# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 21 22:13:59 2020
#   Inital geometry file: a 142 line input string
#   Ligand name: [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(cc1)c2sc3cc(O)ccc3c2C(=O)c4ccc(OCCN5CCCC5)cc4
#
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
 LLC  LLC  '[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone'  ligand  58  33  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_LLC
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
 LLC  C4    C  CR16  0  -0.274   0.6489  -1.1780   1.7373
 LLC  C5    C  CR16  0  -0.317  -0.5356  -1.8506   1.9722
 LLC  C6    C  CR6   0   0.361  -1.2389  -2.4087   0.9072
 LLC  C8    C  CR16  0  -0.352  -0.7254  -2.3070  -0.3837
 LLC  C13   C  CR16  0  -0.315   4.6037   2.2373  -1.3861
 LLC  C15   C  CR6   0   0.353   6.6093   1.9735  -0.0569
 LLC  C20   C  CR6   0  -0.058   0.2306   1.3438  -1.3788
 LLC  C21   C  CR16  0  -0.250  -0.7493   1.1780  -2.3619
 LLC  C22   C  CR16  0  -0.341  -2.0868   1.2170  -2.0388
 LLC  C26   C  CH2   0  -0.294  -5.7581   1.2660   0.8576
 LLC  C28   C  CH2   0  -0.274  -7.5290  -0.2705   0.2756
 LLC  O19   O  O     0  -0.405   2.0396   1.4337  -2.8761
 LLC  C33   C  CR16  0  -0.246  -0.1752   1.6178  -0.0768
 LLC  C32   C  CR16  0  -0.360  -1.5157   1.6850   0.2594
 LLC  C23   C  CR6   0   0.402  -2.4840   1.4496  -0.7169
 LLC  O24   O  O2    0  -0.458  -3.8008   1.4295  -0.4838
 LLC  C25   C  CH2   0  -0.214  -4.2713   1.5391   0.8507
 LLC  N27   N  NT    0  -0.420  -6.0972  -0.0558   0.3944
 LLC  C31   C  CH2   0  -0.289  -5.6275  -1.1438   1.2322
 LLC  C30   C  CH2   0  -0.460  -6.3527  -2.3608   0.6625
 LLC  C29   C  CH2   0  -0.469  -7.6690  -1.7866   0.0987
 LLC  C1    C  CR5   0   0.083   2.6161   0.7238  -0.7218
 LLC  C12   C  CR56  0   0.188   3.9658   1.2359  -0.6407
 LLC  C14   C  CR16  0  -0.328   5.9008   2.5974  -1.0973
 LLC  O17   O  OH1   0  -0.629   7.8755   2.3795   0.1540
 LLC  C16   C  CR16  0  -0.414   6.0051   0.9865   0.7031
 LLC  C11   C  CR56  0  -0.218   4.6936   0.6375   0.3979
 LLC  S10   S  S2    0   0.247   3.7506  -0.5630   1.2110
 LLC  C2    C  CR5   0  -0.290   2.3671  -0.2485   0.2079
 LLC  C3    C  CR6   0   0.023   1.1593  -1.0409   0.4450
 LLC  C9    C  CR16  0  -0.276   0.4624  -1.6355  -0.6054
 LLC  O7    O  OH1   0  -0.630  -2.3961  -3.0398   1.1797
 LLC  H4    H  HCR6  0   0.258   1.1631  -0.7198   2.5736
 LLC  H5    H  HCR6  0   0.267  -0.9250  -1.9326   2.9788
 LLC  H8    H  HCR6  0   0.274  -1.2514  -2.7545  -1.2188
 LLC  H13   H  HCR6  0   0.256   4.0883   2.7339  -2.1952
 LLC  H21   H  HCR6  0   0.260  -0.4588   0.9721  -3.3840
 LLC  H22   H  HCR6  0   0.264  -2.8406   1.0505  -2.7979
 LLC  H261  H  HCH2  0   0.204  -6.1140   1.4496   1.8865
 LLC  H262  H  HCH2  0   0.244  -6.2593   2.0014   0.2219
 LLC  H282  H  HCH2  0   0.232  -7.9393   0.3023  -0.5592
 LLC  H33   H  HCR6  0   0.271   0.5609   1.7879   0.6982
 LLC  H32   H  HCR6  0   0.280  -1.7848   1.9081   1.2820
 LLC  H251  H  HCH2  0   0.244  -4.0865   2.5450   1.2416
 LLC  H252  H  HCH2  0   0.230  -3.7420   0.8340   1.5003
