# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 12:42:17 2020
#   Inital geometry file: a 123 line input string
#   Ligand name: (3S,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
 1FM  1FM  (3S,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  .  2021-08-03  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1FM
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
 1FM  C2    C  CR6   0  -0.229  -1.6032   0.7818   0.4177
 1FM  C3    C  CR6   0   0.107  -1.4770  -0.6041   0.6551
 1FM  C11   C  CR6   0   0.394  -2.8344   1.2842  -0.0233
 1FM  C14   C  CR16  0  -0.427  -2.5742  -1.4301   0.4989
 1FM  C15   C  CR6   0   0.425  -3.8144  -0.9061   0.1171
 1FM  O15   O  O2    0  -0.500  -0.3143   2.5698  -0.3397
 1FM  C16   C  CR16  0  -0.485  -3.9440   0.4480  -0.1458
 1FM  C17   C  C1    0  -0.186   0.3243  -2.2147   0.2428
 1FM  C18   C  CH2   0  -0.529   2.0922   2.7006  -0.8135
 1FM  C23   C  C1    0  -0.301  -0.1748  -1.2245   0.9786
 1FM  C24   C  CH1   0   0.050   2.5566  -2.9305  -0.6982
 1FM  C26   C  C     0   0.574  -0.4381   1.6673   0.6353
 1FM  C31   C  CH1   0   0.002   0.8241   3.4636  -0.4149
 1FM  C34   C  CH2   0  -0.547   1.6027  -2.9405   0.5068
 1FM  O38   O  O     0  -0.422   0.3077   1.5895   1.5758
 1FM  C39   C  CH1   0  -0.063   3.5404  -1.7498  -0.6974
 1FM  C40   C  C     0   0.325   2.8312  -0.4015  -0.7971
 1FM  O40   O  O     0  -0.415   2.1176  -0.2097  -1.7640
 1FM  C41   C  C1    0  -0.351   3.0900   0.5893   0.2545
 1FM  C42   C  C1    0  -0.113   2.7419   1.8838   0.2512
 1FM  O42   O  OH1   0  -0.680   3.3939  -4.0695  -0.7142
 1FM  O44   O  OH1   0  -0.663   4.3857  -1.7881   0.4196
 1FM  O46   O  OH1   0  -0.625  -3.0489   2.5755  -0.3184
 1FM  O48   O  O2    0  -0.465  -4.8181  -1.7871   0.0211
 1FM  C59   C  CH3   0  -0.441  -6.0950  -1.3268  -0.3824
 1FM  C62   C  CH3   0  -0.700   0.9541   4.3936   0.7771
 1FM  H14   H  HCR6  0   0.262  -2.4803  -2.4923   0.6824
 1FM  H16   H  HCR6  0   0.290  -4.8814   0.8877  -0.4585
 1FM  H17   H  H     0   0.248  -0.2322  -2.5516  -0.6289
 1FM  H18   H  HCH2  0   0.280   1.8846   2.1188  -1.7068
 1FM  H18A  H  HCH2  0   0.271   2.8106   3.4775  -1.1004
 1FM  H23   H  H     0   0.261   0.3876  -0.8436   1.8215
 1FM  H24   H  HCH1  0   0.221   1.9646  -2.8770  -1.6209
 1FM  H31   H  HCH1  0   0.272   0.5630   4.0738  -1.2794
 1FM  H34   H  HCH2  0   0.253   2.0994  -2.5606   1.4030
 1FM  H34A  H  HCH2  0   0.260   1.3418  -3.9844   0.7188
 1FM  H39   H  HCH1  0   0.259   4.1277  -1.8290  -1.6272
 1FM  H41   H  H     0   0.262   3.6175   0.2319   1.1273
 1FM  H42   H  H     0   0.262   3.0329   2.4443   1.1340
 1FM  HO42  H  HOH1  0   0.457   2.8499  -4.8588  -0.6317
