# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 07:29:11 2021
#   Inital geometry file: a 134 line input string
#   Ligand name: ~{N}-[(10~{S})-3,4,5-trimethoxy-16-methylidene-14-oxatetracyclo[9.7.0.0^{2,7}.0^{13,17}]octadeca-1(18),2,4,6,11,13(17)-hexaen-10-yl]ethanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc2CC[C@H](NC(C)=O)c3cc4OCC(=C)c4cc3c2c(OC)c1OC
#
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
 N3Z  N3Z  ~{N}-[(10~{S})-3,4,5-trimethoxy-16-methylidene-14-oxatetracyclo[9.7.0.0^{2,7}.0^{13,17}]octadeca-1(18),2,4,6,11,13(17)-hexaen-10-yl]ethanamide  ligand  54  29  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_N3Z
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
 N3Z  C19  C  CH2   0  -0.421   6.3125  54.5514  84.7889
 N3Z  C17  C  CH3   0  -0.418   9.3484  56.1188  89.1073
 N3Z  C22  C  CH3   0  -0.780   9.2431  50.8164  85.4584
 N3Z  C15  C  CH3   0  -0.409   8.5468  60.3054  88.7418
 N3Z  C8   C  CR56  0   0.029   5.3793  54.1086  89.7286
 N3Z  C9   C  CR6   0  -0.085   6.9088  56.4778  87.2406
 N3Z  C12  C  CR6   0   0.325   7.7473  58.8504  85.9951
 N3Z  C13  C  CH3   0  -0.439   7.7567  60.3887  84.1949
 N3Z  C14  C  CR6   0   0.196   8.2241  58.5202  87.2706
 N3Z  C10  C  CR6   0   0.113   6.4767  56.7929  85.9501
 N3Z  C11  C  CR16  0  -0.481   6.8934  57.9708  85.3382
 N3Z  C6   C  CR6   0   0.046   6.4437  55.2361  87.8973
 N3Z  C5   C  CR6   0   0.110   6.5866  54.0039  87.2340
 N3Z  C2   C  CH2   0  -0.199   4.4946  52.3215  90.9753
 N3Z  C3   C  CR56  0   0.395   5.5243  52.9032  89.0522
 N3Z  C4   C  CR16  0  -0.417   6.1216  52.8261  87.8078
 N3Z  C7   C  CR16  0  -0.374   5.8385  55.2797  89.1511
 N3Z  C1   C  CR5   0   0.069   4.7116  53.8193  90.9909
 N3Z  O1   O  O2    0  -0.461   8.1873  60.0141  85.4885
 N3Z  O2   O  O2    0  -0.481   9.1244  59.3278  87.8878
 N3Z  O4   O  O     0  -0.489   9.5943  52.7978  86.7545
 N3Z  C21  C  C     0   0.520   8.8905  52.1949  85.9570
 N3Z  C20  C  CH1   0  -0.136   7.2491  54.0034  85.8723
 N3Z  C18  C  CH2   0  -0.556   5.5819  55.8291  85.2205
 N3Z  C16  C  CR6   0   0.258   7.7973  57.3471  87.8816
 N3Z  C    C  C2    0  -0.641   4.3550  54.6545  91.9639
 N3Z  O    O  O     0  -0.492   5.0278  51.8508  89.7284
 N3Z  H1   H  HCH2  0   0.241   5.5656  53.7966  84.5265
 N3Z  H2   H  HCH2  0   0.251   6.9074  54.7440  83.8930
 N3Z  H3   H  HCH3  0   0.239   9.6130  55.9194  90.1438
 N3Z  H4   H  HCH3  0   0.229   9.0604  55.1777  88.6303
 N3Z  H5   H  HCH3  0   0.224  10.2226  56.5214  88.5892
