# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 13:06:23 2020
#   Inital geometry file: a 98 line input string
#   Ligand name: (4R)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(cc1OC2CCCC2)[C@@H]3CNC(=O)C3
#
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
 4SR  4SR  (4R)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one  ligand  41  20  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_4SR
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
 4SR  O15   O  O     0  -0.495  -5.7590  -1.4634   0.9611
 4SR  C14   C  C     0   0.510  -4.7649  -1.0923   0.3586
 4SR  C16   C  CH2   0  -0.568  -3.4488  -0.6508   0.9672
 4SR  C11   C  CH1   0  -0.397  -2.4693  -0.6650  -0.2102
 4SR  C12   C  CH2   0  -0.227  -3.3879  -0.4136  -1.4183
 4SR  N13   N  NH1   0  -0.622  -4.6435  -0.9778  -0.9755
 4SR  C10   C  CR6   0   0.191  -1.3054   0.2823  -0.1142
 4SR  C17   C  CR16  0  -0.338  -1.4826   1.6427   0.0688
 4SR  C18   C  CR16  0  -0.368  -0.3859   2.4975   0.1491
 4SR  C1    C  CR6   0   0.278   0.9048   2.0045   0.0457
 4SR  O19   O  O2    0  -0.465   2.0259   2.7504   0.1063
 4SR  C20   C  CH3   0  -0.436   1.8864   4.1470   0.2621
 4SR  C2    C  CR6   0   0.341   1.1005   0.6215  -0.1417
 4SR  C9    C  CR16  0  -0.459  -0.0034  -0.2140  -0.2179
 4SR  O3    O  O2    0  -0.483   2.3841   0.2311  -0.2440
 4SR  C4    C  CH1   0   0.026   2.6888  -1.1389  -0.4806
 4SR  C5    C  CH2   0  -0.472   4.1711  -1.2501  -0.8938
 4SR  C6    C  CH2   0  -0.445   4.8532  -2.0951   0.1860
 4SR  C7    C  CH2   0  -0.448   3.7244  -2.9793   0.7084
 4SR  C8    C  CH2   0  -0.482   2.5401  -2.0183   0.7734
 4SR  H161  H  HCH2  0   0.280  -3.1480  -1.2978   1.7904
 4SR  H162  H  HCH2  0   0.274  -3.5844   0.3549   1.3777
 4SR  H11   H  HCH1  0   0.277  -2.0795  -1.6821  -0.3045
 4SR  H121  H  HCH2  0   0.238  -3.4863   0.6548  -1.6333
 4SR  H122  H  HCH2  0   0.257  -3.0240  -0.9063  -2.3195
 4SR  H13   H  HNH1  0   0.398  -5.4270  -1.1099  -1.5964
 4SR  H17   H  HCR6  0   0.247  -2.4768   2.0645   0.1537
 4SR  H18   H  HCR6  0   0.280  -0.5609   3.5553   0.2921
 4SR  H201  H  HCH3  0   0.226   1.3241   4.5963  -0.5610
 4SR  H202  H  HCH3  0   0.226   1.3963   4.4083   1.2042
 4SR  H203  H  HCH3  0   0.258   2.8921   4.5604   0.2655
 4SR  H9    H  HCR6  0   0.271   0.1270  -1.2788  -0.3590
 4SR  H4    H  HCH1  0   0.236   2.0528  -1.5088  -1.2921
 4SR  H51   H  HCH2  0   0.240   4.2365  -1.7542  -1.8591
 4SR  H52   H  HCH2  0   0.247   4.6249  -0.2664  -1.0206
 4SR  H61   H  HCH2  0   0.235   5.7017  -2.6610  -0.2004
 4SR  H62   H  HCH2  0   0.224   5.2287  -1.4607   0.9928
 4SR  H71   H  HCH2  0   0.224   3.5197  -3.7861  -0.0011
 4SR  H72   H  HCH2  0   0.237   3.9424  -3.4404   1.6725
 4SR  H81   H  HCH2  0   0.238   2.6298  -1.3860   1.6618
 4SR  H82   H  HCH2  0   0.243   1.5781  -2.5281   0.8335

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
 4SR  O15  C14   double    1.220  0.020  1.220
 4SR  C14  C16   single    1.516  0.020  1.516
 4SR  C14  N13   single    1.344  0.020  1.344
 4SR  C16  C11   single    1.532  0.020  1.532
 4SR  C16  H161  single    0.970  0.020  1.090
 4SR  C16  H162  single    0.970  0.020  1.090
 4SR  C11  C12   single    1.538  0.020  1.538
 4SR  C11  C10   single    1.504  0.020  1.504
