# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 05:47:41 2020
#   Inital geometry file: a 85 line input string
#   Ligand name: [(6,7-dimethyl-2-oxo-2H-1-benzopyran-4-yl)methyl]phosphonic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc2OC(=O)C=C(C[P](O)(O)=O)c2cc1C
#
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
 TWB  TWB  '[(6,7-dimethyl-2-oxo-2H-1-benzopyran-4-yl)methyl]phosphonic acid'  ligand  29  18  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_TWB
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
 TWB  C01  C  CH3    0  -0.735   5.2569   0.3691   0.0385
 TWB  C02  C  CR6    0   0.059   3.7616   0.2772   0.0240
 TWB  C03  C  CR16   0  -0.377   3.1424  -0.9618   0.0027
 TWB  C04  C  CR66   0   0.370   1.7576  -1.0535  -0.0182
 TWB  C06  C  CR6    0   0.545  -0.1179  -2.5094  -0.1073
 TWB  C08  C  CR16   0  -0.581  -0.9716  -1.3494  -0.1059
 TWB  C09  C  CR6    0   0.303  -0.4908  -0.0857  -0.0445
 TWB  C10  C  CH2    0  -0.848  -1.3725   1.1188  -0.0207
 TWB  C15  C  CR66   0  -0.032   0.9534   0.0818  -0.0118
 TWB  C16  C  CR16   0  -0.386   1.5977   1.3251   0.0112
 TWB  C17  C  CR6    0   0.095   2.9745   1.4455   0.0277
 TWB  C18  C  CH3    0  -0.735   3.6217   2.7989   0.0547
 TWB  O05  O  O      0  -0.470   1.2221  -2.2972  -0.0481
 TWB  O07  O  O      0  -0.455  -0.4846  -3.6623  -0.1501
 TWB  O12  O  OP    -1  -0.901  -3.4537   0.2021   1.4752
 TWB  O13  O  OP    -1  -0.895  -3.7179   2.3678   0.1148
 TWB  O14  O  O      0  -0.899  -3.6614   0.0918  -1.0811
 TWB  P11  P  P      0   1.197  -3.2310   0.9143   0.1393
 TWB  H1   H  HCH3   0   0.249   5.6140   0.9120   0.9157
 TWB  H2   H  HCH3   0   0.255   5.7147  -0.6185   0.0467
 TWB  H3   H  HCH3   0   0.249   5.6287   0.9055  -0.8367
 TWB  H4   H  HCR6   0   0.267   3.7374  -1.8673  -0.0009
 TWB  H5   H  HCR6   0   0.267  -2.0336  -1.5305  -0.1784
 TWB  H6   H  HCH2   0   0.228  -1.0323   1.7638   0.7976
 TWB  H7   H  HCH2   0   0.234  -1.1615   1.7000  -0.9269
 TWB  H8   H  HCR6   0   0.256   0.9931   2.2232   0.0107
 TWB  H9   H  HCH3   0   0.243   4.3153   2.9326  -0.7781
 TWB  H10  H  HCH3   0   0.253   2.8787   3.5932   0.0026
 TWB  H11  H  HCH3   0   0.245   4.2000   2.9443   0.9692

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
 TWB  O07  C06  double    1.211  0.020  1.211
 TWB  O05  C06  single    1.358  0.020  1.358
 TWB  O05  C04  single    1.354  0.020  1.354
 TWB  C01  C02  single    1.498  0.020  1.498
 TWB  C03  C04  aromatic  1.388  0.020  1.388
 TWB  C03  C02  aromatic  1.385  0.020  1.385
 TWB  C06  C08  single    1.440  0.020  1.440
 TWB  C04  C15  aromatic  1.391  0.020  1.391
 TWB  C02  C17  aromatic  1.409  0.020  1.409
 TWB  C08  C09  double    1.353  0.020  1.353
 TWB  C15  C09  single    1.454  0.020  1.454
 TWB  C15  C16  aromatic  1.400  0.020  1.400
 TWB  C17  C16  aromatic  1.382  0.020  1.382
 TWB  C17  C18  single    1.500  0.020  1.500
 TWB  C09  C10  single    1.493  0.020  1.493
 TWB  C10  P11  single    1.877  0.020  1.877
 TWB  O14  P11  deloc     1.533  0.020  1.533
 TWB  O13  P11  deloc     1.533  0.020  1.533
 TWB  P11  O12  deloc     1.530  0.020  1.530
 TWB  C01  H1   single    0.970  0.020  1.090
 TWB  C01  H2   single    0.970  0.020  1.090
 TWB  C01  H3   single    0.970  0.020  1.090
 TWB  C03  H4   single    0.930  0.020  1.080
 TWB  C08  H5   single    0.930  0.020  1.080
 TWB  C10  H6   single    0.970  0.020  1.090
 TWB  C10  H7   single    0.970  0.020  1.090
 TWB  C16  H8   single    0.930  0.020  1.080
 TWB  C18  H9   single    0.970  0.020  1.090
