# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 03:08:23 2020
#   Inital geometry file: a 101 line input string
#   Ligand name: 2,3-dimethoxy-5-[(1S)-1-phenylpropyl]benzene-1,4-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@@H](c1ccccc1)c2cc(O)c(OC)c(OC)c2O
#
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
 REV  REV  2,3-dimethoxy-5-[(1S)-1-phenylpropyl]benzene-1,4-diol  ligand  41  21  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_REV
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
 REV  C01  C  CR6   0   0.160  -2.5770   0.5995  -0.4233
 REV  C02  C  CR6   0   0.316  -1.8335   1.0039  -1.5289
 REV  C03  C  CR16  0  -0.466  -0.5350   0.5386  -1.6844
 REV  C04  C  CR6   0   0.057   0.0460  -0.3191  -0.7571
 REV  C05  C  CR6   0   0.211  -0.6991  -0.7070   0.3620
 REV  C06  C  CR6   0   0.226  -2.0065  -0.2490   0.5233
 REV  C07  C  CR16  0  -0.313   3.1472  -1.2187   0.9240
 REV  C08  C  CR6   0   0.079   2.3569  -0.3410   0.1854
 REV  C09  C  CR16  0  -0.278   2.4281   1.0225   0.4702
 REV  C10  C  CR16  0  -0.241   3.2704   1.4943   1.4648
 REV  C11  C  CR16  0  -0.265   4.0533   0.6091   2.1985
 REV  C12  C  CR16  0  -0.242   3.9898  -0.7488   1.9259
 REV  O13  O  O2    0  -0.485  -2.7246  -0.6102   1.6174
 REV  C14  C  CH3   0  -0.408  -3.5045  -1.7863   1.4440
 REV  O15  O  O2    0  -0.495  -3.8622   1.0354  -0.3016
 REV  C16  C  CH3   0  -0.412  -4.0383   2.1161   0.6119
 REV  O17  O  OH1   0  -0.638  -2.3483   1.8330  -2.4638
 REV  O18  O  OH1   0  -0.633  -0.2259  -1.5555   1.3095
 REV  C19  C  CH1   0  -0.376   1.4548  -0.8538  -0.9212
 REV  C20  C  CH2   0  -0.426   2.0723  -0.5811  -2.2983
 REV  C21  C  CH3   0  -0.661   3.4217  -1.2591  -2.4834
 REV  H1   H  HCR6  0   0.264   0.0204   0.8579  -2.5565
 REV  H2   H  HCR6  0   0.264   3.1092  -2.2812   0.7090
 REV  H3   H  HCR6  0   0.253   1.8156   1.7209  -0.0883
 REV  H4   H  HCR6  0   0.257   3.3135   2.5555   1.6741
 REV  H5   H  HCR6  0   0.257   4.7051   0.9789   2.9795
 REV  H6   H  HCR6  0   0.258   4.5952  -1.4461   2.4903
 REV  H7   H  HCH3  0   0.222  -4.2106  -1.6840   0.6171
 REV  H8   H  HCH3  0   0.223  -2.8785  -2.6643   1.2663
 REV  H9   H  HCH3  0   0.239  -4.0640  -1.9376   2.3652
 REV  H10  H  HCH3  0   0.232  -3.8105   1.8176   1.6360
 REV  H11  H  HCH3  0   0.223  -3.4140   2.9719   0.3435
 REV  H12  H  HCH3  0   0.243  -5.0834   2.4136   0.5552
 REV  H13  H  HOH1  0   0.468  -3.2822   1.9903  -2.2770
 REV  H14  H  HOH1  0   0.476   0.7254  -1.4383   1.4254
 REV  H15  H  HCH1  0   0.263   1.4044  -1.9454  -0.8195
 REV  H16  H  HCH2  0   0.238   1.3817  -0.9417  -3.0651
 REV  H17  H  HCH2  0   0.227   2.1808   0.4957  -2.4544
 REV  H18  H  HCH3  0   0.236   3.7780  -1.1296  -3.5054
 REV  H19  H  HCH3  0   0.227   4.1781  -0.8460  -1.8159
 REV  H20  H  HCH3  0   0.220   3.3556  -2.3309  -2.2864

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
 REV  O17  C02  single    1.351  0.020  1.351
 REV  O15  C16  single    1.426  0.020  1.426
 REV  O15  C01  single    1.363  0.020  1.363
 REV  C02  C01  aromatic  1.392  0.020  1.392
 REV  C02  C03  aromatic  1.388  0.020  1.388
 REV  C01  C06  aromatic  1.393  0.020  1.393
 REV  C03  C04  aromatic  1.390  0.020  1.390
 REV  C14  O13  single    1.422  0.020  1.422
