# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 08:52:50 2022
#   Inital geometry file: a 148 line input string
#   Ligand name: (6aS,8aR,12aS,12bR,13aR)-5,6a,9,9,12a,13a-hexamethyl-7,8,8a,9,11,12,12a,12b,13,13a-decahydro-3H-benzo[a]furo[3,4-j]xanthene-3,4,10(1H,6aH)-trione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1=C2O[C@@]3(C)CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3C[C@]2(C)C5=C(C(=O)OC5)C1=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
 9FR  9FR  (6aS,8aR,12aS,12bR,13aR)-5,6a,9,9,12a,13a-hexamethyl-7,8,8a,9,11,12,12a,12b,13,13a-decahydro-3H-benzo[a]furo[3,4-j]xanthene-3,4,10(1H,6aH)-trione  ligand  62  30  .  2022-03-11  2022-03-11
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_9FR
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
 9FR  C10  C  CR6   0   0.456   4.9781  -1.3185  -0.1353
 9FR  C13  C  CH3   0  -0.650   5.5897   0.9574  -0.9497
 9FR  C15  C  CT    0  -0.255  -1.5410  -0.4698   0.4410
 9FR  C17  C  C     0  -0.185  -2.7467   1.7481   0.1893
 9FR  C20  C  CR5   0   0.130  -2.8530  -1.0818   0.1254
 9FR  C21  C  CR5   0   0.572  -5.0939  -1.3373  -0.1784
 9FR  C22  C  CH2   0  -0.184  -3.1566  -2.5305  -0.0126
 9FR  C24  C  CH3   0  -0.662  -1.3830  -0.7023   1.9718
 9FR  C01  C  CH1   0  -0.192   0.8213  -0.2575  -0.7729
 9FR  C02  C  CT    0   0.189   0.3911   1.2099  -0.9478
 9FR  C03  C  CH2   0  -0.441   1.5487   2.2003  -1.0290
 9FR  C04  C  CH2   0  -0.452   2.7407   1.8893  -0.1411
 9FR  C05  C  CR16  0  -0.176   3.1891   0.4555  -0.4092
 9FR  C06  C  CR6   0  -0.069   2.0984  -0.5292   0.0836
 9FR  C07  C  CH3   0  -0.699   1.8206  -0.4301   1.5818
 9FR  C08  C  C     0  -0.438   2.5720  -1.9526  -0.2405
 9FR  C09  C  C     0  -0.562   3.9318  -2.2699   0.3763
 9FR  C11  C  CR6   0  -0.226   4.6718   0.1709  -0.0094
 9FR  O01  O  O     0  -0.401   6.0181  -1.7211  -0.6093
 9FR  C12  C  CH3   0  -0.665   5.0367   0.5786   1.4308
 9FR  O02  O  O2    0  -0.489  -0.4083   1.6176   0.2007
 9FR  C14  C  C     0   0.439  -1.6112   1.0222   0.2462
 9FR  C16  C  CH2   0  -0.488  -0.4248  -1.1118  -0.4312
 9FR  C18  C  C     0   0.341  -4.0476   1.0683   0.1384
 9FR  C19  C  CR5   0  -0.248  -3.9907  -0.3902   0.0275
 9FR  O03  O  O     0  -0.455  -4.5641  -2.5775  -0.1993
 9FR  O04  O  O     0  -0.415  -6.2711  -1.1532  -0.3150
 9FR  O05  O  O     0  -0.402  -5.1027   1.6790   0.1318
 9FR  C23  C  CH3   0  -0.708  -2.7644   3.2424   0.1017
 9FR  C25  C  CH3   0  -0.688  -0.4491   1.3644  -2.2188
 9FR  H1   H  HCH3  0   0.231   5.3934   0.7248  -1.9974
 9FR  H2   H  HCH3  0   0.233   5.4511   2.0299  -0.8167
 9FR  H3   H  HCH3  0   0.237   6.6388   0.7466  -0.7485
