# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 21 07:01:58 2020
#   Inital geometry file: a 116 line input string
#   Ligand name: 3,4-di-1H-indol-3-yl-1H-pyrrole-2,5-dicarboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1[nH]c(C(O)=O)c(c2c[nH]c3ccccc23)c1c4c[nH]c5ccccc45
#
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
 CRR  CRR  '3,4-di-1H-indol-3-yl-1H-pyrrole-2,5-dicarboxylic acid'  ligand  42  29  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_CRR
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
 CRR  C5   C  CR56   0   0.025   2.4360  -1.0191  -0.0098
 CRR  C4   C  CR16   0  -0.380   2.7603  -1.0470  -1.3684
 CRR  C3   C  CR16   0  -0.278   3.6405  -2.0072  -1.8288
 CRR  C2   C  CR16   0  -0.288   4.2152  -2.9424  -0.9507
 CRR  C1   C  CR16   0  -0.313   3.9172  -2.9358   0.3989
 CRR  C20  C  CR56   0   0.341   3.0239  -1.9667   0.8557
 CRR  N3   N  NR15   0  -0.693   2.5436  -1.7209   2.1086
 CRR  C19  C  CR15   0  -0.108   1.6728  -0.6656   2.0584
 CRR  C6   C  CR5    0   0.011   1.5698  -0.1923   0.7798
 CRR  C7   C  CR5    0  -0.037   0.7043   0.8746   0.2842
 CRR  C8   C  CR5    0   0.076   1.1043   2.0254  -0.3834
 CRR  C36  C  C      0   0.339   2.4490   2.6096  -0.6914
 CRR  O39  O  O      0  -0.582   3.4435   2.0362  -0.2137
 CRR  O40  O  OC    -1  -0.619   2.4405   3.6405  -1.4014
 CRR  N1   N  NR15   0  -0.635  -0.0212   2.6797  -0.7563
 CRR  C9   C  CR5    0   0.075  -1.1385   2.0203  -0.3681
 CRR  C35  C  C      0   0.339  -2.4908   2.6035  -0.6448
 CRR  O37  O  O      0  -0.581  -3.4793   1.9784  -0.2225
 CRR  O38  O  OC    -1  -0.619  -2.4957   3.6860  -1.2722
 CRR  C10  C  CR5    0  -0.038  -0.7237   0.8700   0.2914
 CRR  C11  C  CR5    0   0.011  -1.5793  -0.2014   0.7940
 CRR  C12  C  CR56   0   0.027  -2.4444  -1.0317   0.0074
 CRR  C13  C  CR16   0  -0.378  -2.7717  -1.0610  -1.3502
 CRR  C14  C  CR16   0  -0.279  -3.6532  -2.0214  -1.8073
 CRR  C15  C  CR16   0  -0.287  -4.2266  -2.9550  -0.9264
 CRR  C16  C  CR16   0  -0.313  -3.9249  -2.9474   0.4223
 CRR  C17  C  CR56   0   0.340  -3.0292  -1.9785   0.8755
 CRR  N2   N  NR15   0  -0.693  -2.5464  -1.7301   2.1270
 CRR  C18  C  CR15   0  -0.109  -1.6775  -0.6733   2.0735
 CRR  H4   H  HCR6   0   0.228   2.3205  -0.3264  -2.0468
 CRR  H3   H  HCR6   0   0.239   3.8993  -2.0413  -2.8796
 CRR  H2   H  HCR6   0   0.243   4.9038  -3.6821  -1.3392
 CRR  H1   H  HCR6   0   0.253   4.3613  -3.6574   1.0734
 CRR  HN3  H  HNR5   0   0.403   2.7751  -2.2371   2.9399
 CRR  H19  H  HCR5   0   0.268   1.1994  -0.3124   2.9600
