# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  1 09:08:58 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: 3-(7-hydroxy-2-oxo-4-phenyl-2H-chromen-6-yl)propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)CCc1cc2c(OC(=O)C=C2c3ccccc3)cc1O
#
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
 31R  31R  '3-(7-hydroxy-2-oxo-4-phenyl-2H-chromen-6-yl)propanoic acid'  ligand  36  23  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_31R
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
 31R  O11  O  O      0  -0.441  -4.2261   2.8529  -0.6587
 31R  C6   C  CR6    0   0.557  -3.2815   2.1396  -0.4202
 31R  O1   O  O      0  -0.468  -2.0911   2.7473  -0.1778
 31R  C2   C  CR66   0   0.378  -0.9518   2.0631   0.0760
 31R  C7   C  CR16   0  -0.418   0.1972   2.8088   0.2625
 31R  C8   C  CR6    0   0.318   1.3979   2.1554   0.5038
 31R  O12  O  OH1    0  -0.612   2.4780   2.9309   0.6779
 31R  C5   C  CR16   0  -0.562  -3.3018   0.6997  -0.3500
 31R  C4   C  CR6    0   0.254  -2.1920  -0.0216  -0.0659
 31R  C13  C  CR6    0   0.026  -2.2755  -1.4925   0.0253
 31R  C14  C  CR16   0  -0.292  -1.8759  -2.1596   1.1834
 31R  C15  C  CR16   0  -0.242  -1.9952  -3.5383   1.2724
 31R  C16  C  CR16   0  -0.255  -2.5041  -4.2665   0.2045
 31R  C17  C  CR16   0  -0.242  -2.9029  -3.6083  -0.9508
 31R  C18  C  CR16   0  -0.285  -2.7949  -2.2276  -1.0385
 31R  C3   C  CR66   0  -0.020  -0.9420   0.6681   0.1392
 31R  C10  C  CR16   0  -0.407   0.2915   0.0444   0.3642
 31R  C9   C  CR6    0   0.044   1.4629   0.7482   0.5521
 31R  C19  C  CH2    0  -0.557   2.7684   0.0268   0.7484
 31R  C20  C  CH2    0  -0.573   3.5767  -0.0837  -0.5435
 31R  C21  C  C      0   0.419   4.9312  -0.8048  -0.4039
 31R  O23  O  OC    -1  -0.626   5.5641  -0.9789  -1.4651
 31R  O22  O  O      0  -0.605   5.2880  -1.1499   0.7391
 31R  H1   H  HCR6   0   0.287   0.1622   3.8900   0.2177
 31R  H2   H  HOH1   0   0.484   3.2590   2.4040   0.8815
 31R  H3   H  HCR6   0   0.282  -4.2594   0.2214  -0.5041
 31R  H4   H  HCR6   0   0.270  -1.4897  -1.6015   2.0272
 31R  H5   H  HCR6   0   0.264  -1.6896  -4.0435   2.1791
 31R  H6   H  HCR6   0   0.263  -2.5909  -5.3429   0.2742
 31R  H7   H  HCR6   0   0.263  -3.2993  -4.1679  -1.7878
 31R  H8   H  HCR6   0   0.262  -3.1042  -1.7192  -1.9429
 31R  H9   H  HCR6   0   0.270   0.3384  -1.0368   0.3839
 31R  H10  H  HCH2   0   0.237   3.3701   0.5016   1.5299
 31R  H11  H  HCH2   0   0.258   2.5585  -0.9734   1.1301
 31R  H12  H  HCH2   0   0.237   2.9780  -0.6037  -1.2979
 31R  H13  H  HCH2   0   0.229   3.7624   0.9100  -0.9678

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
 31R  C15  C16  aromatic  1.389  0.020  1.389
 31R  C15  C14  aromatic  1.387  0.020  1.387
 31R  C16  C17  aromatic  1.388  0.020  1.388
 31R  C14  C13  aromatic  1.395  0.020  1.395
 31R  C17  C18  aromatic  1.388  0.020  1.388
 31R  C13  C18  aromatic  1.394  0.020  1.394
 31R  C13  C4   single    1.476  0.020  1.476
 31R  O22  C21  deloc     1.246  0.020  1.246
 31R  C5   C4   double    1.354  0.020  1.354
