# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 07:17:01 2020
#   Inital geometry file: a 134 line input string
#   Ligand name: (5Z,9beta,11alpha,12alpha,13E,15S)-9-chloro-11,15-dihydroxyprosta-5,13-dien-1-oic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](Cl)[C@@H]1C\C=C/CCCC(O)=O
#
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
 ON5  ON5  '(5Z,9beta,11alpha,12alpha,13E,15S)-9-chloro-11,15-dihydroxyprosta-5,13-dien-1-oic acid'  ligand  57  25  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_ON5
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
 ON5  C20  C   CH3    0  -0.663   8.2751   4.0761  -0.4340
 ON5  C19  C   CH2    0  -0.418   7.2736   3.3512   0.4542
 ON5  C18  C   CH2    0  -0.408   6.2385   2.5611  -0.3379
 ON5  C17  C   CH2    0  -0.412   5.2164   1.8608   0.5482
 ON5  C16  C   CH2    0  -0.459   4.1796   1.0773  -0.2478
 ON5  C15  C   CH1    0   0.008   3.0667   0.4805   0.6154
 ON5  O15  O   OH1    0  -0.662   3.5646  -0.3848   1.6099
 ON5  C14  C   C1     0  -0.263   2.0123  -0.1574  -0.2452
 ON5  C13  C   C1     0  -0.188   1.5095  -1.3769  -0.0871
 ON5  C12  C   CH1    0  -0.344   0.4416  -1.9571  -0.9606
 ON5  C11  C   CH1    0   0.049   0.8027  -3.3704  -1.4456
 ON5  O11  O   OH1    0  -0.672   0.1552  -3.5650  -2.6866
 ON5  C10  C   CH2    0  -0.464   0.2180  -4.2715  -0.3646
 ON5  C9   C   CH1    0  -0.274  -1.1401  -3.6367  -0.1248
 ON5  CL9  CL  CL     0  -0.167  -1.8604  -4.1710   1.4406
 ON5  C8   C   CH1    0  -0.179  -0.9000  -2.1208  -0.1824
 ON5  C7   C   CH2    0  -0.508  -2.0394  -1.3355  -0.8346
 ON5  C6   C   C1     0  -0.208  -3.3551  -1.4740  -0.1316
 ON5  C5   C   C1     0  -0.210  -3.9478  -0.5549   0.6294
 ON5  C4   C   CH2    0  -0.489  -3.4406   0.8137   0.9603
 ON5  C3   C   CH2    0  -0.402  -4.2260   1.9207   0.2522
 ON5  C2   C   CH2    0  -0.581  -3.7620   3.3079   0.6650
 ON5  C1   C   C      0   0.409  -4.5029   4.4908   0.0170
 ON5  O1A  O   O      0  -0.609  -5.4881   4.2386  -0.7042
 ON5  O1B  O   OC    -1  -0.634  -4.0541   5.6267   0.2817
 ON5  H1   H   HCH3   0   0.226   8.9928   4.6483   0.1549
 ON5  H2   H   HCH3   0   0.216   8.8403   3.3729  -1.0483
 ON5  H3   H   HCH3   0   0.215   7.7734   4.7717  -1.1098
 ON5  H4   H   HCH2   0   0.210   7.8062   2.6744   1.1294
 ON5  H5   H   HCH2   0   0.210   6.7606   4.0755   1.0950
 ON5  H6   H   HCH2   0   0.206   5.7195   3.2362  -1.0275
 ON5  H7   H   HCH2   0   0.207   6.7495   1.8220  -0.9651
 ON5  H8   H   HCH2   0   0.214   5.7346   1.1937   1.2425
 ON5  H9   H   HCH2   0   0.209   4.7052   2.6081   1.1657
 ON5  H10  H   HCH2   0   0.224   3.7168   1.7372  -0.9883
 ON5  H11  H   HCH2   0   0.224   4.6672   0.2770  -0.8177
 ON5  H12  H   HCH1   0   0.234   2.5954   1.3085   1.1607
 ON5  H13  H   HOH1   0   0.443   4.0475  -1.0952   1.1726
 ON5  H14  H   H      0   0.239   1.6424   0.4646  -1.0572
