# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 04:41:26 2020
#   Inital geometry file: a 164 line input string
#   Ligand name: methyl [(1E,5R)-5-{3-[(2E,4E)-2,5-dimethylnona-2,4-dienoyl]-4-hydroxy-2-oxo-2H-pyran-6-yl}hex-1-en-1-yl]carbamate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC(/C)=C/C=C(C)/C(=O)C1=C(O)C=C(OC1=O)[C@H](C)CC/C=C/NC(=O)OC
#
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
 4C4  4C4  'methyl [(1E,5R)-5-{3-[(2E,4E)-2,5-dimethylnona-2,4-dienoyl]-4-hydroxy-2-oxo-2H-pyran-6-yl}hex-1-en-1-yl]carbamate'  ligand  64  31  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_4C4
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
 4C4  C1   C  CR6   0  -0.463    1.2894   2.0655  -0.0028
 4C4  C2   C  C     0   0.369    2.6768   1.9994  -0.5441
 4C4  C3   C  C     0  -0.026    3.6924   1.2398   0.2186
 4C4  O4   O  O     0  -0.506   -8.2695  -2.7638   0.6395
 4C4  O5   O  O     0  -0.453   -0.6775   0.9444   0.7542
 4C4  C7   C  C     0   0.128    6.9814  -0.3273  -0.5562
 4C4  C8   C  CH3   0  -0.733    7.2518  -0.0758  -2.0059
 4C4  C9   C  CH2   0  -0.492    8.0326  -1.1236   0.1630
 4C4  C10  C  CH2   0  -0.411    7.9462  -2.6225  -0.1446
 4C4  C11  C  CH2   0  -0.420    9.0254  -3.4286   0.5671
 4C4  C12  C  CH3   0  -0.662    8.9363  -4.9182   0.2656
 4C4  C13  C  CR6   0   0.515    0.6238   3.2598   0.1454
 4C4  C14  C  CR16  0  -0.551   -0.7153   3.2757   0.6315
 4C4  C15  C  CR6   0   0.493   -1.3153   2.1053   0.9239
 4C4  C16  C  CH1   0  -0.350   -2.7027   1.9599   1.4557
 4C4  C20  C  C1    0  -0.297   -5.9095   0.5390  -0.2039
 4C4  C21  C  C1    0  -0.002   -6.6591  -0.5170   0.1042
 4C4  C22  C  C     0   0.752   -8.1918  -2.2904  -0.4730
 4C4  O3   O  O2    0  -0.478   -8.8374  -2.7581  -1.5392
 4C4  C23  C  CH3   0  -0.417   -9.6681  -3.8985  -1.3390
 4C4  N    N  NH1   0  -0.689   -7.4387  -1.2141  -0.8103
 4C4  C18  C  CH2   0  -0.411   -3.5797   1.1714   0.4702
 4C4  C17  C  CH3   0  -0.662   -2.6814   1.3318   2.8523
 4C4  C    C  CR6   0   0.552    0.6130   0.8423   0.2889
 4C4  O    O  O     0  -0.438    1.0447  -0.2785   0.1546
 4C4  O2   O  OH1   0  -0.574    1.2479   4.3896  -0.1304
 4C4  O1   O  O     0  -0.406    2.9403   2.5799  -1.5824
 4C4  C4   C  CH3   0  -0.746    3.4850   0.9582   1.6802
 4C4  C5   C  C1    0  -0.243    4.7945   0.8434  -0.4546
 4C4  C6   C  C1    0  -0.299    5.8866   0.0927   0.1096
 4C4  H8   H  HCH3  0   0.252    8.1162   0.5848  -2.1115
 4C4  H7   H  HCH3  0   0.249    7.5128  -1.0055  -2.5157
 4C4  H6   H  HCH3  0   0.251    6.4209   0.3735  -2.5439
 4C4  H10  H  HCH2  0   0.235    9.0249  -0.7591  -0.1250