 N3Z  H6   H  HCH3  0   0.265  10.2805  50.8017  85.1272
 N3Z  H7   H  HCH3  0   0.268   9.1534  50.1042  86.2794
 N3Z  H8   H  HCH3  0   0.250   8.6111  50.4747  84.6407
 N3Z  H9   H  HCH3  0   0.237   9.3658  60.8609  89.1953
 N3Z  H10  H  HCH3  0   0.221   7.9143  61.0041  88.1887
 N3Z  H11  H  HCH3  0   0.221   7.9519  59.8478  89.5358
 N3Z  H12  H  HCH3  0   0.262   8.2141  61.3521  83.9844
 N3Z  H13  H  HCH3  0   0.229   8.0789  59.6725  83.4346
 N3Z  H14  H  HCH3  0   0.229   6.6701  60.4947  84.1410
 N3Z  H15  H  HCR6  0   0.275   6.5310  58.1901  84.3424
 N3Z  H16  H  HCH2  0   0.261   3.4374  52.0537  91.0291
 N3Z  H17  H  HCH2  0   0.261   5.0172  51.8194  91.7920
 N3Z  H18  H  HCR6  0   0.250   6.2330  51.8747  87.3042
 N3Z  H19  H  HCR6  0   0.245   5.7121  56.2273  89.6594
 N3Z  H20  H  HNH1  0   0.401   7.1853  52.1539  84.8454
 N3Z  H21  H  HCH1  0   0.267   8.1111  54.6735  85.9305
 N3Z  H22  H  HCH2  0   0.264   5.1585  56.3052  84.3356
 N3Z  H23  H  HCH2  0   0.255   4.7387  55.5587  85.8610
 N3Z  H24  H  H     0   0.250   3.8568  54.3039  92.8582
 N3Z  H25  H  H     0   0.245   4.5493  55.7168  91.8961
 N3Z  O3   O  O2    0  -0.480   8.2780  57.0545  89.1185
 N3Z  N    N  NH1   0  -0.642   7.7436  52.7100  85.4726

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
 N3Z  C13  O1   single    1.414  0.020  1.414
 N3Z  C19  C18  single    1.534  0.020  1.534
 N3Z  C19  C20  single    1.533  0.020  1.533
 N3Z  C18  C10  single    1.504  0.020  1.504
 N3Z  C22  C21  single    1.508  0.020  1.508
 N3Z  C11  C10  aromatic  1.391  0.020  1.391
 N3Z  C11  C12  aromatic  1.391  0.020  1.391
 N3Z  O1   C12  single    1.343  0.020  1.343
 N3Z  N    C20  single    1.441  0.020  1.441
 N3Z  N    C21  single    1.347  0.020  1.347
 N3Z  C20  C5   single    1.514  0.020  1.514
 N3Z  C21  O4   double    1.223  0.020  1.223
 N3Z  C10  C9   aromatic  1.397  0.020  1.397
 N3Z  C12  C14  aromatic  1.401  0.020  1.401
 N3Z  C9   C6   aromatic  1.480  0.020  1.480
 N3Z  C9   C16  aromatic  1.399  0.020  1.399
 N3Z  C5   C4   aromatic  1.390  0.020  1.390
 N3Z  C5   C6   aromatic  1.407  0.020  1.407
 N3Z  C14  C16  aromatic  1.390  0.020  1.390
 N3Z  C14  O2   single    1.358  0.020  1.358
 N3Z  C4   C3   aromatic  1.382  0.020  1.382
 N3Z  C6   C7   aromatic  1.393  0.020  1.393
 N3Z  C16  O3   single    1.359  0.020  1.359
 N3Z  O2   C15  single    1.421  0.020  1.421
 N3Z  C3   O    single    1.346  0.020  1.346
 N3Z  C3   C8   aromatic  1.390  0.020  1.390
