# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 18:09:56 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: (2Z,3E)-2-(7-bromo-2-oxo-1H-indol-3-ylidene)-3-hydroxyimino-1H-indole-5-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O\N=C1\C(Nc2ccc(cc12)C(O)=O)=C3\C(=O)Nc4c(Br)cccc34
#
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
 IRB  IRB  '(2Z,3E)-2-(7-bromo-2-oxo-1H-indol-3-ylidene)-3-hydroxyimino-1H-indole-5-carboxylic acid'  ligand  34  25  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_IRB
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
 IRB  OAA   O   O      0  -0.593  -7.0187   1.5364   0.0645
 IRB  OAC   O   OH1    0  -0.504  -2.3678   2.7953   0.0120
 IRB  OAD   O   OC    -1  -0.594  -7.8168  -0.5441   0.0215
 IRB  BRAE  BR  BR     0  -0.037   5.6711  -0.5205  -0.1108
 IRB  CAF   C   CR16   0  -0.253   2.9075   2.5687  -0.0503
 IRB  CAG   C   CR16   0  -0.273   4.1013   1.8631  -0.0695
 IRB  CAH   C   CR16   0  -0.288  -5.2459  -1.6250  -0.0056
 IRB  CAI   C   CR16   0  -0.417   1.6767   1.9203  -0.0450
 IRB  CAJ   C   CR16   0  -0.310  -3.9659  -2.1649  -0.0262
 IRB  CAK   C   CR16   0  -0.365  -4.3875   0.6244   0.0113
 IRB  NAL   N   N      0  -0.109  -1.3671   1.9073  -0.0097
 IRB  NAM   N   NR15   0  -0.767   2.5976  -1.5291  -0.0909
 IRB  NAN   N   NR15   0  -0.799  -1.5552  -1.5524  -0.0477
 IRB  CAO   C   C      0   0.406  -6.8971   0.2965   0.0349
 IRB  CAP   C   CR6    0  -0.105  -5.4758  -0.2484   0.0131
 IRB  CAQ   C   CR6    0  -0.188   4.0696   0.4736  -0.0842
 IRB  CAR   C   CR5    0   0.541   1.2552  -1.7816  -0.0818
 IRB  CAS   C   CR5    0   0.427  -0.7963  -0.4315  -0.0435
 IRB  CAT   C   CR5    0   0.077  -1.7627   0.6941  -0.0190
 IRB  CAU   C   CR5    0  -0.164   0.5798  -0.4753  -0.0603
 IRB  CAV   C   CR56   0   0.361  -2.9070  -1.2779  -0.0288
 IRB  CAW   C   CR56   0   0.004   1.6300   0.5309  -0.0590
 IRB  CAX   C   CR56   0   0.052  -3.1006   0.1063  -0.0102
 IRB  CAY   C   CR56   0   0.456   2.8525  -0.1782  -0.0787
 IRB  HOAC  H   HOH1   0   0.495  -1.9359   3.6585   0.0165
 IRB  HAF   H   HCR6   0   0.261   2.9375   3.6499  -0.0392
 IRB  HAG   H   HCR6   0   0.277   5.0454   2.3911  -0.0727
 IRB  HAH   H   HCR6   0   0.255  -6.0951  -2.2948  -0.0042
 IRB  HAI   H   HCR6   0   0.282   0.7696   2.4997  -0.0297
 IRB  HAJ   H   HCR6   0   0.268  -3.8071  -3.2352  -0.0401
 IRB  HAK   H   HCR6   0   0.253  -4.5654   1.6885   0.0266
 IRB  HNAM  H   HNR5   0   0.412   3.2940  -2.2582  -0.1101
 IRB  HNAN  H   HNR5   0   0.430  -1.1369  -2.4749  -0.0670
 IRB  OAB   O   O      0  -0.491   0.7640  -2.9069  -0.0905

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
 IRB  OAA   CAO   deloc     1.246  0.020  1.246
 IRB  OAB   CAR   double    1.228  0.020  1.228
 IRB  OAC   NAL   single    1.338  0.020  1.338
 IRB  OAD   CAO   deloc     1.246  0.020  1.246
 IRB  BRAE  CAQ   single    1.885  0.020  1.885
 IRB  CAF   CAG   aromatic  1.387  0.020  1.387
 IRB  CAF   CAI   aromatic  1.391  0.020  1.391
 IRB  CAG   CAQ   aromatic  1.390  0.020  1.390
 IRB  CAH   CAJ   aromatic  1.389  0.020  1.389