 4C4  H9   H  HCH2  0   0.239    7.9401  -0.9766   1.2419
 4C4  H12  H  HCH2  0   0.222    6.9591  -2.9904   0.1516
 4C4  H11  H  HCH2  0   0.219    8.0272  -2.7883  -1.2230
 4C4  H14  H  HCH2  0   0.215   10.0101  -3.0535   0.2723
 4C4  H13  H  HCH2  0   0.215    8.9477  -3.2651   1.6462
 4C4  H17  H  HCH3  0   0.217    7.9707  -5.3270   0.5694
 4C4  H16  H  HCH3  0   0.217    9.0543  -5.1108  -0.8023
 4C4  H15  H  HCH3  0   0.227    9.7120  -5.4787   0.7887
 4C4  H19  H  HCR6  0   0.306   -1.2463   4.2059   0.7819
 4C4  H    H  HCH1  0   0.270   -3.1045   2.9741   1.5386
 4C4  H26  H  HCH2  0   0.234   -5.3577   2.3216   0.8262
 4C4  H25  H  HCH2  0   0.241   -5.2679   0.8653   1.7969
 4C4  H27  H  H     0   0.247   -5.8782   0.8989  -1.2292
 4C4  H28  H  H     0   0.272   -6.7042  -0.8983   1.1162
 4C4  H30  H  HCH3  0   0.237   -9.0916  -4.7614  -1.0059
 4C4  H31  H  HCH3  0   0.237  -10.4620  -3.6963  -0.6204
 4C4  H32  H  HCH3  0   0.251  -10.1097  -4.1161  -2.3069
 4C4  H23  H  HCH2  0   0.243   -3.4203   1.5540  -0.5425
 4C4  H24  H  HCH2  0   0.236   -3.2741   0.1219   0.4610
 4C4  H20  H  HCH3  0   0.234   -2.3461   0.2948   2.8177
 4C4  H22  H  HCH3  0   0.246   -2.0256   1.8833   3.5263
 4C4  H21  H  HCH3  0   0.248   -3.6797   1.3440   3.2868
 4C4  H18  H  HOH1  0   0.496    0.6845   5.1543   0.0434
 4C4  H2   H  HCH3  0   0.250    3.2352  -0.0866   1.8685
 4C4  H1   H  HCH3  0   0.251    4.3863   1.1842   2.2503
 4C4  H3   H  HCH3  0   0.247    2.6870   1.5675   2.1013
 4C4  H4   H  H     0   0.253    4.8538   1.0975  -1.5064
 4C4  H5   H  H     0   0.243    5.8239  -0.1565   1.1640
 4C4  H29  H  HNH1  0   0.412   -7.4457  -0.9047  -1.7710
 4C4  C19  C  CH2   0  -0.493   -5.0704   1.2645   0.7992

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
 4C4  C12  C11  single  1.522  0.020  1.522
 4C4  C11  C10  single  1.524  0.020  1.524
 4C4  C10  C9   single  1.533  0.020  1.533
 4C4  C9   C7   single  1.502  0.020  1.502
 4C4  C7   C6   double  1.348  0.020  1.348
 4C4  C7   C8   single  1.496  0.020  1.496
 4C4  C6   C5   single  1.440  0.020  1.440
 4C4  C4   C3   single  1.503  0.020  1.503
 4C4  C5   C3   double  1.351  0.020  1.351
 4C4  C3   C2   single  1.480  0.020  1.480
 4C4  O4   C22  double  1.212  0.020  1.212
 4C4  O2   C13  single  1.320  0.020  1.320
 4C4  C2   O1   double  1.218  0.020  1.218
 4C4  C2   C1   single  1.491  0.020  1.491
 4C4  C22  O3   single  1.331  0.020  1.331
 4C4  C22  N    single  1.356  0.020  1.356
 4C4  O3   C23  single  1.425  0.020  1.425
 4C4  N    C21  single  1.389  0.020  1.389
 4C4  C13  C1   double  1.375  0.020  1.375
