# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May 21 11:38:09 2020
#   Inital geometry file: a 146 line input string
#   Ligand name: 4-(2-hydroxypropan-2-yl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCc1nc(c(n1Cc2ccc(cc2)c3ccccc3c4[nH]nnn4)C(O)=O)C(C)(C)O
#
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
 OLM  OLM  '4-(2-hydroxypropan-2-yl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid'  ligand  59  33  .  2021-08-19  2021-08-19  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OLM
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
 OLM  C4   C  CR16  0  -0.282   2.1080   1.8310   1.2016
 OLM  C3   C  CR16  0  -0.283   0.8396   1.7296   1.7504
 OLM  O3   O  OH1   0  -0.664  -5.1360  -2.7260  -0.2253
 OLM  C2   C  CR6   0   0.079  -0.1101   0.8768   1.1976
 OLM  O2   O  OH1   0  -0.595  -2.6879  -1.8497   2.7443
 OLM  C1   C  CH2   0  -0.395  -1.4707   0.7804   1.8426
 OLM  O1   O  O     0  -0.419  -2.4370  -3.1633   0.9586
 OLM  C20  C  CH3   0  -0.666  -3.2676   4.9903   0.6587
 OLM  C19  C  CH2   0  -0.428  -3.5705   3.5066   0.8032
 OLM  C15  C  CR5   0   0.461  -3.0029   1.2008  -0.0466
 OLM  N6   N  N     0  -0.462  -3.7914   0.5472  -0.8681
 OLM  C16  C  CR5   0   0.157  -3.7968  -0.7470  -0.4630
 OLM  C22  C  CT    0   0.125  -4.6404  -1.7892  -1.1642
 OLM  C23  C  CH3   0  -0.661  -3.7772  -2.5701  -2.1520
 OLM  C24  C  CH3   0  -0.668  -5.8008  -1.1227  -1.9016
 OLM  C17  C  CR5   0   0.137  -2.9937  -0.8839   0.6468
 OLM  C21  C  C     0   0.463  -2.6759  -2.0823   1.4340
 OLM  N1   N  NR5   0  -0.482  -2.5139   0.3872   0.9143
 OLM  C7   C  CR16  0  -0.270   0.2365   0.1276   0.0787
 OLM  C6   C  CR16  0  -0.274   1.5049   0.2287  -0.4706
 OLM  C5   C  CR6   0   0.038   2.4591   1.0777   0.0847
 OLM  C8   C  CR6   0   0.113   3.7959   1.2192  -0.5310
 OLM  C9   C  CR16  0  -0.297   4.2361   2.4800  -0.9280
 OLM  C10  C  CR16  0  -0.232   5.4548   2.6471  -1.5683
 OLM  C11  C  CR16  0  -0.254   6.2582   1.5470  -1.8315
 OLM  C12  C  CR16  0  -0.259   5.8450   0.2871  -1.4303
 OLM  C13  C  CR6   0   0.026   4.6273   0.1181  -0.7741
 OLM  C14  C  CR5   0   0.384   4.2701  -1.2175  -0.2954
 OLM  N5   N  NR15  0  -0.461   4.2993  -2.3326  -1.0293
 OLM  N4   N  N     0  -0.077   3.9563  -3.3583  -0.2731
 OLM  N3   N  N     0  -0.150   3.7271  -2.8847   0.8888
 OLM  N2   N  N     0  -0.317   3.9107  -1.5668   0.9186
 OLM  H1   H  HCR6  0   0.258   2.8302   2.4997   1.6530
 OLM  H2   H  HCR6  0   0.258   0.5874   2.3265   2.6189
 OLM  H3   H  HOH1  0   0.443  -5.7558  -2.2706   0.3550
 OLM  H4   H  HOH1  0   0.490  -2.4081  -2.6452   3.2230
 OLM  H5   H  HCH2  0   0.310  -1.4459   0.0754   2.6700
 OLM  H6   H  HCH2  0   0.288  -1.7454   1.7405   2.2793
 OLM  H7   H  HCH3  0   0.223  -3.4450   5.3324  -0.3624
 OLM  H8   H  HCH3  0   0.235  -3.8942   5.5862   1.3221
 OLM  H9   H  HCH3  0   0.223  -2.2265   5.2063   0.9037
 OLM  H10  H  HCH2  0   0.230  -3.4138   3.1996   1.8411
