# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 11:07:57 2020
#   Inital geometry file: a 144 line input string
#   Ligand name: N-[(1R)-3-(4-hydroxyphenyl)-1-methylpropyl]-2-(2-phenyl-1H-indol-3-yl)acetamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](CCc1ccc(O)cc1)NC(=O)Cc2c([nH]c3ccccc23)c4ccccc4
#
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
 IOK  IOK  N-[(1R)-3-(4-hydroxyphenyl)-1-methylpropyl]-2-(2-phenyl-1H-indol-3-yl)acetamide  ligand  56  30  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_IOK
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
 IOK  C1    C  CR6   0   0.117   -1.6308   6.6934   2.9847
 IOK  C2    C  CR16  0  -0.290   -0.8979   7.8761   2.9955
 IOK  C3    C  CR16  0  -0.372   -0.0389   8.2095   1.9583
 IOK  C4    C  CR6   0   0.333    0.1075   7.3498   0.8732
 IOK  O5    O  OH1   0  -0.637    0.9230   7.6211  -0.1690
 IOK  C6    C  CR16  0  -0.324   -0.6138   6.1590   0.8461
 IOK  C7    C  CR16  0  -0.302   -1.4675   5.8443   1.8924
 IOK  C8    C  CH2   0  -0.511   -2.5306   6.3300   4.1318
 IOK  C9    C  CH2   0  -0.438   -1.7736   5.6139   5.2513
 IOK  C10   C  CH1   0  -0.080   -2.6664   5.1457   6.3961
 IOK  C11   C  CH3   0  -0.647   -1.8756   4.3624   7.4379
 IOK  N12   N  NH1   0  -0.617   -3.3401   6.2878   6.9897
 IOK  C13   C  C     0   0.544   -4.5600   6.2331   7.5468
 IOK  O14   O  O     0  -0.496   -5.2247   5.2080   7.6090
 IOK  C15   C  CH2   0  -0.687   -5.1015   7.5619   8.0464
 IOK  C16   C  CR5   0  -0.026   -6.1230   8.0792   7.0820
 IOK  C17   C  CR5   0   0.308   -5.9375   8.9548   6.0375
 IOK  N18   N  NR15  0  -0.742   -7.1093   9.0631   5.3302
 IOK  C19   C  CR56  0   0.339   -8.0717   8.2884   5.9044
 IOK  C20   C  CR16  0  -0.317   -9.4089   8.1006   5.5576
 IOK  C21   C  CR16  0  -0.284  -10.1496   7.2305   6.3342
 IOK  C22   C  CR16  0  -0.270   -9.5772   6.5605   7.4293
 IOK  C23   C  CR16  0  -0.357   -8.2529   6.7512   7.7694
 IOK  C24   C  CR56  0   0.063   -7.4814   7.6376   7.0082
 IOK  C25   C  CR6   0   0.042   -4.7436   9.6768   5.5927
 IOK  C26   C  CR16  0  -0.299   -4.4232   9.7309   4.2337
 IOK  C27   C  CR16  0  -0.238   -3.2988  10.4164   3.8004
 IOK  C28   C  CR16  0  -0.259   -2.4705  11.0509   4.7166
 IOK  C29   C  CR16  0  -0.241   -2.7821  11.0059   6.0692
 IOK  C30   C  CR16  0  -0.319   -3.9136  10.3321   6.5040
 IOK  H2    H  HCR6  0   0.249   -1.0024   8.5608   3.8289
 IOK  H3    H  HCR6  0   0.265    0.5138   9.1417   1.9956
 IOK  HO5   H  HOH1  0   0.472    1.3532   8.4738  -0.0425
 IOK  H6    H  HCR6  0   0.258   -0.5090   5.4843   0.0053
 IOK  H7    H  HCR6  0   0.245   -2.0241   4.9148   1.8513
 IOK  H81   H  HCH2  0   0.248   -3.0054   7.2338   4.5226
 IOK  H82   H  HCH2  0   0.237   -3.3406   5.6856   3.7782
 IOK  H91   H  HCH2  0   0.229   -0.9828   6.2653   5.6421
