# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 09:51:53 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  59  34  .  2022-07-25  2022-11-17
;
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  OH1   0  -0.596  -7.1822  -1.4870  -2.8260
 G6F  C48  C  C     0   0.552  -7.1297  -0.8684  -1.6502
 G6F  O55  O  O     0  -0.444  -8.0565  -0.2480  -1.1918
 G6F  C47  C  CH2   0  -0.574  -5.7937  -1.0485  -0.9841
 G6F  C46  C  CH2   0  -0.514  -5.6757  -0.3093   0.3448
 G6F  C42  C  CR6   0   0.147  -4.3365  -0.5641   0.9799
 G6F  C41  C  CR16  0  -0.368  -3.2512   0.2585   0.6985
 G6F  C43  C  CR16  0  -0.316  -4.1450  -1.6597   1.8178
 G6F  C44  C  CR16  0  -0.224  -2.8945  -1.9219   2.3591
 G6F  C45  C  CR16  0  -0.322  -1.8193  -1.0963   2.0685
 G6F  C34  C  CR6   0   0.102  -1.9875   0.0067   1.2315
 G6F  C20  C  CR6   0   0.122  -0.8467   0.8887   0.9132
 G6F  C19  C  CR16  0  -0.500  -1.0133   2.2733   0.8706
 G6F  C18  C  CR6   0   0.590   0.0810   3.0512   0.5680
 G6F  F35  F  F     0  -0.317  -0.0668   4.3862   0.5314
 G6F  C17  C  CR16  0  -0.528   1.3328   2.5252   0.3060
 G6F  C21  C  CR16  0  -0.358   0.4071   0.3474   0.6494
 G6F  C16  C  CR6   0   0.212   1.5071   1.1466   0.3470
 G6F  C4   C  CR6   0  -0.171   2.8334   0.4677  -0.0180
 G6F  C14  C  CH1   0  -0.214   4.0448   1.4470   0.0018
 G6F  C36  C  CH3   0  -0.678   4.3533   2.0080   1.3888
 G6F  C15  C  CH3   0  -0.662   5.3091   0.8138  -0.5692
 G6F  C3   C  CR6   0  -0.219   3.0737  -0.7211   0.9105
 G6F  C8   C  CSP   0   0.033   2.8937  -0.5505   2.2948
 G6F  N9   N  NS    0  -0.288   2.7257  -0.4378   3.4354
 G6F  C2   C  CR6   0   0.605   3.4350  -1.9796   0.4989
 G6F  N7   N  NH2   0  -0.835   3.8029  -2.9896   1.2987
 G6F  C5   C  CR56  0  -0.146   2.6753  -0.1238  -1.3873
 G6F  C10  C  CR5   0   0.368   2.2574   0.3770  -2.6084
 G6F  C13  C  CH3   0  -0.750   1.7589   1.7143  -3.0205
 G6F  N11  N  NR15  0  -0.491   2.3819  -0.6422  -3.4774
 G6F  N12  N  N     0  -0.295   2.8440  -1.7726  -2.9356
 G6F  C6   C  CR56  0   0.459   3.0141  -1.4394  -1.6837
 G6F  O1   O  O     0  -0.453   3.4898  -2.3412  -0.7921
 G6F  H1   H  HOH1  0   0.479  -8.0577  -1.3652  -3.2222
 G6F  H2   H  HCH2  0   0.288  -5.6262  -2.1205  -0.8412
 G6F  H3   H  HCH2  0   0.287  -5.0133  -0.7209  -1.6772
 G6F  H4   H  HCH2  0   0.255  -5.8138   0.7615   0.1836
 G6F  H5   H  HCH2  0   0.256  -6.4701  -0.6338   1.0192
 G6F  H6   H  HCR6  0   0.249  -3.3914   1.1014   0.0305
 G6F  H7   H  HCR6  0   0.250  -4.9795  -2.3109   2.0512
 G6F  H8   H  HCR6  0   0.257  -2.7584  -2.7688   3.0189
 G6F  H9   H  HCR6  0   0.252  -0.8523  -1.2954   2.5142
 G6F  H10  H  HCR6  0   0.275  -1.9679   2.7336   1.0922
 G6F  H11  H  HCR6  0   0.279   2.1396   3.2051   0.0693
 G6F  H12  H  HCR6  0   0.254   0.5236  -0.7292   0.6519
 G6F  H13  H  HCH1  0   0.233   3.7851   2.2800  -0.6609
 G6F  H14  H  HCH3  0   0.231   4.8261   1.2554   2.0214
 G6F  H15  H  HCH3  0   0.242   5.0550   2.8383   1.3006
 G6F  H16  H  HCH3  0   0.237   3.4738   2.3781   1.9145