 ON5  H15  H   H      0   0.241   1.8548  -1.9963   0.7374
 ON5  H16  H   HCH1   0   0.256   0.3065  -1.2964  -1.8222
 ON5  H17  H   HCH1   0   0.228   1.8876  -3.5032  -1.5436
 ON5  H18  H   HOH1   0   0.450   0.2600  -4.4872  -2.9423
 ON5  H19  H   HCH2   0   0.264   0.1605  -5.3234  -0.6504
 ON5  H20  H   HCH2   0   0.248   0.8307  -4.2113   0.5390
 ON5  H21  H   HCH1   0   0.291  -1.8523  -3.9514  -0.8874
 ON5  H22  H   HCH1   0   0.256  -0.7657  -1.7487   0.8373
 ON5  H23  H   HCH2   0   0.244  -1.7404  -0.2867  -0.8936
 ON5  H24  H   HCH2   0   0.240  -2.1478  -1.6817  -1.8683
 ON5  H25  H   H      0   0.229  -3.8674  -2.4217  -0.2688
 ON5  H26  H   H      0   0.227  -4.9170  -0.8038   1.0537
 ON5  H27  H   HCH2   0   0.225  -3.5189   0.9628   2.0431
 ON5  H28  H   HCH2   0   0.221  -2.3791   0.9100   0.7192
 ON5  H29  H   HCH2   0   0.208  -4.1187   1.7947  -0.8288
 ON5  H30  H   HCH2   0   0.208  -5.2915   1.8054   0.4673
 ON5  H31  H   HCH2   0   0.220  -3.8495   3.4104   1.7538
 ON5  H32  H   HCH2   0   0.216  -2.6909   3.4150   0.4593

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
 ON5  O15  C15  single  1.409  0.020  1.409
 ON5  C18  C17  single  1.523  0.020  1.523
 ON5  C18  C19  single  1.524  0.020  1.524
 ON5  C20  C19  single  1.522  0.020  1.522
 ON5  C16  C17  single  1.524  0.020  1.524
 ON5  C16  C15  single  1.530  0.020  1.530
 ON5  C15  C14  single  1.503  0.020  1.503
 ON5  C14  C13  double  1.329  0.020  1.329
 ON5  C13  C12  single  1.497  0.020  1.497
 ON5  O11  C11  single  1.413  0.020  1.413
 ON5  C11  C12  single  1.537  0.020  1.537
 ON5  C11  C10  single  1.524  0.020  1.524
 ON5  C12  C8   single  1.560  0.020  1.560
 ON5  C10  C9   single  1.518  0.020  1.518
 ON5  C8   C7   single  1.530  0.020  1.530
 ON5  C8   C9   single  1.536  0.020  1.536
 ON5  C7   C6   single  1.498  0.020  1.498
 ON5  C6   C5   double  1.332  0.020  1.332
 ON5  C9   CL9  single  1.804  0.020  1.804
 ON5  C5   C4   single  1.497  0.020  1.497
 ON5  C4   C3   single  1.531  0.020  1.531
 ON5  C3   C2   single  1.520  0.020  1.520
 ON5  C2   C1   single  1.539  0.020  1.539
 ON5  O1A  C1   deloc   1.247  0.020  1.247
 ON5  C1   O1B  deloc   1.250  0.020  1.250
 ON5  C20  H1   single  0.970  0.020  1.090
 ON5  C20  H2   single  0.970  0.020  1.090
 ON5  C20  H3   single  0.970  0.020  1.090
 ON5  C19  H4   single  0.970  0.020  1.090
 ON5  C19  H5   single  0.970  0.020  1.090
 ON5  C18  H6   single  0.970  0.020  1.090
 ON5  C18  H7   single  0.970  0.020  1.090
 ON5  C17  H8   single  0.970  0.020  1.090
 ON5  C17  H9   single  0.970  0.020  1.090
 ON5  C16  H10  single  0.970  0.020  1.090
 ON5  C16  H11  single  0.970  0.020  1.090
 ON5  C15  H12  single  0.970  0.020  1.090
 ON5  O15  H13  single  0.850  0.020  0.980
 ON5  C14  H14  single  0.930  0.020  1.080
 ON5  C13  H15  single  0.930  0.020  1.080
 ON5  C12  H16  single  0.970  0.020  1.090
