# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Aug  4 14:51:15 2022
#   Inital geometry file: a 108 line input string
#   Ligand name: N-cyclopropyl-6-(furan-2-yl)-2-hydroxy-N-[(pyridin-2-yl)methyl]pyridine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1nc(ccc1C(=O)N(Cc2ccccn2)C3CC3)c4occc4
#
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
 ZSY  ZSY  "N-cyclopropyl-6-(furan-2-yl)-2-hydroxy-N-[(pyridin-2-yl)methyl]pyridine-3-carboxamide"
  ligand  42  25  .  2022-08-11  2022-08-11
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ZSY
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
 ZSY  N1   N  NT    0  -0.458  28.6812   8.3826  58.6924
 ZSY  C7   C  CR15  0  -0.330  32.2002   8.8120  66.4807
 ZSY  C8   C  CR15  0   0.007  31.1328   9.6013  66.7551
 ZSY  N2   N  N     0  -0.430  26.2127   8.1326  55.9914
 ZSY  C9   C  CR6   0   0.471  29.9651   7.6126  61.4894
 ZSY  O1   O  O     0  -0.410  30.2693   9.5953  65.7242
 ZSY  C1   C  CR6   0  -0.212  28.7782   8.2619  61.1247
 ZSY  C5   C  CR5   0   0.352  30.7801   8.7929  64.7654
 ZSY  C6   C  CR15  0  -0.349  31.9719   8.2817  65.1810
 ZSY  C4   C  CR6   0   0.164  30.0305   8.6324  63.5334
 ZSY  C3   C  CR16  0  -0.328  28.8341   9.2978  63.2944
 ZSY  C2   C  CR16  0  -0.157  28.2066   9.0872  62.0750
 ZSY  N    N  N     0  -0.488  30.5678   7.7963  62.6399
 ZSY  C    C  C     0   0.526  28.0742   7.9913  59.8358
 ZSY  O    O  O     0  -0.461  26.9792   7.4512  59.8379
 ZSY  C10  C  CH2   0  -0.357  28.1002   7.9516  57.4385
 ZSY  C11  C  CR6   0   0.256  26.8562   8.6919  57.0119
 ZSY  C12  C  CR16  0  -0.333  26.4252   9.8748  57.6011
 ZSY  C13  C  CR16  0  -0.152  25.2874  10.4906  57.1030
 ZSY  C14  C  CR16  0  -0.328  24.6178   9.9096  56.0373
 ZSY  C15  C  CR16  0  -0.078  25.1260   8.7288  55.5191
 ZSY  C16  C  CH1   0  -0.112  29.9411   9.0659  58.6610
 ZSY  C17  C  CH2   0  -0.492  30.0626  10.3169  57.8469
 ZSY  C18  C  CH2   0  -0.481  30.0939  10.3888  59.3395
 ZSY  H3   H  HCR5  0   0.269  33.0449   8.6304  67.1247
 ZSY  H4   H  HCR5  0   0.282  30.8632  10.2025  67.6083
 ZSY  H2   H  HCR5  0   0.265  32.6079   7.6116  64.6266
 ZSY  H1   H  HCR6  0   0.270  28.3978   9.9620  64.0259
 ZSY  H    H  HCR6  0   0.277  27.2746   9.5929  61.8558
 ZSY  H7   H  HCH2  0   0.286  28.8600   8.0782  56.6655
 ZSY  H6   H  HCH2  0   0.272  27.8696   6.8848  57.4725
 ZSY  H8   H  HCR6  0   0.267  26.9617  10.3083  58.4342
 ZSY  H9   H  HCR6  0   0.271  24.9298  11.4119  57.5442
 ZSY  H10  H  HCR6  0   0.266  23.7263  10.3550  55.6178
 ZSY  H11  H  HCR6  0   0.261  24.6318   8.2397  54.6864
 ZSY  H12  H  HCH1  0   0.274  30.8111   8.4177  58.6529
 ZSY  H14  H  HCH2  0   0.264  30.9819  10.4558  57.2935
