# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 23 22:11:31 2020
#   Inital geometry file: a 80 line input string
#   Ligand name: 4-(4-methylpiperazin-1-yl)benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN1CCN(CC1)c2ccc(cc2)C(O)=O
#
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
 14N  14N  '4-(4-methylpiperazin-1-yl)benzoic acid'  ligand  32  16  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_14N
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
 14N  C3   C  CH2   0  -0.312  -2.0860   1.2476  -0.0972
 14N  C2   C  CH2   0  -0.280  -3.5153   1.0817   0.3850
 14N  N1   N  NT    0  -0.413  -4.1970   0.0329  -0.3398
 14N  C1   C  CH3   0  -0.519  -5.5857  -0.0728   0.0455
 14N  C5   C  CH2   0  -0.284  -3.4910  -1.2147  -0.1516
 14N  C4   C  CH2   0  -0.307  -2.0653  -1.1098  -0.6539
 14N  N2   N  NT    0  -0.518  -1.3588  -0.0060  -0.0180
 14N  C6   C  CR6   0   0.404   0.0149   0.0059  -0.0016
 14N  C7   C  CR16  0  -0.355   0.7504   1.2074  -0.0399
 14N  C8   C  CR16  0  -0.241   2.1287   1.2043   0.0177
 14N  C9   C  CR6   0  -0.122   2.8524   0.0163   0.1038
 14N  C12  C  C     0   0.518   4.3205   0.0727   0.1521
 14N  O2   O  O     0  -0.456   4.9653   1.0982   0.1376
 14N  O1   O  OH1   0  -0.601   4.8906  -1.1281   0.2136
 14N  C10  C  CR16  0  -0.244   2.1332  -1.1815   0.1332
 14N  C11  C  CR16  0  -0.336   0.7568  -1.1907   0.0801
 14N  H1   H  HCH2  0   0.226  -2.0846   1.6411  -1.1230
 14N  H2   H  HCH2  0   0.258  -1.6116   1.9899   0.5427
 14N  H3   H  HCH2  0   0.197  -3.5102   0.8883   1.4723
 14N  H4   H  HCH2  0   0.245  -4.0373   2.0285   0.2301
 14N  H6   H  HCH3  0   0.235  -6.1017   0.8681  -0.1513
 14N  H7   H  HCH3  0   0.235  -6.0749  -0.8520  -0.5408
 14N  H8   H  HCH3  0   0.194  -5.7235  -0.3175   1.1101
 14N  H9   H  HCH2  0   0.197  -3.4815  -1.5244   0.9082
 14N  H10  H  HCH2  0   0.245  -3.9944  -2.0054  -0.7122
 14N  H11  H  HCH2  0   0.261  -1.5696  -2.0538  -0.4469
 14N  H12  H  HCH2  0   0.229  -2.0692  -0.9734  -1.7436
 14N  H13  H  HCR6  0   0.273   0.2515   2.1604  -0.1366
 14N  H14  H  HCR6  0   0.260   2.6511   2.1514  -0.0225
 14N  H15  H  HOH1  0   0.483   5.8530  -1.0284   0.2430
 14N  H16  H  HCR6  0   0.262   2.6463  -2.1310   0.2063
 14N  H17  H  HCR6  0   0.269   0.2574  -2.1476   0.1269

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
 14N  C2   C3   single    1.518  0.020  1.518
 14N  C2   N1   single    1.446  0.020  1.446
 14N  C3   N2   single    1.451  0.020  1.451
 14N  C5   C4   single    1.515  0.020  1.515
 14N  C5   N1   single    1.446  0.020  1.446
 14N  C4   N2   single    1.457  0.020  1.457
 14N  N1   C1   single    1.445  0.020  1.445
 14N  N2   C6   single    1.374  0.020  1.374
 14N  C6   C11  aromatic  1.410  0.020  1.410
 14N  C6   C7   aromatic  1.409  0.020  1.409
 14N  C11  C10  aromatic  1.377  0.020  1.377
 14N  C7   C8   aromatic  1.380  0.020  1.380
 14N  C10  C9   aromatic  1.397  0.020  1.397
 14N  C8   C9   aromatic  1.394  0.020  1.394
 14N  C9   C12  single    1.470  0.020  1.470
 14N  C12  O2   double    1.211  0.020  1.211
 14N  C12  O1   single    1.331  0.020  1.331
 14N  C3   H1   single    0.970  0.020  1.090
 14N  C3   H2   single    0.970  0.020  1.090
 14N  C2   H3   single    0.970  0.020  1.090
 14N  C2   H4   single    0.970  0.020  1.090
 14N  C1   H6   single    0.970  0.020  1.090
 14N  C1   H7   single    0.970  0.020  1.090
 14N  C1   H8   single    0.970  0.020  1.090
 14N  C5   H9   single    0.970  0.020  1.090
 14N  C5   H10  single    0.970  0.020  1.090
 14N  C4   H11  single    0.970  0.020  1.090
 14N  C4   H12  single    0.970  0.020  1.090
 14N  C7   H13  single    0.930  0.020  1.080
 14N  C8   H14  single    0.930  0.020  1.080
 14N  O1   H15  single    0.850  0.020  0.980
 14N  C10  H16  single    0.930  0.020  1.080
