# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 19:50:40 2020
#   Inital geometry file: a 153 line input string
#   Ligand name: 3-[3-[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]phenyl]propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@]1(c2cc(F)cc(c2)c3cccc(CCC(O)=O)c3)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
 G6F  G6F  '3-[3-[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]phenyl]propanoic acid'  ligand  58  34  .  2022-07-25  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_G6F
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
 G6F  O58  O  OC    -1  -0.629  -8.8559   0.1331  -0.4483
 G6F  C48  C  C      0   0.414  -8.0213   0.0630   0.4779
 G6F  O55  O  O      0  -0.606  -8.2262   0.3211   1.6798
 G6F  C47  C  CH2    0  -0.577  -6.6064  -0.3851   0.0684
 G6F  C46  C  CH2    0  -0.499  -5.6099  -0.5523   1.2132
 G6F  C42  C  C      0   0.161  -4.2672  -1.0011   0.7083
 G6F  C41  C  C1     0  -0.389  -3.2282  -0.0921   0.5416
 G6F  C43  C  C1     0  -0.319  -4.0451  -2.3311   0.3534
 G6F  C44  C  C1     0  -0.224  -2.8194  -2.7288  -0.1592
 G6F  C45  C  C1     0  -0.336  -1.7945  -1.8087  -0.3246
 G6F  C34  C  C      0   0.117  -1.9864  -0.4738   0.0303
 G6F  C20  C  C      0   0.133  -0.8991   0.5146  -0.1240
 G6F  C19  C  C1     0  -0.512  -1.1868   1.8395  -0.4573
 G6F  C18  C  C      0   0.596  -0.1405   2.7230  -0.5877
 G6F  F35  F  F      0  -0.317  -0.4114   3.9974  -0.9171
 G6F  C17  C  C1     0  -0.534   1.1819   2.3613  -0.4068
 G6F  C21  C  C1     0  -0.367   0.4287   0.1416   0.0642
 G6F  C16  C  C      0   0.215   1.4795   1.0456  -0.0731
 G6F  C4   C  CT     0  -0.169   2.9177   0.5319   0.0743
 G6F  C14  C  CH1    0  -0.216   3.9689   1.6732   0.2191
 G6F  C36  C  CH3    0  -0.677   3.8116   2.4976   1.4953
 G6F  C15  C  CH3    0  -0.662   5.3984   1.1452   0.1401
 G6F  C3   C  C      0  -0.220   2.9958  -0.4370   1.2532
 G6F  C8   C  CSP    0   0.033   2.4190  -0.0613   2.4795
 G6F  N9   N  NS     0  -0.287   1.9281   0.2152   3.4915
 G6F  C2   C  C      0   0.606   3.5744  -1.6810   1.2137
 G6F  N7   N  NH2    0  -0.835   3.7916  -2.4780   2.2686
 G6F  C5   C  CR5    0  -0.145   3.2270  -0.2939  -1.1397
 G6F  C10  C  CR5    0   0.369   3.1419  -0.0675  -2.5028
 G6F  C13  C  CH3    0  -0.749   2.6763   1.1009  -3.2935
 G6F  N11  N  NR15   0  -0.491   3.6071  -1.1878  -3.0840
 G6F  N12  N  N      0  -0.295   3.9890  -2.1352  -2.2231
 G6F  C6   C  CR5    0   0.458   3.7551  -1.5779  -1.0645
 G6F  O1   O  O2     0  -0.452   4.0291  -2.2426   0.0833
 G6F  H2   H  HCH2   0   0.227  -6.6877  -1.3256  -0.4874
 G6F  H3   H  HCH2   0   0.230  -6.2107   0.3366  -0.6549
 G6F  H4   H  HCH2   0   0.229  -5.5050   0.3914   1.7523
 G6F  H5   H  HCH2   0   0.231  -5.9979  -1.2780   1.9318
 G6F  H6   H  H      0   0.245  -3.3889   0.9383   0.8388
