# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 12:59:50 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: 4-[6,6-dimethyl-4-oxo-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]-2-[(cis-4-hydroxycyclohexyl)amino]benzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1(C)CC(=O)c2c(C1)n(nc2C(F)(F)F)c3ccc(C(N)=O)c(N[C@H]4CC[C@@H](O)CC4)c3
#
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
 HIE  HIE  4-[6,6-dimethyl-4-oxo-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]-2-[(cis-4-hydroxycyclohexyl)amino]benzamide  ligand  60  33  .  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_HIE
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
 HIE  C8    C  CH1   0  -0.067   3.5111   0.9067   0.2094
 HIE  C5    C  CR6   0   0.417   2.3670  -1.2706  -0.1547
 HIE  C6    C  CR6   0  -0.146   2.4271  -2.6657  -0.4283
 HIE  N1    N  NH2   0  -0.806   3.7231  -4.4722  -1.3536
 HIE  C2    C  CR16  0  -0.320  -0.0032  -2.8239  -0.3363
 HIE  O2    O  O     0  -0.502   4.7769  -2.9142  -0.1287
 HIE  N2    N  NH1   0  -0.715   3.4809  -0.5118  -0.0694
 HIE  N3    N  NR5   0  -0.493  -1.3106  -0.8247   0.0444
 HIE  C3    C  CR6   0   0.372  -0.0524  -1.4549  -0.1079
 HIE  C4    C  CR16  0  -0.415   1.0913  -0.6921  -0.0035
 HIE  N4    N  N     0  -0.265  -2.2677  -1.4405   0.7499
 HIE  C10   C  CH2   0  -0.458   3.3546   2.7402   1.9267
 HIE  C11   C  CH1   0   0.040   4.6620   3.3488   1.4395
 HIE  C12   C  CH2   0  -0.482   4.9030   2.9855  -0.0234
 HIE  C13   C  CH2   0  -0.439   4.8411   1.4819  -0.2695
 HIE  C14   C  CR5   0   0.010  -3.3037  -0.6452   0.7057
 HIE  C15   C  CR5   0  -0.320  -3.0272   0.5183  -0.0423
 HIE  C16   C  CR5   0   0.514  -1.7227   0.3553  -0.4601
 HIE  C19   C  CH2   0  -0.549  -3.0517   2.7205  -1.2024
 HIE  C1    C  CR16  0  -0.281   1.2432  -3.3982  -0.4878
 HIE  F1    F  F     0  -0.305  -4.4440  -2.1885   2.0336
 HIE  F2    F  F     0  -0.309  -4.9152  -0.1069   2.3112
 HIE  F3    F  F     0  -0.310  -5.5830  -1.1354   0.5421
 HIE  O3    O  OH1   0  -0.676   5.6954   2.8668   2.2796
 HIE  C7    C  C     0   0.518   3.7352  -3.3481  -0.6203
 HIE  C9    C  CH2   0  -0.441   3.2947   1.2338   1.6891
 HIE  C17   C  CH2   0  -0.494  -0.9843   1.3000  -1.3327
 HIE  C18   C  CT    0  -0.147  -1.9803   2.1483  -2.1471
 HIE  C20   C  C     0   0.347  -3.8183   1.6828  -0.4147
 HIE  C22   C  CH3   0  -0.635  -2.6378   1.3039  -3.2408
 HIE  C23   C  CT    0   1.078  -4.5661  -1.0212   1.4016
 HIE  H8    H  HCH1  0   0.222   2.7200   1.3913  -0.3774
 HIE  HN1   H  HNH2  0   0.413   2.9343  -4.7483  -1.9114
 HIE  HN1A  H  HNH2  0   0.406   4.5888  -4.9600  -1.5175
 HIE  H2    H  HCR6  0   0.273  -0.9020  -3.4195  -0.3951
 HIE  HN2   H  HNH1  0   0.397   4.3498  -1.0208   0.0024
 HIE  H4    H  HCR6  0   0.281   1.0033   0.3546   0.2447
 HIE  H10   H  HCH2  0   0.241   3.2092   2.9647   2.9862
 HIE  H10A  H  HCH2  0   0.225   2.5330   3.2275   1.3928
 HIE  H11   H  HCH1  0   0.214   4.5899   4.4427   1.5194