 9FR  H5   H  HCH2  0   0.288  -2.6570  -2.9787  -0.8752
 9FR  H6   H  HCH2  0   0.289  -2.8808  -3.1045   0.8756
 9FR  H7   H  HCH3  0   0.254  -1.1543  -1.7480   2.1790
 9FR  H8   H  HCH3  0   0.272  -0.5951  -0.0862   2.3906
 9FR  H9   H  HCH3  0   0.265  -2.3095  -0.4448   2.4837
 9FR  H10  H  HCH1  0   0.249   1.1124  -0.5790  -1.7797
 9FR  H11  H  HCH2  0   0.235   1.9047   2.1969  -2.0629
 9FR  H12  H  HCH2  0   0.251   1.1594   3.2048  -0.8446
 9FR  H13  H  HCH2  0   0.246   3.5275   2.6071  -0.3787
 9FR  H14  H  HCH2  0   0.234   2.5068   2.0411   0.9145
 9FR  H15  H  HCR6  0   0.225   3.1942   0.3344  -1.5038
 9FR  H16  H  HCH3  0   0.242   1.3659   0.5169   1.8630
 9FR  H17  H  HCH3  0   0.244   1.1496  -1.2303   1.8897
 9FR  H18  H  HCH3  0   0.244   2.7166  -0.5395   2.1867
 9FR  H19  H  H     0   0.250   1.8483  -2.6916   0.1101
 9FR  H20  H  H     0   0.266   4.2339  -3.2925   0.1471
 9FR  H21  H  HCH3  0   0.244   6.1121   0.4761   1.5835
 9FR  H22  H  HCH3  0   0.249   4.7794   1.6239   1.6014
 9FR  H23  H  HCH3  0   0.240   4.5430  -0.0109   2.1992
 9FR  H25  H  HCH2  0   0.274  -0.1332  -2.0582   0.0269
 9FR  H26  H  HCH2  0   0.275  -0.8827  -1.3834  -1.3843
 9FR  H27  H  HCH3  0   0.243  -3.2302   3.5753  -0.8274
 9FR  H28  H  HCH3  0   0.245  -3.3437   3.6728   0.9198
 9FR  H29  H  HCH3  0   0.249  -1.7622   3.6593   0.1431
 9FR  H30  H  HCH3  0   0.244  -1.2995   0.6834  -2.2681
 9FR  H31  H  HCH3  0   0.251  -0.8288   2.3836  -2.3089
 9FR  H32  H  HCH3  0   0.253   0.1766   1.1643  -3.0881
 9FR  H4   H  H     0   0.238   2.6403  -2.0751  -1.3269
 9FR  H33  H  H     0   0.263   3.8779  -2.1908   1.4663

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
 9FR  O01  C10  double  1.212  0.020  1.212
 9FR  C07  C06  single  1.527  0.020  1.527
 9FR  C12  C11  single  1.541  0.020  1.541
 9FR  C10  C09  single  1.504  0.020  1.504
 9FR  C10  C11  single  1.526  0.020  1.526
 9FR  C09  C08  single  1.527  0.020  1.527
 9FR  C11  C05  single  1.562  0.020  1.562
 9FR  C11  C13  single  1.531  0.020  1.531
 9FR  C08  C06  single  1.535  0.020  1.535
 9FR  C22  O03  single  1.421  0.020  1.421
 9FR  C22  C20  single  1.487  0.020  1.487
 9FR  C06  C05  single  1.550  0.020  1.550
 9FR  C06  C01  single  1.561  0.020  1.561
 9FR  C24  C15  single  1.556  0.020  1.556
 9FR  C16  C01  single  1.549  0.020  1.549
 9FR  C16  C15  single  1.555  0.020  1.555
 9FR  C05  C04  single  1.526  0.020  1.526
 9FR  O03  C21  single  1.349  0.020  1.349
 9FR  C04  C03  single  1.519  0.020  1.519
 9FR  C01  C02  single  1.539  0.020  1.539
 9FR  C15  C20  single  1.482  0.020  1.482
