# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 29 14:14:32 2020
#   Inital geometry file: a 146 line input string
#   Ligand name: 2-[(3~{S})-7-fluoranyl-6-(2-methylpropyl)-4-[(3-oxidanylidene-4~{H}-1,4-benzoxazin-6-yl)carbonyl]-2,3-dihydro-1,4-benzoxazin-3-yl]-~{N}-methyl-ethanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CNC(=O)C[C@H]1COc2cc(F)c(CC(C)C)cc2N1C(=O)c3ccc4OCC(=O)Nc4c3
#
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
 EYN  EYN  2-[(3~{S})-7-fluoranyl-6-(2-methylpropyl)-4-[(3-oxidanylidene-4~{H}-1,4-benzoxazin-6-yl)carbonyl]-2,3-dihydro-1,4-benzoxazin-3-yl]-~{N}-methyl-ethanamide  ligand  59  33  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_EYN
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
 EYN  C1   C  CH3   0  -0.657   6.1252  -3.5086   1.8854
 EYN  C2   C  CH1   0  -0.233   5.2108  -2.8403   0.8646
 EYN  C3   C  CH3   0  -0.650   3.9412  -3.6607   0.6644
 EYN  C7   C  CR66  0   0.265   1.9543   0.1750  -0.5366
 EYN  C8   C  CR66  0   0.375   2.5811   0.7293  -1.6524
 EYN  C9   C  CR16  0  -0.526   3.9593   0.6051  -1.7995
 EYN  C10  C  CR6   0   0.518   4.6703  -0.0772  -0.8385
 EYN  C13  C  C     0  -0.157   0.5069   1.4913  -2.4887
 EYN  C14  C  CR16  0  -0.222   0.0560   1.5437  -1.0354
 EYN  C19  C  CR6   0  -0.107  -1.6880  -0.5182   0.0248
 EYN  C20  C  CR16  0  -0.262  -2.1409   0.2417   1.0964
 EYN  C21  C  CR16  0  -0.347  -3.5024   0.3872   1.3196
 EYN  C22  C  CR6   0   0.346  -4.4084  -0.2301   0.4758
 EYN  C24  C  CR16  0  -0.348  -2.5983  -1.1484  -0.8165
 EYN  N25  N  NH1   0  -0.721  -4.9064  -1.6356  -1.3930
 EYN  C30  C  CH2   0  -0.559   0.5262   2.8265  -0.3414
 EYN  C31  C  C     0   0.546   0.0967   2.8794   1.1077
 EYN  C34  C  CH3   0  -0.515  -1.5876   3.7383   2.6609
 EYN  C4   C  CH2   0  -0.485   4.8931  -1.4024   1.3057
 EYN  C5   C  CR6   0  -0.088   4.0924  -0.6309   0.2975
 EYN  C6   C  CR16  0  -0.320   2.7221  -0.4639   0.4292
 EYN  O12  O  O     0  -0.475   1.9215   1.4335  -2.5937
 EYN  N16  N  NR6   0  -0.532   0.5571   0.3331  -0.3942
 EYN  C17  C  C     0   0.498  -0.2292  -0.7662  -0.1763
 EYN  O18  O  O     0  -0.437   0.2186  -1.8945  -0.1085
 EYN  C23  C  CR6   0   0.336  -3.9573  -0.9987  -0.5982
 EYN  C26  C  C     0   0.484  -6.2156  -1.2976  -1.3867
 EYN  O27  O  O     0  -0.452  -7.0463  -1.8118  -2.1075
 EYN  C28  C  CH2   0  -0.310  -6.5610  -0.1713  -0.4345
 EYN  O29  O  O2    0  -0.471  -5.7344  -0.1344   0.7149
 EYN  O32  O  O     0  -0.492   0.7036   2.2809   1.9861
 EYN  N33  N  NH1   0  -0.616  -1.0015   3.6096   1.3495
 EYN  H1   H  HCH3  0   0.228   6.4007  -4.5151   1.5667
 EYN  H2   H  HCH3  0   0.226   7.0458  -2.9415   2.0335
 EYN  H3   H  HCH3  0   0.215   5.6275  -3.5947   2.8545
 EYN  H4   H  HCH1  0   0.223   5.7456  -2.7923  -0.0902
 EYN  H5   H  HCH3  0   0.234   3.2630  -3.2045  -0.0581
