# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Jun  9 01:19:29 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: (3S,11E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]1CCCC(=O)CCC\C=C\c2cc(O)cc(O)c2C(=O)O1
#
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
 ZER  ZER  (3S,11E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione  ligand  45  23  .  2021-08-25  2021-08-25  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ZER
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
 ZER  O12  O  O     0  -0.413  -0.3447   0.4929  -1.0586
 ZER  C12  C  C     0   0.535   0.4765   0.9352  -0.2991
 ZER  O10  O  O2    0  -0.496   0.2942   2.0193   0.4531
 ZER  C10  C  CH1   0   0.030  -0.9631   2.7553   0.4615
 ZER  C11  C  CH3   0  -0.707  -1.1754   3.5161  -0.8333
 ZER  C9P  C  CH2   0  -0.493  -2.1502   1.9019   0.9409
 ZER  C1   C  CR6   0  -0.207   1.8286   0.3562  -0.0981
 ZER  C2   C  CR6   0   0.379   2.9700   1.1721  -0.1981
 ZER  O2   O  OH1   0  -0.627   2.9083   2.5011  -0.3951
 ZER  C3   C  CR16  0  -0.437   4.2413   0.6197  -0.1426
 ZER  C4   C  CR6   0   0.393   4.3914  -0.7437   0.0682
 ZER  O4   O  OH1   0  -0.624   5.6416  -1.2283   0.1143
 ZER  C5   C  CR16  0  -0.446   3.2702  -1.5521   0.2444
 ZER  C6   C  CR6   0   0.081   1.9938  -1.0160   0.1492
 ZER  C1P  C  C1    0  -0.330   0.8578  -1.9163   0.4661
 ZER  C2P  C  C1    0  -0.139   0.0085  -2.4565  -0.4002
 ZER  C3P  C  CH2   0  -0.495  -1.1019  -3.3856  -0.0232
 ZER  C4P  C  CH2   0  -0.429  -2.4825  -2.8249  -0.3785
 ZER  C5P  C  CH2   0  -0.570  -2.8215  -1.5826   0.4298
 ZER  C6P  C  C     0   0.398  -4.0883  -0.8788   0.0168
 ZER  O6P  O  O     0  -0.410  -4.9197  -1.4159  -0.6830
 ZER  C7P  C  CH2   0  -0.545  -4.2625   0.5393   0.5071
 ZER  C8P  C  CH2   0  -0.471  -3.1951   1.4846  -0.0917
 ZER  H1   H  HCH1  0   0.263  -0.7573   3.4865   1.2422
 ZER  H2   H  HCH3  0   0.245  -1.3518   2.8690  -1.6899
 ZER  H3   H  HCH3  0   0.249  -2.0405   4.1707  -0.7213
 ZER  H4   H  HCH3  0   0.249  -0.3161   4.1520  -1.0501
 ZER  H5   H  HCH2  0   0.247  -1.7690   1.0245   1.4711
 ZER  H6   H  HCH2  0   0.256  -2.6688   2.4864   1.7059
 ZER  H7   H  HOH1  0   0.472   2.0400   2.8449  -0.1488
 ZER  H8   H  HCR6  0   0.276   5.1094   1.2579  -0.2505
 ZER  H9   H  HOH1  0   0.479   5.6315  -2.1815   0.2579
 ZER  H10  H  HCR6  0   0.270   3.3878  -2.6082   0.4590
 ZER  H11  H  H     0   0.261   0.7714  -2.1769   1.5191
 ZER  H12  H  H     0   0.240   0.0952  -2.2161  -1.4557
 ZER  H13  H  HCH2  0   0.247  -0.9676  -4.3340  -0.5522
 ZER  H14  H  HCH2  0   0.232  -1.0536  -3.6124   1.0457
 ZER  H15  H  HCH2  0   0.226  -2.5095  -2.5899  -1.4462
 ZER  H16  H  HCH2  0   0.237  -3.2342  -3.5992  -0.2150
 ZER  H17  H  HCH2  0   0.269  -2.9312  -1.8321   1.4930
 ZER  H18  H  HCH2  0   0.278  -1.9951  -0.8705   0.3944
 ZER  H19  H  HCH2  0   0.260  -5.2664   0.8744   0.2453
 ZER  H20  H  HCH2  0   0.258  -4.1957   0.5474   1.5999
 ZER  H21  H  HCH2  0   0.252  -3.7002   2.3740  -0.4707
 ZER  H22  H  HCH2  0   0.256  -2.7206   1.0205  -0.9558

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
 ZER  C4P  C3P  single    1.532  0.020  1.532
 ZER  C4P  C5P  single    1.520  0.020  1.520
 ZER  C3P  C2P  single    1.496  0.020  1.496
 ZER  C2P  C1P  double    1.328  0.020  1.328
 ZER  C5P  C6P  single    1.507  0.020  1.507
 ZER  O6P  C6P  double    1.212  0.020  1.212
