# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 11:30:26 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: N-[3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl]-2-methyl-2H-pyrazolo[4,3-c]pyridine-7-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(Cl)cc1c2nn(C)cc2NC(=O)c3cncc4cn(C)nc34
#
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
 KEV  KEV  N-[3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl]-2-methyl-2H-pyrazolo[4,3-c]pyridine-7-carboxamide  ligand  45  28  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_KEV
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
 KEV  C4   C   CR16  0  -0.110   1.9309  -1.6595   0.4813
 KEV  C14  C   CR16  0  -0.204  -3.8016  -2.3107  -0.5975
 KEV  C5   C   CR6   0  -0.183   2.4245  -0.3859   0.3356
 KEV  C6   C   CR56  0   0.354   3.7916  -0.2878  -0.0263
 KEV  C11  C   CR6   0  -0.084  -2.6950   0.1740   0.0450
 KEV  C7   C   C     0   0.520   1.6100   0.8243   0.6141
 KEV  C8   C   CR5   0   0.059  -0.6671   1.6857   0.4894
 KEV  C9   C   CR15  0   0.013  -0.5586   3.0077   0.8640
 KEV  C10  C   CR5   0   0.237  -2.0552   1.4495   0.3911
 KEV  C12  C   CR16  0  -0.263  -2.3120  -0.9745   0.7291
 KEV  C13  C   CR6   0  -0.049  -2.8539  -2.2067   0.4025
 KEV  N1   N   N     0  -0.416   2.6302  -2.8042   0.2936
 KEV  N2   N   N     0  -0.312   4.5513   0.7792  -0.2470
 KEV  C3   C   CR16  0  -0.085   3.8881  -2.7268  -0.0563
 KEV  N3   N   NH1   0  -0.733   0.3185   0.7405   0.2233
 KEV  CL   CL  CL    0  -0.133  -2.3317  -3.6196   1.2619
 KEV  C15  C   CR16  0  -0.390  -4.2010  -1.1716  -1.2831
 KEV  C16  C   CR6   0   0.376  -3.6522   0.0721  -0.9795
 KEV  O1   O   O2    0  -0.453  -3.9667   1.2048  -1.6216
 KEV  C17  C   CH3   0  -0.442  -4.9158   1.1543  -2.6702
 KEV  N5   N   N     0  -0.278  -2.7300   2.5516   0.6772
 KEV  N4   N   NR5   0  -0.268  -1.8221   3.4679   0.9591
 KEV  C18  C   CH3   0  -0.505  -2.2316   4.7929   1.3600
 KEV  O    O   O     0  -0.460   2.0795   1.8101   1.1570
 KEV  C2   C   CR56  0  -0.218   4.5219  -1.4881  -0.2307
 KEV  C1   C   CR15  0   0.022   5.7964  -1.0547  -0.5920
 KEV  N    N   NR5   0  -0.243   5.7391   0.2729  -0.5806
 KEV  C    C   CH3   0  -0.507   6.8183   1.1804  -0.9028
 KEV  H1   H   HCR6  0   0.251   0.9032  -1.8112   0.7958
 KEV  H3   H   HCR5  0   0.299   0.2934   3.6356   1.0535
 KEV  H4   H   HCR6  0   0.289  -1.5944  -0.8985   1.5361
 KEV  H5   H   HCR6  0   0.275   4.4257  -3.6571  -0.2079
 KEV  H6   H   HNH1  0   0.417   0.0373  -0.0517  -0.3345
 KEV  H7   H   HCR6  0   0.294  -4.9414  -1.2805  -2.0629
 KEV  H8   H   HCH3  0   0.233  -4.5883   0.5060  -3.4869
 KEV  H9   H   HCH3  0   0.233  -5.8934   0.8155  -2.3188
 KEV  H10  H   HCH3  0   0.264  -5.0108   2.1697  -3.0458
 KEV  H11  H   HCH3  0   0.263  -2.8986   5.2184   0.6138
 KEV  H12  H   HCH3  0   0.261  -2.7409   4.7624   2.3218
 KEV  H13  H   HCH3  0   0.260  -1.3513   5.4226   1.4461
 KEV  H14  H   HCR5  0   0.314   6.6943  -1.5926  -0.8480
 KEV  H15  H   HCH3  0   0.274   6.5713   1.7415  -1.8011
 KEV  H16  H   HCH3  0   0.275   6.9730   1.8697  -0.0766
