# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 10:11:12 2021
#   Inital geometry file: a 130 line input string
#   Ligand name: 5-[5-(4-chloranyl-3-fluoranyl-phenyl)-4-methyl-pyrazol-1-yl]-2-phenylmethoxy-benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cnn(c2ccc(OCc3ccccc3)c(c2)C(O)=O)c1c4ccc(Cl)c(F)c4
#
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
 EGO  EGO  '5-[5-(4-chloranyl-3-fluoranyl-phenyl)-4-methyl-pyrazol-1-yl]-2-phenylmethoxy-benzoic acid'  ligand  49  31  .  2022-03-18  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_EGO
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
 EGO  C5   C   CR16  0  -0.261   -7.2171  13.6940  26.9848
 EGO  C4   C   CR16  0  -0.243   -8.6026  13.5884  27.0275
 EGO  C6   C   CR16  0  -0.242   -6.5293  14.2017  28.0782
 EGO  C23  C   CR16  0  -0.305   -9.7893  16.3636  38.0568
 EGO  C3   C   CR16  0  -0.281   -9.2962  13.9887  28.1599
 EGO  C7   C   CR16  0  -0.303   -7.2268  14.6009  29.2115
 EGO  C1   C   CR16  0  -0.250  -10.1942  14.1457  34.7664
 EGO  C2   C   CR16  0  -0.324   -9.6069  13.9767  33.5276
 EGO  C24  C   CR16  0  -0.190   -8.7642  17.2947  38.0034
 EGO  C27  C   CR16  0  -0.447  -10.6391  17.1573  35.9521
 EGO  C16  C   CR16  0  -0.299  -12.3471  14.2661  33.7069
 EGO  C18  C   CR15  0  -0.077  -13.5828  14.1069  37.6419
 EGO  C28  C   CR6   0   0.048  -10.7325  16.2832  37.0347
 EGO  C15  C   CR6   0  -0.176  -11.7670  14.0715  32.4525
 EGO  C8   C   CR6   0   0.073   -8.6132  14.5017  29.2606
 EGO  C30  C   CR5   0  -0.205  -12.7087  15.0820  38.1556
 EGO  C17  C   CR6   0   0.329  -11.5711  14.3047  34.8509
 EGO  C11  C   CR6   0   0.370  -10.3735  13.9279  32.3679
 EGO  C26  C   CR6   0   0.643   -9.6119  18.0736  35.9080
 EGO  C25  C   CR6   0  -0.243   -8.6693  18.1542  36.9215
 EGO  C29  C   CR5   0   0.423  -11.8222  15.3100  37.1223
 EGO  C31  C   CH3   0  -0.752  -12.7596  15.7429  39.4912
 EGO  C9   C   CH2   0  -0.233   -9.3644  14.9119  30.4893
 EGO  N19  N   N     0  -0.269  -13.2664  13.7568  36.4131
 EGO  N20  N   NR5   0  -0.460  -12.1979  14.4887  36.1018
 EGO  O12  O   O     0  -0.421  -12.2786  13.6486  30.1495
 EGO  O13  O   OH1   0  -0.594  -13.8921  14.3345  31.5171
 EGO  O10  O   O2    0  -0.477   -9.7305  13.7208  31.1960
 EGO  F21  F   F     0  -0.292   -9.5241  18.9107  34.8737
 EGO  CL1  CL  CL    0  -0.085   -7.4066  19.3178  36.8163
 EGO  H1   H   HCR6  0   0.258   -6.6770  13.3816  26.1004
 EGO  H2   H   HCR6  0   0.257   -9.1415  13.1945  26.1755
 EGO  H3   H   HCR6  0   0.257   -5.4507  14.2866  28.0503
 EGO  H5   H   HCR6  0   0.258  -10.3755  13.9062  28.1902
 EGO  H6   H   HCR6  0   0.254   -6.6881  14.9975  30.0641
