# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 11:37:38 2022
#   Inital geometry file: a 92 line input string
#   Ligand name: 6-(1~{H}-indol-5-yl)-~{N}-methyl-2-methylsulfonyl-pyrimidin-4-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CNc1cc(nc(n1)[S](C)(=O)=O)c2ccc3[nH]ccc3c2
#
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
 EUO  EUO  6-(1~{H}-indol-5-yl)-~{N}-methyl-2-methylsulfonyl-pyrimidin-4-amine  ligand  35  21  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_EUO
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
 EUO  C10  C  CR56  0   0.352   6.9768  -6.0889  68.4929
 EUO  C13  C  CR15  0  -0.415   8.4141  -5.2526  66.9297
 EUO  C20  C  CH3   0  -0.790   3.8536  -2.9250  63.0354
 EUO  C01  C  CR6   0   0.181   2.4378  -2.9623  65.5004
 EUO  C03  C  CR6   0   0.555   1.2516  -3.2705  67.3729
 EUO  C04  C  CR16  0  -0.447   2.3615  -3.9520  67.9130
 EUO  C05  C  CR6   0   0.308   3.4870  -4.0988  67.1265
 EUO  C07  C  CR6   0   0.038   4.6979  -4.7976  67.5868
 EUO  C08  C  CR16  0  -0.382   5.8976  -4.6009  66.9147
 EUO  C09  C  CR56  0   0.091   7.0519  -5.2402  67.3649
 EUO  C11  C  CR16  0  -0.281   5.7765  -6.3099  69.1675
 EUO  C12  C  CR16  0  -0.340   4.6545  -5.6599  68.7056
 EUO  C14  C  CR15  0  -0.022   9.0864  -6.0792  67.7808
 EUO  C18  C  CH3   0  -0.535  -0.1149  -3.5536  69.3929
 EUO  N02  N  N     0  -0.450   1.3066  -2.7714  66.1253
 EUO  N06  N  N     0  -0.462   3.5232  -3.5755  65.8809
 EUO  N15  N  NR15  0  -0.678   8.2244  -6.5790  68.7183
 EUO  O19  O  OS    0  -0.670   2.7673  -0.7626  64.0945
 EUO  O21  O  OS    0  -0.665   1.2455  -2.5274  63.1730
 EUO  S16  S  S     0   1.185   2.4770  -2.1768  63.8723
 EUO  H1   H  HCR5  0   0.249   8.8374  -4.7171  66.0952
 EUO  H2   H  HCH3  0   0.298   4.7750  -2.7136  63.5697
 EUO  H3   H  HCH3  0   0.295   3.6962  -3.9972  62.9513
 EUO  H4   H  HCH3  0   0.308   3.8828  -2.4736  62.0438
 EUO  H5   H  HCR6  0   0.287   2.3314  -4.3295  68.9235
 EUO  H6   H  HCR6  0   0.254   5.9379  -3.9466  66.0539
 EUO  H7   H  HCR6  0   0.265   5.7210  -6.9736  70.0207
 EUO  H8   H  HCR6  0   0.250   3.7159  -5.8423  69.2109
 EUO  H9   H  HCR5  0   0.283  10.1286  -6.3551  67.7965
 EUO  H10  H  HCH3  0   0.272  -1.1222  -3.2714  69.6837
 EUO  H11  H  HCH3  0   0.246  -0.0336  -4.6400  69.4607
 EUO  H12  H  HCH3  0   0.246   0.5817  -3.1105  70.1071
 EUO  H13  H  HNR5  0   0.412   8.4793  -7.2186  69.4531
 EUO  H14  H  HNH1  0   0.403  -0.6109  -2.5731  67.5810
 EUO  N17  N  NH1   0  -0.639   0.1199  -3.0825  68.0510

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
 EUO  C20  S16  single    1.776  0.020  1.776
 EUO  O21  S16  double    1.459  0.020  1.459
 EUO  S16  O19  double    1.461  0.020  1.461
 EUO  S16  C01  single    1.808  0.020  1.808
 EUO  C01  N06  aromatic  1.303  0.020  1.303
 EUO  C01  N02  aromatic  1.306  0.020  1.306
 EUO  N06  C05  aromatic  1.352  0.020  1.352
 EUO  N02  C03  aromatic  1.345  0.020  1.345
 EUO  C13  C09  aromatic  1.430  0.020  1.430
 EUO  C13  C14  aromatic  1.364  0.020  1.364
 EUO  C08  C09  aromatic  1.394  0.020  1.394
 EUO  C08  C07  aromatic  1.389  0.020  1.389
 EUO  C05  C07  single    1.472  0.020  1.472
 EUO  C05  C04  aromatic  1.381  0.020  1.381
