# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 13:53:59 2022
#   Inital geometry file: a 112 line input string
#   Ligand name: 2-amino-7-[3-(dimethylamino)propyl]-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(C)CCCc1ccc2Oc3nc(N)c(cc3C(=O)c2c1)C(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
 F8M  F8M  '2-amino-7-[3-(dimethylamino)propyl]-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid'  ligand  43  25  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_F8M
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
 F8M  C01  C  CH3    0  -0.520   8.1444   1.8006  -0.4682
 F8M  C03  C  CH3    0  -0.526   7.2220   0.2255  -1.9948
 F8M  C04  C  CH2    0  -0.255   6.2036   0.5698   0.1636
 F8M  C05  C  CH2    0  -0.440   4.7810   0.1548  -0.1846
 F8M  C06  C  CH2    0  -0.507   4.0473  -0.3901   1.0425
 F8M  C07  C  CR6    0   0.150   2.6322  -0.7795   0.7229
 F8M  C08  C  CR16   0  -0.306   2.3313  -2.0582   0.2370
 F8M  C09  C  CR16   0  -0.313   1.0437  -2.4191  -0.1046
 F8M  C10  C  CR66   0   0.339   0.0211  -1.4875   0.0346
 F8M  C12  C  CR66   0   0.480  -2.2667  -1.0528  -0.2125
 F8M  C14  C  CR6    0   0.466  -4.5117  -0.8398  -0.5313
 F8M  C16  C  CR6    0  -0.268  -4.4975   0.5223  -0.0739
 F8M  C17  C  C      0   0.455  -5.7376   1.3972  -0.0028
 F8M  C20  C  CR16   0  -0.207  -3.2833   1.0234   0.3065
 F8M  C21  C  CR66   0  -0.253  -2.1094   0.2533   0.2547
 F8M  C22  C  CR6    0   0.415  -0.8148   0.7635   0.6516
 F8M  C24  C  CR66   0  -0.088   0.2822  -0.2067   0.5134
 F8M  C25  C  CR16   0  -0.371   1.5964   0.1266   0.8524
 F8M  N02  N  NT     0  -0.408   6.9290   1.1724  -0.9398
 F8M  N13  N  N      0  -0.486  -3.4006  -1.5854  -0.5889
 F8M  N15  N  NH2    0  -0.821  -5.6446  -1.4147  -0.9181
 F8M  O11  O  O      0  -0.456  -1.2237  -1.8936  -0.3149
 F8M  O18  O  O      0  -0.600  -6.8248   0.8849  -0.3626
 F8M  O19  O  OC    -1  -0.574  -5.5792   2.5576   0.4071
 F8M  O23  O  O      0  -0.438  -0.6338   1.9011   1.0663
 F8M  H1   H  HCH3   0   0.231   8.6652   2.2794  -1.2984
 F8M  H2   H  HCH3   0   0.232   7.9084   2.5712   0.2675
 F8M  H3   H  HCH3   0   0.189   8.8476   1.0948   0.0029
 F8M  H4   H  HCH3   0   0.234   6.3071  -0.1607  -2.4435
 F8M  H5   H  HCH3   0   0.233   7.7873   0.7194  -2.7862
 F8M  H6   H  HCH3   0   0.189   7.8156  -0.6367  -1.6495
 F8M  H7   H  HCH2   0   0.227   6.1546   1.3075   0.9704
 F8M  H8   H  HCH2   0   0.184   6.7473  -0.3005   0.5744
 F8M  H9   H  HCH2   0   0.229   4.2395   1.0173  -0.5838
 F8M  H10  H  HCH2   0   0.233   4.7761  -0.6115  -0.9641
 F8M  H11  H  HCH2   0   0.244   4.5907  -1.2550   1.4330
 F8M  H12  H  HCH2   0   0.244   4.0491   0.3637   1.8341
