# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 03:04:07 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: (1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(C[C@@H]2N(C)CCc3cc(OC)c(O)cc23)cc1O
#
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
 REN  REN  (1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol  ligand  47  24  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_REN
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
 REN  C2    C  CR16  0  -0.410  -2.3315  -1.2200   0.5405
 REN  C3    C  CR6   0   0.283  -3.6871  -1.4236   0.7095
 REN  C5    C  CR6   0   0.294  -4.5895  -0.4407   0.2762
 REN  C8    C  CR16  0  -0.425  -4.1001   0.7102  -0.3127
 REN  C9    C  CR6   0   0.059  -2.7283   0.9136  -0.4850
 REN  C10   C  CH2   0  -0.520  -2.2595   2.1970  -1.1203
 REN  C11   C  CH2   0  -0.329  -0.7824   2.1301  -1.4898
 REN  N12   N  NT    0  -0.391   0.0276   1.5409  -0.4400
 REN  C14   C  CH1   0  -0.134  -0.3307   0.1414  -0.2771
 REN  C16   C  CH2   0  -0.567   0.5443  -0.5481   0.7748
 REN  C17   C  CR6   0   0.176   2.0193  -0.3740   0.5313
 REN  C25   C  CR16  0  -0.354   2.8459   0.1872   1.4906
 REN  C24   C  CR16  0  -0.365   4.2163   0.3262   1.2719
 REN  C21   C  CR6   0   0.276   4.7767  -0.1004   0.0813
 REN  O22   O  O2    0  -0.491   6.0850  -0.0184  -0.2531
 REN  C23   C  CH3   0  -0.429   6.9857   0.5235   0.6904
 REN  C19   C  CR6   0   0.293   3.9513  -0.6810  -0.8975
 REN  O20   O  OH1   0  -0.635   4.4610  -1.1185  -2.0690
 REN  C18   C  CR16  0  -0.397   2.5956  -0.8128  -0.6630
 REN  C1    C  CR6   0   0.079  -1.8276  -0.0558  -0.0468
 REN  C13   C  CH3   0  -0.542  -0.0004   2.3207   0.7813
 REN  O6    O  O2    0  -0.491  -5.8943  -0.7292   0.4824
 REN  C7    C  CH3   0  -0.430  -6.8661   0.1998   0.0482
 REN  O4    O  OH1   0  -0.637  -4.1153  -2.5674   1.2889
 REN  H2    H  HCR6  0   0.250  -1.6656  -2.0036   0.8792
 REN  H8    H  HCR6  0   0.272  -4.7803   1.4805  -0.6570
 REN  H10   H  HCH2  0   0.249  -2.8572   2.4225  -2.0073
 REN  H10A  H  HCH2  0   0.243  -2.4301   3.0254  -0.4250
 REN  H11   H  HCH2  0   0.234  -0.6530   1.5275  -2.3939
 REN  H11A  H  HCH2  0   0.239  -0.4052   3.1297  -1.7188
 REN  H14   H  HCH1  0   0.252  -0.0941  -0.3368  -1.2373
 REN  H16   H  HCH2  0   0.252   0.2861  -0.1944   1.7758
 REN  H16A  H  HCH2  0   0.265   0.3169  -1.6161   0.7662
 REN  H25   H  HCR6  0   0.245   2.4311   0.5258   2.4320
 REN  H24   H  HCR6  0   0.278   4.8272   0.7738   2.0449
 REN  H23   H  HCH3  0   0.261   7.9725   0.4886   0.2357
 REN  H23A  H  HCH3  0   0.229   6.7442   1.5620   0.9310
 REN  H23B  H  HCH3  0   0.229   7.0011  -0.0582   1.6159
 REN  HO20  H  HOH1  0   0.470   5.4150  -0.9759  -2.0879
 REN  H18   H  HCR6  0   0.252   1.9836  -1.2715  -1.4321
 REN  H13   H  HCH3  0   0.202  -0.9351   2.2530   1.3557
