# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 04:46:20 2020
#   Inital geometry file: a 119 line input string
#   Ligand name: 5-[3-(1~{H}-indol-3-yl)propoxy]-1-phenyl-pyrazole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cnn(c2ccccc2)c1OCCCc3c[nH]c4ccccc34
#
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
 EP8  EP8  '5-[3-(1~{H}-indol-3-yl)propoxy]-1-phenyl-pyrazole-4-carboxylic acid'  ligand  45  27  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_EP8
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
 EP8  C10   C  CH2    0  -0.542  -1.9350  -1.2526  -1.1393
 EP8  C15   C  CR5    0  -0.390   3.5706  -1.5756  -0.0353
 EP8  C20   C  CR16   0  -0.288   3.2523   2.8695  -0.7984
 EP8  C21   C  CR16   0  -0.253   2.7727   4.1687  -0.7348
 EP8  C22   C  CR16   0  -0.257   1.8656   4.5353   0.2509
 EP8  C24   C  CR16   0  -0.282   1.9375   2.2955   1.1408
 EP8  C01   C  CR16   0  -0.269  -4.9031   2.1478   0.0100
 EP8  C02   C  CR16   0  -0.376  -3.8995   1.2817  -0.3783
 EP8  C03   C  CR56   0   0.026  -4.1337  -0.0973  -0.3235
 EP8  C04   C  CR56   0   0.354  -5.3901  -0.5635   0.1251
 EP8  C05   C  CR16   0  -0.306  -6.4059   0.3073   0.5182
 EP8  C06   C  CR16   0  -0.285  -6.1447   1.6628   0.4551
 EP8  N07   N  NR15   0  -0.688  -5.3583  -1.9254   0.0738
 EP8  C08   C  CR15   0  -0.092  -4.1368  -2.3316  -0.3903
 EP8  C09   C  CR5    0   0.025  -3.3454  -1.2492  -0.6501
 EP8  C11   C  CH2    0  -0.464  -0.9268  -0.9125  -0.0391
 EP8  C12   C  CH2    0  -0.146   0.4846  -0.8981  -0.5800
 EP8  O13   O  O2     0  -0.480   1.3720  -0.5537   0.4942
 EP8  C14   C  CR5    0   0.580   2.6685  -0.5557   0.1942
 EP8  C16   C  CR15   0  -0.054   4.7720  -0.8887  -0.2989
 EP8  N17   N  N      0  -0.298   4.6345   0.4164  -0.2407
 EP8  N18   N  NR5    0  -0.430   3.3412   0.6189   0.0630
 EP8  C19   C  CR6    0   0.342   2.8323   1.9322   0.1400
 EP8  C23   C  CR16   0  -0.255   1.4526   3.5951   1.1848
 EP8  O26   O  O      0  -0.591   2.2213  -3.4744   0.2633
 EP8  O27   O  OC    -1  -0.601   4.3837  -3.7498  -0.2179
 EP8  H101  H  HCH2   0   0.244  -1.6945  -2.2321  -1.5597
 EP8  H102  H  HCH2   0   0.234  -1.8303  -0.5327  -1.9580
 EP8  H201  H  HCR6   0   0.269   3.9499   2.5835  -1.5740
 EP8  H211  H  HCR6   0   0.262   3.1041   4.8936  -1.4665
 EP8  H221  H  HCR6   0   0.261   1.4879   5.5482   0.2940
 EP8  H241  H  HCR6   0   0.270   1.6289   1.5835   1.8922
 EP8  H011  H  HCR6   0   0.244  -4.7349   3.2165  -0.0282
 EP8  H021  H  HCR6   0   0.238  -2.9469   1.6651  -0.7248
 EP8  H051  H  HCR6   0   0.257  -7.3642  -0.0628   0.8604
 EP8  H061  H  HCR6   0   0.247  -6.9127   2.3651   0.7532
 EP8  H1    H  HNR5   0   0.407  -6.1134  -2.5411   0.3236
 EP8  H081  H  HCR5   0   0.279  -3.9157  -3.3817  -0.5044
 EP8  H111  H  HCH2   0   0.233  -1.1657   0.0626   0.3942
 EP8  H112  H  HCH2   0   0.235  -1.0049  -1.6494   0.7645
 EP8  H121  H  HCH2   0   0.231   0.7597  -1.8769  -0.9769
 EP8  H122  H  HCH2   0   0.216   0.5817  -0.1577  -1.3814
 EP8  H161  H  HCR5   0   0.257   5.7372  -1.3204  -0.5173
 EP8  H231  H  HCR6   0   0.263   0.7570   3.8731   1.9657
 EP8  C25   C  C      0   0.373   3.3693  -3.0596   0.0065

