# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr  5 12:16:21 2020
#   Inital geometry file: a 124 line input string
#   Ligand name: 5-[(2R)-3-benzoyl-2-(4-bromothiophen-2-yl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-2-chlorobenzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cc(ccc1Cl)N2[C@@H](c3scc(Br)c3)C(=C(O)C2=O)C(=O)c4ccccc4
#
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
 11Y  11Y  '5-[(2R)-3-benzoyl-2-(4-bromothiophen-2-yl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-2-chlorobenzoic acid'  ligand  43  31  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_11Y
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
 11Y  OAA  O   O      0  -0.578  -6.1225  -0.7993  -0.8186
 11Y  CAS  C   C      0   0.375  -4.9191  -0.9087  -1.0942
 11Y  OAD  O   OC    -1  -0.589  -4.4031  -1.3759  -2.1241
 11Y  CBC  C   C      0   0.024  -3.9372  -0.3636  -0.0582
 11Y  CAQ  C   C1     0  -0.328  -2.8807   0.4257  -0.5046
 11Y  CAY  C   C      0  -0.104  -4.0269  -0.6002   1.3102
 11Y  CLA  CL  CL     0  -0.126  -5.2566  -1.6366   1.9609
 11Y  CAM  C   C1     0  -0.203  -3.1072  -0.0676   2.2035
 11Y  CAN  C   C1     0  -0.313  -2.0977   0.7589   1.7438
 11Y  CBB  C   C      0   0.380  -1.9884   1.0098   0.3820
 11Y  NBE  N   NR5    0  -0.605  -0.9533   1.8361  -0.1000
 11Y  CBD  C   CR15   0  -0.216   0.4415   1.6328   0.2667
 11Y  CBA  C   CR5    0  -0.102   0.9210   0.2613  -0.0863
 11Y  SAR  S   S2     0   0.260   0.8993  -0.2838  -1.7197
 11Y  CAO  C   CR15   0  -0.464   1.6040  -1.7846  -1.2918
 11Y  CAX  C   CR5    0  -0.009   1.8436  -1.8398   0.0442
 11Y  BRA  BR  BR     0  -0.025   2.6287  -3.3120   0.8927
 11Y  CAP  C   CR15   0  -0.184   1.4514  -0.6698   0.7477
 11Y  CAV  C   CR5    0   0.479  -1.1256   2.9006  -0.9142
 11Y  OAC  O   O      0  -0.447  -2.1548   3.3576  -1.3657
 11Y  CAU  C   CR5    0   0.240   0.2384   3.4417  -1.1754
 11Y  OAE  O   OH1    0  -0.559   0.4089   4.4724  -1.9661
 11Y  CAW  C   CR5    0  -0.132   1.1523   2.7254  -0.4968
 11Y  CAT  C   C      0   0.374   2.6062   2.8656  -0.5694
 11Y  OAB  O   O      0  -0.383   3.1375   3.5370  -1.4329
 11Y  CAZ  C   C      0  -0.042   3.4144   2.1017   0.4198
 11Y  CAK  C   C1     0  -0.269   4.4352   1.2708  -0.0335
 11Y  CAI  C   C1     0  -0.237   5.1741   0.5255   0.8717
 11Y  CAH  C   C1     0  -0.246   4.9210   0.6329   2.2335
 11Y  CAJ  C   C1     0  -0.242   3.9269   1.4882   2.6902
 11Y  CAL  C   C1     0  -0.283   3.1654   2.2123   1.7850
 11Y  H2   H   H      0   0.268  -2.7594   0.5786  -1.5688
 11Y  H3   H   H      0   0.281  -3.1848  -0.2843   3.2602
 11Y  H4   H   H      0   0.278  -1.4069   1.2002   2.4499
 11Y  H5   H   HCR5   0   0.313   0.5588   1.7642   1.3462
 11Y  H6   H   HCR5   0   0.318   1.7985  -2.5351  -2.0421
 11Y  H7   H   HCR5   0   0.286   1.5816  -0.5217   1.8102
 11Y  H8   H   HOH1   0   0.490  -0.4502   4.7898  -2.2865
 11Y  H9   H   H      0   0.262   4.6326   1.1832  -1.0944