 REN  H13A  H  HCH3  0   0.243   0.8143   2.0302   1.4444
 REN  H13B  H  HCH3  0   0.236   0.1564   3.3718   0.5332
 REN  H7    H  HCH3  0   0.229  -6.8145   0.3639  -1.0313
 REN  H7A   H  HCH3  0   0.261  -7.8354  -0.2263   0.2941
 REN  H7B   H  HCH3  0   0.229  -6.7640   1.1618   0.5573
 REN  HO4   H  HOH1  0   0.470  -5.0790  -2.5790   1.3241

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
 REN  C2   C3    aromatic  1.381  0.020  1.381
 REN  C2   C1    aromatic  1.398  0.020  1.398
 REN  C3   C5    aromatic  1.403  0.020  1.403
 REN  C3   O4    single    1.352  0.020  1.352
 REN  C5   C8    aromatic  1.382  0.020  1.382
 REN  C5   O6    single    1.352  0.020  1.352
 REN  C8   C9    aromatic  1.397  0.020  1.397
 REN  C9   C10   single    1.507  0.020  1.507
 REN  C9   C1    aromatic  1.394  0.020  1.394
 REN  C10  C11   single    1.524  0.020  1.524
 REN  C11  N12   single    1.451  0.020  1.451
 REN  N12  C14   single    1.454  0.020  1.454
 REN  N12  C13   single    1.449  0.020  1.449
 REN  C14  C16   single    1.532  0.020  1.532
 REN  C14  C1    single    1.527  0.020  1.527
 REN  C16  C17   single    1.505  0.020  1.505
 REN  C17  C25   aromatic  1.385  0.020  1.385
 REN  C17  C18   aromatic  1.397  0.020  1.397
 REN  C25  C24   aromatic  1.395  0.020  1.395
 REN  C24  C21   aromatic  1.383  0.020  1.383
 REN  C21  O22   single    1.353  0.020  1.353
 REN  C21  C19   aromatic  1.406  0.020  1.406
 REN  O22  C23   single    1.413  0.020  1.413
 REN  C19  O20   single    1.350  0.020  1.350
 REN  C19  C18   aromatic  1.382  0.020  1.382
 REN  O6   C7    single    1.413  0.020  1.413
 REN  C2   H2    single    0.930  0.020  1.080
 REN  C8   H8    single    0.930  0.020  1.080
 REN  C10  H10   single    0.970  0.020  1.090
 REN  C10  H10A  single    0.970  0.020  1.090
 REN  C11  H11   single    0.970  0.020  1.090
 REN  C11  H11A  single    0.970  0.020  1.090
 REN  C14  H14   single    0.970  0.020  1.090
 REN  C16  H16   single    0.970  0.020  1.090
 REN  C16  H16A  single    0.970  0.020  1.090
 REN  C25  H25   single    0.930  0.020  1.080
 REN  C24  H24   single    0.930  0.020  1.080
 REN  C23  H23   single    0.970  0.020  1.090
 REN  C23  H23A  single    0.970  0.020  1.090
 REN  C23  H23B  single    0.970  0.020  1.090
 REN  O20  HO20  single    0.850  0.020  0.980
 REN  C18  H18   single    0.930  0.020  1.080
 REN  C13  H13   single    0.970  0.020  1.090
 REN  C13  H13A  single    0.970  0.020  1.090
 REN  C13  H13B  single    0.970  0.020  1.090
 REN  C7   H7    single    0.970  0.020  1.090
 REN  C7   H7A   single    0.970  0.020  1.090
 REN  C7   H7B   single    0.970  0.020  1.090
 REN  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
 REN  H2    C2   C1    120.83  3.000
 REN  H2    C2   C3    117.31  3.000
 REN  C1    C2   C3    121.86  3.000