 ON5  C11  H17  single  0.970  0.020  1.090
 ON5  O11  H18  single  0.850  0.020  0.980
 ON5  C10  H19  single  0.970  0.020  1.090
 ON5  C10  H20  single  0.970  0.020  1.090
 ON5  C9   H21  single  0.970  0.020  1.090
 ON5  C8   H22  single  0.970  0.020  1.090
 ON5  C7   H23  single  0.970  0.020  1.090
 ON5  C7   H24  single  0.970  0.020  1.090
 ON5  C6   H25  single  0.930  0.020  1.080
 ON5  C5   H26  single  0.930  0.020  1.080
 ON5  C4   H27  single  0.970  0.020  1.090
 ON5  C4   H28  single  0.970  0.020  1.090
 ON5  C3   H29  single  0.970  0.020  1.090
 ON5  C3   H30  single  0.970  0.020  1.090
 ON5  C2   H31  single  0.970  0.020  1.090
 ON5  C2   H32  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
 ON5  H3   C20  H2   107.46  3.000
 ON5  H3   C20  H1   107.60  3.000
 ON5  H2   C20  H1   107.53  3.000
 ON5  H3   C20  C19  111.24  3.000
 ON5  H2   C20  C19  111.24  3.000
 ON5  H1   C20  C19  111.57  3.000
 ON5  H5   C19  H4   106.03  3.000
 ON5  H5   C19  C18  109.20  3.000
 ON5  H4   C19  C18  109.30  3.000
 ON5  H5   C19  C20  109.56  3.000
 ON5  H4   C19  C20  109.53  3.000
 ON5  C18  C19  C20  112.98  3.000
 ON5  H7   C18  H6   106.04  3.000
 ON5  H7   C18  C17  109.62  3.000
 ON5  H6   C18  C17  109.36  3.000
 ON5  H7   C18  C19  109.29  3.000
 ON5  H6   C18  C19  109.23  3.000
 ON5  C17  C18  C19  113.06  3.000
 ON5  H9   C17  H8   106.22  3.000
 ON5  H9   C17  C16  109.12  3.000
 ON5  H8   C17  C16  109.90  3.000
 ON5  H9   C17  C18  109.10  3.000
 ON5  H8   C17  C18  109.38  3.000
 ON5  C16  C17  C18  112.89  3.000
 ON5  H11  C16  H10  106.04  3.000
 ON5  H11  C16  C15  109.38  3.000
 ON5  H10  C16  C15  108.02  3.000
 ON5  H11  C16  C17  110.13  3.000
 ON5  H10  C16  C17  109.34  3.000
 ON5  C15  C16  C17  113.63  3.000
 ON5  H12  C15  C14  107.65  3.000
 ON5  H12  C15  O15  105.33  3.000
 ON5  C14  C15  O15  113.04  3.000
 ON5  H12  C15  C16  107.36  3.000
 ON5  C14  C15  C16  110.66  3.000
 ON5  O15  C15  C16  112.38  3.000
 ON5  H13  O15  C15  108.02  3.000
 ON5  H14  C14  C13  119.02  3.000
 ON5  H14  C14  C15  115.05  3.000
 ON5  C13  C14  C15  125.94  3.000
 ON5  H15  C13  C12  116.63  3.000
 ON5  H15  C13  C14  119.53  3.000
 ON5  C12  C13  C14  123.81  3.000
 ON5  H16  C12  C8   110.49  3.000
 ON5  H16  C12  C11  109.62  3.000
 ON5  C8   C12  C11  105.25  3.000
 ON5  H16  C12  C13  108.27  3.000
 ON5  C8   C12  C13  111.30  3.000
 ON5  C11  C12  C13  111.90  3.000
 ON5  H17  C11  C10  111.78  3.000
 ON5  H17  C11  O11  110.97  3.000
 ON5  C10  C11  O11  111.45  3.000
 ON5  H17  C11  C12  111.82  3.000
 ON5  C10  C11  C12  103.28  3.000
 ON5  O11  C11  C12  107.22  3.000
 ON5  H18  O11  C11  108.38  3.000
 ON5  H20  C10  H19  107.39  3.000
 ON5  H20  C10  C9   110.35  3.000
 ON5  H19  C10  C9   113.41  3.000
 ON5  H20  C10  C11  109.79  3.000
 ON5  H19  C10  C11  113.85  3.000
 ON5  C9   C10  C11  102.01  3.000
