# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 13 09:08:53 2020
#   Inital geometry file: a 136 line input string
#   Ligand name: 4-[(azepan-1-yl)methyl]-5-hydroxy-2-methyl-N-[4-(trifluoromethyl)phenyl]-1-benzofuran-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1oc2ccc(O)c(CN3CCCCCC3)c2c1C(=O)Nc4ccc(cc4)C(F)(F)F
#
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
 9WP  9WP  4-[(azepan-1-yl)methyl]-5-hydroxy-2-methyl-N-[4-(trifluoromethyl)phenyl]-1-benzofuran-3-carboxamide  ligand  57  32  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9WP
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
 9WP  C1   C  CR16  0  -0.342  -5.0465  -1.9279   0.7483
 9WP  N1   N  NH1   0  -0.747   0.2855  -1.1658  -0.0919
 9WP  O1   O  OH1   0  -0.634  -3.8712   0.4010   3.3098
 9WP  C2   C  CR16  0  -0.409  -4.9931  -1.1705   1.9028
 9WP  N2   N  NT    0  -0.403  -1.3620   1.4772   0.3910
 9WP  O2   O  O     0  -0.452  -3.8031  -2.5196  -1.2568
 9WP  C3   C  CR6   0   0.326  -3.8872  -0.3562   2.1884
 9WP  O3   O  O     0  -0.457  -0.1363  -0.5483  -2.2442
 9WP  C4   C  CR6   0  -0.122  -2.7840  -0.2792   1.3363
 9WP  C5   C  CH2   0  -0.354  -1.6733   0.7056   1.5869
 9WP  C6   C  CR5   0   0.381  -2.5919  -2.1988  -1.7564
 9WP  C7   C  CR5   0  -0.213  -1.9302  -1.3497  -0.9241
 9WP  C8   C  CR56  0   0.170  -2.8124  -1.0961   0.1946
 9WP  C9   C  CR56  0   0.310  -3.9438  -1.8648  -0.0774
 9WP  C10  C  C     0   0.458  -0.5312  -0.9393  -1.1618
 9WP  C11  C  CR6   0  -0.218   4.3063  -0.2453   0.6236
 9WP  C12  C  CR16  0  -0.262   3.4914  -0.7799   1.6167
 9WP  C13  C  CR16  0  -0.341   2.1716  -1.0757   1.3454
 9WP  C14  C  CR6   0   0.383   1.6263  -0.8459   0.0776
 9WP  C15  C  CR16  0  -0.292   2.4490  -0.3202  -0.9206
 9WP  C16  C  CR16  0  -0.269   3.7720  -0.0207  -0.6375
 9WP  C18  C  CH3   0  -0.750  -2.2302  -2.8299  -3.0447
 9WP  C19  C  CH2   0  -0.292  -2.4905   2.3126  -0.0115
 9WP  C20  C  CH2   0  -0.411  -2.6721   2.4641  -1.5155
 9WP  C21  C  CH2   0  -0.440  -1.4217   2.8498  -2.3098
 9WP  C22  C  CH2   0  -0.447  -0.4029   3.6933  -1.5463
 9WP  C23  C  CH2   0  -0.429   0.4806   2.8549  -0.6257
 9WP  C24  C  CH2   0  -0.282  -0.1711   2.2814   0.6224
 9WP  F1   F  F     0  -0.317   5.7997   1.3687   1.4547
 9WP  F2   F  F     0  -0.310   6.2743  -0.6925   1.8318
 9WP  F3   F  F     0  -0.308   6.5000   0.1212  -0.1495
 9WP  H11  H  HCR6  0   0.275  -5.9091  -2.5360   0.5116
 9WP  H17  H  HNH1  0   0.418  -0.1523  -1.5987   0.7072
 9WP  H14  H  HOH1  0   0.475  -4.7166   0.3387   3.7671
 9WP  H2   H  HCR6  0   0.274  -5.8307  -1.1932   2.5902
 9WP  H51  H  HCH2  0   0.234  -0.7651   0.1822   1.8993
 9WP  H52  H  HCH2  0   0.234  -1.9317   1.3552   2.4341
 9WP  H12  H  HCR6  0   0.275   3.8719  -0.9734   2.6110
 9WP  H13  H  HCR6  0   0.278   1.5541  -1.4952   2.1308
