# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Jun  9 17:48:03 2020
#   Inital geometry file: a 119 line input string
#   Ligand name: 3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-8H-pyrrolo[1,2-a]pyrazin-5-ium-1-olate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(C=C)c1[nH]c2ccccc2c1Cc3c[n+]4C=CCc4c([O-])n3
#
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
 ZWP  ZWP  3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-8H-pyrrolo[1,2-a]pyrazin-5-ium-1-olate  ligand  46  25  .  2021-08-25  2021-08-25  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_ZWP
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
 ZWP  C1   C  CR16   0  -0.362   1.7109  -2.4283  -1.0549
 ZWP  C10  C  CT     0  -0.247   1.7237   2.4461   0.4998
 ZWP  C11  C  CH3    0  -0.706   2.5601   2.9144   1.6926
 ZWP  C12  C  CH3    0  -0.638   0.2504   2.7206   0.8403
 ZWP  C13  C  C1     0  -0.120   2.0817   3.1979  -0.7656
 ZWP  C14  C  C2     0  -0.539   3.0545   4.0886  -0.9162
 ZWP  C15  C  CH2    0  -0.665   0.0249   0.2992  -1.4088
 ZWP  C16  C  CR6    0   0.216  -1.2830  -0.0445  -0.7394
 ZWP  C18  C  CR6    0   0.352  -2.4804  -1.5172   0.6235
 ZWP  C19  C  CR56   0   0.200  -3.6346  -0.6962   0.3744
 ZWP  C2   C  CR56   0   0.067   1.9298  -1.1687  -0.4865
 ZWP  C21  C  CR16   0  -0.115  -2.3832   0.7584  -0.9859
 ZWP  C22  C  CH2    0  -0.524  -5.0298  -0.8250   0.8499
 ZWP  C23  C  CR15   0  -0.333  -5.6866   0.3541   0.2165
 ZWP  C24  C  CR15   0   0.052  -4.7931   1.0309  -0.4989
 ZWP  C3   C  CR56   0   0.327   3.0427  -0.9821   0.3555
 ZWP  C4   C  CR16   0  -0.312   3.9401  -2.0085   0.6454
 ZWP  C5   C  CR16   0  -0.290   3.7049  -3.2405   0.0642
 ZWP  C6   C  CR16   0  -0.272   2.6012  -3.4482  -0.7810
 ZWP  C7   C  CR5    0  -0.008   1.2406   0.0823  -0.5663
 ZWP  C8   C  CR5    0   0.395   1.9378   0.9700   0.2225
 ZWP  N17  N  N      0  -0.444  -1.3264  -1.1237   0.0239
 ZWP  N20  N  N      1  -0.431  -3.5356   0.3769  -0.3985
 ZWP  N9   N  NR15   0  -0.753   3.0158   0.3165   0.7671
 ZWP  O25  O  OC    -1  -0.531  -2.5594  -2.5201   1.3441
 ZWP  H1   H  HCR6   0   0.233   0.8547  -2.6026  -1.6952
 ZWP  H2   H  HCH3   0   0.252   2.2976   2.3555   2.5919
 ZWP  H3   H  HCH3   0   0.238   3.6350   2.8227   1.5311
 ZWP  H4   H  HCH3   0   0.255   2.3580   3.9669   1.8910
 ZWP  H5   H  HCH3   0   0.240   0.1272   3.7669   1.1250
 ZWP  H6   H  HCH3   0   0.237  -0.4208   2.5340   0.0047
 ZWP  H7   H  HCH3   0   0.237  -0.0757   2.1001   1.6761
 ZWP  H8   H  H      0   0.245   1.4603   2.9692  -1.6278
 ZWP  H9   H  H      0   0.243   3.2179   4.5705  -1.8715
 ZWP  H10  H  H      0   0.239   3.7199   4.3764  -0.1128
 ZWP  H11  H  HCH2   0   0.281   0.1029  -0.3395  -2.2956
 ZWP  H12  H  HCH2   0   0.266  -0.0253   1.3163  -1.7992
 ZWP  H13  H  HCR6   0   0.314  -2.3911   1.6438  -1.6007
 ZWP  H14  H  HCH2   0   0.313  -5.4831  -1.7723   0.5380
 ZWP  H15  H  HCR5   0   0.298  -6.7274   0.6122   0.3268
 ZWP  H16  H  HCR5   0   0.319  -4.8776   1.9251  -1.0946
