# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 18:52:51 2021
#   Inital geometry file: a 117 line input string
#   Ligand name: ethyl 6-bromanyl-2-[(dimethylamino)methyl]-5-oxidanyl-1-phenyl-indole-3-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1c(CN(C)C)n(c2ccccc2)c3cc(Br)c(O)cc13
#
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
 MLH  MLH  'ethyl 6-bromanyl-2-[(dimethylamino)methyl]-5-oxidanyl-1-phenyl-indole-3-carboxylate'  ligand  47  26  .  2022-03-22  2022-07-25
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_MLH
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
 MLH  CAP  C   CH3   0  -0.689  11.7244  -1.0230  -21.2007
 MLH  CAO  C   CH2   0  -0.194  11.7955   0.2394  -20.3697
 MLH  OAM  O   O2    0  -0.467  13.0822   0.4170  -19.7629
 MLH  CAL  C   C     0   0.516  14.0580   0.9629  -20.4787
 MLH  OAN  O   O     0  -0.464  13.9142   1.3257  -21.6267
 MLH  CAI  C   CR5   0  -0.268  15.3173   1.0943  -19.7575
 MLH  CAH  C   CR5   0   0.421  15.6332   0.7410  -18.4539
 MLH  CAR  C   CH2   0  -0.388  14.8391   0.1221  -17.3468
 MLH  NAY  N   NT    0  -0.394  14.4741   1.1142  -16.3505
 MLH  CAZ  C   CH3   0  -0.516  14.1525   0.4956  -15.0844
 MLH  CBA  C   CH3   0  -0.512  13.4239   2.0014  -16.7997
 MLH  CAF  C   CR56  0   0.177  16.5031   1.6597  -20.3431
 MLH  CAA  C   CR16  0  -0.484  16.8232   2.1954  -21.5901
 MLH  CAB  C   CR6   0   0.422  18.1052   2.6694  -21.8278
 MLH  OAJ  O   OH1   0  -0.625  18.3494   3.1709  -23.0533
 MLH  CAC  C   CR6   0  -0.264  19.0694   2.6048  -20.8011
 MLH  BR1  BR  BR    0  -0.036  20.8180   3.2473  -21.1232
 MLH  CAD  C   CR16  0  -0.263  18.7793   2.0832  -19.5543
 MLH  CAE  C   CR56  0   0.307  17.4921   1.6166  -19.3493
 MLH  NAG  N   NR5   0  -0.665  16.9367   1.0587  -18.2188
 MLH  CAQ  C   CR6   0   0.230  17.6699   0.7935  -17.0303
 MLH  CAT  C   CR16  0  -0.218  17.5529   1.6389  -15.9360
 MLH  CAU  C   CR16  0  -0.263  18.2942   1.3771  -14.7930
 MLH  CAV  C   CR16  0  -0.242  19.1501   0.2839  -14.7486
 MLH  CAW  C   CR16  0  -0.260  19.2663  -0.5534  -15.8502
 MLH  CAX  C   CR16  0  -0.254  18.5247  -0.3006  -16.9957
 MLH  H1   H   HCH3  0   0.240  10.7066  -1.1493  -21.5709
 MLH  H2   H   HCH3  0   0.237  12.3894  -0.9835  -22.0627
 MLH  H3   H   HCH3  0   0.234  11.9739  -1.9028  -20.6073
 MLH  H4   H   HCH2  0   0.235  11.5322   1.1168  -20.9615
 MLH  H5   H   HCH2  0   0.245  11.1049   0.1831  -19.5296
