# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 14:55:50 2020
#   Inital geometry file: a 91 line input string
#   Ligand name: 6-(2-ethylphenyl)-3-hydroxy-4-oxo-1,4-dihydropyridine-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1ccccc1C2=CC(=O)C(=C(N2)C(O)=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
 HNY  HNY  '6-(2-ethylphenyl)-3-hydroxy-4-oxo-1,4-dihydropyridine-2-carboxylic acid'  ligand  31  19  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HNY
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
 HNY  OAB  O  O      0  -0.598   1.8863   2.4815   1.3954
 HNY  CAM  C  C      0   0.420   2.6114   1.5517   0.9869
 HNY  OAD  O  OC    -1  -0.561   3.8465   1.4947   0.9674
 HNY  CAR  C  CR6    0   0.015   1.8442   0.3479   0.4574
 HNY  NAL  N  NR16   0  -0.668   0.4865   0.4654   0.5511
 HNY  CAP  C  CR6    0   0.192   2.3516  -0.7989  -0.0752
 HNY  OAE  O  OH1    0  -0.618   3.6579  -1.0367  -0.2339
 HNY  CAS  C  CR6    0   0.360   1.4770  -1.8758  -0.5243
 HNY  OAC  O  O      0  -0.546   2.0016  -2.9006  -1.0040
 HNY  CAJ  C  CR16   0  -0.506   0.0826  -1.6451  -0.3761
 HNY  CAO  C  CR6    0   0.313  -0.3831  -0.4702   0.1550
 HNY  CAQ  C  CR6    0  -0.013  -1.8263  -0.1854   0.3304
 HNY  CAI  C  CR16   0  -0.258  -2.5242  -0.8979   1.3026
 HNY  CAG  C  CR16   0  -0.263  -3.8753  -0.6702   1.5137
 HNY  CAF  C  CR16   0  -0.240  -4.5345   0.2768   0.7434
 HNY  CAH  C  CR16   0  -0.305  -3.8424   0.9793  -0.2323
 HNY  CAN  C  CR6    0   0.117  -2.4848   0.7649  -0.4609
 HNY  CAK  C  CH2    0  -0.524  -1.7992   1.4840  -1.5925
 HNY  CAA  C  CH3    0  -0.655  -1.7595   0.6352  -2.8632
 HNY  H2   H  HOH1   0   0.454   3.6977  -1.9219  -0.6406
 HNY  H3   H  HCR6   0   0.264  -0.6228  -2.3984  -0.6998
 HNY  H5   H  HCR6   0   0.258  -1.9990  -1.6308   1.9025
 HNY  H6   H  HCR6   0   0.259  -4.4065  -1.2244   2.2760
 HNY  H7   H  HCR6   0   0.259  -5.5882   0.4684   0.8995
 HNY  H8   H  HCR6   0   0.252  -4.3680   1.7095  -0.8364
 HNY  H9   H  HCH2   0   0.250  -2.3312   2.4148  -1.7986
 HNY  H10  H  HCH2   0   0.240  -0.7834   1.7713  -1.3179
 HNY  H11  H  HCH3   0   0.230  -1.2182  -0.2974  -2.7012
 HNY  H12  H  HCH3   0   0.228  -2.7663   0.3828  -3.1975
 HNY  H13  H  HCH3   0   0.235  -1.2615   1.1731  -3.6702
 HNY  H14  H  HNR6   0   0.410   0.1737   1.3352   0.9693

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
 HNY  OAC  CAS  double    1.247  0.020  1.247
 HNY  OAE  CAP  single    1.337  0.020  1.337
 HNY  CAS  CAP  single    1.458  0.020  1.458