 ZWP  H17  H  HCR6   0   0.255   4.7890  -1.8487   1.2981
 ZWP  H18  H  HCR6   0   0.246   4.3823  -4.0606   0.2649
 ZWP  H19  H  HCR6   0   0.242   2.4471  -4.4273  -1.2167
 ZWP  H21  H  HNR5   0   0.411   3.6983   0.7371   1.3745
 ZWP  H22  H  HCH2   0   0.313  -5.0982  -0.8032   1.9429

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
 ZWP  O25  C18  single    1.237  0.020  1.237
 ZWP  N17  C18  aromatic  1.359  0.020  1.359
 ZWP  N17  C16  aromatic  1.323  0.020  1.323
 ZWP  C18  C19  aromatic  1.438  0.020  1.438
 ZWP  C15  C16  single    1.509  0.020  1.509
 ZWP  C15  C7   single    1.495  0.020  1.495
 ZWP  C16  C21  aromatic  1.384  0.020  1.384
 ZWP  C19  C22  single    1.480  0.020  1.480
 ZWP  C19  N20  aromatic  1.326  0.020  1.326
 ZWP  C22  C23  single    1.491  0.020  1.491
 ZWP  C1   C6   aromatic  1.381  0.020  1.381
 ZWP  C1   C2   aromatic  1.399  0.020  1.399
 ZWP  C21  N20  aromatic  1.349  0.020  1.349
 ZWP  N20  C24  single    1.421  0.020  1.421
 ZWP  C6   C5   aromatic  1.406  0.020  1.406
 ZWP  C23  C24  double    1.330  0.020  1.330
 ZWP  C7   C2   aromatic  1.431  0.020  1.431
 ZWP  C7   C8   aromatic  1.377  0.020  1.377
 ZWP  C2   C3   aromatic  1.408  0.020  1.408
 ZWP  C13  C14  double    1.327  0.020  1.327
 ZWP  C13  C10  single    1.515  0.020  1.515
 ZWP  C5   C4   aromatic  1.382  0.020  1.382
 ZWP  C8   C10  single    1.517  0.020  1.517
 ZWP  C8   N9   aromatic  1.373  0.020  1.373
 ZWP  C3   C4   aromatic  1.394  0.020  1.394
 ZWP  C3   N9   aromatic  1.363  0.020  1.363
 ZWP  C12  C10  single    1.537  0.020  1.537
 ZWP  C10  C11  single    1.530  0.020  1.530
 ZWP  C1   H1   single    0.930  0.020  1.080
 ZWP  C11  H2   single    0.970  0.020  1.090
 ZWP  C11  H3   single    0.970  0.020  1.090
 ZWP  C11  H4   single    0.970  0.020  1.090
 ZWP  C12  H5   single    0.970  0.020  1.090
 ZWP  C12  H6   single    0.970  0.020  1.090
 ZWP  C12  H7   single    0.970  0.020  1.090
 ZWP  C13  H8   single    0.930  0.020  1.080
 ZWP  C14  H9   single    0.930  0.020  1.080
 ZWP  C14  H10  single    0.930  0.020  1.080
 ZWP  C15  H11  single    0.970  0.020  1.090
 ZWP  C15  H12  single    0.970  0.020  1.090
 ZWP  C21  H13  single    0.930  0.020  1.080
 ZWP  C22  H14  single    0.970  0.020  1.090
 ZWP  C23  H15  single    0.930  0.020  1.080
 ZWP  C24  H16  single    0.930  0.020  1.080
 ZWP  C4   H17  single    0.930  0.020  1.080
 ZWP  C5   H18  single    0.930  0.020  1.080
 ZWP  C6   H19  single    0.930  0.020  1.080
 ZWP  N9   H21  single    0.860  0.020  1.020
 ZWP  C22  H22  single    0.970  0.020  1.090

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
 ZWP  H1   C1   C6   120.52  3.000
 ZWP  H1   C1   C2   120.58  3.000
 ZWP  C6   C1   C2   118.91  3.000
 ZWP  C8   C10  C13  107.27  3.000
 ZWP  C8   C10  C12  110.46  3.000
 ZWP  C13  C10  C12  108.85  3.000
 ZWP  C12  C10  C11  107.25  3.000
 ZWP  C8   C10  C11  111.29  3.000
 ZWP  C13  C10  C11  111.72  3.000
 ZWP  H4   C11  H3   106.91  3.000
 ZWP  H4   C11  H2   107.46  3.000