 N3Z  C7   C8   aromatic  1.384  0.020  1.384
 N3Z  O3   C17  single    1.422  0.020  1.422
 N3Z  O    C2   single    1.436  0.020  1.436
 N3Z  C8   C1   single    1.457  0.020  1.457
 N3Z  C2   C1   single    1.514  0.020  1.514
 N3Z  C1   C    double    1.331  0.020  1.331
 N3Z  C19  H1   single    0.970  0.020  1.090
 N3Z  C19  H2   single    0.970  0.020  1.090
 N3Z  C17  H3   single    0.970  0.020  1.090
 N3Z  C17  H4   single    0.970  0.020  1.090
 N3Z  C17  H5   single    0.970  0.020  1.090
 N3Z  C22  H6   single    0.970  0.020  1.090
 N3Z  C22  H7   single    0.970  0.020  1.090
 N3Z  C22  H8   single    0.970  0.020  1.090
 N3Z  C15  H9   single    0.970  0.020  1.090
 N3Z  C15  H10  single    0.970  0.020  1.090
 N3Z  C15  H11  single    0.970  0.020  1.090
 N3Z  C13  H12  single    0.970  0.020  1.090
 N3Z  C13  H13  single    0.970  0.020  1.090
 N3Z  C13  H14  single    0.970  0.020  1.090
 N3Z  C11  H15  single    0.930  0.020  1.080
 N3Z  C2   H16  single    0.970  0.020  1.090
 N3Z  C2   H17  single    0.970  0.020  1.090
 N3Z  C4   H18  single    0.930  0.020  1.080
 N3Z  C7   H19  single    0.930  0.020  1.080
 N3Z  N    H20  single    0.860  0.020  1.020
 N3Z  C20  H21  single    0.970  0.020  1.090
 N3Z  C18  H22  single    0.970  0.020  1.090
 N3Z  C18  H23  single    0.970  0.020  1.090
 N3Z  C    H24  single    0.930  0.020  1.080
 N3Z  C    H25  single    0.930  0.020  1.080

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
 N3Z  H2   C19  H1   107.26  3.000
 N3Z  H2   C19  C18  110.07  3.000
 N3Z  H1   C19  C18  108.48  3.000
 N3Z  H2   C19  C20  108.05  3.000
 N3Z  H1   C19  C20  109.88  3.000
 N3Z  C18  C19  C20  112.95  3.000
 N3Z  H5   C17  H4   108.71  3.000
 N3Z  H5   C17  H3   108.94  3.000
 N3Z  H4   C17  H3   108.77  3.000
 N3Z  H5   C17  O3   111.31  3.000
 N3Z  H4   C17  O3   111.81  3.000
 N3Z  H3   C17  O3   107.23  3.000
 N3Z  H8   C22  H7   108.23  3.000
 N3Z  H8   C22  H6   108.68  3.000
 N3Z  H7   C22  H6   107.37  3.000
 N3Z  H8   C22  C21  113.56  3.000
 N3Z  H7   C22  C21  109.20  3.000
 N3Z  H6   C22  C21  109.61  3.000
 N3Z  H11  C15  H10  108.69  3.000
 N3Z  H11  C15  H9   108.70  3.000
 N3Z  H10  C15  H9   108.67  3.000
 N3Z  H11  C15  O2   111.71  3.000
 N3Z  H10  C15  O2   111.78  3.000
 N3Z  H9   C15  O2   107.20  3.000
 N3Z  C1   C8   C7   132.96  3.000
 N3Z  C1   C8   C3   107.30  3.000
 N3Z  C7   C8   C3   119.75  3.000
 N3Z  C16  C9   C6   121.19  3.000
 N3Z  C16  C9   C10  118.67  3.000
 N3Z  C6   C9   C10  120.14  3.000
