# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 19:47:42 2020
#   Inital geometry file: a 89 line input string
#   Ligand name: [naphthalene-2,7-diylbis(difluoromethanediyl)]bis(phosphonic acid)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[P](O)(=O)C(F)(F)c1ccc2ccc(cc2c1)C(F)(F)[P](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
 FNP  FNP  '[naphthalene-2,7-diylbis(difluoromethanediyl)]bis(phosphonic acid)'  ligand  34  24  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FNP
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
 FNP  C1   C  CT    0   0.552  -0.3250   0.8661   3.6242
 FNP  C2   C  CR6   0  -0.118   0.4412  -0.5426  -2.3358
 FNP  C3   C  CR16  0  -0.281   1.8544  -0.4694  -2.3495
 FNP  C4   C  CR16  0  -0.292   2.5385  -0.1514  -1.2110
 FNP  C5   C  CR66  0   0.119   1.8526   0.1115  -0.0046
 FNP  C6   C  CR16  0  -0.294   2.5290   0.4338   1.1934
 FNP  C7   C  CR16  0  -0.268   1.8370   0.6778   2.3446
 FNP  C8   C  CR6   0  -0.118   0.4235   0.6224   2.3510
 FNP  C9   C  CR16  0  -0.360  -0.2592   0.3087   1.2050
 FNP  C10  C  CR66  0   0.171   0.4384   0.0460   0.0052
 FNP  C11  C  CR16  0  -0.345  -0.2504  -0.2823  -1.1827
 FNP  F1   F  F     0  -0.330  -1.5390   1.4252   3.3684
 FNP  F2   F  F     0  -0.328   0.3508   1.7346   4.4228
 FNP  P1   P  P     0   1.314  -0.6673  -0.6573   4.6333
 FNP  OP1  O  O     0  -0.682  -1.4217  -0.3912   5.8727
 FNP  OP2  O  OH1   0  -0.734   0.8168  -1.2234   4.7484
 FNP  OP3  O  OH1   0  -0.734  -1.4839  -1.6086   3.6439
 FNP  F3   F  F     0  -0.332   0.4315  -1.7556  -4.3452
 FNP  F4   F  F     0  -0.326  -1.4838  -1.4604  -3.3329
 FNP  P2   P  P     0   1.314  -0.6302   0.5756  -4.7159
 FNP  OP4  O  O     0  -0.683  -1.2415   0.1902  -6.0025
 FNP  OP5  O  OH1   0  -0.733  -1.4710   1.4814  -3.7119
 FNP  OP6  O  OH1   0  -0.734   0.7967   1.2619  -4.9266
 FNP  HC3  H  HCR6  0   0.279   2.4064  -0.6749  -3.2564
 FNP  HC4  H  HCR6  0   0.270   3.6198  -0.1033  -1.2264
 FNP  HC6  H  HCR6  0   0.270   3.6104   0.4840   1.1922
 FNP  HC7  H  HCR6  0   0.274   2.3802   0.9188   3.2476
 FNP  HC9  H  HCR6  0   0.279  -1.3410   0.2627   1.1880
 FNP  H11  H  HCR6  0   0.273  -1.3315  -0.3261  -1.1526
 FNP  HO2  H  HOH1  0   0.511   0.9587  -1.8911   5.4354
 FNP  HO3  H  HOH1  0   0.503  -0.9793  -2.0709   2.9612
 FNP  HO5  H  HOH1  0   0.510  -1.9625   2.2090  -4.1207
 FNP  HO6  H  HOH1  0   0.504   1.1143   1.8365  -4.2171
 FNP  C12  C  CT    0   0.551  -0.2886  -0.8715  -3.6000

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
 FNP  C1   C8   single    1.497  0.020  1.497
 FNP  C1   F1   single    1.361  0.020  1.361
 FNP  C1   F2   single    1.360  0.020  1.360
 FNP  C1   P1   single    1.859  0.020  1.859
 FNP  C2   C3   aromatic  1.415  0.020  1.415
 FNP  C2   C11  aromatic  1.370  0.020  1.370
