# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 11:10:53 2020
#   Inital geometry file: a 109 line input string
#   Ligand name: N-[3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl]-1H-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[nH]c34
#
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
 KEY  KEY  N-[3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl]-1H-pyrazolo[4,3-c]pyridine-7-carboxamide  ligand  42  27  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_KEY
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
 KEY  C4   C   CR6   0  -0.086  -2.4966  -0.1208   0.1034
 KEY  C14  C   CR16  0  -0.082   4.2549   2.5164  -0.5812
 KEY  C5   C   CR16  0  -0.267  -2.0243   1.0035   0.7724
 KEY  C6   C   CR6   0  -0.049  -2.5604   2.2553   0.5181
 KEY  C11  C   C     0   0.564   1.8208  -0.8782   0.2731
 KEY  C7   C   CR16  0  -0.203  -3.5899   2.4034  -0.3914
 KEY  C8   C   CR16  0  -0.390  -4.0785   1.2892  -1.0594
 KEY  C9   C   CR6   0   0.378  -3.5384   0.0262  -0.8287
 KEY  C10  C   CH3   0  -0.442  -4.9603  -0.9859  -2.4355
 KEY  C12  C   CR6   0  -0.174   2.6634   0.2996  -0.0394
 KEY  C13  C   CR16  0  -0.102   2.2058   1.6018  -0.1227
 KEY  N1   N   N     0  -0.277  -2.5330  -2.5140   0.6783
 KEY  N2   N   NH1   0  -0.746   0.5035  -0.7503   0.0174
 KEY  C3   C   CR5   0   0.237  -1.8605  -1.4187   0.3624
 KEY  N3   N   N     0  -0.415   2.9621   2.6780  -0.3866
 KEY  O1   O   O     0  -0.472   2.3156  -1.8981   0.7316
 KEY  C16  C   CR56  0   0.529   4.0492   0.1471  -0.2124
 KEY  N4   N   NR15  0  -0.541   4.8771  -0.9092  -0.1845
 KEY  N5   N   N     0  -0.213   6.1490  -0.5649  -0.4304
 KEY  C17  C   CR15  0  -0.120   6.1661   0.7251  -0.6246
 KEY  C15  C   CR56  0  -0.183   4.8550   1.2611  -0.4995
 KEY  C2   C   CR5   0   0.057  -0.4750  -1.6862   0.3386
 KEY  C1   C   CR15  0   0.017  -0.3643  -3.0184   0.6739
 KEY  N    N   NR5   0  -0.268  -1.6249  -3.4537   0.8672
 KEY  C    C   CH3   0  -0.505  -2.0323  -4.7932   1.2192
 KEY  O    O   O2    0  -0.453  -3.9399  -1.0846  -1.4598
 KEY  CL   CL  CL    0  -0.133  -1.9257   3.6375   1.3508
 KEY  H2   H   HCR6  0   0.291  -1.2386   0.8931   1.5091
 KEY  H3   H   HCR6  0   0.286  -4.0181   3.3764  -0.5901
 KEY  H4   H   HCR6  0   0.294  -4.8812   1.4309  -1.7693
 KEY  H5   H   HCH3  0   0.264  -5.1039  -1.9881  -2.8302
 KEY  H6   H   HCH3  0   0.233  -5.9030  -0.6382  -2.0060
 KEY  H7   H   HCH3  0   0.233  -4.6777  -0.3211  -3.2556
 KEY  H8   H   HCR6  0   0.245   1.1580   1.8224   0.0547
 KEY  H9   H   HNH1  0   0.420   0.1852   0.0587  -0.4940
 KEY  H10  H   HNR5  0   0.423   4.6413  -1.8682   0.0128
 KEY  H11  H   HCR5  0   0.282   7.0873   1.2422  -0.8434
 KEY  H12  H   HCR5  0   0.301   0.4864  -3.6672   0.7798
 KEY  H13  H   HCH3  0   0.262  -2.5699  -5.2581   0.3949
 KEY  H14  H   HCH3  0   0.260  -1.1487  -5.3838   1.4417
 KEY  H15  H   HCH3  0   0.264  -2.6729  -4.7707   2.0978
