# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 11 22:28:46 2020
#   Inital geometry file: a 132 line input string
#   Ligand name: (8~{R},9~{S},13~{S},14~{S},16~{E})-13-methyl-3-oxidanyl-16-(phenylmethylidene)-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CC(=C/c5ccccc5)\C2=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
 6WN  6WN  (8~{R},9~{S},13~{S},14~{S},16~{E})-13-methyl-3-oxidanyl-16-(phenylmethylidene)-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-one  ligand  53  27  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_6WN
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
 6WN  O01  O  O     0  -0.402  -2.3387  -3.2200  -0.0413
 6WN  C01  C  CR5   0   0.406  -1.8505  -2.1252   0.1344
 6WN  C02  C  CR5   0  -0.216  -0.3923  -1.8196   0.3992
 6WN  C03  C  CH3   0  -0.667  -0.2524  -1.8625   1.9326
 6WN  C04  C  CH2   0  -0.410   0.6395  -2.7153  -0.2682
 6WN  C05  C  CH2   0  -0.453   2.0431  -2.1153  -0.1212
 6WN  C06  C  CR16  0  -0.263   2.1300  -0.6535  -0.5840
 6WN  C07  C  CR66  0   0.100   3.5163  -0.0518  -0.4358
 6WN  C08  C  CR16  0  -0.312   4.6619  -0.8243  -0.6243
 6WN  C09  C  CR16  0  -0.386   5.9394  -0.2960  -0.5321
 6WN  C10  C  CR6   0   0.346   6.1013   1.0548  -0.2442
 6WN  O02  O  OH1   0  -0.638   7.3129   1.6421  -0.1385
 6WN  C11  C  CR16  0  -0.385   4.9737   1.8442  -0.0603
 6WN  C12  C  CR66  0   0.074   3.6919   1.3096  -0.1540
 6WN  C13  C  C     0  -0.509   2.5215   2.2314   0.0822
 6WN  C14  C  C     0  -0.433   1.1982   1.6566  -0.3958
 6WN  C15  C  CR16  0  -0.239   1.0641   0.2236   0.0939
 6WN  C16  C  CR15  0  -0.203  -0.2880  -0.4025  -0.1820
 6WN  C17  C  CH2   0  -0.544  -1.5755   0.2904   0.2701
 6WN  C18  C  CR5   0   0.049  -2.5821  -0.8253   0.1586
 6WN  C19  C  C1    0  -0.353  -3.9119  -0.7864  -0.0037
 6WN  C20  C  CR6   0   0.141  -4.7898   0.3769  -0.0435
 6WN  C21  C  CR16  0  -0.302  -6.0330   0.2425  -0.6725
 6WN  C22  C  CR16  0  -0.242  -6.9021   1.3163  -0.7743
 6WN  C23  C  CR16  0  -0.260  -6.5541   2.5447  -0.2265
 6WN  C24  C  CR16  0  -0.235  -5.3364   2.6862   0.4276
 6WN  C25  C  CR16  0  -0.317  -4.4604   1.6157   0.5185
 6WN  H1   H  HCH3  0   0.246  -0.4539  -2.8731   2.2918
 6WN  H2   H  HCH3  0   0.251   0.7515  -1.5961   2.2595
 6WN  H3   H  HCH3  0   0.245  -0.9459  -1.1904   2.4391
 6WN  H4   H  HCH2  0   0.236   0.6256  -3.7223   0.1553
 6WN  H5   H  HCH2  0   0.230   0.3982  -2.8177  -1.3313
 6WN  H6   H  HCH2  0   0.226   2.3755  -2.1860   0.9190
 6WN  H7   H  HCH2  0   0.244   2.7321  -2.7326  -0.6997
 6WN  H8   H  HCR6  0   0.231   1.8884  -0.6463  -1.6579
 6WN  H9   H  HCR6  0   0.245   4.5706  -1.8778  -0.8535
 6WN  H10  H  HCR6  0   0.263   6.8017  -0.9349  -0.6861
 6WN  H11  H  HOH1  0   0.472   8.0111   0.9952  -0.2868
 6WN  H12  H  HCR6  0   0.249   5.0960   2.9003   0.1564
 6WN  H13  H  H     0   0.244   2.4499   2.4310   1.1570
 6WN  H14  H  H     0   0.248   2.7184   3.1984  -0.3869
 6WN  H15  H  H     0   0.242   0.3788   2.2749  -0.0211
 6WN  H16  H  H     0   0.221   1.1382   1.6836  -1.4894
 6WN  H17  H  HCR6  0   0.226   1.2443   0.2272   1.1775
 6WN  H18  H  HCR5  0   0.239  -0.3705  -0.5103  -1.2746
