# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 04:39:27 2020
#   Inital geometry file: a 136 line input string
#   Ligand name: 1-[3-[[2-fluoranyl-4-(1-methylpyrazol-4-yl)phenyl]amino]-1-[(3~{S})-oxolan-3-yl]-6,7-dihydro-4~{H}-pyrazolo[4,3-c]pyridin-5-yl]ethanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1cc(cn1)c2ccc(Nc3nn([C@H]4CCOC4)c5CCN(Cc35)C(C)=O)c(F)c2
#
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
 6XH  6XH  1-[3-[[2-fluoranyl-4-(1-methylpyrazol-4-yl)phenyl]amino]-1-[(3~{S})-oxolan-3-yl]-6,7-dihydro-4~{H}-pyrazolo[4,3-c]pyridin-5-yl]ethanone  ligand  56  31  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_6XH
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
 6XH  C7   C  CR5   0   0.467   3.4005   0.7633   0.3938
 6XH  C9   C  CR5   0   0.531   1.3805  -0.1019   0.4489
 6XH  C2   C  C     0   0.524   5.4706  -2.1659  -0.7339
 6XH  C6   C  CH2   0  -0.512   4.8797   0.9230   0.4015
 6XH  C1   C  CH3   0  -0.810   4.7320  -3.3064  -1.3938
 6XH  C12  C  CR15  0  -0.175   2.6488   3.1259   0.0272
 6XH  C14  C  CH2   0  -0.495   2.3086   3.5450  -1.4043
 6XH  C15  C  CH2   0  -0.151   0.8139   3.8318  -1.3281
 6XH  C17  C  CH2   0  -0.143   1.6801   3.9914   0.8298
 6XH  C19  C  CR6   0   0.185  -1.0097  -0.7650   0.3970
 6XH  C20  C  CR16  0  -0.317  -1.6092   0.4848   0.2132
 6XH  C21  C  CR16  0  -0.350  -2.9860   0.6023   0.0842
 6XH  C22  C  CR6   0   0.110  -3.8345  -0.5004   0.1361
 6XH  C23  C  CR16  0  -0.513  -3.2425  -1.7536   0.3255
 6XH  C24  C  CR6   0   0.484  -1.8814  -1.8591   0.4464
 6XH  C26  C  CR5   0  -0.121  -5.2814  -0.3652  -0.0001
 6XH  C27  C  CR15  0  -0.108  -6.0560   0.8127  -0.0352
 6XH  C30  C  CR15  0   0.006  -6.2252  -1.3691  -0.1245
 6XH  C32  C  CH2   0  -0.361   3.4691  -1.7403   0.6785
 6XH  C5   C  CH2   0  -0.330   5.4770  -0.3843   0.9296
 6XH  C8   C  CR5   0  -0.278   2.7484  -0.4401   0.5170
 6XH  F25  F  F     0  -0.323  -1.3365  -3.0810   0.6266
 6XH  N10  N  N     0  -0.349   1.2192   1.1972   0.2907
 6XH  N11  N  NR5   0  -0.356   2.4594   1.7127   0.2648
 6XH  N18  N  NH1   0  -0.792   0.3404  -0.9983   0.5327
 6XH  N28  N  N     0  -0.277  -7.3416   0.5480  -0.1674
 6XH  N29  N  NR5   0  -0.267  -7.4256  -0.7762  -0.2188
 6XH  N4   N  NT    0  -0.448   4.8584  -1.5389   0.2995
 6XH  O16  O  O     0  -0.498   0.5494   4.2200   0.0123
 6XH  O3   O  O     0  -0.501   6.5879  -1.8394  -1.1122
 6XH  H1   H  HCH2  0   0.267   5.2540   1.1344  -0.6041
 6XH  H2   H  HCH2  0   0.272   5.1960   1.7510   1.0398
 6XH  H3   H  HCH3  0   0.267   3.8453  -2.9536  -1.9234
 6XH  H4   H  HCH3  0   0.271   5.3907  -3.7808  -2.1164
 6XH  H5   H  HCH3  0   0.267   4.4078  -4.0585  -0.6743
 6XH  H13  H  HCR5  0   0.289   3.6820   3.3538   0.2858
 6XH  H6   H  HCH2  0   0.256   2.8668   4.4503  -1.6492
 6XH  H7   H  HCH2  0   0.265   2.5613   2.7843  -2.1422
 6XH  H8   H  HCH2  0   0.225   0.5148   4.6353  -2.0062
