# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 19:21:54 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: (4~{S})-6-azanyl-4-[3-(2-fluorophenyl)-5-(trifluoromethyl)phenyl]-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@]1(c2cc(cc(c2)C(F)(F)F)c3ccccc3F)C(=C(N)Oc4n[nH]c(C)c14)C#N
#
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
 8B3  8B3  (4~{S})-6-azanyl-4-[3-(2-fluorophenyl)-5-(trifluoromethyl)phenyl]-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile  ligand  53  33  .  2022-07-23  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8B3
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
 8B3  C2   C  CR6   0   0.611   3.0324  -1.4772   1.3146
 8B3  C3   C  CR6   0  -0.219   2.1464  -0.4310   1.4052
 8B3  C4   C  CR6   0  -0.174   1.7751   0.4990   0.2517
 8B3  C5   C  CR56  0  -0.143   2.2206  -0.2132  -0.9900
 8B3  C6   C  CR56  0   0.460   3.0693  -1.3130  -0.9672
 8B3  N11  N  N     0  -0.294   3.3735  -1.7848  -2.1472
 8B3  C13  C  CH1   0  -0.218   2.5110   1.8663   0.3740
 8B3  C14  C  CH3   0  -0.678   2.1939   2.6208   1.6638
 8B3  C15  C  CR6   0   0.210   0.2502   0.6419   0.1658
 8B3  C16  C  CR16  0  -0.387  -0.3764   1.8412  -0.1409
 8B3  C17  C  CR6   0  -0.149  -1.7590   1.9000  -0.2812
 8B3  C18  C  CR16  0  -0.367  -2.5334   0.7632  -0.1311
 8B3  C19  C  CR6   0   0.142  -1.9208  -0.4523   0.1671
 8B3  C20  C  CR16  0  -0.318  -0.5395  -0.4955   0.3114
 8B3  C39  C  CR6   0   0.520  -2.4814  -2.8529  -0.3074
 8B3  C40  C  CR16  0  -0.402  -3.2568  -3.9855  -0.1560
 8B3  C41  C  CR16  0  -0.245  -4.3568  -3.9355   0.6881
 8B3  C42  C  CR16  0  -0.256  -4.6660  -2.7592   1.3576
 8B3  C43  C  CR16  0  -0.277  -3.8703  -1.6370   1.1856
 8B3  C32  C  CR6   0  -0.148  -2.7524  -1.6594   0.3507
 8B3  C33  C  CT    0   1.056  -2.3908   3.1989  -0.6725
 8B3  F48  F  F     0  -0.310  -1.7958   4.2455  -0.0867
 8B3  F47  F  F     0  -0.315  -2.3080   3.4045  -1.9965
 8B3  F46  F  F     0  -0.305  -3.6875   3.2558  -0.3529
 8B3  C34  C  CH3   0  -0.660   4.0228   1.7204   0.2363
 8B3  C8   C  CSP   0   0.030   1.5501  -0.2274   2.6617
 8B3  N9   N  NS    0  -0.287   1.0417  -0.0862   3.6930
 8B3  N7   N  NH2   0  -0.835   3.4957  -2.2004   2.3398
 8B3  C10  C  CR5   0   0.371   1.9964  -0.0137  -2.3404
 8B3  N51  N  NR15  0  -0.493   2.7052  -0.9689  -2.9681
 8B3  O1   O  O     0  -0.453   3.5705  -1.8839   0.1542
 8B3  H2   H  HCH3  0   0.261   1.4005   1.9947  -2.7566
 8B3  H3   H  HCH3  0   0.270   1.3250   0.9141  -4.1452
 8B3  H4   H  HCH3  0   0.262   0.1052   0.8150  -2.8757
 8B3  H5   H  HCH1  0   0.231   2.1796   2.4774  -0.4729
