# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Thu Jun 25 10:02:13 2020
#   Inital geometry file: a 176 line input string
#   Ligand name: (1R,2R)-2-[(2S,6E,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadec-6-en-2-yl]cyclobutanecarboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]1C[C@@H](C)C[C@H](C)[C@@H](O)C(=C/CCC[C@H](OC(=O)C[C@H](O)[C@@H](C)C1)[C@@H]2CC[C@H]2C(O)=O)/C#N
#
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
 BC9  BC9  '(1R,2R)-2-[(2S,6E,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadec-6-en-2-yl]cyclobutanecarboxylic acid'  ligand  76  34  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_BC9
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
 BC9  C1   C  C      0  -0.222  -4.1287  -2.1213  -0.1170
 BC9  C2   C  C      0  -0.340  -5.3755  -1.4440  -0.7194
 BC9  C3   C  C      0  -0.442  -6.0484  -2.8258  -0.7904
 BC9  C5   C  C      0  -0.449  -4.6494  -3.4606  -0.6763
 BC9  C6   C  CH1    0   0.029  -2.7571  -1.6644  -0.5607
 BC9  C7   C  CH2    0  -0.440  -1.6380  -2.6010  -0.1270
 BC9  C8   C  CH2    0  -0.438  -0.2632  -2.1692  -0.6299
 BC9  C9   C  CH2    0  -0.499   0.8333  -3.1961  -0.3229
 BC9  C10  C  C1     0  -0.177   2.1432  -2.7411  -0.8693
 BC9  C11  C  C      0  -0.016   3.2671  -2.4811  -0.1916
 BC9  C12  C  CSP    0   0.050   3.3299  -2.6949   1.2203
 BC9  C13  C  CH1    0   0.046   4.5422  -1.9628  -0.8284
 BC9  C14  C  CH1    0  -0.295   4.9503  -0.5819  -0.2937
 BC9  C15  C  CH3    0  -0.662   6.2012  -0.0690  -1.0004
 BC9  C16  C  CH2    0  -0.399   3.7845   0.3922  -0.4430
 BC9  C17  C  CH1    0  -0.226   3.9621   1.8294   0.0820
 BC9  C18  C  CH3    0  -0.668   4.4704   1.8160   1.5202
 BC9  C19  C  CH2    0  -0.422   2.5722   2.4625  -0.0751
 BC9  C20  C  CH1    0  -0.211   2.2940   3.9557   0.0919
 BC9  C21  C  CH3    0  -0.681   2.7092   4.5470   1.4401
 BC9  C22  C  CH2    0  -0.448   0.8292   4.2924  -0.2935
 BC9  C23  C  CH1    0  -0.237  -0.4041   3.6378   0.3955
 BC9  C24  C  CH3    0  -0.684  -0.2098   3.3366   1.8780
 BC9  C25  C  CH1    0   0.039  -1.0023   2.4632  -0.4058
 BC9  C26  C  CH2    0  -0.577  -2.3390   1.9579   0.1470
 BC9  C27  C  C      0   0.624  -2.7332   0.7345  -0.6428
 BC9  O28  O  O      0  -0.484  -3.1410   0.7827  -1.7796
 BC9  O29  O  O2     0  -0.458  -2.4889  -0.3799   0.0244
 BC9  C30  C  C      0   0.407  -6.0686  -0.3010   0.0120
 BC9  O31  O  O      0  -0.596  -5.3535   0.4691   0.6869
 BC9  O32  O  OC    -1  -0.622  -7.3047  -0.2160  -0.1452
 BC9  O33  O  OH1    0  -0.658   5.6014  -2.8564  -0.5791
 BC9  O34  O  OH1    0  -0.656  -0.1869   1.3138  -0.4763
 BC9  N35  N  NS     0  -0.260   3.4118  -2.8536   2.3598
 BC9  H1   H  H      0   0.218  -4.1820  -2.1210   0.9772
 BC9  H2   H  H      0   0.234  -5.1375  -1.1024  -1.7341
 BC9  H3   H  H      0   0.215  -6.6565  -3.0246   0.0943
 BC9  H4   H  H      0   0.217  -6.6400  -3.0658  -1.6744
 BC9  H5   H  H      0   0.218  -4.2231  -3.6766  -1.6591
 BC9  H6   H  H      0   0.227  -4.5371  -4.3460  -0.0494
