# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 15:51:27 2022
#   Inital geometry file: a 132 line input string
#   Ligand name: 4-methyl-3-(morpholin-4-ylmethyl)-7-[(1~{R})-1-phenylethoxy]chromen-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H](Oc1ccc2C(=C(CN3CCOCC3)C(=O)Oc2c1)C)c4ccccc4
#
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
 9ZW  9ZW  4-methyl-3-(morpholin-4-ylmethyl)-7-[(1~{R})-1-phenylethoxy]chromen-2-one  ligand  53  28  .  2022-03-11  2022-03-11
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9ZW
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
 9ZW  O    O  O     0  -0.426   6.3979  -19.1357  -37.0264
 9ZW  C    C  CR6   0   0.531   5.4863  -18.5950  -36.4479
 9ZW  C17  C  CR6   0  -0.219   5.5805  -17.3697  -35.6647
 9ZW  C18  C  CH2   0  -0.403   6.9317  -16.6814  -35.6847
 9ZW  N    N  NT    0  -0.404   7.1288  -15.6766  -36.7161
 9ZW  C22  C  CH2   0  -0.305   6.3029  -14.4937  -36.5744
 9ZW  C21  C  CH2   0  -0.175   6.7377  -13.4438  -37.5815
 9ZW  O3   O  O2    0  -0.481   6.6879  -13.9330  -38.9019
 9ZW  C20  C  CH2   0  -0.179   7.4912  -15.0835  -39.0395
 9ZW  C19  C  CH2   0  -0.303   7.0698  -16.1771  -38.0763
 9ZW  C15  C  CR6   0   0.222   4.4962  -16.9342  -34.9655
 9ZW  C16  C  CH3   0  -0.768   4.5246  -15.7576  -34.0430
 9ZW  C14  C  CR66  0  -0.040   3.2375  -17.6379  -35.0894
 9ZW  C1   C  CR66  0   0.392   3.1772  -18.7666  -35.8986
 9ZW  O1   O  O     0  -0.464   4.2806  -19.2132  -36.5308
 9ZW  C13  C  CR16  0  -0.310   2.0460  -17.2498  -34.4565
 9ZW  C12  C  CR16  0  -0.341   0.8811  -17.9554  -34.6273
 9ZW  C3   C  CR6   0   0.400   0.8552  -19.0922  -35.4506
 9ZW  C2   C  CR16  0  -0.445   2.0151  -19.5026  -36.0925
 9ZW  O2   O  O2    0  -0.477  -0.3327  -19.7025  -35.5530
 9ZW  C4   C  CH1   0  -0.044  -0.4819  -20.8688  -36.3565
 9ZW  C11  C  CH3   0  -0.661  -1.9757  -21.1058  -36.4898
 9ZW  C5   C  CR6   0   0.065   0.2123  -22.0661  -35.7500
 9ZW  C10  C  CR16  0  -0.288   0.2703  -22.2505  -34.3719
 9ZW  C9   C  CR16  0  -0.237   0.8741  -23.3824  -33.8416
 9ZW  C8   C  CR16  0  -0.263   1.4160  -24.3466  -34.6817
 9ZW  C7   C  CR16  0  -0.239   1.3553  -24.1703  -36.0574
 9ZW  C6   C  CR16  0  -0.291   0.7594  -23.0336  -36.5862
 9ZW  H1   H  HCH2  0   0.261   7.7094  -17.4358  -35.8082
 9ZW  H2   H  HCH2  0   0.259   7.1246  -16.2086  -34.7205
 9ZW  H4   H  HCH2  0   0.239   6.4276  -14.0800  -35.5713
 9ZW  H5   H  HCH2  0   0.200   5.2296  -14.7074  -36.7122
