# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 07:16:42 2020
#   Inital geometry file: a 137 line input string
#   Ligand name: 2-(1~{H}-benzimidazol-2-yl)-~{N}-[[4-(2-ethylphenyl)-3-methoxy-phenyl]methyl]ethanamine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1ccccc1c2ccc(CNCCc3[nH]c4ccccc4n3)cc2OC
#
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
 AUH  AUH  2-(1~{H}-benzimidazol-2-yl)-~{N}-[[4-(2-ethylphenyl)-3-methoxy-phenyl]methyl]ethanamine  ligand  56  29  .  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_AUH
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
 AUH  C1   C  CH2   0  -0.523    5.8753   0.9217   1.6292
 AUH  N1   N  NR15  0  -0.693   -5.5229   0.9868   0.0558
 AUH  C2   C  CR6   0   0.103    6.1880   0.2047   0.3436
 AUH  N2   N  N     0  -0.475   -5.7532  -0.8750  -1.1262
 AUH  C3   C  CR16  0  -0.306    7.5055   0.1595  -0.1075
 AUH  C4   C  CR16  0  -0.252    7.8607  -0.5481  -1.2472
 AUH  C5   C  CR16  0  -0.262    6.8880  -1.2342  -1.9590
 AUH  C6   C  CR16  0  -0.278    5.5707  -1.1960  -1.5238
 AUH  C7   C  CR6   0   0.050    5.2074  -0.4830  -0.3832
 AUH  C8   C  CR6   0  -0.089    3.7824  -0.4915   0.0345
 AUH  C9   C  CR16  0  -0.251    3.2203  -1.6174   0.6141
 AUH  C10  C  CR16  0  -0.342    1.8765  -1.6576   0.9721
 AUH  C11  C  CR6   0   0.100    1.0680  -0.5552   0.7465
 AUH  C12  C  CH2   0  -0.328   -0.3906  -0.5709   1.1170
 AUH  C13  C  CH2   0  -0.254   -2.6357  -0.2733   0.2821
 AUH  C14  C  CH2   0  -0.558   -3.4534   0.0529  -0.9678
 AUH  C15  C  CR5   0   0.433   -4.9166   0.0344  -0.7035
 AUH  C16  C  CR56  0   0.334   -6.8540   0.6746   0.1284
 AUH  C17  C  CR16  0  -0.309   -7.9357   1.2825   0.7541
 AUH  C18  C  CR16  0  -0.279   -9.1669   0.6664   0.6047
 AUH  C19  C  CR16  0  -0.273   -9.3115  -0.5124  -0.1422
 AUH  C20  C  CR16  0  -0.337   -8.2281  -1.1102  -0.7624
 AUH  C21  C  CR56  0   0.133   -6.9794  -0.5055  -0.6240
 AUH  C22  C  CR16  0  -0.417    1.6143   0.5829   0.1521
 AUH  C23  C  CR6   0   0.379    2.9575   0.6207  -0.2005
 AUH  C24  C  CH3   0  -0.439    2.7918   2.8476  -1.0083
 AUH  O    O  O2    0  -0.465    3.5532   1.6793  -0.7816
 AUH  C    C  CH3   0  -0.656    5.8684  -0.0326   2.8231
 AUH  N    N  NH1   0  -0.593   -1.2233  -0.2802  -0.0363
 AUH  H1   H  HCH2  0   0.240    6.6263   1.6973   1.7940
 AUH  H2   H  HCH2  0   0.245    4.9142   1.4338   1.5665
 AUH  H5   H  HCR6  0   0.245    8.2686   0.6931   0.4479
 AUH  H6   H  HCR6  0   0.252    8.8922  -0.5634  -1.5751
 AUH  H7   H  HCR6  0   0.252    7.1486  -1.7912  -2.8497
 AUH  H8   H  HCR6  0   0.245    4.8066  -1.7263  -2.0793
 AUH  H9   H  HCR6  0   0.249    3.8478  -2.4832   0.7881
 AUH  H10  H  HCR6  0   0.246    1.4642  -2.5527   1.4212
 AUH  H11  H  HCH2  0   0.217   -0.6350  -1.5339   1.5893
 AUH  H12  H  HCH2  0   0.239   -0.5829   0.1981   1.8722
 AUH  H13  H  HCH2  0   0.227   -2.8088   0.4898   1.0464
