# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 20:35:17 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  30  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 GRAND
;

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  -0.303  -2.6849  -0.7111   1.4442
 6EO  C15  C   CR16   0  -0.304  -2.9707  -0.7374  -0.9296
 6EO  C17  C   CR16   0  -0.134   2.4861   1.8657  -0.6947
 6EO  C20  C   CR16   0  -0.344   4.8868   1.0034   0.2008
 6EO  O01  O   O      0  -0.596   3.0148  -1.9171   1.2498
 6EO  O03  O   OC    -1  -0.551   5.1851  -1.4650   1.3944
 6EO  C04  C   CR6    0  -0.126   3.8017   0.1577   0.3817
 6EO  C05  C   CR6    0   0.275   2.5504   0.6052  -0.0850
 6EO  N06  N   NH1    0  -0.769   1.4538  -0.2309   0.0867
 6EO  C07  C   C      0   0.548   0.1687  -0.0612  -0.2905
 6EO  C08  C   CH2    0  -0.691  -0.7015  -1.2744   0.0131
 6EO  C09  C   CR6    0   0.157  -2.1455  -0.9102   0.1777
 6EO  C11  C   CR16   0  -0.197  -4.0144  -0.3496   1.6116
 6EO  C12  C   CR6    0  -0.055  -4.8115  -0.1846   0.4908
 6EO  CL1  CL  CL     0  -0.134  -6.4770   0.2608   0.6849
 6EO  C14  C   CR16   0  -0.201  -4.3016  -0.3773  -0.7839
 6EO  O16  O   O      0  -0.464  -0.2786   0.9274  -0.8450
 6EO  N18  N   N      0  -0.392   3.5400   2.6527  -0.8530
 6EO  C19  C   CR16   0  -0.086   4.7186   2.2307  -0.4147
 6EO  H1   H   HCR6   0   0.262  -2.0633  -0.8425   2.3215
 6EO  H2   H   HCR6   0   0.261  -2.5782  -0.8953  -1.9263
 6EO  H3   H   HCR6   0   0.277   1.5449   2.2450  -1.0623
 6EO  H4   H   HCR6   0   0.263   5.8662   0.6982   0.5408
 6EO  H6   H   HNH1   0   0.432   1.7435  -1.0967   0.5751
 6EO  H7   H   HCH2   0   0.303  -0.5776  -1.9713  -0.8219
 6EO  H8   H   HCH2   0   0.282  -0.3320  -1.7928   0.8997
 6EO  H9   H   HCR6   0   0.278  -4.4191  -0.2012   2.6035
 6EO  H10  H   HCR6   0   0.278  -4.9315  -0.2489  -1.6537
 6EO  H11  H   HCR6   0   0.257   5.5631   2.8950  -0.5596
 6EO  C02  C   C      0   0.473   4.0258  -1.1911   1.0680

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  1.325  0.020  1.325
 6EO  N18  C19  aromatic  1.326  0.020  1.326
 6EO  O16  C07  double    1.219  0.020  1.219
 6EO  C17  C05  aromatic  1.402  0.020  1.402
 6EO  C14  C15  aromatic  1.386  0.020  1.386
 6EO  C14  C12  aromatic  1.386  0.020  1.386
 6EO  C15  C09  aromatic  1.392  0.020  1.392
 6EO  CL1  C12  single    1.735  0.020  1.735
 6EO  C19  C20  aromatic  1.383  0.020  1.383
 6EO  C12  C11  aromatic  1.385  0.020  1.385
 6EO  C07  C08  single    1.524  0.020  1.524
 6EO  C07  N06  single    1.350  0.020  1.350
 6EO  C05  N06  single    1.390  0.020  1.390
 6EO  C05  C04  aromatic  1.409  0.020  1.409
 6EO  C09  C08  single    1.498  0.020  1.498
 6EO  C09  C10  aromatic  1.391  0.020  1.391
 6EO  C20  C04  aromatic  1.388  0.020  1.388
 6EO  C11  C10  aromatic  1.388  0.020  1.388
 6EO  C04  C02  single    1.530  0.020  1.530
 6EO  C02  O01  deloc     1.258  0.020  1.258
 6EO  C02  O03  deloc     1.235  0.020  1.235
 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  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  118.92  3.000
 6EO  H1   C10  C09  119.84  3.000
 6EO  C11  C10  C09  121.24  3.000
 6EO  H2   C15  C14  118.85  3.000
 6EO  H2   C15  C09  119.96  3.000
 6EO  C14  C15  C09  121.19  3.000
 6EO  H3   C17  N18  116.38  3.000
 6EO  H3   C17  C05  120.27  3.000
 6EO  N18  C17  C05  123.35  3.000
 6EO  H4   C20  C19  120.05  3.000
 6EO  H4   C20  C04  119.70  3.000
 6EO  C19  C20  C04  120.25  3.000
 6EO  C05  C04  C02  123.98  3.000
 6EO  C02  C04  C20  118.77  3.000
 6EO  C05  C04  C20  117.25  3.000
 6EO  N06  C05  C04  117.97  3.000
 6EO  C04  C05  C17  118.07  3.000
 6EO  N06  C05  C17  123.96  3.000
 6EO  H6   N06  C07  120.22  3.000
 6EO  H6   N06  C05  109.91  3.000
 6EO  C07  N06  C05  129.87  3.000
 6EO  O16  C07  C08  121.81  3.000
 6EO  C08  C07  N06  112.82  3.000
 6EO  O16  C07  N06  125.35  3.000
 6EO  H8   C08  H7   106.20  3.000
 6EO  H8   C08  C09  110.64  3.000
 6EO  H7   C08  C09  110.34  3.000
 6EO  H8   C08  C07  110.29  3.000
 6EO  H7   C08  C07  106.88  3.000
 6EO  C09  C08  C07  112.25  3.000
 6EO  C08  C09  C15  120.94  3.000
 6EO  C08  C09  C10  120.57  3.000
 6EO  C15  C09  C10  118.48  3.000
 6EO  H9   C11  C12  120.69  3.000
 6EO  H9   C11  C10  120.32  3.000
 6EO  C12  C11  C10  118.99  3.000
 6EO  C14  C12  CL1  119.45  3.000
 6EO  CL1  C12  C11  119.51  3.000
 6EO  C14  C12  C11  121.05  3.000
 6EO  H10  C14  C12  120.58  3.000
 6EO  H10  C14  C15  120.36  3.000
 6EO  C12  C14  C15  119.06  3.000
 6EO  C19  N18  C17  118.58  3.000
 6EO  H11  C19  N18  116.94  3.000
 6EO  H11  C19  C20  120.56  3.000
 6EO  N18  C19  C20  122.50  3.000
 6EO  C04  C02  O03  116.84  3.000
 6EO  O03  C02  O01  126.03  3.000
 6EO  C04  C02  O01  117.13  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  Var_01    C07  C08  C09  C10  -96.95  30.0  2
 6EO  Var_02    O01  C02  C04  C20  178.06  30.0  2
 6EO  Var_03    C09  C08  C07  N06  154.57  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  C02  0.020