 G6F  H17  H  HCH3  0   0.238   5.1896   0.4968  -1.6046
 G6F  H18  H  HCH3  0   0.239   6.1255   1.5369  -0.5430
 G6F  H19  H  HCH3  0   0.223   5.6245  -0.0505   0.0195
 G6F  H20  H  HNH2  0   0.419   3.7486  -2.8804   2.2974
 G6F  H21  H  HNH2  0   0.416   3.7275  -3.9353   0.9594
 G6F  H22  H  HCH3  0   0.261   2.5124   2.4848  -2.8586
 G6F  H23  H  HCH3  0   0.267   1.4947   1.7253  -4.0772
 G6F  H24  H  HCH3  0   0.264   0.8741   1.9947  -2.4502
 G6F  H25  H  HNR5  0   0.421   2.1631  -0.6224  -4.4609

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  1.388  0.020  1.388
 G6F  C44  C45  aromatic  1.386  0.020  1.386
 G6F  C43  C42  aromatic  1.393  0.020  1.393
 G6F  O55  C48  double    1.206  0.020  1.206
 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    1.504  0.020  1.504
 G6F  C42  C41  aromatic  1.391  0.020  1.391
 G6F  C13  C10  single    1.486  0.020  1.486
 G6F  C46  C47  single    1.525  0.020  1.525
 G6F  C10  C5   aromatic  1.384  0.020  1.384
 G6F  C48  O58  single    1.330  0.020  1.330
 G6F  C48  C47  single    1.504  0.020  1.504
 G6F  C34  C41  aromatic  1.394  0.020  1.394
 G6F  C34  C20  single    1.477  0.020  1.477
 G6F  C6   C5   aromatic  1.390  0.020  1.390
 G6F  C6   O1   single    1.355  0.020  1.355
 G6F  C5   C4   single    1.500  0.020  1.500
 G6F  C21  C20  aromatic  1.391  0.020  1.391
 G6F  C21  C16  aromatic  1.393  0.020  1.393
 G6F  C20  C19  aromatic  1.395  0.020  1.395
 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    1.527  0.020  1.527
 G6F  C16  C17  aromatic  1.390  0.020  1.390
 G6F  C15  C14  single    1.525  0.020  1.525
 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  O58  H1   single    0.850  0.020  0.980
 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  H1   O58  C48  109.81  3.000
 G6F  C47  C48  O55  125.18  3.000
 G6F  C47  C48  O58  111.78  3.000
 G6F  O55  C48  O58  123.04  3.000
 G6F  H3   C47  H2   105.48  3.000
 G6F  H3   C47  C46  110.59  3.000
 G6F  H2   C47  C46  110.43  3.000
 G6F  H3   C47  C48  108.50  3.000
 G6F  H2   C47  C48  108.13  3.000
 G6F  C46  C47  C48  113.37  3.000
 G6F  H5   C46  H4   106.90  3.000
 G6F  H5   C46  C42  109.69  3.000
 G6F  H4   C46  C42  109.95  3.000
 G6F  H5   C46  C47  109.75  3.000
 G6F  H4   C46  C47  109.69  3.000
 G6F  C42  C46  C47  110.78  3.000
 G6F  C43  C42  C41  118.68  3.000
 G6F  C41  C42  C46  120.62  3.000
 G6F  C43  C42  C46  120.65  3.000
 G6F  H6   C41  C34  119.53  3.000
 G6F  H6   C41  C42  118.91  3.000
 G6F  C34  C41  C42  121.54  3.000
 G6F  H7   C43  C44  119.76  3.000
 G6F  H7   C43  C42  119.76  3.000
 G6F  C44  C43  C42  120.48  3.000
 G6F  H8   C44  C45  119.75  3.000
 G6F  H8   C44  C43  119.94  3.000
 G6F  C45  C44  C43  120.31  3.000
 G6F  H9   C45  C34  120.00  3.000
 G6F  H9   C45  C44  119.78  3.000
 G6F  C34  C45  C44  120.21  3.000
 G6F  C20  C34  C45  120.56  3.000
 G6F  C20  C34  C41  120.65  3.000
 G6F  C45  C34  C41  118.78  3.000
 G6F  C21  C20  C19  119.21  3.000
 G6F  C19  C20  C34  120.47  3.000
 G6F  C21  C20  C34  120.32  3.000
 G6F  H10  C19  C18  120.38  3.000
