# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 15:25:06 2020
#   Inital geometry file: a 112 line input string
#   Ligand name: 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)-1H-pyrazole-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)c1n[nH]c(c2cc(Cl)c(O)cc2O)c1c3ccc(OC)cc3
#
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
 BSM  BSM  5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)-1H-pyrazole-3-carboxamide  ligand  45  27  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_BSM
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
 BSM  C22   C   CH3   0  -0.436  -5.7626   0.8837  -0.3345
 BSM  O21   O   O2    0  -0.472  -5.1142   0.0285   0.5844
 BSM  C18   C   CR6   0   0.365  -3.7694   0.0731   0.6640
 BSM  C19   C   CR16  0  -0.339  -3.1752  -0.7923   1.5871
 BSM  C20   C   CR16  0  -0.269  -1.8041  -0.8146   1.7388
 BSM  C17   C   CR16  0  -0.372  -2.9622   0.9090  -0.1007
 BSM  C16   C   CR16  0  -0.301  -1.5819   0.8722   0.0665
 BSM  C7    C   CR6   0   0.035  -0.9790   0.0203   0.9828
 BSM  C3    C   CR5   0  -0.163   0.4815  -0.0265   1.1054
 BSM  C2    C   CR5   0   0.121   1.3195   0.0891   2.2377
 BSM  C8    C   C     0   0.497   0.9399   0.3423   3.6499
 BSM  O9    O   O     0  -0.485  -0.2085   0.6234   3.9664
 BSM  N10   N   NH1   0  -0.645   1.9434   0.2453   4.5327
 BSM  C26   C   CH2   0  -0.257   1.7720   0.5075   5.9467
 BSM  C27   C   CH3   0  -0.701   3.0450   0.1786   6.7028
 BSM  N1    N   N     0  -0.281   2.5977  -0.0014   1.8999
 BSM  N5    N   NR15  0  -0.478   2.6020  -0.1702   0.5967
 BSM  C4    C   CR5   0   0.452   1.3669  -0.1976   0.0555
 BSM  C6    C   CR6   0  -0.133   1.1433  -0.3627  -1.3808
 BSM  C11   C   CR16  0  -0.227   1.6807   0.5415  -2.2878
 BSM  C12   C   CR6   0  -0.192   1.4687   0.4002  -3.6459
 BSM  CL25  CL  CL    0  -0.119   2.1373   1.5495  -4.7613
 BSM  C13   C   CR6   0   0.439   0.7032  -0.6578  -4.1384
 BSM  O24   O   OH1   0  -0.607   0.4576  -0.8473  -5.4381
 BSM  C14   C   CR16  0  -0.475   0.1677  -1.5704  -3.2361
 BSM  C15   C   CR6   0   0.378   0.3844  -1.4343  -1.8718
 BSM  O23   O   OH1   0  -0.605  -0.0929  -2.3135  -0.9838
 BSM  H221  H   HCH3  0   0.259  -6.8283   0.6908  -0.2389
 BSM  H222  H   HCH3  0   0.227  -5.5764   1.9383  -0.1145
 BSM  H223  H   HCH3  0   0.227  -5.4597   0.6824  -1.3653
 BSM  H19   H   HCR6  0   0.257  -3.8015  -1.4492   2.1781
 BSM  H20   H   HCR6  0   0.238  -1.3651  -1.5016   2.4499
 BSM  H17   H   HCR6  0   0.274  -3.3823   1.5947  -0.8242
 BSM  H16   H   HCR6  0   0.247  -0.9684   1.5355  -0.5305
 BSM  H10   H   HNH1  0   0.403   2.8686   0.0439   4.1869
 BSM  H261  H   HCH2  0   0.235   0.9440  -0.0918   6.3309
 BSM  H262  H   HCH2  0   0.233   1.5033   1.5554   6.1069
 BSM  H271  H   HCH3  0   0.245   2.9112   0.3816   7.7642
 BSM  H272  H   HCH3  0   0.234   3.3115  -0.8732   6.5934
 BSM  H273  H   HCH3  0   0.234   3.8838   0.7820   6.3526
 BSM  H5    H   HNR5  0   0.425   3.4775  -0.2897   0.1088
 BSM  H11   H   HCR6  0   0.287   2.2589   1.3818  -1.9258
 BSM  H24   H   HOH1  0   0.472   0.8699  -0.1584  -5.9755