 6WN  H19  H  HCH2  0   0.254  -1.4938   0.6651   1.2965
 6WN  H20  H  HCH2  0   0.266  -1.8374   1.1435  -0.3585
 6WN  H21  H  H     0   0.257  -4.4079  -1.7403  -0.1656
 6WN  H22  H  HCR6  0   0.259  -6.3129  -0.7158  -1.0938
 6WN  H23  H  HCR6  0   0.261  -7.8527   1.1941  -1.2770
 6WN  H24  H  HCR6  0   0.262  -7.2317   3.3851  -0.3009
 6WN  H25  H  HCR6  0   0.262  -5.0681   3.6349   0.8740
 6WN  H26  H  HCR6  0   0.272  -3.5301   1.7443   1.0538

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
 6WN  C23  C24  aromatic  1.389  0.020  1.389
 6WN  C23  C22  aromatic  1.389  0.020  1.389
 6WN  C24  C25  aromatic  1.386  0.020  1.386
 6WN  C22  C21  aromatic  1.385  0.020  1.385
 6WN  C25  C20  aromatic  1.400  0.020  1.400
 6WN  C21  C20  aromatic  1.400  0.020  1.400
 6WN  C20  C19  single    1.458  0.020  1.458
 6WN  C19  C18  double    1.340  0.020  1.340
 6WN  C18  C17  single    1.507  0.020  1.507
 6WN  C18  C01  single    1.492  0.020  1.492
 6WN  C17  C16  single    1.530  0.020  1.530
 6WN  O01  C01  double    1.211  0.020  1.211
 6WN  C01  C02  single    1.513  0.020  1.513
 6WN  C03  C02  single    1.540  0.020  1.540
 6WN  C02  C16  single    1.535  0.020  1.535
 6WN  C02  C04  single    1.521  0.020  1.521
 6WN  C16  C15  single    1.515  0.020  1.515
 6WN  C15  C14  single    1.520  0.020  1.520
 6WN  C15  C06  single    1.538  0.020  1.538
 6WN  C14  C13  single    1.520  0.020  1.520
 6WN  C04  C05  single    1.534  0.020  1.534
 6WN  C13  C12  single    1.508  0.020  1.508
 6WN  C05  C06  single    1.536  0.020  1.536
 6WN  C06  C07  single    1.519  0.020  1.519
 6WN  C12  C07  aromatic  1.401  0.020  1.401
 6WN  C12  C11  aromatic  1.392  0.020  1.392
 6WN  C07  C08  aromatic  1.394  0.020  1.394
 6WN  C11  C10  aromatic  1.389  0.020  1.389
 6WN  C08  C09  aromatic  1.386  0.020  1.386
 6WN  C10  C09  aromatic  1.391  0.020  1.391
 6WN  C10  O02  single    1.351  0.020  1.351
 6WN  C03  H1   single    0.970  0.020  1.090
 6WN  C03  H2   single    0.970  0.020  1.090
 6WN  C03  H3   single    0.970  0.020  1.090
 6WN  C04  H4   single    0.970  0.020  1.090
 6WN  C04  H5   single    0.970  0.020  1.090
 6WN  C05  H6   single    0.970  0.020  1.090
 6WN  C05  H7   single    0.970  0.020  1.090
 6WN  C06  H8   single    0.970  0.020  1.090
 6WN  C08  H9   single    0.930  0.020  1.080
 6WN  C09  H10  single    0.930  0.020  1.080
 6WN  O02  H11  single    0.850  0.020  0.980
 6WN  C11  H12  single    0.930  0.020  1.080
 6WN  C13  H13  single    0.970  0.020  1.090
 6WN  C13  H14  single    0.970  0.020  1.090
 6WN  C14  H15  single    0.970  0.020  1.090
 6WN  C14  H16  single    0.970  0.020  1.090
 6WN  C15  H17  single    0.970  0.020  1.090
 6WN  C16  H18  single    0.970  0.020  1.090
 6WN  C17  H19  single    0.970  0.020  1.090
 6WN  C17  H20  single    0.970  0.020  1.090
 6WN  C19  H21  single    0.930  0.020  1.080
 6WN  C21  H22  single    0.930  0.020  1.080
 6WN  C22  H23  single    0.930  0.020  1.080
 6WN  C23  H24  single    0.930  0.020  1.080
 6WN  C24  H25  single    0.930  0.020  1.080
 6WN  C25  H26  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