 KEY  H1   H   HCR6  0   0.281   4.8390   3.4029  -0.8033

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
 KEY  C10  O    single    1.415  0.020  1.415
 KEY  C8   C9   aromatic  1.393  0.020  1.393
 KEY  C8   C7   aromatic  1.388  0.020  1.388
 KEY  O    C9   single    1.339  0.020  1.339
 KEY  C9   C4   aromatic  1.406  0.020  1.406
 KEY  C7   C6   aromatic  1.382  0.020  1.382
 KEY  N5   C17  aromatic  1.305  0.020  1.305
 KEY  N5   N4   aromatic  1.340  0.020  1.340
 KEY  C17  C15  aromatic  1.422  0.020  1.422
 KEY  N4   C16  aromatic  1.342  0.020  1.342
 KEY  C15  C16  aromatic  1.405  0.020  1.405
 KEY  C15  C14  aromatic  1.394  0.020  1.394
 KEY  C4   C3   single    1.468  0.020  1.468
 KEY  C4   C5   aromatic  1.391  0.020  1.391
 KEY  C6   C5   aromatic  1.385  0.020  1.385
 KEY  C6   CL   single    1.734  0.020  1.734
 KEY  C16  C12  aromatic  1.405  0.020  1.405
 KEY  C14  N3   aromatic  1.317  0.020  1.317
 KEY  C3   C2   aromatic  1.411  0.020  1.411
 KEY  C3   N1   aromatic  1.324  0.020  1.324
 KEY  N2   C2   single    1.392  0.020  1.392
 KEY  N2   C11  single    1.348  0.020  1.348
 KEY  C12  C11  single    1.482  0.020  1.482
 KEY  C12  C13  aromatic  1.383  0.020  1.383
 KEY  N3   C13  aromatic  1.342  0.020  1.342
 KEY  C2   C1   aromatic  1.378  0.020  1.378
 KEY  N1   N    aromatic  1.320  0.020  1.320
 KEY  C11  O1   double    1.223  0.020  1.223
 KEY  C1   N    aromatic  1.348  0.020  1.348
 KEY  N    C    single    1.444  0.020  1.444
 KEY  C14  H1   single    0.930  0.020  1.080
 KEY  C5   H2   single    0.930  0.020  1.080
 KEY  C7   H3   single    0.930  0.020  1.080
 KEY  C8   H4   single    0.930  0.020  1.080
 KEY  C10  H5   single    0.970  0.020  1.090
 KEY  C10  H6   single    0.970  0.020  1.090
 KEY  C10  H7   single    0.970  0.020  1.090
 KEY  C13  H8   single    0.930  0.020  1.080
 KEY  N2   H9   single    0.860  0.020  1.020
 KEY  N4   H10  single    0.860  0.020  1.020
 KEY  C17  H11  single    0.930  0.020  1.080
 KEY  C1   H12  single    0.930  0.020  1.080
 KEY  C    H13  single    0.970  0.020  1.090
 KEY  C    H14  single    0.970  0.020  1.090
 KEY  C    H15  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
 KEY  C3   C4   C9   122.03  3.000
 KEY  C3   C4   C5   118.85  3.000
 KEY  C9   C4   C5   119.08  3.000
 KEY  H1   C14  C15  121.08  3.000
 KEY  H1   C14  N3   117.29  3.000
 KEY  C15  C14  N3   121.63  3.000
 KEY  H2   C5   C6   119.86  3.000
 KEY  H2   C5   C4   119.42  3.000
 KEY  C6   C5   C4   120.71  3.000
 KEY  CL   C6   C7   120.23  3.000
 KEY  CL   C6   C5   119.37  3.000
 KEY  C7   C6   C5   120.40  3.000
 KEY  O1   C11  N2   123.08  3.000
 KEY  O1   C11  C12  120.80  3.000
 KEY  N2   C11  C12  116.12  3.000
 KEY  H3   C7   C8   119.63  3.000
 KEY  H3   C7   C6   120.82  3.000
 KEY  C8   C7   C6   119.54  3.000
 KEY  H4   C8   C9   121.04  3.000
 KEY  H4   C8   C7   118.18  3.000
 KEY  C9   C8   C7   120.78  3.000
 KEY  O    C9   C8   123.91  3.000
