# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 08:39:46 2022
#   Inital geometry file: a 111 line input string
#   Ligand name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1(C)Oc2ccc3C[C@@H](COc3c2C=C1)c4ccc(O)cc4O
#
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
 GBJ  GBJ  4-[(3R)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol  ligand  44  24  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GBJ
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
 GBJ  C1   C  CH3   0  -0.666   6.6636   0.5618   0.3920
 GBJ  C2   C  CT    0   0.149   5.3116   0.4003  -0.2833
 GBJ  C3   C  C1    0  -0.253   4.4723   1.6375  -0.1143
 GBJ  C4   C  C1    0  -0.203   3.1494   1.5490   0.0130
 GBJ  C5   C  CR6   0  -0.150   2.5194   0.2378   0.0508
 GBJ  C6   C  CR6   0   0.356   3.3475  -0.8697   0.2442
 GBJ  C7   C  CR16  0  -0.373   2.8131  -2.1456   0.3658
 GBJ  C8   C  CR16  0  -0.320   1.4392  -2.3059   0.2836
 GBJ  C9   C  CR6   0  -0.012   0.5772  -1.2351   0.0689
 GBJ  C10  C  CR6   0   0.344   1.1365   0.0375  -0.0461
 GBJ  O1   O  O2    0  -0.478   0.3904   1.1452  -0.2291
 GBJ  C11  C  CH2   0  -0.152  -0.9861   0.9765  -0.5415
 GBJ  C12  C  CH1   0  -0.371  -1.6365  -0.1299   0.2824
 GBJ  C13  C  CH2   0  -0.467  -0.9113  -1.4315  -0.0364
 GBJ  C14  C  CR6   0   0.024  -3.1249  -0.1450   0.0300
 GBJ  C15  C  CR16  0  -0.308  -3.7348  -0.9943  -0.8870
 GBJ  C16  C  CR16  0  -0.355  -5.0981  -0.9758  -1.1390
 GBJ  C17  C  CR6   0   0.363  -5.8999  -0.0693  -0.4542
 GBJ  C18  C  CR16  0  -0.512  -5.3260   0.7974   0.4697
 GBJ  C19  C  CR6   0   0.351  -3.9560   0.7590   0.7065
 GBJ  O2   O  OH1   0  -0.629  -3.3789   1.5930   1.5941
 GBJ  O3   O  OH1   0  -0.635  -7.2213  -0.0660  -0.7162
 GBJ  O4   O  O2    0  -0.497   4.6804  -0.7121   0.3793
 GBJ  C20  C  CH3   0  -0.650   5.4789   0.0764  -1.7662
 GBJ  H1   H  HCH3  0   0.242   6.5520   0.7914   1.4523
 GBJ  H2   H  HCH3  0   0.242   7.2630  -0.3438   0.2920
 GBJ  H3   H  HCH3  0   0.235   7.2143   1.3798  -0.0726
 GBJ  H4   H  H     0   0.258   4.9745   2.5972  -0.1372
 GBJ  H6   H  H     0   0.254   2.5415   2.4389   0.1075
 GBJ  H8   H  HCR6  0   0.255   3.4627  -2.9952   0.5314
 GBJ  H9   H  HCR6  0   0.252   1.0186  -3.2999   0.3846
 GBJ  H10  H  HCH2  0   0.252  -1.4493   1.9436  -0.3504
 GBJ  H11  H  HCH2  0   0.224  -1.0975   0.7509  -1.6092
 GBJ  H12  H  HCH1  0   0.263  -1.4664   0.0965   1.3401
 GBJ  H13  H  HCH2  0   0.251  -1.1516  -1.7680  -1.0490
 GBJ  H14  H  HCH2  0   0.261  -1.2349  -2.2265   0.6390
 GBJ  H15  H  HCR6  0   0.250  -3.1313  -1.7075  -1.4327
 GBJ  H16  H  HCR6  0   0.258  -5.5345  -1.6549  -1.8602
