# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:01:02 2022
#   Inital geometry file: a 85 line input string
#   Ligand name: (2S,3S,4R,5S)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(cc1)[C@H]2[C@H](O)[C@H](O)[C@H](C)N2C
#
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
 16Z  16Z  (2S,3S,4R,5S)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol  ligand  36  17  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_16Z
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
 16Z  CAQ  C  CH3   0  -0.436   5.2546   0.4541   1.1333
 16Z  OAP  O  O2    0  -0.472   4.6432  -0.1597   0.0166
 16Z  CAM  C  CR6   0   0.366   3.2971  -0.1781  -0.0508
 16Z  CAN  C  CR16  0  -0.373   2.4528   0.3566   0.9214
 16Z  CAO  C  CR16  0  -0.286   1.0764   0.2853   0.7555
 16Z  CAL  C  CR16  0  -0.329   2.7374  -0.7752  -1.1799
 16Z  CAK  C  CR16  0  -0.317   1.3617  -0.8275  -1.3273
 16Z  CAJ  C  CR6   0   0.115   0.5014  -0.3057  -0.3651
 16Z  CAE  C  CH1   0  -0.117  -0.9940  -0.3640  -0.5601
 16Z  CAG  C  CH1   0  -0.016  -1.7029  -1.1113   0.5833
 16Z  OAD  O  OH1   0  -0.663  -1.8543  -2.4685   0.2537
 16Z  CAA  C  CH1   0   0.007  -3.0197  -0.3574   0.7716
 16Z  OAC  O  OH1   0  -0.676  -3.9734  -0.7494  -0.1837
 16Z  CAF  C  CH1   0  -0.049  -2.5730   1.0753   0.5210
 16Z  CAB  C  CH3   0  -0.674  -3.7045   2.0561   0.2661
 16Z  NAH  N  NT    0  -0.438  -1.6752   0.9282  -0.6117
 16Z  CAI  C  CH3   0  -0.521  -0.9347   2.0899  -1.0205
 16Z  H1   H  HCH3  0   0.227   4.9941   1.5130   1.2119
 16Z  H2   H  HCH3  0   0.227   4.9908  -0.0433   2.0705
 16Z  H3   H  HCH3  0   0.259   6.3282   0.3684   0.9846
 16Z  H4   H  HCR6  0   0.277   2.8444   0.8270   1.8129
 16Z  H5   H  HCR6  0   0.252   0.4490   0.7115   1.5308
 16Z  H6   H  HCR6  0   0.258   3.3846  -1.1926  -1.9417
 16Z  H7   H  HCR6  0   0.250   0.9478  -1.2832  -2.2196
 16Z  H8   H  HCH1  0   0.231  -1.1784  -0.9093  -1.4962
 16Z  H9   H  HCH1  0   0.231  -1.1188  -1.0008   1.5056
 16Z  H10  H  HOH1  0   0.460  -2.0584  -2.9568   1.0578
 16Z  H11  H  HCH1  0   0.216  -3.4092  -0.4777   1.7924
 16Z  H12  H  HOH1  0   0.441  -3.8718  -1.6991  -0.3170
 16Z  H13  H  HCH1  0   0.198  -2.0397   1.4128   1.4291
 16Z  H14  H  HCH3  0   0.229  -4.4079   2.0455   1.1000
 16Z  H15  H  HCH3  0   0.232  -3.3312   3.0764   0.1729
 16Z  H16  H  HCH3  0   0.225  -4.2454   1.8083  -0.6464
 16Z  H18  H  HCH3  0   0.235  -0.2999   1.8483  -1.8735
 16Z  H19  H  HCH3  0   0.237  -1.6181   2.8769  -1.3441
 16Z  H20  H  HCH3  0   0.193  -0.2870   2.5182  -0.2413

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
 16Z  OAC  CAA  single    1.406  0.020  1.406
 16Z  OAD  CAG  single    1.405  0.020  1.405
 16Z  CAA  CAG  single    1.529  0.020  1.529
