# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 18:56:55 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: (4~{S})-6-azanyl-4-[3-(2-chlorophenyl)-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)c3ccccc3Cl)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
 8AU  8AU  (4~{S})-6-azanyl-4-[3-(2-chlorophenyl)-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_8AU
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
 8AU  C4   C   CR6   0  -0.172  -2.0260  -0.2974   0.4285
 8AU  C6   C   CR56  0   0.460  -3.3590   1.4958  -0.7721
 8AU  C8   C   CSP   0   0.030  -1.3734   0.6354   2.6856
 8AU  C15  C   CH3   0  -0.679  -2.4226  -2.2099   2.1157
 8AU  C17  C   CR16  0  -0.384  -0.0484  -1.8605  -0.0675
 8AU  C22  C   CR6   0   0.156   2.5358   1.4995  -0.4671
 8AU  C2   C   CR6   0   0.609  -2.9772   1.8578   1.4548
 8AU  C3   C   CR6   0  -0.216  -2.1486   0.7640   1.5202
 8AU  N9   N   NS    0  -0.286  -0.7211   0.5599   3.6400
 8AU  C14  C   CH1   0  -0.215  -2.8442  -1.5715   0.7929
 8AU  C18  C   CR6   0  -0.149   1.2936  -2.0488  -0.3951
 8AU  C25  C   CR6   0  -0.122   3.7180   1.6947   0.2464
 8AU  C26  C   CR16  0  -0.193   4.5081   2.8182   0.0527
 8AU  C27  C   CR16  0  -0.271   4.1188   3.7795  -0.8671
 8AU  C28  C   CR16  0  -0.229   2.9410   3.6169  -1.5822
 8AU  C29  C   CR16  0  -0.308   2.1643   2.4878  -1.3793
 8AU  C20  C   CR6   0   0.106   1.6667   0.3156  -0.2943
 8AU  C19  C   CR16  0  -0.359   2.1538  -0.9739  -0.5085
 8AU  C23  C   CT    0   1.056   1.7651  -3.4472  -0.6420
 8AU  F32  F   F     0  -0.314   1.1528  -3.9953  -1.7022
 8AU  F31  F   F     0  -0.302   3.0791  -3.5200  -0.8693
 8AU  F30  F   F     0  -0.315   1.5035  -4.2481   0.4016
 8AU  C21  C   CR16  0  -0.314   0.3309   0.4900   0.0312
 8AU  C16  C   CR6   0   0.208  -0.5467  -0.5875   0.1529
 8AU  C24  C   CH3   0  -0.665  -4.3448  -1.3001   0.8277
 8AU  N7   N   NH2   0  -0.835  -3.2362   2.7037   2.4580
 8AU  C5   C   CR56  0  -0.146  -2.5906   0.3386  -0.8055
 8AU  C10  C   CR5   0   0.370  -2.5648   0.0131  -2.1496
 8AU  C13  C   CH3   0  -0.750  -1.9019  -1.0938  -2.8857
 8AU  N11  N   NR15  0  -0.493  -3.2937   0.9622  -2.7636
 8AU  N12  N   N     0  -0.294  -3.7924   1.8895  -1.9403
 8AU  O1   O   O     0  -0.454  -3.6613   2.1934   0.3492
 8AU  H1   H   HCH3  0   0.243  -2.8484  -3.2108   2.1946
 8AU  H2   H   HCH3  0   0.236  -1.3431  -2.3064   2.2296
 8AU  H3   H   HCH3  0   0.232  -2.7942  -1.6359   2.9657
 8AU  H4   H   HCR6  0   0.278  -0.6994  -2.7216  -0.0022
 8AU  H5   H   HCH1  0   0.232  -2.6750  -2.2957  -0.0121
