# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 04:06:38 2020
#   Inital geometry file: a 67 line input string
#   Ligand name: 6-(hydroxymethyl)[2,2'-bipyridin]-4-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCc1cc(O)cc(n1)c2ccccn2
#
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
 67L  67L  6-(hydroxymethyl)[2,2'-bipyridin]-4-ol  ligand  25  15  .  2021-08-05  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_67L
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
 67L  CAC  C  CR16  0  -0.304  -2.1556   1.3607  -0.0039
 67L  CAB  C  CR16  0  -0.152  -3.5261   1.5599   0.0208
 67L  CAA  C  CR16  0  -0.322  -4.3662   0.4572   0.0284
 67L  CAF  C  CR16  0  -0.073  -3.7857  -0.8033   0.0099
 67L  NAE  N  N     0  -0.432  -2.4767  -1.0017  -0.0140
 67L  CAD  C  CR6   0   0.196  -1.6680   0.0555  -0.0205
 67L  CAG  C  CR6   0   0.202  -0.2077  -0.2132  -0.0456
 67L  NAL  N  N     0  -0.479   0.5925   0.8488  -0.0332
 67L  CAH  C  CR16  0  -0.405   0.2686  -1.5158  -0.0801
 67L  CAI  C  CR6   0   0.470   1.6452  -1.7100  -0.1015
 67L  OAM  O  OH1   0  -0.614   2.1023  -2.9656  -0.1332
 67L  CAJ  C  CR16  0  -0.466   2.4863  -0.6002  -0.0874
 67L  CAK  C  CR6   0   0.192   1.9057   0.6580  -0.0531
 67L  CAN  C  CH2   0  -0.186   2.7272   1.9173  -0.0278
 67L  OAO  O  OH1   0  -0.664   4.0931   1.6115  -0.1002
 67L  H1   H  HCR6  0   0.270  -1.4702   2.1953  -0.0098
 67L  H2   H  HCR6  0   0.274  -3.9308   2.5634   0.0349
 67L  H3   H  HCR6  0   0.273  -5.4418   0.5638   0.0480
 67L  H4   H  HCR6  0   0.263  -4.4086  -1.6909   0.0153
 67L  H5   H  HCR6  0   0.273  -0.4119  -2.3553  -0.0880
 67L  H6   H  HOH1  0   0.481   3.0669  -2.9799  -0.1386
 67L  H7   H  HCR6  0   0.284   3.5619  -0.7167  -0.1016
 67L  H8   H  HCH2  0   0.225   2.4008   2.5519  -0.8621
 67L  H9   H  HCH2  0   0.227   2.4761   2.4636   0.8907
 67L  H10  H  HOH1  0   0.466   4.5898   2.4309  -0.0223

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
 67L  OAO  CAN  single    1.402  0.020  1.402
 67L  CAN  CAK  single    1.504  0.020  1.504
 67L  CAK  NAL  aromatic  1.327  0.020  1.327
 67L  CAK  CAJ  aromatic  1.386  0.020  1.386
 67L  NAL  CAG  aromatic  1.330  0.020  1.330
 67L  CAJ  CAI  aromatic  1.393  0.020  1.393
 67L  NAE  CAF  aromatic  1.324  0.020  1.324
 67L  NAE  CAD  aromatic  1.331  0.020  1.331
 67L  CAG  CAD  single    1.485  0.020  1.485
 67L  CAG  CAH  aromatic  1.387  0.020  1.387
 67L  CAI  CAH  aromatic  1.390  0.020  1.390
 67L  CAI  OAM  single    1.337  0.020  1.337
 67L  CAF  CAA  aromatic  1.388  0.020  1.388
 67L  CAD  CAC  aromatic  1.393  0.020  1.393
 67L  CAA  CAB  aromatic  1.386  0.020  1.386
 67L  CAC  CAB  aromatic  1.385  0.020  1.385
 67L  CAC  H1   single    0.930  0.020  1.080
 67L  CAB  H2   single    0.930  0.020  1.080
 67L  CAA  H3   single    0.930  0.020  1.080
 67L  CAF  H4   single    0.930  0.020  1.080
 67L  CAH  H5   single    0.930  0.020  1.080
 67L  OAM  H6   single    0.850  0.020  0.980
 67L  CAJ  H7   single    0.930  0.020  1.080
 67L  CAN  H8   single    0.970  0.020  1.090
 67L  CAN  H9   single    0.970  0.020  1.090
 67L  OAO  H10  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
 67L  H1   CAC  CAD  120.12  3.000
 67L  H1   CAC  CAB  121.12  3.000
 67L  CAD  CAC  CAB  118.76  3.000
 67L  H2   CAB  CAA  120.73  3.000
 67L  H2   CAB  CAC  120.24  3.000
 67L  CAA  CAB  CAC  119.03  3.000
 67L  H3   CAA  CAF  120.40  3.000
