# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 10 20:47:26 2020
#   Inital geometry file: a 78 line input string
#   Ligand name: ~{N}-ethyl-4-oxidanyl-2-oxidanylidene-1~{H}-1,7-naphthyridine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)C1=C(O)c2ccncc2NC1=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
 6QN  6QN  ~{N}-ethyl-4-oxidanyl-2-oxidanylidene-1~{H}-1,7-naphthyridine-3-carboxamide  ligand  28  17  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_6QN
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
 6QN  C4   C  C     0   0.674  -1.9160  -0.6494   0.0447
 6QN  C6   C  CR6   0  -0.482  -0.5529  -0.0837   0.0291
 6QN  C7   C  CR6   0   0.502   0.5020  -0.9815   0.0154
 6QN  C8   C  CR66  0   0.033   1.8637  -0.5014   0.0018
 6QN  C9   C  CR16  0  -0.347   2.9822  -1.3381  -0.0114
 6QN  C10  C  CR16  0  -0.081   4.2347  -0.7668  -0.0231
 6QN  C12  C  CR16  0  -0.113   3.3885   1.3540  -0.0097
 6QN  C13  C  CR66  0   0.295   2.0702   0.8759   0.0022
 6QN  N3   N  NH1   0  -0.659  -2.9645   0.1565   0.0620
 6QN  C1   C  CH3   0  -0.704  -5.3056   0.8265   0.0913
 6QN  C2   C  CH2   0  -0.265  -4.3309  -0.3340   0.0791
 6QN  O5   O  O     0  -0.577  -2.0598  -1.8946   0.0414
 6QN  N11  N  N     0  -0.380   4.4309   0.5566  -0.0219
 6QN  N14  N  NR16  0  -0.760   1.0061   1.7288   0.0142
 6QN  C16  C  CR6   0   0.555  -0.3075   1.3463   0.0282
 6QN  O17  O  O     0  -0.496  -1.1866   2.2069   0.0385
 6QN  O18  O  OH1   0  -0.587   0.3307  -2.2718   0.0147
 6QN  H25  H  HCR6  0   0.285   2.8748  -2.4133  -0.0126
 6QN  H26  H  HCR6  0   0.274   5.1207  -1.3891  -0.0324
 6QN  H27  H  HCR6  0   0.289   3.5706   2.4241  -0.0094
 6QN  H24  H  HNH1  0   0.422  -2.7840   1.1536   0.0607
 6QN  H19  H  HCH3  0   0.237  -5.1722   1.4518   0.9748
 6QN  H20  H  HCH3  0   0.237  -5.1913   1.4537  -0.7934
 6QN  H21  H  HCH3  0   0.248  -6.3267   0.4487   0.1021
 6QN  H23  H  HCH2  0   0.242  -4.5060  -0.9639  -0.7957
 6QN  H22  H  HCH2  0   0.242  -4.4836  -0.9642   0.9579
 6QN  H15  H  HNR6  0   0.423   1.1828   2.7253   0.0126
 6QN  H28  H  HOH1  0   0.493  -0.6906  -2.4021   0.0245

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
 6QN  C1   C2   single    1.516  0.020  1.516
 6QN  C2   N3   single    1.452  0.020  1.452
 6QN  N3   C4   single    1.323  0.020  1.323
 6QN  O17  C16  double    1.230  0.020  1.230
 6QN  C4   O5   double    1.254  0.020  1.254
 6QN  C4   C6   single    1.476  0.020  1.476
 6QN  C16  C6   single    1.451  0.020  1.451
 6QN  C16  N14  single    1.368  0.020  1.368
 6QN  C6   C7   double    1.385  0.020  1.385
 6QN  N14  C13  single    1.364  0.020  1.364
 6QN  C7   O18  single    1.302  0.020  1.302
 6QN  C7   C8   single    1.444  0.020  1.444
 6QN  C13  C8   aromatic  1.393  0.020  1.393
 6QN  C13  C12  aromatic  1.402  0.020  1.402
 6QN  C8   C9   aromatic  1.397  0.020  1.397
 6QN  C12  N11  aromatic  1.312  0.020  1.312
 6QN  C9   C10  aromatic  1.377  0.020  1.377
 6QN  N11  C10  aromatic  1.338  0.020  1.338
 6QN  C9   H25  single    0.930  0.020  1.080
 6QN  C10  H26  single    0.930  0.020  1.080
 6QN  C12  H27  single    0.930  0.020  1.080
 6QN  N3   H24  single    0.860  0.020  1.020
 6QN  C1   H19  single    0.970  0.020  1.090
 6QN  C1   H20  single    0.970  0.020  1.090
 6QN  C1   H21  single    0.970  0.020  1.090
 6QN  C2   H23  single    0.970  0.020  1.090