 EUO  C09  C10  aromatic  1.414  0.020  1.414
 EUO  C03  C04  aromatic  1.410  0.020  1.410
 EUO  C03  N17  single    1.333  0.020  1.333
 EUO  C07  C12  aromatic  1.413  0.020  1.413
 EUO  C14  N15  aromatic  1.368  0.020  1.368
 EUO  N17  C18  single    1.441  0.020  1.441
 EUO  C10  N15  aromatic  1.359  0.020  1.359
 EUO  C10  C11  aromatic  1.395  0.020  1.395
 EUO  C12  C11  aromatic  1.377  0.020  1.377
 EUO  C13  H1   single    0.930  0.020  1.080
 EUO  C20  H2   single    0.970  0.020  1.090
 EUO  C20  H3   single    0.970  0.020  1.090
 EUO  C20  H4   single    0.970  0.020  1.090
 EUO  C04  H5   single    0.930  0.020  1.080
 EUO  C08  H6   single    0.930  0.020  1.080
 EUO  C11  H7   single    0.930  0.020  1.080
 EUO  C12  H8   single    0.930  0.020  1.080
 EUO  C14  H9   single    0.930  0.020  1.080
 EUO  C18  H10  single    0.970  0.020  1.090
 EUO  C18  H11  single    0.970  0.020  1.090
 EUO  C18  H12  single    0.970  0.020  1.090
 EUO  N15  H13  single    0.860  0.020  1.020
 EUO  N17  H14  single    0.860  0.020  1.020

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
 EUO  N15  C10  C11  130.74  3.000
 EUO  C11  C10  C09  121.80  3.000
 EUO  N15  C10  C09  107.46  3.000
 EUO  H1   C13  C14  126.20  3.000
 EUO  H1   C13  C09  127.25  3.000
 EUO  C14  C13  C09  106.55  3.000
 EUO  H4   C20  H3   110.00  3.000
 EUO  H4   C20  H2   110.14  3.000
 EUO  H3   C20  H2   110.67  3.000
 EUO  H4   C20  S16  105.96  3.000
 EUO  H3   C20  S16  109.86  3.000
 EUO  H2   C20  S16  110.11  3.000
 EUO  S16  C01  N06  116.69  3.000
 EUO  N06  C01  N02  130.56  3.000
 EUO  S16  C01  N02  112.71  3.000
 EUO  N17  C03  N02  117.03  3.000
 EUO  N17  C03  C04  122.80  3.000
 EUO  N02  C03  C04  120.17  3.000
 EUO  H5   C04  C05  121.26  3.000
 EUO  H5   C04  C03  120.39  3.000
 EUO  C05  C04  C03  118.34  3.000
 EUO  N06  C05  C07  116.74  3.000
 EUO  C07  C05  C04  122.88  3.000
 EUO  N06  C05  C04  120.37  3.000
 EUO  C12  C07  C08  119.73  3.000
 EUO  C12  C07  C05  120.80  3.000
 EUO  C08  C07  C05  119.47  3.000
 EUO  H6   C08  C09  120.22  3.000
 EUO  H6   C08  C07  120.18  3.000
 EUO  C09  C08  C07  119.60  3.000
 EUO  C08  C09  C13  133.98  3.000
 EUO  C08  C09  C10  119.27  3.000
 EUO  C13  C09  C10  106.75  3.000
 EUO  H7   C11  C12  120.82  3.000
 EUO  H7   C11  C10  121.51  3.000
 EUO  C12  C11  C10  117.67  3.000
 EUO  H8   C12  C11  118.10  3.000
 EUO  H8   C12  C07  119.96  3.000
 EUO  C11  C12  C07  121.92  3.000
 EUO  H9   C14  N15  120.37  3.000
 EUO  H9   C14  C13  129.85  3.000
 EUO  N15  C14  C13  109.79  3.000
 EUO  H12  C18  H11  108.40  3.000
 EUO  H12  C18  H10  108.14  3.000
 EUO  H11  C18  H10  108.13  3.000
 EUO  H12  C18  N17  111.87  3.000
 EUO  H11  C18  N17  111.77  3.000
 EUO  H10  C18  N17  108.40  3.000
 EUO  C03  N02  C01  115.15  3.000
 EUO  C05  N06  C01  115.40  3.000
 EUO  H13  N15  C14  124.93  3.000
 EUO  H13  N15  C10  125.62  3.000
 EUO  C14  N15  C10  109.44  3.000
 EUO  O21  S16  O19  118.25  3.000
 EUO  O19  S16  C01  106.73  3.000
 EUO  O21  S16  C01  108.00  3.000
 EUO  C01  S16  C20  104.96  3.000
 EUO  O19  S16  C20  108.99  3.000
 EUO  O21  S16  C20  109.09  3.000
 EUO  H14  N17  C18  118.78  3.000
