# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 12 06:29:29 2020
#   Inital geometry file: a 119 line input string
#   Ligand name: (1S,6R)-3-{[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]carbonyl}-6-(2,4,5-trifluorophenyl)cyclohex-3-en-1-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: N[C@H]1CC(=CC[C@@H]1c2cc(F)c(F)cc2F)C(=O)N3CCn4c(C3)nnc4C(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
 KIQ  KIQ  (1S,6R)-3-{[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]carbonyl}-6-(2,4,5-trifluorophenyl)cyclohex-3-en-1-amine  ligand  48  31  .  2021-08-12  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_KIQ
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
 KIQ  C4    C  C     0  -0.069  -1.1097   0.3341   0.5041
 KIQ  C5    C  C     0   0.540  -1.1987   1.8157   0.6383
 KIQ  C8    C  CH2   0  -0.360  -3.3984   1.6593   1.8120
 KIQ  C15   C  CR5   0   0.168  -6.0527   3.9000   0.4722
 KIQ  C20   C  C1    0  -0.226  -1.9846  -0.3311  -0.2493
 KIQ  C21   C  CH2   0  -0.450  -1.8688  -1.7870  -0.5588
 KIQ  C22   C  CH1   0  -0.368  -0.4764  -2.3364  -0.2400
 KIQ  C24   C  CR16  0  -0.448  -1.2627  -4.6185   0.4936
 KIQ  C30   C  CR6   0   0.509   0.3938  -4.5208  -1.1945
 KIQ  C29   C  CR16  0  -0.556   0.4432  -5.9015  -1.2780
 KIQ  C27   C  CR6   0   0.401  -0.3799  -6.6339  -0.4524
 KIQ  F28   F  F     0  -0.300  -0.3639  -7.9669  -0.5007
 KIQ  C25   C  CR6   0   0.409  -1.2298  -5.9932   0.4328
 KIQ  F26   F  F     0  -0.305  -2.0172  -6.7268   1.2263
 KIQ  C23   C  CR6   0  -0.028  -0.4463  -3.8395  -0.3281
 KIQ  C     C  CH1   0  -0.070  -0.0060  -1.8391   1.1425
 KIQ  N     N  NH2   0  -0.789   1.2605  -2.3810   1.5940
 KIQ  C3    C  CH2   0  -0.484   0.0891  -0.3172   1.1302
 KIQ  O     O  O     0  -0.480  -0.2395   2.5128   0.3437
 KIQ  N7    N  NT    0  -0.479  -2.3717   2.3549   1.0605
 KIQ  C12   C  CH2   0  -0.356  -2.5302   3.7948   1.0586
 KIQ  C11   C  CR5   0   0.434  -3.9508   4.1245   0.7496
 KIQ  N13   N  N     0  -0.333  -4.4333   5.2889   0.4105
 KIQ  N14   N  N     0  -0.301  -5.7630   5.1440   0.2374
 KIQ  F19   F  F     0  -0.288  -8.2907   4.2130  -0.0414
 KIQ  F18   F  F     0  -0.307  -7.4530   2.2600  -0.4199
 KIQ  F     F  F     0  -0.307  -7.8334   2.8915   1.5987
 KIQ  N10   N  NR5   0  -0.504  -4.9394   3.2075   0.8085
 KIQ  C9    C  CH2   0  -0.287  -4.7440   1.7992   1.1269
 KIQ  H81   H  HCH2  0   0.289  -3.4515   2.0845   2.8191
 KIQ  H82   H  HCH2  0   0.306  -3.1560   0.6067   1.9168
 KIQ  H20   H  H     0   0.259  -2.8292   0.1911  -0.6873
 KIQ  H211  H  HCH2  0   0.254  -2.6406  -2.3244   0.0034
 KIQ  H212  H  HCH2  0   0.266  -2.1051  -1.9567  -1.6121
 KIQ  H22   H  HCH1  0   0.264   0.2156  -1.9237  -0.9795
 KIQ  H24   H  HCR6  0   0.296  -1.9388  -4.1505   1.1995
 KIQ  H29   H  HCR6  0   0.314   1.1110  -6.3960  -1.9715
 KIQ  H     H  HCH1  0   0.236  -0.7659  -2.1244   1.8798
 KIQ  HN1   H  HNH2  0   0.340   1.9763  -2.2190   0.8940
 KIQ  HN2   H  HNH2  0   0.351   1.1963  -3.3850   1.7061
 KIQ  H31   H  HCH2  0   0.249   0.9949  -0.0079   0.5962