 LLC  H311  H  HCH2  0   0.233  -4.5424  -1.2517   1.1908
 LLC  H312  H  HCH2  0   0.191  -5.9015  -0.9906   2.2909
 LLC  H301  H  HCH2  0   0.231  -5.7597  -2.8141  -0.1327
 LLC  H302  H  HCH2  0   0.234  -6.5132  -3.1263   1.4210
 LLC  H291  H  HCH2  0   0.234  -8.5445  -2.1622   0.6273
 LLC  H292  H  HCH2  0   0.236  -7.7921  -2.0513  -0.9515
 LLC  H14   H  HCR6  0   0.269   6.3901   3.3693  -1.6779
 LLC  HO17  H  HOH1  0   0.477   8.2709   1.8898   0.8839
 LLC  H16   H  HCR6  0   0.285   6.5376   0.4995   1.5116
 LLC  H9    H  HCR6  0   0.264   0.8504  -1.5787  -1.6142
 LLC  HO7   H  HOH1  0   0.474  -2.7847  -3.3956   0.3728
 LLC  C18   C  C     0   0.326   1.6513   1.1921  -1.7460
 LLC  H281  H  HCH2  0   0.191  -8.0626   0.0545   1.1851

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
 LLC  C29  C28   single    1.533  0.020  1.533
 LLC  C29  C30   single    1.543  0.020  1.543
 LLC  C28  N27   single    1.453  0.020  1.453
 LLC  C30  C31   single    1.527  0.020  1.527
 LLC  N27  C31   single    1.451  0.020  1.451
 LLC  N27  C26   single    1.441  0.020  1.441
 LLC  C26  C25   single    1.512  0.020  1.512
 LLC  C25  O24   single    1.419  0.020  1.419
 LLC  O24  C23   single    1.337  0.020  1.337
 LLC  C23  C22   aromatic  1.400  0.020  1.400
 LLC  C23  C32   aromatic  1.395  0.020  1.395
 LLC  C22  C21   aromatic  1.377  0.020  1.377
 LLC  C32  C33   aromatic  1.384  0.020  1.384
 LLC  C21  C20   aromatic  1.398  0.020  1.398
 LLC  C33  C20   aromatic  1.391  0.020  1.391
 LLC  C20  C18   single    1.475  0.020  1.475
 LLC  C14  C13   aromatic  1.377  0.020  1.377
 LLC  C14  C15   aromatic  1.405  0.020  1.405
 LLC  C13  C12   aromatic  1.402  0.020  1.402
 LLC  O17  C15   single    1.346  0.020  1.346
 LLC  C15  C16   aromatic  1.384  0.020  1.384
 LLC  C18  C1    single    1.483  0.020  1.483
 LLC  C18  O19   double    1.219  0.020  1.219
 LLC  C9   C8    aromatic  1.382  0.020  1.382
 LLC  C9   C3    aromatic  1.394  0.020  1.394
 LLC  C12  C1    aromatic  1.446  0.020  1.446
 LLC  C12  C11   aromatic  1.402  0.020  1.402
 LLC  C1   C2    aromatic  1.368  0.020  1.368
 LLC  C16  C11   aromatic  1.391  0.020  1.391
 LLC  C11  S10   aromatic  1.730  0.020  1.730
 LLC  C8   C6    aromatic  1.393  0.020  1.393
 LLC  C2   S10   aromatic  1.738  0.020  1.738
 LLC  C2   C3    single    1.464  0.020  1.464
 LLC  C3   C4    aromatic  1.396  0.020  1.396
 LLC  C6   O7    single    1.346  0.020  1.346
 LLC  C6   C5    aromatic  1.393  0.020  1.393
 LLC  C4   C5    aromatic  1.382  0.020  1.382
 LLC  C4   H4    single    0.930  0.020  1.080
 LLC  C5   H5    single    0.930  0.020  1.080
 LLC  C8   H8    single    0.930  0.020  1.080
 LLC  C13  H13   single    0.930  0.020  1.080
 LLC  C21  H21   single    0.930  0.020  1.080
 LLC  C22  H22   single    0.930  0.020  1.080
 LLC  C26  H261  single    0.970  0.020  1.090
 LLC  C26  H262  single    0.970  0.020  1.090
 LLC  C28  H281  single    0.970  0.020  1.090
 LLC  C28  H282  single    0.970  0.020  1.090
 LLC  C33  H33   single    0.930  0.020  1.080
 LLC  C32  H32   single    0.930  0.020  1.080
