# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 25 20:44:14 2020
#   Inital geometry file: a 111 line input string
#   Ligand name: 1-(4-fluorophenyl)-2-[2-(4-fluorophenyl)-2-oxoethyl]pyrrolo[1,2-a]pyrazin-2-ium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Fc1ccc(cc1)C(=O)C[n+]2ccn3cccc3c2c4ccc(F)cc4
#
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
 NRY  NRY  1-(4-fluorophenyl)-2-[2-(4-fluorophenyl)-2-oxoethyl]pyrrolo[1,2-a]pyrazin-2-ium  ligand  41  26  .  2021-08-15  2021-08-15  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_NRY
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
 NRY  C26  C  CR16  0  -0.076  -1.3287   2.5641   0.8547
 NRY  C25  C  CR16  0  -0.017  -2.5694   3.0096   0.6135
 NRY  C22  C  CR15  0  -0.333  -5.3301   1.0858  -0.5505
 NRY  C23  C  CR15  0   0.010  -4.8093   2.3076  -0.1342
 NRY  C15  C  CR16  0  -0.397  -1.6597  -3.3486   0.7327
 NRY  C14  C  CR16  0  -0.222  -1.9665  -2.0114   0.9233
 NRY  C13  C  CR6   0  -0.080  -1.5287  -1.0564   0.0097
 NRY  C12  C  CR6   0   0.405  -1.8840   0.3586   0.2251
 NRY  C16  C  CR6   0   0.548  -0.9268  -3.7052  -0.3835
 NRY  C06  C  CR6   0   0.548   5.4143   0.2665   0.2053
 NRY  C05  C  CR16  0  -0.396   4.9439   0.7899  -0.9873
 NRY  C02  C  C     0   0.376   1.2923   1.1233  -0.2002
 NRY  C03  C  CR6   0  -0.021   2.7243   0.8116  -0.0346
 NRY  C04  C  CR16  0  -0.233   3.5942   1.0603  -1.0998
 NRY  O01  O  O     0  -0.369   0.8335   1.5769  -1.2228
 NRY  C08  C  CR16  0  -0.392   4.5844   0.0044   1.2793
 NRY  C09  C  CR16  0  -0.270   3.2347   0.2812   1.1514
 NRY  N11  N  NR6   1  -0.452  -0.9925   1.2344   0.6833
 NRY  F17  F  F     0  -0.302  -0.6338  -4.9947  -0.5759
 NRY  C18  C  CR16  0  -0.395  -0.4921  -2.7783  -1.3127
 NRY  C19  C  CR16  0  -0.234  -0.7972  -1.4427  -1.1103
 NRY  C20  C  CR56  0   0.332  -3.1785   0.7848  -0.0350
 NRY  C21  C  CR15  0  -0.346  -4.3202   0.1328  -0.4953
 NRY  N24  N  N     0  -0.505  -3.5189   2.1271   0.1748
 NRY  H1   H  HCR6  0   0.349  -0.5509   3.2224   1.2045
 NRY  H2   H  HCR6  0   0.345  -2.8537   4.0407   0.7507
 NRY  H3   H  HCR5  0   0.287  -6.3488   0.9253  -0.8635
 NRY  H4   H  HCR5  0   0.321  -5.2771   3.2743  -0.0459
 NRY  H5   H  HCR6  0   0.296  -1.9876  -4.0986   1.4399
 NRY  H6   H  HCR6  0   0.290  -2.5407  -1.7129   1.7906
 NRY  H7   H  HCR6  0   0.295   5.6224   0.9827  -1.8074
 NRY  H8   H  HCR6  0   0.282   3.2133   1.4700  -2.0251
 NRY  H9   H  HCR6  0   0.297   4.9835  -0.4054   2.1969
 NRY  H10  H  HCR6  0   0.285   2.5941   0.0742   1.9986
 NRY  H11  H  HCH2  0   0.342   0.4130  -0.1924   1.2810
 NRY  H12  H  HCH2  0   0.347   0.7032   1.4335   1.8539
 NRY  H13  H  HCR6  0   0.297   0.0680  -3.0908  -2.1835
 NRY  H14  H  HCR6  0   0.289  -0.4790  -0.7107  -1.8402
 NRY  H15  H  HCR5  0   0.284  -4.3889  -0.9112  -0.7536
 NRY  C10  C  CH2   0  -0.485   0.3770   0.8560   0.9877
 NRY  F07  F  F     0  -0.299   6.7181   0.0073   0.3224