 AUH  H14  H  HCH2  0   0.210   -2.9854  -1.2266   0.7069
 AUH  H15  H  HCH2  0   0.264   -3.1542   1.0327  -1.3486
 AUH  H16  H  HCH2  0   0.264   -3.2452  -0.6804  -1.7484
 AUH  H17  H  HCR6  0   0.265   -7.8257   2.1907   1.3319
 AUH  H18  H  HCR6  0   0.254  -10.0376   1.1034   1.0759
 AUH  H19  H  HCR6  0   0.251  -10.2922  -0.9605  -0.2341
 AUH  H20  H  HCR6  0   0.252   -8.3429  -2.0200  -1.3378
 AUH  H21  H  HCR6  0   0.270    0.9647   1.4281  -0.0355
 AUH  H22  H  HCH3  0   0.259    3.4669   3.5726  -1.4565
 AUH  H23  H  HCH3  0   0.228    1.9617   2.6695  -1.6968
 AUH  H24  H  HCH3  0   0.228    2.3947   3.2640  -0.0791
 AUH  H25  H  HCH3  0   0.230    5.6776   0.5061   3.7520
 AUH  H26  H  HCH3  0   0.228    5.0959  -0.7937   2.7124
 AUH  H27  H  HCH3  0   0.224    6.8281  -0.5413   2.9220
 AUH  H28  H  HNH1  0   0.345   -1.0487  -0.9826  -0.7464
 AUH  H3   H  HNR5  0   0.418   -5.0732   1.7866   0.4726

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
 AUH  C20  C19  aromatic  1.384  0.020  1.384
 AUH  C20  C21  aromatic  1.394  0.020  1.394
 AUH  C19  C18  aromatic  1.403  0.020  1.403
 AUH  N2   C21  aromatic  1.376  0.020  1.376
 AUH  N2   C15  aromatic  1.306  0.020  1.306
 AUH  C21  C16  aromatic  1.405  0.020  1.405
 AUH  C18  C17  aromatic  1.385  0.020  1.385
 AUH  C14  C15  single    1.487  0.020  1.487
 AUH  C14  C13  single    1.529  0.020  1.529
 AUH  C15  N1   aromatic  1.361  0.020  1.361
 AUH  C16  C17  aromatic  1.390  0.020  1.390
 AUH  C16  N1   aromatic  1.369  0.020  1.369
 AUH  C5   C6   aromatic  1.388  0.020  1.388
 AUH  C5   C4   aromatic  1.387  0.020  1.387
 AUH  C6   C7   aromatic  1.393  0.020  1.393
 AUH  C13  N    single    1.448  0.020  1.448
 AUH  N    C12  single    1.452  0.020  1.452
 AUH  C4   C3   aromatic  1.388  0.020  1.388
 AUH  C7   C8   single    1.485  0.020  1.485
 AUH  C7   C2   aromatic  1.401  0.020  1.401
 AUH  C12  C11  single    1.505  0.020  1.505
 AUH  C11  C22  aromatic  1.395  0.020  1.395
 AUH  C11  C10  aromatic  1.386  0.020  1.386
 AUH  C22  C23  aromatic  1.389  0.020  1.389
 AUH  C8   C9   aromatic  1.385  0.020  1.385
 AUH  C8   C23  aromatic  1.404  0.020  1.404
 AUH  C10  C9   aromatic  1.391  0.020  1.391
 AUH  C23  O    single    1.347  0.020  1.347
 AUH  O    C24  single    1.413  0.020  1.413
 AUH  C3   C2   aromatic  1.393  0.020  1.393
 AUH  C2   C1   single    1.505  0.020  1.505
 AUH  C1   C    single    1.528  0.020  1.528
 AUH  C1   H1   single    0.970  0.020  1.090
 AUH  C1   H2   single    0.970  0.020  1.090
 AUH  N1   H3   single    0.860  0.020  1.020
 AUH  C3   H5   single    0.930  0.020  1.080
 AUH  C4   H6   single    0.930  0.020  1.080
 AUH  C5   H7   single    0.930  0.020  1.080
 AUH  C6   H8   single    0.930  0.020  1.080
 AUH  C9   H9   single    0.930  0.020  1.080
 AUH  C10  H10  single    0.930  0.020  1.080
 AUH  C12  H11  single    0.970  0.020  1.090