 FNP  C2   C12  single    1.496  0.020  1.496
 FNP  C3   C4   aromatic  1.366  0.020  1.366
 FNP  C3   HC3  single    0.930  0.020  1.080
 FNP  C4   C5   aromatic  1.412  0.020  1.412
 FNP  C4   HC4  single    0.930  0.020  1.080
 FNP  C5   C6   aromatic  1.413  0.020  1.413
 FNP  C5   C10  aromatic  1.416  0.020  1.416
 FNP  C6   C7   aromatic  1.365  0.020  1.365
 FNP  C6   HC6  single    0.930  0.020  1.080
 FNP  C7   C8   aromatic  1.415  0.020  1.415
 FNP  C7   HC7  single    0.930  0.020  1.080
 FNP  C8   C9   aromatic  1.370  0.020  1.370
 FNP  C9   C10  aromatic  1.413  0.020  1.413
 FNP  C9   HC9  single    0.930  0.020  1.080
 FNP  C10  C11  aromatic  1.412  0.020  1.412
 FNP  C11  H11  single    0.930  0.020  1.080
 FNP  C12  F3   single    1.362  0.020  1.362
 FNP  C12  F4   single    1.359  0.020  1.359
 FNP  C12  P2   single    1.859  0.020  1.859
 FNP  P1   OP1  double    1.475  0.020  1.475
 FNP  P1   OP2  single    1.593  0.020  1.593
 FNP  P1   OP3  single    1.597  0.020  1.597
 FNP  OP2  HO2  single    0.850  0.020  0.980
 FNP  OP3  HO3  single    0.850  0.020  0.980
 FNP  P2   OP4  double    1.476  0.020  1.476
 FNP  P2   OP5  single    1.592  0.020  1.592
 FNP  P2   OP6  single    1.597  0.020  1.597
 FNP  OP5  HO5  single    0.850  0.020  0.980
 FNP  OP6  HO6  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
 FNP  P1   C1   F2   107.23  3.000
 FNP  P1   C1   F1   105.93  3.000
 FNP  F2   C1   F1   106.94  3.000
 FNP  P1   C1   C8   114.86  3.000
 FNP  F2   C1   C8   110.80  3.000
 FNP  F1   C1   C8   110.67  3.000
 FNP  C12  C2   C11  120.45  3.000
 FNP  C12  C2   C3   119.36  3.000
 FNP  C11  C2   C3   120.17  3.000
 FNP  HC3  C3   C4   119.19  3.000
 FNP  HC3  C3   C2   120.53  3.000
 FNP  C4   C3   C2   120.28  3.000
 FNP  HC4  C4   C5   119.28  3.000
 FNP  HC4  C4   C3   119.92  3.000
 FNP  C5   C4   C3   120.80  3.000
 FNP  C10  C5   C6   118.88  3.000
 FNP  C10  C5   C4   118.84  3.000
 FNP  C6   C5   C4   122.28  3.000
 FNP  HC6  C6   C7   119.93  3.000
 FNP  HC6  C6   C5   119.20  3.000
 FNP  C7   C6   C5   120.87  3.000
 FNP  HC7  C7   C8   120.47  3.000
 FNP  HC7  C7   C6   119.31  3.000
 FNP  C8   C7   C6   120.22  3.000
 FNP  C9   C8   C7   120.20  3.000
 FNP  C9   C8   C1   119.97  3.000
 FNP  C7   C8   C1   119.81  3.000
 FNP  HC9  C9   C10  118.18  3.000
 FNP  HC9  C9   C8   121.37  3.000
 FNP  C10  C9   C8   120.45  3.000
 FNP  C11  C10  C9   121.12  3.000
 FNP  C11  C10  C5   119.50  3.000
 FNP  C9   C10  C5   119.38  3.000
 FNP  H11  C11  C10  118.26  3.000
 FNP  H11  C11  C2   121.33  3.000
 FNP  C10  C11  C2   120.41  3.000
 FNP  OP3  P1   OP2  108.03  3.000
 FNP  OP3  P1   OP1  111.50  3.000
 FNP  OP2  P1   OP1  118.68  3.000
 FNP  OP3  P1   C1   104.24  3.000
 FNP  OP2  P1   C1    99.14  3.000
