# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 10 07:29:28 2020
#   Inital geometry file: a 143 line input string
#   Ligand name: (2S)-3-(3-{[4-(2-aminoethoxy)-2',6-dimethyl[1,1'-biphenyl]-3-yl]amino}-1H-pyrazol-1-yl)-2-methoxypropan-1-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@H](CO)Cn1ccc(Nc2cc(c(C)cc2OCCN)c3ccccc3C)n1
#
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
 6HU  6HU  (2S)-3-(3-{[4-(2-aminoethoxy)-2',6-dimethyl[1,1'-biphenyl]-3-yl]amino}-1H-pyrazol-1-yl)-2-methoxypropan-1-ol  ligand  60  30  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_6HU
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
 6HU  C1   C  CH3   0  -0.404   3.3569   0.1390   1.8756
 6HU  C3   C  CH1   0   0.005   3.7919   0.8118  -0.3427
 6HU  C6   C  CH2   0  -0.290   3.4440   2.0474  -1.1648
 6HU  C8   C  CR15  0   0.065   1.8474   3.7765  -0.3202
 6HU  C10  C  CR5   0   0.519   0.0759   2.4838  -0.3965
 6HU  C12  C  CR6   0   0.243  -1.5870   0.7030   0.0143
 6HU  C13  C  CR16  0  -0.357  -0.7115  -0.3742   0.0810
 6HU  C14  C  CR6   0   0.016  -1.1443  -1.6527   0.4304
 6HU  C15  C  CR6   0   0.061  -2.4854  -1.8859   0.7146
 6HU  C16  C  CH3   0  -0.746  -2.9827  -3.2483   1.1063
 6HU  C21  C  CH2   0  -0.317  -5.7911   2.7519   0.2654
 6HU  C23  C  CR6   0   0.021  -0.1370  -2.7430   0.5024
 6HU  C24  C  CR16  0  -0.274   0.6193  -2.9023   1.6598
 6HU  C25  C  CR16  0  -0.258   1.5763  -3.9033   1.7596
 6HU  C26  C  CR16  0  -0.255   1.7805  -4.7585   0.6876
 6HU  C27  C  CR16  0  -0.298   1.0343  -4.6005  -0.4729
 6HU  C28  C  CR6   0   0.068   0.0736  -3.5985  -0.5868
 6HU  O2   O  O2    0  -0.488   3.7572   1.1761   1.0158
 6HU  C4   C  CH2   0  -0.166   5.1302   0.2270  -0.7564
 6HU  O5   O  OH1   0  -0.672   6.1340   1.2034  -0.6140
 6HU  N7   N  NR5   0  -0.258   2.1469   2.5657  -0.8083
 6HU  C9   C  CR15  0  -0.586   0.5011   3.7814  -0.0395
 6HU  C17  C  CR16  0  -0.436  -3.3739  -0.8102   0.6357
 6HU  C18  C  CR6   0   0.333  -2.9482   0.4610   0.2901
 6HU  O19  O  O2    0  -0.493  -3.7524   1.5442   0.2078
 6HU  C20  C  CH2   0  -0.177  -5.1371   1.4079   0.4831
 6HU  N22  N  NH2   0  -0.799  -5.7311   3.1480  -1.1315
 6HU  C29  C  CH3   0  -0.742  -0.7028  -3.4290  -1.8606
 6HU  N30  N  N     0  -0.352   1.0780   1.7665  -0.8717
 6HU  H35  H  HCH3  0   0.207   2.3594  -0.2397   1.6201
 6HU  H36  H  HCH3  0   0.205   4.0491  -0.7112   1.8728
 6HU  H37  H  HCH3  0   0.235   3.3226   0.5407   2.8878
 6HU  H31  H  HCH1  0   0.228   3.0336   0.0436  -0.5523
 6HU  H41  H  HCH2  0   0.264   4.1696   2.8438  -1.0060
 6HU  H42  H  HCH2  0   0.259   3.4606   1.7913  -2.2265
 6HU  H43  H  HCR5  0   0.292   2.5972   4.5416  -0.1991
 6HU  H46  H  HCR6  0   0.280   0.3328  -0.2206  -0.1471
 6HU  H47  H  HCH3  0   0.242  -2.4326  -3.6450   1.9609
 6HU  H49  H  HCH3  0   0.245  -4.0386  -3.2197   1.3739
