# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 17 22:15:45 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  26  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   0.667  -0.9630   2.2895  -0.1304
 8RK  C5   C   CH2    0  -0.311  -2.0940   0.1533  -0.7235
 8RK  C6   C   CH2    0  -0.596  -2.6871  -0.4854   0.5213
 8RK  C7   C   C      0   0.424  -3.9250  -1.3579   0.2428
 8RK  C8   C   CR56   0   0.326   0.3638   0.4994  -0.2424
 8RK  C10  C   CR6    0  -0.117   2.3145  -0.8114  -0.1259
 8RK  CL   CL  CL     0  -0.121   3.0789  -2.3603  -0.2989
 8RK  C1   C   CR6    0   0.148   3.0911   0.2839   0.2589
 8RK  C    C   CH3    0  -0.721   4.5602   0.1543   0.5270
 8RK  C9   C   CR16   0  -0.250   0.9474  -0.7411  -0.3829
 8RK  C3   C   CR56   0   0.333   1.1161   1.5985   0.1368
 8RK  C2   C   CR16   0  -0.394   2.4612   1.5270   0.3915
 8RK  N    N   NR5    0  -0.587  -0.9250   0.9605  -0.4177
 8RK  O1   O   O      0  -0.455  -1.8976   3.0461  -0.1452
 8RK  O    O   O      0  -0.470   0.3004   2.6867   0.1996
 8RK  O3   O   O      0  -0.605  -4.2910  -1.4633  -0.9440
 8RK  O2   O   OC    -1  -0.621  -4.4554  -1.8860   1.2392
 8RK  H1   H   HCH2   0   0.261  -1.7925  -0.6011  -1.4493
 8RK  H2   H   HCH2   0   0.267  -2.8172   0.7960  -1.2216
 8RK  H3   H   HCH2   0   0.240  -1.9301  -1.0979   1.0229
 8RK  H4   H   HCH2   0   0.242  -2.9565   0.2948   1.2396
 8RK  H5   H   HCH3   0   0.253   5.0996  -0.1906  -0.3561
 8RK  H6   H   HCH3   0   0.255   4.9828   1.1125   0.8232
 8RK  H7   H   HCH3   0   0.252   4.7603  -0.5608   1.3261
 8RK  H8   H   HCR6   0   0.299   0.3861  -1.6175  -0.6766
 8RK  H9   H   HCR6   0   0.283   3.0264   2.4008   0.6881

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   deloc     1.246  0.020  1.246
 8RK  C7   O2   deloc     1.246  0.020  1.246
 8RK  C7   C6   single    1.540  0.020  1.540
 8RK  CL   C10  single    1.736  0.020  1.736
 8RK  C6   C5   single    1.520  0.020  1.520
 8RK  C5   N    single    1.453  0.020  1.453
 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    1.380  0.020  1.380
 8RK  C8   C3   aromatic  1.385  0.020  1.385
 8RK  N    C4   single    1.360  0.020  1.360
 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    1.361  0.020  1.361
 8RK  C4   O1   double    1.202  0.020  1.202
 8RK  C4   O    single    1.365  0.020  1.365
 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

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   122.63  3.000
 8RK  O    C4   N    108.03  3.000
 8RK  O1   C4   N    129.34  3.000
 8RK  H2   C5   H1   106.74  3.000
 8RK  H2   C5   N    107.63  3.000
 8RK  H1   C5   N    107.59  3.000
 8RK  H2   C5   C6   111.34  3.000
 8RK  H1   C5   C6   111.27  3.000
 8RK  N    C5   C6   112.03  3.000
 8RK  H4   C6   H3   105.56  3.000
 8RK  H4   C6   C7   108.95  3.000
 8RK  H3   C6   C7   108.76  3.000
 8RK  H4   C6   C5   109.52  3.000
 8RK  H3   C6   C5   109.90  3.000
 8RK  C7   C6   C5   113.81  3.000
 8RK  O2   C7   O3   126.90  3.000
 8RK  O2   C7   C6   115.95  3.000
 8RK  O3   C7   C6   117.14  3.000
 8RK  N    C8   C3   106.08  3.000
 8RK  C3   C8   C9   120.82  3.000
 8RK  N    C8   C9   133.10  3.000
 8RK  C9   C10  C1   123.85  3.000
 8RK  C1   C10  CL   118.84  3.000
 8RK  C9   C10  CL   117.31  3.000
 8RK  C2   C1   C    120.05  3.000
 8RK  C2   C1   C10  118.18  3.000
 8RK  C    C1   C10  121.76  3.000
 8RK  H7   C    H6   107.85  3.000
 8RK  H7   C    H5   107.16  3.000
 8RK  H6   C    H5   107.86  3.000
 8RK  H7   C    C1   111.56  3.000
 8RK  H6   C    C1   110.68  3.000
 8RK  H5   C    C1   111.54  3.000
 8RK  H8   C9   C10  121.25  3.000
 8RK  H8   C9   C8   122.51  3.000
 8RK  C10  C9   C8   116.25  3.000
 8RK  O    C3   C2   128.39  3.000
 8RK  O    C3   C8   108.76  3.000
 8RK  C2   C3   C8   122.85  3.000
 8RK  H9   C2   C3   121.42  3.000
 8RK  H9   C2   C1   120.53  3.000
 8RK  C3   C2   C1   118.05  3.000
 8RK  C8   N    C5   126.33  3.000
 8RK  C8   N    C4   109.01  3.000
 8RK  C5   N    C4   124.38  3.000
 8RK  C3   O    C4   108.11  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  Var_01    C6  C5   N    C4    -91.13  30.0  3
 8RK  Var_02    H5  C    C1   C10    60.51  30.0  2
 8RK  Var_03    N   C5   C6   C7   -179.66  30.0  3
 8RK  Var_04    O3  C7   C6   C5      1.00  30.0  2

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

