# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 22:33:13 2020
#   Inital geometry file: a 112 line input string
#   Ligand name: 3-chloro-5-ethyl-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-6-hydroxy-2-methoxybenzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN1CCC[C@H]1CNC(=O)c2c(O)c(CC)cc(Cl)c2OC
#
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
 ETQ  ETQ  3-chloro-5-ethyl-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-6-hydroxy-2-methoxybenzamide  ligand  48  23  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ETQ
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
 ETQ  C1    C   CR6   0   0.335   1.6747  -1.1293   1.1219
 ETQ  N1    N   NH1   0  -0.600  -1.3485  -0.3141   0.6978
 ETQ  O1    O   OH1   0  -0.610   0.9937  -1.7188   2.1234
 ETQ  CL1   CL  CL    0  -0.110   3.8009   1.1017  -2.1532
 ETQ  C2    C   CR6   0   0.007   2.9568  -1.5349   0.7356
 ETQ  N2    N   NT    0  -0.423  -3.7825   0.2095  -0.8556
 ETQ  O2    O   O2    0  -0.475   1.0334   1.6379  -1.1572
 ETQ  C3    C   CR16  0  -0.277   3.5805  -0.8348  -0.2866
 ETQ  O3    O   O     0  -0.476  -0.3185   1.4094   1.7379
 ETQ  C4    C   CR6   0  -0.148   2.9545   0.2208  -0.9270
 ETQ  C5    C   CR6   0   0.421   1.6713   0.6078  -0.5561
 ETQ  C6    C   CH3   0  -0.425   0.4794   1.3321  -2.4354
 ETQ  C7    C   CR6   0  -0.278   1.0328  -0.0735   0.4749
 ETQ  C8    C   C     0   0.515  -0.2796   0.4235   1.0182
 ETQ  C9    C   CH2   0  -0.276  -2.6515  -0.1342   1.3025
 ETQ  C10   C   CH1   0  -0.070  -3.6082   0.7433   0.4981
 ETQ  C11   C   CH2   0  -0.477  -5.0078   0.7311   1.1264
 ETQ  C12   C   CH2   0  -0.466  -5.7571  -0.3091   0.2985
 ETQ  C13   C   CH2   0  -0.261  -5.1923  -0.0638  -1.0903
 ETQ  C15   C   CH3   0  -0.680  -2.9354   0.1304  -3.1678
 ETQ  C16   C   CH2   0  -0.554   3.6405  -2.7127   1.3760
 ETQ  C17   C   CH3   0  -0.649   3.1339  -4.0491   0.8333
 ETQ  HN1   H   HNH1  0   0.403  -1.2238  -1.0930   0.0722
 ETQ  HO1   H   HOH1  0   0.483   1.5444  -2.3498   2.6004
 ETQ  H3    H   HCR6  0   0.280   4.5814  -1.1196  -0.5860
 ETQ  H6    H   HCH3  0   0.249  -0.1377   2.1808  -2.7228
 ETQ  H6A   H   HCH3  0   0.237   1.2509   1.1866  -3.1925
 ETQ  H6B   H   HCH3  0   0.225  -0.1434   0.4358  -2.3905
 ETQ  H9    H   HCH2  0   0.245  -3.0912  -1.1262   1.4278
 ETQ  H9A   H   HCH2  0   0.240  -2.5155   0.2869   2.2996
 ETQ  H10   H   HCH1  0   0.229  -3.2061   1.7630   0.4688
 ETQ  H11   H   HCH2  0   0.241  -4.9893   0.5049   2.1943
 ETQ  H11A  H   HCH2  0   0.238  -5.4794   1.7089   1.0111
 ETQ  H12   H   HCH2  0   0.228  -5.5201  -1.3207   0.6365
 ETQ  H12A  H   HCH2  0   0.241  -6.8399  -0.1923   0.3391
 ETQ  H13   H   HCH2  0   0.186  -5.7031   0.7970  -1.5542
 ETQ  H13A  H   HCH2  0   0.227  -5.3290  -0.9154  -1.7615
 ETQ  H14   H   HCH2  0   0.188  -3.6990   1.8738  -2.1604
