# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 17:14:00 2020
#   Inital geometry file: a 145 line input string
#   Ligand name: 1-[3-[(4~{S})-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazol-4-yl]-5-fluoranyl-phenyl]piperidine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@]1(c2cc(F)cc(c2)N3CCC(CC3)C(O)=O)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
 8UL  8UL  '1-[3-[(4~{S})-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazol-4-yl]-5-fluoranyl-phenyl]piperidine-4-carboxylic acid'  ligand  57  32  .  2022-07-24  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_8UL
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
 8UL  C2   C  C      0   0.602   2.3395   2.3377  -1.1194
 8UL  C3   C  C      0  -0.216   2.1333   1.0019  -1.3543
 8UL  C4   C  CT     0  -0.166   2.4597  -0.1205  -0.3697
 8UL  C5   C  CR5    0  -0.148   2.6234   0.5564   0.9580
 8UL  C6   C  CR5    0   0.457   2.7550   1.9333   1.0937
 8UL  C10  C  CR5    0   0.364   2.7204   0.0999   2.2602
 8UL  C14  C  CH1    0  -0.213   3.7870  -0.8374  -0.7618
 8UL  C15  C  CH3    0  -0.679   3.7649  -1.4605  -2.1572
 8UL  C17  C  CR16   0  -0.564   1.4191  -2.4630  -0.2108
 8UL  C18  C  CR6    0   0.601   0.2813  -3.2266  -0.0607
 8UL  C19  C  CR6    0   0.424  -1.1586  -1.3143  -0.0053
 8UL  N23  N  NT     0  -0.516  -2.4061  -0.7236   0.1245
 8UL  C24  C  CH2    0  -0.296  -2.6936   0.4456  -0.7019
 8UL  C25  C  CH2    0  -0.418  -3.8807   1.2384  -0.1823
 8UL  O32  O  OC    -1  -0.613  -7.2712   0.4490   0.9696
 8UL  C29  C  C      0   0.432  -6.3653   1.1294   0.4457
 8UL  O31  O  O      0  -0.607  -6.3895   2.3622   0.2564
 8UL  C26  C  CH1    0  -0.398  -5.1171   0.3653  -0.0425
 8UL  C27  C  CH2    0  -0.417  -4.7662  -0.8254   0.8373
 8UL  C28  C  CH2    0  -0.304  -3.5578  -1.5885   0.3144
 8UL  C30  C  CR16   0  -0.568  -0.9914  -2.7076   0.0297
 8UL  F21  F  F      0  -0.325   0.4167  -4.5662  -0.0201
 8UL  C20  C  CR16   0  -0.388  -0.0032  -0.5303  -0.1512
 8UL  C16  C  CR6    0   0.211   1.2649  -1.0798  -0.2661
 8UL  C22  C  CH3    0  -0.662   4.9958   0.0869  -0.6568
 8UL  C8   C  CSP    0   0.036   1.5698   0.6707  -2.5996
 8UL  N9   N  NS     0  -0.290   1.0865   0.4216  -3.6224
 8UL  N7   N  NH2    0  -0.835   2.2194   3.3213  -2.0226
 8UL  C13  C  CH3    0  -0.746   2.6533  -1.2679   2.8349
 8UL  N11  N  NR15   0  -0.493   2.8965   1.1987   3.0162
 8UL  N12  N  N      0  -0.296   2.9188   2.3420   2.3246
 8UL  O1   O  O2     0  -0.454   2.7273   2.8219   0.0717
 8UL  H1   H  HCH1   0   0.233   3.9371  -1.6337  -0.0251
 8UL  H2   H  HCH3   0   0.229   3.8586  -0.6979  -2.9319
