# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 06:32:50 2022
#   Inital geometry file: a 61 line input string
#   Ligand name: 3-(4-hydroxyphenyl)-2-oxopropanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)C(=O)Cc1ccc(O)cc1
#
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
 ENO  ENO  '3-(4-hydroxyphenyl)-2-oxopropanoic acid'  ligand  20  13  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ENO
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
 ENO  O4   O  O      0  -0.385   1.3958  -0.0183   1.3439
 ENO  C9   C  CR16   0  -0.295  -0.4723  -1.1708  -1.2955
 ENO  C8   C  CR16   0  -0.371  -0.1478  -1.1441  -2.6449
 ENO  C7   C  CR6    0   0.336   0.0304   0.0749  -3.2922
 ENO  C6   C  CR16   0  -0.325  -0.1224   1.2574  -2.5721
 ENO  C5   C  CR16   0  -0.290  -0.4462   1.2090  -1.2258
 ENO  C4   C  CR6    0   0.145  -0.6297  -0.0011  -0.5610
 ENO  C3   C  CH2    0  -0.668  -0.9496  -0.0378   0.9008
 ENO  C2   C  C      0   0.246   0.2745  -0.0205   1.7908
 ENO  C1   C  C      0   0.347   0.0235  -0.0099   3.3269
 ENO  O2   O  O      0  -0.577  -1.1543  -0.1991   3.6748
 ENO  O1   O  OC    -1  -0.581   1.0225   0.1849   4.0316
 ENO  H9   H  HCR6   0   0.250  -0.6130  -2.1307  -0.8123
 ENO  H8   H  HCR6   0   0.267  -0.0354  -2.0749  -3.1900
 ENO  H6   H  HCR6   0   0.259   0.0139   2.2107  -3.0680
 ENO  H5   H  HCR6   0   0.248  -0.5662   2.1400  -0.6841
 ENO  HO3  H  HOH1   0   0.472   0.4395  -0.7101  -4.9858
 ENO  H31  H  HCH2   0   0.281  -1.5345  -0.9259   1.1562
 ENO  H32  H  HCH2   0   0.278  -1.5851   0.8058   1.1873
 ENO  O3   O  OH1    0  -0.636   0.3438   0.1683  -4.6025

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
 ENO  O4  C2   double    1.207  0.020  1.207
 ENO  C9  C8   aromatic  1.388  0.020  1.388
 ENO  C9  C4   aromatic  1.390  0.020  1.390
 ENO  C9  H9   single    0.930  0.020  1.080
 ENO  C8  C7   aromatic  1.392  0.020  1.392
 ENO  C8  H8   single    0.930  0.020  1.080
 ENO  C7  C6   aromatic  1.393  0.020  1.393
 ENO  C7  O3   single    1.350  0.020  1.350
 ENO  C6  C5   aromatic  1.386  0.020  1.386
 ENO  C6  H6   single    0.930  0.020  1.080
 ENO  C5  C4   aromatic  1.393  0.020  1.393
 ENO  C5  H5   single    0.930  0.020  1.080
 ENO  C4  C3   single    1.497  0.020  1.497
 ENO  O3  HO3  single    0.850  0.020  0.980
 ENO  C3  C2   single    1.514  0.020  1.514
 ENO  C3  H31  single    0.970  0.020  1.090
 ENO  C3  H32  single    0.970  0.020  1.090
 ENO  C2  C1   single    1.557  0.020  1.557
 ENO  C1  O2   deloc     1.243  0.020  1.243
 ENO  C1  O1   deloc     1.238  0.020  1.238

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
 ENO  H9   C9  C4   119.67  3.000
 ENO  H9   C9  C8   118.74  3.000
 ENO  C4   C9  C8   121.60  3.000
 ENO  H8   C8  C7   120.32  3.000
 ENO  H8   C8  C9   119.75  3.000
 ENO  C7   C8  C9   119.93  3.000
 ENO  O3   C7  C6   117.93  3.000
 ENO  O3   C7  C8   122.79  3.000
 ENO  C6   C7  C8   119.28  3.000
 ENO  H6   C6  C5   120.33  3.000
 ENO  H6   C6  C7   119.78  3.000
 ENO  C5   C6  C7   119.89  3.000
 ENO  H5   C5  C4   119.55  3.000
 ENO  H5   C5  C6   118.78  3.000
 ENO  C4   C5  C6   121.67  3.000
 ENO  C3   C4  C5   121.04  3.000
 ENO  C3   C4  C9   121.30  3.000
 ENO  C5   C4  C9   117.64  3.000
 ENO  H32  C3  H31  104.73  3.000
 ENO  H32  C3  C2   107.87  3.000
 ENO  H31  C3  C2   107.72  3.000
 ENO  H32  C3  C4   111.16  3.000
 ENO  H31  C3  C4   111.24  3.000
 ENO  C2   C3  C4   113.65  3.000
 ENO  C1   C2  C3   116.74  3.000
 ENO  C1   C2  O4   121.01  3.000
 ENO  C3   C2  O4   122.25  3.000
 ENO  O1   C1  O2   129.01  3.000
 ENO  O1   C1  C2   115.64  3.000
 ENO  O2   C1  C2   115.34  3.000
 ENO  HO3  O3  C7   110.25  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
 ENO  CONST_01  C6  C7  C8  C9     0.00   0.0  0
 ENO  CONST_02  C6  C5  C4  C9     0.00   0.0  0
 ENO  CONST_03  C5  C4  C9  C8     0.00   0.0  0
 ENO  CONST_04  C5  C6  C7  C8     0.00   0.0  0
 ENO  CONST_05  C4  C9  C8  C7     0.00   0.0  0
 ENO  CONST_06  C4  C5  C6  C7     0.00   0.0  0
 ENO  CONST_07  O3  C7  C8  C9   180.00   0.0  0
 ENO  CONST_08  C3  C4  C9  C8   180.00   0.0  0
 ENO  CONST_09  C3  C4  C5  C6   180.00   0.0  0
 ENO  CONST_10  O3  C7  C6  C5   180.00   0.0  0
 ENO  CONST_11  H5  C5  C4  C9   180.00   0.0  0
 ENO  CONST_12  H6  C6  C7  C8   180.00   0.0  0
 ENO  CONST_13  H9  C9  C8  C7   180.00   0.0  0
 ENO  CONST_14  H8  C8  C7  C6   180.00   0.0  0
 ENO  Var_01    C2  C3  C4  C9    91.49  30.0  2
 ENO  Var_02    C4  C3  C2  O4    -2.11  30.0  1
 ENO  Var_03    O2  C1  C2  O4  -170.47  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
 ENO  plan-1  C9  0.020
 ENO  plan-1  C8  0.020
 ENO  plan-1  C7  0.020
 ENO  plan-1  C6  0.020
 ENO  plan-1  C5  0.020
 ENO  plan-1  C4  0.020
 ENO  plan-1  C3  0.020
 ENO  plan-1  H9  0.020
 ENO  plan-1  H8  0.020
 ENO  plan-1  H6  0.020
 ENO  plan-1  H5  0.020
 ENO  plan-1  O3  0.020
 ENO  plan-2  O4  0.020
 ENO  plan-2  C3  0.020
 ENO  plan-2  C2  0.020
 ENO  plan-2  C1  0.020
 ENO  plan-3  C2  0.020
 ENO  plan-3  C1  0.020
 ENO  plan-3  O2  0.020
 ENO  plan-3  O1  0.020

