# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 16:33:49 2020
#   Inital geometry file: a 155 line input string
#   Ligand name: (5E,9E,11E)-13-chloro-14,16-dihydroxy-11-{[2-oxo-2-(piperidin-1-yl)ethoxy]imino}-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecin-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(O)c2C(=O)OCC\C=C\CC/C=C/C(Cc2c1Cl)=N/OCC(=O)N3CCCCC3
#
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
 JZB  JZB  (5E,9E,11E)-13-chloro-14,16-dihydroxy-11-{[2-oxo-2-(piperidin-1-yl)ethoxy]imino}-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecin-1-one  ligand  62  33  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_JZB
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
 JZB  CL    CL  CL    0  -0.118  -1.6744   1.4440   1.8504
 JZB  C1    C   CR16  0  -0.467  -0.8061   3.0732  -1.6675
 JZB  N1    N   N     0  -0.142   0.3806  -1.7400   0.7515
 JZB  O1    O   O2    0  -0.492   3.2368   1.8450  -1.9946
 JZB  C2    C   CR6   0   0.474  -1.4708   2.6771  -0.5201
 JZB  N2    N   NT    0  -0.453  -4.2791  -1.4818   0.2526
 JZB  O2    O   O     0  -0.392   2.5375  -0.1554  -1.2897
 JZB  C3    C   CR6   0  -0.253  -0.8114   1.8595   0.4035
 JZB  O3    O   OH1   0  -0.609  -2.7121   3.1301  -0.3358
 JZB  C4    C   CR6   0   0.302   0.4521   1.3579   0.1534
 JZB  O4    O   OH1   0  -0.626   1.0377   3.0409  -3.0685
 JZB  C5    C   CR6   0  -0.288   1.0979   1.7169  -1.0422
 JZB  O5    O   O2    0  -0.399  -0.7186  -1.0916   0.2339
 JZB  C6    C   CR6   0   0.382   0.4772   2.6146  -1.9272
 JZB  O6    O   O     0  -0.477  -2.8432  -0.1503  -0.8782
 JZB  C7    C   CH2   0  -0.644   1.1985   0.5798   1.2047
 JZB  C8    C   C     0   0.559   2.3489   1.0229  -1.4286
 JZB  C9    C   C     0   0.248   1.2847  -0.9273   1.1244
 JZB  C10   C   C1    0  -0.290   2.5558  -1.4700   1.6118
 JZB  C11   C   CH2   0  -0.202   4.4340   1.2965  -2.5837
 JZB  C12   C   CH2   0  -0.519   5.4975   0.8489  -1.5847
 JZB  C13   C   C1    0  -0.178   5.4411  -0.5916  -1.1786
 JZB  C14   C   C1    0  -0.196   5.6485  -1.0697   0.0423
 JZB  C15   C   CH2   0  -0.489   5.6364  -2.5275   0.3863
 JZB  C16   C   C1    0  -0.143   3.2297  -2.4695   1.0511
 JZB  C17   C   CH2   0  -0.501   4.6025  -2.8744   1.4710
 JZB  C18   C   CH2   0  -0.250  -1.8785  -1.8184   0.5309
 JZB  C19   C   C     0   0.508  -3.0453  -1.0736  -0.1074
 JZB  C20   C   CH2   0  -0.310  -5.4630  -0.8239  -0.2760
 JZB  C21   C   CH2   0  -0.434  -6.2473  -1.7599  -1.1854
 JZB  C22   C   CH2   0  -0.447  -6.5823  -3.0606  -0.4624
 JZB  C23   C   CH2   0  -0.426  -5.3255  -3.6903   0.1291
 JZB  C24   C   CH2   0  -0.325  -4.5714  -2.6932   1.0013
 JZB  H1    H   HCR6  0   0.282  -1.2960   3.7350  -2.3706
 JZB  HO3   H   HOH1  0   0.468  -3.1135   2.7350   0.4491
 JZB  HO4   H   HOH1  0   0.480   1.9834   2.8373  -3.0772
 JZB  H7    H   HCH2  0   0.286   2.2226   0.9530   1.2422
 JZB  H7A   H   HCH2  0   0.301   0.7869   0.8132   2.1903