 BSM  H14   H   HCR6  0   0.290  -0.4127  -2.4025  -3.6188
 BSM  H23   H   HOH1  0   0.480  -0.6264  -2.9858  -1.4229

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
 BSM  C22  O21   single    1.413  0.020  1.413
 BSM  C22  H221  single    0.970  0.020  1.090
 BSM  C22  H222  single    0.970  0.020  1.090
 BSM  C22  H223  single    0.970  0.020  1.090
 BSM  O21  C18   single    1.348  0.020  1.348
 BSM  C18  C19   aromatic  1.398  0.020  1.398
 BSM  C18  C17   aromatic  1.391  0.020  1.391
 BSM  C19  C20   aromatic  1.380  0.020  1.380
 BSM  C19  H19   single    0.930  0.020  1.080
 BSM  C20  C7    aromatic  1.396  0.020  1.396
 BSM  C20  H20   single    0.930  0.020  1.080
 BSM  C17  C16   aromatic  1.391  0.020  1.391
 BSM  C17  H17   single    0.930  0.020  1.080
 BSM  C16  C7    aromatic  1.389  0.020  1.389
 BSM  C16  H16   single    0.930  0.020  1.080
 BSM  C7   C3    single    1.466  0.020  1.466
 BSM  C3   C2    aromatic  1.413  0.020  1.413
 BSM  C3   C4    aromatic  1.384  0.020  1.384
 BSM  C2   C8    single    1.484  0.020  1.484
 BSM  C2   N1    aromatic  1.325  0.020  1.325
 BSM  C8   O9    double    1.224  0.020  1.224
 BSM  C8   N10   single    1.340  0.020  1.340
 BSM  N10  C26   single    1.448  0.020  1.448
 BSM  N10  H10   single    0.860  0.020  1.020
 BSM  C26  C27   single    1.517  0.020  1.517
 BSM  C26  H261  single    0.970  0.020  1.090
 BSM  C26  H262  single    0.970  0.020  1.090
 BSM  C27  H271  single    0.970  0.020  1.090
 BSM  C27  H272  single    0.970  0.020  1.090
 BSM  C27  H273  single    0.970  0.020  1.090
 BSM  N1   N5    aromatic  1.314  0.020  1.314
 BSM  N5   C4    aromatic  1.349  0.020  1.349
 BSM  N5   H5    single    0.860  0.020  1.020
 BSM  C4   C6    single    1.463  0.020  1.463
 BSM  C6   C11   aromatic  1.389  0.020  1.389
 BSM  C6   C15   aromatic  1.402  0.020  1.402
 BSM  C11  C12   aromatic  1.382  0.020  1.382
 BSM  C11  H11   single    0.930  0.020  1.080
 BSM  C12  CL25  single    1.736  0.020  1.736
 BSM  C12  C13   aromatic  1.396  0.020  1.396
 BSM  C13  O24   single    1.336  0.020  1.336
 BSM  C13  C14   aromatic  1.391  0.020  1.391
 BSM  O24  H24   single    0.850  0.020  0.980
 BSM  C14  C15   aromatic  1.388  0.020  1.388
 BSM  C14  H14   single    0.930  0.020  1.080
 BSM  C15  O23   single    1.338  0.020  1.338
 BSM  O23  H23   single    0.850  0.020  0.980

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
 BSM  H223  C22  H222  108.68  3.000
 BSM  H223  C22  H221  108.78  3.000
 BSM  H222  C22  H221  108.69  3.000
 BSM  H223  C22  O21   112.00  3.000
 BSM  H222  C22  O21   112.02  3.000
 BSM  H221  C22  O21   106.57  3.000
 BSM  C18   O21  C22   118.44  3.000
 BSM  C17   C18  C19   119.23  3.000
 BSM  C17   C18  O21   124.49  3.000
 BSM  C19   C18  O21   116.27  3.000
 BSM  H19   C19  C20   120.32  3.000
 BSM  H19   C19  C18   119.34  3.000
 BSM  C20   C19  C18   120.34  3.000
 BSM  H20   C20  C7    119.72  3.000
 BSM  H20   C20  C19   119.07  3.000
 BSM  C7    C20  C19   121.21  3.000
 BSM  H17   C17  C16   118.85  3.000
