# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 13:32:08 2021
#   Inital geometry file: a 136 line input string
#   Ligand name: 6-[2-[2,4-bis(fluoranyl)phenoxy]-5-(ethylsulfonylmethyl)pyridin-3-yl]-8-methyl-4~{H}-pyrrolo[1,2-a]pyrazin-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[S](=O)(=O)Cc1cnc(Oc2ccc(F)cc2F)c(c1)c3cc(C)c4n3CC=NC4=O
#
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
 D89  D89  6-[2-[2,4-bis(fluoranyl)phenoxy]-5-(ethylsulfonylmethyl)pyridin-3-yl]-8-methyl-4~{H}-pyrrolo[1,2-a]pyrazin-1-one  ligand  51  32  .  2022-03-18  2022-07-24
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_D89
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
 D89  C10   C  CH3   0  -0.737  -12.3606   -2.5884  -1.5771
 D89  C13   C  CR16  0  -0.177   -8.0013   -6.3538  -1.5936
 D89  C15   C  CR16  0  -0.058   -6.2881   -7.1842  -0.1779
 D89  C17   C  CR6   0   0.498   -8.1072   -6.2214   0.7657
 D89  C22   C  CH2   0  -0.600   -5.5453   -9.6355  -4.4247
 D89  C26   C  CR16  0  -0.423   -7.2262   -5.2684   5.1314
 D89  C28   C  CR16  0  -0.565   -7.8135   -7.6078   4.9011
 D89  N1    N  N     0  -0.396  -13.8122   -6.4790   0.4883
 D89  C2    C  CR16  0  -0.014  -12.8482   -7.2692   0.7264
 D89  C3    C  C     0  -0.350  -11.3970   -7.0362   0.4972
 D89  N4    N  N     0  -0.536  -11.1620   -5.7673  -0.1310
 D89  C5    C  CR56  0   0.150  -12.1790   -4.8897  -0.4183
 D89  C6    C  CR6   0   0.427  -13.5430   -5.2141  -0.0834
 D89  C7    C  CR5   0   0.373   -9.9945   -5.2675  -0.5910
 D89  C8    C  CR15  0  -0.424  -10.2626   -4.0461  -1.1861
 D89  C9    C  CR5   0   0.048  -11.6392   -3.7939  -1.0782
 D89  O11   O  O     0  -0.413  -14.4720   -4.4588  -0.2836
 D89  C12   C  CR6   0  -0.125   -8.7118   -5.9629  -0.4714
 D89  C14   C  CR6   0   0.025   -6.7606   -6.9731  -1.4623
 D89  N16   N  N     0  -0.433   -6.9471   -6.8070   0.9113
 D89  C19   C  CR6   0   0.204   -8.2392   -6.0572   3.0983
 D89  S21   S  S     0   1.210   -6.5801   -9.1061  -3.0628
 D89  O23   O  OS    0  -0.675   -7.9638   -8.9930  -3.5267
 D89  O24   O  OS    0  -0.677   -6.3108   -9.9662  -1.9106
 D89  C25   C  CR16  0  -0.289   -7.7051   -5.0282   3.8505
 D89  C27   C  CR6   0   0.544   -7.2871   -6.5548   5.6279
 D89  C29   C  CR6   0   0.526   -8.2876   -7.3340   3.6363
 D89  F30   F  F     0  -0.298   -8.8121   -8.3186   2.9030
 D89  F31   F  F     0  -0.307   -6.8242   -6.8036   6.8587
 D89  C32   C  CH3   0  -0.679   -5.7583   -8.8288  -5.6905
 D89  H102  H  HCH3  0   0.245  -13.1458   -2.8506  -2.2862
 D89  H103  H  HCH3  0   0.245  -12.8370   -2.0383  -0.7654
 D89  H101  H  HCH3  0   0.241  -11.6691   -1.9135  -2.0786
 D89  H131  H  HCR6  0   0.276   -8.4198   -6.1675  -2.5744
