# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 06:20:29 2020
#   Inital geometry file: a 123 line input string
#   Ligand name: (3R,5Z,8S,9S,11E)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(O)c2C(=O)O[C@H](C)C\C=C/C(=O)[C@@H](O)[C@@H](O)C/C=C/c2c1
#
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
 FRR  FRR  (3R,5Z,8S,9S,11E)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione  ligand  48  26  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FRR
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
 FRR  C11   C  CR6   0   0.416  -1.6162   0.0015  -1.4309
 FRR  C2    C  CR6   0  -0.215  -2.1439   0.5327  -2.6092
 FRR  C3    C  CR6   0   0.190  -1.4416   1.5480  -3.2778
 FRR  C14   C  CR16  0  -0.464  -0.2480   2.0186  -2.7461
 FRR  C15   C  CR6   0   0.433   0.2734   1.4738  -1.5743
 FRR  C16   C  CR16  0  -0.540  -0.4077   0.4577  -0.9135
 FRR  C23   C  C1    0  -0.310  -1.9813   2.1356  -4.5105
 FRR  C17   C  C1    0  -0.195  -1.2561   2.7059  -5.4729
 FRR  O15   O  O2    0  -0.451  -3.3756  -0.5884  -4.2630
 FRR  C26   C  C     0   0.519  -3.4550  -0.0004  -3.0756
 FRR  C31   C  CH1   0   0.010  -4.5392  -1.2859  -4.7613
 FRR  C18   C  CH2   0  -0.511  -4.4131  -1.3457  -6.2760
 FRR  C24   C  CH1   0   0.003  -1.4417   2.4041  -7.9422
 FRR  C34   C  CH2   0  -0.519  -1.8623   3.2428  -6.7272
 FRR  C39   C  CH1   0  -0.084  -2.5306   2.3627  -9.0324
 FRR  C40   C  C     0   0.334  -3.8059   1.7742  -8.4634
 FRR  C41   C  C1    0  -0.373  -3.6611   0.4367  -7.8577
 FRR  C42   C  C1    0  -0.127  -4.5120  -0.0143  -6.9358
 FRR  O38   O  O     0  -0.434  -4.4673   0.0736  -2.4255
 FRR  O40   O  O     0  -0.397  -4.8524   2.3848  -8.4765
 FRR  O42   O  OH1   0  -0.664  -0.2544   2.9630  -8.4604
 FRR  O44   O  OH1   0  -0.658  -2.8016   3.6273  -9.5503
 FRR  O46   O  OH1   0  -0.621  -2.3003  -0.9886  -0.8352
 FRR  O48   O  O2    0  -0.468   1.4321   1.9950  -1.1449
 FRR  C59   C  CH3   0  -0.441   1.9971   1.5085   0.0580
 FRR  C62   C  CH3   0  -0.679  -4.6050  -2.6712  -4.1449
 FRR  H46   H  HOH1  0   0.482  -1.8310  -1.3021  -0.0536
 FRR  H16   H  HCR6  0   0.297  -0.0282   0.0144  -0.0011
 FRR  H591  H  HCH3  0   0.264   2.9113   2.0739   0.2196
 FRR  H592  H  HCH3  0   0.233   2.2466   0.4468  -0.0098
 FRR  H593  H  HCH3  0   0.233   1.3325   1.6639   0.9113
 FRR  H14   H  HCR6  0   0.260   0.2796   2.8343  -3.2234
 FRR  H23   H  H     0   0.244  -3.0576   2.0932  -4.6448
 FRR  H17   H  H     0   0.256  -0.1731   2.7415  -5.3944
 FRR  H341  H  HCH2  0   0.257  -2.9480   3.2551  -6.6165
 FRR  H342  H  HCH2  0   0.262  -1.5605   4.2807  -6.8922
 FRR  H24   H  HCH1  0   0.239  -1.2614   1.3739  -7.6137
 FRR  H42   H  HOH1  0   0.459   0.1617   2.3201  -9.0445
 FRR  H39   H  HCH1  0   0.256  -2.1807   1.6650  -9.8156