 EGO  H7   H   HCR6  0   0.291   -9.5784  14.1446  35.6557
 EGO  H8   H   HCR6  0   0.282   -8.5344  13.8534  33.4525
 EGO  H9   H   HCR6  0   0.295   -8.0335  17.3473  38.7985
 EGO  H10  H   HCR6  0   0.291  -11.3656  17.1448  35.1499
 EGO  H11  H   HCR6  0   0.287  -13.4170  14.3822  33.8026
 EGO  H12  H   HCR5  0   0.267  -14.4315  13.6560  38.1351
 EGO  H13  H   HCH3  0   0.254  -13.7749  15.7393  39.8858
 EGO  H14  H   HCH3  0   0.248  -12.1245  15.2376  40.2210
 EGO  H15  H   HCH3  0   0.245  -12.4286  16.7800  39.4370
 EGO  H16  H   HCH2  0   0.244   -8.7417  15.5453  31.1300
 EGO  H17  H   HCH2  0   0.238  -10.2591  15.4816  30.2229
 EGO  H18  H   HOH1  0   0.489  -14.4332  14.2456  30.7183
 EGO  C14  C   C     0   0.553  -12.6376  13.9915  31.2480
 EGO  H4   H   HCR6  0   0.273   -9.8383  15.6834  38.8960

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
 EGO  C5   C4   aromatic  1.390  0.020  1.390
 EGO  C5   C6   aromatic  1.388  0.020  1.388
 EGO  C4   C3   aromatic  1.387  0.020  1.387
 EGO  C6   C7   aromatic  1.389  0.020  1.389
 EGO  C3   C8   aromatic  1.393  0.020  1.393
 EGO  C7   C8   aromatic  1.391  0.020  1.391
 EGO  C8   C9   single    1.497  0.020  1.497
 EGO  O12  C14  double    1.206  0.020  1.206
 EGO  C9   O10  single    1.433  0.020  1.433
 EGO  O10  C11  single    1.353  0.020  1.353
 EGO  C14  O13  single    1.328  0.020  1.328
 EGO  C14  C15  single    1.488  0.020  1.488
 EGO  C11  C15  aromatic  1.403  0.020  1.403
 EGO  C11  C2   aromatic  1.391  0.020  1.391
 EGO  C15  C16  aromatic  1.396  0.020  1.396
 EGO  C2   C1   aromatic  1.381  0.020  1.381
 EGO  C16  C17  aromatic  1.383  0.020  1.383
 EGO  F21  C26  single    1.333  0.020  1.333
 EGO  C1   C17  aromatic  1.389  0.020  1.389
 EGO  C17  N20  single    1.411  0.020  1.411
 EGO  C26  C27  aromatic  1.377  0.020  1.377
 EGO  C26  C25  aromatic  1.386  0.020  1.386
 EGO  C27  C28  aromatic  1.395  0.020  1.395
 EGO  CL1  C25  single    1.720  0.020  1.720
 EGO  N20  N19  aromatic  1.332  0.020  1.332
 EGO  N20  C29  aromatic  1.363  0.020  1.363
 EGO  C25  C24  aromatic  1.385  0.020  1.385
 EGO  N19  C18  aromatic  1.316  0.020  1.316
 EGO  C28  C29  single    1.464  0.020  1.464
 EGO  C28  C23  aromatic  1.393  0.020  1.393
 EGO  C29  C30  aromatic  1.380  0.020  1.380
 EGO  C24  C23  aromatic  1.386  0.020  1.386
 EGO  C18  C30  aromatic  1.407  0.020  1.407
 EGO  C30  C31  single    1.491  0.020  1.491
 EGO  C5   H1   single    0.930  0.020  1.080
 EGO  C4   H2   single    0.930  0.020  1.080
 EGO  C6   H3   single    0.930  0.020  1.080
 EGO  C23  H4   single    0.930  0.020  1.080
 EGO  C3   H5   single    0.930  0.020  1.080
 EGO  C7   H6   single    0.930  0.020  1.080
