# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 17:51:32 2022
#   Inital geometry file: a 124 line input string
#   Ligand name: (3R)-1-(3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonyl)piperidine-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)[C@@H]1CCCN(C1)[S](=O)(=O)c2cc3C(=O)c4ccccc4C(=O)c3cc2O
#
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
 I99  I99  "(3R)-1-(3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonyl)piperidine-3-carboxylic acid"  ligand  45  29  .  2022-08-10  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_I99
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
 I99  O5   O  OS     0  -0.669   -5.9424  -59.1381  41.1320
 I99  S    S  S      0   1.397   -6.5303  -60.2349  41.9057
 I99  O4   O  OS     0  -0.624   -6.0554  -60.4600  43.2565
 I99  N    N  N      0  -0.561   -6.3240  -61.6167  41.0456
 I99  C17  C  CH2    0  -0.310   -6.6084  -62.8780  41.7435
 I99  C16  C  CH2    0  -0.432   -5.9501  -64.0219  40.9919
 I99  C15  C  CH2    0  -0.432   -6.4023  -64.0630  39.5414
 I99  C13  C  CH1    0  -0.390   -6.1609  -62.7200  38.8574
 I99  C14  C  C      0   0.438   -6.6360  -62.7444  37.3849
 I99  O3   O  O      0  -0.592   -7.4260  -61.8518  37.0198
 I99  O2   O  OC    -1  -0.605   -6.1761  -63.6678  36.6861
 I99  C12  C  CH2    0  -0.291   -6.8092  -61.5949  39.6529
 I99  C11  C  C      0  -0.313   -8.2784  -59.9216  41.9610
 I99  C18  C  C      0   0.432   -8.9017  -59.0185  41.0803
 I99  O6   O  OH1    0  -0.602   -8.2658  -58.2681  40.1947
 I99  C19  C  C1     0  -0.373  -10.2927  -58.8959  41.1388
 I99  C8   C  CR6    0   0.001  -11.0335  -59.6358  42.0366
 I99  C    C  CR6    0   0.319  -12.5140  -59.4669  42.0534
 I99  O    O  O      0  -0.354  -13.0578  -58.6950  41.2950
 I99  C10  C  C1     0  -0.257   -9.0267  -60.6474  42.8745
 I99  C9   C  CR6    0  -0.029  -10.4056  -60.5218  42.9206
 I99  C7   C  CR6    0   0.326  -11.1726  -61.3198  43.8960
 I99  O1   O  O      0  -0.370  -10.6193  -62.0783  44.6656
 I99  C6   C  CR66   0  -0.024  -12.6472  -61.1608  43.9005
 I99  C1   C  CR66   0  -0.027  -13.2857  -60.2768  43.0235
 I99  C5   C  CR16   0  -0.269  -13.4045  -61.9085  44.7966
 I99  C4   C  CR16   0  -0.229  -14.7831  -61.7789  44.8220
 I99  C3   C  CR16   0  -0.231  -15.4170  -60.9000  43.9519
 I99  C2   C  CR16   0  -0.266  -14.6715  -60.1512  43.0570
 I99  H13  H  HCH2   0   0.235   -7.6922  -63.0458  41.7996
 I99  H14  H  HCH2   0   0.275   -6.2217  -62.8268  42.7583
 I99  H11  H  HCH2   0   0.244   -6.1993  -64.9538  41.5034
 I99  H12  H  HCH2   0   0.228   -4.8641  -63.9057  41.0439
 I99  H9   H  HCH2   0   0.212   -7.4709  -64.3057  39.5026
 I99  H10  H  HCH2   0   0.236   -5.8798  -64.8531  39.0027
 I99  H7   H  HCH1   0   0.231   -5.0779  -62.5397  38.8519
