# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 17:52:24 2020
#   Inital geometry file: a 129 line input string
#   Ligand name: 1,1'-heptane-1,7-diylbis{2-[(E)-(hydroxyimino)methyl]pyridinium}
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O\N=C\c1cccc[n+]1CCCCCCC[n+]2ccccc2\C=N\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
 HBP  HBP  1,1'-heptane-1,7-diylbis{2-[(E)-(hydroxyimino)methyl]pyridinium}  ligand  51  25  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HBP
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
 HBP  C1    C  CH2   0  -0.380   3.6809  -0.5260   1.1788
 HBP  C5    C  CH2   0  -0.427   1.2127  -0.0958   1.1807
 HBP  O10   O  OH1   0  -0.504   5.6763   3.5705  -0.4730
 HBP  N9    N  N     0  -0.066   6.0882   2.3058  -0.5848
 HBP  C8A   C  C1    0  -0.079   5.2417   1.4573  -0.1613
 HBP  C7    C  CR6   0   0.395   5.6030   0.0453  -0.2721
 HBP  C6    C  CR16  0  -0.330   6.6914  -0.3693  -1.0296
 HBP  C4    C  CR16  0  -0.333   6.2197  -2.6426  -0.4682
 HBP  C3    C  CR16  0   0.062   5.1570  -2.1958   0.2721
 HBP  N2    N  NR6   1  -0.481   4.8656  -0.8870   0.3718
 HBP  C2    C  CH2   0  -0.441   2.4342  -0.3883   0.3190
 HBP  C5A   C  CR16  0  -0.087   7.0065  -1.7081  -1.1278
 HBP  C8    C  CH2   0  -0.420  -0.0516   0.0777   0.3496
 HBP  C11   C  CH2   0  -0.426  -1.2909   0.2886   1.2088
 HBP  C14   C  CH2   0  -0.440  -2.5453   0.4966   0.3704
 HBP  C17   C  CH2   0  -0.377  -3.7709   0.6384   1.2589
 HBP  N20   N  NR6   1  -0.480  -4.9965   0.8709   0.4668
 HBP  C21   C  CR16  0   0.061  -5.4400   2.1364   0.3766
 HBP  C22   C  CR16  0  -0.333  -6.5315   2.4640  -0.3850
 HBP  C23   C  CR16  0  -0.087  -7.1851   1.4532  -1.0762
 HBP  C24   C  CR16  0  -0.331  -6.7227   0.1575  -0.9758
 HBP  C25   C  CR6   0   0.393  -5.6104  -0.1348  -0.1976
 HBP  C26   C  C1    0  -0.085  -5.0974  -1.4977  -0.0753
 HBP  N27   N  N     0  -0.064  -5.5381  -2.3623  -0.8961
 HBP  O28   O  OH1   0  -0.505  -5.0388  -3.5847  -0.6950
 HBP  H1A   H  HCH2  0   0.310   3.5517  -1.3176   1.9136
 HBP  H1B   H  HCH2  0   0.304   3.9020   0.3794   1.7398
 HBP  H6    H  HCH2  0   0.231   1.0714  -0.9113   1.8969
 HBP  H7    H  HCH2  0   0.231   1.3863   0.8081   1.7730
 HBP  H10A  H  HOH1  0   0.495   6.4058   4.1027  -0.8141
 HBP  H8    H  H     0   0.288   4.2846   1.7619   0.2492
 HBP  H6A   H  HCR6  0   0.314   7.2792   0.3739  -1.5465
 HBP  H4A   H  HCR6  0   0.316   6.4228  -3.7013  -0.5191
 HBP  H3A   H  HCR6  0   0.349   4.5122  -2.8706   0.8140
 HBP  H4    H  HCH2  0   0.256   2.2803  -1.3156  -0.2393
 HBP  H3    H  HCH2  0   0.248   2.5654   0.4047  -0.4228
 HBP  H5    H  HCR6  0   0.314   7.8552  -2.0218  -1.7190
 HBP  H10   H  HCH2  0   0.224   0.0737   0.9261  -0.3308
 HBP  H9    H  HCH2  0   0.223  -0.1965  -0.8036  -0.2838
 HBP  H12   H  HCH2  0   0.230  -1.4287  -0.5758   1.8664
 HBP  H13   H  HCH2  0   0.232  -1.1429   1.1527   1.8642
 HBP  H15   H  HCH2  0   0.257  -2.4419   1.3949  -0.2440
 HBP  H16   H  HCH2  0   0.249  -2.6688  -0.3427  -0.3202
