# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 07:15:50 2021
#   Inital geometry file: a 137 line input string
#   Ligand name: 2-[4-(4-cyano-3-methylphenoxy)phenyl]-N-ethyl-N-[2-(1H-pyrazol-1-yl)ethyl]acetamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(CCn1cccn1)C(=O)Cc2ccc(Oc3ccc(C#N)c(C)c3)cc2
#
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
 OAV  OAV  2-[4-(4-cyano-3-methylphenoxy)phenyl]-N-ethyl-N-[2-(1H-pyrazol-1-yl)ethyl]acetamide  ligand  53  29  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OAV
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
 OAV  C25  C  CR6   0   0.154  40.7651  6.4714  11.8428
 OAV  C28  C  CSP   0   0.027  40.9555  8.8939  12.1419
 OAV  C14  C  CR6   0   0.178  36.9631  3.3429  17.3409
 OAV  C18  C  CR16  0  -0.293  39.0919  3.5027  16.2043
 OAV  C19  C  CR16  0  -0.282  38.3545  3.2844  17.3563
 OAV  C21  C  CR6   0   0.409  39.5610  5.1867  13.5018
 OAV  C22  C  CR16  0  -0.355  39.2882  6.3349  14.2399
 OAV  C23  C  CR16  0  -0.222  39.7563  7.5499  13.7760
 OAV  C01  C  CH3   0  -0.650  33.2184  3.3238  20.5991
 OAV  C02  C  CH2   0  -0.338  34.6506  3.0205  21.0119
 OAV  C04  C  CH2   0  -0.328  35.7252  5.1043  21.7752
 OAV  C05  C  CH2   0  -0.307  36.7341  4.6447  22.8267
 OAV  C07  C  CR15  0   0.031  38.4365  3.1460  21.7891
 OAV  C08  C  CR15  0  -0.500  39.6571  3.3527  21.1902
 OAV  C09  C  CR15  0  -0.049  39.8792  4.7316  21.3376
 OAV  C11  C  C     0   0.584  36.2599  4.2501  19.5717
 OAV  C15  C  CR16  0  -0.320  36.3233  3.6291  16.1414
 OAV  C16  C  CR16  0  -0.284  37.0470  3.8536  14.9770
 OAV  C17  C  CR6   0   0.280  38.4279  3.7841  15.0198
 OAV  C24  C  CR6   0  -0.045  40.4871  7.6274  12.5926
 OAV  C26  C  CR16  0  -0.388  40.2925  5.2617  12.3164
 OAV  C27  C  CH3   0  -0.746  41.5492  6.5459  10.5697
 OAV  N03  N  NT    0  -0.455  35.5648  4.1177  20.7276
 OAV  N06  N  NR5   0  -0.247  38.0199  4.3416  22.2484
 OAV  N10  N  N     0  -0.287  38.8815  5.3161  21.9739
 OAV  N29  N  NS    0  -0.260  41.3399  9.9164  11.7714
 OAV  O12  O  O     0  -0.472  36.9360  5.2336  19.3225
 OAV  O20  O  O2    0  -0.504  39.1545  3.9507  13.8606
 OAV  H1   H  HCH2  0   0.291  35.1400  2.8634  18.3486
 OAV  H2   H  HCH2  0   0.292  36.5673  2.1905  19.0902
 OAV  H3   H  HCR6  0   0.273  40.1730  3.4486  16.2243
 OAV  H4   H  HCR6  0   0.260  38.8715  3.0618  18.2819
 OAV  H5   H  HCR6  0   0.291  38.7219  6.2990  15.1601
 OAV  H6   H  HCR6  0   0.285  39.5511  8.4491  14.3412
 OAV  H7   H  HCH3  0   0.236  32.5654  2.4940  20.8696
 OAV  H8   H  HCH3  0   0.232  32.8443  4.2178  21.0987
 OAV  H9   H  HCH3  0   0.229  33.1363  3.4796  19.5228
