# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 12 02:41:56 2020
#   Inital geometry file: a 94 line input string
#   Ligand name: N-(2-chlorophenyl)-5-phenylimidazo[1,5-a]pyrazin-8-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccccc1Nc2ncc(n3cncc23)c4ccccc4
#
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
 KSF  KSF  N-(2-chlorophenyl)-5-phenylimidazo[1,5-a]pyrazin-8-amine  ligand  36  23  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_KSF
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
 KSF  CL23  CL  CL    0  -0.118  -4.4264  -1.6407   0.2147
 KSF  C18   C   CR6   0  -0.158  -4.2074   0.0621  -0.0590
 KSF  C17   C   CR6   0   0.455  -2.9171   0.5718  -0.2700
 KSF  C22   C   CR16  0  -0.313  -2.7985   1.9481  -0.4847
 KSF  C21   C   CR16  0  -0.240  -3.9190   2.7637  -0.4813
 KSF  C20   C   CR16  0  -0.280  -5.1850   2.2393  -0.2720
 KSF  C19   C   CR16  0  -0.208  -5.3255   0.8762  -0.0626
 KSF  N16   N   NH1   0  -0.784  -1.8494  -0.3145  -0.2875
 KSF  C2    C   CR6   0   0.501  -0.5136  -0.0746  -0.1858
 KSF  N3    N   N     0  -0.463  -0.0301   1.1203  -0.0270
 KSF  C4    C   CR16  0  -0.160   1.3214   1.2670   0.0682
 KSF  C5    C   CR6   0   0.263   2.2258   0.2611   0.0221
 KSF  N6    N   N     0  -0.541   1.7032  -1.0173  -0.1327
 KSF  C7    C   CR15  0   0.087   2.2853  -2.2365  -0.1606
 KSF  N8    N   N     0  -0.424   1.3903  -3.1896  -0.2948
 KSF  C9    C   CR15  0  -0.246   0.1840  -2.5880  -0.3515
 KSF  C1    C   CR56  0   0.224   0.3407  -1.2228  -0.2476
 KSF  C10   C   CR6   0   0.048   3.6792   0.4561   0.1069
 KSF  C11   C   CR16  0  -0.287   4.2144   1.2203   1.1434
 KSF  C12   C   CR16  0  -0.240   5.5807   1.4534   1.2126
 KSF  C13   C   CR16  0  -0.257   6.4294   0.9172   0.2543
 KSF  C14   C   CR16  0  -0.241   5.9042   0.1531  -0.7807
 KSF  C15   C   CR16  0  -0.295   4.5391  -0.0745  -0.8573
 KSF  H22   H   HCR6  0   0.293  -1.8242   2.3760  -0.6524
 KSF  H21   H   HCR6  0   0.265  -3.7920   3.8249  -0.6490
 KSF  H20   H   HCR6  0   0.267  -6.0572   2.8781  -0.2723
 KSF  H19   H   HCR6  0   0.282  -6.3026   0.4434   0.1033
 KSF  HN16  H   HNH1  0   0.406  -2.1093  -1.2879  -0.3255
 KSF  H4    H   HCR6  0   0.271   1.6779   2.2837   0.1716
 KSF  H7    H   HCR5  0   0.301   3.3497  -2.3795  -0.0748
 KSF  H9    H   HCR5  0   0.270  -0.7293  -3.1538  -0.4611
 KSF  H11   H   HCR6  0   0.261   3.5601   1.6268   1.9041
 KSF  H12   H   HCR6  0   0.263   5.9823   2.0456   2.0243
 KSF  H13   H   HCR6  0   0.263   7.4954   1.0944   0.3119
 KSF  H14   H   HCR6  0   0.263   6.5580  -0.2607  -1.5371
 KSF  H15   H   HCR6  0   0.272   4.1423  -0.6469  -1.6868

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
 KSF  CL23  C18   single    1.739  0.020  1.739