 BC9  H7   H  HCH1   0   0.219  -2.7433  -1.5818  -1.6529
 BC9  H8   H  HCH2   0   0.225  -1.6332  -2.6944   0.9640
 BC9  H9   H  HCH2   0   0.238  -1.8717  -3.5952  -0.5197
 BC9  H10  H  HCH2   0   0.222  -0.3098  -2.0160  -1.7128
 BC9  H11  H  HCH2   0   0.254   0.0109  -1.2079  -0.1947
 BC9  H12  H  HCH2   0   0.246   0.8924  -3.3778   0.7526
 BC9  H13  H  HCH2   0   0.256   0.5718  -4.1500  -0.7927
 BC9  H14  H  H      0   0.272   2.1734  -2.5650  -1.9413
 BC9  H15  H  HCH1   0   0.223   4.3450  -1.8692  -1.9065
 BC9  H16  H  HCH1   0   0.232   5.1766  -0.7039   0.7725
 BC9  H17  H  HCH3   0   0.216   6.0068   0.1012  -2.0622
 BC9  H18  H  HCH3   0   0.234   6.5226   0.8808  -0.5721
 BC9  H19  H  HCH3   0   0.236   7.0355  -0.7637  -0.9178
 BC9  H20  H  HCH2   0   0.219   3.5033   0.4405  -1.5018
 BC9  H21  H  HCH2   0   0.224   2.9116  -0.0202   0.0735
 BC9  H22  H  HCH1   0   0.215   4.6831   2.3658  -0.5463
 BC9  H23  H  HCH3   0   0.230   5.4073   1.2637   1.6064
 BC9  H24  H  HCH3   0   0.237   4.6582   2.8156   1.9040
 BC9  H25  H  HCH3   0   0.211   3.7468   1.3332   2.1825
 BC9  H26  H  HCH2   0   0.197   2.2625   2.2294  -1.1021
 BC9  H27  H  HCH2   0   0.229   1.9064   1.9066   0.5881
 BC9  H28  H  HCH1   0   0.215   2.8888   4.4807  -0.6653
 BC9  H29  H  HCH3   0   0.230   3.7916   4.6586   1.5000
 BC9  H30  H  HCH3   0   0.225   2.2810   5.5427   1.5754
 BC9  H31  H  HCH3   0   0.220   2.3974   3.9388   2.2886
 BC9  H32  H  HCH2   0   0.231   0.7310   5.3735  -0.1603
 BC9  H33  H  HCH2   0   0.223   0.7280   4.1339  -1.3738
 BC9  H34  H  HCH1   0   0.228  -1.1876   4.4030   0.3336
 BC9  H35  H  HCH3   0   0.236   0.1413   4.2214   2.4074
 BC9  H36  H  HCH3   0   0.237  -1.1456   3.0421   2.3531
 BC9  H37  H  HCH3   0   0.224   0.5120   2.5391   2.0520
 BC9  H38  H  HCH1   0   0.215  -1.1932   2.8447  -1.4196
 BC9  H39  H  HCH2   0   0.252  -2.2606   1.7104   1.2052
 BC9  H40  H  HCH2   0   0.263  -3.1041   2.7272   0.0365
 BC9  H42  H  HOH1   0   0.455   5.4140  -3.6858  -1.0301
 BC9  H43  H  HOH1   0   0.451   0.5667   1.4955  -1.0423

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
 BC9  O33  C13  single  1.408  0.020  1.408
 BC9  C15  C14  single  1.526  0.020  1.526
 BC9  C13  C14  single  1.536  0.020  1.536
 BC9  C13  C11  single  1.517  0.020  1.517
 BC9  C14  C16  single  1.527  0.020  1.527
 BC9  C11  C10  double  1.338  0.020  1.338
 BC9  C11  C12  single  1.429  0.020  1.429
 BC9  C16  C17  single  1.540  0.020  1.540
 BC9  C10  C9   single  1.490  0.020  1.490
 BC9  C12  N35  triple  1.153  0.020  1.153
 BC9  O34  C25  single  1.411  0.020  1.411
 BC9  C21  C20  single  1.530  0.020  1.530
 BC9  C17  C18  single  1.525  0.020  1.525
 BC9  C17  C19  single  1.535  0.020  1.535
 BC9  C8   C9   single  1.533  0.020  1.533
 BC9  C8   C7   single  1.526  0.020  1.526
 BC9  C20  C19  single  1.528  0.020  1.528
 BC9  C20  C22  single  1.552  0.020  1.552
 BC9  C7   C6   single  1.522  0.020  1.522
 BC9  C25  C23  single  1.543  0.020  1.543