 HIE  H12   H  HCH2  0   0.226   4.1414   3.4840  -0.6312
 HIE  H12A  H  HCH2  0   0.242   5.8655   3.3841  -0.3572
 HIE  H13   H  HCH2  0   0.224   5.6616   0.9810   0.2546
 HIE  H13A  H  HCH2  0   0.244   4.9709   1.2730  -1.3338
 HIE  H19   H  HCH2  0   0.282  -2.5678   3.3772  -0.4671
 HIE  H19A  H  HCH2  0   0.272  -3.7597   3.3405  -1.7566
 HIE  H21   H  HCH3  0   0.232  -0.7319   3.9287  -2.0473
 HIE  H21A  H  HCH3  0   0.237  -0.4505   2.9279  -3.4730
 HIE  H21B  H  HCH3  0   0.238  -1.8952   3.9348  -3.3740
 HIE  H1    H  HCR6  0   0.266   1.2874  -4.4675  -0.6474
 HIE  HO3   H  HOH1  0   0.447   6.5326   3.2158   1.9581
 HIE  H9    H  HCH2  0   0.239   2.3325   0.8450   2.0316
 HIE  H9A   H  HCH2  0   0.226   4.0631   0.7240   2.2766
 HIE  H17   H  HCH2  0   0.281  -0.3746   1.9653  -0.7115
 HIE  H17A  H  HCH2  0   0.287  -0.2970   0.7721  -1.9978
 HIE  H22   H  HCH3  0   0.238  -3.3229   1.9135  -3.8324
 HIE  H22A  H  HCH3  0   0.236  -1.8859   0.8983  -3.9200
 HIE  H22B  H  HCH3  0   0.234  -3.2082   0.4621  -2.8438
 HIE  C21   C  CH3   0  -0.644  -1.2205   3.3020  -2.7957
 HIE  O1    O  O     0  -0.400  -4.9811   1.8205  -0.0940

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
 HIE  C8   N2    single    1.446  0.020  1.446
 HIE  C8   C13   single    1.526  0.020  1.526
 HIE  C8   C9    single    1.531  0.020  1.531
 HIE  C5   C6    aromatic  1.423  0.020  1.423
 HIE  C5   N2    single    1.350  0.020  1.350
 HIE  C5   C4    aromatic  1.409  0.020  1.409
 HIE  C6   C1    aromatic  1.393  0.020  1.393
 HIE  C6   C7    single    1.488  0.020  1.488
 HIE  N1   C7    single    1.342  0.020  1.342
 HIE  C2   C3    aromatic  1.389  0.020  1.389
 HIE  C2   C1    aromatic  1.381  0.020  1.381
 HIE  O2   C7    double    1.231  0.020  1.231
 HIE  N3   C3    single    1.415  0.020  1.415
 HIE  N3   N4    aromatic  1.339  0.020  1.339
 HIE  N3   C16   aromatic  1.348  0.020  1.348
 HIE  C3   C4    aromatic  1.379  0.020  1.379
 HIE  N4   C14   aromatic  1.307  0.020  1.307
 HIE  C10  C11   single    1.522  0.020  1.522
 HIE  C10  C9    single    1.526  0.020  1.526
 HIE  C11  C12   single    1.527  0.020  1.527
 HIE  C11  O3    single    1.416  0.020  1.416
 HIE  C12  C13   single    1.525  0.020  1.525
 HIE  C14  C15   aromatic  1.411  0.020  1.411
 HIE  C14  C23   single    1.490  0.020  1.490
 HIE  C15  C16   aromatic  1.379  0.020  1.379
 HIE  C15  C20   single    1.456  0.020  1.456
 HIE  C16  C17   single    1.483  0.020  1.483
 HIE  C19  C18   single    1.539  0.020  1.539
 HIE  C19  C20   single    1.512  0.020  1.512
 HIE  C21  C18   single    1.526  0.020  1.526
 HIE  F1   C23   single    1.333  0.020  1.333
 HIE  O1   C20   double    1.214  0.020  1.214
 HIE  F2   C23   single    1.336  0.020  1.336
 HIE  F3   C23   single    1.336  0.020  1.336
 HIE  C17  C18   single    1.541  0.020  1.541
 HIE  C18  C22   single    1.530  0.020  1.530
 HIE  C8   H8    single    0.970  0.020  1.090