 JZB  H10   H   H     0   0.254   3.0079  -0.9188   2.4329
 JZB  H11   H   HCH2  0   0.245   4.1711   0.4867  -3.2682
 JZB  H11A  H   HCH2  0   0.262   4.8159   2.1246  -3.1762
 JZB  H12   H   HCH2  0   0.257   6.4542   1.0210  -2.0904
 JZB  H12A  H   HCH2  0   0.254   5.5009   1.5111  -0.7150
 JZB  H13   H   H     0   0.221   5.2635  -1.2961  -1.9889
 JZB  H14   H   H     0   0.218   5.8214  -0.3781   0.8651
 JZB  H15   H   HCH2  0   0.231   5.4350  -3.1162  -0.5127
 JZB  H15A  H   HCH2  0   0.240   6.6217  -2.8386   0.7476
 JZB  H16   H   H     0   0.238   2.8140  -2.9721   0.1823
 JZB  H17   H   HCH2  0   0.245   4.6434  -3.9510   1.6596
 JZB  H17A  H   HCH2  0   0.235   4.8710  -2.3764   2.4063
 JZB  H18   H   HCH2  0   0.248  -1.8173  -2.8439   0.1418
 JZB  H18A  H   HCH2  0   0.240  -2.0216  -1.8886   1.6152
 JZB  H20   H   HCH2  0   0.235  -6.0872  -0.5232   0.5727
 JZB  H20A  H   HCH2  0   0.262  -5.1661   0.0819  -0.7977
 JZB  H21   H   HCH2  0   0.238  -7.1582  -1.2581  -1.5185
 JZB  H21A  H   HCH2  0   0.224  -5.6540  -1.9737  -2.0795
 JZB  H22   H   HCH2  0   0.218  -7.2991  -2.8573   0.3404
 JZB  H22A  H   HCH2  0   0.239  -7.0718  -3.7596  -1.1436
 JZB  H23   H   HCH2  0   0.240  -5.5769  -4.5690   0.7266
 JZB  H23A  H   HCH2  0   0.224  -4.6662  -4.0285  -0.6764
 JZB  H24   H   HCH2  0   0.269  -3.6606  -3.1451   1.3848
 JZB  H24A  H   HCH2  0   0.243  -5.1786  -2.4250   1.8721

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
 JZB  CL   C3    single    1.735  0.020  1.735
 JZB  C1   C2    aromatic  1.384  0.020  1.384
 JZB  C1   C6    aromatic  1.387  0.020  1.387
 JZB  N1   O5    single    1.377  0.020  1.377
 JZB  N1   C9    double    1.272  0.020  1.272
 JZB  O1   C8    single    1.336  0.020  1.336
 JZB  O1   C11   single    1.443  0.020  1.443
 JZB  C2   C3    aromatic  1.399  0.020  1.399
 JZB  C2   O3    single    1.334  0.020  1.334
 JZB  N2   C19   single    1.348  0.020  1.348
 JZB  N2   C20   single    1.454  0.020  1.454
 JZB  N2   C24   single    1.454  0.020  1.454
 JZB  O2   C8    double    1.201  0.020  1.201
 JZB  C3   C4    single    1.382  0.020  1.382
 JZB  C4   C5    aromatic  1.406  0.020  1.406
 JZB  C4   C7    single    1.506  0.020  1.506
 JZB  O4   C6    single    1.341  0.020  1.341
 JZB  C5   C6    single    1.405  0.020  1.405
 JZB  C5   C8    single    1.482  0.020  1.482
 JZB  O5   C18   single    1.401  0.020  1.401
 JZB  O6   C19   double    1.220  0.020  1.220
 JZB  C7   C9    single    1.512  0.020  1.512
 JZB  C9   C10   single    1.466  0.020  1.466
 JZB  C10  C16   double    1.329  0.020  1.329
 JZB  C11  C12   single    1.526  0.020  1.526
 JZB  C12  C13   single    1.498  0.020  1.498
 JZB  C13  C14   double    1.328  0.020  1.328
 JZB  C14  C15   single    1.498  0.020  1.498
 JZB  C15  C17   single    1.538  0.020  1.538
 JZB  C16  C17   single    1.492  0.020  1.492
 JZB  C18  C19   single    1.524  0.020  1.524
 JZB  C20  C21   single    1.523  0.020  1.523