 9WP  H15  H  HCR6  0   0.289   2.0740  -0.1419  -1.9138
 9WP  H16  H  HCR6  0   0.272   4.3795   0.3906  -1.4327
 9WP  H54  H  HCH3  0   0.264  -2.4405  -3.8995  -3.0258
 9WP  H18  H  HCH3  0   0.269  -2.8064  -2.3936  -3.8632
 9WP  H53  H  HCH3  0   0.264  -1.1772  -2.6877  -3.2680
 9WP  H19  H  HCH2  0   0.240  -3.4144   1.8842   0.3811
 9WP  H55  H  HCH2  0   0.199  -2.4062   3.3055   0.4568
 9WP  H20  H  HCH2  0   0.217  -3.0755   1.5325  -1.9205
 9WP  H56  H  HCH2  0   0.209  -3.4484   3.2216  -1.6607
 9WP  H21  H  HCH2  0   0.228  -0.9182   1.9432  -2.6504
 9WP  H57  H  HCH2  0   0.218  -1.7340   3.3797  -3.2137
 9WP  H58  H  HCH2  0   0.225   0.2479   4.1943  -2.2678
 9WP  H22  H  HCH2  0   0.210  -0.8979   4.4949  -0.9868
 9WP  H59  H  HCH2  0   0.223   0.9040   2.0335  -1.2087
 9WP  H23  H  HCH2  0   0.219   1.3292   3.4566  -0.2865
 9WP  H24  H  HCH2  0   0.190  -0.3971   3.1060   1.3226
 9WP  H6A  H  HCH2  0   0.225   0.5720   1.6563   1.1251
 9WP  C17  C  CT    0   1.050   5.7156   0.1315   0.9350

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
 9WP  F3   C17  single    1.339  0.020  1.339
 9WP  O3   C10  double    1.217  0.020  1.217
 9WP  C5   C4   single    1.505  0.020  1.505
 9WP  C5   N2   single    1.457  0.020  1.457
 9WP  C17  F1   single    1.345  0.020  1.345
 9WP  C17  C11  single    1.492  0.020  1.492
 9WP  C17  F2   single    1.340  0.020  1.340
 9WP  O1   C3   single    1.353  0.020  1.353
 9WP  C12  C11  aromatic  1.391  0.020  1.391
 9WP  C12  C13  aromatic  1.379  0.020  1.379
 9WP  C11  C16  aromatic  1.388  0.020  1.388
 9WP  C4   C3   aromatic  1.396  0.020  1.396
 9WP  C4   C8   aromatic  1.404  0.020  1.404
 9WP  C3   C2   aromatic  1.403  0.020  1.403
 9WP  C19  N2   single    1.461  0.020  1.461
 9WP  C19  C20  single    1.522  0.020  1.522
 9WP  C13  C14  aromatic  1.399  0.020  1.399
 9WP  N2   C24  single    1.456  0.020  1.456
 9WP  C10  C7   single    1.477  0.020  1.477
 9WP  C10  N1   single    1.365  0.020  1.365
 9WP  C24  C23  single    1.520  0.020  1.520
 9WP  C8   C7   aromatic  1.447  0.020  1.447
 9WP  C8   C9   aromatic  1.395  0.020  1.395
 9WP  C16  C15  aromatic  1.386  0.020  1.386
 9WP  C2   C1   aromatic  1.382  0.020  1.382
 9WP  C14  C15  aromatic  1.396  0.020  1.396
 9WP  C14  N1   single    1.389  0.020  1.389
 9WP  C7   C6   aromatic  1.361  0.020  1.361
 9WP  C9   C1   aromatic  1.379  0.020  1.379
 9WP  C9   O2   aromatic  1.356  0.020  1.356
 9WP  C20  C21  single    1.531  0.020  1.531
 9WP  C6   O2   aromatic  1.349  0.020  1.349
 9WP  C6   C18  single    1.479  0.020  1.479
 9WP  C23  C22  single    1.527  0.020  1.527
 9WP  C22  C21  single    1.527  0.020  1.527
 9WP  C1   H11  single    0.930  0.020  1.080
 9WP  N1   H17  single    0.860  0.020  1.020
 9WP  O1   H14  single    0.850  0.020  0.980