 6QN  C2   H22  single    0.970  0.020  1.090
 6QN  N14  H15  single    0.860  0.020  1.020
 6QN  O18  H28  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
 6QN  O5   C4   N3   120.96  3.000
 6QN  O5   C4   C6   119.12  3.000
 6QN  N3   C4   C6   119.92  3.000
 6QN  C16  C6   C7   120.66  3.000
 6QN  C7   C6   C4   117.06  3.000
 6QN  C16  C6   C4   122.27  3.000
 6QN  O18  C7   C8   116.98  3.000
 6QN  C8   C7   C6   120.18  3.000
 6QN  O18  C7   C6   122.84  3.000
 6QN  C13  C8   C9   118.27  3.000
 6QN  C9   C8   C7   123.78  3.000
 6QN  C13  C8   C7   117.95  3.000
 6QN  H25  C9   C10  120.22  3.000
 6QN  H25  C9   C8   121.09  3.000
 6QN  C10  C9   C8   118.68  3.000
 6QN  H26  C10  N11  116.65  3.000
 6QN  H26  C10  C9   120.40  3.000
 6QN  N11  C10  C9   122.96  3.000
 6QN  H27  C12  N11  117.75  3.000
 6QN  H27  C12  C13  119.59  3.000
 6QN  N11  C12  C13  122.66  3.000
 6QN  N14  C13  C12  121.36  3.000
 6QN  C12  C13  C8   118.46  3.000
 6QN  N14  C13  C8   120.18  3.000
 6QN  H24  N3   C2   120.01  3.000
 6QN  H24  N3   C4   117.28  3.000
 6QN  C2   N3   C4   122.71  3.000
 6QN  H21  C1   H20  107.81  3.000
 6QN  H21  C1   H19  107.80  3.000
 6QN  H20  C1   H19  108.34  3.000
 6QN  H21  C1   C2   109.73  3.000
 6QN  H20  C1   C2   111.49  3.000
 6QN  H19  C1   C2   111.53  3.000
 6QN  H22  C2   H23  106.82  3.000
 6QN  H22  C2   C1   110.20  3.000
 6QN  H23  C2   C1   110.18  3.000
 6QN  H22  C2   N3   109.63  3.000
 6QN  H23  C2   N3   109.66  3.000
 6QN  C1   C2   N3   110.28  3.000
 6QN  C12  N11  C10  118.98  3.000
 6QN  H15  N14  C16  116.28  3.000
 6QN  H15  N14  C13  118.66  3.000
 6QN  C16  N14  C13  125.06  3.000
 6QN  O17  C16  N14  119.38  3.000
 6QN  N14  C16  C6   115.97  3.000
 6QN  O17  C16  C6   124.65  3.000
 6QN  H28  O18  C7   104.84  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
 6QN  CONST_01  N11  C12  C13  C8      0.00   0.0  0
 6QN  CONST_02  N11  C10  C9   C8      0.00   0.0  0
 6QN  CONST_03  C12  C13  C8   C9      0.00   0.0  0
 6QN  CONST_04  C12  N11  C10  C9      0.00   0.0  0
 6QN  CONST_05  C13  C8   C9   C10     0.00   0.0  0
 6QN  CONST_06  C13  C12  N11  C10     0.00   0.0  0
 6QN  CONST_07  C13  N14  C16  C6      0.00   0.0  0
 6QN  CONST_08  O17  C16  N14  C13   180.00   0.0  0
 6QN  CONST_09  H25  C9   C8   C7      0.00   0.0  0
 6QN  CONST_10  H27  C12  C13  C8    180.00   0.0  0
 6QN  CONST_11  H26  C10  C9   C8    180.00   0.0  0
 6QN  CONST_12  H15  N14  C16  C6    180.00   0.0  0
 6QN  CONST_13  C2   N3   C4   C6    180.00   0.0  0
 6QN  CONST_14  H24  N3   C4   C6      0.00   0.0  0
 6QN  CONST_15  O5   C4   N3   C2      0.00   0.0  0
 6QN  Var_01    N3   C4   C6   C7    179.81  30.0  2
 6QN  Var_02    C1   C2   N3   C4   -179.79  30.0  2
 6QN  Var_03    H19  C1   C2   N3    -60.74  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
 6QN  plan-1  C4   0.020
 6QN  plan-1  C6   0.020
 6QN  plan-1  C7   0.020
 6QN  plan-1  C8   0.020
 6QN  plan-1  C9   0.020
 6QN  plan-1  C10  0.020
 6QN  plan-1  C12  0.020
 6QN  plan-1  C13  0.020
 6QN  plan-1  N11  0.020
 6QN  plan-1  N14  0.020
 6QN  plan-1  C16  0.020
 6QN  plan-1  O17  0.020
 6QN  plan-1  O18  0.020
 6QN  plan-1  H25  0.020
 6QN  plan-1  H26  0.020
 6QN  plan-1  H27  0.020
 6QN  plan-1  H15  0.020
 6QN  plan-2  C4   0.020
 6QN  plan-2  C6   0.020
 6QN  plan-2  N3   0.020
 6QN  plan-2  C2   0.020
 6QN  plan-2  O5   0.020
 6QN  plan-2  H24  0.020