 EUO  H14  N17  C03  116.75  3.000
 EUO  C18  N17  C03  124.47  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
 EUO  CONST_01  C14  C13  C09  C10     0.00   0.0  0
 EUO  CONST_02  C07  C08  C09  C10     0.00   0.0  0
 EUO  CONST_03  C13  C14  N15  C10     0.00   0.0  0
 EUO  CONST_04  C07  C12  C11  C10     0.00   0.0  0
 EUO  CONST_05  C07  C08  C09  C13   180.00   0.0  0
 EUO  CONST_06  N15  C10  C09  C13     0.00   0.0  0
 EUO  CONST_07  C11  C10  C09  C13   180.00   0.0  0
 EUO  CONST_08  C07  C05  N06  C01   180.00   0.0  0
 EUO  CONST_09  C04  C05  N06  C01     0.00   0.0  0
 EUO  CONST_10  C04  C03  N02  C01     0.00   0.0  0
 EUO  CONST_11  N06  C01  N02  C03     0.00   0.0  0
 EUO  CONST_12  N06  C05  C04  C03     0.00   0.0  0
 EUO  CONST_13  C07  C05  C04  C03   180.00   0.0  0
 EUO  CONST_16  N02  C01  N06  C05     0.00   0.0  0
 EUO  CONST_17  C09  C08  C07  C05   180.00   0.0  0
 EUO  CONST_18  C11  C12  C07  C05   180.00   0.0  0
 EUO  CONST_19  N02  C03  C04  C05     0.00   0.0  0
 EUO  CONST_20  C14  C13  C09  C08   180.00   0.0  0
 EUO  CONST_21  N15  C10  C09  C08   180.00   0.0  0
 EUO  CONST_22  C11  C10  C09  C08     0.00   0.0  0
 EUO  CONST_24  C11  C12  C07  C08     0.00   0.0  0
 EUO  CONST_25  N15  C14  C13  C09     0.00   0.0  0
 EUO  CONST_26  C12  C07  C08  C09     0.00   0.0  0
 EUO  CONST_27  C14  N15  C10  C09     0.00   0.0  0
 EUO  CONST_28  C12  C11  C10  C09     0.00   0.0  0
 EUO  CONST_29  C14  N15  C10  C11   180.00   0.0  0
 EUO  CONST_31  N15  C10  C11  C12   180.00   0.0  0
 EUO  CONST_32  N17  C03  N02  C01   180.00   0.0  0
 EUO  CONST_33  S16  C01  N02  C03   180.00   0.0  0
 EUO  CONST_34  S16  C01  N06  C05   180.00   0.0  0
 EUO  CONST_35  N17  C03  C04  C05   180.00   0.0  0
 EUO  CONST_36  H1   C13  C09  C10   180.00   0.0  0
 EUO  CONST_37  H6   C08  C09  C10   180.00   0.0  0
 EUO  CONST_38  H9   C14  N15  C10   180.00   0.0  0
 EUO  CONST_39  H8   C12  C11  C10   180.00   0.0  0
 EUO  CONST_40  H13  N15  C14  C13   180.00   0.0  0
 EUO  CONST_41  H5   C04  C05  C07     0.00   0.0  0
 EUO  CONST_42  H7   C11  C12  C07   180.00   0.0  0
 EUO  CONST_43  C18  N17  C03  C04     0.00   0.0  0
 EUO  CONST_44  N02  C03  N17  C18   180.00   0.0  0
 EUO  CONST_45  H14  N17  C03  C04   180.00   0.0  0
 EUO  Var_01    N06  C01  S16  C20    17.79  30.0  2
 EUO  Var_02    H2   C20  S16  C01   -61.79  30.0  3
 EUO  Var_03    H10  C18  N17  C03  -179.15  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
 EUO  plan-1  C01  0.020
 EUO  plan-1  C03  0.020
 EUO  plan-1  C04  0.020
 EUO  plan-1  C05  0.020
 EUO  plan-1  C07  0.020
 EUO  plan-1  N02  0.020
 EUO  plan-1  N06  0.020
 EUO  plan-1  S16  0.020
 EUO  plan-1  H5   0.020
 EUO  plan-1  N17  0.020
 EUO  plan-2  C10  0.020
 EUO  plan-2  C13  0.020
 EUO  plan-2  C05  0.020
 EUO  plan-2  C07  0.020
 EUO  plan-2  C08  0.020
 EUO  plan-2  C09  0.020
 EUO  plan-2  C11  0.020
 EUO  plan-2  C12  0.020
 EUO  plan-2  C14  0.020
 EUO  plan-2  N15  0.020
 EUO  plan-2  H1   0.020
 EUO  plan-2  H6   0.020
 EUO  plan-2  H7   0.020
 EUO  plan-2  H8   0.020
 EUO  plan-2  H9   0.020
 EUO  plan-2  H13  0.020
 EUO  plan-3  C03  0.020
 EUO  plan-3  C18  0.020
 EUO  plan-3  H14  0.020
 EUO  plan-3  N17  0.020

