# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 29 13:28:47 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: 4-chloro-N-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorobenzyl]-2-(hydroxymethyl)-1H-imidazole-5-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCc1[nH]c(C(=O)NCc2ccc(Cl)c(Oc3cc(Cl)cc(c3)C#N)c2F)c(Cl)n1
#
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
 EUR  EUR  4-chloro-N-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorobenzyl]-2-(hydroxymethyl)-1H-imidazole-5-carboxamide  ligand  42  30  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_EUR
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
 EUR  O01   O   OH1   0  -0.688  -1.3898   3.2650  -0.9249
 EUR  C02   C   CH2   0  -0.247  -2.7738   3.4653  -0.8015
 EUR  C03   C   CR5   0   0.457  -3.3463   2.2599  -0.1365
 EUR  N04   N   N     0  -0.458  -4.4773   2.1935   0.5303
 EUR  C05   C   CR5   0   0.040  -4.5603   0.9182   0.9531
 EUR  CL1   CL  CL    0  -0.118  -5.8973   0.3753   1.8610
 EUR  C07   C   CR5   0   0.217  -3.4846   0.1747   0.5421
 EUR  N08   N   NR15  0  -0.591  -2.7268   1.0729  -0.1693
 EUR  C09   C   C     0   0.509  -3.1152  -1.2242   0.7825
 EUR  O10   O   O     0  -0.556  -3.4454  -1.8059   1.8007
 EUR  N11   N   NH1   0  -0.587  -2.3613  -1.7780  -0.1957
 EUR  C12   C   CH2   0  -0.373  -1.7265  -3.0696  -0.0752
 EUR  C13   C   CR6   0  -0.054  -0.2664  -2.9770  -0.4246
 EUR  C14   C   CR16  0  -0.215   0.2942  -3.6981  -1.4708
 EUR  C15   C   CR16  0  -0.263   1.6358  -3.5840  -1.8000
 EUR  C16   C   CR6   0  -0.039   2.4431  -2.7185  -1.0809
 EUR  CL2   CL  CL    0  -0.046   4.1030  -2.5206  -1.4742
 EUR  C18   C   CR6   0   0.093   1.9149  -1.9869  -0.0242
 EUR  O19   O   O2    0  -0.426   2.6931  -1.1603   0.7219
 EUR  C20   C   CR6   0   0.421   2.6895   0.1714   0.4396
 EUR  C21   C   CR16  0  -0.236   2.1433   0.6994  -0.7217
 EUR  C22   C   CR6   0   0.033   2.2068   2.0701  -0.9263
 EUR  CL3   CL  CL    0  -0.088   1.5427   2.7271  -2.3735
 EUR  C24   C   CR16  0  -0.319   2.7992   2.9197  -0.0143
 EUR  C25   C   CR6   0   0.126   3.3405   2.3605   1.1413
 EUR  C28   C   CR16  0  -0.419   3.2913   0.9929   1.3799
 EUR  C26   C   CSP   0   0.051   3.9553   3.2148   2.1086
 EUR  N27   N   NS    0  -0.176   4.4496   3.9015   2.8888
 EUR  C29   C   CR6   0   0.467   0.5726  -2.1342   0.2857
 EUR  F30   F   F     0  -0.284   0.0893  -1.4191   1.3024
 EUR  H01   H   HOH1  0   0.470  -1.0720   3.7189  -1.7080
 EUR  H021  H   HCH2  0   0.231  -3.0220   4.3481  -0.2028
 EUR  H022  H   HCH2  0   0.256  -3.2601   3.5973  -1.7747
 EUR  H08   H   HNR5  0   0.429  -1.8008   0.9287  -0.5419
 EUR  H11   H   HNH1  0   0.400  -2.3733  -1.3628  -1.1135
 EUR  H121  H   HCH2  0   0.275  -1.8610  -3.4197   0.9472
 EUR  H122  H   HCH2  0   0.280  -2.2128  -3.8010  -0.7229
 EUR  H14   H   HCR6  0   0.288  -0.3320  -4.3649  -2.0481
