# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 04:47:32 2022
#   Inital geometry file: a 118 line input string
#   Ligand name: (2S)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-9,11-dihydroindolizino[1,2-b]quinolin-7-yl]butanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@@](O)(C(O)=O)C1=C(CO)C(=O)N2Cc3cc4ccccc4nc3C2=C1
#
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
 EHF  EHF  '(2S)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-9,11-dihydroindolizino[1,2-b]quinolin-7-yl]butanoic acid'  ligand  44  27  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_EHF
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
 EHF  C1   C  CR16   0  -0.250  -6.6766  -0.9654   0.3064
 EHF  C2   C  CR16   0  -0.257  -5.9549  -2.1732   0.2003
 EHF  C3   C  CR16   0  -0.307  -4.5931  -2.1615   0.0706
 EHF  C4   C  CR66   0   0.200  -3.8875  -0.9370   0.0431
 EHF  C5   C  CR66   0   0.103  -4.6156   0.2824   0.1499
 EHF  C6   C  CR16   0  -0.315  -6.0212   0.2352   0.2819
 EHF  N7   N  N      0  -0.449  -2.5394  -0.9700  -0.0825
 EHF  C8   C  CR56   0   0.034  -1.9328   0.1809  -0.1012
 EHF  C9   C  CR56   0   0.068  -2.5516   1.4477  -0.0051
 EHF  C10  C  CR16   0  -0.253  -3.9045   1.5053   0.1231
 EHF  C11  C  CR56   0   0.532  -0.4962   0.3944  -0.2216
 EHF  N12  N  N      0  -0.627  -0.2853   1.7364  -0.1978
 EHF  C13  C  CH2    0  -0.297  -1.5116   2.5182  -0.0618
 EHF  C14  C  CR16   0  -0.445   0.5305  -0.4763  -0.3385
 EHF  C15  C  CR6    0   0.199   1.8641   0.0213  -0.4327
 EHF  C16  C  CR6    0  -0.244   2.0754   1.3857  -0.3952
 EHF  C17  C  CR6    0   0.541   0.9563   2.3112  -0.2639
 EHF  O18  O  O      0  -0.517   1.0492   3.5379  -0.2141
 EHF  C19  C  CH2    0  -0.254   3.4281   2.0604  -0.3804
 EHF  C20  C  CT     0   0.072   2.9270  -1.0950  -0.4781
 EHF  C21  C  C      0   0.457   3.2081  -1.4562   1.0160
 EHF  O22  O  OC    -1  -0.552   2.8647  -2.5674   1.4187
 EHF  O23  O  O      0  -0.601   3.7687  -0.5541   1.6858
 EHF  O24  O  OH1    0  -0.653   2.3610  -2.2320  -1.0869
 EHF  C25  C  CH2    0  -0.482   4.2555  -0.7804  -1.1881
 EHF  C26  C  CH3    0  -0.656   5.1605  -2.0003  -1.3243
 EHF  O27  O  OH1    0  -0.713   4.0820   1.9463   0.8608
 EHF  H1   H  HCR6   0   0.266  -7.7533  -0.9937   0.4071
 EHF  H2   H  HCR6   0   0.267  -6.4873  -3.1149   0.2229
 EHF  H3   H  HCR6   0   0.265  -4.0302  -3.0823  -0.0135
 EHF  H4   H  HCR6   0   0.265  -6.5721   1.1639   0.3653
 EHF  H5   H  HCR6   0   0.273  -4.4383   2.4446   0.2064
 EHF  H6   H  HCH2   0   0.293  -1.6362   3.1894  -0.9137
 EHF  H7   H  HCR6   0   0.270   0.3201  -1.5334  -0.3435
 EHF  H9   H  HCH2   0   0.200   4.0369   1.6866  -1.2065
 EHF  H10  H  HCH2   0   0.235   3.2857   3.1222  -0.5765