 9FR  C15  C14  single  1.506  0.020  1.506
 9FR  C20  C19  double  1.335  0.020  1.335
 9FR  C21  C19  single  1.468  0.020  1.468
 9FR  C21  O04  double  1.199  0.020  1.199
 9FR  C03  C02  single  1.526  0.020  1.526
 9FR  C02  O02  single  1.457  0.020  1.457
 9FR  C02  C25  single  1.531  0.020  1.531
 9FR  C19  C18  single  1.464  0.020  1.464
 9FR  C14  O02  single  1.343  0.020  1.343
 9FR  C14  C17  double  1.349  0.020  1.349
 9FR  C18  C17  single  1.469  0.020  1.469
 9FR  C18  O05  double  1.219  0.020  1.219
 9FR  C17  C23  single  1.497  0.020  1.497
 9FR  C13  H1   single  0.970  0.020  1.090
 9FR  C13  H2   single  0.970  0.020  1.090
 9FR  C13  H3   single  0.970  0.020  1.090
 9FR  C22  H5   single  0.970  0.020  1.090
 9FR  C22  H6   single  0.970  0.020  1.090
 9FR  C24  H7   single  0.970  0.020  1.090
 9FR  C24  H8   single  0.970  0.020  1.090
 9FR  C24  H9   single  0.970  0.020  1.090
 9FR  C01  H10  single  0.970  0.020  1.090
 9FR  C03  H11  single  0.970  0.020  1.090
 9FR  C03  H12  single  0.970  0.020  1.090
 9FR  C04  H13  single  0.970  0.020  1.090
 9FR  C04  H14  single  0.970  0.020  1.090
 9FR  C05  H15  single  0.970  0.020  1.090
 9FR  C07  H16  single  0.970  0.020  1.090
 9FR  C07  H17  single  0.970  0.020  1.090
 9FR  C07  H18  single  0.970  0.020  1.090
 9FR  C08  H19  single  0.970  0.020  1.090
 9FR  C09  H20  single  0.970  0.020  1.090
 9FR  C12  H21  single  0.970  0.020  1.090
 9FR  C12  H22  single  0.970  0.020  1.090
 9FR  C12  H23  single  0.970  0.020  1.090
 9FR  C16  H25  single  0.970  0.020  1.090
 9FR  C16  H26  single  0.970  0.020  1.090
 9FR  C23  H27  single  0.970  0.020  1.090
 9FR  C23  H28  single  0.970  0.020  1.090
 9FR  C23  H29  single  0.970  0.020  1.090
 9FR  C25  H30  single  0.970  0.020  1.090
 9FR  C25  H31  single  0.970  0.020  1.090
 9FR  C25  H32  single  0.970  0.020  1.090
 9FR  C08  H4   single  0.970  0.020  1.090
 9FR  C09  H33  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
 9FR  O01  C10  C11  121.93  3.000
 9FR  C11  C10  C09  116.73  3.000
 9FR  O01  C10  C09  121.33  3.000
 9FR  H3   C13  H2   106.89  3.000
 9FR  H3   C13  H1   108.03  3.000
 9FR  H2   C13  H1   107.71  3.000
 9FR  H3   C13  C11  111.39  3.000
 9FR  H2   C13  C11  110.76  3.000
 9FR  H1   C13  C11  111.86  3.000
 9FR  C16  C15  C14  111.70  3.000
 9FR  C14  C15  C24  106.26  3.000
 9FR  C16  C15  C24  114.65  3.000
 9FR  C14  C15  C20  109.90  3.000
 9FR  C16  C15  C20  110.21  3.000
 9FR  C24  C15  C20  103.74  3.000
 9FR  C23  C17  C18  116.72  3.000
 9FR  C23  C17  C14  123.33  3.000
 9FR  C18  C17  C14  119.87  3.000