 ETQ  H14A  H   HCH2  0   0.234  -2.1639   1.2888  -1.5433
 ETQ  H15   H   HCH3  0   0.218  -2.3592  -0.7692  -2.9451
 ETQ  H15A  H   HCH3  0   0.232  -3.8839  -0.1798  -3.6083
 ETQ  H15B  H   HCH3  0   0.226  -2.3955   0.7029  -3.9228
 ETQ  H16   H   HCH2  0   0.269   4.7136  -2.6352   1.1965
 ETQ  H16A  H   HCH2  0   0.246   3.5343  -2.6861   2.4656
 ETQ  H17   H   HCH3  0   0.224   2.0639  -4.1773   1.0000
 ETQ  H17A  H   HCH3  0   0.234   3.3103  -4.1209  -0.2399
 ETQ  H17B  H   HCH3  0   0.240   3.6466  -4.8807   1.3164
 ETQ  C14   C   CH2   0  -0.286  -3.1362   0.9579  -1.9090

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
 ETQ  C1   O1    single    1.347  0.020  1.347
 ETQ  C1   C2    aromatic  1.399  0.020  1.399
 ETQ  C1   C7    aromatic  1.395  0.020  1.395
 ETQ  N1   C8    single    1.338  0.020  1.338
 ETQ  N1   C9    single    1.448  0.020  1.448
 ETQ  CL1  C4    single    1.731  0.020  1.731
 ETQ  C2   C3    aromatic  1.387  0.020  1.387
 ETQ  C2   C16   single    1.505  0.020  1.505
 ETQ  N2   C10   single    1.466  0.020  1.466
 ETQ  N2   C13   single    1.455  0.020  1.455
 ETQ  N2   C14   single    1.445  0.020  1.445
 ETQ  O2   C5    single    1.353  0.020  1.353
 ETQ  O2   C6    single    1.426  0.020  1.426
 ETQ  C3   C4    aromatic  1.384  0.020  1.384
 ETQ  O3   C8    double    1.221  0.020  1.221
 ETQ  C4   C5    aromatic  1.391  0.020  1.391
 ETQ  C5   C7    aromatic  1.391  0.020  1.391
 ETQ  C7   C8    single    1.505  0.020  1.505
 ETQ  C9   C10   single    1.527  0.020  1.527
 ETQ  C10  C11   single    1.534  0.020  1.534
 ETQ  C11  C12   single    1.526  0.020  1.526
 ETQ  C12  C13   single    1.519  0.020  1.519
 ETQ  C14  C15   single    1.520  0.020  1.520
 ETQ  C16  C17   single    1.529  0.020  1.529
 ETQ  N1   HN1   single    0.860  0.020  1.020
 ETQ  O1   HO1   single    0.850  0.020  0.980
 ETQ  C3   H3    single    0.930  0.020  1.080
 ETQ  C6   H6    single    0.970  0.020  1.090
 ETQ  C6   H6A   single    0.970  0.020  1.090
 ETQ  C6   H6B   single    0.970  0.020  1.090
 ETQ  C9   H9    single    0.970  0.020  1.090
 ETQ  C9   H9A   single    0.970  0.020  1.090
 ETQ  C10  H10   single    0.970  0.020  1.090
 ETQ  C11  H11   single    0.970  0.020  1.090
 ETQ  C11  H11A  single    0.970  0.020  1.090
 ETQ  C12  H12   single    0.970  0.020  1.090
 ETQ  C12  H12A  single    0.970  0.020  1.090
 ETQ  C13  H13   single    0.970  0.020  1.090
 ETQ  C13  H13A  single    0.970  0.020  1.090
 ETQ  C14  H14   single    0.970  0.020  1.090
 ETQ  C14  H14A  single    0.970  0.020  1.090
 ETQ  C15  H15   single    0.970  0.020  1.090
 ETQ  C15  H15A  single    0.970  0.020  1.090
 ETQ  C15  H15B  single    0.970  0.020  1.090
 ETQ  C16  H16   single    0.970  0.020  1.090
 ETQ  C16  H16A  single    0.970  0.020  1.090
 ETQ  C17  H17   single    0.970  0.020  1.090
