# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 21:59:27 2020
#   Inital geometry file: a 69 line input string
#   Ligand name: (2Z)-4-(2-bromo-4-hydroxyphenyl)-2-hydroxy-4-oxobut-2-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(c(Br)c1)C(=O)\C=C(O)\C(O)=O
#
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
 ENG  ENG  '(2Z)-4-(2-bromo-4-hydroxyphenyl)-2-hydroxy-4-oxobut-2-enoic acid'  ligand  22  16  .  2021-08-08  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ENG
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
 ENG  C10   C   CR16   0  -0.274  -0.5912   2.0117  -0.4588
 ENG  C15   C   CR6    0  -0.138  -1.8096   0.0571   0.1451
 ENG  C02   C   C      0   0.386   4.4069   0.5912   0.5636
 ENG  C04   C   C      0   0.227   3.1081  -0.0695   0.0725
 ENG  C06   C   C1     0  -0.529   1.8954   0.5477   0.1799
 ENG  C07   C   C      0   0.382   0.6997  -0.1006  -0.2803
 ENG  C09   C   CR6    0   0.036  -0.5832   0.6426  -0.1746
 ENG  C11   C   CR16   0  -0.326  -1.7463   2.7645  -0.4493
 ENG  C12   C   CR6    0   0.377  -2.9562   2.1543  -0.1265
 ENG  C14   C   CR16   0  -0.349  -2.9809   0.7955   0.1831
 ENG  O01   O   OC    -1  -0.579   5.4432  -0.0529   0.3542
 ENG  O03   O   O      0  -0.573   4.2701   1.6959   1.1119
 ENG  O05   O   OH1    0  -0.587   3.2524  -1.2634  -0.4529
 ENG  O08   O   O      0  -0.491   0.7191  -1.2397  -0.7686
 ENG  O13   O   OH1    0  -0.617  -4.0601   2.9108  -0.1170
 ENG  BR16  BR  BR     0  -0.029  -1.9502  -1.7596   0.6421
 ENG  H1    H   HCR6   0   0.279   0.3386   2.4980  -0.7236
 ENG  H3    H   H      0   0.268   1.8533   1.5192   0.6447
 ENG  H5    H   HCR6   0   0.279  -1.7164   3.8187  -0.6909
 ENG  H6    H   HCR6   0   0.298  -3.9177   0.3255   0.4575
 ENG  H8    H   HOH1   0   0.476   2.3445  -1.5773  -0.7052
 ENG  H9    H   HOH1   0   0.483  -4.8395   2.3845   0.0970

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
 ENG  BR16  C15  single    1.889  0.020  1.889
 ENG  O08   C07  double    1.239  0.020  1.239
 ENG  C15   C14  aromatic  1.385  0.020  1.385
 ENG  C15   C09  aromatic  1.396  0.020  1.396
 ENG  O05   C04  single    1.312  0.020  1.312
 ENG  C14   C12  aromatic  1.394  0.020  1.394
 ENG  C07   C09  single    1.486  0.020  1.486
 ENG  C07   C06  single    1.436  0.020  1.436
 ENG  C09   C10  aromatic  1.398  0.020  1.398
 ENG  C12   O13  single    1.338  0.020  1.338
 ENG  C12   C11  aromatic  1.393  0.020  1.393
 ENG  C06   C04  double    1.365  0.020  1.365
 ENG  C04   C02  single    1.538  0.020  1.538
 ENG  C10   C11  aromatic  1.379  0.020  1.379
 ENG  O03   C02  deloc     1.241  0.020  1.241
 ENG  C02   O01  deloc     1.238  0.020  1.238
 ENG  C10   H1   single    0.930  0.020  1.080
 ENG  C06   H3   single    0.930  0.020  1.080
 ENG  C11   H5   single    0.930  0.020  1.080
 ENG  C14   H6   single    0.930  0.020  1.080
 ENG  O05   H8   single    0.850  0.020  0.980
 ENG  O13   H9   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