 CRR  HN1  H  HNR5   0   0.377  -0.0268   3.5617  -1.2432
 CRR  H13  H  HCR6   0   0.228  -2.3347  -0.3402  -2.0300
 CRR  H14  H  HCR6   0   0.239  -3.9150  -2.0565  -2.8573
 CRR  H15  H  HCR6   0   0.243  -4.9175  -3.6941  -1.3120
 CRR  H16  H  HCR6   0   0.252  -4.3687  -3.6670   1.0991
 CRR  HN2  H  HNR5   0   0.403  -2.7751  -2.2456   2.9595
 CRR  H18  H  HCR5   0   0.268  -1.2032  -0.3177   2.9737

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
 CRR  C5   C20  aromatic  1.412  0.020  1.412
 CRR  C5   C4   aromatic  1.397  0.020  1.397
 CRR  C5   C6   aromatic  1.434  0.020  1.434
 CRR  C4   C3   aromatic  1.381  0.020  1.381
 CRR  C4   H4   single    0.930  0.020  1.080
 CRR  C3   C2   aromatic  1.406  0.020  1.406
 CRR  C3   H3   single    0.930  0.020  1.080
 CRR  C2   C1   aromatic  1.382  0.020  1.382
 CRR  C2   H2   single    0.930  0.020  1.080
 CRR  C1   C20  aromatic  1.395  0.020  1.395
 CRR  C1   H1   single    0.930  0.020  1.080
 CRR  C20  N3   aromatic  1.364  0.020  1.364
 CRR  N3   C19  aromatic  1.369  0.020  1.369
 CRR  N3   HN3  single    0.860  0.020  1.020
 CRR  C19  C6   aromatic  1.367  0.020  1.367
 CRR  C19  H19  single    0.930  0.020  1.080
 CRR  C6   C7   single    1.461  0.020  1.461
 CRR  C7   C8   aromatic  1.389  0.020  1.389
 CRR  C7   C10  aromatic  1.428  0.020  1.428
 CRR  C8   C36  single    1.498  0.020  1.498
 CRR  C8   N1   aromatic  1.354  0.020  1.354
 CRR  C36  O39  deloc     1.243  0.020  1.243
 CRR  C36  O40  deloc     1.252  0.020  1.252
 CRR  N1   C9   aromatic  1.354  0.020  1.354
 CRR  N1   HN1  single    0.860  0.020  1.020
 CRR  C9   C10  aromatic  1.389  0.020  1.389
 CRR  C9   C35  single    1.498  0.020  1.498
 CRR  C35  O37  deloc     1.243  0.020  1.243
 CRR  C35  O38  deloc     1.251  0.020  1.251
 CRR  C10  C11  single    1.460  0.020  1.460
 CRR  C11  C12  aromatic  1.434  0.020  1.434
 CRR  C11  C18  aromatic  1.367  0.020  1.367
 CRR  C12  C13  aromatic  1.397  0.020  1.397
 CRR  C12  C17  aromatic  1.411  0.020  1.411
 CRR  C13  C14  aromatic  1.381  0.020  1.381
 CRR  C13  H13  single    0.930  0.020  1.080
 CRR  C14  C15  aromatic  1.406  0.020  1.406
 CRR  C14  H14  single    0.930  0.020  1.080
 CRR  C15  C16  aromatic  1.382  0.020  1.382
 CRR  C15  H15  single    0.930  0.020  1.080
 CRR  C16  C17  aromatic  1.395  0.020  1.395
 CRR  C16  H16  single    0.930  0.020  1.080
 CRR  C17  N2   aromatic  1.364  0.020  1.364
 CRR  N2   C18  aromatic  1.369  0.020  1.369
 CRR  N2   HN2  single    0.860  0.020  1.020
 CRR  C18  H18  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