 OAV  H10  H  HCH2  0   0.260  34.6889  2.8261  22.0853
 OAV  H11  H  HCH2  0   0.264  34.9968  2.1027  20.5400
 OAV  H12  H  HCH2  0   0.269  36.0382  6.0538  21.3480
 OAV  H13  H  HCH2  0   0.264  34.7653  5.2708  22.2679
 OAV  H14  H  HCH2  0   0.279  36.8619  5.4212  23.5800
 OAV  H15  H  HCH2  0   0.261  36.3764  3.7503  23.3379
 OAV  H16  H  HCR5  0   0.288  37.8546  2.2489  21.9284
 OAV  H17  H  HCR5  0   0.257  40.2955  2.6189  20.7272
 OAV  H18  H  HCR5  0   0.256  40.7310  5.3103  21.0127
 OAV  H19  H  HCR6  0   0.257  35.2417  3.6745  16.1050
 OAV  H20  H  HCR6  0   0.274  36.5376  4.0721  14.0469
 OAV  H21  H  HCR6  0   0.276  40.4902  4.3526  11.7619
 OAV  H22  H  HCH3  0   0.261  41.0543  7.1855   9.8372
 OAV  H23  H  HCH3  0   0.260  42.5433  6.9614  10.7418
 OAV  H24  H  HCH3  0   0.265  41.6697  5.5601  10.1253
 OAV  C13  C  CH2   0  -0.712  36.1812  3.0852  18.5924

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
 OAV  C27  C25  single    1.497  0.020  1.497
 OAV  N29  C28  triple    1.153  0.020  1.153
 OAV  C25  C26  aromatic  1.382  0.020  1.382
 OAV  C25  C24  aromatic  1.406  0.020  1.406
 OAV  C28  C24  single    1.424  0.020  1.424
 OAV  C26  C21  aromatic  1.395  0.020  1.395
 OAV  C24  C23  aromatic  1.393  0.020  1.393
 OAV  C21  O20  single    1.350  0.020  1.350
 OAV  C21  C22  aromatic  1.392  0.020  1.392
 OAV  C23  C22  aromatic  1.382  0.020  1.382
 OAV  O20  C17  single    1.378  0.020  1.378
 OAV  C17  C16  aromatic  1.383  0.020  1.383
 OAV  C17  C18  aromatic  1.387  0.020  1.387
 OAV  C16  C15  aromatic  1.389  0.020  1.389
 OAV  C18  C19  aromatic  1.385  0.020  1.385
 OAV  C15  C14  aromatic  1.389  0.020  1.389
 OAV  C19  C14  aromatic  1.393  0.020  1.393
 OAV  C14  C13  single    1.498  0.020  1.498
 OAV  C13  C11  single    1.524  0.020  1.524
 OAV  O12  C11  double    1.219  0.020  1.219
 OAV  C11  N03  single    1.355  0.020  1.355
 OAV  C01  C02  single    1.521  0.020  1.521
 OAV  C08  C09  aromatic  1.404  0.020  1.404
 OAV  C08  C07  aromatic  1.375  0.020  1.375
 OAV  N03  C02  single    1.456  0.020  1.456
 OAV  N03  C04  single    1.448  0.020  1.448
 OAV  C09  N10  aromatic  1.320  0.020  1.320
 OAV  C07  N06  aromatic  1.347  0.020  1.347
 OAV  N10  N06  aromatic  1.329  0.020  1.329
 OAV  C04  C05  single    1.528  0.020  1.528
 OAV  N06  C05  single    1.442  0.020  1.442
 OAV  C13  H1   single    0.970  0.020  1.090
 OAV  C13  H2   single    0.970  0.020  1.090
 OAV  C18  H3   single    0.930  0.020  1.080
 OAV  C19  H4   single    0.930  0.020  1.080
 OAV  C22  H5   single    0.930  0.020  1.080
 OAV  C23  H6   single    0.930  0.020  1.080
