# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 12:11:57 2020
#   Inital geometry file: a 132 line input string
#   Ligand name: [2-chloro-5-(hydroxymethyl)phenyl]{5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}methanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCc1ccc(Cl)c(c1)C(=O)c2c[nH]c3ncc(cc23)c4cnn(c4)C5CCNCC5
#
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
 2K0  2K0  '[2-chloro-5-(hydroxymethyl)phenyl]{5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}methanone'  ligand  53  31  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_2K0
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
 2K0  C1   C   CR16  0  -0.184   6.3048  -0.2491   1.8953
 2K0  C2   C   CR6   0  -0.116   4.9239  -0.2069   1.8051
 2K0  C3   C   CR6   0   0.030   4.2996   0.2698   0.6594
 2K0  C7   C   C     0   0.319   2.8058   0.3727   0.5661
 2K0  C8   C   CR5   0  -0.201   2.1429  -0.5048  -0.3663
 2K0  C9   C   CR15  0   0.035   2.7340  -1.4971  -1.1266
 2K0  C10  C   CR56  0   0.463   0.5688  -1.5828  -1.6091
 2K0  C11  C   CR56  0   0.071   0.7386  -0.5520  -0.6681
 2K0  C12  C   CR16  0  -0.321  -0.4028   0.1282  -0.2622
 2K0  C13  C   CR6   0  -0.001  -1.6217  -0.2438  -0.8216
 2K0  C14  C   CR16  0  -0.138  -1.6363  -1.2872  -1.7663
 2K0  C15  C   CR5   0  -0.161  -2.8599   0.4346  -0.4510
 2K0  C16  C   CR15  0  -0.092  -3.0130   1.7177   0.1104
 2K0  C19  C   CH2   0  -0.422  -6.8290   0.4919   1.4221
 2K0  C20  C   CH2   0  -0.300  -8.3469   0.5204   1.5360
 2K0  C21  C   CH2   0  -0.296  -8.6039   0.1387  -0.8233
 2K0  C22  C   CH2   0  -0.456  -7.0959   0.0786  -1.0315
 2K0  CL   CL  CL    0  -0.124   3.9756  -0.7973   3.1299
 2K0  C4   C   CR16  0  -0.328   5.0852   0.7056  -0.4019
 2K0  C5   C   CR6   0   0.083   6.4739   0.6869  -0.3278
 2K0  C6   C   CH2   0  -0.195   7.3207   1.1316  -1.4878
 2K0  O    O   OH1   0  -0.665   6.6842   2.1893  -2.1612
 2K0  C    C   CR16  0  -0.311   7.0697   0.2085   0.8336
 2K0  O1   O   O     0  -0.394   2.2049   1.1757   1.2571
 2K0  N1   N   N     0  -0.408  -0.5682  -1.9611  -2.1589
 2K0  N    N   NR15  0  -0.657   1.8020  -2.1312  -1.8591
 2K0  C17  C   CR15  0   0.029  -4.1598  -0.0200  -0.5780
 2K0  N3   N   NR5   0  -0.291  -4.9652   0.9550  -0.1258
 2K0  N2   N   N     0  -0.278  -4.2832   2.0140   0.3003
 2K0  C18  C   CH1   0  -0.069  -6.4124   0.9384   0.0231
 2K0  N4   N   NH1   0  -0.595  -8.9369  -0.3218   0.5117
 2K0  H1   H   HCR6  0   0.284   6.7821  -0.6275   2.7887
 2K0  H2   H   HCR5  0   0.312   3.7696  -1.7929  -1.1808
 2K0  H3   H   HCR6  0   0.258  -0.3482   0.9155   0.4768
 2K0  H4   H   HCR6  0   0.258  -2.5739  -1.5753  -2.2292
 2K0  H5   H   HCR5  0   0.259  -2.2448   2.4350   0.3599
 2K0  H7   H   HCH2  0   0.229  -6.4620  -0.5222   1.6053
 2K0  H8   H   HCH2  0   0.241  -8.6498   0.1527   2.5176