 MLH  H6   H   HCH2  0   0.252  13.9760  -0.4170  -17.7495
 MLH  H7   H   HCH2  0   0.267  15.4730  -0.6251  -16.8614
 MLH  H9   H   HCH3  0   0.233  13.9321   1.2660  -14.3445
 MLH  H10  H   HCH3  0   0.196  13.2849  -0.1804  -15.1316
 MLH  H11  H   HCH3  0   0.233  15.0083  -0.0759  -14.7215
 MLH  H12  H   HCH3  0   0.232  13.2588   2.7775  -16.0515
 MLH  H13  H   HCH3  0   0.233  13.7123   2.4973  -17.7265
 MLH  H14  H   HCH3  0   0.194  12.4657   1.4905  -16.9764
 MLH  H15  H   HCR6  0   0.267  16.0913   2.2528  -22.3828
 MLH  H16  H   HOH1  0   0.471  19.2489   3.5079  -23.1399
 MLH  H17  H   HCR6  0   0.291  19.5272   2.0429  -18.7736
 MLH  H18  H   HCR6  0   0.266  16.8791   2.4825  -15.9771
 MLH  H19  H   HCR6  0   0.264  18.2037   2.0309  -13.9358
 MLH  H20  H   HCR6  0   0.263  19.7278   0.0851  -13.8553
 MLH  H21  H   HCR6  0   0.265  19.9320  -1.4055  -15.8197
 MLH  H22  H   HCR6  0   0.273  18.6041  -0.9513  -17.8574

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
 MLH  OAJ  CAB  single    1.347  0.020  1.347
 MLH  CAB  CAA  aromatic  1.387  0.020  1.387
 MLH  CAB  CAC  aromatic  1.410  0.020  1.410
 MLH  OAN  CAL  double    1.213  0.020  1.213
 MLH  CAA  CAF  aromatic  1.395  0.020  1.395
 MLH  CAP  CAO  single    1.513  0.020  1.513
 MLH  BR1  CAC  single    1.891  0.020  1.891
 MLH  CAC  CAD  aromatic  1.382  0.020  1.382
 MLH  CAL  CAI  single    1.457  0.020  1.457
 MLH  CAL  OAM  single    1.328  0.020  1.328
 MLH  CAF  CAI  aromatic  1.438  0.020  1.438
 MLH  CAF  CAE  aromatic  1.403  0.020  1.403
 MLH  CAO  OAM  single    1.434  0.020  1.434
 MLH  CAI  CAH  aromatic  1.387  0.020  1.387
 MLH  CAD  CAE  aromatic  1.384  0.020  1.384
 MLH  CAE  NAG  aromatic  1.378  0.020  1.378
 MLH  CAH  NAG  aromatic  1.362  0.020  1.362
 MLH  CAH  CAR  single    1.497  0.020  1.497
 MLH  NAG  CAQ  single    1.421  0.020  1.421
 MLH  CAX  CAQ  aromatic  1.389  0.020  1.389
 MLH  CAX  CAW  aromatic  1.388  0.020  1.388
 MLH  CAR  NAY  single    1.453  0.020  1.453
 MLH  CAQ  CAT  aromatic  1.388  0.020  1.388
 MLH  CBA  NAY  single    1.446  0.020  1.446
 MLH  NAY  CAZ  single    1.445  0.020  1.445
 MLH  CAW  CAV  aromatic  1.389  0.020  1.389
 MLH  CAT  CAU  aromatic  1.387  0.020  1.387
 MLH  CAV  CAU  aromatic  1.389  0.020  1.389
 MLH  CAP  H1   single    0.970  0.020  1.090
 MLH  CAP  H2   single    0.970  0.020  1.090
 MLH  CAP  H3   single    0.970  0.020  1.090
 MLH  CAO  H4   single    0.970  0.020  1.090