 I99  H5   H  HCH2   0   0.232   -7.9007  -61.7046  39.6375
 I99  H6   H  HCH2   0   0.263   -6.5596  -60.6388  39.1992
 I99  H15  H  HOH1   0   0.488   -7.2974  -58.3553  40.3042
 I99  H16  H  H      0   0.291  -10.7784  -58.2018  40.4651
 I99  H4   H  H      0   0.302   -8.5371  -61.3219  43.5650
 I99  H3   H  HCR6   0   0.274  -12.9143  -62.5930  45.4754
 I99  H2   H  HCR6   0   0.277  -15.3657  -62.3638  45.5210
 I99  H1   H  HCR6   0   0.277  -16.4938  -60.7983  43.9727
 I99  H    H  HCR6   0   0.274  -15.1668  -59.4678  42.3810

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
 I99  O    C    double    1.211  0.020  1.211
 I99  C    C1   single    1.481  0.020  1.481
 I99  C1   C2   aromatic  1.392  0.020  1.392
 I99  C2   C3   aromatic  1.385  0.020  1.385
 I99  C3   C4   aromatic  1.390  0.020  1.390
 I99  C4   C5   aromatic  1.385  0.020  1.385
 I99  C1   C6   aromatic  1.399  0.020  1.399
 I99  C5   C6   aromatic  1.391  0.020  1.391
 I99  C6   C7   single    1.483  0.020  1.483
 I99  O1   C7   double    1.214  0.020  1.214
 I99  C    C8   single    1.490  0.020  1.490
 I99  C8   C9   aromatic  1.400  0.020  1.400
 I99  C7   C9   single    1.475  0.020  1.475
 I99  C9   C10  aromatic  1.385  0.020  1.385
 I99  C10  C11  aromatic  1.386  0.020  1.386
 I99  C11  S    single    1.777  0.020  1.777
 I99  N    S    single    1.641  0.020  1.641
 I99  N    C12  single    1.475  0.020  1.475
 I99  C12  C13  single    1.523  0.020  1.523
 I99  C14  C13  single    1.547  0.020  1.547
 I99  O2   C14  deloc     1.246  0.020  1.246
 I99  O3   C14  deloc     1.247  0.020  1.247
 I99  C13  C15  single    1.526  0.020  1.526
 I99  C15  C16  single    1.520  0.020  1.520
 I99  C16  C17  single    1.519  0.020  1.519
 I99  C17  N    single    1.469  0.020  1.469
 I99  O4   S    double    1.449  0.020  1.449
 I99  S    O5   double    1.465  0.020  1.465
 I99  C18  C11  aromatic  1.407  0.020  1.407
 I99  O6   C18  single    1.324  0.020  1.324
 I99  C19  C18  aromatic  1.398  0.020  1.398
 I99  C8   C19  aromatic  1.379  0.020  1.379
 I99  C17  H13  single    0.970  0.020  1.090
 I99  C17  H14  single    0.970  0.020  1.090
 I99  C16  H11  single    0.970  0.020  1.090
 I99  C16  H12  single    0.970  0.020  1.090
 I99  C15  H9   single    0.970  0.020  1.090
 I99  C15  H10  single    0.970  0.020  1.090
 I99  C13  H7   single    0.970  0.020  1.090
 I99  C12  H5   single    0.970  0.020  1.090
 I99  C12  H6   single    0.970  0.020  1.090
 I99  O6   H15  single    0.850  0.020  0.980
 I99  C19  H16  single    0.930  0.020  1.080
 I99  C10  H4   single    0.930  0.020  1.080
 I99  C5   H3   single    0.930  0.020  1.080
 I99  C4   H2   single    0.930  0.020  1.080
 I99  C3   H1   single    0.930  0.020  1.080