 KEY  O    C9   C4   116.61  3.000
 KEY  C8   C9   C4   119.48  3.000
 KEY  H7   C10  H6   108.94  3.000
 KEY  H7   C10  H5   108.83  3.000
 KEY  H6   C10  H5   108.79  3.000
 KEY  H7   C10  O    111.93  3.000
 KEY  H6   C10  O    111.91  3.000
 KEY  H5   C10  O    106.34  3.000
 KEY  C16  C12  C13  114.91  3.000
 KEY  C13  C12  C11  124.97  3.000
 KEY  C16  C12  C11  120.05  3.000
 KEY  H8   C13  N3   114.42  3.000
 KEY  H8   C13  C12  120.07  3.000
 KEY  N3   C13  C12  125.50  3.000
 KEY  N    N1   C3   105.89  3.000
 KEY  H9   N2   C2   115.76  3.000
 KEY  H9   N2   C11  118.73  3.000
 KEY  C2   N2   C11  125.42  3.000
 KEY  C2   C3   N1   110.24  3.000
 KEY  N1   C3   C4   123.61  3.000
 KEY  C2   C3   C4   126.14  3.000
 KEY  C13  N3   C14  118.94  3.000
 KEY  C15  C16  N4   105.93  3.000
 KEY  C15  C16  C12  120.34  3.000
 KEY  N4   C16  C12  133.73  3.000
 KEY  H10  N4   N5   120.18  3.000
 KEY  H10  N4   C16  127.51  3.000
 KEY  N5   N4   C16  112.29  3.000
 KEY  C17  N5   N4   107.08  3.000
 KEY  H11  C17  C15  128.65  3.000
 KEY  H11  C17  N5   121.02  3.000
 KEY  C15  C17  N5   110.34  3.000
 KEY  C17  C15  C16  104.36  3.000
 KEY  C16  C15  C14  118.64  3.000
 KEY  C17  C15  C14  137.00  3.000
 KEY  C1   C2   C3   104.95  3.000
 KEY  C1   C2   N2   130.53  3.000
 KEY  C3   C2   N2   124.52  3.000
 KEY  H12  C1   N    122.08  3.000
 KEY  H12  C1   C2   132.13  3.000
 KEY  N    C1   C2   105.79  3.000
 KEY  C    N    C1   126.78  3.000
 KEY  C    N    N1   120.08  3.000
 KEY  C1   N    N1   113.13  3.000
 KEY  H15  C    H14  108.97  3.000
 KEY  H15  C    H13  109.25  3.000
 KEY  H14  C    H13  108.96  3.000
 KEY  H15  C    N    110.12  3.000
 KEY  H14  C    N    108.96  3.000
 KEY  H13  C    N    110.55  3.000
 KEY  C10  O    C9   118.89  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
 KEY  CONST_01  C7   C8   C9   C4     0.00   0.0  0
 KEY  CONST_02  C1   C2   C3   C4   180.00   0.0  0
 KEY  CONST_03  N    N1   C3   C4   180.00   0.0  0
 KEY  CONST_04  C7   C6   C5   C4     0.00   0.0  0
 KEY  CONST_05  N5   C17  C15  C14  180.00   0.0  0
 KEY  CONST_06  N4   C16  C15  C14  180.00   0.0  0
 KEY  CONST_07  C12  C16  C15  C14    0.00   0.0  0
 KEY  CONST_08  C12  C13  N3   C14    0.00   0.0  0
 KEY  CONST_09  C8   C9   C4   C5     0.00   0.0  0
 KEY  CONST_12  C8   C7   C6   C5     0.00   0.0  0
 KEY  CONST_13  C9   C8   C7   C6     0.00   0.0  0
 KEY  CONST_14  C9   C4   C5   C6     0.00   0.0  0
 KEY  CONST_15  C3   C4   C5   C6   180.00   0.0  0
 KEY  CONST_16  C3   C4   C9   C8   180.00   0.0  0
 KEY  CONST_19  N5   N4   C16  C12  180.00   0.0  0
 KEY  CONST_20  C17  C15  C16  C12  180.00   0.0  0
 KEY  CONST_21  N4   C16  C12  C13  180.00   0.0  0
 KEY  CONST_22  C15  C16  C12  C13    0.00   0.0  0
 KEY  CONST_23  C15  C14  N3   C13    0.00   0.0  0
 KEY  CONST_24  C1   C2   C3   N1     0.00   0.0  0
 KEY  CONST_25  C2   C1   N    N1     0.00   0.0  0
 KEY  CONST_26  N    C1   C2   C3     0.00   0.0  0