 AUH  C12  H12  single    0.970  0.020  1.090
 AUH  C13  H13  single    0.970  0.020  1.090
 AUH  C13  H14  single    0.970  0.020  1.090
 AUH  C14  H15  single    0.970  0.020  1.090
 AUH  C14  H16  single    0.970  0.020  1.090
 AUH  C17  H17  single    0.930  0.020  1.080
 AUH  C18  H18  single    0.930  0.020  1.080
 AUH  C19  H19  single    0.930  0.020  1.080
 AUH  C20  H20  single    0.930  0.020  1.080
 AUH  C22  H21  single    0.930  0.020  1.080
 AUH  C24  H22  single    0.970  0.020  1.090
 AUH  C24  H23  single    0.970  0.020  1.090
 AUH  C24  H24  single    0.970  0.020  1.090
 AUH  C    H25  single    0.970  0.020  1.090
 AUH  C    H26  single    0.970  0.020  1.090
 AUH  C    H27  single    0.970  0.020  1.090
 AUH  N    H28  single    0.890  0.020  1.040

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
 AUH  H2   C1   H1   106.32  3.000
 AUH  H2   C1   C    109.51  3.000
 AUH  H1   C1   C    109.19  3.000
 AUH  H2   C1   C2   110.95  3.000
 AUH  H1   C1   C2   108.93  3.000
 AUH  C    C1   C2   111.77  3.000
 AUH  H3   N1   C16  126.36  3.000
 AUH  H3   N1   C15  125.97  3.000
 AUH  C16  N1   C15  107.65  3.000
 AUH  C7   C2   C3   118.56  3.000
 AUH  C3   C2   C1   119.24  3.000
 AUH  C7   C2   C1   122.11  3.000
 AUH  C21  N2   C15  105.42  3.000
 AUH  H5   C3   C4   119.44  3.000
 AUH  H5   C3   C2   118.93  3.000
 AUH  C4   C3   C2   121.63  3.000
 AUH  H6   C4   C5   120.38  3.000
 AUH  H6   C4   C3   119.99  3.000
 AUH  C5   C4   C3   119.62  3.000
 AUH  H7   C5   C6   120.05  3.000
 AUH  H7   C5   C4   120.54  3.000
 AUH  C6   C5   C4   119.41  3.000
 AUH  H8   C6   C7   119.10  3.000
 AUH  H8   C6   C5   119.68  3.000
 AUH  C7   C6   C5   121.22  3.000
 AUH  C8   C7   C6   118.53  3.000
 AUH  C8   C7   C2   121.91  3.000
 AUH  C6   C7   C2   119.56  3.000
 AUH  C23  C8   C9   118.37  3.000
 AUH  C23  C8   C7   120.80  3.000
 AUH  C9   C8   C7   120.77  3.000
 AUH  H9   C9   C10  119.67  3.000
 AUH  H9   C9   C8   118.80  3.000
 AUH  C10  C9   C8   121.53  3.000
 AUH  H10  C10  C11  120.20  3.000
 AUH  H10  C10  C9   119.89  3.000
 AUH  C11  C10  C9   119.92  3.000
 AUH  C22  C11  C12  119.52  3.000
 AUH  C22  C11  C10  119.33  3.000
 AUH  C12  C11  C10  121.14  3.000
 AUH  H12  C12  H11  106.24  3.000
 AUH  H12  C12  N    107.85  3.000
 AUH  H11  C12  N    112.89  3.000
 AUH  H12  C12  C11  109.44  3.000
 AUH  H11  C12  C11  109.27  3.000
 AUH  N    C12  C11  110.99  3.000
 AUH  H14  C13  H13  106.51  3.000
 AUH  H14  C13  N    113.00  3.000
 AUH  H13  C13  N    108.14  3.000
 AUH  H14  C13  C14  109.29  3.000
 AUH  H13  C13  C14  109.74  3.000
 AUH  N    C13  C14  110.06  3.000
 AUH  H16  C14  H15  107.52  3.000
 AUH  H16  C14  C15  107.86  3.000
 AUH  H15  C14  C15  110.03  3.000
 AUH  H16  C14  C13  109.84  3.000
 AUH  H15  C14  C13  109.25  3.000
 AUH  C15  C14  C13  112.23  3.000
 AUH  C14  C15  N2   125.55  3.000
 AUH  C14  C15  N1   121.94  3.000
