# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 23 00:12:16 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: 2,9-dihydroxy-3,10-dimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc2cc3c4cc(O)c(OC)cc4CC[n+]3cc2c1O
#
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
 DEH  DEH  2,9-dihydroxy-3,10-dimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium  ligand  42  24  .  2022-07-24  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_DEH
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
 DEH  C2    C  CR16  0  -0.432  -2.4198  -1.2943   0.4044
 DEH  C3    C  CR6   0   0.303  -3.7910  -1.4212   0.3666
 DEH  C5    C  CR6   0   0.318  -4.5826  -0.3064   0.0243
 DEH  C8    C  CR16  0  -0.447  -3.9753   0.9060  -0.2580
 DEH  C9    C  CR66  0   0.113  -2.5913   1.0304  -0.2196
 DEH  C10   C  C     0  -0.538  -1.9043   2.3309  -0.5024
 DEH  C11   C  C     0  -0.318  -0.7038   2.4543   0.4056
 DEH  N12   N  N     1  -0.504   0.2001   1.3062   0.2021
 DEH  C14   C  CR66  0   0.402  -0.3489   0.0447   0.0809
 DEH  C16   C  CR16  0  -0.453   0.5017  -1.0124  -0.0793
 DEH  C17   C  CR66  0   0.281   1.8992  -0.8484  -0.0976
 DEH  C25   C  CR16  0  -0.331   2.7951  -1.9130  -0.2506
 DEH  C24   C  CR16  0  -0.349   4.1483  -1.6710  -0.2592
 DEH  C21   C  CR6   0   0.323   4.6676  -0.3736  -0.1210
 DEH  O22   O  O2    0  -0.482   5.9737  -0.0623  -0.1189
 DEH  C23   C  CH3   0  -0.439   6.9337  -1.1036  -0.1856
 DEH  C19   C  CR6   0   0.246   3.8052   0.7038   0.0237
 DEH  O20   O  OH1   0  -0.601   4.2356   1.9598   0.1533
 DEH  C18   C  CR66  0  -0.117   2.4138   0.4695   0.0378
 DEH  C1    C  CR66  0   0.069  -1.8071  -0.0727   0.1026
 DEH  C13   C  CR16  0   0.081   1.5017   1.5147   0.1803
 DEH  O6    O  O2    0  -0.480  -5.9049  -0.5339   0.0240
 DEH  C7    C  CH3   0  -0.437  -6.7832   0.5432  -0.2516
 DEH  O4    O  OH1   0  -0.627  -4.3497  -2.6071   0.6713
 DEH  H2    H  HCR6  0   0.270  -1.8332  -2.1565   0.6957
 DEH  H8    H  HCR6  0   0.290  -4.5679   1.7773  -0.5052
 DEH  H10   H  H     0   0.280  -1.5920   2.3953  -1.5490
 DEH  H10A  H  H     0   0.289  -2.5696   3.1736  -0.3151
 DEH  H11   H  H     0   0.299  -0.1384   3.3612   0.2101
 DEH  H11A  H  H     0   0.303  -1.0081   2.4508   1.4534
 DEH  H16   H  HCR6  0   0.294   0.0938  -2.0043  -0.2144
 DEH  H25   H  HCR6  0   0.278   2.4244  -2.9227  -0.3600
 DEH  H24   H  HCR6  0   0.310   4.8229  -2.5085  -0.3754
 DEH  H23   H  HCH3  0   0.270   7.9064  -0.6259  -0.1120
 DEH  H23A  H  HCH3  0   0.240   6.8195  -1.8089   0.6402
 DEH  H23B  H  HCH3  0   0.240   6.8768  -1.6451  -1.1324
 DEH  HO20  H  HOH1  0   0.490   5.2014   1.9979   0.1356
 DEH  H13   H  HCR6  0   0.345   1.8218   2.5413   0.2830
 DEH  H7    H  HCH3  0   0.269  -7.7912   0.1456  -0.1739
 DEH  H7A   H  HCH3  0   0.237  -6.6611   1.3530   0.4710