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
 NRY  F07  C06  single    1.334  0.020  1.334
 NRY  C06  C05  aromatic  1.385  0.020  1.385
 NRY  C06  C08  aromatic  1.382  0.020  1.382
 NRY  C05  C04  aromatic  1.381  0.020  1.381
 NRY  C08  C09  aromatic  1.384  0.020  1.384
 NRY  C04  C03  aromatic  1.398  0.020  1.398
 NRY  C25  N24  aromatic  1.368  0.020  1.368
 NRY  C25  C26  aromatic  1.340  0.020  1.340
 NRY  C23  N24  aromatic  1.339  0.020  1.339
 NRY  C23  C22  aromatic  1.392  0.020  1.392
 NRY  C09  C03  aromatic  1.396  0.020  1.396
 NRY  N24  C20  aromatic  1.401  0.020  1.401
 NRY  C03  C02  single    1.475  0.020  1.475
 NRY  C26  N11  aromatic  1.382  0.020  1.382
 NRY  C22  C21  aromatic  1.390  0.020  1.390
 NRY  C20  C21  aromatic  1.393  0.020  1.393
 NRY  C20  C12  aromatic  1.387  0.020  1.387
 NRY  N11  C12  aromatic  1.331  0.020  1.331
 NRY  N11  C10  single    1.453  0.020  1.453
 NRY  C02  O01  double    1.209  0.020  1.209
 NRY  C02  C10  single    1.523  0.020  1.523
 NRY  C12  C13  single    1.475  0.020  1.475
 NRY  C13  C14  aromatic  1.392  0.020  1.392
 NRY  C13  C19  aromatic  1.392  0.020  1.392
 NRY  C14  C15  aromatic  1.385  0.020  1.385
 NRY  C19  C18  aromatic  1.385  0.020  1.385
 NRY  C15  C16  aromatic  1.382  0.020  1.382
 NRY  C18  C16  aromatic  1.383  0.020  1.383
 NRY  C16  F17  single    1.336  0.020  1.336
 NRY  C26  H1   single    0.930  0.020  1.080
 NRY  C25  H2   single    0.930  0.020  1.080
 NRY  C22  H3   single    0.930  0.020  1.080
 NRY  C23  H4   single    0.930  0.020  1.080
 NRY  C15  H5   single    0.930  0.020  1.080
 NRY  C14  H6   single    0.930  0.020  1.080
 NRY  C05  H7   single    0.930  0.020  1.080
 NRY  C04  H8   single    0.930  0.020  1.080
 NRY  C08  H9   single    0.930  0.020  1.080
 NRY  C09  H10  single    0.930  0.020  1.080
 NRY  C10  H11  single    0.970  0.020  1.090
 NRY  C10  H12  single    0.970  0.020  1.090
 NRY  C18  H13  single    0.930  0.020  1.080
 NRY  C19  H14  single    0.930  0.020  1.080
 NRY  C21  H15  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
 NRY  H1   C26  N11  116.91  3.000
 NRY  H1   C26  C25  121.58  3.000
 NRY  N11  C26  C25  121.51  3.000
 NRY  H2   C25  N24  118.33  3.000
 NRY  H2   C25  C26  122.62  3.000
 NRY  N24  C25  C26  119.06  3.000
 NRY  H3   C22  C21  126.61  3.000
 NRY  H3   C22  C23  124.83  3.000
 NRY  C21  C22  C23  108.56  3.000
 NRY  H4   C23  N24  121.36  3.000
 NRY  H4   C23  C22  130.51  3.000
 NRY  N24  C23  C22  108.13  3.000
 NRY  H5   C15  C16  120.65  3.000
 NRY  H5   C15  C14  120.81  3.000
 NRY  C16  C15  C14  118.53  3.000
 NRY  H6   C14  C13  120.24  3.000
 NRY  H6   C14  C15  119.61  3.000
 NRY  C13  C14  C15  120.15  3.000
 NRY  C19  C13  C12  120.68  3.000
 NRY  C19  C13  C14  120.18  3.000
 NRY  C12  C13  C14  119.11  3.000
 NRY  C20  C12  N11  119.16  3.000
 NRY  N11  C12  C13  121.35  3.000
 NRY  C20  C12  C13  119.48  3.000
 NRY  C18  C16  F17  118.77  3.000
