# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 01:44:32 2020
#   Inital geometry file: a 108 line input string
#   Ligand name: 4-(1,3-benzodioxol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-pyrazole-5-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1cc(c(O)cc1O)c2n[nH]c(C(O)=O)c2c3ccc4OCOc4c3
#
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
 4BC  4BC  '4-(1,3-benzodioxol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-pyrazole-5-carboxylic acid'  ligand  42  27  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_4BC
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
 4BC  C15   C  CR16   0  -0.357   0.5030  -0.7578  -2.1219
 4BC  C12   C  CR6    0   0.300   1.8055  -0.5581  -2.5003
 4BC  O17   O  O2     0  -0.490   2.5856  -1.3399  -3.2910
 4BC  C19   C  CH2    0   0.067   3.7706  -0.5942  -3.5305
 4BC  O18   O  O2     0  -0.488   3.7990   0.4571  -2.5748
 4BC  C16   C  CR6    0   0.282   2.5428   0.5322  -2.0666
 4BC  C22   C  CR16   0  -0.323   2.0033   1.4798  -1.2338
 4BC  C20   C  CR16   0  -0.308   0.6739   1.2892  -0.8411
 4BC  C8    C  CR6    0  -0.006  -0.0714   0.1942  -1.2634
 4BC  C4    C  CR5    0  -0.201  -1.4413   0.0097  -0.7608
 4BC  C1    C  CR5    0   0.226  -2.6264   0.0157  -1.4809
 4BC  C7    C  C      0   0.373  -2.9540   0.1755  -2.9460
 4BC  O21   O  OC    -1  -0.600  -4.1685   0.1225  -3.2193
 4BC  O23   O  O      0  -0.563  -1.9958   0.3439  -3.7129
 4BC  N5    N  NR15   0  -0.454  -3.6099  -0.1269  -0.5799
 4BC  C2    C  CR5    0   0.362  -1.8445  -0.1650   0.5866
 4BC  N3    N  N      0  -0.380  -3.1715  -0.2393   0.6596
 4BC  C6    C  CR6    0  -0.112  -1.0532  -0.2391   1.8175
 4BC  C10   C  CR16   0  -0.364   0.2899  -0.6217   1.8054
 4BC  C14   C  CR6    0   0.025   1.0930  -0.6522   2.9320
 4BC  C26   C  CH2    0  -0.488   2.5458  -1.0283   2.8318
 4BC  C27   C  CH3    0  -0.656   3.4608   0.1882   2.6963
 4BC  C13   C  CR6    0   0.328   0.5064  -0.2770   4.1471
 4BC  O25   O  OH1    0  -0.628   1.2864  -0.2810   5.2466
 4BC  C11   C  CR16   0  -0.481  -0.8364   0.0697   4.2094
 4BC  C9    C  CR6    0   0.328  -1.6249   0.0789   3.0623
 4BC  O24   O  OH1    0  -0.645  -2.9188   0.4070   3.2098
 4BC  H15   H  HCR6   0   0.256  -0.0592  -1.6181  -2.4580
 4BC  H191  H  HCH2   0   0.230   3.7487  -0.1754  -4.5431
 4BC  H192  H  HCH2   0   0.244   4.6429  -1.2345  -3.4016
 4BC  H22   H  HCR6   0   0.268   2.5729   2.3327  -0.8906
 4BC  H20   H  HCR6   0   0.246   0.2168   2.0131  -0.1792
 4BC  HN5   H  HNR5   0   0.409  -4.5967  -0.1513  -0.7847
 4BC  H10   H  HCR6   0   0.250   0.7344  -0.9189   0.8646
 4BC  H261  H  HCH2   0   0.235   2.6806  -1.6730   1.9603
 4BC  H262  H  HCH2   0   0.233   2.8521  -1.6202   3.6968
 4BC  H271  H  HCH3   0   0.226   4.5066  -0.1155   2.6309
 4BC  H272  H  HCH3   0   0.222   3.2202   0.7544   1.7953
 4BC  H273  H  HCH3   0   0.224   3.3615   0.8593   3.5496