 DEH  H7B   H  HCH3  0   0.237  -6.6326   0.9370  -1.2592
 DEH  HO4   H  HOH1  0   0.476  -5.3116  -2.5481   0.6234

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
 DEH  C2   C3    aromatic  1.378  0.020  1.378
 DEH  C2   C1    aromatic  1.400  0.020  1.400
 DEH  C2   H2    single    0.930  0.020  1.080
 DEH  C3   C5    aromatic  1.409  0.020  1.409
 DEH  C3   O4    single    1.346  0.020  1.346
 DEH  C5   C8    aromatic  1.385  0.020  1.385
 DEH  C5   O6    single    1.342  0.020  1.342
 DEH  C8   C9    aromatic  1.390  0.020  1.390
 DEH  C8   H8    single    0.930  0.020  1.080
 DEH  C9   C10   single    1.498  0.020  1.498
 DEH  C9   C1    aromatic  1.391  0.020  1.391
 DEH  C10  C11   single    1.510  0.020  1.510
 DEH  C10  H10   single    0.970  0.020  1.090
 DEH  C10  H10A  single    0.970  0.020  1.090
 DEH  C11  N12   single    1.475  0.020  1.475
 DEH  C11  H11   single    0.970  0.020  1.090
 DEH  C11  H11A  single    0.970  0.020  1.090
 DEH  N12  C14   aromatic  1.381  0.020  1.381
 DEH  N12  C13   aromatic  1.318  0.020  1.318
 DEH  C14  C16   aromatic  1.366  0.020  1.366
 DEH  C14  C1    aromatic  1.463  0.020  1.463
 DEH  C16  C17   aromatic  1.407  0.020  1.407
 DEH  C16  H16   single    0.930  0.020  1.080
 DEH  C17  C25   aromatic  1.400  0.020  1.400
 DEH  C17  C18   aromatic  1.421  0.020  1.421
 DEH  C25  C24   aromatic  1.375  0.020  1.375
 DEH  C25  H25   single    0.930  0.020  1.080
 DEH  C24  C21   aromatic  1.404  0.020  1.404
 DEH  C24  H24   single    0.930  0.020  1.080
 DEH  C21  O22   single    1.343  0.020  1.343
 DEH  C21  C19   aromatic  1.388  0.020  1.388
 DEH  O22  C23   single    1.418  0.020  1.418
 DEH  C23  H23   single    0.970  0.020  1.090
 DEH  C23  H23A  single    0.970  0.020  1.090
 DEH  C23  H23B  single    0.970  0.020  1.090
 DEH  C19  O20   single    1.334  0.020  1.334
 DEH  C19  C18   aromatic  1.411  0.020  1.411
 DEH  O20  HO20  single    0.850  0.020  0.980
 DEH  C18  C13   aromatic  1.395  0.020  1.395
 DEH  C13  H13   single    0.930  0.020  1.080
 DEH  O6   C7    single    1.417  0.020  1.417
 DEH  C7   H7    single    0.970  0.020  1.090
 DEH  C7   H7A   single    0.970  0.020  1.090
 DEH  C7   H7B   single    0.970  0.020  1.090
 DEH  O4   HO4   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
 DEH  H2    C2   C1    121.06  3.000
 DEH  H2    C2   C3    118.25  3.000
 DEH  C1    C2   C3    120.68  3.000
 DEH  O4    C3   C5    121.25  3.000
 DEH  O4    C3   C2    119.21  3.000
 DEH  C5    C3   C2    119.53  3.000
 DEH  O6    C5   C8    125.48  3.000
 DEH  O6    C5   C3    114.80  3.000
 DEH  C8    C5   C3    119.71  3.000
 DEH  H8    C8   C9    118.64  3.000
 DEH  H8    C8   C5    120.74  3.000
 DEH  C9    C8   C5    120.61  3.000
 DEH  C1    C9   C10   118.27  3.000
 DEH  C1    C9   C8    119.78  3.000
 DEH  C10   C9   C8    121.95  3.000