 2K0  H9   H   HCH2  0   0.194  -8.6850   1.5678   1.4687
 2K0  H10  H   HCH2  0   0.195  -8.9486   1.1678  -1.0175
 2K0  H11  H   HCH2  0   0.242  -9.0970  -0.5037  -1.5545
 2K0  H12  H   HCH2  0   0.231  -6.7771  -0.9637  -0.9458
 2K0  H13  H   HCH2  0   0.253  -6.8403   0.4261  -2.0344
 2K0  H14  H   HCR6  0   0.269   4.5962   1.0768  -1.2937
 2K0  H15  H   HCH2  0   0.217   8.3119   1.4207  -1.1163
 2K0  H16  H   HCH2  0   0.228   7.4773   0.2724  -2.1529
 2K0  H17  H   HOH1  0   0.462   7.1190   2.3081  -3.0104
 2K0  H18  H   HCR6  0   0.267   8.1492   0.1889   0.9204
 2K0  H19  H   HNR5  0   0.426   1.9812  -2.8965  -2.4913
 2K0  H20  H   HCR5  0   0.293  -4.5448  -0.9575  -0.9443
 2K0  H21  H   HCH1  0   0.258  -6.7284   1.9753  -0.1227
 2K0  H22  H   HNH1  0   0.355  -9.9420  -0.3355   0.6237
 2K0  H6   H   HCH2  0   0.245  -6.3859   1.1471   2.1745

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
 2K0  N1   C14  aromatic  1.323  0.020  1.323
 2K0  N1   C10  aromatic  1.318  0.020  1.318
 2K0  C14  C13  aromatic  1.408  0.020  1.408
 2K0  C16  N2   aromatic  1.318  0.020  1.318
 2K0  C16  C15  aromatic  1.409  0.020  1.409
 2K0  N2   N3   aromatic  1.330  0.020  1.330
 2K0  C10  N    aromatic  1.373  0.020  1.373
 2K0  C10  C11  aromatic  1.406  0.020  1.406
 2K0  C15  C13  single    1.460  0.020  1.460
 2K0  C15  C17  aromatic  1.383  0.020  1.383
 2K0  C13  C12  aromatic  1.392  0.020  1.392
 2K0  N    C9   aromatic  1.344  0.020  1.344
 2K0  N3   C17  aromatic  1.343  0.020  1.343
 2K0  N3   C18  single    1.455  0.020  1.455
 2K0  C22  C18  single    1.523  0.020  1.523
 2K0  C22  C21  single    1.523  0.020  1.523
 2K0  C11  C12  aromatic  1.389  0.020  1.389
 2K0  C11  C8   aromatic  1.437  0.020  1.437
 2K0  C9   C8   aromatic  1.383  0.020  1.383
 2K0  C19  C18  single    1.527  0.020  1.527
 2K0  C19  C20  single    1.522  0.020  1.522
 2K0  N4   C21  single    1.451  0.020  1.451
 2K0  N4   C20  single    1.451  0.020  1.451
 2K0  C8   C7   single    1.442  0.020  1.442
 2K0  C7   O1   double    1.218  0.020  1.218
 2K0  C7   C3   single    1.500  0.020  1.500
 2K0  CL   C2   single    1.733  0.020  1.733
 2K0  C3   C2   aromatic  1.389  0.020  1.389
 2K0  C3   C4   aromatic  1.390  0.020  1.390
 2K0  C2   C1   aromatic  1.384  0.020  1.384
 2K0  C4   C5   aromatic  1.391  0.020  1.391
 2K0  C1   C    aromatic  1.386  0.020  1.386
 2K0  C5   C    aromatic  1.390  0.020  1.390
 2K0  C5   C6   single    1.503  0.020  1.503
 2K0  O    C6   single    1.406  0.020  1.406
 2K0  C1   H1   single    0.930  0.020  1.080
 2K0  C9   H2   single    0.930  0.020  1.080
 2K0  C12  H3   single    0.930  0.020  1.080
 2K0  C14  H4   single    0.930  0.020  1.080
 2K0  C16  H5   single    0.930  0.020  1.080
 2K0  C19  H6   single    0.970  0.020  1.090
 2K0  C19  H7   single    0.970  0.020  1.090