 HBP  H18   H  HCH2  0   0.304  -3.9220  -0.2305   1.8968
 HBP  H19   H  HCH2  0   0.309  -3.6613   1.4904   1.9260
 HBP  H21   H  HCR6  0   0.350  -4.8898   2.8763   0.9373
 HBP  H22   H  HCR6  0   0.316  -6.8582   3.4917  -0.4269
 HBP  H23   H  HCR6  0   0.314  -8.0529   1.6719  -1.6823
 HBP  H24   H  HCR6  0   0.314  -7.2208  -0.6475  -1.4941
 HBP  H26   H  H     0   0.291  -4.3827  -1.7562   0.6997
 HBP  H28   H  HOH1  0   0.495  -5.4399  -4.1359  -1.3782

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
 HBP  C1   N2    single    1.478  0.020  1.478
 HBP  C1   C2    single    1.521  0.020  1.521
 HBP  C1   H1A   single    0.970  0.020  1.090
 HBP  C1   H1B   single    0.970  0.020  1.090
 HBP  C5   C2    single    1.523  0.020  1.523
 HBP  C5   C8    single    1.523  0.020  1.523
 HBP  C5   H6    single    0.970  0.020  1.090
 HBP  C5   H7    single    0.970  0.020  1.090
 HBP  O10  N9    single    1.335  0.020  1.335
 HBP  O10  H10A  single    0.850  0.020  0.980
 HBP  N9   C8A   double    1.271  0.020  1.271
 HBP  C8A  C7    single    1.462  0.020  1.462
 HBP  C8A  H8    single    0.930  0.020  1.080
 HBP  C7   C6    aromatic  1.389  0.020  1.389
 HBP  C7   N2    aromatic  1.352  0.020  1.352
 HBP  C6   C5A   aromatic  1.379  0.020  1.379
 HBP  C6   H6A   single    0.930  0.020  1.080
 HBP  C4   C3    aromatic  1.370  0.020  1.370
 HBP  C4   C5A   aromatic  1.388  0.020  1.388
 HBP  C4   H4A   single    0.930  0.020  1.080
 HBP  C3   N2    aromatic  1.345  0.020  1.345
 HBP  C3   H3A   single    0.930  0.020  1.080
 HBP  C2   H4    single    0.970  0.020  1.090
 HBP  C2   H3    single    0.970  0.020  1.090
 HBP  C5A  H5    single    0.930  0.020  1.080
 HBP  C8   C11   single    1.523  0.020  1.523
 HBP  C8   H10   single    0.970  0.020  1.090
 HBP  C8   H9    single    0.970  0.020  1.090
 HBP  C11  C14   single    1.523  0.020  1.523
 HBP  C11  H12   single    0.970  0.020  1.090
 HBP  C11  H13   single    0.970  0.020  1.090
 HBP  C14  C17   single    1.520  0.020  1.520
 HBP  C14  H15   single    0.970  0.020  1.090
 HBP  C14  H16   single    0.970  0.020  1.090
 HBP  C17  N20   single    1.478  0.020  1.478
 HBP  C17  H18   single    0.970  0.020  1.090
 HBP  C17  H19   single    0.970  0.020  1.090
 HBP  N20  C21   aromatic  1.344  0.020  1.344
 HBP  N20  C25   aromatic  1.353  0.020  1.353
 HBP  C21  C22   aromatic  1.371  0.020  1.371
 HBP  C21  H21   single    0.930  0.020  1.080
 HBP  C22  C23   aromatic  1.388  0.020  1.388
 HBP  C22  H22   single    0.930  0.020  1.080
 HBP  C23  C24   aromatic  1.379  0.020  1.379
 HBP  C23  H23   single    0.930  0.020  1.080
 HBP  C24  C25   aromatic  1.389  0.020  1.389
 HBP  C24  H24   single    0.930  0.020  1.080
 HBP  C25  C26   single    1.461  0.020  1.461
 HBP  C26  N27   double    1.271  0.020  1.271
 HBP  C26  H26   single    0.930  0.020  1.080
 HBP  N27  O28   single    1.336  0.020  1.336
 HBP  O28  H28   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
 HBP  H1B   C1   H1A  106.34  3.000
 HBP  H1B   C1   C2   112.51  3.000