 IOK  H92   H  HCH2  0   0.244   -1.2675   4.7359   4.8415
 IOK  H10   H  HCH1  0   0.242   -3.4418   4.4977   5.9807
 IOK  H111  H  HCH3  0   0.221   -1.0897   4.9807   7.8749
 IOK  H112  H  HCH3  0   0.235   -2.5229   4.0143   8.2428
 IOK  H113  H  HCH3  0   0.228   -1.4047   3.4890   6.9850
 IOK  HN12  H  HNH1  0   0.389   -2.8242   7.1519   7.0444
 IOK  H151  H  HCH2  0   0.267   -4.2997   8.2827   8.2007
 IOK  H152  H  HCH2  0   0.279   -5.5634   7.3963   9.0220
 IOK  HN18  H  HNR5  0   0.408   -7.2582   9.7081   4.5714
 IOK  H20   H  HCR6  0   0.258   -9.8498   8.6121   4.7114
 IOK  H21   H  HCR6  0   0.250  -11.1905   7.0586   6.0926
 IOK  H22   H  HCR6  0   0.246  -10.1878   5.8797   8.0081
 IOK  H23   H  HCR6  0   0.238   -7.8172   6.2215   8.6071
 IOK  H26   H  HCR6  0   0.258   -5.0451   9.2183   3.5099
 IOK  H27   H  HCR6  0   0.260   -3.0611  10.4424   2.7451
 IOK  H28   H  HCR6  0   0.261   -1.5895  11.5805   4.3780
 IOK  H29   H  HCR6  0   0.261   -2.1506  11.5102   6.7890
 IOK  H30   H  HCR6  0   0.259   -4.1661  10.3387   7.5566

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
 IOK  C1   C7    aromatic  1.393  0.020  1.393
 IOK  C1   C8    single    1.503  0.020  1.503
 IOK  C1   C2    aromatic  1.391  0.020  1.391
 IOK  C2   C3    aromatic  1.387  0.020  1.387
 IOK  C2   H2    single    0.930  0.020  1.080
 IOK  C3   C4    aromatic  1.392  0.020  1.392
 IOK  C3   H3    single    0.930  0.020  1.080
 IOK  C4   C6    aromatic  1.393  0.020  1.393
 IOK  C4   O5    single    1.351  0.020  1.351
 IOK  O5   HO5   single    0.850  0.020  0.980
 IOK  C6   C7    aromatic  1.387  0.020  1.387
 IOK  C6   H6    single    0.930  0.020  1.080
 IOK  C7   H7    single    0.930  0.020  1.080
 IOK  C8   C9    single    1.529  0.020  1.529
 IOK  C8   H81   single    0.970  0.020  1.090
 IOK  C8   H82   single    0.970  0.020  1.090
 IOK  C9   C10   single    1.525  0.020  1.525
 IOK  C9   H91   single    0.970  0.020  1.090
 IOK  C9   H92   single    0.970  0.020  1.090
 IOK  C10  C11   single    1.525  0.020  1.525
 IOK  C10  N12   single    1.453  0.020  1.453
 IOK  C10  H10   single    0.970  0.020  1.090
 IOK  C11  H111  single    0.970  0.020  1.090
 IOK  C11  H112  single    0.970  0.020  1.090
 IOK  C11  H113  single    0.970  0.020  1.090
 IOK  N12  C13   single    1.342  0.020  1.342
 IOK  N12  HN12  single    0.860  0.020  1.020
 IOK  C13  O14   double    1.223  0.020  1.223
 IOK  C13  C15   single    1.519  0.020  1.519
 IOK  C15  C16   single    1.497  0.020  1.497
 IOK  C15  H151  single    0.970  0.020  1.090
 IOK  C15  H152  single    0.970  0.020  1.090
 IOK  C16  C24   single    1.430  0.020  1.430
 IOK  C16  C17   double    1.376  0.020  1.376
 IOK  C17  N18   single    1.373  0.020  1.373
 IOK  C17  C25   single    1.464  0.020  1.464
 IOK  N18  C19   single    1.362  0.020  1.362