 HIE  N1   HN1   single    0.860  0.020  1.020
 HIE  N1   HN1A  single    0.860  0.020  1.020
 HIE  C2   H2    single    0.930  0.020  1.080
 HIE  N2   HN2   single    0.860  0.020  1.020
 HIE  C4   H4    single    0.930  0.020  1.080
 HIE  C10  H10   single    0.970  0.020  1.090
 HIE  C10  H10A  single    0.970  0.020  1.090
 HIE  C11  H11   single    0.970  0.020  1.090
 HIE  C12  H12   single    0.970  0.020  1.090
 HIE  C12  H12A  single    0.970  0.020  1.090
 HIE  C13  H13   single    0.970  0.020  1.090
 HIE  C13  H13A  single    0.970  0.020  1.090
 HIE  C19  H19   single    0.970  0.020  1.090
 HIE  C19  H19A  single    0.970  0.020  1.090
 HIE  C21  H21   single    0.970  0.020  1.090
 HIE  C21  H21A  single    0.970  0.020  1.090
 HIE  C21  H21B  single    0.970  0.020  1.090
 HIE  C1   H1    single    0.930  0.020  1.080
 HIE  O3   HO3   single    0.850  0.020  0.980
 HIE  C9   H9    single    0.970  0.020  1.090
 HIE  C9   H9A   single    0.970  0.020  1.090
 HIE  C17  H17   single    0.970  0.020  1.090
 HIE  C17  H17A  single    0.970  0.020  1.090
 HIE  C22  H22   single    0.970  0.020  1.090
 HIE  C22  H22A  single    0.970  0.020  1.090
 HIE  C22  H22B  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
 HIE  H8    C8   C9    108.69  3.000
 HIE  H8    C8   C13   107.09  3.000
 HIE  C9    C8   C13   110.24  3.000
 HIE  H8    C8   N2    108.36  3.000
 HIE  C9    C8   N2    113.15  3.000
 HIE  C13   C8   N2    109.12  3.000
 HIE  C4    C5   N2    120.62  3.000
 HIE  C4    C5   C6    117.48  3.000
 HIE  N2    C5   C6    121.88  3.000
 HIE  C7    C6   C1    120.02  3.000
 HIE  C7    C6   C5    120.78  3.000
 HIE  C1    C6   C5    119.19  3.000
 HIE  HN1A  N1   HN1   116.83  3.000
 HIE  HN1A  N1   C7    119.13  3.000
 HIE  HN1   N1   C7    122.72  3.000
 HIE  H2    C2   C1    121.07  3.000
 HIE  H2    C2   C3    121.54  3.000
 HIE  C1    C2   C3    117.39  3.000
 HIE  HN2   N2   C5    115.54  3.000
 HIE  HN2   N2   C8    117.57  3.000
 HIE  C5    N2   C8    125.50  3.000
 HIE  C16   N3   N4    112.41  3.000
 HIE  C16   N3   C3    128.41  3.000
 HIE  N4    N3   C3    119.17  3.000
 HIE  C4    C3   N3    118.88  3.000
 HIE  C4    C3   C2    121.90  3.000
 HIE  N3    C3   C2    119.22  3.000
 HIE  H4    C4   C3    119.10  3.000
 HIE  H4    C4   C5    119.79  3.000
 HIE  C3    C4   C5    121.05  3.000
 HIE  C14   N4   N3    105.60  3.000
 HIE  H10A  C10  H10   106.36  3.000
 HIE  H10A  C10  C9    109.52  3.000
 HIE  H10   C10  C9    110.40  3.000
 HIE  H10A  C10  C11   108.10  3.000
 HIE  H10   C10  C11   110.03  3.000
 HIE  C9    C10  C11   112.24  3.000
 HIE  H11   C11  O3    110.09  3.000
 HIE  H11   C11  C12   108.47  3.000
 HIE  O3    C11  C12   111.85  3.000
 HIE  H11   C11  C10   108.56  3.000
 HIE  O3    C11  C10   107.51  3.000
 HIE  C12   C11  C10   110.31  3.000
 HIE  H12A  C12  H12   106.07  3.000
 HIE  H12A  C12  C13   110.23  3.000
 HIE  H12   C12  C13   109.35  3.000
 HIE  H12A  C12  C11   110.15  3.000