 EHF  H12  H  HOH1   0   0.444   2.2473  -2.0405  -2.0249
 EHF  H13  H  HCH2   0   0.233   4.0484  -0.3694  -2.1818
 EHF  H14  H  HCH2   0   0.239   4.8134  -0.0204  -0.6488
 EHF  H15  H  HCH3   0   0.223   4.7159  -2.7883  -1.9293
 EHF  H16  H  HCH3   0   0.229   6.0957  -1.7079  -1.8027
 EHF  H17  H  HCH3   0   0.223   5.4155  -2.4270  -0.3530
 EHF  H18  H  HOH1   0   0.448   4.0044   1.0084   1.1618
 EHF  H8   H  HCH2   0   0.294  -1.4821   3.1276   0.8434

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
 EHF  C1   C6   aromatic  1.368  0.020  1.368
 EHF  C1   C2   aromatic  1.411  0.020  1.411
 EHF  C6   C5   aromatic  1.413  0.020  1.413
 EHF  C2   C3   aromatic  1.368  0.020  1.368
 EHF  C5   C10  aromatic  1.415  0.020  1.415
 EHF  C5   C4   aromatic  1.424  0.020  1.424
 EHF  C3   C4   aromatic  1.414  0.020  1.414
 EHF  C10  C9   aromatic  1.360  0.020  1.360
 EHF  C4   N7   aromatic  1.354  0.020  1.354
 EHF  C9   C8   aromatic  1.413  0.020  1.413
 EHF  C9   C13  single    1.494  0.020  1.494
 EHF  N7   C8   aromatic  1.301  0.020  1.301
 EHF  C8   C11  single    1.457  0.020  1.457
 EHF  C13  N12  single    1.461  0.020  1.461
 EHF  C11  N12  single    1.359  0.020  1.359
 EHF  C11  C14  double    1.351  0.020  1.351
 EHF  N12  C17  single    1.370  0.020  1.370
 EHF  C14  C15  single    1.427  0.020  1.427
 EHF  C26  C25  single    1.525  0.020  1.525
 EHF  C17  O18  double    1.231  0.020  1.231
 EHF  C17  C16  single    1.458  0.020  1.458
 EHF  C15  C16  double    1.381  0.020  1.381
 EHF  C15  C20  single    1.542  0.020  1.542
 EHF  C16  C19  single    1.512  0.020  1.512
 EHF  C25  C20  single    1.539  0.020  1.539
 EHF  O24  C20  single    1.408  0.020  1.408
 EHF  C20  C21  single    1.563  0.020  1.563
 EHF  C19  O27  single    1.407  0.020  1.407
 EHF  C21  O23  deloc     1.256  0.020  1.256
 EHF  C21  O22  deloc     1.231  0.020  1.231
 EHF  C1   H1   single    0.930  0.020  1.080
 EHF  C2   H2   single    0.930  0.020  1.080
 EHF  C3   H3   single    0.930  0.020  1.080
 EHF  C6   H4   single    0.930  0.020  1.080
 EHF  C10  H5   single    0.930  0.020  1.080
 EHF  C13  H6   single    0.970  0.020  1.090
 EHF  C14  H7   single    0.930  0.020  1.080
 EHF  C19  H9   single    0.970  0.020  1.090
 EHF  C19  H10  single    0.970  0.020  1.090
 EHF  O24  H12  single    0.850  0.020  0.980
 EHF  C25  H13  single    0.970  0.020  1.090
 EHF  C25  H14  single    0.970  0.020  1.090
 EHF  C26  H15  single    0.970  0.020  1.090
 EHF  C26  H16  single    0.970  0.020  1.090
 EHF  C26  H17  single    0.970  0.020  1.090
 EHF  O27  H18  single    0.850  0.020  0.980
 EHF  C13  H8   single    0.970  0.020  1.090

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
