# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 02:56:02 2020
#   Inital geometry file: a 99 line input string
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@H]1C[C@@H]2[N@@]3C[C@H](O)[C@@]2(C=C1)c4cc5OCOc5cc4C3
#
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
 HN8  HN8  'None                     '  ligand  41  22  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HN8
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
 HN8  C1   C  CT    0  -0.277  -0.8252  -0.2764   0.6325
 HN8  C2   C  CH1   0  -0.105  -1.5903  -0.7033  -0.6330
 HN8  O2   O  O     0  -0.490   3.7326   1.8028   0.8229
 HN8  C10  C  C1    0  -0.262  -2.6384   1.3880   0.9697
 HN8  C11  C  CR16  0  -0.434   1.4535   0.8763   0.8295
 HN8  C12  C  CR16  0  -0.383   2.4794  -0.8321  -1.1734
 HN8  C13  C  CR56  0   0.315   2.7579   0.9491   0.4158
 HN8  C14  C  CR56  0   0.299   3.2627   0.1126  -0.5651
 HN8  C15  C  CH3   0  -0.400  -3.9187   2.8660  -1.2180
 HN8  C16  C  CH2   0   0.067   4.9363   1.3222   0.2404
 HN8  C17  C  CH2   0  -0.469  -3.0944  -0.6249  -0.4393
 HN8  C3   C  CH1   0   0.077  -0.8627  -1.5633   1.5073
 HN8  C4   C  CH2   0  -0.360  -1.0653  -2.6774   0.4430
 HN8  C5   C  CR6   0   0.175   0.6276  -0.0826   0.2190
 HN8  C6   C  CH2   0  -0.378   0.2450  -1.9405  -1.4514
 HN8  C7   C  C1    0  -0.143  -1.4472   0.9038   1.3063
 HN8  C8   C  CR6   0   0.002   1.1405  -0.9291  -0.7641
 HN8  C9   C  CH1   0   0.001  -3.5032   0.8048  -0.1200
 HN8  N1   N  NT    0  -0.397  -1.0856  -2.0490  -0.8769
 HN8  O1   O  O2    0  -0.489  -3.4238   1.5552  -1.3217
 HN8  O3   O  O     0  -0.489   4.5653   0.4189  -0.7919
 HN8  O4   O  OH1   0  -0.660  -1.9061  -1.4933   2.4482
 HN8  H1   H  HCH1  0   0.255  -1.3242  -0.0612  -1.4784
 HN8  H2   H  H     0   0.252  -3.0277   2.2425   1.5134
 HN8  H3   H  HCR6  0   0.260   1.0829   1.5409   1.5971
 HN8  H4   H  HCR6  0   0.264   2.8741  -1.4825  -1.9450
 HN8  H5   H  HCH3  0   0.234  -3.9352   3.2948  -2.2198
 HN8  H6   H  HCH3  0   0.201  -4.9402   2.8872  -0.8187
 HN8  H7   H  HCH3  0   0.206  -3.2963   3.5077  -0.5850
 HN8  H8   H  HCH2  0   0.245   5.5008   2.1534  -0.1811
 HN8  H9   H  HCH2  0   0.230   5.5319   0.7982   0.9966
 HN8  H10  H  HCH2  0   0.243  -3.6107  -0.9683  -1.3390
 HN8  H11  H  HCH2  0   0.243  -3.4202  -1.2665   0.3811
 HN8  H12  H  HCH1  0   0.227   0.0956  -1.6869   2.0244
 HN8  H13  H  HCH2  0   0.252  -0.2935  -3.4470   0.4852
 HN8  H14  H  HCH2  0   0.247  -2.0220  -3.1720   0.6324
 HN8  H15  H  HCH2  0   0.258   0.1448  -1.6604  -2.5054
 HN8  H16  H  HCH2  0   0.257   0.7164  -2.9267  -1.4461
 HN8  H17  H  H     0   0.251  -0.9134   1.3608   2.1326
 HN8  H18  H  HCH1  0   0.224  -4.5460   0.8100   0.2319
 HN8  H20  H  HOH1  0   0.451  -1.8792  -2.2960   2.9791

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
 HN8  C16  O2   single    1.421  0.020  1.421
 HN8  C16  O3   single    1.421  0.020  1.421
 HN8  O2   C13  single    1.358  0.020  1.358
 HN8  O3   C14  single    1.357  0.020  1.357
 HN8  C13  C14  aromatic  1.384  0.020  1.384
 HN8  C13  C11  aromatic  1.370  0.020  1.370