 KEV  H17  H   HCH3  0   0.267   7.7246   0.6082  -1.0717
 KEV  H2   H   HCR6  0   0.286  -4.2350  -3.2680  -0.8533

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
 KEV  C17  O1   single    1.415  0.020  1.415
 KEV  C15  C16  aromatic  1.393  0.020  1.393
 KEV  C15  C14  aromatic  1.388  0.020  1.388
 KEV  O1   C16  single    1.339  0.020  1.339
 KEV  C    N    single    1.446  0.020  1.446
 KEV  C16  C11  aromatic  1.406  0.020  1.406
 KEV  C14  C13  aromatic  1.382  0.020  1.382
 KEV  N    C1   aromatic  1.329  0.020  1.329
 KEV  N    N2   aromatic  1.334  0.020  1.334
 KEV  C1   C2   aromatic  1.394  0.020  1.394
 KEV  N2   C6   aromatic  1.328  0.020  1.328
 KEV  C2   C6   aromatic  1.420  0.020  1.420
 KEV  C2   C3   aromatic  1.402  0.020  1.402
 KEV  C11  C12  aromatic  1.391  0.020  1.391
 KEV  C11  C10  single    1.468  0.020  1.468
 KEV  C13  C12  aromatic  1.385  0.020  1.385
 KEV  C13  CL   single    1.734  0.020  1.734
 KEV  C6   C5   aromatic  1.418  0.020  1.418
 KEV  C3   N1   aromatic  1.308  0.020  1.308
 KEV  C10  C8   aromatic  1.411  0.020  1.411
 KEV  C10  N5   aromatic  1.324  0.020  1.324
 KEV  N1   C4   aromatic  1.354  0.020  1.354
 KEV  N3   C8   single    1.391  0.020  1.391
 KEV  N3   C7   single    1.352  0.020  1.352
 KEV  C5   C4   aromatic  1.374  0.020  1.374
 KEV  C5   C7   single    1.485  0.020  1.485
 KEV  C8   C9   aromatic  1.378  0.020  1.378
 KEV  N5   N4   aromatic  1.320  0.020  1.320
 KEV  C7   O    double    1.219  0.020  1.219
 KEV  C9   N4   aromatic  1.348  0.020  1.348
 KEV  N4   C18  single    1.444  0.020  1.444
 KEV  C4   H1   single    0.930  0.020  1.080
 KEV  C14  H2   single    0.930  0.020  1.080
 KEV  C9   H3   single    0.930  0.020  1.080
 KEV  C12  H4   single    0.930  0.020  1.080
 KEV  C3   H5   single    0.930  0.020  1.080
 KEV  N3   H6   single    0.860  0.020  1.020
 KEV  C15  H7   single    0.930  0.020  1.080
 KEV  C17  H8   single    0.970  0.020  1.090
 KEV  C17  H9   single    0.970  0.020  1.090
 KEV  C17  H10  single    0.970  0.020  1.090
 KEV  C18  H11  single    0.970  0.020  1.090
 KEV  C18  H12  single    0.970  0.020  1.090
 KEV  C18  H13  single    0.970  0.020  1.090
 KEV  C1   H14  single    0.930  0.020  1.080
 KEV  C    H15  single    0.970  0.020  1.090
 KEV  C    H16  single    0.970  0.020  1.090
 KEV  C    H17  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
 KEV  H1   C4   N1   114.27  3.000
 KEV  H1   C4   C5   120.03  3.000
 KEV  N1   C4   C5   125.69  3.000
 KEV  H2   C14  C15  119.62  3.000
 KEV  H2   C14  C13  120.84  3.000
 KEV  C15  C14  C13  119.54  3.000
 KEV  C7   C5   C6   121.36  3.000
 KEV  C7   C5   C4   122.59  3.000
 KEV  C6   C5   C4   115.96  3.000
 KEV  C2   C6   N2   111.16  3.000
 KEV  C2   C6   C5   118.32  3.000
 KEV  N2   C6   C5   130.51  3.000
 KEV  C16  C11  C12  119.10  3.000
 KEV  C12  C11  C10  118.78  3.000
 KEV  C16  C11  C10  122.10  3.000
 KEV  O    C7   N3   123.14  3.000
 KEV  O    C7   C5   122.08  3.000
 KEV  N3   C7   C5   114.78  3.000
 KEV  N3   C8   C10  124.72  3.000
 KEV  N3   C8   C9   130.38  3.000
 KEV  C10  C8   C9   104.88  3.000