 8UL  H3   H  HCH3   0   0.239   4.6145  -2.1362  -2.2686
 8UL  H4   H  HCH3   0   0.238   2.8631  -2.0361  -2.3628
 8UL  H5   H  HCR6   0   0.269   2.3787  -2.9532  -0.2849
 8UL  H6   H  HCH2   0   0.247  -1.8267   1.1002  -0.7296
 8UL  H7   H  HCH2   0   0.209  -2.8873   0.1326  -1.7394
 8UL  H8   H  HCH2   0   0.209  -3.6222   1.6757   0.7875
 8UL  H9   H  HCH2   0   0.227  -4.0633   2.0674  -0.8667
 8UL  H11  H  HCH1   0   0.220  -5.3634  -0.0253  -1.0429
 8UL  H12  H  HCH2   0   0.210  -4.5570  -0.4811   1.8557
 8UL  H13  H  HCH2   0   0.229  -5.6042  -1.5196   0.9034
 8UL  H14  H  HCH2   0   0.206  -3.8273  -2.0982  -0.6247
 8UL  H15  H  HCH2   0   0.246  -3.3072  -2.3639   1.0388
 8UL  H16  H  HCR6   0   0.282  -1.8249  -3.3906   0.1034
 8UL  H17  H  HCR6   0   0.253  -0.0851   0.5475  -0.1547
 8UL  H18  H  HCH3   0   0.237   5.1465   0.4677   0.3525
 8UL  H19  H  HCH3   0   0.237   5.8989  -0.4580  -0.9354
 8UL  H20  H  HCH3   0   0.222   4.9104   0.9366  -1.3376
 8UL  H21  H  HNH2   0   0.418   1.8750   3.1101  -2.9442
 8UL  H22  H  HNH2   0   0.414   2.0538   4.2618  -1.7013
 8UL  H23  H  HCH3   0   0.259   3.4348  -1.9053   2.4215
 8UL  H24  H  HCH3   0   0.265   2.7723  -1.2497   3.9173
 8UL  H25  H  HCH3   0   0.264   1.6963  -1.7351   2.6038
 8UL  H26  H  HNR5   0   0.420   2.9971   1.2276   4.0184

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
 8UL  O31  C29  deloc     1.247  0.020  1.247
 8UL  C29  O32  deloc     1.248  0.020  1.248
 8UL  C29  C26  single    1.543  0.020  1.543
 8UL  C25  C26  single    1.520  0.020  1.520
 8UL  C25  C24  single    1.519  0.020  1.519
 8UL  C26  C27  single    1.522  0.020  1.522
 8UL  N11  N12  aromatic  1.336  0.020  1.336
 8UL  N11  C10  aromatic  1.345  0.020  1.345
 8UL  C24  N23  single    1.460  0.020  1.460
 8UL  N12  C6   aromatic  1.307  0.020  1.307
 8UL  C13  C10  single    1.485  0.020  1.485
 8UL  C10  C5   aromatic  1.383  0.020  1.383
 8UL  C27  C28  single    1.522  0.020  1.522
 8UL  C6   C5   aromatic  1.390  0.020  1.390
 8UL  C6   O1   single    1.355  0.020  1.355
 8UL  N23  C28  single    1.453  0.020  1.453
 8UL  N23  C19  single    1.386  0.020  1.386
 8UL  C5   C4   single    1.499  0.020  1.499
 8UL  O1   C2   single    1.343  0.020  1.343
 8UL  C20  C19  aromatic  1.404  0.020  1.404
 8UL  C20  C16  aromatic  1.387  0.020  1.387
 8UL  C19  C30  aromatic  1.404  0.020  1.404
 8UL  C4   C16  single    1.536  0.020  1.536
 8UL  C4   C14  single    1.559  0.020  1.559
 8UL  C4   C3   single    1.528  0.020  1.528
 8UL  C15  C14  single    1.528  0.020  1.528
 8UL  C16  C17  aromatic  1.393  0.020  1.393
 8UL  C30  C18  aromatic  1.377  0.020  1.377
