# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 23 19:34:36 2020
#   Inital geometry file: a 137 line input string
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(=O)N1CCN2[C@@H](COc3cnc4cc(c(Cl)cc4c23)c5c(C)ccc6n[nH]cc56)C1
#
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
 MKW  MKW  'None                     '  ligand  57  33  .  2021-08-14  2021-08-14  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_MKW
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
 MKW  C1   C   CH2   0  -0.594  -6.5155   1.9031   0.9911
 MKW  C2   C   C     0   0.562  -6.2658   0.9601  -0.1696
 MKW  C3   C   CH2   0  -0.343  -3.9205   1.8013  -0.3060
 MKW  C7   C   CR16  0  -0.271   0.2950   0.5495  -0.3970
 MKW  C8   C   CR6   0  -0.108   1.6145   0.8472  -0.1978
 MKW  C9   C   CR6   0   0.077   2.5188  -0.0735   0.3814
 MKW  C10  C   CR16  0  -0.356   2.0406  -1.3180   0.7060
 MKW  C11  C   CR66  0   0.192   0.6905  -1.6729   0.5086
 MKW  C12  C   CR16  0  -0.171  -0.9398  -3.2626   0.6150
 MKW  C13  C   CR6   0   0.278  -1.9237  -2.3708   0.1256
 MKW  C14  C   CH2   0  -0.164  -4.1881  -1.9250  -0.3592
 MKW  C15  C   CH1   0  -0.181  -3.6252  -0.8755  -1.3072
 MKW  C16  C   CH2   0  -0.337  -4.6738   0.1057  -1.8144
 MKW  C19  C   CR16  0  -0.294   5.7735   1.3330   1.7664
 MKW  C20  C   CR16  0  -0.296   6.7268   0.8339   0.9271
 MKW  C21  C   CR56  0   0.235   6.2958   0.0067  -0.1338
 MKW  C22  C   CR56  0  -0.085   4.9118  -0.2755  -0.2913
 MKW  CL   CL  CL    0  -0.119   2.2052   2.3947  -0.7015
 MKW  C17  C   CR6   0   0.041   3.9448   0.2597   0.5937
 MKW  C23  C   CR15  0  -0.052   4.8600  -1.0977  -1.4129
 MKW  N3   N   NR15  0  -0.402   6.1279  -1.2357  -1.8098
 MKW  N4   N   N     0  -0.314   7.0255  -0.5948  -1.0780
 MKW  C18  C   CR6   0   0.029   4.3775   1.0629   1.6208
 MKW  C6   C   CR66  0   0.041  -0.2035  -0.7132  -0.0187
 MKW  N2   N   N     0  -0.426   0.3028  -2.9342   0.8169
 MKW  C5   C   CR6   0   0.271  -1.5662  -1.0773  -0.1832
 MKW  O1   O   O2    0  -0.473  -3.1697  -2.8568  -0.0005
 MKW  N1   N   NT    0  -0.495  -2.5107  -0.1691  -0.6768
 MKW  C4   C   CH2   0  -0.310  -2.9072   0.8508   0.3007
 MKW  N    N   NT    0  -0.457  -5.0603   1.0462  -0.7858
 MKW  O    O   O     0  -0.495  -7.1186   0.1664  -0.5406
 MKW  C    C   CH3   0  -0.651  -7.9114   1.7693   1.5732
 MKW  H1   H   HCH2  0   0.265  -5.7702   1.7146   1.7697
 MKW  H2   H   HCH2  0   0.270  -6.3439   2.9320   0.6629
 MKW  H3   H   HCH2  0   0.286  -4.2096   2.5474   0.4287
 MKW  H4   H   HCH2  0   0.264  -3.4764   2.3354  -1.1506
 MKW  H5   H   HCR6  0   0.287  -0.3590   1.2687  -0.8707
 MKW  H6   H   HCR6  0   0.263   2.7060  -2.0595   1.1309
 MKW  H7   H   HCR6  0   0.275  -1.2394  -4.2774   0.8607
 MKW  H8   H   HCH2  0   0.235  -4.5945  -1.4684   0.5492
 MKW  H9   H   HCH2  0   0.260  -4.9803  -2.5044  -0.8327
 MKW  H10  H   HCH1  0   0.288  -3.2278  -1.3919  -2.1869
 MKW  H11  H   HCH2  0   0.271  -4.2487   0.6644  -2.6521
 MKW  H12  H   HCH2  0   0.280  -5.5427  -0.4332  -2.1821