 EUR  H15   H   HCR6  0   0.279   2.0476  -4.1534  -2.6203
 EUR  H21   H   HCR6  0   0.285   1.6848   0.0692  -1.4718
 EUR  H28   H   HCR6  0   0.279   3.7118   0.5721   2.2827
 EUR  H24   H   HCR6  0   0.297   2.8451   3.9841  -0.1892

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
 EUR  O01  C02   single    1.404  0.020  1.404
 EUR  C02  C03   single    1.491  0.020  1.491
 EUR  C03  N04   aromatic  1.315  0.020  1.315
 EUR  C03  N08   aromatic  1.339  0.020  1.339
 EUR  N04  C05   aromatic  1.346  0.020  1.346
 EUR  C05  CL1   single    1.705  0.020  1.705
 EUR  C05  C07   aromatic  1.371  0.020  1.371
 EUR  C07  N08   aromatic  1.374  0.020  1.374
 EUR  C07  C09   single    1.467  0.020  1.467
 EUR  C09  O10   double    1.218  0.020  1.218
 EUR  C09  N11   single    1.353  0.020  1.353
 EUR  N11  C12   single    1.444  0.020  1.444
 EUR  C12  C13   single    1.504  0.020  1.504
 EUR  C13  C14   aromatic  1.389  0.020  1.389
 EUR  C13  C29   aromatic  1.385  0.020  1.385
 EUR  C14  C15   aromatic  1.386  0.020  1.386
 EUR  C15  C16   aromatic  1.385  0.020  1.385
 EUR  C16  CL2   single    1.717  0.020  1.717
 EUR  C16  C18   aromatic  1.390  0.020  1.390
 EUR  C18  O19   single    1.359  0.020  1.359
 EUR  C18  C29   aromatic  1.385  0.020  1.385
 EUR  O19  C20   single    1.361  0.020  1.361
 EUR  C20  C21   aromatic  1.388  0.020  1.388
 EUR  C20  C28   aromatic  1.386  0.020  1.386
 EUR  C21  C22   aromatic  1.387  0.020  1.387
 EUR  C22  CL3   single    1.723  0.020  1.723
 EUR  C22  C24   aromatic  1.380  0.020  1.380
 EUR  C24  C25   aromatic  1.393  0.020  1.393
 EUR  C25  C28   aromatic  1.389  0.020  1.389
 EUR  C25  C26   single    1.429  0.020  1.429
 EUR  C26  N27   triple    1.151  0.020  1.151
 EUR  C29  F30   single    1.334  0.020  1.334
 EUR  O01  H01   single    0.850  0.020  0.980
 EUR  C02  H021  single    0.970  0.020  1.090
 EUR  C02  H022  single    0.970  0.020  1.090
 EUR  N08  H08   single    0.860  0.020  1.020
 EUR  N11  H11   single    0.860  0.020  1.020
 EUR  C12  H121  single    0.970  0.020  1.090
 EUR  C12  H122  single    0.970  0.020  1.090
 EUR  C14  H14   single    0.930  0.020  1.080
 EUR  C15  H15   single    0.930  0.020  1.080
 EUR  C21  H21   single    0.930  0.020  1.080
 EUR  C28  H28   single    0.930  0.020  1.080
 EUR  C24  H24   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
 EUR  H01   O01  C02   109.32  3.000
 EUR  H022  C02  H021  106.72  3.000
 EUR  H022  C02  C03   108.85  3.000
 EUR  H021  C02  C03   108.71  3.000
 EUR  H022  C02  O01   112.12  3.000
 EUR  H021  C02  O01   112.74  3.000
 EUR  C03   C02  O01   107.60  3.000
 EUR  N08   C03  N04   111.45  3.000
 EUR  N08   C03  C02   121.87  3.000
 EUR  N04   C03  C02   126.68  3.000
 EUR  C05   N04  C03   105.08  3.000
 EUR  C07   C05  CL1   127.05  3.000
 EUR  C07   C05  N04   111.79  3.000
 EUR  CL1   C05  N04   121.15  3.000
 EUR  C09   C07  N08   124.72  3.000