 ZWP  H3   C11  H2   108.43  3.000
 ZWP  H4   C11  C10  109.64  3.000
 ZWP  H3   C11  C10  113.42  3.000
 ZWP  H2   C11  C10  110.75  3.000
 ZWP  H7   C12  H6   107.84  3.000
 ZWP  H7   C12  H5   108.17  3.000
 ZWP  H6   C12  H5   107.17  3.000
 ZWP  H7   C12  C10  110.78  3.000
 ZWP  H6   C12  C10  112.99  3.000
 ZWP  H5   C12  C10  109.71  3.000
 ZWP  H8   C13  C14  118.04  3.000
 ZWP  H8   C13  C10  115.02  3.000
 ZWP  C14  C13  C10  126.94  3.000
 ZWP  H10  C14  H9   116.36  3.000
 ZWP  H10  C14  C13  123.01  3.000
 ZWP  H9   C14  C13  120.63  3.000
 ZWP  H12  C15  H11  104.91  3.000
 ZWP  H12  C15  C7   111.99  3.000
 ZWP  H11  C15  C7   108.28  3.000
 ZWP  H12  C15  C16  109.35  3.000
 ZWP  H11  C15  C16  106.74  3.000
 ZWP  C7   C15  C16  114.95  3.000
 ZWP  N17  C16  C21  123.37  3.000
 ZWP  C21  C16  C15  118.54  3.000
 ZWP  N17  C16  C15  118.06  3.000
 ZWP  O25  C18  N17  123.09  3.000
 ZWP  N17  C18  C19  116.10  3.000
 ZWP  O25  C18  C19  120.82  3.000
 ZWP  N20  C19  C22  109.15  3.000
 ZWP  N20  C19  C18  120.20  3.000
 ZWP  C22  C19  C18  130.65  3.000
 ZWP  C7   C2   C3   107.35  3.000
 ZWP  C3   C2   C1   119.07  3.000
 ZWP  C7   C2   C1   133.57  3.000
 ZWP  H13  C21  N20  118.33  3.000
 ZWP  H13  C21  C16  125.72  3.000
 ZWP  N20  C21  C16  115.95  3.000
 ZWP  H22  C22  H14  105.99  3.000
 ZWP  H22  C22  C23  112.37  3.000
 ZWP  H14  C22  C23  112.37  3.000
 ZWP  H22  C22  C19  112.20  3.000
 ZWP  H14  C22  C19  111.96  3.000
 ZWP  C23  C22  C19  102.13  3.000
 ZWP  H15  C23  C24  125.59  3.000
 ZWP  H15  C23  C22  124.84  3.000
 ZWP  C24  C23  C22  109.57  3.000
 ZWP  H16  C24  N20  119.36  3.000
 ZWP  H16  C24  C23  131.83  3.000
 ZWP  N20  C24  C23  108.81  3.000
 ZWP  N9   C3   C4   130.67  3.000
 ZWP  N9   C3   C2   106.94  3.000
 ZWP  C4   C3   C2   122.39  3.000
 ZWP  H17  C4   C5   121.22  3.000
 ZWP  H17  C4   C3   121.44  3.000
 ZWP  C5   C4   C3   117.34  3.000
 ZWP  H18  C5   C6   119.40  3.000
 ZWP  H18  C5   C4   119.40  3.000
 ZWP  C6   C5   C4   121.21  3.000
 ZWP  H19  C6   C5   119.17  3.000
 ZWP  H19  C6   C1   119.75  3.000
 ZWP  C5   C6   C1   121.08  3.000
 ZWP  C8   C7   C2   106.73  3.000
 ZWP  C8   C7   C15  129.87  3.000
 ZWP  C2   C7   C15  123.37  3.000
 ZWP  N9   C8   C7   108.53  3.000
 ZWP  N9   C8   C10  120.09  3.000
 ZWP  C7   C8   C10  131.34  3.000
 ZWP  C18  N17  C16  121.25  3.000
 ZWP  C24  N20  C21  126.53  3.000
 ZWP  C24  N20  C19  110.34  3.000
 ZWP  C21  N20  C19  123.13  3.000
 ZWP  H21  N9   C8   124.97  3.000
 ZWP  H21  N9   C3   124.58  3.000
 ZWP  C8   N9   C3   110.44  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
 ZWP  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 ZWP  CONST_02  C8   C7   C2   C1    180.00   0.0  0
 ZWP  CONST_03  C4   C3   C2   C1      0.00   0.0  0
 ZWP  CONST_04  N9   C3   C2   C1    180.00   0.0  0
 ZWP  CONST_05  C19  C18  N17  C16     0.00   0.0  0
 ZWP  CONST_06  C19  N20  C21  C16     0.00   0.0  0
 ZWP  CONST_07  C21  C16  N17  C18     0.00   0.0  0
 ZWP  CONST_08  C21  N20  C19  C18     0.00   0.0  0