 OAV  C01  H7   single    0.970  0.020  1.090
 OAV  C01  H8   single    0.970  0.020  1.090
 OAV  C01  H9   single    0.970  0.020  1.090
 OAV  C02  H10  single    0.970  0.020  1.090
 OAV  C02  H11  single    0.970  0.020  1.090
 OAV  C04  H12  single    0.970  0.020  1.090
 OAV  C04  H13  single    0.970  0.020  1.090
 OAV  C05  H14  single    0.970  0.020  1.090
 OAV  C05  H15  single    0.970  0.020  1.090
 OAV  C07  H16  single    0.930  0.020  1.080
 OAV  C08  H17  single    0.930  0.020  1.080
 OAV  C09  H18  single    0.930  0.020  1.080
 OAV  C15  H19  single    0.930  0.020  1.080
 OAV  C16  H20  single    0.930  0.020  1.080
 OAV  C26  H21  single    0.930  0.020  1.080
 OAV  C27  H22  single    0.970  0.020  1.090
 OAV  C27  H23  single    0.970  0.020  1.090
 OAV  C27  H24  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
 OAV  C27  C25  C26  120.93  3.000
 OAV  C26  C25  C24  117.99  3.000
 OAV  C27  C25  C24  121.09  3.000
 OAV  N29  C28  C24  180.00  3.000
 OAV  C15  C14  C19  118.58  3.000
 OAV  C19  C14  C13  120.33  3.000
 OAV  C15  C14  C13  121.09  3.000
 OAV  H3   C18  C17  120.27  3.000
 OAV  H3   C18  C19  120.56  3.000
 OAV  C17  C18  C19  119.17  3.000
 OAV  H4   C19  C18  119.27  3.000
 OAV  H4   C19  C14  119.66  3.000
 OAV  C18  C19  C14  121.07  3.000
 OAV  O20  C21  C26  115.66  3.000
 OAV  O20  C21  C22  123.74  3.000
 OAV  C26  C21  C22  120.60  3.000
 OAV  H5   C22  C23  119.49  3.000
 OAV  H5   C22  C21  121.77  3.000
 OAV  C23  C22  C21  118.74  3.000
 OAV  H6   C23  C24  119.81  3.000
 OAV  H6   C23  C22  119.41  3.000
 OAV  C24  C23  C22  120.77  3.000
 OAV  H9   C01  H8   108.02  3.000
 OAV  H9   C01  H7   107.98  3.000
 OAV  H8   C01  H7   107.76  3.000
 OAV  H9   C01  C02  111.54  3.000
 OAV  H8   C01  C02  111.23  3.000
 OAV  H7   C01  C02  110.18  3.000
 OAV  H11  C02  H10  105.36  3.000
 OAV  H11  C02  N03  110.55  3.000
 OAV  H10  C02  N03  107.71  3.000
 OAV  H11  C02  C01  110.48  3.000
 OAV  H10  C02  C01  109.60  3.000
 OAV  N03  C02  C01  112.83  3.000
 OAV  H13  C04  H12  107.29  3.000
 OAV  H13  C04  N03  109.45  3.000
 OAV  H12  C04  N03  110.04  3.000
 OAV  H13  C04  C05  108.42  3.000
 OAV  H12  C04  C05  110.06  3.000
 OAV  N03  C04  C05  111.47  3.000
 OAV  H15  C05  H14  107.40  3.000
 OAV  H15  C05  N06  107.94  3.000
 OAV  H14  C05  N06  108.82  3.000
 OAV  H15  C05  C04  110.65  3.000
 OAV  H14  C05  C04  109.81  3.000
 OAV  N06  C05  C04  112.09  3.000
 OAV  H16  C07  N06  121.84  3.000
 OAV  H16  C07  C08  131.32  3.000
 OAV  N06  C07  C08  106.83  3.000
 OAV  H17  C08  C09  128.33  3.000
 OAV  H17  C08  C07  127.64  3.000
 OAV  C09  C08  C07  104.02  3.000
