# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 14:36:25 2020
#   Inital geometry file: a 73 line input string
#   Ligand name: 3-(5-chloranyl-6-methyl-2-oxidanylidene-1,3-benzoxazol-3-yl)propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc2OC(=O)N(CCC(O)=O)c2cc1Cl
#
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
 8RK  8RK  '3-(5-chloranyl-6-methyl-2-oxidanylidene-1,3-benzoxazol-3-yl)propanoic acid'  ligand  27  17  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_8RK
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
 8RK  C4   C   CR5   0   0.674  -0.9385   2.2697  -0.1422
 8RK  C5   C   CH2   0  -0.317  -2.0680   0.1488  -0.7631
 8RK  C6   C   CH2   0  -0.593  -2.6752  -0.4772   0.4843
 8RK  C7   C   C     0   0.560  -3.8846  -1.3111   0.1678
 8RK  C8   C   CR56  0   0.328   0.3857   0.4717  -0.2588
 8RK  C10  C   CR6   0  -0.116   2.3319  -0.8436  -0.1400
 8RK  CL   CL  CL    0  -0.118   3.0935  -2.3924  -0.3172
 8RK  C1   C   CR6   0   0.149   3.1084   0.2491   0.2527
 8RK  C    C   CH3   0  -0.721   4.5760   0.1158   0.5262
 8RK  C9   C   CR16  0  -0.247   0.9660  -0.7694  -0.4025
 8RK  C3   C   CR56  0   0.334   1.1370   1.5681   0.1274
 8RK  C2   C   CR16  0  -0.392   2.4807   1.4929   0.3878
 8RK  N    N   NR5   0  -0.596  -0.9029   0.9386  -0.4344
 8RK  O1   O   O     0  -0.449  -1.8738   3.0233  -0.1572
 8RK  O    O   O     0  -0.467   0.3232   2.6590   0.1920
 8RK  O3   O   O     0  -0.442  -4.3295  -1.4795  -0.9398
 8RK  O2   O   OH1   0  -0.591  -4.4150  -1.8437   1.2604
 8RK  H1   H   HCH2  0   0.285  -1.7678  -0.6133  -1.4814
 8RK  H2   H   HCH2  0   0.291  -2.7836   0.7963  -1.2662
 8RK  H3   H   HCH2  0   0.297  -1.9424  -1.1037   1.0014
 8RK  H4   H   HCH2  0   0.299  -2.9627   0.3004   1.1970
 8RK  H5   H   HCH3  0   0.254   5.1180  -0.2226  -0.3578
 8RK  H6   H   HCH3  0   0.256   4.9986   1.0711   0.8312
 8RK  H7   H   HCH3  0   0.253   4.7718  -0.6062   1.3199
 8RK  H8   H   HCR6  0   0.301   0.4049  -1.6432  -0.7038
 8RK  H9   H   HCR6  0   0.285   3.0460   2.3647   0.6894
 8RK  H10  H   HOH1  0   0.482  -5.1977  -2.3665   1.0300

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
 8RK  O3   C7   double    1.205  0.020  1.205
 8RK  C7   O2   single    1.326  0.020  1.326
 8RK  C7   C6   single    1.503  0.020  1.503
 8RK  CL   C10  single    1.735  0.020  1.735
 8RK  C6   C5   single    1.522  0.020  1.522
 8RK  C5   N    single    1.445  0.020  1.445
 8RK  C9   C10  aromatic  1.393  0.020  1.393
 8RK  C9   C8   aromatic  1.378  0.020  1.378
 8RK  C10  C1   aromatic  1.397  0.020  1.397
 8RK  C8   N    single    1.382  0.020  1.382
 8RK  C8   C3   aromatic  1.384  0.020  1.384
 8RK  N    C4   single    1.363  0.020  1.363
 8RK  C1   C    single    1.499  0.020  1.499
 8RK  C1   C2   aromatic  1.400  0.020  1.400
 8RK  C3   C2   aromatic  1.371  0.020  1.371
 8RK  C3   O    single    1.363  0.020  1.363
 8RK  C4   O1   double    1.201  0.020  1.201
 8RK  C4   O    single    1.362  0.020  1.362
 8RK  C5   H1   single    0.970  0.020  1.090
 8RK  C5   H2   single    0.970  0.020  1.090
 8RK  C6   H3   single    0.970  0.020  1.090
 8RK  C6   H4   single    0.970  0.020  1.090
 8RK  C    H5   single    0.970  0.020  1.090
 8RK  C    H6   single    0.970  0.020  1.090
 8RK  C    H7   single    0.970  0.020  1.090
