# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 08:07:27 2022
#   Inital geometry file: a 72 line input string
#   Ligand name: 1-[(4-hydroxyphenyl)methyl]imidazole-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(Cn2ccnc2C(O)=O)cc1
#
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
 HN9  HN9  "1-[(4-hydroxyphenyl)methyl]imidazole-2-carboxylic acid"  ligand  25  16  .  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_HN9
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
 HN9  C11  C  CR16   0  -0.324  32.5198  22.9525   -8.4762
 HN9  C12  C  CR16   0  -0.280  32.2113  21.9752   -9.4063
 HN9  O13  O  OH1    0  -0.633  33.2904  23.5759   -6.3455
 HN9  O16  O  O      0  -0.577  29.4831  19.3117   -8.9873
 HN9  N01  N  N      0  -0.447  31.4544  16.3408   -8.7856
 HN9  C02  C  CR5    0   0.262  31.0513  17.5584   -9.0820
 HN9  N03  N  NR5    0  -0.436  32.0402  18.2417   -9.7269
 HN9  C04  C  CR15   0  -0.119  33.1151  17.4074   -9.8235
 HN9  C05  C  CR15   0  -0.219  32.7316  16.2362   -9.2356
 HN9  C06  C  CH2    0  -0.327  32.0580  19.6097  -10.1970
 HN9  C07  C  CR6    0   0.078  32.3766  20.6207   -9.1248
 HN9  C08  C  CR16   0  -0.287  32.8616  20.2725   -7.8724
 HN9  C09  C  CR16   0  -0.368  33.1740  21.2408   -6.9261
 HN9  C10  C  CR6    0   0.339  33.0056  22.5891   -7.2213
 HN9  O15  O  OC    -1  -0.580  28.8751  17.2797   -8.2832
 HN9  H1   H  HCR6   0   0.258  32.3816  23.9993   -8.7175
 HN9  H2   H  HCR6   0   0.248  31.8299  22.2780  -10.3752
 HN9  H3   H  HOH1   0   0.470  33.6209  23.2071   -5.5186
 HN9  H4   H  HCR5   0   0.282  34.0330  17.7134  -10.2989
 HN9  H5   H  HCR5   0   0.239  33.3105  15.3316   -9.1222
 HN9  H6   H  HCH2   0   0.264  32.8141  19.6623  -10.9832
 HN9  H7   H  HCH2   0   0.273  31.1030  19.8441  -10.6582
 HN9  H8   H  HCR6   0   0.253  33.0043  19.2319   -7.6083
 HN9  H9   H  HCR6   0   0.265  33.5489  20.9376   -5.9546
 HN9  C14  C  C      0   0.363  29.6746  18.1031   -8.7551

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
 HN9  C06  N03  single    1.447  0.020  1.447
 HN9  C06  C07  single    1.508  0.020  1.508
 HN9  C04  N03  aromatic  1.364  0.020  1.364
 HN9  C04  C05  aromatic  1.365  0.020  1.365
 HN9  N03  C02  aromatic  1.364  0.020  1.364
 HN9  C12  C07  aromatic  1.393  0.020  1.393
 HN9  C12  C11  aromatic  1.384  0.020  1.384
 HN9  O16  C14  deloc     1.246  0.020  1.246
 HN9  C05  N01  aromatic  1.358  0.020  1.358
 HN9  C07  C08  aromatic  1.388  0.020  1.388
 HN9  C02  C14  single    1.516  0.020  1.516
 HN9  C02  N01  aromatic  1.316  0.020  1.316
 HN9  C14  O15  deloc     1.241  0.020  1.241
