# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 05:29:00 2022
#   Inital geometry file: a 62 line input string
#   Ligand name: 1-but-3-enylimidazole-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1nccn1CCC=C
#
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
 HLF  HLF  "1-but-3-enylimidazole-2-carboxylic acid"  ligand  21  12  .  2022-08-10  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HLF
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
 HLF  C01  C  CR15   0  -0.224  21.8215  13.5412   9.8969
 HLF  C02  C  CR15   0  -0.115  22.2922  12.9550   8.7569
 HLF  N03  N  NR5    0  -0.422  21.5142  11.8547   8.5533
 HLF  C04  C  CR5    0   0.267  20.5953  11.8141   9.5613
 HLF  N05  N  N      0  -0.453  20.7759  12.8274  10.3855
 HLF  C06  C  C      0   0.369  19.5191  10.7596   9.7629
 HLF  O07  O  OC    -1  -0.577  18.8054  10.9231  10.7639
 HLF  O08  O  O      0  -0.579  19.4540   9.8391   8.9248
 HLF  C09  C  CH2    0  -0.321  21.6612  11.0072   7.3830
 HLF  C10  C  CH2    0  -0.502  21.0471  11.6400   6.1339
 HLF  C11  C  C1     0  -0.140  19.5828  11.9050   6.2694
 HLF  C12  C  C2     0  -0.536  19.0272  13.1093   6.1995
 HLF  H1   H  HCR5   0   0.237  22.1887  14.4328  10.3834
 HLF  H2   H  HCR5   0   0.278  23.0994  13.2143   8.0907
 HLF  H4   H  HCH2   0   0.275  21.2017  10.0493   7.5959
 HLF  H5   H  HCH2   0   0.257  22.7273  10.8465   7.2188
 HLF  H6   H  HCH2   0   0.248  21.2231  10.9457   5.3063
 HLF  H7   H  HCH2   0   0.239  21.5758  12.5644   5.8871
 HLF  H8   H  H      0   0.239  18.9547  11.0393   6.4526
 HLF  H9   H  H      0   0.232  17.9593  13.2490   6.3058
 HLF  H10  H  H      0   0.228  19.6209  14.0005   6.0312

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
 HLF  C10  C11  single    1.494  0.020  1.494
 HLF  C10  C09  single    1.529  0.020  1.529
 HLF  C11  C12  double    1.328  0.020  1.328
 HLF  C09  N03  single    1.452  0.020  1.452
 HLF  N03  C02  aromatic  1.363  0.020  1.363
 HLF  N03  C04  aromatic  1.365  0.020  1.365
 HLF  C02  C01  aromatic  1.366  0.020  1.366
 HLF  O08  C06  deloc     1.247  0.020  1.247
 HLF  C04  C06  single    1.520  0.020  1.520
 HLF  C04  N05  aromatic  1.319  0.020  1.319
 HLF  C06  O07  deloc     1.240  0.020  1.240
 HLF  C01  N05  aromatic  1.357  0.020  1.357
 HLF  C01  H1   single    0.930  0.020  1.080
 HLF  C02  H2   single    0.930  0.020  1.080
 HLF  C09  H4   single    0.970  0.020  1.090
 HLF  C09  H5   single    0.970  0.020  1.090
 HLF  C10  H6   single    0.970  0.020  1.090
 HLF  C10  H7   single    0.970  0.020  1.090
 HLF  C11  H8   single    0.930  0.020  1.080
 HLF  C12  H9   single    0.930  0.020  1.080
 HLF  C12  H10  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
 HLF  H1   C01  N05  122.27  3.000
 HLF  H1   C01  C02  127.83  3.000
 HLF  N05  C01  C02  109.90  3.000
 HLF  H2   C02  N03  121.95  3.000
 HLF  H2   C02  C01  132.11  3.000
 HLF  N03  C02  C01  105.93  3.000
 HLF  C09  N03  C04  130.24  3.000
 HLF  C04  N03  C02  107.34  3.000
 HLF  C09  N03  C02  122.26  3.000
 HLF  C06  C04  N05  123.17  3.000
 HLF  N05  C04  N03  110.28  3.000
 HLF  C06  C04  N03  126.53  3.000
 HLF  C04  N05  C01  106.54  3.000
