# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 21:52:42 2022
#   Inital geometry file: a 122 line input string
#   Ligand name: 1-butyl-3-chloranyl-4-(4-phenylpiperidin-1-yl)pyridin-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCN1C=CC(=C(Cl)C1=O)N2CCC(CC2)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
 HZR  HZR  1-butyl-3-chloranyl-4-(4-phenylpiperidin-1-yl)pyridin-2-one  ligand  49  24  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_HZR
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
 HZR  C14  C   CR16  0  -0.235  212.9638  197.4804  206.5482
 HZR  C11  C   CR16  0  -0.314  215.1068  195.8605  207.2224
 HZR  C10  C   CR6   0   0.167  214.9179  197.0557  207.9176
 HZR  C12  C   CR16  0  -0.235  214.2436  195.4829  206.2041
 HZR  C13  C   CR16  0  -0.274  213.1668  196.2922  205.8618
 HZR  C02  C   C     0   0.609  220.8475  193.8532  211.4610
 HZR  C03  C   C     0  -0.352  220.1454  195.0185  210.9891
 HZR  C05  C   C     0   0.525  218.7801  195.1807  211.0646
 HZR  C07  C   C     0  -0.337  216.9110  196.7547  211.1672
 HZR  C08  C   C     0  -0.445  215.7085  196.5593  210.2591
 HZR  C09  C   CR16  0  -0.323  215.8421  197.4762  209.0319
 HZR  C15  C   CR16  0  -0.333  213.8347  197.8559  207.5643
 HZR  C16  C   C     0  -0.471  217.3279  197.5831  208.6130
 HZR  C17  C   C     0  -0.299  218.1820  196.4165  209.0811
 HZR  C18  C   C1    0  -0.468  218.0466  194.1244  211.6782
 HZR  C19  C   C1    0   0.056  218.6979  193.0304  212.1355
 HZR  C22  C   CH2   0  -0.421  220.9324  190.6444  211.4439
 HZR  C23  C   CH2   0  -0.427  221.5548  189.3720  212.0054
 HZR  C24  C   CH3   0  -0.659  221.8607  188.3486  210.9213
 HZR  N06  N   NR6   0  -0.498  218.1528  196.2996  210.5448
 HZR  N20  N   NT    0  -0.520  220.0396  192.8861  212.0427
 HZR  O01  O   O     0  -0.495  222.0619  193.7019  211.3946
 HZR  CL4  CL  CL    0  -0.100  221.1667  196.2734  210.3896
 HZR  H1   H   HCR6  0   0.250  212.1290  198.1205  206.2922
 HZR  H2   H   HCR6  0   0.250  215.9352  195.2092  207.4756
 HZR  H3   H   HCR6  0   0.250  214.4112  194.5524  205.6765
 HZR  H4   H   HCR6  0   0.250  212.4931  195.9969  205.0678
 HZR  H7   H   H     0   0.250  217.0098  197.8187  211.4088
 HZR  H8   H   H     0   0.259  216.7729  196.2497  212.1224
 HZR  H9   H   H     0   0.250  214.7868  196.7891  210.7965
 HZR  H10  H   HCR6  0   0.245  213.6688  198.7894  208.0904
 HZR  H11  H   H     0   0.254  217.4204  197.6584  207.5285
 HZR  H12  H   H     0   0.249  217.7513  198.5055  209.0171
 HZR  H13  H   H     0   0.227  217.8330  195.4850  208.6175
 HZR  H14  H   H     0   0.247  219.2040  196.5696  208.7363
 HZR  H15  H   H     0   0.287  216.9706  194.1578  211.7542
 HZR  H17  H   H     0   0.309  218.1643  192.2058  212.5869
 HZR  H19  H   HCH2  0   0.261  220.0027  191.2419  213.2949