 4C4  C13  C14  single  1.425  0.020  1.425
 4C4  C1   C    single  1.428  0.020  1.428
 4C4  C21  C20  double  1.331  0.020  1.331
 4C4  C14  C15  double  1.347  0.020  1.347
 4C4  C    O    double  1.209  0.020  1.209
 4C4  C    O5   single  1.376  0.020  1.376
 4C4  C20  C19  single  1.496  0.020  1.496
 4C4  C19  C18  single  1.529  0.020  1.529
 4C4  C18  C16  single  1.537  0.020  1.537
 4C4  C15  O5   single  1.335  0.020  1.335
 4C4  C15  C16  single  1.493  0.020  1.493
 4C4  C16  C17  single  1.532  0.020  1.532
 4C4  C8   H8   single  0.970  0.020  1.090
 4C4  C8   H7   single  0.970  0.020  1.090
 4C4  C8   H6   single  0.970  0.020  1.090
 4C4  C9   H10  single  0.970  0.020  1.090
 4C4  C9   H9   single  0.970  0.020  1.090
 4C4  C10  H12  single  0.970  0.020  1.090
 4C4  C10  H11  single  0.970  0.020  1.090
 4C4  C11  H14  single  0.970  0.020  1.090
 4C4  C11  H13  single  0.970  0.020  1.090
 4C4  C12  H17  single  0.970  0.020  1.090
 4C4  C12  H16  single  0.970  0.020  1.090
 4C4  C12  H15  single  0.970  0.020  1.090
 4C4  C14  H19  single  0.930  0.020  1.080
 4C4  C16  H    single  0.970  0.020  1.090
 4C4  C19  H26  single  0.970  0.020  1.090
 4C4  C19  H25  single  0.970  0.020  1.090
 4C4  C20  H27  single  0.930  0.020  1.080
 4C4  C21  H28  single  0.930  0.020  1.080
 4C4  C23  H30  single  0.970  0.020  1.090
 4C4  C23  H31  single  0.970  0.020  1.090
 4C4  C23  H32  single  0.970  0.020  1.090
 4C4  C18  H23  single  0.970  0.020  1.090
 4C4  C18  H24  single  0.970  0.020  1.090
 4C4  C17  H20  single  0.970  0.020  1.090
 4C4  C17  H22  single  0.970  0.020  1.090
 4C4  C17  H21  single  0.970  0.020  1.090
 4C4  O2   H18  single  0.850  0.020  0.980
 4C4  C4   H2   single  0.970  0.020  1.090
 4C4  C4   H1   single  0.970  0.020  1.090
 4C4  C4   H3   single  0.970  0.020  1.090
 4C4  C5   H4   single  0.930  0.020  1.080
 4C4  C6   H5   single  0.930  0.020  1.080
 4C4  N    H29  single  0.860  0.020  1.020

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
 4C4  C    C1   C13  119.51  3.000
 4C4  C    C1   C2   118.49  3.000
 4C4  C13  C1   C2   121.88  3.000
 4C4  O1   C2   C3   122.37  3.000
 4C4  O1   C2   C1   119.31  3.000
 4C4  C3   C2   C1   118.31  3.000
 4C4  C5   C3   C4   122.84  3.000
 4C4  C5   C3   C2   116.97  3.000
 4C4  C4   C3   C2   120.18  3.000
 4C4  C    O5   C15  123.75  3.000
 4C4  C6   C7   C9   119.80  3.000
 4C4  C6   C7   C8   124.95  3.000
 4C4  C9   C7   C8   115.25  3.000
 4C4  H6   C8   H7   107.67  3.000
 4C4  H6   C8   H8   107.86  3.000
 4C4  H7   C8   H8   106.28  3.000
 4C4  H6   C8   C7   114.27  3.000