 9WP  C2   H2   single    0.930  0.020  1.080
 9WP  C5   H51  single    0.970  0.020  1.090
 9WP  C5   H52  single    0.970  0.020  1.090
 9WP  C12  H12  single    0.930  0.020  1.080
 9WP  C13  H13  single    0.930  0.020  1.080
 9WP  C15  H15  single    0.930  0.020  1.080
 9WP  C16  H16  single    0.930  0.020  1.080
 9WP  C18  H54  single    0.970  0.020  1.090
 9WP  C18  H18  single    0.970  0.020  1.090
 9WP  C18  H53  single    0.970  0.020  1.090
 9WP  C19  H19  single    0.970  0.020  1.090
 9WP  C19  H55  single    0.970  0.020  1.090
 9WP  C20  H20  single    0.970  0.020  1.090
 9WP  C20  H56  single    0.970  0.020  1.090
 9WP  C21  H21  single    0.970  0.020  1.090
 9WP  C21  H57  single    0.970  0.020  1.090
 9WP  C22  H58  single    0.970  0.020  1.090
 9WP  C22  H22  single    0.970  0.020  1.090
 9WP  C23  H59  single    0.970  0.020  1.090
 9WP  C23  H23  single    0.970  0.020  1.090
 9WP  C24  H24  single    0.970  0.020  1.090
 9WP  C24  H6A  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
 9WP  H11  C1   C9   122.17  3.000
 9WP  H11  C1   C2   121.45  3.000
 9WP  C9   C1   C2   116.38  3.000
 9WP  H17  N1   C14  114.91  3.000
 9WP  H17  N1   C10  115.62  3.000
 9WP  C14  N1   C10  129.43  3.000
 9WP  H14  O1   C3   110.30  3.000
 9WP  H2   C2   C3   119.49  3.000
 9WP  H2   C2   C1   119.25  3.000
 9WP  C3   C2   C1   121.25  3.000
 9WP  C24  N2   C19  111.10  3.000
 9WP  C24  N2   C5   109.69  3.000
 9WP  C19  N2   C5   111.34  3.000
 9WP  C9   O2   C6   107.48  3.000
 9WP  C4   C3   C2   122.06  3.000
 9WP  C2   C3   O1   120.19  3.000
 9WP  C4   C3   O1   117.75  3.000
 9WP  C8   C4   C5   122.06  3.000
 9WP  C8   C4   C3   116.63  3.000
 9WP  C5   C4   C3   121.17  3.000
 9WP  H52  C5   H51  104.95  3.000
 9WP  H52  C5   C4   109.98  3.000
 9WP  H51  C5   C4   110.31  3.000
 9WP  H52  C5   N2   111.73  3.000
 9WP  H51  C5   N2   108.09  3.000
 9WP  C4   C5   N2   111.56  3.000
 9WP  C18  C6   C7   132.83  3.000
 9WP  C18  C6   O2   116.14  3.000
 9WP  C7   C6   O2   111.01  3.000
 9WP  C10  C7   C8   130.78  3.000
 9WP  C8   C7   C6   106.60  3.000
 9WP  C10  C7   C6   122.38  3.000
 9WP  C9   C8   C7   104.32  3.000
 9WP  C9   C8   C4   119.71  3.000
 9WP  C7   C8   C4   135.90  3.000
 9WP  C8   C9   O2   110.58  3.000
 9WP  O2   C9   C1   125.56  3.000
 9WP  C8   C9   C1   123.86  3.000
 9WP  C7   C10  O3   122.67  3.000
 9WP  C7   C10  N1   113.23  3.000
 9WP  O3   C10  N1   123.81  3.000
 9WP  C17  C11  C16  120.83  3.000
 9WP  C16  C11  C12  119.03  3.000
 9WP  C17  C11  C12  120.09  3.000
 9WP  H12  C12  C13  118.61  3.000
 9WP  H12  C12  C11  121.23  3.000
 9WP  C13  C12  C11  120.15  3.000
 9WP  H13  C13  C14  119.89  3.000
 9WP  H13  C13  C12  119.05  3.000
 9WP  C14  C13  C12  121.06  3.000
 9WP  C15  C14  C13  118.69  3.000
