# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 20:47:47 2020
#   Inital geometry file: a 116 line input string
#   Ligand name: 4-[1-(2-fluorophenyl)-1H-pyrazol-4-yl]-3-[(piperidin-4-yl)methoxy]pyridine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Fc1ccccc1n2cc(cn2)c3ccncc3OCC4CCNCC4
#
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
 6BB  6BB  4-[1-(2-fluorophenyl)-1H-pyrazol-4-yl]-3-[(piperidin-4-yl)methoxy]pyridine  ligand  47  26  .  2022-07-23  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_6BB
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
 6BB  C1   C  CR5   0  -0.136   0.5519   1.1956  -0.4998
 6BB  C2   C  CR6   0   0.050  -0.3916   2.2858  -0.2706
 6BB  C3   C  CR16  0  -0.383   0.0584   3.5873  -0.0726
 6BB  C11  C  CH2   0  -0.292  -5.5322  -2.7719  -0.4852
 6BB  C12  C  CH2   0  -0.421  -5.3037  -1.2705  -0.3840
 6BB  C13  C  CR15  0  -0.070   0.3966  -0.0333  -1.1877
 6BB  C14  C  CR15  0   0.035   1.8668   1.1702  -0.0845
 6BB  C15  C  CR6   0   0.167   3.7189  -0.4301  -0.3383
 6BB  C16  C  CR6   0   0.531   3.9856  -1.6886   0.1858
 6BB  C17  C  CR16  0  -0.414   5.2795  -2.1322   0.3665
 6BB  C18  C  CR16  0  -0.236   6.3338  -1.2934   0.0326
 6BB  C19  C  CR16  0  -0.265   6.0874  -0.0269  -0.4789
 6BB  C20  C  CR16  0  -0.276   4.7822   0.3985  -0.6725
 6BB  C4   C  CR16  0  -0.087  -0.8454   4.6083   0.1712
 6BB  N1   N  N     0  -0.393  -2.1543   4.4116   0.2189
 6BB  C5   C  CR16  0  -0.196  -2.6088   3.1785   0.0282
 6BB  C6   C  CR6   0   0.286  -1.7807   2.0845  -0.2167
 6BB  C7   C  CH2   0  -0.162  -3.6095   0.5497  -0.2711
 6BB  C8   C  CH1   0  -0.289  -3.8115  -0.9439  -0.4357
 6BB  C9   C  CH2   0  -0.414  -3.0649  -1.7601   0.6188
 6BB  C10  C  CH2   0  -0.295  -3.3836  -3.2411   0.4789
 6BB  N2   N  NH1   0  -0.595  -4.8165  -3.4558   0.5768
 6BB  N3   N  N     0  -0.270   1.5095  -0.7302  -1.1949
 6BB  N4   N  NR5   0  -0.384   2.3926   0.0078  -0.5144
 6BB  F1   F  F     0  -0.296   2.9689  -2.4788   0.5390
 6BB  H1   H  HCR6  0   0.265   1.1160   3.8121  -0.1196
 6BB  H3   H  HCH2  0   0.186  -5.2202  -3.1095  -1.4882
 6BB  H4   H  HCH2  0   0.233  -5.8329  -0.7655  -1.1963
 6BB  H5   H  HCH2  0   0.216  -5.7295  -0.9057   0.5572
 6BB  H6   H  HCR5  0   0.265  -0.4769  -0.4165  -1.6885
 6BB  H7   H  HCR5  0   0.309   2.4405   1.8679   0.5042
 6BB  H8   H  HCR6  0   0.290   5.4574  -3.1172   0.7776
 6BB  H9   H  HCR6  0   0.277   7.3495  -1.6353   0.1762
 6BB  H10  H  HCR6  0   0.272   6.9086   0.6256  -0.7412
 6BB  H11  H  HCR6  0   0.290   4.5797   1.3753  -1.0927
 6BB  H12  H  HCR6  0   0.260  -0.4936   5.6219   0.3244
 6BB  H13  H  HCR6  0   0.279  -3.6846   3.0580   0.0747
 6BB  H14  H  HCH2  0   0.221  -3.9733   0.8729   0.7125
 6BB  H15  H  HCH2  0   0.236  -4.1793   1.0941  -1.0335
 6BB  H16  H  HCH1  0   0.229  -3.4377  -1.2339  -1.4268
 6BB  H17  H  HCH2  0   0.236  -1.9867  -1.6125   0.5317
 6BB  H18  H  HCH2  0   0.211  -3.3595  -1.4194   1.6177
 6BB  H19  H  HCH2  0   0.185  -2.9689  -3.6018  -0.4779