 CRR  C6   C5   C20  107.51  3.000
 CRR  C6   C5   C4   133.40  3.000
 CRR  C20  C5   C4   119.09  3.000
 CRR  H4   C4   C3   120.83  3.000
 CRR  H4   C4   C5   120.10  3.000
 CRR  C3   C4   C5   119.07  3.000
 CRR  H3   C3   C2   119.18  3.000
 CRR  H3   C3   C4   119.84  3.000
 CRR  C2   C3   C4   120.98  3.000
 CRR  H2   C2   C1   119.39  3.000
 CRR  H2   C2   C3   119.37  3.000
 CRR  C1   C2   C3   121.24  3.000
 CRR  H1   C1   C20  121.43  3.000
 CRR  H1   C1   C2   121.10  3.000
 CRR  C20  C1   C2   117.46  3.000
 CRR  N3   C20  C1   130.65  3.000
 CRR  N3   C20  C5   107.19  3.000
 CRR  C1   C20  C5   122.16  3.000
 CRR  HN3  N3   C19  124.92  3.000
 CRR  HN3  N3   C20  125.86  3.000
 CRR  C19  N3   C20  109.22  3.000
 CRR  H19  C19  C6   129.47  3.000
 CRR  H19  C19  N3   120.09  3.000
 CRR  C6   C19  N3   110.42  3.000
 CRR  C7   C6   C19  127.94  3.000
 CRR  C7   C6   C5   126.31  3.000
 CRR  C19  C6   C5   105.65  3.000
 CRR  C10  C7   C8   107.04  3.000
 CRR  C10  C7   C6   126.06  3.000
 CRR  C8   C7   C6   126.69  3.000
 CRR  N1   C8   C36  120.06  3.000
 CRR  N1   C8   C7   107.06  3.000
 CRR  C36  C8   C7   132.86  3.000
 CRR  O40  C36  O39  127.10  3.000
 CRR  O40  C36  C8   115.57  3.000
 CRR  O39  C36  C8   117.33  3.000
 CRR  HN1  N1   C9   124.07  3.000
 CRR  HN1  N1   C8   124.10  3.000
 CRR  C9   N1   C8   111.80  3.000
 CRR  C10  C9   C35  132.80  3.000
 CRR  C35  C9   N1   120.14  3.000
 CRR  C10  C9   N1   107.03  3.000
 CRR  O38  C35  O37  127.02  3.000
 CRR  O38  C35  C9   115.65  3.000
 CRR  O37  C35  C9   117.32  3.000
 CRR  C11  C10  C9   126.57  3.000
 CRR  C11  C10  C7   126.16  3.000
 CRR  C9   C10  C7   107.07  3.000
 CRR  C18  C11  C12  105.67  3.000
 CRR  C18  C11  C10  128.12  3.000
 CRR  C12  C11  C10  126.12  3.000
 CRR  C17  C12  C13  119.12  3.000
 CRR  C17  C12  C11  107.52  3.000
 CRR  C13  C12  C11  133.36  3.000
 CRR  H13  C13  C14  120.84  3.000
 CRR  H13  C13  C12  120.11  3.000
 CRR  C14  C13  C12  119.05  3.000
 CRR  H14  C14  C15  119.18  3.000
 CRR  H14  C14  C13  119.84  3.000
 CRR  C15  C14  C13  120.98  3.000
 CRR  H15  C15  C16  119.38  3.000
 CRR  H15  C15  C14  119.37  3.000
 CRR  C16  C15  C14  121.25  3.000
 CRR  H16  C16  C17  121.44  3.000
 CRR  H16  C16  C15  121.11  3.000
 CRR  C17  C16  C15  117.45  3.000
 CRR  N2   C17  C16  130.67  3.000
 CRR  N2   C17  C12  107.18  3.000
 CRR  C16  C17  C12  122.15  3.000
 CRR  HN2  N2   C18  124.92  3.000
 CRR  HN2  N2   C17  125.85  3.000
 CRR  C18  N2   C17  109.22  3.000
 CRR  H18  C18  N2   120.08  3.000