 MKW  H14  H   HCR6  0   0.258   7.7756   1.0585   1.0712
 MKW  H15  H   HCH3  0   0.246   3.0979   2.6745   2.2470
 MKW  H16  H   HCH3  0   0.244   2.5290   1.0881   2.7441
 MKW  H17  H   HCH3  0   0.248   3.8946   1.8357   3.5670
 MKW  H18  H   HCR5  0   0.292   4.0441  -1.5717  -1.9324
 MKW  H19  H   HNR5  0   0.431   6.4382  -1.7757  -2.6040
 MKW  H20  H   HCH2  0   0.272  -2.0247   1.4091   0.6134
 MKW  H21  H   HCH2  0   0.236  -3.3357   0.4012   1.2075
 MKW  H22  H   HCH3  0   0.232  -8.0366   2.4741   2.3945
 MKW  H23  H   HCH3  0   0.228  -8.6801   1.9836   0.8319
 MKW  H24  H   HCH3  0   0.228  -8.0910   0.7689   1.9645
 MKW  H13  H   HCR6  0   0.250   6.0805   1.9619   2.5937
 MKW  C24  C   CH3   0  -0.741   3.4236   1.6913   2.5949

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
 MKW  N2   C12  aromatic  1.301  0.020  1.301
 MKW  N2   C11  aromatic  1.355  0.020  1.355
 MKW  C12  C13  aromatic  1.415  0.020  1.415
 MKW  C10  C11  aromatic  1.410  0.020  1.410
 MKW  C10  C9   aromatic  1.372  0.020  1.372
 MKW  C11  C6   aromatic  1.414  0.020  1.414
 MKW  C13  O1   single    1.343  0.020  1.343
 MKW  C13  C5   aromatic  1.377  0.020  1.377
 MKW  O1   C14  single    1.426  0.020  1.426
 MKW  N3   N4   aromatic  1.324  0.020  1.324
 MKW  N3   C23  aromatic  1.336  0.020  1.336
 MKW  N4   C21  aromatic  1.336  0.020  1.336
 MKW  C23  C22  aromatic  1.392  0.020  1.392
 MKW  C21  C22  aromatic  1.421  0.020  1.421
 MKW  C21  C20  aromatic  1.413  0.020  1.413
 MKW  C22  C17  aromatic  1.416  0.020  1.416
 MKW  C20  C19  aromatic  1.365  0.020  1.365
 MKW  C17  C9   single    1.480  0.020  1.480
 MKW  C17  C18  aromatic  1.374  0.020  1.374
 MKW  C19  C18  aromatic  1.429  0.020  1.429
 MKW  C9   C8   aromatic  1.415  0.020  1.415
 MKW  C18  C24  single    1.501  0.020  1.501
 MKW  C6   C5   aromatic  1.420  0.020  1.420
 MKW  C6   C7   aromatic  1.409  0.020  1.409
 MKW  C5   N1   single    1.400  0.020  1.400
 MKW  C14  C15  single    1.522  0.020  1.522
 MKW  C8   C7   aromatic  1.367  0.020  1.367
 MKW  C8   CL   single    1.731  0.020  1.731
 MKW  C15  N1   single    1.462  0.020  1.462
 MKW  C15  C16  single    1.523  0.020  1.523
 MKW  N1   C4   single    1.467  0.020  1.467
 MKW  C4   C3   single    1.516  0.020  1.516
 MKW  C16  N    single    1.446  0.020  1.446
 MKW  N    C3   single    1.449  0.020  1.449
 MKW  N    C2   single    1.357  0.020  1.357
 MKW  C2   C1   single    1.516  0.020  1.516
 MKW  C2   O    double    1.223  0.020  1.223
 MKW  C1   C    single    1.518  0.020  1.518
 MKW  C1   H1   single    0.970  0.020  1.090
 MKW  C1   H2   single    0.970  0.020  1.090
 MKW  C3   H3   single    0.970  0.020  1.090
 MKW  C3   H4   single    0.970  0.020  1.090
 MKW  C7   H5   single    0.930  0.020  1.080
 MKW  C10  H6   single    0.930  0.020  1.080
 MKW  C12  H7   single    0.930  0.020  1.080
 MKW  C14  H8   single    0.970  0.020  1.090
 MKW  C14  H9   single    0.970  0.020  1.090
 MKW  C15  H10  single    0.970  0.020  1.090
 MKW  C16  H11  single    0.970  0.020  1.090