 EGO  C1   H7   single    0.930  0.020  1.080
 EGO  C2   H8   single    0.930  0.020  1.080
 EGO  C24  H9   single    0.930  0.020  1.080
 EGO  C27  H10  single    0.930  0.020  1.080
 EGO  C16  H11  single    0.930  0.020  1.080
 EGO  C18  H12  single    0.930  0.020  1.080
 EGO  C31  H13  single    0.970  0.020  1.090
 EGO  C31  H14  single    0.970  0.020  1.090
 EGO  C31  H15  single    0.970  0.020  1.090
 EGO  C9   H16  single    0.970  0.020  1.090
 EGO  C9   H17  single    0.970  0.020  1.090
 EGO  O13  H18  single    0.850  0.020  0.980

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
 EGO  H1   C5   C6   120.13  3.000
 EGO  H1   C5   C4   120.03  3.000
 EGO  C6   C5   C4   119.84  3.000
 EGO  H2   C4   C3   119.92  3.000
 EGO  H2   C4   C5   119.98  3.000
 EGO  C3   C4   C5   120.10  3.000
 EGO  H3   C6   C7   119.92  3.000
 EGO  H3   C6   C5   120.15  3.000
 EGO  C7   C6   C5   119.93  3.000
 EGO  H4   C23  C28  120.16  3.000
 EGO  H4   C23  C24  119.08  3.000
 EGO  C28  C23  C24  120.75  3.000
 EGO  H5   C3   C8   119.64  3.000
 EGO  H5   C3   C4   119.95  3.000
 EGO  C8   C3   C4   120.41  3.000
 EGO  H6   C7   C8   119.59  3.000
 EGO  H6   C7   C6   119.83  3.000
 EGO  C8   C7   C6   120.58  3.000
 EGO  H7   C1   C17  120.97  3.000
 EGO  H7   C1   C2   119.68  3.000
 EGO  C17  C1   C2   119.35  3.000
 EGO  H8   C2   C11  118.96  3.000
 EGO  H8   C2   C1   119.84  3.000
 EGO  C11  C2   C1   121.18  3.000
 EGO  H9   C24  C25  119.87  3.000
 EGO  H9   C24  C23  120.28  3.000
 EGO  C25  C24  C23  119.85  3.000
 EGO  H10  C27  C26  118.99  3.000
 EGO  H10  C27  C28  121.54  3.000
 EGO  C26  C27  C28  119.46  3.000
 EGO  H11  C16  C17  118.64  3.000
 EGO  H11  C16  C15  120.41  3.000
 EGO  C17  C16  C15  120.94  3.000
 EGO  H12  C18  N19  120.27  3.000
 EGO  H12  C18  C30  127.65  3.000
 EGO  N19  C18  C30  112.08  3.000
 EGO  C29  C28  C27  120.87  3.000
 EGO  C29  C28  C23  119.91  3.000
 EGO  C27  C28  C23  119.21  3.000
 EGO  C14  C15  C11  121.77  3.000
 EGO  C11  C15  C16  118.76  3.000
 EGO  C14  C15  C16  119.45  3.000
 EGO  C9   C8   C7   120.63  3.000
 EGO  C9   C8   C3   120.21  3.000
 EGO  C7   C8   C3   119.14  3.000
 EGO  C31  C30  C29  128.26  3.000
 EGO  C31  C30  C18  127.82  3.000
 EGO  C29  C30  C18  103.90  3.000
 EGO  N20  C17  C16  119.19  3.000
 EGO  N20  C17  C1   120.61  3.000
 EGO  C16  C17  C1   120.19  3.000
 EGO  O10  C11  C15  122.67  3.000
 EGO  C15  C11  C2   119.56  3.000
 EGO  O10  C11  C2   117.76  3.000
 EGO  F21  C26  C25  119.06  3.000
 EGO  C25  C26  C27  121.49  3.000
 EGO  F21  C26  C27  119.44  3.000
 EGO  CL1  C25  C26  119.58  3.000
 EGO  CL1  C25  C24  121.19  3.000
 EGO  C26  C25  C24  119.23  3.000
