# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 11:15:04 2020
#   Inital geometry file: a 135 line input string
#   Ligand name: (2Z)-4-[1-benzyl-4-(4-chlorobenzyl)piperidin-4-yl]-2-hydroxy-4-oxobut-2-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)C(/O)=C/C(=O)C1(CCN(CC1)Cc2ccccc2)Cc3ccc(Cl)cc3
#
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
 0N8  0N8  '(2Z)-4-[1-benzyl-4-(4-chlorobenzyl)piperidin-4-yl]-2-hydroxy-4-oxobut-2-enoic acid'  ligand  52  29  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_0N8
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
 0N8  CL2  CL  CL     0  -0.137  -4.7525   4.4497  -0.2839
 0N8  C19  C   CR6    0  -0.058  -3.6908   3.2435   0.3722
 0N8  C18  C   CR16   0  -0.199  -2.4942   3.6302   0.9532
 0N8  C17  C   CR16   0  -0.324  -1.6559   2.6571   1.4779
 0N8  C20  C   CR16   0  -0.200  -4.0569   1.9082   0.3164
 0N8  C21  C   CR16   0  -0.306  -3.2037   0.9516   0.8464
 0N8  C16  C   CR6    0   0.161  -1.9884   1.3050   1.4297
 0N8  C15  C   CH2    0  -0.503  -1.0591   0.2645   1.9890
 0N8  C11  C   CT     0  -0.228  -0.0471  -0.3296   0.9751
 0N8  C10  C   CH2    0  -0.415   0.9036   0.7530   0.4596
 0N8  C9   C   CH2    0  -0.277   2.0853   0.1955  -0.3216
 0N8  C14  C   C      0   0.437  -0.8489  -0.9648  -0.1692
 0N8  O27  O   O      0  -0.428  -0.8605  -0.4540  -1.2772
 0N8  C22  C   C1     0  -0.497  -1.6261  -2.1513   0.1541
 0N8  C23  C   C      0   0.211  -2.4265  -2.8165  -0.7064
 0N8  O28  O   OH1    0  -0.586  -2.6127  -2.5015  -1.9727
 0N8  C24  C   C      0   0.400  -3.2381  -4.0567  -0.2950
 0N8  O26  O   OC    -1  -0.604  -3.9087  -4.5126  -1.2484
 0N8  O25  O   O      0  -0.549  -3.1614  -4.4644   0.8659
 0N8  C12  C   CH2    0  -0.425   0.8130  -1.3648   1.7154
 0N8  C13  C   CH2    0  -0.280   1.9621  -1.8756   0.8641
 0N8  N8   N   NT     0  -0.411   2.8256  -0.7854   0.4523
 0N8  C7   C   CH2    0  -0.316   3.9835  -1.2708  -0.2668
 0N8  C2   C   CR6    0   0.086   5.0479  -0.2178  -0.4422
 0N8  C3   C   CR16   0  -0.284   5.3976   0.6222   0.6135
 0N8  C4   C   CR16   0  -0.242   6.4038   1.5654   0.4638
 0N8  C5   C   CR16   0  -0.272   7.0795   1.6831  -0.7458
 0N8  C6   C   CR16   0  -0.241   6.7371   0.8524  -1.8033
 0N8  C1   C   CR16   0  -0.315   5.7252  -0.0883  -1.6502
 0N8  H1   H   HCR6   0   0.276  -2.2168   4.6745   1.0036
 0N8  H2   H   HCR6   0   0.258  -0.7255   2.9648   1.9394
 0N8  H3   H   HCR6   0   0.276  -4.9972   1.6127  -0.1292
 0N8  H4   H   HCR6   0   0.260  -3.5013  -0.0894   0.8057
 0N8  H5   H   HCH2   0   0.257  -0.4761   0.7035   2.8030
 0N8  H6   H   HCH2   0   0.259  -1.6400  -0.5497   2.4293
 0N8  H7   H   HCH2   0   0.239   0.3797   1.4808  -0.1604
 0N8  H8   H   HCH2   0   0.225   1.2915   1.2980   1.3264
 0N8  H9   H   HCH2   0   0.196   1.7428  -0.2349  -1.2766
 0N8  H10  H   HCH2   0   0.237   2.7523   1.0223  -0.5743
 0N8  H11  H   H      0   0.258  -1.5919  -2.5442   1.1592
 0N8  H14  H   HOH1   0   0.456  -3.2486  -3.1949  -2.2724
 0N8  H16  H   HCH2   0   0.233   1.2247  -0.8846   2.6091
 0N8  H17  H   HCH2   0   0.243   0.2205  -2.2109   2.0665