 EUR  C09   C07  C05   131.75  3.000
 EUR  N08   C07  C05   103.51  3.000
 EUR  H08   N08  C07   127.18  3.000
 EUR  H08   N08  C03   124.09  3.000
 EUR  C07   N08  C03   108.15  3.000
 EUR  N11   C09  O10   124.03  3.000
 EUR  N11   C09  C07   114.33  3.000
 EUR  O10   C09  C07   121.61  3.000
 EUR  H11   N11  C12   116.73  3.000
 EUR  H11   N11  C09   118.90  3.000
 EUR  C12   N11  C09   123.40  3.000
 EUR  H122  C12  H121  106.66  3.000
 EUR  H122  C12  C13   109.63  3.000
 EUR  H121  C12  C13   110.96  3.000
 EUR  H122  C12  N11   110.74  3.000
 EUR  H121  C12  N11   108.16  3.000
 EUR  C13   C12  N11   110.62  3.000
 EUR  C29   C13  C14   117.24  3.000
 EUR  C29   C13  C12   120.41  3.000
 EUR  C14   C13  C12   122.33  3.000
 EUR  H14   C14  C15   118.96  3.000
 EUR  H14   C14  C13   119.24  3.000
 EUR  C15   C14  C13   121.79  3.000
 EUR  H15   C15  C16   120.10  3.000
 EUR  H15   C15  C14   120.40  3.000
 EUR  C16   C15  C14   119.49  3.000
 EUR  C18   C16  CL2   118.74  3.000
 EUR  C18   C16  C15   120.15  3.000
 EUR  CL2   C16  C15   121.10  3.000
 EUR  C29   C18  O19   119.79  3.000
 EUR  C29   C18  C16   118.84  3.000
 EUR  O19   C18  C16   121.35  3.000
 EUR  C20   O19  C18   118.67  3.000
 EUR  C28   C20  C21   120.87  3.000
 EUR  C28   C20  O19   115.97  3.000
 EUR  C21   C20  O19   123.15  3.000
 EUR  H21   C21  C22   119.52  3.000
 EUR  H21   C21  C20   121.70  3.000
 EUR  C22   C21  C20   118.77  3.000
 EUR  C24   C22  CL3   119.08  3.000
 EUR  C24   C22  C21   122.03  3.000
 EUR  CL3   C22  C21   118.89  3.000
 EUR  H24   C24  C25   120.90  3.000
 EUR  H24   C24  C22   121.20  3.000
 EUR  C25   C24  C22   117.90  3.000
 EUR  C26   C25  C28   119.17  3.000
 EUR  C26   C25  C24   119.25  3.000
 EUR  C28   C25  C24   121.59  3.000
 EUR  H28   C28  C25   120.85  3.000
 EUR  H28   C28  C20   120.31  3.000
 EUR  C25   C28  C20   118.84  3.000
 EUR  N27   C26  C25   180.00  3.000
 EUR  F30   C29  C18   117.69  3.000
 EUR  F30   C29  C13   119.84  3.000
 EUR  C18   C29  C13   122.47  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
 EUR  CONST_01  C07  C05  N04  C03     0.00   0.0  0
 EUR  CONST_02  C05  C07  N08  C03     0.00   0.0  0
 EUR  CONST_03  C07  N08  C03  N04     0.00   0.0  0
 EUR  CONST_04  N08  C07  C05  N04     0.00   0.0  0
 EUR  CONST_05  N08  C03  N04  C05     0.00   0.0  0
 EUR  CONST_06  C16  C15  C14  C13     0.00   0.0  0
 EUR  CONST_07  C16  C18  C29  C13     0.00   0.0  0
 EUR  CONST_08  C18  C29  C13  C14     0.00   0.0  0
 EUR  CONST_09  C18  C16  C15  C14     0.00   0.0  0
 EUR  CONST_10  C29  C13  C14  C15     0.00   0.0  0
 EUR  CONST_11  C29  C18  C16  C15     0.00   0.0  0
 EUR  CONST_12  C24  C22  C21  C20     0.00   0.0  0
 EUR  CONST_13  C24  C25  C28  C20     0.00   0.0  0
 EUR  CONST_14  C25  C28  C20  C21     0.00   0.0  0
 EUR  CONST_15  C25  C24  C22  C21     0.00   0.0  0
 EUR  CONST_16  C28  C20  C21  C22     0.00   0.0  0