 F8M  H13  H  HCR6   0   0.263   3.1244  -2.7884   0.1304
 F8M  H14  H  HCR6   0   0.279   0.8242  -3.4124  -0.4738
 F8M  H15  H  HCR6   0   0.262  -3.2228   2.0448   0.6589
 F8M  H16  H  HCR6   0   0.257   1.7963   1.1240   1.2255
 F8M  H18  H  HNH2   0   0.413  -6.4829  -0.8423  -0.8763
 F8M  H19  H  HNH2   0   0.392  -5.6479  -2.3628  -1.2522

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
 F8M  O18  C17  deloc     1.255  0.020  1.255
 F8M  N15  C14  single    1.328  0.020  1.328
 F8M  C17  O19  deloc     1.241  0.020  1.241
 F8M  C17  C16  single    1.519  0.020  1.519
 F8M  C14  C16  aromatic  1.437  0.020  1.437
 F8M  C14  N13  aromatic  1.339  0.020  1.339
 F8M  C16  C20  aromatic  1.368  0.020  1.368
 F8M  N13  C12  aromatic  1.308  0.020  1.308
 F8M  C20  C21  aromatic  1.405  0.020  1.405
 F8M  C12  C21  aromatic  1.396  0.020  1.396
 F8M  C12  O11  single    1.344  0.020  1.344
 F8M  C21  C22  single    1.447  0.020  1.447
 F8M  O11  C10  single    1.355  0.020  1.355
 F8M  C10  C09  aromatic  1.390  0.020  1.390
 F8M  C10  C24  aromatic  1.392  0.020  1.392
 F8M  C22  O23  double    1.224  0.020  1.224
 F8M  C22  C24  single    1.471  0.020  1.471
 F8M  C09  C08  aromatic  1.380  0.020  1.380
 F8M  C24  C25  aromatic  1.398  0.020  1.398
 F8M  C08  C07  aromatic  1.401  0.020  1.401
 F8M  C25  C07  aromatic  1.382  0.020  1.382
 F8M  C07  C06  single    1.502  0.020  1.502
 F8M  C06  C05  single    1.530  0.020  1.530
 F8M  C04  C05  single    1.522  0.020  1.522
 F8M  C04  N02  single    1.451  0.020  1.451
 F8M  C03  N02  single    1.448  0.020  1.448
 F8M  N02  C01  single    1.447  0.020  1.447
 F8M  C01  H1   single    0.970  0.020  1.090
 F8M  C01  H2   single    0.970  0.020  1.090
 F8M  C01  H3   single    0.970  0.020  1.090
 F8M  C03  H4   single    0.970  0.020  1.090
 F8M  C03  H5   single    0.970  0.020  1.090
 F8M  C03  H6   single    0.970  0.020  1.090
 F8M  C04  H7   single    0.970  0.020  1.090
 F8M  C04  H8   single    0.970  0.020  1.090
 F8M  C05  H9   single    0.970  0.020  1.090
 F8M  C05  H10  single    0.970  0.020  1.090
 F8M  C06  H11  single    0.970  0.020  1.090
 F8M  C06  H12  single    0.970  0.020  1.090
 F8M  C08  H13  single    0.930  0.020  1.080
 F8M  C09  H14  single    0.930  0.020  1.080
 F8M  C20  H15  single    0.930  0.020  1.080
 F8M  C25  H16  single    0.930  0.020  1.080
 F8M  N15  H18  single    0.860  0.020  1.020
 F8M  N15  H19  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
 F8M  H3   C01  H2   107.58  3.000
 F8M  H3   C01  H1   107.56  3.000
 F8M  H2   C01  H1   107.85  3.000
 F8M  H3   C01  N02  113.41  3.000
 F8M  H2   C01  N02  110.16  3.000