 HNY  CAS  CAJ  single    1.421  0.020  1.421
 HNY  CAP  CAR  double    1.363  0.020  1.363
 HNY  CAJ  CAO  double    1.371  0.020  1.371
 HNY  OAB  CAM  deloc     1.248  0.020  1.248
 HNY  CAR  CAM  single    1.522  0.020  1.522
 HNY  CAR  NAL  single    1.366  0.020  1.366
 HNY  CAM  OAD  deloc     1.237  0.020  1.237
 HNY  CAA  CAK  single    1.529  0.020  1.529
 HNY  CAO  NAL  single    1.337  0.020  1.337
 HNY  CAO  CAQ  single    1.482  0.020  1.482
 HNY  CAK  CAN  single    1.506  0.020  1.506
 HNY  CAQ  CAN  aromatic  1.401  0.020  1.401
 HNY  CAQ  CAI  aromatic  1.393  0.020  1.393
 HNY  CAN  CAH  aromatic  1.393  0.020  1.393
 HNY  CAI  CAG  aromatic  1.386  0.020  1.386
 HNY  CAH  CAF  aromatic  1.387  0.020  1.387
 HNY  CAG  CAF  aromatic  1.387  0.020  1.387
 HNY  OAE  H2   single    0.850  0.020  0.980
 HNY  CAJ  H3   single    0.930  0.020  1.080
 HNY  CAI  H5   single    0.930  0.020  1.080
 HNY  CAG  H6   single    0.930  0.020  1.080
 HNY  CAF  H7   single    0.930  0.020  1.080
 HNY  CAH  H8   single    0.930  0.020  1.080
 HNY  CAK  H9   single    0.970  0.020  1.090
 HNY  CAK  H10  single    0.970  0.020  1.090
 HNY  CAA  H11  single    0.970  0.020  1.090
 HNY  CAA  H12  single    0.970  0.020  1.090
 HNY  CAA  H13  single    0.970  0.020  1.090
 HNY  NAL  H14  single    0.860  0.020  1.020

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
 HNY  CAR  CAM  OAD  117.48  3.000
 HNY  OAD  CAM  OAB  128.31  3.000
 HNY  CAR  CAM  OAB  114.21  3.000
 HNY  CAP  CAR  NAL  117.99  3.000
 HNY  NAL  CAR  CAM  114.14  3.000
 HNY  CAP  CAR  CAM  127.87  3.000
 HNY  H14  NAL  CAO  121.43  3.000
 HNY  H14  NAL  CAR  114.11  3.000
 HNY  CAO  NAL  CAR  124.46  3.000
 HNY  CAS  CAP  OAE  114.71  3.000
 HNY  CAS  CAP  CAR  121.25  3.000
 HNY  OAE  CAP  CAR  124.04  3.000
 HNY  H2   OAE  CAP  104.52  3.000
 HNY  CAJ  CAS  OAC  125.89  3.000
 HNY  CAJ  CAS  CAP  115.88  3.000
 HNY  OAC  CAS  CAP  118.23  3.000
 HNY  H3   CAJ  CAO  119.43  3.000
 HNY  H3   CAJ  CAS  119.71  3.000
 HNY  CAO  CAJ  CAS  120.85  3.000
 HNY  CAQ  CAO  CAJ  122.79  3.000
 HNY  CAQ  CAO  NAL  117.64  3.000
 HNY  CAJ  CAO  NAL  119.57  3.000
 HNY  CAN  CAQ  CAI  120.38  3.000
 HNY  CAI  CAQ  CAO  118.19  3.000
 HNY  CAN  CAQ  CAO  121.42  3.000
 HNY  H5   CAI  CAG  119.96  3.000
 HNY  H5   CAI  CAQ  119.33  3.000
 HNY  CAG  CAI  CAQ  120.70  3.000
 HNY  H6   CAG  CAF  120.50  3.000
 HNY  H6   CAG  CAI  120.11  3.000
 HNY  CAF  CAG  CAI  119.38  3.000
