# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 22 16:10:29 2022
#   Inital geometry file: a 82 line input string
#   Ligand name: 2-[(3-chloro-2-methylphenyl)amino]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1c(Cl)cccc1Nc2ccccc2C(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
 TLF  TLF  '2-[(3-chloro-2-methylphenyl)amino]benzoic acid'  ligand  29  18  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_TLF
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
 TLF  C4   C   CR16   0  -0.277   1.8137  -0.6032   2.4844
 TLF  C5   C   CR16   0  -0.309   0.6614  -0.4118   1.7427
 TLF  C6   C   CR6    0   0.295   0.7233  -0.2805   0.3527
 TLF  C8   C   CR6    0   0.354  -1.7076  -0.3670  -0.1721
 TLF  C9   C   CR16   0  -0.337  -2.0695  -1.4210   0.6807
 TLF  C10  C   CR16   0  -0.255  -3.3979  -1.7393   0.8943
 TLF  C11  C   CR16   0  -0.279  -4.4070  -1.0248   0.2598
 TLF  C12  C   CR16   0  -0.282  -4.0544  -0.0026  -0.6052
 TLF  C13  C   CR6    0  -0.232  -2.7277   0.3462  -0.8477
 TLF  C14  C   C      0   0.452  -2.4432   1.4563  -1.8476
 TLF  O16  O   OC    -1  -0.570  -3.4139   2.0747  -2.3078
 TLF  O15  O   O      0  -0.603  -1.2391   1.6676  -2.1555
 TLF  N7   N   NH1    0  -0.821  -0.3937  -0.0479  -0.4281
 TLF  C1   C   CR6    0   0.090   1.9745  -0.3293  -0.3033
 TLF  C17  C   CH3    0  -0.736   2.0338  -0.1907  -1.7947
 TLF  C2   C   CR6    0  -0.106   3.1057  -0.4937   0.4892
 TLF  CL   CL  CL     0  -0.142   4.6842  -0.5244  -0.2483
 TLF  C3   C   CR16   0  -0.236   3.0526  -0.6444   1.8674
 TLF  H1   H   HCR6   0   0.262   1.7477  -0.6995   3.5601
 TLF  H2   H   HCR6   0   0.274  -0.2883  -0.3373   2.2540
 TLF  H3   H   HCR6   0   0.269  -1.3049  -2.0153   1.1620
 TLF  H4   H   HCR6   0   0.251  -3.6423  -2.5623   1.5544
 TLF  H5   H   HCR6   0   0.242  -5.4472  -1.2710   0.4270
 TLF  H6   H   HCR6   0   0.245  -4.8277   0.5522  -1.1194
 TLF  H8   H   HNH1   0   0.427  -0.3376   0.6401  -1.1949
 TLF  H9   H   HCH3   0   0.254   1.9654   0.8562  -2.1020
 TLF  H10  H   HCH3   0   0.253   2.9567  -0.5879  -2.2082
 TLF  H11  H   HCH3   0   0.249   1.2019  -0.7165  -2.2631
 TLF  H12  H   HCR6   0   0.270   3.9573  -0.7808   2.4430

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
 TLF  CL   C2   single    1.743  0.020  1.743
 TLF  C2   C3   aromatic  1.387  0.020  1.387
 TLF  C2   C1   aromatic  1.391  0.020  1.391
 TLF  C3   C4   aromatic  1.385  0.020  1.385
 TLF  C1   C17  single    1.499  0.020  1.499
 TLF  C1   C6   aromatic  1.414  0.020  1.414
 TLF  C4   C5   aromatic  1.384  0.020  1.384
 TLF  C6   C5   aromatic  1.398  0.020  1.398