 6HU  H48  H  HCH3  0   0.241  -2.8708  -3.9712   0.2955
 6HU  H54  H  HCH2  0   0.235  -6.8391   2.6421   0.5518
 6HU  H53  H  HCH2  0   0.207  -5.3537   3.4808   0.9618
 6HU  H55  H  HCR6  0   0.240   0.4528  -2.2304   2.4936
 6HU  H56  H  HCR6  0   0.249   2.1552  -4.0125   2.6677
 6HU  H57  H  HCR6  0   0.251   2.5218  -5.5449   0.7487
 6HU  H58  H  HCR6  0   0.244   1.2055  -5.2670  -1.3103
 6HU  H38  H  HCH2  0   0.214   5.3377  -0.6608  -0.1449
 6HU  H39  H  HCH2  0   0.204   5.0405  -0.1246  -1.7928
 6HU  H40  H  HOH1  0   0.459   6.9722   0.8143  -0.8784
 6HU  H44  H  HCR5  0   0.267  -0.0861   4.5854   0.3725
 6HU  H45  H  HNH1  0   0.397  -1.9031   2.7055  -0.0906
 6HU  H50  H  HCR6  0   0.270  -4.4179  -0.9905   0.8589
 6HU  H52  H  HCH2  0   0.227  -5.2908   1.0777   1.5163
 6HU  H51  H  HCH2  0   0.221  -5.5867   0.6643  -0.1839
 6HU  H32  H  HNH2  0   0.352  -6.2665   3.9958  -1.2643
 6HU  H33  H  HNH2  0   0.342  -4.7790   3.3823  -1.3810
 6HU  H59  H  HCH3  0   0.245  -0.5765  -2.4263  -2.2716
 6HU  H61  H  HCH3  0   0.245  -0.3806  -4.1443  -2.6168
 6HU  H60  H  HCH3  0   0.244  -1.7740  -3.5713  -1.7055
 6HU  N11  N  NH1   0  -0.773  -1.2136   2.0024  -0.2998

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
 6HU  C25  C24  aromatic  1.388  0.020  1.388
 6HU  C25  C26  aromatic  1.386  0.020  1.386
 6HU  C24  C23  aromatic  1.392  0.020  1.392
 6HU  C26  C27  aromatic  1.389  0.020  1.389
 6HU  C16  C15  single    1.502  0.020  1.502
 6HU  C23  C14  single    1.486  0.020  1.486
 6HU  C23  C28  aromatic  1.401  0.020  1.401
 6HU  C27  C28  aromatic  1.393  0.020  1.393
 6HU  C15  C14  aromatic  1.391  0.020  1.391
 6HU  C15  C17  aromatic  1.397  0.020  1.397
 6HU  C14  C13  aromatic  1.394  0.020  1.394
 6HU  C9   C8   aromatic  1.375  0.020  1.375
 6HU  C9   C10  aromatic  1.411  0.020  1.411
 6HU  C8   N7   aromatic  1.339  0.020  1.339
 6HU  C28  C29  single    1.501  0.020  1.501
 6HU  C17  C18  aromatic  1.384  0.020  1.384
 6HU  C13  C12  aromatic  1.390  0.020  1.390
 6HU  C18  C12  aromatic  1.410  0.020  1.410
 6HU  C18  O19  single    1.352  0.020  1.352
 6HU  C12  N11  single    1.388  0.020  1.388
 6HU  C20  O19  single    1.418  0.020  1.418
 6HU  C20  C21  single    1.510  0.020  1.510
 6HU  C10  N11  single    1.380  0.020  1.380
 6HU  C10  N30  aromatic  1.321  0.020  1.321
 6HU  N7   C6   single    1.442  0.020  1.442
 6HU  N7   N30  aromatic  1.336  0.020  1.336
 6HU  C21  N22  single    1.453  0.020  1.453
 6HU  C6   C3   single    1.524  0.020  1.524
 6HU  O2   C3   single    1.407  0.020  1.407
 6HU  O2   C1   single    1.405  0.020  1.405
 6HU  C3   C4   single    1.518  0.020  1.518
 6HU  C4   O5   single    1.408  0.020  1.408
 6HU  C1   H35  single    0.970  0.020  1.090
 6HU  C1   H36  single    0.970  0.020  1.090
 6HU  C1   H37  single    0.970  0.020  1.090
 6HU  C3   H31  single    0.970  0.020  1.090