 GBJ  H17  H  HCR6  0   0.280  -5.9474   1.5074   1.0075
 GBJ  H18  H  HOH1  0   0.477  -4.0387   2.1612   2.0072
 GBJ  H19  H  HOH1  0   0.475  -7.6664   0.6216  -0.2085
 GBJ  H20  H  HCH3  0   0.237   6.1089  -0.8043  -1.9052
 GBJ  H21  H  HCH3  0   0.237   4.5152  -0.1041  -2.2456
 GBJ  H22  H  HCH3  0   0.238   5.9522   0.9140  -2.2800

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
 GBJ  C20  C2   single    1.527  0.020  1.527
 GBJ  C1   C2   single    1.520  0.020  1.520
 GBJ  C2   C3   single    1.505  0.020  1.505
 GBJ  C2   O4   single    1.440  0.020  1.440
 GBJ  C3   C4   double    1.332  0.020  1.332
 GBJ  O4   C6   single    1.349  0.020  1.349
 GBJ  C6   C7   aromatic  1.389  0.020  1.389
 GBJ  C6   C5   aromatic  1.396  0.020  1.396
 GBJ  C4   C5   single    1.455  0.020  1.455
 GBJ  C7   C8   aromatic  1.386  0.020  1.386
 GBJ  C5   C10  aromatic  1.401  0.020  1.401
 GBJ  C8   C9   aromatic  1.391  0.020  1.391
 GBJ  C10  C9   aromatic  1.395  0.020  1.395
 GBJ  C10  O1   single    1.348  0.020  1.348
 GBJ  C9   C13  single    1.505  0.020  1.505
 GBJ  O1   C11  single    1.421  0.020  1.421
 GBJ  C11  C12  single    1.525  0.020  1.525
 GBJ  C13  C12  single    1.524  0.020  1.524
 GBJ  C12  C14  single    1.510  0.020  1.510
 GBJ  C14  C15  aromatic  1.391  0.020  1.391
 GBJ  C14  C19  aromatic  1.402  0.020  1.402
 GBJ  O2   C19  single    1.348  0.020  1.348
 GBJ  C15  C16  aromatic  1.386  0.020  1.386
 GBJ  C19  C18  aromatic  1.391  0.020  1.391
 GBJ  C16  C17  aromatic  1.391  0.020  1.391
 GBJ  C18  C17  aromatic  1.391  0.020  1.391
 GBJ  C17  O3   single    1.347  0.020  1.347
 GBJ  C1   H1   single    0.970  0.020  1.090
 GBJ  C1   H2   single    0.970  0.020  1.090
 GBJ  C1   H3   single    0.970  0.020  1.090
 GBJ  C3   H4   single    0.930  0.020  1.080
 GBJ  C4   H6   single    0.930  0.020  1.080
 GBJ  C7   H8   single    0.930  0.020  1.080
 GBJ  C8   H9   single    0.930  0.020  1.080
 GBJ  C11  H10  single    0.970  0.020  1.090
 GBJ  C11  H11  single    0.970  0.020  1.090
 GBJ  C12  H12  single    0.970  0.020  1.090
 GBJ  C13  H13  single    0.970  0.020  1.090
 GBJ  C13  H14  single    0.970  0.020  1.090
 GBJ  C15  H15  single    0.930  0.020  1.080
 GBJ  C16  H16  single    0.930  0.020  1.080
 GBJ  C18  H17  single    0.930  0.020  1.080
 GBJ  O2   H18  single    0.850  0.020  0.980
 GBJ  O3   H19  single    0.850  0.020  0.980
 GBJ  C20  H20  single    0.970  0.020  1.090
 GBJ  C20  H21  single    0.970  0.020  1.090
 GBJ  C20  H22  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
 GBJ  H3   C1   H2   107.84  3.000
