# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 17:58:12 2020
#   Inital geometry file: a 74 line input string
#   Ligand name: 5-chloro-2-(2-chloro-4-nitrophenoxy)phenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(Cl)ccc1Oc2ccc(cc2Cl)[N+]([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
 TN2  TN2  5-chloro-2-(2-chloro-4-nitrophenoxy)phenol  ligand  26  19  .  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_TN2
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
 TN2  O19   O   O     -1  -0.379  -4.1537  -3.0886  -0.0448
 TN2  N17   N   N      1   0.329  -4.2832  -1.8867  -0.0585
 TN2  O18   O   O      0  -0.380  -5.3473  -1.3239  -0.1729
 TN2  C14   C   CR6    0   0.238  -3.0915  -1.0731   0.0690
 TN2  C13   C   CR16   0  -0.228  -3.2160   0.3095   0.0450
 TN2  C11   C   CR6    0  -0.139  -2.0796   1.0789   0.1627
 TN2  CL12  CL  CL     0  -0.079  -2.1958   2.7957   0.1348
 TN2  C15   C   CR16   0  -0.253  -1.8559  -1.6843   0.2133
 TN2  C16   C   CR16   0  -0.344  -0.7236  -0.9021   0.3316
 TN2  C10   C   CR6    0   0.479  -0.8212   0.4848   0.3053
 TN2  O9    O   O2     0  -0.476   0.2230   1.3165   0.4355
 TN2  C6    C   CR6    0   0.238   1.5011   0.8203   0.3344
 TN2  C4    C   CR6    0   0.333   2.0006   0.4916  -0.9282
 TN2  O5    O   OH1    0  -0.608   1.1691   0.6117  -1.9698
 TN2  C3    C   CR16   0  -0.340   3.3157   0.0561  -1.0367
 TN2  C7    C   CR16   0  -0.306   2.2910   0.7175   1.4610
 TN2  C8    C   CR16   0  -0.243   3.6069   0.2874   1.3576
 TN2  C2    C   CR6    0  -0.027   4.0974  -0.0373   0.1047
 TN2  CL20  CL  CL     0  -0.118   5.7354  -0.5750  -0.0527
 TN2  H13   H   HCR6   0   0.319  -4.1780   0.7870  -0.0705
 TN2  H15   H   HCR6   0   0.309  -1.7598  -2.7595   0.2382
 TN2  H16   H   HCR6   0   0.307   0.2367  -1.3837   0.4572
 TN2  HO5   H   HOH1   0   0.487   1.6041   0.3485  -2.7893
 TN2  H3    H   HCR6   0   0.303   3.7231  -0.2030  -2.0062
 TN2  H7    H   HCR6   0   0.290   1.8799   0.9809   2.4267
 TN2  H8    H   HCR6   0   0.286   4.2272   0.2066   2.2384

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
 TN2  O19  N17   single    1.209  0.020  1.209
 TN2  N17  O18   double    1.209  0.020  1.209
 TN2  N17  C14   single    1.449  0.020  1.449
 TN2  C14  C13   aromatic  1.388  0.020  1.388
 TN2  C14  C15   aromatic  1.386  0.020  1.386
 TN2  C13  C11   aromatic  1.377  0.020  1.377
 TN2  C13  H13   single    0.930  0.020  1.080
 TN2  C11  CL12  single    1.721  0.020  1.721
 TN2  C11  C10   aromatic  1.399  0.020  1.399
 TN2  C15  C16   aromatic  1.381  0.020  1.381
 TN2  C15  H15   single    0.930  0.020  1.080
 TN2  C16  C10   aromatic  1.391  0.020  1.391
 TN2  C16  H16   single    0.930  0.020  1.080
 TN2  C10  O9    single    1.341  0.020  1.341
 TN2  O9   C6    single    1.375  0.020  1.375
 TN2  C6   C4    aromatic  1.397  0.020  1.397
 TN2  C6   C7    aromatic  1.380  0.020  1.380
 TN2  C4   O5    single    1.338  0.020  1.338
 TN2  C4   C3    aromatic  1.390  0.020  1.390
 TN2  O5   HO5   single    0.850  0.020  0.980
 TN2  C3   C2    aromatic  1.387  0.020  1.387
 TN2  C3   H3    single    0.930  0.020  1.080
 TN2  C7   C8    aromatic  1.388  0.020  1.388
 TN2  C7   H7    single    0.930  0.020  1.080
 TN2  C8   C2    aromatic  1.384  0.020  1.384
 TN2  C8   H8    single    0.930  0.020  1.080
 TN2  C2   CL20  single    1.731  0.020  1.731

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
 TN2  C14   N17  O18   118.09  3.000
 TN2  C14   N17  O19   117.99  3.000
 TN2  O18   N17  O19   123.92  3.000
 TN2  C15   C14  C13   121.39  3.000
 TN2  C15   C14  N17   119.66  3.000
 TN2  C13   C14  N17   118.95  3.000
 TN2  H13   C13  C11   119.80  3.000
 TN2  H13   C13  C14   121.46  3.000
 TN2  C11   C13  C14   118.74  3.000
 TN2  C10   C11  CL12  119.08  3.000
 TN2  C10   C11  C13   120.91  3.000