 REN  O4    C3   C5    121.43  3.000
 REN  O4    C3   C2    119.21  3.000
 REN  C5    C3   C2    119.36  3.000
 REN  O6    C5   C8    125.75  3.000
 REN  O6    C5   C3    115.10  3.000
 REN  C8    C5   C3    119.15  3.000
 REN  H8    C8   C9    118.26  3.000
 REN  H8    C8   C5    120.32  3.000
 REN  C9    C8   C5    121.42  3.000
 REN  C1    C9   C10   121.59  3.000
 REN  C1    C9   C8    119.62  3.000
 REN  C10   C9   C8    118.77  3.000
 REN  H10A  C10  H10   105.90  3.000
 REN  H10A  C10  C11   109.76  3.000
 REN  H10   C10  C11   110.01  3.000
 REN  H10A  C10  C9    109.16  3.000
 REN  H10   C10  C9    110.35  3.000
 REN  C11   C10  C9    111.49  3.000
 REN  H11A  C11  H11   106.84  3.000
 REN  H11A  C11  N12   109.30  3.000
 REN  H11   C11  N12   107.94  3.000
 REN  H11A  C11  C10   110.20  3.000
 REN  H11   C11  C10   109.82  3.000
 REN  N12   C11  C10   112.55  3.000
 REN  C13   N12  C14   114.76  3.000
 REN  C13   N12  C11   112.36  3.000
 REN  C14   N12  C11   109.54  3.000
 REN  H14   C14  C1    106.66  3.000
 REN  H14   C14  C16   106.34  3.000
 REN  C1    C14  C16   113.46  3.000
 REN  H14   C14  N12   105.55  3.000
 REN  C1    C14  N12   112.50  3.000
 REN  C16   C14  N12   111.68  3.000
 REN  H16A  C16  H16   105.94  3.000
 REN  H16A  C16  C17   108.42  3.000
 REN  H16   C16  C17   110.02  3.000
 REN  H16A  C16  C14   108.41  3.000
 REN  H16   C16  C14   110.39  3.000
 REN  C17   C16  C14   113.36  3.000
 REN  C18   C17  C25   118.25  3.000
 REN  C18   C17  C16   120.42  3.000
 REN  C25   C17  C16   121.31  3.000
 REN  H25   C25  C24   118.78  3.000
 REN  H25   C25  C17   120.01  3.000
 REN  C24   C25  C17   121.21  3.000
 REN  H24   C24  C21   120.91  3.000
 REN  H24   C24  C25   118.94  3.000
 REN  C21   C24  C25   120.15  3.000
 REN  C19   C21  O22   114.88  3.000
 REN  C19   C21  C24   119.26  3.000
 REN  O22   C21  C24   125.86  3.000
 REN  C23   O22  C21   118.35  3.000
 REN  H23B  C23  H23A  108.81  3.000
 REN  H23B  C23  H23   108.92  3.000
 REN  H23A  C23  H23   108.85  3.000
 REN  H23B  C23  O22   111.73  3.000
 REN  H23A  C23  O22   111.75  3.000
 REN  H23   C23  O22   106.68  3.000
 REN  C18   C19  O20   119.12  3.000
 REN  C18   C19  C21   119.81  3.000
 REN  O20   C19  C21   121.08  3.000
 REN  HO20  O20  C19   110.02  3.000
 REN  H18   C18  C19   118.26  3.000
 REN  H18   C18  C17   120.42  3.000
 REN  C19   C18  C17   121.32  3.000
 REN  C14   C1   C9    119.74  3.000
 REN  C14   C1   C2    121.61  3.000
 REN  C9    C1   C2    118.58  3.000
 REN  H13B  C13  H13A  106.72  3.000
 REN  H13B  C13  H13   107.48  3.000
 REN  H13A  C13  H13   107.53  3.000
 REN  H13B  C13  N12   108.90  3.000
 REN  H13A  C13  N12   110.79  3.000
 REN  H13   C13  N12   115.06  3.000
 REN  C7    O6   C5    118.46  3.000
 REN  H7B   C7   H7A   108.83  3.000
 REN  H7B   C7   H7    108.86  3.000
