# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  9 06:09:57 2020
#   Inital geometry file: a 65 line input string
#   Ligand name: 4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CNC[C@@H](O)c1ccc(O)c(O)c1
#
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
 XDE  XDE  4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol  ligand  26  13  .  2021-08-24  2021-08-24  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_XDE
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
 XDE  C1   C  CR6   0   0.146  -0.0712  -0.1046   0.4600
 XDE  C2   C  CR16  0  -0.393   0.8148   0.9088   0.8136
 XDE  C3   C  CR6   0   0.320   2.1601   0.8365   0.4873
 XDE  C4   C  CR6   0   0.248   2.6409  -0.2881  -0.1906
 XDE  C5   C  CR16  0  -0.325   1.7681  -1.3019  -0.5420
 XDE  C6   C  CR16  0  -0.314   0.4194  -1.2098  -0.2248
 XDE  O1   O  OH1   0  -0.621   2.9813   1.8509   0.8305
 XDE  O2   O  OH1   0  -0.634   3.9701  -0.2915  -0.4645
 XDE  O3   O  OH1   0  -0.625  -2.0040  -1.0635   1.5881
 XDE  C9   C  CH3   0  -0.494  -4.6014   0.6330  -1.2782
 XDE  C8   C  CH2   0  -0.249  -2.3796   0.2055  -0.4526
 XDE  C7   C  CH1   0  -0.082  -1.5365   0.0164   0.8048
 XDE  H1   H  HCR6  0   0.243   0.4576   1.7824   1.3467
 XDE  H2   H  HCR6  0   0.239   2.1331  -2.1727  -1.0739
 XDE  H3   H  HCR6  0   0.212  -0.2302  -2.0164  -0.5435
 XDE  H4   H  HOH1  0   0.454   3.8889   1.6312   0.5969
 XDE  H5   H  HOH1  0   0.450   4.2376  -1.1394  -0.8275
 XDE  H6   H  HOH1  0   0.419  -1.7631  -1.8874   1.1561
 XDE  H7   H  HCH3  0   0.176  -4.5668  -0.2134  -1.9804
 XDE  H8   H  HCH3  0   0.222  -5.6364   0.7644  -0.9635
 XDE  H9   H  HCH3  0   0.214  -4.3177   1.5280  -1.8356
 XDE  H10  H  HNH1  0   0.330  -4.1098  -0.2483   0.4804
 XDE  H12  H  HCH2  0   0.167  -2.2575  -0.6742  -1.1138
 XDE  H13  H  HCH2  0   0.221  -1.9733   1.0545  -1.0107
 XDE  H14  H  HCH1  0   0.237  -1.6789   0.9027   1.4291
 XDE  N1   N  NH1   0  -0.563  -3.7535   0.4826  -0.1199

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
 XDE  O3  C7   single    1.414  0.020  1.414
 XDE  C7  C8   single    1.526  0.020  1.526
 XDE  C7  C1   single    1.510  0.020  1.510
 XDE  C2  C1   aromatic  1.392  0.020  1.392
 XDE  C2  C3   aromatic  1.386  0.020  1.386
 XDE  O1  C3   single    1.350  0.020  1.350
 XDE  C8  N1   single    1.440  0.020  1.440
 XDE  C1  C6   aromatic  1.390  0.020  1.390
 XDE  C3  C4   aromatic  1.398  0.020  1.398
 XDE  N1  C9   single    1.443  0.020  1.443
 XDE  C6  C5   aromatic  1.389  0.020  1.389
 XDE  C4  C5   aromatic  1.383  0.020  1.383
 XDE  C4  O2   single    1.357  0.020  1.357
 XDE  C2  H1   single    0.930  0.020  1.080
 XDE  C5  H2   single    0.930  0.020  1.080
 XDE  C6  H3   single    0.930  0.020  1.080
 XDE  O1  H4   single    0.850  0.020  0.980
 XDE  O2  H5   single    0.850  0.020  0.980
 XDE  O3  H6   single    0.850  0.020  0.980
 XDE  C9  H7   single    0.970  0.020  1.090
 XDE  C9  H8   single    0.970  0.020  1.090
