# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 17 19:14:32 2020
#   Inital geometry file: a 77 line input string
#   Ligand name: (7R)-2-hydroxy-7-(propan-2-yl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@H]1Cc2nc(O)c(cc2CO1)C#N
#
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
 0E1  0E1  (7R)-2-hydroxy-7-(propan-2-yl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile  ligand  30  16  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_0E1
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
 0E1  C1   C  CR6   0  -0.157  -2.6749   0.3998  -0.0579
 0E1  C2   C  CSP   0   0.062  -4.0368   0.7918  -0.1341
 0E1  N3   N  NS    0  -0.250  -5.1420   1.1148  -0.1886
 0E1  C4   C  CR16  0  -0.139  -1.6461   1.3321  -0.0354
 0E1  C5   C  CR6   0  -0.052  -0.3332   0.9025   0.0433
 0E1  C6   C  CR6   0   0.261  -0.0986  -0.4691   0.0873
 0E1  N7   N  N     0  -0.477  -1.0837  -1.3672   0.0713
 0E1  C8   C  CR6   0   0.481  -2.3284  -0.9597   0.0034
 0E1  O9   O  OH1   0  -0.592  -3.3079  -1.8524  -0.0114
 0E1  C10  C  CH2   0  -0.214   0.8220   1.8670   0.0691
 0E1  O11  O  O2    0  -0.486   1.9911   1.2628   0.5468
 0E1  C12  C  CH1   0   0.083   2.3273   0.0849  -0.1655
 0E1  C13  C  CH1   0  -0.272   3.7559  -0.3012   0.2048
 0E1  C14  C  CH3   0  -0.673   4.1537  -1.6272  -0.4390
 0E1  C15  C  CH3   0  -0.656   4.7394   0.7957  -0.1928
 0E1  C16  C  CH2   0  -0.530   1.3015  -0.9965   0.1574
 0E1  H1   H  HCR6  0   0.290  -1.8795   2.3890  -0.0769
 0E1  H3   H  HCH2  0   0.231   0.9766   2.2811  -0.9378
 0E1  H4   H  HCH2  0   0.257   0.5955   2.7059   0.7305
 0E1  H5   H  HCH1  0   0.210   2.2909   0.2897  -1.2488
 0E1  H6   H  HCH1  0   0.226   3.7924  -0.4272   1.2939
 0E1  H7   H  HCH3  0   0.236   3.5708  -2.4673  -0.0610
 0E1  H8   H  HCH3  0   0.221   4.0304  -1.5941  -1.5243
 0E1  H9   H  HCH3  0   0.237   5.2030  -1.8447  -0.2362
 0E1  H10  H  HCH3  0   0.233   4.4916   1.7543   0.2608
 0E1  H11  H  HCH3  0   0.229   5.7517   0.5331   0.1172
 0E1  H12  H  HCH3  0   0.214   4.7507   0.9310  -1.2772
 0E1  H13  H  HCH2  0   0.271   1.4803  -1.3970   1.1620
 0E1  H14  H  HCH2  0   0.271   1.3916  -1.8362  -0.5339
 0E1  H2   H  HOH1  0   0.485  -2.9304  -2.7424   0.0308

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
 0E1  N3   C2   triple    1.153  0.020  1.153
 0E1  C2   C1   single    1.419  0.020  1.419
 0E1  O9   C8   single    1.325  0.020  1.325
 0E1  C1   C8   aromatic  1.404  0.020  1.404
 0E1  C1   C4   aromatic  1.389  0.020  1.389
 0E1  C8   N7   aromatic  1.311  0.020  1.311
 0E1  C4   C5   aromatic  1.384  0.020  1.384
 0E1  N7   C6   aromatic  1.333  0.020  1.333
 0E1  C5   C6   aromatic  1.392  0.020  1.392
 0E1  C5   C10  single    1.505  0.020  1.505
 0E1  C6   C16  single    1.498  0.020  1.498
 0E1  C10  O11  single    1.400  0.020  1.400
 0E1  C16  C12  single    1.525  0.020  1.525
 0E1  O11  C12  single    1.417  0.020  1.417
 0E1  C12  C13  single    1.525  0.020  1.525
 0E1  C13  C15  single    1.526  0.020  1.526
 0E1  C13  C14  single    1.527  0.020  1.527
 0E1  C4   H1   single    0.930  0.020  1.080
 0E1  C10  H3   single    0.970  0.020  1.090
 0E1  C10  H4   single    0.970  0.020  1.090
 0E1  C12  H5   single    0.970  0.020  1.090
 0E1  C13  H6   single    0.970  0.020  1.090
 0E1  C14  H7   single    0.970  0.020  1.090
 0E1  C14  H8   single    0.970  0.020  1.090
 0E1  C14  H9   single    0.970  0.020  1.090
 0E1  C15  H10  single    0.970  0.020  1.090
