# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 18 12:31:39 2020
#   Inital geometry file: a 61 line input string
#   Ligand name: (4-hydroxy-3-nitrophenyl)acetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)Cc1ccc(O)c(c1)[N+]([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
 NPA  NPA  '(4-hydroxy-3-nitrophenyl)acetic acid'  ligand  21  14  .  2021-08-15  2021-08-15  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_NPA
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
 NPA  C1   C  CR6    0   0.129   0.3643  -0.6437   0.9898
 NPA  C2   C  CR16   0  -0.278  -0.5907  -0.4923   0.0044
 NPA  C3   C  CR6    0   0.171  -0.2273  -0.2084  -1.3091
 NPA  C4   C  CR6    0   0.260   1.1169  -0.0439  -1.6714
 NPA  C5   C  CR16   0  -0.320   2.0710  -0.1834  -0.6622
 NPA  C6   C  CR16   0  -0.228   1.7021  -0.4812   0.6329
 NPA  C7   C  CH2    0  -0.689  -0.0295  -0.9487   2.4019
 NPA  C8   C  C      0   0.500  -0.2418   0.3037   3.2186
 NPA  N1   N  N      1   0.352  -1.2888  -0.0873  -2.2842
 NPA  O1   O  O     -1  -0.254  -1.0424  -0.3345  -3.4407
 NPA  O2   O  O      0  -0.496  -2.3834   0.2456  -1.8862
 NPA  O3   O  OH1    0  -0.641   1.4573   0.2661  -2.9207
 NPA  O4   O  O      0  -0.259  -0.1184   1.4266   2.8030
 NPA  O5   O  OH1    0  -0.633  -0.5857   0.0141   4.4671
 NPA  H2   H  HCR6   0   0.290  -1.6370  -0.6155   0.2493
 NPA  H5   H  HCR6   0   0.291   3.1189  -0.0560  -0.9064
 NPA  H6   H  HCR6   0   0.276   2.4756  -0.5897   1.3831
 NPA  H71  H  HCH2   0   0.283   0.7314  -1.5577   2.8975
 NPA  H72  H  HCH2   0   0.298  -0.9485  -1.5399   2.4341
 NPA  HO3  H  HOH1   0   0.482   2.4094   0.4141  -2.9769
 NPA  HO5  H  HOH1   0   0.467  -0.7179   0.8287   4.9752

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
 NPA  C1  C2   aromatic  1.380  0.020  1.380
 NPA  C1  C6   aromatic  1.394  0.020  1.394
 NPA  C1  C7   single    1.497  0.020  1.497
 NPA  C2  C3   aromatic  1.392  0.020  1.392
 NPA  C2  H2   single    0.930  0.020  1.080
 NPA  C3  C4   aromatic  1.402  0.020  1.402
 NPA  C3  N1   single    1.446  0.020  1.446
 NPA  C4  C5   aromatic  1.396  0.020  1.396
 NPA  C4  O3   single    1.331  0.020  1.331
 NPA  C5  C6   aromatic  1.379  0.020  1.379
 NPA  C5  H5   single    0.930  0.020  1.080
 NPA  C6  H6   single    0.930  0.020  1.080
 NPA  C7  C8   single    1.510  0.020  1.510
 NPA  C7  H71  single    0.970  0.020  1.090
 NPA  C7  H72  single    0.970  0.020  1.090
 NPA  C8  O4   double    1.204  0.020  1.204
 NPA  C8  O5   single    1.327  0.020  1.327
 NPA  N1  O1   single    1.208  0.020  1.208
 NPA  N1  O2   double    1.211  0.020  1.211
 NPA  O3  HO3  single    0.850  0.020  0.980