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
 EP8  O26  C25   deloc     1.247  0.020  1.247
 EP8  C25  O27   deloc     1.247  0.020  1.247
 EP8  C25  C15   single    1.498  0.020  1.498
 EP8  C16  C15   aromatic  1.409  0.020  1.409
 EP8  C16  N17   aromatic  1.314  0.020  1.314
 EP8  C15  C14   aromatic  1.381  0.020  1.381
 EP8  N17  N18   aromatic  1.344  0.020  1.344
 EP8  N07  C08   aromatic  1.368  0.020  1.368
 EP8  N07  C04   aromatic  1.363  0.020  1.363
 EP8  C08  C09   aromatic  1.366  0.020  1.366
 EP8  C14  N18   aromatic  1.360  0.020  1.360
 EP8  C14  O13   single    1.331  0.020  1.331
 EP8  C04  C05   aromatic  1.395  0.020  1.395
 EP8  C04  C03   aromatic  1.413  0.020  1.413
 EP8  C05  C06   aromatic  1.382  0.020  1.382
 EP8  N18  C19   single    1.411  0.020  1.411
 EP8  C09  C03   aromatic  1.434  0.020  1.434
 EP8  C09  C10   single    1.493  0.020  1.493
 EP8  C12  O13   single    1.435  0.020  1.435
 EP8  C12  C11   single    1.512  0.020  1.512
 EP8  C03  C02   aromatic  1.400  0.020  1.400
 EP8  C06  C01   aromatic  1.405  0.020  1.405
 EP8  C10  C11   single    1.531  0.020  1.531
 EP8  C19  C24   aromatic  1.391  0.020  1.391
 EP8  C19  C20   aromatic  1.391  0.020  1.391
 EP8  C02  C01   aromatic  1.381  0.020  1.381
 EP8  C24  C23   aromatic  1.388  0.020  1.388
 EP8  C20  C21   aromatic  1.386  0.020  1.386
 EP8  C23  C22   aromatic  1.388  0.020  1.388
 EP8  C21  C22   aromatic  1.389  0.020  1.389
 EP8  C10  H101  single    0.970  0.020  1.090
 EP8  C10  H102  single    0.970  0.020  1.090
 EP8  C20  H201  single    0.930  0.020  1.080
 EP8  C21  H211  single    0.930  0.020  1.080
 EP8  C22  H221  single    0.930  0.020  1.080
 EP8  C24  H241  single    0.930  0.020  1.080
 EP8  C01  H011  single    0.930  0.020  1.080
 EP8  C02  H021  single    0.930  0.020  1.080
 EP8  C05  H051  single    0.930  0.020  1.080
 EP8  C06  H061  single    0.930  0.020  1.080
 EP8  N07  H1    single    0.860  0.020  1.020
 EP8  C08  H081  single    0.930  0.020  1.080
 EP8  C11  H111  single    0.970  0.020  1.090
 EP8  C11  H112  single    0.970  0.020  1.090
 EP8  C12  H121  single    0.970  0.020  1.090
 EP8  C12  H122  single    0.970  0.020  1.090
 EP8  C16  H161  single    0.930  0.020  1.080
 EP8  C23  H231  single    0.930  0.020  1.080

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
 EP8  H102  C10  H101  106.29  3.000
 EP8  H102  C10  C11   109.16  3.000
 EP8  H101  C10  C11   109.31  3.000
 EP8  H102  C10  C09   109.50  3.000
 EP8  H101  C10  C09   109.63  3.000
 EP8  C11   C10  C09   112.73  3.000
 EP8  C25   C15  C16   127.07  3.000
 EP8  C16   C15  C14   103.19  3.000
 EP8  C25   C15  C14   129.73  3.000
 EP8  H201  C20  C19   120.01  3.000
 EP8  H201  C20  C21   120.25  3.000
 EP8  C19   C20  C21   119.73  3.000
 EP8  H211  C21  C22   120.21  3.000
 EP8  H211  C21  C20   119.40  3.000
 EP8  C22   C21  C20   120.39  3.000
 EP8  H221  C22  C23   120.23  3.000
 EP8  H221  C22  C21   120.23  3.000
 EP8  C23   C22  C21   119.54  3.000
 EP8  H241  C24  C23   119.70  3.000
 EP8  H241  C24  C19   120.81  3.000
 EP8  C23   C24  C19   119.48  3.000
 EP8  H011  C01  C06   119.28  3.000
 EP8  H011  C01  C02   119.75  3.000
