# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 07:23:37 2022
#   Inital geometry file: a 104 line input string
#   Ligand name: (3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)[C@H](CO)c3ccccc3
#
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
 OIN  OIN  '(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate'  ligand  44  21  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OIN
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
 OIN  C10   C  CH3   0  -0.529  -0.7619  -2.1126  1.8371
 OIN  N     N  NT    0  -0.394   0.1177  -1.2017  2.5430
 OIN  C11   C  CH1   0  -0.134   1.0670  -0.5247  1.6614
 OIN  C17   C  CH2   0  -0.476   0.2444   0.5794  0.9528
 OIN  C16   C  CH2   0  -0.475  -0.8934   0.8787  1.9507
 OIN  C15   C  CH1   0  -0.138  -0.5926  -0.0697  3.1353
 OIN  C14   C  CH2   0  -0.435   0.3310   0.5784  4.1674
 OIN  C13   C  CH1   0   0.028   1.5936   1.0949  3.4920
 OIN  C12   C  CH2   0  -0.442   2.1774   0.0642  2.5320
 OIN  O2    O  O2    0  -0.461   2.5264   1.4232  4.5373
 OIN  C7    C  C     0   0.638   3.5121   2.2676  4.2876
 OIN  O3    O  O     0  -0.448   3.6815   2.8179  3.2285
 OIN  C9    C  CH1   0  -0.524   4.3622   2.5240  5.5194
 OIN  C8    C  CH2   0  -0.162   5.7343   3.0931  5.1430
 OIN  OH    O  OH1   0  -0.659   6.5314   2.1972  4.4128
 OIN  C6    C  CR6   0   0.154   4.4928   1.3428  6.4469
 OIN  C5    C  CR16  0  -0.313   4.3450   1.5283  7.8186
 OIN  C4    C  CR16  0  -0.240   4.5397   0.4795  8.7076
 OIN  C3    C  CR16  0  -0.269   4.8886  -0.7772  8.2335
 OIN  C2    C  CR16  0  -0.242   5.0390  -0.9748  6.8670
 OIN  C1    C  CR16  0  -0.307   4.8451   0.0757  5.9808
 OIN  H101  H  HCH3  0   0.233  -1.4346  -2.5955  2.5472
 OIN  H102  H  HCH3  0   0.233  -0.1702  -2.8953  1.3608
 OIN  H103  H  HCH3  0   0.200  -1.3823  -1.6472  1.0587
 OIN  H11   H  HCH1  0   0.243   1.5050  -1.2346  0.9568
 OIN  H171  H  HCH2  0   0.246  -0.1482   0.2149  0.0030
 OIN  H172  H  HCH2  0   0.240   0.8473   1.4599  0.7213
 OIN  H161  H  HCH2  0   0.241  -0.9240   1.9246  2.2614
 OIN  H162  H  HCH2  0   0.245  -1.8677   0.6525  1.5161
 OIN  H15   H  HCH1  0   0.244  -1.5024  -0.4106  3.6340
 OIN  H141  H  HCH2  0   0.242  -0.1845   1.3989  4.6728
 OIN  H142  H  HCH2  0   0.236   0.5852  -0.1683  4.9241
 OIN  H13   H  HCH1  0   0.242   1.3560   2.0093  2.9413
 OIN  H121  H  HCH2  0   0.235   2.6480  -0.7432  3.0996
 OIN  H122  H  HCH2  0   0.244   2.9442   0.5213  1.9031
 OIN  H9    H  HCH1  0   0.308   3.8410   3.3241  6.0617
 OIN  H81   H  HCH2  0   0.228   6.2279   3.4178  6.0656
 OIN  H82   H  HCH2  0   0.236   5.5985   3.9817  4.5259
 OIN  HOH   H  HOH1  0   0.454   6.8592   1.5201  5.0128
 OIN  H5    H  HCR6  0   0.253   4.0692   2.5057  8.1970
 OIN  H4    H  HCR6  0   0.256   4.4163   0.6458  9.7700
 OIN  H3    H  HCR6  0   0.256   5.0398  -1.5976  8.9230
 OIN  H2    H  HCR6  0   0.257   5.3087  -1.9519  6.4875
 OIN  H1    H  HCR6  0   0.254   4.9542  -0.1097  4.9193

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
 OIN  C10  N     single    1.450  0.020  1.450
 OIN  C10  H101  single    0.970  0.020  1.090
 OIN  C10  H102  single    0.970  0.020  1.090
 OIN  C10  H103  single    0.970  0.020  1.090
 OIN  N    C11   single    1.462  0.020  1.462
 OIN  N    C15   single    1.462  0.020  1.462