 ZSY  H13  H  HCH2  0   0.260  29.1784  10.6900  57.3455
 ZSY  H15  H  HCH2  0   0.262  31.0313  10.5886  59.8418
 ZSY  H16  H  HCH2  0   0.265  29.2251  10.8030  59.8341
 ZSY  H5   H  HOH1  0   0.476  31.3117   6.3837  61.0050
 ZSY  O2   O  OH1   0  -0.607  30.4955   6.7426  60.6294

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
 ZSY  C    O    double    1.221  0.020  1.221
 ZSY  C1   C    single    1.493  0.020  1.493
 ZSY  C1   C2   aromatic  1.382  0.020  1.382
 ZSY  C2   C3   aromatic  1.387  0.020  1.387
 ZSY  C3   C4   aromatic  1.390  0.020  1.390
 ZSY  C5   C4   single    1.451  0.020  1.451
 ZSY  C5   C6   aromatic  1.362  0.020  1.362
 ZSY  C6   C7   aromatic  1.422  0.020  1.422
 ZSY  C7   C8   aromatic  1.356  0.020  1.356
 ZSY  C8   O1   aromatic  1.345  0.020  1.345
 ZSY  O1   C5   aromatic  1.351  0.020  1.351
 ZSY  C4   N    aromatic  1.336  0.020  1.336
 ZSY  N    C9   aromatic  1.312  0.020  1.312
 ZSY  C9   C1   aromatic  1.401  0.020  1.401
 ZSY  O2   C9   single    1.333  0.020  1.333
 ZSY  N1   C    single    1.352  0.020  1.352
 ZSY  C10  N1   single    1.448  0.020  1.448
 ZSY  C11  C10  single    1.509  0.020  1.509
 ZSY  C11  C12  aromatic  1.390  0.020  1.390
 ZSY  C12  C13  aromatic  1.386  0.020  1.386
 ZSY  C13  C14  aromatic  1.386  0.020  1.386
 ZSY  C14  C15  aromatic  1.386  0.020  1.386
 ZSY  C15  N2   aromatic  1.326  0.020  1.326
 ZSY  N2   C11  aromatic  1.330  0.020  1.330
 ZSY  C16  N1   single    1.434  0.020  1.434
 ZSY  C16  C17  single    1.498  0.020  1.498
 ZSY  C17  C18  single    1.495  0.020  1.495
 ZSY  C18  C16  single    1.495  0.020  1.495
 ZSY  C7   H3   single    0.930  0.020  1.080
 ZSY  C8   H4   single    0.930  0.020  1.080
 ZSY  C6   H2   single    0.930  0.020  1.080
 ZSY  C3   H1   single    0.930  0.020  1.080
 ZSY  C2   H    single    0.930  0.020  1.080
 ZSY  C10  H7   single    0.970  0.020  1.090
 ZSY  C10  H6   single    0.970  0.020  1.090
 ZSY  C12  H8   single    0.930  0.020  1.080
 ZSY  C13  H9   single    0.930  0.020  1.080
 ZSY  C14  H10  single    0.930  0.020  1.080
 ZSY  C15  H11  single    0.930  0.020  1.080
 ZSY  C16  H12  single    0.970  0.020  1.090
 ZSY  C17  H14  single    0.970  0.020  1.090
 ZSY  C17  H13  single    0.970  0.020  1.090
 ZSY  C18  H15  single    0.970  0.020  1.090
 ZSY  C18  H16  single    0.970  0.020  1.090
 ZSY  O2   H5   single    0.850  0.020  0.980

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
 ZSY  C16  N1   C10  118.40  3.000
 ZSY  C16  N1   C    123.43  3.000
 ZSY  C10  N1   C    117.78  3.000
 ZSY  H3   C7   C6   127.53  3.000
 ZSY  H3   C7   C8   126.47  3.000
 ZSY  C6   C7   C8   106.00  3.000
 ZSY  H4   C8   O1   116.65  3.000