 FRR  H44   H  HOH1  0   0.452  -1.9573   4.0265  -9.7882
 FRR  H41   H  H     0   0.274  -2.8028  -0.1612  -8.1468
 FRR  H1    H  H     0   0.270  -5.3500   0.6113  -6.6385
 FRR  H181  H  HCH2  0   0.271  -5.2479  -1.9582  -6.6332
 FRR  H182  H  HCH2  0   0.260  -3.4961  -1.8620  -6.5688
 FRR  H31   H  HCH1  0   0.251  -5.4376  -0.7229  -4.4969
 FRR  H621  H  HCH3  0   0.249  -4.6942  -2.6260  -3.0604
 FRR  H622  H  HCH3  0   0.243  -5.4805  -3.1985  -4.5238
 FRR  H623  H  HCH3  0   0.235  -3.7206  -3.2577  -4.3966

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
 FRR  C11  O46   single    1.343  0.020  1.343
 FRR  C11  C16   aromatic  1.392  0.020  1.392
 FRR  C11  C2    single    1.396  0.020  1.396
 FRR  C2   C26   single    1.490  0.020  1.490
 FRR  C2   C3    aromatic  1.404  0.020  1.404
 FRR  C3   C14   single    1.389  0.020  1.389
 FRR  C3   C23   single    1.468  0.020  1.468
 FRR  C14  C15   aromatic  1.393  0.020  1.393
 FRR  C14  H14   single    0.930  0.020  1.080
 FRR  C15  C16   aromatic  1.390  0.020  1.390
 FRR  C15  O48   single    1.341  0.020  1.341
 FRR  C16  H16   single    0.930  0.020  1.080
 FRR  C23  H23   single    0.930  0.020  1.080
 FRR  C23  C17   double    1.333  0.020  1.333
 FRR  C17  H17   single    0.930  0.020  1.080
 FRR  C17  C34   single    1.493  0.020  1.493
 FRR  O15  C31   single    1.445  0.020  1.445
 FRR  O15  C26   single    1.327  0.020  1.327
 FRR  C26  O38   double    1.205  0.020  1.205
 FRR  C31  C18   single    1.521  0.020  1.521
 FRR  C31  H31   single    0.970  0.020  1.090
 FRR  C31  C62   single    1.518  0.020  1.518
 FRR  C18  C42   single    1.489  0.020  1.489
 FRR  C18  H181  single    0.970  0.020  1.090
 FRR  C18  H182  single    0.970  0.020  1.090
 FRR  C24  C34   single    1.535  0.020  1.535
 FRR  C24  H24   single    0.970  0.020  1.090
 FRR  C24  O42   single    1.411  0.020  1.411
 FRR  C24  C39   single    1.541  0.020  1.541
 FRR  C34  H341  single    0.970  0.020  1.090
 FRR  C34  H342  single    0.970  0.020  1.090
 FRR  C39  H39   single    0.970  0.020  1.090
 FRR  C39  O44   single    1.393  0.020  1.393
 FRR  C39  C40   single    1.515  0.020  1.515
 FRR  C40  O40   double    1.212  0.020  1.212
 FRR  C40  C41   single    1.475  0.020  1.475
 FRR  C41  H41   single    0.930  0.020  1.080
 FRR  C41  C42   double    1.333  0.020  1.333
 FRR  C42  H1    single    0.930  0.020  1.080
 FRR  O42  H42   single    0.850  0.020  0.980
 FRR  O44  H44   single    0.850  0.020  0.980
 FRR  O46  H46   single    0.850  0.020  0.980
 FRR  O48  C59   single    1.415  0.020  1.415
 FRR  C59  H591  single    0.970  0.020  1.090
 FRR  C59  H592  single    0.970  0.020  1.090
 FRR  C59  H593  single    0.970  0.020  1.090