 8B3  H6   H  HCH3  0   0.233   2.6989   2.1724   2.5199
 8B3  H7   H  HCH3  0   0.243   2.5482   3.6491   1.5818
 8B3  H8   H  HCH3  0   0.236   1.1292   2.6613   1.8920
 8B3  H9   H  HCR6  0   0.279   0.2073   2.7402  -0.2793
 8B3  H10  H  HCR6  0   0.273  -3.6081   0.7999  -0.2527
 8B3  H11  H  HCR6  0   0.256  -0.0622  -1.4347   0.5599
 8B3  H12  H  HCR6  0   0.281  -3.0063  -4.8879  -0.6984
 8B3  H13  H  HCR6  0   0.271  -4.9702  -4.8170   0.8178
 8B3  H14  H  HCR6  0   0.265  -5.5218  -2.7160   2.0173
 8B3  H15  H  HCR6  0   0.269  -4.1070  -0.7244   1.7185
 8B3  H16  H  HCH3  0   0.224   4.4381   1.0814   1.0183
 8B3  H17  H  HCH3  0   0.238   4.3144   1.3123  -0.7305
 8B3  H18  H  HCH3  0   0.239   4.4952   2.6985   0.3337
 8B3  H19  H  HNH2  0   0.418   3.9101  -3.1016   2.1648
 8B3  H20  H  HNH2  0   0.420   3.1422  -2.0467   3.2691
 8B3  H22  H  HNR5  0   0.421   2.7629  -1.1179  -3.9631
 8B3  C12  C  CH3   0  -0.750   1.1656   0.9785  -3.0697
 8B3  F50  F  F     0  -0.304  -1.4341  -2.9076  -1.1459

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
 8B3  F46  C33  single    1.337  0.020  1.337
 8B3  N9   C8   triple    1.158  0.020  1.158
 8B3  F48  C33  single    1.339  0.020  1.339
 8B3  C33  F47  single    1.342  0.020  1.342
 8B3  C33  C17  single    1.496  0.020  1.496
 8B3  C8   C3   single    1.406  0.020  1.406
 8B3  C17  C16  aromatic  1.391  0.020  1.391
 8B3  C17  C18  aromatic  1.384  0.020  1.384
 8B3  C16  C15  aromatic  1.388  0.020  1.388
 8B3  N7   C2   single    1.337  0.020  1.337
 8B3  C3   C2   double    1.374  0.020  1.374
 8B3  C3   C4   single    1.528  0.020  1.528
 8B3  C13  C34  single    1.525  0.020  1.525
 8B3  C13  C14  single    1.527  0.020  1.527
 8B3  C13  C4   single    1.558  0.020  1.558
 8B3  C2   O1   single    1.342  0.020  1.342
 8B3  C18  C19  aromatic  1.393  0.020  1.393
 8B3  C4   C15  single    1.534  0.020  1.534
 8B3  C4   C5   single    1.499  0.020  1.499
 8B3  C15  C20  aromatic  1.392  0.020  1.392
 8B3  O1   C6   single    1.354  0.020  1.354
 8B3  C19  C20  aromatic  1.389  0.020  1.389
 8B3  C19  C32  single    1.477  0.020  1.477
 8B3  C5   C6   aromatic  1.389  0.020  1.389
 8B3  C5   C10  aromatic  1.383  0.020  1.383
 8B3  C43  C32  aromatic  1.395  0.020  1.395
 8B3  C43  C42  aromatic  1.386  0.020  1.386
 8B3  C6   N11  aromatic  1.307  0.020  1.307
 8B3  C32  C39  aromatic  1.390  0.020  1.390
 8B3  C10  C12  single    1.485  0.020  1.485
 8B3  C10  N51  aromatic  1.345  0.020  1.345
 8B3  C42  C41  aromatic  1.388  0.020  1.388
 8B3  N11  N51  aromatic  1.337  0.020  1.337