 F8M  H1   C01  N02  110.09  3.000
 F8M  H6   C03  H5   107.60  3.000
 F8M  H6   C03  H4   107.69  3.000
 F8M  H5   C03  H4   107.27  3.000
 F8M  H6   C03  N02  113.11  3.000
 F8M  H5   C03  N02  109.73  3.000
 F8M  H4   C03  N02  111.22  3.000
 F8M  H8   C04  H7   106.19  3.000
 F8M  H8   C04  N02  111.32  3.000
 F8M  H7   C04  N02  107.64  3.000
 F8M  H8   C04  C05  109.27  3.000
 F8M  H7   C04  C05  108.10  3.000
 F8M  N02  C04  C05  113.97  3.000
 F8M  H10  C05  H9   106.88  3.000
 F8M  H10  C05  C06  108.67  3.000
 F8M  H9   C05  C06  109.64  3.000
 F8M  H10  C05  C04  111.00  3.000
 F8M  H9   C05  C04  109.34  3.000
 F8M  C06  C05  C04  111.21  3.000
 F8M  H12  C06  H11  106.62  3.000
 F8M  H12  C06  C07  109.54  3.000
 F8M  H11  C06  C07  109.83  3.000
 F8M  H12  C06  C05  109.53  3.000
 F8M  H11  C06  C05  109.25  3.000
 F8M  C07  C06  C05  111.93  3.000
 F8M  C25  C07  C08  118.03  3.000
 F8M  C25  C07  C06  121.07  3.000
 F8M  C08  C07  C06  120.86  3.000
 F8M  H13  C08  C09  118.84  3.000
 F8M  H13  C08  C07  119.49  3.000
 F8M  C09  C08  C07  121.67  3.000
 F8M  H14  C09  C10  120.00  3.000
 F8M  H14  C09  C08  120.91  3.000
 F8M  C10  C09  C08  119.09  3.000
 F8M  O11  C10  C24  122.46  3.000
 F8M  C24  C10  C09  120.86  3.000
 F8M  O11  C10  C09  116.68  3.000
 F8M  O11  C12  N13  113.34  3.000
 F8M  O11  C12  C21  121.57  3.000
 F8M  N13  C12  C21  125.10  3.000
 F8M  N15  C14  N13  117.01  3.000
 F8M  N13  C14  C16  122.22  3.000
 F8M  N15  C14  C16  120.77  3.000
 F8M  C20  C16  C17  120.04  3.000
 F8M  C20  C16  C14  116.40  3.000
 F8M  C17  C16  C14  123.55  3.000
 F8M  O19  C17  O18  125.97  3.000
 F8M  O19  C17  C16  116.73  3.000
 F8M  O18  C17  C16  117.30  3.000
 F8M  H15  C20  C21  118.86  3.000
 F8M  H15  C20  C16  119.08  3.000
 F8M  C21  C20  C16  122.06  3.000
 F8M  C22  C21  C20  122.96  3.000
 F8M  C22  C21  C12  121.50  3.000
 F8M  C20  C21  C12  115.53  3.000
 F8M  O23  C22  C24  122.31  3.000
 F8M  C24  C22  C21  114.13  3.000
 F8M  O23  C22  C21  123.56  3.000
 F8M  C25  C24  C22  121.41  3.000
 F8M  C25  C24  C10  118.64  3.000
 F8M  C22  C24  C10  119.95  3.000
 F8M  H16  C25  C24  118.46  3.000
 F8M  H16  C25  C07  119.83  3.000
 F8M  C24  C25  C07  121.70  3.000
 F8M  C04  N02  C03  112.56  3.000
 F8M  C03  N02  C01  110.57  3.000
 F8M  C04  N02  C01  110.62  3.000
 F8M  C14  N13  C12  118.69  3.000
 F8M  H19  N15  H18  122.85  3.000
 F8M  H19  N15  C14  120.53  3.000
 F8M  H18  N15  C14  116.61  3.000
 F8M  C12  O11  C10  120.38  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
 F8M  CONST_01  C10  C09  C08  C07     0.00   0.0  0
 F8M  CONST_02  C10  C24  C25  C07     0.00   0.0  0