 EHF  H1   C1   C6   120.10  3.000
 EHF  H1   C1   C2   119.59  3.000
 EHF  C6   C1   C2   120.32  3.000
 EHF  H2   C2   C3   119.95  3.000
 EHF  H2   C2   C1   119.45  3.000
 EHF  C3   C2   C1   120.60  3.000
 EHF  H3   C3   C4   118.41  3.000
 EHF  H3   C3   C2   121.19  3.000
 EHF  C4   C3   C2   120.41  3.000
 EHF  N7   C4   C5   122.46  3.000
 EHF  N7   C4   C3   118.53  3.000
 EHF  C5   C4   C3   119.01  3.000
 EHF  C10  C5   C6   122.06  3.000
 EHF  C10  C5   C4   118.79  3.000
 EHF  C6   C5   C4   119.15  3.000
 EHF  H4   C6   C5   118.99  3.000
 EHF  H4   C6   C1   120.49  3.000
 EHF  C5   C6   C1   120.51  3.000
 EHF  C8   N7   C4   116.35  3.000
 EHF  C11  C8   C9   107.81  3.000
 EHF  C11  C8   N7   126.18  3.000
 EHF  C9   C8   N7   126.01  3.000
 EHF  C13  C9   C10  131.75  3.000
 EHF  C13  C9   C8   109.57  3.000
 EHF  C10  C9   C8   118.68  3.000
 EHF  H5   C10  C9   122.27  3.000
 EHF  H5   C10  C5   120.02  3.000
 EHF  C9   C10  C5   117.71  3.000
 EHF  C14  C11  N12  121.33  3.000
 EHF  C14  C11  C8   131.43  3.000
 EHF  N12  C11  C8   107.24  3.000
 EHF  C17  N12  C13  122.74  3.000
 EHF  C17  N12  C11  123.67  3.000
 EHF  C13  N12  C11  113.58  3.000
 EHF  H8   C13  H6   107.87  3.000
 EHF  H8   C13  N12  110.69  3.000
 EHF  H6   C13  N12  110.63  3.000
 EHF  H8   C13  C9   112.79  3.000
 EHF  H6   C13  C9   113.01  3.000
 EHF  N12  C13  C9   101.80  3.000
 EHF  H7   C14  C15  121.62  3.000
 EHF  H7   C14  C11  118.95  3.000
 EHF  C15  C14  C11  119.43  3.000
 EHF  C20  C15  C16  127.62  3.000
 EHF  C20  C15  C14  113.19  3.000
 EHF  C16  C15  C14  119.06  3.000
 EHF  C19  C16  C17  113.74  3.000
 EHF  C19  C16  C15  125.32  3.000
 EHF  C17  C16  C15  120.80  3.000
 EHF  O18  C17  C16  125.31  3.000
 EHF  C16  C17  N12  115.70  3.000
 EHF  O18  C17  N12  118.99  3.000
 EHF  H10  C19  H9   105.69  3.000
 EHF  H10  C19  O27  107.38  3.000
 EHF  H9   C19  O27  112.35  3.000
 EHF  H10  C19  C16  108.44  3.000
 EHF  H9   C19  C16  109.79  3.000
 EHF  O27  C19  C16  112.84  3.000
 EHF  C25  C20  O24  108.21  3.000
 EHF  O24  C20  C21  107.40  3.000
 EHF  C25  C20  C21  109.46  3.000
 EHF  C21  C20  C15  105.26  3.000
 EHF  O24  C20  C15  108.67  3.000
 EHF  C25  C20  C15  117.43  3.000
 EHF  O23  C21  O22  126.77  3.000
 EHF  O22  C21  C20  118.12  3.000
 EHF  O23  C21  C20  115.11  3.000
 EHF  H12  O24  C20  107.91  3.000
 EHF  H14  C25  H13  106.56  3.000
 EHF  H14  C25  C26  107.42  3.000
 EHF  H13  C25  C26  109.36  3.000
 EHF  H14  C25  C20  110.94  3.000
 EHF  H13  C25  C20  109.40  3.000
 EHF  C26  C25  C20  112.95  3.000
 EHF  H17  C26  H16  107.16  3.000
 EHF  H17  C26  H15  107.89  3.000
 EHF  H16  C26  H15  107.50  3.000
 EHF  H17  C26  C25  111.84  3.000
 EHF  H16  C26  C25  109.49  3.000