 HN9  C11  C10  aromatic  1.394  0.020  1.394
 HN9  C08  C09  aromatic  1.389  0.020  1.389
 HN9  C10  C09  aromatic  1.390  0.020  1.390
 HN9  C10  O13  single    1.350  0.020  1.350
 HN9  C11  H1   single    0.930  0.020  1.080
 HN9  C12  H2   single    0.930  0.020  1.080
 HN9  O13  H3   single    0.850  0.020  0.980
 HN9  C04  H4   single    0.930  0.020  1.080
 HN9  C05  H5   single    0.930  0.020  1.080
 HN9  C06  H6   single    0.970  0.020  1.090
 HN9  C06  H7   single    0.970  0.020  1.090
 HN9  C08  H8   single    0.930  0.020  1.080
 HN9  C09  H9   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
 HN9  H1   C11  C10  119.80  3.000
 HN9  H1   C11  C12  120.29  3.000
 HN9  C10  C11  C12  119.91  3.000
 HN9  H2   C12  C07  119.58  3.000
 HN9  H2   C12  C11  118.80  3.000
 HN9  C07  C12  C11  121.62  3.000
 HN9  H3   O13  C10  110.44  3.000
 HN9  C05  N01  C02  106.54  3.000
 HN9  N03  C02  N01  110.36  3.000
 HN9  N01  C02  C14  124.18  3.000
 HN9  N03  C02  C14  125.46  3.000
 HN9  C06  N03  C04  123.07  3.000
 HN9  C04  N03  C02  107.35  3.000
 HN9  C06  N03  C02  129.51  3.000
 HN9  H4   C04  C05  132.26  3.000
 HN9  H4   C04  N03  121.91  3.000
 HN9  C05  C04  N03  105.83  3.000
 HN9  H5   C05  C04  127.81  3.000
 HN9  H5   C05  N01  122.26  3.000
 HN9  C04  C05  N01  109.92  3.000
 HN9  H7   C06  H6   107.02  3.000
 HN9  H7   C06  C07  110.07  3.000
 HN9  H6   C06  C07  109.48  3.000
 HN9  H7   C06  N03  109.34  3.000
 HN9  H6   C06  N03  106.73  3.000
 HN9  C07  C06  N03  113.93  3.000
 HN9  C08  C07  C06  123.20  3.000
 HN9  C08  C07  C12  117.89  3.000
 HN9  C06  C07  C12  118.89  3.000
 HN9  H8   C08  C09  118.29  3.000
 HN9  H8   C08  C07  120.49  3.000
 HN9  C09  C08  C07  121.23  3.000
 HN9  H9   C09  C10  120.21  3.000
 HN9  H9   C09  C08  119.53  3.000
 HN9  C10  C09  C08  120.26  3.000
 HN9  C09  C10  O13  123.06  3.000
 HN9  O13  C10  C11  117.85  3.000
 HN9  C09  C10  C11  119.09  3.000
 HN9  O15  C14  C02  115.38  3.000
 HN9  O15  C14  O16  128.00  3.000
 HN9  C02  C14  O16  116.62  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
 HN9  CONST_01  C08  C07  C12  C11     0.00   0.0  0
 HN9  CONST_02  C08  C09  C10  C11     0.00   0.0  0
 HN9  CONST_03  C09  C08  C07  C12     0.00   0.0  0
 HN9  CONST_04  C09  C10  C11  C12     0.00   0.0  0
 HN9  CONST_05  N03  C04  C05  N01     0.00   0.0  0
 HN9  CONST_06  C04  N03  C02  N01     0.00   0.0  0
 HN9  CONST_07  C05  C04  N03  C02     0.00   0.0  0
 HN9  CONST_08  C04  C05  N01  C02     0.00   0.0  0
 HN9  CONST_09  C05  N01  C02  N03     0.00   0.0  0
 HN9  CONST_10  C10  C11  C12  C07     0.00   0.0  0