 OLM  H11  H  HCH2  0   0.236  -4.6234   3.3165   0.5824
 OLM  H12  H  HCH2  0   0.267  -2.8758   2.9657  -1.1640
 OLM  H13  H  HCH2  0   0.252  -1.6450   2.8391   0.0740
 OLM  H14  H  HCH3  0   0.229  -3.3318  -1.8937  -2.8814
 OLM  H15  H  HCH3  0   0.243  -2.9727  -3.0958  -1.6394
 OLM  H16  H  HCH3  0   0.231  -4.3804  -3.2998  -2.6957
 OLM  H17  H  HCH3  0   0.230  -6.4411  -0.5649  -1.2153
 OLM  H18  H  HCH3  0   0.231  -5.4503  -0.4280  -2.6622
 OLM  H19  H  HCH3  0   0.234  -6.4074  -1.8852  -2.3922
 OLM  H20  H  HCR6  0   0.256  -0.4801  -0.5371  -0.3889
 OLM  H21  H  HCR6  0   0.257   1.7415  -0.3473  -1.3568
 OLM  H22  H  HCR6  0   0.264   3.6012   3.3397  -0.7549
 OLM  H23  H  HCR6  0   0.269   5.7714   3.6368  -1.8691
 OLM  H24  H  HCR6  0   0.269   7.2068   1.6685  -2.3366
 OLM  H25  H  HCR6  0   0.272   6.4871  -0.5672  -1.6048
 OLM  H26  H  HNR5  0   0.452   4.5106  -2.4576  -2.0100
 OLM  C18  C  CH2   0  -0.537  -2.7035   2.6567  -0.1316

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
 OLM  C23  C22  single    1.527  0.020  1.527
 OLM  O1   C21  double    1.205  0.020  1.205
 OLM  O2   C21  single    1.331  0.020  1.331
 OLM  C21  C17  single    1.469  0.020  1.469
 OLM  C22  C24  single    1.528  0.020  1.528
 OLM  C22  O3   single    1.416  0.020  1.416
 OLM  C22  C16  single    1.513  0.020  1.513
 OLM  C17  C16  aromatic  1.377  0.020  1.377
 OLM  C17  N1   aromatic  1.385  0.020  1.385
 OLM  C16  N6   aromatic  1.356  0.020  1.356
 OLM  N4   N3   aromatic  1.275  0.020  1.275
 OLM  N4   N5   aromatic  1.320  0.020  1.320
 OLM  N3   N2   aromatic  1.331  0.020  1.331
 OLM  N1   C1   single    1.451  0.020  1.451
 OLM  N1   C15  aromatic  1.351  0.020  1.351
 OLM  C1   C2   single    1.509  0.020  1.509
 OLM  N5   C14  aromatic  1.335  0.020  1.335
 OLM  N6   C15  aromatic  1.313  0.020  1.313
 OLM  C15  C18  single    1.489  0.020  1.489
 OLM  C2   C3   aromatic  1.391  0.020  1.391
 OLM  C2   C7   aromatic  1.390  0.020  1.390
 OLM  N2   C14  aromatic  1.313  0.020  1.313
 OLM  C3   C4   aromatic  1.386  0.020  1.386
 OLM  C14  C13  single    1.463  0.020  1.463
 OLM  C7   C6   aromatic  1.386  0.020  1.386
 OLM  C4   C5   aromatic  1.392  0.020  1.392
 OLM  C18  C19  single    1.532  0.020  1.532
 OLM  C6   C5   aromatic  1.393  0.020  1.393
 OLM  C5   C8   single    1.479  0.020  1.479
 OLM  C13  C8   aromatic  1.401  0.020  1.401
 OLM  C13  C12  aromatic  1.394  0.020  1.394
 OLM  C8   C9   aromatic  1.393  0.020  1.393
 OLM  C19  C20  single    1.521  0.020  1.521
 OLM  C12  C11  aromatic  1.385  0.020  1.385
 OLM  C9   C10  aromatic  1.387  0.020  1.387
 OLM  C11  C10  aromatic  1.387  0.020  1.387
 OLM  C4   H1   single    0.930  0.020  1.080
 OLM  C3   H2   single    0.930  0.020  1.080
 OLM  O3   H3   single    0.850  0.020  0.980
 OLM  O2   H4   single    0.850  0.020  0.980
 OLM  C1   H5   single    0.970  0.020  1.090
 OLM  C1   H6   single    0.970  0.020  1.090
 OLM  C20  H7   single    0.970  0.020  1.090