 4BC  H25   H  HOH1   0   0.474   0.7718  -0.0345   6.0230
 4BC  H11   H  HCR6   0   0.268  -1.2912   0.3312   5.1592
 4BC  H24   H  HOH1   0   0.468  -3.3840   0.2483   2.3611

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
 4BC  C15  C12   aromatic  1.371  0.020  1.371
 4BC  C15  C8    aromatic  1.405  0.020  1.405
 4BC  C15  H15   single    0.930  0.020  1.080
 4BC  C12  O17   single    1.358  0.020  1.358
 4BC  C12  C16   aromatic  1.386  0.020  1.386
 4BC  O17  C19   single    1.420  0.020  1.420
 4BC  C19  O18   single    1.421  0.020  1.421
 4BC  C19  H191  single    0.970  0.020  1.090
 4BC  C19  H192  single    0.970  0.020  1.090
 4BC  O18  C16   single    1.357  0.020  1.357
 4BC  C16  C22   aromatic  1.372  0.020  1.372
 4BC  C22  C20   aromatic  1.399  0.020  1.399
 4BC  C22  H22   single    0.930  0.020  1.080
 4BC  C20  C8    aromatic  1.390  0.020  1.390
 4BC  C20  H20   single    0.930  0.020  1.080
 4BC  C8   C4    single    1.471  0.020  1.471
 4BC  C4   C1    aromatic  1.387  0.020  1.387
 4BC  C4   C2    aromatic  1.417  0.020  1.417
 4BC  C1   C7    single    1.510  0.020  1.510
 4BC  C1   N5    aromatic  1.341  0.020  1.341
 4BC  C7   O21   deloc     1.246  0.020  1.246
 4BC  C7   O23   deloc     1.239  0.020  1.239
 4BC  N5   N3    aromatic  1.320  0.020  1.320
 4BC  N5   HN5   single    0.860  0.020  1.020
 4BC  C2   N3    aromatic  1.331  0.020  1.331
 4BC  C2   C6    single    1.465  0.020  1.465
 4BC  C6   C10   aromatic  1.397  0.020  1.397
 4BC  C6   C9    aromatic  1.406  0.020  1.406
 4BC  C10  C14   aromatic  1.384  0.020  1.384
 4BC  C10  H10   single    0.930  0.020  1.080
 4BC  C14  C26   single    1.504  0.020  1.504
 4BC  C14  C13   aromatic  1.400  0.020  1.400
 4BC  C26  C27   single    1.528  0.020  1.528
 4BC  C26  H261  single    0.970  0.020  1.090
 4BC  C26  H262  single    0.970  0.020  1.090
 4BC  C27  H271  single    0.970  0.020  1.090
 4BC  C27  H272  single    0.970  0.020  1.090
 4BC  C27  H273  single    0.970  0.020  1.090
 4BC  C13  O25   single    1.348  0.020  1.348
 4BC  C13  C11   aromatic  1.388  0.020  1.388
 4BC  O25  H25   single    0.850  0.020  0.980
 4BC  C11  C9    aromatic  1.392  0.020  1.392
 4BC  C11  H11   single    0.930  0.020  1.080
 4BC  C9   O24   single    1.343  0.020  1.343
 4BC  O24  H24   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
 4BC  H15   C15  C8    121.10  3.000
 4BC  H15   C15  C12   121.61  3.000
 4BC  C8    C15  C12   117.29  3.000
 4BC  C16   C12  O17   109.23  3.000
 4BC  C16   C12  C15   122.25  3.000
 4BC  O17   C12  C15   128.50  3.000
 4BC  C19   O17  C12   105.97  3.000
 4BC  H192  C19  H191  110.47  3.000
 4BC  H192  C19  O18   109.82  3.000
 4BC  H191  C19  O18   109.82  3.000
 4BC  H192  C19  O17   109.84  3.000
 4BC  H191  C19  O17   109.86  3.000
 4BC  O18   C19  O17   106.96  3.000
 4BC  C16   O18  C19   105.91  3.000