 I99  C2   H    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
 I99  C11  S    N    106.77  3.000
 I99  N    S    O4   108.46  3.000
 I99  C11  S    O4   108.71  3.000
 I99  O4   S    O5   118.48  3.000
 I99  N    S    O5   107.65  3.000
 I99  C11  S    O5   106.21  3.000
 I99  C12  N    C17  113.42  3.000
 I99  C17  N    S    116.72  3.000
 I99  C12  N    S    116.18  3.000
 I99  H14  C17  H13  108.09  3.000
 I99  H14  C17  C16  110.07  3.000
 I99  H13  C17  C16  109.76  3.000
 I99  H14  C17  N    109.51  3.000
 I99  H13  C17  N    110.27  3.000
 I99  C16  C17  N    109.12  3.000
 I99  H12  C16  H11  107.16  3.000
 I99  H12  C16  C15  110.11  3.000
 I99  H11  C16  C15  110.85  3.000
 I99  H12  C16  C17  109.09  3.000
 I99  H11  C16  C17  108.18  3.000
 I99  C15  C16  C17  111.32  3.000
 I99  H10  C15  H9   106.82  3.000
 I99  H10  C15  C13  109.91  3.000
 I99  H9   C15  C13  109.46  3.000
 I99  H10  C15  C16  110.41  3.000
 I99  H9   C15  C16  109.25  3.000
 I99  C13  C15  C16  110.90  3.000
 I99  H7   C13  C12  107.53  3.000
 I99  H7   C13  C14  107.50  3.000
 I99  C12  C13  C14  112.21  3.000
 I99  H7   C13  C15  107.63  3.000
 I99  C14  C13  C15  111.35  3.000
 I99  C12  C13  C15  110.40  3.000
 I99  O2   C14  O3   126.89  3.000
 I99  O3   C14  C13  117.51  3.000
 I99  O2   C14  C13  115.59  3.000
 I99  H6   C12  H5   108.09  3.000
 I99  H6   C12  C13  109.51  3.000
 I99  H5   C12  C13  110.02  3.000
 I99  H6   C12  N    109.36  3.000
 I99  H5   C12  N    109.82  3.000
 I99  C13  C12  N    110.01  3.000
 I99  C10  C11  C18  120.63  3.000
 I99  C18  C11  S    121.97  3.000
 I99  C10  C11  S    117.35  3.000
 I99  C19  C18  O6   117.16  3.000
 I99  C19  C18  C11  118.10  3.000
 I99  O6   C18  C11  124.75  3.000
 I99  H15  O6   C18  110.49  3.000
 I99  H16  C19  C8   120.54  3.000
 I99  H16  C19  C18  118.48  3.000
 I99  C8   C19  C18  120.98  3.000
 I99  C9   C8   C    120.67  3.000
 I99  C9   C8   C19  120.63  3.000
 I99  C    C8   C19  118.70  3.000
 I99  C1   C    O    121.66  3.000
 I99  C1   C    C8   117.59  3.000
 I99  O    C    C8   120.75  3.000
 I99  H4   C10  C9   119.04  3.000
 I99  H4   C10  C11  120.17  3.000
 I99  C9   C10  C11  120.79  3.000
 I99  C7   C9   C10  119.37  3.000
 I99  C10  C9   C8   118.86  3.000
 I99  C7   C9   C8   121.77  3.000
 I99  C6   C7   O1   121.21  3.000
 I99  O1   C7   C9   121.34  3.000
 I99  C6   C7   C9   117.44  3.000
 I99  C5   C6   C1   119.65  3.000
 I99  C5   C6   C7   119.05  3.000
 I99  C1   C6   C7   121.30  3.000
 I99  C2   C1   C6   119.75  3.000
 I99  C6   C1   C    121.22  3.000
 I99  C2   C1   C    119.03  3.000
 I99  H3   C5   C4   119.93  3.000
 I99  H3   C5   C6   119.85  3.000
 I99  C4   C5   C6   120.23  3.000
 I99  H2   C4   C3   120.06  3.000