 OLM  C20  H8   single    0.970  0.020  1.090
 OLM  C20  H9   single    0.970  0.020  1.090
 OLM  C19  H10  single    0.970  0.020  1.090
 OLM  C19  H11  single    0.970  0.020  1.090
 OLM  C18  H12  single    0.970  0.020  1.090
 OLM  C18  H13  single    0.970  0.020  1.090
 OLM  C23  H14  single    0.970  0.020  1.090
 OLM  C23  H15  single    0.970  0.020  1.090
 OLM  C23  H16  single    0.970  0.020  1.090
 OLM  C24  H17  single    0.970  0.020  1.090
 OLM  C24  H18  single    0.970  0.020  1.090
 OLM  C24  H19  single    0.970  0.020  1.090
 OLM  C7   H20  single    0.930  0.020  1.080
 OLM  C6   H21  single    0.930  0.020  1.080
 OLM  C9   H22  single    0.930  0.020  1.080
 OLM  C10  H23  single    0.930  0.020  1.080
 OLM  C11  H24  single    0.930  0.020  1.080
 OLM  C12  H25  single    0.930  0.020  1.080
 OLM  N5   H26  single    0.860  0.020  1.020

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
 OLM  H1   C4   C5   120.02  3.000
 OLM  H1   C4   C3   119.38  3.000
 OLM  C5   C4   C3   120.60  3.000
 OLM  H2   C3   C2   119.82  3.000
 OLM  H2   C3   C4   119.35  3.000
 OLM  C2   C3   C4   120.82  3.000
 OLM  H3   O3   C22  108.17  3.000
 OLM  C7   C2   C1   122.30  3.000
 OLM  C7   C2   C3   118.68  3.000
 OLM  C1   C2   C3   119.01  3.000
 OLM  H4   O2   C21  109.88  3.000
 OLM  H6   C1   H5   105.79  3.000
 OLM  H6   C1   N1   108.29  3.000
 OLM  H5   C1   N1   109.12  3.000
 OLM  H6   C1   C2   110.01  3.000
 OLM  H5   C1   C2   110.25  3.000
 OLM  N1   C1   C2   113.10  3.000
 OLM  H9   C20  H8   107.68  3.000
 OLM  H9   C20  H7   107.65  3.000
 OLM  H8   C20  H7   107.74  3.000
 OLM  H9   C20  C19  111.21  3.000
 OLM  H8   C20  C19  111.16  3.000
 OLM  H7   C20  C19  111.23  3.000
 OLM  H11  C19  H10  106.33  3.000
 OLM  H11  C19  C18  109.00  3.000
 OLM  H10  C19  C18  110.01  3.000
 OLM  H11  C19  C20  110.03  3.000
 OLM  H10  C19  C20  109.60  3.000
 OLM  C18  C19  C20  111.73  3.000
 OLM  N1   C15  N6   111.27  3.000
 OLM  N6   C15  C18  124.88  3.000
 OLM  N1   C15  C18  123.84  3.000
 OLM  C16  N6   C15  106.89  3.000
 OLM  C17  C16  C22  129.07  3.000
 OLM  C17  C16  N6   109.48  3.000
 OLM  C22  C16  N6   121.41  3.000
 OLM  C24  C22  C23  109.90  3.000
 OLM  C24  C22  C16  110.28  3.000
 OLM  C23  C22  C16  109.69  3.000
 OLM  C16  C22  O3   110.09  3.000
 OLM  C24  C22  O3   110.05  3.000
 OLM  C23  C22  O3   106.77  3.000
 OLM  H16  C23  H15  108.66  3.000
 OLM  H16  C23  H14  107.89  3.000
 OLM  H15  C23  H14  108.22  3.000
 OLM  H16  C23  C22  110.59  3.000
 OLM  H15  C23  C22  111.10  3.000
 OLM  H14  C23  C22  110.28  3.000
 OLM  H19  C24  H18  108.12  3.000
 OLM  H19  C24  H17  108.28  3.000
 OLM  H18  C24  H17  107.58  3.000
 OLM  H19  C24  C22  109.54  3.000
 OLM  H18  C24  C22  111.79  3.000
 OLM  H17  C24  C22  111.40  3.000
 OLM  N1   C17  C21  124.79  3.000
 OLM  N1   C17  C16  105.46  3.000
 OLM  C21  C17  C16  129.75  3.000
 OLM  C17  C21  O1   124.30  3.000
 OLM  C17  C21  O2   112.53  3.000
 OLM  O1   C21  O2   123.17  3.000
