# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 11:30:10 2020
#   Inital geometry file: a 130 line input string
#   Ligand name: 5-(3-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl}phenyl)-4-(hydroxymethyl)isoxazole-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)c1c(O)cccc1OC/C=C/c2cccc(c2)c3onc(C(O)=O)c3CO
#
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
 IX1  IX1  '5-(3-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl}phenyl)-4-(hydroxymethyl)isoxazole-3-carboxylic acid'  ligand  50  31  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_IX1
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
 IX1  C1    C  CR16  0  -0.318   2.1242  -0.8392   3.1396
 IX1  C2    C  CR6   0   0.041   0.8100  -0.3772   3.1372
 IX1  C3    C  CR16  0  -0.350   0.0439  -0.4940   1.9775
 IX1  C4    C  CR6   0   0.169   0.5684  -1.0695   0.8227
 IX1  C5    C  CR16  0  -0.318   1.8812  -1.5502   0.8533
 IX1  C6    C  CR16  0  -0.219   2.6478  -1.4313   1.9987
 IX1  C7    C  CR5   0   0.438   0.2424   0.2303   4.3345
 IX1  O12   O  O     0  -0.331  -0.5942   1.2643   4.1525
 IX1  N13   N  N     0  -0.129  -1.0524   1.7097   5.3360
 IX1  C14   C  CR5   0   0.125  -0.4908   0.9613   6.2412
 IX1  C15   C  CR5   0  -0.160   0.3592  -0.0203   5.6669
 IX1  C16   C  C     0   0.515  -0.7213   1.2209   7.6823
 IX1  O1    O  OH1   0  -0.581  -1.8042   1.9438   7.8917
 IX1  O2    O  O     0  -0.412   0.0220   0.8217   8.5393
 IX1  C8    C  C1    0  -0.276  -0.2816  -1.1401  -0.3691
 IX1  C32   C  CR6   0   0.419  -0.9941  -0.5622  -4.9293
 IX1  C33   C  CR16  0  -0.413  -2.1378  -1.2884  -5.2466
 IX1  C34   C  CR16  0  -0.226  -2.6917  -1.1493  -6.5126
 IX1  C35   C  CR16  0  -0.405  -2.1360  -0.3146  -7.4644
 IX1  C36   C  CR6   0   0.384  -0.9858   0.4048  -7.1450
 IX1  C37   C  CR6   0  -0.264  -0.4118   0.2840  -5.8810
 IX1  C38   C  C     0   0.557   0.7906   1.0847  -5.5186
 IX1  O11   O  O     0  -0.436   0.8072   1.9339  -4.6643
 IX1  O13   O  O2    0  -0.438   1.8412   0.7474  -6.2471
 IX1  C39   C  CH3   0  -0.425   3.0527   1.4736  -6.0308
 IX1  O14   O  OH1   0  -0.618  -0.4006   1.2514  -8.0069
 IX1  O3    O  O2    0  -0.464  -0.3623  -0.6205  -3.7470
 IX1  C40   C  CH2   0  -0.243  -0.8323  -1.5242  -2.7528
 IX1  C41   C  C1    0  -0.248   0.1123  -1.4482  -1.6038
 IX1  C9    C  CH2   0  -0.255   1.0718  -1.1220   6.3750
 IX1  O4    O  OH1   0  -0.663   0.1196  -1.8798   7.0868
 IX1  H1    H  HCR6  0   0.273   2.7481  -0.7197   4.0152
 IX1  H3    H  HCR6  0   0.265  -0.9809  -0.1423   1.9671
 IX1  H5    H  HCR6  0   0.263   2.3100  -2.0250  -0.0195
 IX1  H6    H  HCR6  0   0.271   3.6657  -1.7968   2.0060
 IX1  HO1   H  HOH1  0   0.495  -1.9043   2.1311   8.8381
 IX1  H8    H  H     0   0.259  -1.3273  -0.8948  -0.2055
 IX1  H33   H  HCR6  0   0.283  -2.6054  -1.9527  -4.5345
 IX1  H34   H  HCR6  0   0.271  -3.5848  -1.7088  -6.7581
 IX1  H35   H  HCR6  0   0.275  -2.5876  -0.2187  -8.4445
 IX1  H391  H  HCH3  0   0.253   3.7778   1.0548  -6.7220
 IX1  H392  H  HCH3  0   0.241   2.9233   2.5352  -6.2407
 IX1  H393  H  HCH3  0   0.241   3.4129   1.3500  -5.0097
 IX1  H14   H  HOH1  0   0.482  -0.8877   1.2758  -8.8384
 IX1  H401  H  HCH2  0   0.247  -1.8489  -1.2657  -2.4389
