# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:12:13 2022
#   Inital geometry file: a 122 line input string
#   Ligand name: 5-(2-fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl}phenyl)isoxazole-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)c1c(O)cccc1OC/C=C/c2ccc(F)c(c2)c3onc(c3)C(O)=O
#
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
 234  234  '5-(2-fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl}phenyl)isoxazole-3-carboxylic acid'  ligand  45  30  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_234
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
 234  C1    C  CR6    0   0.519   1.8728  -1.1004   3.4665
 234  C2    C  CR6    0  -0.191   0.6020  -0.5377   3.4676
 234  C3    C  CR16   0  -0.344  -0.1192  -0.5971   2.2723
 234  C4    C  CR6    0   0.164   0.3990  -1.1854   1.1229
 234  C5    C  CR16   0  -0.308   1.6788  -1.7450   1.1802
 234  C6    C  CR16   0  -0.378   2.4161  -1.7008   2.3479
 234  C7    C  CR5    0   0.510   0.0410   0.0876   4.6572
 234  O12   O  O      0  -0.355  -1.0941   0.7805   4.4807
 234  N13   N  N      0  -0.152  -1.5187   1.2912   5.6661
 234  C14   C  CR5    0   0.071  -0.6497   0.9151   6.5600
 234  C15   C  CR15   0  -0.534   0.3800   0.1401   5.9715
 234  C16   C  C      0   0.391  -0.7888   1.2927   8.0246
 234  O1    O  OC    -1  -0.585  -1.7740   1.9815   8.3275
 234  O2    O  O      0  -0.579   0.1152   0.8589   8.7577
 234  C8    C  C1     0  -0.272  -0.4240  -1.1928  -0.0891
 234  C32   C  CR6    0   0.419  -1.0501  -0.5452  -4.6501
 234  C33   C  CR16   0  -0.413  -2.2101  -1.2344  -4.9918
 234  C34   C  CR16   0  -0.226  -2.7365  -1.0727  -6.2665
 234  C35   C  CR16   0  -0.406  -2.1377  -0.2508  -7.2031
 234  C36   C  CR6    0   0.384  -0.9729   0.4321  -6.8587
 234  C37   C  CR6    0  -0.264  -0.4249   0.2870  -5.5855
 234  C38   C  C      0   0.558   0.7912   1.0537  -5.1967
 234  O11   O  O      0  -0.436   0.8171   1.8898  -4.3300
 234  O4    O  O2     0  -0.438   1.8423   0.7042  -5.9191
 234  C39   C  CH3    0  -0.425   3.0633   1.4085  -5.6862
 234  O14   O  OH1    0  -0.617  -0.3493   1.2661  -7.7061
 234  O3    O  O2     0  -0.464  -0.4424  -0.6304  -3.4569
 234  C40   C  CH2    0  -0.244  -0.9533  -1.5335  -2.4821
 234  C41   C  C1     0  -0.251  -0.0235  -1.5111  -1.3190
 234  F1    F  F      0  -0.299   2.6049  -1.0646   4.5856
 234  H3    H  HCR6   0   0.273  -1.1152  -0.1752   2.2309
 234  H5    H  HCR6   0   0.272   2.1073  -2.2320   0.3145
 234  H6    H  HCR6   0   0.290   3.4059  -2.1346   2.3982
 234  H15   H  HCR5   0   0.273   1.2151  -0.3062   6.4784
 234  H8    H  H      0   0.259  -1.4589  -0.8958   0.0563
 234  H33   H  HCR6   0   0.283  -2.7101  -1.8878  -4.2919
 234  H34   H  HCR6   0   0.271  -3.6418  -1.6030  -6.5313
 234  H35   H  HCR6   0   0.274  -2.5675  -0.1362  -8.1907
 234  H391  H  HCH3   0   0.253   3.7856   0.9889  -6.3801
 234  H392  H  HCH3   0   0.241   2.9510   2.4748  -5.8814
 234  H393  H  HCH3   0   0.241   3.4170   1.2652  -4.6654
 234  H14   H  HOH1   0   0.482  -0.8253   1.3119  -8.5433