 G6F  H7   H  H      0   0.247  -4.8375  -3.0603   0.4778
 G6F  H8   H  H      0   0.254  -2.6598  -3.7626  -0.4378
 G6F  H9   H  H      0   0.249  -0.8520  -2.1323  -0.7480
 G6F  H10  H  H      0   0.275  -2.2018   2.1720  -0.6327
 G6F  H11  H  H      0   0.280   1.9468   3.1137  -0.5359
 G6F  H12  H  H      0   0.251   0.6524  -0.8808   0.3405
 G6F  H13  H  HCH1   0   0.235   3.8320   2.3395  -0.6397
 G6F  H14  H  HCH3   0   0.230   4.1505   1.9414   2.3701
 G6F  H15  H  HCH3   0   0.241   4.4297   3.3943   1.4289
 G6F  H16  H  HCH3   0   0.237   2.7875   2.8194   1.6828
 G6F  H17  H  HCH3   0   0.238   5.6235   0.6916  -0.8247
 G6F  H18  H  HCH3   0   0.238   6.1024   1.9653   0.2866
 G6F  H19  H  HCH3   0   0.223   5.5943   0.4057   0.9200
 G6F  H20  H  HNH2   0   0.419   3.4462  -2.2101   3.1750
 G6F  H21  H  HNH2   0   0.416   3.8978  -3.4689   2.1192
 G6F  H22  H  HCH3   0   0.262   3.3441   1.9538  -3.1691
 G6F  H23  H  HCH3   0   0.266   2.6378   0.8645  -4.3561
 G6F  H24  H  HCH3   0   0.264   1.6807   1.4125  -2.9806
 G6F  H25  H  HNR5   0   0.421   3.6769  -1.3656  -4.0735

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
 G6F  C44  C43  aromatic  1.387  0.020  1.387
 G6F  C44  C45  aromatic  1.387  0.020  1.387
 G6F  C43  C42  aromatic  1.394  0.020  1.394
 G6F  O55  C48  deloc     1.246  0.020  1.246
 G6F  N11  N12  aromatic  1.336  0.020  1.336
 G6F  N11  C10  aromatic  1.345  0.020  1.345
 G6F  C45  C34  aromatic  1.395  0.020  1.395
 G6F  N12  C6   aromatic  1.307  0.020  1.307
 G6F  C42  C46  single    1.503  0.020  1.503
 G6F  C42  C41  aromatic  1.391  0.020  1.391
 G6F  C13  C10  single    1.486  0.020  1.486
 G6F  C46  C47  single    1.527  0.020  1.527
 G6F  C10  C5   aromatic  1.384  0.020  1.384
 G6F  C48  O58  deloc     1.249  0.020  1.249
 G6F  C48  C47  single    1.540  0.020  1.540
 G6F  C34  C41  aromatic  1.396  0.020  1.396
 G6F  C34  C20  single    1.478  0.020  1.478
 G6F  C6   C5   aromatic  1.390  0.020  1.390
 G6F  C6   O1   single    1.354  0.020  1.354
 G6F  C5   C4   single    1.500  0.020  1.500
 G6F  C21  C20  aromatic  1.392  0.020  1.392
 G6F  C21  C16  aromatic  1.393  0.020  1.393
 G6F  C20  C19  aromatic  1.396  0.020  1.396
 G6F  O1   C2   single    1.342  0.020  1.342
 G6F  C4   C16  single    1.534  0.020  1.534
 G6F  C4   C14  single    1.558  0.020  1.558
 G6F  C4   C3   single    1.528  0.020  1.528
 G6F  C16  C17  aromatic  1.390  0.020  1.390
 G6F  C15  C14  single    1.526  0.020  1.526
 G6F  C19  C18  aromatic  1.376  0.020  1.376
 G6F  C2   C3   double    1.373  0.020  1.373
 G6F  C2   N7   single    1.340  0.020  1.340
 G6F  C36  C14  single    1.528  0.020  1.528
 G6F  C3   C8   single    1.406  0.020  1.406
 G6F  C17  C18  aromatic  1.383  0.020  1.383
 G6F  C18  F35  single    1.344  0.020  1.344