 KEV  H3   C9   N4   122.07  3.000
 KEV  H3   C9   C8   132.10  3.000
 KEV  N4   C9   C8   105.83  3.000
 KEV  N5   C10  C8   110.30  3.000
 KEV  N5   C10  C11  123.51  3.000
 KEV  C8   C10  C11  126.18  3.000
 KEV  H4   C12  C13  119.84  3.000
 KEV  H4   C12  C11  119.43  3.000
 KEV  C13  C12  C11  120.73  3.000
 KEV  CL   C13  C12  119.35  3.000
 KEV  CL   C13  C14  120.26  3.000
 KEV  C12  C13  C14  120.39  3.000
 KEV  C3   N1   C4   118.92  3.000
 KEV  N    N2   C6   104.24  3.000
 KEV  H5   C3   C2   121.06  3.000
 KEV  H5   C3   N1   117.59  3.000
 KEV  C2   C3   N1   121.35  3.000
 KEV  H6   N3   C8   116.22  3.000
 KEV  H6   N3   C7   118.35  3.000
 KEV  C8   N3   C7   125.40  3.000
 KEV  H7   C15  C16  121.13  3.000
 KEV  H7   C15  C14  118.09  3.000
 KEV  C16  C15  C14  120.78  3.000
 KEV  O1   C16  C15  123.92  3.000
 KEV  O1   C16  C11  116.61  3.000
 KEV  C15  C16  C11  119.46  3.000
 KEV  C17  O1   C16  118.85  3.000
 KEV  H10  C17  H9   108.82  3.000
 KEV  H10  C17  H8   108.79  3.000
 KEV  H9   C17  H8   108.94  3.000
 KEV  H10  C17  O1   106.34  3.000
 KEV  H9   C17  O1   111.89  3.000
 KEV  H8   C17  O1   111.96  3.000
 KEV  N4   N5   C10  105.87  3.000
 KEV  C18  N4   N5   120.08  3.000
 KEV  C18  N4   C9   126.78  3.000
 KEV  N5   N4   C9   113.11  3.000
 KEV  H13  C18  H12  108.99  3.000
 KEV  H13  C18  H11  108.95  3.000
 KEV  H12  C18  H11  109.28  3.000
 KEV  H13  C18  N4   108.93  3.000
 KEV  H12  C18  N4   110.63  3.000
 KEV  H11  C18  N4   110.03  3.000
 KEV  C1   C2   C3   136.07  3.000
 KEV  C3   C2   C6   119.76  3.000
 KEV  C1   C2   C6   104.18  3.000
 KEV  H14  C1   N    122.45  3.000
 KEV  H14  C1   C2   131.94  3.000
 KEV  N    C1   C2   105.60  3.000
 KEV  C    N    C1   126.35  3.000
 KEV  C1   N    N2   114.82  3.000
 KEV  C    N    N2   118.82  3.000
 KEV  H17  C    H16  109.50  3.000
 KEV  H17  C    H15  109.46  3.000
 KEV  H16  C    H15  109.45  3.000
 KEV  H17  C    N    109.09  3.000
 KEV  H16  C    N    109.56  3.000
 KEV  H15  C    N    109.77  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
 KEV  CONST_01  C2   C3   N1   C4     0.00   0.0  0
 KEV  CONST_02  N2   C6   C5   C4   180.00   0.0  0
 KEV  CONST_03  C2   C6   C5   C4     0.00   0.0  0
 KEV  CONST_04  C11  C16  C15  C14    0.00   0.0  0
 KEV  CONST_05  C11  C12  C13  C14    0.00   0.0  0
 KEV  CONST_06  N    N2   C6   C5   180.00   0.0  0
 KEV  CONST_07  C1   C2   C6   C5   180.00   0.0  0
 KEV  CONST_08  C3   C2   C6   C5     0.00   0.0  0
 KEV  CONST_09  C3   N1   C4   C5     0.00   0.0  0
 KEV  CONST_10  C1   N    N2   C6     0.00   0.0  0
 KEV  CONST_11  N    C1   C2   C6     0.00   0.0  0
 KEV  CONST_12  N1   C3   C2   C6     0.00   0.0  0
 KEV  CONST_13  N1   C4   C5   C6     0.00   0.0  0
 KEV  CONST_14  C9   C8   C10  C11  180.00   0.0  0
 KEV  CONST_15  N4   N5   C10  C11  180.00   0.0  0
 KEV  CONST_18  N4   N5   C10  C8     0.00   0.0  0
 KEV  CONST_19  N5   N4   C9   C8     0.00   0.0  0
 KEV  CONST_20  N5   C10  C8   C9     0.00   0.0  0
 KEV  CONST_21  C10  N5   N4   C9     0.00   0.0  0
 KEV  CONST_22  C15  C16  C11  C10  180.00   0.0  0
 KEV  CONST_23  C13  C12  C11  C10  180.00   0.0  0