 6HU  C6   H41  single    0.970  0.020  1.090
 6HU  C6   H42  single    0.970  0.020  1.090
 6HU  C8   H43  single    0.930  0.020  1.080
 6HU  C13  H46  single    0.930  0.020  1.080
 6HU  C16  H47  single    0.970  0.020  1.090
 6HU  C16  H49  single    0.970  0.020  1.090
 6HU  C16  H48  single    0.970  0.020  1.090
 6HU  C21  H54  single    0.970  0.020  1.090
 6HU  C21  H53  single    0.970  0.020  1.090
 6HU  C24  H55  single    0.930  0.020  1.080
 6HU  C25  H56  single    0.930  0.020  1.080
 6HU  C26  H57  single    0.930  0.020  1.080
 6HU  C27  H58  single    0.930  0.020  1.080
 6HU  C4   H38  single    0.970  0.020  1.090
 6HU  C4   H39  single    0.970  0.020  1.090
 6HU  O5   H40  single    0.850  0.020  0.980
 6HU  C9   H44  single    0.930  0.020  1.080
 6HU  N11  H45  single    0.890  0.020  1.040
 6HU  C17  H50  single    0.930  0.020  1.080
 6HU  C20  H52  single    0.970  0.020  1.090
 6HU  C20  H51  single    0.970  0.020  1.090
 6HU  N22  H32  single    0.890  0.020  1.040
 6HU  N22  H33  single    0.890  0.020  1.040
 6HU  C29  H59  single    0.970  0.020  1.090
 6HU  C29  H61  single    0.970  0.020  1.090
 6HU  C29  H60  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
 6HU  H37  C1   H36  107.95  3.000
 6HU  H37  C1   H35  108.36  3.000
 6HU  H36  C1   H35  107.80  3.000
 6HU  H37  C1   O2   107.78  3.000
 6HU  H36  C1   O2   113.01  3.000
 6HU  H35  C1   O2   111.79  3.000
 6HU  H31  C3   C4   106.67  3.000
 6HU  H31  C3   O2   110.37  3.000
 6HU  C4   C3   O2   112.62  3.000
 6HU  H31  C3   C6   107.83  3.000
 6HU  C4   C3   C6   111.50  3.000
 6HU  O2   C3   C6   107.78  3.000
 6HU  H42  C6   H41  107.64  3.000
 6HU  H42  C6   N7   109.78  3.000
 6HU  H41  C6   N7   107.49  3.000
 6HU  H42  C6   C3   109.31  3.000
 6HU  H41  C6   C3   111.23  3.000
 6HU  N7   C6   C3   111.31  3.000
 6HU  H43  C8   C9   130.95  3.000
 6HU  H43  C8   N7   121.80  3.000
 6HU  C9   C8   N7   107.25  3.000
 6HU  N30  C10  N11  123.01  3.000
 6HU  N30  C10  C9   111.21  3.000
 6HU  N11  C10  C9   125.77  3.000
 6HU  C18  C12  N11  117.70  3.000
 6HU  N11  C12  C13  124.54  3.000
 6HU  C18  C12  C13  117.76  3.000
 6HU  H46  C13  C14  118.92  3.000
 6HU  H46  C13  C12  119.26  3.000
 6HU  C14  C13  C12  121.82  3.000
 6HU  C23  C14  C15  121.38  3.000
 6HU  C15  C14  C13  120.29  3.000
 6HU  C23  C14  C13  118.33  3.000
 6HU  C17  C15  C16  120.15  3.000
 6HU  C17  C15  C14  118.20  3.000
 6HU  C16  C15  C14  121.64  3.000
 6HU  H48  C16  H49  107.40  3.000
 6HU  H48  C16  H47  106.81  3.000
 6HU  H49  C16  H47  107.80  3.000
 6HU  H48  C16  C15  111.89  3.000
 6HU  H49  C16  C15  111.16  3.000
 6HU  H47  C16  C15  111.53  3.000
 6HU  H53  C21  H54  106.41  3.000
 6HU  H53  C21  N22  114.33  3.000
 6HU  H54  C21  N22  108.61  3.000
 6HU  H53  C21  C20  109.05  3.000
 6HU  H54  C21  C20  106.76  3.000
 6HU  N22  C21  C20  111.30  3.000