 MLH  CAO  H5   single    0.970  0.020  1.090
 MLH  CAR  H6   single    0.970  0.020  1.090
 MLH  CAR  H7   single    0.970  0.020  1.090
 MLH  CAZ  H9   single    0.970  0.020  1.090
 MLH  CAZ  H10  single    0.970  0.020  1.090
 MLH  CAZ  H11  single    0.970  0.020  1.090
 MLH  CBA  H12  single    0.970  0.020  1.090
 MLH  CBA  H13  single    0.970  0.020  1.090
 MLH  CBA  H14  single    0.970  0.020  1.090
 MLH  CAA  H15  single    0.930  0.020  1.080
 MLH  OAJ  H16  single    0.850  0.020  0.980
 MLH  CAD  H17  single    0.930  0.020  1.080
 MLH  CAT  H18  single    0.930  0.020  1.080
 MLH  CAU  H19  single    0.930  0.020  1.080
 MLH  CAV  H20  single    0.930  0.020  1.080
 MLH  CAW  H21  single    0.930  0.020  1.080
 MLH  CAX  H22  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
 MLH  H3   CAP  H2   108.68  3.000
 MLH  H3   CAP  H1   107.75  3.000
 MLH  H2   CAP  H1   107.78  3.000
 MLH  H3   CAP  CAO  111.33  3.000
 MLH  H2   CAP  CAO  112.07  3.000
 MLH  H1   CAP  CAO  109.08  3.000
 MLH  H5   CAO  H4   107.89  3.000
 MLH  H5   CAO  OAM  104.43  3.000
 MLH  H4   CAO  OAM  110.28  3.000
 MLH  H5   CAO  CAP  110.54  3.000
 MLH  H4   CAO  CAP  111.21  3.000
 MLH  OAM  CAO  CAP  112.20  3.000
 MLH  CAL  OAM  CAO  118.85  3.000
 MLH  CAI  CAL  OAN  122.96  3.000
 MLH  CAI  CAL  OAM  113.92  3.000
 MLH  OAN  CAL  OAM  123.12  3.000
 MLH  CAF  CAI  CAH  107.15  3.000
 MLH  CAH  CAI  CAL  129.72  3.000
 MLH  CAF  CAI  CAL  123.13  3.000
 MLH  NAG  CAH  CAR  118.46  3.000
 MLH  CAR  CAH  CAI  132.83  3.000
 MLH  NAG  CAH  CAI  108.71  3.000
 MLH  H7   CAR  H6   106.50  3.000
 MLH  H7   CAR  NAY  107.93  3.000
 MLH  H6   CAR  NAY  113.00  3.000
 MLH  H7   CAR  CAH  107.66  3.000
 MLH  H6   CAR  CAH  110.48  3.000
 MLH  NAY  CAR  CAH  110.99  3.000
 MLH  CBA  NAY  CAZ  111.91  3.000
 MLH  CAZ  NAY  CAR  111.37  3.000
 MLH  CBA  NAY  CAR  112.85  3.000
 MLH  H11  CAZ  H10  108.11  3.000
 MLH  H11  CAZ  H9   107.63  3.000
 MLH  H10  CAZ  H9   107.67  3.000
 MLH  H11  CAZ  NAY  109.94  3.000
 MLH  H10  CAZ  NAY  113.61  3.000
 MLH  H9   CAZ  NAY  109.69  3.000
 MLH  H14  CBA  H13  107.77  3.000
 MLH  H14  CBA  H12  107.98  3.000
 MLH  H13  CBA  H12  107.43  3.000
 MLH  H14  CBA  NAY  113.42  3.000
 MLH  H13  CBA  NAY  110.55  3.000
 MLH  H12  CBA  NAY  109.48  3.000
 MLH  CAE  CAF  CAA  118.92  3.000
 MLH  CAE  CAF  CAI  106.31  3.000
 MLH  CAA  CAF  CAI  134.77  3.000
 MLH  H15  CAA  CAB  118.83  3.000
 MLH  H15  CAA  CAF  121.40  3.000