 16Z  CAA  CAF  single    1.521  0.020  1.521
 16Z  CAG  CAE  single    1.539  0.020  1.539
 16Z  CAE  NAH  single    1.462  0.020  1.462
 16Z  CAE  CAJ  single    1.509  0.020  1.509
 16Z  NAH  CAF  single    1.453  0.020  1.453
 16Z  NAH  CAI  single    1.437  0.020  1.437
 16Z  CAB  CAF  single    1.519  0.020  1.519
 16Z  CAO  CAJ  aromatic  1.391  0.020  1.391
 16Z  CAO  CAN  aromatic  1.388  0.020  1.388
 16Z  CAJ  CAK  aromatic  1.392  0.020  1.392
 16Z  CAN  CAM  aromatic  1.394  0.020  1.394
 16Z  CAK  CAL  aromatic  1.385  0.020  1.385
 16Z  CAM  CAL  aromatic  1.395  0.020  1.395
 16Z  CAM  OAP  single    1.348  0.020  1.348
 16Z  OAP  CAQ  single    1.413  0.020  1.413
 16Z  CAQ  H1   single    0.970  0.020  1.090
 16Z  CAQ  H2   single    0.970  0.020  1.090
 16Z  CAQ  H3   single    0.970  0.020  1.090
 16Z  CAN  H4   single    0.930  0.020  1.080
 16Z  CAO  H5   single    0.930  0.020  1.080
 16Z  CAL  H6   single    0.930  0.020  1.080
 16Z  CAK  H7   single    0.930  0.020  1.080
 16Z  CAE  H8   single    0.970  0.020  1.090
 16Z  CAG  H9   single    0.970  0.020  1.090
 16Z  OAD  H10  single    0.850  0.020  0.980
 16Z  CAA  H11  single    0.970  0.020  1.090
 16Z  OAC  H12  single    0.850  0.020  0.980
 16Z  CAF  H13  single    0.970  0.020  1.090
 16Z  CAB  H14  single    0.970  0.020  1.090
 16Z  CAB  H15  single    0.970  0.020  1.090
 16Z  CAB  H16  single    0.970  0.020  1.090
 16Z  CAI  H18  single    0.970  0.020  1.090
 16Z  CAI  H19  single    0.970  0.020  1.090
 16Z  CAI  H20  single    0.970  0.020  1.090

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
 16Z  H3   CAQ  H2   108.64  3.000
 16Z  H3   CAQ  H1   108.75  3.000
 16Z  H2   CAQ  H1   108.75  3.000
 16Z  H3   CAQ  OAP  106.55  3.000
 16Z  H2   CAQ  OAP  112.04  3.000
 16Z  H1   CAQ  OAP  111.99  3.000
 16Z  CAM  OAP  CAQ  118.52  3.000
 16Z  CAL  CAM  CAN  119.06  3.000
 16Z  CAL  CAM  OAP  116.56  3.000
 16Z  CAN  CAM  OAP  124.37  3.000
 16Z  H4   CAN  CAO  118.68  3.000
 16Z  H4   CAN  CAM  121.50  3.000
 16Z  CAO  CAN  CAM  119.82  3.000
 16Z  H5   CAO  CAJ  120.24  3.000
 16Z  H5   CAO  CAN  117.90  3.000
 16Z  CAJ  CAO  CAN  121.86  3.000
 16Z  H6   CAL  CAK  120.28  3.000
 16Z  H6   CAL  CAM  119.64  3.000
 16Z  CAK  CAL  CAM  120.08  3.000
 16Z  H7   CAK  CAJ  119.38  3.000
 16Z  H7   CAK  CAL  118.87  3.000
 16Z  CAJ  CAK  CAL  121.75  3.000
 16Z  CAE  CAJ  CAK  120.56  3.000
 16Z  CAK  CAJ  CAO  117.42  3.000
 16Z  CAE  CAJ  CAO  122.01  3.000
 16Z  H8   CAE  NAH  109.29  3.000
 16Z  H8   CAE  CAG  108.34  3.000
 16Z  NAH  CAE  CAG  103.94  3.000
 16Z  H8   CAE  CAJ  107.19  3.000
 16Z  NAH  CAE  CAJ  115.60  3.000
 16Z  CAG  CAE  CAJ  112.28  3.000