 6BB  H20  H  HCH2  0   0.231  -2.8871  -3.8051   1.2713
 6BB  H21  H  HNH1  0   0.351  -5.0123  -4.4471   0.5306
 6BB  O1   O  O2    0  -0.470  -2.2241   0.8343  -0.3992
 6BB  H2   H  HCH2  0   0.232  -6.5977  -2.9923  -0.3939

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
 6BB  C19  C18  aromatic  1.388  0.020  1.388
 6BB  C19  C20  aromatic  1.386  0.020  1.386
 6BB  C18  C17  aromatic  1.388  0.020  1.388
 6BB  C20  C15  aromatic  1.389  0.020  1.389
 6BB  C17  C16  aromatic  1.380  0.020  1.380
 6BB  C15  C16  aromatic  1.389  0.020  1.389
 6BB  C15  N4   single    1.408  0.020  1.408
 6BB  C16  F1   single    1.335  0.020  1.335
 6BB  N3   N4   aromatic  1.337  0.020  1.337
 6BB  N3   C13  aromatic  1.313  0.020  1.313
 6BB  N4   C14  aromatic  1.346  0.020  1.346
 6BB  C13  C1   aromatic  1.417  0.020  1.417
 6BB  C14  C1   aromatic  1.379  0.020  1.379
 6BB  C1   C2   single    1.460  0.020  1.460
 6BB  C10  C9   single    1.521  0.020  1.521
 6BB  C10  N2   single    1.452  0.020  1.452
 6BB  C2   C3   aromatic  1.391  0.020  1.391
 6BB  C2   C6   aromatic  1.405  0.020  1.405
 6BB  C9   C8   single    1.528  0.020  1.528
 6BB  O1   C6   single    1.339  0.020  1.339
 6BB  O1   C7   single    1.420  0.020  1.420
 6BB  C3   C4   aromatic  1.385  0.020  1.385
 6BB  C8   C7   single    1.516  0.020  1.516
 6BB  C8   C12  single    1.528  0.020  1.528
 6BB  N2   C11  single    1.452  0.020  1.452
 6BB  C11  C12  single    1.522  0.020  1.522
 6BB  C6   C5   aromatic  1.394  0.020  1.394
 6BB  C4   N1   aromatic  1.324  0.020  1.324
 6BB  C5   N1   aromatic  1.328  0.020  1.328
 6BB  C3   H1   single    0.930  0.020  1.080
 6BB  C11  H2   single    0.970  0.020  1.090
 6BB  C11  H3   single    0.970  0.020  1.090
 6BB  C12  H4   single    0.970  0.020  1.090
 6BB  C12  H5   single    0.970  0.020  1.090
 6BB  C13  H6   single    0.930  0.020  1.080
 6BB  C14  H7   single    0.930  0.020  1.080
 6BB  C17  H8   single    0.930  0.020  1.080
 6BB  C18  H9   single    0.930  0.020  1.080
 6BB  C19  H10  single    0.930  0.020  1.080
 6BB  C20  H11  single    0.930  0.020  1.080
 6BB  C4   H12  single    0.930  0.020  1.080
 6BB  C5   H13  single    0.930  0.020  1.080
 6BB  C7   H14  single    0.970  0.020  1.090
 6BB  C7   H15  single    0.970  0.020  1.090
 6BB  C8   H16  single    0.970  0.020  1.090
 6BB  C9   H17  single    0.970  0.020  1.090
 6BB  C9   H18  single    0.970  0.020  1.090
 6BB  C10  H19  single    0.970  0.020  1.090
 6BB  C10  H20  single    0.970  0.020  1.090
 6BB  N2   H21  single    0.890  0.020  1.040

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
 6BB  C14  C1   C13  103.58  3.000
 6BB  C14  C1   C2   125.64  3.000
 6BB  C13  C1   C2   130.77  3.000
 6BB  C6   C2   C3   116.64  3.000
 6BB  C6   C2   C1   122.56  3.000
 6BB  C3   C2   C1   120.79  3.000
 6BB  H1   C3   C4   119.48  3.000
 6BB  H1   C3   C2   120.28  3.000
 6BB  C4   C3   C2   120.24  3.000
 6BB  H3   C11  H2   106.87  3.000
 6BB  H3   C11  N2   112.42  3.000