 OIN  C11  C17   single    1.548  0.020  1.548
 OIN  C11  C12   single    1.529  0.020  1.529
 OIN  C11  H11   single    0.970  0.020  1.090
 OIN  C17  C16   single    1.543  0.020  1.543
 OIN  C17  H171  single    0.970  0.020  1.090
 OIN  C17  H172  single    0.970  0.020  1.090
 OIN  C16  C15   single    1.547  0.020  1.547
 OIN  C16  H161  single    0.970  0.020  1.090
 OIN  C16  H162  single    0.970  0.020  1.090
 OIN  C15  C14   single    1.529  0.020  1.529
 OIN  C15  H15   single    0.970  0.020  1.090
 OIN  C14  C13   single    1.522  0.020  1.522
 OIN  C14  H141  single    0.970  0.020  1.090
 OIN  C14  H142  single    0.970  0.020  1.090
 OIN  C13  C12   single    1.525  0.020  1.525
 OIN  C13  O2    single    1.439  0.020  1.439
 OIN  C13  H13   single    0.970  0.020  1.090
 OIN  C12  H121  single    0.970  0.020  1.090
 OIN  C12  H122  single    0.970  0.020  1.090
 OIN  O2   C7    single    1.322  0.020  1.322
 OIN  C7   O3    double    1.206  0.020  1.206
 OIN  C7   C9    single    1.518  0.020  1.518
 OIN  C9   C8    single    1.532  0.020  1.532
 OIN  C9   C6    single    1.507  0.020  1.507
 OIN  C9   H9    single    0.970  0.020  1.090
 OIN  C8   OH    single    1.404  0.020  1.404
 OIN  C8   H81   single    0.970  0.020  1.090
 OIN  C8   H82   single    0.970  0.020  1.090
 OIN  OH   HOH   single    0.850  0.020  0.980
 OIN  C6   C5    aromatic  1.392  0.020  1.392
 OIN  C6   C1    aromatic  1.395  0.020  1.395
 OIN  C5   C4    aromatic  1.389  0.020  1.389
 OIN  C5   H5    single    0.930  0.020  1.080
 OIN  C4   C3    aromatic  1.388  0.020  1.388
 OIN  C4   H4    single    0.930  0.020  1.080
 OIN  C3   C2    aromatic  1.389  0.020  1.389
 OIN  C3   H3    single    0.930  0.020  1.080
 OIN  C2   C1    aromatic  1.388  0.020  1.388
 OIN  C2   H2    single    0.930  0.020  1.080
 OIN  C1   H1    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
 OIN  H103  C10  H102  107.51  3.000
 OIN  H103  C10  H101  107.49  3.000
 OIN  H102  C10  H101  107.53  3.000
 OIN  H103  C10  N     114.92  3.000
 OIN  H102  C10  N     109.53  3.000
 OIN  H101  C10  N     109.59  3.000
 OIN  C15   N    C11   101.61  3.000
 OIN  C15   N    C10   112.89  3.000
 OIN  C11   N    C10   113.04  3.000
 OIN  H11   C11  C12   109.06  3.000
 OIN  H11   C11  C17   112.42  3.000
 OIN  C12   C11  C17   111.82  3.000
 OIN  H11   C11  N     110.40  3.000
 OIN  C12   C11  N     107.86  3.000
 OIN  C17   C11  N     105.14  3.000
 OIN  H172  C17  H171  106.47  3.000
 OIN  H172  C17  C16   112.82  3.000
 OIN  H171  C17  C16   111.27  3.000
 OIN  H172  C17  C11   112.25  3.000
 OIN  H171  C17  C11   110.58  3.000
 OIN  C16   C17  C11   103.54  3.000
 OIN  H162  C16  H161  106.69  3.000
 OIN  H162  C16  C15   110.59  3.000
 OIN  H161  C16  C15   112.02  3.000
 OIN  H162  C16  C17   111.16  3.000
 OIN  H161  C16  C17   113.00  3.000
 OIN  C15   C16  C17   103.47  3.000
 OIN  H15   C15  C14   109.10  3.000
 OIN  H15   C15  C16   112.28  3.000
 OIN  C14   C15  C16   111.99  3.000
 OIN  H15   C15  N     110.38  3.000
 OIN  C14   C15  N     107.95  3.000
 OIN  C16   C15  N     105.01  3.000
 OIN  H142  C14  H141  107.60  3.000
 OIN  H142  C14  C13   110.25  3.000
 OIN  H141  C14  C13   109.98  3.000
 OIN  H142  C14  C15   108.55  3.000
 OIN  H141  C14  C15   110.20  3.000
