# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 16:11:02 2022
#   Inital geometry file: a 94 line input string
#   Ligand name: ~{N}-[3-(4-chloranylphenoxy)-4-methyl-phenyl]propanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(=O)Nc1ccc(C)c(Oc2ccc(Cl)cc2)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
 KK9  KK9  ~{N}-[3-(4-chloranylphenoxy)-4-methyl-phenyl]propanamide  ligand  36  20  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_KK9
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
 KK9  C1   C   CR6   0  -0.056  48.1871  27.3248   9.4174
 KK9  C10  C   CH3   0  -0.718  46.6185  20.6473   2.7245
 KK9  C11  C   CR16  0  -0.308  46.1158  20.5379   7.9893
 KK9  C12  C   CR16  0  -0.295  46.4803  20.8965   9.2802
 KK9  C13  C   CR6   0   0.034  47.4522  21.8506   9.5540
 KK9  C14  C   CH3   0  -0.722  47.8389  22.2181  10.9549
 KK9  C15  C   CR16  0  -0.336  47.4239  25.1526   8.7413
 KK9  C16  C   CR16  0  -0.202  47.1630  26.4904   9.0058
 KK9  C2   C   CR16  0  -0.203  49.4773  26.8369   9.5675
 KK9  C3   C   CR16  0  -0.331  49.7389  25.5031   9.3075
 KK9  C4   C   CR6   0   0.374  48.7140  24.6582   8.8926
 KK9  C5   C   CR6   0   0.288  48.0612  22.4420   8.4493
 KK9  C6   C   CR16  0  -0.411  47.7255  22.1078   7.1527
 KK9  C7   C   CR6   0   0.374  46.7446  21.1453   6.9032
 KK9  C8   C   C     0   0.524  45.5758  19.9994   5.0272
 KK9  C9   C   CH2   0  -0.544  45.5014  19.9776   3.5123
 KK9  N1   N   NH1   0  -0.756  46.4682  20.8717   5.5609
 KK9  O1   O   O2    0  -0.507  49.0593  23.3665   8.6449
 KK9  O2   O   O     0  -0.472  44.8517  19.2826   5.6961
 KK9  CL1  CL  CL    0  -0.135  47.8575  28.9951   9.7483
 KK9  H1   H   HCH3  0   0.261  46.4676  20.4764   1.6598
 KK9  H2   H   HCH3  0   0.236  46.6406  21.7289   2.8674
 KK9  H3   H   HCH3  0   0.241  47.5989  20.2443   2.9815
 KK9  H4   H   HCR6  0   0.280  45.3544  19.7902   7.8457
 KK9  H5   H   HCR6  0   0.256  45.9826  20.4078  10.1092
 KK9  H6   H   HCH3  0   0.246  47.6073  23.2608  11.1810
 KK9  H7   H   HCH3  0   0.252  47.3033  21.6006  11.6741
 KK9  H8   H   HCH3  0   0.248  48.9072  22.0822  11.1275
 KK9  H9   H   HCR6  0   0.290  46.6118  24.5159   8.4163
 KK9  H10  H   HCR6  0   0.282  46.1574  26.8708   8.8869
 KK9  H11  H   HCR6  0   0.281  50.2783  27.4882   9.8900
 KK9  H12  H   HCR6  0   0.278  50.7426  25.1158   9.4270
 KK9  H13  H   HCR6  0   0.281  48.2330  22.5992   6.3297
 KK9  H14  H   HCH2  0   0.272  44.5403  20.4272   3.2457
 KK9  H15  H   HCH2  0   0.266  45.4230  18.9270   3.2272
 KK9  H16  H   HNH1  0   0.432  47.0130  21.4125   4.9072

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
 KK9  C10  C9   single    1.522  0.020  1.522
 KK9  C9   C8   single    1.517  0.020  1.517
 KK9  C8   N1   single    1.357  0.020  1.357
 KK9  C8   O2   double    1.219  0.020  1.219
 KK9  N1   C7   single    1.398  0.020  1.398
 KK9  C7   C6   aromatic  1.397  0.020  1.397
 KK9  C7   C11  aromatic  1.394  0.020  1.394
 KK9  C6   C5   aromatic  1.380  0.020  1.380
 KK9  C11  C12  aromatic  1.388  0.020  1.388
 KK9  C5   O1   single    1.375  0.020  1.375