 HBP  H1A   C1   C2   110.52  3.000
 HBP  H1B   C1   N2   108.78  3.000
 HBP  H1A   C1   N2   106.63  3.000
 HBP  C2    C1   N2   111.75  3.000
 HBP  H7    C5   H6   106.36  3.000
 HBP  H7    C5   C8   109.45  3.000
 HBP  H6    C5   C8   109.56  3.000
 HBP  H7    C5   C2   109.73  3.000
 HBP  H6    C5   C2   109.30  3.000
 HBP  C8    C5   C2   112.27  3.000
 HBP  H10A  O10  N9   105.04  3.000
 HBP  C8A   N9   O10  113.52  3.000
 HBP  H8    C8A  C7   121.19  3.000
 HBP  H8    C8A  N9   121.74  3.000
 HBP  C7    C8A  N9   117.06  3.000
 HBP  N2    C7   C6   118.77  3.000
 HBP  N2    C7   C8A  119.69  3.000
 HBP  C6    C7   C8A  121.55  3.000
 HBP  H6A   C6   C5A  120.66  3.000
 HBP  H6A   C6   C7   118.84  3.000
 HBP  C5A   C6   C7   120.50  3.000
 HBP  H4A   C4   C5A  122.09  3.000
 HBP  H4A   C4   C3   119.43  3.000
 HBP  C5A   C4   C3   118.48  3.000
 HBP  H3A   C3   N2   116.22  3.000
 HBP  H3A   C3   C4   122.07  3.000
 HBP  N2    C3   C4   121.71  3.000
 HBP  C3    N2   C7   121.18  3.000
 HBP  C3    N2   C1   116.86  3.000
 HBP  C7    N2   C1   121.92  3.000
 HBP  H3    C2   H4   106.59  3.000
 HBP  H3    C2   C5   109.91  3.000
 HBP  H4    C2   C5   109.81  3.000
 HBP  H3    C2   C1   110.54  3.000
 HBP  H4    C2   C1   109.11  3.000
 HBP  C5    C2   C1   110.79  3.000
 HBP  H5    C5A  C4   120.63  3.000
 HBP  H5    C5A  C6   120.02  3.000
 HBP  C4    C5A  C6   119.35  3.000
 HBP  H9    C8   H10  106.23  3.000
 HBP  H9    C8   C11  109.28  3.000
 HBP  H10   C8   C11  109.66  3.000
 HBP  H9    C8   C5   109.51  3.000
 HBP  H10   C8   C5   109.41  3.000
 HBP  C11   C8   C5   112.55  3.000
 HBP  H13   C11  H12  106.30  3.000
 HBP  H13   C11  C14  109.46  3.000
 HBP  H12   C11  C14  109.56  3.000
 HBP  H13   C11  C8   109.71  3.000
 HBP  H12   C11  C8   109.38  3.000
 HBP  C14   C11  C8   112.25  3.000
 HBP  H16   C14  H15  106.63  3.000
 HBP  H16   C14  C17  110.46  3.000
 HBP  H15   C14  C17  109.15  3.000
 HBP  H16   C14  C11  109.62  3.000
 HBP  H15   C14  C11  110.10  3.000
 HBP  C17   C14  C11  110.79  3.000
 HBP  H19   C17  H18  106.25  3.000
 HBP  H19   C17  N20  106.81  3.000
 HBP  H18   C17  N20  108.94  3.000
 HBP  H19   C17  C14  110.51  3.000
 HBP  H18   C17  C14  112.33  3.000
 HBP  N20   C17  C14  111.71  3.000
 HBP  C25   N20  C21  121.15  3.000
 HBP  C25   N20  C17  121.52  3.000
 HBP  C21   N20  C17  117.24  3.000
 HBP  H21   C21  C22  122.06  3.000
 HBP  H21   C21  N20  116.26  3.000
 HBP  C22   C21  N20  121.68  3.000
 HBP  H22   C22  C23  122.11  3.000
 HBP  H22   C22  C21  119.35  3.000
 HBP  C23   C22  C21  118.53  3.000
 HBP  H23   C23  C24  120.00  3.000
 HBP  H23   C23  C22  120.67  3.000
 HBP  C24   C23  C22  119.33  3.000
 HBP  H24   C24  C25  118.80  3.000
 HBP  H24   C24  C23  120.73  3.000
 HBP  C25   C24  C23  120.47  3.000
 HBP  C26   C25  C24  121.63  3.000
 HBP  C26   C25  N20  119.54  3.000
 HBP  C24   C25  N20  118.84  3.000
 HBP  H26   C26  N27  121.83  3.000
 HBP  H26   C26  C25  120.86  3.000
 HBP  N27   C26  C25  117.30  3.000
 HBP  O28   N27  C26  113.31  3.000