 OIN  C13   C14  C15   110.20  3.000
 OIN  H13   C13  O2    108.42  3.000
 OIN  H13   C13  C12   109.36  3.000
 OIN  O2    C13  C12   111.31  3.000
 OIN  H13   C13  C14   109.08  3.000
 OIN  O2    C13  C14   107.02  3.000
 OIN  C12   C13  C14   111.57  3.000
 OIN  H122  C12  H121  107.81  3.000
 OIN  H122  C12  C13   110.39  3.000
 OIN  H121  C12  C13   109.70  3.000
 OIN  H122  C12  C11   110.08  3.000
 OIN  H121  C12  C11   108.89  3.000
 OIN  C13   C12  C11   109.93  3.000
 OIN  C7    O2   C13   119.47  3.000
 OIN  C9    C7   O3    123.84  3.000
 OIN  C9    C7   O2    111.85  3.000
 OIN  O3    C7   O2    124.22  3.000
 OIN  H9    C9   C6    107.95  3.000
 OIN  H9    C9   C8    106.00  3.000
 OIN  C6    C9   C8    111.38  3.000
 OIN  H9    C9   C7    104.95  3.000
 OIN  C6    C9   C7    114.54  3.000
 OIN  C8    C9   C7    111.39  3.000
 OIN  H82   C8   H81   106.94  3.000
 OIN  H82   C8   OH    107.24  3.000
 OIN  H81   C8   OH    111.79  3.000
 OIN  H82   C8   C9    109.28  3.000
 OIN  H81   C8   C9    107.85  3.000
 OIN  OH    C8   C9    113.52  3.000
 OIN  HOH   OH   C8    108.56  3.000
 OIN  C1    C6   C5    118.48  3.000
 OIN  C1    C6   C9    121.87  3.000
 OIN  C5    C6   C9    119.52  3.000
 OIN  H5    C5   C4    119.56  3.000
 OIN  H5    C5   C6    119.42  3.000
 OIN  C4    C5   C6    121.02  3.000
 OIN  H4    C4   C3    120.20  3.000
 OIN  H4    C4   C5    119.77  3.000
 OIN  C3    C4   C5    120.03  3.000
 OIN  H3    C3   C2    120.26  3.000
 OIN  H3    C3   C4    120.26  3.000
 OIN  C2    C3   C4    119.48  3.000
 OIN  H2    C2   C1    119.62  3.000
 OIN  H2    C2   C3    120.03  3.000
 OIN  C1    C2   C3    120.36  3.000
 OIN  H1    C1   C2    118.82  3.000
 OIN  H1    C1   C6    120.55  3.000
 OIN  C2    C1   C6    120.62  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
 OIN  CONST_01  C3    C4   C5   C6     0.00   0.0  0
 OIN  CONST_02  C3    C2   C1   C6     0.00   0.0  0
 OIN  CONST_03  C2    C1   C6   C5     0.00   0.0  0
 OIN  CONST_04  C2    C3   C4   C5     0.00   0.0  0
 OIN  CONST_05  C1    C6   C5   C4     0.00   0.0  0
 OIN  CONST_06  C1    C2   C3   C4     0.00   0.0  0
 OIN  CONST_07  C4    C5   C6   C9   180.00   0.0  0
 OIN  CONST_08  C2    C1   C6   C9   180.00   0.0  0
 OIN  CONST_09  H4    C4   C5   C6   180.00   0.0  0
 OIN  CONST_10  H2    C2   C1   C6   180.00   0.0  0
 OIN  CONST_11  H1    C1   C6   C5   180.00   0.0  0
 OIN  CONST_12  H3    C3   C4   C5   180.00   0.0  0
 OIN  CONST_13  H5    C5   C4   C3   180.00   0.0  0
 OIN  Var_01    C15   C16  C17  C11    0.79  30.0  3
 OIN  Var_02    H101  C10  N    C11  179.21  30.0  3
 OIN  Var_03    O3    C7   O2   C13    1.40  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
 OIN  chir_01  C11  N   C17  C12  negativ
 OIN  chir_02  C15  N   C16  C14  positiv
 OIN  chir_03  C13  O2  C12  C14  negativ
 OIN  chir_04  C9   C6  C8   C7   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
 OIN  plan-1  C9  0.020
 OIN  plan-1  C6  0.020
 OIN  plan-1  C5  0.020
 OIN  plan-1  C4  0.020
 OIN  plan-1  C3  0.020
 OIN  plan-1  C2  0.020
 OIN  plan-1  C1  0.020
 OIN  plan-1  H5  0.020
 OIN  plan-1  H4  0.020
 OIN  plan-1  H3  0.020
 OIN  plan-1  H2  0.020
 OIN  plan-1  H1  0.020
 OIN  plan-2  O2  0.020
 OIN  plan-2  C7  0.020
 OIN  plan-2  O3  0.020
 OIN  plan-2  C9  0.020

