# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 05:59:12 2020
#   Inital geometry file: a 95 line input string
#   Ligand name: 3-[5-chloranyl-6-(cyclobutylmethoxy)-2-oxidanylidene-1,3-benzoxazol-3-yl]propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)CCN1C(=O)Oc2cc(OCC3CCC3)c(Cl)cc12
#
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
 OK1  OK1  '3-[5-chloranyl-6-(cyclobutylmethoxy)-2-oxidanylidene-1,3-benzoxazol-3-yl]propanoic acid'  ligand  37  22  .  2022-09-22  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_OK1
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
 OK1  C4   C   CR16   0  -0.256   0.6633  -0.8410   0.4510
 OK1  C5   C   CR6    0  -0.177  -0.7000  -1.0372   0.2675
 OK1  C6   C   CR6    0   0.456  -1.5851   0.0101  -0.0290
 OK1  C7   C   CH2    0  -0.183  -3.8103   0.6996  -0.5139
 OK1  C8   C   CH1    0  -0.265  -5.1619   0.0525  -0.6434
 OK1  C10  C   CH2    0  -0.456  -7.1765   0.0450   0.0980
 OK1  C13  C   CR56   0   0.346   0.2583   1.4859   0.0366
 OK1  C14  C   CR5    0   0.663   2.2787   2.3587   0.2167
 OK1  N    N   NR5    0  -0.586   2.3793   1.0260   0.4522
 OK1  C2   C   CH2    0  -0.310   3.6280   0.3172   0.6736
 OK1  C1   C   CH2    0  -0.597   4.1742  -0.2980  -0.6035
 OK1  C    C   C      0   0.424   5.4875  -1.0774  -0.4027
 OK1  O1   O   O      0  -0.605   5.9596  -1.1082   0.7505
 OK1  O    O   OC    -1  -0.621   5.9673  -1.6100  -1.4218
 OK1  O3   O   O      0  -0.471   0.9637   2.6462  -0.0282
 OK1  C3   C   CR56   0   0.316   1.1266   0.4518   0.3290
 OK1  C12  C   CR16   0  -0.483  -1.0924   1.3142  -0.1474
 OK1  CL   CL  CL     0  -0.104  -1.3391  -2.6371   0.4057
 OK1  O2   O   O2     0  -0.456  -2.8734  -0.3178  -0.1835
 OK1  C11  C   CH2    0  -0.431  -5.8394  -0.5172   0.6181
 OK1  C9   C   CH2    0  -0.440  -6.3753   0.9859  -0.8228
 OK1  H1   H   HCR6   0   0.300   1.3168  -1.6731   0.6748
 OK1  H2   H   HCH2   0   0.236  -3.5260   1.1886  -1.4533
 OK1  H3   H   HCH2   0   0.222  -3.8295   1.4655   0.2712
 OK1  H4   H   HCH1   0   0.246  -5.1412  -0.6966  -1.4402
 OK1  H5   H   HCH2   0   0.228  -7.7309  -0.6993  -0.4750
 OK1  H6   H   HCH2   0   0.230  -7.8527   0.5001   0.8217
 OK1  H7   H   HCH2   0   0.266   4.3338   1.0238   1.1049
 OK1  H8   H   HCH2   0   0.260   3.4445  -0.4437   1.4321
 OK1  H9   H   HCH2   0   0.239   3.4308  -0.9689  -1.0469
 OK1  H10  H   HCH2   0   0.243   4.3399   0.4878  -1.3472
 OK1  H12  H   HCR6   0   0.310  -1.7308   2.1573  -0.3704
 OK1  H13  H   HCH2   0   0.232  -5.7668  -1.5905   0.7931
 OK1  H14  H   HCH2   0   0.223  -5.5067   0.0042   1.5185
 OK1  H15  H   HCH2   0   0.225  -6.2076   1.9588  -0.3546
 OK1  H16  H   HCH2   0   0.235  -6.7411   1.1492  -1.8365
 OK1  O4   O   O      0  -0.458   3.1361   3.2029   0.2095

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
 OK1  O1   C    deloc     1.247  0.020  1.247
 OK1  C    O    deloc     1.246  0.020  1.246