 HN8  C14  C12  aromatic  1.370  0.020  1.370
 HN8  C11  C5   aromatic  1.405  0.020  1.405
 HN8  C12  C8   aromatic  1.403  0.020  1.403
 HN8  C5   C8   aromatic  1.395  0.020  1.395
 HN8  C5   C1   single    1.523  0.020  1.523
 HN8  C8   C6   single    1.516  0.020  1.516
 HN8  C7   C1   single    1.495  0.020  1.495
 HN8  C7   C10  double    1.329  0.020  1.329
 HN8  C1   C3   single    1.557  0.020  1.557
 HN8  C1   C2   single    1.539  0.020  1.539
 HN8  C10  C9   single    1.508  0.020  1.508
 HN8  C3   O4   single    1.407  0.020  1.407
 HN8  C3   C4   single    1.554  0.020  1.554
 HN8  C6   N1   single    1.453  0.020  1.453
 HN8  O1   C15  single    1.405  0.020  1.405
 HN8  O1   C9   single    1.419  0.020  1.419
 HN8  C2   N1   single    1.458  0.020  1.458
 HN8  C2   C17  single    1.519  0.020  1.519
 HN8  C9   C17  single    1.521  0.020  1.521
 HN8  N1   C4   single    1.462  0.020  1.462
 HN8  C2   H1   single    0.970  0.020  1.090
 HN8  C10  H2   single    0.930  0.020  1.080
 HN8  C11  H3   single    0.930  0.020  1.080
 HN8  C12  H4   single    0.930  0.020  1.080
 HN8  C15  H5   single    0.970  0.020  1.090
 HN8  C15  H6   single    0.970  0.020  1.090
 HN8  C15  H7   single    0.970  0.020  1.090
 HN8  C16  H8   single    0.970  0.020  1.090
 HN8  C16  H9   single    0.970  0.020  1.090
 HN8  C17  H10  single    0.970  0.020  1.090
 HN8  C17  H11  single    0.970  0.020  1.090
 HN8  C3   H12  single    0.970  0.020  1.090
 HN8  C4   H13  single    0.970  0.020  1.090
 HN8  C4   H14  single    0.970  0.020  1.090
 HN8  C6   H15  single    0.970  0.020  1.090
 HN8  C6   H16  single    0.970  0.020  1.090
 HN8  C7   H17  single    0.930  0.020  1.080
 HN8  C9   H18  single    0.970  0.020  1.090
 HN8  O4   H20  single    0.850  0.020  0.980

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
 HN8  C7   C1   C5   114.77  3.000
 HN8  C7   C1   C3   112.92  3.000
 HN8  C5   C1   C3   106.31  3.000
 HN8  C3   C1   C2   102.75  3.000
 HN8  C7   C1   C2   112.51  3.000
 HN8  C5   C1   C2   106.63  3.000
 HN8  H1   C2   N1   109.15  3.000
 HN8  H1   C2   C17  108.00  3.000
 HN8  N1   C2   C17  114.33  3.000
 HN8  H1   C2   C1   110.58  3.000
 HN8  C17  C2   C1   111.91  3.000
 HN8  N1   C2   C1   102.80  3.000
 HN8  C16  O2   C13  105.81  3.000
 HN8  H2   C10  C9   117.43  3.000
 HN8  H2   C10  C7   118.79  3.000
 HN8  C9   C10  C7   123.77  3.000
 HN8  H3   C11  C5   121.78  3.000
 HN8  H3   C11  C13  120.54  3.000
 HN8  C5   C11  C13  117.68  3.000
 HN8  H4   C12  C8   120.91  3.000
 HN8  H4   C12  C14  121.47  3.000
 HN8  C8   C12  C14  117.63  3.000
 HN8  C14  C13  C11  121.93  3.000
 HN8  C11  C13  O2   128.75  3.000
 HN8  C14  C13  O2   109.30  3.000
 HN8  O3   C14  C13  109.39  3.000
 HN8  C13  C14  C12  121.53  3.000
 HN8  O3   C14  C12  129.07  3.000
 HN8  H7   C15  H6   107.90  3.000
 HN8  H7   C15  H5   108.02  3.000
 HN8  H6   C15  H5   108.23  3.000
 HN8  H7   C15  O1   112.89  3.000
 HN8  H6   C15  O1   111.90  3.000
 HN8  H5   C15  O1   107.73  3.000
 HN8  H9   C16  H8   110.50  3.000