 ENG  H1    C10  C11  118.44  3.000
 ENG  H1    C10  C09  118.99  3.000
 ENG  C11   C10  C09  122.55  3.000
 ENG  BR16  C15  C14  116.27  3.000
 ENG  C14   C15  C09  121.71  3.000
 ENG  BR16  C15  C09  121.94  3.000
 ENG  O03   C02  O01  129.07  3.000
 ENG  O01   C02  C04  115.43  3.000
 ENG  O03   C02  C04  115.50  3.000
 ENG  O05   C04  C06  122.72  3.000
 ENG  C06   C04  C02  122.07  3.000
 ENG  O05   C04  C02  115.21  3.000
 ENG  H3    C06  C07  120.84  3.000
 ENG  H3    C06  C04  118.44  3.000
 ENG  C07   C06  C04  120.69  3.000
 ENG  O08   C07  C09  120.07  3.000
 ENG  C09   C07  C06  118.05  3.000
 ENG  O08   C07  C06  121.88  3.000
 ENG  C07   C09  C15  124.39  3.000
 ENG  C07   C09  C10  118.69  3.000
 ENG  C15   C09  C10  116.88  3.000
 ENG  H5    C11  C12  120.17  3.000
 ENG  H5    C11  C10  120.48  3.000
 ENG  C12   C11  C10  119.34  3.000
 ENG  O13   C12  C14  122.34  3.000
 ENG  O13   C12  C11  118.06  3.000
 ENG  C14   C12  C11  119.60  3.000
 ENG  H6    C14  C12  119.64  3.000
 ENG  H6    C14  C15  120.46  3.000
 ENG  C12   C14  C15  119.90  3.000
 ENG  H8    O05  C04  106.78  3.000
 ENG  H9    O13  C12  111.08  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
 ENG  CONST_01  C14   C15  C09  C10     0.00   0.0  0
 ENG  CONST_02  C14   C12  C11  C10     0.00   0.0  0
 ENG  CONST_03  C11   C12  C14  C15     0.00   0.0  0
 ENG  CONST_04  C11   C10  C09  C15     0.00   0.0  0
 ENG  CONST_05  C12   C14  C15  C09     0.00   0.0  0
 ENG  CONST_06  C12   C11  C10  C09     0.00   0.0  0
 ENG  CONST_07  BR16  C15  C09  C10   180.00   0.0  0
 ENG  CONST_08  O13   C12  C11  C10   180.00   0.0  0
 ENG  CONST_09  O13   C12  C14  C15   180.00   0.0  0
 ENG  CONST_10  C14   C15  C09  C07   180.00   0.0  0
 ENG  CONST_11  C11   C10  C09  C07   180.00   0.0  0
 ENG  CONST_12  BR16  C15  C14  C12   180.00   0.0  0
 ENG  CONST_13  H1    C10  C09  C15   180.00   0.0  0
 ENG  CONST_14  H6    C14  C15  C09   180.00   0.0  0
 ENG  CONST_15  H5    C11  C10  C09   180.00   0.0  0
 ENG  Var_01    O08   C07  C09  C10  -139.74  30.0  2
 ENG  Var_02    C09   C07  C06  C04  -178.08  30.0  2
 ENG  Var_03    C07   C06  C04  C02  -179.57   0.0  2
 ENG  Var_04    O03   C02  C04  C06     2.83  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
 ENG  plan-1  C10   0.020
 ENG  plan-1  C15   0.020
 ENG  plan-1  C07   0.020
 ENG  plan-1  C09   0.020
 ENG  plan-1  C11   0.020
 ENG  plan-1  C12   0.020
 ENG  plan-1  C14   0.020
 ENG  plan-1  O13   0.020
 ENG  plan-1  BR16  0.020
 ENG  plan-1  H1    0.020
 ENG  plan-1  H5    0.020
 ENG  plan-1  H6    0.020
 ENG  plan-2  C06   0.020
 ENG  plan-2  C07   0.020
 ENG  plan-2  C09   0.020
 ENG  plan-2  O08   0.020
 ENG  plan-3  C02   0.020
 ENG  plan-3  C04   0.020
 ENG  plan-3  O01   0.020
 ENG  plan-3  O03   0.020
 ENG  plan-4  C02   0.020
 ENG  plan-4  C04   0.020
 ENG  plan-4  C06   0.020
 ENG  plan-4  C07   0.020
 ENG  plan-4  O05   0.020
 ENG  plan-4  H3    0.020