 HIE  H12   C12  C11   108.30  3.000
 HIE  C13   C12  C11   112.52  3.000
 HIE  H13A  C13  H13   106.85  3.000
 HIE  H13A  C13  C12   109.94  3.000
 HIE  H13   C13  C12   110.09  3.000
 HIE  H13A  C13  C8    109.71  3.000
 HIE  H13   C13  C8    109.29  3.000
 HIE  C12   C13  C8    110.88  3.000
 HIE  C23   C14  C15   128.46  3.000
 HIE  C23   C14  N4    120.16  3.000
 HIE  C15   C14  N4    111.38  3.000
 HIE  C20   C15  C16   122.06  3.000
 HIE  C20   C15  C14   133.53  3.000
 HIE  C16   C15  C14   104.39  3.000
 HIE  C17   C16  C15   125.01  3.000
 HIE  C17   C16  N3    128.74  3.000
 HIE  C15   C16  N3    106.22  3.000
 HIE  H19A  C19  H19   106.61  3.000
 HIE  H19A  C19  C20   108.99  3.000
 HIE  H19   C19  C20   106.56  3.000
 HIE  H19A  C19  C18   110.54  3.000
 HIE  H19   C19  C18   109.06  3.000
 HIE  C20   C19  C18   114.70  3.000
 HIE  H1    C1   C2    117.66  3.000
 HIE  H1    C1   C6    119.41  3.000
 HIE  C2    C1   C6    122.93  3.000
 HIE  HO3   O3   C11   108.25  3.000
 HIE  O2    C7   N1    121.40  3.000
 HIE  O2    C7   C6    122.06  3.000
 HIE  N1    C7   C6    116.54  3.000
 HIE  H9A   C9   H9    106.52  3.000
 HIE  H9A   C9   C10   110.43  3.000
 HIE  H9    C9   C10   109.69  3.000
 HIE  H9A   C9   C8    108.69  3.000
 HIE  H9    C9   C8    110.57  3.000
 HIE  C10   C9   C8    110.85  3.000
 HIE  H17A  C17  H17   106.77  3.000
 HIE  H17A  C17  C18   110.54  3.000
 HIE  H17   C17  C18   108.97  3.000
 HIE  H17A  C17  C16   111.32  3.000
 HIE  H17   C17  C16   109.29  3.000
 HIE  C18   C17  C16   109.87  3.000
 HIE  C22   C18  C17   110.59  3.000
 HIE  C22   C18  C21   109.11  3.000
 HIE  C17   C18  C21   108.60  3.000
 HIE  C22   C18  C19   110.17  3.000
 HIE  C17   C18  C19   109.28  3.000
 HIE  C21   C18  C19   109.06  3.000
 HIE  O1    C20  C19   123.06  3.000
 HIE  O1    C20  C15   122.92  3.000
 HIE  C19   C20  C15   114.00  3.000
 HIE  H22B  C22  H22A  107.45  3.000
 HIE  H22B  C22  H22   107.45  3.000
 HIE  H22A  C22  H22   107.62  3.000
 HIE  H22B  C22  C18   112.97  3.000
 HIE  H22A  C22  C18   110.72  3.000
 HIE  H22   C22  C18   110.42  3.000
 HIE  F3    C23  F2    107.31  3.000
 HIE  F3    C23  F1    107.45  3.000
 HIE  F2    C23  F1    107.48  3.000
 HIE  F3    C23  C14   111.46  3.000
 HIE  F2    C23  C14   111.51  3.000
 HIE  F1    C23  C14   111.40  3.000
 HIE  H21B  C21  H21A  107.83  3.000
 HIE  H21B  C21  H21   107.89  3.000
 HIE  H21A  C21  H21   107.85  3.000
 HIE  H21B  C21  C18   110.85  3.000
 HIE  H21A  C21  C18   110.84  3.000
 HIE  H21   C21  C18   111.44  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
 HIE  CONST_01  C2    C1   C6   C5      0.00   0.0  0
 HIE  CONST_02  C2    C3   C4   C5      0.00   0.0  0
 HIE  CONST_03  N3    C3   C4   C5    180.00   0.0  0
 HIE  CONST_04  C3    C4   C5   C6      0.00   0.0  0
 HIE  CONST_05  C3    C2   C1   C6      0.00   0.0  0
 HIE  CONST_08  C1    C2   C3   N3    180.00   0.0  0
 HIE  CONST_09  C15   C14  N4   N3      0.00   0.0  0