 KSF  C18   C17   aromatic  1.403  0.020  1.403
 KSF  C18   C19   aromatic  1.383  0.020  1.383
 KSF  C17   C22   aromatic  1.398  0.020  1.398
 KSF  C17   N16   single    1.388  0.020  1.388
 KSF  C22   C21   aromatic  1.386  0.020  1.386
 KSF  C21   C20   aromatic  1.386  0.020  1.386
 KSF  C20   C19   aromatic  1.386  0.020  1.386
 KSF  N16   C2    single    1.361  0.020  1.361
 KSF  C2    N3    aromatic  1.299  0.020  1.299
 KSF  C2    C1    aromatic  1.432  0.020  1.432
 KSF  N3    C4    aromatic  1.363  0.020  1.363
 KSF  C4    C5    aromatic  1.354  0.020  1.354
 KSF  C5    N6    aromatic  1.390  0.020  1.390
 KSF  C5    C10   single    1.469  0.020  1.469
 KSF  N6    C7    aromatic  1.351  0.020  1.351
 KSF  N6    C1    aromatic  1.383  0.020  1.383
 KSF  C7    N8    aromatic  1.314  0.020  1.314
 KSF  N8    C9    aromatic  1.349  0.020  1.349
 KSF  C9    C1    aromatic  1.378  0.020  1.378
 KSF  C10   C11   aromatic  1.395  0.020  1.395
 KSF  C10   C15   aromatic  1.397  0.020  1.397
 KSF  C11   C12   aromatic  1.388  0.020  1.388
 KSF  C12   C13   aromatic  1.388  0.020  1.388
 KSF  C13   C14   aromatic  1.390  0.020  1.390
 KSF  C14   C15   aromatic  1.386  0.020  1.386
 KSF  C22   H22   single    0.930  0.020  1.080
 KSF  C21   H21   single    0.930  0.020  1.080
 KSF  C20   H20   single    0.930  0.020  1.080
 KSF  C19   H19   single    0.930  0.020  1.080
 KSF  N16   HN16  single    0.860  0.020  1.020
 KSF  C4    H4    single    0.930  0.020  1.080
 KSF  C7    H7    single    0.930  0.020  1.080
 KSF  C9    H9    single    0.930  0.020  1.080
 KSF  C11   H11   single    0.930  0.020  1.080
 KSF  C12   H12   single    0.930  0.020  1.080
 KSF  C13   H13   single    0.930  0.020  1.080
 KSF  C14   H14   single    0.930  0.020  1.080
 KSF  C15   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
 KSF  C19   C18  C17   121.95  3.000
 KSF  C19   C18  CL23  118.37  3.000
 KSF  C17   C18  CL23  119.69  3.000
 KSF  N16   C17  C22   124.16  3.000
 KSF  N16   C17  C18   118.51  3.000
 KSF  C22   C17  C18   117.30  3.000
 KSF  H22   C22  C21   119.86  3.000
 KSF  H22   C22  C17   119.45  3.000
 KSF  C21   C22  C17   120.69  3.000
 KSF  H21   C21  C20   120.11  3.000
 KSF  H21   C21  C22   118.82  3.000
 KSF  C20   C21  C22   121.07  3.000
 KSF  H20   C20  C19   119.95  3.000
 KSF  H20   C20  C21   120.88  3.000
 KSF  C19   C20  C21   119.17  3.000
 KSF  H19   C19  C20   120.55  3.000
 KSF  H19   C19  C18   119.63  3.000
 KSF  C20   C19  C18   119.82  3.000
 KSF  HN16  N16  C2    115.22  3.000
 KSF  HN16  N16  C17   114.75  3.000
 KSF  C2    N16  C17   129.91  3.000
 KSF  C1    C2   N3    121.38  3.000
 KSF  C1    C2   N16   116.16  3.000
 KSF  N3    C2   N16   122.46  3.000