 1FM  HO44  H  HOH1  0   0.458   4.7713  -2.6704   0.4666
 1FM  HO46  H  HOH1  0   0.477  -2.2111   3.0474  -0.4220
 1FM  H59   H  HCH3  0   0.233  -6.0689  -0.8837  -1.3807
 1FM  H59A  H  HCH3  0   0.264  -6.7440  -2.1982  -0.4012
 1FM  H59B  H  HCH3  0   0.234  -6.5040  -0.5964   0.3198
 1FM  H62   H  HCH3  0   0.248   1.3097   3.9080   1.6809
 1FM  H62A  H  HCH3  0   0.247   1.6598   5.1831   0.5163
 1FM  H62B  H  HCH3  0   0.250  -0.0013   4.8721   0.9941

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
 1FM  C3   C2    aromatic  1.412  0.020  1.412
 1FM  C2   C11   single    1.401  0.020  1.401
 1FM  C2   C26   single    1.479  0.020  1.479
 1FM  C23  C3    single    1.478  0.020  1.478
 1FM  C14  C3    single    1.382  0.020  1.382
 1FM  C16  C11   aromatic  1.395  0.020  1.395
 1FM  C11  O46   single    1.342  0.020  1.342
 1FM  C14  C15   aromatic  1.399  0.020  1.399
 1FM  C14  H14   single    0.930  0.020  1.080
 1FM  O48  C15   single    1.339  0.020  1.339
 1FM  C15  C16   aromatic  1.385  0.020  1.385
 1FM  O15  C31   single    1.449  0.020  1.449
 1FM  O15  C26   single    1.334  0.020  1.334
 1FM  C16  H16   single    0.930  0.020  1.080
 1FM  C34  C17   single    1.494  0.020  1.494
 1FM  C17  C23   double    1.331  0.020  1.331
 1FM  C17  H17   single    0.930  0.020  1.080
 1FM  C42  C18   single    1.491  0.020  1.491
 1FM  C18  C31   single    1.533  0.020  1.533
 1FM  C18  H18   single    0.970  0.020  1.090
 1FM  C18  H18A  single    0.970  0.020  1.090
 1FM  C23  H23   single    0.930  0.020  1.080
 1FM  O42  C24   single    1.414  0.020  1.414
 1FM  C39  C24   single    1.537  0.020  1.537
 1FM  C24  C34   single    1.537  0.020  1.537
 1FM  C24  H24   single    0.970  0.020  1.090
 1FM  C26  O38   double    1.203  0.020  1.203
 1FM  C31  C62   single    1.517  0.020  1.517
 1FM  C31  H31   single    0.970  0.020  1.090
 1FM  C34  H34   single    0.970  0.020  1.090
 1FM  C34  H34A  single    0.970  0.020  1.090
 1FM  O44  C39   single    1.401  0.020  1.401
 1FM  C39  C40   single    1.527  0.020  1.527
 1FM  C39  H39   single    0.970  0.020  1.090
 1FM  C41  C40   single    1.468  0.020  1.468
 1FM  C40  O40   double    1.217  0.020  1.217
 1FM  C41  C42   double    1.341  0.020  1.341
 1FM  C41  H41   single    0.930  0.020  1.080
 1FM  C42  H42   single    0.930  0.020  1.080
 1FM  O42  HO42  single    0.850  0.020  0.980
 1FM  O44  HO44  single    0.850  0.020  0.980
 1FM  O46  HO46  single    0.850  0.020  0.980
 1FM  C59  O48   single    1.416  0.020  1.416
 1FM  C59  H59   single    0.970  0.020  1.090
 1FM  C59  H59A  single    0.970  0.020  1.090
 1FM  C59  H59B  single    0.970  0.020  1.090
 1FM  C62  H62   single    0.970  0.020  1.090