 0N8  H18  H   HCH2   0   0.239   2.5527  -2.5876   1.4463
 0N8  H19  H   HCH2   0   0.188   1.5674  -2.4350  -0.0040
 0N8  H21  H   HCH2   0   0.250   4.4061  -2.1043   0.3040
 0N8  H22  H   HCH2   0   0.208   3.7158  -1.6835  -1.2547
 0N8  H23  H   HCR6   0   0.243   4.8645   0.5413   1.5529
 0N8  H24  H   HCR6   0   0.251   6.6629   2.2121   1.2926
 0N8  H25  H   HCR6   0   0.253   7.8644   2.4194  -0.8613
 0N8  H26  H   HCR6   0   0.252   7.2524   0.9390  -2.7516
 0N8  H27  H   HCR6   0   0.246   5.4584  -0.7289  -2.4834

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
 0N8  C6   C1   aromatic  1.390  0.020  1.390
 0N8  C6   C5   aromatic  1.388  0.020  1.388
 0N8  C1   C2   aromatic  1.391  0.020  1.391
 0N8  O27  C14  double    1.220  0.020  1.220
 0N8  C12  C13  single    1.519  0.020  1.519
 0N8  C12  C11  single    1.536  0.020  1.536
 0N8  C5   C4   aromatic  1.391  0.020  1.391
 0N8  C13  N8   single    1.450  0.020  1.450
 0N8  C2   C7   single    1.508  0.020  1.508
 0N8  C2   C3   aromatic  1.394  0.020  1.394
 0N8  O28  C23  single    1.318  0.020  1.318
 0N8  C7   N8   single    1.447  0.020  1.447
 0N8  C15  C11  single    1.551  0.020  1.551
 0N8  C15  C16  single    1.503  0.020  1.503
 0N8  C14  C11  single    1.535  0.020  1.535
 0N8  C14  C22  single    1.455  0.020  1.455
 0N8  C11  C10  single    1.530  0.020  1.530
 0N8  N8   C9   single    1.452  0.020  1.452
 0N8  C4   C3   aromatic  1.387  0.020  1.387
 0N8  C16  C21  aromatic  1.394  0.020  1.394
 0N8  C16  C17  aromatic  1.393  0.020  1.393
 0N8  C23  C22  double    1.350  0.020  1.350
 0N8  C23  C24  single    1.538  0.020  1.538
 0N8  C21  C20  aromatic  1.387  0.020  1.387
 0N8  C17  C18  aromatic  1.387  0.020  1.387
 0N8  O25  C24  deloc     1.233  0.020  1.233
 0N8  C10  C9   single    1.522  0.020  1.522
 0N8  C24  O26  deloc     1.252  0.020  1.252
 0N8  C20  C19  aromatic  1.386  0.020  1.386
 0N8  C18  C19  aromatic  1.385  0.020  1.385
 0N8  C19  CL2  single    1.736  0.020  1.736
 0N8  C18  H1   single    0.930  0.020  1.080
 0N8  C17  H2   single    0.930  0.020  1.080
 0N8  C20  H3   single    0.930  0.020  1.080
 0N8  C21  H4   single    0.930  0.020  1.080
 0N8  C15  H5   single    0.970  0.020  1.090
 0N8  C15  H6   single    0.970  0.020  1.090
 0N8  C10  H7   single    0.970  0.020  1.090
 0N8  C10  H8   single    0.970  0.020  1.090
 0N8  C9   H9   single    0.970  0.020  1.090
 0N8  C9   H10  single    0.970  0.020  1.090
 0N8  C22  H11  single    0.930  0.020  1.080
 0N8  O28  H14  single    0.850  0.020  0.980
 0N8  C12  H16  single    0.970  0.020  1.090
 0N8  C12  H17  single    0.970  0.020  1.090
 0N8  C13  H18  single    0.970  0.020  1.090
 0N8  C13  H19  single    0.970  0.020  1.090
 0N8  C7   H21  single    0.970  0.020  1.090
 0N8  C7   H22  single    0.970  0.020  1.090
 0N8  C3   H23  single    0.930  0.020  1.080
 0N8  C4   H24  single    0.930  0.020  1.080
 0N8  C5   H25  single    0.930  0.020  1.080
 0N8  C6   H26  single    0.930  0.020  1.080
 0N8  C1   H27  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
 0N8  C20  C19  C18  120.94  3.000
 0N8  C18  C19  CL2  119.53  3.000