 8AU  H6   H   HCR6  0   0.282   5.4187   2.9437   0.6223
 8AU  H7   H   HCR6  0   0.271   4.7376   4.6540  -1.0166
 8AU  H8   H   HCR6  0   0.266   2.6289   4.3641  -2.2992
 8AU  H9   H   HCR6  0   0.264   1.2517   2.3567  -1.9474
 8AU  H10  H   HCR6  0   0.271   3.1908  -1.1155  -0.7793
 8AU  H11  H   HCR6  0   0.263  -0.0403   1.4948   0.1946
 8AU  H12  H   HCH3  0   0.239  -4.7374  -0.9889  -0.1394
 8AU  H13  H   HCH3  0   0.240  -4.8749  -2.2082   1.1175
 8AU  H14  H   HCH3  0   0.224  -4.5942  -0.5323   1.5632
 8AU  H15  H   HNH2  0   0.417  -3.6129   3.6157   2.2554
 8AU  H16  H   HNH2  0   0.421  -2.7591   2.6055   3.3385
 8AU  H17  H   HCH3  0   0.261  -2.2081  -2.0652  -2.4993
 8AU  H18  H   HCH3  0   0.269  -2.1439  -1.0641  -3.9471
 8AU  H19  H   HCH3  0   0.262  -0.8179  -1.0306  -2.7856
 8AU  H20  H   HNR5  0   0.422  -3.4758   1.0324  -3.7523
 8AU  CL3  CL  CL    0  -0.124   4.2173   0.5455   1.4465

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
 8AU  F31  C23  single    1.335  0.020  1.335
 8AU  N9   C8   triple    1.158  0.020  1.158
 8AU  F30  C23  single    1.341  0.020  1.341
 8AU  C23  F32  single    1.341  0.020  1.341
 8AU  C23  C18  single    1.496  0.020  1.496
 8AU  C8   C3   single    1.406  0.020  1.406
 8AU  C18  C17  aromatic  1.394  0.020  1.394
 8AU  C18  C19  aromatic  1.381  0.020  1.381
 8AU  C17  C16  aromatic  1.385  0.020  1.385
 8AU  N7   C2   single    1.337  0.020  1.337
 8AU  C3   C2   double    1.374  0.020  1.374
 8AU  C3   C4   single    1.528  0.020  1.528
 8AU  C14  C24  single    1.525  0.020  1.525
 8AU  C14  C15  single    1.528  0.020  1.528
 8AU  C14  C4   single    1.557  0.020  1.557
 8AU  C2   O1   single    1.343  0.020  1.343
 8AU  C19  C20  aromatic  1.395  0.020  1.395
 8AU  C16  C4   single    1.532  0.020  1.532
 8AU  C16  C21  aromatic  1.395  0.020  1.395
 8AU  C4   C5   single    1.499  0.020  1.499
 8AU  O1   C6   single    1.355  0.020  1.355
 8AU  C20  C21  aromatic  1.386  0.020  1.386
 8AU  C20  C22  single    1.479  0.020  1.479
 8AU  C5   C6   aromatic  1.389  0.020  1.389
 8AU  C5   C10  aromatic  1.383  0.020  1.383
 8AU  C29  C22  aromatic  1.395  0.020  1.395
 8AU  C29  C28  aromatic  1.385  0.020  1.385
 8AU  C6   N12  aromatic  1.307  0.020  1.307
 8AU  C22  C25  aromatic  1.395  0.020  1.395
 8AU  C10  C13  single    1.485  0.020  1.485
 8AU  C10  N11  aromatic  1.345  0.020  1.345
 8AU  C28  C27  aromatic  1.387  0.020  1.387
 8AU  N12  N11  aromatic  1.337  0.020  1.337
 8AU  C25  CL3  single    1.735  0.020  1.735
 8AU  C25  C26  aromatic  1.387  0.020  1.387
 8AU  C27  C26  aromatic  1.386  0.020  1.386