 KIQ  H32   H  HCH2  0   0.261   0.2120   0.0370   2.1576
 KIQ  H121  H  HCH2  0   0.307  -1.8845   4.2455   0.3079
 KIQ  H122  H  HCH2  0   0.292  -2.2567   4.2245   2.0290
 KIQ  H91   H  HCH2  0   0.287  -4.7796   1.2141   0.2082
 KIQ  H92   H  HCH2  0   0.292  -5.5331   1.4576   1.7932
 KIQ  F31   F  F     0  -0.304   1.2080  -3.8270  -2.0042
 KIQ  C16   C  CT    0   1.078  -7.4201   3.3165   0.3993

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
 KIQ  C4   C20   double    1.333  0.020  1.333
 KIQ  C4   C5    single    1.490  0.020  1.490
 KIQ  C4   C3    single    1.501  0.020  1.501
 KIQ  C5   N7    single    1.358  0.020  1.358
 KIQ  C5   O     double    1.222  0.020  1.222
 KIQ  C8   C9    single    1.517  0.020  1.517
 KIQ  C8   N7    single    1.450  0.020  1.450
 KIQ  C8   H81   single    0.970  0.020  1.090
 KIQ  C8   H82   single    0.970  0.020  1.090
 KIQ  C15  C16   single    1.489  0.020  1.489
 KIQ  C15  N10   aromatic  1.353  0.020  1.353
 KIQ  C15  N14   aromatic  1.299  0.020  1.299
 KIQ  C20  C21   single    1.493  0.020  1.493
 KIQ  C20  H20   single    0.930  0.020  1.080
 KIQ  C21  C22   single    1.530  0.020  1.530
 KIQ  C21  H211  single    0.970  0.020  1.090
 KIQ  C21  H212  single    0.970  0.020  1.090
 KIQ  C22  C23   single    1.506  0.020  1.506
 KIQ  C22  C     single    1.543  0.020  1.543
 KIQ  C22  H22   single    0.970  0.020  1.090
 KIQ  C24  C25   aromatic  1.376  0.020  1.376
 KIQ  C24  C23   aromatic  1.396  0.020  1.396
 KIQ  C24  H24   single    0.930  0.020  1.080
 KIQ  F31  C30   single    1.342  0.020  1.342
 KIQ  C30  C29   aromatic  1.384  0.020  1.384
 KIQ  C30  C23   aromatic  1.386  0.020  1.386
 KIQ  C29  C27   aromatic  1.377  0.020  1.377
 KIQ  C29  H29   single    0.930  0.020  1.080
 KIQ  C27  F28   single    1.334  0.020  1.334
 KIQ  C27  C25   aromatic  1.384  0.020  1.384
 KIQ  C25  F26   single    1.337  0.020  1.337
 KIQ  C    N     single    1.450  0.020  1.450
 KIQ  C    C3    single    1.525  0.020  1.525
 KIQ  C    H     single    0.970  0.020  1.090
 KIQ  N    HN1   single    0.890  0.020  1.040
 KIQ  N    HN2   single    0.890  0.020  1.040
 KIQ  C3   H31   single    0.970  0.020  1.090
 KIQ  C3   H32   single    0.970  0.020  1.090
 KIQ  N7   C12   single    1.449  0.020  1.449
 KIQ  C12  C11   single    1.491  0.020  1.491
 KIQ  C12  H121  single    0.970  0.020  1.090
 KIQ  C12  H122  single    0.970  0.020  1.090
 KIQ  C11  N10   aromatic  1.350  0.020  1.350
 KIQ  C11  N13   aromatic  1.305  0.020  1.305
 KIQ  N13  N14   aromatic  1.349  0.020  1.349
 KIQ  C16  F19   single    1.325  0.020  1.325
 KIQ  C16  F18   single    1.337  0.020  1.337
 KIQ  C16  F     single    1.338  0.020  1.338
 KIQ  N10  C9    single    1.457  0.020  1.457
 KIQ  C9   H91   single    0.970  0.020  1.090
 KIQ  C9   H92   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
 KIQ  C3    C4   C20   122.93  3.000
 KIQ  C3    C4   C5    116.20  3.000
 KIQ  C20   C4   C5    120.53  3.000
 KIQ  N7    C5   O     121.77  3.000
