  C1   N1   123.41  3.000
 4U9  H1   N1   C2   125.35  3.000
 4U9  H1   N1   C1   125.81  3.000
 4U9  C2   N1   C1   108.53  3.000
 4U9  H2   C5   N3   115.90  3.000
 4U9  H2   C5   C4   120.11  3.000
 4U9  N3   C5   C4   123.98  3.000
 4U9  C17  C4   C2   122.49  3.000
 4U9  C2   C4   C5   120.27  3.000
 4U9  C17  C4   C5   117.23  3.000
 4U9  N2   C3   C2   111.81  3.000
 4U9  N2   C3   BR1  120.91  3.000
 4U9  C2   C3   BR1  127.20  3.000
 4U9  C3   C2   C4   133.34  3.000
 4U9  C3   C2   N1   103.35  3.000
 4U9  C4   C2   N1   123.21  3.000
 4U9  C18  C23  C22  121.57  3.000
 4U9  C22  C23  CL1  118.58  3.000
 4U9  C18  C23  CL1  119.85  3.000
 4U9  H3   C22  C21  120.49  3.000
 4U9  H3   C22  C23  120.10  3.000
 4U9  C21  C22  C23  119.41  3.000
 4U9  H4   C21  C20  119.65  3.000
 4U9  H4   C21  C22  119.53  3.000
 4U9  C20  C21  C22  120.82  3.000
 4U9  H5   C20  C19  120.31  3.000
 4U9  H5   C20  C21  121.52  3.000
 4U9  C19  C20  C21  118.17  3.000
 4U9  C18  C19  F4   117.83  3.000
 4U9  C18  C19  C20  123.32  3.000
 4U9  F4   C19  C20  118.84  3.000
 4U9  C19  C18  C23  116.71  3.000
 4U9  C23  C18  C1   123.08  3.000
 4U9  C19  C18  C1   120.18  3.000
 4U9  C3   N2   C1   105.30  3.000
 4U9  H7   C17  C16  119.71  3.000
 4U9  H7   C17  C4   121.01  3.000
 4U9  C16  C17  C4   119.27  3.000
 4U9  H8   C16  C17  120.80  3.000
 4U9  H8   C16  C6   120.45  3.000
 4U9  C17  C16  C6   118.75  3.000
 4U9  C5   N3   C6   118.28  3.000
 4U9  C9   C8   C7   180.00  3.000
 4U9  C10  C9   C15  119.34  3.000
 4U9  C10  C9   C8   120.34  3.000
 4U9  C15  C9   C8   120.32  3.000
 4U9  H9   C15  C14  119.86  3.000
 4U9  H9   C15  C9   119.90  3.000
 4U9  C14  C15  C9   120.24  3.000
 4U9  H10  C14  C12  121.09  3.000
 4U9  H10  C14  C15  118.85  3.000
 4U9  C12  C14  C15  120.06  3.000
 4U9  C11  C12  C13  120.75  3.000
 4U9  C11  C12  C14  120.08  3.000
 4U9  C13  C12  C14  119.14  3.000
 4U9  F1   C13  F2   107.14  3.000
 4U9  F2   C13  F3   106.92  3.000
 4U9  F1   C13  F3   106.59  3.000
 4U9  F3   C13  C12  111.37  3.000
 4U9  F2   C13  C12  112.54  3.000
 4U9  F1   C13  C12  111.93  3.000
 4U9  H11  C11  C10  118.81  3.000
 4U9  H11  C11  C12  121.21  3.000
 4U9  C10  C11  C12  119.98  3.000
 4U9  H12  C10  C11  119.73  3.000
 4U9  H12  C10  C9   119.96  3.000
 4U9  C11  C10  C9   120.31  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
 4U9  CONST_01  C4   C5   N3   C6     0.00   0.0  0
 4U9  CONST_02  C4   C17  C16  C6     0.00   0.0  0
 4U9  CONST_03  C4   C2   N1   C1   180.00   0.0  0
 4U9  CONST_04  C3   C2   N1   C1     0.00   0.0  0
 4U9  CONST_05  C20  C19  C18  C1   180.00   0.0  0
 4U9  CONST_06  C22  C23  C18  C1   180.00   0.0  0
 4U9  CONST_07  C2   C3   N2   C1     0.00   0.0  0
 4U9  CONST_10  N2   C3   C2   N1     0.00   0.0  0
 4U9  CONST_13  C3   N2   C1   N1     0.00   0.0  0
 4U9  CONST_14  C16  C6   N3   C5     0.00   0.0  0
 4U9  CONST_15  C16  C17  C4   C5     0.00   0.0  0
 4U9  CONST_17  N2   C3   C2   C4   180.00   0.0  0
 4U9  CONST_19  C18  C1   N2   C3   180.00   0.0  0
 4U9  CONST_20  N3   C5   C4   C2   180.00   0.0  0
 4U9  CONST_21  C16  C17  C4   C2   180.00   0.0  0
 4U9  CONST_22  C18  C1   N1   C2   180.00   0.0  0
 4U9  CONST_23  N2   C1   N1   C2     0.00   0.0  0
 4U9  CONST_25  C20  C19  C18  C23    0.00   0.0  0