 4SR  C11  H11   single    0.970  0.020  1.090
 4SR  C12  N13   single    1.446  0.020  1.446
 4SR  C12  H121  single    0.970  0.020  1.090
 4SR  C12  H122  single    0.970  0.020  1.090
 4SR  N13  H13   single    0.860  0.020  1.020
 4SR  C10  C17   aromatic  1.384  0.020  1.384
 4SR  C10  C9    aromatic  1.397  0.020  1.397
 4SR  C17  C18   aromatic  1.393  0.020  1.393
 4SR  C17  H17   single    0.930  0.020  1.080
 4SR  C18  C1    aromatic  1.386  0.020  1.386
 4SR  C18  H18   single    0.930  0.020  1.080
 4SR  C1   O19   single    1.348  0.020  1.348
 4SR  C1   C2    aromatic  1.409  0.020  1.409
 4SR  O19  C20   single    1.412  0.020  1.412
 4SR  C20  H201  single    0.970  0.020  1.090
 4SR  C20  H202  single    0.970  0.020  1.090
 4SR  C20  H203  single    0.970  0.020  1.090
 4SR  C2   C9    aromatic  1.387  0.020  1.387
 4SR  C2   O3    single    1.346  0.020  1.346
 4SR  C9   H9    single    0.930  0.020  1.080
 4SR  O3   C4    single    1.423  0.020  1.423
 4SR  C4   C5    single    1.543  0.020  1.543
 4SR  C4   C8    single    1.539  0.020  1.539
 4SR  C4   H4    single    0.970  0.020  1.090
 4SR  C5   C6    single    1.531  0.020  1.531
 4SR  C5   H51   single    0.970  0.020  1.090
 4SR  C5   H52   single    0.970  0.020  1.090
 4SR  C6   C7    single    1.526  0.020  1.526
 4SR  C6   H61   single    0.970  0.020  1.090
 4SR  C6   H62   single    0.970  0.020  1.090
 4SR  C7   C8    single    1.527  0.020  1.527
 4SR  C7   H71   single    0.970  0.020  1.090
 4SR  C7   H72   single    0.970  0.020  1.090
 4SR  C8   H81   single    0.970  0.020  1.090
 4SR  C8   H82   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
 4SR  N13   C14  C16   107.17  3.000
 4SR  N13   C14  O15   126.12  3.000
 4SR  C16   C14  O15   126.71  3.000
 4SR  H162  C16  H161  107.24  3.000
 4SR  H162  C16  C11   112.09  3.000
 4SR  H161  C16  C11   113.51  3.000
 4SR  H162  C16  C14   108.10  3.000
 4SR  H161  C16  C14   111.72  3.000
 4SR  C11   C16  C14   104.12  3.000
 4SR  H11   C11  C10   108.39  3.000
 4SR  H11   C11  C12   107.29  3.000
 4SR  C10   C11  C12   114.17  3.000
 4SR  H11   C11  C16   107.64  3.000
 4SR  C10   C11  C16   116.11  3.000
 4SR  C12   C11  C16   102.73  3.000
 4SR  H122  C12  H121  108.00  3.000
 4SR  H122  C12  N13   111.52  3.000
 4SR  H121  C12  N13   111.29  3.000
 4SR  H122  C12  C11   112.10  3.000
 4SR  H121  C12  C11   111.56  3.000
 4SR  N13   C12  C11   102.37  3.000
 4SR  H13   N13  C12   122.49  3.000
 4SR  H13   N13  C14   121.98  3.000
 4SR  C12   N13  C14   114.55  3.000
 4SR  C9    C10  C17   118.57  3.000
 4SR  C9    C10  C11   119.53  3.000
 4SR  C17   C10  C11   121.90  3.000
 4SR  H17   C17  C18   118.63  3.000
 4SR  H17   C17  C10   120.70  3.000
 4SR  C18   C17  C10   120.67  3.000
 4SR  H18   C18  C1    120.56  3.000
 4SR  H18   C18  C17   118.72  3.000
 4SR  C1    C18  C17   120.72  3.000
 4SR  C2    C1   O19   115.69  3.000
 4SR  C2    C1   C18   119.24  3.000
 4SR  O19   C1   C18   125.07  3.000
 4SR  C20   O19  C1    118.04  3.000
 4SR  H203  C20  H202  108.73  3.000
 4SR  H203  C20  H201  108.77  3.000
 4SR  H202  C20  H201  108.65  3.000
 4SR  H203  C20  O19   106.56  3.000
 4SR  H202  C20  O19   112.06  3.000
 4SR  H201  C20  O19   111.97  3.000
 4SR  O3    C2   C9    125.49  3.000
 4SR  O3    C2   C1    115.30  3.000