 TN2  CL12  C11  C13   120.01  3.000
 TN2  H15   C15  C16   119.28  3.000
 TN2  H15   C15  C14   121.39  3.000
 TN2  C16   C15  C14   119.34  3.000
 TN2  H16   C16  C10   120.57  3.000
 TN2  H16   C16  C15   119.05  3.000
 TN2  C10   C16  C15   120.38  3.000
 TN2  O9    C10  C16   124.20  3.000
 TN2  O9    C10  C11   116.54  3.000
 TN2  C16   C10  C11   119.25  3.000
 TN2  C6    O9   C10   119.52  3.000
 TN2  C7    C6   C4    121.05  3.000
 TN2  C7    C6   O9    119.94  3.000
 TN2  C4    C6   O9    118.93  3.000
 TN2  C3    C4   O5    123.74  3.000
 TN2  C3    C4   C6    118.86  3.000
 TN2  O5    C4   C6    117.40  3.000
 TN2  HO5   O5   C4    110.90  3.000
 TN2  H3    C3   C2    120.57  3.000
 TN2  H3    C3   C4    120.06  3.000
 TN2  C2    C3   C4    119.37  3.000
 TN2  H7    C7   C8    120.13  3.000
 TN2  H7    C7   C6    119.54  3.000
 TN2  C8    C7   C6    120.32  3.000
 TN2  H8    C8   C2    121.13  3.000
 TN2  H8    C8   C7    120.44  3.000
 TN2  C2    C8   C7    118.42  3.000
 TN2  CL20  C2   C8    119.37  3.000
 TN2  CL20  C2   C3    118.66  3.000
 TN2  C8    C2   C3    121.97  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
 TN2  CONST_01  C10   C11  C13  C14     0.00   0.0  0
 TN2  CONST_02  C10   C16  C15  C14     0.00   0.0  0
 TN2  CONST_03  C16   C15  C14  C13     0.00   0.0  0
 TN2  CONST_04  C16   C10  C11  C13     0.00   0.0  0
 TN2  CONST_05  C15   C14  C13  C11     0.00   0.0  0
 TN2  CONST_06  C15   C16  C10  C11     0.00   0.0  0
 TN2  CONST_07  C2    C3   C4   C6      0.00   0.0  0
 TN2  CONST_08  C2    C8   C7   C6      0.00   0.0  0
 TN2  CONST_09  C8    C7   C6   C4      0.00   0.0  0
 TN2  CONST_10  C8    C2   C3   C4      0.00   0.0  0
 TN2  CONST_11  C7    C6   C4   C3      0.00   0.0  0
 TN2  CONST_12  C7    C8   C2   C3      0.00   0.0  0
 TN2  CONST_13  C11   C13  C14  N17   180.00   0.0  0
 TN2  CONST_14  C16   C15  C14  N17   180.00   0.0  0
 TN2  CONST_15  CL12  C11  C13  C14   180.00   0.0  0
 TN2  CONST_16  O9    C10  C11  C13   180.00   0.0  0
 TN2  CONST_17  C16   C10  C11  CL12  180.00   0.0  0
 TN2  CONST_18  O9    C10  C16  C15   180.00   0.0  0
 TN2  CONST_19  C3    C4   C6   O9    180.00   0.0  0
 TN2  CONST_20  C8    C7   C6   O9    180.00   0.0  0
 TN2  CONST_21  CL20  C2   C3   C4    180.00   0.0  0
 TN2  CONST_22  C7    C6   C4   O5    180.00   0.0  0
 TN2  CONST_23  C2    C3   C4   O5    180.00   0.0  0
 TN2  CONST_24  CL20  C2   C8   C7    180.00   0.0  0
 TN2  CONST_25  H16   C16  C15  C14   180.00   0.0  0
 TN2  CONST_26  H15   C15  C14  C13   180.00   0.0  0
 TN2  CONST_27  H13   C13  C14  C15   180.00   0.0  0
 TN2  CONST_28  H3    C3   C4   C6    180.00   0.0  0
 TN2  CONST_29  H8    C8   C7   C6    180.00   0.0  0
 TN2  CONST_30  H7    C7   C6   C4    180.00   0.0  0
 TN2  CONST_31  C13   C14  N17  O19   180.00   0.0  0
 TN2  CONST_32  C15   C14  N17  O19     0.00   0.0  0
 TN2  CONST_33  C13   C14  N17  O18     0.00   0.0  0
 TN2  CONST_34  C15   C14  N17  O18   180.00   0.0  0
 TN2  Var_01    C4    C6   O9   C10    75.26  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
 TN2  plan-1  N17   0.020
 TN2  plan-1  C14   0.020
 TN2  plan-1  C13   0.020
 TN2  plan-1  C11   0.020
 TN2  plan-1  CL12  0.020
 TN2  plan-1  C15   0.020
 TN2  plan-1  C16   0.020
 TN2  plan-1  C10   0.020
 TN2  plan-1  O9    0.020
 TN2  plan-1  H13   0.020
 TN2  plan-1  H15   0.020
 TN2  plan-1  H16   0.020
 TN2  plan-2  O9    0.020
 TN2  plan-2  C6    0.020
 TN2  plan-2  C4    0.020
 TN2  plan-2  O5    0.020
 TN2  plan-2  C3    0.020
 TN2  plan-2  C7    0.020
 TN2  plan-2  C8    0.020
 TN2  plan-2  C2    0.020
 TN2  plan-2  CL20  0.020
 TN2  plan-2  H3    0.020
 TN2  plan-2  H7    0.020
 TN2  plan-2  H8    0.020
 TN2  plan-3  O19   0.020
 TN2  plan-3  N17   0.020
 TN2  plan-3  O18   0.020
 TN2  plan-3  C14   0.020

