# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 02:07:45 2021
#   Inital geometry file: a 104 line input string
#   Ligand name: ethyl 1-(4-azanylbutyl)-3-(3,4-dichlorophenyl)pyrazole-4-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1cn(CCCCN)nc1c2ccc(Cl)c(Cl)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
 KXH  KXH  'ethyl 1-(4-azanylbutyl)-3-(3,4-dichlorophenyl)pyrazole-4-carboxylate'  ligand  42  23  .  2022-07-25  2022-07-25
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_KXH
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
 KXH  O1   O   O     0  -0.455  43.0895  30.7007  -33.8284
 KXH  N    N   NR5   0  -0.262  46.5962  28.5620  -33.0599
 KXH  C15  C   CR16  0  -0.287  44.3372  26.3287  -30.3229
 KXH  C14  C   CR16  0  -0.206  43.6823  25.7896  -29.2289
 KXH  O    O   O2    0  -0.461  42.2369  29.2133  -32.3841
 KXH  C13  C   CR6   0  -0.013  42.9068  26.6001  -28.4143
 KXH  C12  C   CR6   0   0.017  42.8016  27.9578  -28.6974
 KXH  C11  C   CR16  0  -0.249  43.4617  28.4959  -29.7883
 KXH  C10  C   CR6   0   0.063  44.2245  27.6844  -30.6211
 KXH  C9   C   CR5   0   0.316  44.9436  28.2485  -31.7704
 KXH  C8   C   CH2   0  -0.268  49.7792  31.4275  -31.7893
 KXH  C7   C   CH2   0  -0.436  48.7562  30.7063  -32.6538
 KXH  C1   C   CH2   0  -0.200  40.9195  29.7763  -32.4693
 KXH  C2   C   C     0   0.503  43.2278  29.7845  -33.0509
 KXH  C3   C   CR5   0  -0.343  44.5193  29.1609  -32.7691
 KXH  C4   C   CR15  0   0.095  45.6350  29.3321  -33.5678
 KXH  C6   C   CH2   0  -0.440  48.9478  29.1962  -32.6302
 KXH  CL   CL  CL    0  -0.094  41.8529  28.9929  -27.6983
 KXH  N2   N   N     0  -0.291  46.2026  27.9077  -31.9697
 KXH  N1   N   NH2   0  -0.800  49.5867  32.8693  -31.8450
 KXH  H1   H   HCR6  0   0.270  44.9307  25.6821  -30.9546
 KXH  H2   H   HCR6  0   0.291  43.7685  24.7344  -29.0096
 KXH  H3   H   HCR6  0   0.281  43.3902  29.5587  -29.9712
 KXH  H4   H   HCH2  0   0.214  49.6545  31.1077  -30.7511
 KXH  H5   H   HCH2  0   0.190  50.7874  31.1069  -32.0898
 KXH  H6   H   HCH2  0   0.218  48.8376  31.0621  -33.6871
 KXH  H7   H   HCH2  0   0.223  47.7532  30.9744  -32.3095
 KXH  H8   H   HCH3  0   0.245  39.7048  31.2640  -31.5333
 KXH  H9   H   HCH3  0   0.227  40.9470  30.6073  -30.4708
 KXH  H10  H   HCH3  0   0.238  41.3791  31.7671  -31.7379
 KXH  H11  H   HCH2  0   0.240  40.7054  30.0896  -33.4914
 KXH  H12  H   HCH2  0   0.249  40.2529  28.9518  -32.2232
 KXH  H13  H   HCR5  0   0.313  45.7813  29.9256  -34.4557
 KXH  H14  H   HCH2  0   0.280  48.2127  27.3768  -33.5403
 KXH  H15  H   HCH2  0   0.266  48.0029  28.8088  -34.5389
 KXH  H16  H   HCH2  0   0.236  48.8764  28.8191  -31.6063
 KXH  H17  H   HCH2  0   0.241  49.9530  28.9467  -32.9798
 KXH  H18  H   HNH2  0   0.346  50.2489  33.3198  -31.2263
 KXH  H19  H   HNH2  0   0.337  49.8173  33.2012  -32.7739
 KXH  C5   C   CH2   0  -0.312  47.9686  28.4382  -33.5145
 KXH  CL1  CL  CL    0  -0.094  42.0866  25.9166  -27.0642
 KXH  C    C   CH3   0  -0.687  40.7386  30.9200  -31.4946

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
 KXH  C5   N    single    1.451  0.020  1.451
 KXH  C5   C6   single    1.522  0.020  1.522
 KXH  C4   N    aromatic  1.332  0.020  1.332
 KXH  C4   C3   aromatic  1.383  0.020  1.383
 KXH  C1   O    single    1.435  0.020  1.435
 KXH  C1   C    single    1.513  0.020  1.513
 KXH  O    C2   single    1.324  0.020  1.324
 KXH  N    N2   aromatic  1.331  0.020  1.331
