# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 02:57:45 2022
#   Inital geometry file: a 64 line input string
#   Ligand name: 3-azanylnaphthalene-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1cc2ccccc2cc1C(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
 NYE  NYE  '3-azanylnaphthalene-2-carboxylic acid'  ligand  22  14  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_NYE
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
 NYE  C2   C  CR16   0  -0.279  18.7466  5.5386  -1.2831
 NYE  C3   C  CR16   0  -0.309  19.8904  5.0241  -1.8321
 NYE  C4   C  CR66   0   0.114  20.8546  5.8715  -2.4242
 NYE  C5   C  CR66   0   0.131  20.6333  7.2729  -2.4498
 NYE  C6   C  CR16   0  -0.428  21.5954  8.1046  -3.0464
 NYE  C7   C  CR6    0   0.295  22.7587  7.6015  -3.6074
 NYE  O    O  O      0  -0.571  24.2856  4.2928  -4.1673
 NYE  O1   O  OC    -1  -0.593  25.2154  6.2944  -4.4241
 NYE  C8   C  CR6    0  -0.176  22.9952  6.1826  -3.5692
 NYE  N    N  NH2    0  -0.871  23.6437  8.4347  -4.2322
 NYE  C    C  CR16   0  -0.331  19.4408  7.7782  -1.8718
 NYE  C9   C  CR16   0  -0.366  22.0460  5.3766  -2.9947
 NYE  C1   C  CR16   0  -0.256  18.5248  6.9333  -1.3059
 NYE  H2   H  HCR6   0   0.244  18.0121  4.8840  -0.8325
 NYE  H3   H  HCR6   0   0.244  20.0720  3.9554  -1.8190
 NYE  H4   H  HCR6   0   0.237  21.4168  9.1749  -3.0729
 NYE  H8   H  HNH2   0   0.366  23.6113  9.4075  -3.9772
 NYE  H7   H  HNH2   0   0.385  24.5593  8.0227  -4.3716
 NYE  H    H  HCR6   0   0.241  19.2620  8.8471  -1.8845
 NYE  H5   H  HCR6   0   0.239  22.2229  4.3082  -2.9711
 NYE  H1   H  HCR6   0   0.247  17.6194  7.3360  -0.8692
 NYE  C10  C  C      0   0.435  24.2710  5.5334  -4.1043

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
 NYE  O1   C10  deloc     1.254  0.020  1.254
 NYE  N    C7   single    1.367  0.020  1.367
 NYE  O    C10  deloc     1.242  0.020  1.242
 NYE  C10  C8   single    1.528  0.020  1.528
 NYE  C7   C8   aromatic  1.439  0.020  1.439
 NYE  C7   C6   aromatic  1.386  0.020  1.386
 NYE  C8   C9   aromatic  1.371  0.020  1.371
 NYE  C6   C5   aromatic  1.405  0.020  1.405
 NYE  C9   C4   aromatic  1.411  0.020  1.411
 NYE  C5   C4   aromatic  1.419  0.020  1.419
 NYE  C5   C    aromatic  1.418  0.020  1.418
 NYE  C4   C3   aromatic  1.414  0.020  1.414
 NYE  C    C1   aromatic  1.369  0.020  1.369
 NYE  C3   C2   aromatic  1.369  0.020  1.369
 NYE  C1   C2   aromatic  1.412  0.020  1.412
 NYE  C2   H2   single    0.930  0.020  1.080
 NYE  C3   H3   single    0.930  0.020  1.080
 NYE  C6   H4   single    0.930  0.020  1.080
 NYE  N    H8   single    0.890  0.020  1.040
 NYE  N    H7   single    0.890  0.020  1.040
 NYE  C    H    single    0.930  0.020  1.080
 NYE  C9   H5   single    0.930  0.020  1.080
 NYE  C1   H1   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
 NYE  H2   C2   C1   119.83  3.000
 NYE  H2   C2   C3   120.44  3.000
 NYE  C1   C2   C3   119.72  3.000
 NYE  H3   C3   C4   118.80  3.000
 NYE  H3   C3   C2   120.37  3.000
 NYE  C4   C3   C2   120.83  3.000
 NYE  C9   C4   C5   118.09  3.000
 NYE  C5   C4   C3   119.55  3.000
 NYE  C9   C4   C3   122.36  3.000