 MKW  C16  H12  single    0.970  0.020  1.090
 MKW  C19  H13  single    0.930  0.020  1.080
 MKW  C20  H14  single    0.930  0.020  1.080
 MKW  C24  H15  single    0.970  0.020  1.090
 MKW  C24  H16  single    0.970  0.020  1.090
 MKW  C24  H17  single    0.970  0.020  1.090
 MKW  C23  H18  single    0.930  0.020  1.080
 MKW  N3   H19  single    0.860  0.020  1.020
 MKW  C4   H20  single    0.970  0.020  1.090
 MKW  C4   H21  single    0.970  0.020  1.090
 MKW  C    H22  single    0.970  0.020  1.090
 MKW  C    H23  single    0.970  0.020  1.090
 MKW  C    H24  single    0.970  0.020  1.090

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
 MKW  H2   C1   H1   105.60  3.000
 MKW  H2   C1   C    110.02  3.000
 MKW  H1   C1   C    109.76  3.000
 MKW  H2   C1   C2   109.25  3.000
 MKW  H1   C1   C2   108.99  3.000
 MKW  C    C1   C2   112.96  3.000
 MKW  O    C2   N    121.55  3.000
 MKW  O    C2   C1   121.41  3.000
 MKW  N    C2   C1   117.03  3.000
 MKW  H4   C3   H3   107.16  3.000
 MKW  H4   C3   N    108.56  3.000
 MKW  H3   C3   N    111.87  3.000
 MKW  H4   C3   C4   110.11  3.000
 MKW  H3   C3   C4   109.74  3.000
 MKW  N    C3   C4   109.36  3.000
 MKW  H5   C7   C6   119.97  3.000
 MKW  H5   C7   C8   120.18  3.000
 MKW  C6   C7   C8   119.83  3.000
 MKW  CL   C8   C9   118.87  3.000
 MKW  CL   C8   C7   118.78  3.000
 MKW  C9   C8   C7   122.34  3.000
 MKW  C17  C9   C10  120.41  3.000
 MKW  C17  C9   C8   121.88  3.000
 MKW  C10  C9   C8   117.67  3.000
 MKW  H6   C10  C11  118.09  3.000
 MKW  H6   C10  C9   119.98  3.000
 MKW  C11  C10  C9   121.93  3.000
 MKW  N2   C11  C6   122.40  3.000
 MKW  C6   C11  C10  119.14  3.000
 MKW  N2   C11  C10  118.45  3.000
 MKW  H7   C12  N2   117.65  3.000
 MKW  H7   C12  C13  118.37  3.000
 MKW  N2   C12  C13  123.96  3.000
 MKW  O1   C13  C5   124.02  3.000
 MKW  C5   C13  C12  119.27  3.000
 MKW  O1   C13  C12  116.70  3.000
 MKW  H9   C14  H8   108.20  3.000
 MKW  H9   C14  O1   106.32  3.000
 MKW  H8   C14  O1   109.20  3.000
 MKW  H9   C14  C15  111.40  3.000
 MKW  H8   C14  C15  111.50  3.000
 MKW  O1   C14  C15  110.06  3.000
 MKW  H10  C15  N1   107.31  3.000
 MKW  H10  C15  C16  106.63  3.000
 MKW  N1   C15  C16  110.92  3.000
 MKW  H10  C15  C14  108.03  3.000
 MKW  C16  C15  C14  113.39  3.000
 MKW  N1   C15  C14  110.27  3.000
 MKW  H12  C16  H11  107.77  3.000
 MKW  H12  C16  N    110.45  3.000
 MKW  H11  C16  N    108.46  3.000
 MKW  H12  C16  C15  110.10  3.000
 MKW  H11  C16  C15  108.47  3.000
 MKW  N    C16  C15  111.48  3.000
 MKW  H13  C19  C18  117.66  3.000
 MKW  H13  C19  C20  118.94  3.000
 MKW  C18  C19  C20  123.40  3.000
 MKW  H14  C20  C21  121.15  3.000
 MKW  H14  C20  C19  121.28  3.000
 MKW  C21  C20  C19  117.57  3.000
 MKW  N4   C21  C22  111.35  3.000
 MKW  C22  C21  C20  119.78  3.000
 MKW  N4   C21  C20  128.87  3.000
 MKW  C23  C22  C17  134.56  3.000
 MKW  C17  C22  C21  121.38  3.000
 MKW  C23  C22  C21  104.06  3.000
 MKW  C18  C17  C22  118.24  3.000
 MKW  C18  C17  C9   122.86  3.000
 MKW  C22  C17  C9   118.90  3.000