 HLF  O08  C06  O07  127.58  3.000
 HLF  O07  C06  C04  115.02  3.000
 HLF  O08  C06  C04  117.39  3.000
 HLF  H5   C09  H4   108.30  3.000
 HLF  H5   C09  C10  109.31  3.000
 HLF  H4   C09  C10  110.86  3.000
 HLF  H5   C09  N03  107.83  3.000
 HLF  H4   C09  N03  108.33  3.000
 HLF  C10  C09  N03  112.09  3.000
 HLF  H7   C10  H6   106.73  3.000
 HLF  H7   C10  C11  110.15  3.000
 HLF  H6   C10  C11  109.80  3.000
 HLF  H7   C10  C09  109.89  3.000
 HLF  H6   C10  C09  106.89  3.000
 HLF  C11  C10  C09  113.14  3.000
 HLF  H8   C11  C12  119.35  3.000
 HLF  H8   C11  C10  116.17  3.000
 HLF  C12  C11  C10  124.47  3.000
 HLF  H10  C12  H9   116.72  3.000
 HLF  H10  C12  C11  121.64  3.000
 HLF  H9   C12  C11  121.65  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
 HLF  CONST_01  C04  N03  C02  C01     0.00   0.0  0
 HLF  CONST_02  N03  C04  N05  C01     0.00   0.0  0
 HLF  CONST_03  N05  C04  N03  C02     0.00   0.0  0
 HLF  CONST_04  C04  N05  C01  C02     0.00   0.0  0
 HLF  CONST_05  N05  C01  C02  N03     0.00   0.0  0
 HLF  CONST_06  C09  N03  C02  C01   180.00   0.0  0
 HLF  CONST_07  C06  C04  N05  C01   180.00   0.0  0
 HLF  CONST_08  C06  C04  N03  C02   180.00   0.0  0
 HLF  CONST_09  C09  N03  C04  N05   180.00   0.0  0
 HLF  CONST_10  H1   C01  C02  N03   180.00   0.0  0
 HLF  CONST_11  H2   C02  N03  C04   180.00   0.0  0
 HLF  CONST_12  H1   C01  N05  C04   180.00   0.0  0
 HLF  CONST_13  H2   C02  C01  N05   180.00   0.0  0
 HLF  Var_01    C10  C09  N03  C02   -76.45  30.0  2
 HLF  Var_02    O08  C06  C04  N03    -0.51  30.0  2
 HLF  Var_03    O07  C06  C04  N03   179.19  30.0  2
 HLF  Var_04    C10  C09  N03  C04    98.31  30.0  2
 HLF  Var_05    O08  C06  C04  N05  -179.21  30.0  2
 HLF  Var_06    O07  C06  C04  N05     0.49  30.0  2
 HLF  Var_07    H4   C09  N03  C02   160.91  30.0  2
 HLF  Var_08    H5   C09  N03  C02    43.91  30.0  2
 HLF  Var_09    H4   C09  N03  C04   -24.33  30.0  2
 HLF  Var_10    H5   C09  N03  C04  -141.33  30.0  2
 HLF  Var_11    C11  C10  C09  N03   -60.20  30.0  2
 HLF  Var_12    H6   C10  C09  N03   178.83  30.0  2
 HLF  Var_13    H7   C10  C09  N03    63.37  30.0  2
 HLF  Var_14    C12  C11  C10  C09   118.68  30.0  3
 HLF  Var_15    H9   C12  C11  C10  -179.90   0.0  2
 HLF  Var_16    H10  C12  C11  C10     0.23   0.0  2
 HLF  Var_17    H8   C11  C10  C09   -60.30  30.0  3
 HLF  Var_18    H4   C09  C10  C11    61.00  30.0  3
 HLF  Var_19    H5   C09  C10  C11  -179.69  30.0  3
 HLF  Var_20    H6   C10  C11  C12  -122.00  30.0  1
 HLF  Var_21    H7   C10  C11  C12    -4.74  30.0  1
 HLF  Var_22    H9   C12  C11  H8     -0.95   0.0  2
 HLF  Var_23    H10  C12  C11  H8    179.18   0.0  2

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
 HLF  plan-1  C01  0.020
 HLF  plan-1  C02  0.020
 HLF  plan-1  N03  0.020
 HLF  plan-1  C04  0.020
 HLF  plan-1  N05  0.020
 HLF  plan-1  C06  0.020
 HLF  plan-1  C09  0.020
 HLF  plan-1  H1   0.020
 HLF  plan-1  H2   0.020
 HLF  plan-2  C04  0.020
 HLF  plan-2  C06  0.020
 HLF  plan-2  O07  0.020
 HLF  plan-2  O08  0.020
 HLF  plan-3  C10  0.020
 HLF  plan-3  C11  0.020
 HLF  plan-3  C12  0.020
 HLF  plan-3  H8   0.020
 HLF  plan-3  H9   0.020
 HLF  plan-3  H10  0.020