 BSM  H17   C17  C18   121.55  3.000
 BSM  C16   C17  C18   119.59  3.000
 BSM  H16   C16  C7    119.57  3.000
 BSM  H16   C16  C17   118.66  3.000
 BSM  C7    C16  C17   121.76  3.000
 BSM  C3    C7   C16   120.47  3.000
 BSM  C3    C7   C20   121.62  3.000
 BSM  C16   C7   C20   117.87  3.000
 BSM  C4    C3   C2    103.80  3.000
 BSM  C4    C3   C7    125.29  3.000
 BSM  C2    C3   C7    130.91  3.000
 BSM  N1    C2   C8    120.06  3.000
 BSM  N1    C2   C3    111.23  3.000
 BSM  C8    C2   C3    128.66  3.000
 BSM  N10   C8   O9    123.29  3.000
 BSM  N10   C8   C2    115.03  3.000
 BSM  O9    C8   C2    121.68  3.000
 BSM  H10   N10  C26   118.67  3.000
 BSM  H10   N10  C8    118.41  3.000
 BSM  C26   N10  C8    122.79  3.000
 BSM  H262  C26  H261  106.74  3.000
 BSM  H262  C26  C27   109.94  3.000
 BSM  H261  C26  C27   110.00  3.000
 BSM  H262  C26  N10   110.22  3.000
 BSM  H261  C26  N10   109.50  3.000
 BSM  C27   C26  N10   110.37  3.000
 BSM  H273  C27  H272  108.26  3.000
 BSM  H273  C27  H271  107.71  3.000
 BSM  H272  C27  H271  107.92  3.000
 BSM  H273  C27  C26   111.43  3.000
 BSM  H272  C27  C26   111.36  3.000
 BSM  H271  C27  C26   110.02  3.000
 BSM  N5    N1   C2    105.35  3.000
 BSM  H5    N5   C4    126.72  3.000
 BSM  H5    N5   N1    119.83  3.000
 BSM  C4    N5   N1    113.42  3.000
 BSM  C6    C4   N5    122.42  3.000
 BSM  C6    C4   C3    131.38  3.000
 BSM  N5    C4   C3    106.19  3.000
 BSM  C15   C6   C11   118.58  3.000
 BSM  C15   C6   C4    120.85  3.000
 BSM  C11   C6   C4    120.57  3.000
 BSM  H11   C11  C12   119.34  3.000
 BSM  H11   C11  C6    119.58  3.000
 BSM  C12   C11  C6    121.06  3.000
 BSM  C13   C12  CL25  119.11  3.000
 BSM  C13   C12  C11   120.56  3.000
 BSM  CL25  C12  C11   120.32  3.000
 BSM  C14   C13  O24   117.86  3.000
 BSM  C14   C13  C12   118.66  3.000
 BSM  O24   C13  C12   123.48  3.000
 BSM  H24   O24  C13   111.19  3.000
 BSM  H14   C14  C15   120.38  3.000
 BSM  H14   C14  C13   118.73  3.000
 BSM  C15   C14  C13   120.89  3.000
 BSM  O23   C15  C14   122.17  3.000
 BSM  O23   C15  C6    117.58  3.000
 BSM  C14   C15  C6    120.24  3.000
 BSM  H23   O23  C15   110.69  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
 BSM  CONST_01  C7    C20  C19  C18      0.00   0.0  0
 BSM  CONST_02  C7    C16  C17  C18      0.00   0.0  0
 BSM  CONST_03  C16   C17  C18  C19      0.00   0.0  0
 BSM  CONST_04  C16   C7   C20  C19      0.00   0.0  0
 BSM  CONST_05  C3    C7   C20  C19    180.00   0.0  0
 BSM  CONST_06  C17   C18  C19  C20      0.00   0.0  0
 BSM  CONST_07  C17   C16  C7   C20      0.00   0.0  0
 BSM  CONST_10  C3    C7   C16  C17    180.00   0.0  0
 BSM  CONST_13  N1    C2   C3   C7     180.00   0.0  0
 BSM  CONST_14  N5    C4   C3   C7     180.00   0.0  0
 BSM  CONST_15  C6    C4   C3   C7       0.00   0.0  0
 BSM  CONST_16  N5    N1   C2   C3       0.00   0.0  0
 BSM  CONST_17  N1    N5   C4   C3       0.00   0.0  0
 BSM  CONST_20  N5    C4   C3   C2       0.00   0.0  0
 BSM  CONST_21  C6    C4   C3   C2     180.00   0.0  0
 BSM  CONST_22  C4    N5   N1   C2       0.00   0.0  0
