# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Jul 20 22:05:54 2021
#   Inital geometry file: a 75 line input string
#   Ligand name: 4-(1-methyl-3,6-dihydro-2~{H}-pyridin-4-yl)phenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN1CCC(=CC1)c2ccc(O)cc2
#
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
 E3X  E3X  4-(1-methyl-3,6-dihydro-2~{H}-pyridin-4-yl)phenol  ligand  29  14  .  2022-03-18  2022-07-24
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_E3X
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
 E3X  C4   C  CR6   0   0.108  3.7354  5.7464   1.1697
 E3X  C5   C  C     0  -0.518  1.8478  6.6756  -0.2926
 E3X  C6   C  C     0  -0.286  2.4623  4.7050  -2.3368
 E3X  C11  C  CR16  0  -0.363  4.0912  6.6842   3.3901
 E3X  C7   C  CR16  0  -0.324  4.8996  4.9911   1.3676
 E3X  C8   C  CR16  0  -0.319  3.3643  6.5989   2.2109
 E3X  C9   C  C     0  -0.281  0.9486  6.3081  -1.4608
 E3X  C10  C  CR6   0   0.336  5.2306  5.9102   3.5659
 E3X  C12  C  CR16  0  -0.314  5.6320  5.0597   2.5362
 E3X  N3   N  NR6   0  -0.414  1.7355  5.9233  -2.6127
 E3X  C1   C  CR6   0   0.113  2.9479  5.6689  -0.0806
 E3X  C2   C  CR16  0  -0.356  3.1739  4.7485  -1.0239
 E3X  O14  O  OH1   0  -0.632  5.9799  5.9473   4.6862
 E3X  H1   H  H     0   0.244  2.2770  7.6718  -0.4414
 E3X  H2   H  H     0   0.240  1.2221  6.7447   0.6005
 E3X  H3   H  H     0   0.202  1.8003  3.8170  -2.3545
 E3X  H4   H  H     0   0.243  3.1974  4.5388  -3.1317
 E3X  H5   H  HCR6  0   0.270  3.7607  7.3606   4.1702
 E3X  H6   H  HCR6  0   0.248  5.2627  4.3342   0.5884
 E3X  H7   H  HCR6  0   0.254  2.4872  7.2252   2.1233
 E3X  H8   H  H     0   0.237  0.3297  7.1686  -1.7239
 E3X  H9   H  H     0   0.193  0.2562  5.5031  -1.1574
 E3X  H10  H  HCR6  0   0.263  6.5257  4.4591   2.6505
 E3X  H12  H  HCH3  0   0.234  0.4421  6.7428  -4.0315
 E3X  H13  H  HCH3  0   0.232  1.5663  5.5386  -4.6579
 E3X  H14  H  HCH3  0   0.191  0.1536  5.0213  -3.7253
 E3X  H15  H  HCR6  0   0.244  3.9166  3.9726  -0.8825
 E3X  H16  H  HOH1  0   0.474  5.6020  6.5670   5.3194
 E3X  C15  C  CH3   0  -0.518  0.9332  5.7949  -3.8066

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
 E3X  C15  N3   single    1.444  0.020  1.444
 E3X  N3   C6   single    1.445  0.020  1.445
 E3X  N3   C9   single    1.447  0.020  1.447
 E3X  C6   C2   single    1.494  0.020  1.494
 E3X  C9   C5   single    1.519  0.020  1.519
 E3X  C2   C1   double    1.337  0.020  1.337
 E3X  C5   C1   single    1.506  0.020  1.506
 E3X  C1   C4   single    1.480  0.020  1.480
 E3X  C4   C7   aromatic  1.402  0.020  1.402
 E3X  C4   C8   aromatic  1.396  0.020  1.396
 E3X  C7   C12  aromatic  1.381  0.020  1.381
 E3X  C8   C11  aromatic  1.388  0.020  1.388
 E3X  C12  C10  aromatic  1.395  0.020  1.395
 E3X  C11  C10  aromatic  1.389  0.020  1.389
 E3X  C10  O14  single    1.348  0.020  1.348
 E3X  C5   H1   single    0.970  0.020  1.090
 E3X  C5   H2   single    0.970  0.020  1.090
 E3X  C6   H3   single    0.970  0.020  1.090
 E3X  C6   H4   single    0.970  0.020  1.090
 E3X  C11  H5   single    0.930  0.020  1.080
 E3X  C7   H6   single    0.930  0.020  1.080
 E3X  C8   H7   single    0.930  0.020  1.080
 E3X  C9   H8   single    0.970  0.020  1.090
 E3X  C9   H9   single    0.970  0.020  1.090
 E3X  C12  H10  single    0.930  0.020  1.080
 E3X  C15  H12  single    0.970  0.020  1.090
 E3X  C15  H13  single    0.970  0.020  1.090
 E3X  C15  H14  single    0.970  0.020  1.090