 6WN  C18  C01  C02  107.08  3.000
 6WN  C02  C01  O01  126.60  3.000
 6WN  C18  C01  O01  126.31  3.000
 6WN  C16  C02  C04  109.36  3.000
 6WN  C04  C02  C03  111.03  3.000
 6WN  C16  C02  C03  113.36  3.000
 6WN  C04  C02  C01  117.26  3.000
 6WN  C16  C02  C01  100.70  3.000
 6WN  C03  C02  C01  104.84  3.000
 6WN  H3   C03  H2   107.22  3.000
 6WN  H3   C03  H1   107.48  3.000
 6WN  H2   C03  H1   107.34  3.000
 6WN  H3   C03  C02  112.79  3.000
 6WN  H2   C03  C02  112.07  3.000
 6WN  H1   C03  C02  109.68  3.000
 6WN  H5   C04  H4   106.70  3.000
 6WN  H5   C04  C05  109.35  3.000
 6WN  H4   C04  C05  109.58  3.000
 6WN  H5   C04  C02  109.37  3.000
 6WN  H4   C04  C02  111.36  3.000
 6WN  C05  C04  C02  110.39  3.000
 6WN  H7   C05  H6   106.00  3.000
 6WN  H7   C05  C06  110.06  3.000
 6WN  H6   C05  C06  109.31  3.000
 6WN  H7   C05  C04  107.81  3.000
 6WN  H6   C05  C04  110.12  3.000
 6WN  C06  C05  C04  113.29  3.000
 6WN  H8   C06  C15  105.91  3.000
 6WN  H8   C06  C07  107.04  3.000
 6WN  C15  C06  C07  111.33  3.000
 6WN  H8   C06  C05  106.73  3.000
 6WN  C07  C06  C05  113.54  3.000
 6WN  C15  C06  C05  111.77  3.000
 6WN  C12  C07  C08  117.54  3.000
 6WN  C08  C07  C06  121.15  3.000
 6WN  C12  C07  C06  121.26  3.000
 6WN  H9   C08  C09  117.59  3.000
 6WN  H9   C08  C07  119.92  3.000
 6WN  C09  C08  C07  122.49  3.000
 6WN  H10  C09  C10  120.61  3.000
 6WN  H10  C09  C08  119.94  3.000
 6WN  C10  C09  C08  119.44  3.000
 6WN  C11  C10  O02  118.09  3.000
 6WN  O02  C10  C09  122.89  3.000
 6WN  C11  C10  C09  119.01  3.000
 6WN  H11  O02  C10  110.26  3.000
 6WN  H12  C11  C12  119.42  3.000
 6WN  H12  C11  C10  119.22  3.000
 6WN  C12  C11  C10  121.36  3.000
 6WN  C13  C12  C11  117.98  3.000
 6WN  C11  C12  C07  120.14  3.000
 6WN  C13  C12  C07  121.87  3.000
 6WN  H14  C13  H13  105.77  3.000
 6WN  H14  C13  C14  110.89  3.000
 6WN  H13  C13  C14  108.69  3.000
 6WN  H14  C13  C12  109.50  3.000
 6WN  H13  C13  C12  108.40  3.000
 6WN  C14  C13  C12  113.28  3.000
 6WN  H16  C14  H15  106.69  3.000
 6WN  H16  C14  C15  109.87  3.000
 6WN  H15  C14  C15  110.90  3.000
 6WN  H16  C14  C13  110.63  3.000
 6WN  H15  C14  C13  109.33  3.000
 6WN  C15  C14  C13  109.39  3.000
 6WN  H17  C15  C16  109.10  3.000
 6WN  H17  C15  C14  107.47  3.000
 6WN  C16  C15  C14  114.18  3.000
 6WN  H17  C15  C06  108.85  3.000
 6WN  C14  C15  C06  109.54  3.000
 6WN  C16  C15  C06  107.60  3.000
 6WN  H18  C16  C17  105.93  3.000
 6WN  H18  C16  C15  106.74  3.000
 6WN  C17  C16  C15  120.65  3.000
 6WN  H18  C16  C02  106.28  3.000
 6WN  C15  C16  C02  111.91  3.000
 6WN  C17  C16  C02  104.41  3.000
 6WN  H20  C17  H19  106.86  3.000
 6WN  H20  C17  C18  112.07  3.000
 6WN  H19  C17  C18  111.86  3.000
 6WN  H20  C17  C16  112.68  3.000
 6WN  H19  C17  C16  111.65  3.000
 6WN  C18  C17  C16  101.82  3.000
 6WN  C19  C18  C17  130.56  3.000
 6WN  C17  C18  C01  108.59  3.000
 6WN  C19  C18  C01  120.66  3.000
 6WN  H21  C19  C20  114.91  3.000
 6WN  H21  C19  C18  116.44  3.000
 6WN  C20  C19  C18  128.61  3.000
 6WN  C25  C20  C21  118.33  3.000
 6WN  C21  C20  C19  118.06  3.000
 6WN  C25  C20  C19  123.61  3.000