 6HU  C28  C23  C24  119.67  3.000
 6HU  C28  C23  C14  120.82  3.000
 6HU  C24  C23  C14  119.51  3.000
 6HU  H55  C24  C25  119.84  3.000
 6HU  H55  C24  C23  119.04  3.000
 6HU  C25  C24  C23  121.12  3.000
 6HU  H56  C25  C26  120.51  3.000
 6HU  H56  C25  C24  120.11  3.000
 6HU  C26  C25  C24  119.39  3.000
 6HU  H57  C26  C27  119.86  3.000
 6HU  H57  C26  C25  120.35  3.000
 6HU  C27  C26  C25  119.79  3.000
 6HU  H58  C27  C28  119.22  3.000
 6HU  H58  C27  C26  119.39  3.000
 6HU  C28  C27  C26  121.39  3.000
 6HU  C29  C28  C27  120.48  3.000
 6HU  C29  C28  C23  120.86  3.000
 6HU  C27  C28  C23  118.65  3.000
 6HU  C3   O2   C1   114.00  3.000
 6HU  H39  C4   H38  106.39  3.000
 6HU  H39  C4   O5   112.07  3.000
 6HU  H38  C4   O5   111.70  3.000
 6HU  H39  C4   C3   107.97  3.000
 6HU  H38  C4   C3   109.05  3.000
 6HU  O5   C4   C3   109.51  3.000
 6HU  H40  O5   C4   108.26  3.000
 6HU  N30  N7   C8   112.28  3.000
 6HU  N30  N7   C6   119.54  3.000
 6HU  C8   N7   C6   128.05  3.000
 6HU  H44  C9   C10  128.21  3.000
 6HU  H44  C9   C8   127.89  3.000
 6HU  C10  C9   C8   103.89  3.000
 6HU  H50  C17  C18  120.06  3.000
 6HU  H50  C17  C15  118.24  3.000
 6HU  C18  C17  C15  121.69  3.000
 6HU  O19  C18  C17  124.62  3.000
 6HU  O19  C18  C12  115.14  3.000
 6HU  C17  C18  C12  120.23  3.000
 6HU  C20  O19  C18  119.47  3.000
 6HU  H51  C20  H52  108.18  3.000
 6HU  H51  C20  O19  110.35  3.000
 6HU  H52  C20  O19  110.42  3.000
 6HU  H51  C20  C21  109.79  3.000
 6HU  H52  C20  C21  110.09  3.000
 6HU  O19  C20  C21  108.01  3.000
 6HU  H33  N22  H32  105.76  3.000
 6HU  H33  N22  C21  109.81  3.000
 6HU  H32  N22  C21  109.44  3.000
 6HU  H60  C29  H61  107.65  3.000
 6HU  H60  C29  H59  106.68  3.000
 6HU  H61  C29  H59  107.91  3.000
 6HU  H60  C29  C28  111.85  3.000
 6HU  H61  C29  C28  111.21  3.000
 6HU  H59  C29  C28  111.32  3.000
 6HU  N7   N30  C10  105.37  3.000
 6HU  H45  N11  C12  115.00  3.000
 6HU  H45  N11  C10  114.27  3.000
 6HU  C12  N11  C10  126.43  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
 6HU  CONST_01  N30  C10  C9   C8      0.00   0.0  0
 6HU  CONST_02  C10  N30  N7   C8      0.00   0.0  0
 6HU  CONST_03  N7   C8   C9   C10     0.00   0.0  0
 6HU  CONST_04  C23  C14  C13  C12   180.00   0.0  0
 6HU  CONST_05  C15  C14  C13  C12     0.00   0.0  0
 6HU  CONST_06  C15  C17  C18  C12     0.00   0.0  0
 6HU  CONST_09  C17  C15  C14  C13     0.00   0.0  0
 6HU  CONST_10  C17  C18  C12  C13     0.00   0.0  0
 6HU  CONST_11  C25  C24  C23  C14   180.00   0.0  0
 6HU  CONST_12  C27  C28  C23  C14   180.00   0.0  0
 6HU  CONST_13  C18  C17  C15  C14     0.00   0.0  0
 6HU  CONST_14  C18  C12  C13  C14     0.00   0.0  0
 6HU  CONST_17  C26  C25  C24  C23     0.00   0.0  0
 6HU  CONST_18  C17  C15  C14  C23   180.00   0.0  0
 6HU  CONST_19  C26  C27  C28  C23     0.00   0.0  0
 6HU  CONST_20  C27  C26  C25  C24     0.00   0.0  0