 KSF  C4    N3   C2    118.48  3.000
 KSF  H4    C4   C5    118.77  3.000
 KSF  H4    C4   N3    115.75  3.000
 KSF  C5    C4   N3    125.47  3.000
 KSF  C10   C5   N6    120.05  3.000
 KSF  C10   C5   C4    124.09  3.000
 KSF  N6    C5   C4    115.86  3.000
 KSF  C1    N6   C7    106.78  3.000
 KSF  C1    N6   C5    121.10  3.000
 KSF  C7    N6   C5    132.08  3.000
 KSF  H7    C7   N8    125.78  3.000
 KSF  H7    C7   N6    122.94  3.000
 KSF  N8    C7   N6    111.28  3.000
 KSF  C9    N8   C7    106.85  3.000
 KSF  H9    C9   C1    128.52  3.000
 KSF  H9    C9   N8    121.79  3.000
 KSF  C1    C9   N8    109.68  3.000
 KSF  C9    C1   N6    105.40  3.000
 KSF  C9    C1   C2    136.84  3.000
 KSF  N6    C1   C2    117.71  3.000
 KSF  C15   C10  C11   119.02  3.000
 KSF  C15   C10  C5    121.25  3.000
 KSF  C11   C10  C5    119.70  3.000
 KSF  H11   C11  C12   119.80  3.000
 KSF  H11   C11  C10   119.74  3.000
 KSF  C12   C11  C10   120.46  3.000
 KSF  H12   C12  C13   120.16  3.000
 KSF  H12   C12  C11   119.65  3.000
 KSF  C13   C12  C11   120.18  3.000
 KSF  H13   C13  C14   120.13  3.000
 KSF  H13   C13  C12   120.16  3.000
 KSF  C14   C13  C12   119.71  3.000
 KSF  H14   C14  C15   119.58  3.000
 KSF  H14   C14  C13   120.18  3.000
 KSF  C15   C14  C13   120.24  3.000
 KSF  H15   C15  C14   119.33  3.000
 KSF  H15   C15  C10   120.26  3.000
 KSF  C14   C15  C10   120.38  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
 KSF  CONST_01  C21  C22  C17  C18      0.00   0.0  0
 KSF  CONST_02  C21  C20  C19  C18      0.00   0.0  0
 KSF  CONST_03  C20  C19  C18  C17      0.00   0.0  0
 KSF  CONST_04  C20  C21  C22  C17      0.00   0.0  0
 KSF  CONST_05  C19  C18  C17  C22      0.00   0.0  0
 KSF  CONST_06  C19  C20  C21  C22      0.00   0.0  0
 KSF  CONST_07  C5   C4   N3   C2       0.00   0.0  0
 KSF  CONST_08  C5   N6   C1   C2       0.00   0.0  0
 KSF  CONST_09  C7   N6   C1   C2     180.00   0.0  0
 KSF  CONST_10  N8   C9   C1   C2     180.00   0.0  0
 KSF  CONST_11  N6   C1   C2   N3       0.00   0.0  0
 KSF  CONST_12  C9   C1   C2   N3     180.00   0.0  0
 KSF  CONST_13  N6   C5   C4   N3       0.00   0.0  0
 KSF  CONST_14  C10  C5   C4   N3     180.00   0.0  0
 KSF  CONST_15  C1   C2   N3   C4       0.00   0.0  0
 KSF  CONST_16  C7   N6   C5   C4     180.00   0.0  0
 KSF  CONST_17  C1   N6   C5   C4       0.00   0.0  0
 KSF  CONST_20  N8   C7   N6   C5     180.00   0.0  0
 KSF  CONST_21  C9   C1   N6   C5     180.00   0.0  0
 KSF  CONST_22  C12  C11  C10  C5     180.00   0.0  0
 KSF  CONST_23  C14  C15  C10  C5     180.00   0.0  0
 KSF  CONST_26  C9   N8   C7   N6       0.00   0.0  0
 KSF  CONST_27  N8   C9   C1   N6       0.00   0.0  0
 KSF  CONST_28  C10  C5   N6   C7       0.00   0.0  0
