# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 14 13:29:17 2020
#   Inital geometry file: a 128 line input string
#   Ligand name: 6-{(1E)-3-[3-(3-methyl-1-benzofuran-2-yl)azetidin-1-yl]-3-oxoprop-1-en-1-yl}-1,8-naphthyridin-2(1H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1c(oc2ccccc12)[C@H]3CN(C3)C(=O)\C=C\c4cnc5NC(=O)C=Cc5c4
#
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
 AE6  AE6  6-{(1E)-3-[3-(3-methyl-1-benzofuran-2-yl)azetidin-1-yl]-3-oxoprop-1-en-1-yl}-1,8-naphthyridin-2(1H)-one  ligand  48  29  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_AE6
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
 AE6  O3   O  O     0  -0.475  -8.9337   2.1964   0.6197
 AE6  C21  C  CR6   0   0.540  -8.0084   1.3997   0.5983
 AE6  N3   N  NR16  0  -0.714  -6.7202   1.8177   0.3497
 AE6  C18  C  CR66  0   0.503  -5.6220   1.0138   0.3032
 AE6  N2   N  N     0  -0.419  -4.4524   1.5933   0.0486
 AE6  C17  C  CR16  0  -0.087  -3.3838   0.8267   0.0000
 AE6  C22  C  CR16  0  -0.442  -8.1492  -0.0318   0.8243
 AE6  C23  C  CR16  0  -0.144  -7.0902  -0.8619   0.7876
 AE6  C19  C  CR66  0  -0.035  -5.7736  -0.3629   0.5242
 AE6  C20  C  CR16  0  -0.246  -4.6257  -1.1459   0.4698
 AE6  C16  C  CR6   0   0.061  -3.3949  -0.5638   0.2003
 AE6  C15  C  C1    0  -0.232  -2.1983  -1.3913   0.1402
 AE6  C14  C  C1    0  -0.425  -0.9692  -0.9995  -0.2091
 AE6  C13  C  C     0   0.546   0.1529  -1.9634  -0.2177
 AE6  O2   O  O     0  -0.505   0.0503  -3.1283   0.1588
 AE6  N1   N  N     0  -0.467   1.3128  -1.4764  -0.6686
 AE6  C11  C  C     0  -0.237   2.5880  -2.1449  -0.8296
 AE6  C12  C  C     0  -0.252   1.7429  -0.2087  -1.2386
 AE6  C10  C  C     0  -0.486   3.1298  -0.8550  -1.5059
 AE6  C7   C  CR5   0   0.399   4.3059  -0.2074  -0.8978
 AE6  O1   O  O     0  -0.476   4.2318   0.0388   0.4454
 AE6  C4   C  CR56  0   0.350   5.3919   0.6298   0.8029
 AE6  C3   C  CR16  0  -0.343   5.7446   1.0512   2.0722
 AE6  C2   C  CR16  0  -0.276   6.9961   1.6367   2.2003
 AE6  C8   C  CR5   0  -0.035   5.4843   0.2084  -1.4193
 AE6  C9   C  CH3   0  -0.751   5.9613   0.1255  -2.8266
 AE6  C5   C  CR56  0   0.064   6.2191   0.7654  -0.3118
 AE6  C6   C  CR16  0  -0.361   7.4736   1.3556  -0.1626
 AE6  C1   C  CR16  0  -0.260   7.8482   1.7874   1.0994
 AE6  H1   H  HNR6  0   0.418  -6.5724   2.8070   0.1906
 AE6  H2   H  HCR6  0   0.276  -2.4516   1.3403  -0.2067
 AE6  H3   H  HCR6  0   0.287  -9.1459  -0.4011   1.0217
 AE6  H4   H  HCR6  0   0.287  -7.2206  -1.9236   0.9559
 AE6  H5   H  HCR6  0   0.282  -4.7013  -2.2145   0.6342
 AE6  H6   H  H     0   0.266  -2.3460  -2.4342   0.4033
 AE6  H7   H  H     0   0.279  -0.7631   0.0253  -0.4947
 AE6  H8   H  H     0   0.253   3.0647  -2.4189   0.1135