 HN8  H9   C16  O3   109.83  3.000
 HN8  H8   C16  O3   109.82  3.000
 HN8  H9   C16  O2   109.83  3.000
 HN8  H8   C16  O2   109.84  3.000
 HN8  O3   C16  O2   106.95  3.000
 HN8  H11  C17  H10  107.05  3.000
 HN8  H11  C17  C9   108.34  3.000
 HN8  H10  C17  C9   109.96  3.000
 HN8  H11  C17  C2   111.18  3.000
 HN8  H10  C17  C2   110.29  3.000
 HN8  C9   C17  C2   109.97  3.000
 HN8  H12  C3   O4   109.79  3.000
 HN8  H12  C3   C4   110.87  3.000
 HN8  O4   C3   C4   113.40  3.000
 HN8  H12  C3   C1   109.71  3.000
 HN8  C4   C3   C1   102.18  3.000
 HN8  O4   C3   C1   110.65  3.000
 HN8  H14  C4   H13  107.05  3.000
 HN8  H14  C4   N1   109.80  3.000
 HN8  H13  C4   N1   110.37  3.000
 HN8  H14  C4   C3   108.64  3.000
 HN8  H13  C4   C3   112.77  3.000
 HN8  N1   C4   C3   108.18  3.000
 HN8  C8   C5   C11  120.28  3.000
 HN8  C8   C5   C1   117.70  3.000
 HN8  C11  C5   C1   121.98  3.000
 HN8  H16  C6   H15  105.95  3.000
 HN8  H16  C6   N1   109.00  3.000
 HN8  H15  C6   N1   108.40  3.000
 HN8  H16  C6   C8   110.19  3.000
 HN8  H15  C6   C8   108.65  3.000
 HN8  N1   C6   C8   114.30  3.000
 HN8  H17  C7   C10  118.72  3.000
 HN8  H17  C7   C1   118.12  3.000
 HN8  C10  C7   C1   123.12  3.000
 HN8  C6   C8   C5   120.48  3.000
 HN8  C6   C8   C12  118.53  3.000
 HN8  C5   C8   C12  120.95  3.000
 HN8  H18  C9   O1   108.74  3.000
 HN8  H18  C9   C17  109.04  3.000
 HN8  O1   C9   C17  107.71  3.000
 HN8  H18  C9   C10  108.08  3.000
 HN8  C17  C9   C10  111.16  3.000
 HN8  O1   C9   C10  112.04  3.000
 HN8  C6   N1   C4   112.10  3.000
 HN8  C4   N1   C2   104.51  3.000
 HN8  C6   N1   C2   108.31  3.000
 HN8  C9   O1   C15  114.28  3.000
 HN8  C16  O3   C14  105.82  3.000
 HN8  H20  O4   C3   107.86  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
 HN8  CONST_01  C12  C14  C13  C11     0.00   0.0  0
 HN8  CONST_02  C12  C8   C5   C11     0.00   0.0  0
 HN8  CONST_03  C8   C12  C14  C13     0.00   0.0  0
 HN8  CONST_04  C8   C5   C11  C13     0.00   0.0  0
 HN8  CONST_05  C5   C11  C13  C14     0.00   0.0  0
 HN8  CONST_06  C5   C8   C12  C14     0.00   0.0  0
 HN8  CONST_07  H3   C11  C5   C1      0.00   0.0  0
 HN8  CONST_08  H4   C12  C14  C13   180.00   0.0  0
 HN8  Var_01    C9   C10  C7   C1      0.33  30.0  1
 HN8  Var_02    C8   C6   N1   C2     44.55  30.0  1
 HN8  Var_03    C3   C4   N1   C2    -28.36  30.0  3
 HN8  Var_04    N1   C6   C8   C12   174.71  30.0  1
 HN8  Var_05    O3   C16  O2   C13    16.12  30.0  1
 HN8  Var_06    H5   C15  O1   C9   -172.32  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 HN8  chir_01  C1  C7  C5   C2   positiv
 HN8  chir_02  C2  N1  C1   C17  positiv
 HN8  chir_03  C3  O4  C4   C1   negativ
 HN8  chir_04  C9  O1  C10  C17  positiv

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
 HN8  plan-1  C1   0.020
 HN8  plan-1  O2   0.020
 HN8  plan-1  C11  0.020
 HN8  plan-1  C12  0.020
 HN8  plan-1  C13  0.020
 HN8  plan-1  C14  0.020
 HN8  plan-1  C5   0.020
 HN8  plan-1  C6   0.020
 HN8  plan-1  C8   0.020
 HN8  plan-1  O3   0.020
 HN8  plan-1  H3   0.020
 HN8  plan-1  H4   0.020