 OK1  C    C1   single    1.540  0.020  1.540
 OK1  CL   C5   single    1.728  0.020  1.728
 OK1  C2   C1   single    1.519  0.020  1.519
 OK1  C2   N    single    1.453  0.020  1.453
 OK1  C4   C5   aromatic  1.389  0.020  1.389
 OK1  C4   C3   aromatic  1.379  0.020  1.379
 OK1  C5   C6   aromatic  1.403  0.020  1.403
 OK1  N    C3   single    1.384  0.020  1.384
 OK1  N    C14  single    1.357  0.020  1.357
 OK1  C3   C13  aromatic  1.382  0.020  1.382
 OK1  C6   O2   single    1.338  0.020  1.338
 OK1  C6   C12  aromatic  1.399  0.020  1.399
 OK1  O2   C7   single    1.422  0.020  1.422
 OK1  C14  O4   double    1.203  0.020  1.203
 OK1  C14  O3   single    1.368  0.020  1.368
 OK1  C13  C12  aromatic  1.374  0.020  1.374
 OK1  C13  O3   single    1.359  0.020  1.359
 OK1  C11  C8   single    1.541  0.020  1.541
 OK1  C11  C10  single    1.541  0.020  1.541
 OK1  C7   C8   single    1.504  0.020  1.504
 OK1  C8   C9   single    1.541  0.020  1.541
 OK1  C10  C9   single    1.541  0.020  1.541
 OK1  C4   H1   single    0.930  0.020  1.080
 OK1  C7   H2   single    0.970  0.020  1.090
 OK1  C7   H3   single    0.970  0.020  1.090
 OK1  C8   H4   single    0.970  0.020  1.090
 OK1  C10  H5   single    0.970  0.020  1.090
 OK1  C10  H6   single    0.970  0.020  1.090
 OK1  C2   H7   single    0.970  0.020  1.090
 OK1  C2   H8   single    0.970  0.020  1.090
 OK1  C1   H9   single    0.970  0.020  1.090
 OK1  C1   H10  single    0.970  0.020  1.090
 OK1  C12  H12  single    0.930  0.020  1.080
 OK1  C11  H13  single    0.970  0.020  1.090
 OK1  C11  H14  single    0.970  0.020  1.090
 OK1  C9   H15  single    0.970  0.020  1.090
 OK1  C9   H16  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
 OK1  H1   C4   C3   122.46  3.000
 OK1  H1   C4   C5   120.77  3.000
 OK1  C3   C4   C5   116.78  3.000
 OK1  CL   C5   C6   118.34  3.000
 OK1  C6   C5   C4   122.78  3.000
 OK1  CL   C5   C4   118.88  3.000
 OK1  O2   C6   C12  123.89  3.000
 OK1  C12  C6   C5   119.44  3.000
 OK1  O2   C6   C5   116.66  3.000
 OK1  H3   C7   H2   107.84  3.000
 OK1  H3   C7   O2   110.17  3.000
 OK1  H2   C7   O2   110.33  3.000
 OK1  H3   C7   C8   110.26  3.000
 OK1  H2   C7   C8   110.55  3.000
 OK1  O2   C7   C8   107.71  3.000
 OK1  H4   C8   C9   110.17  3.000
 OK1  H4   C8   C11  110.57  3.000
 OK1  C9   C8   C11   88.45  3.000
 OK1  H4   C8   C7   109.90  3.000
 OK1  C9   C8   C7   117.19  3.000
 OK1  C11  C8   C7   118.92  3.000
 OK1  H6   C10  H5   108.57  3.000
 OK1  H6   C10  C9   117.66  3.000
 OK1  H5   C10  C9   111.53  3.000
 OK1  H6   C10  C11  117.81  3.000
 OK1  H5   C10  C11  111.68  3.000
 OK1  C9   C10  C11   88.47  3.000
 OK1  C12  C13  C3   123.55  3.000
 OK1  C12  C13  O3   127.61  3.000
 OK1  C3   C13  O3   108.83  3.000
 OK1  O3   C14  N    107.98  3.000
 OK1  O3   C14  O4   122.44  3.000
 OK1  N    C14  O4   129.58  3.000
 OK1  C3   N    C2   126.11  3.000