 MKW  H18  C23  N3   122.02  3.000
 MKW  H18  C23  C22  132.60  3.000
 MKW  N3   C23  C22  105.38  3.000
 MKW  H19  N3   N4   119.06  3.000
 MKW  H19  N3   C23  125.52  3.000
 MKW  N4   N3   C23  115.42  3.000
 MKW  N3   N4   C21  103.79  3.000
 MKW  C17  C18  C24  121.98  3.000
 MKW  C24  C18  C19  118.39  3.000
 MKW  C17  C18  C19  119.62  3.000
 MKW  C5   C6   C11  118.42  3.000
 MKW  C5   C6   C7   122.55  3.000
 MKW  C11  C6   C7   118.99  3.000
 MKW  C12  N2   C11  118.22  3.000
 MKW  N1   C5   C6   121.45  3.000
 MKW  N1   C5   C13  120.88  3.000
 MKW  C6   C5   C13  117.65  3.000
 MKW  C14  O1   C13  116.72  3.000
 MKW  C4   N1   C5   113.47  3.000
 MKW  C4   N1   C15  114.64  3.000
 MKW  C5   N1   C15  110.65  3.000
 MKW  H21  C4   H20  106.77  3.000
 MKW  H21  C4   N1   111.76  3.000
 MKW  H20  C4   N1   109.17  3.000
 MKW  H21  C4   C3   109.03  3.000
 MKW  H20  C4   C3   109.56  3.000
 MKW  N1   C4   C3   110.48  3.000
 MKW  C16  N    C3   111.35  3.000
 MKW  C3   N    C2   125.57  3.000
 MKW  C16  N    C2   121.28  3.000
 MKW  H24  C    H23  107.99  3.000
 MKW  H24  C    H22  107.73  3.000
 MKW  H23  C    H22  107.74  3.000
 MKW  H24  C    C1   111.74  3.000
 MKW  H23  C    C1   111.75  3.000
 MKW  H22  C    C1   109.73  3.000
 MKW  H17  C24  H16  107.83  3.000
 MKW  H17  C24  H15  107.07  3.000
 MKW  H16  C24  H15  107.29  3.000
 MKW  H17  C24  C18  111.07  3.000
 MKW  H16  C24  C18  112.27  3.000
 MKW  H15  C24  C18  111.06  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
 MKW  CONST_01  N2   C11  C6   C7    180.00   0.0  0
 MKW  CONST_02  C10  C11  C6   C7      0.00   0.0  0
 MKW  CONST_03  C13  C5   C6   C7    180.00   0.0  0
 MKW  CONST_04  C10  C9   C8   C7      0.00   0.0  0
 MKW  CONST_05  C17  C9   C8   C7    180.00   0.0  0
 MKW  CONST_06  C11  C10  C9   C8      0.00   0.0  0
 MKW  CONST_09  C11  C6   C7   C8      0.00   0.0  0
 MKW  CONST_10  C5   C6   C7   C8    180.00   0.0  0
 MKW  CONST_11  N2   C11  C10  C9    180.00   0.0  0
 MKW  CONST_12  C6   C11  C10  C9      0.00   0.0  0
 MKW  CONST_13  C23  C22  C17  C9      0.00   0.0  0
 MKW  CONST_14  C21  C22  C17  C9    180.00   0.0  0
 MKW  CONST_15  C19  C18  C17  C9    180.00   0.0  0
 MKW  CONST_16  C6   C7   C8   C9      0.00   0.0  0
 MKW  CONST_17  C12  N2   C11  C10   180.00   0.0  0
 MKW  CONST_18  C5   C6   C11  C10   180.00   0.0  0
 MKW  CONST_21  C13  C12  N2   C11     0.00   0.0  0
 MKW  CONST_22  C17  C9   C10  C11   180.00   0.0  0
 MKW  CONST_23  C13  C5   C6   C11     0.00   0.0  0
 MKW  CONST_24  C6   C11  N2   C12     0.00   0.0  0
 MKW  CONST_25  C6   C5   C13  C12     0.00   0.0  0
 MKW  CONST_26  N4   C21  C20  C19   180.00   0.0  0
 MKW  CONST_27  C22  C21  C20  C19     0.00   0.0  0
 MKW  CONST_28  C22  C17  C18  C19     0.00   0.0  0
 MKW  CONST_29  N3   N4   C21  C20   180.00   0.0  0
 MKW  CONST_30  C23  C22  C21  C20   180.00   0.0  0
 MKW  CONST_31  C17  C22  C21  C20     0.00   0.0  0
 MKW  CONST_32  C17  C18  C19  C20     0.00   0.0  0
 MKW  CONST_33  C23  N3   N4   C21     0.00   0.0  0