 0E1  C15  H11  single    0.970  0.020  1.090
 0E1  C15  H12  single    0.970  0.020  1.090
 0E1  C16  H13  single    0.970  0.020  1.090
 0E1  C16  H14  single    0.970  0.020  1.090
 0E1  O9   H2   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
 0E1  C8   C1   C4   117.80  3.000
 0E1  C4   C1   C2   121.77  3.000
 0E1  C8   C1   C2   120.43  3.000
 0E1  N3   C2   C1   180.00  3.000
 0E1  H1   C4   C5   120.63  3.000
 0E1  H1   C4   C1   119.66  3.000
 0E1  C5   C4   C1   119.71  3.000
 0E1  C10  C5   C6   120.10  3.000
 0E1  C10  C5   C4   122.02  3.000
 0E1  C6   C5   C4   117.87  3.000
 0E1  C16  C6   N7   117.01  3.000
 0E1  C16  C6   C5   120.39  3.000
 0E1  N7   C6   C5   122.60  3.000
 0E1  C8   N7   C6   119.52  3.000
 0E1  O9   C8   N7   119.52  3.000
 0E1  N7   C8   C1   122.49  3.000
 0E1  O9   C8   C1   117.98  3.000
 0E1  H2   O9   C8   109.31  3.000
 0E1  H4   C10  H3   107.13  3.000
 0E1  H4   C10  O11  107.34  3.000
 0E1  H3   C10  O11  110.95  3.000
 0E1  H4   C10  C5   110.09  3.000
 0E1  H3   C10  C5   109.48  3.000
 0E1  O11  C10  C5   111.72  3.000
 0E1  C12  O11  C10  112.67  3.000
 0E1  H5   C12  C16  108.50  3.000
 0E1  H5   C12  C13  108.44  3.000
 0E1  C16  C12  C13  113.52  3.000
 0E1  H5   C12  O11  109.36  3.000
 0E1  C13  C12  O11  108.09  3.000
 0E1  C16  C12  O11  108.87  3.000
 0E1  H6   C13  C15  108.65  3.000
 0E1  H6   C13  C14  108.07  3.000
 0E1  C15  C13  C14  110.27  3.000
 0E1  H6   C13  C12  107.53  3.000
 0E1  C14  C13  C12  111.19  3.000
 0E1  C15  C13  C12  111.01  3.000
 0E1  H9   C14  H8   107.41  3.000
 0E1  H9   C14  H7   107.24  3.000
 0E1  H8   C14  H7   107.90  3.000
 0E1  H9   C14  C13  110.21  3.000
 0E1  H8   C14  C13  111.29  3.000
 0E1  H7   C14  C13  112.57  3.000
 0E1  H12  C15  H11  107.59  3.000
 0E1  H12  C15  H10  107.86  3.000
 0E1  H11  C15  H10  107.74  3.000
 0E1  H12  C15  C13  110.74  3.000
 0E1  H11  C15  C13  110.56  3.000
 0E1  H10  C15  C13  112.18  3.000
 0E1  H14  C16  H13  106.62  3.000
 0E1  H14  C16  C12  110.85  3.000
 0E1  H13  C16  C12  110.08  3.000
 0E1  H14  C16  C6   108.57  3.000
 0E1  H13  C16  C6   108.90  3.000
 0E1  C12  C16  C6   111.66  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
 0E1  CONST_01  C6   N7   C8   C1     0.00   0.0  0
 0E1  CONST_02  C6   C5   C4   C1     0.00   0.0  0
 0E1  CONST_03  N7   C8   C1   C4     0.00   0.0  0
 0E1  CONST_04  N7   C6   C5   C4     0.00   0.0  0
 0E1  CONST_05  C8   C1   C4   C5     0.00   0.0  0
 0E1  CONST_06  C8   N7   C6   C5     0.00   0.0  0
 0E1  CONST_07  N7   C8   C1   C2   180.00   0.0  0
 0E1  CONST_08  C5   C4   C1   C2   180.00   0.0  0
 0E1  CONST_09  O9   C8   C1   C4   180.00   0.0  0
 0E1  CONST_10  O9   C8   N7   C6   180.00   0.0  0
 0E1  CONST_11  H1   C4   C5   C6   180.00   0.0  0
 0E1  Var_01    O11  C10  C5   C4   162.10  30.0  1
 0E1  Var_02    C12  C16  C6   C5   -13.75  30.0  1
 0E1  Var_03    H10  C15  C13  C12   57.06  30.0  3
 0E1  Var_04    H7   C14  C13  C12  -65.26  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
 0E1  chir_01  C12  C16  O11  C13  negativ

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
 0E1  plan-1  C1   0.020
 0E1  plan-1  C2   0.020
 0E1  plan-1  N3   0.020
 0E1  plan-1  C4   0.020
 0E1  plan-1  C5   0.020
 0E1  plan-1  C6   0.020
 0E1  plan-1  N7   0.020
 0E1  plan-1  C8   0.020
 0E1  plan-1  O9   0.020
 0E1  plan-1  C10  0.020
 0E1  plan-1  C16  0.020
 0E1  plan-1  H1   0.020