 8UL  C22  C14  single    1.525  0.020  1.525
 8UL  C2   C3   double    1.372  0.020  1.372
 8UL  C2   N7   single    1.341  0.020  1.341
 8UL  C3   C8   single    1.406  0.020  1.406
 8UL  C17  C18  aromatic  1.378  0.020  1.378
 8UL  C18  F21  single    1.347  0.020  1.347
 8UL  C8   N9   triple    1.158  0.020  1.158
 8UL  C14  H1   single    0.970  0.020  1.090
 8UL  C15  H2   single    0.970  0.020  1.090
 8UL  C15  H3   single    0.970  0.020  1.090
 8UL  C15  H4   single    0.970  0.020  1.090
 8UL  C17  H5   single    0.930  0.020  1.080
 8UL  C24  H6   single    0.970  0.020  1.090
 8UL  C24  H7   single    0.970  0.020  1.090
 8UL  C25  H8   single    0.970  0.020  1.090
 8UL  C25  H9   single    0.970  0.020  1.090
 8UL  C26  H11  single    0.970  0.020  1.090
 8UL  C27  H12  single    0.970  0.020  1.090
 8UL  C27  H13  single    0.970  0.020  1.090
 8UL  C28  H14  single    0.970  0.020  1.090
 8UL  C28  H15  single    0.970  0.020  1.090
 8UL  C30  H16  single    0.930  0.020  1.080
 8UL  C20  H17  single    0.930  0.020  1.080
 8UL  C22  H18  single    0.970  0.020  1.090
 8UL  C22  H19  single    0.970  0.020  1.090
 8UL  C22  H20  single    0.970  0.020  1.090
 8UL  N7   H21  single    0.890  0.020  1.040
 8UL  N7   H22  single    0.890  0.020  1.040
 8UL  C13  H23  single    0.970  0.020  1.090
 8UL  C13  H24  single    0.970  0.020  1.090
 8UL  C13  H25  single    0.970  0.020  1.090
 8UL  N11  H26  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
 8UL  O1   C2   N7   111.03  3.000
 8UL  N7   C2   C3   125.84  3.000
 8UL  O1   C2   C3   123.12  3.000
 8UL  C8   C3   C4   118.88  3.000
 8UL  C8   C3   C2   116.18  3.000
 8UL  C4   C3   C2   124.94  3.000
 8UL  C16  C4   C14  113.09  3.000
 8UL  C14  C4   C5   109.72  3.000
 8UL  C16  C4   C5   107.89  3.000
 8UL  C14  C4   C3   110.95  3.000
 8UL  C16  C4   C3   109.64  3.000
 8UL  C5   C4   C3   105.20  3.000
 8UL  C10  C5   C6   103.20  3.000
 8UL  C6   C5   C4   122.96  3.000
 8UL  C10  C5   C4   133.81  3.000
 8UL  O1   C6   N12  120.52  3.000
 8UL  O1   C6   C5   125.05  3.000
 8UL  N12  C6   C5   114.43  3.000
 8UL  N11  C10  C13  122.73  3.000
 8UL  C13  C10  C5   131.69  3.000
 8UL  N11  C10  C5   105.58  3.000
 8UL  H1   C14  C22  106.60  3.000
 8UL  H1   C14  C15  108.64  3.000
 8UL  C22  C14  C15  108.75  3.000
 8UL  H1   C14  C4   106.38  3.000
 8UL  C22  C14  C4   112.26  3.000
 8UL  C15  C14  C4   113.89  3.000
 8UL  H4   C15  H3   107.34  3.000
 8UL  H4   C15  H2   107.84  3.000
 8UL  H3   C15  H2   107.06  3.000
 8UL  H4   C15  C14  113.56  3.000
 8UL  H3   C15  C14  109.53  3.000
 8UL  H2   C15  C14  111.22  3.000