 OLM  C17  N1   C15  106.86  3.000
 OLM  C15  N1   C1   123.52  3.000
 OLM  C17  N1   C1   128.43  3.000
 OLM  H20  C7   C6   118.62  3.000
 OLM  H20  C7   C2   120.86  3.000
 OLM  C6   C7   C2   120.51  3.000
 OLM  H21  C6   C5   120.05  3.000
 OLM  H21  C6   C7   119.04  3.000
 OLM  C5   C6   C7   120.90  3.000
 OLM  C8   C5   C6   120.78  3.000
 OLM  C8   C5   C4   120.69  3.000
 OLM  C6   C5   C4   118.48  3.000
 OLM  C13  C8   C9   118.31  3.000
 OLM  C9   C8   C5   119.41  3.000
 OLM  C13  C8   C5   122.24  3.000
 OLM  H22  C9   C10  119.58  3.000
 OLM  H22  C9   C8   119.19  3.000
 OLM  C10  C9   C8   121.22  3.000
 OLM  H23  C10  C11  120.21  3.000
 OLM  H23  C10  C9   119.72  3.000
 OLM  C11  C10  C9   120.07  3.000
 OLM  H24  C11  C12  119.93  3.000
 OLM  H24  C11  C10  120.49  3.000
 OLM  C12  C11  C10  119.57  3.000
 OLM  H25  C12  C13  119.89  3.000
 OLM  H25  C12  C11  119.61  3.000
 OLM  C13  C12  C11  120.48  3.000
 OLM  C14  C13  C12  118.56  3.000
 OLM  C12  C13  C8   120.33  3.000
 OLM  C14  C13  C8   121.05  3.000
 OLM  N2   C14  N5   106.97  3.000
 OLM  N2   C14  C13  127.74  3.000
 OLM  N5   C14  C13  125.25  3.000
 OLM  H26  N5   N4   120.94  3.000
 OLM  H26  N5   C14  129.86  3.000
 OLM  N4   N5   C14  109.18  3.000
 OLM  N3   N4   N5   106.27  3.000
 OLM  N2   N3   N4   111.30  3.000
 OLM  N3   N2   C14  106.29  3.000
 OLM  H13  C18  H12  106.47  3.000
 OLM  H13  C18  C15  110.30  3.000
 OLM  H12  C18  C15  107.41  3.000
 OLM  H13  C18  C19  109.91  3.000
 OLM  H12  C18  C19  109.32  3.000
 OLM  C15  C18  C19  113.18  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
 OLM  CONST_01  C7   C2   C3   C4      0.00   0.0  0
 OLM  CONST_02  C7   C6   C5   C4      0.00   0.0  0
 OLM  CONST_05  C6   C7   C2   C3      0.00   0.0  0
 OLM  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 OLM  CONST_07  C8   C5   C4   C3    180.00   0.0  0
 OLM  CONST_08  C5   C4   C3   C2      0.00   0.0  0
 OLM  CONST_09  C5   C6   C7   C2      0.00   0.0  0
 OLM  CONST_10  C16  C17  N1   C15     0.00   0.0  0
 OLM  CONST_11  C17  C16  N6   C15     0.00   0.0  0
 OLM  CONST_12  N1   C17  C16  N6      0.00   0.0  0
 OLM  CONST_13  C17  N1   C15  N6      0.00   0.0  0
 OLM  CONST_14  N1   C15  N6   C16     0.00   0.0  0
 OLM  CONST_15  C8   C5   C6   C7    180.00   0.0  0
 OLM  CONST_18  C14  C13  C8   C5      0.00   0.0  0
 OLM  CONST_19  C12  C13  C8   C5    180.00   0.0  0
 OLM  CONST_20  C10  C9   C8   C5    180.00   0.0  0
 OLM  CONST_23  C11  C12  C13  C8      0.00   0.0  0
 OLM  CONST_24  C11  C10  C9   C8      0.00   0.0  0
 OLM  CONST_25  C14  C13  C8   C9    180.00   0.0  0
 OLM  CONST_26  C12  C13  C8   C9      0.00   0.0  0
 OLM  CONST_27  C12  C11  C10  C9      0.00   0.0  0
 OLM  CONST_28  C13  C8   C9   C10     0.00   0.0  0
 OLM  CONST_29  C13  C12  C11  C10     0.00   0.0  0
 OLM  CONST_30  C14  C13  C12  C11   180.00   0.0  0
 OLM  CONST_33  N4   N5   C14  C13   180.00   0.0  0
 OLM  CONST_34  N3   N2   C14  C13   180.00   0.0  0