 8AU  C15  H1   single    0.970  0.020  1.090
 8AU  C15  H2   single    0.970  0.020  1.090
 8AU  C15  H3   single    0.970  0.020  1.090
 8AU  C17  H4   single    0.930  0.020  1.080
 8AU  C14  H5   single    0.970  0.020  1.090
 8AU  C26  H6   single    0.930  0.020  1.080
 8AU  C27  H7   single    0.930  0.020  1.080
 8AU  C28  H8   single    0.930  0.020  1.080
 8AU  C29  H9   single    0.930  0.020  1.080
 8AU  C19  H10  single    0.930  0.020  1.080
 8AU  C21  H11  single    0.930  0.020  1.080
 8AU  C24  H12  single    0.970  0.020  1.090
 8AU  C24  H13  single    0.970  0.020  1.090
 8AU  C24  H14  single    0.970  0.020  1.090
 8AU  N7   H15  single    0.890  0.020  1.040
 8AU  N7   H16  single    0.890  0.020  1.040
 8AU  C13  H17  single    0.970  0.020  1.090
 8AU  C13  H18  single    0.970  0.020  1.090
 8AU  C13  H19  single    0.970  0.020  1.090
 8AU  N11  H20  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
 8AU  C5   C4   C16  107.21  3.000
 8AU  C5   C4   C14  109.99  3.000
 8AU  C16  C4   C14  113.23  3.000
 8AU  C5   C4   C3   105.27  3.000
 8AU  C16  C4   C3   109.73  3.000
 8AU  C14  C4   C3   111.04  3.000
 8AU  O1   C6   N12  120.72  3.000
 8AU  N12  C6   C5   114.39  3.000
 8AU  O1   C6   C5   124.89  3.000
 8AU  N9   C8   C3   180.00  3.000
 8AU  H3   C15  H2   107.61  3.000
 8AU  H3   C15  H1   107.07  3.000
 8AU  H2   C15  H1   107.33  3.000
 8AU  H3   C15  C14  111.14  3.000
 8AU  H2   C15  C14  113.62  3.000
 8AU  H1   C15  C14  109.77  3.000
 8AU  H4   C17  C16  120.39  3.000
 8AU  H4   C17  C18  119.08  3.000
 8AU  C16  C17  C18  120.53  3.000
 8AU  C20  C22  C29  119.14  3.000
 8AU  C29  C22  C25  117.45  3.000
 8AU  C20  C22  C25  123.40  3.000
 8AU  O1   C2   N7   111.15  3.000
 8AU  O1   C2   C3   123.05  3.000
 8AU  N7   C2   C3   125.78  3.000
 8AU  C2   C3   C8   116.42  3.000
 8AU  C2   C3   C4   124.59  3.000
 8AU  C8   C3   C4   118.99  3.000
 8AU  H5   C14  C24  106.63  3.000
 8AU  H5   C14  C15  108.49  3.000
 8AU  C24  C14  C15  109.02  3.000
 8AU  H5   C14  C4   106.72  3.000
 8AU  C15  C14  C4   113.54  3.000
 8AU  C24  C14  C4   112.13  3.000
 8AU  C23  C18  C19  121.16  3.000
 8AU  C19  C18  C17  120.90  3.000
 8AU  C23  C18  C17  117.92  3.000
 8AU  C26  C25  CL3  117.98  3.000
 8AU  C26  C25  C22  121.65  3.000
 8AU  CL3  C25  C22  120.34  3.000
 8AU  H6   C26  C27  120.36  3.000
 8AU  H6   C26  C25  120.01  3.000
 8AU  C27  C26  C25  119.63  3.000
 8AU  H7   C27  C28  120.60  3.000
 8AU  H7   C27  C26  119.45  3.000
 8AU  C28  C27  C26  119.94  3.000
 8AU  H8   C28  C29  119.89  3.000