 MLH  CAB  CAA  CAF  119.77  3.000
 MLH  CAC  CAB  OAJ  123.76  3.000
 MLH  CAC  CAB  CAA  119.44  3.000
 MLH  OAJ  CAB  CAA  116.79  3.000
 MLH  H16  OAJ  CAB  112.40  3.000
 MLH  CAD  CAC  BR1  118.43  3.000
 MLH  CAD  CAC  CAB  122.04  3.000
 MLH  BR1  CAC  CAB  119.53  3.000
 MLH  H17  CAD  CAE  121.56  3.000
 MLH  H17  CAD  CAC  121.32  3.000
 MLH  CAE  CAD  CAC  117.12  3.000
 MLH  NAG  CAE  CAD  129.26  3.000
 MLH  NAG  CAE  CAF  108.03  3.000
 MLH  CAD  CAE  CAF  122.71  3.000
 MLH  CAQ  NAG  CAE  123.62  3.000
 MLH  CAQ  NAG  CAH  126.48  3.000
 MLH  CAE  NAG  CAH  109.79  3.000
 MLH  CAX  CAQ  CAT  120.81  3.000
 MLH  CAT  CAQ  NAG  120.14  3.000
 MLH  CAX  CAQ  NAG  119.03  3.000
 MLH  H18  CAT  CAU  120.80  3.000
 MLH  H18  CAT  CAQ  119.88  3.000
 MLH  CAU  CAT  CAQ  119.32  3.000
 MLH  H19  CAU  CAV  120.12  3.000
 MLH  H19  CAU  CAT  119.60  3.000
 MLH  CAV  CAU  CAT  120.27  3.000
 MLH  H20  CAV  CAW  119.95  3.000
 MLH  H20  CAV  CAU  120.00  3.000
 MLH  CAW  CAV  CAU  120.05  3.000
 MLH  H21  CAW  CAX  119.71  3.000
 MLH  H21  CAW  CAV  120.28  3.000
 MLH  CAX  CAW  CAV  120.02  3.000
 MLH  H22  CAX  CAW  120.54  3.000
 MLH  H22  CAX  CAQ  119.92  3.000
 MLH  CAW  CAX  CAQ  119.54  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
 MLH  CONST_01  CAB  CAA  CAF  CAI   180.00   0.0  0
 MLH  CONST_02  CAD  CAE  CAF  CAI   180.00   0.0  0
 MLH  CONST_03  NAG  CAE  CAF  CAI     0.00   0.0  0
 MLH  CONST_04  CAE  NAG  CAH  CAI     0.00   0.0  0
 MLH  CONST_05  CAQ  NAG  CAH  CAI   180.00   0.0  0
 MLH  CONST_06  CAA  CAF  CAI  CAH   180.00   0.0  0
 MLH  CONST_07  CAE  CAF  CAI  CAH     0.00   0.0  0
 MLH  CONST_08  CAF  CAE  NAG  CAH     0.00   0.0  0
 MLH  CONST_09  CAD  CAE  NAG  CAH   180.00   0.0  0
 MLH  CONST_12  CAC  CAB  CAA  CAF     0.00   0.0  0
 MLH  CONST_13  NAG  CAH  CAI  CAF     0.00   0.0  0
 MLH  CONST_14  CAC  CAD  CAE  CAF     0.00   0.0  0
 MLH  CONST_15  CAQ  NAG  CAE  CAF   180.00   0.0  0
 MLH  CONST_16  CAD  CAC  CAB  CAA     0.00   0.0  0
 MLH  CONST_17  CAD  CAE  CAF  CAA     0.00   0.0  0
 MLH  CONST_18  NAG  CAE  CAF  CAA   180.00   0.0  0
 MLH  CONST_19  CAE  CAF  CAA  CAB     0.00   0.0  0
 MLH  CONST_20  CAE  CAD  CAC  CAB     0.00   0.0  0
 MLH  CONST_21  NAG  CAE  CAD  CAC   180.00   0.0  0
 MLH  CONST_22  CAQ  NAG  CAE  CAD     0.00   0.0  0
 MLH  CONST_25  CAW  CAX  CAQ  NAG   180.00   0.0  0
 MLH  CONST_26  CAU  CAT  CAQ  NAG   180.00   0.0  0