 8B3  C39  F50  single    1.343  0.020  1.343
 8B3  C39  C40  aromatic  1.381  0.020  1.381
 8B3  C41  C40  aromatic  1.387  0.020  1.387
 8B3  C12  H2   single    0.970  0.020  1.090
 8B3  C12  H3   single    0.970  0.020  1.090
 8B3  C12  H4   single    0.970  0.020  1.090
 8B3  C13  H5   single    0.970  0.020  1.090
 8B3  C14  H6   single    0.970  0.020  1.090
 8B3  C14  H7   single    0.970  0.020  1.090
 8B3  C14  H8   single    0.970  0.020  1.090
 8B3  C16  H9   single    0.930  0.020  1.080
 8B3  C18  H10  single    0.930  0.020  1.080
 8B3  C20  H11  single    0.930  0.020  1.080
 8B3  C40  H12  single    0.930  0.020  1.080
 8B3  C41  H13  single    0.930  0.020  1.080
 8B3  C42  H14  single    0.930  0.020  1.080
 8B3  C43  H15  single    0.930  0.020  1.080
 8B3  C34  H16  single    0.970  0.020  1.090
 8B3  C34  H17  single    0.970  0.020  1.090
 8B3  C34  H18  single    0.970  0.020  1.090
 8B3  N7   H19  single    0.890  0.020  1.040
 8B3  N7   H20  single    0.890  0.020  1.040
 8B3  N51  H22  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
 8B3  O1   C2   N7   111.10  3.000
 8B3  O1   C2   C3   123.11  3.000
 8B3  N7   C2   C3   125.77  3.000
 8B3  C8   C3   C4   118.93  3.000
 8B3  C4   C3   C2   124.78  3.000
 8B3  C8   C3   C2   116.28  3.000
 8B3  C15  C4   C13  113.10  3.000
 8B3  C15  C4   C5   107.06  3.000
 8B3  C13  C4   C5   109.98  3.000
 8B3  C5   C4   C3   105.31  3.000
 8B3  C15  C4   C3   109.91  3.000
 8B3  C13  C4   C3   111.12  3.000
 8B3  C10  C5   C6   103.25  3.000
 8B3  C10  C5   C4   133.78  3.000
 8B3  C6   C5   C4   122.96  3.000
 8B3  O1   C6   N11  120.62  3.000
 8B3  N11  C6   C5   114.40  3.000
 8B3  O1   C6   C5   124.98  3.000
 8B3  N51  N11  C6   102.58  3.000
 8B3  H5   C13  C34  106.46  3.000
 8B3  H5   C13  C14  108.32  3.000
 8B3  C34  C13  C14  109.22  3.000
 8B3  H5   C13  C4   106.62  3.000
 8B3  C14  C13  C4   113.70  3.000
 8B3  C34  C13  C4   112.17  3.000
 8B3  H8   C14  H7   107.34  3.000
 8B3  H8   C14  H6   107.66  3.000
 8B3  H7   C14  H6   107.24  3.000
 8B3  H8   C14  C13  113.46  3.000
 8B3  H7   C14  C13  109.56  3.000
 8B3  H6   C14  C13  111.32  3.000
 8B3  C20  C15  C16  118.23  3.000
 8B3  C20  C15  C4   118.81  3.000
 8B3  C16  C15  C4   122.81  3.000
 8B3  H9   C16  C17  119.26  3.000
 8B3  H9   C16  C15  120.22  3.000
 8B3  C17  C16  C15  120.51  3.000
 8B3  C33  C17  C18  120.34  3.000
 8B3  C18  C17  C16  120.71  3.000
 8B3  C33  C17  C16  118.86  3.000
 8B3  H10  C18  C19  119.36  3.000
 8B3  H10  C18  C17  121.05  3.000
 8B3  C19  C18  C17  119.59  3.000
 8B3  C32  C19  C20  121.42  3.000
 8B3  C32  C19  C18  119.46  3.000