 HIE  CONST_10  C14   C15  C16  N3      0.00   0.0  0
 HIE  CONST_11  C14   N4   N3   C3    180.00   0.0  0
 HIE  CONST_12  C15   C16  N3   C3    180.00   0.0  0
 HIE  CONST_13  C1    C6   C5   C4      0.00   0.0  0
 HIE  CONST_14  C1    C2   C3   C4      0.00   0.0  0
 HIE  CONST_17  C15   C16  N3   N4      0.00   0.0  0
 HIE  CONST_18  C16   C15  C14  N4      0.00   0.0  0
 HIE  CONST_19  C16   N3   N4   C14     0.00   0.0  0
 HIE  CONST_20  C17   C16  N3   C3      0.00   0.0  0
 HIE  CONST_21  C7    C6   C1   C2    180.00   0.0  0
 HIE  CONST_22  C1    C6   C5   N2    180.00   0.0  0
 HIE  CONST_23  C3    C4   C5   N2    180.00   0.0  0
 HIE  CONST_24  C23   C14  N4   N3    180.00   0.0  0
 HIE  CONST_25  C7    C6   C5   C4    180.00   0.0  0
 HIE  CONST_26  C23   C14  C15  C16   180.00   0.0  0
 HIE  CONST_27  C23   C14  C15  C20     0.00   0.0  0
 HIE  CONST_28  C6    C5   N2   C8    180.00   0.0  0
 HIE  CONST_29  C4    C5   N2   C8      0.00   0.0  0
 HIE  CONST_30  H1    C1   C6   C5    180.00   0.0  0
 HIE  CONST_31  H4    C4   C5   C6    180.00   0.0  0
 HIE  CONST_32  H2    C2   C1   C6    180.00   0.0  0
 HIE  CONST_33  HN2   N2   C5   C6      0.00   0.0  0
 HIE  CONST_34  HN1   N1   C7   C6      0.00   0.0  0
 HIE  CONST_35  HN1A  N1   C7   C6    180.00   0.0  0
 HIE  Var_01    C11   C12  C13  C8     55.81  30.0  1
 HIE  Var_02    C11   C10  C9   C8    -56.29  30.0  1
 HIE  Var_03    C18   C17  C16  N3    154.96  30.0  1
 HIE  Var_04    C19   C20  C15  C14   177.83  30.0  1
 HIE  Var_05    C18   C19  C20  C15    33.95  30.0  1
 HIE  Var_06    C19   C18  C17  C16    48.93  30.0  1
 HIE  Var_07    C20   C19  C18  C17   -57.29  30.0  1
 HIE  Var_08    N1    C7   C6   C5   -155.09  30.0  2
 HIE  Var_09    F1    C23  C14  N4      1.08  30.0  2
 HIE  Var_10    H21   C21  C18  C19    59.83  30.0  3
 HIE  Var_11    H22   C22  C18  C19    60.57  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
 HIE  chir_01  C8   N2  C13  C9   positiv
 HIE  chir_02  C11  O3  C10  C12  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
 HIE  plan-1  C5    0.020
 HIE  plan-1  C6    0.020
 HIE  plan-1  C2    0.020
 HIE  plan-1  N2    0.020
 HIE  plan-1  N3    0.020
 HIE  plan-1  C3    0.020
 HIE  plan-1  C4    0.020
 HIE  plan-1  C1    0.020
 HIE  plan-1  C7    0.020
 HIE  plan-1  H2    0.020
 HIE  plan-1  H4    0.020
 HIE  plan-1  H1    0.020
 HIE  plan-2  N3    0.020
 HIE  plan-2  C3    0.020
 HIE  plan-2  N4    0.020
 HIE  plan-2  C14   0.020
 HIE  plan-2  C15   0.020
 HIE  plan-2  C16   0.020
 HIE  plan-2  C17   0.020
 HIE  plan-2  C20   0.020
 HIE  plan-2  C23   0.020
 HIE  plan-3  C6    0.020
 HIE  plan-3  N1    0.020
 HIE  plan-3  O2    0.020
 HIE  plan-3  C7    0.020
 HIE  plan-3  HN1   0.020
 HIE  plan-3  HN1A  0.020
 HIE  plan-4  C8    0.020
 HIE  plan-4  C5    0.020
 HIE  plan-4  N2    0.020
 HIE  plan-4  HN2   0.020
 HIE  plan-5  C15   0.020
 HIE  plan-5  C19   0.020
 HIE  plan-5  C20   0.020
 HIE  plan-5  O1    0.020