 9ZW  H6   H  HCH2  0   0.197   7.7551  -13.1067  -37.3356
 9ZW  H7   H  HCH2  0   0.232   6.0756  -12.5779  -37.5287
 9ZW  H8   H  HCH2  0   0.196   8.5488  -14.8359  -38.8678
 9ZW  H9   H  HCH2  0   0.232   7.3903  -15.4314  -40.0690
 9ZW  H10  H  HCH2  0   0.197   6.0623  -16.5291  -38.3530
 9ZW  H11  H  HCH2  0   0.240   7.7505  -17.0234  -38.1838
 9ZW  H12  H  HCH3  0   0.270   4.1407  -16.0392  -33.0615
 9ZW  H13  H  HCH3  0   0.267   5.5185  -15.3490  -33.9015
 9ZW  H14  H  HCH3  0   0.267   3.8865  -14.9558  -34.4191
 9ZW  H15  H  HCR6  0   0.271   2.0310  -16.3744  -33.8222
 9ZW  H16  H  HCR6  0   0.271  -0.0277  -17.6386  -34.1322
 9ZW  H17  H  HCR6  0   0.302   2.0533  -20.3756  -36.7291
 9ZW  H18  H  HCH1  0   0.254  -0.0671  -20.6799  -37.3544
 9ZW  H19  H  HCH3  0   0.244  -2.1514  -21.9808  -37.1141
 9ZW  H20  H  HCH3  0   0.238  -2.4329  -21.2873  -35.5165
 9ZW  H21  H  HCH3  0   0.245  -2.4673  -20.2526  -36.9577
 9ZW  H22  H  HCR6  0   0.254  -0.1499  -21.5104  -33.7020
 9ZW  H23  H  HCR6  0   0.255   0.9200  -23.5120  -32.7679
 9ZW  H24  H  HCR6  0   0.255   1.8859  -25.2285  -34.2660
 9ZW  H25  H  HCR6  0   0.255   1.7783  -24.9140  -36.7204
 9ZW  H26  H  HCR6  0   0.254   0.7245  -22.8950  -37.6611

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
 9ZW  C20  C19  single    1.517  0.020  1.517
 9ZW  C20  O3   single    1.410  0.020  1.410
 9ZW  C19  N    single    1.451  0.020  1.451
 9ZW  O3   C21  single    1.409  0.020  1.409
 9ZW  O    C    double    1.207  0.020  1.207
 9ZW  O1   C    single    1.357  0.020  1.357
 9ZW  O1   C1   single    1.348  0.020  1.348
 9ZW  C    C17  single    1.457  0.020  1.457
 9ZW  C11  C4   single    1.518  0.020  1.518
 9ZW  C21  C22  single    1.518  0.020  1.518
 9ZW  N    C22  single    1.450  0.020  1.450
 9ZW  N    C18  single    1.453  0.020  1.453
 9ZW  C4   O2   single    1.424  0.020  1.424
 9ZW  C4   C5   single    1.511  0.020  1.511
 9ZW  C2   C1   aromatic  1.389  0.020  1.389
 9ZW  C2   C3   aromatic  1.388  0.020  1.388
 9ZW  C1   C14  aromatic  1.390  0.020  1.390
 9ZW  C18  C17  single    1.516  0.020  1.516
 9ZW  C17  C15  double    1.362  0.020  1.362
 9ZW  C6   C5   aromatic  1.391  0.020  1.391
 9ZW  C6   C7   aromatic  1.388  0.020  1.388
 9ZW  O2   C3   single    1.339  0.020  1.339
 9ZW  C3   C12  aromatic  1.404  0.020  1.404
 9ZW  C5   C10  aromatic  1.392  0.020  1.392
 9ZW  C14  C15  single    1.447  0.020  1.447
 9ZW  C14  C13  aromatic  1.404  0.020  1.404
 9ZW  C15  C16  single    1.495  0.020  1.495
