# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 22 17:49:14 2020
#   Inital geometry file: a 97 line input string
#   Ligand name: (3aS,4R,9bR)-2,2-difluoro-4-(4-hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(cc1)[C@@H]2Oc3ccc(O)cc3[C@@H]4CC(F)(F)C[C@H]24
#
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
 DC8  DC8  (3aS,4R,9bR)-2,2-difluoro-4-(4-hydroxyphenyl)-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromen-8-ol  ligand  39  23  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_DC8
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
 DC8  C4    C  CR6   0   0.330  -1.3119  -1.3142  -0.2455
 DC8  C6    C  CH1   0   0.003   0.7590  -0.7259   0.7034
 DC8  C8    C  CR15  0  -0.289   0.2145   0.6557   1.0418
 DC8  C10   C  CH2   0  -0.566   0.3147   1.6837  -0.1008
 DC8  C15   C  CR15  0  -0.325  -1.2763   0.5879   1.4167
 DC8  C17   C  CR6   0   0.070  -2.0028  -0.4490   0.5951
 DC8  C20   C  CR16  0  -0.286   3.1663  -0.6338   1.3649
 DC8  C21   C  CR16  0  -0.324   4.5209  -0.5557   1.0921
 DC8  C22   C  CR6   0   0.343   4.9622  -0.5460  -0.2298
 DC8  C24   C  CR16  0  -0.369   4.0287  -0.6145  -1.2587
 DC8  C1    C  CR6   0   0.356  -4.0855  -1.4941  -0.0801
 DC8  C2    C  CR16  0  -0.341  -3.3814  -2.3389  -0.9369
 DC8  C3    C  CR16  0  -0.343  -2.0045  -2.2507  -1.0085
 DC8  O5    O  O2    0  -0.502   0.0418  -1.2922  -0.3756
 DC8  C11   C  CR5   0   0.770  -1.0366   2.3881  -0.1332
 DC8  F12   F  F     0  -0.350  -0.9206   3.7411  -0.2903
 DC8  F13   F  F     0  -0.349  -1.7636   1.9728  -1.2190
 DC8  C14   C  CH2   0  -0.561  -1.7534   2.0174   1.1462
 DC8  C18   C  CR16  0  -0.443  -3.3898  -0.5623   0.6753
 DC8  C19   C  CR6   0   0.059   2.2202  -0.6974   0.3442
 DC8  O23   O  OH1   0  -0.633   6.2905  -0.4742  -0.4516
 DC8  C25   C  CR16  0  -0.301   2.6727  -0.6875  -0.9696
 DC8  O26   O  OH1   0  -0.641  -5.4309  -1.6271  -0.0270
 DC8  H6    H  HCH1  0   0.253   0.6258  -1.3606   1.5920
 DC8  H8    H  HCR5  0   0.283   0.7682   1.0236   1.9088
 DC8  H101  H  HCH2  0   0.274   1.1109   2.4038   0.0854
 DC8  H102  H  HCH2  0   0.270   0.5208   1.2276  -1.0699
 DC8  H15   H  HCR5  0   0.286  -1.3964   0.3444   2.4752
 DC8  H20   H  HCR6  0   0.252   2.8416  -0.6474   2.3995
 DC8  H21   H  HCR6  0   0.264   5.2398  -0.5097   1.9004
 DC8  H24   H  HCR6  0   0.269   4.3545  -0.6124  -2.2930
 DC8  H2    H  HCR6  0   0.263  -3.9120  -3.0711  -1.5327
 DC8  H3    H  HCR6  0   0.262  -1.4539  -2.9155  -1.6628
 DC8  H141  H  HCH2  0   0.275  -2.8354   2.1358   1.0790
 DC8  H142  H  HCH2  0   0.274  -1.3921   2.6663   1.9478
 DC8  H18   H  HCR6  0   0.267  -3.9326   0.1025   1.3405
 DC8  HO23  H  HOH1  0   0.474   6.4724  -0.4764  -1.3980
 DC8  H25   H  HCR6  0   0.256   1.9737  -0.7415  -1.7933
 DC8  HO26  H  HOH1  0   0.472  -5.8045  -0.9937   0.5952

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
 DC8  C4   C3    aromatic  1.392  0.020  1.392
 DC8  C4   O5    single    1.360  0.020  1.360
 DC8  C4   C17   aromatic  1.390  0.020  1.390
 DC8  C6   O5    single    1.414  0.020  1.414
 DC8  C6   C19   single    1.505  0.020  1.505
 DC8  C6   C8    single    1.523  0.020  1.523
 DC8  C6   H6    single    0.970  0.020  1.090
 DC8  C8   C15   single    1.539  0.020  1.539
 DC8  C8   C10   single    1.540  0.020  1.540
 DC8  C8   H8    single    0.970  0.020  1.090