 EGO  N20  C29  C30  106.50  3.000
 EGO  C30  C29  C28  129.25  3.000
 EGO  N20  C29  C28  124.13  3.000
 EGO  H15  C31  H14  107.28  3.000
 EGO  H15  C31  H13  107.71  3.000
 EGO  H14  C31  H13  107.38  3.000
 EGO  H15  C31  C30  111.52  3.000
 EGO  H14  C31  C30  111.95  3.000
 EGO  H13  C31  C30  110.78  3.000
 EGO  H17  C9   H16  107.84  3.000
 EGO  H17  C9   O10  110.14  3.000
 EGO  H16  C9   O10  109.73  3.000
 EGO  H17  C9   C8   110.68  3.000
 EGO  H16  C9   C8   110.68  3.000
 EGO  O10  C9   C8   107.77  3.000
 EGO  N20  N19  C18  105.36  3.000
 EGO  N19  N20  C29  112.16  3.000
 EGO  C29  N20  C17  128.32  3.000
 EGO  N19  N20  C17  119.46  3.000
 EGO  H18  O13  C14  109.68  3.000
 EGO  C9   O10  C11  114.93  3.000
 EGO  O13  C14  O12  122.65  3.000
 EGO  O13  C14  C15  112.01  3.000
 EGO  O12  C14  C15  125.35  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
 EGO  CONST_01  C8   C3   C4   C5      0.00   0.0  0
 EGO  CONST_02  C8   C7   C6   C5      0.00   0.0  0
 EGO  CONST_03  C7   C6   C5   C4      0.00   0.0  0
 EGO  CONST_04  C7   C8   C3   C4      0.00   0.0  0
 EGO  CONST_05  C3   C4   C5   C6      0.00   0.0  0
 EGO  CONST_06  C3   C8   C7   C6      0.00   0.0  0
 EGO  CONST_07  C26  C27  C28  C23     0.00   0.0  0
 EGO  CONST_10  C26  C25  C24  C23     0.00   0.0  0
 EGO  CONST_11  C15  C11  C2   C1      0.00   0.0  0
 EGO  CONST_12  C15  C16  C17  C1      0.00   0.0  0
 EGO  CONST_15  C16  C15  C11  C2      0.00   0.0  0
 EGO  CONST_16  C16  C17  C1   C2      0.00   0.0  0
 EGO  CONST_17  N20  C17  C1   C2    180.00   0.0  0
 EGO  CONST_18  C27  C26  C25  C24     0.00   0.0  0
 EGO  CONST_19  C27  C28  C23  C24     0.00   0.0  0
 EGO  CONST_20  C29  C28  C23  C24   180.00   0.0  0
 EGO  CONST_25  C17  N20  N19  C18   180.00   0.0  0
 EGO  CONST_26  C29  N20  N19  C18     0.00   0.0  0
 EGO  CONST_27  N20  C29  C30  C18     0.00   0.0  0
 EGO  CONST_28  C28  C29  C30  C18   180.00   0.0  0
 EGO  CONST_29  C25  C26  C27  C28     0.00   0.0  0
 EGO  CONST_30  C17  N20  C29  C28     0.00   0.0  0
 EGO  CONST_31  N19  N20  C29  C28   180.00   0.0  0
 EGO  CONST_32  C25  C24  C23  C28     0.00   0.0  0
 EGO  CONST_33  N20  C17  C16  C15   180.00   0.0  0
 EGO  CONST_34  C17  N20  C29  C30   180.00   0.0  0
 EGO  CONST_35  N19  N20  C29  C30     0.00   0.0  0
 EGO  CONST_36  N20  N19  C18  C30     0.00   0.0  0
 EGO  CONST_37  C11  C15  C16  C17     0.00   0.0  0
 EGO  CONST_38  C11  C2   C1   C17     0.00   0.0  0
 EGO  CONST_39  C29  C28  C27  C26   180.00   0.0  0
 EGO  CONST_40  N19  C18  C30  C29     0.00   0.0  0
 EGO  CONST_41  C9   C8   C3   C4    180.00   0.0  0
 EGO  CONST_42  C9   C8   C7   C6    180.00   0.0  0