 4C4  H7   C8   C7   110.64  3.000
 4C4  H8   C8   C7   109.77  3.000
 4C4  H9   C9   H10  106.94  3.000
 4C4  H9   C9   C10  108.96  3.000
 4C4  H10  C9   C10  108.89  3.000
 4C4  H9   C9   C7   110.01  3.000
 4C4  H10  C9   C7   109.37  3.000
 4C4  C10  C9   C7   112.52  3.000
 4C4  H11  C10  H12  106.41  3.000
 4C4  H11  C10  C11  109.14  3.000
 4C4  H12  C10  C11  109.55  3.000
 4C4  H11  C10  C9   109.99  3.000
 4C4  H12  C10  C9   108.99  3.000
 4C4  C11  C10  C9   112.57  3.000
 4C4  H13  C11  H14  106.16  3.000
 4C4  H13  C11  C12  109.72  3.000
 4C4  H14  C11  C12  109.56  3.000
 4C4  H13  C11  C10  109.35  3.000
 4C4  H14  C11  C10  109.28  3.000
 4C4  C12  C11  C10  112.57  3.000
 4C4  H15  C12  H16  107.56  3.000
 4C4  H15  C12  H17  107.65  3.000
 4C4  H16  C12  H17  107.56  3.000
 4C4  H15  C12  C11  111.48  3.000
 4C4  H16  C12  C11  111.10  3.000
 4C4  H17  C12  C11  111.29  3.000
 4C4  O2   C13  C14  120.41  3.000
 4C4  C14  C13  C1   120.09  3.000
 4C4  O2   C13  C1   119.47  3.000
 4C4  H19  C14  C15  119.89  3.000
 4C4  H19  C14  C13  121.23  3.000
 4C4  C15  C14  C13  118.87  3.000
 4C4  C16  C15  C14  125.15  3.000
 4C4  C16  C15  O5   113.86  3.000
 4C4  C14  C15  O5   120.99  3.000
 4C4  H    C16  C17  108.43  3.000
 4C4  H    C16  C18  108.34  3.000
 4C4  C17  C16  C18  112.47  3.000
 4C4  H    C16  C15  106.15  3.000
 4C4  C17  C16  C15  110.60  3.000
 4C4  C18  C16  C15  110.60  3.000
 4C4  H27  C20  C21  119.80  3.000
 4C4  H27  C20  C19  117.12  3.000
 4C4  C21  C20  C19  123.07  3.000
 4C4  H28  C21  N    114.54  3.000
 4C4  H28  C21  C20  121.28  3.000
 4C4  N    C21  C20  124.18  3.000
 4C4  N    C22  O3   110.42  3.000
 4C4  N    C22  O4   125.03  3.000
 4C4  O3   C22  O4   124.54  3.000
 4C4  C23  O3   C22  116.83  3.000
 4C4  H32  C23  H31  109.19  3.000
 4C4  H32  C23  H30  109.20  3.000
 4C4  H31  C23  H30  109.32  3.000
 4C4  H32  C23  O3   105.79  3.000
 4C4  H31  C23  O3   111.64  3.000
 4C4  H30  C23  O3   111.60  3.000
 4C4  H29  N    C22  118.43  3.000
 4C4  H29  N    C21  118.47  3.000
 4C4  C22  N    C21  123.10  3.000
 4C4  H24  C18  H23  106.69  3.000
 4C4  H24  C18  C19  109.44  3.000
 4C4  H23  C18  C19  108.65  3.000
 4C4  H24  C18  C16  109.78  3.000
 4C4  H23  C18  C16  109.32  3.000
 4C4  C19  C18  C16  112.77  3.000
 4C4  H21  C17  H22  107.41  3.000
 4C4  H21  C17  H20  107.77  3.000
 4C4  H22  C17  H20  108.41  3.000
 4C4  H21  C17  C16  110.28  3.000
 4C4  H22  C17  C16  111.39  3.000
 4C4  H20  C17  C16  111.43  3.000
 4C4  O    C    O5   116.20  3.000
 4C4  O5   C    C1   116.74  3.000
 4C4  O    C    C1   127.05  3.000
 4C4  H18  O2   C13  111.37  3.000