 6XH  H9   H  HCH2  0   0.210   0.2291   2.9426  -1.5791
 6XH  H10  H  HCH2  0   0.234   1.3780   3.5155   1.7648
 6XH  H11  H  HCH2  0   0.223   2.1709   4.9395   1.0769
 6XH  H12  H  HCR6  0   0.309  -0.9922   1.3692   0.1715
 6XH  H14  H  HCR6  0   0.245  -3.3931   1.5938  -0.0677
 6XH  H15  H  HCR6  0   0.268  -3.8390  -2.6558   0.3822
 6XH  H16  H  HCR5  0   0.255  -5.7238   1.8374   0.0382
 6XH  H17  H  HCR5  0   0.291  -6.1268  -2.4424  -0.1563
 6XH  H18  H  HCH3  0   0.260  -9.1388  -1.1601  -1.3534
 6XH  H19  H  HCH3  0   0.258  -8.5706  -2.4942  -0.3385
 6XH  H20  H  HCH3  0   0.261  -9.3886  -1.1113   0.4024
 6XH  H21  H  HCH2  0   0.263   3.4248  -2.0941   1.7144
 6XH  H22  H  HCH2  0   0.275   3.0174  -2.5193   0.0682
 6XH  H23  H  HCH2  0   0.274   6.5503  -0.4093   0.7680
 6XH  H24  H  HCH2  0   0.262   5.3040  -0.4548   2.0063
 6XH  H25  H  HNH1  0   0.409   0.6130  -1.9565   0.6714
 6XH  C31  C  CH3   0  -0.506  -8.7070  -1.4180  -0.3880

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
 6XH  N28  C27  aromatic  1.319  0.020  1.319
 6XH  N28  N29  aromatic  1.328  0.020  1.328
 6XH  C27  C26  aromatic  1.410  0.020  1.410
 6XH  F25  C24  single    1.350  0.020  1.350
 6XH  N29  C31  single    1.443  0.020  1.443
 6XH  N29  C30  aromatic  1.342  0.020  1.342
 6XH  C23  C24  aromatic  1.371  0.020  1.371
 6XH  C23  C22  aromatic  1.399  0.020  1.399
 6XH  C26  C30  aromatic  1.383  0.020  1.383
 6XH  C26  C22  single    1.460  0.020  1.460
 6XH  C24  C19  aromatic  1.400  0.020  1.400
 6XH  C22  C21  aromatic  1.392  0.020  1.392
 6XH  C19  N18  single    1.377  0.020  1.377
 6XH  C19  C20  aromatic  1.398  0.020  1.398
 6XH  C1   C2   single    1.511  0.020  1.511
 6XH  C21  C20  aromatic  1.388  0.020  1.388
 6XH  N18  C9   single    1.376  0.020  1.376
 6XH  C32  N4   single    1.454  0.020  1.454
 6XH  C32  C8   single    1.495  0.020  1.495
 6XH  C2   N4   single    1.355  0.020  1.355
 6XH  C2   O3   double    1.224  0.020  1.224
 6XH  C9   C8   aromatic  1.411  0.020  1.411
 6XH  C9   N10  aromatic  1.319  0.020  1.319
 6XH  N4   C5   single    1.454  0.020  1.454
 6XH  C8   C7   aromatic  1.374  0.020  1.374
 6XH  N10  N11  aromatic  1.343  0.020  1.343
 6XH  C5   C6   single    1.531  0.020  1.531
 6XH  C7   N11  aromatic  1.343  0.020  1.343
 6XH  C7   C6   single    1.488  0.020  1.488
 6XH  N11  C12  single    1.446  0.020  1.446
 6XH  C12  C17  single    1.527  0.020  1.527
 6XH  C12  C14  single    1.530  0.020  1.530
 6XH  C17  O16  single    1.414  0.020  1.414
 6XH  O16  C15  single    1.420  0.020  1.420
 6XH  C14  C15  single    1.524  0.020  1.524
 6XH  C6   H1   single    0.970  0.020  1.090
 6XH  C6   H2   single    0.970  0.020  1.090
 6XH  C1   H3   single    0.970  0.020  1.090
 6XH  C1   H4   single    0.970  0.020  1.090
 6XH  C1   H5   single    0.970  0.020  1.090
 6XH  C12  H13  single    0.970  0.020  1.090