 OAV  H18  C09  N10  120.26  3.000
 OAV  H18  C09  C08  128.27  3.000
 OAV  N10  C09  C08  111.46  3.000
 OAV  O12  C11  N03  122.52  3.000
 OAV  N03  C11  C13  116.55  3.000
 OAV  O12  C11  C13  120.93  3.000
 OAV  H19  C15  C16  119.03  3.000
 OAV  H19  C15  C14  119.84  3.000
 OAV  C16  C15  C14  121.13  3.000
 OAV  H20  C16  C17  120.43  3.000
 OAV  H20  C16  C15  120.50  3.000
 OAV  C17  C16  C15  119.07  3.000
 OAV  O20  C17  C16  119.61  3.000
 OAV  C16  C17  C18  120.97  3.000
 OAV  O20  C17  C18  119.38  3.000
 OAV  C23  C24  C28  119.41  3.000
 OAV  C23  C24  C25  120.74  3.000
 OAV  C28  C24  C25  119.84  3.000
 OAV  H21  C26  C21  119.05  3.000
 OAV  H21  C26  C25  119.79  3.000
 OAV  C21  C26  C25  121.16  3.000
 OAV  H24  C27  H23  107.97  3.000
 OAV  H24  C27  H22  107.89  3.000
 OAV  H23  C27  H22  107.21  3.000
 OAV  H24  C27  C25  111.11  3.000
 OAV  H23  C27  C25  111.22  3.000
 OAV  H22  C27  C25  111.26  3.000
 OAV  C11  N03  C04  119.58  3.000
 OAV  C04  N03  C02  116.21  3.000
 OAV  C11  N03  C02  124.20  3.000
 OAV  N10  N06  C07  112.32  3.000
 OAV  N10  N06  C05  120.44  3.000
 OAV  C07  N06  C05  126.81  3.000
 OAV  N06  N10  C09  105.36  3.000
 OAV  C17  O20  C21  119.54  3.000
 OAV  H2   C13  H1   105.78  3.000
 OAV  H2   C13  C11  108.33  3.000
 OAV  H1   C13  C11  110.37  3.000
 OAV  H2   C13  C14  109.66  3.000
 OAV  H1   C13  C14  110.25  3.000
 OAV  C11  C13  C14  112.24  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
 OAV  CONST_01  C22  C21  C26  C25     0.00   0.0  0
 OAV  CONST_02  C22  C23  C24  C25     0.00   0.0  0
 OAV  CONST_03  C17  C16  C15  C14     0.00   0.0  0
 OAV  CONST_04  C17  C18  C19  C14     0.00   0.0  0
 OAV  CONST_05  C15  C16  C17  C18     0.00   0.0  0
 OAV  CONST_06  C15  C14  C19  C18     0.00   0.0  0
 OAV  CONST_07  C16  C17  C18  C19     0.00   0.0  0
 OAV  CONST_08  C16  C15  C14  C19     0.00   0.0  0
 OAV  CONST_09  C24  C25  C26  C21     0.00   0.0  0
 OAV  CONST_10  C24  C23  C22  C21     0.00   0.0  0
 OAV  CONST_11  C26  C25  C24  C23     0.00   0.0  0
 OAV  CONST_12  C26  C21  C22  C23     0.00   0.0  0
 OAV  CONST_13  N10  C09  C08  C07     0.00   0.0  0
 OAV  CONST_14  C09  N10  N06  C07     0.00   0.0  0
 OAV  CONST_15  N06  N10  C09  C08     0.00   0.0  0
 OAV  CONST_16  N10  N06  C07  C08     0.00   0.0  0
 OAV  CONST_17  N06  C07  C08  C09     0.00   0.0  0
 OAV  CONST_18  O20  C21  C26  C25   180.00   0.0  0
 OAV  CONST_19  C26  C25  C24  C28   180.00   0.0  0
 OAV  CONST_20  C22  C23  C24  C28   180.00   0.0  0
 OAV  CONST_21  C16  C15  C14  C13   180.00   0.0  0
 OAV  CONST_22  C18  C19  C14  C13   180.00   0.0  0
 OAV  CONST_23  O20  C17  C18  C19   180.00   0.0  0