 I99  H2   C4   C5   119.83  3.000
 I99  C3   C4   C5   120.12  3.000
 I99  H1   C3   C2   119.84  3.000
 I99  H1   C3   C4   120.09  3.000
 I99  C2   C3   C4   120.07  3.000
 I99  H    C2   C3   119.95  3.000
 I99  H    C2   C1   119.87  3.000
 I99  C3   C2   C1   120.19  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
 I99  CONST_01  C8   C9   C10  C11     0.00   0.0  0
 I99  CONST_02  C8   C19  C18  C11     0.00   0.0  0
 I99  CONST_03  C9   C10  C11  C18     0.00   0.0  0
 I99  CONST_04  C9   C8   C19  C18     0.00   0.0  0
 I99  CONST_05  C10  C11  C18  C19     0.00   0.0  0
 I99  CONST_06  C1   C    C8   C19   180.00   0.0  0
 I99  CONST_07  C10  C9   C8   C19     0.00   0.0  0
 I99  CONST_08  C2   C1   C    C8    180.00   0.0  0
 I99  CONST_09  C6   C1   C    C8      0.00   0.0  0
 I99  CONST_10  C6   C7   C9   C8      0.00   0.0  0
 I99  CONST_11  C6   C7   C9   C10   180.00   0.0  0
 I99  CONST_12  C1   C    C8   C9      0.00   0.0  0
 I99  CONST_13  C1   C6   C7   C9      0.00   0.0  0
 I99  CONST_14  C5   C6   C7   C9    180.00   0.0  0
 I99  CONST_15  C3   C2   C1   C6      0.00   0.0  0
 I99  CONST_16  C3   C4   C5   C6      0.00   0.0  0
 I99  CONST_17  C4   C3   C2   C1      0.00   0.0  0
 I99  CONST_18  C4   C5   C6   C1      0.00   0.0  0
 I99  CONST_19  C2   C3   C4   C5      0.00   0.0  0
 I99  CONST_20  C2   C1   C6   C5      0.00   0.0  0
 I99  CONST_21  C9   C10  C11  S     180.00   0.0  0
 I99  CONST_22  C19  C18  C11  S     180.00   0.0  0
 I99  CONST_23  C10  C11  C18  O6    180.00   0.0  0
 I99  CONST_24  C8   C19  C18  O6    180.00   0.0  0
 I99  CONST_25  O    C    C8   C19     0.00   0.0  0
 I99  CONST_26  O1   C7   C9   C8    180.00   0.0  0
 I99  CONST_27  C2   C1   C    O       0.00   0.0  0
 I99  CONST_28  C6   C1   C    O     180.00   0.0  0
 I99  CONST_29  C9   C8   C    O     180.00   0.0  0
 I99  CONST_30  O1   C7   C9   C10     0.00   0.0  0
 I99  CONST_31  C1   C6   C7   O1    180.00   0.0  0
 I99  CONST_32  C5   C6   C7   O1      0.00   0.0  0
 I99  CONST_33  H16  C19  C18  C11   180.00   0.0  0
 I99  CONST_34  H4   C10  C11  C18   180.00   0.0  0
 I99  CONST_35  H4   C10  C9   C8    180.00   0.0  0
 I99  CONST_36  H    C2   C1   C       0.00   0.0  0
 I99  CONST_37  H16  C19  C8   C       0.00   0.0  0
 I99  CONST_38  H16  C19  C8   C9    180.00   0.0  0
 I99  CONST_39  H3   C5   C6   C7      0.00   0.0  0
 I99  CONST_40  H4   C10  C9   C7      0.00   0.0  0
 I99  CONST_41  H    C2   C1   C6    180.00   0.0  0
 I99  CONST_42  H2   C4   C5   C6    180.00   0.0  0
 I99  CONST_43  H1   C3   C2   C1    180.00   0.0  0
 I99  CONST_44  H3   C5   C6   C1    180.00   0.0  0
 I99  CONST_45  H1   C3   C4   C5    180.00   0.0  0
 I99  CONST_46  H    C2   C3   C4    180.00   0.0  0
