# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 19:11:39 2020
#   Inital geometry file: a 71 line input string
#   Ligand name: 2-(4-amino-2-chlorophenoxy)-5-chlorophenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1ccc(Oc2ccc(Cl)cc2O)c(Cl)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
 TN5  TN5  2-(4-amino-2-chlorophenoxy)-5-chlorophenol  ligand  26  17  .  2021-08-23  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_TN5
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
 TN5  CL13  CL  CL    0  -0.125   5.2925  -0.0736   0.1837
 TN5  C12   C   CR6   0  -0.031   3.5928  -0.3207  -0.0470
 TN5  C11   C   CR16  0  -0.244   3.0999  -0.5096  -1.3253
 TN5  C10   C   CR16  0  -0.320   1.7328  -0.6987  -1.4840
 TN5  C9    C   CR6   0   0.250   0.8889  -0.7122  -0.3907
 TN5  C8    C   CR6   0   0.327   1.3994  -0.5294   0.9000
 TN5  O2    O   OH1   0  -0.609   0.5296  -0.5593   1.9181
 TN5  C7    C   CR16  0  -0.343   2.7641  -0.3271   1.0653
 TN5  O1    O   O2    0  -0.497  -0.4436  -0.9597  -0.5659
 TN5  C1    C   CR6   0   0.410  -1.3262   0.0526  -0.3211
 TN5  C6    C   CR16  0  -0.330  -0.9945   1.3989  -0.3519
 TN5  C5    C   CR16  0  -0.315  -1.9530   2.3721  -0.1239
 TN5  C4    C   CR6   0   0.290  -3.2830   2.0298   0.1365
 TN5  N1    N   NH2   0  -0.862  -4.2284   2.9947   0.4238
 TN5  C3    C   CR16  0  -0.288  -3.6174   0.6728   0.1544
 TN5  C2    C   CR6   0  -0.133  -2.6479  -0.2900  -0.0663
 TN5  CL14  CL  CL    0  -0.115  -3.0896  -1.9622  -0.0311
 TN5  H11   H   HCR6  0   0.282   3.7558  -0.5025  -2.1838
 TN5  H10   H   HCR6  0   0.283   1.3197  -0.8470  -2.4734
 TN5  HO2   H   HOH1  0   0.484   0.9844  -0.4341   2.7593
 TN5  H7    H   HCR6  0   0.298   3.1750  -0.1817   2.0570
 TN5  H6    H   HCR6  0   0.282   0.0231   1.7037  -0.5622
 TN5  H5    H   HCR6  0   0.267  -1.6615   3.4148  -0.1548
 TN5  HN11  H   HNH2  0   0.380  -4.0228   3.9146   0.0676
 TN5  HN12  H   HNH2  0   0.380  -5.1834   2.7355   0.2347
 TN5  H3    H   HCR6  0   0.279  -4.6369   0.3663   0.3518

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
 TN5  CL13  C12   single    1.733  0.020  1.733
 TN5  C12   C11   aromatic  1.383  0.020  1.383
 TN5  C12   C7    aromatic  1.387  0.020  1.387
 TN5  C11   C10   aromatic  1.389  0.020  1.389
 TN5  C11   H11   single    0.930  0.020  1.080
 TN5  C10   C9    aromatic  1.381  0.020  1.381
 TN5  C10   H10   single    0.930  0.020  1.080
 TN5  C9    C8    aromatic  1.400  0.020  1.400
 TN5  C9    O1    single    1.367  0.020  1.367
 TN5  C8    O2    single    1.339  0.020  1.339
 TN5  C8    C7    aromatic  1.390  0.020  1.390
 TN5  O2    HO2   single    0.850  0.020  0.980
 TN5  C7    H7    single    0.930  0.020  1.080
 TN5  O1    C1    single    1.365  0.020  1.365
 TN5  C1    C6    aromatic  1.387  0.020  1.387
 TN5  C1    C2    aromatic  1.389  0.020  1.389
 TN5  C6    C5    aromatic  1.385  0.020  1.385
 TN5  C6    H6    single    0.930  0.020  1.080
 TN5  C5    C4    aromatic  1.398  0.020  1.398
 TN5  C5    H5    single    0.930  0.020  1.080
 TN5  C4    N1    single    1.381  0.020  1.381
 TN5  C4    C3    aromatic  1.398  0.020  1.398
 TN5  N1    HN11  single    0.890  0.020  1.040
 TN5  N1    HN12  single    0.890  0.020  1.040
 TN5  C3    C2    aromatic  1.384  0.020  1.384
 TN5  C3    H3    single    0.930  0.020  1.080
 TN5  C2    CL14  single    1.730  0.020  1.730

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
 TN5  C7    C12  C11   121.84  3.000
 TN5  C7    C12  CL13  118.67  3.000
 TN5  C11   C12  CL13  119.48  3.000
 TN5  H11   C11  C10   120.50  3.000
 TN5  H11   C11  C12   121.14  3.000
 TN5  C10   C11  C12   118.36  3.000
 TN5  H10   C10  C9    119.28  3.000
 TN5  H10   C10  C11   119.91  3.000