 TWB  C18  H10  single    0.970  0.020  1.090
 TWB  C18  H11  single    0.970  0.020  1.090

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
 TWB  H3   C01  H2   107.97  3.000
 TWB  H3   C01  H1   106.76  3.000
 TWB  H2   C01  H1   107.91  3.000
 TWB  H3   C01  C02  111.24  3.000
 TWB  H2   C01  C02  111.36  3.000
 TWB  H1   C01  C02  111.40  3.000
 TWB  C17  C02  C03  119.47  3.000
 TWB  C17  C02  C01  120.45  3.000
 TWB  C03  C02  C01  120.08  3.000
 TWB  H4   C03  C04  119.51  3.000
 TWB  H4   C03  C02  120.14  3.000
 TWB  C04  C03  C02  120.35  3.000
 TWB  O05  C04  C15  121.39  3.000
 TWB  C15  C04  C03  121.52  3.000
 TWB  O05  C04  C03  117.09  3.000
 TWB  O07  C06  O05  116.69  3.000
 TWB  O05  C06  C08  117.32  3.000
 TWB  O07  C06  C08  125.98  3.000
 TWB  H5   C08  C09  120.60  3.000
 TWB  H5   C08  C06  116.60  3.000
 TWB  C09  C08  C06  122.79  3.000
 TWB  C15  C09  C10  119.55  3.000
 TWB  C10  C09  C08  122.97  3.000
 TWB  C15  C09  C08  117.48  3.000
 TWB  H7   C10  H6   104.20  3.000
 TWB  H7   C10  P11  108.58  3.000
 TWB  H6   C10  P11  107.93  3.000
 TWB  H7   C10  C09  107.50  3.000
 TWB  H6   C10  C09  107.66  3.000
 TWB  P11  C10  C09  119.89  3.000
 TWB  C16  C15  C09  124.02  3.000
 TWB  C16  C15  C04  117.30  3.000
 TWB  C09  C15  C04  118.68  3.000
 TWB  H8   C16  C17  118.95  3.000
 TWB  H8   C16  C15  118.65  3.000
 TWB  C17  C16  C15  122.40  3.000
 TWB  C18  C17  C16  120.56  3.000
 TWB  C18  C17  C02  120.47  3.000
 TWB  C16  C17  C02  118.97  3.000
 TWB  H11  C18  H10  107.73  3.000
 TWB  H11  C18  H9   106.62  3.000
 TWB  H10  C18  H9   107.92  3.000
 TWB  H11  C18  C17  111.33  3.000
 TWB  H10  C18  C17  111.27  3.000
 TWB  H9   C18  C17  111.75  3.000
 TWB  C06  O05  C04  122.31  3.000
 TWB  O14  P11  O13  114.00  3.000
 TWB  O13  P11  O12  114.14  3.000
 TWB  O14  P11  O12  113.85  3.000
 TWB  O12  P11  C10  105.62  3.000
 TWB  O13  P11  C10  102.11  3.000
 TWB  O14  P11  C10  105.58  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
 TWB  CONST_01  C15  C04  C03  C02     0.00   0.0  0
 TWB  CONST_02  C15  C16  C17  C02     0.00   0.0  0
 TWB  CONST_03  C16  C15  C04  C03     0.00   0.0  0
 TWB  CONST_04  C16  C17  C02  C03     0.00   0.0  0
 TWB  CONST_05  C17  C02  C03  C04     0.00   0.0  0
 TWB  CONST_06  C17  C16  C15  C04     0.00   0.0  0
 TWB  CONST_07  C04  C03  C02  C01   180.00   0.0  0
 TWB  CONST_08  C16  C17  C02  C01   180.00   0.0  0
 TWB  CONST_09  C18  C17  C02  C03   180.00   0.0  0
 TWB  CONST_10  C18  C17  C16  C15   180.00   0.0  0
 TWB  CONST_11  H8   C16  C17  C02   180.00   0.0  0
 TWB  CONST_12  H4   C03  C04  C15   180.00   0.0  0
 TWB  Var_01    C08  C06  O05  C04    -1.44  30.0  1
 TWB  Var_02    C08  C09  C15  C04    -1.26  30.0  1
 TWB  Var_03    C15  C04  O05  C06     1.70  30.0  1
 TWB  Var_04    C15  C09  C08  C06     1.51  30.0  1
 TWB  Var_05    O05  C06  C08  C09    -0.22  30.0  1
 TWB  Var_06    P11  C10  C09  C08     7.63  30.0  3
 TWB  Var_07    H9   C18  C17  C02    56.37  30.0  2
 TWB  Var_08    H1   C01  C02  C03  -121.47  30.0  2
 TWB  Var_09    O14  P11  C10  C09   -60.32  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
 TWB  plan-1  C06  0.020
 TWB  plan-1  C08  0.020
 TWB  plan-1  O05  0.020
 TWB  plan-1  O07  0.020
 TWB  plan-2  C01  0.020
 TWB  plan-2  C02  0.020
 TWB  plan-2  C03  0.020
 TWB  plan-2  C04  0.020
 TWB  plan-2  C09  0.020
 TWB  plan-2  C15  0.020
 TWB  plan-2  C16  0.020
 TWB  plan-2  C17  0.020
 TWB  plan-2  C18  0.020
 TWB  plan-2  O05  0.020
 TWB  plan-2  H4   0.020
 TWB  plan-2  H8   0.020