 XDE  C9  H9   single    0.970  0.020  1.090
 XDE  N1  H10  single    0.890  0.020  1.040
 XDE  C8  H12  single    0.970  0.020  1.090
 XDE  C8  H13  single    0.970  0.020  1.090
 XDE  C7  H14  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
 XDE  C7   C1  C6   121.25  3.000
 XDE  C6   C1  C2   118.65  3.000
 XDE  C7   C1  C2   120.09  3.000
 XDE  H1   C2  C3   118.53  3.000
 XDE  H1   C2  C1   120.13  3.000
 XDE  C3   C2  C1   121.34  3.000
 XDE  O1   C3  C4   121.24  3.000
 XDE  C4   C3  C2   119.32  3.000
 XDE  O1   C3  C2   119.44  3.000
 XDE  O2   C4  C5   124.40  3.000
 XDE  O2   C4  C3   115.89  3.000
 XDE  C5   C4  C3   119.71  3.000
 XDE  H2   C5  C6   119.51  3.000
 XDE  H2   C5  C4   120.07  3.000
 XDE  C6   C5  C4   120.41  3.000
 XDE  H3   C6  C5   117.76  3.000
 XDE  H3   C6  C1   121.69  3.000
 XDE  C5   C6  C1   120.55  3.000
 XDE  H4   O1  C3   109.91  3.000
 XDE  H5   O2  C4   110.57  3.000
 XDE  H6   O3  C7   108.84  3.000
 XDE  H9   C9  H8   107.18  3.000
 XDE  H9   C9  H7   107.25  3.000
 XDE  H8   C9  H7   107.87  3.000
 XDE  H9   C9  N1   110.03  3.000
 XDE  H8   C9  N1   109.80  3.000
 XDE  H7   C9  N1   114.43  3.000
 XDE  H13  C8  H12  105.71  3.000
 XDE  H13  C8  C7   108.14  3.000
 XDE  H12  C8  C7   109.43  3.000
 XDE  H13  C8  N1   108.83  3.000
 XDE  H12  C8  N1   113.33  3.000
 XDE  C7   C8  N1   111.14  3.000
 XDE  H14  C7  C8   107.34  3.000
 XDE  H14  C7  O3   105.05  3.000
 XDE  C8   C7  O3   111.63  3.000
 XDE  H14  C7  C1   108.77  3.000
 XDE  C8   C7  C1   110.98  3.000
 XDE  O3   C7  C1   112.72  3.000
 XDE  H10  N1  C8   109.53  3.000
 XDE  H10  N1  C9   110.18  3.000
 XDE  C8   N1  C9   113.26  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
 XDE  CONST_01  C4  C3  C2  C1     0.00   0.0  0
 XDE  CONST_02  C4  C5  C6  C1     0.00   0.0  0
 XDE  CONST_03  C5  C6  C1  C2     0.00   0.0  0
 XDE  CONST_04  C5  C4  C3  C2     0.00   0.0  0
 XDE  CONST_05  C6  C1  C2  C3     0.00   0.0  0
 XDE  CONST_06  C6  C5  C4  C3     0.00   0.0  0
 XDE  CONST_07  O1  C3  C2  C1   180.00   0.0  0
 XDE  CONST_08  O2  C4  C3  C2   180.00   0.0  0
 XDE  CONST_09  C7  C1  C2  C3   180.00   0.0  0
 XDE  CONST_10  C7  C1  C6  C5   180.00   0.0  0
 XDE  CONST_11  O1  C3  C4  C5   180.00   0.0  0
 XDE  CONST_12  O2  C4  C5  C6   180.00   0.0  0
 XDE  CONST_13  H2  C5  C6  C1   180.00   0.0  0
 XDE  CONST_14  H3  C6  C1  C2   180.00   0.0  0
 XDE  CONST_15  H1  C2  C3  C4   180.00   0.0  0
 XDE  Var_01    C7  C8  N1  C9  -178.38  30.0  1
 XDE  Var_02    H7  C9  N1  C8    54.25  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 XDE  chir_01  C7  O3  C8  C1  positiv

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
 XDE  plan-1  C1  0.020
 XDE  plan-1  C2  0.020
 XDE  plan-1  C3  0.020
 XDE  plan-1  C4  0.020
 XDE  plan-1  C5  0.020
 XDE  plan-1  C6  0.020
 XDE  plan-1  O1  0.020
 XDE  plan-1  O2  0.020
 XDE  plan-1  C7  0.020
 XDE  plan-1  H1  0.020
 XDE  plan-1  H2  0.020
 XDE  plan-1  H3  0.020