 11Y  H10  H   H      0   0.262   5.9499  -0.1388   0.5144
 11Y  H11  H   H      0   0.263   5.5021   0.0528   2.9383
 11Y  H12  H   H      0   0.264   3.7390   1.5881   3.7511
 11Y  H13  H   H      0   0.272   2.3938   2.8792   2.1512

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
 11Y  CAH  CAJ  aromatic  1.389  0.020  1.389
 11Y  CAH  CAI  aromatic  1.389  0.020  1.389
 11Y  CAJ  CAL  aromatic  1.387  0.020  1.387
 11Y  CAI  CAK  aromatic  1.386  0.020  1.386
 11Y  CAL  CAZ  aromatic  1.392  0.020  1.392
 11Y  CAO  SAR  aromatic  1.712  0.020  1.712
 11Y  CAO  CAX  aromatic  1.358  0.020  1.358
 11Y  SAR  CBA  aromatic  1.722  0.020  1.722
 11Y  CAK  CAZ  aromatic  1.392  0.020  1.392
 11Y  CAZ  CAT  single    1.488  0.020  1.488
 11Y  BRA  CAX  single    1.872  0.020  1.872
 11Y  CAX  CAP  aromatic  1.420  0.020  1.420
 11Y  OAE  CAU  single    1.310  0.020  1.310
 11Y  CAT  OAB  double    1.216  0.020  1.216
 11Y  CAT  CAW  single    1.462  0.020  1.462
 11Y  CBA  CAP  aromatic  1.358  0.020  1.358
 11Y  CBA  CBD  single    1.495  0.020  1.495
 11Y  CAW  CAU  double    1.345  0.020  1.345
 11Y  CAW  CBD  single    1.511  0.020  1.511
 11Y  CAU  CAV  single    1.491  0.020  1.491
 11Y  CAV  OAC  double    1.213  0.020  1.213
 11Y  CAV  NBE  single    1.351  0.020  1.351
 11Y  CBD  NBE  single    1.456  0.020  1.456
 11Y  OAA  CAS  deloc     1.239  0.020  1.239
 11Y  NBE  CBB  single    1.410  0.020  1.410
 11Y  CAQ  CBB  aromatic  1.387  0.020  1.387
 11Y  CAQ  CBC  aromatic  1.392  0.020  1.392
 11Y  CAS  CBC  single    1.528  0.020  1.528
 11Y  CAS  OAD  deloc     1.243  0.020  1.243
 11Y  CBB  CAN  aromatic  1.389  0.020  1.389
 11Y  CBC  CAY  aromatic  1.392  0.020  1.392
 11Y  CAN  CAM  aromatic  1.383  0.020  1.383
 11Y  CAY  CAM  aromatic  1.388  0.020  1.388
 11Y  CAY  CLA  single    1.735  0.020  1.735
 11Y  CAQ  H2   single    0.930  0.020  1.080
 11Y  CAM  H3   single    0.930  0.020  1.080
 11Y  CAN  H4   single    0.930  0.020  1.080
 11Y  CBD  H5   single    0.970  0.020  1.090
 11Y  CAO  H6   single    0.930  0.020  1.080
 11Y  CAP  H7   single    0.930  0.020  1.080
 11Y  OAE  H8   single    0.850  0.020  0.980
 11Y  CAK  H9   single    0.930  0.020  1.080
 11Y  CAI  H10  single    0.930  0.020  1.080
 11Y  CAH  H11  single    0.930  0.020  1.080
 11Y  CAJ  H12  single    0.930  0.020  1.080
 11Y  CAL  H13  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
 11Y  CBC  CAS  OAD  115.41  3.000
 11Y  OAD  CAS  OAA  128.34  3.000
 11Y  CBC  CAS  OAA  116.22  3.000
 11Y  CAY  CBC  CAQ  117.42  3.000
 11Y  CAY  CBC  CAS  124.38  3.000
 11Y  CAQ  CBC  CAS  118.20  3.000
 11Y  H2   CAQ  CBB  119.81  3.000
 11Y  H2   CAQ  CBC  118.72  3.000
 11Y  CBB  CAQ  CBC  121.47  3.000
 11Y  CAM  CAY  CLA  117.22  3.000
 11Y  CLA  CAY  CBC  121.07  3.000
 11Y  CAM  CAY  CBC  121.66  3.000
 11Y  H3   CAM  CAN  119.79  3.000
 11Y  H3   CAM  CAY  120.28  3.000
 11Y  CAN  CAM  CAY  119.92  3.000
 11Y  H4   CAN  CBB  121.06  3.000
