# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 25 11:32:32 2022
#   Inital geometry file: a 99 line input string
#   Ligand name: N-butyl-4-(furan-2-carbonyl)piperazine-1-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCNC(=O)N1CCN(CC1)C(=O)c2occc2
#
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
 Y0A  Y0A  N-butyl-4-(furan-2-carbonyl)piperazine-1-carboxamide  ligand  41  20  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_Y0A
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
 Y0A  N1   N  NT    0  -0.489  -18.9109  17.1584  26.1059
 Y0A  C4   C  C     0   0.734  -17.8400  17.8388  26.6466
 Y0A  C5   C  CH2   0  -0.323  -19.7050  16.3259  26.9917
 Y0A  C6   C  CH2   0  -0.310  -19.1967  14.8926  26.9730
 Y0A  C7   C  C     0   0.501  -19.4209  13.0877  25.2668
 Y0A  C8   C  CR5   0   0.213  -20.3542  12.2924  26.0888
 Y0A  C10  C  CR15  0  -0.332  -21.5376  10.6821  27.0682
 Y0A  C13  C  CH2   0  -0.358  -18.9496  16.6378  24.7517
 Y0A  N    N  NH1   0  -0.676  -16.9639  18.4062  25.7822
 Y0A  C    C  CH3   0  -0.667  -13.6768  17.7197  24.3163
 Y0A  O    O  O     0  -0.536  -17.7180  17.9737  27.8603
 Y0A  C1   C  CH2   0  -0.439  -14.2518  17.0641  25.5656
 Y0A  C11  C  CR15  0   0.012  -22.0986  11.8895  27.3229
 Y0A  C12  C  CH2   0  -0.297  -18.4204  15.2113  24.6885
 Y0A  C2   C  CH2   0  -0.433  -14.6522  18.0552  26.6540
 Y0A  C3   C  CH2   0  -0.304  -15.7451  19.0388  26.2420
 Y0A  C9   C  CR15  0  -0.317  -20.4031  10.9442  26.2525
 Y0A  N2   N  NT    0  -0.475  -19.1777  14.3759  25.6083
 Y0A  O1   O  O     0  -0.468  -18.9289  12.5548  24.2816
 Y0A  O2   O  O     0  -0.403  -21.3920  12.8700  26.7352
 Y0A  H10  H  HCH2  0   0.271  -19.6726  16.7147  28.0049
 Y0A  H11  H  HCH2  0   0.252  -20.7450  16.3537  26.6557
 Y0A  H13  H  HCH2  0   0.248  -18.1750  14.8698  27.3694
 Y0A  H12  H  HCH2  0   0.277  -19.8064  14.2751  27.6240
 Y0A  H15  H  HCR5  0   0.271  -21.8906   9.7246  27.4137
 Y0A  H20  H  HCH2  0   0.267  -18.4078  17.2642  24.0471
 Y0A  H19  H  HCH2  0   0.263  -19.9904  16.6490  24.4179
 Y0A  H9   H  HNH1  0   0.398  -17.0246  18.2279  24.7964
 Y0A  H    H  HCH3  0   0.228  -13.3434  16.9710  23.5972
 Y0A  H2   H  HCH3  0   0.220  -14.4086  18.3501  23.8083
 Y0A  H1   H  HCH3  0   0.217  -12.8186  18.3482  24.5621
 Y0A  H4   H  HCH2  0   0.221  -15.1137  16.4469  25.2941
 Y0A  H3   H  HCH2  0   0.225  -13.5131  16.3741  25.9808
 Y0A  H16  H  HCR5  0   0.286  -22.9720  12.1905  27.8789
 Y0A  H17  H  HCH2  0   0.248  -17.3535  15.1948  24.9434
 Y0A  H18  H  HCH2  0   0.269  -18.5251  14.8286  23.6761
 Y0A  H6   H  HCH2  0   0.228  -14.9802  17.5097  27.5417
 Y0A  H5   H  HCH2  0   0.219  -13.7756  18.6364  26.9577
 Y0A  H7   H  HCH2  0   0.246  -15.9715  19.7069  27.0732
 Y0A  H8   H  HCH2  0   0.243  -15.3942  19.6727  25.4274
 Y0A  H14  H  HCR5  0   0.271  -19.7100  10.2262  25.8453

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
 Y0A  C    C1   single    1.524  0.020  1.524
 Y0A  C1   C2   single    1.525  0.020  1.525
 Y0A  C2   C3   single    1.527  0.020  1.527
 Y0A  C3   N    single    1.448  0.020  1.448
 Y0A  N    C4   single    1.355  0.020  1.355
 Y0A  O    C4   double    1.227  0.020  1.227