 EYN  H6   H  HCH3  0   0.227   4.1788  -4.6650   0.3097
 EYN  H7   H  HCH3  0   0.211   3.3970  -3.7630   1.6070
 EYN  H8   H  HCR6  0   0.286   4.4593   1.0371  -2.6571
 EYN  H9   H  H     0   0.253   0.0608   0.6183  -2.9761
 EYN  H10  H  H     0   0.261   0.1918   2.3829  -3.0298
 EYN  H11  H  HCR6  0   0.312  -1.0330   1.5230  -1.0327
 EYN  H12  H  HCR6  0   0.267  -1.4355   0.7072   1.7711
 EYN  H13  H  HCR6  0   0.277  -3.8661   0.9563   2.1655
 EYN  H14  H  HCR6  0   0.284  -2.2549  -1.7565  -1.6447
 EYN  H15  H  HNH1  0   0.419  -4.5978  -2.3372  -2.0528
 EYN  H16  H  HCH2  0   0.280   1.6124   2.9217  -0.3767
 EYN  H17  H  HCH2  0   0.279   0.1127   3.6656  -0.9041
 EYN  H18  H  HCH3  0   0.253  -2.2341   4.6112   2.6716
 EYN  H19  H  HCH3  0   0.234  -2.1874   2.8660   2.9310
 EYN  H20  H  HCH3  0   0.245  -0.8174   3.8693   3.4185
 EYN  H21  H  HCH2  0   0.239   4.3326  -1.4411   2.2449
 EYN  H22  H  HCH2  0   0.245   5.8286  -0.8831   1.5294
 EYN  H23  H  HCR6  0   0.265   2.2356  -0.8526   1.3136
 EYN  H24  H  HCH2  0   0.274  -6.5017   0.7747  -0.9882
 EYN  H25  H  HCH2  0   0.287  -7.5840  -0.2973  -0.0879
 EYN  H26  H  HNH1  0   0.405  -1.4564   4.0740   0.5820
 EYN  F11  F  F     0  -0.313   5.9980  -0.2043  -1.0119

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
 EYN  C34  N33  single    1.442  0.020  1.442
 EYN  N33  C31  single    1.341  0.020  1.341
 EYN  O27  C26  double    1.214  0.020  1.214
 EYN  O18  C17  double    1.216  0.020  1.216
 EYN  N25  C26  single    1.352  0.020  1.352
 EYN  N25  C23  single    1.392  0.020  1.392
 EYN  O32  C31  double    1.224  0.020  1.224
 EYN  C26  C28  single    1.515  0.020  1.515
 EYN  C31  C30  single    1.512  0.020  1.512
 EYN  C24  C23  aromatic  1.385  0.020  1.385
 EYN  C24  C19  aromatic  1.391  0.020  1.391
 EYN  C23  C22  aromatic  1.396  0.020  1.396
 EYN  C17  C19  single    1.493  0.020  1.493
 EYN  C17  N16  single    1.369  0.020  1.369
 EYN  C19  C20  aromatic  1.390  0.020  1.390
 EYN  C30  C14  single    1.532  0.020  1.532
 EYN  C14  N16  single    1.459  0.020  1.459
 EYN  C14  C13  single    1.523  0.020  1.523
 EYN  C28  O29  single    1.416  0.020  1.416
 EYN  N16  C7   single    1.413  0.020  1.413
 EYN  C22  O29  single    1.351  0.020  1.351
 EYN  C22  C21  aromatic  1.383  0.020  1.383
 EYN  C20  C21  aromatic  1.387  0.020  1.387
 EYN  C13  O12  single    1.420  0.020  1.420
 EYN  C7   C6   aromatic  1.389  0.020  1.389
 EYN  C7   C8   aromatic  1.395  0.020  1.395
 EYN  C6   C5   aromatic  1.387  0.020  1.387
 EYN  O12  C8   single    1.348  0.020  1.348
 EYN  C8   C9   aromatic  1.392  0.020  1.392
 EYN  C5   C4   single    1.501  0.020  1.501
 EYN  C5   C10  aromatic  1.390  0.020  1.390
 EYN  C4   C2   single    1.537  0.020  1.537
 EYN  C2   C3   single    1.525  0.020  1.525
 EYN  C2   C1   single    1.525  0.020  1.525
 EYN  C9   C10  aromatic  1.376  0.020  1.376