 11Y  H4   CAN  CAM  119.53  3.000
 11Y  CBB  CAN  CAM  119.42  3.000
 11Y  NBE  CBB  CAN  119.93  3.000
 11Y  CAN  CBB  CAQ  120.00  3.000
 11Y  NBE  CBB  CAQ  120.05  3.000
 11Y  CAV  NBE  CBD  112.57  3.000
 11Y  CBD  NBE  CBB  122.37  3.000
 11Y  CAV  NBE  CBB  125.05  3.000
 11Y  H5   CBD  CAW  111.19  3.000
 11Y  H5   CBD  CBA  107.99  3.000
 11Y  CAW  CBD  CBA  113.16  3.000
 11Y  H5   CBD  NBE  109.53  3.000
 11Y  CAW  CBD  NBE  102.85  3.000
 11Y  CBA  CBD  NBE  112.07  3.000
 11Y  CAP  CBA  SAR  111.74  3.000
 11Y  CAP  CBA  CBD  127.53  3.000
 11Y  SAR  CBA  CBD  120.68  3.000
 11Y  CAO  SAR  CBA   92.02  3.000
 11Y  H6   CAO  CAX  128.60  3.000
 11Y  H6   CAO  SAR  120.67  3.000
 11Y  CAX  CAO  SAR  110.73  3.000
 11Y  CAP  CAX  BRA  122.63  3.000
 11Y  CAP  CAX  CAO  113.88  3.000
 11Y  BRA  CAX  CAO  123.49  3.000
 11Y  H7   CAP  CAX  124.51  3.000
 11Y  H7   CAP  CBA  123.85  3.000
 11Y  CAX  CAP  CBA  111.62  3.000
 11Y  CAU  CAV  OAC  125.06  3.000
 11Y  OAC  CAV  NBE  128.99  3.000
 11Y  CAU  CAV  NBE  105.95  3.000
 11Y  CAW  CAU  OAE  129.43  3.000
 11Y  CAW  CAU  CAV  109.88  3.000
 11Y  OAE  CAU  CAV  120.69  3.000
 11Y  H8   OAE  CAU  109.96  3.000
 11Y  CAT  CAW  CAU  126.83  3.000
 11Y  CAU  CAW  CBD  108.69  3.000
 11Y  CAT  CAW  CBD  124.21  3.000
 11Y  CAZ  CAT  OAB  121.21  3.000
 11Y  OAB  CAT  CAW  121.50  3.000
 11Y  CAZ  CAT  CAW  117.23  3.000
 11Y  CAL  CAZ  CAK  119.86  3.000
 11Y  CAK  CAZ  CAT  119.22  3.000
 11Y  CAL  CAZ  CAT  120.92  3.000
 11Y  H9   CAK  CAI  119.95  3.000
 11Y  H9   CAK  CAZ  120.07  3.000
 11Y  CAI  CAK  CAZ  119.95  3.000
 11Y  H10  CAI  CAH  120.11  3.000
 11Y  H10  CAI  CAK  119.79  3.000
 11Y  CAH  CAI  CAK  120.10  3.000
 11Y  H11  CAH  CAJ  120.02  3.000
 11Y  H11  CAH  CAI  119.95  3.000
 11Y  CAJ  CAH  CAI  120.03  3.000
 11Y  H12  CAJ  CAL  119.76  3.000
 11Y  H12  CAJ  CAH  120.24  3.000
 11Y  CAL  CAJ  CAH  120.00  3.000
 11Y  H13  CAL  CAJ  119.45  3.000
 11Y  H13  CAL  CAZ  120.51  3.000
 11Y  CAJ  CAL  CAZ  120.02  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
 11Y  CONST_01  CAN  CBB  CAQ  CBC     0.00   0.0  0
 11Y  CONST_02  CAN  CAM  CAY  CBC     0.00   0.0  0
 11Y  CONST_03  CAM  CAN  CBB  CAQ     0.00   0.0  0
 11Y  CONST_04  CAM  CAY  CBC  CAQ     0.00   0.0  0
 11Y  CONST_05  CBB  CAQ  CBC  CAY     0.00   0.0  0
 11Y  CONST_06  CBB  CAN  CAM  CAY     0.00   0.0  0
 11Y  CONST_07  CAX  CAO  SAR  CBA     0.00   0.0  0
 11Y  CONST_08  CAO  CAX  CAP  CBA     0.00   0.0  0
 11Y  CONST_09  CAP  CAX  CAO  SAR     0.00   0.0  0
 11Y  CONST_10  CAX  CAP  CBA  SAR     0.00   0.0  0
 11Y  CONST_11  CAP  CBA  SAR  CAO     0.00   0.0  0
 11Y  CONST_12  CAH  CAJ  CAL  CAZ     0.00   0.0  0
 11Y  CONST_13  CAH  CAI  CAK  CAZ     0.00   0.0  0
 11Y  CONST_14  CAJ  CAH  CAI  CAK     0.00   0.0  0
 11Y  CONST_15  CAJ  CAL  CAZ  CAK     0.00   0.0  0
 11Y  CONST_16  CAL  CAJ  CAH  CAI     0.00   0.0  0
 11Y  CONST_17  CAL  CAZ  CAK  CAI     0.00   0.0  0