 GBJ  H3   C1   H1   107.94  3.000
 GBJ  H2   C1   H1   108.68  3.000
 GBJ  H3   C1   C2   109.86  3.000
 GBJ  H2   C1   C2   111.10  3.000
 GBJ  H1   C1   C2   111.31  3.000
 GBJ  C20  C2   O4   109.32  3.000
 GBJ  O4   C2   C3   109.81  3.000
 GBJ  C20  C2   C3   110.16  3.000
 GBJ  O4   C2   C1   105.51  3.000
 GBJ  C3   C2   C1   111.03  3.000
 GBJ  C20  C2   C1   110.89  3.000
 GBJ  H4   C3   C4   121.42  3.000
 GBJ  H4   C3   C2   117.87  3.000
 GBJ  C4   C3   C2   120.68  3.000
 GBJ  H6   C4   C5   119.72  3.000
 GBJ  H6   C4   C3   120.78  3.000
 GBJ  C5   C4   C3   119.49  3.000
 GBJ  C10  C5   C6   118.79  3.000
 GBJ  C10  C5   C4   123.67  3.000
 GBJ  C6   C5   C4   117.49  3.000
 GBJ  O4   C6   C7   118.61  3.000
 GBJ  C7   C6   C5   120.85  3.000
 GBJ  O4   C6   C5   120.47  3.000
 GBJ  H8   C7   C8   120.89  3.000
 GBJ  H8   C7   C6   120.25  3.000
 GBJ  C8   C7   C6   118.86  3.000
 GBJ  H9   C8   C9   118.66  3.000
 GBJ  H9   C8   C7   119.03  3.000
 GBJ  C9   C8   C7   122.30  3.000
 GBJ  C13  C9   C10  120.65  3.000
 GBJ  C13  C9   C8   121.54  3.000
 GBJ  C10  C9   C8   117.81  3.000
 GBJ  O1   C10  C9   122.61  3.000
 GBJ  O1   C10  C5   116.00  3.000
 GBJ  C9   C10  C5   121.38  3.000
 GBJ  C11  O1   C10  117.92  3.000
 GBJ  H11  C11  H10  108.07  3.000
 GBJ  H11  C11  C12  109.47  3.000
 GBJ  H10  C11  C12  111.59  3.000
 GBJ  H11  C11  O1   109.67  3.000
 GBJ  H10  C11  O1   105.54  3.000
 GBJ  C12  C11  O1   112.36  3.000
 GBJ  H12  C12  C14  108.47  3.000
 GBJ  H12  C12  C13  107.75  3.000
 GBJ  C14  C12  C13  115.19  3.000
 GBJ  H12  C12  C11  107.79  3.000
 GBJ  C14  C12  C11  109.72  3.000
 GBJ  C13  C12  C11  107.68  3.000
 GBJ  H14  C13  H13  106.47  3.000
 GBJ  H14  C13  C12  110.57  3.000
 GBJ  H13  C13  C12  110.61  3.000
 GBJ  H14  C13  C9   110.16  3.000
 GBJ  H13  C13  C9   108.79  3.000
 GBJ  C12  C13  C9   110.16  3.000
 GBJ  C19  C14  C15  116.87  3.000
 GBJ  C19  C14  C12  119.82  3.000
 GBJ  C15  C14  C12  123.28  3.000
 GBJ  H15  C15  C16  117.74  3.000
 GBJ  H15  C15  C14  119.37  3.000
 GBJ  C16  C15  C14  122.88  3.000
 GBJ  H16  C16  C17  120.31  3.000
 GBJ  H16  C16  C15  120.61  3.000
 GBJ  C17  C16  C15  119.09  3.000
 GBJ  O3   C17  C18  122.17  3.000
 GBJ  O3   C17  C16  118.13  3.000
 GBJ  C18  C17  C16  119.70  3.000
 GBJ  H17  C18  C19  119.82  3.000
 GBJ  H17  C18  C17  120.02  3.000
 GBJ  C19  C18  C17  120.16  3.000
 GBJ  O2   C19  C18  121.12  3.000
 GBJ  C18  C19  C14  121.30  3.000
 GBJ  O2   C19  C14  117.58  3.000
 GBJ  H18  O2   C19  110.73  3.000
 GBJ  H19  O3   C17  110.63  3.000
 GBJ  C6   O4   C2   118.50  3.000
 GBJ  H22  C20  H21  107.65  3.000