 IOK  N18  HN18  single    0.860  0.020  1.020
 IOK  C19  C24   aromatic  1.411  0.020  1.411
 IOK  C19  C20   aromatic  1.394  0.020  1.394
 IOK  C20  C21   aromatic  1.382  0.020  1.382
 IOK  C20  H20   single    0.930  0.020  1.080
 IOK  C21  C22   aromatic  1.406  0.020  1.406
 IOK  C21  H21   single    0.930  0.020  1.080
 IOK  C22  C23   aromatic  1.380  0.020  1.380
 IOK  C22  H22   single    0.930  0.020  1.080
 IOK  C23  C24   aromatic  1.400  0.020  1.400
 IOK  C23  H23   single    0.930  0.020  1.080
 IOK  C25  C26   aromatic  1.397  0.020  1.397
 IOK  C25  C30   aromatic  1.396  0.020  1.396
 IOK  C26  C27   aromatic  1.386  0.020  1.386
 IOK  C26  H26   single    0.930  0.020  1.080
 IOK  C27  C28   aromatic  1.389  0.020  1.389
 IOK  C27  H27   single    0.930  0.020  1.080
 IOK  C28  C29   aromatic  1.389  0.020  1.389
 IOK  C28  H28   single    0.930  0.020  1.080
 IOK  C29  C30   aromatic  1.387  0.020  1.387
 IOK  C29  H29   single    0.930  0.020  1.080
 IOK  C30  H30   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
 IOK  C8    C1   C7    121.43  3.000
 IOK  C8    C1   C2    121.00  3.000
 IOK  C7    C1   C2    117.54  3.000
 IOK  H2    C2   C3    118.87  3.000
 IOK  H2    C2   C1    119.49  3.000
 IOK  C3    C2   C1    121.64  3.000
 IOK  H3    C3   C4    120.27  3.000
 IOK  H3    C3   C2    119.77  3.000
 IOK  C4    C3   C2    119.96  3.000
 IOK  C6    C4   O5    118.00  3.000
 IOK  O5    C4   C3    122.74  3.000
 IOK  C6    C4   C3    119.26  3.000
 IOK  HO5   O5   C4    110.25  3.000
 IOK  H6    C6   C7    120.26  3.000
 IOK  H6    C6   C4    119.84  3.000
 IOK  C7    C6   C4    119.89  3.000
 IOK  H7    C7   C6    118.82  3.000
 IOK  H7    C7   C1    119.47  3.000
 IOK  C6    C7   C1    121.70  3.000
 IOK  H82   C8   H81   106.32  3.000
 IOK  H82   C8   C9    109.11  3.000
 IOK  H81   C8   C9    109.90  3.000
 IOK  H82   C8   C1    109.83  3.000
 IOK  H81   C8   C1    109.45  3.000
 IOK  C9    C8   C1    112.06  3.000
 IOK  H92   C9   H91   106.07  3.000
 IOK  H92   C9   C10   107.81  3.000
 IOK  H91   C9   C10   109.69  3.000
 IOK  H92   C9   C8    109.32  3.000
 IOK  H91   C9   C8    109.86  3.000
 IOK  C10   C9   C8    113.78  3.000
 IOK  H10   C10  N12   107.01  3.000
 IOK  H10   C10  C11   108.86  3.000
 IOK  N12   C10  C11   111.42  3.000
 IOK  H10   C10  C9    108.18  3.000
 IOK  N12   C10  C9    109.68  3.000
 IOK  C11   C10  C9    111.52  3.000
 IOK  H113  C11  H112  107.89  3.000
 IOK  H113  C11  H111  108.00  3.000
 IOK  H112  C11  H111  108.24  3.000
 IOK  H113  C11  C10   110.59  3.000
 IOK  H112  C11  C10   111.14  3.000
 IOK  H111  C11  C10   110.87  3.000
 IOK  HN12  N12  C13   118.53  3.000
 IOK  HN12  N12  C10   117.31  3.000
 IOK  C13   N12  C10   123.99  3.000
 IOK  C15   C13  O14   121.50  3.000
 IOK  C15   C13  N12   115.13  3.000
 IOK  O14   C13  N12   123.31  3.000