 NRY  F17  C16  C15  118.78  3.000
 NRY  C18  C16  C15  122.45  3.000
 NRY  C08  C06  F07  118.78  3.000
 NRY  C08  C06  C05  122.47  3.000
 NRY  F07  C06  C05  118.74  3.000
 NRY  H7   C05  C04  121.08  3.000
 NRY  H7   C05  C06  120.48  3.000
 NRY  C04  C05  C06  118.43  3.000
 NRY  C10  C02  O01  119.83  3.000
 NRY  C10  C02  C03  117.31  3.000
 NRY  O01  C02  C03  122.86  3.000
 NRY  C09  C03  C04  119.18  3.000
 NRY  C09  C03  C02  122.05  3.000
 NRY  C04  C03  C02  118.76  3.000
 NRY  H8   C04  C03  120.02  3.000
 NRY  H8   C04  C05  119.22  3.000
 NRY  C03  C04  C05  120.75  3.000
 NRY  H9   C08  C09  120.95  3.000
 NRY  H9   C08  C06  120.64  3.000
 NRY  C09  C08  C06  118.41  3.000
 NRY  H10  C09  C08  117.82  3.000
 NRY  H10  C09  C03  121.43  3.000
 NRY  C08  C09  C03  120.74  3.000
 NRY  C10  N11  C12  122.14  3.000
 NRY  C10  N11  C26  116.98  3.000
 NRY  C12  N11  C26  120.85  3.000
 NRY  H13  C18  C19  120.69  3.000
 NRY  H13  C18  C16  120.68  3.000
 NRY  C19  C18  C16  118.63  3.000
 NRY  H14  C19  C18  119.30  3.000
 NRY  H14  C19  C13  120.64  3.000
 NRY  C18  C19  C13  120.05  3.000
 NRY  N24  C20  C21  107.39  3.000
 NRY  C21  C20  C12  133.07  3.000
 NRY  N24  C20  C12  119.55  3.000
 NRY  H15  C21  C20  125.79  3.000
 NRY  H15  C21  C22  127.49  3.000
 NRY  C20  C21  C22  106.72  3.000
 NRY  C20  N24  C23  109.20  3.000
 NRY  C20  N24  C25  119.83  3.000
 NRY  C23  N24  C25  130.96  3.000
 NRY  H12  C10  H11  106.60  3.000
 NRY  H12  C10  N11  108.08  3.000
 NRY  H11  C10  N11  109.77  3.000
 NRY  H12  C10  C02  110.28  3.000
 NRY  H11  C10  C02  111.04  3.000
 NRY  N11  C10  C02  110.93  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
 NRY  CONST_01  C23  N24  C25  C26  180.00   0.0  0
 NRY  CONST_02  C20  N24  C25  C26    0.00   0.0  0
 NRY  CONST_03  C20  C12  N11  C26    0.00   0.0  0
 NRY  CONST_04  C13  C12  N11  C26  180.00   0.0  0
 NRY  CONST_05  C22  C23  N24  C25  180.00   0.0  0
 NRY  CONST_06  C21  C20  N24  C25  180.00   0.0  0
 NRY  CONST_07  C12  C20  N24  C25    0.00   0.0  0
 NRY  CONST_08  C12  N11  C26  C25    0.00   0.0  0
 NRY  CONST_09  C20  N24  C23  C22    0.00   0.0  0
 NRY  CONST_10  N24  C20  C21  C22    0.00   0.0  0
 NRY  CONST_11  C12  C20  C21  C22  180.00   0.0  0
 NRY  CONST_12  C21  C20  N24  C23    0.00   0.0  0
 NRY  CONST_13  C12  C20  N24  C23  180.00   0.0  0
 NRY  CONST_14  C20  C21  C22  C23    0.00   0.0  0
 NRY  CONST_15  C12  C13  C14  C15  180.00   0.0  0
 NRY  CONST_16  C19  C13  C14  C15    0.00   0.0  0
 NRY  CONST_17  C19  C18  C16  C15    0.00   0.0  0
 NRY  CONST_20  C18  C19  C13  C14    0.00   0.0  0
 NRY  CONST_21  C18  C16  C15  C14    0.00   0.0  0
 NRY  CONST_22  N24  C20  C12  C13  180.00   0.0  0
 NRY  CONST_23  C21  C20  C12  C13    0.00   0.0  0
 NRY  CONST_24  C16  C15  C14  C13    0.00   0.0  0
 NRY  CONST_25  C16  C18  C19  C13    0.00   0.0  0
 NRY  CONST_26  C18  C19  C13  C12  180.00   0.0  0