 KEY  CONST_27  C1   N    N1   C3     0.00   0.0  0
 KEY  CONST_28  C17  C15  C14  N3   180.00   0.0  0
 KEY  CONST_29  C16  C15  C14  N3     0.00   0.0  0
 KEY  CONST_30  C16  C12  C13  N3     0.00   0.0  0
 KEY  CONST_31  C17  N5   N4   C16    0.00   0.0  0
 KEY  CONST_32  N5   C17  C15  C16    0.00   0.0  0
 KEY  CONST_33  C15  C17  N5   N4     0.00   0.0  0
 KEY  CONST_34  C17  C15  C16  N4     0.00   0.0  0
 KEY  CONST_35  C15  C16  N4   N5     0.00   0.0  0
 KEY  CONST_36  N    N1   C3   C2     0.00   0.0  0
 KEY  CONST_37  N2   C2   C3   C4     0.00   0.0  0
 KEY  CONST_38  CL   C6   C5   C4   180.00   0.0  0
 KEY  CONST_39  O    C9   C4   C5   180.00   0.0  0
 KEY  CONST_40  N4   C16  C12  C11    0.00   0.0  0
 KEY  CONST_41  C15  C16  C12  C11  180.00   0.0  0
 KEY  CONST_42  N3   C13  C12  C11  180.00   0.0  0
 KEY  CONST_43  O    C9   C8   C7   180.00   0.0  0
 KEY  CONST_44  CL   C6   C7   C8   180.00   0.0  0
 KEY  CONST_45  N2   C2   C3   N1   180.00   0.0  0
 KEY  CONST_46  N    C1   C2   N2   180.00   0.0  0
 KEY  CONST_47  O    C9   C4   C3     0.00   0.0  0
 KEY  CONST_48  C    N    N1   C3   180.00   0.0  0
 KEY  CONST_49  C    N    C1   C2   180.00   0.0  0
 KEY  CONST_50  H4   C8   C9   C4   180.00   0.0  0
 KEY  CONST_51  H11  C17  C15  C14    0.00   0.0  0
 KEY  CONST_52  H8   C13  N3   C14  180.00   0.0  0
 KEY  CONST_53  H3   C7   C6   C5   180.00   0.0  0
 KEY  CONST_54  H2   C5   C6   C7   180.00   0.0  0
 KEY  CONST_55  H10  N4   C16  C12    0.00   0.0  0
 KEY  CONST_56  H1   C14  N3   C13  180.00   0.0  0
 KEY  CONST_57  H12  C1   N    N1   180.00   0.0  0
 KEY  CONST_58  C2   N2   C11  C12  180.00   0.0  0
 KEY  CONST_62  C2   N2   C11  O1     0.00   0.0  0
 KEY  Var_01    N2   C11  C12  C13   23.12  30.0  2
 KEY  Var_02    H13  C    N    N1    66.74  30.0  2
 KEY  Var_03    H5   C10  O    C9   178.49  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
 KEY  plan-1  C4   0.020
 KEY  plan-1  N1   0.020
 KEY  plan-1  N2   0.020
 KEY  plan-1  C3   0.020
 KEY  plan-1  C2   0.020
 KEY  plan-1  C1   0.020
 KEY  plan-1  N    0.020
 KEY  plan-1  C    0.020
 KEY  plan-1  H12  0.020
 KEY  plan-2  C4   0.020
 KEY  plan-2  C5   0.020
 KEY  plan-2  C6   0.020
 KEY  plan-2  C7   0.020
 KEY  plan-2  C8   0.020
 KEY  plan-2  C9   0.020
 KEY  plan-2  C3   0.020
 KEY  plan-2  O    0.020
 KEY  plan-2  CL   0.020
 KEY  plan-2  H2   0.020
 KEY  plan-2  H3   0.020
 KEY  plan-2  H4   0.020
 KEY  plan-3  C14  0.020
 KEY  plan-3  C11  0.020
 KEY  plan-3  C12  0.020
 KEY  plan-3  C13  0.020
 KEY  plan-3  N3   0.020
 KEY  plan-3  C16  0.020
 KEY  plan-3  N4   0.020
 KEY  plan-3  N5   0.020
 KEY  plan-3  C17  0.020
 KEY  plan-3  C15  0.020
 KEY  plan-3  H8   0.020
 KEY  plan-3  H10  0.020
 KEY  plan-3  H11  0.020
 KEY  plan-3  H1   0.020
 KEY  plan-4  C11  0.020
 KEY  plan-4  C12  0.020
 KEY  plan-4  N2   0.020
 KEY  plan-4  O1   0.020
 KEY  plan-4  C2   0.020
 KEY  plan-4  H9   0.020