 9ZW  C7   C8   aromatic  1.388  0.020  1.388
 9ZW  C12  C13  aromatic  1.373  0.020  1.373
 9ZW  C10  C9   aromatic  1.388  0.020  1.388
 9ZW  C8   C9   aromatic  1.389  0.020  1.389
 9ZW  C18  H1   single    0.970  0.020  1.090
 9ZW  C18  H2   single    0.970  0.020  1.090
 9ZW  C22  H4   single    0.970  0.020  1.090
 9ZW  C22  H5   single    0.970  0.020  1.090
 9ZW  C21  H6   single    0.970  0.020  1.090
 9ZW  C21  H7   single    0.970  0.020  1.090
 9ZW  C20  H8   single    0.970  0.020  1.090
 9ZW  C20  H9   single    0.970  0.020  1.090
 9ZW  C19  H10  single    0.970  0.020  1.090
 9ZW  C19  H11  single    0.970  0.020  1.090
 9ZW  C16  H12  single    0.970  0.020  1.090
 9ZW  C16  H13  single    0.970  0.020  1.090
 9ZW  C16  H14  single    0.970  0.020  1.090
 9ZW  C13  H15  single    0.930  0.020  1.080
 9ZW  C12  H16  single    0.930  0.020  1.080
 9ZW  C2   H17  single    0.930  0.020  1.080
 9ZW  C4   H18  single    0.970  0.020  1.090
 9ZW  C11  H19  single    0.970  0.020  1.090
 9ZW  C11  H20  single    0.970  0.020  1.090
 9ZW  C11  H21  single    0.970  0.020  1.090
 9ZW  C10  H22  single    0.930  0.020  1.080
 9ZW  C9   H23  single    0.930  0.020  1.080
 9ZW  C8   H24  single    0.930  0.020  1.080
 9ZW  C7   H25  single    0.930  0.020  1.080
 9ZW  C6   H26  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
 9ZW  O1   C    C17  118.24  3.000
 9ZW  C17  C    O    125.82  3.000
 9ZW  O1   C    O    115.94  3.000
 9ZW  C15  C17  C18  124.83  3.000
 9ZW  C15  C17  C    119.56  3.000
 9ZW  C18  C17  C    115.60  3.000
 9ZW  H2   C18  H1   105.88  3.000
 9ZW  H2   C18  N    107.67  3.000
 9ZW  H1   C18  N    107.53  3.000
 9ZW  H2   C18  C17  110.03  3.000
 9ZW  H1   C18  C17  108.84  3.000
 9ZW  N    C18  C17  116.36  3.000
 9ZW  C19  N    C22  110.49  3.000
 9ZW  C22  N    C18  114.68  3.000
 9ZW  C19  N    C18  114.92  3.000
 9ZW  H5   C22  H4   107.42  3.000
 9ZW  H5   C22  C21  109.25  3.000
 9ZW  H4   C22  C21  108.33  3.000
 9ZW  H5   C22  N    112.59  3.000
 9ZW  H4   C22  N    109.50  3.000
 9ZW  C21  C22  N    109.65  3.000
 9ZW  H7   C21  H6   107.89  3.000
 9ZW  H7   C21  O3   107.42  3.000
 9ZW  H6   C21  O3   110.41  3.000
 9ZW  H7   C21  C22  110.05  3.000
 9ZW  H6   C21  C22  109.19  3.000
 9ZW  O3   C21  C22  111.80  3.000
 9ZW  C20  O3   C21  110.77  3.000
 9ZW  H9   C20  H8   107.94  3.000
 9ZW  H9   C20  C19  110.08  3.000
 9ZW  H8   C20  C19  109.29  3.000
 9ZW  H9   C20  O3   107.43  3.000
 9ZW  H8   C20  O3   110.42  3.000