 EHF  H15  C26  C25  112.73  3.000
 EHF  H18  O27  C19  108.01  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
 EHF  CONST_01  C10  C5   C6   C1   180.00   0.0  0
 EHF  CONST_02  C4   C5   C6   C1     0.00   0.0  0
 EHF  CONST_03  C4   C3   C2   C1     0.00   0.0  0
 EHF  CONST_04  C5   C6   C1   C2     0.00   0.0  0
 EHF  CONST_05  C5   C4   C3   C2     0.00   0.0  0
 EHF  CONST_06  N7   C4   C3   C2   180.00   0.0  0
 EHF  CONST_07  C6   C1   C2   C3     0.00   0.0  0
 EHF  CONST_08  C6   C5   C4   C3     0.00   0.0  0
 EHF  CONST_09  C10  C5   C4   C3   180.00   0.0  0
 EHF  CONST_10  C8   N7   C4   C3   180.00   0.0  0
 EHF  CONST_11  C9   C10  C5   C4     0.00   0.0  0
 EHF  CONST_12  C9   C8   N7   C4     0.00   0.0  0
 EHF  CONST_13  C8   C9   C10  C5     0.00   0.0  0
 EHF  CONST_14  C8   N7   C4   C5     0.00   0.0  0
 EHF  CONST_15  C9   C10  C5   C6   180.00   0.0  0
 EHF  CONST_16  N7   C4   C5   C6   180.00   0.0  0
 EHF  CONST_17  C10  C5   C4   N7     0.00   0.0  0
 EHF  CONST_18  C10  C9   C8   N7     0.00   0.0  0
 EHF  CONST_19  C15  C14  C11  C8   180.00   0.0  0
 EHF  CONST_20  C16  C17  N12  C11    0.00   0.0  0
 EHF  CONST_21  C15  C14  C11  N12    0.00   0.0  0
 EHF  CONST_22  C16  C17  N12  C13  180.00   0.0  0
 EHF  CONST_23  O18  C17  N12  C11  180.00   0.0  0
 EHF  CONST_24  O18  C17  N12  C13    0.00   0.0  0
 EHF  CONST_25  H3   C3   C2   C1   180.00   0.0  0
 EHF  CONST_26  H4   C6   C1   C2   180.00   0.0  0
 EHF  CONST_27  H1   C1   C2   C3   180.00   0.0  0
 EHF  CONST_28  H5   C10  C5   C4   180.00   0.0  0
 EHF  CONST_29  H2   C2   C3   C4   180.00   0.0  0
 EHF  CONST_30  H7   C14  C11  C8     0.00   0.0  0
 EHF  Var_01    H6   C13  C9   C8   118.75  30.0  1
 EHF  Var_02    O27  C19  C16  C15  -73.82  30.0  3
 EHF  Var_03    H15  C26  C25  C20   62.29  30.0  3

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
 EHF  chir_01  C20  C15  O24  C21  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
 EHF  plan-1  C1   0.020
 EHF  plan-1  C2   0.020
 EHF  plan-1  C3   0.020
 EHF  plan-1  C4   0.020
 EHF  plan-1  C5   0.020
 EHF  plan-1  C6   0.020
 EHF  plan-1  N7   0.020
 EHF  plan-1  C8   0.020
 EHF  plan-1  C9   0.020
 EHF  plan-1  C10  0.020
 EHF  plan-1  C11  0.020
 EHF  plan-1  N12  0.020
 EHF  plan-1  C13  0.020
 EHF  plan-1  C14  0.020
 EHF  plan-1  C15  0.020
 EHF  plan-1  C16  0.020
 EHF  plan-1  C17  0.020
 EHF  plan-1  O18  0.020
 EHF  plan-1  C19  0.020
 EHF  plan-1  C20  0.020
 EHF  plan-1  H1   0.020
 EHF  plan-1  H2   0.020
 EHF  plan-1  H3   0.020
 EHF  plan-1  H4   0.020
 EHF  plan-1  H5   0.020
 EHF  plan-1  H7   0.020
 EHF  plan-2  C20  0.020
 EHF  plan-2  C21  0.020
 EHF  plan-2  O22  0.020
 EHF  plan-2  O23  0.020