 KIQ  O     C5   C4    119.90  3.000
 KIQ  N7    C5   C4    118.31  3.000
 KIQ  H82   C8   H81   107.39  3.000
 KIQ  H82   C8   C9    109.35  3.000
 KIQ  H81   C8   C9    109.68  3.000
 KIQ  H82   C8   N7    110.93  3.000
 KIQ  H81   C8   N7    108.96  3.000
 KIQ  C9    C8   N7    110.48  3.000
 KIQ  N10   C15  C16   124.55  3.000
 KIQ  N10   C15  N14   110.58  3.000
 KIQ  C16   C15  N14   124.86  3.000
 KIQ  H20   C20  C21   116.49  3.000
 KIQ  H20   C20  C4    119.93  3.000
 KIQ  C21   C20  C4    123.58  3.000
 KIQ  H212  C21  H211  105.43  3.000
 KIQ  H212  C21  C22   109.99  3.000
 KIQ  H211  C21  C22   110.97  3.000
 KIQ  H212  C21  C20   109.54  3.000
 KIQ  H211  C21  C20   108.49  3.000
 KIQ  C22   C21  C20   112.18  3.000
 KIQ  H22   C22  C     106.94  3.000
 KIQ  H22   C22  C23   108.93  3.000
 KIQ  C     C22  C23   111.60  3.000
 KIQ  H22   C22  C21   107.42  3.000
 KIQ  C     C22  C21   110.39  3.000
 KIQ  C23   C22  C21   111.36  3.000
 KIQ  H24   C24  C23   120.49  3.000
 KIQ  H24   C24  C25   118.36  3.000
 KIQ  C23   C24  C25   121.15  3.000
 KIQ  C23   C30  C29   123.35  3.000
 KIQ  C23   C30  F31   119.41  3.000
 KIQ  C29   C30  F31   117.25  3.000
 KIQ  H29   C29  C27   120.67  3.000
 KIQ  H29   C29  C30   121.09  3.000
 KIQ  C27   C29  C30   118.24  3.000
 KIQ  C25   C27  F28   119.54  3.000
 KIQ  C25   C27  C29   120.29  3.000
 KIQ  F28   C27  C29   120.17  3.000
 KIQ  F26   C25  C27   119.15  3.000
 KIQ  F26   C25  C24   120.51  3.000
 KIQ  C27   C25  C24   120.34  3.000
 KIQ  C30   C23  C24   116.63  3.000
 KIQ  C30   C23  C22   122.64  3.000
 KIQ  C24   C23  C22   120.72  3.000
 KIQ  H     C    C3    107.96  3.000
 KIQ  H     C    N     107.38  3.000
 KIQ  C3    C    N     108.73  3.000
 KIQ  H     C    C22   107.90  3.000
 KIQ  C3    C    C22   109.48  3.000
 KIQ  N     C    C22   115.15  3.000
 KIQ  HN2   N    HN1   106.24  3.000
 KIQ  HN2   N    C     110.48  3.000
 KIQ  HN1   N    C     109.99  3.000
 KIQ  H32   C3   H31   105.87  3.000
 KIQ  H32   C3   C     108.83  3.000
 KIQ  H31   C3   C     109.70  3.000
 KIQ  H32   C3   C4    109.94  3.000
 KIQ  H31   C3   C4    109.53  3.000
 KIQ  C     C3   C4    112.74  3.000
 KIQ  C12   N7   C8    113.58  3.000
 KIQ  C12   N7   C5    119.25  3.000
 KIQ  C8    N7   C5    125.60  3.000
 KIQ  H122  C12  H121  107.48  3.000
 KIQ  H122  C12  C11   109.55  3.000
 KIQ  H121  C12  C11   109.32  3.000
 KIQ  H122  C12  N7    111.18  3.000
 KIQ  H121  C12  N7    110.35  3.000
 KIQ  C11   C12  N7    108.93  3.000
 KIQ  N10   C11  N13   110.28  3.000
 KIQ  N13   C11  C12   127.12  3.000
 KIQ  N10   C11  C12   122.60  3.000
 KIQ  N14   N13  C11   107.58  3.000
 KIQ  N13   N14  C15   107.43  3.000
 KIQ  C9    N10  C11   124.61  3.000
 KIQ  C9    N10  C15   131.23  3.000
 KIQ  C11   N10  C15   104.13  3.000
 KIQ  H92   C9   H91   108.91  3.000
 KIQ  H92   C9   N10   109.88  3.000
 KIQ  H91   C9   N10   109.29  3.000
 KIQ  H92   C9   C8    109.75  3.000
 KIQ  H91   C9   C8    111.12  3.000
 KIQ  N10   C9   C8    107.87  3.000
 KIQ  F     C16  F18   106.89  3.000