 0N8  C20  C19  CL2  119.53  3.000
 0N8  H1   C18  C17  120.31  3.000
 0N8  H1   C18  C19  120.70  3.000
 0N8  C17  C18  C19  118.99  3.000
 0N8  H2   C17  C16  119.69  3.000
 0N8  H2   C17  C18  118.74  3.000
 0N8  C16  C17  C18  121.57  3.000
 0N8  H3   C20  C21  120.25  3.000
 0N8  H3   C20  C19  120.63  3.000
 0N8  C21  C20  C19  119.12  3.000
 0N8  H4   C21  C16  119.93  3.000
 0N8  H4   C21  C20  118.64  3.000
 0N8  C16  C21  C20  121.43  3.000
 0N8  C15  C16  C21  121.29  3.000
 0N8  C21  C16  C17  117.95  3.000
 0N8  C15  C16  C17  120.76  3.000
 0N8  H6   C15  H5   106.42  3.000
 0N8  H6   C15  C11  108.96  3.000
 0N8  H5   C15  C11  107.02  3.000
 0N8  H6   C15  C16  109.70  3.000
 0N8  H5   C15  C16  109.19  3.000
 0N8  C11  C15  C16  115.17  3.000
 0N8  C12  C11  C14  111.90  3.000
 0N8  C14  C11  C10  111.48  3.000
 0N8  C12  C11  C10  106.93  3.000
 0N8  C10  C11  C15  110.77  3.000
 0N8  C14  C11  C15  107.76  3.000
 0N8  C12  C11  C15  107.96  3.000
 0N8  H8   C10  H7   106.75  3.000
 0N8  H8   C10  C9   108.28  3.000
 0N8  H7   C10  C9   109.01  3.000
 0N8  H8   C10  C11  107.79  3.000
 0N8  H7   C10  C11  111.43  3.000
 0N8  C9   C10  C11  113.33  3.000
 0N8  H10  C9   H9   106.56  3.000
 0N8  H10  C9   N8   108.86  3.000
 0N8  H9   C9   N8   110.88  3.000
 0N8  H10  C9   C10  108.40  3.000
 0N8  H9   C9   C10  110.27  3.000
 0N8  N8   C9   C10  111.69  3.000
 0N8  C22  C14  O27  122.56  3.000
 0N8  C22  C14  C11  116.80  3.000
 0N8  O27  C14  C11  120.58  3.000
 0N8  H11  C22  C23  115.64  3.000
 0N8  H11  C22  C14  119.13  3.000
 0N8  C23  C22  C14  125.22  3.000
 0N8  C24  C23  O28  112.03  3.000
 0N8  C24  C23  C22  122.65  3.000
 0N8  O28  C23  C22  125.33  3.000
 0N8  H14  O28  C23  102.40  3.000
 0N8  O25  C24  O26  129.07  3.000
 0N8  O26  C24  C23  111.88  3.000
 0N8  O25  C24  C23  119.05  3.000
 0N8  H17  C12  H16  106.36  3.000
 0N8  H17  C12  C13  109.30  3.000
 0N8  H16  C12  C13  108.70  3.000
 0N8  H17  C12  C11  111.94  3.000
 0N8  H16  C12  C11  107.96  3.000
 0N8  C13  C12  C11  112.35  3.000
 0N8  H19  C13  H18  106.35  3.000
 0N8  H19  C13  N8   111.71  3.000
 0N8  H18  C13  N8   108.61  3.000
 0N8  H19  C13  C12  109.89  3.000
 0N8  H18  C13  C12  109.23  3.000
 0N8  N8   C13  C12  110.91  3.000
 0N8  C7   N8   C13  111.44  3.000
 0N8  C7   N8   C9   111.70  3.000
 0N8  C13  N8   C9   110.82  3.000
 0N8  H22  C7   H21  106.00  3.000
 0N8  H22  C7   C2   109.17  3.000
 0N8  H21  C7   C2   108.65  3.000
 0N8  H22  C7   N8   112.10  3.000
 0N8  H21  C7   N8   107.77  3.000
 0N8  C2   C7   N8   112.86  3.000
 0N8  C1   C2   C3   118.66  3.000
 0N8  C3   C2   C7   120.67  3.000
 0N8  C1   C2   C7   120.65  3.000
 0N8  H23  C3   C4   120.10  3.000
 0N8  H23  C3   C2   119.24  3.000
 0N8  C4   C3   C2   120.66  3.000
 0N8  H24  C4   C5   119.94  3.000
 0N8  H24  C4   C3   119.80  3.000
 0N8  C5   C4   C3   120.26  3.000
 0N8  H25  C5   C6   120.32  3.000
 0N8  H25  C5   C4   120.18  3.000
 0N8  C6   C5   C4   119.50  3.000
 0N8  H26  C6   C1   119.80  3.000
 0N8  H26  C6   C5   120.14  3.000
 0N8  C1   C6   C5   120.05  3.000
 0N8  H27  C1   C6   119.63  3.000
 0N8  H27  C1   C2   119.50  3.000