 FNP  OP1  P1   C1   113.73  3.000
 FNP  HO2  OP2  P1   115.65  3.000
 FNP  HO3  OP3  P1   117.10  3.000
 FNP  OP6  P2   OP5  108.09  3.000
 FNP  OP6  P2   OP4  111.55  3.000
 FNP  OP5  P2   OP4  118.66  3.000
 FNP  OP6  P2   C12  104.45  3.000
 FNP  OP5  P2   C12   99.28  3.000
 FNP  OP4  P2   C12  113.34  3.000
 FNP  HO5  OP5  P2   115.41  3.000
 FNP  HO6  OP6  P2   116.88  3.000
 FNP  P2   C12  F4   107.08  3.000
 FNP  P2   C12  F3   105.90  3.000
 FNP  F4   C12  F3   106.93  3.000
 FNP  P2   C12  C2   115.20  3.000
 FNP  F4   C12  C2   110.99  3.000
 FNP  F3   C12  C2   110.31  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
 FNP  CONST_01  C5   C4   C3   C2      0.00   0.0  0
 FNP  CONST_02  C5   C10  C11  C2      0.00   0.0  0
 FNP  CONST_03  C9   C10  C11  C2    180.00   0.0  0
 FNP  CONST_04  C10  C11  C2   C3      0.00   0.0  0
 FNP  CONST_05  C6   C5   C4   C3    180.00   0.0  0
 FNP  CONST_06  C10  C5   C4   C3      0.00   0.0  0
 FNP  CONST_07  C11  C2   C3   C4      0.00   0.0  0
 FNP  CONST_08  C7   C6   C5   C4    180.00   0.0  0
 FNP  CONST_09  C9   C10  C5   C4    180.00   0.0  0
 FNP  CONST_10  C11  C10  C5   C4      0.00   0.0  0
 FNP  CONST_11  C8   C7   C6   C5      0.00   0.0  0
 FNP  CONST_12  C8   C9   C10  C5      0.00   0.0  0
 FNP  CONST_13  C9   C10  C5   C6      0.00   0.0  0
 FNP  CONST_14  C11  C10  C5   C6    180.00   0.0  0
 FNP  CONST_15  C9   C8   C7   C6      0.00   0.0  0
 FNP  CONST_16  C10  C5   C6   C7      0.00   0.0  0
 FNP  CONST_17  C10  C9   C8   C7      0.00   0.0  0
 FNP  CONST_18  C11  C10  C9   C8    180.00   0.0  0
 FNP  CONST_19  C6   C7   C8   C1    180.00   0.0  0
 FNP  CONST_20  C10  C9   C8   C1    180.00   0.0  0
 FNP  CONST_21  C12  C2   C3   C4    180.00   0.0  0
 FNP  CONST_22  C12  C2   C11  C10   180.00   0.0  0
 FNP  CONST_23  HC4  C4   C3   C2    180.00   0.0  0
 FNP  CONST_24  H11  C11  C2   C3    180.00   0.0  0
 FNP  CONST_25  HC6  C6   C5   C4      0.00   0.0  0
 FNP  CONST_26  HC3  C3   C4   C5    180.00   0.0  0
 FNP  CONST_27  HC7  C7   C6   C5    180.00   0.0  0
 FNP  CONST_28  HC9  C9   C10  C5    180.00   0.0  0
 FNP  Var_01    F3   C12  C2   C3     34.98  30.0  2
 FNP  Var_02    F1   C1   C8   C7    149.43  30.0  2
 FNP  Var_03    OP4  P2   C12  C2    174.82  30.0  3
 FNP  Var_04    OP1  P1   C1   C8   -179.21  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
 FNP  plan-1  C1   0.020
 FNP  plan-1  C2   0.020
 FNP  plan-1  C3   0.020
 FNP  plan-1  C4   0.020
 FNP  plan-1  C5   0.020
 FNP  plan-1  C6   0.020
 FNP  plan-1  C7   0.020
 FNP  plan-1  C8   0.020
 FNP  plan-1  C9   0.020
 FNP  plan-1  C10  0.020
 FNP  plan-1  C11  0.020
 FNP  plan-1  HC3  0.020
 FNP  plan-1  HC4  0.020
 FNP  plan-1  HC6  0.020
 FNP  plan-1  HC7  0.020
 FNP  plan-1  HC9  0.020
 FNP  plan-1  H11  0.020
 FNP  plan-1  C12  0.020