 MLH  CONST_27  CAV  CAW  CAX  CAQ     0.00   0.0  0
 MLH  CONST_28  CAV  CAU  CAT  CAQ     0.00   0.0  0
 MLH  CONST_29  CAW  CAX  CAQ  CAT     0.00   0.0  0
 MLH  CONST_30  CAW  CAV  CAU  CAT     0.00   0.0  0
 MLH  CONST_31  CAX  CAQ  CAT  CAU     0.00   0.0  0
 MLH  CONST_32  CAX  CAW  CAV  CAU     0.00   0.0  0
 MLH  CONST_33  CAA  CAF  CAI  CAL     0.00   0.0  0
 MLH  CONST_34  CAE  CAF  CAI  CAL   180.00   0.0  0
 MLH  CONST_35  NAG  CAH  CAI  CAL   180.00   0.0  0
 MLH  CONST_36  CAF  CAI  CAH  CAR   180.00   0.0  0
 MLH  CONST_37  CAE  NAG  CAH  CAR   180.00   0.0  0
 MLH  CONST_38  CAQ  NAG  CAH  CAR     0.00   0.0  0
 MLH  CONST_39  OAJ  CAB  CAA  CAF   180.00   0.0  0
 MLH  CONST_40  BR1  CAC  CAB  CAA   180.00   0.0  0
 MLH  CONST_41  CAD  CAC  CAB  OAJ   180.00   0.0  0
 MLH  CONST_42  CAE  CAD  CAC  BR1   180.00   0.0  0
 MLH  CONST_43  H15  CAA  CAF  CAI     0.00   0.0  0
 MLH  CONST_44  H17  CAD  CAE  CAF   180.00   0.0  0
 MLH  CONST_45  H22  CAX  CAQ  NAG     0.00   0.0  0
 MLH  CONST_46  H18  CAT  CAQ  NAG     0.00   0.0  0
 MLH  CONST_47  H21  CAW  CAX  CAQ   180.00   0.0  0
 MLH  CONST_48  H19  CAU  CAT  CAQ   180.00   0.0  0
 MLH  CONST_49  H20  CAV  CAU  CAT   180.00   0.0  0
 MLH  Var_01    CAF  CAI  CAL  OAM  -179.96  30.0  2
 MLH  Var_02    NAY  CAR  CAH  CAI  -104.36  30.0  2
 MLH  Var_03    CAI  CAL  OAM  CAO   179.92  30.0  1
 MLH  Var_04    CBA  NAY  CAR  CAH    73.99  30.0  3
 MLH  Var_05    H1   CAP  CAO  OAM   175.50  30.0  3
 MLH  Var_06    H4   CAO  OAM  CAL   -41.72  30.0  1
 MLH  Var_07    H12  CBA  NAY  CAR  -174.74  30.0  3
 MLH  Var_08    H9   CAZ  NAY  CAR   177.16  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
 MLH  plan-1  NAG  0.020
 MLH  plan-1  CAQ  0.020
 MLH  plan-1  CAT  0.020
 MLH  plan-1  CAU  0.020
 MLH  plan-1  CAV  0.020
 MLH  plan-1  CAW  0.020
 MLH  plan-1  CAX  0.020
 MLH  plan-1  H18  0.020
 MLH  plan-1  H19  0.020
 MLH  plan-1  H20  0.020
 MLH  plan-1  H21  0.020
 MLH  plan-1  H22  0.020
 MLH  plan-2  CAL  0.020
 MLH  plan-2  CAI  0.020
 MLH  plan-2  CAH  0.020
 MLH  plan-2  CAR  0.020
 MLH  plan-2  CAF  0.020
 MLH  plan-2  CAA  0.020
 MLH  plan-2  CAB  0.020
 MLH  plan-2  OAJ  0.020
 MLH  plan-2  CAC  0.020
 MLH  plan-2  BR1  0.020
 MLH  plan-2  CAD  0.020
 MLH  plan-2  CAE  0.020
 MLH  plan-2  NAG  0.020
 MLH  plan-2  CAQ  0.020
 MLH  plan-2  H15  0.020
 MLH  plan-2  H17  0.020
 MLH  plan-3  OAM  0.020
 MLH  plan-3  CAL  0.020
 MLH  plan-3  OAN  0.020
 MLH  plan-3  CAI  0.020