 G6F  C8   N9   triple    1.158  0.020  1.158
 G6F  C47  H2   single    0.970  0.020  1.090
 G6F  C47  H3   single    0.970  0.020  1.090
 G6F  C46  H4   single    0.970  0.020  1.090
 G6F  C46  H5   single    0.970  0.020  1.090
 G6F  C41  H6   single    0.930  0.020  1.080
 G6F  C43  H7   single    0.930  0.020  1.080
 G6F  C44  H8   single    0.930  0.020  1.080
 G6F  C45  H9   single    0.930  0.020  1.080
 G6F  C19  H10  single    0.930  0.020  1.080
 G6F  C17  H11  single    0.930  0.020  1.080
 G6F  C21  H12  single    0.930  0.020  1.080
 G6F  C14  H13  single    0.970  0.020  1.090
 G6F  C36  H14  single    0.970  0.020  1.090
 G6F  C36  H15  single    0.970  0.020  1.090
 G6F  C36  H16  single    0.970  0.020  1.090
 G6F  C15  H17  single    0.970  0.020  1.090
 G6F  C15  H18  single    0.970  0.020  1.090
 G6F  C15  H19  single    0.970  0.020  1.090
 G6F  N7   H20  single    0.890  0.020  1.040
 G6F  N7   H21  single    0.890  0.020  1.040
 G6F  C13  H22  single    0.970  0.020  1.090
 G6F  C13  H23  single    0.970  0.020  1.090
 G6F  C13  H24  single    0.970  0.020  1.090
 G6F  N11  H25  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
 G6F  C47  C48  O55  117.90  3.000
 G6F  C47  C48  O58  115.68  3.000
 G6F  O55  C48  O58  126.42  3.000
 G6F  H3   C47  H2   104.91  3.000
 G6F  H3   C47  C46  109.35  3.000
 G6F  H2   C47  C46  109.56  3.000
 G6F  H3   C47  C48  108.41  3.000
 G6F  H2   C47  C48  108.46  3.000
 G6F  C46  C47  C48  115.61  3.000
 G6F  H5   C46  H4   106.47  3.000
 G6F  H5   C46  C42  109.87  3.000
 G6F  H4   C46  C42  109.76  3.000
 G6F  H5   C46  C47  109.52  3.000
 G6F  H4   C46  C47  109.77  3.000
 G6F  C42  C46  C47  111.34  3.000
 G6F  C43  C42  C41  118.30  3.000
 G6F  C41  C42  C46  120.83  3.000
 G6F  C43  C42  C46  120.84  3.000
 G6F  H6   C41  C34  119.47  3.000
 G6F  H6   C41  C42  118.53  3.000
 G6F  C34  C41  C42  121.99  3.000
 G6F  H7   C43  C44  119.71  3.000
 G6F  H7   C43  C42  119.74  3.000
 G6F  C44  C43  C42  120.56  3.000
 G6F  H8   C44  C45  119.59  3.000
 G6F  H8   C44  C43  119.96  3.000
 G6F  C45  C44  C43  120.45  3.000
 G6F  H9   C45  C34  120.35  3.000
 G6F  H9   C45  C44  119.45  3.000
 G6F  C34  C45  C44  120.19  3.000
 G6F  C20  C34  C45  120.83  3.000
 G6F  C20  C34  C41  120.66  3.000
 G6F  C45  C34  C41  118.51  3.000
 G6F  C21  C20  C19  118.89  3.000
 G6F  C19  C20  C34  120.53  3.000
 G6F  C21  C20  C34  120.57  3.000
 G6F  H10  C19  C18  120.04  3.000
 G6F  H10  C19  C20  121.56  3.000
 G6F  C18  C19  C20  118.38  3.000
 G6F  C17  C18  F35  118.22  3.000
 G6F  F35  C18  C19  118.62  3.000
 G6F  C17  C18  C19  123.16  3.000
 G6F  H11  C17  C16  122.44  3.000
 G6F  H11  C17  C18  118.63  3.000
 G6F  C16  C17  C18  118.93  3.000
 G6F  H12  C21  C16  118.83  3.000
 G6F  H12  C21  C20  119.00  3.000