 FRR  C62  H621  single    0.970  0.020  1.090
 FRR  C62  H622  single    0.970  0.020  1.090
 FRR  C62  H623  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
 FRR  O46   C11  C16   121.28  3.000
 FRR  C16   C11  C2    121.15  3.000
 FRR  O46   C11  C2    117.55  3.000
 FRR  C26   C2   C3    123.35  3.000
 FRR  C3    C2   C11   119.21  3.000
 FRR  C26   C2   C11   117.42  3.000
 FRR  C23   C3   C14   120.11  3.000
 FRR  C23   C3   C2    120.35  3.000
 FRR  C14   C3   C2    119.52  3.000
 FRR  H14   C14  C15   118.88  3.000
 FRR  H14   C14  C3    120.36  3.000
 FRR  C15   C14  C3    120.74  3.000
 FRR  O48   C15  C16   123.72  3.000
 FRR  O48   C15  C14   116.15  3.000
 FRR  C16   C15  C14   120.14  3.000
 FRR  H16   C16  C15   121.86  3.000
 FRR  H16   C16  C11   118.91  3.000
 FRR  C15   C16  C11   119.23  3.000
 FRR  H23   C23  C17   117.82  3.000
 FRR  C17   C23  C3    125.26  3.000
 FRR  H23   C23  C3    116.92  3.000
 FRR  H17   C17  C34   116.99  3.000
 FRR  C34   C17  C23   122.65  3.000
 FRR  H17   C17  C23   120.27  3.000
 FRR  C31   O15  C26   118.30  3.000
 FRR  O38   C26  O15   124.05  3.000
 FRR  O38   C26  C2    123.24  3.000
 FRR  O15   C26  C2    112.70  3.000
 FRR  H31   C31  C62   109.66  3.000
 FRR  C62   C31  C18   111.85  3.000
 FRR  H31   C31  C18   109.23  3.000
 FRR  C62   C31  O15   109.60  3.000
 FRR  H31   C31  O15   109.26  3.000
 FRR  C18   C31  O15   107.19  3.000
 FRR  H182  C18  H181  106.74  3.000
 FRR  H182  C18  C42   111.07  3.000
 FRR  H181  C18  C42   107.75  3.000
 FRR  H182  C18  C31   110.80  3.000
 FRR  H181  C18  C31   106.47  3.000
 FRR  C42   C18  C31   113.61  3.000
 FRR  H24   C24  O42   110.12  3.000
 FRR  O42   C24  C39   110.20  3.000
 FRR  H24   C24  C39   107.63  3.000
 FRR  C39   C24  C34   112.39  3.000
 FRR  O42   C24  C34   107.75  3.000
 FRR  H24   C24  C34   108.74  3.000
 FRR  H342  C34  H341  106.21  3.000
 FRR  H342  C34  C24   108.87  3.000
 FRR  H341  C34  C24   111.04  3.000
 FRR  H342  C34  C17   110.86  3.000
 FRR  H341  C34  C17   108.83  3.000
 FRR  C24   C34  C17   110.93  3.000
 FRR  H39   C39  O44   111.78  3.000
 FRR  O44   C39  C40   109.17  3.000
 FRR  H39   C39  C40   106.69  3.000
 FRR  C40   C39  C24   109.84  3.000
 FRR  O44   C39  C24   112.09  3.000
 FRR  H39   C39  C24   107.12  3.000
 FRR  O40   C40  C41   123.10  3.000
 FRR  C41   C40  C39   115.06  3.000
 FRR  O40   C40  C39   121.80  3.000
 FRR  H41   C41  C42   120.17  3.000
 FRR  C42   C41  C40   121.87  3.000
 FRR  H41   C41  C40   117.88  3.000
 FRR  H1    C42  C41   119.10  3.000
 FRR  H1    C42  C18   116.39  3.000
 FRR  C41   C42  C18   124.50  3.000
 FRR  H42   O42  C24   108.77  3.000
 FRR  H44   O44  C39   107.30  3.000
 FRR  H46   O46  C11   110.58  3.000
 FRR  C59   O48  C15   118.91  3.000