 JZB  C21  C22   single    1.525  0.020  1.525
 JZB  C22  C23   single    1.525  0.020  1.525
 JZB  C23  C24   single    1.524  0.020  1.524
 JZB  C1   H1    single    0.930  0.020  1.080
 JZB  O3   HO3   single    0.850  0.020  0.980
 JZB  O4   HO4   single    0.850  0.020  0.980
 JZB  C7   H7    single    0.970  0.020  1.090
 JZB  C7   H7A   single    0.970  0.020  1.090
 JZB  C10  H10   single    0.930  0.020  1.080
 JZB  C11  H11   single    0.970  0.020  1.090
 JZB  C11  H11A  single    0.970  0.020  1.090
 JZB  C12  H12   single    0.970  0.020  1.090
 JZB  C12  H12A  single    0.970  0.020  1.090
 JZB  C13  H13   single    0.930  0.020  1.080
 JZB  C14  H14   single    0.930  0.020  1.080
 JZB  C15  H15   single    0.970  0.020  1.090
 JZB  C15  H15A  single    0.970  0.020  1.090
 JZB  C16  H16   single    0.930  0.020  1.080
 JZB  C17  H17   single    0.970  0.020  1.090
 JZB  C17  H17A  single    0.970  0.020  1.090
 JZB  C18  H18   single    0.970  0.020  1.090
 JZB  C18  H18A  single    0.970  0.020  1.090
 JZB  C20  H20   single    0.970  0.020  1.090
 JZB  C20  H20A  single    0.970  0.020  1.090
 JZB  C21  H21   single    0.970  0.020  1.090
 JZB  C21  H21A  single    0.970  0.020  1.090
 JZB  C22  H22   single    0.970  0.020  1.090
 JZB  C22  H22A  single    0.970  0.020  1.090
 JZB  C23  H23   single    0.970  0.020  1.090
 JZB  C23  H23A  single    0.970  0.020  1.090
 JZB  C24  H24   single    0.970  0.020  1.090
 JZB  C24  H24A  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
 JZB  H1    C1   C6   119.94  3.000
 JZB  H1    C1   C2   119.74  3.000
 JZB  C6    C1   C2   120.32  3.000
 JZB  C9    N1   O5   112.14  3.000
 JZB  C11   O1   C8   119.38  3.000
 JZB  O3    C2   C3   123.08  3.000
 JZB  O3    C2   C1   117.66  3.000
 JZB  C3    C2   C1   119.24  3.000
 JZB  C24   N2   C20  113.61  3.000
 JZB  C24   N2   C19  125.01  3.000
 JZB  C20   N2   C19  120.73  3.000
 JZB  C4    C3   C2   121.57  3.000
 JZB  C4    C3   CL   121.24  3.000
 JZB  C2    C3   CL   117.14  3.000
 JZB  HO3   O3   C2   111.09  3.000
 JZB  C7    C4   C5   119.87  3.000
 JZB  C7    C4   C3   120.95  3.000
 JZB  C5    C4   C3   118.77  3.000
 JZB  HO4   O4   C6   110.45  3.000
 JZB  C8    C5   C6   120.53  3.000
 JZB  C8    C5   C4   119.35  3.000
 JZB  C6    C5   C4   119.73  3.000
 JZB  C18   O5   N1   109.69  3.000
 JZB  C5    C6   O4   123.67  3.000
 JZB  C5    C6   C1   120.13  3.000
 JZB  O4    C6   C1   116.16  3.000
 JZB  H7A   C7   H7   104.44  3.000
 JZB  H7A   C7   C9   106.39  3.000
 JZB  H7    C7   C9   106.82  3.000
 JZB  H7A   C7   C4   109.42  3.000
 JZB  H7    C7   C4   108.22  3.000
 JZB  C9    C7   C4   120.42  3.000
 JZB  C5    C8   O2   124.18  3.000
 JZB  C5    C8   O1   112.54  3.000
 JZB  O2    C8   O1   123.25  3.000
 JZB  C10   C9   C7   113.64  3.000
 JZB  C10   C9   N1   118.52  3.000
 JZB  C7    C9   N1   127.75  3.000
 JZB  H10   C10  C16  119.26  3.000
 JZB  H10   C10  C9   115.09  3.000