 ZSY  H4   C8   C7   132.99  3.000
 ZSY  O1   C8   C7   110.36  3.000
 ZSY  C15  N2   C11  118.73  3.000
 ZSY  O2   C9   N    118.31  3.000
 ZSY  O2   C9   C1   118.13  3.000
 ZSY  N    C9   C1   123.54  3.000
 ZSY  C5   O1   C8   107.70  3.000
 ZSY  C    C1   C2   120.44  3.000
 ZSY  C2   C1   C9   116.61  3.000
 ZSY  C    C1   C9   122.68  3.000
 ZSY  C4   C5   C6   132.04  3.000
 ZSY  C6   C5   O1   109.71  3.000
 ZSY  C4   C5   O1   118.24  3.000
 ZSY  H2   C6   C5   126.37  3.000
 ZSY  H2   C6   C7   127.40  3.000
 ZSY  C5   C6   C7   106.22  3.000
 ZSY  N    C4   C3   122.05  3.000
 ZSY  N    C4   C5   115.41  3.000
 ZSY  C3   C4   C5   122.54  3.000
 ZSY  H1   C3   C2   120.39  3.000
 ZSY  H1   C3   C4   121.71  3.000
 ZSY  C2   C3   C4   117.90  3.000
 ZSY  H    C2   C3   119.76  3.000
 ZSY  H    C2   C1   119.70  3.000
 ZSY  C3   C2   C1   120.52  3.000
 ZSY  C4   N    C9   119.29  3.000
 ZSY  O    C    C1   120.10  3.000
 ZSY  C1   C    N1   117.75  3.000
 ZSY  O    C    N1   122.14  3.000
 ZSY  H6   C10  H7   106.40  3.000
 ZSY  H6   C10  C11  108.29  3.000
 ZSY  H7   C10  C11  108.47  3.000
 ZSY  H6   C10  N1   110.40  3.000
 ZSY  H7   C10  N1   107.44  3.000
 ZSY  C11  C10  N1   115.45  3.000
 ZSY  C12  C11  C10  123.59  3.000
 ZSY  C12  C11  N2   122.22  3.000
 ZSY  C10  C11  N2   114.18  3.000
 ZSY  H8   C12  C13  120.39  3.000
 ZSY  H8   C12  C11  120.91  3.000
 ZSY  C13  C12  C11  118.70  3.000
 ZSY  H9   C13  C14  120.70  3.000
 ZSY  H9   C13  C12  120.19  3.000
 ZSY  C14  C13  C12  119.11  3.000
 ZSY  H10  C14  C15  120.55  3.000
 ZSY  H10  C14  C13  121.59  3.000
 ZSY  C15  C14  C13  117.86  3.000
 ZSY  H11  C15  C14  120.27  3.000
 ZSY  H11  C15  N2   116.36  3.000
 ZSY  C14  C15  N2   123.38  3.000
 ZSY  H12  C16  C18  116.76  3.000
 ZSY  H12  C16  C17  115.47  3.000
 ZSY  C18  C16  C17   59.94  3.000
 ZSY  H12  C16  N1   114.84  3.000
 ZSY  C18  C16  N1   120.12  3.000
 ZSY  C17  C16  N1   118.78  3.000
 ZSY  H13  C17  H14  114.38  3.000
 ZSY  H13  C17  C18  117.58  3.000
 ZSY  H14  C17  C18  119.13  3.000
 ZSY  H13  C17  C16  118.25  3.000
 ZSY  H14  C17  C16  117.02  3.000
 ZSY  C18  C17  C16   59.93  3.000
 ZSY  H16  C18  H15  114.37  3.000
 ZSY  H16  C18  C17  117.26  3.000
 ZSY  H15  C18  C17  119.38  3.000
 ZSY  H16  C18  C16  117.66  3.000
 ZSY  H15  C18  C16  117.57  3.000
 ZSY  C17  C18  C16   60.13  3.000
 ZSY  H5   O2   C9   109.10  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
 ZSY  CONST_01  C4   C5   C6   C7    180.00   0.0  0
 ZSY  CONST_02  O1   C5   C6   C7      0.00   0.0  0
 ZSY  CONST_03  C5   O1   C8   C7      0.00   0.0  0
 ZSY  CONST_04  C5   C6   C7   C8      0.00   0.0  0
 ZSY  CONST_05  C4   C5   O1   C8    180.00   0.0  0