 REV  C06  O13  single    1.358  0.020  1.358
 REV  C06  C05  aromatic  1.395  0.020  1.395
 REV  C21  C20  single    1.521  0.020  1.521
 REV  C04  C05  aromatic  1.399  0.020  1.399
 REV  C04  C19  single    1.516  0.020  1.516
 REV  C20  C19  single    1.534  0.020  1.534
 REV  C05  O18  single    1.357  0.020  1.357
 REV  C09  C10  aromatic  1.386  0.020  1.386
 REV  C09  C08  aromatic  1.395  0.020  1.395
 REV  C19  C08  single    1.517  0.020  1.517
 REV  C10  C11  aromatic  1.391  0.020  1.391
 REV  C08  C07  aromatic  1.393  0.020  1.393
 REV  C11  C12  aromatic  1.387  0.020  1.387
 REV  C07  C12  aromatic  1.391  0.020  1.391
 REV  C03  H1   single    0.930  0.020  1.080
 REV  C07  H2   single    0.930  0.020  1.080
 REV  C09  H3   single    0.930  0.020  1.080
 REV  C10  H4   single    0.930  0.020  1.080
 REV  C11  H5   single    0.930  0.020  1.080
 REV  C12  H6   single    0.930  0.020  1.080
 REV  C14  H7   single    0.970  0.020  1.090
 REV  C14  H8   single    0.970  0.020  1.090
 REV  C14  H9   single    0.970  0.020  1.090
 REV  C16  H10  single    0.970  0.020  1.090
 REV  C16  H11  single    0.970  0.020  1.090
 REV  C16  H12  single    0.970  0.020  1.090
 REV  O17  H13  single    0.850  0.020  0.980
 REV  O18  H14  single    0.850  0.020  0.980
 REV  C19  H15  single    0.970  0.020  1.090
 REV  C20  H16  single    0.970  0.020  1.090
 REV  C20  H17  single    0.970  0.020  1.090
 REV  C21  H18  single    0.970  0.020  1.090
 REV  C21  H19  single    0.970  0.020  1.090
 REV  C21  H20  single    0.970  0.020  1.090

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
 REV  O15  C01  C06  121.35  3.000
 REV  C06  C01  C02  119.85  3.000
 REV  O15  C01  C02  118.80  3.000
 REV  O17  C02  C03  118.98  3.000
 REV  C03  C02  C01  119.42  3.000
 REV  O17  C02  C01  121.60  3.000
 REV  H1   C03  C04  120.33  3.000
 REV  H1   C03  C02  118.13  3.000
 REV  C04  C03  C02  121.53  3.000
 REV  C19  C04  C05  118.93  3.000
 REV  C19  C04  C03  122.26  3.000
 REV  C05  C04  C03  118.81  3.000
 REV  O18  C05  C06  116.84  3.000
 REV  O18  C05  C04  123.09  3.000
 REV  C06  C05  C04  120.04  3.000
 REV  O13  C06  C05  120.11  3.000
 REV  C05  C06  C01  120.35  3.000
 REV  O13  C06  C01  119.54  3.000
 REV  H2   C07  C12  119.67  3.000
 REV  H2   C07  C08  119.49  3.000
 REV  C12  C07  C08  120.84  3.000
 REV  C19  C08  C09  120.65  3.000
 REV  C19  C08  C07  120.74  3.000
 REV  C09  C08  C07  118.61  3.000
 REV  H3   C09  C10  119.59  3.000
 REV  H3   C09  C08  119.73  3.000
 REV  C10  C09  C08  120.68  3.000
 REV  H4   C10  C11  119.96  3.000
 REV  H4   C10  C09  119.78  3.000
 REV  C11  C10  C09  120.26  3.000
 REV  H5   C11  C12  120.27  3.000
 REV  H5   C11  C10  120.15  3.000
 REV  C12  C11  C10  119.59  3.000
 REV  H6   C12  C11  120.18  3.000
 REV  H6   C12  C07  119.80  3.000
 REV  C11  C12  C07  120.02  3.000
 REV  C14  O13  C06  114.32  3.000
 REV  H9   C14  H8   108.69  3.000
 REV  H9   C14  H7   108.75  3.000
 REV  H8   C14  H7   108.81  3.000
 REV  H9   C14  O13  107.08  3.000
 REV  H8   C14  O13  111.73  3.000
 REV  H7   C14  O13  111.68  3.000
 REV  C16  O15  C01  114.60  3.000
 REV  H12  C16  H11  108.77  3.000
 REV  H12  C16  H10  108.92  3.000
 REV  H11  C16  H10  109.00  3.000
 REV  H12  C16  O15  107.01  3.000