 ZER  C6P  C7P  single    1.511  0.020  1.511
 ZER  O4   C4   single    1.342  0.020  1.342
 ZER  C5   C4   aromatic  1.393  0.020  1.393
 ZER  C5   C6   single    1.388  0.020  1.388
 ZER  C1P  C6   single    1.484  0.020  1.484
 ZER  C4   C3   aromatic  1.388  0.020  1.388
 ZER  C6   C1   aromatic  1.404  0.020  1.404
 ZER  C7P  C8P  single    1.546  0.020  1.546
 ZER  C8P  C9P  single    1.527  0.020  1.527
 ZER  C3   C2   aromatic  1.387  0.020  1.387
 ZER  C1   C2   single    1.407  0.020  1.407
 ZER  C1   C12  single    1.485  0.020  1.485
 ZER  O10  C12  single    1.332  0.020  1.332
 ZER  O10  C10  single    1.457  0.020  1.457
 ZER  C2   O2   single    1.345  0.020  1.345
 ZER  C12  O12  double    1.203  0.020  1.203
 ZER  C9P  C10  single    1.539  0.020  1.539
 ZER  C10  C11  single    1.517  0.020  1.517
 ZER  C10  H1   single    0.970  0.020  1.090
 ZER  C11  H2   single    0.970  0.020  1.090
 ZER  C11  H3   single    0.970  0.020  1.090
 ZER  C11  H4   single    0.970  0.020  1.090
 ZER  C9P  H5   single    0.970  0.020  1.090
 ZER  C9P  H6   single    0.970  0.020  1.090
 ZER  O2   H7   single    0.850  0.020  0.980
 ZER  C3   H8   single    0.930  0.020  1.080
 ZER  O4   H9   single    0.850  0.020  0.980
 ZER  C5   H10  single    0.930  0.020  1.080
 ZER  C1P  H11  single    0.930  0.020  1.080
 ZER  C2P  H12  single    0.930  0.020  1.080
 ZER  C3P  H13  single    0.970  0.020  1.090
 ZER  C3P  H14  single    0.970  0.020  1.090
 ZER  C4P  H15  single    0.970  0.020  1.090
 ZER  C4P  H16  single    0.970  0.020  1.090
 ZER  C5P  H17  single    0.970  0.020  1.090
 ZER  C5P  H18  single    0.970  0.020  1.090
 ZER  C7P  H19  single    0.970  0.020  1.090
 ZER  C7P  H20  single    0.970  0.020  1.090
 ZER  C8P  H21  single    0.970  0.020  1.090
 ZER  C8P  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
 ZER  C1   C12  O10  111.45  3.000
 ZER  O10  C12  O12  124.23  3.000
 ZER  C1   C12  O12  124.32  3.000
 ZER  C10  O10  C12  122.17  3.000
 ZER  H1   C10  C9P  107.14  3.000
 ZER  H1   C10  C11  107.56  3.000
 ZER  C9P  C10  C11  115.86  3.000
 ZER  H1   C10  O10  100.38  3.000
 ZER  C11  C10  O10  111.67  3.000
 ZER  C9P  C10  O10  112.79  3.000
 ZER  H4   C11  H3   107.18  3.000
 ZER  H4   C11  H2   108.54  3.000
 ZER  H3   C11  H2   108.02  3.000
 ZER  H4   C11  C10  110.60  3.000
 ZER  H3   C11  C10  108.93  3.000
 ZER  H2   C11  C10  113.36  3.000
 ZER  H6   C9P  H5   104.77  3.000
 ZER  H6   C9P  C8P  107.13  3.000
 ZER  H5   C9P  C8P  110.31  3.000
 ZER  H6   C9P  C10  106.70  3.000
 ZER  H5   C9P  C10  109.09  3.000
 ZER  C8P  C9P  C10  117.95  3.000
 ZER  C6   C1   C2   118.94  3.000
 ZER  C2   C1   C12  120.21  3.000
 ZER  C6   C1   C12  120.81  3.000
 ZER  C3   C2   O2   116.19  3.000
 ZER  O2   C2   C1   123.12  3.000
 ZER  C3   C2   C1   120.66  3.000
 ZER  H7   O2   C2   110.83  3.000
 ZER  H8   C3   C4   120.50  3.000
 ZER  H8   C3   C2   119.74  3.000
 ZER  C4   C3   C2   119.76  3.000
 ZER  C5   C4   O4   122.40  3.000
 ZER  C5   C4   C3   120.14  3.000
 ZER  O4   C4   C3   117.44  3.000
 ZER  H9   O4   C4   110.64  3.000
 ZER  H10  C5   C6   119.32  3.000
 ZER  H10  C5   C4   120.20  3.000
 ZER  C6   C5   C4   120.48  3.000
 ZER  C1P  C6   C5   117.07  3.000
 ZER  C1P  C6   C1   122.72  3.000
 ZER  C5   C6   C1   119.86  3.000
 ZER  H11  C1P  C2P  118.88  3.000
 ZER  H11  C1P  C6   114.38  3.000
 ZER  C2P  C1P  C6   126.67  3.000