 KK9  C5   C13  aromatic  1.393  0.020  1.393
 KK9  O1   C4   single    1.360  0.020  1.360
 KK9  C4   C15  aromatic  1.390  0.020  1.390
 KK9  C4   C3   aromatic  1.392  0.020  1.392
 KK9  C15  C16  aromatic  1.388  0.020  1.388
 KK9  C12  C13  aromatic  1.389  0.020  1.389
 KK9  C3   C2   aromatic  1.384  0.020  1.384
 KK9  C16  C1   aromatic  1.384  0.020  1.384
 KK9  C2   C1   aromatic  1.387  0.020  1.387
 KK9  C1   CL1  single    1.734  0.020  1.734
 KK9  C13  C14  single    1.499  0.020  1.499
 KK9  C10  H1   single    0.970  0.020  1.090
 KK9  C10  H2   single    0.970  0.020  1.090
 KK9  C10  H3   single    0.970  0.020  1.090
 KK9  C11  H4   single    0.930  0.020  1.080
 KK9  C12  H5   single    0.930  0.020  1.080
 KK9  C14  H6   single    0.970  0.020  1.090
 KK9  C14  H7   single    0.970  0.020  1.090
 KK9  C14  H8   single    0.970  0.020  1.090
 KK9  C15  H9   single    0.930  0.020  1.080
 KK9  C16  H10  single    0.930  0.020  1.080
 KK9  C2   H11  single    0.930  0.020  1.080
 KK9  C3   H12  single    0.930  0.020  1.080
 KK9  C6   H13  single    0.930  0.020  1.080
 KK9  C9   H14  single    0.970  0.020  1.090
 KK9  C9   H15  single    0.970  0.020  1.090
 KK9  N1   H16  single    0.860  0.020  1.020

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
 KK9  CL1  C1   C2   119.65  3.000
 KK9  CL1  C1   C16  119.79  3.000
 KK9  C2   C1   C16  120.56  3.000
 KK9  H3   C10  H2   108.49  3.000
 KK9  H3   C10  H1   107.27  3.000
 KK9  H2   C10  H1   106.64  3.000
 KK9  H3   C10  C9   112.04  3.000
 KK9  H2   C10  C9   112.53  3.000
 KK9  H1   C10  C9   109.59  3.000
 KK9  H4   C11  C7   121.17  3.000
 KK9  H4   C11  C12  119.27  3.000
 KK9  C7   C11  C12  119.56  3.000
 KK9  H5   C12  C13  118.71  3.000
 KK9  H5   C12  C11  118.31  3.000
 KK9  C13  C12  C11  122.98  3.000
 KK9  C5   C13  C14  121.62  3.000
 KK9  C14  C13  C12  122.21  3.000
 KK9  C5   C13  C12  116.17  3.000
 KK9  H8   C14  H7   107.86  3.000
 KK9  H8   C14  H6   107.10  3.000
 KK9  H7   C14  H6   107.50  3.000
 KK9  H8   C14  C13  111.71  3.000
 KK9  H7   C14  C13  110.57  3.000
 KK9  H6   C14  C13  111.90  3.000
 KK9  H9   C15  C4   121.34  3.000
 KK9  H9   C15  C16  118.90  3.000
 KK9  C4   C15  C16  119.76  3.000
 KK9  H10  C16  C15  119.51  3.000
 KK9  H10  C16  C1   120.58  3.000
 KK9  C15  C16  C1   119.91  3.000
 KK9  H11  C2   C3   119.77  3.000
 KK9  H11  C2   C1   120.61  3.000
 KK9  C3   C2   C1   119.63  3.000
 KK9  H12  C3   C4   119.90  3.000
 KK9  H12  C3   C2   119.96  3.000
 KK9  C4   C3   C2   120.14  3.000
 KK9  O1   C4   C3   116.37  3.000
 KK9  C3   C4   C15  120.01  3.000
 KK9  O1   C4   C15  123.63  3.000
 KK9  O1   C5   C6   118.24  3.000
 KK9  O1   C5   C13  119.34  3.000
 KK9  C6   C5   C13  122.40  3.000
 KK9  H13  C6   C7   120.35  3.000
 KK9  H13  C6   C5   119.29  3.000
 KK9  C7   C6   C5   120.36  3.000
 KK9  N1   C7   C6   116.45  3.000
 KK9  C6   C7   C11  118.54  3.000
 KK9  N1   C7   C11  125.01  3.000
 KK9  O2   C8   N1   123.56  3.000
 KK9  O2   C8   C9   120.70  3.000
 KK9  N1   C8   C9   115.74  3.000
 KK9  H15  C9   H14  105.59  3.000
 KK9  H15  C9   C8   106.15  3.000