 KSF  CONST_29  C9   C1   N6   C7       0.00   0.0  0
 KSF  CONST_30  C1   C9   N8   C7       0.00   0.0  0
 KSF  CONST_31  C1   N6   C7   N8       0.00   0.0  0
 KSF  CONST_32  C10  C5   N6   C1     180.00   0.0  0
 KSF  CONST_33  C13  C12  C11  C10      0.00   0.0  0
 KSF  CONST_34  C13  C14  C15  C10      0.00   0.0  0
 KSF  CONST_35  C14  C15  C10  C11      0.00   0.0  0
 KSF  CONST_36  C14  C13  C12  C11      0.00   0.0  0
 KSF  CONST_37  C15  C10  C11  C12      0.00   0.0  0
 KSF  CONST_38  C15  C14  C13  C12      0.00   0.0  0
 KSF  CONST_39  C22  C17  C18  CL23   180.00   0.0  0
 KSF  CONST_40  C20  C19  C18  CL23   180.00   0.0  0
 KSF  CONST_41  N16  C17  C22  C21    180.00   0.0  0
 KSF  CONST_42  N16  C17  C18  C19    180.00   0.0  0
 KSF  CONST_43  C4   N3   C2   N16    180.00   0.0  0
 KSF  CONST_44  N6   C1   C2   N16    180.00   0.0  0
 KSF  CONST_45  C9   C1   C2   N16      0.00   0.0  0
 KSF  CONST_46  H22  C22  C17  C18    180.00   0.0  0
 KSF  CONST_47  H20  C20  C19  C18    180.00   0.0  0
 KSF  CONST_48  H19  C19  C18  C17    180.00   0.0  0
 KSF  CONST_49  H21  C21  C22  C17    180.00   0.0  0
 KSF  CONST_50  H4   C4   N3   C2     180.00   0.0  0
 KSF  CONST_51  H9   C9   C1   C2       0.00   0.0  0
 KSF  CONST_52  H7   C7   N6   C5       0.00   0.0  0
 KSF  CONST_53  H11  C11  C10  C5       0.00   0.0  0
 KSF  CONST_54  H15  C15  C10  C5       0.00   0.0  0
 KSF  CONST_55  H12  C12  C11  C10    180.00   0.0  0
 KSF  CONST_56  H14  C14  C15  C10    180.00   0.0  0
 KSF  CONST_57  H13  C13  C12  C11    180.00   0.0  0
 KSF  Var_01    C2   N16  C17  C18   -164.35  30.0  2
 KSF  Var_02    N3   C2   N16  C17      1.07  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
 KSF  plan-1  CL23  0.020
 KSF  plan-1  C18   0.020
 KSF  plan-1  C17   0.020
 KSF  plan-1  C22   0.020
 KSF  plan-1  C21   0.020
 KSF  plan-1  C20   0.020
 KSF  plan-1  C19   0.020
 KSF  plan-1  N16   0.020
 KSF  plan-1  H22   0.020
 KSF  plan-1  H21   0.020
 KSF  plan-1  H20   0.020
 KSF  plan-1  H19   0.020
 KSF  plan-2  C5    0.020
 KSF  plan-2  C10   0.020
 KSF  plan-2  C11   0.020
 KSF  plan-2  C12   0.020
 KSF  plan-2  C13   0.020
 KSF  plan-2  C14   0.020
 KSF  plan-2  C15   0.020
 KSF  plan-2  H11   0.020
 KSF  plan-2  H12   0.020
 KSF  plan-2  H13   0.020
 KSF  plan-2  H14   0.020
 KSF  plan-2  H15   0.020
 KSF  plan-3  N16   0.020
 KSF  plan-3  C2    0.020
 KSF  plan-3  N3    0.020
 KSF  plan-3  C4    0.020
 KSF  plan-3  C5    0.020
 KSF  plan-3  N6    0.020
 KSF  plan-3  C7    0.020
 KSF  plan-3  N8    0.020
 KSF  plan-3  C9    0.020
 KSF  plan-3  C1    0.020
 KSF  plan-3  C10   0.020
 KSF  plan-3  H4    0.020
 KSF  plan-3  H7    0.020
 KSF  plan-3  H9    0.020