 KEV  CONST_24  N4   C9   C8   C10    0.00   0.0  0
 KEV  CONST_25  C15  C16  C11  C12    0.00   0.0  0
 KEV  CONST_27  C15  C14  C13  C12    0.00   0.0  0
 KEV  CONST_28  C16  C15  C14  C13    0.00   0.0  0
 KEV  CONST_29  C16  C11  C12  C13    0.00   0.0  0
 KEV  CONST_30  C1   C2   C3   N1   180.00   0.0  0
 KEV  CONST_31  C2   C1   N    N2     0.00   0.0  0
 KEV  CONST_32  C1   C2   C6   N2     0.00   0.0  0
 KEV  CONST_33  C3   C2   C6   N2   180.00   0.0  0
 KEV  CONST_34  N    C1   C2   C3   180.00   0.0  0
 KEV  CONST_36  N    N2   C6   C2     0.00   0.0  0
 KEV  CONST_37  O1   C16  C15  C14  180.00   0.0  0
 KEV  CONST_38  C    N    N2   C6   180.00   0.0  0
 KEV  CONST_39  CL   C13  C12  C11  180.00   0.0  0
 KEV  CONST_40  N3   C8   C10  C11    0.00   0.0  0
 KEV  CONST_41  N2   C6   C5   C7     0.00   0.0  0
 KEV  CONST_42  C2   C6   C5   C7   180.00   0.0  0
 KEV  CONST_43  N1   C4   C5   C7   180.00   0.0  0
 KEV  CONST_44  C18  N4   C9   C8   180.00   0.0  0
 KEV  CONST_45  O1   C16  C11  C10    0.00   0.0  0
 KEV  CONST_46  C18  N4   N5   C10  180.00   0.0  0
 KEV  CONST_47  O1   C16  C11  C12  180.00   0.0  0
 KEV  CONST_48  N5   C10  C8   N3   180.00   0.0  0
 KEV  CONST_49  N4   C9   C8   N3   180.00   0.0  0
 KEV  CONST_50  C15  C14  C13  CL   180.00   0.0  0
 KEV  CONST_51  C    N    C1   C2   180.00   0.0  0
 KEV  CONST_52  H5   C3   N1   C4   180.00   0.0  0
 KEV  CONST_53  H4   C12  C13  C14  180.00   0.0  0
 KEV  CONST_54  H14  C1   C2   C6   180.00   0.0  0
 KEV  CONST_55  H1   C4   C5   C6   180.00   0.0  0
 KEV  CONST_56  H7   C15  C16  C11  180.00   0.0  0
 KEV  CONST_57  H3   C9   C8   C10  180.00   0.0  0
 KEV  CONST_58  H2   C14  C13  C12  180.00   0.0  0
 KEV  CONST_59  C8   N3   C7   C5   180.00   0.0  0
 KEV  CONST_63  O    C7   N3   C8     0.00   0.0  0
 KEV  Var_01    N3   C7   C5   C4   -38.84  30.0  2
 KEV  Var_02    H11  C18  N4   C9   127.19  30.0  2
 KEV  Var_03    H15  C    N    N2   -64.53  30.0  2
 KEV  Var_04    H8   C17  O1   C16  -60.98  30.0  3

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
 KEV  plan-1  C11  0.020
 KEV  plan-1  C8   0.020
 KEV  plan-1  C9   0.020
 KEV  plan-1  C10  0.020
 KEV  plan-1  N3   0.020
 KEV  plan-1  N5   0.020
 KEV  plan-1  N4   0.020
 KEV  plan-1  C18  0.020
 KEV  plan-1  H3   0.020
 KEV  plan-2  C14  0.020
 KEV  plan-2  C11  0.020
 KEV  plan-2  C10  0.020
 KEV  plan-2  C12  0.020
 KEV  plan-2  C13  0.020
 KEV  plan-2  CL   0.020
 KEV  plan-2  C15  0.020
 KEV  plan-2  C16  0.020
 KEV  plan-2  O1   0.020
 KEV  plan-2  H4   0.020
 KEV  plan-2  H7   0.020
 KEV  plan-2  H2   0.020
 KEV  plan-3  C4   0.020
 KEV  plan-3  C5   0.020
 KEV  plan-3  C6   0.020
 KEV  plan-3  C7   0.020
 KEV  plan-3  N1   0.020
 KEV  plan-3  N2   0.020
 KEV  plan-3  C3   0.020
 KEV  plan-3  C2   0.020
 KEV  plan-3  C1   0.020
 KEV  plan-3  N    0.020
 KEV  plan-3  C    0.020
 KEV  plan-3  H1   0.020
 KEV  plan-3  H5   0.020
 KEV  plan-3  H14  0.020
 KEV  plan-4  C5   0.020
 KEV  plan-4  C7   0.020
 KEV  plan-4  C8   0.020
 KEV  plan-4  N3   0.020
 KEV  plan-4  O    0.020
 KEV  plan-4  H6   0.020