 6XH  C14  H6   single    0.970  0.020  1.090
 6XH  C14  H7   single    0.970  0.020  1.090
 6XH  C15  H8   single    0.970  0.020  1.090
 6XH  C15  H9   single    0.970  0.020  1.090
 6XH  C17  H10  single    0.970  0.020  1.090
 6XH  C17  H11  single    0.970  0.020  1.090
 6XH  C20  H12  single    0.930  0.020  1.080
 6XH  C21  H14  single    0.930  0.020  1.080
 6XH  C23  H15  single    0.930  0.020  1.080
 6XH  C27  H16  single    0.930  0.020  1.080
 6XH  C30  H17  single    0.930  0.020  1.080
 6XH  C31  H18  single    0.970  0.020  1.090
 6XH  C31  H19  single    0.970  0.020  1.090
 6XH  C31  H20  single    0.970  0.020  1.090
 6XH  C32  H21  single    0.970  0.020  1.090
 6XH  C32  H22  single    0.970  0.020  1.090
 6XH  C5   H23  single    0.970  0.020  1.090
 6XH  C5   H24  single    0.970  0.020  1.090
 6XH  N18  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
 6XH  N11  C7   C8   107.17  3.000
 6XH  N11  C7   C6   128.41  3.000
 6XH  C8   C7   C6   124.43  3.000
 6XH  N18  C9   N10  123.84  3.000
 6XH  N10  C9   C8   111.14  3.000
 6XH  N18  C9   C8   125.03  3.000
 6XH  O3   C2   N4   121.65  3.000
 6XH  O3   C2   C1   120.85  3.000
 6XH  N4   C2   C1   117.49  3.000
 6XH  H2   C6   H1   106.96  3.000
 6XH  H2   C6   C5   109.43  3.000
 6XH  H1   C6   C5   110.40  3.000
 6XH  H2   C6   C7   111.86  3.000
 6XH  H1   C6   C7   110.87  3.000
 6XH  C5   C6   C7   107.33  3.000
 6XH  H5   C1   H4   108.54  3.000
 6XH  H5   C1   H3   107.56  3.000
 6XH  H4   C1   H3   108.11  3.000
 6XH  H5   C1   C2   112.21  3.000
 6XH  H4   C1   C2   108.88  3.000
 6XH  H3   C1   C2   111.42  3.000
 6XH  H13  C12  N11  106.85  3.000
 6XH  H13  C12  C17  111.00  3.000
 6XH  N11  C12  C17  112.62  3.000
 6XH  H13  C12  C14  112.08  3.000
 6XH  C17  C12  C14  101.27  3.000
 6XH  N11  C12  C14  113.11  3.000
 6XH  H7   C14  H6   107.97  3.000
 6XH  H7   C14  C15  113.13  3.000
 6XH  H6   C14  C15  110.90  3.000
 6XH  H7   C14  C12  113.01  3.000
 6XH  H6   C14  C12  108.87  3.000
 6XH  C15  C14  C12  102.88  3.000
 6XH  H9   C15  H8   108.01  3.000
 6XH  H9   C15  O16  109.84  3.000
 6XH  H8   C15  O16  109.49  3.000
 6XH  H9   C15  C14  111.10  3.000
 6XH  H8   C15  C14  112.06  3.000
 6XH  O16  C15  C14  106.34  3.000
 6XH  H11  C17  H10  107.94  3.000
 6XH  H11  C17  O16  110.40  3.000
 6XH  H10  C17  O16  110.15  3.000
 6XH  H11  C17  C12  108.95  3.000
 6XH  H10  C17  C12  112.25  3.000
 6XH  O16  C17  C12  107.16  3.000
 6XH  N18  C19  C24  118.34  3.000
 6XH  N18  C19  C20  125.79  3.000
 6XH  C24  C19  C20  115.87  3.000
 6XH  H12  C20  C21  119.62  3.000
 6XH  H12  C20  C19  119.51  3.000
 6XH  C21  C20  C19  120.88  3.000
 6XH  H14  C21  C22  120.09  3.000
 6XH  H14  C21  C20  117.63  3.000
 6XH  C22  C21  C20  122.28  3.000
 6XH  C26  C22  C23  121.00  3.000
 6XH  C26  C22  C21  121.83  3.000
 6XH  C23  C22  C21  117.17  3.000