 DC8  C10  C11   single    1.524  0.020  1.524
 DC8  C10  H101  single    0.970  0.020  1.090
 DC8  C10  H102  single    0.970  0.020  1.090
 DC8  C15  C17   single    1.509  0.020  1.509
 DC8  C15  C14   single    1.531  0.020  1.531
 DC8  C15  H15   single    0.970  0.020  1.090
 DC8  C17  C18   aromatic  1.394  0.020  1.394
 DC8  C20  C19   aromatic  1.393  0.020  1.393
 DC8  C20  C21   aromatic  1.384  0.020  1.384
 DC8  C20  H20   single    0.930  0.020  1.080
 DC8  C21  C22   aromatic  1.394  0.020  1.394
 DC8  C21  H21   single    0.930  0.020  1.080
 DC8  C22  C24   aromatic  1.391  0.020  1.391
 DC8  C22  O23   single    1.349  0.020  1.349
 DC8  C24  C25   aromatic  1.388  0.020  1.388
 DC8  C24  H24   single    0.930  0.020  1.080
 DC8  C1   C2    aromatic  1.394  0.020  1.394
 DC8  C1   O26   single    1.353  0.020  1.353
 DC8  C1   C18   aromatic  1.387  0.020  1.387
 DC8  C2   C3    aromatic  1.382  0.020  1.382
 DC8  C2   H2    single    0.930  0.020  1.080
 DC8  C3   H3    single    0.930  0.020  1.080
 DC8  C11  C14   single    1.513  0.020  1.513
 DC8  C11  F13   single    1.371  0.020  1.371
 DC8  C11  F12   single    1.367  0.020  1.367
 DC8  C14  H141  single    0.970  0.020  1.090
 DC8  C14  H142  single    0.970  0.020  1.090
 DC8  C18  H18   single    0.930  0.020  1.080
 DC8  C19  C25   aromatic  1.390  0.020  1.390
 DC8  O23  HO23  single    0.850  0.020  0.980
 DC8  C25  H25   single    0.930  0.020  1.080
 DC8  O26  HO26  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
 DC8  O5    C4   C3    116.97  3.000
 DC8  O5    C4   C17   122.85  3.000
 DC8  C3    C4   C17   120.18  3.000
 DC8  H6    C6   C19   108.74  3.000
 DC8  H6    C6   O5    108.90  3.000
 DC8  C19   C6   O5    108.54  3.000
 DC8  H6    C6   C8    107.49  3.000
 DC8  C19   C6   C8    112.52  3.000
 DC8  O5    C6   C8    110.58  3.000
 DC8  H8    C8   C15   108.21  3.000
 DC8  H8    C8   C10   109.33  3.000
 DC8  C15   C8   C10   105.85  3.000
 DC8  H8    C8   C6    107.49  3.000
 DC8  C10   C8   C6    114.67  3.000
 DC8  C15   C8   C6    111.13  3.000
 DC8  H102  C10  H101  106.86  3.000
 DC8  H102  C10  C11   109.99  3.000
 DC8  H101  C10  C11   110.25  3.000
 DC8  H102  C10  C8    113.10  3.000
 DC8  H101  C10  C8    111.22  3.000
 DC8  C11   C10  C8    105.46  3.000
 DC8  H15   C15  C14   110.18  3.000
 DC8  H15   C15  C17   108.74  3.000
 DC8  C14   C15  C17   113.28  3.000
 DC8  H15   C15  C8    110.63  3.000
 DC8  C14   C15  C8    102.58  3.000
 DC8  C17   C15  C8    111.35  3.000
 DC8  C18   C17  C15   120.23  3.000
 DC8  C18   C17  C4    118.60  3.000
 DC8  C15   C17  C4    121.16  3.000
 DC8  H20   C20  C19   119.68  3.000
 DC8  H20   C20  C21   118.80  3.000
 DC8  C19   C20  C21   121.52  3.000
 DC8  H21   C21  C22   119.84  3.000
 DC8  H21   C21  C20   120.34  3.000
 DC8  C22   C21  C20   119.82  3.000
 DC8  O23   C22  C24   122.82  3.000
 DC8  O23   C22  C21   117.92  3.000
 DC8  C24   C22  C21   119.26  3.000
 DC8  H24   C24  C25   119.48  3.000
 DC8  H24   C24  C22   120.25  3.000
 DC8  C25   C24  C22   120.27  3.000
 DC8  O26   C1   C18   122.93  3.000
 DC8  C18   C1   C2    119.25  3.000
 DC8  O26   C1   C2    117.82  3.000
 DC8  H2    C2   C3    120.20  3.000
 DC8  H2    C2   C1    120.03  3.000
 DC8  C3    C2   C1    119.77  3.000