 8UL  H5   C17  C16  123.12  3.000
 8UL  H5   C17  C18  119.30  3.000
 8UL  C16  C17  C18  117.59  3.000
 8UL  F21  C18  C30  117.75  3.000
 8UL  F21  C18  C17  118.12  3.000
 8UL  C30  C18  C17  124.13  3.000
 8UL  C20  C19  C30  117.31  3.000
 8UL  C30  C19  N23  121.86  3.000
 8UL  C20  C19  N23  120.82  3.000
 8UL  C28  N23  C24  113.24  3.000
 8UL  C28  N23  C19  118.16  3.000
 8UL  C24  N23  C19  117.73  3.000
 8UL  H7   C24  H6   106.72  3.000
 8UL  H7   C24  C25  109.46  3.000
 8UL  H6   C24  C25  108.53  3.000
 8UL  H7   C24  N23  109.90  3.000
 8UL  H6   C24  N23  109.85  3.000
 8UL  C25  C24  N23  112.22  3.000
 8UL  H9   C25  H8   106.97  3.000
 8UL  H9   C25  C26  110.99  3.000
 8UL  H8   C25  C26  109.88  3.000
 8UL  H9   C25  C24  108.24  3.000
 8UL  H8   C25  C24  109.08  3.000
 8UL  C26  C25  C24  111.55  3.000
 8UL  C26  C29  O31  117.20  3.000
 8UL  C26  C29  O32  116.74  3.000
 8UL  O31  C29  O32  126.04  3.000
 8UL  H11  C26  C27  107.40  3.000
 8UL  H11  C26  C29  106.39  3.000
 8UL  C27  C26  C29  113.03  3.000
 8UL  H11  C26  C25  107.57  3.000
 8UL  C27  C26  C25  108.36  3.000
 8UL  C29  C26  C25  113.75  3.000
 8UL  H13  C27  H12  106.89  3.000
 8UL  H13  C27  C28  108.17  3.000
 8UL  H12  C27  C28  109.00  3.000
 8UL  H13  C27  C26  110.86  3.000
 8UL  H12  C27  C26  109.62  3.000
 8UL  C28  C27  C26  112.14  3.000
 8UL  H15  C28  H14  107.06  3.000
 8UL  H15  C28  C27  108.11  3.000
 8UL  H14  C28  C27  109.30  3.000
 8UL  H15  C28  N23  109.15  3.000
 8UL  H14  C28  N23  110.96  3.000
 8UL  C27  C28  N23  112.08  3.000
 8UL  H16  C30  C19  122.51  3.000
 8UL  H16  C30  C18  118.63  3.000
 8UL  C19  C30  C18  118.84  3.000
 8UL  H17  C20  C16  117.66  3.000
 8UL  H17  C20  C19  119.66  3.000
 8UL  C16  C20  C19  122.67  3.000
 8UL  C20  C16  C17  119.43  3.000
 8UL  C17  C16  C4   122.47  3.000
 8UL  C20  C16  C4   118.00  3.000
 8UL  H20  C22  H19  107.10  3.000
 8UL  H20  C22  H18  108.45  3.000
 8UL  H19  C22  H18  107.26  3.000
 8UL  H20  C22  C14  111.50  3.000
 8UL  H19  C22  C14  109.62  3.000
 8UL  H18  C22  C14  112.67  3.000
 8UL  N9   C8   C3   180.00  3.000
 8UL  H22  N7   H21  115.58  3.000
 8UL  H22  N7   C2   118.99  3.000
 8UL  H21  N7   C2   119.58  3.000
 8UL  H25  C13  H24  108.30  3.000
 8UL  H25  C13  H23  107.37  3.000
 8UL  H24  C13  H23  107.96  3.000
 8UL  H25  C13  C10  110.64  3.000
 8UL  H24  C13  C10  111.36  3.000
 8UL  H23  C13  C10  111.06  3.000
 8UL  H26  N11  N12  119.24  3.000
 8UL  H26  N11  C10  126.54  3.000
 8UL  N12  N11  C10  114.22  3.000
 8UL  N11  N12  C6   102.57  3.000
 8UL  C6   O1   C2   116.01  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
