# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 14:48:00 2020
#   Inital geometry file: a 122 line input string
#   Ligand name: ethyl 5-hydroxy-2-phenyl-4-(pyrrolidin-1-ylmethyl)-1-benzofuran-3-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1c(oc2ccc(O)c(CN3CCCC3)c12)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
 I66  I66  'ethyl 5-hydroxy-2-phenyl-4-(pyrrolidin-1-ylmethyl)-1-benzofuran-3-carboxylate'  ligand  50  27  .  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_I66
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
 I66  O1   O  O     0  -0.443  -0.5735  -1.8564  -1.0793
 I66  C2   C  C     0   0.454  -0.3451  -1.2930  -0.0378
 I66  O3   O  O2    0  -0.452  -0.1386  -1.9100   1.1162
 I66  C4   C  CH2   0  -0.196  -0.0801  -3.3431   1.1054
 I66  C5   C  CH3   0  -0.690   0.3609  -3.7956   2.4761
 I66  C6   C  CR5   0  -0.177  -0.4190   0.1728   0.1432
 I66  C7   C  CR56  0   0.183   0.5434   1.0895   0.7028
 I66  C8   C  CR6   0  -0.114   1.8656   0.9926   1.1614
 I66  C9   C  CR6   0   0.317   2.4558   2.1690   1.6195
 I66  O10  O  OH1   0  -0.633   3.7193   2.0964   2.0990
 I66  C11  C  CR16  0  -0.405   1.7825   3.4006   1.5848
 I66  C12  C  CR16  0  -0.346   0.5011   3.5063   1.0805
 I66  C13  C  CR56  0   0.317  -0.0842   2.3335   0.6488
 I66  O14  O  O     0  -0.458  -1.3204   2.2196   0.1085
 I66  C15  C  CR5   0   0.403  -1.5113   0.9157  -0.1884
 I66  C16  C  CR6   0   0.007  -2.8116   0.5727  -0.7547
 I66  C17  C  CR16  0  -0.289  -3.4149   1.4212  -1.6856
 I66  C18  C  CR16  0  -0.243  -4.6500   1.0982  -2.2261
 I66  C19  C  CR16  0  -0.255  -5.2993  -0.0677  -1.8417
 I66  C20  C  CR16  0  -0.241  -4.7105  -0.9082  -0.9057
 I66  C21  C  CR16  0  -0.296  -3.4764  -0.5891  -0.3620
 I66  C22  C  CH2   0  -0.331   2.6326  -0.2983   1.1013
 I66  N23  N  NT    0  -0.431   2.3906  -1.0002  -0.1370
 I66  C24  C  CH2   0  -0.272   2.7753  -0.2871  -1.3432
 I66  C25  C  CH2   0  -0.457   2.7104  -1.3624  -2.4307
 I66  C26  C  CH2   0  -0.463   2.9107  -2.6909  -1.6717
 I66  C27  C  CH2   0  -0.280   3.1046  -2.2612  -0.2196
 I66  H1   H  HCH2  0   0.243  -1.0654  -3.7457   0.8584
 I66  H2   H  HCH2  0   0.236   0.6183  -3.6815   0.3384
 I66  H3   H  HCH3  0   0.240   0.4118  -4.8838   2.4964
 I66  H4   H  HCH3  0   0.232   1.3502  -3.4095   2.7242
 I66  H5   H  HCH3  0   0.239  -0.3387  -3.4793   3.2497
 I66  H6   H  HOH1  0   0.474   4.0492   2.9768   2.3086
 I66  H7   H  HCR6  0   0.275   2.2841   4.2921   1.9428
 I66  H8   H  HCR6  0   0.277  -0.0069   4.4595   1.0255
 I66  H9   H  HCR6  0   0.262  -2.9154   2.3280  -2.0013
 I66  H10  H  HCR6  0   0.264  -5.1055   1.7591  -2.9517
 I66  H11  H  HCR6  0   0.264  -6.2639  -0.3165  -2.2640
 I66  H12  H  HCR6  0   0.264  -5.2180  -1.8093  -0.5875
 I66  H13  H  HCR6  0   0.254  -3.0486  -1.2323   0.3956
 I66  H14  H  HCH2  0   0.223   3.7057  -0.1038   1.2433
 I66  H15  H  HCH2  0   0.249   2.3308  -0.9501   1.9282
 I66  H17  H  HCH2  0   0.236   2.1087   0.5535  -1.5396
 I66  H18  H  HCH2  0   0.196   3.7992   0.1155  -1.2610
 I66  H19  H  HCH2  0   0.233   1.7408  -1.3488  -2.9276
 I66  H20  H  HCH2  0   0.232   3.4697  -1.1984  -3.1947
 I66  H21  H  HCH2  0   0.234   2.0277  -3.3232  -1.7656