 HBP  H28   O28  N27  105.11  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
 HBP  CONST_01  C4   C5A  C6   C7      0.00   0.0  0
 HBP  CONST_02  C4   C3   N2   C7      0.00   0.0  0
 HBP  CONST_03  C3   N2   C7   C6      0.00   0.0  0
 HBP  CONST_04  C3   C4   C5A  C6      0.00   0.0  0
 HBP  CONST_05  C5A  C6   C7   N2      0.00   0.0  0
 HBP  CONST_06  C5A  C4   C3   N2      0.00   0.0  0
 HBP  CONST_07  C23  C22  C21  N20     0.00   0.0  0
 HBP  CONST_08  C23  C24  C25  N20     0.00   0.0  0
 HBP  CONST_09  C24  C25  N20  C21     0.00   0.0  0
 HBP  CONST_10  C24  C23  C22  C21     0.00   0.0  0
 HBP  CONST_11  C25  N20  C21  C22     0.00   0.0  0
 HBP  CONST_12  C25  C24  C23  C22     0.00   0.0  0
 HBP  CONST_13  C6   C7   N2   C1    180.00   0.0  0
 HBP  CONST_14  C4   C3   N2   C1    180.00   0.0  0
 HBP  CONST_15  C5A  C6   C7   C8A   180.00   0.0  0
 HBP  CONST_16  C3   N2   C7   C8A   180.00   0.0  0
 HBP  CONST_17  C22  C21  N20  C17   180.00   0.0  0
 HBP  CONST_18  C24  C25  N20  C17   180.00   0.0  0
 HBP  CONST_19  C26  C25  N20  C21   180.00   0.0  0
 HBP  CONST_20  C26  C25  C24  C23   180.00   0.0  0
 HBP  CONST_21  H5   C5A  C6   C7    180.00   0.0  0
 HBP  CONST_22  H3A  C3   N2   C7    180.00   0.0  0
 HBP  CONST_23  H4A  C4   C5A  C6    180.00   0.0  0
 HBP  CONST_24  H6A  C6   C5A  C4    180.00   0.0  0
 HBP  CONST_25  H22  C22  C21  N20   180.00   0.0  0
 HBP  CONST_26  H24  C24  C25  N20   180.00   0.0  0
 HBP  CONST_27  H23  C23  C22  C21   180.00   0.0  0
 HBP  CONST_28  H21  C21  C22  C23   180.00   0.0  0
 HBP  Var_01    C6   C7   C8A  N9    -12.05  30.0  2
 HBP  Var_02    C2   C1   N2   C7     84.14  30.0  2
 HBP  Var_03    C21  N20  C17  C14  -100.13  30.0  2
 HBP  Var_04    N27  C26  C25  N20  -167.30  30.0  2
 HBP  Var_05    C7   C8A  N9   O10   178.81   0.0  2
 HBP  Var_06    N2   C1   C2   C5    176.73  30.0  1
 HBP  Var_07    N20  C17  C14  C11   178.75  30.0  3
 HBP  Var_08    C8   C5   C2   C1    178.80  30.0  1
 HBP  Var_09    C14  C11  C8   C5    178.54  30.0  3
 HBP  Var_10    C11  C8   C5   C2    176.61  30.0  3
 HBP  Var_11    C17  C14  C11  C8    177.34  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
 HBP  plan-1  C1   0.020
 HBP  plan-1  C8A  0.020
 HBP  plan-1  C7   0.020
 HBP  plan-1  C6   0.020
 HBP  plan-1  C4   0.020
 HBP  plan-1  C3   0.020
 HBP  plan-1  N2   0.020
 HBP  plan-1  C5A  0.020
 HBP  plan-1  H6A  0.020
 HBP  plan-1  H4A  0.020
 HBP  plan-1  H3A  0.020
 HBP  plan-1  H5   0.020
 HBP  plan-2  C17  0.020
 HBP  plan-2  N20  0.020
 HBP  plan-2  C21  0.020
 HBP  plan-2  C22  0.020
 HBP  plan-2  C23  0.020
 HBP  plan-2  C24  0.020
 HBP  plan-2  C25  0.020
 HBP  plan-2  C26  0.020
 HBP  plan-2  H21  0.020
 HBP  plan-2  H22  0.020
 HBP  plan-2  H23  0.020
 HBP  plan-2  H24  0.020
 HBP  plan-3  O10  0.020
 HBP  plan-3  N9   0.020
 HBP  plan-3  C8A  0.020
 HBP  plan-3  C7   0.020
 HBP  plan-3  H8   0.020
 HBP  plan-4  C25  0.020
 HBP  plan-4  C26  0.020
 HBP  plan-4  N27  0.020
 HBP  plan-4  O28  0.020
 HBP  plan-4  H26  0.020