 234  H401  H  HCH2   0   0.246  -1.9648  -1.2458  -2.1768
 234  H402  H  HCH2   0   0.244  -1.0037  -2.5446  -2.9027
 234  H41   H  H      0   0.265   1.0045  -1.7939  -1.5228

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
 234  C1   C2    aromatic  1.390  0.020  1.390
 234  C1   C6    aromatic  1.381  0.020  1.381
 234  C1   F1    single    1.338  0.020  1.338
 234  C2   C3    aromatic  1.397  0.020  1.397
 234  C2   C7    single    1.456  0.020  1.456
 234  C3   C4    aromatic  1.391  0.020  1.391
 234  C3   H3    single    0.930  0.020  1.080
 234  C4   C5    aromatic  1.398  0.020  1.398
 234  C4   C8    single    1.465  0.020  1.465
 234  C5   C6    aromatic  1.382  0.020  1.382
 234  C5   H5    single    0.930  0.020  1.080
 234  C6   H6    single    0.930  0.020  1.080
 234  C7   O12   aromatic  1.342  0.020  1.342
 234  C7   C15   aromatic  1.358  0.020  1.358
 234  O12  N13   aromatic  1.359  0.020  1.359
 234  N13  C14   aromatic  1.302  0.020  1.302
 234  C14  C15   aromatic  1.417  0.020  1.417
 234  C14  C16   single    1.519  0.020  1.519
 234  C15  H15   single    0.930  0.020  1.080
 234  C16  O1    deloc     1.240  0.020  1.240
 234  C16  O2    deloc     1.242  0.020  1.242
 234  C8   C41   double    1.332  0.020  1.332
 234  C8   H8    single    0.930  0.020  1.080
 234  C32  C33   aromatic  1.392  0.020  1.392
 234  C32  C37   aromatic  1.399  0.020  1.399
 234  C32  O3    single    1.342  0.020  1.342
 234  C33  C34   aromatic  1.389  0.020  1.389
 234  C33  H33   single    0.930  0.020  1.080
 234  C34  C35   aromatic  1.382  0.020  1.382
 234  C34  H34   single    0.930  0.020  1.080
 234  C35  C36   aromatic  1.393  0.020  1.393
 234  C35  H35   single    0.930  0.020  1.080
 234  C36  C37   aromatic  1.394  0.020  1.394
 234  C36  O14   single    1.343  0.020  1.343
 234  C37  C38   single    1.489  0.020  1.489
 234  C38  O11   double    1.205  0.020  1.205
 234  C38  O4    single    1.322  0.020  1.322
 234  O4   C39   single    1.429  0.020  1.429
 234  C39  H391  single    0.970  0.020  1.090
 234  C39  H392  single    0.970  0.020  1.090
 234  C39  H393  single    0.970  0.020  1.090
 234  O14  H14   single    0.850  0.020  0.980
 234  O3   C40   single    1.424  0.020  1.424
 234  C40  C41   single    1.489  0.020  1.489
 234  C40  H401  single    0.970  0.020  1.090
 234  C40  H402  single    0.970  0.020  1.090
 234  C41  H41   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
 234  F1    C1   C6    118.30  3.000
 234  F1    C1   C2    119.27  3.000
 234  C6    C1   C2    122.44  3.000
 234  C7    C2   C3    121.21  3.000
 234  C7    C2   C1    121.79  3.000
 234  C3    C2   C1    117.00  3.000
 234  H3    C3   C4    118.42  3.000
 234  H3    C3   C2    119.41  3.000
 234  C4    C3   C2    122.17  3.000
 234  C8    C4   C5    123.10  3.000
 234  C8    C4   C3    118.45  3.000
 234  C5    C4   C3    118.45  3.000
 234  H5    C5   C6    118.64  3.000
 234  H5    C5   C4    120.67  3.000
 234  C6    C5   C4    120.68  3.000
 234  H6    C6   C5    120.98  3.000
 234  H6    C6   C1    119.77  3.000