 CRR  H18  C18  C11  129.50  3.000
 CRR  N2   C18  C11  110.40  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
 CRR  CONST_01  C2   C1   C20  C5      0.00   0.0  0
 CRR  CONST_02  C19  N3   C20  C5      0.00   0.0  0
 CRR  CONST_03  C2   C3   C4   C5      0.00   0.0  0
 CRR  CONST_04  N3   C19  C6   C5      0.00   0.0  0
 CRR  CONST_07  C1   C20  C5   C4      0.00   0.0  0
 CRR  CONST_08  N3   C20  C5   C4    180.00   0.0  0
 CRR  CONST_09  C19  C6   C5   C4    180.00   0.0  0
 CRR  CONST_10  C7   C6   C5   C4      0.00   0.0  0
 CRR  CONST_11  C1   C2   C3   C4      0.00   0.0  0
 CRR  CONST_12  C20  C5   C4   C3      0.00   0.0  0
 CRR  CONST_13  C6   C5   C4   C3    180.00   0.0  0
 CRR  CONST_14  C20  C1   C2   C3      0.00   0.0  0
 CRR  CONST_15  N3   C20  C1   C2    180.00   0.0  0
 CRR  CONST_16  C6   C5   C20  C1    180.00   0.0  0
 CRR  CONST_17  C19  N3   C20  C1    180.00   0.0  0
 CRR  CONST_18  C19  C6   C5   C20     0.00   0.0  0
 CRR  CONST_19  C7   C6   C5   C20   180.00   0.0  0
 CRR  CONST_20  C6   C19  N3   C20     0.00   0.0  0
 CRR  CONST_21  C6   C5   C20  N3      0.00   0.0  0
 CRR  CONST_22  C7   C6   C19  N3    180.00   0.0  0
 CRR  CONST_25  N1   C8   C7   C6    180.00   0.0  0
 CRR  CONST_26  C9   C10  C7   C6    180.00   0.0  0
 CRR  CONST_27  C11  C10  C7   C6      0.00   0.0  0
 CRR  CONST_28  C9   N1   C8   C7      0.00   0.0  0
 CRR  CONST_29  N1   C9   C10  C7      0.00   0.0  0
 CRR  CONST_32  C9   C10  C7   C8      0.00   0.0  0
 CRR  CONST_33  C11  C10  C7   C8    180.00   0.0  0
 CRR  CONST_34  C10  C9   N1   C8      0.00   0.0  0
 CRR  CONST_35  C10  C7   C8   N1      0.00   0.0  0
 CRR  CONST_36  C11  C10  C9   N1    180.00   0.0  0
 CRR  CONST_39  C13  C12  C11  C10     0.00   0.0  0
 CRR  CONST_40  C17  C12  C11  C10   180.00   0.0  0
 CRR  CONST_41  N2   C18  C11  C10   180.00   0.0  0
 CRR  CONST_42  C14  C13  C12  C11   180.00   0.0  0
 CRR  CONST_43  C16  C17  C12  C11   180.00   0.0  0
 CRR  CONST_44  N2   C17  C12  C11     0.00   0.0  0
 CRR  CONST_45  C17  N2   C18  C11     0.00   0.0  0
 CRR  CONST_46  N2   C18  C11  C12     0.00   0.0  0
 CRR  CONST_47  C15  C14  C13  C12     0.00   0.0  0
 CRR  CONST_48  C15  C16  C17  C12     0.00   0.0  0
 CRR  CONST_49  C18  N2   C17  C12     0.00   0.0  0
 CRR  CONST_50  C18  C11  C12  C13   180.00   0.0  0
 CRR  CONST_51  C16  C17  C12  C13     0.00   0.0  0
 CRR  CONST_52  N2   C17  C12  C13   180.00   0.0  0
 CRR  CONST_53  C16  C15  C14  C13     0.00   0.0  0
 CRR  CONST_54  C17  C12  C13  C14     0.00   0.0  0
 CRR  CONST_55  C17  C16  C15  C14     0.00   0.0  0