 IX1  H402  H  HCH2  0   0.245  -0.8532  -2.5434  -3.1559
 IX1  H41   H  H     0   0.267   1.1501  -1.6783  -1.8235
 IX1  H91   H  HCH2  0   0.217   1.6034  -1.7426   5.6463
 IX1  H92   H  HCH2  0   0.239   1.8305  -0.6973   7.0374
 IX1  HO4   H  HOH1  0   0.461   0.5207  -2.1713   7.9096

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
 IX1  C1   C2    aromatic  1.393  0.020  1.393
 IX1  C1   C6    aromatic  1.388  0.020  1.388
 IX1  C1   H1    single    0.930  0.020  1.080
 IX1  C2   C3    aromatic  1.395  0.020  1.395
 IX1  C2   C7    single    1.458  0.020  1.458
 IX1  C3   C4    aromatic  1.393  0.020  1.393
 IX1  C3   H3    single    0.930  0.020  1.080
 IX1  C4   C5    aromatic  1.398  0.020  1.398
 IX1  C4   C8    single    1.466  0.020  1.466
 IX1  C5   C6    aromatic  1.383  0.020  1.383
 IX1  C5   H5    single    0.930  0.020  1.080
 IX1  C6   H6    single    0.930  0.020  1.080
 IX1  C7   O12   aromatic  1.342  0.020  1.342
 IX1  C7   C15   aromatic  1.361  0.020  1.361
 IX1  O12  N13   aromatic  1.345  0.020  1.345
 IX1  N13  C14   aromatic  1.302  0.020  1.302
 IX1  C14  C15   aromatic  1.420  0.020  1.420
 IX1  C14  C16   single    1.482  0.020  1.482
 IX1  C15  C9    single    1.491  0.020  1.491
 IX1  C16  O1    single    1.319  0.020  1.319
 IX1  C16  O2    double    1.203  0.020  1.203
 IX1  O1   HO1   single    0.850  0.020  0.980
 IX1  C8   C41   double    1.332  0.020  1.332
 IX1  C8   H8    single    0.930  0.020  1.080
 IX1  C32  C33   aromatic  1.392  0.020  1.392
 IX1  C32  C37   aromatic  1.400  0.020  1.400
 IX1  C32  O3    single    1.342  0.020  1.342
 IX1  C33  C34   aromatic  1.389  0.020  1.389
 IX1  C33  H33   single    0.930  0.020  1.080
 IX1  C34  C35   aromatic  1.383  0.020  1.383
 IX1  C34  H34   single    0.930  0.020  1.080
 IX1  C35  C36   aromatic  1.394  0.020  1.394
 IX1  C35  H35   single    0.930  0.020  1.080
 IX1  C36  C37   aromatic  1.393  0.020  1.393
 IX1  C36  O14   single    1.342  0.020  1.342
 IX1  C37  C38   single    1.489  0.020  1.489
 IX1  C38  O11   double    1.205  0.020  1.205
 IX1  C38  O13   single    1.322  0.020  1.322
 IX1  O13  C39   single    1.429  0.020  1.429
 IX1  C39  H391  single    0.970  0.020  1.090
 IX1  C39  H392  single    0.970  0.020  1.090
 IX1  C39  H393  single    0.970  0.020  1.090
 IX1  O14  H14   single    0.850  0.020  0.980
 IX1  O3   C40   single    1.423  0.020  1.423
 IX1  C40  C41   single    1.489  0.020  1.489
 IX1  C40  H401  single    0.970  0.020  1.090
 IX1  C40  H402  single    0.970  0.020  1.090
 IX1  C41  H41   single    0.930  0.020  1.080
 IX1  C9   O4    single    1.410  0.020  1.410
 IX1  C9   H91   single    0.970  0.020  1.090
 IX1  C9   H92   single    0.970  0.020  1.090
 IX1  O4   HO4   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
 IX1  H1    C1   C6    119.67  3.000
 IX1  H1    C1   C2    120.59  3.000
 IX1  C6    C1   C2    119.73  3.000
 IX1  C7    C2   C3    120.26  3.000
 IX1  C7    C2   C1    120.27  3.000
 IX1  C3    C2   C1    119.46  3.000
 IX1  H3    C3   C4    118.84  3.000
 IX1  H3    C3   C2    120.01  3.000
 IX1  C4    C3   C2    121.14  3.000
 IX1  C8    C4   C5    123.07  3.000
 IX1  C8    C4   C3    118.41  3.000
 IX1  C5    C4   C3    118.52  3.000
 IX1  H5    C5   C6    119.08  3.000