 ZER  H12  C2P  C3P  116.21  3.000
 ZER  H12  C2P  C1P  119.53  3.000
 ZER  C3P  C2P  C1P  124.26  3.000
 ZER  H14  C3P  H13  106.70  3.000
 ZER  H14  C3P  C4P  110.02  3.000
 ZER  H13  C3P  C4P  108.40  3.000
 ZER  H14  C3P  C2P  110.02  3.000
 ZER  H13  C3P  C2P  108.98  3.000
 ZER  C4P  C3P  C2P  112.53  3.000
 ZER  H16  C4P  H15  106.36  3.000
 ZER  H16  C4P  C5P  110.27  3.000
 ZER  H15  C4P  C5P  109.76  3.000
 ZER  H16  C4P  C3P  109.04  3.000
 ZER  H15  C4P  C3P  109.11  3.000
 ZER  C5P  C4P  C3P  112.13  3.000
 ZER  H18  C5P  H17  104.79  3.000
 ZER  H18  C5P  C6P  108.84  3.000
 ZER  H17  C5P  C6P  106.72  3.000
 ZER  H18  C5P  C4P  110.30  3.000
 ZER  H17  C5P  C4P  110.58  3.000
 ZER  C6P  C5P  C4P  115.05  3.000
 ZER  C7P  C6P  O6P  121.62  3.000
 ZER  C7P  C6P  C5P  116.52  3.000
 ZER  O6P  C6P  C5P  121.86  3.000
 ZER  H20  C7P  H19  107.07  3.000
 ZER  H20  C7P  C8P  109.87  3.000
 ZER  H19  C7P  C8P  110.78  3.000
 ZER  H20  C7P  C6P  108.90  3.000
 ZER  H19  C7P  C6P  108.47  3.000
 ZER  C8P  C7P  C6P  111.63  3.000
 ZER  H22  C8P  H21  105.87  3.000
 ZER  H22  C8P  C7P  110.32  3.000
 ZER  H21  C8P  C7P  108.26  3.000
 ZER  H22  C8P  C9P  110.77  3.000
 ZER  H21  C8P  C9P  109.20  3.000
 ZER  C7P  C8P  C9P  112.18  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
 ZER  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 ZER  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 ZER  CONST_03  C5   C4   C3   C2      0.00   0.0  0
 ZER  CONST_04  C5   C6   C1   C2      0.00   0.0  0
 ZER  CONST_05  C6   C5   C4   C3      0.00   0.0  0
 ZER  CONST_06  C6   C1   C2   C3      0.00   0.0  0
 ZER  CONST_07  O2   C2   C1   C12     0.00   0.0  0
 ZER  CONST_08  O4   C4   C3   C2    180.00   0.0  0
 ZER  CONST_09  C4   C3   C2   O2    180.00   0.0  0
 ZER  CONST_10  C6   C1   C2   O2    180.00   0.0  0
 ZER  CONST_11  C6   C5   C4   O4    180.00   0.0  0
 ZER  CONST_12  H10  C5   C6   C1    180.00   0.0  0
 ZER  CONST_13  H8   C3   C2   C1    180.00   0.0  0
 ZER  Var_01    C3P  C2P  C1P  C6    178.50   0.0  0
 ZER  Var_02    C6   C1   C12  O10   131.03  30.0  1
 ZER  Var_03    C1   C12  O10  C10  -178.55  30.0  1
 ZER  Var_04    C7P  C8P  C9P  C10   175.35  30.0  1
 ZER  Var_05    C6P  C7P  C8P  C9P  -107.44  30.0  1
 ZER  Var_06    C2P  C1P  C6   C1     80.15  30.0  1
 ZER  Var_07    C4P  C3P  C2P  C1P   118.40  30.0  1
 ZER  Var_08    C5P  C4P  C3P  C2P   -65.69  30.0  1
 ZER  Var_09    C6P  C5P  C4P  C3P   172.84  30.0  1
 ZER  Var_10    C7P  C6P  C5P  C4P  -163.27  30.0  1
 ZER  Var_11    C8P  C7P  C6P  C5P    64.88  30.0  1
 ZER  Var_12    H11  C1P  C2P  C3P     1.75   0.0  0

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
 ZER  chir_01  C10  O10  C9P  C11  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
 ZER  plan-1  C12  0.020
 ZER  plan-1  C1   0.020
 ZER  plan-1  C2   0.020
 ZER  plan-1  O2   0.020
 ZER  plan-1  C3   0.020
 ZER  plan-1  C4   0.020
 ZER  plan-1  O4   0.020
 ZER  plan-1  C5   0.020
 ZER  plan-1  C6   0.020
 ZER  plan-1  C1P  0.020
 ZER  plan-1  H8   0.020
 ZER  plan-1  H10  0.020
 ZER  plan-2  C5P  0.020
 ZER  plan-2  C6P  0.020
 ZER  plan-2  O6P  0.020
 ZER  plan-2  C7P  0.020
 ZER  plan-3  C6   0.020
 ZER  plan-3  C1P  0.020
 ZER  plan-3  C2P  0.020
 ZER  plan-3  C3P  0.020
 ZER  plan-3  H11  0.020
 ZER  plan-3  H12  0.020
 ZER  plan-4  O12  0.020
 ZER  plan-4  C12  0.020
 ZER  plan-4  O10  0.020
 ZER  plan-4  C1   0.020