 8AU  H8   C28  C27  120.38  3.000
 8AU  C29  C28  C27  119.73  3.000
 8AU  H9   C29  C28  119.63  3.000
 8AU  H9   C29  C22  118.79  3.000
 8AU  C28  C29  C22  121.58  3.000
 8AU  C21  C20  C19  119.27  3.000
 8AU  C21  C20  C22  119.55  3.000
 8AU  C19  C20  C22  121.12  3.000
 8AU  H10  C19  C20  119.64  3.000
 8AU  H10  C19  C18  121.06  3.000
 8AU  C20  C19  C18  119.29  3.000
 8AU  F30  C23  F31  106.96  3.000
 8AU  F30  C23  F32  106.37  3.000
 8AU  F31  C23  F32  107.00  3.000
 8AU  F32  C23  C18  111.62  3.000
 8AU  F30  C23  C18  111.61  3.000
 8AU  F31  C23  C18  112.90  3.000
 8AU  H11  C21  C16  119.19  3.000
 8AU  H11  C21  C20  118.83  3.000
 8AU  C16  C21  C20  121.98  3.000
 8AU  C21  C16  C17  118.02  3.000
 8AU  C21  C16  C4   118.47  3.000
 8AU  C17  C16  C4   123.37  3.000
 8AU  H14  C24  H13  107.18  3.000
 8AU  H14  C24  H12  108.35  3.000
 8AU  H13  C24  H12  107.37  3.000
 8AU  H14  C24  C14  111.42  3.000
 8AU  H13  C24  C14  109.64  3.000
 8AU  H12  C24  C14  112.66  3.000
 8AU  H16  N7   H15  116.20  3.000
 8AU  H16  N7   C2   120.19  3.000
 8AU  H15  N7   C2   119.62  3.000
 8AU  C10  C5   C6   103.28  3.000
 8AU  C10  C5   C4   133.88  3.000
 8AU  C6   C5   C4   122.82  3.000
 8AU  N11  C10  C13  122.78  3.000
 8AU  N11  C10  C5   105.51  3.000
 8AU  C13  C10  C5   131.70  3.000
 8AU  H19  C13  H18  107.99  3.000
 8AU  H19  C13  H17  107.37  3.000
 8AU  H18  C13  H17  107.91  3.000
 8AU  H19  C13  C10  110.79  3.000
 8AU  H18  C13  C10  111.31  3.000
 8AU  H17  C13  C10  111.30  3.000
 8AU  H20  N11  N12  119.24  3.000
 8AU  H20  N11  C10  126.51  3.000
 8AU  N12  N11  C10  114.24  3.000
 8AU  N11  N12  C6   102.58  3.000
 8AU  C2   O1   C6   116.05  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
 8AU  CONST_01  N11  C10  C5   C6      0.00   0.0  0
 8AU  CONST_02  C10  N11  N12  C6      0.00   0.0  0
 8AU  CONST_03  C20  C19  C18  C17     0.00   0.0  0
 8AU  CONST_04  C20  C21  C16  C17     0.00   0.0  0
 8AU  CONST_05  C18  C19  C20  C22   180.00   0.0  0
 8AU  CONST_06  C16  C21  C20  C22   180.00   0.0  0
 8AU  CONST_07  C27  C28  C29  C22     0.00   0.0  0
 8AU  CONST_08  C27  C26  C25  C22     0.00   0.0  0
 8AU  CONST_09  C21  C16  C17  C18     0.00   0.0  0
 8AU  CONST_10  C21  C20  C19  C18     0.00   0.0  0
 8AU  CONST_13  C28  C29  C22  C25     0.00   0.0  0
 8AU  CONST_14  C28  C27  C26  C25     0.00   0.0  0
 8AU  CONST_15  C20  C22  C25  C26   180.00   0.0  0
 8AU  CONST_16  C29  C22  C25  C26     0.00   0.0  0
 8AU  CONST_17  C29  C28  C27  C26     0.00   0.0  0
 8AU  CONST_18  C20  C22  C29  C28   180.00   0.0  0