 IX1  H5    C5   C4    120.34  3.000
 IX1  C6    C5   C4    120.58  3.000
 IX1  H6    C6   C5    119.87  3.000
 IX1  H6    C6   C1    119.58  3.000
 IX1  C5    C6   C1    120.55  3.000
 IX1  C15   C7   O12   109.15  3.000
 IX1  C15   C7   C2    133.95  3.000
 IX1  O12   C7   C2    116.89  3.000
 IX1  N13   O12  C7    110.37  3.000
 IX1  C14   N13  O12   105.94  3.000
 IX1  C16   C14  C15   127.40  3.000
 IX1  C16   C14  N13   120.54  3.000
 IX1  C15   C14  N13   111.99  3.000
 IX1  C9    C15  C14   127.22  3.000
 IX1  C9    C15  C7    129.95  3.000
 IX1  C14   C15  C7    102.55  3.000
 IX1  O2    C16  O1    125.20  3.000
 IX1  O2    C16  C14   122.58  3.000
 IX1  O1    C16  C14   112.21  3.000
 IX1  HO1   O1   C16   110.21  3.000
 IX1  H8    C8   C41   118.45  3.000
 IX1  H8    C8   C4    115.14  3.000
 IX1  C41   C8   C4    126.40  3.000
 IX1  O3    C32  C37   115.43  3.000
 IX1  O3    C32  C33   124.42  3.000
 IX1  C37   C32  C33   120.15  3.000
 IX1  H33   C33  C34   119.33  3.000
 IX1  H33   C33  C32   121.76  3.000
 IX1  C34   C33  C32   118.91  3.000
 IX1  H34   C34  C35   119.20  3.000
 IX1  H34   C34  C33   118.96  3.000
 IX1  C35   C34  C33   121.85  3.000
 IX1  H35   C35  C36   120.38  3.000
 IX1  H35   C35  C34   120.57  3.000
 IX1  C36   C35  C34   119.05  3.000
 IX1  O14   C36  C37   117.23  3.000
 IX1  O14   C36  C35   122.55  3.000
 IX1  C37   C36  C35   120.20  3.000
 IX1  C38   C37  C36   120.44  3.000
 IX1  C38   C37  C32   119.68  3.000
 IX1  C36   C37  C32   119.84  3.000
 IX1  O13   C38  O11   124.02  3.000
 IX1  O13   C38  C37   111.73  3.000
 IX1  O11   C38  C37   124.24  3.000
 IX1  C39   O13  C38   117.43  3.000
 IX1  H393  C39  H392  109.28  3.000
 IX1  H393  C39  H391  109.39  3.000
 IX1  H392  C39  H391  109.41  3.000
 IX1  H393  C39  O13   111.38  3.000
 IX1  H392  C39  O13   111.42  3.000
 IX1  H391  C39  O13   105.89  3.000
 IX1  H14   O14  C36   110.46  3.000
 IX1  C40   O3   C32   119.18  3.000
 IX1  H402  C40  H401  107.89  3.000
 IX1  H402  C40  C41   110.07  3.000
 IX1  H401  C40  C41   110.83  3.000
 IX1  H402  C40  O3    109.86  3.000
 IX1  H401  C40  O3    110.91  3.000
 IX1  C41   C40  O3    107.28  3.000
 IX1  H41   C41  C40   116.07  3.000
 IX1  H41   C41  C8    121.29  3.000
 IX1  C40   C41  C8    122.64  3.000
 IX1  H92   C9   H91   106.64  3.000
 IX1  H92   C9   O4    111.82  3.000
 IX1  H91   C9   O4    111.06  3.000
 IX1  H92   C9   C15   109.41  3.000
 IX1  H91   C9   C15   109.56  3.000
 IX1  O4    C9   C15   108.31  3.000
 IX1  HO4   O4   C9    108.28  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
 IX1  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 IX1  CONST_04  C4    C5   C6   C1      0.00   0.0  0
 IX1  CONST_05  C5    C6   C1   C2      0.00   0.0  0
 IX1  CONST_06  C5    C4   C3   C2      0.00   0.0  0
 IX1  CONST_07  N13   O12  C7   C2    180.00   0.0  0
 IX1  CONST_08  C14   C15  C7   C2    180.00   0.0  0
 IX1  CONST_09  C6    C1   C2   C3      0.00   0.0  0
 IX1  CONST_12  C6    C5   C4   C3      0.00   0.0  0
 IX1  CONST_13  C7    C2   C3   C4    180.00   0.0  0
 IX1  CONST_14  C7    C2   C1   C6    180.00   0.0  0
 IX1  CONST_15  C14   N13  O12  C7      0.00   0.0  0
 IX1  CONST_16  N13   C14  C15  C7      0.00   0.0  0