 DEH  H10A  C10  H10   107.05  3.000
 DEH  H10A  C10  C11   108.58  3.000
 DEH  H10   C10  C11   110.09  3.000
 DEH  H10A  C10  C9    111.03  3.000
 DEH  H10   C10  C9    111.27  3.000
 DEH  C11   C10  C9    108.79  3.000
 DEH  H11A  C11  H11   108.70  3.000
 DEH  H11A  C11  N12   107.50  3.000
 DEH  H11   C11  N12   107.81  3.000
 DEH  H11A  C11  C10   110.82  3.000
 DEH  H11   C11  C10   111.94  3.000
 DEH  N12   C11  C10   109.90  3.000
 DEH  C13   N12  C14   122.37  3.000
 DEH  C13   N12  C11   118.95  3.000
 DEH  C14   N12  C11   118.65  3.000
 DEH  C1    C14  C16   124.06  3.000
 DEH  C1    C14  N12   117.91  3.000
 DEH  C16   C14  N12   118.01  3.000
 DEH  H16   C16  C17   118.69  3.000
 DEH  H16   C16  C14   119.32  3.000
 DEH  C17   C16  C14   121.97  3.000
 DEH  C18   C17  C25   118.94  3.000
 DEH  C18   C17  C16   117.80  3.000
 DEH  C25   C17  C16   123.25  3.000
 DEH  H25   C25  C24   120.09  3.000
 DEH  H25   C25  C17   120.13  3.000
 DEH  C24   C25  C17   119.79  3.000
 DEH  H24   C24  C21   119.69  3.000
 DEH  H24   C24  C25   118.57  3.000
 DEH  C21   C24  C25   121.74  3.000
 DEH  C19   C21  O22   115.11  3.000
 DEH  C19   C21  C24   119.86  3.000
 DEH  O22   C21  C24   125.03  3.000
 DEH  C23   O22  C21   119.23  3.000
 DEH  H23B  C23  H23A  109.27  3.000
 DEH  H23B  C23  H23   108.87  3.000
 DEH  H23A  C23  H23   109.06  3.000
 DEH  H23B  C23  O22   111.68  3.000
 DEH  H23A  C23  O22   111.59  3.000
 DEH  H23   C23  O22   106.27  3.000
 DEH  C18   C19  O20   118.26  3.000
 DEH  C18   C19  C21   119.01  3.000
 DEH  O20   C19  C21   122.73  3.000
 DEH  HO20  O20  C19   110.96  3.000
 DEH  C13   C18  C19   121.43  3.000
 DEH  C13   C18  C17   117.90  3.000
 DEH  C19   C18  C17   120.67  3.000
 DEH  C14   C1   C9    119.65  3.000
 DEH  C14   C1   C2    120.63  3.000
 DEH  C9    C1   C2    119.69  3.000
 DEH  H13   C13  C18   121.89  3.000
 DEH  H13   C13  N12   116.19  3.000
 DEH  C18   C13  N12   121.93  3.000
 DEH  C7    O6   C5    118.82  3.000
 DEH  H7B   C7   H7A   109.12  3.000
 DEH  H7B   C7   H7    109.02  3.000
 DEH  H7A   C7   H7    109.14  3.000
 DEH  H7B   C7   O6    111.59  3.000
 DEH  H7A   C7   O6    111.45  3.000
 DEH  H7    C7   O6    106.44  3.000
 DEH  HO4   O4   C3    110.41  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
 DEH  CONST_01  C8   C5   C3   C2      0.00   0.0  0
 DEH  CONST_02  C8   C9   C1   C2      0.00   0.0  0
 DEH  CONST_05  C9   C1   C2   C3      0.00   0.0  0
 DEH  CONST_06  C14  C1   C2   C3    180.00   0.0  0
 DEH  CONST_07  C9   C8   C5   C3      0.00   0.0  0
 DEH  CONST_08  C1   C2   C3   C5      0.00   0.0  0
 DEH  CONST_09  C1   C9   C8   C5      0.00   0.0  0
 DEH  CONST_10  C14  C1   C9   C8    180.00   0.0  0
 DEH  CONST_13  C17  C16  C14  N12     0.00   0.0  0
 DEH  CONST_14  C17  C18  C13  N12     0.00   0.0  0