 4SR  C9    C2   C1    119.21  3.000
 4SR  H9    C9   C2    120.28  3.000
 4SR  H9    C9   C10   118.13  3.000
 4SR  C2    C9   C10   121.59  3.000
 4SR  C4    O3   C2    119.74  3.000
 4SR  H4    C4   C8    110.78  3.000
 4SR  H4    C4   C5    109.57  3.000
 4SR  C8    C4   C5    105.66  3.000
 4SR  H4    C4   O3    108.90  3.000
 4SR  C8    C4   O3    113.20  3.000
 4SR  C5    C4   O3    108.63  3.000
 4SR  H52   C5   H51   106.80  3.000
 4SR  H52   C5   C6    113.22  3.000
 4SR  H51   C5   C6    110.01  3.000
 4SR  H52   C5   C4    111.46  3.000
 4SR  H51   C5   C4    109.14  3.000
 4SR  C6    C5   C4    106.19  3.000
 4SR  H62   C6   H61   107.18  3.000
 4SR  H62   C6   C7    109.74  3.000
 4SR  H61   C6   C7    113.34  3.000
 4SR  H62   C6   C5    110.68  3.000
 4SR  H61   C6   C5    112.52  3.000
 4SR  C7    C6   C5    103.39  3.000
 4SR  H72   C7   H71   107.40  3.000
 4SR  H72   C7   C8    112.56  3.000
 4SR  H71   C7   C8    110.29  3.000
 4SR  H72   C7   C6    113.55  3.000
 4SR  H71   C7   C6    110.10  3.000
 4SR  C8    C7   C6    102.93  3.000
 4SR  H82   C8   H81   107.32  3.000
 4SR  H82   C8   C7    113.10  3.000
 4SR  H81   C8   C7    109.56  3.000
 4SR  H82   C8   C4    113.42  3.000
 4SR  H81   C8   C4    108.88  3.000
 4SR  C7    C8   C4    104.48  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
 4SR  CONST_01  C1    C18  C17  C10    0.00   0.0  0
 4SR  CONST_02  C1    C2   C9   C10    0.00   0.0  0
 4SR  CONST_03  C2    C9   C10  C17    0.00   0.0  0
 4SR  CONST_04  C2    C1   C18  C17    0.00   0.0  0
 4SR  CONST_05  C9    C10  C17  C18    0.00   0.0  0
 4SR  CONST_06  C9    C2   C1   C18    0.00   0.0  0
 4SR  CONST_07  C18   C17  C10  C11  180.00   0.0  0
 4SR  CONST_08  C2    C9   C10  C11  180.00   0.0  0
 4SR  CONST_09  C12   N13  C14  C16    0.00   0.0  0
 4SR  CONST_10  O3    C2   C9   C10  180.00   0.0  0
 4SR  CONST_11  O19   C1   C18  C17  180.00   0.0  0
 4SR  CONST_12  O3    C2   C1   C18  180.00   0.0  0
 4SR  CONST_13  C9    C2   C1   O19  180.00   0.0  0
 4SR  CONST_14  C12   N13  C14  O15  180.00   0.0  0
 4SR  CONST_15  H17   C17  C10  C11    0.00   0.0  0
 4SR  CONST_16  H9    C9   C10  C11    0.00   0.0  0
 4SR  CONST_17  H18   C18  C17  C10  180.00   0.0  0
 4SR  CONST_18  H13   N13  C14  C16  180.00   0.0  0
 4SR  Var_01    C11   C12  N13  C14   21.21  30.0  1
 4SR  Var_02    N13   C14  C16  C11  -15.76  30.0  1
 4SR  Var_03    C7    C6   C5   C4    27.96  30.0  1
 4SR  Var_04    C6    C7   C8   C4    38.60  30.0  1
 4SR  Var_05    C8    C7   C6   C5   -41.08  30.0  1
 4SR  Var_06    C2    C1   O19  C20  178.57  30.0  2
 4SR  Var_07    H201  C20  O19  C1   -59.94  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
 4SR  chir_01  C11  C16  C12  C10  negativ
 4SR  chir_02  C4   O3   C5   C8   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
 4SR  plan-1  O15  0.020
 4SR  plan-1  C14  0.020
 4SR  plan-1  C16  0.020
 4SR  plan-1  C12  0.020
 4SR  plan-1  N13  0.020
 4SR  plan-1  H13  0.020
 4SR  plan-2  C11  0.020
 4SR  plan-2  C10  0.020
 4SR  plan-2  C17  0.020
 4SR  plan-2  C18  0.020
 4SR  plan-2  C1   0.020
 4SR  plan-2  O19  0.020
 4SR  plan-2  C2   0.020
 4SR  plan-2  C9   0.020
 4SR  plan-2  O3   0.020
 4SR  plan-2  H17  0.020
 4SR  plan-2  H18  0.020
 4SR  plan-2  H9   0.020