 2K0  C20  H8   single    0.970  0.020  1.090
 2K0  C20  H9   single    0.970  0.020  1.090
 2K0  C21  H10  single    0.970  0.020  1.090
 2K0  C21  H11  single    0.970  0.020  1.090
 2K0  C22  H12  single    0.970  0.020  1.090
 2K0  C22  H13  single    0.970  0.020  1.090
 2K0  C4   H14  single    0.930  0.020  1.080
 2K0  C6   H15  single    0.970  0.020  1.090
 2K0  C6   H16  single    0.970  0.020  1.090
 2K0  O    H17  single    0.850  0.020  0.980
 2K0  C    H18  single    0.930  0.020  1.080
 2K0  N    H19  single    0.860  0.020  1.020
 2K0  C17  H20  single    0.930  0.020  1.080
 2K0  C18  H21  single    0.970  0.020  1.090
 2K0  N4   H22  single    0.890  0.020  1.040

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
 2K0  H1   C1   C    120.31  3.000
 2K0  H1   C1   C2   120.32  3.000
 2K0  C    C1   C2   119.37  3.000
 2K0  CL   C2   C3   120.10  3.000
 2K0  C3   C2   C1   120.83  3.000
 2K0  CL   C2   C1   119.05  3.000
 2K0  C4   C3   C7   119.58  3.000
 2K0  C4   C3   C2   118.89  3.000
 2K0  C7   C3   C2   121.48  3.000
 2K0  O1   C7   C8   122.77  3.000
 2K0  O1   C7   C3   120.08  3.000
 2K0  C8   C7   C3   117.14  3.000
 2K0  C11  C8   C9   106.18  3.000
 2K0  C9   C8   C7   126.57  3.000
 2K0  C11  C8   C7   127.23  3.000
 2K0  H2   C9   N    120.60  3.000
 2K0  H2   C9   C8   129.42  3.000
 2K0  N    C9   C8   109.98  3.000
 2K0  N    C10  N1   125.75  3.000
 2K0  N    C10  C11  107.84  3.000
 2K0  N1   C10  C11  126.41  3.000
 2K0  C12  C11  C10  117.08  3.000
 2K0  C12  C11  C8   136.50  3.000
 2K0  C10  C11  C8   106.42  3.000
 2K0  H3   C12  C13  120.90  3.000
 2K0  H3   C12  C11  120.98  3.000
 2K0  C13  C12  C11  118.11  3.000
 2K0  C15  C13  C14  120.40  3.000
 2K0  C15  C13  C12  121.11  3.000
 2K0  C14  C13  C12  118.49  3.000
 2K0  H4   C14  N1   115.85  3.000
 2K0  H4   C14  C13  119.49  3.000
 2K0  N1   C14  C13  124.65  3.000
 2K0  C17  C15  C16  103.52  3.000
 2K0  C17  C15  C13  128.41  3.000
 2K0  C16  C15  C13  128.07  3.000
 2K0  H5   C16  N2   120.19  3.000
 2K0  H5   C16  C15  128.28  3.000
 2K0  N2   C16  C15  111.52  3.000
 2K0  H7   C19  H6   107.75  3.000
 2K0  H7   C19  C18  109.46  3.000
 2K0  H6   C19  C18  110.20  3.000
 2K0  H7   C19  C20  109.84  3.000
 2K0  H6   C19  C20  109.99  3.000
 2K0  C18  C19  C20  109.58  3.000
 2K0  H9   C20  H8   106.85  3.000
 2K0  H9   C20  N4   112.55  3.000
 2K0  H8   C20  N4   109.06  3.000
 2K0  H9   C20  C19  108.60  3.000
 2K0  H8   C20  C19  109.74  3.000
 2K0  N4   C20  C19  109.98  3.000
 2K0  H11  C21  H10  106.87  3.000
 2K0  H11  C21  N4   109.03  3.000
 2K0  H10  C21  N4   112.74  3.000
 2K0  H11  C21  C22  109.42  3.000
 2K0  H10  C21  C22  108.80  3.000
 2K0  N4   C21  C22  109.90  3.000
 2K0  H13  C22  H12  107.89  3.000
 2K0  H13  C22  C18  110.57  3.000
 2K0  H12  C22  C18  110.68  3.000