 9WP  C15  C14  N1   124.64  3.000
 9WP  C13  C14  N1   116.68  3.000
 9WP  H15  C15  C16  119.03  3.000
 9WP  H15  C15  C14  121.11  3.000
 9WP  C16  C15  C14  119.86  3.000
 9WP  H16  C16  C15  117.91  3.000
 9WP  H16  C16  C11  120.88  3.000
 9WP  C15  C16  C11  121.21  3.000
 9WP  H53  C18  H18  107.78  3.000
 9WP  H53  C18  H54  108.60  3.000
 9WP  H18  C18  H54  107.65  3.000
 9WP  H53  C18  C6   111.12  3.000
 9WP  H18  C18  C6   110.69  3.000
 9WP  H54  C18  C6   110.87  3.000
 9WP  H55  C19  H19  105.41  3.000
 9WP  H55  C19  C20  109.85  3.000
 9WP  H19  C19  C20  107.06  3.000
 9WP  H55  C19  N2   109.84  3.000
 9WP  H19  C19  N2   109.30  3.000
 9WP  C20  C19  N2   114.91  3.000
 9WP  H56  C20  H20  106.20  3.000
 9WP  H56  C20  C21  109.64  3.000
 9WP  H20  C20  C21  108.90  3.000
 9WP  H56  C20  C19  106.53  3.000
 9WP  H20  C20  C19  108.98  3.000
 9WP  C21  C20  C19  116.12  3.000
 9WP  H57  C21  H21  106.04  3.000
 9WP  H57  C21  C22  109.64  3.000
 9WP  H21  C21  C22  107.88  3.000
 9WP  H57  C21  C20  108.54  3.000
 9WP  H21  C21  C20  109.24  3.000
 9WP  C22  C21  C20  115.13  3.000
 9WP  H22  C22  H58  105.70  3.000
 9WP  H22  C22  C23  110.81  3.000
 9WP  H58  C22  C23  107.77  3.000
 9WP  H22  C22  C21  110.97  3.000
 9WP  H58  C22  C21  108.68  3.000
 9WP  C23  C22  C21  112.59  3.000
 9WP  H23  C23  H59  106.16  3.000
 9WP  H23  C23  C24  106.58  3.000
 9WP  H59  C23  C24  108.70  3.000
 9WP  H23  C23  C22  109.50  3.000
 9WP  H59  C23  C22  108.38  3.000
 9WP  C24  C23  C22  117.01  3.000
 9WP  H6A  C24  H24  105.91  3.000
 9WP  H6A  C24  C23  107.57  3.000
 9WP  H24  C24  C23  109.05  3.000
 9WP  H6A  C24  N2   108.26  3.000
 9WP  H24  C24  N2   110.22  3.000
 9WP  C23  C24  N2   115.38  3.000
 9WP  F3   C17  F2   107.05  3.000
 9WP  F2   C17  F1   106.33  3.000
 9WP  F3   C17  F1   106.47  3.000
 9WP  F2   C17  C11  112.23  3.000
 9WP  F1   C17  C11  111.85  3.000
 9WP  F3   C17  C11  112.49  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
 9WP  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 9WP  CONST_02  C4   C8   C9   C1      0.00   0.0  0
 9WP  CONST_03  C7   C8   C9   C1    180.00   0.0  0
 9WP  CONST_04  C6   O2   C9   C1    180.00   0.0  0
 9WP  CONST_05  C8   C4   C3   C2      0.00   0.0  0
 9WP  CONST_06  C8   C9   C1   C2      0.00   0.0  0
 9WP  CONST_07  O2   C9   C1   C2    180.00   0.0  0
 9WP  CONST_08  C4   C8   C9   O2    180.00   0.0  0
 9WP  CONST_09  C7   C8   C9   O2      0.00   0.0  0
 9WP  CONST_10  C8   C7   C6   O2      0.00   0.0  0
 9WP  CONST_11  C7   C8   C4   C3    180.00   0.0  0
 9WP  CONST_12  C9   C8   C4   C3      0.00   0.0  0
 9WP  CONST_13  C9   C1   C2   C3      0.00   0.0  0
 9WP  CONST_14  C6   C7   C8   C4    180.00   0.0  0
 9WP  CONST_15  C9   C8   C7   C6      0.00   0.0  0