 HNY  H7   CAF  CAH  119.84  3.000
 HNY  H7   CAF  CAG  120.22  3.000
 HNY  CAH  CAF  CAG  119.94  3.000
 HNY  H8   CAH  CAN  119.00  3.000
 HNY  H8   CAH  CAF  119.42  3.000
 HNY  CAN  CAH  CAF  121.58  3.000
 HNY  CAK  CAN  CAH  119.57  3.000
 HNY  CAH  CAN  CAQ  118.01  3.000
 HNY  CAK  CAN  CAQ  122.30  3.000
 HNY  H10  CAK  H9   106.07  3.000
 HNY  H10  CAK  CAA  109.35  3.000
 HNY  H9   CAK  CAA  109.22  3.000
 HNY  H10  CAK  CAN  111.14  3.000
 HNY  H9   CAK  CAN  109.09  3.000
 HNY  CAA  CAK  CAN  111.80  3.000
 HNY  H13  CAA  H12  108.00  3.000
 HNY  H13  CAA  H11  107.77  3.000
 HNY  H12  CAA  H11  107.81  3.000
 HNY  H13  CAA  CAK  110.69  3.000
 HNY  H12  CAA  CAK  111.06  3.000
 HNY  H11  CAA  CAK  111.36  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
 HNY  CONST_01  CAF  CAH  CAN  CAQ    0.00   0.0  0
 HNY  CONST_02  CAF  CAG  CAI  CAQ    0.00   0.0  0
 HNY  CONST_03  CAH  CAN  CAQ  CAI    0.00   0.0  0
 HNY  CONST_04  CAH  CAF  CAG  CAI    0.00   0.0  0
 HNY  CONST_05  CAN  CAQ  CAI  CAG    0.00   0.0  0
 HNY  CONST_06  CAN  CAH  CAF  CAG    0.00   0.0  0
 HNY  CONST_07  CAH  CAN  CAQ  CAO  180.00   0.0  0
 HNY  CONST_08  CAG  CAI  CAQ  CAO  180.00   0.0  0
 HNY  CONST_09  CAK  CAN  CAQ  CAO    0.00   0.0  0
 HNY  CONST_10  CAK  CAN  CAQ  CAI  180.00   0.0  0
 HNY  CONST_11  CAK  CAN  CAH  CAF  180.00   0.0  0
 HNY  CONST_12  H5   CAI  CAQ  CAO    0.00   0.0  0
 HNY  CONST_13  H8   CAH  CAN  CAQ  180.00   0.0  0
 HNY  CONST_14  H6   CAG  CAI  CAQ  180.00   0.0  0
 HNY  CONST_15  H7   CAF  CAG  CAI  180.00   0.0  0
 HNY  Var_01    CAN  CAQ  CAO  NAL   71.21  30.0  2
 HNY  Var_02    CAP  CAR  CAM  OAB  178.60  30.0  2
 HNY  Var_03    CAA  CAK  CAN  CAQ   81.37  30.0  1
 HNY  Var_04    H11  CAA  CAK  CAN  -60.23  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
 HNY  plan-1  CAM  0.020
 HNY  plan-1  CAR  0.020
 HNY  plan-1  NAL  0.020
 HNY  plan-1  CAP  0.020
 HNY  plan-1  OAE  0.020
 HNY  plan-1  CAS  0.020
 HNY  plan-1  OAC  0.020
 HNY  plan-1  CAJ  0.020
 HNY  plan-1  CAO  0.020
 HNY  plan-1  CAQ  0.020
 HNY  plan-1  H3   0.020
 HNY  plan-1  H14  0.020
 HNY  plan-2  CAO  0.020
 HNY  plan-2  CAQ  0.020
 HNY  plan-2  CAI  0.020
 HNY  plan-2  CAG  0.020
 HNY  plan-2  CAF  0.020
 HNY  plan-2  CAH  0.020
 HNY  plan-2  CAN  0.020
 HNY  plan-2  CAK  0.020
 HNY  plan-2  H5   0.020
 HNY  plan-2  H6   0.020
 HNY  plan-2  H7   0.020
 HNY  plan-2  H8   0.020
 HNY  plan-3  OAB  0.020
 HNY  plan-3  CAM  0.020
 HNY  plan-3  OAD  0.020
 HNY  plan-3  CAR  0.020