 8UL  CONST_01  N12  N11  C10  C5      0.00   0.0  0
 8UL  CONST_02  N11  N12  C6   C5      0.00   0.0  0
 8UL  CONST_03  C10  N11  N12  C6      0.00   0.0  0
 8UL  CONST_04  N11  C10  C5   C6      0.00   0.0  0
 8UL  CONST_05  N12  C6   C5   C10     0.00   0.0  0
 8UL  CONST_06  C19  C20  C16  C17     0.00   0.0  0
 8UL  CONST_07  C19  C30  C18  C17     0.00   0.0  0
 8UL  CONST_08  C20  C19  C30  C18     0.00   0.0  0
 8UL  CONST_09  C20  C16  C17  C18     0.00   0.0  0
 8UL  CONST_10  C16  C20  C19  C30     0.00   0.0  0
 8UL  CONST_11  C16  C17  C18  C30     0.00   0.0  0
 8UL  CONST_12  C19  C20  C16  C4    180.00   0.0  0
 8UL  CONST_13  C18  C17  C16  C4    180.00   0.0  0
 8UL  CONST_14  N23  C19  C30  C18   180.00   0.0  0
 8UL  CONST_15  C16  C20  C19  N23   180.00   0.0  0
 8UL  CONST_16  C13  C10  C5   C4      0.00   0.0  0
 8UL  CONST_17  C13  C10  C5   C6    180.00   0.0  0
 8UL  CONST_18  F21  C18  C30  C19   180.00   0.0  0
 8UL  CONST_19  C16  C17  C18  F21   180.00   0.0  0
 8UL  CONST_20  N12  N11  C10  C13   180.00   0.0  0
 8UL  CONST_21  H17  C20  C16  C4      0.00   0.0  0
 8UL  CONST_22  H5   C17  C16  C4      0.00   0.0  0
 8UL  CONST_23  H26  N11  C10  C5    180.00   0.0  0
 8UL  CONST_24  H16  C30  C18  C17   180.00   0.0  0
 8UL  Var_01    N12  C6   O1   C2   -169.52  30.0  1
 8UL  Var_02    O1   C2   C3   C4     -7.24  30.0  1
 8UL  Var_03    C25  C24  N23  C19  -162.52  30.0  1
 8UL  Var_04    C27  C28  N23  C19   163.40  30.0  1
 8UL  Var_05    C26  C25  C24  N23   -55.26  30.0  1
 8UL  Var_06    C26  C27  C28  N23    54.35  30.0  1
 8UL  Var_07    C20  C19  N23  C24    40.00  30.0  2
 8UL  Var_08    H21  N7   C2   C3      5.58  30.0  2
 8UL  Var_09    H23  C13  C10  C5     59.59  30.0  2
 8UL  Var_10    H2   C15  C14  C4     75.30  30.0  3
 8UL  Var_11    H18  C22  C14  C4     60.38  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
 8UL  chir_01  C4   C16  C5   C3   positiv
 8UL  chir_02  C26  C29  C25  C27  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
 8UL  plan-1  C4   0.020
 8UL  plan-1  C17  0.020
 8UL  plan-1  C18  0.020
 8UL  plan-1  C19  0.020
 8UL  plan-1  N23  0.020
 8UL  plan-1  C30  0.020
 8UL  plan-1  F21  0.020
 8UL  plan-1  C20  0.020
 8UL  plan-1  C16  0.020
 8UL  plan-1  H5   0.020
 8UL  plan-1  H16  0.020
 8UL  plan-1  H17  0.020
 8UL  plan-2  C4   0.020
 8UL  plan-2  C5   0.020
 8UL  plan-2  C6   0.020
 8UL  plan-2  C10  0.020
 8UL  plan-2  C13  0.020
 8UL  plan-2  N11  0.020
 8UL  plan-2  N12  0.020
 8UL  plan-2  O1   0.020
 8UL  plan-2  H26  0.020
 8UL  plan-3  O32  0.020
 8UL  plan-3  C29  0.020
 8UL  plan-3  O31  0.020
 8UL  plan-3  C26  0.020