 ZSY  CONST_06  C6   C5   O1   C8      0.00   0.0  0
 ZSY  CONST_07  C13  C14  C15  N2      0.00   0.0  0
 ZSY  CONST_08  C13  C12  C11  N2      0.00   0.0  0
 ZSY  CONST_09  C3   C4   N    C9      0.00   0.0  0
 ZSY  CONST_10  C5   C4   N    C9    180.00   0.0  0
 ZSY  CONST_11  C3   C2   C1   C9      0.00   0.0  0
 ZSY  CONST_12  C6   C7   C8   O1      0.00   0.0  0
 ZSY  CONST_13  C3   C4   C5   O1      0.00   0.0  0
 ZSY  CONST_14  N    C4   C5   O1    180.00   0.0  0
 ZSY  CONST_15  C4   C3   C2   C1      0.00   0.0  0
 ZSY  CONST_16  C4   N    C9   C1      0.00   0.0  0
 ZSY  CONST_17  C2   C3   C4   C5    180.00   0.0  0
 ZSY  CONST_18  C3   C4   C5   C6    180.00   0.0  0
 ZSY  CONST_19  N    C4   C5   C6      0.00   0.0  0
 ZSY  CONST_20  N    C9   C1   C2      0.00   0.0  0
 ZSY  CONST_21  N    C4   C3   C2      0.00   0.0  0
 ZSY  CONST_22  C14  C13  C12  C11     0.00   0.0  0
 ZSY  CONST_23  C14  C15  N2   C11     0.00   0.0  0
 ZSY  CONST_24  C15  N2   C11  C12     0.00   0.0  0
 ZSY  CONST_25  C15  C14  C13  C12     0.00   0.0  0
 ZSY  CONST_26  O2   C9   N    C4    180.00   0.0  0
 ZSY  CONST_27  C    C1   C2   C3    180.00   0.0  0
 ZSY  CONST_28  O2   C9   C1   C2    180.00   0.0  0
 ZSY  CONST_29  C    C1   C9   N     180.00   0.0  0
 ZSY  CONST_30  C13  C12  C11  C10   180.00   0.0  0
 ZSY  CONST_31  C15  N2   C11  C10   180.00   0.0  0
 ZSY  CONST_32  H2   C6   C7   C8    180.00   0.0  0
 ZSY  CONST_33  H10  C14  C15  N2    180.00   0.0  0
 ZSY  CONST_34  H8   C12  C11  N2    180.00   0.0  0
 ZSY  CONST_35  H    C2   C1   C9    180.00   0.0  0
 ZSY  CONST_36  H3   C7   C8   O1    180.00   0.0  0
 ZSY  CONST_37  H2   C6   C5   O1    180.00   0.0  0
 ZSY  CONST_38  H1   C3   C2   C1    180.00   0.0  0
 ZSY  CONST_39  H1   C3   C4   C5      0.00   0.0  0
 ZSY  CONST_40  H3   C7   C6   C5    180.00   0.0  0
 ZSY  CONST_41  H4   C8   O1   C5    180.00   0.0  0
 ZSY  CONST_42  H4   C8   C7   C6    180.00   0.0  0
 ZSY  CONST_43  H    C2   C3   C4    180.00   0.0  0
 ZSY  CONST_44  H2   C6   C5   C4      0.00   0.0  0
 ZSY  CONST_45  H1   C3   C4   N     180.00   0.0  0
 ZSY  CONST_46  H9   C13  C12  C11   180.00   0.0  0
 ZSY  CONST_47  H11  C15  N2   C11   180.00   0.0  0
 ZSY  CONST_48  H10  C14  C13  C12   180.00   0.0  0
 ZSY  CONST_49  H11  C15  C14  C13   180.00   0.0  0
 ZSY  CONST_50  H8   C12  C13  C14   180.00   0.0  0
 ZSY  CONST_51  H9   C13  C14  C15   180.00   0.0  0
 ZSY  CONST_52  C16  N1   C    C1      0.00   0.0  0
 ZSY  CONST_53  C10  N1   C    C1    180.00   0.0  0
 ZSY  CONST_54  C16  N1   C    O     180.00   0.0  0
 ZSY  CONST_55  C10  N1   C    O       0.00   0.0  0
 ZSY  Var_01    C18  C17  C16  N1    110.10  30.0  1