 Y0A  C4   N1   single    1.379  0.020  1.379
 Y0A  N1   C5   single    1.452  0.020  1.452
 Y0A  C5   C6   single    1.521  0.020  1.521
 Y0A  C6   N2   single    1.459  0.020  1.459
 Y0A  N2   C7   single    1.355  0.020  1.355
 Y0A  C7   O1   double    1.223  0.020  1.223
 Y0A  C8   C7   single    1.476  0.020  1.476
 Y0A  C8   C9   aromatic  1.359  0.020  1.359
 Y0A  C9   C10  aromatic  1.422  0.020  1.422
 Y0A  C10  C11  aromatic  1.356  0.020  1.356
 Y0A  C11  O2   aromatic  1.344  0.020  1.344
 Y0A  O2   C8   aromatic  1.352  0.020  1.352
 Y0A  C12  N2   single    1.455  0.020  1.455
 Y0A  C13  C12  single    1.523  0.020  1.523
 Y0A  N1   C13  single    1.451  0.020  1.451
 Y0A  C5   H10  single    0.970  0.020  1.090
 Y0A  C5   H11  single    0.970  0.020  1.090
 Y0A  C6   H13  single    0.970  0.020  1.090
 Y0A  C6   H12  single    0.970  0.020  1.090
 Y0A  C10  H15  single    0.930  0.020  1.080
 Y0A  C13  H20  single    0.970  0.020  1.090
 Y0A  C13  H19  single    0.970  0.020  1.090
 Y0A  N    H9   single    0.860  0.020  1.020
 Y0A  C    H    single    0.970  0.020  1.090
 Y0A  C    H2   single    0.970  0.020  1.090
 Y0A  C    H1   single    0.970  0.020  1.090
 Y0A  C1   H4   single    0.970  0.020  1.090
 Y0A  C1   H3   single    0.970  0.020  1.090
 Y0A  C11  H16  single    0.930  0.020  1.080
 Y0A  C12  H17  single    0.970  0.020  1.090
 Y0A  C12  H18  single    0.970  0.020  1.090
 Y0A  C2   H6   single    0.970  0.020  1.090
 Y0A  C2   H5   single    0.970  0.020  1.090
 Y0A  C3   H7   single    0.970  0.020  1.090
 Y0A  C3   H8   single    0.970  0.020  1.090
 Y0A  C9   H14  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
 Y0A  C13  N1   C5   110.42  3.000
 Y0A  C13  N1   C4   124.30  3.000
 Y0A  C5   N1   C4   117.93  3.000
 Y0A  O    C4   N    121.36  3.000
 Y0A  O    C4   N1   121.27  3.000
 Y0A  N    C4   N1   117.29  3.000
 Y0A  H11  C5   H10  107.82  3.000
 Y0A  H11  C5   C6   109.76  3.000
 Y0A  H10  C5   C6   109.81  3.000
 Y0A  H11  C5   N1   108.56  3.000
 Y0A  H10  C5   N1   110.34  3.000
 Y0A  C6   C5   N1   110.49  3.000
 Y0A  H12  C6   H13  107.16  3.000
 Y0A  H12  C6   N2   111.53  3.000
 Y0A  H13  C6   N2   108.58  3.000
 Y0A  H12  C6   C5   109.95  3.000
 Y0A  H13  C6   C5   109.07  3.000
 Y0A  N2   C6   C5   110.46  3.000
 Y0A  O1   C7   N2   123.03  3.000
 Y0A  O1   C7   C8   117.90  3.000
 Y0A  N2   C7   C8   119.04  3.000
 Y0A  O2   C8   C9   109.79  3.000
 Y0A  O2   C8   C7   121.42  3.000
 Y0A  C9   C8   C7   128.63  3.000
 Y0A  H15  C10  C9   127.54  3.000
 Y0A  H15  C10  C11  126.56  3.000
 Y0A  C9   C10  C11  105.90  3.000
 Y0A  H19  C13  H20  105.70  3.000
 Y0A  H19  C13  C12  109.14  3.000
 Y0A  H20  C13  C12  109.85  3.000
 Y0A  H19  C13  N1   107.86  3.000
 Y0A  H20  C13  N1   112.62  3.000
 Y0A  C12  C13  N1   111.43  3.000
 Y0A  H9   N    C3   116.13  3.000
 Y0A  H9   N    C4   120.86  3.000
 Y0A  C3   N    C4   121.64  3.000
 Y0A  H1   C    H2   107.42  3.000
 Y0A  H1   C    H    107.66  3.000
 Y0A  H2   C    H    107.14  3.000
 Y0A  H1   C    C1   111.09  3.000
 Y0A  H2   C    C1   112.16  3.000
 Y0A  H    C    C1   111.15  3.000
 Y0A  H3   C1   H4   105.70  3.000
 Y0A  H3   C1   C2   108.46  3.000