 OLM  CONST_35  N3   N4   N5   C14     0.00   0.0  0
 OLM  CONST_36  N4   N3   N2   C14     0.00   0.0  0
 OLM  CONST_37  N2   N3   N4   N5      0.00   0.0  0
 OLM  CONST_38  N3   N2   C14  N5      0.00   0.0  0
 OLM  CONST_39  N2   C14  N5   N4      0.00   0.0  0
 OLM  CONST_40  C1   C2   C3   C4    180.00   0.0  0
 OLM  CONST_41  C16  C17  N1   C1    180.00   0.0  0
 OLM  CONST_42  N6   C15  N1   C1    180.00   0.0  0
 OLM  CONST_43  C6   C7   C2   C1    180.00   0.0  0
 OLM  CONST_44  C17  N1   C15  C18   180.00   0.0  0
 OLM  CONST_45  C16  N6   C15  C18   180.00   0.0  0
 OLM  CONST_46  C21  C17  N1   C15   180.00   0.0  0
 OLM  CONST_47  C22  C16  N6   C15   180.00   0.0  0
 OLM  CONST_48  C21  C17  C16  N6    180.00   0.0  0
 OLM  CONST_49  N1   C17  C16  C22   180.00   0.0  0
 OLM  CONST_50  H21  C6   C5   C4    180.00   0.0  0
 OLM  CONST_51  H20  C7   C2   C3    180.00   0.0  0
 OLM  CONST_52  H1   C4   C3   C2    180.00   0.0  0
 OLM  CONST_53  H2   C3   C2   C7    180.00   0.0  0
 OLM  CONST_54  H22  C9   C8   C5      0.00   0.0  0
 OLM  CONST_55  H25  C12  C13  C8    180.00   0.0  0
 OLM  CONST_56  H23  C10  C9   C8    180.00   0.0  0
 OLM  CONST_57  H24  C11  C10  C9    180.00   0.0  0
 OLM  CONST_58  H26  N5   C14  C13     0.00   0.0  0
 OLM  CONST_59  H4   O2   C21  C17   180.00   0.0  0
 OLM  Var_01    N1   C1   C2   C3    153.70  30.0  1
 OLM  Var_02    C17  N1   C1   C2     93.55  30.0  2
 OLM  Var_03    C17  C16  C22  O3     32.82  30.0  2
 OLM  Var_04    C16  C17  C21  O2   -137.79  30.0  2
 OLM  Var_05    N1   C15  C18  C19   -81.39  30.0  2
 OLM  Var_06    C15  C18  C19  C20  -178.24  30.0  1
 OLM  Var_07    H14  C23  C22  C16   -58.46  30.0  3
 OLM  Var_08    H17  C24  C22  C16   -59.54  30.0  3
 OLM  Var_09    H7   C20  C19  C18    59.53  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
 OLM  plan-1  C1   0.020
 OLM  plan-1  C15  0.020
 OLM  plan-1  N6   0.020
 OLM  plan-1  C16  0.020
 OLM  plan-1  C22  0.020
 OLM  plan-1  C17  0.020
 OLM  plan-1  C21  0.020
 OLM  plan-1  N1   0.020
 OLM  plan-1  C18  0.020
 OLM  plan-2  C13  0.020
 OLM  plan-2  C14  0.020
 OLM  plan-2  N5   0.020
 OLM  plan-2  N4   0.020
 OLM  plan-2  N3   0.020
 OLM  plan-2  N2   0.020
 OLM  plan-2  H26  0.020
 OLM  plan-3  C4   0.020
 OLM  plan-3  C3   0.020
 OLM  plan-3  C2   0.020
 OLM  plan-3  C1   0.020
 OLM  plan-3  C7   0.020
 OLM  plan-3  C6   0.020
 OLM  plan-3  C5   0.020
 OLM  plan-3  C8   0.020
 OLM  plan-3  H1   0.020
 OLM  plan-3  H2   0.020
 OLM  plan-3  H20  0.020
 OLM  plan-3  H21  0.020
 OLM  plan-4  C5   0.020
 OLM  plan-4  C8   0.020
 OLM  plan-4  C9   0.020
 OLM  plan-4  C10  0.020
 OLM  plan-4  C11  0.020
 OLM  plan-4  C12  0.020
 OLM  plan-4  C13  0.020
 OLM  plan-4  C14  0.020
 OLM  plan-4  H22  0.020
 OLM  plan-4  H23  0.020
 OLM  plan-4  H24  0.020
 OLM  plan-4  H25  0.020
 OLM  plan-5  O2   0.020
 OLM  plan-5  O1   0.020
 OLM  plan-5  C17  0.020
 OLM  plan-5  C21  0.020
 OLM  plan-5  H4   0.020