 IX1  CONST_17  C14   C15  C7   O12     0.00   0.0  0
 IX1  CONST_18  C15   C14  N13  O12     0.00   0.0  0
 IX1  CONST_19  C15   C7   O12  N13     0.00   0.0  0
 IX1  CONST_20  C35   C34  C33  C32     0.00   0.0  0
 IX1  CONST_21  C35   C36  C37  C32     0.00   0.0  0
 IX1  CONST_22  C36   C37  C32  C33     0.00   0.0  0
 IX1  CONST_23  C36   C35  C34  C33     0.00   0.0  0
 IX1  CONST_24  C37   C32  C33  C34     0.00   0.0  0
 IX1  CONST_25  C37   C36  C35  C34     0.00   0.0  0
 IX1  CONST_26  C8    C4   C3   C2    180.00   0.0  0
 IX1  CONST_27  C9    C15  C7   C2      0.00   0.0  0
 IX1  CONST_28  C8    C4   C5   C6    180.00   0.0  0
 IX1  CONST_29  C16   C14  C15  C7    180.00   0.0  0
 IX1  CONST_30  C9    C15  C7   O12   180.00   0.0  0
 IX1  CONST_31  C16   C14  N13  O12   180.00   0.0  0
 IX1  CONST_32  C9    C15  C14  N13   180.00   0.0  0
 IX1  CONST_33  O14   C36  C37  C32   180.00   0.0  0
 IX1  CONST_34  C38   C37  C32  C33   180.00   0.0  0
 IX1  CONST_35  O3    C32  C33  C34   180.00   0.0  0
 IX1  CONST_36  O14   C36  C35  C34   180.00   0.0  0
 IX1  CONST_37  C38   C37  C36  C35   180.00   0.0  0
 IX1  CONST_38  O3    C32  C37  C36   180.00   0.0  0
 IX1  CONST_39  H3    C3   C2   C1    180.00   0.0  0
 IX1  CONST_40  H5    C5   C6   C1    180.00   0.0  0
 IX1  CONST_41  H6    C6   C1   C2    180.00   0.0  0
 IX1  CONST_42  H1    C1   C2   C3    180.00   0.0  0
 IX1  CONST_43  H34   C34  C33  C32   180.00   0.0  0
 IX1  CONST_44  H35   C35  C34  C33   180.00   0.0  0
 IX1  CONST_45  H33   C33  C34  C35   180.00   0.0  0
 IX1  CONST_46  HO1   O1   C16  C14   180.00   0.0  0
 IX1  Var_01    C41   C8   C4   C3    168.23  30.0  2
 IX1  Var_02    O4    C9   C15  C7   -117.29  30.0  2
 IX1  Var_03    O1    C16  C14  N13    19.61  30.0  2
 IX1  Var_04    O11   C38  C37  C32   -62.75  30.0  2
 IX1  Var_05    C40   C41  C8   C4    178.64   0.0  2
 IX1  Var_06    C41   C40  O3   C32   175.71  30.0  3
 IX1  Var_07    O3    C40  C41  C8    123.00  30.0  1
 IX1  Var_08    H391  C39  O13  C38  -179.53  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
 IX1  plan-1  C2   0.020
 IX1  plan-1  C7   0.020
 IX1  plan-1  O12  0.020
 IX1  plan-1  N13  0.020
 IX1  plan-1  C14  0.020
 IX1  plan-1  C15  0.020
 IX1  plan-1  C16  0.020
 IX1  plan-1  C9   0.020
 IX1  plan-2  C1   0.020
 IX1  plan-2  C2   0.020
 IX1  plan-2  C3   0.020
 IX1  plan-2  C4   0.020
 IX1  plan-2  C5   0.020
 IX1  plan-2  C6   0.020
 IX1  plan-2  C7   0.020
 IX1  plan-2  C8   0.020
 IX1  plan-2  H1   0.020
 IX1  plan-2  H3   0.020
 IX1  plan-2  H5   0.020
 IX1  plan-2  H6   0.020
 IX1  plan-3  C32  0.020
 IX1  plan-3  C33  0.020
 IX1  plan-3  C34  0.020
 IX1  plan-3  C35  0.020
 IX1  plan-3  C36  0.020
 IX1  plan-3  C37  0.020
 IX1  plan-3  C38  0.020
 IX1  plan-3  O14  0.020
 IX1  plan-3  O3   0.020
 IX1  plan-3  H33  0.020
 IX1  plan-3  H34  0.020
 IX1  plan-3  H35  0.020
 IX1  plan-4  C14  0.020
 IX1  plan-4  C16  0.020
 IX1  plan-4  O1   0.020
 IX1  plan-4  O2   0.020
 IX1  plan-4  HO1  0.020
 IX1  plan-5  C4   0.020
 IX1  plan-5  C8   0.020
 IX1  plan-5  C40  0.020
 IX1  plan-5  C41  0.020
 IX1  plan-5  H8   0.020
 IX1  plan-5  H41  0.020
 IX1  plan-6  C37  0.020
 IX1  plan-6  C38  0.020
 IX1  plan-6  O11  0.020
 IX1  plan-6  O13  0.020