 NPA  O5  HO5  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
 NPA  C7   C1  C6   121.16  3.000
 NPA  C7   C1  C2   120.90  3.000
 NPA  C6   C1  C2   117.93  3.000
 NPA  H2   C2  C3   119.29  3.000
 NPA  H2   C2  C1   119.68  3.000
 NPA  C3   C2  C1   121.02  3.000
 NPA  N1   C3  C4   121.31  3.000
 NPA  N1   C3  C2   117.49  3.000
 NPA  C4   C3  C2   121.20  3.000
 NPA  O3   C4  C5   121.80  3.000
 NPA  O3   C4  C3   121.00  3.000
 NPA  C5   C4  C3   117.18  3.000
 NPA  H5   C5  C6   119.72  3.000
 NPA  H5   C5  C4   119.10  3.000
 NPA  C6   C5  C4   121.18  3.000
 NPA  H6   C6  C5   118.75  3.000
 NPA  H6   C6  C1   119.77  3.000
 NPA  C5   C6  C1   121.48  3.000
 NPA  H72  C7  H71  105.69  3.000
 NPA  H72  C7  C8   108.32  3.000
 NPA  H71  C7  C8   108.34  3.000
 NPA  H72  C7  C1   111.04  3.000
 NPA  H71  C7  C1   110.97  3.000
 NPA  C8   C7  C1   112.21  3.000
 NPA  O5   C8  O4   123.71  3.000
 NPA  O5   C8  C7   111.36  3.000
 NPA  O4   C8  C7   124.92  3.000
 NPA  O2   N1  O1   123.71  3.000
 NPA  O2   N1  C3   117.69  3.000
 NPA  O1   N1  C3   118.59  3.000
 NPA  HO3  O3  C4   110.03  3.000
 NPA  HO5  O5  C8   110.20  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
 NPA  CONST_01  C4   C3  C2  C1    0.00   0.0  0
 NPA  CONST_02  C4   C5  C6  C1    0.00   0.0  0
 NPA  CONST_03  C5   C6  C1  C2    0.00   0.0  0
 NPA  CONST_04  C5   C4  C3  C2    0.00   0.0  0
 NPA  CONST_05  C6   C1  C2  C3    0.00   0.0  0
 NPA  CONST_06  C6   C5  C4  C3    0.00   0.0  0
 NPA  CONST_07  N1   C3  C2  C1  180.00   0.0  0
 NPA  CONST_08  O3   C4  C3  C2  180.00   0.0  0
 NPA  CONST_09  C7   C1  C2  C3  180.00   0.0  0
 NPA  CONST_10  N1   C3  C4  C5  180.00   0.0  0
 NPA  CONST_11  C7   C1  C6  C5  180.00   0.0  0
 NPA  CONST_12  O3   C4  C5  C6  180.00   0.0  0
 NPA  CONST_13  H5   C5  C6  C1  180.00   0.0  0
 NPA  CONST_14  H6   C6  C1  C2  180.00   0.0  0
 NPA  CONST_15  H2   C2  C3  C4  180.00   0.0  0
 NPA  CONST_20  HO5  O5  C8  C7  180.00   0.0  0
 NPA  Var_01    C8   C7  C1  C2  -90.26  30.0  2
 NPA  Var_02    O4   C8  C7  C1    0.20  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
 NPA  plan-1  C1   0.020
 NPA  plan-1  C2   0.020
 NPA  plan-1  C3   0.020
 NPA  plan-1  C4   0.020
 NPA  plan-1  C5   0.020
 NPA  plan-1  C6   0.020
 NPA  plan-1  C7   0.020
 NPA  plan-1  N1   0.020
 NPA  plan-1  O3   0.020
 NPA  plan-1  H2   0.020
 NPA  plan-1  H5   0.020
 NPA  plan-1  H6   0.020
 NPA  plan-2  C3   0.020
 NPA  plan-2  N1   0.020
 NPA  plan-2  O1   0.020
 NPA  plan-2  O2   0.020
 NPA  plan-3  C7   0.020
 NPA  plan-3  C8   0.020
 NPA  plan-3  O4   0.020
 NPA  plan-3  O5   0.020
 NPA  plan-3  HO5  0.020