 ZWP  CONST_09  C5   C6   C1   C2      0.00   0.0  0
 ZWP  CONST_10  N9   C8   C7   C2      0.00   0.0  0
 ZWP  CONST_11  C5   C4   C3   C2      0.00   0.0  0
 ZWP  CONST_12  C8   N9   C3   C2      0.00   0.0  0
 ZWP  CONST_13  C6   C1   C2   C3      0.00   0.0  0
 ZWP  CONST_14  C8   C7   C2   C3      0.00   0.0  0
 ZWP  CONST_15  C6   C5   C4   C3      0.00   0.0  0
 ZWP  CONST_16  C7   C8   N9   C3      0.00   0.0  0
 ZWP  CONST_17  C7   C2   C3   C4    180.00   0.0  0
 ZWP  CONST_18  C8   N9   C3   C4    180.00   0.0  0
 ZWP  CONST_19  N9   C3   C4   C5    180.00   0.0  0
 ZWP  CONST_20  C7   C2   C1   C6    180.00   0.0  0
 ZWP  CONST_21  N9   C3   C2   C7      0.00   0.0  0
 ZWP  CONST_22  N20  C19  C18  N17     0.00   0.0  0
 ZWP  CONST_23  N20  C21  C16  N17     0.00   0.0  0
 ZWP  CONST_24  C15  C7   C2   C1      0.00   0.0  0
 ZWP  CONST_25  C2   C7   C8   C10   180.00   0.0  0
 ZWP  CONST_26  C3   N9   C8   C10   180.00   0.0  0
 ZWP  CONST_27  C18  N17  C16  C15   180.00   0.0  0
 ZWP  CONST_28  N20  C21  C16  C15   180.00   0.0  0
 ZWP  CONST_29  C3   C2   C7   C15   180.00   0.0  0
 ZWP  CONST_30  N9   C8   C7   C15   180.00   0.0  0
 ZWP  CONST_31  O25  C18  N17  C16   180.00   0.0  0
 ZWP  CONST_32  O25  C18  C19  C22     0.00   0.0  0
 ZWP  CONST_33  O25  C18  C19  N20   180.00   0.0  0
 ZWP  CONST_34  H18  C5   C6   C1    180.00   0.0  0
 ZWP  CONST_35  H13  C21  N20  C19   180.00   0.0  0
 ZWP  CONST_36  H19  C6   C1   C2    180.00   0.0  0
 ZWP  CONST_37  H17  C4   C3   C2    180.00   0.0  0
 ZWP  CONST_38  H21  N9   C3   C2    180.00   0.0  0
 ZWP  CONST_39  H1   C1   C2   C3    180.00   0.0  0
 ZWP  Var_01    C2   C7   C15  C16    87.09  30.0  2
 ZWP  Var_02    C7   C15  C16  C21   142.20  30.0  1
 ZWP  Var_03    C7   C8   C10  C11   166.64  30.0  2
 ZWP  Var_04    C8   C10  C13  C14  -117.32  30.0  3
 ZWP  Var_05    H5   C12  C10  C8    174.92  30.0  3
 ZWP  Var_06    H2   C11  C10  C8    -59.48  30.0  3
 ZWP  Var_07    H9   C14  C13  C10  -179.71   0.0  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
 ZWP  plan-1  C1   0.020
 ZWP  plan-1  C10  0.020
 ZWP  plan-1  C15  0.020
 ZWP  plan-1  C2   0.020
 ZWP  plan-1  C3   0.020
 ZWP  plan-1  C4   0.020
 ZWP  plan-1  C5   0.020
 ZWP  plan-1  C6   0.020
 ZWP  plan-1  C7   0.020
 ZWP  plan-1  C8   0.020
 ZWP  plan-1  N9   0.020
 ZWP  plan-1  H1   0.020
 ZWP  plan-1  H17  0.020
 ZWP  plan-1  H18  0.020
 ZWP  plan-1  H19  0.020
 ZWP  plan-1  H21  0.020
 ZWP  plan-2  C15  0.020
 ZWP  plan-2  C16  0.020
 ZWP  plan-2  C18  0.020
 ZWP  plan-2  C19  0.020
 ZWP  plan-2  C21  0.020
 ZWP  plan-2  C22  0.020
 ZWP  plan-2  C23  0.020
 ZWP  plan-2  C24  0.020
 ZWP  plan-2  N17  0.020
 ZWP  plan-2  N20  0.020
 ZWP  plan-2  O25  0.020
 ZWP  plan-2  H13  0.020
 ZWP  plan-2  H14  0.020
 ZWP  plan-2  H15  0.020
 ZWP  plan-2  H16  0.020
 ZWP  plan-2  H22  0.020
 ZWP  plan-3  C10  0.020
 ZWP  plan-3  C13  0.020
 ZWP  plan-3  C14  0.020
 ZWP  plan-3  H8   0.020
 ZWP  plan-3  H9   0.020
 ZWP  plan-3  H10  0.020

