# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 19:10:09 2022
#   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  48  31  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

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  -0.263   -7.6394  13.8253  26.7289
 EGO  C4   C   CR16   0  -0.241   -8.8683  13.3334  27.1559
 EGO  C6   C   CR16   0  -0.240   -6.8962  14.6404  27.5694
 EGO  C23  C   CR16   0  -0.312   -9.9628  16.3502  38.1876
 EGO  C3   C   CR16   0  -0.293   -9.3520  13.6572  28.4141
 EGO  C7   C   CR16   0  -0.311   -7.3799  14.9596  28.8331
 EGO  C1   C   CR16   0  -0.276  -10.1227  13.9550  34.9136
 EGO  C2   C   CR16   0  -0.335   -9.4290  13.7961  33.7255
 EGO  C24  C   CR16   0  -0.190   -8.8988  17.2379  38.1978
 EGO  C27  C   CR16   0  -0.451  -10.5099  17.0090  35.9417
 EGO  C16  C   CR16   0  -0.316  -12.1476  14.2694  33.6510
 EGO  C18  C   CR15   0  -0.085  -13.7272  14.1420  37.4932
 EGO  C28  C   CR6    0   0.065  -10.7755  16.2221  37.0625
 EGO  C15  C   CR6    0  -0.110  -11.4742  14.0496  32.4553
 EGO  C8   C   CR6    0   0.072   -8.6106  14.4774  29.2639
 EGO  C30  C   CR5    0  -0.201  -12.8764  15.1144  38.0457
 EGO  C17  C   CR6    0   0.298  -11.4848  14.2115  34.8684
 EGO  C11  C   CR6    0   0.327  -10.0944  13.8325  32.5059
 EGO  C26  C   CR6    0   0.641   -9.4433  17.8800  35.9611
 EGO  C25  C   CR6    0  -0.244   -8.6292  18.0045  37.0765
 EGO  C29  C   CR5    0   0.416  -11.8999  15.2858  37.0827
 EGO  C31  C   CH3    0  -0.752  -13.0254  15.8208  39.3504
 EGO  C9   C   CH2    0  -0.229   -9.1475  14.8485  30.6144
 EGO  N19  N   N      0  -0.270  -13.3157  13.7404  36.3076
 EGO  N20  N   NR5    0  -0.455  -12.2079  14.4364  36.0637
 EGO  O12  O   O      0  -0.577  -12.1863  13.0052  30.4699
 EGO  O13  O   OC    -1  -0.584  -12.9589  15.0536  30.9336
 EGO  O10  O   O2     0  -0.487   -9.3604  13.6595  31.3702
 EGO  F21  F   F      0  -0.293   -9.1863  18.6256  34.8851
 EGO  CL1  CL  CL     0  -0.087   -7.3065  19.1049  37.0456
 EGO  H1   H   HCR6   0   0.254   -7.2655  13.5739  25.7446
 EGO  H2   H   HCR6   0   0.253   -9.4523  12.6977  26.5025
 EGO  H3   H   HCR6   0   0.254   -5.9382  15.0269  27.2462
 EGO  H5   H   HCR6   0   0.261  -10.3141  13.2785  28.7382
 EGO  H6   H   HCR6   0   0.252   -6.7936  15.5934  29.4882
 EGO  H7   H   HCR6   0   0.275   -9.6012  13.8932  35.8597
 EGO  H8   H   HCR6   0   0.262   -8.3601  13.6239  33.7435
 EGO  H9   H   HCR6   0   0.291   -8.2704  17.3253  39.0735
 EGO  H10  H   HCR6   0   0.292  -11.1306  16.9595  35.0561
 EGO  H11  H   HCR6   0   0.262  -13.2095  14.4809  33.6342
 EGO  H12  H   HCR5   0   0.261  -14.6263  13.7291  37.9274
 EGO  H13  H   HCH3   0   0.251  -14.0657  15.8148  39.6740
 EGO  H14  H   HCH3   0   0.246  -12.4372  15.3494  40.1398
 EGO  H15  H   HCH3   0   0.244  -12.7037  16.8603  39.2835
 EGO  H16  H   HCH2   0   0.241   -8.4433  15.5059  31.1378
 EGO  H17  H   HCH2   0   0.232  -10.0855  15.4031  30.5048
 EGO  H4   H   HCR6   0   0.273  -10.1477  15.7395  39.0607
 EGO  C14  C   C      0   0.379  -12.2756  14.0393  31.1547

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  1.391  0.020  1.391
 EGO  C5   C6   aromatic  1.387  0.020  1.387
 EGO  C4   C3   aromatic  1.386  0.020  1.386
 EGO  C6   C7   aromatic  1.390  0.020  1.390
 EGO  C3   C8   aromatic  1.395  0.020  1.395
 EGO  C7   C8   aromatic  1.390  0.020  1.390
 EGO  C8   C9   single    1.500  0.020  1.500
 EGO  O12  C14  deloc     1.243  0.020  1.243
 EGO  C9   O10  single    1.425  0.020  1.425
 EGO  O10  C11  single    1.363  0.020  1.363
 EGO  C14  O13  deloc     1.243  0.020  1.243
 EGO  C14  C15  single    1.528  0.020  1.528
 EGO  C11  C15  aromatic  1.398  0.020  1.398
 EGO  C11  C2   aromatic  1.390  0.020  1.390
 EGO  C15  C16  aromatic  1.390  0.020  1.390
 EGO  C2   C1   aromatic  1.385  0.020  1.385
 EGO  C16  C17  aromatic  1.387  0.020  1.387
 EGO  F21  C26  single    1.334  0.020  1.334
 EGO  C1   C17  aromatic  1.387  0.020  1.387
 EGO  C17  N20  single    1.415  0.020  1.415
 EGO  C26  C27  aromatic  1.377  0.020  1.377
 EGO  C26  C25  aromatic  1.387  0.020  1.387
 EGO  C27  C28  aromatic  1.395  0.020  1.395
 EGO  CL1  C25  single    1.721  0.020  1.721
 EGO  N20  N19  aromatic  1.331  0.020  1.331
 EGO  N20  C29  aromatic  1.362  0.020  1.362
 EGO  C25  C24  aromatic  1.385  0.020  1.385
 EGO  N19  C18  aromatic  1.318  0.020  1.318
 EGO  C28  C29  single    1.463  0.020  1.463
 EGO  C28  C23  aromatic  1.394  0.020  1.394
 EGO  C29  C30  aromatic  1.382  0.020  1.382
 EGO  C24  C23  aromatic  1.386  0.020  1.386
 EGO  C18  C30  aromatic  1.405  0.020  1.405
 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