 EP8  C06   C01  C02   120.96  3.000
 EP8  H021  C02  C03   120.53  3.000
 EP8  H021  C02  C01   120.44  3.000
 EP8  C03   C02  C01   119.03  3.000
 EP8  C09   C03  C04   107.23  3.000
 EP8  C09   C03  C02   133.69  3.000
 EP8  C04   C03  C02   119.08  3.000
 EP8  N07   C04  C05   130.64  3.000
 EP8  C05   C04  C03   122.09  3.000
 EP8  N07   C04  C03   107.27  3.000
 EP8  H051  C05  C06   121.13  3.000
 EP8  H051  C05  C04   121.36  3.000
 EP8  C06   C05  C04   117.51  3.000
 EP8  H061  C06  C05   119.32  3.000
 EP8  H061  C06  C01   119.34  3.000
 EP8  C05   C06  C01   121.33  3.000
 EP8  H1    N07  C08   124.94  3.000
 EP8  H1    N07  C04   125.78  3.000
 EP8  C08   N07  C04   109.28  3.000
 EP8  H081  C08  C09   129.22  3.000
 EP8  H081  C08  N07   120.51  3.000
 EP8  C09   C08  N07   110.27  3.000
 EP8  C08   C09  C03   105.95  3.000
 EP8  C03   C09  C10   126.58  3.000
 EP8  C08   C09  C10   127.45  3.000
 EP8  H112  C11  H111  107.11  3.000
 EP8  H112  C11  C12   109.65  3.000
 EP8  H111  C11  C12   109.71  3.000
 EP8  H112  C11  C10   109.36  3.000
 EP8  H111  C11  C10   109.82  3.000
 EP8  C12   C11  C10   111.10  3.000
 EP8  H122  C12  H121  108.53  3.000
 EP8  H122  C12  O13   109.30  3.000
 EP8  H121  C12  O13   109.36  3.000
 EP8  H122  C12  C11   110.55  3.000
 EP8  H121  C12  C11   110.91  3.000
 EP8  O13   C12  C11   108.16  3.000
 EP8  C14   O13  C12   115.67  3.000
 EP8  N18   C14  O13   120.16  3.000
 EP8  O13   C14  C15   132.46  3.000
 EP8  N18   C14  C15   107.38  3.000
 EP8  H161  C16  N17   119.99  3.000
 EP8  H161  C16  C15   127.25  3.000
 EP8  N17   C16  C15   112.76  3.000
 EP8  N18   N17  C16   105.10  3.000
 EP8  C19   N18  N17   119.99  3.000
 EP8  C19   N18  C14   128.35  3.000
 EP8  N17   N18  C14   111.58  3.000
 EP8  N18   C19  C24   120.97  3.000
 EP8  C24   C19  C20   120.24  3.000
 EP8  N18   C19  C20   118.79  3.000
 EP8  H231  C23  C24   119.21  3.000
 EP8  H231  C23  C22   120.19  3.000
 EP8  C24   C23  C22   120.60  3.000
 EP8  O27   C25  O26   126.98  3.000
 EP8  O27   C25  C15   115.71  3.000
 EP8  O26   C25  C15   117.31  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
 EP8  CONST_01  N18   N17  C16  C15     0.00   0.0  0
 EP8  CONST_02  N17   N18  C14  C15     0.00   0.0  0
 EP8  CONST_03  C19   N18  C14  C15   180.00   0.0  0
 EP8  CONST_06  C23   C24  C19  C20     0.00   0.0  0
 EP8  CONST_07  C23   C22  C21  C20     0.00   0.0  0
 EP8  CONST_08  N18   C19  C20  C21   180.00   0.0  0
 EP8  CONST_09  C24   C19  C20  C21     0.00   0.0  0
 EP8  CONST_10  C24   C23  C22  C21     0.00   0.0  0
 EP8  CONST_11  C19   C24  C23  C22     0.00   0.0  0
 EP8  CONST_12  C19   C20  C21  C22     0.00   0.0  0
 EP8  CONST_15  C04   C05  C06  C01     0.00   0.0  0
 EP8  CONST_16  C04   C03  C02  C01     0.00   0.0  0
 EP8  CONST_17  C09   C03  C02  C01   180.00   0.0  0
 EP8  CONST_18  N07   C04  C03  C02   180.00   0.0  0
 EP8  CONST_19  C05   C04  C03  C02     0.00   0.0  0
 EP8  CONST_20  C08   C09  C03  C02   180.00   0.0  0
 EP8  CONST_21  C05   C06  C01  C02     0.00   0.0  0
 EP8  CONST_22  C08   N07  C04  C03     0.00   0.0  0
 EP8  CONST_23  C06   C05  C04  C03     0.00   0.0  0