 TLF  C6   N7   single    1.382  0.020  1.382
 TLF  N7   C8   single    1.376  0.020  1.376
 TLF  C8   C9   aromatic  1.403  0.020  1.403
 TLF  C8   C13  aromatic  1.416  0.020  1.416
 TLF  C9   C10  aromatic  1.383  0.020  1.383
 TLF  O15  C14  deloc     1.261  0.020  1.261
 TLF  O16  C14  deloc     1.240  0.020  1.240
 TLF  C14  C13  single    1.521  0.020  1.521
 TLF  C13  C12  aromatic  1.393  0.020  1.393
 TLF  C10  C11  aromatic  1.390  0.020  1.390
 TLF  C12  C11  aromatic  1.385  0.020  1.385
 TLF  C4   H1   single    0.930  0.020  1.080
 TLF  C5   H2   single    0.930  0.020  1.080
 TLF  C9   H3   single    0.930  0.020  1.080
 TLF  C10  H4   single    0.930  0.020  1.080
 TLF  C11  H5   single    0.930  0.020  1.080
 TLF  C12  H6   single    0.930  0.020  1.080
 TLF  N7   H8   single    0.860  0.020  1.020
 TLF  C17  H9   single    0.970  0.020  1.090
 TLF  C17  H10  single    0.970  0.020  1.090
 TLF  C17  H11  single    0.970  0.020  1.090
 TLF  C3   H12  single    0.930  0.020  1.080

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
 TLF  H1   C4   C3   119.66  3.000
 TLF  H1   C4   C5   119.63  3.000
 TLF  C3   C4   C5   120.69  3.000
 TLF  H2   C5   C6   120.19  3.000
 TLF  H2   C5   C4   119.18  3.000
 TLF  C6   C5   C4   120.61  3.000
 TLF  C1   C6   N7   117.31  3.000
 TLF  N7   C6   C5   122.80  3.000
 TLF  C1   C6   C5   119.83  3.000
 TLF  N7   C8   C13  118.83  3.000
 TLF  C13  C8   C9   118.84  3.000
 TLF  N7   C8   C9   122.24  3.000
 TLF  H3   C9   C10  118.95  3.000
 TLF  H3   C9   C8   120.06  3.000
 TLF  C10  C9   C8   120.97  3.000
 TLF  H4   C10  C11  120.34  3.000
 TLF  H4   C10  C9   119.07  3.000
 TLF  C11  C10  C9   120.58  3.000
 TLF  H5   C11  C12  120.62  3.000
 TLF  H5   C11  C10  120.70  3.000
 TLF  C12  C11  C10  118.67  3.000
 TLF  H6   C12  C13  118.01  3.000
 TLF  H6   C12  C11  119.57  3.000
 TLF  C13  C12  C11  122.42  3.000
 TLF  C14  C13  C12  118.38  3.000
 TLF  C12  C13  C8   118.48  3.000
 TLF  C14  C13  C8   123.13  3.000
 TLF  O15  C14  O16  125.01  3.000
 TLF  O16  C14  C13  117.50  3.000
 TLF  O15  C14  C13  117.49  3.000
 TLF  H8   N7   C8   110.17  3.000
 TLF  H8   N7   C6   119.21  3.000
 TLF  C8   N7   C6   128.85  3.000
 TLF  C2   C1   C17  123.07  3.000
 TLF  C17  C1   C6   119.57  3.000
 TLF  C2   C1   C6   117.36  3.000
 TLF  H11  C17  H10  107.96  3.000
 TLF  H11  C17  H9   107.07  3.000
 TLF  H10  C17  H9   107.24  3.000
 TLF  H11  C17  C1   110.65  3.000
 TLF  H10  C17  C1   112.24  3.000
 TLF  H9   C17  C1   111.46  3.000
 TLF  C3   C2   CL   116.95  3.000
 TLF  C3   C2   C1   123.21  3.000
 TLF  CL   C2   C1   119.84  3.000