 KK9  H14  C9   C8   106.29  3.000
 KK9  H15  C9   C10  109.94  3.000
 KK9  H14  C9   C10  109.75  3.000
 KK9  C8   C9   C10  118.33  3.000
 KK9  H16  N1   C8   116.42  3.000
 KK9  H16  N1   C7   114.26  3.000
 KK9  C8   N1   C7   129.31  3.000
 KK9  C5   O1   C4   118.71  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
 KK9  CONST_01  C4   C15  C16  C1      0.00   0.0  0
 KK9  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 KK9  CONST_03  C5   C6   C7   C11     0.00   0.0  0
 KK9  CONST_04  C5   C13  C12  C11     0.00   0.0  0
 KK9  CONST_05  C6   C7   C11  C12     0.00   0.0  0
 KK9  CONST_06  C6   C5   C13  C12     0.00   0.0  0
 KK9  CONST_07  C7   C6   C5   C13     0.00   0.0  0
 KK9  CONST_08  C7   C11  C12  C13     0.00   0.0  0
 KK9  CONST_09  C2   C3   C4   C15     0.00   0.0  0
 KK9  CONST_10  C2   C1   C16  C15     0.00   0.0  0
 KK9  CONST_11  C3   C4   C15  C16     0.00   0.0  0
 KK9  CONST_12  C3   C2   C1   C16     0.00   0.0  0
 KK9  CONST_13  C14  C13  C12  C11   180.00   0.0  0
 KK9  CONST_14  N1   C7   C11  C12   180.00   0.0  0
 KK9  CONST_15  O1   C5   C13  C12   180.00   0.0  0
 KK9  CONST_16  C6   C5   C13  C14   180.00   0.0  0
 KK9  CONST_17  CL1  C1   C16  C15   180.00   0.0  0
 KK9  CONST_18  O1   C4   C15  C16   180.00   0.0  0
 KK9  CONST_19  O1   C4   C3   C2    180.00   0.0  0
 KK9  CONST_20  CL1  C1   C2   C3    180.00   0.0  0
 KK9  CONST_21  N1   C7   C6   C5    180.00   0.0  0
 KK9  CONST_22  O1   C5   C6   C7    180.00   0.0  0
 KK9  CONST_23  H9   C15  C16  C1    180.00   0.0  0
 KK9  CONST_24  H12  C3   C2   C1    180.00   0.0  0
 KK9  CONST_25  H13  C6   C7   C11   180.00   0.0  0
 KK9  CONST_26  H4   C11  C12  C13   180.00   0.0  0
 KK9  CONST_27  H11  C2   C1   C16   180.00   0.0  0
 KK9  CONST_28  H10  C16  C1   C2    180.00   0.0  0
 KK9  CONST_29  H5   C12  C13  C5    180.00   0.0  0
 KK9  CONST_30  C8   N1   C7   C11     0.00   0.0  0
 KK9  CONST_31  C8   N1   C7   C6    180.00   0.0  0
 KK9  CONST_32  H16  N1   C7   C11   180.00   0.0  0
 KK9  CONST_33  C9   C8   N1   C7    180.00   0.0  0
 KK9  CONST_34  O2   C8   N1   C7      0.00   0.0  0
 KK9  Var_01    C6   C5   O1   C4     98.33  30.0  3
 KK9  Var_02    H6   C14  C13  C12  -116.44  30.0  2
 KK9  Var_03    N1   C8   C9   C10    14.45  30.0  3
 KK9  Var_04    H1   C10  C9   C8    175.30  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
 KK9  plan-1  C1   0.020
 KK9  plan-1  C15  0.020
 KK9  plan-1  C16  0.020
 KK9  plan-1  C2   0.020
 KK9  plan-1  C3   0.020
 KK9  plan-1  C4   0.020
 KK9  plan-1  O1   0.020
 KK9  plan-1  CL1  0.020
 KK9  plan-1  H9   0.020
 KK9  plan-1  H10  0.020
 KK9  plan-1  H11  0.020
 KK9  plan-1  H12  0.020
 KK9  plan-2  C11  0.020
 KK9  plan-2  C12  0.020
 KK9  plan-2  C13  0.020
 KK9  plan-2  C14  0.020
 KK9  plan-2  C5   0.020
 KK9  plan-2  C6   0.020
 KK9  plan-2  C7   0.020
 KK9  plan-2  N1   0.020
 KK9  plan-2  O1   0.020
 KK9  plan-2  H4   0.020
 KK9  plan-2  H5   0.020
 KK9  plan-2  H13  0.020
 KK9  plan-3  C7   0.020
 KK9  plan-3  C8   0.020
 KK9  plan-3  C9   0.020
 KK9  plan-3  N1   0.020
 KK9  plan-3  O2   0.020
 KK9  plan-3  H16  0.020