 REN  H7A   C7   H7    108.92  3.000
 REN  H7B   C7   O6    111.80  3.000
 REN  H7A   C7   O6    106.63  3.000
 REN  H7    C7   O6    111.70  3.000
 REN  HO4   O4   C3    110.02  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
 REN  CONST_01  C8   C5   C3   C2      0.00   0.0  0
 REN  CONST_02  C8   C9   C1   C2      0.00   0.0  0
 REN  CONST_03  C9   C1   C2   C3      0.00   0.0  0
 REN  CONST_04  C9   C8   C5   C3      0.00   0.0  0
 REN  CONST_05  C1   C2   C3   C5      0.00   0.0  0
 REN  CONST_06  C1   C9   C8   C5      0.00   0.0  0
 REN  CONST_07  C21  C24  C25  C17     0.00   0.0  0
 REN  CONST_08  C21  C19  C18  C17     0.00   0.0  0
 REN  CONST_09  C19  C18  C17  C25     0.00   0.0  0
 REN  CONST_10  C19  C21  C24  C25     0.00   0.0  0
 REN  CONST_11  C18  C17  C25  C24     0.00   0.0  0
 REN  CONST_12  C18  C19  C21  C24     0.00   0.0  0
 REN  CONST_13  O6   C5   C3   C2    180.00   0.0  0
 REN  CONST_14  O4   C3   C5   C8    180.00   0.0  0
 REN  CONST_15  O6   C5   C8   C9    180.00   0.0  0
 REN  CONST_16  C24  C25  C17  C16   180.00   0.0  0
 REN  CONST_17  C19  C18  C17  C16   180.00   0.0  0
 REN  CONST_18  O20  C19  C18  C17   180.00   0.0  0
 REN  CONST_19  O22  C21  C24  C25   180.00   0.0  0
 REN  CONST_20  O20  C19  C21  C24   180.00   0.0  0
 REN  CONST_21  C18  C19  C21  O22   180.00   0.0  0
 REN  CONST_22  O4   C3   C2   C1    180.00   0.0  0
 REN  CONST_23  H8   C8   C5   C3    180.00   0.0  0
 REN  CONST_24  H2   C2   C3   C5    180.00   0.0  0
 REN  CONST_25  H24  C24  C25  C17   180.00   0.0  0
 REN  CONST_26  H18  C18  C17  C25   180.00   0.0  0
 REN  CONST_27  H25  C25  C24  C21   180.00   0.0  0
 REN  Var_01    C11  C10  C9   C8   -168.27  30.0  1
 REN  Var_02    N12  C11  C10  C9    -44.04  30.0  1
 REN  Var_03    C14  N12  C11  C10    66.14  30.0  1
 REN  Var_04    C25  C17  C16  C14   123.06  30.0  2
 REN  Var_05    C19  C21  O22  C23  -178.49  30.0  2
 REN  Var_06    H13  C13  N12  C11    73.87  30.0  3
 REN  Var_07    H7   C7   O6   C5     60.33  30.0  3
 REN  Var_08    H23  C23  O22  C21   179.35  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
 REN  chir_01  C14  N12  C16  C1  negativ

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
 REN  plan-1  C16  0.020
 REN  plan-1  C17  0.020
 REN  plan-1  C25  0.020
 REN  plan-1  C24  0.020
 REN  plan-1  C21  0.020
 REN  plan-1  O22  0.020
 REN  plan-1  C19  0.020
 REN  plan-1  O20  0.020
 REN  plan-1  C18  0.020
 REN  plan-1  H25  0.020
 REN  plan-1  H24  0.020
 REN  plan-1  H18  0.020
 REN  plan-2  C2   0.020
 REN  plan-2  C3   0.020
 REN  plan-2  C5   0.020
 REN  plan-2  C8   0.020
 REN  plan-2  C9   0.020
 REN  plan-2  C10  0.020
 REN  plan-2  C14  0.020
 REN  plan-2  C1   0.020
 REN  plan-2  O6   0.020
 REN  plan-2  O4   0.020
 REN  plan-2  H2   0.020
 REN  plan-2  H8   0.020