 234  C5    C6   C1    119.25  3.000
 234  C15   C7   O12   108.57  3.000
 234  C15   C7   C2    135.30  3.000
 234  O12   C7   C2    116.12  3.000
 234  N13   O12  C7    110.11  3.000
 234  C14   N13  O12   106.37  3.000
 234  C16   C14  C15   127.09  3.000
 234  C16   C14  N13   121.94  3.000
 234  C15   C14  N13   110.97  3.000
 234  H15   C15  C14   126.61  3.000
 234  H15   C15  C7    129.40  3.000
 234  C14   C15  C7    103.99  3.000
 234  O2    C16  O1    128.92  3.000
 234  O2    C16  C14   114.56  3.000
 234  O1    C16  C14   116.52  3.000
 234  H8    C8   C41   118.38  3.000
 234  H8    C8   C4    115.03  3.000
 234  C41   C8   C4    126.59  3.000
 234  O3    C32  C37   115.45  3.000
 234  O3    C32  C33   124.36  3.000
 234  C37   C32  C33   120.18  3.000
 234  H33   C33  C34   119.32  3.000
 234  H33   C33  C32   121.75  3.000
 234  C34   C33  C32   118.93  3.000
 234  H34   C34  C35   119.20  3.000
 234  H34   C34  C33   119.00  3.000
 234  C35   C34  C33   121.80  3.000
 234  H35   C35  C36   120.34  3.000
 234  H35   C35  C34   120.58  3.000
 234  C36   C35  C34   119.08  3.000
 234  O14   C36  C37   117.30  3.000
 234  O14   C36  C35   122.46  3.000
 234  C37   C36  C35   120.23  3.000
 234  C38   C37  C36   120.40  3.000
 234  C38   C37  C32   119.77  3.000
 234  C36   C37  C32   119.79  3.000
 234  O4    C38  O11   124.01  3.000
 234  O4    C38  C37   111.74  3.000
 234  O11   C38  C37   124.25  3.000
 234  C39   O4   C38   117.39  3.000
 234  H393  C39  H392  109.26  3.000
 234  H393  C39  H391  109.38  3.000
 234  H392  C39  H391  109.40  3.000
 234  H393  C39  O4    111.42  3.000
 234  H392  C39  O4    111.41  3.000
 234  H391  C39  O4    105.89  3.000
 234  H14   O14  C36   110.38  3.000
 234  C40   O3   C32   119.12  3.000
 234  H402  C40  H401  107.87  3.000
 234  H402  C40  C41   110.01  3.000
 234  H401  C40  C41   110.80  3.000
 234  H402  C40  O3    109.80  3.000
 234  H401  C40  O3    110.84  3.000
 234  C41   C40  O3    107.53  3.000
 234  H41   C41  C40   116.15  3.000
 234  H41   C41  C8    121.36  3.000
 234  C40   C41  C8    122.48  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
 234  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 234  CONST_02  O12   C7   C2   C1    180.00   0.0  0
 234  CONST_03  C15   C7   C2   C1      0.00   0.0  0
 234  CONST_04  C4    C5   C6   C1      0.00   0.0  0
 234  CONST_05  C5    C6   C1   C2      0.00   0.0  0
 234  CONST_06  C5    C4   C3   C2      0.00   0.0  0
 234  CONST_07  N13   O12  C7   C2    180.00   0.0  0
 234  CONST_08  C14   C15  C7   C2    180.00   0.0  0
 234  CONST_09  C6    C1   C2   C3      0.00   0.0  0
 234  CONST_10  O12   C7   C2   C3      0.00   0.0  0
 234  CONST_11  C15   C7   C2   C3    180.00   0.0  0
 234  CONST_12  C6    C5   C4   C3      0.00   0.0  0
 234  CONST_13  C7    C2   C3   C4    180.00   0.0  0
 234  CONST_14  C7    C2   C1   C6    180.00   0.0  0
 234  CONST_15  C14   N13  O12  C7      0.00   0.0  0
 234  CONST_16  N13   C14  C15  C7      0.00   0.0  0
 234  CONST_17  C14   C15  C7   O12     0.00   0.0  0