 IOK  H152  C15  H151  106.56  3.000
 IOK  H152  C15  C16   109.83  3.000
 IOK  H151  C15  C16   111.41  3.000
 IOK  H152  C15  C13   108.17  3.000
 IOK  H151  C15  C13   111.28  3.000
 IOK  C16   C15  C13   109.49  3.000
 IOK  C24   C16  C17   106.59  3.000
 IOK  C17   C16  C15   128.10  3.000
 IOK  C24   C16  C15   125.07  3.000
 IOK  C25   C17  N18   120.03  3.000
 IOK  C25   C17  C16   130.88  3.000
 IOK  N18   C17  C16   109.04  3.000
 IOK  HN18  N18  C19   125.27  3.000
 IOK  HN18  N18  C17   124.40  3.000
 IOK  C19   N18  C17   109.93  3.000
 IOK  C24   C19  C20   122.26  3.000
 IOK  C20   C19  N18   130.49  3.000
 IOK  C24   C19  N18   107.25  3.000
 IOK  H20   C20  C21   121.23  3.000
 IOK  H20   C20  C19   121.43  3.000
 IOK  C21   C20  C19   117.34  3.000
 IOK  H21   C21  C22   119.32  3.000
 IOK  H21   C21  C20   119.36  3.000
 IOK  C22   C21  C20   121.32  3.000
 IOK  H22   C22  C23   119.76  3.000
 IOK  H22   C22  C21   119.13  3.000
 IOK  C23   C22  C21   121.11  3.000
 IOK  H23   C23  C24   120.57  3.000
 IOK  H23   C23  C22   120.61  3.000
 IOK  C24   C23  C22   118.82  3.000
 IOK  C23   C24  C19   119.14  3.000
 IOK  C23   C24  C16   133.69  3.000
 IOK  C19   C24  C16   107.18  3.000
 IOK  C30   C25  C26   118.71  3.000
 IOK  C30   C25  C17   121.19  3.000
 IOK  C26   C25  C17   120.10  3.000
 IOK  H26   C26  C27   119.39  3.000
 IOK  H26   C26  C25   120.00  3.000
 IOK  C27   C26  C25   120.60  3.000
 IOK  H27   C27  C28   120.10  3.000
 IOK  H27   C27  C26   119.66  3.000
 IOK  C28   C27  C26   120.23  3.000
 IOK  H28   C28  C29   120.21  3.000
 IOK  H28   C28  C27   120.18  3.000
 IOK  C29   C28  C27   119.60  3.000
 IOK  H29   C29  C30   119.60  3.000
 IOK  H29   C29  C28   120.12  3.000
 IOK  C30   C29  C28   120.28  3.000
 IOK  H30   C30  C29   119.48  3.000
 IOK  H30   C30  C25   119.93  3.000
 IOK  C29   C30  C25   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
 IOK  CONST_01  C4    C6   C7   C1      0.00   0.0  0
 IOK  CONST_02  C4    C3   C2   C1      0.00   0.0  0
 IOK  CONST_03  C6    C7   C1   C2      0.00   0.0  0
 IOK  CONST_04  C6    C4   C3   C2      0.00   0.0  0
 IOK  CONST_05  C7    C1   C2   C3      0.00   0.0  0
 IOK  CONST_06  C7    C6   C4   C3      0.00   0.0  0
 IOK  CONST_07  C22   C23  C24  C19     0.00   0.0  0
 IOK  CONST_08  C22   C21  C20  C19     0.00   0.0  0
 IOK  CONST_09  C23   C24  C19  C20     0.00   0.0  0
 IOK  CONST_10  C23   C22  C21  C20     0.00   0.0  0
 IOK  CONST_11  C24   C19  C20  C21     0.00   0.0  0
 IOK  CONST_12  C24   C23  C22  C21     0.00   0.0  0
 IOK  CONST_13  C28   C27  C26  C25     0.00   0.0  0
 IOK  CONST_14  C28   C29  C30  C25     0.00   0.0  0
 IOK  CONST_15  C29   C30  C25  C26     0.00   0.0  0
 IOK  CONST_16  C29   C28  C27  C26     0.00   0.0  0
 IOK  CONST_17  C30   C25  C26  C27     0.00   0.0  0