 BC9  C25  C26  single  1.532  0.020  1.532
 BC9  O28  C27  double  1.209  0.020  1.209
 BC9  C23  C22  single  1.557  0.020  1.557
 BC9  C23  C24  single  1.525  0.020  1.525
 BC9  C6   O29  single  1.437  0.020  1.437
 BC9  C6   C1   single  1.512  0.020  1.512
 BC9  C27  O29  single  1.322  0.020  1.322
 BC9  C27  C26  single  1.509  0.020  1.509
 BC9  C5   C1   single  1.542  0.020  1.542
 BC9  C5   C3   single  1.541  0.020  1.541
 BC9  C1   C2   single  1.541  0.020  1.541
 BC9  C3   C2   single  1.539  0.020  1.539
 BC9  C2   C30  single  1.524  0.020  1.524
 BC9  C30  O31  deloc   1.249  0.020  1.249
 BC9  C30  O32  deloc   1.249  0.020  1.249
 BC9  C1   H1   single  0.970  0.020  1.090
 BC9  C2   H2   single  0.970  0.020  1.090
 BC9  C3   H3   single  0.970  0.020  1.090
 BC9  C3   H4   single  0.970  0.020  1.090
 BC9  C5   H5   single  0.970  0.020  1.090
 BC9  C5   H6   single  0.970  0.020  1.090
 BC9  C6   H7   single  0.970  0.020  1.090
 BC9  C7   H8   single  0.970  0.020  1.090
 BC9  C7   H9   single  0.970  0.020  1.090
 BC9  C8   H10  single  0.970  0.020  1.090
 BC9  C8   H11  single  0.970  0.020  1.090
 BC9  C9   H12  single  0.970  0.020  1.090
 BC9  C9   H13  single  0.970  0.020  1.090
 BC9  C10  H14  single  0.930  0.020  1.080
 BC9  C13  H15  single  0.970  0.020  1.090
 BC9  C14  H16  single  0.970  0.020  1.090
 BC9  C15  H17  single  0.970  0.020  1.090
 BC9  C15  H18  single  0.970  0.020  1.090
 BC9  C15  H19  single  0.970  0.020  1.090
 BC9  C16  H20  single  0.970  0.020  1.090
 BC9  C16  H21  single  0.970  0.020  1.090
 BC9  C17  H22  single  0.970  0.020  1.090
 BC9  C18  H23  single  0.970  0.020  1.090
 BC9  C18  H24  single  0.970  0.020  1.090
 BC9  C18  H25  single  0.970  0.020  1.090
 BC9  C19  H26  single  0.970  0.020  1.090
 BC9  C19  H27  single  0.970  0.020  1.090
 BC9  C20  H28  single  0.970  0.020  1.090
 BC9  C21  H29  single  0.970  0.020  1.090
 BC9  C21  H30  single  0.970  0.020  1.090
 BC9  C21  H31  single  0.970  0.020  1.090
 BC9  C22  H32  single  0.970  0.020  1.090
 BC9  C22  H33  single  0.970  0.020  1.090
 BC9  C23  H34  single  0.970  0.020  1.090
 BC9  C24  H35  single  0.970  0.020  1.090
 BC9  C24  H36  single  0.970  0.020  1.090
 BC9  C24  H37  single  0.970  0.020  1.090
 BC9  C25  H38  single  0.970  0.020  1.090
 BC9  C26  H39  single  0.970  0.020  1.090
 BC9  C26  H40  single  0.970  0.020  1.090
 BC9  O33  H42  single  0.850  0.020  0.980
 BC9  O34  H43  single  0.850  0.020  0.980

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
 BC9  H1   C1   C6   109.70  3.000
 BC9  H1   C1   C5   110.24  3.000
 BC9  C6   C1   C5   117.53  3.000
 BC9  H1   C1   C2   110.54  3.000
 BC9  C5   C1   C2    88.10  3.000
 BC9  C6   C1   C2   119.09  3.000
 BC9  H2   C2   C30  108.01  3.000
 BC9  H2   C2   C3   109.39  3.000
 BC9  C30  C2   C3   119.79  3.000
 BC9  H2   C2   C1   108.84  3.000
 BC9  C30  C2   C1   120.66  3.000
 BC9  C3   C2   C1    88.69  3.000
 BC9  H4   C3   H3   108.34  3.000