 EGO  CONST_43  CL1  C25  C24  C23   180.00   0.0  0
 EGO  CONST_44  O10  C11  C2   C1    180.00   0.0  0
 EGO  CONST_45  C14  C15  C11  C2    180.00   0.0  0
 EGO  CONST_46  F21  C26  C25  C24   180.00   0.0  0
 EGO  CONST_47  CL1  C25  C26  C27   180.00   0.0  0
 EGO  CONST_48  O10  C11  C15  C16   180.00   0.0  0
 EGO  CONST_49  F21  C26  C27  C28   180.00   0.0  0
 EGO  CONST_50  C31  C30  C29  C28     0.00   0.0  0
 EGO  CONST_51  C14  C15  C16  C17   180.00   0.0  0
 EGO  CONST_52  N20  C29  C30  C31   180.00   0.0  0
 EGO  CONST_53  N19  C18  C30  C31   180.00   0.0  0
 EGO  CONST_54  H5   C3   C4   C5    180.00   0.0  0
 EGO  CONST_55  H6   C7   C6   C5    180.00   0.0  0
 EGO  CONST_56  H3   C6   C5   C4    180.00   0.0  0
 EGO  CONST_57  H2   C4   C5   C6    180.00   0.0  0
 EGO  CONST_58  H10  C27  C28  C23   180.00   0.0  0
 EGO  CONST_59  H1   C5   C4   C3    180.00   0.0  0
 EGO  CONST_60  H11  C16  C17  C1    180.00   0.0  0
 EGO  CONST_61  H4   C23  C28  C27   180.00   0.0  0
 EGO  CONST_62  H7   C1   C17  C16   180.00   0.0  0
 EGO  CONST_63  H9   C24  C23  C28   180.00   0.0  0
 EGO  CONST_64  H8   C2   C11  C15   180.00   0.0  0
 EGO  CONST_65  H12  C18  C30  C29   180.00   0.0  0
 EGO  CONST_66  H18  O13  C14  C15   180.00   0.0  0
 EGO  Var_01    O10  C9   C8   C3     76.27  30.0  2
 EGO  Var_02    O12  C14  C15  C16  -169.35  30.0  2
 EGO  Var_03    H13  C31  C30  C18   -25.47  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
 EGO  plan-1  C18  0.020
 EGO  plan-1  C28  0.020
 EGO  plan-1  C30  0.020
 EGO  plan-1  C17  0.020
 EGO  plan-1  C29  0.020
 EGO  plan-1  C31  0.020
 EGO  plan-1  N19  0.020
 EGO  plan-1  N20  0.020
 EGO  plan-1  H12  0.020
 EGO  plan-2  C5   0.020
 EGO  plan-2  C4   0.020
 EGO  plan-2  C6   0.020
 EGO  plan-2  C3   0.020
 EGO  plan-2  C7   0.020
 EGO  plan-2  C8   0.020
 EGO  plan-2  C9   0.020
 EGO  plan-2  H1   0.020
 EGO  plan-2  H2   0.020
 EGO  plan-2  H3   0.020
 EGO  plan-2  H5   0.020
 EGO  plan-2  H6   0.020
 EGO  plan-3  C1   0.020
 EGO  plan-3  C2   0.020
 EGO  plan-3  C16  0.020
 EGO  plan-3  C15  0.020
 EGO  plan-3  C17  0.020
 EGO  plan-3  C11  0.020
 EGO  plan-3  N20  0.020
 EGO  plan-3  O10  0.020
 EGO  plan-3  H7   0.020
 EGO  plan-3  H8   0.020
 EGO  plan-3  H11  0.020
 EGO  plan-3  C14  0.020
 EGO  plan-4  C23  0.020
 EGO  plan-4  C24  0.020
 EGO  plan-4  C27  0.020
 EGO  plan-4  C28  0.020
 EGO  plan-4  C26  0.020
 EGO  plan-4  C25  0.020
 EGO  plan-4  C29  0.020
 EGO  plan-4  F21  0.020
 EGO  plan-4  CL1  0.020
 EGO  plan-4  H9   0.020
 EGO  plan-4  H10  0.020
 EGO  plan-4  H4   0.020
 EGO  plan-5  C15  0.020
 EGO  plan-5  O12  0.020
 EGO  plan-5  O13  0.020
 EGO  plan-5  H18  0.020
 EGO  plan-5  C14  0.020