 BSM  CONST_23  C4    C3   C2   N1       0.00   0.0  0
 BSM  CONST_24  C6    C4   N5   N1     180.00   0.0  0
 BSM  CONST_27  C12   C11  C6   C4     180.00   0.0  0
 BSM  CONST_28  C14   C15  C6   C4     180.00   0.0  0
 BSM  CONST_29  C13   C12  C11  C6       0.00   0.0  0
 BSM  CONST_30  C13   C14  C15  C6       0.00   0.0  0
 BSM  CONST_31  C14   C15  C6   C11      0.00   0.0  0
 BSM  CONST_32  C14   C13  C12  C11      0.00   0.0  0
 BSM  CONST_33  C15   C6   C11  C12      0.00   0.0  0
 BSM  CONST_34  C15   C14  C13  C12      0.00   0.0  0
 BSM  CONST_35  C20   C19  C18  O21    180.00   0.0  0
 BSM  CONST_36  C16   C17  C18  O21    180.00   0.0  0
 BSM  CONST_37  C8    C2   C3   C7       0.00   0.0  0
 BSM  CONST_38  C4    C3   C2   C8     180.00   0.0  0
 BSM  CONST_39  N5    N1   C2   C8     180.00   0.0  0
 BSM  CONST_40  O23   C15  C6   C4       0.00   0.0  0
 BSM  CONST_41  CL25  C12  C11  C6     180.00   0.0  0
 BSM  CONST_42  O23   C15  C6   C11    180.00   0.0  0
 BSM  CONST_43  O24   C13  C12  C11    180.00   0.0  0
 BSM  CONST_44  C14   C13  C12  CL25   180.00   0.0  0
 BSM  CONST_45  O23   C15  C14  C13    180.00   0.0  0
 BSM  CONST_46  C15   C14  C13  O24    180.00   0.0  0
 BSM  CONST_47  H20   C20  C19  C18    180.00   0.0  0
 BSM  CONST_48  H16   C16  C17  C18    180.00   0.0  0
 BSM  CONST_49  H17   C17  C18  C19    180.00   0.0  0
 BSM  CONST_50  H19   C19  C18  C17    180.00   0.0  0
 BSM  CONST_51  H5    N5   C4   C3     180.00   0.0  0
 BSM  CONST_52  H11   C11  C6   C4       0.00   0.0  0
 BSM  CONST_53  H14   C14  C15  C6     180.00   0.0  0
 BSM  CONST_54  C26   N10  C8   C2     180.00   0.0  0
 BSM  CONST_55  H10   N10  C8   C2       0.00   0.0  0
 BSM  CONST_56  C26   N10  C8   O9       0.00   0.0  0
 BSM  Var_01    C19   C18  O21  C22   -179.97  30.0  2
 BSM  Var_02    O9    C8   C2   C3      -7.77  30.0  2
 BSM  Var_03    H221  C22  O21  C18   -179.98  30.0  3
 BSM  Var_04    C27   C26  N10  C8     174.22  30.0  3
 BSM  Var_05    H271  C27  C26  N10    179.77  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
 BSM  plan-1  C7    0.020
 BSM  plan-1  C3    0.020
 BSM  plan-1  C2    0.020
 BSM  plan-1  C8    0.020
 BSM  plan-1  N1    0.020
 BSM  plan-1  N5    0.020
 BSM  plan-1  C4    0.020
 BSM  plan-1  C6    0.020
 BSM  plan-1  H5    0.020
 BSM  plan-2  O21   0.020
 BSM  plan-2  C18   0.020
 BSM  plan-2  C19   0.020
 BSM  plan-2  C20   0.020
 BSM  plan-2  C17   0.020
 BSM  plan-2  C16   0.020
 BSM  plan-2  C7    0.020
 BSM  plan-2  C3    0.020
 BSM  plan-2  H19   0.020
 BSM  plan-2  H20   0.020
 BSM  plan-2  H17   0.020
 BSM  plan-2  H16   0.020
 BSM  plan-3  C4    0.020
 BSM  plan-3  C6    0.020
 BSM  plan-3  C11   0.020
 BSM  plan-3  C12   0.020
 BSM  plan-3  CL25  0.020
 BSM  plan-3  C13   0.020
 BSM  plan-3  O24   0.020
 BSM  plan-3  C14   0.020
 BSM  plan-3  C15   0.020
 BSM  plan-3  O23   0.020
 BSM  plan-3  H11   0.020
 BSM  plan-3  H14   0.020
 BSM  plan-4  C2    0.020
 BSM  plan-4  C8    0.020
 BSM  plan-4  O9    0.020
 BSM  plan-4  N10   0.020
 BSM  plan-4  C26   0.020
 BSM  plan-4  H10   0.020