 9ZW  C19  C20  O3   111.59  3.000
 9ZW  H11  C19  H10  107.32  3.000
 9ZW  H11  C19  C20  108.85  3.000
 9ZW  H10  C19  C20  108.94  3.000
 9ZW  H11  C19  N    109.55  3.000
 9ZW  H10  C19  N    112.50  3.000
 9ZW  C20  C19  N    109.59  3.000
 9ZW  C14  C15  C16  116.86  3.000
 9ZW  C16  C15  C17  123.59  3.000
 9ZW  C14  C15  C17  119.54  3.000
 9ZW  H14  C16  H13  107.71  3.000
 9ZW  H14  C16  H12  107.09  3.000
 9ZW  H13  C16  H12  107.61  3.000
 9ZW  H14  C16  C15  110.75  3.000
 9ZW  H13  C16  C15  113.24  3.000
 9ZW  H12  C16  C15  110.19  3.000
 9ZW  C13  C14  C1   116.75  3.000
 9ZW  C13  C14  C15  124.41  3.000
 9ZW  C1   C14  C15  118.84  3.000
 9ZW  C2   C1   O1   116.35  3.000
 9ZW  C2   C1   C14  123.21  3.000
 9ZW  O1   C1   C14  120.43  3.000
 9ZW  C1   O1   C    123.20  3.000
 9ZW  H15  C13  C12  118.52  3.000
 9ZW  H15  C13  C14  120.01  3.000
 9ZW  C12  C13  C14  121.47  3.000
 9ZW  H16  C12  C3   119.33  3.000
 9ZW  H16  C12  C13  120.35  3.000
 9ZW  C3   C12  C13  120.32  3.000
 9ZW  O2   C3   C2   124.83  3.000
 9ZW  O2   C3   C12  115.48  3.000
 9ZW  C2   C3   C12  119.69  3.000
 9ZW  H17  C2   C3   122.73  3.000
 9ZW  H17  C2   C1   118.71  3.000
 9ZW  C3   C2   C1   118.55  3.000
 9ZW  C4   O2   C3   120.62  3.000
 9ZW  H18  C4   C5   109.13  3.000
 9ZW  H18  C4   C11  108.60  3.000
 9ZW  C5   C4   C11  111.32  3.000
 9ZW  H18  C4   O2   109.42  3.000
 9ZW  C5   C4   O2   111.98  3.000
 9ZW  C11  C4   O2   106.29  3.000
 9ZW  H21  C11  H20  108.92  3.000
 9ZW  H21  C11  H19  108.06  3.000
 9ZW  H20  C11  H19  108.07  3.000
 9ZW  H21  C11  C4   111.05  3.000
 9ZW  H20  C11  C4   111.10  3.000
 9ZW  H19  C11  C4   109.54  3.000
 9ZW  C6   C5   C10  119.13  3.000
 9ZW  C10  C5   C4   121.44  3.000
 9ZW  C6   C5   C4   119.38  3.000
 9ZW  H22  C10  C9   119.32  3.000
 9ZW  H22  C10  C5   120.39  3.000
 9ZW  C9   C10  C5   120.29  3.000
 9ZW  H23  C9   C8   120.02  3.000
 9ZW  H23  C9   C10  119.67  3.000
 9ZW  C8   C9   C10  120.31  3.000
 9ZW  H24  C8   C7   120.20  3.000
 9ZW  H24  C8   C9   120.18  3.000
 9ZW  C7   C8   C9   119.62  3.000
 9ZW  H25  C7   C6   119.81  3.000
 9ZW  H25  C7   C8   120.17  3.000
 9ZW  C6   C7   C8   120.02  3.000
 9ZW  H26  C6   C7   119.75  3.000
 9ZW  H26  C6   C5   119.63  3.000
 9ZW  C7   C6   C5   120.62  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
 9ZW  CONST_01  C3   C2   C1   C14     0.00   0.0  0
 9ZW  CONST_02  C3   C12  C13  C14     0.00   0.0  0
 9ZW  CONST_03  C12  C3   C2   C1      0.00   0.0  0