 TN5  C9    C10  C11   120.81  3.000
 TN5  O1    C9   C8    119.83  3.000
 TN5  O1    C9   C10   119.74  3.000
 TN5  C8    C9   C10   120.38  3.000
 TN5  C7    C8   O2    123.41  3.000
 TN5  C7    C8   C9    119.13  3.000
 TN5  O2    C8   C9    117.46  3.000
 TN5  HO2   O2   C8    110.72  3.000
 TN5  H7    C7   C8    120.06  3.000
 TN5  H7    C7   C12   120.46  3.000
 TN5  C8    C7   C12   119.48  3.000
 TN5  C1    O1   C9    118.23  3.000
 TN5  C2    C1   C6    118.11  3.000
 TN5  C2    C1   O1    117.72  3.000
 TN5  C6    C1   O1    124.14  3.000
 TN5  H6    C6   C5    118.99  3.000
 TN5  H6    C6   C1    120.15  3.000
 TN5  C5    C6   C1    120.86  3.000
 TN5  H5    C5   C4    119.81  3.000
 TN5  H5    C5   C6    119.05  3.000
 TN5  C4    C5   C6    121.14  3.000
 TN5  C3    C4   N1    120.79  3.000
 TN5  C3    C4   C5    117.89  3.000
 TN5  N1    C4   C5    121.26  3.000
 TN5  HN12  N1   HN11  111.22  3.000
 TN5  HN12  N1   C4    115.47  3.000
 TN5  HN11  N1   C4    115.12  3.000
 TN5  H3    C3   C2    119.45  3.000
 TN5  H3    C3   C4    120.16  3.000
 TN5  C2    C3   C4    120.38  3.000
 TN5  CL14  C2   C3    119.36  3.000
 TN5  CL14  C2   C1    119.02  3.000
 TN5  C3    C2   C1    121.62  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
 TN5  CONST_01  C9    C10  C11  C12     0.00   0.0  0
 TN5  CONST_02  C9    C8   C7   C12     0.00   0.0  0
 TN5  CONST_03  C8    C7   C12  C11     0.00   0.0  0
 TN5  CONST_04  C8    C9   C10  C11     0.00   0.0  0
 TN5  CONST_05  C7    C12  C11  C10     0.00   0.0  0
 TN5  CONST_06  C7    C8   C9   C10     0.00   0.0  0
 TN5  CONST_07  C4    C5   C6   C1      0.00   0.0  0
 TN5  CONST_08  C4    C3   C2   C1      0.00   0.0  0
 TN5  CONST_09  C3    C2   C1   C6      0.00   0.0  0
 TN5  CONST_10  C3    C4   C5   C6      0.00   0.0  0
 TN5  CONST_11  C2    C1   C6   C5      0.00   0.0  0
 TN5  CONST_12  C2    C3   C4   C5      0.00   0.0  0
 TN5  CONST_13  C10   C11  C12  CL13  180.00   0.0  0
 TN5  CONST_14  C8    C7   C12  CL13  180.00   0.0  0
 TN5  CONST_15  O2    C8   C7   C12   180.00   0.0  0
 TN5  CONST_16  O1    C9   C10  C11   180.00   0.0  0
 TN5  CONST_17  O2    C8   C9   C10   180.00   0.0  0
 TN5  CONST_18  O1    C9   C8   C7    180.00   0.0  0
 TN5  CONST_19  C5    C6   C1   O1    180.00   0.0  0
 TN5  CONST_20  C3    C2   C1   O1    180.00   0.0  0
 TN5  CONST_21  CL14  C2   C1   C6    180.00   0.0  0
 TN5  CONST_22  N1    C4   C5   C6    180.00   0.0  0
 TN5  CONST_23  CL14  C2   C3   C4    180.00   0.0  0
 TN5  CONST_24  C2    C3   C4   N1    180.00   0.0  0
 TN5  CONST_25  H10   C10  C11  C12   180.00   0.0  0
 TN5  CONST_26  H7    C7   C12  C11   180.00   0.0  0
 TN5  CONST_27  H11   C11  C10  C9    180.00   0.0  0
 TN5  CONST_28  H5    C5   C6   C1    180.00   0.0  0
 TN5  CONST_29  H3    C3   C2   C1    180.00   0.0  0
 TN5  CONST_30  H6    C6   C5   C4    180.00   0.0  0
 TN5  Var_01    C6    C1   O1   C9     22.91  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
 TN5  plan-1  CL13  0.020
 TN5  plan-1  C12   0.020
 TN5  plan-1  C11   0.020
 TN5  plan-1  C10   0.020
 TN5  plan-1  C9    0.020
 TN5  plan-1  C8    0.020
 TN5  plan-1  O2    0.020
 TN5  plan-1  C7    0.020
 TN5  plan-1  O1    0.020
 TN5  plan-1  H11   0.020
 TN5  plan-1  H10   0.020
 TN5  plan-1  H7    0.020
 TN5  plan-2  O1    0.020
 TN5  plan-2  C1    0.020
 TN5  plan-2  C6    0.020
 TN5  plan-2  C5    0.020
 TN5  plan-2  C4    0.020
 TN5  plan-2  N1    0.020
 TN5  plan-2  C3    0.020
 TN5  plan-2  C2    0.020
 TN5  plan-2  CL14  0.020
 TN5  plan-2  H6    0.020
 TN5  plan-2  H5    0.020
 TN5  plan-2  H3    0.020
 TN5  plan-3  C4    0.020
 TN5  plan-3  N1    0.020
 TN5  plan-3  HN11  0.020
 TN5  plan-3  HN12  0.020