 6XH  H15  C23  C24  118.56  3.000
 6XH  H15  C23  C22  121.36  3.000
 6XH  C24  C23  C22  120.08  3.000
 6XH  F25  C24  C23  118.84  3.000
 6XH  C23  C24  C19  123.72  3.000
 6XH  F25  C24  C19  117.44  3.000
 6XH  C30  C26  C27  103.24  3.000
 6XH  C30  C26  C22  128.13  3.000
 6XH  C27  C26  C22  128.62  3.000
 6XH  H16  C27  N28  119.81  3.000
 6XH  H16  C27  C26  128.46  3.000
 6XH  N28  C27  C26  111.73  3.000
 6XH  H17  C30  N29  121.28  3.000
 6XH  H17  C30  C26  131.50  3.000
 6XH  N29  C30  C26  107.22  3.000
 6XH  H22  C32  H21  106.40  3.000
 6XH  H22  C32  N4   110.47  3.000
 6XH  H21  C32  N4   109.26  3.000
 6XH  H22  C32  C8   111.22  3.000
 6XH  H21  C32  C8   111.32  3.000
 6XH  N4   C32  C8   108.17  3.000
 6XH  H24  C5   H23  107.56  3.000
 6XH  H24  C5   N4   107.97  3.000
 6XH  H23  C5   N4   109.75  3.000
 6XH  H24  C5   C6   109.46  3.000
 6XH  H23  C5   C6   110.73  3.000
 6XH  N4   C5   C6   111.26  3.000
 6XH  C32  C8   C9   132.92  3.000
 6XH  C9   C8   C7   104.23  3.000
 6XH  C32  C8   C7   122.85  3.000
 6XH  N11  N10  C9   105.51  3.000
 6XH  N10  N11  C12  119.95  3.000
 6XH  C12  N11  C7   127.96  3.000
 6XH  N10  N11  C7   111.95  3.000
 6XH  H25  N18  C19  116.15  3.000
 6XH  H25  N18  C9   115.11  3.000
 6XH  C19  N18  C9   128.68  3.000
 6XH  N29  N28  C27  105.41  3.000
 6XH  N28  N29  C31  120.28  3.000
 6XH  C31  N29  C30  127.29  3.000
 6XH  N28  N29  C30  112.41  3.000
 6XH  C5   N4   C32  113.81  3.000
 6XH  C5   N4   C2   120.39  3.000
 6XH  C32  N4   C2   124.50  3.000
 6XH  C17  O16  C15  110.65  3.000
 6XH  H20  C31  H19  108.96  3.000
 6XH  H20  C31  H18  109.20  3.000
 6XH  H19  C31  H18  108.97  3.000
 6XH  H20  C31  N29  110.23  3.000
 6XH  H19  C31  N29  108.90  3.000
 6XH  H18  C31  N29  110.54  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
 6XH  CONST_01  N10  C9   C8   C7      0.00   0.0  0
 6XH  CONST_02  C9   N10  N11  C7      0.00   0.0  0
 6XH  CONST_03  N11  C7   C8   C9      0.00   0.0  0
 6XH  CONST_04  C22  C23  C24  C19     0.00   0.0  0
 6XH  CONST_05  C22  C21  C20  C19     0.00   0.0  0
 6XH  CONST_06  C23  C24  C19  C20     0.00   0.0  0
 6XH  CONST_07  C23  C22  C21  C20     0.00   0.0  0
 6XH  CONST_08  C26  C22  C21  C20   180.00   0.0  0
 6XH  CONST_09  C24  C23  C22  C21     0.00   0.0  0
 6XH  CONST_10  C27  C26  C22  C21     0.00   0.0  0
 6XH  CONST_11  C30  C26  C22  C21   180.00   0.0  0
 6XH  CONST_12  C24  C19  C20  C21     0.00   0.0  0
 6XH  CONST_13  N28  C27  C26  C22   180.00   0.0  0
 6XH  CONST_14  N29  C30  C26  C22   180.00   0.0  0
 6XH  CONST_15  C27  C26  C22  C23   180.00   0.0  0
 6XH  CONST_16  C30  C26  C22  C23     0.00   0.0  0
 6XH  CONST_17  C26  C22  C23  C24   180.00   0.0  0
 6XH  CONST_18  N29  N28  C27  C26     0.00   0.0  0
 6XH  CONST_19  N28  N29  C30  C26     0.00   0.0  0
 6XH  CONST_20  C30  N29  N28  C27     0.00   0.0  0
 6XH  CONST_21  N29  C30  C26  C27     0.00   0.0  0