 16Z  H9   CAG  CAA  107.78  3.000
 16Z  H9   CAG  OAD  110.60  3.000
 16Z  CAA  CAG  OAD  114.36  3.000
 16Z  H9   CAG  CAE  109.29  3.000
 16Z  CAA  CAG  CAE  104.41  3.000
 16Z  OAD  CAG  CAE  110.14  3.000
 16Z  H10  OAD  CAG  108.47  3.000
 16Z  H11  CAA  CAF  111.11  3.000
 16Z  H11  CAA  OAC  111.11  3.000
 16Z  CAF  CAA  OAC  110.48  3.000
 16Z  H11  CAA  CAG  111.44  3.000
 16Z  CAF  CAA  CAG  101.02  3.000
 16Z  OAC  CAA  CAG  111.29  3.000
 16Z  H12  OAC  CAA  107.28  3.000
 16Z  H13  CAF  NAH  111.91  3.000
 16Z  H13  CAF  CAB  107.45  3.000
 16Z  NAH  CAF  CAB  113.26  3.000
 16Z  H13  CAF  CAA  107.08  3.000
 16Z  CAB  CAF  CAA  114.65  3.000
 16Z  NAH  CAF  CAA  102.39  3.000
 16Z  H16  CAB  H15  108.14  3.000
 16Z  H16  CAB  H14  108.54  3.000
 16Z  H15  CAB  H14  107.17  3.000
 16Z  H16  CAB  CAF  111.31  3.000
 16Z  H15  CAB  CAF  111.32  3.000
 16Z  H14  CAB  CAF  110.22  3.000
 16Z  CAI  NAH  CAF  117.29  3.000
 16Z  CAI  NAH  CAE  118.99  3.000
 16Z  CAF  NAH  CAE  110.48  3.000
 16Z  H20  CAI  H19  107.33  3.000
 16Z  H20  CAI  H18  107.31  3.000
 16Z  H19  CAI  H18  107.00  3.000
 16Z  H20  CAI  NAH  114.63  3.000
 16Z  H19  CAI  NAH  110.16  3.000
 16Z  H18  CAI  NAH  110.09  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
 16Z  CONST_01  CAJ  CAO  CAN  CAM    0.00   0.0  0
 16Z  CONST_02  CAJ  CAK  CAL  CAM    0.00   0.0  0
 16Z  CONST_03  CAK  CAJ  CAO  CAN    0.00   0.0  0
 16Z  CONST_04  CAK  CAL  CAM  CAN    0.00   0.0  0
 16Z  CONST_05  CAL  CAK  CAJ  CAO    0.00   0.0  0
 16Z  CONST_06  CAL  CAM  CAN  CAO    0.00   0.0  0
 16Z  CONST_07  CAE  CAJ  CAO  CAN  180.00   0.0  0
 16Z  CONST_08  CAE  CAJ  CAK  CAL  180.00   0.0  0
 16Z  CONST_09  CAO  CAN  CAM  OAP  180.00   0.0  0
 16Z  CONST_10  CAK  CAL  CAM  OAP  180.00   0.0  0
 16Z  CONST_11  H5   CAO  CAN  CAM  180.00   0.0  0
 16Z  CONST_12  H7   CAK  CAL  CAM  180.00   0.0  0
 16Z  CONST_13  H6   CAL  CAM  CAN  180.00   0.0  0
 16Z  CONST_14  H4   CAN  CAM  CAL  180.00   0.0  0
 16Z  Var_01    CAN  CAM  OAP  CAQ   -0.84  30.0  2
 16Z  Var_02    H18  CAI  NAH  CAE   42.47  30.0  3
 16Z  Var_03    H1   CAQ  OAP  CAM  -60.61  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
 16Z  chir_01  CAE  CAG  NAH  CAJ  negativ
 16Z  chir_02  CAG  OAD  CAA  CAE  positiv
 16Z  chir_03  CAA  OAC  CAF  CAG  positiv
 16Z  chir_04  CAF  NAH  CAB  CAA  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
 16Z  plan-1  OAP  0.020
 16Z  plan-1  CAM  0.020
 16Z  plan-1  CAN  0.020
 16Z  plan-1  CAO  0.020
 16Z  plan-1  CAL  0.020
 16Z  plan-1  CAK  0.020
 16Z  plan-1  CAJ  0.020
 16Z  plan-1  CAE  0.020
 16Z  plan-1  H4   0.020
 16Z  plan-1  H5   0.020
 16Z  plan-1  H6   0.020
 16Z  plan-1  H7   0.020