 Y0A  H4   C1   C2   109.68  3.000
 Y0A  H3   C1   C    109.15  3.000
 Y0A  H4   C1   C    109.66  3.000
 Y0A  C2   C1   C    113.86  3.000
 Y0A  H16  C11  O2   116.60  3.000
 Y0A  H16  C11  C10  132.90  3.000
 Y0A  O2   C11  C10  110.49  3.000
 Y0A  H18  C12  H17  107.74  3.000
 Y0A  H18  C12  N2   109.65  3.000
 Y0A  H17  C12  N2   110.53  3.000
 Y0A  H18  C12  C13  109.56  3.000
 Y0A  H17  C12  C13  110.03  3.000
 Y0A  N2   C12  C13  109.31  3.000
 Y0A  H5   C2   H6   106.26  3.000
 Y0A  H5   C2   C3   107.82  3.000
 Y0A  H6   C2   C3   109.03  3.000
 Y0A  H5   C2   C1   109.43  3.000
 Y0A  H6   C2   C1   109.52  3.000
 Y0A  C3   C2   C1   114.45  3.000
 Y0A  H8   C3   H7   106.27  3.000
 Y0A  H8   C3   C2   110.23  3.000
 Y0A  H7   C3   C2   109.73  3.000
 Y0A  H8   C3   N    106.72  3.000
 Y0A  H7   C3   N    109.57  3.000
 Y0A  C2   C3   N    114.00  3.000
 Y0A  H14  C9   C10  127.38  3.000
 Y0A  H14  C9   C8   126.32  3.000
 Y0A  C10  C9   C8   106.30  3.000
 Y0A  C12  N2   C7   118.69  3.000
 Y0A  C12  N2   C6   113.24  3.000
 Y0A  C7   N2   C6   124.76  3.000
 Y0A  C11  O2   C8   107.52  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
 Y0A  CONST_01  C11  C10  C9   C8      0.00   0.0  0
 Y0A  CONST_02  C10  C11  O2   C8      0.00   0.0  0
 Y0A  CONST_03  O2   C8   C9   C10     0.00   0.0  0
 Y0A  CONST_04  C9   C8   O2   C11     0.00   0.0  0
 Y0A  CONST_05  O2   C11  C10  C9      0.00   0.0  0
 Y0A  CONST_06  C10  C9   C8   C7    180.00   0.0  0
 Y0A  CONST_07  C11  O2   C8   C7    180.00   0.0  0
 Y0A  CONST_09  C12  N2   C7   C8    180.00   0.0  0
 Y0A  CONST_10  H15  C10  C9   C8    180.00   0.0  0
 Y0A  CONST_11  H16  C11  O2   C8    180.00   0.0  0
 Y0A  CONST_12  H14  C9   C10  C11   180.00   0.0  0
 Y0A  CONST_16  O1   C7   N2   C12     0.00   0.0  0
 Y0A  CONST_17  N    C4   N1   C5    180.00   0.0  0
 Y0A  CONST_19  C3   N    C4   N1    180.00   0.0  0
 Y0A  CONST_20  H9   N    C4   N1      0.00   0.0  0
 Y0A  CONST_21  C3   N    C4   O       0.00   0.0  0
 Y0A  Var_01    N2   C6   C5   N1    -55.52  30.0  1
 Y0A  Var_02    N2   C12  C13  N1     56.04  30.0  1
 Y0A  Var_03    C12  C13  N1   C5    -59.00  30.0  1
 Y0A  Var_04    C12  N2   C6   C5     54.72  30.0  1
 Y0A  Var_05    C13  N1   C5   C6     58.19  30.0  1
 Y0A  Var_06    C13  C12  N2   C6    -54.35  30.0  1
 Y0A  Var_07    N2   C7   C8   C9   -154.49  30.0  2
 Y0A  Var_08    C2   C3   N    C4     75.68  30.0  1
 Y0A  Var_09    C1   C2   C3   N      56.61  30.0  2
 Y0A  Var_10    C3   C2   C1   C      61.62  30.0  3
 Y0A  Var_11    H    C    C1   C2    176.12  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
 Y0A  plan-1  C7   0.020
 Y0A  plan-1  C8   0.020
 Y0A  plan-1  C10  0.020
 Y0A  plan-1  C11  0.020
 Y0A  plan-1  C9   0.020
 Y0A  plan-1  O2   0.020
 Y0A  plan-1  H15  0.020
 Y0A  plan-1  H16  0.020
 Y0A  plan-1  H14  0.020
 Y0A  plan-2  N1   0.020
 Y0A  plan-2  C4   0.020
 Y0A  plan-2  C5   0.020
 Y0A  plan-2  C13  0.020
 Y0A  plan-2  N    0.020
 Y0A  plan-2  O    0.020
 Y0A  plan-2  C3   0.020
 Y0A  plan-2  H9   0.020
 Y0A  plan-3  C6   0.020
 Y0A  plan-3  C7   0.020
 Y0A  plan-3  C8   0.020
 Y0A  plan-3  C12  0.020
 Y0A  plan-3  N2   0.020
 Y0A  plan-3  O1   0.020