 D89  H151  H  HCR6  0   0.279   -5.3296   -7.6636  -0.0155
 D89  H202  H  HCH2  0   0.330   -4.9239   -7.5248  -2.4467
 D89  H201  H  HCH2  0   0.329   -6.1411   -6.8064  -3.5188
 D89  H222  H  HCH2  0   0.318   -5.8072  -10.6864  -4.5678
 D89  H221  H  HCH2  0   0.303   -4.5157   -9.5909  -4.0673
 D89  H261  H  HCR6  0   0.294   -6.8124   -4.4653   5.7256
 D89  H281  H  HCR6  0   0.312   -7.8567   -8.6108   5.3051
 D89  H021  H  HCR6  0   0.296  -13.0808   -8.2362   1.1650
 D89  H031  H  H     0   0.310  -11.0021   -7.8572  -0.1081
 D89  H1    H  H     0   0.301  -10.9050   -7.1008   1.4714
 D89  H081  H  HCR5  0   0.260   -9.5235   -3.4012  -1.6370
 D89  H251  H  HCR6  0   0.295   -7.6693   -4.0289   3.4373
 D89  H321  H  HCH3  0   0.268   -5.1270   -9.2382  -6.4777
 D89  H323  H  HCH3  0   0.252   -6.7905   -8.8818  -6.0307
 D89  H322  H  HCH3  0   0.247   -5.4833   -7.7819  -5.5676
 D89  O18   O  O2    0  -0.509   -8.7753   -5.8037   1.8627
 D89  C20   C  CH2   0  -0.721   -5.9928   -7.4463  -2.6490

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
 D89  C22  C32   single    1.516  0.020  1.516
 D89  C22  S21   single    1.790  0.020  1.790
 D89  O24  S21   double    1.463  0.020  1.463
 D89  S21  O23   double    1.464  0.020  1.464
 D89  S21  C20   single    1.809  0.020  1.809
 D89  C10  C9    single    1.491  0.020  1.491
 D89  C20  C14   single    1.491  0.020  1.491
 D89  C8   C9    aromatic  1.404  0.020  1.404
 D89  C8   C7    aromatic  1.385  0.020  1.385
 D89  C9   C5    aromatic  1.388  0.020  1.388
 D89  C13  C14   aromatic  1.393  0.020  1.393
 D89  C13  C12   aromatic  1.385  0.020  1.385
 D89  C14  C15   aromatic  1.385  0.020  1.385
 D89  C7   C12   single    1.464  0.020  1.464
 D89  C7   N4    aromatic  1.351  0.020  1.351
 D89  O11  C6    double    1.214  0.020  1.214
 D89  C5   C6    single    1.441  0.020  1.441
 D89  C5   N4    aromatic  1.374  0.020  1.374
 D89  C12  C17   aromatic  1.401  0.020  1.401
 D89  C6   N1    single    1.414  0.020  1.414
 D89  N4   C3    single    1.435  0.020  1.435
 D89  C15  N16   aromatic  1.328  0.020  1.328
 D89  N1   C2    double    1.269  0.020  1.269
 D89  C3   C2    single    1.487  0.020  1.487
 D89  C17  N16   aromatic  1.308  0.020  1.308
 D89  C17  O18   single    1.351  0.020  1.351
 D89  O18  C19   single    1.370  0.020  1.370
 D89  C25  C19   aromatic  1.382  0.020  1.382
 D89  C25  C26   aromatic  1.388  0.020  1.388
 D89  C19  C29   aromatic  1.386  0.020  1.386
 D89  C26  C27   aromatic  1.380  0.020  1.380
 D89  C29  F30   single    1.335  0.020  1.335
 D89  C29  C28   aromatic  1.378  0.020  1.378
 D89  C27  C28   aromatic  1.384  0.020  1.384
 D89  C27  F31   single    1.338  0.020  1.338