 AUH  N2   C15  N1   112.49  3.000
 AUH  C21  C16  C17  122.61  3.000
 AUH  C17  C16  N1   132.92  3.000
 AUH  C21  C16  N1   104.47  3.000
 AUH  H17  C17  C18  121.43  3.000
 AUH  H17  C17  C16  121.90  3.000
 AUH  C18  C17  C16  116.67  3.000
 AUH  H18  C18  C19  119.23  3.000
 AUH  H18  C18  C17  119.25  3.000
 AUH  C19  C18  C17  121.52  3.000
 AUH  H19  C19  C20  119.50  3.000
 AUH  H19  C19  C18  119.11  3.000
 AUH  C20  C19  C18  121.39  3.000
 AUH  H20  C20  C21  120.81  3.000
 AUH  H20  C20  C19  121.21  3.000
 AUH  C21  C20  C19  117.98  3.000
 AUH  C20  C21  C16  119.82  3.000
 AUH  C16  C21  N2   109.96  3.000
 AUH  C20  C21  N2   130.21  3.000
 AUH  H21  C22  C23  121.00  3.000
 AUH  H21  C22  C11  118.41  3.000
 AUH  C23  C22  C11  120.59  3.000
 AUH  O    C23  C22  123.96  3.000
 AUH  O    C23  C8   115.78  3.000
 AUH  C22  C23  C8   120.26  3.000
 AUH  H24  C24  H23  108.76  3.000
 AUH  H24  C24  H22  108.78  3.000
 AUH  H23  C24  H22  108.70  3.000
 AUH  H24  C24  O    111.99  3.000
 AUH  H23  C24  O    112.06  3.000
 AUH  H22  C24  O    106.43  3.000
 AUH  C24  O    C23  118.74  3.000
 AUH  H27  C    H26  107.88  3.000
 AUH  H27  C    H25  107.89  3.000
 AUH  H26  C    H25  107.90  3.000
 AUH  H27  C    C1   110.98  3.000
 AUH  H26  C    C1   111.09  3.000
 AUH  H25  C    C1   110.96  3.000
 AUH  H28  N    C13  108.98  3.000
 AUH  H28  N    C12  108.59  3.000
 AUH  C13  N    C12  112.69  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
 AUH  CONST_01  C21  N2   C15  N1      0.00   0.0  0
 AUH  CONST_02  C20  C21  C16  N1    180.00   0.0  0
 AUH  CONST_03  N2   C21  C16  N1      0.00   0.0  0
 AUH  CONST_04  C18  C17  C16  N1    180.00   0.0  0
 AUH  CONST_05  C5   C6   C7   C2      0.00   0.0  0
 AUH  CONST_08  C5   C4   C3   C2      0.00   0.0  0
 AUH  CONST_09  C19  C20  C21  N2    180.00   0.0  0
 AUH  CONST_10  C17  C16  C21  N2    180.00   0.0  0
 AUH  CONST_11  C16  N1   C15  N2      0.00   0.0  0
 AUH  CONST_12  C6   C5   C4   C3      0.00   0.0  0
 AUH  CONST_13  C6   C7   C2   C3      0.00   0.0  0
 AUH  CONST_14  C8   C7   C2   C3    180.00   0.0  0
 AUH  CONST_15  C7   C6   C5   C4      0.00   0.0  0
 AUH  CONST_16  C7   C2   C3   C4      0.00   0.0  0
 AUH  CONST_17  C8   C7   C6   C5    180.00   0.0  0
 AUH  CONST_20  C10  C9   C8   C7    180.00   0.0  0
 AUH  CONST_21  C22  C23  C8   C7    180.00   0.0  0
 AUH  CONST_22  C11  C10  C9   C8      0.00   0.0  0
 AUH  CONST_23  C11  C22  C23  C8      0.00   0.0  0
 AUH  CONST_24  C22  C23  C8   C9      0.00   0.0  0
 AUH  CONST_25  C22  C11  C10  C9      0.00   0.0  0
 AUH  CONST_26  C23  C22  C11  C10     0.00   0.0  0
 AUH  CONST_27  C23  C8   C9   C10     0.00   0.0  0
 AUH  CONST_28  C20  C21  N2   C15   180.00   0.0  0
 AUH  CONST_29  C16  C21  N2   C15     0.00   0.0  0
 AUH  CONST_30  C21  C16  N1   C15     0.00   0.0  0
 AUH  CONST_31  C17  C16  N1   C15   180.00   0.0  0