 9WP  CONST_16  C8   C9   O2   C6      0.00   0.0  0
 9WP  CONST_17  C9   O2   C6   C7      0.00   0.0  0
 9WP  CONST_18  C14  C13  C12  C11     0.00   0.0  0
 9WP  CONST_19  C14  C15  C16  C11     0.00   0.0  0
 9WP  CONST_20  C15  C16  C11  C12     0.00   0.0  0
 9WP  CONST_21  C15  C14  C13  C12     0.00   0.0  0
 9WP  CONST_22  C16  C11  C12  C13     0.00   0.0  0
 9WP  CONST_23  C16  C15  C14  C13     0.00   0.0  0
 9WP  CONST_24  O1   C3   C2   C1    180.00   0.0  0
 9WP  CONST_25  C12  C13  C14  N1    180.00   0.0  0
 9WP  CONST_26  C16  C15  C14  N1    180.00   0.0  0
 9WP  CONST_27  C8   C4   C3   O1    180.00   0.0  0
 9WP  CONST_28  C5   C4   C3   C2    180.00   0.0  0
 9WP  CONST_29  C10  C7   C6   O2    180.00   0.0  0
 9WP  CONST_30  C10  C7   C8   C4      0.00   0.0  0
 9WP  CONST_31  C7   C8   C4   C5      0.00   0.0  0
 9WP  CONST_32  C9   C8   C4   C5    180.00   0.0  0
 9WP  CONST_33  C18  C6   C7   C8    180.00   0.0  0
 9WP  CONST_34  C10  C7   C8   C9    180.00   0.0  0
 9WP  CONST_35  C18  C6   O2   C9    180.00   0.0  0
 9WP  CONST_36  C17  C11  C12  C13   180.00   0.0  0
 9WP  CONST_37  C17  C11  C16  C15   180.00   0.0  0
 9WP  CONST_38  H11  C1   C9   O2      0.00   0.0  0
 9WP  CONST_39  H2   C2   C3   C4    180.00   0.0  0
 9WP  CONST_40  H13  C13  C12  C11   180.00   0.0  0
 9WP  CONST_41  H15  C15  C16  C11   180.00   0.0  0
 9WP  CONST_42  H16  C16  C11  C12   180.00   0.0  0
 9WP  CONST_43  H12  C12  C13  C14   180.00   0.0  0
 9WP  CONST_44  C14  N1   C10  C7    180.00   0.0  0
 9WP  CONST_45  C13  C14  N1   C10   180.00   0.0  0
 9WP  CONST_46  C15  C14  N1   C10     0.00   0.0  0
 9WP  CONST_47  H17  N1   C14  C13     0.00   0.0  0
 9WP  CONST_48  C14  N1   C10  O3      0.00   0.0  0
 9WP  Var_01    C3   C4   C5   N2   -129.75  30.0  2
 9WP  Var_02    C8   C7   C10  N1     47.54  30.0  2
 9WP  Var_03    F3   C17  C11  C12   155.38  30.0  3
 9WP  Var_04    H54  C18  C6   O2    -47.20  30.0  2

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
 9WP  plan-1  N1   0.020
 9WP  plan-1  C11  0.020
 9WP  plan-1  C12  0.020
 9WP  plan-1  C13  0.020
 9WP  plan-1  C14  0.020
 9WP  plan-1  C15  0.020
 9WP  plan-1  C16  0.020
 9WP  plan-1  H12  0.020
 9WP  plan-1  H13  0.020
 9WP  plan-1  H15  0.020
 9WP  plan-1  H16  0.020
 9WP  plan-1  C17  0.020
 9WP  plan-2  C1   0.020
 9WP  plan-2  O1   0.020
 9WP  plan-2  C2   0.020
 9WP  plan-2  O2   0.020
 9WP  plan-2  C3   0.020
 9WP  plan-2  C4   0.020
 9WP  plan-2  C5   0.020
 9WP  plan-2  C6   0.020
 9WP  plan-2  C7   0.020
 9WP  plan-2  C8   0.020
 9WP  plan-2  C9   0.020
 9WP  plan-2  C10  0.020
 9WP  plan-2  C18  0.020
 9WP  plan-2  H11  0.020
 9WP  plan-2  H2   0.020
 9WP  plan-3  N1   0.020
 9WP  plan-3  O3   0.020
 9WP  plan-3  C7   0.020
 9WP  plan-3  C10  0.020
 9WP  plan-3  C14  0.020
 9WP  plan-3  H17  0.020