 8B3  C20  C19  C18  119.11  3.000
 8B3  H11  C20  C19  119.28  3.000
 8B3  H11  C20  C15  118.86  3.000
 8B3  C19  C20  C15  121.84  3.000
 8B3  C32  C39  C40  122.89  3.000
 8B3  C40  C39  F50  118.23  3.000
 8B3  C32  C39  F50  118.87  3.000
 8B3  H12  C40  C41  121.23  3.000
 8B3  H12  C40  C39  119.93  3.000
 8B3  C41  C40  C39  118.84  3.000
 8B3  H13  C41  C42  120.42  3.000
 8B3  H13  C41  C40  119.55  3.000
 8B3  C42  C41  C40  120.03  3.000
 8B3  H14  C42  C43  119.84  3.000
 8B3  H14  C42  C41  120.28  3.000
 8B3  C43  C42  C41  119.88  3.000
 8B3  H15  C43  C32  118.88  3.000
 8B3  H15  C43  C42  119.71  3.000
 8B3  C32  C43  C42  121.40  3.000
 8B3  C43  C32  C39  116.96  3.000
 8B3  C39  C32  C19  122.22  3.000
 8B3  C43  C32  C19  120.81  3.000
 8B3  F46  C33  F47  106.80  3.000
 8B3  F47  C33  F48  106.52  3.000
 8B3  F46  C33  F48  107.05  3.000
 8B3  F47  C33  C17  111.40  3.000
 8B3  F48  C33  C17  112.12  3.000
 8B3  F46  C33  C17  112.58  3.000
 8B3  H18  C34  H17  107.42  3.000
 8B3  H18  C34  H16  107.22  3.000
 8B3  H17  C34  H16  108.34  3.000
 8B3  H18  C34  C13  109.60  3.000
 8B3  H17  C34  C13  112.42  3.000
 8B3  H16  C34  C13  111.61  3.000
 8B3  N9   C8   C3   180.00  3.000
 8B3  H20  N7   H19  116.22  3.000
 8B3  H20  N7   C2   120.25  3.000
 8B3  H19  N7   C2   119.55  3.000
 8B3  N51  C10  C12  122.68  3.000
 8B3  N51  C10  C5   105.53  3.000
 8B3  C12  C10  C5   131.78  3.000
 8B3  H22  N51  C10  126.58  3.000
 8B3  H22  N51  N11  119.18  3.000
 8B3  C10  N51  N11  114.23  3.000
 8B3  C6   O1   C2   116.08  3.000
 8B3  H4   C12  H3   108.01  3.000
 8B3  H4   C12  H2   107.37  3.000
 8B3  H3   C12  H2   107.91  3.000
 8B3  H4   C12  C10  110.88  3.000
 8B3  H3   C12  C10  111.32  3.000
 8B3  H2   C12  C10  111.19  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
 8B3  CONST_01  N51  N11  C6   C5      0.00   0.0  0
 8B3  CONST_02  N11  N51  C10  C5      0.00   0.0  0
 8B3  CONST_03  N51  C10  C5   C6      0.00   0.0  0
 8B3  CONST_04  C10  N51  N11  C6      0.00   0.0  0
 8B3  CONST_05  C10  C5   C6   N11     0.00   0.0  0
 8B3  CONST_06  C18  C17  C16  C15     0.00   0.0  0
 8B3  CONST_07  C18  C19  C20  C15     0.00   0.0  0
 8B3  CONST_08  C32  C19  C20  C15   180.00   0.0  0
 8B3  CONST_09  C19  C18  C17  C16     0.00   0.0  0
 8B3  CONST_10  C19  C20  C15  C16     0.00   0.0  0
 8B3  CONST_11  C20  C15  C16  C17     0.00   0.0  0
 8B3  CONST_12  C20  C19  C18  C17     0.00   0.0  0
 8B3  CONST_13  C32  C19  C18  C17   180.00   0.0  0
 8B3  CONST_16  C42  C43  C32  C19   180.00   0.0  0
 8B3  CONST_17  C40  C39  C32  C19   180.00   0.0  0