 4C4  H3   C4   H1   106.72  3.000
 4C4  H3   C4   H2   107.55  3.000
 4C4  H1   C4   H2   107.33  3.000
 4C4  H3   C4   C3   111.87  3.000
 4C4  H1   C4   C3   110.83  3.000
 4C4  H2   C4   C3   112.27  3.000
 4C4  H4   C5   C6   117.45  3.000
 4C4  H4   C5   C3   117.36  3.000
 4C4  C6   C5   C3   125.19  3.000
 4C4  H5   C6   C5   117.16  3.000
 4C4  H5   C6   C7   117.07  3.000
 4C4  C5   C6   C7   125.77  3.000
 4C4  H25  C19  H26  106.42  3.000
 4C4  H25  C19  C18  110.51  3.000
 4C4  H26  C19  C18  108.64  3.000
 4C4  H25  C19  C20  109.50  3.000
 4C4  H26  C19  C20  109.72  3.000
 4C4  C18  C19  C20  111.90  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
 4C4  Var_01  C15  C14  C13  C1     -0.83  30.0  1
 4C4  Var_02  C13  C1   C    O5     -2.21  30.0  1
 4C4  Var_03  C13  C14  C15  O5     -0.53  30.0  1
 4C4  Var_04  C    C1   C13  C14     2.20  30.0  1
 4C4  Var_05  C4   C3   C2   C1    -20.74  30.0  2
 4C4  Var_06  C6   C5   C3   C2   -179.72   0.0  2
 4C4  Var_07  C5   C6   C7   C8      0.33   0.0  2
 4C4  Var_08  N    C21  C20  C19  -179.48   0.0  2
 4C4  Var_09  C7   C6   C5   C3    178.86  30.0  2
 4C4  Var_10  C21  N    C22  O4     -0.23  30.0  2
 4C4  Var_11  C11  C10  C9   C7    179.11  30.0  1
 4C4  Var_12  C10  C9   C7   C8    -77.33  30.0  2
 4C4  Var_13  C12  C11  C10  C9    179.79  30.0  2
 4C4  Var_14  C20  C19  C18  C16   177.59  30.0  2
 4C4  Var_15  C22  N    C21  C20   179.81  30.0  1
 4C4  Var_16  C18  C19  C20  C21   116.49  30.0  3
 4C4  Var_17  N    C22  O3   C23   179.70  30.0  2
 4C4  Var_18  H2   C4   C3   C2    106.93  30.0  3
 4C4  Var_19  H8   C8   C7   C9    -67.11  30.0  3
 4C4  Var_20  H17  C12  C11  C10   -59.42  30.0  3
 4C4  Var_21  H30  C23  O3   C22   -62.02  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
 4C4  chir_01  C16  C18  C15  C17  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
 4C4  plan-1  C1   0.020
 4C4  plan-1  C2   0.020
 4C4  plan-1  C3   0.020
 4C4  plan-1  O1   0.020
 4C4  plan-2  C1   0.020
 4C4  plan-2  O5   0.020
 4C4  plan-2  C    0.020
 4C4  plan-2  O    0.020
 4C4  plan-3  C7   0.020
 4C4  plan-3  C8   0.020
 4C4  plan-3  C9   0.020
 4C4  plan-3  C5   0.020
 4C4  plan-3  C6   0.020
 4C4  plan-3  H5   0.020
 4C4  plan-4  C2   0.020
 4C4  plan-4  C3   0.020
 4C4  plan-4  C4   0.020
 4C4  plan-4  C5   0.020
 4C4  plan-4  C6   0.020
 4C4  plan-4  H4   0.020
 4C4  plan-5  O4   0.020
 4C4  plan-5  C22  0.020
 4C4  plan-5  O3   0.020
 4C4  plan-5  N    0.020
 4C4  plan-6  C20  0.020
 4C4  plan-6  C21  0.020
 4C4  plan-6  N    0.020
 4C4  plan-6  H27  0.020
 4C4  plan-6  H28  0.020
 4C4  plan-6  C19  0.020