 KIQ  F     C16  F19   108.06  3.000
 KIQ  F18   C16  F19   108.34  3.000
 KIQ  F     C16  C15   111.38  3.000
 KIQ  F18   C16  C15   111.24  3.000
 KIQ  F19   C16  C15   110.77  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
 KIQ  CONST_01  N13  C11  N10  C15     0.00   0.0  0
 KIQ  CONST_02  C11  N13  N14  C15     0.00   0.0  0
 KIQ  CONST_03  C29  C27  C25  C24     0.00   0.0  0
 KIQ  CONST_04  C29  C30  C23  C24     0.00   0.0  0
 KIQ  CONST_05  C25  C27  C29  C30     0.00   0.0  0
 KIQ  CONST_06  C25  C24  C23  C30     0.00   0.0  0
 KIQ  CONST_07  C23  C30  C29  C27     0.00   0.0  0
 KIQ  CONST_08  C23  C24  C25  C27     0.00   0.0  0
 KIQ  CONST_09  N14  C15  N10  C11     0.00   0.0  0
 KIQ  CONST_10  N10  C15  N14  N13     0.00   0.0  0
 KIQ  CONST_11  N10  C11  N13  N14     0.00   0.0  0
 KIQ  CONST_12  C25  C24  C23  C22   180.00   0.0  0
 KIQ  CONST_13  C29  C30  C23  C22   180.00   0.0  0
 KIQ  CONST_14  F31  C30  C23  C22     0.00   0.0  0
 KIQ  CONST_15  F28  C27  C25  C24   180.00   0.0  0
 KIQ  CONST_16  F31  C30  C23  C24   180.00   0.0  0
 KIQ  CONST_17  C27  C29  C30  F31   180.00   0.0  0
 KIQ  CONST_18  F28  C27  C29  C30   180.00   0.0  0
 KIQ  CONST_19  F26  C25  C27  C29   180.00   0.0  0
 KIQ  CONST_20  C23  C24  C25  F26   180.00   0.0  0
 KIQ  CONST_21  C16  C15  N10  C11   180.00   0.0  0
 KIQ  CONST_22  C16  C15  N14  N13   180.00   0.0  0
 KIQ  CONST_23  C9   N10  C15  C16     0.00   0.0  0
 KIQ  CONST_25  C12  N7   C5   C4    180.00   0.0  0
 KIQ  CONST_26  H24  C24  C23  C22     0.00   0.0  0
 KIQ  CONST_27  H29  C29  C27  C25   180.00   0.0  0
 KIQ  CONST_29  C12  N7   C5   O       0.00   0.0  0
 KIQ  Var_01    C22  C21  C20  C4    -15.13  30.0  1
 KIQ  Var_02    C15  N10  C9   C8   -163.71  30.0  1
 KIQ  Var_03    C11  C12  N7   C8    -47.03  30.0  1
 KIQ  Var_04    C    C3   C4   C20   -15.83  30.0  1
 KIQ  Var_05    C3   C4   C20  C21    -0.30  30.0  1
 KIQ  Var_06    N10  C9   C8   N7    -48.63  30.0  1
 KIQ  Var_07    N10  C11  C12  N7     14.95  30.0  1
 KIQ  Var_08    C9   C8   N7   C12    67.45  30.0  1
 KIQ  Var_09    N7   C5   C4   C20    55.09  30.0  2
 KIQ  Var_10    F19  C16  C15  N14     4.97  30.0  2

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
 KIQ  chir_01  C22  C21  C23  C    positiv
 KIQ  chir_02  C    N    C3   C22  negativ

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
 KIQ  plan-1  C22  0.020
 KIQ  plan-1  C24  0.020
 KIQ  plan-1  C30  0.020
 KIQ  plan-1  C29  0.020
 KIQ  plan-1  C27  0.020
 KIQ  plan-1  F28  0.020
 KIQ  plan-1  C25  0.020
 KIQ  plan-1  F26  0.020
 KIQ  plan-1  C23  0.020
 KIQ  plan-1  H24  0.020
 KIQ  plan-1  H29  0.020
 KIQ  plan-1  F31  0.020
 KIQ  plan-2  C15  0.020
 KIQ  plan-2  C12  0.020
 KIQ  plan-2  C11  0.020
 KIQ  plan-2  N13  0.020
 KIQ  plan-2  N14  0.020
 KIQ  plan-2  N10  0.020
 KIQ  plan-2  C9   0.020
 KIQ  plan-2  C16  0.020
 KIQ  plan-3  C4   0.020
 KIQ  plan-3  C5   0.020
 KIQ  plan-3  C8   0.020
 KIQ  plan-3  O    0.020
 KIQ  plan-3  N7   0.020
 KIQ  plan-3  C12  0.020