 HZR  H20  H   HCH2  0   0.262  221.5953  191.9347  213.0459
 HZR  H21  H   HCH2  0   0.232  221.5956  191.0764  210.6907
 HZR  H22  H   HCH2  0   0.226  219.9920  190.4031  210.9392
 HZR  H23  H   HCH2  0   0.219  220.8808  188.9335  212.7472
 HZR  H24  H   HCH2  0   0.219  222.4747  189.6249  212.5406
 HZR  H25  H   HCH3  0   0.228  222.3031  187.4444  211.3400
 HZR  H26  H   HCH3  0   0.218  220.9553  188.0569  210.3863
 HZR  H27  H   HCH3  0   0.218  222.5611  188.7515  210.1879
 HZR  H5   H   H     0   0.238  215.6437  195.5088  209.9592
 HZR  H6   H   HCR6  0   0.256  215.5288  198.4748  209.3486
 HZR  C21  C   CH2   0  -0.307  220.6685  191.6640  212.5420

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
 HZR  C13  C14  aromatic  1.387  0.020  1.387
 HZR  C13  C12  aromatic  1.390  0.020  1.390
 HZR  C14  C15  aromatic  1.390  0.020  1.390
 HZR  C12  C11  aromatic  1.387  0.020  1.387
 HZR  C15  C10  aromatic  1.392  0.020  1.392
 HZR  C11  C10  aromatic  1.396  0.020  1.396
 HZR  C10  C09  single    1.508  0.020  1.508
 HZR  C16  C09  single    1.547  0.020  1.547
 HZR  C16  C17  single    1.520  0.020  1.520
 HZR  C09  C08  single    1.538  0.020  1.538
 HZR  C17  N06  single    1.469  0.020  1.469
 HZR  C24  C23  single    1.522  0.020  1.522
 HZR  C08  C07  single    1.519  0.020  1.519
 HZR  N06  C07  single    1.462  0.020  1.462
 HZR  N06  C05  single    1.384  0.020  1.384
 HZR  C23  C22  single    1.524  0.020  1.524
 HZR  C22  C21  single    1.522  0.020  1.522
 HZR  C03  CL4  single    1.725  0.020  1.725
 HZR  C03  C05  double    1.377  0.020  1.377
 HZR  C03  C02  single    1.440  0.020  1.440
 HZR  C05  C18  single    1.425  0.020  1.425
 HZR  C18  C19  double    1.353  0.020  1.353
 HZR  C02  O01  double    1.226  0.020  1.226
 HZR  C02  N20  single    1.388  0.020  1.388
 HZR  N20  C21  single    1.462  0.020  1.462
 HZR  N20  C19  single    1.353  0.020  1.353
 HZR  C14  H1   single    0.930  0.020  1.080
 HZR  C11  H2   single    0.930  0.020  1.080
 HZR  C12  H3   single    0.930  0.020  1.080
 HZR  C13  H4   single    0.930  0.020  1.080
 HZR  C07  H7   single    0.970  0.020  1.090
 HZR  C07  H8   single    0.970  0.020  1.090
 HZR  C08  H9   single    0.970  0.020  1.090
 HZR  C15  H10  single    0.930  0.020  1.080
 HZR  C16  H11  single    0.970  0.020  1.090
 HZR  C16  H12  single    0.970  0.020  1.090
 HZR  C17  H13  single    0.970  0.020  1.090
 HZR  C17  H14  single    0.970  0.020  1.090
 HZR  C18  H15  single    0.930  0.020  1.080
 HZR  C19  H17  single    0.930  0.020  1.080
 HZR  C21  H19  single    0.970  0.020  1.090
 HZR  C21  H20  single    0.970  0.020  1.090
 HZR  C22  H21  single    0.970  0.020  1.090
 HZR  C22  H22  single    0.970  0.020  1.090
 HZR  C23  H23  single    0.970  0.020  1.090
 HZR  C23  H24  single    0.970  0.020  1.090
 HZR  C24  H25  single    0.970  0.020  1.090