 N3Z  O1   C12  C11  124.81  3.000
 N3Z  O1   C12  C14  115.84  3.000
 N3Z  C11  C12  C14  119.33  3.000
 N3Z  H14  C13  H13  108.81  3.000
 N3Z  H14  C13  H12  108.83  3.000
 N3Z  H13  C13  H12  108.78  3.000
 N3Z  H14  C13  O1   111.93  3.000
 N3Z  H13  C13  O1   111.90  3.000
 N3Z  H12  C13  O1   106.48  3.000
 N3Z  C16  C14  O2   120.39  3.000
 N3Z  O2   C14  C12  119.95  3.000
 N3Z  C16  C14  C12  119.64  3.000
 N3Z  C18  C10  C11  120.49  3.000
 N3Z  C11  C10  C9   120.31  3.000
 N3Z  C18  C10  C9   119.19  3.000
 N3Z  H15  C11  C10  118.43  3.000
 N3Z  H15  C11  C12  120.80  3.000
 N3Z  C10  C11  C12  120.77  3.000
 N3Z  C7   C6   C5   119.74  3.000
 N3Z  C7   C6   C9   120.65  3.000
 N3Z  C5   C6   C9   119.59  3.000
 N3Z  C20  C5   C4   121.15  3.000
 N3Z  C4   C5   C6   120.89  3.000
 N3Z  C20  C5   C6   117.96  3.000
 N3Z  H17  C2   H16  108.29  3.000
 N3Z  H17  C2   O    108.73  3.000
 N3Z  H16  C2   O    108.78  3.000
 N3Z  H17  C2   C1   112.26  3.000
 N3Z  H16  C2   C1   112.39  3.000
 N3Z  O    C2   C1   106.27  3.000
 N3Z  O    C3   C4   124.61  3.000
 N3Z  O    C3   C8   113.28  3.000
 N3Z  C4   C3   C8   122.11  3.000
 N3Z  H18  C4   C3   120.82  3.000
 N3Z  H18  C4   C5   121.22  3.000
 N3Z  C3   C4   C5   117.96  3.000
 N3Z  H19  C7   C6   120.05  3.000
 N3Z  H19  C7   C8   120.39  3.000
 N3Z  C6   C7   C8   119.55  3.000
 N3Z  C    C1   C2   126.17  3.000
 N3Z  C    C1   C8   129.17  3.000
 N3Z  C2   C1   C8   104.67  3.000
 N3Z  C13  O1   C12  118.34  3.000
 N3Z  C14  O2   C15  114.39  3.000
 N3Z  N    C21  O4   122.41  3.000
 N3Z  O4   C21  C22  122.14  3.000
 N3Z  N    C21  C22  115.45  3.000
 N3Z  H21  C20  N    107.11  3.000
 N3Z  H21  C20  C5   107.27  3.000
 N3Z  N    C20  C5   113.56  3.000
 N3Z  H21  C20  C19  107.47  3.000
 N3Z  C5   C20  C19  111.59  3.000
 N3Z  N    C20  C19  109.54  3.000
 N3Z  H23  C18  H22  106.50  3.000
 N3Z  H23  C18  C10  109.47  3.000
 N3Z  H22  C18  C10  110.18  3.000
 N3Z  H23  C18  C19  109.05  3.000
 N3Z  H22  C18  C19  108.68  3.000
 N3Z  C10  C18  C19  112.77  3.000
 N3Z  C14  C16  O3   118.24  3.000
 N3Z  O3   C16  C9   120.54  3.000
 N3Z  C14  C16  C9   121.22  3.000
 N3Z  H25  C    H24  116.91  3.000
 N3Z  H25  C    C1   121.48  3.000
 N3Z  H24  C    C1   121.61  3.000
 N3Z  C3   O    C2   108.48  3.000
 N3Z  C16  O3   C17  113.63  3.000
 N3Z  H20  N    C20  118.55  3.000
 N3Z  H20  N    C21  118.99  3.000
 N3Z  C20  N    C21  122.38  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
 N3Z  CONST_01  C5   C4   C3   C8      0.00   0.0  0