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   120.16  3.000
 EGO  H1   C5   C4   120.15  3.000
 EGO  C6   C5   C4   119.69  3.000
 EGO  H2   C4   C3   119.78  3.000
 EGO  H2   C4   C5   119.93  3.000
 EGO  C3   C4   C5   120.29  3.000
 EGO  H3   C6   C7   119.83  3.000
 EGO  H3   C6   C5   120.21  3.000
 EGO  C7   C6   C5   119.96  3.000
 EGO  H4   C23  C28  120.01  3.000
 EGO  H4   C23  C24  119.14  3.000
 EGO  C28  C23  C24  120.84  3.000
 EGO  H5   C3   C8   119.70  3.000
 EGO  H5   C3   C4   119.97  3.000
 EGO  C8   C3   C4   120.33  3.000
 EGO  H6   C7   C8   119.63  3.000
 EGO  H6   C7   C6   119.70  3.000
 EGO  C8   C7   C6   120.67  3.000
 EGO  H7   C1   C17  120.82  3.000
 EGO  H7   C1   C2   120.14  3.000
 EGO  C17  C1   C2   119.03  3.000
 EGO  H8   C2   C11  119.43  3.000
 EGO  H8   C2   C1   119.90  3.000
 EGO  C11  C2   C1   120.67  3.000
 EGO  H9   C24  C25  119.86  3.000
 EGO  H9   C24  C23  120.26  3.000
 EGO  C25  C24  C23  119.87  3.000
 EGO  H10  C27  C26  118.98  3.000
 EGO  H10  C27  C28  121.49  3.000
 EGO  C26  C27  C28  119.53  3.000
 EGO  H11  C16  C17  119.36  3.000
 EGO  H11  C16  C15  119.51  3.000
 EGO  C17  C16  C15  121.13  3.000
 EGO  H12  C18  N19  120.33  3.000
 EGO  H12  C18  C30  127.61  3.000
 EGO  N19  C18  C30  112.06  3.000
 EGO  C29  C28  C27  121.22  3.000
 EGO  C29  C28  C23  119.72  3.000
 EGO  C27  C28  C23  119.06  3.000
 EGO  C14  C15  C11  123.21  3.000
 EGO  C11  C15  C16  118.14  3.000
 EGO  C14  C15  C16  118.64  3.000
 EGO  C9   C8   C7   120.67  3.000
 EGO  C9   C8   C3   120.26  3.000
 EGO  C7   C8   C3   119.07  3.000
 EGO  C31  C30  C29  128.43  3.000
 EGO  C31  C30  C18  127.68  3.000
 EGO  C29  C30  C18  103.86  3.000
 EGO  N20  C17  C16  119.37  3.000
 EGO  N20  C17  C1   120.25  3.000
 EGO  C16  C17  C1   120.37  3.000
 EGO  O10  C11  C15  121.40  3.000
 EGO  C15  C11  C2   120.56  3.000
 EGO  O10  C11  C2   118.03  3.000
 EGO  F21  C26  C25  119.04  3.000
 EGO  C25  C26  C27  121.52  3.000
 EGO  F21  C26  C27  119.43  3.000
 EGO  CL1  C25  C26  119.62  3.000
 EGO  CL1  C25  C24  121.21  3.000
 EGO  C26  C25  C24  119.17  3.000
 EGO  N20  C29  C30  106.51  3.000
 EGO  C30  C29  C28  129.18  3.000
 EGO  N20  C29  C28  124.23  3.000
 EGO  H15  C31  H14  107.29  3.000
 EGO  H15  C31  H13  107.77  3.000
 EGO  H14  C31  H13  107.30  3.000
 EGO  H15  C31  C30  111.62  3.000
 EGO  H14  C31  C30  111.98  3.000
 EGO  H13  C31  C30  110.65  3.000
 EGO  H17  C9   H16  107.11  3.000
 EGO  H17  C9   O10  110.34  3.000
 EGO  H16  C9   O10  110.07  3.000
 EGO  H17  C9   C8   109.98  3.000
 EGO  H16  C9   C8   110.38  3.000
 EGO  O10  C9   C8   108.94  3.000
 EGO  N20  N19  C18  105.40  3.000
 EGO  N19  N20  C29  112.17  3.000
 EGO  C29  N20  C17  127.99  3.000
 EGO  N19  N20  C17  119.81  3.000
 EGO  C9   O10  C11  114.61  3.000
 EGO  O13  C14  O12  128.33  3.000
 EGO  O13  C14  C15  115.74  3.000
 EGO  O12  C14  C15  115.90  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  Var_01    O10  C9   C8   C3     59.83  30.0  2
 EGO  Var_02    O12  C14  C15  C16  -123.07  30.0  3
 EGO  Var_03    H13  C31  C30  C18   -23.17  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  C14  0.020