 G6F  C16  C21  C20  122.17  3.000
 G6F  C4   C16  C21  118.71  3.000
 G6F  C4   C16  C17  122.74  3.000
 G6F  C21  C16  C17  118.47  3.000
 G6F  C5   C4   C3   105.35  3.000
 G6F  C3   C4   C14  110.99  3.000
 G6F  C5   C4   C14  109.83  3.000
 G6F  C3   C4   C16  109.53  3.000
 G6F  C14  C4   C16  113.33  3.000
 G6F  C5   C4   C16  107.44  3.000
 G6F  H13  C14  C15  106.68  3.000
 G6F  H13  C14  C36  108.28  3.000
 G6F  C15  C14  C36  109.05  3.000
 G6F  H13  C14  C4   106.76  3.000
 G6F  C36  C14  C4   113.79  3.000
 G6F  C15  C14  C4   111.94  3.000
 G6F  H16  C36  H15  107.47  3.000
 G6F  H16  C36  H14  107.73  3.000
 G6F  H15  C36  H14  106.97  3.000
 G6F  H16  C36  C14  113.58  3.000
 G6F  H15  C36  C14  109.54  3.000
 G6F  H14  C36  C14  111.28  3.000
 G6F  H19  C15  H18  107.30  3.000
 G6F  H19  C15  H17  108.25  3.000
 G6F  H18  C15  H17  107.37  3.000
 G6F  H19  C15  C14  111.43  3.000
 G6F  H18  C15  C14  109.73  3.000
 G6F  H17  C15  C14  112.54  3.000
 G6F  C2   C3   C8   116.11  3.000
 G6F  C8   C3   C4   118.85  3.000
 G6F  C2   C3   C4   125.04  3.000
 G6F  N9   C8   C3   180.00  3.000
 G6F  O1   C2   N7   111.06  3.000
 G6F  N7   C2   C3   125.79  3.000
 G6F  O1   C2   C3   123.12  3.000
 G6F  H21  N7   H20  115.56  3.000
 G6F  H21  N7   C2   119.03  3.000
 G6F  H20  N7   C2   119.68  3.000
 G6F  C6   C5   C10  103.16  3.000
 G6F  C6   C5   C4   122.87  3.000
 G6F  C10  C5   C4   133.95  3.000
 G6F  N11  C10  C13  122.24  3.000
 G6F  C13  C10  C5   132.22  3.000
 G6F  N11  C10  C5   105.55  3.000
 G6F  H24  C13  H23  108.06  3.000
 G6F  H24  C13  H22  107.66  3.000
 G6F  H23  C13  H22  107.62  3.000
 G6F  H24  C13  C10  111.01  3.000
 G6F  H23  C13  C10  111.07  3.000
 G6F  H22  C13  C10  111.25  3.000
 G6F  H25  N11  N12  119.20  3.000
 G6F  H25  N11  C10  126.53  3.000
 G6F  N12  N11  C10  114.27  3.000
 G6F  C6   N12  N11  102.58  3.000
 G6F  O1   C6   N12  120.39  3.000
 G6F  O1   C6   C5   125.16  3.000
 G6F  N12  C6   C5   114.45  3.000
 G6F  C6   O1   C2   116.11  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
 G6F  CONST_01  C45  C44  C43  C42     0.00   0.0  0
 G6F  CONST_02  C45  C34  C41  C42     0.00   0.0  0
 G6F  CONST_03  C20  C34  C41  C42   180.00   0.0  0
 G6F  CONST_04  C44  C43  C42  C41     0.00   0.0  0
 G6F  CONST_05  C44  C45  C34  C41     0.00   0.0  0
 G6F  CONST_08  C34  C45  C44  C43     0.00   0.0  0
 G6F  CONST_09  C34  C41  C42  C43     0.00   0.0  0
 G6F  CONST_10  C20  C34  C45  C44   180.00   0.0  0
 G6F  CONST_13  C16  C21  C20  C34   180.00   0.0  0
 G6F  CONST_14  C18  C19  C20  C34   180.00   0.0  0
 G6F  CONST_15  C17  C16  C21  C20     0.00   0.0  0
 G6F  CONST_16  C17  C18  C19  C20     0.00   0.0  0
 G6F  CONST_17  C16  C21  C20  C19     0.00   0.0  0
 G6F  CONST_18  C16  C17  C18  C19     0.00   0.0  0
 G6F  CONST_19  C21  C20  C19  C18     0.00   0.0  0