 I66  H22  H  HCH2  0   0.233   3.7620  -3.2633  -2.0389
 I66  H23  H  HCH2  0   0.203   4.1771  -2.1248   0.0023
 I66  H24  H  HCH2  0   0.230   2.7176  -2.9841   0.5014

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
 I66  C5   C4   single    1.509  0.020  1.509
 I66  C4   O3   single    1.434  0.020  1.434
 I66  O3   C2   single    1.325  0.020  1.325
 I66  C2   O1   double    1.206  0.020  1.206
 I66  C2   C6   single    1.479  0.020  1.479
 I66  C22  C8   single    1.503  0.020  1.503
 I66  C22  N23  single    1.444  0.020  1.444
 I66  C19  C20  aromatic  1.389  0.020  1.389
 I66  C19  C18  aromatic  1.389  0.020  1.389
 I66  C20  C21  aromatic  1.386  0.020  1.386
 I66  C24  N23  single    1.453  0.020  1.453
 I66  C24  C25  single    1.531  0.020  1.531
 I66  C6   C15  aromatic  1.362  0.020  1.362
 I66  C6   C7   aromatic  1.442  0.020  1.442
 I66  C18  C17  aromatic  1.386  0.020  1.386
 I66  C21  C16  aromatic  1.395  0.020  1.395
 I66  C17  C16  aromatic  1.397  0.020  1.397
 I66  C16  C15  single    1.459  0.020  1.459
 I66  C15  O14  aromatic  1.351  0.020  1.351
 I66  C8   C7   aromatic  1.403  0.020  1.403
 I66  C8   C9   aromatic  1.394  0.020  1.394
 I66  C7   C13  aromatic  1.394  0.020  1.394
 I66  N23  C27  single    1.451  0.020  1.451
 I66  C25  C26  single    1.543  0.020  1.543
 I66  O14  C13  aromatic  1.354  0.020  1.354
 I66  O10  C9   single    1.353  0.020  1.353
 I66  C9   C11  aromatic  1.404  0.020  1.404
 I66  C13  C12  aromatic  1.380  0.020  1.380
 I66  C11  C12  aromatic  1.381  0.020  1.381
 I66  C27  C26  single    1.527  0.020  1.527
 I66  C4   H1   single    0.970  0.020  1.090
 I66  C4   H2   single    0.970  0.020  1.090
 I66  C5   H3   single    0.970  0.020  1.090
 I66  C5   H4   single    0.970  0.020  1.090
 I66  C5   H5   single    0.970  0.020  1.090
 I66  O10  H6   single    0.850  0.020  0.980
 I66  C11  H7   single    0.930  0.020  1.080
 I66  C12  H8   single    0.930  0.020  1.080
 I66  C17  H9   single    0.930  0.020  1.080
 I66  C18  H10  single    0.930  0.020  1.080
 I66  C19  H11  single    0.930  0.020  1.080
 I66  C20  H12  single    0.930  0.020  1.080
 I66  C21  H13  single    0.930  0.020  1.080
 I66  C22  H14  single    0.970  0.020  1.090
 I66  C22  H15  single    0.970  0.020  1.090
 I66  C24  H17  single    0.970  0.020  1.090
 I66  C24  H18  single    0.970  0.020  1.090
 I66  C25  H19  single    0.970  0.020  1.090
 I66  C25  H20  single    0.970  0.020  1.090
 I66  C26  H21  single    0.970  0.020  1.090
 I66  C26  H22  single    0.970  0.020  1.090
 I66  C27  H23  single    0.970  0.020  1.090
 I66  C27  H24  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
 I66  C6   C2   O3   111.27  3.000
 I66  C6   C2   O1   124.01  3.000
 I66  O3   C2   O1   124.35  3.000
 I66  C4   O3   C2   117.72  3.000
 I66  H2   C4   H1   107.69  3.000
 I66  H2   C4   C5   111.00  3.000
 I66  H1   C4   C5   111.00  3.000
 I66  H2   C4   O3   109.95  3.000
 I66  H1   C4   O3   109.46  3.000
 I66  C5   C4   O3   107.74  3.000
 I66  H5   C5   H4   108.55  3.000
 I66  H5   C5   H3   107.85  3.000
 I66  H4   C5   H3   107.88  3.000
 I66  H5   C5   C4   111.72  3.000
 I66  H4   C5   C4   111.44  3.000