 11Y  CONST_18  NBE  CBB  CAQ  CBC   180.00   0.0  0
 11Y  CONST_19  NBE  CBB  CAN  CAM   180.00   0.0  0
 11Y  CONST_20  CAO  SAR  CBA  CBD   180.00   0.0  0
 11Y  CONST_21  CAX  CAP  CBA  CBD   180.00   0.0  0
 11Y  CONST_22  CAU  CAV  NBE  CBB   180.00   0.0  0
 11Y  CONST_23  CAU  CAV  NBE  CBD     0.00   0.0  0
 11Y  CONST_24  CBB  CAQ  CBC  CAS   180.00   0.0  0
 11Y  CONST_25  CAM  CAY  CBC  CAS   180.00   0.0  0
 11Y  CONST_26  CLA  CAY  CBC  CAQ   180.00   0.0  0
 11Y  CONST_27  CAN  CAM  CAY  CLA   180.00   0.0  0
 11Y  CONST_28  BRA  CAX  CAP  CBA   180.00   0.0  0
 11Y  CONST_29  BRA  CAX  CAO  SAR   180.00   0.0  0
 11Y  CONST_30  CAJ  CAL  CAZ  CAT   180.00   0.0  0
 11Y  CONST_31  CAI  CAK  CAZ  CAT   180.00   0.0  0
 11Y  CONST_32  OAC  CAV  NBE  CBB     0.00   0.0  0
 11Y  CONST_33  OAC  CAV  NBE  CBD   180.00   0.0  0
 11Y  CONST_34  H3   CAM  CAY  CBC   180.00   0.0  0
 11Y  CONST_35  H4   CAN  CBB  CAQ   180.00   0.0  0
 11Y  CONST_36  H2   CAQ  CBC  CAY   180.00   0.0  0
 11Y  CONST_37  H7   CAP  CBA  CBD     0.00   0.0  0
 11Y  CONST_38  H6   CAO  SAR  CBA   180.00   0.0  0
 11Y  CONST_39  H12  CAJ  CAL  CAZ   180.00   0.0  0
 11Y  CONST_40  H10  CAI  CAK  CAZ   180.00   0.0  0
 11Y  CONST_41  H11  CAH  CAI  CAK   180.00   0.0  0
 11Y  CONST_42  H13  CAL  CAZ  CAK   180.00   0.0  0
 11Y  CONST_43  H9   CAK  CAI  CAH   180.00   0.0  0
 11Y  Var_01    CAV  NBE  CBB  CAQ    53.34  30.0  3
 11Y  Var_02    CAW  CAU  CAV  NBE    -1.69  30.0  1
 11Y  Var_03    CAV  CAU  CAW  CBD     0.44  30.0  1
 11Y  Var_04    CAZ  CAT  CAW  CBD   -15.40  30.0  2
 11Y  Var_05    CAL  CAZ  CAT  CAW   -53.47  30.0  2
 11Y  Var_06    CAQ  CBC  CAS  OAA  -134.00  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 11Y  chir_01  CBD  CBA  CAW  NBE  negativ

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
 11Y  plan-1  CBD  0.020
 11Y  plan-1  CBA  0.020
 11Y  plan-1  SAR  0.020
 11Y  plan-1  CAO  0.020
 11Y  plan-1  CAX  0.020
 11Y  plan-1  BRA  0.020
 11Y  plan-1  CAP  0.020
 11Y  plan-1  H6   0.020
 11Y  plan-1  H7   0.020
 11Y  plan-2  CAS  0.020
 11Y  plan-2  CBC  0.020
 11Y  plan-2  CAQ  0.020
 11Y  plan-2  CAY  0.020
 11Y  plan-2  CLA  0.020
 11Y  plan-2  CAM  0.020
 11Y  plan-2  CAN  0.020
 11Y  plan-2  CBB  0.020
 11Y  plan-2  NBE  0.020
 11Y  plan-2  H2   0.020
 11Y  plan-2  H3   0.020
 11Y  plan-2  H4   0.020
 11Y  plan-3  CAT  0.020
 11Y  plan-3  CAZ  0.020
 11Y  plan-3  CAK  0.020
 11Y  plan-3  CAI  0.020
 11Y  plan-3  CAH  0.020
 11Y  plan-3  CAJ  0.020
 11Y  plan-3  CAL  0.020
 11Y  plan-3  H9   0.020
 11Y  plan-3  H10  0.020
 11Y  plan-3  H11  0.020
 11Y  plan-3  H12  0.020
 11Y  plan-3  H13  0.020
 11Y  plan-4  CBB  0.020
 11Y  plan-4  NBE  0.020
 11Y  plan-4  CBD  0.020
 11Y  plan-4  CAV  0.020
 11Y  plan-4  OAC  0.020
 11Y  plan-4  CAU  0.020
 11Y  plan-5  OAA  0.020
 11Y  plan-5  CAS  0.020
 11Y  plan-5  OAD  0.020
 11Y  plan-5  CBC  0.020
 11Y  plan-6  CAW  0.020
 11Y  plan-6  CAT  0.020
 11Y  plan-6  OAB  0.020
 11Y  plan-6  CAZ  0.020