 NYE  C    C5   C6   122.55  3.000
 NYE  C    C5   C4   118.40  3.000
 NYE  C6   C5   C4   119.05  3.000
 NYE  H4   C6   C7   119.09  3.000
 NYE  H4   C6   C5   118.78  3.000
 NYE  C7   C6   C5   122.13  3.000
 NYE  N    C7   C8   120.45  3.000
 NYE  C8   C7   C6   119.02  3.000
 NYE  N    C7   C6   120.48  3.000
 NYE  C9   C8   C10  118.35  3.000
 NYE  C9   C8   C7   118.48  3.000
 NYE  C10  C8   C7   123.15  3.000
 NYE  H7   N    H8   117.19  3.000
 NYE  H7   N    C7   113.58  3.000
 NYE  H8   N    C7   116.92  3.000
 NYE  H    C    C1   120.21  3.000
 NYE  H    C    C5   119.04  3.000
 NYE  C1   C    C5   120.75  3.000
 NYE  H5   C9   C8   118.41  3.000
 NYE  H5   C9   C4   118.37  3.000
 NYE  C8   C9   C4   123.22  3.000
 NYE  H1   C1   C    119.79  3.000
 NYE  H1   C1   C2   119.47  3.000
 NYE  C    C1   C2   120.74  3.000
 NYE  C8   C10  O1   117.39  3.000
 NYE  C8   C10  O    116.86  3.000
 NYE  O1   C10  O    125.74  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
 NYE  CONST_01  C9   C4   C3  C2  180.00   0.0  0
 NYE  CONST_02  C5   C4   C3  C2    0.00   0.0  0
 NYE  CONST_03  C5   C    C1  C2    0.00   0.0  0
 NYE  CONST_04  C8   C9   C4  C3  180.00   0.0  0
 NYE  CONST_05  C6   C5   C4  C3  180.00   0.0  0
 NYE  CONST_06  C    C5   C4  C3    0.00   0.0  0
 NYE  CONST_07  C    C1   C2  C3    0.00   0.0  0
 NYE  CONST_08  C7   C8   C9  C4    0.00   0.0  0
 NYE  CONST_09  C7   C6   C5  C4    0.00   0.0  0
 NYE  CONST_10  C1   C    C5  C4    0.00   0.0  0
 NYE  CONST_11  C1   C2   C3  C4    0.00   0.0  0
 NYE  CONST_12  C8   C7   C6  C5    0.00   0.0  0
 NYE  CONST_13  C8   C9   C4  C5    0.00   0.0  0
 NYE  CONST_14  C9   C8   C7  C6    0.00   0.0  0
 NYE  CONST_15  C9   C4   C5  C6    0.00   0.0  0
 NYE  CONST_16  C1   C    C5  C6  180.00   0.0  0
 NYE  CONST_17  C    C5   C6  C7  180.00   0.0  0
 NYE  CONST_18  C9   C4   C5  C   180.00   0.0  0
 NYE  CONST_19  C10  C8   C9  C4  180.00   0.0  0
 NYE  CONST_20  N    C7   C6  C5  180.00   0.0  0
 NYE  CONST_21  C10  C8   C7  C6  180.00   0.0  0
 NYE  CONST_22  C9   C8   C7  N   180.00   0.0  0
 NYE  CONST_23  H    C    C1  C2  180.00   0.0  0
 NYE  CONST_24  H5   C9   C4  C3    0.00   0.0  0
 NYE  CONST_25  H1   C1   C2  C3  180.00   0.0  0
 NYE  CONST_26  H4   C6   C5  C4  180.00   0.0  0
 NYE  CONST_27  H2   C2   C3  C4  180.00   0.0  0
 NYE  CONST_28  H3   C3   C4  C5  180.00   0.0  0
 NYE  Var_01    O1   C10  C8  C7    9.66  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
 NYE  plan-1  C2   0.020
 NYE  plan-1  C3   0.020
 NYE  plan-1  C4   0.020
 NYE  plan-1  C5   0.020
 NYE  plan-1  C6   0.020
 NYE  plan-1  C7   0.020
 NYE  plan-1  C8   0.020
 NYE  plan-1  N    0.020
 NYE  plan-1  C    0.020
 NYE  plan-1  C9   0.020
 NYE  plan-1  C1   0.020
 NYE  plan-1  H2   0.020
 NYE  plan-1  H3   0.020
 NYE  plan-1  H4   0.020
 NYE  plan-1  H    0.020
 NYE  plan-1  H5   0.020
 NYE  plan-1  H1   0.020
 NYE  plan-1  C10  0.020
 NYE  plan-2  C7   0.020
 NYE  plan-2  N    0.020
 NYE  plan-2  H8   0.020
 NYE  plan-2  H7   0.020
 NYE  plan-3  O    0.020
 NYE  plan-3  O1   0.020
 NYE  plan-3  C8   0.020
 NYE  plan-3  C10  0.020