 BC9  H4   C3   C5   117.52  3.000
 BC9  H3   C3   C5   111.76  3.000
 BC9  H4   C3   C2   118.19  3.000
 BC9  H3   C3   C2   111.70  3.000
 BC9  C5   C3   C2    88.25  3.000
 BC9  H6   C5   H5   108.44  3.000
 BC9  H6   C5   C3   118.07  3.000
 BC9  H5   C5   C3   111.66  3.000
 BC9  H6   C5   C1   117.51  3.000
 BC9  H5   C5   C1   111.48  3.000
 BC9  C3   C5   C1    88.60  3.000
 BC9  H7   C6   O29  109.65  3.000
 BC9  H7   C6   C7   108.74  3.000
 BC9  O29  C6   C7   107.26  3.000
 BC9  H7   C6   C1   109.07  3.000
 BC9  O29  C6   C1   108.66  3.000
 BC9  C7   C6   C1   113.41  3.000
 BC9  H9   C7   H8   106.32  3.000
 BC9  H9   C7   C8   109.34  3.000
 BC9  H8   C7   C8   110.40  3.000
 BC9  H9   C7   C6   107.43  3.000
 BC9  H8   C7   C6   109.85  3.000
 BC9  C8   C7   C6   113.22  3.000
 BC9  H11  C8   H10  106.38  3.000
 BC9  H11  C8   C9   109.32  3.000
 BC9  H10  C8   C9   108.80  3.000
 BC9  H11  C8   C7   110.14  3.000
 BC9  H10  C8   C7   109.10  3.000
 BC9  C9   C8   C7   112.88  3.000
 BC9  H13  C9   H12  106.89  3.000
 BC9  H13  C9   C10  108.58  3.000
 BC9  H12  C9   C10  111.36  3.000
 BC9  H13  C9   C8   109.07  3.000
 BC9  H12  C9   C8   110.31  3.000
 BC9  C10  C9   C8   110.53  3.000
 BC9  H14  C10  C11  116.41  3.000
 BC9  H14  C10  C9   115.82  3.000
 BC9  C11  C10  C9   127.73  3.000
 BC9  C13  C11  C12  115.40  3.000
 BC9  C12  C11  C10  120.54  3.000
 BC9  C13  C11  C10  124.06  3.000
 BC9  N35  C12  C11  180.00  3.000
 BC9  H15  C13  O33  111.25  3.000
 BC9  H15  C13  C14  108.20  3.000
 BC9  O33  C13  C14  108.00  3.000
 BC9  H15  C13  C11  106.85  3.000
 BC9  C14  C13  C11  112.61  3.000
 BC9  O33  C13  C11  109.95  3.000
 BC9  H16  C14  C16  108.88  3.000
 BC9  H16  C14  C15  108.58  3.000
 BC9  C16  C14  C15  111.49  3.000
 BC9  H16  C14  C13  107.05  3.000
 BC9  C16  C14  C13  109.68  3.000
 BC9  C15  C14  C13  111.03  3.000
 BC9  H19  C15  H18  107.46  3.000
 BC9  H19  C15  H17  108.03  3.000
 BC9  H18  C15  H17  107.37  3.000
 BC9  H19  C15  C14  112.25  3.000
 BC9  H18  C15  C14  110.65  3.000
 BC9  H17  C15  C14  110.89  3.000
 BC9  H21  C16  H20  105.52  3.000
 BC9  H21  C16  C17  106.42  3.000
 BC9  H20  C16  C17  108.52  3.000
 BC9  H21  C16  C14  108.81  3.000
 BC9  H20  C16  C14  108.56  3.000
 BC9  C17  C16  C14  118.30  3.000
 BC9  H22  C17  C19  109.56  3.000
 BC9  H22  C17  C18  108.99  3.000
 BC9  C19  C17  C18  113.69  3.000
 BC9  H22  C17  C16  109.69  3.000
 BC9  C19  C17  C16  104.21  3.000
 BC9  C18  C17  C16  110.58  3.000
 BC9  H25  C18  H24  107.84  3.000
 BC9  H25  C18  H23  107.27  3.000
 BC9  H24  C18  H23  106.82  3.000
 BC9  H25  C18  C17  110.76  3.000
 BC9  H24  C18  C17  112.48  3.000
 BC9  H23  C18  C17  111.42  3.000
 BC9  H27  C19  H26  106.74  3.000
 BC9  H27  C19  C20  108.67  3.000
 BC9  H26  C19  C20  104.97  3.000
 BC9  H27  C19  C17  106.26  3.000
 BC9  H26  C19  C17  105.28  3.000
 BC9  C20  C19  C17  123.82  3.000
 BC9  H28  C20  C22  103.69  3.000
 BC9  H28  C20  C21  106.04  3.000