 4BC  C22   C16  O18   129.01  3.000
 4BC  C22   C16  C12   121.61  3.000
 4BC  O18   C16  C12   109.38  3.000
 4BC  H22   C22  C20   121.25  3.000
 4BC  H22   C22  C16   122.02  3.000
 4BC  C20   C22  C16   116.74  3.000
 4BC  H20   C20  C8    119.09  3.000
 4BC  H20   C20  C22   118.81  3.000
 4BC  C8    C20  C22   122.10  3.000
 4BC  C4    C8   C20   119.62  3.000
 4BC  C4    C8   C15   120.32  3.000
 4BC  C20   C8   C15   120.01  3.000
 4BC  C2    C4   C1    104.54  3.000
 4BC  C2    C4   C8    127.25  3.000
 4BC  C1    C4   C8    128.17  3.000
 4BC  N5    C1   C7    120.26  3.000
 4BC  N5    C1   C4    106.10  3.000
 4BC  C7    C1   C4    133.61  3.000
 4BC  O23   C7   O21   128.60  3.000
 4BC  O23   C7   C1    116.57  3.000
 4BC  O21   C7   C1    114.82  3.000
 4BC  HN5   N5   N3    120.93  3.000
 4BC  HN5   N5   C1    125.72  3.000
 4BC  N3    N5   C1    113.35  3.000
 4BC  C6    C2   N3    119.31  3.000
 4BC  C6    C2   C4    130.64  3.000
 4BC  N3    C2   C4    110.04  3.000
 4BC  C2    N3   N5    105.96  3.000
 4BC  C9    C6   C10   117.43  3.000
 4BC  C9    C6   C2    120.84  3.000
 4BC  C10   C6   C2    121.74  3.000
 4BC  H10   C10  C14   117.61  3.000
 4BC  H10   C10  C6    118.53  3.000
 4BC  C14   C10  C6    123.86  3.000
 4BC  C13   C14  C26   121.97  3.000
 4BC  C13   C14  C10   117.22  3.000
 4BC  C26   C14  C10   120.78  3.000
 4BC  H262  C26  H261  106.10  3.000
 4BC  H262  C26  C27   109.50  3.000
 4BC  H261  C26  C27   108.98  3.000
 4BC  H262  C26  C14   110.72  3.000
 4BC  H261  C26  C14   108.66  3.000
 4BC  C27   C26  C14   112.66  3.000
 4BC  H273  C27  H272  107.87  3.000
 4BC  H273  C27  H271  107.80  3.000
 4BC  H272  C27  H271  107.84  3.000
 4BC  H273  C27  C26   111.48  3.000
 4BC  H272  C27  C26   110.75  3.000
 4BC  H271  C27  C26   110.96  3.000
 4BC  C11   C13  O25   121.58  3.000
 4BC  C11   C13  C14   120.73  3.000
 4BC  O25   C13  C14   117.68  3.000
 4BC  H25   O25  C13   110.34  3.000
 4BC  H11   C11  C9    118.84  3.000
 4BC  H11   C11  C13   120.32  3.000
 4BC  C9    C11  C13   120.83  3.000
 4BC  O24   C9   C11   117.19  3.000
 4BC  O24   C9   C6    122.97  3.000
 4BC  C11   C9   C6    119.84  3.000
 4BC  H24   O24  C9    108.81  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
 4BC  CONST_01  C22   C16  C12  C15     0.00   0.0  0
 4BC  CONST_02  C22   C20  C8   C15     0.00   0.0  0
 4BC  CONST_05  C20   C8   C15  C12     0.00   0.0  0
 4BC  CONST_06  C4    C8   C15  C12   180.00   0.0  0
 4BC  CONST_07  C20   C22  C16  C12     0.00   0.0  0
 4BC  CONST_08  C8    C15  C12  C16     0.00   0.0  0
 4BC  CONST_09  C8    C20  C22  C16     0.00   0.0  0
 4BC  CONST_10  C4    C8   C20  C22   180.00   0.0  0
 4BC  CONST_13  N5    C1   C4   C8    180.00   0.0  0
 4BC  CONST_14  N3    C2   C4   C8    180.00   0.0  0
 4BC  CONST_15  C6    C2   C4   C8      0.00   0.0  0
 4BC  CONST_16  N3    N5   C1   C4      0.00   0.0  0