 67L  H3   CAA  CAB  121.64  3.000
 67L  CAF  CAA  CAB  117.96  3.000
 67L  H4   CAF  NAE  116.44  3.000
 67L  H4   CAF  CAA  120.21  3.000
 67L  NAE  CAF  CAA  123.35  3.000
 67L  CAD  NAE  CAF  118.79  3.000
 67L  CAG  CAD  NAE  116.99  3.000
 67L  CAG  CAD  CAC  120.92  3.000
 67L  NAE  CAD  CAC  122.10  3.000
 67L  CAH  CAG  NAL  122.92  3.000
 67L  CAH  CAG  CAD  120.52  3.000
 67L  NAL  CAG  CAD  116.56  3.000
 67L  CAK  NAL  CAG  118.72  3.000
 67L  H5   CAH  CAI  120.98  3.000
 67L  H5   CAH  CAG  120.89  3.000
 67L  CAI  CAH  CAG  118.12  3.000
 67L  CAJ  CAI  OAM  122.85  3.000
 67L  OAM  CAI  CAH  118.04  3.000
 67L  CAJ  CAI  CAH  119.11  3.000
 67L  H6   OAM  CAI  110.85  3.000
 67L  H7   CAJ  CAK  120.96  3.000
 67L  H7   CAJ  CAI  120.96  3.000
 67L  CAK  CAJ  CAI  118.08  3.000
 67L  CAN  CAK  CAJ  122.12  3.000
 67L  CAJ  CAK  NAL  123.05  3.000
 67L  CAN  CAK  NAL  114.83  3.000
 67L  H9   CAN  H8   106.27  3.000
 67L  H9   CAN  OAO  112.01  3.000
 67L  H8   CAN  OAO  112.13  3.000
 67L  H9   CAN  CAK  107.81  3.000
 67L  H8   CAN  CAK  107.99  3.000
 67L  OAO  CAN  CAK  110.42  3.000
 67L  H10  OAO  CAN  108.26  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
 67L  CONST_01  CAF  NAE  CAD  CAC     0.00   0.0  0
 67L  CONST_02  NAL  CAG  CAD  CAC     0.00   0.0  0
 67L  CONST_03  CAH  CAG  CAD  CAC   180.00   0.0  0
 67L  CONST_04  CAF  CAA  CAB  CAC     0.00   0.0  0
 67L  CONST_05  NAE  CAF  CAA  CAB     0.00   0.0  0
 67L  CONST_06  NAE  CAD  CAC  CAB     0.00   0.0  0
 67L  CONST_07  CAG  CAD  CAC  CAB   180.00   0.0  0
 67L  CONST_08  CAD  NAE  CAF  CAA     0.00   0.0  0
 67L  CONST_09  CAD  CAC  CAB  CAA     0.00   0.0  0
 67L  CONST_10  CAG  CAD  NAE  CAF   180.00   0.0  0
 67L  CONST_11  NAL  CAG  CAD  NAE   180.00   0.0  0
 67L  CONST_12  CAH  CAG  CAD  NAE     0.00   0.0  0
 67L  CONST_13  CAK  NAL  CAG  CAD   180.00   0.0  0
 67L  CONST_14  CAI  CAH  CAG  CAD   180.00   0.0  0
 67L  CONST_15  CAJ  CAK  NAL  CAG     0.00   0.0  0
 67L  CONST_16  CAJ  CAI  CAH  CAG     0.00   0.0  0
 67L  CONST_17  CAI  CAJ  CAK  NAL     0.00   0.0  0
 67L  CONST_18  CAI  CAH  CAG  NAL     0.00   0.0  0
 67L  CONST_19  CAK  NAL  CAG  CAH     0.00   0.0  0
 67L  CONST_20  CAK  CAJ  CAI  CAH     0.00   0.0  0
 67L  CONST_21  CAN  CAK  NAL  CAG   180.00   0.0  0
 67L  CONST_22  OAM  CAI  CAH  CAG   180.00   0.0  0
 67L  CONST_23  CAN  CAK  CAJ  CAI   180.00   0.0  0
 67L  CONST_24  CAK  CAJ  CAI  OAM   180.00   0.0  0
 67L  CONST_25  H3   CAA  CAB  CAC   180.00   0.0  0
 67L  CONST_26  H4   CAF  CAA  CAB   180.00   0.0  0
 67L  CONST_27  H1   CAC  CAB  CAA   180.00   0.0  0
 67L  CONST_28  H2   CAB  CAA  CAF   180.00   0.0  0
 67L  CONST_29  H5   CAH  CAG  CAD     0.00   0.0  0
 67L  CONST_30  H7   CAJ  CAK  NAL   180.00   0.0  0
 67L  Var_01    OAO  CAN  CAK  NAL  -177.87  30.0  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
 67L  plan-1  CAC  0.020
 67L  plan-1  CAB  0.020
 67L  plan-1  CAA  0.020
 67L  plan-1  CAF  0.020
 67L  plan-1  NAE  0.020
 67L  plan-1  CAD  0.020
 67L  plan-1  CAG  0.020
 67L  plan-1  H1   0.020
 67L  plan-1  H2   0.020
 67L  plan-1  H3   0.020
 67L  plan-1  H4   0.020
 67L  plan-2  CAD  0.020
 67L  plan-2  CAG  0.020
 67L  plan-2  NAL  0.020
 67L  plan-2  CAH  0.020
 67L  plan-2  CAI  0.020
 67L  plan-2  OAM  0.020
 67L  plan-2  CAJ  0.020
 67L  plan-2  CAK  0.020
 67L  plan-2  CAN  0.020
 67L  plan-2  H5   0.020
 67L  plan-2  H7   0.020