 9FR  C19  C20  C22  108.90  3.000
 9FR  C19  C20  C15  123.80  3.000
 9FR  C22  C20  C15  127.09  3.000
 9FR  O04  C21  O03  121.66  3.000
 9FR  O04  C21  C19  130.87  3.000
 9FR  O03  C21  C19  107.46  3.000
 9FR  H6   C22  H5   108.10  3.000
 9FR  H6   C22  O03  109.84  3.000
 9FR  H5   C22  O03  109.61  3.000
 9FR  H6   C22  C20  112.64  3.000
 9FR  H5   C22  C20  112.31  3.000
 9FR  O03  C22  C20  104.29  3.000
 9FR  H9   C24  H8   107.59  3.000
 9FR  H9   C24  H7   108.42  3.000
 9FR  H8   C24  H7   108.61  3.000
 9FR  H9   C24  C15  109.91  3.000
 9FR  H8   C24  C15  111.63  3.000
 9FR  H7   C24  C15  110.58  3.000
 9FR  H10  C01  C16  104.74  3.000
 9FR  H10  C01  C06  103.63  3.000
 9FR  C16  C01  C06  116.17  3.000
 9FR  H10  C01  C02  104.44  3.000
 9FR  C16  C01  C02  109.03  3.000
 9FR  C06  C01  C02  117.18  3.000
 9FR  C25  C02  O02  108.96  3.000
 9FR  C25  C02  C03  107.86  3.000
 9FR  O02  C02  C03  106.06  3.000
 9FR  C25  C02  C01  110.11  3.000
 9FR  O02  C02  C01  109.29  3.000
 9FR  C03  C02  C01  114.39  3.000
 9FR  H12  C03  H11  106.16  3.000
 9FR  H12  C03  C04  111.66  3.000
 9FR  H11  C03  C04  107.26  3.000
 9FR  H12  C03  C02  108.50  3.000
 9FR  H11  C03  C02  107.18  3.000
 9FR  C04  C03  C02  115.56  3.000
 9FR  H14  C04  H13  105.87  3.000
 9FR  H14  C04  C05  111.31  3.000
 9FR  H13  C04  C05  111.59  3.000
 9FR  H14  C04  C03  111.63  3.000
 9FR  H13  C04  C03  107.70  3.000
 9FR  C05  C04  C03  108.68  3.000
 9FR  H15  C05  C11  103.30  3.000
 9FR  H15  C05  C06  104.44  3.000
 9FR  C11  C05  C06  118.10  3.000
 9FR  H15  C05  C04  106.22  3.000
 9FR  C06  C05  C04  109.53  3.000
 9FR  C11  C05  C04  113.90  3.000
 9FR  C08  C06  C07  108.87  3.000
 9FR  C08  C06  C05  107.75  3.000
 9FR  C07  C06  C05  113.50  3.000
 9FR  C05  C06  C01  106.90  3.000
 9FR  C08  C06  C01  107.33  3.000
 9FR  C07  C06  C01  112.22  3.000
 9FR  H18  C07  H17  106.07  3.000
 9FR  H18  C07  H16  106.77  3.000
 9FR  H17  C07  H16  108.01  3.000
 9FR  H18  C07  C06  112.94  3.000
 9FR  H17  C07  C06  109.99  3.000
 9FR  H16  C07  C06  112.72  3.000
 9FR  H4   C08  H19  106.50  3.000
 9FR  H4   C08  C09  108.78  3.000
 9FR  H19  C08  C09  108.66  3.000
 9FR  H4   C08  C06  109.41  3.000
 9FR  H19  C08  C06  110.81  3.000
 9FR  C09  C08  C06  112.48  3.000
 9FR  H33  C09  H20  106.91  3.000
 9FR  H33  C09  C08  110.09  3.000
 9FR  H20  C09  C08  110.90  3.000
 9FR  H33  C09  C10  109.11  3.000
 9FR  H20  C09  C10  109.21  3.000
 9FR  C08  C09  C10  110.53  3.000
 9FR  C12  C11  C05  114.58  3.000
 9FR  C05  C11  C13  108.56  3.000
 9FR  C12  C11  C13  107.22  3.000
 9FR  C13  C11  C10  109.29  3.000