 6XH  CONST_22  N28  C27  C26  C30     0.00   0.0  0
 6XH  CONST_23  N11  N10  C9   C8      0.00   0.0  0
 6XH  CONST_24  N10  N11  C7   C8      0.00   0.0  0
 6XH  CONST_25  C12  N11  N10  C9    180.00   0.0  0
 6XH  CONST_26  C12  N11  C7   C6      0.00   0.0  0
 6XH  CONST_27  C8   C7   N11  C12   180.00   0.0  0
 6XH  CONST_28  N18  C9   C8   C7    180.00   0.0  0
 6XH  CONST_29  F25  C24  C19  C20   180.00   0.0  0
 6XH  CONST_30  N18  C19  C20  C21   180.00   0.0  0
 6XH  CONST_31  F25  C24  C23  C22   180.00   0.0  0
 6XH  CONST_32  N18  C19  C24  C23   180.00   0.0  0
 6XH  CONST_33  C31  N29  C30  C26   180.00   0.0  0
 6XH  CONST_34  C31  N29  N28  C27   180.00   0.0  0
 6XH  CONST_35  N18  C9   C8   C32     0.00   0.0  0
 6XH  CONST_36  N18  C9   N10  N11   180.00   0.0  0
 6XH  CONST_37  H15  C23  C24  C19   180.00   0.0  0
 6XH  CONST_38  H14  C21  C20  C19   180.00   0.0  0
 6XH  CONST_39  H16  C27  C26  C22     0.00   0.0  0
 6XH  CONST_40  H17  C30  C26  C22     0.00   0.0  0
 6XH  CONST_41  H12  C20  C21  C22   180.00   0.0  0
 6XH  CONST_42  C32  N4   C2   C1      0.00   0.0  0
 6XH  CONST_43  C5   N4   C2   C1    180.00   0.0  0
 6XH  CONST_44  O3   C2   N4   C32   180.00   0.0  0
 6XH  CONST_45  O3   C2   N4   C5      0.00   0.0  0
 6XH  Var_01    N4   C32  C8   C7    -16.03  30.0  1
 6XH  Var_02    N4   C5   C6   C7     45.93  30.0  1
 6XH  Var_03    C32  N4   C5   C6    -68.61  30.0  1
 6XH  Var_04    O16  C15  C14  C12    27.55  30.0  1
 6XH  Var_05    C8   C32  N4   C5     49.49  30.0  1
 6XH  Var_06    C8   C7   C6   C5    -14.64  30.0  1
 6XH  Var_07    C24  C19  N18  C9    176.30  30.0  2
 6XH  Var_08    C8   C9   N18  C19  -175.75  30.0  2
 6XH  Var_09    H10  C17  O16  C15  -134.81  30.0  1
 6XH  Var_10    H18  C31  N29  C30  -114.53  30.0  2
 6XH  Var_11    H3   C1   C2   N4     67.56  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
 6XH  chir_01  C12  N11  C17  C14  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
 6XH  plan-1  C22  0.020
 6XH  plan-1  C26  0.020
 6XH  plan-1  C27  0.020
 6XH  plan-1  C30  0.020
 6XH  plan-1  N28  0.020
 6XH  plan-1  N29  0.020
 6XH  plan-1  H16  0.020
 6XH  plan-1  H17  0.020
 6XH  plan-1  C31  0.020
 6XH  plan-2  C7   0.020
 6XH  plan-2  C9   0.020
 6XH  plan-2  C6   0.020
 6XH  plan-2  C12  0.020
 6XH  plan-2  C32  0.020
 6XH  plan-2  C8   0.020
 6XH  plan-2  N10  0.020
 6XH  plan-2  N11  0.020
 6XH  plan-2  N18  0.020
 6XH  plan-3  C19  0.020
 6XH  plan-3  C20  0.020
 6XH  plan-3  C21  0.020
 6XH  plan-3  C22  0.020
 6XH  plan-3  C23  0.020
 6XH  plan-3  C24  0.020
 6XH  plan-3  C26  0.020
 6XH  plan-3  F25  0.020
 6XH  plan-3  N18  0.020
 6XH  plan-3  H12  0.020
 6XH  plan-3  H14  0.020
 6XH  plan-3  H15  0.020
 6XH  plan-4  C2   0.020
 6XH  plan-4  C1   0.020
 6XH  plan-4  C32  0.020
 6XH  plan-4  C5   0.020
 6XH  plan-4  N4   0.020
 6XH  plan-4  O3   0.020