 LLC  C25  H251  single    0.970  0.020  1.090
 LLC  C25  H252  single    0.970  0.020  1.090
 LLC  C31  H311  single    0.970  0.020  1.090
 LLC  C31  H312  single    0.970  0.020  1.090
 LLC  C30  H301  single    0.970  0.020  1.090
 LLC  C30  H302  single    0.970  0.020  1.090
 LLC  C29  H291  single    0.970  0.020  1.090
 LLC  C29  H292  single    0.970  0.020  1.090
 LLC  C14  H14   single    0.930  0.020  1.080
 LLC  O17  HO17  single    0.850  0.020  0.980
 LLC  C16  H16   single    0.930  0.020  1.080
 LLC  C9   H9    single    0.930  0.020  1.080
 LLC  O7   HO7   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
 LLC  H4    C4   C3    119.96  3.000
 LLC  H4    C4   C5    118.77  3.000
 LLC  C3    C4   C5    121.22  3.000
 LLC  H5    C5   C6    119.93  3.000
 LLC  H5    C5   C4    120.21  3.000
 LLC  C6    C5   C4    119.85  3.000
 LLC  O7    C6   C8    122.60  3.000
 LLC  O7    C6   C5    117.85  3.000
 LLC  C8    C6   C5    119.54  3.000
 LLC  H8    C8   C9    119.61  3.000
 LLC  H8    C8   C6    120.34  3.000
 LLC  C9    C8   C6    120.06  3.000
 LLC  H13   C13  C14   119.10  3.000
 LLC  H13   C13  C12   120.63  3.000
 LLC  C14   C13  C12   120.27  3.000
 LLC  C16   C15  O17   122.65  3.000
 LLC  C16   C15  C14   120.20  3.000
 LLC  O17   C15  C14   117.16  3.000
 LLC  C33   C20  C18   122.29  3.000
 LLC  C18   C20  C21   119.19  3.000
 LLC  C33   C20  C21   118.50  3.000
 LLC  H21   C21  C22   119.19  3.000
 LLC  H21   C21  C20   119.91  3.000
 LLC  C22   C21  C20   120.84  3.000
 LLC  H22   C22  C23   119.35  3.000
 LLC  H22   C22  C21   120.51  3.000
 LLC  C23   C22  C21   120.13  3.000
 LLC  H262  C26  H261  106.39  3.000
 LLC  H262  C26  N27   108.79  3.000
 LLC  H261  C26  N27   112.10  3.000
 LLC  H262  C26  C25   109.06  3.000
 LLC  H261  C26  C25   106.94  3.000
 LLC  N27   C26  C25   113.30  3.000
 LLC  H282  C28  H281  107.08  3.000
 LLC  H282  C28  C29   113.34  3.000
 LLC  H281  C28  C29   110.02  3.000
 LLC  H282  C28  N27   110.81  3.000
 LLC  H281  C28  N27   111.45  3.000
 LLC  C29   C28  N27   104.22  3.000
 LLC  H33   C33  C32   118.51  3.000
 LLC  H33   C33  C20   120.18  3.000
 LLC  C32   C33  C20   121.31  3.000
 LLC  H32   C32  C23   121.61  3.000
 LLC  H32   C32  C33   118.76  3.000
 LLC  C23   C32  C33   119.62  3.000
 LLC  O24   C23  C32   124.33  3.000
 LLC  C32   C23  C22   119.47  3.000
 LLC  O24   C23  C22   116.19  3.000
 LLC  C25   O24  C23   119.28  3.000
 LLC  H252  C25  H251  107.35  3.000
 LLC  H252  C25  O24   110.36  3.000
 LLC  H251  C25  O24   110.53  3.000
 LLC  H252  C25  C26   110.87  3.000
 LLC  H251  C25  C26   109.28  3.000
 LLC  O24   C25  C26   108.44  3.000
 LLC  C31   N27  C28   104.79  3.000
 LLC  C31   N27  C26   115.21  3.000
 LLC  C28   N27  C26   113.19  3.000
 LLC  H312  C31  H311  107.26  3.000
 LLC  H312  C31  C30   110.52  3.000
 LLC  H311  C31  C30   112.29  3.000
 LLC  H312  C31  N27   111.66  3.000
 LLC  H311  C31  N27   111.96  3.000
 LLC  C30   C31  N27   103.21  3.000
 LLC  H302  C30  H301  107.20  3.000
 LLC  H302  C30  C29   112.97  3.000