 6HU  CONST_21  C27  C28  C23  C24     0.00   0.0  0
 6HU  CONST_22  C28  C23  C24  C25     0.00   0.0  0
 6HU  CONST_23  C28  C27  C26  C25     0.00   0.0  0
 6HU  CONST_24  C9   C10  N30  N7      0.00   0.0  0
 6HU  CONST_25  N30  N7   C8   C9      0.00   0.0  0
 6HU  CONST_26  C9   C8   N7   C6    180.00   0.0  0
 6HU  CONST_27  C10  N30  N7   C6    180.00   0.0  0
 6HU  CONST_28  N11  C10  C9   C8    180.00   0.0  0
 6HU  CONST_29  C16  C15  C14  C13   180.00   0.0  0
 6HU  CONST_30  O19  C18  C12  C13   180.00   0.0  0
 6HU  CONST_31  C29  C28  C23  C14     0.00   0.0  0
 6HU  CONST_32  N11  C12  C13  C14   180.00   0.0  0
 6HU  CONST_33  O19  C18  C17  C15   180.00   0.0  0
 6HU  CONST_34  C23  C14  C15  C16     0.00   0.0  0
 6HU  CONST_35  C18  C17  C15  C16   180.00   0.0  0
 6HU  CONST_36  C29  C28  C23  C24   180.00   0.0  0
 6HU  CONST_37  C29  C28  C27  C26   180.00   0.0  0
 6HU  CONST_38  N11  C10  N30  N7    180.00   0.0  0
 6HU  CONST_39  C17  C18  C12  N11   180.00   0.0  0
 6HU  CONST_40  H43  C8   C9   C10   180.00   0.0  0
 6HU  CONST_41  H50  C17  C18  C12   180.00   0.0  0
 6HU  CONST_42  H55  C24  C23  C14     0.00   0.0  0
 6HU  CONST_43  H46  C13  C14  C15   180.00   0.0  0
 6HU  CONST_44  H56  C25  C24  C23   180.00   0.0  0
 6HU  CONST_45  H58  C27  C28  C23   180.00   0.0  0
 6HU  CONST_46  H57  C26  C25  C24   180.00   0.0  0
 6HU  CONST_47  H44  C9   C8   N7    180.00   0.0  0
 6HU  Var_01    C13  C12  N11  C10   -10.45  30.0  3
 6HU  Var_02    C9   C10  N11  C12  -145.40  30.0  2
 6HU  Var_03    C8   N7   C6   C3    119.68  30.0  3
 6HU  Var_04    H47  C16  C15  C14    54.68  30.0  2
 6HU  Var_05    H59  C29  C28  C23    56.84  30.0  2
 6HU  Var_06    H52  C20  O19  C18    61.67  30.0  2
 6HU  Var_07    N22  C21  C20  O19    65.65  30.0  3
 6HU  Var_08    H35  C1   O2   C3    -58.53  30.0  3
 6HU  Var_09    H32  N22  C21  C20   173.57  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 6HU  chir_01  C3  C6  O2  C4  positiv

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
 6HU  plan-1  C6   0.020
 6HU  plan-1  C8   0.020
 6HU  plan-1  C10  0.020
 6HU  plan-1  N7   0.020
 6HU  plan-1  C9   0.020
 6HU  plan-1  N30  0.020
 6HU  plan-1  H43  0.020
 6HU  plan-1  H44  0.020
 6HU  plan-1  N11  0.020
 6HU  plan-2  C12  0.020
 6HU  plan-2  C13  0.020
 6HU  plan-2  C14  0.020
 6HU  plan-2  C15  0.020
 6HU  plan-2  C16  0.020
 6HU  plan-2  C23  0.020
 6HU  plan-2  C17  0.020
 6HU  plan-2  C18  0.020
 6HU  plan-2  O19  0.020
 6HU  plan-2  H46  0.020
 6HU  plan-2  H50  0.020
 6HU  plan-2  N11  0.020
 6HU  plan-3  C14  0.020
 6HU  plan-3  C23  0.020
 6HU  plan-3  C24  0.020
 6HU  plan-3  C25  0.020
 6HU  plan-3  C26  0.020
 6HU  plan-3  C27  0.020
 6HU  plan-3  C28  0.020
 6HU  plan-3  C29  0.020
 6HU  plan-3  H55  0.020
 6HU  plan-3  H56  0.020
 6HU  plan-3  H57  0.020
 6HU  plan-3  H58  0.020