 I99  CONST_47  H3   C5   C4   C3    180.00   0.0  0
 I99  CONST_48  H2   C4   C3   C2    180.00   0.0  0
 I99  Var_01    C15  C16  C17  N     -56.05  30.0  1
 I99  Var_02    C13  C15  C16  C17    54.77  30.0  1
 I99  Var_03    C13  C12  N    C17   -59.33  30.0  1
 I99  Var_04    C12  N    C17  C16    59.22  30.0  1
 I99  Var_05    C13  C12  N    S     161.29  30.0  1
 I99  Var_06    C16  C17  N    S    -161.64  30.0  1
 I99  Var_07    C10  C11  S    N      79.15  30.0  1
 I99  Var_08    C18  C11  S    N     -98.17  30.0  1
 I99  Var_09    C11  S    N    C17   -77.60  30.0  3
 I99  Var_10    C11  S    N    C12    60.42  30.0  3
 I99  Var_11    H11  C16  C17  N    -178.09  30.0  1
 I99  Var_12    H12  C16  C17  N      65.66  30.0  1
 I99  Var_13    H9   C15  C16  C17   -65.97  30.0  1
 I99  Var_14    H10  C15  C16  C17   176.84  30.0  1
 I99  Var_15    H5   C12  N    C17    61.91  30.0  1
 I99  Var_16    H6   C12  N    C17  -179.64  30.0  1
 I99  Var_17    H13  C17  C16  C15    64.90  30.0  1
 I99  Var_18    H14  C17  C16  C15  -176.25  30.0  1
 I99  Var_19    H11  C16  C15  C13   175.24  30.0  1
 I99  Var_20    H12  C16  C15  C13   -66.35  30.0  1
 I99  Var_21    H13  C17  N    C12   -61.41  30.0  1
 I99  Var_22    H14  C17  N    C12   179.77  30.0  1
 I99  Var_23    C10  C11  S    O5   -166.19  30.0  1
 I99  Var_24    C18  C11  S    O5     16.50  30.0  1
 I99  Var_25    C12  N    S    O5    -53.27  30.0  2
 I99  Var_26    C17  N    S    O5    168.71  30.0  2
 I99  Var_27    C10  C11  S    O4    -37.67  30.0  1
 I99  Var_28    C18  C11  S    O4    145.02  30.0  1
 I99  Var_29    C12  N    S    O4    177.40  30.0  2
 I99  Var_30    C17  N    S    O4     39.38  30.0  2
 I99  Var_31    H5   C12  N    S     -77.47  30.0  1
 I99  Var_32    H6   C12  N    S      40.98  30.0  1
 I99  Var_33    H13  C17  N    S      77.73  30.0  1
 I99  Var_34    H14  C17  N    S     -41.09  30.0  1

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
 I99  chir_01  C13  C12  C14  C15  positiv

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
 I99  plan-1  S    0.020
 I99  plan-1  C11  0.020
 I99  plan-1  C18  0.020
 I99  plan-1  O6   0.020
 I99  plan-1  C19  0.020
 I99  plan-1  C8   0.020
 I99  plan-1  C    0.020
 I99  plan-1  O    0.020
 I99  plan-1  C10  0.020
 I99  plan-1  C9   0.020
 I99  plan-1  C7   0.020
 I99  plan-1  O1   0.020
 I99  plan-1  C6   0.020
 I99  plan-1  C1   0.020
 I99  plan-1  C5   0.020
 I99  plan-1  C4   0.020
 I99  plan-1  C3   0.020
 I99  plan-1  C2   0.020
 I99  plan-1  H16  0.020
 I99  plan-1  H4   0.020
 I99  plan-1  H3   0.020
 I99  plan-1  H2   0.020
 I99  plan-1  H1   0.020
 I99  plan-1  H    0.020
 I99  plan-2  C13  0.020
 I99  plan-2  C14  0.020
 I99  plan-2  O3   0.020
 I99  plan-2  O2   0.020