 0N8  C6   C1   C2   120.87  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
 0N8  CONST_01  C16  C21  C20  C19     0.00   0.0  0
 0N8  CONST_02  C16  C17  C18  C19     0.00   0.0  0
 0N8  CONST_03  C21  C16  C17  C18     0.00   0.0  0
 0N8  CONST_04  C21  C20  C19  C18     0.00   0.0  0
 0N8  CONST_05  C20  C21  C16  C17     0.00   0.0  0
 0N8  CONST_06  C20  C19  C18  C17     0.00   0.0  0
 0N8  CONST_07  C5   C6   C1   C2      0.00   0.0  0
 0N8  CONST_08  C5   C4   C3   C2      0.00   0.0  0
 0N8  CONST_09  C6   C1   C2   C3      0.00   0.0  0
 0N8  CONST_10  C6   C5   C4   C3      0.00   0.0  0
 0N8  CONST_11  C1   C6   C5   C4      0.00   0.0  0
 0N8  CONST_12  C1   C2   C3   C4      0.00   0.0  0
 0N8  CONST_13  C21  C20  C19  CL2   180.00   0.0  0
 0N8  CONST_14  C17  C18  C19  CL2   180.00   0.0  0
 0N8  CONST_15  C15  C16  C17  C18   180.00   0.0  0
 0N8  CONST_16  C15  C16  C21  C20   180.00   0.0  0
 0N8  CONST_17  C6   C1   C2   C7    180.00   0.0  0
 0N8  CONST_18  C4   C3   C2   C7    180.00   0.0  0
 0N8  CONST_19  H4   C21  C20  C19   180.00   0.0  0
 0N8  CONST_20  H2   C17  C18  C19   180.00   0.0  0
 0N8  CONST_21  H3   C20  C19  C18   180.00   0.0  0
 0N8  CONST_22  H1   C18  C19  C20   180.00   0.0  0
 0N8  CONST_23  H26  C6   C1   C2    180.00   0.0  0
 0N8  CONST_24  H24  C4   C3   C2    180.00   0.0  0
 0N8  CONST_25  H27  C1   C2   C3    180.00   0.0  0
 0N8  CONST_26  H25  C5   C4   C3    180.00   0.0  0
 0N8  CONST_27  H23  C3   C4   C5    180.00   0.0  0
 0N8  Var_01    N8   C13  C12  C11    58.95  30.0  1
 0N8  Var_02    N8   C9   C10  C11   -55.19  30.0  1
 0N8  Var_03    C13  N8   C9   C10    57.71  30.0  1
 0N8  Var_04    C12  C13  N8   C9    -59.66  30.0  1
 0N8  Var_05    C11  C15  C16  C17   -91.56  30.0  2
 0N8  Var_06    C2   C7   N8   C9     68.24  30.0  1
 0N8  Var_07    C1   C2   C7   N8   -138.32  30.0  2
 0N8  Var_08    C23  C22  C14  C11   177.57  30.0  2
 0N8  Var_09    O28  C23  C22  C14     0.85   0.0  2
 0N8  Var_10    O25  C24  C23  C22     0.12  30.0  2

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
 0N8  chir_01  C11  C12  C14  C10  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
 0N8  plan-1  CL2  0.020
 0N8  plan-1  C19  0.020
 0N8  plan-1  C18  0.020
 0N8  plan-1  C17  0.020
 0N8  plan-1  C20  0.020
 0N8  plan-1  C21  0.020
 0N8  plan-1  C16  0.020
 0N8  plan-1  C15  0.020
 0N8  plan-1  H1   0.020
 0N8  plan-1  H2   0.020
 0N8  plan-1  H3   0.020
 0N8  plan-1  H4   0.020
 0N8  plan-2  C7   0.020
 0N8  plan-2  C2   0.020
 0N8  plan-2  C3   0.020
 0N8  plan-2  C4   0.020
 0N8  plan-2  C5   0.020
 0N8  plan-2  C6   0.020
 0N8  plan-2  C1   0.020
 0N8  plan-2  H23  0.020
 0N8  plan-2  H24  0.020
 0N8  plan-2  H25  0.020
 0N8  plan-2  H26  0.020
 0N8  plan-2  H27  0.020
 0N8  plan-3  C23  0.020
 0N8  plan-3  C24  0.020
 0N8  plan-3  O26  0.020
 0N8  plan-3  O25  0.020
 0N8  plan-4  C11  0.020
 0N8  plan-4  C14  0.020
 0N8  plan-4  O27  0.020
 0N8  plan-4  C22  0.020
 0N8  plan-5  C14  0.020
 0N8  plan-5  C22  0.020
 0N8  plan-5  C23  0.020
 0N8  plan-5  O28  0.020
 0N8  plan-5  C24  0.020
 0N8  plan-5  H11  0.020

