# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 06:22:10 2020
#   Inital geometry file: a 86 line input string
#   Ligand name: 3-{[(4-chlorophenyl)acetyl]amino}pyridine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1ccncc1NC(=O)Cc2ccc(Cl)cc2
#
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
 6EO  6EO  '3-{[(4-chlorophenyl)acetyl]amino}pyridine-4-carboxylic acid'  ligand  31  20  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_6EO
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
 6EO  C10  C   CR16  0  -0.304  -2.9957  -0.1453   1.4291
 6EO  C15  C   CR16  0  -0.298  -2.6205  -1.2029  -0.6832
 6EO  C17  C   CR16  0  -0.121   2.5038   2.0169   0.1743
 6EO  C20  C   CR16  0  -0.325   4.8894   0.8893  -0.4353
 6EO  O01  O   O     0  -0.451   3.1360  -2.2487  -0.0509
 6EO  O03  O   OH1   0  -0.577   5.2479  -1.7754  -0.5501
 6EO  C04  C   CR6   0  -0.087   3.8160   0.0390  -0.1841
 6EO  C05  C   CR6   0   0.313   2.5678   0.6137   0.1302
 6EO  N06  N   NH1   0  -0.772   1.4739  -0.1974   0.3849
 6EO  C07  C   C     0   0.569   0.1808   0.1459   0.6447
 6EO  C08  C   CH2   0  -0.701  -0.7042  -1.0570   0.9284
 6EO  C09  C   CR6   0   0.156  -2.1344  -0.8036   0.5573
 6EO  C11  C   CR16  0  -0.200  -4.3126   0.1109   1.0779
 6EO  C12  C   CR6   0  -0.054  -4.7695  -0.2962  -0.1659
 6EO  CL1  CL  CL    0  -0.132  -6.4153   0.0181  -0.6144
 6EO  C14  C   CR16  0  -0.197  -3.9345  -0.9551  -1.0536
 6EO  O16  O   O     0  -0.441  -0.2406   1.2830   0.6828
 6EO  N18  N   N     0  -0.376   3.5379   2.8016  -0.0671
 6EO  C19  C   CR16  0  -0.073   4.7084   2.2558  -0.3690
 6EO  H1   H   HCR6  0   0.263  -2.6442   0.1683   2.4040
 6EO  H2   H   HCR6  0   0.263  -1.9701  -1.7222  -1.3765
 6EO  H3   H   HCR6  0   0.295   1.5752   2.5088   0.4156
 6EO  H4   H   HCR6  0   0.290   5.8648   0.4981  -0.6826
 6EO  H5   H   HOH1  0   0.498   5.3340  -2.7408  -0.5743
 6EO  H6   H   HNH1  0   0.434   1.6820  -1.1892   0.3364
 6EO  H7   H   HCH2  0   0.285  -0.3292  -1.9446   0.4156
 6EO  H8   H   HCH2  0   0.314  -0.6174  -1.2636   1.9998
 6EO  H9   H   HCR6  0   0.280  -4.9717   0.6215   1.7668
 6EO  H10  H   HCR6  0   0.280  -4.2987  -1.2751  -2.0203
 6EO  H11  H   HCR6  0   0.274   5.5334   2.9298  -0.5637
 6EO  C02  C   C     0   0.596   4.0120  -1.4336  -0.2508

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
 6EO  N18  C17  aromatic  1.320  0.020  1.320
 6EO  N18  C19  aromatic  1.326  0.020  1.326
 6EO  O16  C07  double    1.213  0.020  1.213
 6EO  C17  C05  aromatic  1.405  0.020  1.405
 6EO  C14  C15  aromatic  1.387  0.020  1.387
 6EO  C14  C12  aromatic  1.385  0.020  1.385
 6EO  C15  C09  aromatic  1.391  0.020  1.391
 6EO  CL1  C12  single    1.734  0.020  1.734
 6EO  C19  C20  aromatic  1.380  0.020  1.380
 6EO  C12  C11  aromatic  1.386  0.020  1.386