 G6F  H10  C19  C20  121.39  3.000
 G6F  C18  C19  C20  118.21  3.000
 G6F  C17  C18  F35  118.18  3.000
 G6F  F35  C18  C19  118.69  3.000
 G6F  C17  C18  C19  123.13  3.000
 G6F  H11  C17  C16  122.44  3.000
 G6F  H11  C17  C18  118.54  3.000
 G6F  C16  C17  C18  119.01  3.000
 G6F  H12  C21  C16  119.08  3.000
 G6F  H12  C21  C20  118.91  3.000
 G6F  C16  C21  C20  121.99  3.000
 G6F  C4   C16  C21  118.72  3.000
 G6F  C4   C16  C17  122.70  3.000
 G6F  C21  C16  C17  118.45  3.000
 G6F  C5   C4   C3   105.34  3.000
 G6F  C3   C4   C14  111.05  3.000
 G6F  C5   C4   C14  109.97  3.000
 G6F  C3   C4   C16  109.62  3.000
 G6F  C14  C4   C16  113.02  3.000
 G6F  C5   C4   C16  107.49  3.000
 G6F  H13  C14  C15  106.60  3.000
 G6F  H13  C14  C36  108.53  3.000
 G6F  C15  C14  C36  108.97  3.000
 G6F  H13  C14  C4   106.61  3.000
 G6F  C36  C14  C4   113.54  3.000
 G6F  C15  C14  C4   112.27  3.000
 G6F  H16  C36  H15  107.45  3.000
 G6F  H16  C36  H14  107.73  3.000
 G6F  H15  C36  H14  107.05  3.000
 G6F  H16  C36  C14  113.57  3.000
 G6F  H15  C36  C14  109.64  3.000
 G6F  H14  C36  C14  111.14  3.000
 G6F  H19  C15  H18  107.19  3.000
 G6F  H19  C15  H17  108.28  3.000
 G6F  H18  C15  H17  107.32  3.000
 G6F  H19  C15  C14  111.48  3.000
 G6F  H18  C15  C14  109.65  3.000
 G6F  H17  C15  C14  112.69  3.000
 G6F  C2   C3   C8   116.11  3.000
 G6F  C8   C3   C4   118.93  3.000
 G6F  C2   C3   C4   124.94  3.000
 G6F  N9   C8   C3   180.00  3.000
 G6F  O1   C2   N7   111.10  3.000
 G6F  N7   C2   C3   125.77  3.000
 G6F  O1   C2   C3   123.12  3.000
 G6F  H21  N7   H20  115.60  3.000
 G6F  H21  N7   C2   119.07  3.000
 G6F  H20  N7   C2   119.73  3.000
 G6F  C6   C5   C10  103.17  3.000
 G6F  C6   C5   C4   122.82  3.000
 G6F  C10  C5   C4   133.98  3.000
 G6F  N11  C10  C13  122.27  3.000
 G6F  C13  C10  C5   132.20  3.000
 G6F  N11  C10  C5   105.53  3.000
 G6F  H24  C13  H23  107.95  3.000
 G6F  H24  C13  H22  107.57  3.000
 G6F  H23  C13  H22  107.74  3.000
 G6F  H24  C13  C10  111.04  3.000
 G6F  H23  C13  C10  111.08  3.000
 G6F  H22  C13  C10  111.30  3.000
 G6F  H25  N11  N12  119.18  3.000
 G6F  H25  N11  C10  126.55  3.000
 G6F  N12  N11  C10  114.27  3.000
 G6F  C6   N12  N11  102.58  3.000
 G6F  O1   C6   N12  120.44  3.000
 G6F  O1   C6   C5   125.11  3.000
 G6F  N12  C6   C5   114.44  3.000
 G6F  C6   O1   C2   116.08  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  CONST_43  H1   O58  C48  O55     0.00   0.0  0
 G6F  Var_01    O1   C2   C3   C4     -6.85  30.0  1
 G6F  Var_02    N12  C6   O1   C2   -169.97  30.0  1
 G6F  Var_03    C43  C42  C46  C47   -88.06  30.0  2
 G6F  Var_04    C2   C3   C8   N9    -49.11  30.0  1
 G6F  Var_05    H20  N7   C2   C3      5.60  30.0  2
 G6F  Var_06    H22  C13  C10  C5     61.63  30.0  2
 G6F  Var_07    C42  C46  C47  C48   178.20  30.0  2
 G6F  Var_08    H17  C15  C14  C4     60.03  30.0  3
 G6F  Var_09    H14  C36  C14  C4     74.16  30.0  3
 G6F  Var_10    C46  C47  C48  O58   177.84  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
 G6F  plan-4  H1   0.020