 NRY  CONST_27  C03  C04  C05  C06    0.00   0.0  0
 NRY  CONST_28  C03  C09  C08  C06    0.00   0.0  0
 NRY  CONST_29  C09  C08  C06  C05    0.00   0.0  0
 NRY  CONST_30  C09  C03  C04  C05    0.00   0.0  0
 NRY  CONST_31  C08  C06  C05  C04    0.00   0.0  0
 NRY  CONST_32  C08  C09  C03  C04    0.00   0.0  0
 NRY  CONST_33  N24  C25  C26  N11    0.00   0.0  0
 NRY  CONST_34  N24  C20  C12  N11    0.00   0.0  0
 NRY  CONST_35  C21  C20  C12  N11  180.00   0.0  0
 NRY  CONST_38  N24  C23  C22  C21    0.00   0.0  0
 NRY  CONST_39  C10  N11  C26  C25  180.00   0.0  0
 NRY  CONST_40  F17  C16  C15  C14  180.00   0.0  0
 NRY  CONST_41  C10  N11  C12  C13    0.00   0.0  0
 NRY  CONST_42  C02  C03  C04  C05  180.00   0.0  0
 NRY  CONST_43  C08  C09  C03  C02  180.00   0.0  0
 NRY  CONST_44  F07  C06  C05  C04  180.00   0.0  0
 NRY  CONST_45  C09  C08  C06  F07  180.00   0.0  0
 NRY  CONST_46  C20  C12  N11  C10  180.00   0.0  0
 NRY  CONST_47  C19  C18  C16  F17  180.00   0.0  0
 NRY  CONST_48  H4   C23  N24  C25    0.00   0.0  0
 NRY  CONST_49  H2   C25  N24  C23    0.00   0.0  0
 NRY  CONST_50  H15  C21  C22  C23  180.00   0.0  0
 NRY  CONST_51  H13  C18  C16  C15  180.00   0.0  0
 NRY  CONST_52  H14  C19  C13  C14  180.00   0.0  0
 NRY  CONST_53  H5   C15  C14  C13  180.00   0.0  0
 NRY  CONST_54  H1   C26  N11  C12  180.00   0.0  0
 NRY  CONST_55  H6   C14  C13  C12    0.00   0.0  0
 NRY  CONST_56  H8   C04  C05  C06  180.00   0.0  0
 NRY  CONST_57  H10  C09  C08  C06  180.00   0.0  0
 NRY  CONST_58  H9   C08  C06  C05  180.00   0.0  0
 NRY  CONST_59  H7   C05  C04  C03  180.00   0.0  0
 NRY  CONST_60  H3   C22  C21  C20  180.00   0.0  0
 NRY  Var_01    C02  C10  N11  C26  -83.92  30.0  2
 NRY  Var_02    N11  C10  C02  C03  178.92  30.0  3
 NRY  Var_03    O01  C02  C03  C04    0.56  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
 NRY  plan-1  C15  0.020
 NRY  plan-1  C14  0.020
 NRY  plan-1  C13  0.020
 NRY  plan-1  C12  0.020
 NRY  plan-1  C16  0.020
 NRY  plan-1  F17  0.020
 NRY  plan-1  C18  0.020
 NRY  plan-1  C19  0.020
 NRY  plan-1  H5   0.020
 NRY  plan-1  H6   0.020
 NRY  plan-1  H13  0.020
 NRY  plan-1  H14  0.020
 NRY  plan-2  C06  0.020
 NRY  plan-2  C05  0.020
 NRY  plan-2  C02  0.020
 NRY  plan-2  C03  0.020
 NRY  plan-2  C04  0.020
 NRY  plan-2  C08  0.020
 NRY  plan-2  C09  0.020
 NRY  plan-2  H7   0.020
 NRY  plan-2  H8   0.020
 NRY  plan-2  H9   0.020
 NRY  plan-2  H10  0.020
 NRY  plan-2  F07  0.020
 NRY  plan-3  C26  0.020
 NRY  plan-3  C25  0.020
 NRY  plan-3  C22  0.020
 NRY  plan-3  C23  0.020
 NRY  plan-3  C13  0.020
 NRY  plan-3  C12  0.020
 NRY  plan-3  N11  0.020
 NRY  plan-3  C20  0.020
 NRY  plan-3  C21  0.020
 NRY  plan-3  N24  0.020
 NRY  plan-3  H1   0.020
 NRY  plan-3  H2   0.020
 NRY  plan-3  H3   0.020
 NRY  plan-3  H4   0.020
 NRY  plan-3  H15  0.020
 NRY  plan-3  C10  0.020
 NRY  plan-4  C02  0.020
 NRY  plan-4  C03  0.020
 NRY  plan-4  O01  0.020
 NRY  plan-4  C10  0.020