 6WN  H22  C21  C22  119.66  3.000
 6WN  H22  C21  C20  119.28  3.000
 6WN  C22  C21  C20  121.05  3.000
 6WN  H23  C22  C23  120.20  3.000
 6WN  H23  C22  C21  119.85  3.000
 6WN  C23  C22  C21  119.95  3.000
 6WN  H24  C23  C24  120.14  3.000
 6WN  H24  C23  C22  120.18  3.000
 6WN  C24  C23  C22  119.68  3.000
 6WN  H25  C24  C25  119.55  3.000
 6WN  H25  C24  C23  120.05  3.000
 6WN  C25  C24  C23  120.40  3.000
 6WN  H26  C25  C24  118.98  3.000
 6WN  H26  C25  C20  120.44  3.000
 6WN  C24  C25  C20  120.56  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
 6WN  CONST_01  C10  C11  C12  C07     0.00   0.0  0
 6WN  CONST_02  C10  C09  C08  C07     0.00   0.0  0
 6WN  CONST_03  C11  C12  C07  C08     0.00   0.0  0
 6WN  CONST_04  C11  C10  C09  C08     0.00   0.0  0
 6WN  CONST_05  C12  C07  C08  C09     0.00   0.0  0
 6WN  CONST_06  C12  C11  C10  C09     0.00   0.0  0
 6WN  CONST_07  C23  C24  C25  C20     0.00   0.0  0
 6WN  CONST_08  C23  C22  C21  C20     0.00   0.0  0
 6WN  CONST_09  C24  C23  C22  C21     0.00   0.0  0
 6WN  CONST_10  C24  C25  C20  C21     0.00   0.0  0
 6WN  CONST_11  C25  C24  C23  C22     0.00   0.0  0
 6WN  CONST_12  C25  C20  C21  C22     0.00   0.0  0
 6WN  CONST_13  O02  C10  C09  C08   180.00   0.0  0
 6WN  CONST_14  C12  C11  C10  O02   180.00   0.0  0
 6WN  CONST_15  C24  C25  C20  C19   180.00   0.0  0
 6WN  CONST_16  C22  C21  C20  C19   180.00   0.0  0
 6WN  CONST_17  H9   C08  C07  C06     0.00   0.0  0
 6WN  CONST_18  H12  C11  C12  C07   180.00   0.0  0
 6WN  CONST_19  H10  C09  C08  C07   180.00   0.0  0
 6WN  CONST_20  H25  C24  C25  C20   180.00   0.0  0
 6WN  CONST_21  H23  C22  C21  C20   180.00   0.0  0
 6WN  CONST_22  H24  C23  C22  C21   180.00   0.0  0
 6WN  CONST_23  H26  C25  C20  C21   180.00   0.0  0
 6WN  CONST_24  H22  C21  C22  C23   180.00   0.0  0
 6WN  Var_01    C16  C17  C18  C01    19.00  30.0  1
 6WN  Var_02    C17  C18  C01  C02     6.68  30.0  1
 6WN  Var_03    C06  C05  C04  C02   -52.19  30.0  1
 6WN  Var_04    C14  C13  C12  C07   -16.39  30.0  1
 6WN  Var_05    C15  C14  C13  C12    47.24  30.0  1
 6WN  Var_06    C20  C19  C18  C01  -178.33  30.0  2
 6WN  Var_07    C25  C20  C19  C18   -22.37  30.0  2

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
 6WN  chir_01  C02  C01  C16  C04  positiv
 6WN  chir_02  C06  C15  C05  C07  positiv
 6WN  chir_03  C15  C06  C14  C16  negativ
 6WN  chir_04  C16  C17  C02  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
 6WN  plan-1  C19  0.020
 6WN  plan-1  C20  0.020
 6WN  plan-1  C21  0.020
 6WN  plan-1  C22  0.020
 6WN  plan-1  C23  0.020
 6WN  plan-1  C24  0.020
 6WN  plan-1  C25  0.020
 6WN  plan-1  H22  0.020
 6WN  plan-1  H23  0.020
 6WN  plan-1  H24  0.020
 6WN  plan-1  H25  0.020
 6WN  plan-1  H26  0.020
 6WN  plan-2  C06  0.020
 6WN  plan-2  C07  0.020
 6WN  plan-2  C08  0.020
 6WN  plan-2  C09  0.020
 6WN  plan-2  C10  0.020
 6WN  plan-2  O02  0.020
 6WN  plan-2  C11  0.020
 6WN  plan-2  C12  0.020
 6WN  plan-2  C13  0.020
 6WN  plan-2  H9   0.020
 6WN  plan-2  H10  0.020
 6WN  plan-2  H12  0.020
 6WN  plan-3  O01  0.020
 6WN  plan-3  C01  0.020
 6WN  plan-3  C02  0.020
 6WN  plan-3  C18  0.020