 OAV  CONST_24  C27  C25  C26  C21   180.00   0.0  0
 OAV  CONST_25  C27  C25  C24  C23   180.00   0.0  0
 OAV  CONST_26  O20  C21  C22  C23   180.00   0.0  0
 OAV  CONST_27  C08  C07  N06  C05   180.00   0.0  0
 OAV  CONST_28  C09  N10  N06  C05   180.00   0.0  0
 OAV  CONST_29  O20  C17  C16  C15   180.00   0.0  0
 OAV  CONST_30  H6   C23  C24  C25   180.00   0.0  0
 OAV  CONST_31  H20  C16  C15  C14   180.00   0.0  0
 OAV  CONST_32  H3   C18  C19  C14   180.00   0.0  0
 OAV  CONST_33  H19  C15  C14  C19   180.00   0.0  0
 OAV  CONST_34  H21  C26  C21  C22   180.00   0.0  0
 OAV  CONST_35  H18  C09  C08  C07   180.00   0.0  0
 OAV  CONST_36  H16  C07  C08  C09   180.00   0.0  0
 OAV  CONST_37  H4   C19  C14  C15   180.00   0.0  0
 OAV  CONST_38  H5   C22  C23  C24   180.00   0.0  0
 OAV  CONST_39  H17  C08  C07  N06   180.00   0.0  0
 OAV  CONST_40  C02  N03  C11  C13     0.00   0.0  0
 OAV  CONST_41  C04  N03  C11  C13   180.00   0.0  0
 OAV  CONST_42  O12  C11  N03  C02   180.00   0.0  0
 OAV  CONST_43  O12  C11  N03  C04     0.00   0.0  0
 OAV  Var_01    C16  C17  O20  C21    90.21  30.0  2
 OAV  Var_02    C26  C21  O20  C17   179.88  30.0  2
 OAV  Var_03    C11  C13  C14  C19    74.18  30.0  2
 OAV  Var_04    C07  N06  C05  C04   -90.88  30.0  3
 OAV  Var_05    H22  C27  C25  C24   -59.85  30.0  2
 OAV  Var_06    O12  C11  C13  C14    -2.18  30.0  3
 OAV  Var_07    N06  C05  C04  N03    56.79  30.0  3
 OAV  Var_08    C11  N03  C02  C01   -91.04  30.0  2
 OAV  Var_09    C05  C04  N03  C02    82.56  30.0  3
 OAV  Var_10    H7   C01  C02  N03  -177.57  30.0  3

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
 OAV  plan-1  C05  0.020
 OAV  plan-1  C07  0.020
 OAV  plan-1  C08  0.020
 OAV  plan-1  C09  0.020
 OAV  plan-1  N06  0.020
 OAV  plan-1  N10  0.020
 OAV  plan-1  H16  0.020
 OAV  plan-1  H17  0.020
 OAV  plan-1  H18  0.020
 OAV  plan-2  C25  0.020
 OAV  plan-2  C28  0.020
 OAV  plan-2  C21  0.020
 OAV  plan-2  C22  0.020
 OAV  plan-2  C23  0.020
 OAV  plan-2  C24  0.020
 OAV  plan-2  C26  0.020
 OAV  plan-2  C27  0.020
 OAV  plan-2  N29  0.020
 OAV  plan-2  O20  0.020
 OAV  plan-2  H5   0.020
 OAV  plan-2  H6   0.020
 OAV  plan-2  H21  0.020
 OAV  plan-3  C14  0.020
 OAV  plan-3  C18  0.020
 OAV  plan-3  C19  0.020
 OAV  plan-3  C15  0.020
 OAV  plan-3  C16  0.020
 OAV  plan-3  C17  0.020
 OAV  plan-3  O20  0.020
 OAV  plan-3  H3   0.020
 OAV  plan-3  H4   0.020
 OAV  plan-3  H19  0.020
 OAV  plan-3  H20  0.020
 OAV  plan-3  C13  0.020
 OAV  plan-4  C02  0.020
 OAV  plan-4  C04  0.020
 OAV  plan-4  C11  0.020
 OAV  plan-4  N03  0.020
 OAV  plan-4  O12  0.020
 OAV  plan-4  C13  0.020