 DC8  H3    C3   C2    119.92  3.000
 DC8  H3    C3   C4    119.40  3.000
 DC8  C2    C3   C4    120.68  3.000
 DC8  C6    O5   C4    116.00  3.000
 DC8  C14   C11  F13   110.14  3.000
 DC8  F13   C11  F12   104.70  3.000
 DC8  C14   C11  F12   112.33  3.000
 DC8  F12   C11  C10   112.62  3.000
 DC8  F13   C11  C10   110.30  3.000
 DC8  C14   C11  C10   106.79  3.000
 DC8  H142  C14  H141  107.99  3.000
 DC8  H142  C14  C11   108.55  3.000
 DC8  H141  C14  C11   113.05  3.000
 DC8  H142  C14  C15   108.77  3.000
 DC8  H141  C14  C15   114.93  3.000
 DC8  C11   C14  C15   103.33  3.000
 DC8  H18   C18  C1    119.62  3.000
 DC8  H18   C18  C17   118.87  3.000
 DC8  C1    C18  C17   121.50  3.000
 DC8  C25   C19  C20   118.11  3.000
 DC8  C25   C19  C6    122.82  3.000
 DC8  C20   C19  C6    119.04  3.000
 DC8  HO23  O23  C22   110.33  3.000
 DC8  H25   C25  C19   120.61  3.000
 DC8  H25   C25  C24   118.38  3.000
 DC8  C19   C25  C24   121.02  3.000
 DC8  HO26  O26  C1    110.27  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
 DC8  CONST_01  C1   C2   C3   C4      0.00   0.0  0
 DC8  CONST_02  C1   C18  C17  C4      0.00   0.0  0
 DC8  CONST_03  C2   C3   C4   C17     0.00   0.0  0
 DC8  CONST_04  C2   C1   C18  C17     0.00   0.0  0
 DC8  CONST_05  C24  C25  C19  C20     0.00   0.0  0
 DC8  CONST_06  C24  C22  C21  C20     0.00   0.0  0
 DC8  CONST_07  C25  C19  C20  C21     0.00   0.0  0
 DC8  CONST_08  C25  C24  C22  C21     0.00   0.0  0
 DC8  CONST_09  C19  C20  C21  C22     0.00   0.0  0
 DC8  CONST_10  C19  C25  C24  C22     0.00   0.0  0
 DC8  CONST_11  C18  C17  C4   C3      0.00   0.0  0
 DC8  CONST_12  C18  C1   C2   C3      0.00   0.0  0
 DC8  CONST_13  C21  C20  C19  C6    180.00   0.0  0
 DC8  CONST_14  C24  C25  C19  C6    180.00   0.0  0
 DC8  CONST_15  O26  C1   C18  C17   180.00   0.0  0
 DC8  CONST_16  O23  C22  C21  C20   180.00   0.0  0
 DC8  CONST_17  O26  C1   C2   C3    180.00   0.0  0
 DC8  CONST_18  C25  C24  C22  O23   180.00   0.0  0
 DC8  CONST_19  H2   C2   C3   C4    180.00   0.0  0
 DC8  CONST_20  H18  C18  C17  C4    180.00   0.0  0
 DC8  CONST_21  H20  C20  C19  C6      0.00   0.0  0
 DC8  CONST_22  H25  C25  C19  C6      0.00   0.0  0
 DC8  CONST_23  H3   C3   C4   C17   180.00   0.0  0
 DC8  CONST_24  H24  C24  C22  C21   180.00   0.0  0
 DC8  CONST_25  H21  C21  C22  C24   180.00   0.0  0
 DC8  Var_01    C3   C4   O5   C6   -157.67  30.0  1
 DC8  Var_02    C14  C11  C10  C8     13.07  30.0  1
 DC8  Var_03    C15  C14  C11  C10   -33.36  30.0  1

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
 DC8  chir_01  C6   O5   C19  C8  negativ
 DC8  chir_02  C8   C10  C15  C6  negativ
 DC8  chir_03  C15  C14  C17  C8  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
 DC8  plan-1  C6   0.020
 DC8  plan-1  C20  0.020
 DC8  plan-1  C21  0.020
 DC8  plan-1  C22  0.020
 DC8  plan-1  C24  0.020
 DC8  plan-1  C19  0.020
 DC8  plan-1  O23  0.020
 DC8  plan-1  C25  0.020
 DC8  plan-1  H20  0.020
 DC8  plan-1  H21  0.020
 DC8  plan-1  H24  0.020
 DC8  plan-1  H25  0.020
 DC8  plan-2  C4   0.020
 DC8  plan-2  C15  0.020
 DC8  plan-2  C17  0.020
 DC8  plan-2  C1   0.020
 DC8  plan-2  C2   0.020
 DC8  plan-2  C3   0.020
 DC8  plan-2  O5   0.020
 DC8  plan-2  C18  0.020
 DC8  plan-2  O26  0.020
 DC8  plan-2  H2   0.020
 DC8  plan-2  H3   0.020
 DC8  plan-2  H18  0.020