 8AU  CONST_21  C16  C17  C18  C19     0.00   0.0  0
 8AU  CONST_22  C16  C21  C20  C19     0.00   0.0  0
 8AU  CONST_23  N11  N12  C6   C5      0.00   0.0  0
 8AU  CONST_24  N12  N11  C10  C5      0.00   0.0  0
 8AU  CONST_25  N12  C6   C5   C10     0.00   0.0  0
 8AU  CONST_26  C18  C17  C16  C4    180.00   0.0  0
 8AU  CONST_27  C20  C21  C16  C4    180.00   0.0  0
 8AU  CONST_28  C13  C10  C5   C4      0.00   0.0  0
 8AU  CONST_29  C13  C10  C5   C6    180.00   0.0  0
 8AU  CONST_30  C20  C22  C25  CL3     0.00   0.0  0
 8AU  CONST_31  C29  C22  C25  CL3   180.00   0.0  0
 8AU  CONST_32  C27  C26  C25  CL3   180.00   0.0  0
 8AU  CONST_33  C23  C18  C19  C20   180.00   0.0  0
 8AU  CONST_34  C16  C17  C18  C23   180.00   0.0  0
 8AU  CONST_35  N12  N11  C10  C13   180.00   0.0  0
 8AU  CONST_36  H4   C17  C16  C4      0.00   0.0  0
 8AU  CONST_37  H11  C21  C16  C4      0.00   0.0  0
 8AU  CONST_38  H20  N11  N12  C6    180.00   0.0  0
 8AU  CONST_39  H10  C19  C18  C17   180.00   0.0  0
 8AU  CONST_40  H8   C28  C29  C22   180.00   0.0  0
 8AU  CONST_41  H6   C26  C25  C22   180.00   0.0  0
 8AU  CONST_42  H9   C29  C22  C25   180.00   0.0  0
 8AU  CONST_43  H7   C27  C26  C25   180.00   0.0  0
 8AU  Var_01    O1   C2   C3   C4     -7.86  30.0  1
 8AU  Var_02    C3   C2   O1   C6     -8.51  30.0  1
 8AU  Var_03    C5   C6   O1   C2     11.78  30.0  1
 8AU  Var_04    F31  C23  C18  C17  -176.27  30.0  2
 8AU  Var_05    H15  N7   C2   C3    161.06  30.0  2
 8AU  Var_06    H17  C13  C10  C5     56.72  30.0  2
 8AU  Var_07    H12  C24  C14  C4     62.32  30.0  3
 8AU  Var_08    H1   C15  C14  C4   -166.18  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
 8AU  chir_01  C4  C3  C16  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
 8AU  plan-1  C4   0.020
 8AU  plan-1  C17  0.020
 8AU  plan-1  C22  0.020
 8AU  plan-1  C18  0.020
 8AU  plan-1  C20  0.020
 8AU  plan-1  C19  0.020
 8AU  plan-1  C23  0.020
 8AU  plan-1  C21  0.020
 8AU  plan-1  C16  0.020
 8AU  plan-1  H4   0.020
 8AU  plan-1  H10  0.020
 8AU  plan-1  H11  0.020
 8AU  plan-2  C22  0.020
 8AU  plan-2  C25  0.020
 8AU  plan-2  C26  0.020
 8AU  plan-2  C27  0.020
 8AU  plan-2  C28  0.020
 8AU  plan-2  C29  0.020
 8AU  plan-2  C20  0.020
 8AU  plan-2  H6   0.020
 8AU  plan-2  H7   0.020
 8AU  plan-2  H8   0.020
 8AU  plan-2  H9   0.020
 8AU  plan-2  CL3  0.020
 8AU  plan-3  C4   0.020
 8AU  plan-3  C6   0.020
 8AU  plan-3  C5   0.020
 8AU  plan-3  C10  0.020
 8AU  plan-3  C13  0.020
 8AU  plan-3  N11  0.020
 8AU  plan-3  N12  0.020
 8AU  plan-3  O1   0.020
 8AU  plan-3  H20  0.020