 TLF  H12  C3   C2   120.71  3.000
 TLF  H12  C3   C4   121.02  3.000
 TLF  C2   C3   C4   118.27  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
 TLF  CONST_01  C1   C2   C3   C4     0.00   0.0  0
 TLF  CONST_02  C1   C6   C5   C4     0.00   0.0  0
 TLF  CONST_03  C2   C3   C4   C5     0.00   0.0  0
 TLF  CONST_04  C2   C1   C6   C5     0.00   0.0  0
 TLF  CONST_05  C3   C2   C1   C6     0.00   0.0  0
 TLF  CONST_06  C3   C4   C5   C6     0.00   0.0  0
 TLF  CONST_07  C11  C10  C9   C8     0.00   0.0  0
 TLF  CONST_08  C11  C12  C13  C8     0.00   0.0  0
 TLF  CONST_09  C12  C13  C8   C9     0.00   0.0  0
 TLF  CONST_10  C12  C11  C10  C9     0.00   0.0  0
 TLF  CONST_11  C13  C8   C9   C10    0.00   0.0  0
 TLF  CONST_12  C13  C12  C11  C10    0.00   0.0  0
 TLF  CONST_13  CL   C2   C3   C4   180.00   0.0  0
 TLF  CONST_14  N7   C6   C5   C4   180.00   0.0  0
 TLF  CONST_15  C17  C1   C6   C5   180.00   0.0  0
 TLF  CONST_16  CL   C2   C1   C6   180.00   0.0  0
 TLF  CONST_17  C14  C13  C8   C9   180.00   0.0  0
 TLF  CONST_18  N7   C8   C9   C10  180.00   0.0  0
 TLF  CONST_19  C14  C13  C12  C11  180.00   0.0  0
 TLF  CONST_20  N7   C8   C13  C12  180.00   0.0  0
 TLF  CONST_21  C2   C1   C6   N7   180.00   0.0  0
 TLF  CONST_22  C3   C2   C1   C17  180.00   0.0  0
 TLF  CONST_23  H12  C3   C4   C5   180.00   0.0  0
 TLF  CONST_24  H1   C4   C5   C6   180.00   0.0  0
 TLF  CONST_25  H4   C10  C9   C8   180.00   0.0  0
 TLF  CONST_26  H6   C12  C13  C8   180.00   0.0  0
 TLF  CONST_27  H5   C11  C10  C9   180.00   0.0  0
 TLF  CONST_28  H3   C9   C10  C11  180.00   0.0  0
 TLF  CONST_29  H2   C5   C6   C1   180.00   0.0  0
 TLF  Var_01    C8   N7   C6   C5   -25.88  30.0  2
 TLF  Var_02    C9   C8   N7   C6   -25.23  30.0  2
 TLF  Var_03    O15  C14  C13  C8     5.66  30.0  2
 TLF  Var_04    H9   C17  C1   C6    80.14  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
 TLF  plan-1  C8   0.020
 TLF  plan-1  C9   0.020
 TLF  plan-1  C10  0.020
 TLF  plan-1  C11  0.020
 TLF  plan-1  C12  0.020
 TLF  plan-1  C13  0.020
 TLF  plan-1  C14  0.020
 TLF  plan-1  N7   0.020
 TLF  plan-1  H3   0.020
 TLF  plan-1  H4   0.020
 TLF  plan-1  H5   0.020
 TLF  plan-1  H6   0.020
 TLF  plan-2  C4   0.020
 TLF  plan-2  C5   0.020
 TLF  plan-2  C6   0.020
 TLF  plan-2  N7   0.020
 TLF  plan-2  C1   0.020
 TLF  plan-2  C17  0.020
 TLF  plan-2  C2   0.020
 TLF  plan-2  CL   0.020
 TLF  plan-2  C3   0.020
 TLF  plan-2  H1   0.020
 TLF  plan-2  H2   0.020
 TLF  plan-2  H12  0.020
 TLF  plan-3  C13  0.020
 TLF  plan-3  C14  0.020
 TLF  plan-3  O16  0.020
 TLF  plan-3  O15  0.020