 GBJ  H22  C20  H20  108.01  3.000
 GBJ  H21  C20  H20  108.68  3.000
 GBJ  H22  C20  C2   110.00  3.000
 GBJ  H21  C20  C2   111.40  3.000
 GBJ  H20  C20  C2   110.97  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
 GBJ  CONST_01  C8   C7   C6   C5     0.00   0.0  0
 GBJ  CONST_02  C8   C9   C10  C5     0.00   0.0  0
 GBJ  CONST_03  C9   C8   C7   C6     0.00   0.0  0
 GBJ  CONST_04  C9   C10  C5   C6     0.00   0.0  0
 GBJ  CONST_05  C10  C5   C6   C7     0.00   0.0  0
 GBJ  CONST_06  C10  C9   C8   C7     0.00   0.0  0
 GBJ  CONST_07  C17  C16  C15  C14    0.00   0.0  0
 GBJ  CONST_08  C17  C18  C19  C14    0.00   0.0  0
 GBJ  CONST_09  C18  C19  C14  C15    0.00   0.0  0
 GBJ  CONST_10  C18  C17  C16  C15    0.00   0.0  0
 GBJ  CONST_11  C19  C14  C15  C16    0.00   0.0  0
 GBJ  CONST_12  C19  C18  C17  C16    0.00   0.0  0
 GBJ  CONST_13  C16  C15  C14  C12  180.00   0.0  0
 GBJ  CONST_14  C18  C19  C14  C12  180.00   0.0  0
 GBJ  CONST_15  O2   C19  C14  C12    0.00   0.0  0
 GBJ  CONST_16  O2   C19  C14  C15  180.00   0.0  0
 GBJ  CONST_17  O3   C17  C16  C15  180.00   0.0  0
 GBJ  CONST_18  O2   C19  C18  C17  180.00   0.0  0
 GBJ  CONST_19  O3   C17  C18  C19  180.00   0.0  0
 GBJ  CONST_20  H8   C7   C6   C5   180.00   0.0  0
 GBJ  CONST_21  H9   C8   C7   C6   180.00   0.0  0
 GBJ  CONST_22  H15  C15  C14  C12    0.00   0.0  0
 GBJ  CONST_23  H16  C16  C15  C14  180.00   0.0  0
 GBJ  CONST_24  H17  C18  C19  C14  180.00   0.0  0
 GBJ  Var_01    C5   C4   C3   C2     2.87  30.0  1
 GBJ  Var_02    C7   C6   O4   C2   153.42  30.0  1
 GBJ  Var_03    C6   C5   C4   C3    13.67  30.0  1
 GBJ  Var_04    O4   C2   C3   C4   -29.63  30.0  1
 GBJ  Var_05    C12  C13  C9   C8   157.61  30.0  1
 GBJ  Var_06    C12  C11  O1   C10   41.55  30.0  1
 GBJ  Var_07    H20  C20  C2   C3   178.46  30.0  3
 GBJ  Var_08    H1   C1   C2   C3    57.29  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
 GBJ  chir_01  C12  C11  C13  C14  positiv

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
 GBJ  plan-1  C12  0.020
 GBJ  plan-1  C14  0.020
 GBJ  plan-1  C15  0.020
 GBJ  plan-1  C16  0.020
 GBJ  plan-1  C17  0.020
 GBJ  plan-1  C18  0.020
 GBJ  plan-1  C19  0.020
 GBJ  plan-1  O2   0.020
 GBJ  plan-1  O3   0.020
 GBJ  plan-1  H15  0.020
 GBJ  plan-1  H16  0.020
 GBJ  plan-1  H17  0.020
 GBJ  plan-2  C4   0.020
 GBJ  plan-2  C5   0.020
 GBJ  plan-2  C6   0.020
 GBJ  plan-2  C7   0.020
 GBJ  plan-2  C8   0.020
 GBJ  plan-2  C9   0.020
 GBJ  plan-2  C10  0.020
 GBJ  plan-2  O1   0.020
 GBJ  plan-2  C13  0.020
 GBJ  plan-2  O4   0.020
 GBJ  plan-2  H8   0.020
 GBJ  plan-2  H9   0.020