 KXH  C7   C6   single    1.522  0.020  1.522
 KXH  C7   C8   single    1.521  0.020  1.521
 KXH  C3   C2   single    1.462  0.020  1.462
 KXH  C3   C9   aromatic  1.418  0.020  1.418
 KXH  C2   O1   double    1.210  0.020  1.210
 KXH  N2   C9   aromatic  1.320  0.020  1.320
 KXH  C9   C10  single    1.468  0.020  1.468
 KXH  C8   N1   single    1.456  0.020  1.456
 KXH  C10  C15  aromatic  1.393  0.020  1.393
 KXH  C10  C11  aromatic  1.391  0.020  1.391
 KXH  C15  C14  aromatic  1.384  0.020  1.384
 KXH  C11  C12  aromatic  1.384  0.020  1.384
 KXH  C14  C13  aromatic  1.386  0.020  1.386
 KXH  C12  C13  aromatic  1.391  0.020  1.391
 KXH  C12  CL   single    1.723  0.020  1.723
 KXH  C13  CL1  single    1.721  0.020  1.721
 KXH  C15  H1   single    0.930  0.020  1.080
 KXH  C14  H2   single    0.930  0.020  1.080
 KXH  C11  H3   single    0.930  0.020  1.080
 KXH  C8   H4   single    0.970  0.020  1.090
 KXH  C8   H5   single    0.970  0.020  1.090
 KXH  C7   H6   single    0.970  0.020  1.090
 KXH  C7   H7   single    0.970  0.020  1.090
 KXH  C    H8   single    0.970  0.020  1.090
 KXH  C    H9   single    0.970  0.020  1.090
 KXH  C    H10  single    0.970  0.020  1.090
 KXH  C1   H11  single    0.970  0.020  1.090
 KXH  C1   H12  single    0.970  0.020  1.090
 KXH  C4   H13  single    0.930  0.020  1.080
 KXH  C5   H14  single    0.970  0.020  1.090
 KXH  C5   H15  single    0.970  0.020  1.090
 KXH  C6   H16  single    0.970  0.020  1.090
 KXH  C6   H17  single    0.970  0.020  1.090
 KXH  N1   H18  single    0.890  0.020  1.040
 KXH  N1   H19  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
 KXH  N2   N    C5   119.63  3.000
 KXH  N2   N    C4   112.53  3.000
 KXH  C5   N    C4   127.75  3.000
 KXH  H1   C15  C10  120.09  3.000
 KXH  H1   C15  C14  119.24  3.000
 KXH  C10  C15  C14  120.67  3.000
 KXH  H2   C14  C13  119.73  3.000
 KXH  H2   C14  C15  120.18  3.000
 KXH  C13  C14  C15  120.09  3.000
 KXH  C2   O    C1   119.20  3.000
 KXH  CL1  C13  C12  120.75  3.000
 KXH  CL1  C13  C14  119.69  3.000
 KXH  C12  C13  C14  119.56  3.000
 KXH  CL   C12  C11  119.08  3.000
 KXH  CL   C12  C13  120.66  3.000
 KXH  C11  C12  C13  120.26  3.000
 KXH  H3   C11  C10  120.58  3.000
 KXH  H3   C11  C12  118.96  3.000
 KXH  C10  C11  C12  120.45  3.000
 KXH  C9   C10  C11  120.88  3.000
 KXH  C11  C10  C15  118.95  3.000
 KXH  C9   C10  C15  120.13  3.000
 KXH  N2   C9   C3   110.20  3.000
 KXH  N2   C9   C10  119.10  3.000
 KXH  C3   C9   C10  130.70  3.000
 KXH  H5   C8   H4   106.18  3.000
 KXH  H5   C8   N1   113.55  3.000
 KXH  H4   C8   N1   108.11  3.000
 KXH  H5   C8   C7   108.84  3.000
 KXH  H4   C8   C7   108.91  3.000
 KXH  N1   C8   C7   111.03  3.000
 KXH  H7   C7   H6   106.58  3.000
 KXH  H7   C7   C6   110.71  3.000
 KXH  H6   C7   C6   109.11  3.000
 KXH  H7   C7   C8   108.76  3.000
 KXH  H6   C7   C8   109.38  3.000
 KXH  C6   C7   C8   112.14  3.000
 KXH  H12  C1   H11  108.02  3.000
 KXH  H12  C1   C    110.70  3.000
 KXH  H11  C1   C    111.29  3.000
 KXH  H12  C1   O    104.58  3.000
 KXH  H11  C1   O    110.40  3.000
 KXH  C    C1   O    111.59  3.000
 KXH  C3   C2   O    112.34  3.000
 KXH  C3   C2   O1   123.24  3.000
 KXH  O    C2   O1   124.40  3.000
 KXH  C4   C3   C2   123.28  3.000
 KXH  C2   C3   C9   132.44  3.000
 KXH  C4   C3   C9   104.19  3.000
 KXH  H13  C4   C3   130.80  3.000
 KXH  H13  C4   N    122.30  3.000
 KXH  C3   C4   N    106.88  3.000