 8RK  C9   H8   single    0.930  0.020  1.080
 8RK  C2   H9   single    0.930  0.020  1.080
 8RK  O2   H10  single    0.850  0.020  0.980

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
 8RK  O    C4   O1   123.03  3.000
 8RK  O    C4   N    107.91  3.000
 8RK  O1   C4   N    129.06  3.000
 8RK  H2   C5   H1   107.01  3.000
 8RK  H2   C5   N    108.06  3.000
 8RK  H1   C5   N    108.06  3.000
 8RK  H2   C5   C6   111.18  3.000
 8RK  H1   C5   C6   111.26  3.000
 8RK  N    C5   C6   111.10  3.000
 8RK  H4   C6   H3   105.98  3.000
 8RK  H4   C6   C7   108.68  3.000
 8RK  H3   C6   C7   108.72  3.000
 8RK  H4   C6   C5   110.28  3.000
 8RK  H3   C6   C5   110.83  3.000
 8RK  C7   C6   C5   112.13  3.000
 8RK  O2   C7   O3   123.59  3.000
 8RK  O2   C7   C6   111.80  3.000
 8RK  O3   C7   C6   124.61  3.000
 8RK  N    C8   C3   105.90  3.000
 8RK  C3   C8   C9   120.94  3.000
 8RK  N    C8   C9   133.16  3.000
 8RK  C9   C10  C1   123.81  3.000
 8RK  C1   C10  CL   118.89  3.000
 8RK  C9   C10  CL   117.31  3.000
 8RK  C2   C1   C    120.04  3.000
 8RK  C2   C1   C10  118.23  3.000
 8RK  C    C1   C10  121.73  3.000
 8RK  H7   C    H6   107.90  3.000
 8RK  H7   C    H5   107.17  3.000
 8RK  H6   C    H5   107.84  3.000
 8RK  H7   C    C1   111.56  3.000
 8RK  H6   C    C1   110.69  3.000
 8RK  H5   C    C1   111.49  3.000
 8RK  H8   C9   C10  121.22  3.000
 8RK  H8   C9   C8   122.58  3.000
 8RK  C10  C9   C8   116.20  3.000
 8RK  O    C3   C2   128.34  3.000
 8RK  O    C3   C8   108.86  3.000
 8RK  C2   C3   C8   122.79  3.000
 8RK  H9   C2   C3   121.40  3.000
 8RK  H9   C2   C1   120.57  3.000
 8RK  C3   C2   C1   118.03  3.000
 8RK  C8   N    C5   126.58  3.000
 8RK  C8   N    C4   109.09  3.000
 8RK  C5   N    C4   124.14  3.000
 8RK  C3   O    C4   108.23  3.000
 8RK  H10  O2   C7   110.11  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
 8RK  CONST_01  C1   C10  C9   C8      0.00   0.0  0
 8RK  CONST_02  C1   C2   C3   C8      0.00   0.0  0
 8RK  CONST_03  C3   C8   C9   C10     0.00   0.0  0
 8RK  CONST_04  C3   C2   C1   C10     0.00   0.0  0
 8RK  CONST_05  C2   C1   C10  C9      0.00   0.0  0
 8RK  CONST_06  C2   C3   C8   C9      0.00   0.0  0
 8RK  CONST_07  CL   C10  C9   C8    180.00   0.0  0
 8RK  CONST_08  C2   C1   C10  CL    180.00   0.0  0
 8RK  CONST_09  C9   C10  C1   C     180.00   0.0  0
 8RK  CONST_10  C3   C2   C1   C     180.00   0.0  0
 8RK  CONST_11  H9   C2   C3   C8    180.00   0.0  0
 8RK  CONST_12  H8   C9   C10  C1    180.00   0.0  0
 8RK  CONST_13  H10  O2   C7   C6    180.00   0.0  0
 8RK  Var_01    C6   C5   N    C4    -91.00  30.0  3
 8RK  Var_02    H5   C    C1   C10    60.73  30.0  2
 8RK  Var_03    N    C5   C6   C7   -179.66  30.0  3
 8RK  Var_04    O3   C7   C6   C5      0.36  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
 8RK  plan-1  C4   0.020
 8RK  plan-1  C5   0.020
 8RK  plan-1  C8   0.020
 8RK  plan-1  C10  0.020
 8RK  plan-1  CL   0.020
 8RK  plan-1  C1   0.020
 8RK  plan-1  C    0.020
 8RK  plan-1  C9   0.020
 8RK  plan-1  C3   0.020
 8RK  plan-1  C2   0.020
 8RK  plan-1  N    0.020
 8RK  plan-1  O1   0.020
 8RK  plan-1  O    0.020
 8RK  plan-1  H8   0.020
 8RK  plan-1  H9   0.020
 8RK  plan-2  C6   0.020
 8RK  plan-2  C7   0.020
 8RK  plan-2  O3   0.020
 8RK  plan-2  O2   0.020
 8RK  plan-2  H10  0.020