 HN9  CONST_11  C10  C09  C08  C07     0.00   0.0  0
 HN9  CONST_12  C06  C07  C12  C11   180.00   0.0  0
 HN9  CONST_13  O13  C10  C11  C12   180.00   0.0  0
 HN9  CONST_14  C08  C09  C10  O13   180.00   0.0  0
 HN9  CONST_15  C04  N03  C02  C14   180.00   0.0  0
 HN9  CONST_16  C05  N01  C02  C14   180.00   0.0  0
 HN9  CONST_17  C06  N03  C02  N01   180.00   0.0  0
 HN9  CONST_18  C06  N03  C04  C05   180.00   0.0  0
 HN9  CONST_19  C09  C08  C07  C06   180.00   0.0  0
 HN9  CONST_20  H9   C09  C10  C11   180.00   0.0  0
 HN9  CONST_21  H8   C08  C07  C12   180.00   0.0  0
 HN9  CONST_22  H4   C04  C05  N01   180.00   0.0  0
 HN9  CONST_23  H4   C04  N03  C02   180.00   0.0  0
 HN9  CONST_24  H5   C05  N01  C02   180.00   0.0  0
 HN9  CONST_25  H5   C05  C04  N03   180.00   0.0  0
 HN9  CONST_26  H1   C11  C12  C07   180.00   0.0  0
 HN9  CONST_27  H9   C09  C08  C07   180.00   0.0  0
 HN9  CONST_28  H2   C12  C07  C08   180.00   0.0  0
 HN9  CONST_29  H1   C11  C10  C09   180.00   0.0  0
 HN9  CONST_30  H2   C12  C11  C10   180.00   0.0  0
 HN9  CONST_31  H8   C08  C09  C10   180.00   0.0  0
 HN9  Var_01    N03  C06  C07  C12  -169.77  30.0  3
 HN9  Var_02    C07  C06  N03  C02    81.42  30.0  2
 HN9  Var_03    C08  C07  C06  N03    11.90  30.0  2
 HN9  Var_04    C07  C06  N03  C04   -95.44  30.0  2
 HN9  Var_05    N03  C02  C14  O16    -7.00  30.0  2
 HN9  Var_06    N01  C02  C14  O16   173.54  30.0  2
 HN9  Var_07    O15  C14  C02  N01    -6.34  30.0  2
 HN9  Var_08    O15  C14  C02  N03   173.12  30.0  2
 HN9  Var_09    H6   C06  C07  C12    70.82  30.0  3
 HN9  Var_10    H7   C06  C07  C12   -46.55  30.0  3
 HN9  Var_11    H6   C06  N03  C02  -157.63  30.0  2
 HN9  Var_12    H7   C06  N03  C02   -42.20  30.0  2
 HN9  Var_13    H6   C06  N03  C04    25.51  30.0  2
 HN9  Var_14    H7   C06  N03  C04   140.95  30.0  2
 HN9  Var_15    H6   C06  C07  C08  -107.51  30.0  3
 HN9  Var_16    H7   C06  C07  C08   135.13  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
 HN9  plan-1  N01  0.020
 HN9  plan-1  C02  0.020
 HN9  plan-1  N03  0.020
 HN9  plan-1  C04  0.020
 HN9  plan-1  C05  0.020
 HN9  plan-1  C06  0.020
 HN9  plan-1  H4   0.020
 HN9  plan-1  H5   0.020
 HN9  plan-1  C14  0.020
 HN9  plan-2  C11  0.020
 HN9  plan-2  C12  0.020
 HN9  plan-2  O13  0.020
 HN9  plan-2  C06  0.020
 HN9  plan-2  C07  0.020
 HN9  plan-2  C08  0.020
 HN9  plan-2  C09  0.020
 HN9  plan-2  C10  0.020
 HN9  plan-2  H1   0.020
 HN9  plan-2  H2   0.020
 HN9  plan-2  H8   0.020
 HN9  plan-2  H9   0.020
 HN9  plan-3  O16  0.020
 HN9  plan-3  C02  0.020
 HN9  plan-3  O15  0.020
 HN9  plan-3  C14  0.020