 EYN  C10  F11  single    1.345  0.020  1.345
 EYN  C1   H1   single    0.970  0.020  1.090
 EYN  C1   H2   single    0.970  0.020  1.090
 EYN  C1   H3   single    0.970  0.020  1.090
 EYN  C2   H4   single    0.970  0.020  1.090
 EYN  C3   H5   single    0.970  0.020  1.090
 EYN  C3   H6   single    0.970  0.020  1.090
 EYN  C3   H7   single    0.970  0.020  1.090
 EYN  C9   H8   single    0.930  0.020  1.080
 EYN  C13  H9   single    0.970  0.020  1.090
 EYN  C13  H10  single    0.970  0.020  1.090
 EYN  C14  H11  single    0.970  0.020  1.090
 EYN  C20  H12  single    0.930  0.020  1.080
 EYN  C21  H13  single    0.930  0.020  1.080
 EYN  C24  H14  single    0.930  0.020  1.080
 EYN  N25  H15  single    0.860  0.020  1.020
 EYN  C30  H16  single    0.970  0.020  1.090
 EYN  C30  H17  single    0.970  0.020  1.090
 EYN  C34  H18  single    0.970  0.020  1.090
 EYN  C34  H19  single    0.970  0.020  1.090
 EYN  C34  H20  single    0.970  0.020  1.090
 EYN  C4   H21  single    0.970  0.020  1.090
 EYN  C4   H22  single    0.970  0.020  1.090
 EYN  C6   H23  single    0.930  0.020  1.080
 EYN  C28  H24  single    0.970  0.020  1.090
 EYN  C28  H25  single    0.970  0.020  1.090
 EYN  N33  H26  single    0.860  0.020  1.020

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
 EYN  H3   C1   H2   107.74  3.000
 EYN  H3   C1   H1   107.54  3.000
 EYN  H2   C1   H1   107.82  3.000
 EYN  H3   C1   C2   110.80  3.000
 EYN  H2   C1   C2   111.65  3.000
 EYN  H1   C1   C2   111.12  3.000
 EYN  H4   C2   C4   108.06  3.000
 EYN  H4   C2   C3   108.40  3.000
 EYN  C4   C2   C3   111.65  3.000
 EYN  H4   C2   C1   108.05  3.000
 EYN  C3   C2   C1   110.57  3.000
 EYN  C4   C2   C1   109.99  3.000
 EYN  H7   C3   H6   107.61  3.000
 EYN  H7   C3   H5   107.50  3.000
 EYN  H6   C3   H5   107.76  3.000
 EYN  H7   C3   C2   110.59  3.000
 EYN  H6   C3   C2   110.89  3.000
 EYN  H5   C3   C2   112.30  3.000
 EYN  N16  C7   C6   121.85  3.000
 EYN  C6   C7   C8   119.37  3.000
 EYN  N16  C7   C8   118.71  3.000
 EYN  O12  C8   C9   117.22  3.000
 EYN  C9   C8   C7   119.62  3.000
 EYN  O12  C8   C7   123.12  3.000
 EYN  H8   C9   C10  120.82  3.000
 EYN  H8   C9   C8   120.36  3.000
 EYN  C10  C9   C8   118.82  3.000
 EYN  F11  C10  C5   118.57  3.000
 EYN  F11  C10  C9   117.82  3.000
 EYN  C5   C10  C9   123.61  3.000
 EYN  H10  C13  H9   108.27  3.000
 EYN  H10  C13  O12  106.55  3.000
 EYN  H9   C13  O12  109.91  3.000
 EYN  H10  C13  C14  111.12  3.000
 EYN  H9   C13  C14  109.38  3.000
 EYN  O12  C13  C14  111.54  3.000
 EYN  H11  C14  N16  109.06  3.000
 EYN  H11  C14  C30  108.76  3.000
 EYN  N16  C14  C30  112.97  3.000
 EYN  H11  C14  C13  107.33  3.000
 EYN  N16  C14  C13  106.81  3.000
 EYN  C30  C14  C13  111.73  3.000
 EYN  C17  C19  C24  118.86  3.000
 EYN  C17  C19  C20  120.86  3.000
 EYN  C24  C19  C20  120.08  3.000