 9ZW  CONST_04  C12  C13  C14  C1      0.00   0.0  0
 9ZW  CONST_05  C2   C1   C14  C13     0.00   0.0  0
 9ZW  CONST_06  C2   C3   C12  C13     0.00   0.0  0
 9ZW  CONST_07  C8   C7   C6   C5      0.00   0.0  0
 9ZW  CONST_08  C8   C9   C10  C5      0.00   0.0  0
 9ZW  CONST_09  C7   C6   C5   C10     0.00   0.0  0
 9ZW  CONST_10  C7   C8   C9   C10     0.00   0.0  0
 9ZW  CONST_11  C6   C5   C10  C9      0.00   0.0  0
 9ZW  CONST_12  C6   C7   C8   C9      0.00   0.0  0
 9ZW  CONST_13  O2   C3   C2   C1    180.00   0.0  0
 9ZW  CONST_14  O2   C3   C12  C13   180.00   0.0  0
 9ZW  CONST_15  C7   C6   C5   C4    180.00   0.0  0
 9ZW  CONST_16  C9   C10  C5   C4    180.00   0.0  0
 9ZW  CONST_17  H15  C13  C14  C15     0.00   0.0  0
 9ZW  CONST_18  H17  C2   C1   C14   180.00   0.0  0
 9ZW  CONST_19  H16  C12  C13  C14   180.00   0.0  0
 9ZW  CONST_20  H25  C7   C6   C5    180.00   0.0  0
 9ZW  CONST_21  H23  C9   C10  C5    180.00   0.0  0
 9ZW  CONST_22  H26  C6   C5   C10   180.00   0.0  0
 9ZW  CONST_23  H24  C8   C9   C10   180.00   0.0  0
 9ZW  CONST_24  H22  C10  C9   C8    180.00   0.0  0
 9ZW  Var_01    C2   C1   O1   C     179.41  30.0  1
 9ZW  Var_02    C14  C15  C17  C      -4.62  30.0  1
 9ZW  Var_03    C1   C14  C15  C17     1.58  30.0  1
 9ZW  Var_04    O3   C20  C19  N     -57.29  30.0  1
 9ZW  Var_05    O3   C21  C22  N      56.74  30.0  1
 9ZW  Var_06    C20  C19  N    C22    56.64  30.0  1
 9ZW  Var_07    C19  C20  O3   C21    57.63  30.0  1
 9ZW  Var_08    C19  N    C22  C21   -56.31  30.0  1
 9ZW  Var_09    O1   C    C17  C15     4.71  30.0  1
 9ZW  Var_10    N    C18  C17  C      91.20  30.0  3
 9ZW  Var_11    H12  C16  C15  C17  -126.83  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
 9ZW  chir_01  C4  C11  O2  C5  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
 9ZW  plan-1  C4   0.020
 9ZW  plan-1  C5   0.020
 9ZW  plan-1  C10  0.020
 9ZW  plan-1  C9   0.020
 9ZW  plan-1  C8   0.020
 9ZW  plan-1  C7   0.020
 9ZW  plan-1  C6   0.020
 9ZW  plan-1  H22  0.020
 9ZW  plan-1  H23  0.020
 9ZW  plan-1  H24  0.020
 9ZW  plan-1  H25  0.020
 9ZW  plan-1  H26  0.020
 9ZW  plan-2  C15  0.020
 9ZW  plan-2  C14  0.020
 9ZW  plan-2  C1   0.020
 9ZW  plan-2  O1   0.020
 9ZW  plan-2  C13  0.020
 9ZW  plan-2  C12  0.020
 9ZW  plan-2  C3   0.020
 9ZW  plan-2  C2   0.020
 9ZW  plan-2  O2   0.020
 9ZW  plan-2  H15  0.020
 9ZW  plan-2  H16  0.020
 9ZW  plan-2  H17  0.020
 9ZW  plan-3  O    0.020
 9ZW  plan-3  C    0.020
 9ZW  plan-3  C17  0.020
 9ZW  plan-3  O1   0.020