 AUH  CONST_32  C19  C20  C21  C16     0.00   0.0  0
 AUH  CONST_33  C19  C18  C17  C16     0.00   0.0  0
 AUH  CONST_34  C20  C19  C18  C17     0.00   0.0  0
 AUH  CONST_35  C20  C21  C16  C17     0.00   0.0  0
 AUH  CONST_36  C21  C20  C19  C18     0.00   0.0  0
 AUH  CONST_37  C21  C16  C17  C18     0.00   0.0  0
 AUH  CONST_38  C6   C7   C2   C1    180.00   0.0  0
 AUH  CONST_39  C8   C7   C2   C1      0.00   0.0  0
 AUH  CONST_40  C4   C3   C2   C1    180.00   0.0  0
 AUH  CONST_41  O    C23  C8   C7      0.00   0.0  0
 AUH  CONST_42  O    C23  C8   C9    180.00   0.0  0
 AUH  CONST_43  C12  C11  C10  C9    180.00   0.0  0
 AUH  CONST_44  O    C23  C22  C11   180.00   0.0  0
 AUH  CONST_45  C23  C22  C11  C12   180.00   0.0  0
 AUH  CONST_46  C21  N2   C15  C14   180.00   0.0  0
 AUH  CONST_47  C16  N1   C15  C14   180.00   0.0  0
 AUH  CONST_48  H17  C17  C16  N1      0.00   0.0  0
 AUH  CONST_49  H8   C6   C7   C2    180.00   0.0  0
 AUH  CONST_50  H6   C4   C3   C2    180.00   0.0  0
 AUH  CONST_51  H20  C20  C21  N2      0.00   0.0  0
 AUH  CONST_52  H3   N1   C15  N2    180.00   0.0  0
 AUH  CONST_53  H7   C5   C4   C3    180.00   0.0  0
 AUH  CONST_54  H5   C3   C4   C5    180.00   0.0  0
 AUH  CONST_55  H9   C9   C8   C7      0.00   0.0  0
 AUH  CONST_56  H10  C10  C9   C8    180.00   0.0  0
 AUH  CONST_57  H21  C22  C23  C8    180.00   0.0  0
 AUH  CONST_58  H18  C18  C17  C16   180.00   0.0  0
 AUH  CONST_59  H19  C19  C18  C17   180.00   0.0  0
 AUH  Var_01    C13  C14  C15  N1     70.01  30.0  2
 AUH  Var_02    C    C1   C2   C3    -93.95  30.0  2
 AUH  Var_03    N    C12  C11  C10  -123.25  30.0  2
 AUH  Var_04    C13  N    C12  C11  -179.45  30.0  1
 AUH  Var_05    N    C13  C14  C15   178.36  30.0  3
 AUH  Var_06    H25  C    C1   C2    177.87  30.0  3
 AUH  Var_07    H22  C24  O    C23   178.62  30.0  3
 AUH  Var_08    C14  C13  N    C12   179.39  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
 AUH  plan-1  C1   0.020
 AUH  plan-1  C2   0.020
 AUH  plan-1  C3   0.020
 AUH  plan-1  C4   0.020
 AUH  plan-1  C5   0.020
 AUH  plan-1  C6   0.020
 AUH  plan-1  C7   0.020
 AUH  plan-1  C8   0.020
 AUH  plan-1  H5   0.020
 AUH  plan-1  H6   0.020
 AUH  plan-1  H7   0.020
 AUH  plan-1  H8   0.020
 AUH  plan-2  C7   0.020
 AUH  plan-2  C8   0.020
 AUH  plan-2  C9   0.020
 AUH  plan-2  C10  0.020
 AUH  plan-2  C11  0.020
 AUH  plan-2  C12  0.020
 AUH  plan-2  C22  0.020
 AUH  plan-2  C23  0.020
 AUH  plan-2  O    0.020
 AUH  plan-2  H9   0.020
 AUH  plan-2  H10  0.020
 AUH  plan-2  H21  0.020
 AUH  plan-3  N1   0.020
 AUH  plan-3  N2   0.020
 AUH  plan-3  C14  0.020
 AUH  plan-3  C15  0.020
 AUH  plan-3  C16  0.020
 AUH  plan-3  C17  0.020
 AUH  plan-3  C18  0.020
 AUH  plan-3  C19  0.020
 AUH  plan-3  C20  0.020
 AUH  plan-3  C21  0.020
 AUH  plan-3  H17  0.020
 AUH  plan-3  H18  0.020
 AUH  plan-3  H19  0.020
 AUH  plan-3  H20  0.020
 AUH  plan-3  H3   0.020