 FRR  H593  C59  H592  109.00  3.000
 FRR  H593  C59  H591  108.75  3.000
 FRR  H592  C59  H591  108.82  3.000
 FRR  H593  C59  O48   111.84  3.000
 FRR  H592  C59  O48   111.87  3.000
 FRR  H591  C59  O48   106.46  3.000
 FRR  H623  C62  H622  108.12  3.000
 FRR  H623  C62  H621  108.57  3.000
 FRR  H622  C62  H621  107.48  3.000
 FRR  H623  C62  C31   111.23  3.000
 FRR  H622  C62  C31   109.59  3.000
 FRR  H621  C62  C31   111.72  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
 FRR  CONST_01  C14   C15  C16  C11     0.00   0.0  0
 FRR  CONST_02  C14   C3   C2   C11     0.00   0.0  0
 FRR  CONST_03  C15   C16  C11  C2      0.00   0.0  0
 FRR  CONST_04  C15   C14  C3   C2      0.00   0.0  0
 FRR  CONST_05  C16   C11  C2   C3      0.00   0.0  0
 FRR  CONST_06  C16   C15  C14  C3      0.00   0.0  0
 FRR  CONST_07  O48   C15  C16  C11   180.00   0.0  0
 FRR  CONST_08  O46   C11  C2   C3    180.00   0.0  0
 FRR  CONST_09  O48   C15  C14  C3    180.00   0.0  0
 FRR  CONST_10  O46   C11  C16  C15   180.00   0.0  0
 FRR  CONST_11  O46   C11  C2   C26     0.00   0.0  0
 FRR  CONST_12  H16   C16  C11  C2    180.00   0.0  0
 FRR  CONST_13  H14   C14  C3   C2    180.00   0.0  0
 FRR  Var_01    C34   C17  C23  C3    177.77   0.0  0
 FRR  Var_02    C40   C41  C42  C18  -179.30   0.0  0
 FRR  Var_03    O15   C26  C2   C11  -118.13  30.0  1
 FRR  Var_04    C17   C23  C3   C2   -154.04  30.0  1
 FRR  Var_05    C24   C34  C17  C23  -111.95  30.0  1
 FRR  Var_06    C41   C42  C18  C31   131.60  30.0  1
 FRR  Var_07    C42   C41  C40  C39   156.31  30.0  1
 FRR  Var_08    H23   C23  C17  C34    -1.85   0.0  0
 FRR  Var_09    H1    C42  C41  C40     1.46   0.0  0
 FRR  Var_10    H591  C59  O48  C15  -179.16  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
 FRR  chir_01  C31  O15  C18  C62  negativ
 FRR  chir_02  C24  O42  C34  C39  negativ
 FRR  chir_03  C39  O44  C24  C40  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
 FRR  plan-1  C11  0.020
 FRR  plan-1  C2   0.020
 FRR  plan-1  C3   0.020
 FRR  plan-1  C14  0.020
 FRR  plan-1  C15  0.020
 FRR  plan-1  C16  0.020
 FRR  plan-1  C23  0.020
 FRR  plan-1  C26  0.020
 FRR  plan-1  O46  0.020
 FRR  plan-1  O48  0.020
 FRR  plan-1  H16  0.020
 FRR  plan-1  H14  0.020
 FRR  plan-2  C39  0.020
 FRR  plan-2  C40  0.020
 FRR  plan-2  C41  0.020
 FRR  plan-2  O40  0.020
 FRR  plan-3  C3   0.020
 FRR  plan-3  C23  0.020
 FRR  plan-3  C17  0.020
 FRR  plan-3  C34  0.020
 FRR  plan-3  H23  0.020
 FRR  plan-3  H17  0.020
 FRR  plan-4  C2   0.020
 FRR  plan-4  O15  0.020
 FRR  plan-4  C26  0.020
 FRR  plan-4  O38  0.020
 FRR  plan-5  C18  0.020
 FRR  plan-5  C40  0.020
 FRR  plan-5  C41  0.020
 FRR  plan-5  C42  0.020
 FRR  plan-5  H41  0.020
 FRR  plan-5  H1   0.020