 8B3  CONST_20  C42  C43  C32  C39     0.00   0.0  0
 8B3  CONST_21  C42  C41  C40  C39     0.00   0.0  0
 8B3  CONST_22  C43  C32  C39  C40     0.00   0.0  0
 8B3  CONST_23  C43  C42  C41  C40     0.00   0.0  0
 8B3  CONST_24  C32  C43  C42  C41     0.00   0.0  0
 8B3  CONST_25  C32  C39  C40  C41     0.00   0.0  0
 8B3  CONST_26  C17  C16  C15  C4    180.00   0.0  0
 8B3  CONST_27  C19  C20  C15  C4    180.00   0.0  0
 8B3  CONST_28  C12  C10  C5   C4      0.00   0.0  0
 8B3  CONST_29  C12  C10  C5   C6    180.00   0.0  0
 8B3  CONST_30  C12  C10  N51  N11   180.00   0.0  0
 8B3  CONST_31  C33  C17  C16  C15   180.00   0.0  0
 8B3  CONST_32  C33  C17  C18  C19   180.00   0.0  0
 8B3  CONST_33  F50  C39  C32  C19     0.00   0.0  0
 8B3  CONST_34  C43  C32  C39  F50   180.00   0.0  0
 8B3  CONST_35  C41  C40  C39  F50   180.00   0.0  0
 8B3  CONST_36  H9   C16  C15  C4      0.00   0.0  0
 8B3  CONST_37  H11  C20  C15  C4      0.00   0.0  0
 8B3  CONST_38  H22  N51  C10  C5    180.00   0.0  0
 8B3  CONST_39  H10  C18  C17  C16   180.00   0.0  0
 8B3  CONST_40  H15  C43  C32  C19     0.00   0.0  0
 8B3  CONST_41  H13  C41  C40  C39   180.00   0.0  0
 8B3  CONST_42  H14  C42  C41  C40   180.00   0.0  0
 8B3  CONST_43  H12  C40  C41  C42   180.00   0.0  0
 8B3  Var_01    C5   C6   O1   C2     10.91  30.0  1
 8B3  Var_02    O1   C2   C3   C4     -7.12  30.0  1
 8B3  Var_03    F46  C33  C17  C16  -159.33  30.0  3
 8B3  Var_04    H19  N7   C2   C3    161.60  30.0  2
 8B3  Var_05    H2   C12  C10  C5     52.64  30.0  2
 8B3  Var_06    H16  C34  C13  C4    -61.06  30.0  3
 8B3  Var_07    H6   C14  C13  C4     74.59  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
 8B3  chir_01  C4  C3  C15  C5  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
 8B3  plan-1  C4   0.020
 8B3  plan-1  C15  0.020
 8B3  plan-1  C16  0.020
 8B3  plan-1  C17  0.020
 8B3  plan-1  C18  0.020
 8B3  plan-1  C19  0.020
 8B3  plan-1  C20  0.020
 8B3  plan-1  C32  0.020
 8B3  plan-1  C33  0.020
 8B3  plan-1  H9   0.020
 8B3  plan-1  H10  0.020
 8B3  plan-1  H11  0.020
 8B3  plan-2  C19  0.020
 8B3  plan-2  C39  0.020
 8B3  plan-2  C40  0.020
 8B3  plan-2  C41  0.020
 8B3  plan-2  C42  0.020
 8B3  plan-2  C43  0.020
 8B3  plan-2  C32  0.020
 8B3  plan-2  H12  0.020
 8B3  plan-2  H13  0.020
 8B3  plan-2  H14  0.020
 8B3  plan-2  H15  0.020
 8B3  plan-2  F50  0.020
 8B3  plan-3  C4   0.020
 8B3  plan-3  C5   0.020
 8B3  plan-3  C6   0.020
 8B3  plan-3  N11  0.020
 8B3  plan-3  C10  0.020
 8B3  plan-3  N51  0.020
 8B3  plan-3  O1   0.020
 8B3  plan-3  H22  0.020
 8B3  plan-3  C12  0.020