 I66  H3   C5   C4   109.27  3.000
 I66  C15  C6   C7   106.44  3.000
 I66  C7   C6   C2   130.10  3.000
 I66  C15  C6   C2   123.43  3.000
 I66  C13  C7   C8   119.90  3.000
 I66  C13  C7   C6   104.58  3.000
 I66  C8   C7   C6   135.40  3.000
 I66  C22  C8   C9   121.47  3.000
 I66  C9   C8   C7   116.64  3.000
 I66  C22  C8   C7   121.83  3.000
 I66  C11  C9   O10  120.23  3.000
 I66  C11  C9   C8   121.95  3.000
 I66  O10  C9   C8   117.81  3.000
 I66  H6   O10  C9   110.35  3.000
 I66  H7   C11  C12  119.15  3.000
 I66  H7   C11  C9   119.44  3.000
 I66  C12  C11  C9   121.41  3.000
 I66  H8   C12  C13  122.27  3.000
 I66  H8   C12  C11  121.46  3.000
 I66  C13  C12  C11  116.28  3.000
 I66  O14  C13  C12  125.70  3.000
 I66  C12  C13  C7   123.72  3.000
 I66  O14  C13  C7   110.57  3.000
 I66  C15  O14  C13  107.33  3.000
 I66  C16  C15  O14  115.98  3.000
 I66  O14  C15  C6   111.08  3.000
 I66  C16  C15  C6   132.92  3.000
 I66  C21  C16  C17  119.19  3.000
 I66  C17  C16  C15  120.06  3.000
 I66  C21  C16  C15  120.74  3.000
 I66  H9   C17  C18  119.51  3.000
 I66  H9   C17  C16  120.27  3.000
 I66  C18  C17  C16  120.21  3.000
 I66  H10  C18  C19  120.10  3.000
 I66  H10  C18  C17  119.62  3.000
 I66  C19  C18  C17  120.28  3.000
 I66  H11  C19  C20  120.12  3.000
 I66  H11  C19  C18  120.12  3.000
 I66  C20  C19  C18  119.76  3.000
 I66  H12  C20  C21  119.60  3.000
 I66  H12  C20  C19  120.22  3.000
 I66  C21  C20  C19  120.17  3.000
 I66  H13  C21  C20  119.34  3.000
 I66  H13  C21  C16  120.25  3.000
 I66  C20  C21  C16  120.38  3.000
 I66  H15  C22  H14  106.06  3.000
 I66  H15  C22  N23  108.18  3.000
 I66  H14  C22  N23  111.12  3.000
 I66  H15  C22  C8   109.89  3.000
 I66  H14  C22  C8   109.93  3.000
 I66  N23  C22  C8   111.49  3.000
 I66  C27  N23  C24  104.41  3.000
 I66  C27  N23  C22  112.88  3.000
 I66  C24  N23  C22  115.40  3.000
 I66  H18  C24  H17  107.42  3.000
 I66  H18  C24  C25  110.40  3.000
 I66  H17  C24  C25  112.81  3.000
 I66  H18  C24  N23  111.28  3.000
 I66  H17  C24  N23  111.47  3.000
 I66  C25  C24  N23  103.52  3.000
 I66  H20  C25  H19  107.37  3.000
 I66  H20  C25  C26  112.58  3.000
 I66  H19  C25  C26  110.52  3.000
 I66  H20  C25  C24  111.28  3.000
 I66  H19  C25  C24  110.67  3.000
 I66  C26  C25  C24  104.47  3.000
 I66  H22  C26  H21  107.41  3.000
 I66  H22  C26  C27  111.66  3.000
 I66  H21  C26  C27  110.37  3.000
 I66  H22  C26  C25  112.83  3.000
 I66  H21  C26  C25  110.60  3.000
 I66  C27  C26  C25  104.01  3.000
 I66  H24  C27  H23  107.07  3.000
 I66  H24  C27  C26  113.38  3.000
 I66  H23  C27  C26  110.46  3.000
 I66  H24  C27  N23  111.29  3.000
 I66  H23  C27  N23  111.05  3.000
 I66  C26  C27  N23  103.66  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
 I66  CONST_03  C13  O14  C15  C6     0.00   0.0  0
 I66  CONST_04  C9   C8   C7   C6   180.00   0.0  0
 I66  CONST_05  O14  C13  C7   C6     0.00   0.0  0
 I66  CONST_06  C12  C13  C7   C6   180.00   0.0  0
 I66  CONST_07  C16  C15  C6   C7   180.00   0.0  0
 I66  CONST_08  O14  C15  C6   C7     0.00   0.0  0
 I66  CONST_09  C11  C9   C8   C7     0.00   0.0  0
 I66  CONST_10  C15  O14  C13  C7     0.00   0.0  0