 31R  C5   C6   single    1.442  0.020  1.442
 31R  O23  C21  deloc     1.248  0.020  1.248
 31R  C4   C3   single    1.442  0.020  1.442
 31R  O11  C6   double    1.208  0.020  1.208
 31R  C21  C20  single    1.541  0.020  1.541
 31R  C6   O1   single    1.358  0.020  1.358
 31R  C3   C10  aromatic  1.400  0.020  1.400
 31R  C3   C2   aromatic  1.396  0.020  1.396
 31R  C10  C9   aromatic  1.379  0.020  1.379
 31R  O1   C2   single    1.353  0.020  1.353
 31R  C2   C7   aromatic  1.382  0.020  1.382
 31R  C20  C19  single    1.528  0.020  1.528
 31R  C9   C19  single    1.504  0.020  1.504
 31R  C9   C8   aromatic  1.409  0.020  1.409
 31R  C7   C8   aromatic  1.388  0.020  1.388
 31R  C8   O12  single    1.341  0.020  1.341
 31R  C7   H1   single    0.930  0.020  1.080
 31R  O12  H2   single    0.850  0.020  0.980
 31R  C5   H3   single    0.930  0.020  1.080
 31R  C14  H4   single    0.930  0.020  1.080
 31R  C15  H5   single    0.930  0.020  1.080
 31R  C16  H6   single    0.930  0.020  1.080
 31R  C17  H7   single    0.930  0.020  1.080
 31R  C18  H8   single    0.930  0.020  1.080
 31R  C10  H9   single    0.930  0.020  1.080
 31R  C19  H10  single    0.970  0.020  1.090
 31R  C19  H11  single    0.970  0.020  1.090
 31R  C20  H12  single    0.970  0.020  1.090
 31R  C20  H13  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
 31R  C5   C6   O1   116.78  3.000
 31R  O1   C6   O11  117.16  3.000
 31R  C5   C6   O11  126.06  3.000
 31R  C2   O1   C6   123.03  3.000
 31R  C3   C2   C7   121.80  3.000
 31R  C7   C2   O1   116.90  3.000
 31R  C3   C2   O1   121.30  3.000
 31R  H1   C7   C8   120.35  3.000
 31R  H1   C7   C2   120.41  3.000
 31R  C8   C7   C2   119.24  3.000
 31R  C9   C8   O12  122.40  3.000
 31R  O12  C8   C7   116.55  3.000
 31R  C9   C8   C7   121.05  3.000
 31R  H2   O12  C8   111.34  3.000
 31R  H3   C5   C4   121.34  3.000
 31R  H3   C5   C6   116.57  3.000
 31R  C4   C5   C6   122.06  3.000
 31R  C3   C4   C13  121.11  3.000
 31R  C3   C4   C5   119.05  3.000
 31R  C13  C4   C5   119.84  3.000
 31R  C18  C13  C14  119.23  3.000
 31R  C18  C13  C4   119.97  3.000
 31R  C14  C13  C4   120.77  3.000
 31R  H4   C14  C15  119.54  3.000
 31R  H4   C14  C13  120.17  3.000
 31R  C15  C14  C13  120.27  3.000
 31R  H5   C15  C16  120.19  3.000
 31R  H5   C15  C14  119.59  3.000
 31R  C16  C15  C14  120.22  3.000
 31R  H6   C16  C17  120.15  3.000
 31R  H6   C16  C15  120.09  3.000
 31R  C17  C16  C15  119.77  3.000
 31R  H7   C17  C18  119.62  3.000
 31R  H7   C17  C16  120.26  3.000
 31R  C18  C17  C16  120.13  3.000
 31R  H8   C18  C17  119.85  3.000
 31R  H8   C18  C13  119.77  3.000
 31R  C17  C18  C13  120.38  3.000
 31R  C10  C3   C4   124.98  3.000
 31R  C10  C3   C2   117.28  3.000
 31R  C4   C3   C2   117.72  3.000
 31R  H9   C10  C9   118.06  3.000
 31R  H9   C10  C3   119.08  3.000
 31R  C9   C10  C3   122.86  3.000
 31R  C19  C9   C10  120.66  3.000
 31R  C19  C9   C8   121.55  3.000
 31R  C10  C9   C8   117.75  3.000
 31R  H11  C19  H10  104.69  3.000
 31R  H11  C19  C20  109.35  3.000
 31R  H10  C19  C20  110.13  3.000