 234  CONST_18  C15   C14  N13  O12     0.00   0.0  0
 234  CONST_19  C15   C7   O12  N13     0.00   0.0  0
 234  CONST_20  C35   C34  C33  C32     0.00   0.0  0
 234  CONST_21  C35   C36  C37  C32     0.00   0.0  0
 234  CONST_22  C36   C37  C32  C33     0.00   0.0  0
 234  CONST_23  C36   C35  C34  C33     0.00   0.0  0
 234  CONST_24  C37   C32  C33  C34     0.00   0.0  0
 234  CONST_25  C37   C36  C35  C34     0.00   0.0  0
 234  CONST_26  C8    C4   C3   C2    180.00   0.0  0
 234  CONST_27  F1    C1   C2   C3    180.00   0.0  0
 234  CONST_28  F1    C1   C6   C5    180.00   0.0  0
 234  CONST_29  C8    C4   C5   C6    180.00   0.0  0
 234  CONST_30  F1    C1   C2   C7      0.00   0.0  0
 234  CONST_31  C16   C14  C15  C7    180.00   0.0  0
 234  CONST_32  C16   C14  N13  O12   180.00   0.0  0
 234  CONST_33  O14   C36  C37  C32   180.00   0.0  0
 234  CONST_34  C38   C37  C32  C33   180.00   0.0  0
 234  CONST_35  O3    C32  C33  C34   180.00   0.0  0
 234  CONST_36  O14   C36  C35  C34   180.00   0.0  0
 234  CONST_37  C38   C37  C36  C35   180.00   0.0  0
 234  CONST_38  O3    C32  C37  C36   180.00   0.0  0
 234  CONST_39  H3    C3   C2   C1    180.00   0.0  0
 234  CONST_40  H5    C5   C6   C1    180.00   0.0  0
 234  CONST_41  H6    C6   C1   C2    180.00   0.0  0
 234  CONST_42  H15   C15  C7   C2      0.00   0.0  0
 234  CONST_43  H34   C34  C33  C32   180.00   0.0  0
 234  CONST_44  H35   C35  C34  C33   180.00   0.0  0
 234  CONST_45  H33   C33  C34  C35   180.00   0.0  0
 234  Var_01    C41   C8   C4   C3    168.52  30.0  2
 234  Var_02    O1    C16  C14  N13    -0.11  30.0  2
 234  Var_03    O11   C38  C37  C32   -61.90  30.0  2
 234  Var_04    C40   C41  C8   C4    177.80   0.0  2
 234  Var_05    C41   C40  O3   C32   174.95  30.0  3
 234  Var_06    O3    C40  C41  C8    122.05  30.0  1
 234  Var_07    H391  C39  O4   C38  -179.08  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
 234  plan-1  C2   0.020
 234  plan-1  C7   0.020
 234  plan-1  O12  0.020
 234  plan-1  N13  0.020
 234  plan-1  C14  0.020
 234  plan-1  C15  0.020
 234  plan-1  C16  0.020
 234  plan-1  H15  0.020
 234  plan-2  C1   0.020
 234  plan-2  C2   0.020
 234  plan-2  C3   0.020
 234  plan-2  C4   0.020
 234  plan-2  C5   0.020
 234  plan-2  C6   0.020
 234  plan-2  C7   0.020
 234  plan-2  C8   0.020
 234  plan-2  F1   0.020
 234  plan-2  H3   0.020
 234  plan-2  H5   0.020
 234  plan-2  H6   0.020
 234  plan-3  C32  0.020
 234  plan-3  C33  0.020
 234  plan-3  C34  0.020
 234  plan-3  C35  0.020
 234  plan-3  C36  0.020
 234  plan-3  C37  0.020
 234  plan-3  C38  0.020
 234  plan-3  O14  0.020
 234  plan-3  O3   0.020
 234  plan-3  H33  0.020
 234  plan-3  H34  0.020
 234  plan-3  H35  0.020
 234  plan-4  C14  0.020
 234  plan-4  C16  0.020
 234  plan-4  O1   0.020
 234  plan-4  O2   0.020
 234  plan-5  C4   0.020
 234  plan-5  C8   0.020
 234  plan-5  C40  0.020
 234  plan-5  C41  0.020
 234  plan-5  H8   0.020
 234  plan-5  H41  0.020
 234  plan-6  C37  0.020
 234  plan-6  C38  0.020
 234  plan-6  O11  0.020
 234  plan-6  O4   0.020