 E3X  C2   H15  single    0.930  0.020  1.080
 E3X  O14  H16  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
 E3X  C1   C4   C8   121.38  3.000
 E3X  C8   C4   C7   116.39  3.000
 E3X  C1   C4   C7   122.21  3.000
 E3X  H2   C5   H1   106.14  3.000
 E3X  H2   C5   C1   110.21  3.000
 E3X  H1   C5   C1   109.93  3.000
 E3X  H2   C5   C9   107.75  3.000
 E3X  H1   C5   C9   110.34  3.000
 E3X  C1   C5   C9   112.27  3.000
 E3X  H4   C6   H3   105.54  3.000
 E3X  H4   C6   C2   108.81  3.000
 E3X  H3   C6   C2   108.79  3.000
 E3X  H4   C6   N3   109.08  3.000
 E3X  H3   C6   N3   111.85  3.000
 E3X  C2   C6   N3   112.50  3.000
 E3X  H5   C11  C10  120.45  3.000
 E3X  H5   C11  C8   119.35  3.000
 E3X  C10  C11  C8   120.21  3.000
 E3X  H6   C7   C12  117.49  3.000
 E3X  H6   C7   C4   120.28  3.000
 E3X  C12  C7   C4   122.23  3.000
 E3X  H7   C8   C11  117.26  3.000
 E3X  H7   C8   C4   120.60  3.000
 E3X  C11  C8   C4   122.14  3.000
 E3X  H9   C9   H8   106.58  3.000
 E3X  H9   C9   N3   111.46  3.000
 E3X  H8   C9   N3   109.03  3.000
 E3X  H9   C9   C5   109.64  3.000
 E3X  H8   C9   C5   109.27  3.000
 E3X  N3   C9   C5   110.76  3.000
 E3X  O14  C10  C12  118.06  3.000
 E3X  O14  C10  C11  123.09  3.000
 E3X  C12  C10  C11  118.86  3.000
 E3X  H10  C12  C10  119.86  3.000
 E3X  H10  C12  C7   119.97  3.000
 E3X  C10  C12  C7   120.16  3.000
 E3X  C15  N3   C9   112.31  3.000
 E3X  C9   N3   C6   110.22  3.000
 E3X  C15  N3   C6   111.24  3.000
 E3X  C2   C1   C5   118.95  3.000
 E3X  C5   C1   C4   118.21  3.000
 E3X  C2   C1   C4   122.84  3.000
 E3X  H15  C2   C1   121.11  3.000
 E3X  H15  C2   C6   114.86  3.000
 E3X  C1   C2   C6   124.03  3.000
 E3X  H16  O14  C10  110.24  3.000
 E3X  H14  C15  H13  107.65  3.000
 E3X  H14  C15  H12  107.87  3.000
 E3X  H13  C15  H12  107.72  3.000
 E3X  H14  C15  N3   113.25  3.000
 E3X  H13  C15  N3   110.09  3.000
 E3X  H12  C15  N3   110.08  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
 E3X  CONST_01  C10  C12  C7   C4      0.00   0.0  0
 E3X  CONST_02  C10  C11  C8   C4      0.00   0.0  0
 E3X  CONST_03  C7   C4   C8   C11     0.00   0.0  0
 E3X  CONST_04  C7   C12  C10  C11     0.00   0.0  0
 E3X  CONST_05  C12  C7   C4   C8      0.00   0.0  0
 E3X  CONST_06  C12  C10  C11  C8      0.00   0.0  0
 E3X  CONST_07  C1   C4   C8   C11   180.00   0.0  0
 E3X  CONST_08  C1   C4   C7   C12   180.00   0.0  0
 E3X  CONST_09  O14  C10  C12  C7    180.00   0.0  0
 E3X  CONST_10  O14  C10  C11  C8    180.00   0.0  0
 E3X  CONST_11  H10  C12  C7   C4    180.00   0.0  0
 E3X  CONST_12  H5   C11  C8   C4    180.00   0.0  0
 E3X  CONST_13  H7   C8   C4   C7    180.00   0.0  0
 E3X  CONST_14  H6   C7   C4   C8    180.00   0.0  0
 E3X  Var_01    C6   C2   C1   C4   -175.46  30.0  1
 E3X  Var_02    C9   C5   C1   C4   -168.19  30.0  1
 E3X  Var_03    C6   N3   C9   C5     65.55  30.0  1
 E3X  Var_04    C7   C4   C1   C5   -170.17  30.0  2
 E3X  Var_05    C2   C6   N3   C9    -47.96  30.0  1
 E3X  Var_06    C1   C2   C6   N3     13.45  30.0  1
 E3X  Var_07    C1   C5   C9   N3    -46.36  30.0  1
 E3X  Var_08    H12  C15  N3   C6   -176.50  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
 E3X  plan-1  C4   0.020
 E3X  plan-1  C11  0.020
 E3X  plan-1  C7   0.020
 E3X  plan-1  C8   0.020
 E3X  plan-1  C10  0.020
 E3X  plan-1  C12  0.020
 E3X  plan-1  C1   0.020
 E3X  plan-1  O14  0.020
 E3X  plan-1  H5   0.020
 E3X  plan-1  H6   0.020
 E3X  plan-1  H7   0.020
 E3X  plan-1  H10  0.020