 1FM  C62  H62A  single    0.970  0.020  1.090
 1FM  C62  H62B  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
 1FM  C26   C2   C11   121.58  3.000
 1FM  C26   C2   C3    119.50  3.000
 1FM  C11   C2   C3    118.91  3.000
 1FM  C23   C3   C14   118.24  3.000
 1FM  C14   C3   C2    119.78  3.000
 1FM  C23   C3   C2    121.84  3.000
 1FM  O46   C11  C16   115.50  3.000
 1FM  O46   C11  C2    123.70  3.000
 1FM  C16   C11  C2    120.78  3.000
 1FM  H14   C14  C15   119.39  3.000
 1FM  H14   C14  C3    119.91  3.000
 1FM  C15   C14  C3    120.70  3.000
 1FM  O48   C15  C16   124.01  3.000
 1FM  C16   C15  C14   120.04  3.000
 1FM  O48   C15  C14   115.95  3.000
 1FM  C31   O15  C26   121.86  3.000
 1FM  H16   C16  C15   122.23  3.000
 1FM  H16   C16  C11   118.11  3.000
 1FM  C15   C16  C11   119.66  3.000
 1FM  H17   C17  C34   115.41  3.000
 1FM  H17   C17  C23   118.80  3.000
 1FM  C34   C17  C23   125.79  3.000
 1FM  H18A  C18  H18   106.84  3.000
 1FM  H18A  C18  C42   106.83  3.000
 1FM  H18   C18  C42   112.15  3.000
 1FM  H18A  C18  C31   104.92  3.000
 1FM  H18   C18  C31   108.81  3.000
 1FM  C42   C18  C31   116.59  3.000
 1FM  H23   C23  C17   119.84  3.000
 1FM  H23   C23  C3    118.71  3.000
 1FM  C17   C23  C3    121.44  3.000
 1FM  H24   C24  O42   110.44  3.000
 1FM  H24   C24  C39   107.95  3.000
 1FM  O42   C24  C39   103.88  3.000
 1FM  H24   C24  C34   108.94  3.000
 1FM  C39   C24  C34   113.69  3.000
 1FM  O42   C24  C34   111.79  3.000
 1FM  O38   C26  O15   123.88  3.000
 1FM  O38   C26  C2    124.38  3.000
 1FM  O15   C26  C2    111.74  3.000
 1FM  H31   C31  C62   107.49  3.000
 1FM  H31   C31  C18   105.70  3.000
 1FM  C62   C31  C18   116.01  3.000
 1FM  H31   C31  O15   101.43  3.000
 1FM  C62   C31  O15   113.86  3.000
 1FM  C18   C31  O15   110.88  3.000
 1FM  H34A  C34  H34   106.29  3.000
 1FM  H34A  C34  C24   107.78  3.000
 1FM  H34   C34  C24   111.02  3.000
 1FM  H34A  C34  C17   107.04  3.000
 1FM  H34   C34  C17   111.41  3.000
 1FM  C24   C34  C17   112.92  3.000
 1FM  H39   C39  O44   110.42  3.000
 1FM  H39   C39  C40   104.82  3.000
 1FM  O44   C39  C40   110.88  3.000
 1FM  H39   C39  C24   106.58  3.000
 1FM  C40   C39  C24   112.41  3.000
 1FM  O44   C39  C24   111.44  3.000
 1FM  C41   C40  O40   124.49  3.000
 1FM  O40   C40  C39   117.61  3.000
 1FM  C41   C40  C39   117.87  3.000
 1FM  H41   C41  C42   116.62  3.000
 1FM  H41   C41  C40   116.20  3.000
 1FM  C42   C41  C40   127.18  3.000
 1FM  H42   C42  C41   115.28  3.000
 1FM  H42   C42  C18   114.50  3.000
 1FM  C41   C42  C18   130.09  3.000
 1FM  HO42  O42  C24   108.97  3.000
 1FM  HO44  O44  C39   107.76  3.000
 1FM  HO46  O46  C11   110.77  3.000
 1FM  C59   O48  C15   118.86  3.000