 DEH  CONST_15  C19  C18  C13  N12   180.00   0.0  0
 DEH  CONST_16  C18  C13  N12  C14     0.00   0.0  0
 DEH  CONST_17  C25  C17  C16  C14   180.00   0.0  0
 DEH  CONST_18  C18  C17  C16  C14     0.00   0.0  0
 DEH  CONST_19  C13  N12  C14  C16     0.00   0.0  0
 DEH  CONST_20  C24  C25  C17  C16   180.00   0.0  0
 DEH  CONST_21  C19  C18  C17  C16   180.00   0.0  0
 DEH  CONST_22  C13  C18  C17  C16     0.00   0.0  0
 DEH  CONST_23  C1   C14  C16  C17   180.00   0.0  0
 DEH  CONST_24  C21  C24  C25  C17     0.00   0.0  0
 DEH  CONST_25  C21  C19  C18  C17     0.00   0.0  0
 DEH  CONST_26  C19  C18  C17  C25     0.00   0.0  0
 DEH  CONST_27  C13  C18  C17  C25   180.00   0.0  0
 DEH  CONST_28  C19  C21  C24  C25     0.00   0.0  0
 DEH  CONST_29  C18  C17  C25  C24     0.00   0.0  0
 DEH  CONST_30  C18  C19  C21  C24     0.00   0.0  0
 DEH  CONST_31  C13  C18  C19  C21   180.00   0.0  0
 DEH  CONST_32  C13  N12  C14  C1    180.00   0.0  0
 DEH  CONST_33  O6   C5   C3   C2    180.00   0.0  0
 DEH  CONST_34  O4   C3   C5   C8    180.00   0.0  0
 DEH  CONST_35  O6   C5   C8   C9    180.00   0.0  0
 DEH  CONST_36  O20  C19  C18  C17   180.00   0.0  0
 DEH  CONST_37  O22  C21  C24  C25   180.00   0.0  0
 DEH  CONST_38  O20  C19  C21  C24   180.00   0.0  0
 DEH  CONST_39  C18  C19  C21  O22   180.00   0.0  0
 DEH  CONST_40  C13  C18  C19  O20     0.00   0.0  0
 DEH  CONST_41  O4   C3   C2   C1    180.00   0.0  0
 DEH  CONST_42  H8   C8   C5   C3    180.00   0.0  0
 DEH  CONST_43  H2   C2   C3   C5    180.00   0.0  0
 DEH  CONST_44  H13  C13  N12  C11     0.00   0.0  0
 DEH  CONST_45  H16  C16  C14  N12   180.00   0.0  0
 DEH  CONST_46  H25  C25  C17  C16     0.00   0.0  0
 DEH  CONST_47  H24  C24  C25  C17   180.00   0.0  0
 DEH  Var_01    C11  C10  C9   C8    143.40  30.0  1
 DEH  Var_02    N12  C11  C10  C9     57.50  30.0  1
 DEH  Var_03    C14  N12  C11  C10   -42.68  30.0  1
 DEH  Var_04    C19  C21  O22  C23   176.48  30.0  1
 DEH  Var_05    H7   C7   O6   C5   -178.52  30.0  3
 DEH  Var_06    H23  C23  O22  C21  -176.78  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
 DEH  plan-1  C2   0.020
 DEH  plan-1  C3   0.020
 DEH  plan-1  C5   0.020
 DEH  plan-1  C8   0.020
 DEH  plan-1  C9   0.020
 DEH  plan-1  C10  0.020
 DEH  plan-1  C14  0.020
 DEH  plan-1  C1   0.020
 DEH  plan-1  O6   0.020
 DEH  plan-1  O4   0.020
 DEH  plan-1  H2   0.020
 DEH  plan-1  H8   0.020
 DEH  plan-2  C11  0.020
 DEH  plan-2  N12  0.020
 DEH  plan-2  C14  0.020
 DEH  plan-2  C16  0.020
 DEH  plan-2  C17  0.020
 DEH  plan-2  C25  0.020
 DEH  plan-2  C24  0.020
 DEH  plan-2  C21  0.020
 DEH  plan-2  O22  0.020
 DEH  plan-2  C19  0.020
 DEH  plan-2  O20  0.020
 DEH  plan-2  C18  0.020
 DEH  plan-2  C1   0.020
 DEH  plan-2  C13  0.020
 DEH  plan-2  H16  0.020
 DEH  plan-2  H25  0.020
 DEH  plan-2  H24  0.020
 DEH  plan-2  H13  0.020