 4BC  CONST_17  N5    N3   C2   C4      0.00   0.0  0
 4BC  CONST_20  N3    C2   C4   C1      0.00   0.0  0
 4BC  CONST_21  C6    C2   C4   C1    180.00   0.0  0
 4BC  CONST_22  C2    N3   N5   C1      0.00   0.0  0
 4BC  CONST_23  C2    C4   C1   N5      0.00   0.0  0
 4BC  CONST_24  C6    C2   N3   N5    180.00   0.0  0
 4BC  CONST_25  C14   C10  C6   C2    180.00   0.0  0
 4BC  CONST_26  C11   C9   C6   C2    180.00   0.0  0
 4BC  CONST_29  C13   C14  C10  C6      0.00   0.0  0
 4BC  CONST_30  C13   C11  C9   C6      0.00   0.0  0
 4BC  CONST_31  C11   C9   C6   C10     0.00   0.0  0
 4BC  CONST_32  C11   C13  C14  C10     0.00   0.0  0
 4BC  CONST_33  C9    C6   C10  C14     0.00   0.0  0
 4BC  CONST_34  C9    C11  C13  C14     0.00   0.0  0
 4BC  CONST_35  C7    C1   C4   C8      0.00   0.0  0
 4BC  CONST_36  C2    C4   C1   C7    180.00   0.0  0
 4BC  CONST_37  N3    N5   C1   C7    180.00   0.0  0
 4BC  CONST_38  O24   C9   C6   C2      0.00   0.0  0
 4BC  CONST_39  C26   C14  C10  C6    180.00   0.0  0
 4BC  CONST_40  O24   C9   C6   C10   180.00   0.0  0
 4BC  CONST_41  O25   C13  C14  C10   180.00   0.0  0
 4BC  CONST_42  C11   C13  C14  C26   180.00   0.0  0
 4BC  CONST_43  O24   C9   C11  C13   180.00   0.0  0
 4BC  CONST_44  C9    C11  C13  O25   180.00   0.0  0
 4BC  CONST_45  H20   C20  C8   C15   180.00   0.0  0
 4BC  CONST_46  H22   C22  C16  C12   180.00   0.0  0
 4BC  CONST_47  H15   C15  C12  O17     0.00   0.0  0
 4BC  CONST_48  HN5   N5   C1   C4    180.00   0.0  0
 4BC  CONST_49  H10   C10  C6   C2      0.00   0.0  0
 4BC  CONST_50  H11   C11  C9   C6    180.00   0.0  0
 4BC  Var_01    O18   C19  O17  C12    15.52  30.0  1
 4BC  Var_02    C16   C12  O17  C19    -9.70  30.0  1
 4BC  Var_03    C22   C16  O18  C19  -171.30  30.0  1
 4BC  Var_04    O21   C7   C1   C4    179.95  30.0  2
 4BC  Var_05    C27   C26  C14  C10    94.39  30.0  2
 4BC  Var_06    H271  C27  C26  C14   179.71  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
 4BC  plan-1  C8   0.020
 4BC  plan-1  C4   0.020
 4BC  plan-1  C1   0.020
 4BC  plan-1  C7   0.020
 4BC  plan-1  N5   0.020
 4BC  plan-1  C2   0.020
 4BC  plan-1  N3   0.020
 4BC  plan-1  C6   0.020
 4BC  plan-1  HN5  0.020
 4BC  plan-2  C2   0.020
 4BC  plan-2  C6   0.020
 4BC  plan-2  C10  0.020
 4BC  plan-2  C14  0.020
 4BC  plan-2  C26  0.020
 4BC  plan-2  C13  0.020
 4BC  plan-2  O25  0.020
 4BC  plan-2  C11  0.020
 4BC  plan-2  C9   0.020
 4BC  plan-2  O24  0.020
 4BC  plan-2  H10  0.020
 4BC  plan-2  H11  0.020
 4BC  plan-3  C15  0.020
 4BC  plan-3  C12  0.020
 4BC  plan-3  O17  0.020
 4BC  plan-3  O18  0.020
 4BC  plan-3  C16  0.020
 4BC  plan-3  C22  0.020
 4BC  plan-3  C20  0.020
 4BC  plan-3  C8   0.020
 4BC  plan-3  C4   0.020
 4BC  plan-3  H15  0.020
 4BC  plan-3  H22  0.020
 4BC  plan-3  H20  0.020
 4BC  plan-4  C1   0.020
 4BC  plan-4  C7   0.020
 4BC  plan-4  O21  0.020
 4BC  plan-4  O23  0.020