 2K0  H13  C22  C21  110.16  3.000
 2K0  H12  C22  C21  108.40  3.000
 2K0  C18  C22  C21  109.11  3.000
 2K0  H14  C4   C5   119.97  3.000
 2K0  H14  C4   C3   118.75  3.000
 2K0  C5   C4   C3   121.28  3.000
 2K0  C    C5   C6   120.33  3.000
 2K0  C6   C5   C4   121.15  3.000
 2K0  C    C5   C4   118.50  3.000
 2K0  H16  C6   H15  106.41  3.000
 2K0  H16  C6   O    111.29  3.000
 2K0  H15  C6   O    111.89  3.000
 2K0  H16  C6   C5   108.44  3.000
 2K0  H15  C6   C5   109.00  3.000
 2K0  O    C6   C5   109.70  3.000
 2K0  H17  O    C6   108.14  3.000
 2K0  H18  C    C5   120.02  3.000
 2K0  H18  C    C1   118.85  3.000
 2K0  C5   C    C1   121.12  3.000
 2K0  C14  N1   C10  115.25  3.000
 2K0  H19  N    C10  125.23  3.000
 2K0  H19  N    C9   125.18  3.000
 2K0  C10  N    C9   109.58  3.000
 2K0  H20  C17  N3   122.13  3.000
 2K0  H20  C17  C15  130.77  3.000
 2K0  N3   C17  C15  107.10  3.000
 2K0  C18  N3   N2   119.11  3.000
 2K0  C18  N3   C17  128.51  3.000
 2K0  N2   N3   C17  112.24  3.000
 2K0  N3   N2   C16  105.61  3.000
 2K0  H21  C18  N3   105.25  3.000
 2K0  H21  C18  C22  108.26  3.000
 2K0  N3   C18  C22  112.46  3.000
 2K0  H21  C18  C19  108.70  3.000
 2K0  C22  C18  C19  110.31  3.000
 2K0  N3   C18  C19  111.62  3.000
 2K0  H22  N4   C21  109.52  3.000
 2K0  H22  N4   C20  109.49  3.000
 2K0  C21  N4   C20  111.83  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
 2K0  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 2K0  CONST_02  C4   C5   C    C1      0.00   0.0  0
 2K0  CONST_03  C5   C4   C3   C2      0.00   0.0  0
 2K0  CONST_04  C5   C    C1   C2      0.00   0.0  0
 2K0  CONST_05  C    C1   C2   C3      0.00   0.0  0
 2K0  CONST_06  C    C5   C4   C3      0.00   0.0  0
 2K0  CONST_07  N1   C10  C11  C8    180.00   0.0  0
 2K0  CONST_08  N    C10  C11  C8      0.00   0.0  0
 2K0  CONST_09  C13  C12  C11  C8    180.00   0.0  0
 2K0  CONST_10  C10  N    C9   C8      0.00   0.0  0
 2K0  CONST_11  N1   C10  N    C9    180.00   0.0  0
 2K0  CONST_12  C11  C10  N    C9      0.00   0.0  0
 2K0  CONST_13  C10  C11  C8   C9      0.00   0.0  0
 2K0  CONST_14  C12  C11  C8   C9    180.00   0.0  0
 2K0  CONST_15  C13  C14  N1   C10     0.00   0.0  0
 2K0  CONST_16  C13  C12  C11  C10     0.00   0.0  0
 2K0  CONST_17  C14  N1   C10  C11     0.00   0.0  0
 2K0  CONST_18  C14  C13  C12  C11     0.00   0.0  0
 2K0  CONST_19  C15  C13  C12  C11   180.00   0.0  0
 2K0  CONST_20  N    C9   C8   C11     0.00   0.0  0
 2K0  CONST_21  N1   C14  C13  C12     0.00   0.0  0
 2K0  CONST_24  N1   C10  C11  C12     0.00   0.0  0
 2K0  CONST_25  N    C10  C11  C12   180.00   0.0  0
 2K0  CONST_26  N2   C16  C15  C13   180.00   0.0  0
 2K0  CONST_27  N3   C17  C15  C13   180.00   0.0  0
 2K0  CONST_28  N    C10  N1   C14   180.00   0.0  0
 2K0  CONST_31  N3   N2   C16  C15     0.00   0.0  0