 N3Z  CONST_02  C12  C14  C16  C9      0.00   0.0  0
 N3Z  CONST_03  C10  C11  C12  C14     0.00   0.0  0
 N3Z  CONST_04  C16  C14  C12  C11     0.00   0.0  0
 N3Z  CONST_05  C3   C8   C7   C6      0.00   0.0  0
 N3Z  CONST_06  C7   C8   C3   C4      0.00   0.0  0
 N3Z  CONST_07  O2   C14  C16  C9    180.00   0.0  0
 N3Z  CONST_08  C12  C14  C16  O3    180.00   0.0  0
 N3Z  CONST_09  O1   C12  C11  C10   180.00   0.0  0
 N3Z  CONST_10  O2   C14  C12  C11   180.00   0.0  0
 N3Z  CONST_11  C16  C14  C12  O1    180.00   0.0  0
 N3Z  CONST_12  H18  C4   C3   C8    180.00   0.0  0
 N3Z  CONST_13  H15  C11  C12  C14   180.00   0.0  0
 N3Z  CONST_14  H19  C7   C8   C3    180.00   0.0  0
 N3Z  CONST_15  C20  N    C21  C22   180.00   0.0  0
 N3Z  CONST_16  C20  N    C21  O4      0.00   0.0  0
 N3Z  CONST_17  H20  N    C21  C22     0.00   0.0  0
 N3Z  Var_01    O    C2   C1   C8     -0.48  30.0  1
 N3Z  Var_02    C4   C3   O    C2    179.86  30.0  1
 N3Z  Var_03    C3   C8   C1   C2      0.33  30.0  1
 N3Z  Var_04    C1   C2   O    C3      0.45  30.0  1
 N3Z  Var_05    C9   C16  O3   C17    79.92  30.0  2
 N3Z  Var_06    C12  C14  O2   C15    92.95  30.0  3
 N3Z  Var_07    C11  C12  O1   C13     0.19  30.0  2
 N3Z  Var_08    H24  C    C1   C8    179.81   0.0  2
 N3Z  Var_09    H12  C13  O1   C12   179.46  30.0  3
 N3Z  Var_10    H9   C15  O2   C14   178.23  30.0  3
 N3Z  Var_11    H3   C17  O3   C16  -176.90  30.0  3
 N3Z  Var_12    H6   C22  C21  O4    -49.14  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
 N3Z  chir_01  C20  C19  N  C5  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
 N3Z  plan-1  C22  0.020
 N3Z  plan-1  O4   0.020
 N3Z  plan-1  C21  0.020
 N3Z  plan-1  C20  0.020
 N3Z  plan-1  H20  0.020
 N3Z  plan-1  N    0.020
 N3Z  plan-2  C9   0.020
 N3Z  plan-2  C12  0.020
 N3Z  plan-2  C14  0.020
 N3Z  plan-2  C10  0.020
 N3Z  plan-2  C11  0.020
 N3Z  plan-2  C6   0.020
 N3Z  plan-2  O1   0.020
 N3Z  plan-2  O2   0.020
 N3Z  plan-2  C18  0.020
 N3Z  plan-2  C16  0.020
 N3Z  plan-2  H15  0.020
 N3Z  plan-2  O3   0.020
 N3Z  plan-3  C8   0.020
 N3Z  plan-3  C9   0.020
 N3Z  plan-3  C6   0.020
 N3Z  plan-3  C5   0.020
 N3Z  plan-3  C3   0.020
 N3Z  plan-3  C4   0.020
 N3Z  plan-3  C7   0.020
 N3Z  plan-3  C1   0.020
 N3Z  plan-3  C20  0.020
 N3Z  plan-3  O    0.020
 N3Z  plan-3  H18  0.020
 N3Z  plan-3  H19  0.020
 N3Z  plan-4  C8   0.020
 N3Z  plan-4  C2   0.020
 N3Z  plan-4  C1   0.020
 N3Z  plan-4  C    0.020
 N3Z  plan-4  H24  0.020
 N3Z  plan-4  H25  0.020