 4U9  CONST_26  C20  C21  C22  C23    0.00   0.0  0
 4U9  CONST_27  C19  C18  C23  C22    0.00   0.0  0
 4U9  CONST_28  C19  C20  C21  C22    0.00   0.0  0
 4U9  CONST_29  C18  C19  C20  C21    0.00   0.0  0
 4U9  CONST_30  C18  C23  C22  C21    0.00   0.0  0
 4U9  CONST_32  N3   C6   C16  C17    0.00   0.0  0
 4U9  CONST_33  N3   C5   C4   C17    0.00   0.0  0
 4U9  CONST_34  C12  C14  C15  C9     0.00   0.0  0
 4U9  CONST_35  C12  C11  C10  C9     0.00   0.0  0
 4U9  CONST_36  C11  C12  C14  C15    0.00   0.0  0
 4U9  CONST_37  C11  C10  C9   C15    0.00   0.0  0
 4U9  CONST_38  C10  C11  C12  C14    0.00   0.0  0
 4U9  CONST_39  C10  C9   C15  C14    0.00   0.0  0
 4U9  CONST_40  C5   N3   C6   C7   180.00   0.0  0
 4U9  CONST_41  C17  C16  C6   C7   180.00   0.0  0
 4U9  CONST_42  F4   C19  C18  C1     0.00   0.0  0
 4U9  CONST_43  CL1  C23  C18  C1     0.00   0.0  0
 4U9  CONST_44  BR1  C3   N2   C1   180.00   0.0  0
 4U9  CONST_45  BR1  C3   C2   N1   180.00   0.0  0
 4U9  CONST_46  BR1  C3   C2   C4     0.00   0.0  0
 4U9  CONST_47  C19  C18  C23  CL1  180.00   0.0  0
 4U9  CONST_48  C21  C22  C23  CL1  180.00   0.0  0
 4U9  CONST_49  F4   C19  C18  C23  180.00   0.0  0
 4U9  CONST_50  F4   C19  C20  C21  180.00   0.0  0
 4U9  CONST_51  C14  C15  C9   C8   180.00   0.0  0
 4U9  CONST_52  C11  C10  C9   C8   180.00   0.0  0
 4U9  CONST_53  C13  C12  C14  C15  180.00   0.0  0
 4U9  CONST_54  C10  C11  C12  C13  180.00   0.0  0
 4U9  CONST_55  H2   C5   N3   C6   180.00   0.0  0
 4U9  CONST_56  H7   C17  C16  C6   180.00   0.0  0
 4U9  CONST_57  H8   C16  C17  C4   180.00   0.0  0
 4U9  CONST_58  H1   N1   C2   C4     0.00   0.0  0
 4U9  CONST_59  H4   C21  C22  C23  180.00   0.0  0
 4U9  CONST_60  H5   C20  C21  C22  180.00   0.0  0
 4U9  CONST_61  H3   C22  C21  C20  180.00   0.0  0
 4U9  CONST_62  H10  C14  C15  C9   180.00   0.0  0
 4U9  CONST_63  H11  C11  C10  C9   180.00   0.0  0
 4U9  CONST_64  H12  C10  C9   C15  180.00   0.0  0
 4U9  CONST_65  H9   C15  C14  C12  180.00   0.0  0
 4U9  Var_01    F1   C13  C12  C14  -41.63  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
 4U9  plan-1  C1   0.020
 4U9  plan-1  N1   0.020
 4U9  plan-1  C4   0.020
 4U9  plan-1  C3   0.020
 4U9  plan-1  C2   0.020
 4U9  plan-1  C18  0.020
 4U9  plan-1  N2   0.020
 4U9  plan-1  H1   0.020
 4U9  plan-1  BR1  0.020
 4U9  plan-2  C7   0.020
 4U9  plan-2  C6   0.020
 4U9  plan-2  C5   0.020
 4U9  plan-2  C4   0.020
 4U9  plan-2  C2   0.020
 4U9  plan-2  C17  0.020
 4U9  plan-2  C16  0.020
 4U9  plan-2  N3   0.020
 4U9  plan-2  C8   0.020
 4U9  plan-2  H2   0.020
 4U9  plan-2  H7   0.020
 4U9  plan-2  H8   0.020
 4U9  plan-3  C1   0.020
 4U9  plan-3  C23  0.020
 4U9  plan-3  C22  0.020
 4U9  plan-3  C21  0.020
 4U9  plan-3  C20  0.020
 4U9  plan-3  C19  0.020
 4U9  plan-3  F4   0.020
 4U9  plan-3  C18  0.020
 4U9  plan-3  H3   0.020
 4U9  plan-3  H4   0.020
 4U9  plan-3  H5   0.020
 4U9  plan-3  CL1  0.020
 4U9  plan-4  C7   0.020
 4U9  plan-4  C8   0.020
 4U9  plan-4  C9   0.020
 4U9  plan-4  C15  0.020
 4U9  plan-4  C14  0.020
 4U9  plan-4  C12  0.020
 4U9  plan-4  C13  0.020
 4U9  plan-4  C11  0.020
 4U9  plan-4  C10  0.020
 4U9  plan-4  H9   0.020
 4U9  plan-4  H10  0.020
 4U9  plan-4  H11  0.020
 4U9  plan-4  H12  0.020