 D89  C10  H102  single    0.970  0.020  1.090
 D89  C10  H103  single    0.970  0.020  1.090
 D89  C10  H101  single    0.970  0.020  1.090
 D89  C13  H131  single    0.930  0.020  1.080
 D89  C15  H151  single    0.930  0.020  1.080
 D89  C20  H202  single    0.970  0.020  1.090
 D89  C20  H201  single    0.970  0.020  1.090
 D89  C22  H222  single    0.970  0.020  1.090
 D89  C22  H221  single    0.970  0.020  1.090
 D89  C26  H261  single    0.930  0.020  1.080
 D89  C28  H281  single    0.930  0.020  1.080
 D89  C2   H021  single    0.930  0.020  1.080
 D89  C3   H031  single    0.970  0.020  1.090
 D89  C3   H1    single    0.970  0.020  1.090
 D89  C8   H081  single    0.930  0.020  1.080
 D89  C25  H251  single    0.930  0.020  1.080
 D89  C32  H321  single    0.970  0.020  1.090
 D89  C32  H323  single    0.970  0.020  1.090
 D89  C32  H322  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
 D89  H101  C10  H103  107.93  3.000
 D89  H101  C10  H102  107.88  3.000
 D89  H103  C10  H102  106.92  3.000
 D89  H101  C10  C9    110.37  3.000
 D89  H103  C10  C9    111.74  3.000
 D89  H102  C10  C9    111.82  3.000
 D89  H131  C13  C14   120.41  3.000
 D89  H131  C13  C12   119.17  3.000
 D89  C14   C13  C12   120.42  3.000
 D89  H151  C15  N16   116.21  3.000
 D89  H151  C15  C14   120.54  3.000
 D89  N16   C15  C14   123.25  3.000
 D89  O18   C17  N16   119.14  3.000
 D89  O18   C17  C12   116.53  3.000
 D89  N16   C17  C12   124.32  3.000
 D89  H221  C22  H222  107.98  3.000
 D89  H221  C22  C32   112.61  3.000
 D89  H222  C22  C32   111.64  3.000
 D89  H221  C22  S21   106.51  3.000
 D89  H222  C22  S21   104.22  3.000
 D89  C32   C22  S21   113.36  3.000
 D89  H261  C26  C27   120.75  3.000
 D89  H261  C26  C25   120.70  3.000
 D89  C27   C26  C25   118.55  3.000
 D89  H281  C28  C29   120.86  3.000
 D89  H281  C28  C27   121.63  3.000
 D89  C29   C28  C27   117.51  3.000
 D89  C6    N1   C2    119.23  3.000
 D89  H021  C2   C3    114.22  3.000
 D89  H021  C2   N1    117.84  3.000
 D89  C3    C2   N1    127.93  3.000
 D89  H1    C3   H031  106.63  3.000
 D89  H1    C3   N4    111.63  3.000
 D89  H031  C3   N4    111.24  3.000
 D89  H1    C3   C2    107.01  3.000
 D89  H031  C3   C2    108.65  3.000
 D89  N4    C3   C2    111.45  3.000
 D89  C7    N4   C5    109.41  3.000
 D89  C5    N4   C3    122.35  3.000
 D89  C7    N4   C3    128.15  3.000
 D89  C9    C5   C6    130.99  3.000
 D89  C6    C5   N4    120.55  3.000
 D89  C9    C5   N4    108.41  3.000
 D89  O11   C6   C5    123.08  3.000
 D89  C5    C6   N1    118.38  3.000
 D89  O11   C6   N1    118.53  3.000
 D89  C12   C7   C8    128.59  3.000
 D89  C12   C7   N4    123.62  3.000
 D89  C8    C7   N4    107.78  3.000
 D89  H081  C8   C9    126.60  3.000