 ETQ  C17  H17A  single    0.970  0.020  1.090
 ETQ  C17  H17B  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
 ETQ  C7    C1   C2    120.87  3.000
 ETQ  C7    C1   O1    116.33  3.000
 ETQ  C2    C1   O1    122.80  3.000
 ETQ  HN1   N1   C9    117.84  3.000
 ETQ  HN1   N1   C8    118.46  3.000
 ETQ  C9    N1   C8    123.41  3.000
 ETQ  HO1   O1   C1    111.45  3.000
 ETQ  C16   C2   C3    120.28  3.000
 ETQ  C16   C2   C1    121.72  3.000
 ETQ  C3    C2   C1    117.98  3.000
 ETQ  C14   N2   C13   114.40  3.000
 ETQ  C14   N2   C10   115.57  3.000
 ETQ  C13   N2   C10   109.43  3.000
 ETQ  C6    O2   C5    114.72  3.000
 ETQ  H3    C3   C4    119.38  3.000
 ETQ  H3    C3   C2    119.12  3.000
 ETQ  C4    C3   C2    121.50  3.000
 ETQ  C5    C4   C3    120.41  3.000
 ETQ  C5    C4   CL1   119.90  3.000
 ETQ  C3    C4   CL1   119.65  3.000
 ETQ  C7    C5   C4    119.00  3.000
 ETQ  C7    C5   O2    119.07  3.000
 ETQ  C4    C5   O2    121.92  3.000
 ETQ  H6B   C6   H6A   108.80  3.000
 ETQ  H6B   C6   H6    109.12  3.000
 ETQ  H6A   C6   H6    108.78  3.000
 ETQ  H6B   C6   O2    111.13  3.000
 ETQ  H6A   C6   O2    112.08  3.000
 ETQ  H6    C6   O2    106.85  3.000
 ETQ  C8    C7   C5    120.41  3.000
 ETQ  C8    C7   C1    118.94  3.000
 ETQ  C5    C7   C1    120.23  3.000
 ETQ  C7    C8   O3    120.48  3.000
 ETQ  C7    C8   N1    115.36  3.000
 ETQ  O3    C8   N1    124.11  3.000
 ETQ  H9A   C9   H9    107.21  3.000
 ETQ  H9A   C9   C10   109.74  3.000
 ETQ  H9    C9   C10   109.27  3.000
 ETQ  H9A   C9   N1    108.51  3.000
 ETQ  H9    C9   N1    107.30  3.000
 ETQ  C10   C9   N1    114.53  3.000
 ETQ  H10   C10  C11   110.66  3.000
 ETQ  H10   C10  C9    108.58  3.000
 ETQ  C11   C10  C9    110.56  3.000
 ETQ  H10   C10  N2    110.96  3.000
 ETQ  C11   C10  N2    105.48  3.000
 ETQ  C9    C10  N2    110.60  3.000
 ETQ  H11A  C11  H11   107.23  3.000
 ETQ  H11A  C11  C12   109.94  3.000
 ETQ  H11   C11  C12   113.44  3.000
 ETQ  H11A  C11  C10   110.10  3.000
 ETQ  H11   C11  C10   112.75  3.000
 ETQ  C12   C11  C10   103.37  3.000
 ETQ  H12A  C12  H12   107.65  3.000
 ETQ  H12A  C12  C13   112.71  3.000
 ETQ  H12   C12  C13   110.59  3.000
 ETQ  H12A  C12  C11   113.24  3.000
 ETQ  H12   C12  C11   110.90  3.000
 ETQ  C13   C12  C11   101.73  3.000
 ETQ  H13A  C13  H13   106.97  3.000
 ETQ  H13A  C13  C12   112.90  3.000
 ETQ  H13   C13  C12   109.77  3.000
 ETQ  H13A  C13  N2    111.51  3.000
 ETQ  H13   C13  N2    111.71  3.000
 ETQ  C12   C13  N2    104.07  3.000
 ETQ  H15B  C15  H15A  107.47  3.000
 ETQ  H15B  C15  H15   108.22  3.000
 ETQ  H15A  C15  H15   107.89  3.000
 ETQ  H15B  C15  C14   110.67  3.000
 ETQ  H15A  C15  C14   111.99  3.000
 ETQ  H15   C15  C14   110.46  3.000
 ETQ  H16A  C16  H16   104.92  3.000
 ETQ  H16A  C16  C17   110.01  3.000
 ETQ  H16   C16  C17   109.25  3.000