 ON5  H21  C9   C8   111.16  3.000
 ON5  H21  C9   CL9  105.11  3.000
 ON5  C8   C9   CL9  112.78  3.000
 ON5  H21  C9   C10  110.69  3.000
 ON5  CL9  C9   C10  111.74  3.000
 ON5  C8   C9   C10  105.48  3.000
 ON5  H22  C8   C7   108.32  3.000
 ON5  H22  C8   C9   108.67  3.000
 ON5  C7   C8   C9   113.97  3.000
 ON5  H22  C8   C12  108.90  3.000
 ON5  C9   C8   C12  104.88  3.000
 ON5  C7   C8   C12  111.97  3.000
 ON5  H24  C7   H23  106.23  3.000
 ON5  H24  C7   C6   109.07  3.000
 ON5  H23  C7   C6   110.76  3.000
 ON5  H24  C7   C8   108.29  3.000
 ON5  H23  C7   C8   108.19  3.000
 ON5  C6   C7   C8   113.99  3.000
 ON5  H25  C6   C5   117.67  3.000
 ON5  H25  C6   C7   115.83  3.000
 ON5  C5   C6   C7   126.51  3.000
 ON5  H26  C5   C4   115.17  3.000
 ON5  H26  C5   C6   117.50  3.000
 ON5  C4   C5   C6   127.33  3.000
 ON5  H28  C4   H27  105.98  3.000
 ON5  H28  C4   C3   109.42  3.000
 ON5  H27  C4   C3   108.79  3.000
 ON5  H28  C4   C5   111.16  3.000
 ON5  H27  C4   C5   108.58  3.000
 ON5  C3   C4   C5   112.65  3.000
 ON5  H30  C3   H29  106.14  3.000
 ON5  H30  C3   C2   109.90  3.000
 ON5  H29  C3   C2   110.10  3.000
 ON5  H30  C3   C4   109.43  3.000
 ON5  H29  C3   C4   108.88  3.000
 ON5  C2   C3   C4   112.20  3.000
 ON5  H32  C2   H31  104.77  3.000
 ON5  H32  C2   C1   108.44  3.000
 ON5  H31  C2   C1   107.92  3.000
 ON5  H32  C2   C3   109.67  3.000
 ON5  H31  C2   C3   109.30  3.000
 ON5  C1   C2   C3   116.12  3.000
 ON5  O1B  C1   O1A  126.17  3.000
 ON5  O1B  C1   C2   115.89  3.000
 ON5  O1A  C1   C2   117.94  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
 ON5  Var_01  C12  C13  C14  C15   178.93   0.0  2
 ON5  Var_02  C5   C6   C7   C8    105.81  30.0  3
 ON5  Var_03  C4   C5   C6   C7     -0.26   0.0  2
 ON5  Var_04  C17  C18  C19  C20  -178.69  30.0  1
 ON5  Var_05  C16  C17  C18  C19   179.74  30.0  3
 ON5  Var_06  C15  C16  C17  C18  -174.36  30.0  2
 ON5  Var_07  C3   C4   C5   C6    108.21  30.0  3
 ON5  Var_08  C2   C3   C4   C5    176.27  30.0  3
 ON5  Var_09  C1   C2   C3   C4   -179.37  30.0  3
 ON5  Var_10  O1A  C1   C2   C3      5.73  30.0  3
 ON5  Var_11  H1   C20  C19  C18   178.94  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
 ON5  chir_01  C15  O15  C16  C14  negativ
 ON5  chir_02  C12  C8   C11  C13  positiv
 ON5  chir_03  C11  O11  C12  C10  negativ
 ON5  chir_04  C9   CL9  C8   C10  negativ
 ON5  chir_05  C8   C12  C7   C9   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
 ON5  plan-1  C2   0.020
 ON5  plan-1  C1   0.020
 ON5  plan-1  O1A  0.020
 ON5  plan-1  O1B  0.020
 ON5  plan-2  C15  0.020
 ON5  plan-2  C14  0.020
 ON5  plan-2  C13  0.020
 ON5  plan-2  C12  0.020
 ON5  plan-2  H14  0.020
 ON5  plan-2  H15  0.020
 ON5  plan-3  C7   0.020
 ON5  plan-3  C6   0.020
 ON5  plan-3  C5   0.020
 ON5  plan-3  C4   0.020
 ON5  plan-3  H25  0.020
 ON5  plan-3  H26  0.020