 BC9  C22  C20  C21  113.04  3.000
 BC9  H28  C20  C19  107.07  3.000
 BC9  C22  C20  C19  110.90  3.000
 BC9  C21  C20  C19  115.13  3.000
 BC9  H31  C21  H30  107.47  3.000
 BC9  H31  C21  H29  107.38  3.000
 BC9  H30  C21  H29  106.81  3.000
 BC9  H31  C21  C20  113.13  3.000
 BC9  H30  C21  C20  110.80  3.000
 BC9  H29  C21  C20  110.96  3.000
 BC9  H33  C22  H32  104.75  3.000
 BC9  H33  C22  C23  107.58  3.000
 BC9  H32  C22  C23  106.90  3.000
 BC9  H33  C22  C20  107.48  3.000
 BC9  H32  C22  C20  105.60  3.000
 BC9  C23  C22  C20  123.14  3.000
 BC9  H34  C23  C25  103.00  3.000
 BC9  H34  C23  C24  106.47  3.000
 BC9  C25  C23  C24  113.82  3.000
 BC9  H34  C23  C22  104.33  3.000
 BC9  C24  C23  C22  114.35  3.000
 BC9  C25  C23  C22  113.42  3.000
 BC9  H37  C24  H36  107.54  3.000
 BC9  H37  C24  H35  107.66  3.000
 BC9  H36  C24  H35  106.51  3.000
 BC9  H37  C24  C23  112.59  3.000
 BC9  H36  C24  C23  111.57  3.000
 BC9  H35  C24  C23  110.68  3.000
 BC9  H38  C25  O34  109.68  3.000
 BC9  H38  C25  C26  107.19  3.000
 BC9  O34  C25  C26  104.69  3.000
 BC9  H38  C25  C23  106.37  3.000
 BC9  C26  C25  C23  113.70  3.000
 BC9  O34  C25  C23  114.97  3.000
 BC9  H40  C26  H39  108.01  3.000
 BC9  H40  C26  C27  109.62  3.000
 BC9  H39  C26  C27  110.06  3.000
 BC9  H40  C26  C25  110.05  3.000
 BC9  H39  C26  C25  111.25  3.000
 BC9  C27  C26  C25  107.85  3.000
 BC9  O29  C27  O28  124.80  3.000
 BC9  O29  C27  C26  111.79  3.000
 BC9  O28  C27  C26  123.24  3.000
 BC9  C27  O29  C6   120.92  3.000
 BC9  O32  C30  O31  126.35  3.000
 BC9  O32  C30  C2   116.16  3.000
 BC9  O31  C30  C2   117.48  3.000
 BC9  H42  O33  C13  108.51  3.000
 BC9  H43  O34  C25  109.21  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
 BC9  Var_01  C13  C11  C10  C9   -177.24   0.0  0
 BC9  Var_02  C2   C3   C5   C1     18.92  30.0  1
 BC9  Var_03  C9   C8   C7   C6   -173.61  30.0  1
 BC9  Var_04  C26  C27  O29  C6   -178.32  30.0  1
 BC9  Var_05  C10  C9   C8   C7    178.40  30.0  1
 BC9  Var_06  C11  C10  C9   C8    118.85  30.0  1
 BC9  Var_07  O29  C27  C26  C25   102.09  30.0  1
 BC9  Var_08  H14  C10  C11  C13     0.23   0.0  0

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
 BC9  chir_01  C1   C6   C5   C2   positiv
 BC9  chir_02  C2   C1   C3   C30  negativ
 BC9  chir_03  C6   O29  C7   C1   negativ
 BC9  chir_04  C13  O33  C14  C11  positiv
 BC9  chir_05  C14  C16  C13  C15  negativ
 BC9  chir_06  C17  C19  C18  C16  negativ
 BC9  chir_07  C20  C21  C19  C22  negativ
 BC9  chir_08  C23  C24  C22  C25  negativ
 BC9  chir_09  C25  O34  C23  C26  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
 BC9  plan-1  C2   0.020
 BC9  plan-1  C30  0.020
 BC9  plan-1  O31  0.020
 BC9  plan-1  O32  0.020
 BC9  plan-2  C9   0.020
 BC9  plan-2  C10  0.020
 BC9  plan-2  C11  0.020
 BC9  plan-2  C12  0.020
 BC9  plan-2  C13  0.020
 BC9  plan-2  H14  0.020
 BC9  plan-3  C26  0.020
 BC9  plan-3  C27  0.020
 BC9  plan-3  O28  0.020
 BC9  plan-3  O29  0.020