 6BB  H2   C11  N2   108.95  3.000
 6BB  H3   C11  C12  108.65  3.000
 6BB  H2   C11  C12  109.88  3.000
 6BB  N2   C11  C12  110.00  3.000
 6BB  H5   C12  H4   107.25  3.000
 6BB  H5   C12  C8   109.71  3.000
 6BB  H4   C12  C8   110.41  3.000
 6BB  H5   C12  C11  109.10  3.000
 6BB  H4   C12  C11  109.49  3.000
 6BB  C8   C12  C11  110.80  3.000
 6BB  H6   C13  N3   119.72  3.000
 6BB  H6   C13  C1   128.55  3.000
 6BB  N3   C13  C1   111.72  3.000
 6BB  H7   C14  N4   121.69  3.000
 6BB  H7   C14  C1   131.28  3.000
 6BB  N4   C14  C1   106.98  3.000
 6BB  N4   C15  C20  120.37  3.000
 6BB  N4   C15  C16  120.66  3.000
 6BB  C20  C15  C16  118.97  3.000
 6BB  F1   C16  C17  119.28  3.000
 6BB  F1   C16  C15  119.33  3.000
 6BB  C17  C16  C15  121.39  3.000
 6BB  H8   C17  C18  121.11  3.000
 6BB  H8   C17  C16  119.78  3.000
 6BB  C18  C17  C16  119.11  3.000
 6BB  H9   C18  C19  120.28  3.000
 6BB  H9   C18  C17  119.37  3.000
 6BB  C19  C18  C17  120.35  3.000
 6BB  H10  C19  C20  119.73  3.000
 6BB  H10  C19  C18  120.35  3.000
 6BB  C20  C19  C18  119.91  3.000
 6BB  H11  C20  C19  120.48  3.000
 6BB  H11  C20  C15  119.25  3.000
 6BB  C19  C20  C15  120.27  3.000
 6BB  H12  C4   N1   117.04  3.000
 6BB  H12  C4   C3   120.16  3.000
 6BB  N1   C4   C3   122.80  3.000
 6BB  C5   N1   C4   118.10  3.000
 6BB  H13  C5   C6   120.67  3.000
 6BB  H13  C5   N1   115.91  3.000
 6BB  C6   C5   N1   123.42  3.000
 6BB  C5   C6   O1   124.06  3.000
 6BB  C5   C6   C2   118.80  3.000
 6BB  O1   C6   C2   117.13  3.000
 6BB  H15  C7   H14  107.74  3.000
 6BB  H15  C7   C8   110.15  3.000
 6BB  H14  C7   C8   110.08  3.000
 6BB  H15  C7   O1   110.17  3.000
 6BB  H14  C7   O1   110.19  3.000
 6BB  C8   C7   O1   108.52  3.000
 6BB  H16  C8   C9   108.38  3.000
 6BB  H16  C8   C7   108.23  3.000
 6BB  C9   C8   C7   112.72  3.000
 6BB  H16  C8   C12  107.84  3.000
 6BB  C7   C8   C12  109.69  3.000
 6BB  C9   C8   C12  109.85  3.000
 6BB  H18  C9   H17  107.23  3.000
 6BB  H18  C9   C10  109.28  3.000
 6BB  H17  C9   C10  109.34  3.000
 6BB  H18  C9   C8   109.36  3.000
 6BB  H17  C9   C8   110.81  3.000
 6BB  C10  C9   C8   110.74  3.000
 6BB  H20  C10  H19  106.83  3.000
 6BB  H20  C10  N2   108.87  3.000
 6BB  H19  C10  N2   112.39  3.000
 6BB  H20  C10  C9   109.93  3.000
 6BB  H19  C10  C9   108.62  3.000
 6BB  N2   C10  C9   110.15  3.000
 6BB  H21  N2   C10  109.44  3.000
 6BB  H21  N2   C11  109.44  3.000
 6BB  C10  N2   C11  111.56  3.000
 6BB  N4   N3   C13  105.31  3.000
 6BB  N3   N4   C15  120.95  3.000
 6BB  N3   N4   C14  112.41  3.000
 6BB  C15  N4   C14  126.62  3.000
 6BB  C7   O1   C6   119.86  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
 6BB  CONST_01  N4   N3   C13  C1      0.00   0.0  0
 6BB  CONST_02  C15  N4   C14  C1    180.00   0.0  0
 6BB  CONST_03  N3   N4   C14  C1      0.00   0.0  0
 6BB  CONST_04  C4   C3   C2   C1    180.00   0.0  0
 6BB  CONST_05  C5   C6   C2   C1    180.00   0.0  0
 6BB  CONST_06  N3   C13  C1   C2    180.00   0.0  0