 6EO  C07  C08  single    1.520  0.020  1.520
 6EO  C07  N06  single    1.363  0.020  1.363
 6EO  C05  N06  single    1.385  0.020  1.385
 6EO  C05  C04  aromatic  1.410  0.020  1.410
 6EO  C09  C08  single    1.499  0.020  1.499
 6EO  C09  C10  aromatic  1.391  0.020  1.391
 6EO  C20  C04  aromatic  1.392  0.020  1.392
 6EO  C11  C10  aromatic  1.387  0.020  1.387
 6EO  C04  C02  single    1.487  0.020  1.487
 6EO  C02  O01  double    1.213  0.020  1.213
 6EO  C02  O03  single    1.317  0.020  1.317
 6EO  C10  H1   single    0.930  0.020  1.080
 6EO  C15  H2   single    0.930  0.020  1.080
 6EO  C17  H3   single    0.930  0.020  1.080
 6EO  C20  H4   single    0.930  0.020  1.080
 6EO  O03  H5   single    0.850  0.020  0.980
 6EO  N06  H6   single    0.860  0.020  1.020
 6EO  C08  H7   single    0.970  0.020  1.090
 6EO  C08  H8   single    0.970  0.020  1.090
 6EO  C11  H9   single    0.930  0.020  1.080
 6EO  C14  H10  single    0.930  0.020  1.080
 6EO  C19  H11  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
 6EO  H1   C10  C11  118.87  3.000
 6EO  H1   C10  C09  120.02  3.000
 6EO  C11  C10  C09  121.11  3.000
 6EO  H2   C15  C14  118.91  3.000
 6EO  H2   C15  C09  119.90  3.000
 6EO  C14  C15  C09  121.18  3.000
 6EO  H3   C17  N18  116.38  3.000
 6EO  H3   C17  C05  120.12  3.000
 6EO  N18  C17  C05  123.50  3.000
 6EO  H4   C20  C19  119.23  3.000
 6EO  H4   C20  C04  121.10  3.000
 6EO  C19  C20  C04  119.67  3.000
 6EO  H5   O03  C02  110.33  3.000
 6EO  C05  C04  C02  122.03  3.000
 6EO  C02  C04  C20  119.68  3.000
 6EO  C05  C04  C20  118.29  3.000
 6EO  N06  C05  C04  120.10  3.000
 6EO  C04  C05  C17  117.03  3.000
 6EO  N06  C05  C17  122.87  3.000
 6EO  H6   N06  C07  116.74  3.000
 6EO  H6   N06  C05  113.68  3.000
 6EO  C07  N06  C05  129.55  3.000
 6EO  O16  C07  C08  122.25  3.000
 6EO  C08  C07  N06  112.87  3.000
 6EO  O16  C07  N06  124.86  3.000
 6EO  H8   C08  H7   106.21  3.000
 6EO  H8   C08  C09  110.48  3.000
 6EO  H7   C08  C09  110.42  3.000
 6EO  H8   C08  C07  106.61  3.000
 6EO  H7   C08  C07  110.84  3.000
 6EO  C09  C08  C07  112.05  3.000
 6EO  C08  C09  C15  120.38  3.000
 6EO  C08  C09  C10  121.03  3.000
 6EO  C15  C09  C10  118.58  3.000
 6EO  H9   C11  C12  120.62  3.000
 6EO  H9   C11  C10  120.30  3.000
 6EO  C12  C11  C10  119.08  3.000
 6EO  C14  C12  CL1  119.50  3.000
 6EO  CL1  C12  C11  119.44  3.000
 6EO  C14  C12  C11  121.06  3.000
 6EO  H10  C14  C12  120.70  3.000
 6EO  H10  C14  C15  120.31  3.000
 6EO  C12  C14  C15  118.99  3.000
 6EO  C19  N18  C17  119.23  3.000
 6EO  H11  C19  N18  117.20  3.000
 6EO  H11  C19  C20  120.51  3.000
 6EO  N18  C19  C20  122.28  3.000
 6EO  C04  C02  O03  113.01  3.000
 6EO  O03  C02  O01  122.74  3.000
 6EO  C04  C02  O01  124.25  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