 EYN  H12  C20  C21  119.65  3.000
 EYN  H12  C20  C19  120.26  3.000
 EYN  C21  C20  C19  120.08  3.000
 EYN  H13  C21  C22  119.42  3.000
 EYN  H13  C21  C20  120.70  3.000
 EYN  C22  C21  C20  119.86  3.000
 EYN  O29  C22  C23  119.51  3.000
 EYN  O29  C22  C21  120.22  3.000
 EYN  C23  C22  C21  120.23  3.000
 EYN  H14  C24  C23  119.50  3.000
 EYN  H14  C24  C19  120.63  3.000
 EYN  C23  C24  C19  119.88  3.000
 EYN  H15  N25  C26  118.16  3.000
 EYN  H15  N25  C23  118.80  3.000
 EYN  C26  N25  C23  122.89  3.000
 EYN  H17  C30  H16  107.06  3.000
 EYN  H17  C30  C31  111.07  3.000
 EYN  H16  C30  C31  108.10  3.000
 EYN  H17  C30  C14  107.09  3.000
 EYN  H16  C30  C14  111.33  3.000
 EYN  C31  C30  C14  112.09  3.000
 EYN  N33  C31  O32  122.89  3.000
 EYN  O32  C31  C30  121.98  3.000
 EYN  N33  C31  C30  115.11  3.000
 EYN  H20  C34  H19  108.21  3.000
 EYN  H20  C34  H18  108.52  3.000
 EYN  H19  C34  H18  108.21  3.000
 EYN  H20  C34  N33  110.86  3.000
 EYN  H19  C34  N33  112.13  3.000
 EYN  H18  C34  N33  108.81  3.000
 EYN  H22  C4   H21  106.23  3.000
 EYN  H22  C4   C5   110.48  3.000
 EYN  H21  C4   C5   108.75  3.000
 EYN  H22  C4   C2   109.04  3.000
 EYN  H21  C4   C2   108.60  3.000
 EYN  C5   C4   C2   113.47  3.000
 EYN  C6   C5   C4   121.69  3.000
 EYN  C4   C5   C10  122.15  3.000
 EYN  C6   C5   C10  116.14  3.000
 EYN  H23  C6   C5   118.61  3.000
 EYN  H23  C6   C7   119.02  3.000
 EYN  C5   C6   C7   122.37  3.000
 EYN  C13  O12  C8   117.21  3.000
 EYN  C17  N16  C14  122.62  3.000
 EYN  C14  N16  C7   112.84  3.000
 EYN  C17  N16  C7   119.61  3.000
 EYN  O18  C17  N16  122.86  3.000
 EYN  N16  C17  C19  116.69  3.000
 EYN  O18  C17  C19  120.42  3.000
 EYN  N25  C23  C24  121.98  3.000
 EYN  C24  C23  C22  119.88  3.000
 EYN  N25  C23  C22  118.10  3.000
 EYN  C28  C26  O27  122.15  3.000
 EYN  C28  C26  N25  114.18  3.000
 EYN  O27  C26  N25  123.63  3.000
 EYN  H25  C28  H24  108.14  3.000
 EYN  H25  C28  O29  107.06  3.000
 EYN  H24  C28  O29  110.81  3.000
 EYN  H25  C28  C26  109.19  3.000
 EYN  H24  C28  C26  108.14  3.000
 EYN  O29  C28  C26  113.36  3.000
 EYN  C28  O29  C22  115.31  3.000
 EYN  H26  N33  C34  117.96  3.000
 EYN  H26  N33  C31  118.97  3.000
 EYN  C34  N33  C31  123.05  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
 EYN  CONST_01  C10  C5   C6   C7     0.00   0.0  0
 EYN  CONST_02  C10  C9   C8   C7     0.00   0.0  0
 EYN  CONST_03  C5   C6   C7   C8     0.00   0.0  0
 EYN  CONST_04  C5   C10  C9   C8     0.00   0.0  0
 EYN  CONST_05  C6   C7   C8   C9     0.00   0.0  0
 EYN  CONST_06  C6   C5   C10  C9     0.00   0.0  0
 EYN  CONST_07  C22  C23  C24  C19    0.00   0.0  0
 EYN  CONST_08  C22  C21  C20  C19    0.00   0.0  0
 EYN  CONST_09  C23  C24  C19  C20    0.00   0.0  0
 EYN  CONST_10  C23  C22  C21  C20    0.00   0.0  0