 D89  H081  C8   C7    125.02  3.000
 D89  C9    C8   C7    108.38  3.000
 D89  C8    C9   C5    106.02  3.000
 D89  C5    C9   C10   127.52  3.000
 D89  C8    C9   C10   126.45  3.000
 D89  C7    C12  C17   122.54  3.000
 D89  C17   C12  C13   116.24  3.000
 D89  C7    C12  C13   121.17  3.000
 D89  C20   C14  C15   120.95  3.000
 D89  C15   C14  C13   117.33  3.000
 D89  C20   C14  C13   121.66  3.000
 D89  C17   N16  C15   118.44  3.000
 D89  C29   C19  C25   119.21  3.000
 D89  C29   C19  O18   120.43  3.000
 D89  C25   C19  O18   120.28  3.000
 D89  O24   S21  O23   117.98  3.000
 D89  O23   S21  C22   109.16  3.000
 D89  O24   S21  C22   108.59  3.000
 D89  O23   S21  C20   107.97  3.000
 D89  O24   S21  C20   107.43  3.000
 D89  C22   S21  C20   104.93  3.000
 D89  H251  C25  C19   119.51  3.000
 D89  H251  C25  C26   120.04  3.000
 D89  C19   C25  C26   120.44  3.000
 D89  F31   C27  C28   118.25  3.000
 D89  F31   C27  C26   119.26  3.000
 D89  C28   C27  C26   122.48  3.000
 D89  F30   C29  C19   118.67  3.000
 D89  F30   C29  C28   119.52  3.000
 D89  C19   C29  C28   121.81  3.000
 D89  H322  C32  H323  108.76  3.000
 D89  H322  C32  H321  107.25  3.000
 D89  H323  C32  H321  107.80  3.000
 D89  H322  C32  C22   112.44  3.000
 D89  H323  C32  C22   111.62  3.000
 D89  H321  C32  C22   108.78  3.000
 D89  C19   O18  C17   118.78  3.000
 D89  H201  C20  H202  108.88  3.000
 D89  H201  C20  S21   108.18  3.000
 D89  H202  C20  S21   107.14  3.000
 D89  H201  C20  C14   112.26  3.000
 D89  H202  C20  C14   112.33  3.000
 D89  S21   C20  C14   107.83  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
 D89  CONST_01  N16   C15  C14  C13     0.00   0.0  0
 D89  CONST_04  N16   C17  C12  C13     0.00   0.0  0
 D89  CONST_05  C12   C13  C14  C15     0.00   0.0  0
 D89  CONST_06  C12   C17  N16  C15     0.00   0.0  0
 D89  CONST_07  C14   C13  C12  C17     0.00   0.0  0
 D89  CONST_10  C14   C15  N16  C17     0.00   0.0  0
 D89  CONST_11  C29   C19  C25  C26     0.00   0.0  0
 D89  CONST_12  C29   C28  C27  C26     0.00   0.0  0
 D89  CONST_13  C25   C19  C29  C28     0.00   0.0  0
 D89  CONST_14  C25   C26  C27  C28     0.00   0.0  0
 D89  CONST_15  C9    C8   C7   N4      0.00   0.0  0
 D89  CONST_16  C8    C9   C5   N4      0.00   0.0  0
 D89  CONST_17  C7    C8   C9   C5      0.00   0.0  0
 D89  CONST_18  C8    C7   N4   C5      0.00   0.0  0
 D89  CONST_19  C12   C7   N4   C5    180.00   0.0  0
 D89  CONST_20  C14   C13  C12  C7    180.00   0.0  0
 D89  CONST_21  N16   C17  C12  C7    180.00   0.0  0
 D89  CONST_22  C9    C5   N4   C7      0.00   0.0  0
 D89  CONST_23  C12   C7   C8   C9    180.00   0.0  0
 D89  CONST_24  C27   C26  C25  C19     0.00   0.0  0