 6BB  CONST_07  N4   C14  C1   C2    180.00   0.0  0
 6BB  CONST_08  N1   C4   C3   C2      0.00   0.0  0
 6BB  CONST_09  N1   C5   C6   C2      0.00   0.0  0
 6BB  CONST_12  C5   C6   C2   C3      0.00   0.0  0
 6BB  CONST_13  C5   N1   C4   C3      0.00   0.0  0
 6BB  CONST_14  C15  N4   N3   C13   180.00   0.0  0
 6BB  CONST_15  C14  N4   N3   C13     0.00   0.0  0
 6BB  CONST_16  N4   C14  C1   C13     0.00   0.0  0
 6BB  CONST_20  N3   C13  C1   C14     0.00   0.0  0
 6BB  CONST_22  C18  C19  C20  C15     0.00   0.0  0
 6BB  CONST_23  C18  C17  C16  C15     0.00   0.0  0
 6BB  CONST_24  C19  C18  C17  C16     0.00   0.0  0
 6BB  CONST_25  C19  C20  C15  C16     0.00   0.0  0
 6BB  CONST_27  C20  C19  C18  C17     0.00   0.0  0
 6BB  CONST_28  C20  C15  C16  C17     0.00   0.0  0
 6BB  CONST_29  N4   C15  C16  C17   180.00   0.0  0
 6BB  CONST_30  N4   C15  C20  C19   180.00   0.0  0
 6BB  CONST_32  C6   C2   C3   C4      0.00   0.0  0
 6BB  CONST_33  C6   C5   N1   C4      0.00   0.0  0
 6BB  CONST_34  O1   C6   C2   C1      0.00   0.0  0
 6BB  CONST_35  O1   C6   C2   C3    180.00   0.0  0
 6BB  CONST_36  N1   C5   C6   O1    180.00   0.0  0
 6BB  CONST_37  F1   C16  C17  C18   180.00   0.0  0
 6BB  CONST_38  F1   C16  C15  C20   180.00   0.0  0
 6BB  CONST_39  F1   C16  C15  N4      0.00   0.0  0
 6BB  CONST_40  H1   C3   C2   C1      0.00   0.0  0
 6BB  CONST_41  H6   C13  C1   C2      0.00   0.0  0
 6BB  CONST_42  H7   C14  C1   C2      0.00   0.0  0
 6BB  CONST_43  H12  C4   C3   C2    180.00   0.0  0
 6BB  CONST_44  H13  C5   C6   C2    180.00   0.0  0
 6BB  CONST_45  H10  C19  C20  C15   180.00   0.0  0
 6BB  CONST_46  H8   C17  C16  C15   180.00   0.0  0
 6BB  CONST_47  H9   C18  C17  C16   180.00   0.0  0
 6BB  CONST_48  H11  C20  C15  C16   180.00   0.0  0
 6BB  Var_01    C9   C10  N2   C11    61.65  30.0  1
 6BB  Var_02    C10  N2   C11  C12   -61.64  30.0  1
 6BB  Var_03    N2   C10  C9   C8    -56.97  30.0  1
 6BB  Var_04    N2   C11  C12  C8     57.09  30.0  1
 6BB  Var_05    C8   C7   O1   C6   -176.25  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 6BB  chir_01  C8  C9  C7  C12  positiv

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
 6BB  plan-1  C1   0.020
 6BB  plan-1  C2   0.020
 6BB  plan-1  C13  0.020
 6BB  plan-1  C14  0.020
 6BB  plan-1  C15  0.020
 6BB  plan-1  N3   0.020
 6BB  plan-1  N4   0.020
 6BB  plan-1  H6   0.020
 6BB  plan-1  H7   0.020
 6BB  plan-2  C1   0.020
 6BB  plan-2  C2   0.020
 6BB  plan-2  C3   0.020
 6BB  plan-2  C4   0.020
 6BB  plan-2  N1   0.020
 6BB  plan-2  C5   0.020
 6BB  plan-2  C6   0.020
 6BB  plan-2  H1   0.020
 6BB  plan-2  H12  0.020
 6BB  plan-2  H13  0.020
 6BB  plan-2  O1   0.020
 6BB  plan-3  C15  0.020
 6BB  plan-3  C16  0.020
 6BB  plan-3  C17  0.020
 6BB  plan-3  C18  0.020
 6BB  plan-3  C19  0.020
 6BB  plan-3  C20  0.020
 6BB  plan-3  N4   0.020
 6BB  plan-3  F1   0.020
 6BB  plan-3  H8   0.020
 6BB  plan-3  H9   0.020
 6BB  plan-3  H10  0.020
 6BB  plan-3  H11  0.020