 14N  C11  H17  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
 14N  H2   C3   H1   107.70  3.000
 14N  H2   C3   N2   109.79  3.000
 14N  H1   C3   N2   111.08  3.000
 14N  H2   C3   C2   107.34  3.000
 14N  H1   C3   C2   109.70  3.000
 14N  N2   C3   C2   111.11  3.000
 14N  H4   C2   H3   107.08  3.000
 14N  H4   C2   N1   109.41  3.000
 14N  H3   C2   N1   111.64  3.000
 14N  H4   C2   C3   108.08  3.000
 14N  H3   C2   C3   109.13  3.000
 14N  N1   C2   C3   111.35  3.000
 14N  C5   N1   C1   111.81  3.000
 14N  C1   N1   C2   111.87  3.000
 14N  C5   N1   C2   109.30  3.000
 14N  H8   C1   H7   107.74  3.000
 14N  H8   C1   H6   107.87  3.000
 14N  H7   C1   H6   107.87  3.000
 14N  H8   C1   N1   113.23  3.000
 14N  H7   C1   N1   109.87  3.000
 14N  H6   C1   N1   110.09  3.000
 14N  H10  C5   H9   107.07  3.000
 14N  H10  C5   C4   108.28  3.000
 14N  H9   C5   C4   109.24  3.000
 14N  H10  C5   N1   109.44  3.000
 14N  H9   C5   N1   111.79  3.000
 14N  C4   C5   N1   110.89  3.000
 14N  H12  C4   H11  107.38  3.000
 14N  H12  C4   N2   109.92  3.000
 14N  H11  C4   N2   110.74  3.000
 14N  H12  C4   C5   109.52  3.000
 14N  H11  C4   C5   107.82  3.000
 14N  N2   C4   C5   111.35  3.000
 14N  C6   N2   C4   119.78  3.000
 14N  C6   N2   C3   119.61  3.000
 14N  C4   N2   C3   112.81  3.000
 14N  C11  C6   C7   116.77  3.000
 14N  C7   C6   N2   121.93  3.000
 14N  C11  C6   N2   121.28  3.000
 14N  H13  C7   C8   117.86  3.000
 14N  H13  C7   C6   120.91  3.000
 14N  C8   C7   C6   121.22  3.000
 14N  H14  C8   C9   119.84  3.000
 14N  H14  C8   C7   118.60  3.000
 14N  C9   C8   C7   121.56  3.000
 14N  C10  C9   C12  123.10  3.000
 14N  C12  C9   C8   119.21  3.000
 14N  C10  C9   C8   117.69  3.000
 14N  O1   C12  O2   122.44  3.000
 14N  O1   C12  C9   113.25  3.000
 14N  O2   C12  C9   124.30  3.000
 14N  H15  O1   C12  109.54  3.000
 14N  H16  C10  C11  118.08  3.000
 14N  H16  C10  C9   120.64  3.000
 14N  C11  C10  C9   121.28  3.000
 14N  H17  C11  C10  117.79  3.000
 14N  H17  C11  C6   120.72  3.000
 14N  C10  C11  C6   121.48  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
 14N  CONST_01  C9   C10  C11  C6     0.00   0.0  0
 14N  CONST_02  C9   C8   C7   C6     0.00   0.0  0
 14N  CONST_03  C10  C11  C6   C7     0.00   0.0  0
 14N  CONST_04  C10  C9   C8   C7     0.00   0.0  0
 14N  CONST_05  C11  C6   C7   C8     0.00   0.0  0
 14N  CONST_06  C11  C10  C9   C8     0.00   0.0  0
 14N  CONST_07  C10  C11  C6   N2   180.00   0.0  0
 14N  CONST_08  C8   C7   C6   N2   180.00   0.0  0
 14N  CONST_09  C12  C9   C8   C7   180.00   0.0  0
 14N  CONST_10  C11  C10  C9   C12  180.00   0.0  0
 14N  CONST_11  H17  C11  C6   N2     0.00   0.0  0
 14N  CONST_12  H13  C7   C6   N2     0.00   0.0  0
 14N  CONST_13  H16  C10  C11  C6   180.00   0.0  0
 14N  CONST_14  H14  C8   C7   C6   180.00   0.0  0
 14N  CONST_15  H15  O1   C12  C9   180.00   0.0  0
 14N  Var_01    C5   N1   C2   C3    59.62  30.0  1
 14N  Var_02    C5   C4   N2   C3   -51.48  30.0  1
 14N  Var_03    C11  C6   N2   C3   179.74  30.0  2
 14N  Var_04    C4   N2   C3   C2    51.06  30.0  1
 14N  Var_05    C4   C5   N1   C2   -59.65  30.0  1
 14N  Var_06    N2   C3   C2   N1   -55.34  30.0  1
 14N  Var_07    N2   C4   C5   N1    55.72  30.0  1
 14N  Var_08    O2   C12  C9   C8     0.89  30.0  2
 14N  Var_09    H6   C1   N1   C2    59.67  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
 14N  plan-1  N2   0.020
 14N  plan-1  C6   0.020
 14N  plan-1  C7   0.020
 14N  plan-1  C8   0.020
 14N  plan-1  C9   0.020
 14N  plan-1  C12  0.020
 14N  plan-1  C10  0.020
 14N  plan-1  C11  0.020
 14N  plan-1  H13  0.020
 14N  plan-1  H14  0.020
 14N  plan-1  H16  0.020
 14N  plan-1  H17  0.020
 14N  plan-2  C9   0.020
 14N  plan-2  C12  0.020
 14N  plan-2  O2   0.020
 14N  plan-2  O1   0.020
 14N  plan-2  H15  0.020