 IRB  CAH   CAP   aromatic  1.396  0.020  1.396
 IRB  CAI   CAW   aromatic  1.390  0.020  1.390
 IRB  CAJ   CAV   aromatic  1.381  0.020  1.381
 IRB  CAK   CAP   aromatic  1.395  0.020  1.395
 IRB  CAK   CAX   aromatic  1.387  0.020  1.387
 IRB  NAL   CAT   double    1.276  0.020  1.276
 IRB  NAM   CAR   single    1.366  0.020  1.366
 IRB  NAM   CAY   single    1.375  0.020  1.375
 IRB  NAN   CAS   single    1.354  0.020  1.354
 IRB  NAN   CAV   single    1.379  0.020  1.379
 IRB  CAO   CAP   single    1.522  0.020  1.522
 IRB  CAQ   CAY   aromatic  1.381  0.020  1.381
 IRB  CAR   CAU   single    1.471  0.020  1.471
 IRB  CAS   CAT   single    1.484  0.020  1.484
 IRB  CAS   CAU   double    1.377  0.020  1.377
 IRB  CAT   CAX   single    1.461  0.020  1.461
 IRB  CAU   CAW   single    1.454  0.020  1.454
 IRB  CAV   CAX   aromatic  1.398  0.020  1.398
 IRB  CAW   CAY   aromatic  1.413  0.020  1.413
 IRB  OAC   HOAC  single    0.850  0.020  0.980
 IRB  CAF   HAF   single    0.930  0.020  1.080
 IRB  CAG   HAG   single    0.930  0.020  1.080
 IRB  CAH   HAH   single    0.930  0.020  1.080
 IRB  CAI   HAI   single    0.930  0.020  1.080
 IRB  CAJ   HAJ   single    0.930  0.020  1.080
 IRB  CAK   HAK   single    0.930  0.020  1.080
 IRB  NAM   HNAM  single    0.860  0.020  1.020
 IRB  NAN   HNAN  single    0.860  0.020  1.020

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
 IRB  HOAC  OAC  NAL   105.01  3.000
 IRB  HAF   CAF  CAI   119.36  3.000
 IRB  HAF   CAF  CAG   119.00  3.000
 IRB  CAI   CAF  CAG   121.63  3.000
 IRB  HAG   CAG  CAQ   120.52  3.000
 IRB  HAG   CAG  CAF   120.20  3.000
 IRB  CAQ   CAG  CAF   119.28  3.000
 IRB  HAH   CAH  CAP   118.78  3.000
 IRB  HAH   CAH  CAJ   118.86  3.000
 IRB  CAP   CAH  CAJ   122.36  3.000
 IRB  HAI   CAI  CAW   120.65  3.000
 IRB  HAI   CAI  CAF   119.65  3.000
 IRB  CAW   CAI  CAF   119.70  3.000
 IRB  HAJ   CAJ  CAV   121.51  3.000
 IRB  HAJ   CAJ  CAH   121.32  3.000
 IRB  CAV   CAJ  CAH   117.18  3.000
 IRB  HAK   CAK  CAX   121.42  3.000
 IRB  HAK   CAK  CAP   119.24  3.000
 IRB  CAX   CAK  CAP   119.34  3.000
 IRB  CAT   NAL  OAC   113.52  3.000
 IRB  HNAM  NAM  CAY   125.63  3.000
 IRB  HNAM  NAM  CAR   123.03  3.000
 IRB  CAY   NAM  CAR   111.34  3.000
 IRB  HNAN  NAN  CAV   125.87  3.000
 IRB  HNAN  NAN  CAS   121.51  3.000
 IRB  CAV   NAN  CAS   112.62  3.000
 IRB  CAP   CAO  OAD   116.58  3.000
 IRB  CAP   CAO  OAA   116.59  3.000
 IRB  OAD   CAO  OAA   126.83  3.000
 IRB  CAO   CAP  CAK   120.29  3.000
 IRB  CAO   CAP  CAH   120.46  3.000
 IRB  CAK   CAP  CAH   119.25  3.000
 IRB  CAY   CAQ  CAG   119.48  3.000
 IRB  CAY   CAQ  BRAE  120.00  3.000
 IRB  CAG   CAQ  BRAE  120.52  3.000
 IRB  CAU   CAR  NAM   106.69  3.000
 IRB  CAU   CAR  OAB   129.08  3.000
 IRB  NAM   CAR  OAB   124.23  3.000
 IRB  CAU   CAS  CAT   132.48  3.000
 IRB  CAU   CAS  NAN   122.27  3.000
 IRB  CAT   CAS  NAN   105.25  3.000
 IRB  CAX   CAT  CAS   106.94  3.000
 IRB  CAX   CAT  NAL   131.77  3.000
 IRB  CAS   CAT  NAL   121.29  3.000
 IRB  CAW   CAU  CAS   134.39  3.000
 IRB  CAW   CAU  CAR   106.44  3.000