 JZB  C16   C10  C9   125.30  3.000
 JZB  H11A  C11  H11  107.91  3.000
 JZB  H11A  C11  C12  109.59  3.000
 JZB  H11   C11  C12  111.13  3.000
 JZB  H11A  C11  O1   102.96  3.000
 JZB  H11   C11  O1   109.75  3.000
 JZB  C12   C11  O1   114.99  3.000
 JZB  H12A  C12  H12  105.62  3.000
 JZB  H12A  C12  C13  111.53  3.000
 JZB  H12   C12  C13  108.00  3.000
 JZB  H12A  C12  C11  110.20  3.000
 JZB  H12   C12  C11  105.09  3.000
 JZB  C13   C12  C11  115.68  3.000
 JZB  H13   C13  C14  118.49  3.000
 JZB  H13   C13  C12  115.27  3.000
 JZB  C14   C13  C12  126.15  3.000
 JZB  H14   C14  C15  116.49  3.000
 JZB  H14   C14  C13  119.41  3.000
 JZB  C15   C14  C13  124.09  3.000
 JZB  H15A  C15  H15  106.51  3.000
 JZB  H15A  C15  C17  107.95  3.000
 JZB  H15   C15  C17  109.55  3.000
 JZB  H15A  C15  C14  110.19  3.000
 JZB  H15   C15  C14  109.67  3.000
 JZB  C17   C15  C14  112.76  3.000
 JZB  H16   C16  C17  116.86  3.000
 JZB  H16   C16  C10  119.42  3.000
 JZB  C17   C16  C10  123.49  3.000
 JZB  H17A  C17  H17  106.96  3.000
 JZB  H17A  C17  C16  110.08  3.000
 JZB  H17   C17  C16  110.49  3.000
 JZB  H17A  C17  C15  109.61  3.000
 JZB  H17   C17  C15  108.57  3.000
 JZB  C16   C17  C15  111.03  3.000
 JZB  H18A  C18  H18  107.33  3.000
 JZB  H18A  C18  C19  110.22  3.000
 JZB  H18   C18  C19  110.52  3.000
 JZB  H18A  C18  O5   110.55  3.000
 JZB  H18   C18  O5   111.29  3.000
 JZB  C19   C18  O5   106.95  3.000
 JZB  C18   C19  O6   120.51  3.000
 JZB  C18   C19  N2   116.14  3.000
 JZB  O6    C19  N2   123.34  3.000
 JZB  H20A  C20  H20  107.38  3.000
 JZB  H20A  C20  C21  111.50  3.000
 JZB  H20   C20  C21  109.75  3.000
 JZB  H20A  C20  N2   109.23  3.000
 JZB  H20   C20  N2   107.84  3.000
 JZB  C21   C20  N2   111.00  3.000
 JZB  H21A  C21  H21  107.03  3.000
 JZB  H21A  C21  C22  109.87  3.000
 JZB  H21   C21  C22  110.68  3.000
 JZB  H21A  C21  C20  109.20  3.000
 JZB  H21   C21  C20  109.23  3.000
 JZB  C22   C21  C20  110.74  3.000
 JZB  H22A  C22  H22  106.42  3.000
 JZB  H22A  C22  C23  110.31  3.000
 JZB  H22   C22  C23  109.37  3.000
 JZB  H22A  C22  C21  110.40  3.000
 JZB  H22   C22  C21  109.45  3.000
 JZB  C23   C22  C21  110.79  3.000
 JZB  H23A  C23  H23  107.03  3.000
 JZB  H23A  C23  C24  108.98  3.000
 JZB  H23   C23  C24  109.09  3.000
 JZB  H23A  C23  C22  109.79  3.000
 JZB  H23   C23  C22  110.78  3.000
 JZB  C24   C23  C22  111.07  3.000
 JZB  H24A  C24  H24  106.62  3.000
 JZB  H24A  C24  C23  109.94  3.000
 JZB  H24   C24  C23  110.15  3.000
 JZB  H24A  C24  N2   108.48  3.000
 JZB  H24   C24  N2   111.08  3.000
 JZB  C23   C24  N2   110.48  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
 JZB  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 JZB  CONST_02  C4   C5   C6   C1      0.00   0.0  0
 JZB  CONST_03  C5   C6   C1   C2      0.00   0.0  0
 JZB  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 JZB  CONST_05  C6   C1   C2   C3      0.00   0.0  0