 IOK  CONST_18  C30   C29  C28  C27     0.00   0.0  0
 IOK  CONST_19  C27   C26  C25  C17   180.00   0.0  0
 IOK  CONST_20  C29   C30  C25  C17   180.00   0.0  0
 IOK  CONST_21  O5    C4   C3   C2    180.00   0.0  0
 IOK  CONST_22  C8    C1   C2   C3    180.00   0.0  0
 IOK  CONST_23  C7    C6   C4   O5    180.00   0.0  0
 IOK  CONST_24  C8    C1   C7   C6    180.00   0.0  0
 IOK  CONST_25  H6    C6   C7   C1    180.00   0.0  0
 IOK  CONST_26  H3    C3   C2   C1    180.00   0.0  0
 IOK  CONST_27  H7    C7   C1   C2    180.00   0.0  0
 IOK  CONST_28  H2    C2   C3   C4    180.00   0.0  0
 IOK  CONST_29  H23   C23  C24  C16     0.00   0.0  0
 IOK  CONST_30  H26   C26  C25  C17     0.00   0.0  0
 IOK  CONST_31  H30   C30  C25  C17     0.00   0.0  0
 IOK  CONST_32  H20   C20  C19  N18     0.00   0.0  0
 IOK  CONST_33  H21   C21  C20  C19   180.00   0.0  0
 IOK  CONST_34  H22   C22  C21  C20   180.00   0.0  0
 IOK  CONST_35  H27   C27  C26  C25   180.00   0.0  0
 IOK  CONST_36  H29   C29  C30  C25   180.00   0.0  0
 IOK  CONST_37  H28   C28  C27  C26   180.00   0.0  0
 IOK  CONST_38  O14   C13  N12  C10     0.00   0.0  0
 IOK  CONST_39  C15   C13  N12  C10   180.00   0.0  0
 IOK  CONST_40  HN12  N12  C13  O14   180.00   0.0  0
 IOK  Var_01    C26   C25  C17  C16   135.42  30.0  2
 IOK  Var_02    C9    C8   C1   C2    -85.53  30.0  2
 IOK  Var_03    C24   C16  C15  C13    79.53  30.0  3
 IOK  Var_04    C10   C9   C8   C1   -176.22  30.0  3
 IOK  Var_05    C16   C15  C13  N12   103.35  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
 IOK  chir_01  C10  C9  C11  N12  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
 IOK  plan-1  C1    0.020
 IOK  plan-1  C2    0.020
 IOK  plan-1  C3    0.020
 IOK  plan-1  C4    0.020
 IOK  plan-1  O5    0.020
 IOK  plan-1  C6    0.020
 IOK  plan-1  C7    0.020
 IOK  plan-1  C8    0.020
 IOK  plan-1  H2    0.020
 IOK  plan-1  H3    0.020
 IOK  plan-1  H6    0.020
 IOK  plan-1  H7    0.020
 IOK  plan-2  C17   0.020
 IOK  plan-2  C25   0.020
 IOK  plan-2  C26   0.020
 IOK  plan-2  C27   0.020
 IOK  plan-2  C28   0.020
 IOK  plan-2  C29   0.020
 IOK  plan-2  C30   0.020
 IOK  plan-2  H26   0.020
 IOK  plan-2  H27   0.020
 IOK  plan-2  H28   0.020
 IOK  plan-2  H29   0.020
 IOK  plan-2  H30   0.020
 IOK  plan-3  C15   0.020
 IOK  plan-3  C16   0.020
 IOK  plan-3  C17   0.020
 IOK  plan-3  N18   0.020
 IOK  plan-3  C19   0.020
 IOK  plan-3  C20   0.020
 IOK  plan-3  C21   0.020
 IOK  plan-3  C22   0.020
 IOK  plan-3  C23   0.020
 IOK  plan-3  C24   0.020
 IOK  plan-3  C25   0.020
 IOK  plan-3  HN18  0.020
 IOK  plan-3  H20   0.020
 IOK  plan-3  H21   0.020
 IOK  plan-3  H22   0.020
 IOK  plan-3  H23   0.020
 IOK  plan-4  C10   0.020
 IOK  plan-4  N12   0.020
 IOK  plan-4  C13   0.020
 IOK  plan-4  O14   0.020
 IOK  plan-4  C15   0.020
 IOK  plan-4  HN12  0.020