 EUR  CONST_17  C28  C25  C24  C22     0.00   0.0  0
 EUR  CONST_18  C05  N04  C03  C02   180.00   0.0  0
 EUR  CONST_19  C07  N08  C03  C02   180.00   0.0  0
 EUR  CONST_20  CL1  C05  N04  C03   180.00   0.0  0
 EUR  CONST_21  C09  C07  N08  C03   180.00   0.0  0
 EUR  CONST_22  C09  C07  C05  N04   180.00   0.0  0
 EUR  CONST_23  N08  C07  C05  CL1   180.00   0.0  0
 EUR  CONST_24  C15  C14  C13  C12   180.00   0.0  0
 EUR  CONST_25  C18  C29  C13  C12   180.00   0.0  0
 EUR  CONST_26  O19  C18  C29  C13   180.00   0.0  0
 EUR  CONST_27  F30  C29  C13  C14   180.00   0.0  0
 EUR  CONST_28  CL2  C16  C15  C14   180.00   0.0  0
 EUR  CONST_29  O19  C18  C16  C15   180.00   0.0  0
 EUR  CONST_30  F30  C29  C18  C16   180.00   0.0  0
 EUR  CONST_31  C29  C18  C16  CL2   180.00   0.0  0
 EUR  CONST_32  C22  C21  C20  O19   180.00   0.0  0
 EUR  CONST_33  C25  C28  C20  O19   180.00   0.0  0
 EUR  CONST_34  CL3  C22  C21  C20   180.00   0.0  0
 EUR  CONST_35  C26  C25  C28  C20   180.00   0.0  0
 EUR  CONST_36  C26  C25  C24  C22   180.00   0.0  0
 EUR  CONST_37  C25  C24  C22  CL3   180.00   0.0  0
 EUR  CONST_38  H08  N08  C03  N04   180.00   0.0  0
 EUR  CONST_39  H15  C15  C14  C13   180.00   0.0  0
 EUR  CONST_40  H14  C14  C15  C16   180.00   0.0  0
 EUR  CONST_41  H28  C28  C20  C21   180.00   0.0  0
 EUR  CONST_42  H24  C24  C22  C21   180.00   0.0  0
 EUR  CONST_43  H21  C21  C22  C24   180.00   0.0  0
 EUR  CONST_44  C12  N11  C09  C07   180.00   0.0  0
 EUR  CONST_46  C12  N11  C09  O10     0.00   0.0  0
 EUR  Var_01    C21  C20  O19  C18   -12.95  30.0  2
 EUR  Var_02    C29  C18  O19  C20   -83.17  30.0  2
 EUR  Var_03    N04  C03  C02  O01   157.24  30.0  2
 EUR  Var_04    O10  C09  C07  C05   -29.43  30.0  2
 EUR  Var_05    C14  C13  C12  N11  -119.59  30.0  2
 EUR  Var_06    C13  C12  N11  C09  -128.79  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
 EUR  plan-1  C02  0.020
 EUR  plan-1  C03  0.020
 EUR  plan-1  N04  0.020
 EUR  plan-1  C05  0.020
 EUR  plan-1  CL1  0.020
 EUR  plan-1  C07  0.020
 EUR  plan-1  N08  0.020
 EUR  plan-1  C09  0.020
 EUR  plan-1  H08  0.020
 EUR  plan-2  C12  0.020
 EUR  plan-2  C13  0.020
 EUR  plan-2  C14  0.020
 EUR  plan-2  C15  0.020
 EUR  plan-2  C16  0.020
 EUR  plan-2  CL2  0.020
 EUR  plan-2  C18  0.020
 EUR  plan-2  O19  0.020
 EUR  plan-2  C29  0.020
 EUR  plan-2  F30  0.020
 EUR  plan-2  H14  0.020
 EUR  plan-2  H15  0.020
 EUR  plan-3  O19  0.020
 EUR  plan-3  C20  0.020
 EUR  plan-3  C21  0.020
 EUR  plan-3  C22  0.020
 EUR  plan-3  CL3  0.020
 EUR  plan-3  C24  0.020
 EUR  plan-3  C25  0.020
 EUR  plan-3  C28  0.020
 EUR  plan-3  C26  0.020
 EUR  plan-3  N27  0.020
 EUR  plan-3  H21  0.020
 EUR  plan-3  H28  0.020
 EUR  plan-3  H24  0.020
 EUR  plan-4  C07  0.020
 EUR  plan-4  C09  0.020
 EUR  plan-4  O10  0.020
 EUR  plan-4  N11  0.020
 EUR  plan-4  C12  0.020
 EUR  plan-4  H11  0.020