 JZB  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 JZB  CONST_07  C1   C2   C3   CL    180.00   0.0  0
 JZB  CONST_08  C5   C4   C3   CL    180.00   0.0  0
 JZB  CONST_09  C7   C4   C3   CL      0.00   0.0  0
 JZB  CONST_10  O4   C6   C1   C2    180.00   0.0  0
 JZB  CONST_11  C6   C1   C2   O3    180.00   0.0  0
 JZB  CONST_12  C4   C3   C2   O3    180.00   0.0  0
 JZB  CONST_13  O4   C6   C5   C4    180.00   0.0  0
 JZB  CONST_14  C8   C5   C6   O4      0.00   0.0  0
 JZB  CONST_15  H1   C1   C2   C3    180.00   0.0  0
 JZB  CONST_16  C20  N2   C19  O6      0.00   0.0  0
 JZB  CONST_17  C24  N2   C19  O6    180.00   0.0  0
 JZB  CONST_18  C20  N2   C19  C18   180.00   0.0  0
 JZB  CONST_19  C24  N2   C19  C18     0.00   0.0  0
 JZB  Var_01    C17  C16  C10  C9    171.71   0.0  0
 JZB  Var_02    C15  C14  C13  C12  -177.35   0.0  0
 JZB  Var_03    C4   C5   C8   O1   -142.08  30.0  1
 JZB  Var_04    C13  C12  C11  O1     92.86  30.0  1
 JZB  Var_05    C22  C21  C20  N2     54.55  30.0  1
 JZB  Var_06    C22  C23  C24  N2    -54.81  30.0  1
 JZB  Var_07    C9   C7   C4   C3    102.75  30.0  1
 JZB  Var_08    C10  C9   C7   C4    145.41  30.0  1
 JZB  Var_09    C16  C10  C9   C7   -139.57  30.0  1
 JZB  Var_10    C12  C11  O1   C8    -75.19  30.0  1
 JZB  Var_11    C15  C17  C16  C10  -110.34  30.0  1
 JZB  Var_12    C14  C13  C12  C11  -140.42  30.0  1
 JZB  Var_13    C17  C15  C14  C13  -122.29  30.0  1
 JZB  Var_14    C16  C17  C15  C14    57.67  30.0  1
 JZB  Var_15    C23  C24  N2   C20    57.99  30.0  1
 JZB  Var_16    C23  C22  C21  C20   -52.85  30.0  1
 JZB  Var_17    C24  N2   C20  C21   -58.12  30.0  1
 JZB  Var_18    C24  C23  C22  C21    53.19  30.0  1
 JZB  Var_19    H13  C13  C14  C15    -0.85   0.0  0
 JZB  Var_20    H10  C10  C16  C17    -1.09   0.0  0
 JZB  Var_21    C7   C9   N1   O5      7.80   0.0  2
 JZB  Var_22    O5   C18  C19  N2   -168.99  30.0  1
 JZB  Var_23    C19  C18  O5   N1   -178.15  30.0  3

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
 JZB  plan-1  CL   0.020
 JZB  plan-1  C1   0.020
 JZB  plan-1  C2   0.020
 JZB  plan-1  C3   0.020
 JZB  plan-1  O3   0.020
 JZB  plan-1  C4   0.020
 JZB  plan-1  O4   0.020
 JZB  plan-1  C5   0.020
 JZB  plan-1  C6   0.020
 JZB  plan-1  C7   0.020
 JZB  plan-1  C8   0.020
 JZB  plan-1  H1   0.020
 JZB  plan-2  N2   0.020
 JZB  plan-2  O6   0.020
 JZB  plan-2  C18  0.020
 JZB  plan-2  C19  0.020
 JZB  plan-2  C20  0.020
 JZB  plan-2  C24  0.020
 JZB  plan-3  N1   0.020
 JZB  plan-3  O5   0.020
 JZB  plan-3  C7   0.020
 JZB  plan-3  C9   0.020
 JZB  plan-3  C10  0.020
 JZB  plan-4  O1   0.020
 JZB  plan-4  O2   0.020
 JZB  plan-4  C5   0.020
 JZB  plan-4  C8   0.020
 JZB  plan-5  C9   0.020
 JZB  plan-5  C10  0.020
 JZB  plan-5  C16  0.020
 JZB  plan-5  C17  0.020
 JZB  plan-5  H10  0.020
 JZB  plan-5  H16  0.020
 JZB  plan-6  C12  0.020
 JZB  plan-6  C13  0.020
 JZB  plan-6  C14  0.020
 JZB  plan-6  C15  0.020
 JZB  plan-6  H13  0.020
 JZB  plan-6  H14  0.020