 IRB  CAS   CAU  CAR   119.17  3.000
 IRB  CAX   CAV  NAN   109.45  3.000
 IRB  CAX   CAV  CAJ   121.98  3.000
 IRB  NAN   CAV  CAJ   128.57  3.000
 IRB  CAY   CAW  CAU   106.11  3.000
 IRB  CAY   CAW  CAI   118.19  3.000
 IRB  CAU   CAW  CAI   135.70  3.000
 IRB  CAV   CAX  CAT   105.75  3.000
 IRB  CAV   CAX  CAK   119.90  3.000
 IRB  CAT   CAX  CAK   134.36  3.000
 IRB  CAW   CAY  CAQ   121.71  3.000
 IRB  CAW   CAY  NAM   109.43  3.000
 IRB  CAQ   CAY  NAM   128.85  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
 IRB  CONST_01  CAY   CAQ  CAG  CAF     0.00   0.0  0
 IRB  CONST_02  CAY   CAW  CAI  CAF     0.00   0.0  0
 IRB  CONST_03  CAW   CAI  CAF  CAG     0.00   0.0  0
 IRB  CONST_04  CAW   CAY  CAQ  CAG     0.00   0.0  0
 IRB  CONST_05  CAX   CAV  CAJ  CAH     0.00   0.0  0
 IRB  CONST_06  CAX   CAK  CAP  CAH     0.00   0.0  0
 IRB  CONST_07  CAQ   CAG  CAF  CAI     0.00   0.0  0
 IRB  CONST_08  CAQ   CAY  CAW  CAI     0.00   0.0  0
 IRB  CONST_09  CAK   CAP  CAH  CAJ     0.00   0.0  0
 IRB  CONST_10  CAK   CAX  CAV  CAJ     0.00   0.0  0
 IRB  CONST_11  CAV   CAJ  CAH  CAP     0.00   0.0  0
 IRB  CONST_12  CAV   CAX  CAK  CAP     0.00   0.0  0
 IRB  CONST_13  CAY   NAM  CAR  CAU     0.00   0.0  0
 IRB  CONST_14  CAF   CAG  CAQ  BRAE  180.00   0.0  0
 IRB  CONST_15  NAM   CAY  CAQ  BRAE    0.00   0.0  0
 IRB  CONST_16  CAW   CAY  CAQ  BRAE  180.00   0.0  0
 IRB  CONST_17  CAO   CAP  CAH  CAJ   180.00   0.0  0
 IRB  CONST_18  CAX   CAK  CAP  CAO   180.00   0.0  0
 IRB  CONST_19  CAY   NAM  CAR  OAB   180.00   0.0  0
 IRB  CONST_20  HAI   CAI  CAF  CAG   180.00   0.0  0
 IRB  CONST_21  HAK   CAK  CAP  CAH   180.00   0.0  0
 IRB  CONST_22  HAG   CAG  CAF  CAI   180.00   0.0  0
 IRB  CONST_23  HAH   CAH  CAP  CAK   180.00   0.0  0
 IRB  CONST_24  HAJ   CAJ  CAV  NAN     0.00   0.0  0
 IRB  CONST_25  HAF   CAF  CAG  CAQ   180.00   0.0  0
 IRB  CONST_26  HNAM  NAM  CAR  CAU   180.00   0.0  0
 IRB  Var_01    CAR   CAU  CAS  NAN    -0.08  30.0  2
 IRB  Var_02    CAH   CAP  CAO  OAA   179.30  30.0  2
 IRB  Var_03    CAS   CAT  NAL  OAC   179.97  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
 IRB  plan-1  BRAE  0.020
 IRB  plan-1  CAF   0.020
 IRB  plan-1  CAG   0.020
 IRB  plan-1  CAI   0.020
 IRB  plan-1  NAM   0.020
 IRB  plan-1  CAQ   0.020
 IRB  plan-1  CAR   0.020
 IRB  plan-1  CAS   0.020
 IRB  plan-1  CAU   0.020
 IRB  plan-1  CAW   0.020
 IRB  plan-1  CAY   0.020
 IRB  plan-1  HAF   0.020
 IRB  plan-1  HAG   0.020
 IRB  plan-1  HAI   0.020
 IRB  plan-1  HNAM  0.020
 IRB  plan-1  OAB   0.020
 IRB  plan-2  CAH   0.020
 IRB  plan-2  CAJ   0.020
 IRB  plan-2  CAK   0.020
 IRB  plan-2  NAL   0.020
 IRB  plan-2  NAN   0.020
 IRB  plan-2  CAO   0.020
 IRB  plan-2  CAP   0.020
 IRB  plan-2  CAS   0.020
 IRB  plan-2  CAT   0.020
 IRB  plan-2  CAU   0.020
 IRB  plan-2  CAV   0.020
 IRB  plan-2  CAX   0.020
 IRB  plan-2  HAH   0.020
 IRB  plan-2  HAJ   0.020
 IRB  plan-2  HAK   0.020
 IRB  plan-2  HNAN  0.020
 IRB  plan-3  OAA   0.020
 IRB  plan-3  OAD   0.020
 IRB  plan-3  CAO   0.020
 IRB  plan-3  CAP   0.020