 MKW  CONST_34  N3   C23  C22  C21     0.00   0.0  0
 MKW  CONST_35  C18  C17  C22  C21     0.00   0.0  0
 MKW  CONST_36  C18  C19  C20  C21     0.00   0.0  0
 MKW  CONST_37  N4   N3   C23  C22     0.00   0.0  0
 MKW  CONST_38  N3   N4   C21  C22     0.00   0.0  0
 MKW  CONST_39  N3   C23  C22  C17   180.00   0.0  0
 MKW  CONST_40  N4   C21  C22  C17   180.00   0.0  0
 MKW  CONST_41  N4   C21  C22  C23     0.00   0.0  0
 MKW  CONST_42  C18  C17  C22  C23   180.00   0.0  0
 MKW  CONST_43  C5   C13  C12  N2      0.00   0.0  0
 MKW  CONST_44  C5   C6   C11  N2      0.00   0.0  0
 MKW  CONST_45  C24  C18  C17  C9      0.00   0.0  0
 MKW  CONST_46  CL   C8   C9   C10   180.00   0.0  0
 MKW  CONST_47  C24  C18  C19  C20   180.00   0.0  0
 MKW  CONST_48  C24  C18  C17  C22   180.00   0.0  0
 MKW  CONST_49  C17  C9   C8   CL      0.00   0.0  0
 MKW  CONST_50  C6   C7   C8   CL    180.00   0.0  0
 MKW  CONST_51  H6   C10  C9   C8    180.00   0.0  0
 MKW  CONST_52  H5   C7   C8   C9    180.00   0.0  0
 MKW  CONST_53  H7   C12  N2   C11   180.00   0.0  0
 MKW  CONST_54  H19  N3   N4   C21   180.00   0.0  0
 MKW  CONST_55  H18  C23  C22  C21   180.00   0.0  0
 MKW  CONST_56  H13  C19  C20  C21   180.00   0.0  0
 MKW  CONST_57  H14  C20  C21  C22   180.00   0.0  0
 MKW  CONST_58  C16  N    C2   C1    180.00   0.0  0
 MKW  CONST_59  C3   N    C2   C1      0.00   0.0  0
 MKW  CONST_60  O    C2   N    C3    180.00   0.0  0
 MKW  CONST_61  O    C2   N    C16     0.00   0.0  0
 MKW  Var_01    C5   N1   C4   C3    179.58  30.0  1
 MKW  Var_02    C15  C16  N    C3     58.77  30.0  1
 MKW  Var_03    C15  C14  O1   C13    34.90  30.0  1
 MKW  Var_04    C5   C13  O1   C14    -5.99  30.0  1
 MKW  Var_05    C4   C3   N    C16   -61.26  30.0  1
 MKW  Var_06    N    C3   C4   N1     56.62  30.0  1
 MKW  Var_07    H15  C24  C18  C19    88.78  30.0  2
 MKW  Var_08    C    C1   C2   N     177.55  30.0  3
 MKW  Var_09    H22  C    C1   C2   -179.49  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
 MKW  chir_01  C15  C14  N1  C16  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
 MKW  plan-1  C9   0.020
 MKW  plan-1  C19  0.020
 MKW  plan-1  C20  0.020
 MKW  plan-1  C21  0.020
 MKW  plan-1  C22  0.020
 MKW  plan-1  C17  0.020
 MKW  plan-1  C23  0.020
 MKW  plan-1  N3   0.020
 MKW  plan-1  N4   0.020
 MKW  plan-1  C18  0.020
 MKW  plan-1  H14  0.020
 MKW  plan-1  H18  0.020
 MKW  plan-1  H19  0.020
 MKW  plan-1  H13  0.020
 MKW  plan-1  C24  0.020
 MKW  plan-2  C7   0.020
 MKW  plan-2  C8   0.020
 MKW  plan-2  C9   0.020
 MKW  plan-2  C10  0.020
 MKW  plan-2  C11  0.020
 MKW  plan-2  C12  0.020
 MKW  plan-2  C13  0.020
 MKW  plan-2  CL   0.020
 MKW  plan-2  C17  0.020
 MKW  plan-2  C6   0.020
 MKW  plan-2  N2   0.020
 MKW  plan-2  C5   0.020
 MKW  plan-2  O1   0.020
 MKW  plan-2  N1   0.020
 MKW  plan-2  H5   0.020
 MKW  plan-2  H6   0.020
 MKW  plan-2  H7   0.020
 MKW  plan-3  C1   0.020
 MKW  plan-3  C2   0.020
 MKW  plan-3  C3   0.020
 MKW  plan-3  C16  0.020
 MKW  plan-3  N    0.020
 MKW  plan-3  O    0.020