 1FM  H59B  C59  H59A  108.88  3.000
 1FM  H59B  C59  H59   108.96  3.000
 1FM  H59A  C59  H59   108.89  3.000
 1FM  H59B  C59  O48   111.82  3.000
 1FM  H59A  C59  O48   106.43  3.000
 1FM  H59   C59  O48   111.75  3.000
 1FM  H62B  C62  H62A  107.27  3.000
 1FM  H62B  C62  H62   108.51  3.000
 1FM  H62A  C62  H62   108.12  3.000
 1FM  H62B  C62  C31   110.50  3.000
 1FM  H62A  C62  C31   108.14  3.000
 1FM  H62   C62  C31   114.07  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
 1FM  CONST_01  C15  C14  C3   C2      0.00   0.0  0
 1FM  CONST_02  C15  C16  C11  C2      0.00   0.0  0
 1FM  CONST_03  C16  C11  C2   C3      0.00   0.0  0
 1FM  CONST_04  C16  C15  C14  C3      0.00   0.0  0
 1FM  CONST_05  C14  C3   C2   C11     0.00   0.0  0
 1FM  CONST_06  C14  C15  C16  C11     0.00   0.0  0
 1FM  CONST_07  O46  C11  C2   C3    180.00   0.0  0
 1FM  CONST_08  O48  C15  C14  C3    180.00   0.0  0
 1FM  CONST_09  O48  C15  C16  C11   180.00   0.0  0
 1FM  CONST_10  O46  C11  C16  C15   180.00   0.0  0
 1FM  CONST_11  O46  C11  C2   C26     0.00   0.0  0
 1FM  CONST_12  H14  C14  C3   C2    180.00   0.0  0
 1FM  CONST_13  H16  C16  C11  C2    180.00   0.0  0
 1FM  Var_01    C34  C17  C23  C3   -177.80   0.0  0
 1FM  Var_02    C40  C41  C42  C18    -4.35   0.0  0
 1FM  Var_03    C17  C23  C3   C2   -123.10  30.0  1
 1FM  Var_04    O15  C26  C2   C3    137.51  30.0  1
 1FM  Var_05    C24  C34  C17  C23  -125.48  30.0  1
 1FM  Var_06    C41  C42  C18  C31   126.48  30.0  1
 1FM  Var_07    C42  C41  C40  C39   168.90  30.0  1
 1FM  Var_08    H23  C23  C17  C34     3.56   0.0  0
 1FM  Var_09    H42  C42  C41  C40  -179.94   0.0  0
 1FM  Var_10    H59  C59  O48  C15    60.70  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
 1FM  chir_01  C24  O42  C39  C34  positiv
 1FM  chir_02  C31  O15  C18  C62  positiv
 1FM  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
 1FM  plan-1  C2   0.020
 1FM  plan-1  C3   0.020
 1FM  plan-1  C11  0.020
 1FM  plan-1  C14  0.020
 1FM  plan-1  C15  0.020
 1FM  plan-1  C16  0.020
 1FM  plan-1  C23  0.020
 1FM  plan-1  C26  0.020
 1FM  plan-1  O46  0.020
 1FM  plan-1  O48  0.020
 1FM  plan-1  H14  0.020
 1FM  plan-1  H16  0.020
 1FM  plan-2  C39  0.020
 1FM  plan-2  C40  0.020
 1FM  plan-2  O40  0.020
 1FM  plan-2  C41  0.020
 1FM  plan-3  C3   0.020
 1FM  plan-3  C17  0.020
 1FM  plan-3  C23  0.020
 1FM  plan-3  C34  0.020
 1FM  plan-3  H17  0.020
 1FM  plan-3  H23  0.020
 1FM  plan-4  C2   0.020
 1FM  plan-4  O15  0.020
 1FM  plan-4  C26  0.020
 1FM  plan-4  O38  0.020
 1FM  plan-5  C18  0.020
 1FM  plan-5  C40  0.020
 1FM  plan-5  C41  0.020
 1FM  plan-5  C42  0.020
 1FM  plan-5  H41  0.020
 1FM  plan-5  H42  0.020