 KXH  H17  C6   H16  106.31  3.000
 KXH  H17  C6   C5   106.99  3.000
 KXH  H16  C6   C5   109.29  3.000
 KXH  H17  C6   C7   109.70  3.000
 KXH  H16  C6   C7   110.39  3.000
 KXH  C5   C6   C7   113.84  3.000
 KXH  C9   N2   N    106.20  3.000
 KXH  H19  N1   H18  105.41  3.000
 KXH  H19  N1   C8   109.24  3.000
 KXH  H18  N1   C8   109.33  3.000
 KXH  H15  C5   H14  107.57  3.000
 KXH  H15  C5   C6   110.89  3.000
 KXH  H14  C5   C6   110.78  3.000
 KXH  H15  C5   N    107.17  3.000
 KXH  H14  C5   N    107.61  3.000
 KXH  C6   C5   N    112.58  3.000
 KXH  H10  C    H9   108.68  3.000
 KXH  H10  C    H8   107.71  3.000
 KXH  H9   C    H8   107.76  3.000
 KXH  H10  C    C1   111.92  3.000
 KXH  H9   C    C1   111.41  3.000
 KXH  H8   C    C1   109.21  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
 KXH  CONST_01  C9   C3   C4   N       0.00   0.0  0
 KXH  CONST_02  C3   C9   N2   N       0.00   0.0  0
 KXH  CONST_03  C10  C9   N2   N     180.00   0.0  0
 KXH  CONST_06  C12  C11  C10  C15     0.00   0.0  0
 KXH  CONST_07  C12  C13  C14  C15     0.00   0.0  0
 KXH  CONST_08  C9   C10  C15  C14   180.00   0.0  0
 KXH  CONST_09  C11  C10  C15  C14     0.00   0.0  0
 KXH  CONST_10  C11  C12  C13  C14     0.00   0.0  0
 KXH  CONST_11  C10  C15  C14  C13     0.00   0.0  0
 KXH  CONST_12  C10  C11  C12  C13     0.00   0.0  0
 KXH  CONST_13  C9   C10  C11  C12   180.00   0.0  0
 KXH  CONST_16  C4   C3   C9   C10   180.00   0.0  0
 KXH  CONST_17  C4   N    N2   C9      0.00   0.0  0
 KXH  CONST_18  N2   N    C4   C3      0.00   0.0  0
 KXH  CONST_19  N2   C9   C3   C4      0.00   0.0  0
 KXH  CONST_20  C2   C3   C4   N     180.00   0.0  0
 KXH  CONST_21  CL1  C13  C14  C15   180.00   0.0  0
 KXH  CONST_22  CL   C12  C13  C14   180.00   0.0  0
 KXH  CONST_23  CL1  C13  C12  C11   180.00   0.0  0
 KXH  CONST_24  C2   C3   C9   C10     0.00   0.0  0
 KXH  CONST_25  CL   C12  C11  C10   180.00   0.0  0
 KXH  CONST_26  C5   N    N2   C9    180.00   0.0  0
 KXH  CONST_27  N2   C9   C3   C2    180.00   0.0  0
 KXH  CONST_28  C5   N    C4   C3    180.00   0.0  0
 KXH  CONST_29  H3   C11  C10  C15   180.00   0.0  0
 KXH  CONST_30  H1   C15  C14  C13   180.00   0.0  0
 KXH  CONST_31  H2   C14  C13  C12   180.00   0.0  0
 KXH  CONST_32  H13  C4   C3   C9    180.00   0.0  0
 KXH  Var_01    C4   C3   C2   O1    -15.54  30.0  2
 KXH  Var_02    C6   C5   N    C4    102.89  30.0  1
 KXH  Var_03    C7   C6   C5   N     -65.22  30.0  3
 KXH  Var_04    C3   C2   O    C1    175.12  30.0  3
 KXH  Var_05    C5   C6   C7   C8   -178.34  30.0  3
 KXH  Var_06    N1   C8   C7   C6    179.15  30.0  3
 KXH  Var_07    H8   C    C1   O    -175.40  30.0  3
 KXH  Var_08    H18  N1   C8   C7    177.18  30.0  3
 KXH  Var_09    H11  C1   O    C2     40.81  30.0  2

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
 KXH  plan-1  N    0.020
 KXH  plan-1  C10  0.020
 KXH  plan-1  C9   0.020
 KXH  plan-1  C2   0.020
 KXH  plan-1  C3   0.020
 KXH  plan-1  C4   0.020
 KXH  plan-1  N2   0.020
 KXH  plan-1  H13  0.020
 KXH  plan-1  C5   0.020
 KXH  plan-2  C15  0.020
 KXH  plan-2  C14  0.020
 KXH  plan-2  C13  0.020
 KXH  plan-2  C12  0.020
 KXH  plan-2  C11  0.020
 KXH  plan-2  C10  0.020
 KXH  plan-2  C9   0.020
 KXH  plan-2  CL   0.020
 KXH  plan-2  H1   0.020
 KXH  plan-2  H2   0.020
 KXH  plan-2  H3   0.020
 KXH  plan-2  CL1  0.020
 KXH  plan-3  O1   0.020
 KXH  plan-3  O    0.020
 KXH  plan-3  C2   0.020
 KXH  plan-3  C3   0.020