 D89  CONST_25  C27   C28  C29  C19     0.00   0.0  0
 D89  CONST_26  C12   C7   N4   C3      0.00   0.0  0
 D89  CONST_27  C7    C8   C9   C10   180.00   0.0  0
 D89  CONST_28  C6    C5   C9   C10     0.00   0.0  0
 D89  CONST_29  N4    C5   C9   C10   180.00   0.0  0
 D89  CONST_30  O18   C17  C12  C13   180.00   0.0  0
 D89  CONST_31  O18   C17  N16  C15   180.00   0.0  0
 D89  CONST_32  C12   C13  C14  C20   180.00   0.0  0
 D89  CONST_33  N16   C15  C14  C20   180.00   0.0  0
 D89  CONST_34  O18   C19  C25  C26   180.00   0.0  0
 D89  CONST_35  O18   C19  C29  C28   180.00   0.0  0
 D89  CONST_36  O18   C17  C12  C7      0.00   0.0  0
 D89  CONST_37  F30   C29  C19  C25   180.00   0.0  0
 D89  CONST_38  F31   C27  C26  C25   180.00   0.0  0
 D89  CONST_39  F30   C29  C28  C27   180.00   0.0  0
 D89  CONST_40  F31   C27  C28  C29   180.00   0.0  0
 D89  CONST_41  H151  C15  C14  C13   180.00   0.0  0
 D89  CONST_42  H131  C13  C14  C15   180.00   0.0  0
 D89  CONST_43  H281  C28  C27  C26   180.00   0.0  0
 D89  CONST_44  H261  C26  C27  C28   180.00   0.0  0
 D89  CONST_45  H081  C8   C7   N4    180.00   0.0  0
 D89  CONST_46  H251  C25  C26  C27   180.00   0.0  0
 D89  Var_01    C9    C5   C6   N1    173.99  30.0  1
 D89  Var_02    N4    C3   C2   N1     -3.27  30.0  1
 D89  Var_03    C5    C6   N1   C2      2.15  30.0  1
 D89  Var_04    C7    N4   C3   C2   -173.89  30.0  1
 D89  Var_05    C25   C19  O18  C17   108.35  30.0  2
 D89  Var_06    S21   C20  C14  C13   -85.50  30.0  2
 D89  Var_07    H102  C10  C9   C5    -58.28  30.0  2
 D89  Var_08    C14   C20  S21  C22  -176.66  30.0  3
 D89  Var_09    C32   C22  S21  C20   -66.49  30.0  1
 D89  Var_10    H321  C32  C22  S21  -177.62  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
 D89  plan-1  C13   0.020
 D89  plan-1  C15   0.020
 D89  plan-1  C17   0.020
 D89  plan-1  C7    0.020
 D89  plan-1  C12   0.020
 D89  plan-1  C14   0.020
 D89  plan-1  N16   0.020
 D89  plan-1  H131  0.020
 D89  plan-1  H151  0.020
 D89  plan-1  O18   0.020
 D89  plan-1  C20   0.020
 D89  plan-2  C26   0.020
 D89  plan-2  C28   0.020
 D89  plan-2  C19   0.020
 D89  plan-2  C25   0.020
 D89  plan-2  C27   0.020
 D89  plan-2  C29   0.020
 D89  plan-2  F30   0.020
 D89  plan-2  F31   0.020
 D89  plan-2  H261  0.020
 D89  plan-2  H281  0.020
 D89  plan-2  H251  0.020
 D89  plan-2  O18   0.020
 D89  plan-3  C10   0.020
 D89  plan-3  C3    0.020
 D89  plan-3  N4    0.020
 D89  plan-3  C5    0.020
 D89  plan-3  C6    0.020
 D89  plan-3  C7    0.020
 D89  plan-3  C8    0.020
 D89  plan-3  C9    0.020
 D89  plan-3  C12   0.020
 D89  plan-3  H081  0.020
 D89  plan-4  N1    0.020
 D89  plan-4  C5    0.020
 D89  plan-4  C6    0.020
 D89  plan-4  O11   0.020