 9FR  C05  C11  C10  110.32  3.000
 9FR  C12  C11  C10  106.73  3.000
 9FR  H23  C12  H22  107.58  3.000
 9FR  H23  C12  H21  107.33  3.000
 9FR  H22  C12  H21  107.51  3.000
 9FR  H23  C12  C11  114.19  3.000
 9FR  H22  C12  C11  110.13  3.000
 9FR  H21  C12  C11  109.85  3.000
 9FR  C14  O02  C02  113.20  3.000
 9FR  O02  C14  C17  120.94  3.000
 9FR  C17  C14  C15  125.29  3.000
 9FR  O02  C14  C15  113.69  3.000
 9FR  H26  C16  H25  105.23  3.000
 9FR  H26  C16  C01  106.38  3.000
 9FR  H25  C16  C01  110.85  3.000
 9FR  H26  C16  C15  106.94  3.000
 9FR  H25  C16  C15  108.32  3.000
 9FR  C01  C16  C15  118.26  3.000
 9FR  O05  C18  C19  122.16  3.000
 9FR  O05  C18  C17  122.34  3.000
 9FR  C19  C18  C17  115.43  3.000
 9FR  C18  C19  C21  128.61  3.000
 9FR  C18  C19  C20  122.94  3.000
 9FR  C21  C19  C20  108.45  3.000
 9FR  C22  O03  C21  110.90  3.000
 9FR  H29  C23  H28  108.05  3.000
 9FR  H29  C23  H27  108.01  3.000
 9FR  H28  C23  H27  106.94  3.000
 9FR  H29  C23  C17  111.72  3.000
 9FR  H28  C23  C17  110.87  3.000
 9FR  H27  C23  C17  111.06  3.000
 9FR  H32  C25  H31  107.78  3.000
 9FR  H32  C25  H30  107.28  3.000
 9FR  H31  C25  H30  107.95  3.000
 9FR  H32  C25  C02  109.18  3.000
 9FR  H31  C25  C02  110.71  3.000
 9FR  H30  C25  C02  113.72  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
 9FR  Var_01  C06  C08  C09  C10   -59.87  30.0  1
 9FR  Var_02  O03  C22  C20  C15   175.06  30.0  1
 9FR  Var_03  C21  C19  C20  C15  -175.11  30.0  1
 9FR  Var_04  C18  C17  C14  C15    -8.29  30.0  1
 9FR  Var_05  C20  C19  C18  C17     7.73  30.0  1
 9FR  Var_06  O03  C21  C19  C20    -0.15  30.0  1
 9FR  Var_07  C19  C21  O03  C22     0.26  30.0  1
 9FR  Var_08  C05  C04  C03  C02    52.87  30.0  1
 9FR  Var_09  C09  C10  C11  C05   -42.81  30.0  1
 9FR  Var_10  C11  C10  C09  C08    52.75  30.0  1
 9FR  Var_11  C19  C18  C17  C14    -5.52  30.0  1
 9FR  Var_12  H21  C12  C11  C10    65.35  30.0  3
 9FR  Var_13  H1   C13  C11  C10    64.71  30.0  3
 9FR  Var_14  H27  C23  C17  C14   117.66  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
 9FR  chir_01  C15  C16  C20  C14  positiv
 9FR  chir_02  C01  C06  C16  C02  negativ
 9FR  chir_03  C02  O02  C03  C01  negativ
 9FR  chir_04  C05  C11  C06  C04  negativ
 9FR  chir_05  C06  C05  C08  C01  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
 9FR  plan-1  C10  0.020
 9FR  plan-1  C09  0.020
 9FR  plan-1  C11  0.020
 9FR  plan-1  O01  0.020
 9FR  plan-2  C17  0.020
 9FR  plan-2  C18  0.020
 9FR  plan-2  C19  0.020
 9FR  plan-2  O05  0.020
 9FR  plan-3  C21  0.020
 9FR  plan-3  C19  0.020
 9FR  plan-3  O03  0.020
 9FR  plan-3  O04  0.020