 I66  CONST_11  C11  C12  C13  C7     0.00   0.0  0
 I66  CONST_12  C15  C6   C7   C8   180.00   0.0  0
 I66  CONST_13  O14  C13  C7   C8   180.00   0.0  0
 I66  CONST_14  C12  C13  C7   C8     0.00   0.0  0
 I66  CONST_15  C12  C11  C9   C8     0.00   0.0  0
 I66  CONST_16  C13  C7   C8   C9     0.00   0.0  0
 I66  CONST_17  C13  C12  C11  C9     0.00   0.0  0
 I66  CONST_18  O14  C13  C12  C11  180.00   0.0  0
 I66  CONST_19  C15  O14  C13  C12  180.00   0.0  0
 I66  CONST_20  C15  C6   C7   C13    0.00   0.0  0
 I66  CONST_21  C16  C15  O14  C13  180.00   0.0  0
 I66  CONST_24  C20  C21  C16  C15  180.00   0.0  0
 I66  CONST_25  C18  C17  C16  C15  180.00   0.0  0
 I66  CONST_26  C19  C20  C21  C16    0.00   0.0  0
 I66  CONST_27  C19  C18  C17  C16    0.00   0.0  0
 I66  CONST_28  C20  C19  C18  C17    0.00   0.0  0
 I66  CONST_29  C20  C21  C16  C17    0.00   0.0  0
 I66  CONST_30  C21  C20  C19  C18    0.00   0.0  0
 I66  CONST_31  C21  C16  C17  C18    0.00   0.0  0
 I66  CONST_32  C16  C15  C6   C2     0.00   0.0  0
 I66  CONST_33  O14  C15  C6   C2   180.00   0.0  0
 I66  CONST_34  C8   C7   C6   C2     0.00   0.0  0
 I66  CONST_35  C13  C7   C6   C2   180.00   0.0  0
 I66  CONST_36  C22  C8   C7   C6     0.00   0.0  0
 I66  CONST_37  O10  C9   C8   C7   180.00   0.0  0
 I66  CONST_38  C12  C11  C9   O10  180.00   0.0  0
 I66  CONST_39  C22  C8   C9   C11  180.00   0.0  0
 I66  CONST_40  C22  C8   C7   C13  180.00   0.0  0
 I66  CONST_41  H8   C12  C13  C7   180.00   0.0  0
 I66  CONST_42  H7   C11  C9   C8   180.00   0.0  0
 I66  CONST_43  H13  C21  C16  C15    0.00   0.0  0
 I66  CONST_44  H9   C17  C16  C15    0.00   0.0  0
 I66  CONST_45  H12  C20  C21  C16  180.00   0.0  0
 I66  CONST_46  H10  C18  C17  C16  180.00   0.0  0
 I66  CONST_47  H11  C19  C18  C17  180.00   0.0  0
 I66  Var_01    C26  C25  C24  N23  -24.77  30.0  1
 I66  Var_02    C25  C26  C27  N23   26.88  30.0  1
 I66  Var_03    C26  C27  N23  C24  -44.04  30.0  1
 I66  Var_04    C27  C26  C25  C24   -1.23  30.0  1
 I66  Var_05    C27  N23  C24  C25   43.06  30.0  1
 I66  Var_06    N23  C22  C8   C7    40.85  30.0  3
 I66  Var_07    C24  N23  C22  C8    60.78  30.0  3
 I66  Var_08    C15  C6   C2   O1    53.08  30.0  2
 I66  Var_09    C6   C2   O3   C4   178.33  30.0  3
 I66  Var_10    C5   C4   O3   C2   171.81  30.0  1
 I66  Var_11    H3   C5   C4   O3   179.88  30.0  3

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
 I66  plan-1  C15  0.020
 I66  plan-1  C16  0.020
 I66  plan-1  C17  0.020
 I66  plan-1  C18  0.020
 I66  plan-1  C19  0.020
 I66  plan-1  C20  0.020
 I66  plan-1  C21  0.020
 I66  plan-1  H9   0.020
 I66  plan-1  H10  0.020
 I66  plan-1  H11  0.020
 I66  plan-1  H12  0.020
 I66  plan-1  H13  0.020
 I66  plan-2  O1   0.020
 I66  plan-2  C2   0.020
 I66  plan-2  O3   0.020
 I66  plan-2  C6   0.020
 I66  plan-3  C2   0.020
 I66  plan-3  C6   0.020
 I66  plan-3  C7   0.020
 I66  plan-3  C8   0.020
 I66  plan-3  C9   0.020
 I66  plan-3  O10  0.020
 I66  plan-3  C11  0.020
 I66  plan-3  C12  0.020
 I66  plan-3  C13  0.020
 I66  plan-3  O14  0.020
 I66  plan-3  C15  0.020
 I66  plan-3  C16  0.020
 I66  plan-3  C22  0.020
 I66  plan-3  H7   0.020
 I66  plan-3  H8   0.020