 CRR  CONST_56  N2   C17  C16  C15   180.00   0.0  0
 CRR  CONST_57  C18  N2   C17  C16   180.00   0.0  0
 CRR  CONST_58  C18  C11  C12  C17     0.00   0.0  0
 CRR  CONST_59  C36  C8   C7   C6      0.00   0.0  0
 CRR  CONST_60  C35  C9   C10  C7    180.00   0.0  0
 CRR  CONST_61  C35  C9   N1   C8    180.00   0.0  0
 CRR  CONST_62  C10  C7   C8   C36   180.00   0.0  0
 CRR  CONST_63  C9   N1   C8   C36   180.00   0.0  0
 CRR  CONST_64  C11  C10  C9   C35     0.00   0.0  0
 CRR  CONST_65  H1   C1   C20  C5    180.00   0.0  0
 CRR  CONST_66  HN3  N3   C20  C5    180.00   0.0  0
 CRR  CONST_67  H3   C3   C4   C5    180.00   0.0  0
 CRR  CONST_68  H19  C19  C6   C5    180.00   0.0  0
 CRR  CONST_69  H2   C2   C3   C4    180.00   0.0  0
 CRR  CONST_70  H4   C4   C3   C2    180.00   0.0  0
 CRR  CONST_71  HN1  N1   C8   C7    180.00   0.0  0
 CRR  CONST_72  H18  C18  C11  C10     0.00   0.0  0
 CRR  CONST_73  H13  C13  C12  C11     0.00   0.0  0
 CRR  CONST_74  HN2  N2   C18  C11   180.00   0.0  0
 CRR  CONST_75  H14  C14  C13  C12   180.00   0.0  0
 CRR  CONST_76  H16  C16  C17  C12   180.00   0.0  0
 CRR  CONST_77  H15  C15  C14  C13   180.00   0.0  0
 CRR  Var_01    O39  C36  C8   C7     -5.04  30.0  2
 CRR  Var_02    O37  C35  C9   N1   -177.43  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
 CRR  plan-1  C6   0.020
 CRR  plan-1  C7   0.020
 CRR  plan-1  C8   0.020
 CRR  plan-1  C36  0.020
 CRR  plan-1  N1   0.020
 CRR  plan-1  C9   0.020
 CRR  plan-1  C35  0.020
 CRR  plan-1  C10  0.020
 CRR  plan-1  C11  0.020
 CRR  plan-1  HN1  0.020
 CRR  plan-2  C5   0.020
 CRR  plan-2  C4   0.020
 CRR  plan-2  C3   0.020
 CRR  plan-2  C2   0.020
 CRR  plan-2  C1   0.020
 CRR  plan-2  C20  0.020
 CRR  plan-2  N3   0.020
 CRR  plan-2  C19  0.020
 CRR  plan-2  C6   0.020
 CRR  plan-2  C7   0.020
 CRR  plan-2  H4   0.020
 CRR  plan-2  H3   0.020
 CRR  plan-2  H2   0.020
 CRR  plan-2  H1   0.020
 CRR  plan-2  HN3  0.020
 CRR  plan-2  H19  0.020
 CRR  plan-3  C10  0.020
 CRR  plan-3  C11  0.020
 CRR  plan-3  C12  0.020
 CRR  plan-3  C13  0.020
 CRR  plan-3  C14  0.020
 CRR  plan-3  C15  0.020
 CRR  plan-3  C16  0.020
 CRR  plan-3  C17  0.020
 CRR  plan-3  N2   0.020
 CRR  plan-3  C18  0.020
 CRR  plan-3  H13  0.020
 CRR  plan-3  H14  0.020
 CRR  plan-3  H15  0.020
 CRR  plan-3  H16  0.020
 CRR  plan-3  HN2  0.020
 CRR  plan-3  H18  0.020
 CRR  plan-4  C8   0.020
 CRR  plan-4  C36  0.020
 CRR  plan-4  O39  0.020
 CRR  plan-4  O40  0.020
 CRR  plan-5  C9   0.020
 CRR  plan-5  C35  0.020
 CRR  plan-5  O37  0.020
 CRR  plan-5  O38  0.020