 HZR  C24  H26  single    0.970  0.020  1.090
 HZR  C24  H27  single    0.970  0.020  1.090
 HZR  C08  H5   single    0.970  0.020  1.090
 HZR  C09  H6   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
 HZR  H1   C14  C15  119.75  3.000
 HZR  H1   C14  C13  120.15  3.000
 HZR  C15  C14  C13  120.10  3.000
 HZR  H2   C11  C12  118.92  3.000
 HZR  H2   C11  C10  120.11  3.000
 HZR  C12  C11  C10  120.97  3.000
 HZR  C15  C10  C09  120.28  3.000
 HZR  C09  C10  C11  121.62  3.000
 HZR  C15  C10  C11  118.10  3.000
 HZR  H3   C12  C13  120.02  3.000
 HZR  H3   C12  C11  119.69  3.000
 HZR  C13  C12  C11  120.29  3.000
 HZR  H4   C13  C12  120.27  3.000
 HZR  H4   C13  C14  120.38  3.000
 HZR  C12  C13  C14  119.36  3.000
 HZR  O01  C02  N20  120.89  3.000
 HZR  N20  C02  C03  114.67  3.000
 HZR  O01  C02  C03  124.42  3.000
 HZR  CL4  C03  C05  121.35  3.000
 HZR  C05  C03  C02  124.11  3.000
 HZR  CL4  C03  C02  114.44  3.000
 HZR  N06  C05  C18  121.85  3.000
 HZR  C18  C05  C03  116.53  3.000
 HZR  N06  C05  C03  121.60  3.000
 HZR  H8   C07  H7   105.56  3.000
 HZR  H8   C07  N06  109.68  3.000
 HZR  H7   C07  N06  108.64  3.000
 HZR  H8   C07  C08  111.36  3.000
 HZR  H7   C07  C08  109.15  3.000
 HZR  N06  C07  C08  112.20  3.000
 HZR  H5   C08  H9   106.68  3.000
 HZR  H5   C08  C09  111.03  3.000
 HZR  H9   C08  C09  109.93  3.000
 HZR  H5   C08  C07  109.51  3.000
 HZR  H9   C08  C07  110.30  3.000
 HZR  C09  C08  C07  109.36  3.000
 HZR  H6   C09  C16  106.89  3.000
 HZR  H6   C09  C08  106.77  3.000
 HZR  C16  C09  C08  109.92  3.000
 HZR  H6   C09  C10  107.05  3.000
 HZR  C08  C09  C10  111.73  3.000
 HZR  C16  C09  C10  114.07  3.000
 HZR  H10  C15  C10  119.39  3.000
 HZR  H10  C15  C14  119.43  3.000
 HZR  C10  C15  C14  121.18  3.000
 HZR  H12  C16  H11  106.05  3.000
 HZR  H12  C16  C17  108.45  3.000
 HZR  H11  C16  C17  108.15  3.000
 HZR  H12  C16  C09  109.29  3.000
 HZR  H11  C16  C09  110.81  3.000
 HZR  C17  C16  C09  113.78  3.000
 HZR  H14  C17  H13  106.49  3.000
 HZR  H14  C17  N06  110.20  3.000
 HZR  H13  C17  N06  110.31  3.000
 HZR  H14  C17  C16  108.77  3.000
 HZR  H13  C17  C16  110.05  3.000
 HZR  N06  C17  C16  110.91  3.000
 HZR  H15  C18  C19  118.77  3.000
 HZR  H15  C18  C05  121.37  3.000
 HZR  C19  C18  C05  119.82  3.000
 HZR  H17  C19  N20  115.91  3.000
 HZR  H17  C19  C18  121.36  3.000
 HZR  N20  C19  C18  122.72  3.000
 HZR  H22  C22  H21  106.91  3.000
 HZR  H22  C22  C23  109.69  3.000
 HZR  H21  C22  C23  109.65  3.000
 HZR  H22  C22  C21  109.36  3.000
 HZR  H21  C22  C21  109.75  3.000
 HZR  C23  C22  C21  111.37  3.000
 HZR  H24  C23  H23  106.20  3.000
 HZR  H24  C23  C24  109.57  3.000
 HZR  H23  C23  C24  109.71  3.000
 HZR  H24  C23  C22  109.31  3.000
 HZR  H23  C23  C22  109.45  3.000
 HZR  C24  C23  C22  112.41  3.000
 HZR  H27  C24  H26  107.56  3.000