 ZSY  Var_02    H15  C18  C17  C16   106.81  30.0  1
 ZSY  Var_03    H16  C18  C17  C16  -107.84  30.0  1
 ZSY  Var_04    H14  C17  C18  C16  -106.16  30.0  1
 ZSY  Var_05    H13  C17  C18  C16   108.34  30.0  1
 ZSY  Var_06    H12  C16  C18  C17   105.34  30.0  1
 ZSY  Var_07    C2   C1   C    N1    118.00  30.0  2
 ZSY  Var_08    C9   C1   C    N1    -68.12  30.0  2
 ZSY  Var_09    C12  C11  C10  N1     12.73  30.0  2
 ZSY  Var_10    N2   C11  C10  N1   -168.84  30.0  2
 ZSY  Var_11    O    C    C1   C9    112.91  30.0  2
 ZSY  Var_12    O    C    C1   C2    -60.98  30.0  2
 ZSY  Var_13    C17  C16  N1   C    -130.24  30.0  2
 ZSY  Var_14    C18  C16  N1   C     -60.24  30.0  2
 ZSY  Var_15    C17  C16  N1   C10    57.12  30.0  2
 ZSY  Var_16    C18  C16  N1   C10   127.11  30.0  2
 ZSY  Var_17    C16  N1   C10  C11  -110.65  30.0  3
 ZSY  Var_18    H14  C17  C16  N1   -140.26  30.0  1
 ZSY  Var_19    H13  C17  C16  N1      2.87  30.0  1
 ZSY  Var_20    H15  C18  C16  N1    142.33  30.0  1
 ZSY  Var_21    H16  C18  C16  N1     -0.72  30.0  1
 ZSY  Var_22    H7   C10  C11  N2     70.58  30.0  2
 ZSY  Var_23    H6   C10  C11  N2    -44.51  30.0  2
 ZSY  Var_24    H7   C10  C11  C12  -107.85  30.0  2
 ZSY  Var_25    H6   C10  C11  C12   137.06  30.0  2
 ZSY  Var_26    C11  C10  N1   C      76.29  30.0  2
 ZSY  Var_27    H12  C16  N1   C      87.12  30.0  2
 ZSY  Var_28    H12  C16  N1   C10   -85.52  30.0  2
 ZSY  Var_29    H7   C10  N1   C16    10.50  30.0  2
 ZSY  Var_30    H6   C10  N1   C16   126.13  30.0  2
 ZSY  Var_31    H7   C10  N1   C    -162.57  30.0  2
 ZSY  Var_32    H6   C10  N1   C     -46.93  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 ZSY  chir_01  C16  N1  C17  C18  both

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
 ZSY  plan-1  C7   0.020
 ZSY  plan-1  C8   0.020
 ZSY  plan-1  O1   0.020
 ZSY  plan-1  C5   0.020
 ZSY  plan-1  C6   0.020
 ZSY  plan-1  C4   0.020
 ZSY  plan-1  H3   0.020
 ZSY  plan-1  H4   0.020
 ZSY  plan-1  H2   0.020
 ZSY  plan-2  C9   0.020
 ZSY  plan-2  C1   0.020
 ZSY  plan-2  C5   0.020
 ZSY  plan-2  C4   0.020
 ZSY  plan-2  C3   0.020
 ZSY  plan-2  C2   0.020
 ZSY  plan-2  N    0.020
 ZSY  plan-2  C    0.020
 ZSY  plan-2  H1   0.020
 ZSY  plan-2  H    0.020
 ZSY  plan-2  O2   0.020
 ZSY  plan-3  N2   0.020
 ZSY  plan-3  C10  0.020
 ZSY  plan-3  C11  0.020
 ZSY  plan-3  C12  0.020
 ZSY  plan-3  C13  0.020
 ZSY  plan-3  C14  0.020
 ZSY  plan-3  C15  0.020
 ZSY  plan-3  H8   0.020
 ZSY  plan-3  H9   0.020
 ZSY  plan-3  H10  0.020
 ZSY  plan-3  H11  0.020
 ZSY  plan-4  N1   0.020
 ZSY  plan-4  C1   0.020
 ZSY  plan-4  C    0.020
 ZSY  plan-4  O    0.020
 ZSY  plan-4  C10  0.020
 ZSY  plan-4  C16  0.020