 31R  H11  C19  C9   108.56  3.000
 31R  H10  C19  C9   111.24  3.000
 31R  C20  C19  C9   112.55  3.000
 31R  H13  C20  H12  104.87  3.000
 31R  H13  C20  C21  108.08  3.000
 31R  H12  C20  C21  108.72  3.000
 31R  H13  C20  C19  110.56  3.000
 31R  H12  C20  C19  109.13  3.000
 31R  C21  C20  C19  114.98  3.000
 31R  O22  C21  O23  126.60  3.000
 31R  O23  C21  C20  115.73  3.000
 31R  O22  C21  C20  117.67  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
 31R  CONST_01  C9   C10  C3   C2      0.00   0.0  0
 31R  CONST_02  C9   C8   C7   C2      0.00   0.0  0
 31R  CONST_03  C10  C3   C2   C7      0.00   0.0  0
 31R  CONST_04  C10  C9   C8   C7      0.00   0.0  0
 31R  CONST_05  C3   C10  C9   C8      0.00   0.0  0
 31R  CONST_06  C3   C2   C7   C8      0.00   0.0  0
 31R  CONST_07  C16  C15  C14  C13     0.00   0.0  0
 31R  CONST_08  C16  C17  C18  C13     0.00   0.0  0
 31R  CONST_09  C17  C16  C15  C14     0.00   0.0  0
 31R  CONST_10  C17  C18  C13  C14     0.00   0.0  0
 31R  CONST_11  C18  C17  C16  C15     0.00   0.0  0
 31R  CONST_12  C18  C13  C14  C15     0.00   0.0  0
 31R  CONST_13  C15  C14  C13  C4    180.00   0.0  0
 31R  CONST_14  C17  C18  C13  C4    180.00   0.0  0
 31R  CONST_15  O12  C8   C7   C2    180.00   0.0  0
 31R  CONST_16  C19  C9   C8   C7    180.00   0.0  0
 31R  CONST_17  C10  C9   C8   O12   180.00   0.0  0
 31R  CONST_18  C19  C9   C10  C3    180.00   0.0  0
 31R  CONST_19  H1   C7   C2   O1      0.00   0.0  0
 31R  CONST_20  H9   C10  C3   C2    180.00   0.0  0
 31R  CONST_21  H4   C14  C13  C4      0.00   0.0  0
 31R  CONST_22  H8   C18  C13  C4      0.00   0.0  0
 31R  CONST_23  H5   C15  C14  C13   180.00   0.0  0
 31R  CONST_24  H7   C17  C18  C13   180.00   0.0  0
 31R  CONST_25  H6   C16  C15  C14   180.00   0.0  0
 31R  Var_01    C13  C4   C5   C6    178.54  30.0  1
 31R  Var_02    C3   C2   O1   C6     -1.75  30.0  1
 31R  Var_03    C4   C5   C6   O1     -0.43  30.0  1
 31R  Var_04    C5   C6   O1   C2      2.17  30.0  1
 31R  Var_05    C14  C13  C4   C5   -123.31  30.0  2
 31R  Var_06    C20  C19  C9   C8    -80.27  30.0  2
 31R  Var_07    C21  C20  C19  C9    179.57  30.0  1
 31R  Var_08    O22  C21  C20  C19    -4.64  30.0  2

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
 31R  plan-1  C4   0.020
 31R  plan-1  C13  0.020
 31R  plan-1  C14  0.020
 31R  plan-1  C15  0.020
 31R  plan-1  C16  0.020
 31R  plan-1  C17  0.020
 31R  plan-1  C18  0.020
 31R  plan-1  H4   0.020
 31R  plan-1  H5   0.020
 31R  plan-1  H6   0.020
 31R  plan-1  H7   0.020
 31R  plan-1  H8   0.020
 31R  plan-2  O1   0.020
 31R  plan-2  C2   0.020
 31R  plan-2  C7   0.020
 31R  plan-2  C8   0.020
 31R  plan-2  O12  0.020
 31R  plan-2  C4   0.020
 31R  plan-2  C3   0.020
 31R  plan-2  C10  0.020
 31R  plan-2  C9   0.020
 31R  plan-2  C19  0.020
 31R  plan-2  H1   0.020
 31R  plan-2  H9   0.020
 31R  plan-3  C20  0.020
 31R  plan-3  C21  0.020
 31R  plan-3  O23  0.020
 31R  plan-3  O22  0.020
 31R  plan-4  O11  0.020
 31R  plan-4  C6   0.020
 31R  plan-4  O1   0.020
 31R  plan-4  C5   0.020