 EP8  CONST_24  N07   C08  C09  C03     0.00   0.0  0
 EP8  CONST_25  C06   C01  C02  C03     0.00   0.0  0
 EP8  CONST_26  C09   C08  N07  C04     0.00   0.0  0
 EP8  CONST_27  C08   C09  C03  C04     0.00   0.0  0
 EP8  CONST_28  C08   N07  C04  C05   180.00   0.0  0
 EP8  CONST_29  C09   C03  C04  C05   180.00   0.0  0
 EP8  CONST_30  N07   C04  C05  C06   180.00   0.0  0
 EP8  CONST_31  C09   C03  C04  N07     0.00   0.0  0
 EP8  CONST_32  N17   C16  C15  C14     0.00   0.0  0
 EP8  CONST_33  C16   N17  N18  C14     0.00   0.0  0
 EP8  CONST_34  N18   C14  C15  C16     0.00   0.0  0
 EP8  CONST_35  C19   N18  N17  C16   180.00   0.0  0
 EP8  CONST_36  C23   C24  C19  N18   180.00   0.0  0
 EP8  CONST_37  N07   C08  C09  C10   180.00   0.0  0
 EP8  CONST_38  C04   C03  C09  C10   180.00   0.0  0
 EP8  CONST_39  C02   C03  C09  C10     0.00   0.0  0
 EP8  CONST_40  C16   C15  C14  O13   180.00   0.0  0
 EP8  CONST_41  N17   N18  C14  O13   180.00   0.0  0
 EP8  CONST_42  C19   N18  C14  O13     0.00   0.0  0
 EP8  CONST_43  C25   C15  C16  N17   180.00   0.0  0
 EP8  CONST_44  C25   C15  C14  N18   180.00   0.0  0
 EP8  CONST_45  H241  C24  C19  C20   180.00   0.0  0
 EP8  CONST_46  H221  C22  C21  C20   180.00   0.0  0
 EP8  CONST_47  H231  C23  C22  C21   180.00   0.0  0
 EP8  CONST_48  H201  C20  C21  C22   180.00   0.0  0
 EP8  CONST_49  H051  C05  C06  C01   180.00   0.0  0
 EP8  CONST_50  H061  C06  C01  C02   180.00   0.0  0
 EP8  CONST_51  H1    N07  C04  C03   180.00   0.0  0
 EP8  CONST_52  H081  C08  C09  C03   180.00   0.0  0
 EP8  CONST_53  H011  C01  C02  C03   180.00   0.0  0
 EP8  CONST_54  H021  C02  C03  C04   180.00   0.0  0
 EP8  CONST_55  H161  C16  C15  C14   180.00   0.0  0
 EP8  CONST_56  H211  C21  C20  C19   180.00   0.0  0
 EP8  Var_01    C11   C10  C09  C03    73.50  30.0  2
 EP8  Var_02    N18   C14  O13  C12   106.65  30.0  1
 EP8  Var_03    O26   C25  C15  C14     1.30  30.0  2
 EP8  Var_04    C12   C11  C10  C09  -178.82  30.0  3
 EP8  Var_05    H121  C12  O13  C14    56.24  30.0  1
 EP8  Var_06    O13   C12  C11  C10   179.12  30.0  1

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
 EP8  plan-1  C15   0.020
 EP8  plan-1  O13   0.020
 EP8  plan-1  C14   0.020
 EP8  plan-1  C16   0.020
 EP8  plan-1  N17   0.020
 EP8  plan-1  N18   0.020
 EP8  plan-1  C19   0.020
 EP8  plan-1  H161  0.020
 EP8  plan-1  C25   0.020
 EP8  plan-2  C20   0.020
 EP8  plan-2  C21   0.020
 EP8  plan-2  C22   0.020
 EP8  plan-2  C24   0.020
 EP8  plan-2  N18   0.020
 EP8  plan-2  C19   0.020
 EP8  plan-2  C23   0.020
 EP8  plan-2  H201  0.020
 EP8  plan-2  H211  0.020
 EP8  plan-2  H221  0.020
 EP8  plan-2  H241  0.020
 EP8  plan-2  H231  0.020
 EP8  plan-3  C10   0.020
 EP8  plan-3  C01   0.020
 EP8  plan-3  C02   0.020
 EP8  plan-3  C03   0.020
 EP8  plan-3  C04   0.020
 EP8  plan-3  C05   0.020
 EP8  plan-3  C06   0.020
 EP8  plan-3  N07   0.020
 EP8  plan-3  C08   0.020
 EP8  plan-3  C09   0.020
 EP8  plan-3  H011  0.020
 EP8  plan-3  H021  0.020
 EP8  plan-3  H051  0.020
 EP8  plan-3  H061  0.020
 EP8  plan-3  H1    0.020
 EP8  plan-3  H081  0.020
 EP8  plan-4  C15   0.020
 EP8  plan-4  O26   0.020
 EP8  plan-4  O27   0.020
 EP8  plan-4  C25   0.020