 HZR  H27  C24  H25  107.70  3.000
 HZR  H26  C24  H25  107.65  3.000
 HZR  H27  C24  C23  111.07  3.000
 HZR  H26  C24  C23  111.23  3.000
 HZR  H25  C24  C23  111.45  3.000
 HZR  C17  N06  C07  114.61  3.000
 HZR  C07  N06  C05  118.48  3.000
 HZR  C17  N06  C05  115.44  3.000
 HZR  C21  N20  C19  119.50  3.000
 HZR  C19  N20  C02  122.13  3.000
 HZR  C21  N20  C02  118.36  3.000
 HZR  H20  C21  H19  107.25  3.000
 HZR  H20  C21  N20  108.43  3.000
 HZR  H19  C21  N20  107.26  3.000
 HZR  H20  C21  C22  110.67  3.000
 HZR  H19  C21  C22  110.18  3.000
 HZR  N20  C21  C22  112.84  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
 HZR  CONST_01  C11  C12  C13  C14     0.00   0.0  0
 HZR  CONST_02  C11  C10  C15  C14     0.00   0.0  0
 HZR  CONST_03  C13  C14  C15  C10     0.00   0.0  0
 HZR  CONST_04  C13  C12  C11  C10     0.00   0.0  0
 HZR  CONST_05  C15  C14  C13  C12     0.00   0.0  0
 HZR  CONST_06  C15  C10  C11  C12     0.00   0.0  0
 HZR  CONST_07  C09  C10  C15  C14   180.00   0.0  0
 HZR  CONST_08  C09  C10  C11  C12   180.00   0.0  0
 HZR  CONST_09  C19  N20  C02  C03     0.00   0.0  0
 HZR  CONST_10  C21  N20  C02  C03   180.00   0.0  0
 HZR  CONST_11  O01  C02  N20  C19   180.00   0.0  0
 HZR  CONST_12  H3   C12  C13  C14   180.00   0.0  0
 HZR  CONST_13  H4   C13  C12  C11   180.00   0.0  0
 HZR  CONST_14  H10  C15  C10  C11   180.00   0.0  0
 HZR  CONST_15  H1   C14  C15  C10   180.00   0.0  0
 HZR  CONST_16  H2   C11  C12  C13   180.00   0.0  0
 HZR  CONST_17  O01  C02  N20  C21     0.00   0.0  0
 HZR  Var_01    C17  N06  C05  C03    67.85  30.0  3
 HZR  Var_02    C16  C17  N06  C05   173.22  30.0  1
 HZR  Var_03    C08  C07  N06  C05  -111.56  30.0  1
 HZR  Var_04    N06  C17  C16  C09   -59.16  30.0  1
 HZR  Var_05    N06  C07  C08  C09   -66.14  30.0  1
 HZR  Var_06    C22  C21  N20  C02   -81.42  30.0  3
 HZR  Var_07    N20  C21  C22  C23  -178.55  30.0  3
 HZR  Var_08    C24  C23  C22  C21  -178.58  30.0  2
 HZR  Var_09    H25  C24  C23  C22  -179.88  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
 HZR  chir_01  C09  C10  C16  C08  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
 HZR  plan-1  C14  0.020
 HZR  plan-1  C11  0.020
 HZR  plan-1  C10  0.020
 HZR  plan-1  C12  0.020
 HZR  plan-1  C13  0.020
 HZR  plan-1  C09  0.020
 HZR  plan-1  C15  0.020
 HZR  plan-1  H1   0.020
 HZR  plan-1  H2   0.020
 HZR  plan-1  H3   0.020
 HZR  plan-1  H4   0.020
 HZR  plan-1  H10  0.020
 HZR  plan-2  C02  0.020
 HZR  plan-2  C03  0.020
 HZR  plan-2  C05  0.020
 HZR  plan-2  C18  0.020
 HZR  plan-2  C19  0.020
 HZR  plan-2  N06  0.020
 HZR  plan-2  N20  0.020
 HZR  plan-2  O01  0.020
 HZR  plan-2  CL4  0.020
 HZR  plan-2  H15  0.020
 HZR  plan-2  H17  0.020
 HZR  plan-2  C21  0.020
 HZR  plan-3  C05  0.020
 HZR  plan-3  C07  0.020
 HZR  plan-3  C17  0.020
 HZR  plan-3  N06  0.020