 LLC  H301  C30  C29   110.62  3.000
 LLC  H302  C30  C31   111.72  3.000
 LLC  H301  C30  C31   110.18  3.000
 LLC  C29   C30  C31   104.17  3.000
 LLC  H292  C29  H291  107.03  3.000
 LLC  H292  C29  C30   110.98  3.000
 LLC  H291  C29  C30   112.33  3.000
 LLC  H292  C29  C28   111.21  3.000
 LLC  H291  C29  C28   111.00  3.000
 LLC  C30   C29  C28   104.36  3.000
 LLC  C2    C1   C12   112.55  3.000
 LLC  C2    C1   C18   125.12  3.000
 LLC  C12   C1   C18   122.29  3.000
 LLC  C11   C12  C1    112.02  3.000
 LLC  C11   C12  C13   117.54  3.000
 LLC  C1    C12  C13   130.39  3.000
 LLC  H14   C14  C15   119.06  3.000
 LLC  H14   C14  C13   119.99  3.000
 LLC  C15   C14  C13   120.95  3.000
 LLC  HO17  O17  C15   110.56  3.000
 LLC  H16   C16  C11   120.95  3.000
 LLC  H16   C16  C15   121.03  3.000
 LLC  C11   C16  C15   118.03  3.000
 LLC  S10   C11  C16   125.81  3.000
 LLC  S10   C11  C12   111.18  3.000
 LLC  C16   C11  C12   123.01  3.000
 LLC  C2    S10  C11    92.13  3.000
 LLC  C3    C2   S10   117.74  3.000
 LLC  C3    C2   C1    130.16  3.000
 LLC  S10   C2   C1    112.08  3.000
 LLC  C9    C3   C2    121.43  3.000
 LLC  C2    C3   C4    120.31  3.000
 LLC  C9    C3   C4    118.22  3.000
 LLC  H9    C9   C3    120.06  3.000
 LLC  H9    C9   C8    118.88  3.000
 LLC  C3    C9   C8    121.07  3.000
 LLC  HO7   O7   C6    110.50  3.000
 LLC  C1    C18  O19   119.71  3.000
 LLC  O19   C18  C20   121.14  3.000
 LLC  C1    C18  C20   119.15  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
 LLC  CONST_01  C8    C9   C3   C4      0.00   0.0  0
 LLC  CONST_04  C8    C6   C5   C4      0.00   0.0  0
 LLC  CONST_05  C9    C8   C6   C5      0.00   0.0  0
 LLC  CONST_06  C9    C3   C4   C5      0.00   0.0  0
 LLC  CONST_07  C2    C3   C4   C5    180.00   0.0  0
 LLC  CONST_08  C3    C9   C8   C6      0.00   0.0  0
 LLC  CONST_09  C3    C4   C5   C6      0.00   0.0  0
 LLC  CONST_10  C2    C3   C9   C8    180.00   0.0  0
 LLC  CONST_11  C16   C15  C14  C13     0.00   0.0  0
 LLC  CONST_12  C2    C1   C12  C13   180.00   0.0  0
 LLC  CONST_13  C16   C11  C12  C13     0.00   0.0  0
 LLC  CONST_14  S10   C11  C12  C13   180.00   0.0  0
 LLC  CONST_15  C12   C13  C14  C15     0.00   0.0  0
 LLC  CONST_16  C12   C11  C16  C15     0.00   0.0  0
 LLC  CONST_17  S10   C11  C16  C15   180.00   0.0  0
 LLC  CONST_18  C23   C22  C21  C20     0.00   0.0  0
 LLC  CONST_19  C23   C32  C33  C20     0.00   0.0  0
 LLC  CONST_20  C32   C23  C22  C21     0.00   0.0  0
 LLC  CONST_21  C32   C33  C20  C21     0.00   0.0  0
 LLC  CONST_22  C33   C32  C23  C22     0.00   0.0  0
 LLC  CONST_23  C33   C20  C21  C22     0.00   0.0  0
 LLC  CONST_24  C14   C13  C12  C1    180.00   0.0  0
 LLC  CONST_25  C16   C11  C12  C1    180.00   0.0  0
 LLC  CONST_26  S10   C11  C12  C1      0.00   0.0  0
 LLC  CONST_27  C11   S10  C2   C1      0.00   0.0  0
 LLC  CONST_29  S10   C2   C1   C12     0.00   0.0  0
 LLC  CONST_30  C3    C2   C1   C12   180.00   0.0  0
 LLC  CONST_31  C2    S10  C11  C12     0.00   0.0  0
 LLC  CONST_32  C11   C12  C13  C14     0.00   0.0  0