 OK1  C3   N    C14  108.96  3.000
 OK1  C2   N    C14  124.70  3.000
 OK1  H8   C2   H7   106.66  3.000
 OK1  H8   C2   C1   111.28  3.000
 OK1  H7   C2   C1   111.29  3.000
 OK1  H8   C2   N    107.57  3.000
 OK1  H7   C2   N    107.52  3.000
 OK1  C1   C2   N    112.25  3.000
 OK1  H10  C1   H9   105.51  3.000
 OK1  H10  C1   C    108.84  3.000
 OK1  H9   C1   C    108.76  3.000
 OK1  H10  C1   C2   109.57  3.000
 OK1  H9   C1   C2   110.14  3.000
 OK1  C    C1   C2   113.70  3.000
 OK1  O    C    O1   126.89  3.000
 OK1  O    C    C1   115.98  3.000
 OK1  O1   C    C1   117.13  3.000
 OK1  C14  O3   C13  108.11  3.000
 OK1  N    C3   C13  106.10  3.000
 OK1  C13  C3   C4   120.62  3.000
 OK1  N    C3   C4   133.28  3.000
 OK1  H12  C12  C13  120.72  3.000
 OK1  H12  C12  C6   122.45  3.000
 OK1  C13  C12  C6   116.83  3.000
 OK1  C7   O2   C6   119.06  3.000
 OK1  H14  C11  H13  108.51  3.000
 OK1  H14  C11  C10  111.62  3.000
 OK1  H13  C11  C10  118.12  3.000
 OK1  H14  C11  C8   111.37  3.000
 OK1  H13  C11  C8   117.79  3.000
 OK1  C10  C11  C8    88.30  3.000
 OK1  H16  C9   H15  108.46  3.000
 OK1  H16  C9   C10  118.21  3.000
 OK1  H15  C9   C10  111.55  3.000
 OK1  H16  C9   C8   117.60  3.000
 OK1  H15  C9   C8   111.62  3.000
 OK1  C10  C9   C8    88.28  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
 OK1  CONST_01  C12  C6   C5   C4      0.00   0.0  0
 OK1  CONST_02  C12  C13  C3   C4      0.00   0.0  0
 OK1  CONST_03  C13  C3   C4   C5      0.00   0.0  0
 OK1  CONST_04  C13  C12  C6   C5      0.00   0.0  0
 OK1  CONST_05  C3   C4   C5   C6      0.00   0.0  0
 OK1  CONST_06  C3   C13  C12  C6      0.00   0.0  0
 OK1  CONST_07  O2   C6   C5   C4    180.00   0.0  0
 OK1  CONST_08  O2   C6   C12  C13   180.00   0.0  0
 OK1  CONST_09  CL   C5   C4   C3    180.00   0.0  0
 OK1  CONST_10  CL   C5   C6   C12   180.00   0.0  0
 OK1  CONST_11  H12  C12  C6   C5    180.00   0.0  0
 OK1  CONST_12  H1   C4   C5   C6    180.00   0.0  0
 OK1  Var_01    C9   C10  C11  C8    -19.11  30.0  1
 OK1  Var_02    C8   C7   O2   C6    179.22  30.0  3
 OK1  Var_03    C12  C6   O2   C7      1.31  30.0  1
 OK1  Var_04    C1   C2   N    C14   -94.74  30.0  2
 OK1  Var_05    C    C1   C2   N    -179.08  30.0  3
 OK1  Var_06    O1   C    C1   C2     -0.79  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
 OK1  chir_01  C8  C11  C7  C9  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
 OK1  plan-1  C4   0.020
 OK1  plan-1  C5   0.020
 OK1  plan-1  C6   0.020
 OK1  plan-1  C13  0.020
 OK1  plan-1  C14  0.020
 OK1  plan-1  N    0.020
 OK1  plan-1  C2   0.020
 OK1  plan-1  O3   0.020
 OK1  plan-1  C3   0.020
 OK1  plan-1  C12  0.020
 OK1  plan-1  CL   0.020
 OK1  plan-1  O2   0.020
 OK1  plan-1  H1   0.020
 OK1  plan-1  H12  0.020
 OK1  plan-1  O4   0.020
 OK1  plan-2  C1   0.020
 OK1  plan-2  C    0.020
 OK1  plan-2  O1   0.020
 OK1  plan-2  O    0.020