 2K0  CONST_32  N1   C14  C13  C15   180.00   0.0  0
 2K0  CONST_33  N2   N3   C17  C15     0.00   0.0  0
 2K0  CONST_34  C17  N3   N2   C16     0.00   0.0  0
 2K0  CONST_35  N3   C17  C15  C16     0.00   0.0  0
 2K0  CONST_36  N2   C16  C15  C17     0.00   0.0  0
 2K0  CONST_37  C18  N3   C17  C15   180.00   0.0  0
 2K0  CONST_38  C18  N3   N2   C16   180.00   0.0  0
 2K0  CONST_39  C7   C3   C2   C1    180.00   0.0  0
 2K0  CONST_40  C6   C5   C    C1    180.00   0.0  0
 2K0  CONST_41  C6   C5   C4   C3    180.00   0.0  0
 2K0  CONST_42  C10  C11  C8   C7    180.00   0.0  0
 2K0  CONST_43  C12  C11  C8   C7      0.00   0.0  0
 2K0  CONST_44  N    C9   C8   C7    180.00   0.0  0
 2K0  CONST_45  C5   C4   C3   C7    180.00   0.0  0
 2K0  CONST_46  C4   C3   C2   CL    180.00   0.0  0
 2K0  CONST_47  C    C1   C2   CL    180.00   0.0  0
 2K0  CONST_48  H14  C4   C3   C2    180.00   0.0  0
 2K0  CONST_49  H18  C    C1   C2    180.00   0.0  0
 2K0  CONST_50  H1   C1   C2   C3    180.00   0.0  0
 2K0  CONST_51  H3   C12  C11  C8      0.00   0.0  0
 2K0  CONST_52  H19  N    C9   C8    180.00   0.0  0
 2K0  CONST_53  H4   C14  N1   C10   180.00   0.0  0
 2K0  CONST_54  H2   C9   N    C10   180.00   0.0  0
 2K0  CONST_55  H5   C16  C15  C13     0.00   0.0  0
 2K0  CONST_56  H20  C17  C15  C13     0.00   0.0  0
 2K0  Var_01    C21  N4   C20  C19   -61.32  30.0  1
 2K0  Var_02    C22  C21  N4   C20    62.02  30.0  1
 2K0  Var_03    N4   C21  C22  C18   -58.34  30.0  1
 2K0  Var_04    N4   C20  C19  C18    57.13  30.0  1
 2K0  Var_05    C8   C7   C3   C2   -112.70  30.0  2
 2K0  Var_06    C11  C8   C7   C3   -177.30  30.0  3
 2K0  Var_07    O    C6   C5   C4     34.75  30.0  2

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
 2K0  chir_01  C18  N3  C22  C19  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
 2K0  plan-1  C13  0.020
 2K0  plan-1  C15  0.020
 2K0  plan-1  C16  0.020
 2K0  plan-1  C17  0.020
 2K0  plan-1  N3   0.020
 2K0  plan-1  N2   0.020
 2K0  plan-1  C18  0.020
 2K0  plan-1  H5   0.020
 2K0  plan-1  H20  0.020
 2K0  plan-2  C1   0.020
 2K0  plan-2  C2   0.020
 2K0  plan-2  C3   0.020
 2K0  plan-2  C7   0.020
 2K0  plan-2  CL   0.020
 2K0  plan-2  C4   0.020
 2K0  plan-2  C5   0.020
 2K0  plan-2  C6   0.020
 2K0  plan-2  C    0.020
 2K0  plan-2  H1   0.020
 2K0  plan-2  H14  0.020
 2K0  plan-2  H18  0.020
 2K0  plan-3  C7   0.020
 2K0  plan-3  C8   0.020
 2K0  plan-3  C9   0.020
 2K0  plan-3  C10  0.020
 2K0  plan-3  C11  0.020
 2K0  plan-3  C12  0.020
 2K0  plan-3  C13  0.020
 2K0  plan-3  C14  0.020
 2K0  plan-3  C15  0.020
 2K0  plan-3  N1   0.020
 2K0  plan-3  N    0.020
 2K0  plan-3  H2   0.020
 2K0  plan-3  H3   0.020
 2K0  plan-3  H4   0.020
 2K0  plan-3  H19  0.020
 2K0  plan-4  C3   0.020
 2K0  plan-4  C7   0.020
 2K0  plan-4  C8   0.020
 2K0  plan-4  O1   0.020