 G6F  CONST_20  C21  C16  C17  C18     0.00   0.0  0
 G6F  CONST_21  N12  N11  C10  C5      0.00   0.0  0
 G6F  CONST_22  N11  N12  C6   C5      0.00   0.0  0
 G6F  CONST_23  C6   N12  N11  C10     0.00   0.0  0
 G6F  CONST_24  N12  C6   C5   C10     0.00   0.0  0
 G6F  CONST_25  C6   C5   C10  N11     0.00   0.0  0
 G6F  CONST_26  C4   C16  C21  C20   180.00   0.0  0
 G6F  CONST_27  C4   C16  C17  C18   180.00   0.0  0
 G6F  CONST_28  C44  C43  C42  C46   180.00   0.0  0
 G6F  CONST_29  C34  C41  C42  C46   180.00   0.0  0
 G6F  CONST_30  F35  C18  C19  C20   180.00   0.0  0
 G6F  CONST_31  C16  C17  C18  F35   180.00   0.0  0
 G6F  CONST_32  C13  C10  C5   C4      0.00   0.0  0
 G6F  CONST_33  N12  N11  C10  C13   180.00   0.0  0
 G6F  CONST_34  C6   C5   C10  C13   180.00   0.0  0
 G6F  CONST_35  H8   C44  C43  C42   180.00   0.0  0
 G6F  CONST_36  H7   C43  C42  C41   180.00   0.0  0
 G6F  CONST_37  H9   C45  C34  C41   180.00   0.0  0
 G6F  CONST_38  H6   C41  C42  C43   180.00   0.0  0
 G6F  CONST_39  H12  C21  C20  C34     0.00   0.0  0
 G6F  CONST_40  H10  C19  C20  C34     0.00   0.0  0
 G6F  CONST_41  H11  C17  C18  C19   180.00   0.0  0
 G6F  CONST_42  H25  N11  C10  C5    180.00   0.0  0
 G6F  Var_01    O1   C2   C3   C4     -6.68  30.0  1
 G6F  Var_02    N12  C6   O1   C2   -170.33  30.0  1
 G6F  Var_03    C43  C42  C46  C47   -77.81  30.0  2
 G6F  Var_04    C2   C3   C8   N9    -46.01  30.0  2
 G6F  Var_05    H20  N7   C2   C3      5.52  30.0  2
 G6F  Var_06    H22  C13  C10  C5     67.36  30.0  2
 G6F  Var_07    C42  C46  C47  C48   179.55  30.0  1
 G6F  Var_08    H17  C15  C14  C4     62.84  30.0  3
 G6F  Var_09    H14  C36  C14  C4     73.94  30.0  3
 G6F  Var_10    C46  C47  C48  O58  -176.43  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
 G6F  chir_01  C4  C16  C5  C3  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
 G6F  plan-1  C46  0.020
 G6F  plan-1  C42  0.020
 G6F  plan-1  C41  0.020
 G6F  plan-1  C43  0.020
 G6F  plan-1  C44  0.020
 G6F  plan-1  C45  0.020
 G6F  plan-1  C34  0.020
 G6F  plan-1  C20  0.020
 G6F  plan-1  H6   0.020
 G6F  plan-1  H7   0.020
 G6F  plan-1  H8   0.020
 G6F  plan-1  H9   0.020
 G6F  plan-2  C34  0.020
 G6F  plan-2  C20  0.020
 G6F  plan-2  C19  0.020
 G6F  plan-2  C18  0.020
 G6F  plan-2  F35  0.020
 G6F  plan-2  C17  0.020
 G6F  plan-2  C21  0.020
 G6F  plan-2  C16  0.020
 G6F  plan-2  C4   0.020
 G6F  plan-2  H10  0.020
 G6F  plan-2  H11  0.020
 G6F  plan-2  H12  0.020
 G6F  plan-3  C4   0.020
 G6F  plan-3  C5   0.020
 G6F  plan-3  C10  0.020
 G6F  plan-3  C13  0.020
 G6F  plan-3  N11  0.020
 G6F  plan-3  N12  0.020
 G6F  plan-3  C6   0.020
 G6F  plan-3  O1   0.020
 G6F  plan-3  H25  0.020
 G6F  plan-4  O58  0.020
 G6F  plan-4  C48  0.020
 G6F  plan-4  O55  0.020
 G6F  plan-4  C47  0.020