 REV  H11  C16  O15  111.45  3.000
 REV  H10  C16  O15  111.61  3.000
 REV  H13  O17  C02  109.55  3.000
 REV  H14  O18  C05  110.58  3.000
 REV  H15  C19  C20  106.18  3.000
 REV  H15  C19  C08  107.21  3.000
 REV  C20  C19  C08  110.82  3.000
 REV  H15  C19  C04  107.35  3.000
 REV  C08  C19  C04  110.76  3.000
 REV  C20  C19  C04  114.12  3.000
 REV  H17  C20  H16  106.70  3.000
 REV  H17  C20  C21  109.48  3.000
 REV  H16  C20  C21  109.15  3.000
 REV  H17  C20  C19  110.07  3.000
 REV  H16  C20  C19  108.47  3.000
 REV  C21  C20  C19  112.77  3.000
 REV  H20  C21  H19  107.67  3.000
 REV  H20  C21  H18  107.79  3.000
 REV  H19  C21  H18  107.59  3.000
 REV  H20  C21  C20  111.21  3.000
 REV  H19  C21  C20  111.85  3.000
 REV  H18  C21  C20  110.55  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
 REV  CONST_01  C04  C03  C02  C01    0.00   0.0  0
 REV  CONST_02  C04  C05  C06  C01    0.00   0.0  0
 REV  CONST_03  C05  C06  C01  C02    0.00   0.0  0
 REV  CONST_04  C05  C04  C03  C02    0.00   0.0  0
 REV  CONST_05  C06  C01  C02  C03    0.00   0.0  0
 REV  CONST_06  C06  C05  C04  C03    0.00   0.0  0
 REV  CONST_07  C10  C09  C08  C07    0.00   0.0  0
 REV  CONST_08  C10  C11  C12  C07    0.00   0.0  0
 REV  CONST_09  C11  C10  C09  C08    0.00   0.0  0
 REV  CONST_10  C11  C12  C07  C08    0.00   0.0  0
 REV  CONST_11  C12  C11  C10  C09    0.00   0.0  0
 REV  CONST_12  C12  C07  C08  C09    0.00   0.0  0
 REV  CONST_13  O18  C05  C06  C01  180.00   0.0  0
 REV  CONST_14  O13  C06  C01  C02  180.00   0.0  0
 REV  CONST_15  C19  C04  C03  C02  180.00   0.0  0
 REV  CONST_16  O15  C01  C02  C03  180.00   0.0  0
 REV  CONST_17  O18  C05  C04  C03  180.00   0.0  0
 REV  CONST_18  O17  C02  C03  C04  180.00   0.0  0
 REV  CONST_19  O13  C06  C05  C04  180.00   0.0  0
 REV  CONST_20  O15  C01  C06  C05  180.00   0.0  0
 REV  CONST_21  O17  C02  C01  C06  180.00   0.0  0
 REV  CONST_22  C19  C04  C05  C06  180.00   0.0  0
 REV  CONST_23  C19  C08  C09  C10  180.00   0.0  0
 REV  CONST_24  C19  C08  C07  C12  180.00   0.0  0
 REV  CONST_25  H1   C03  C02  C01  180.00   0.0  0
 REV  CONST_26  H3   C09  C08  C07  180.00   0.0  0
 REV  CONST_27  H5   C11  C12  C07  180.00   0.0  0
 REV  CONST_28  H4   C10  C09  C08  180.00   0.0  0
 REV  CONST_29  H6   C12  C07  C08  180.00   0.0  0
 REV  CONST_30  H2   C07  C08  C09  180.00   0.0  0
 REV  Var_01    H10  C16  O15  C01  -65.25  30.0  3
 REV  Var_02    H7   C14  O13  C06  -58.27  30.0  3
 REV  Var_03    H18  C21  C20  C19  174.06  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
 REV  chir_01  C19  C04  C20  C08  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
 REV  plan-1  C01  0.020
 REV  plan-1  C02  0.020
 REV  plan-1  C03  0.020
 REV  plan-1  C04  0.020
 REV  plan-1  C05  0.020
 REV  plan-1  C06  0.020
 REV  plan-1  O13  0.020
 REV  plan-1  O15  0.020
 REV  plan-1  O17  0.020
 REV  plan-1  O18  0.020
 REV  plan-1  C19  0.020
 REV  plan-1  H1   0.020
 REV  plan-2  C07  0.020
 REV  plan-2  C08  0.020
 REV  plan-2  C09  0.020
 REV  plan-2  C10  0.020
 REV  plan-2  C11  0.020
 REV  plan-2  C12  0.020
 REV  plan-2  C19  0.020
 REV  plan-2  H2   0.020
 REV  plan-2  H3   0.020
 REV  plan-2  H4   0.020
 REV  plan-2  H5   0.020
 REV  plan-2  H6   0.020