 EYN  CONST_11  C24  C23  C22  C21    0.00   0.0  0
 EYN  CONST_12  C24  C19  C20  C21    0.00   0.0  0
 EYN  CONST_13  C28  C26  N25  C23    0.00   0.0  0
 EYN  CONST_14  C4   C5   C6   C7   180.00   0.0  0
 EYN  CONST_15  F11  C10  C9   C8   180.00   0.0  0
 EYN  CONST_16  C4   C5   C10  C9   180.00   0.0  0
 EYN  CONST_17  C17  C19  C20  C21  180.00   0.0  0
 EYN  CONST_18  F11  C10  C5   C6   180.00   0.0  0
 EYN  CONST_19  C23  C24  C19  C17  180.00   0.0  0
 EYN  CONST_20  C19  C17  N16  C7   180.00   0.0  0
 EYN  CONST_22  O27  C26  N25  C23  180.00   0.0  0
 EYN  CONST_23  H8   C9   C8   C7   180.00   0.0  0
 EYN  CONST_24  H23  C6   C7   C8   180.00   0.0  0
 EYN  CONST_25  H13  C21  C20  C19  180.00   0.0  0
 EYN  CONST_26  H14  C24  C19  C20  180.00   0.0  0
 EYN  CONST_27  H12  C20  C21  C22  180.00   0.0  0
 EYN  CONST_28  H15  N25  C26  C28  180.00   0.0  0
 EYN  CONST_29  O18  C17  N16  C7     0.00   0.0  0
 EYN  CONST_31  C34  N33  C31  C30  180.00   0.0  0
 EYN  CONST_32  O32  C31  N33  C34    0.00   0.0  0
 EYN  CONST_33  H26  N33  C31  C30    0.00   0.0  0
 EYN  Var_01    C14  N16  C7   C8   -28.01  30.0  1
 EYN  Var_02    C14  C13  O12  C8    35.73  30.0  1
 EYN  Var_03    C26  N25  C23  C22   16.58  30.0  1
 EYN  Var_04    C26  C28  O29  C22   47.82  30.0  1
 EYN  Var_05    O29  C28  C26  N25  -31.09  30.0  1
 EYN  Var_06    N16  C17  C19  C20  -62.03  30.0  2
 EYN  Var_07    C6   C5   C4   C2    99.95  30.0  1
 EYN  Var_08    C5   C4   C2   C1   175.05  30.0  2
 EYN  Var_09    N33  C31  C30  C14  -98.68  30.0  1
 EYN  Var_10    H5   C3   C2   C1   179.71  30.0  3
 EYN  Var_11    H1   C1   C2   C3    58.91  30.0  3
 EYN  Var_12    H18  C34  N33  C31  161.18  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
 EYN  chir_01  C14  C30  N16  C13  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
 EYN  plan-1  C7   0.020
 EYN  plan-1  C8   0.020
 EYN  plan-1  C9   0.020
 EYN  plan-1  C10  0.020
 EYN  plan-1  C4   0.020
 EYN  plan-1  C5   0.020
 EYN  plan-1  C6   0.020
 EYN  plan-1  O12  0.020
 EYN  plan-1  N16  0.020
 EYN  plan-1  H8   0.020
 EYN  plan-1  H23  0.020
 EYN  plan-1  F11  0.020
 EYN  plan-2  C19  0.020
 EYN  plan-2  C20  0.020
 EYN  plan-2  C21  0.020
 EYN  plan-2  C22  0.020
 EYN  plan-2  C24  0.020
 EYN  plan-2  N25  0.020
 EYN  plan-2  C17  0.020
 EYN  plan-2  C23  0.020
 EYN  plan-2  O29  0.020
 EYN  plan-2  H12  0.020
 EYN  plan-2  H13  0.020
 EYN  plan-2  H14  0.020
 EYN  plan-3  C30  0.020
 EYN  plan-3  C31  0.020
 EYN  plan-3  C34  0.020
 EYN  plan-3  O32  0.020
 EYN  plan-3  N33  0.020
 EYN  plan-3  H26  0.020
 EYN  plan-4  C7   0.020
 EYN  plan-4  C14  0.020
 EYN  plan-4  C19  0.020
 EYN  plan-4  N16  0.020
 EYN  plan-4  C17  0.020
 EYN  plan-4  O18  0.020
 EYN  plan-5  N25  0.020
 EYN  plan-5  C23  0.020
 EYN  plan-5  C26  0.020
 EYN  plan-5  O27  0.020
 EYN  plan-5  C28  0.020
 EYN  plan-5  H15  0.020