 F8M  CONST_03  C24  C10  C09  C08     0.00   0.0  0
 F8M  CONST_04  C24  C25  C07  C08     0.00   0.0  0
 F8M  CONST_05  C25  C24  C10  C09     0.00   0.0  0
 F8M  CONST_06  C25  C07  C08  C09     0.00   0.0  0
 F8M  CONST_07  C16  C14  N13  C12     0.00   0.0  0
 F8M  CONST_08  C16  C20  C21  C12     0.00   0.0  0
 F8M  CONST_09  C21  C20  C16  C14     0.00   0.0  0
 F8M  CONST_10  C21  C12  N13  C14     0.00   0.0  0
 F8M  CONST_11  N13  C14  C16  C20     0.00   0.0  0
 F8M  CONST_12  N13  C12  C21  C20     0.00   0.0  0
 F8M  CONST_13  C09  C08  C07  C06   180.00   0.0  0
 F8M  CONST_14  C24  C25  C07  C06   180.00   0.0  0
 F8M  CONST_15  N15  C14  N13  C12   180.00   0.0  0
 F8M  CONST_16  N13  C14  C16  C17   180.00   0.0  0
 F8M  CONST_17  C21  C20  C16  C17   180.00   0.0  0
 F8M  CONST_18  N15  C14  C16  C20   180.00   0.0  0
 F8M  CONST_19  H14  C09  C08  C07   180.00   0.0  0
 F8M  CONST_20  H16  C25  C07  C08   180.00   0.0  0
 F8M  CONST_21  H13  C08  C09  C10   180.00   0.0  0
 F8M  CONST_22  H15  C20  C21  C12   180.00   0.0  0
 F8M  CONST_23  H18  N15  C14  C16     0.00   0.0  0
 F8M  CONST_24  H19  N15  C14  C16   180.00   0.0  0
 F8M  Var_01    N13  C12  O11  C10   179.84  30.0  1
 F8M  Var_02    C21  C22  C24  C10     0.01  30.0  1
 F8M  Var_03    C24  C22  C21  C12     0.09  30.0  1
 F8M  Var_04    C24  C10  O11  C12     0.25  30.0  1
 F8M  Var_05    C08  C07  C06  C05    87.01  30.0  2
 F8M  Var_06    O18  C17  C16  C14     0.25  30.0  2
 F8M  Var_07    C07  C06  C05  C04   178.87  30.0  2
 F8M  Var_08    C05  C04  N02  C01   167.42  30.0  3
 F8M  Var_09    N02  C04  C05  C06  -176.43  30.0  1
 F8M  Var_10    H4   C03  N02  C01  -172.85  30.0  3
 F8M  Var_11    H1   C01  N02  C03    56.53  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
 F8M  plan-1  C06  0.020
 F8M  plan-1  C07  0.020
 F8M  plan-1  C08  0.020
 F8M  plan-1  C09  0.020
 F8M  plan-1  C10  0.020
 F8M  plan-1  C22  0.020
 F8M  plan-1  C24  0.020
 F8M  plan-1  C25  0.020
 F8M  plan-1  O11  0.020
 F8M  plan-1  H13  0.020
 F8M  plan-1  H14  0.020
 F8M  plan-1  H16  0.020
 F8M  plan-2  C14  0.020
 F8M  plan-2  N15  0.020
 F8M  plan-2  H18  0.020
 F8M  plan-2  H19  0.020
 F8M  plan-3  C12  0.020
 F8M  plan-3  C14  0.020
 F8M  plan-3  C16  0.020
 F8M  plan-3  C17  0.020
 F8M  plan-3  C20  0.020
 F8M  plan-3  C21  0.020
 F8M  plan-3  C22  0.020
 F8M  plan-3  N13  0.020
 F8M  plan-3  N15  0.020
 F8M  plan-3  O11  0.020
 F8M  plan-3  H15  0.020
 F8M  plan-4  C21  0.020
 F8M  plan-4  C22  0.020
 F8M  plan-4  C24  0.020
 F8M  plan-4  O23  0.020
 F8M  plan-5  C16  0.020
 F8M  plan-5  C17  0.020
 F8M  plan-5  O18  0.020
 F8M  plan-5  O19  0.020