 ETQ  H16A  C16  C2    111.12  3.000
 ETQ  H16   C16  C2    108.74  3.000
 ETQ  C17   C16  C2    112.49  3.000
 ETQ  H17B  C17  H17A  108.06  3.000
 ETQ  H17B  C17  H17   107.71  3.000
 ETQ  H17A  C17  H17   107.56  3.000
 ETQ  H17B  C17  C16   110.71  3.000
 ETQ  H17A  C17  C16   110.70  3.000
 ETQ  H17   C17  C16   111.94  3.000
 ETQ  H14A  C14  H14   106.21  3.000
 ETQ  H14A  C14  C15   108.99  3.000
 ETQ  H14   C14  C15   109.30  3.000
 ETQ  H14A  C14  N2    108.15  3.000
 ETQ  H14   C14  N2    111.57  3.000
 ETQ  C15   C14  N2    112.39  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
 ETQ  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 ETQ  CONST_02  C4   C5   C7   C1      0.00   0.0  0
 ETQ  CONST_03  C5   C7   C1   C2      0.00   0.0  0
 ETQ  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 ETQ  CONST_05  C7   C1   C2   C3      0.00   0.0  0
 ETQ  CONST_06  C7   C5   C4   C3      0.00   0.0  0
 ETQ  CONST_07  O2   C5   C7   C1    180.00   0.0  0
 ETQ  CONST_08  C3   C2   C1   O1    180.00   0.0  0
 ETQ  CONST_09  C5   C7   C1   O1    180.00   0.0  0
 ETQ  CONST_10  C2   C3   C4   CL1   180.00   0.0  0
 ETQ  CONST_11  C7   C5   C4   CL1   180.00   0.0  0
 ETQ  CONST_12  C8   C7   C1   C2    180.00   0.0  0
 ETQ  CONST_13  C3   C4   C5   O2    180.00   0.0  0
 ETQ  CONST_14  C16  C2   C3   C4    180.00   0.0  0
 ETQ  CONST_15  C8   C7   C5   C4    180.00   0.0  0
 ETQ  CONST_16  C16  C2   C1   C7    180.00   0.0  0
 ETQ  CONST_17  H3   C3   C2   C1    180.00   0.0  0
 ETQ  CONST_18  C9   N1   C8   C7    180.00   0.0  0
 ETQ  CONST_19  HN1  N1   C8   C7      0.00   0.0  0
 ETQ  CONST_20  C9   N1   C8   O3      0.00   0.0  0
 ETQ  Var_01    C11  C12  C13  N2     38.75  30.0  1
 ETQ  Var_02    C12  C13  N2   C10   -25.99  30.0  1
 ETQ  Var_03    C13  C12  C11  C10   -36.89  30.0  1
 ETQ  Var_04    C17  C16  C2   C1     78.74  30.0  2
 ETQ  Var_05    N1   C8   C7   C1    -79.38  30.0  2
 ETQ  Var_06    C7   C5   O2   C6   -102.94  30.0  2
 ETQ  Var_07    C15  C14  N2   C10   159.90  30.0  3
 ETQ  Var_08    C10  C9   N1   C8     96.15  30.0  3
 ETQ  Var_09    H17  C17  C16  C2    -59.75  30.0  3
 ETQ  Var_10    H15  C15  C14  N2    -56.93  30.0  3
 ETQ  Var_11    H6   C6   O2   C5    170.65  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
 ETQ  chir_01  C10  N2  C9  C11  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
 ETQ  plan-1  C1   0.020
 ETQ  plan-1  O1   0.020
 ETQ  plan-1  CL1  0.020
 ETQ  plan-1  C2   0.020
 ETQ  plan-1  O2   0.020
 ETQ  plan-1  C3   0.020
 ETQ  plan-1  C4   0.020
 ETQ  plan-1  C5   0.020
 ETQ  plan-1  C7   0.020
 ETQ  plan-1  C8   0.020
 ETQ  plan-1  C16  0.020
 ETQ  plan-1  H3   0.020
 ETQ  plan-2  N1   0.020
 ETQ  plan-2  O3   0.020
 ETQ  plan-2  C7   0.020
 ETQ  plan-2  C8   0.020
 ETQ  plan-2  C9   0.020
 ETQ  plan-2  HN1  0.020