 6EO  CONST_01  C14  C15  C09  C10     0.00   0.0  0
 6EO  CONST_02  C14  C12  C11  C10     0.00   0.0  0
 6EO  CONST_03  C11  C12  C14  C15     0.00   0.0  0
 6EO  CONST_04  C11  C10  C09  C15     0.00   0.0  0
 6EO  CONST_05  C20  C19  N18  C17     0.00   0.0  0
 6EO  CONST_06  C20  C04  C05  C17     0.00   0.0  0
 6EO  CONST_07  N18  C17  C05  C04     0.00   0.0  0
 6EO  CONST_08  N18  C19  C20  C04     0.00   0.0  0
 6EO  CONST_09  C19  N18  C17  C05     0.00   0.0  0
 6EO  CONST_10  C19  C20  C04  C05     0.00   0.0  0
 6EO  CONST_11  C12  C14  C15  C09     0.00   0.0  0
 6EO  CONST_12  C12  C11  C10  C09     0.00   0.0  0
 6EO  CONST_13  CL1  C12  C11  C10   180.00   0.0  0
 6EO  CONST_14  CL1  C12  C14  C15   180.00   0.0  0
 6EO  CONST_15  C02  C04  C05  C17   180.00   0.0  0
 6EO  CONST_16  N06  C05  C04  C20   180.00   0.0  0
 6EO  CONST_17  C19  C20  C04  C02   180.00   0.0  0
 6EO  CONST_18  N18  C17  C05  N06   180.00   0.0  0
 6EO  CONST_19  C14  C15  C09  C08   180.00   0.0  0
 6EO  CONST_20  C11  C10  C09  C08   180.00   0.0  0
 6EO  CONST_21  H2   C15  C09  C10   180.00   0.0  0
 6EO  CONST_22  H1   C10  C09  C15   180.00   0.0  0
 6EO  CONST_23  H11  C19  N18  C17   180.00   0.0  0
 6EO  CONST_24  H3   C17  C05  C04   180.00   0.0  0
 6EO  CONST_25  H4   C20  C04  C05   180.00   0.0  0
 6EO  CONST_26  H10  C14  C15  C09   180.00   0.0  0
 6EO  CONST_27  H9   C11  C10  C09   180.00   0.0  0
 6EO  CONST_28  C07  N06  C05  C17     0.00   0.0  0
 6EO  CONST_29  C07  N06  C05  C04   180.00   0.0  0
 6EO  CONST_30  H6   N06  C05  C17   180.00   0.0  0
 6EO  CONST_31  O16  C07  N06  C05     0.00   0.0  0
 6EO  CONST_32  C08  C07  N06  C05   180.00   0.0  0
 6EO  CONST_33  H5   O03  C02  C04   180.00   0.0  0
 6EO  Var_01    C07  C08  C09  C10   -83.45  30.0  2
 6EO  Var_02    O01  C02  C04  C20  -179.80  30.0  2
 6EO  Var_03    C09  C08  C07  N06  -152.09  30.0  3

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
 6EO  plan-1  C10  0.020
 6EO  plan-1  C15  0.020
 6EO  plan-1  C08  0.020
 6EO  plan-1  C09  0.020
 6EO  plan-1  C11  0.020
 6EO  plan-1  C12  0.020
 6EO  plan-1  CL1  0.020
 6EO  plan-1  C14  0.020
 6EO  plan-1  H1   0.020
 6EO  plan-1  H2   0.020
 6EO  plan-1  H9   0.020
 6EO  plan-1  H10  0.020
 6EO  plan-2  C17  0.020
 6EO  plan-2  C20  0.020
 6EO  plan-2  C04  0.020
 6EO  plan-2  C05  0.020
 6EO  plan-2  N06  0.020
 6EO  plan-2  N18  0.020
 6EO  plan-2  C19  0.020
 6EO  plan-2  H3   0.020
 6EO  plan-2  H4   0.020
 6EO  plan-2  H11  0.020
 6EO  plan-2  C02  0.020
 6EO  plan-3  C05  0.020
 6EO  plan-3  N06  0.020
 6EO  plan-3  C07  0.020
 6EO  plan-3  C08  0.020
 6EO  plan-3  O16  0.020
 6EO  plan-3  H6   0.020
 6EO  plan-4  O01  0.020
 6EO  plan-4  O03  0.020
 6EO  plan-4  C04  0.020
 6EO  plan-4  H5   0.020
 6EO  plan-4  C02  0.020