 LLC  CONST_33  C11   C16  C15  C14     0.00   0.0  0
 LLC  CONST_34  C2    S10  C11  C16   180.00   0.0  0
 LLC  CONST_35  C2    C1   C12  C11     0.00   0.0  0
 LLC  CONST_36  C3    C2   S10  C11   180.00   0.0  0
 LLC  CONST_38  O7    C6   C5   C4    180.00   0.0  0
 LLC  CONST_39  O17   C15  C14  C13   180.00   0.0  0
 LLC  CONST_40  C18   C1   C12  C13     0.00   0.0  0
 LLC  CONST_41  O24   C23  C22  C21   180.00   0.0  0
 LLC  CONST_42  C18   C20  C21  C22   180.00   0.0  0
 LLC  CONST_43  C32   C33  C20  C18   180.00   0.0  0
 LLC  CONST_44  C11   C12  C1   C18   180.00   0.0  0
 LLC  CONST_45  S10   C2   C1   C18   180.00   0.0  0
 LLC  CONST_46  C3    C2   C1   C18     0.00   0.0  0
 LLC  CONST_47  O24   C23  C32  C33   180.00   0.0  0
 LLC  CONST_48  C11   C16  C15  O17   180.00   0.0  0
 LLC  CONST_49  O7    C6   C8   C9    180.00   0.0  0
 LLC  CONST_50  H9    C9   C3   C4    180.00   0.0  0
 LLC  CONST_51  H8    C8   C6   C5    180.00   0.0  0
 LLC  CONST_52  H4    C4   C5   C6    180.00   0.0  0
 LLC  CONST_53  H5    C5   C6   C8    180.00   0.0  0
 LLC  CONST_54  H13   C13  C14  C15   180.00   0.0  0
 LLC  CONST_55  H22   C22  C21  C20   180.00   0.0  0
 LLC  CONST_56  H32   C32  C33  C20   180.00   0.0  0
 LLC  CONST_57  H33   C33  C20  C21   180.00   0.0  0
 LLC  CONST_58  H21   C21  C20  C33   180.00   0.0  0
 LLC  CONST_59  H14   C14  C13  C12   180.00   0.0  0
 LLC  CONST_60  H16   C16  C11  C12   180.00   0.0  0
 LLC  Var_01    C31   C30  C29  C28     5.11  30.0  1
 LLC  Var_02    C30   C31  N27  C28    44.21  30.0  1
 LLC  Var_03    C30   C29  C28  N27    20.99  30.0  1
 LLC  Var_04    C29   C30  C31  N27   -29.44  30.0  1
 LLC  Var_05    C29   C28  N27  C31   -40.93  30.0  1
 LLC  Var_06    C12   C1   C18  C20  -142.84  30.0  2
 LLC  Var_07    C1    C18  C20  C21  -150.98  30.0  2
 LLC  Var_08    C25   C26  N27  C28  -174.24  30.0  3
 LLC  Var_09    N27   C26  C25  O24    61.16  30.0  2
 LLC  Var_10    H251  C25  O24  C23    69.26  30.0  1

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
 LLC  plan-1  C20  0.020
 LLC  plan-1  C21  0.020
 LLC  plan-1  C22  0.020
 LLC  plan-1  C33  0.020
 LLC  plan-1  C32  0.020
 LLC  plan-1  C23  0.020
 LLC  plan-1  O24  0.020
 LLC  plan-1  H21  0.020
 LLC  plan-1  H22  0.020
 LLC  plan-1  H33  0.020
 LLC  plan-1  H32  0.020
 LLC  plan-1  C18  0.020
 LLC  plan-2  C4   0.020
 LLC  plan-2  C5   0.020
 LLC  plan-2  C6   0.020
 LLC  plan-2  C8   0.020
 LLC  plan-2  C2   0.020
 LLC  plan-2  C3   0.020
 LLC  plan-2  C9   0.020
 LLC  plan-2  O7   0.020
 LLC  plan-2  H4   0.020
 LLC  plan-2  H5   0.020
 LLC  plan-2  H8   0.020
 LLC  plan-2  H9   0.020
 LLC  plan-3  C13  0.020
 LLC  plan-3  C15  0.020
 LLC  plan-3  C1   0.020
 LLC  plan-3  C12  0.020
 LLC  plan-3  C14  0.020
 LLC  plan-3  O17  0.020
 LLC  plan-3  C16  0.020
 LLC  plan-3  C11  0.020
 LLC  plan-3  S10  0.020
 LLC  plan-3  C2   0.020
 LLC  plan-3  C3   0.020
 LLC  plan-3  H13  0.020
 LLC  plan-3  H14  0.020
 LLC  plan-3  H16  0.020
 LLC  plan-3  C18  0.020
 LLC  plan-4  C20  0.020
 LLC  plan-4  O19  0.020
 LLC  plan-4  C1   0.020
 LLC  plan-4  C18  0.020