 AE6  H9   H  H     0   0.259   2.5577  -3.0205  -1.4796
 AE6  H10  H  H     0   0.265   1.2046   0.0891  -2.1391
 AE6  H11  H  H     0   0.259   1.7422   0.6218  -0.5304
 AE6  H12  H  H     0   0.296   3.3124  -1.0000  -2.5691
 AE6  H13  H  HCR6  0   0.269   5.0832   0.9318   2.9202
 AE6  H14  H  HCR6  0   0.260   7.3206   1.9820   3.1730
 AE6  H15  H  HCH3  0   0.247   6.2274   1.1122  -3.2091
 AE6  H16  H  HCH3  0   0.248   6.8520  -0.5006  -2.9022
 AE6  H17  H  HCH3  0   0.248   5.2059  -0.2923  -3.4903
 AE6  H18  H  HCR6  0   0.253   8.1392   1.4731  -1.0085
 AE6  H19  H  HCR6  0   0.256   8.8158   2.2508   1.2416

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
 AE6  C1   C6   aromatic  1.385  0.020  1.385
 AE6  C1   C2   aromatic  1.400  0.020  1.400
 AE6  C6   C5   aromatic  1.395  0.020  1.395
 AE6  C9   C8   single    1.488  0.020  1.488
 AE6  C2   C3   aromatic  1.388  0.020  1.388
 AE6  C5   C8   aromatic  1.441  0.020  1.441
 AE6  C5   C4   aromatic  1.395  0.020  1.395
 AE6  C8   C7   aromatic  1.354  0.020  1.354
 AE6  C3   C4   aromatic  1.383  0.020  1.383
 AE6  C4   O1   aromatic  1.350  0.020  1.350
 AE6  C7   O1   aromatic  1.368  0.020  1.368
 AE6  C7   C10  single    1.474  0.020  1.474
 AE6  C10  C12  single    1.553  0.020  1.553
 AE6  C10  C11  single    1.554  0.020  1.554
 AE6  C12  N1   single    1.455  0.020  1.455
 AE6  C11  N1   single    1.449  0.020  1.449
 AE6  N1   C13  single    1.336  0.020  1.336
 AE6  C13  C14  single    1.479  0.020  1.479
 AE6  C13  O2   double    1.229  0.020  1.229
 AE6  C14  C15  double    1.336  0.020  1.336
 AE6  C23  C22  double    1.346  0.020  1.346
 AE6  C23  C19  single    1.432  0.020  1.432
 AE6  C22  C21  single    1.456  0.020  1.456
 AE6  C20  C19  aromatic  1.391  0.020  1.391
 AE6  C20  C16  aromatic  1.388  0.020  1.388
 AE6  C19  C18  aromatic  1.402  0.020  1.402
 AE6  C15  C16  single    1.456  0.020  1.456
 AE6  C16  C17  aromatic  1.405  0.020  1.405
 AE6  C21  O3   double    1.221  0.020  1.221
 AE6  C21  N3   single    1.377  0.020  1.377
 AE6  C18  N3   single    1.362  0.020  1.362
 AE6  C18  N2   aromatic  1.330  0.020  1.330
 AE6  C17  N2   aromatic  1.316  0.020  1.316
 AE6  N3   H1   single    0.860  0.020  1.020
 AE6  C17  H2   single    0.930  0.020  1.080
 AE6  C22  H3   single    0.930  0.020  1.080
 AE6  C23  H4   single    0.930  0.020  1.080
 AE6  C20  H5   single    0.930  0.020  1.080
 AE6  C15  H6   single    0.930  0.020  1.080
 AE6  C14  H7   single    0.930  0.020  1.080
 AE6  C11  H8   single    0.970  0.020  1.090
 AE6  C11  H9   single    0.970  0.020  1.090
 AE6  C12  H10  single    0.970  0.020  1.090
 AE6  C12  H11  single    0.970  0.020  1.090
 AE6  C10  H12  single    0.970  0.020  1.090
 AE6  C3   H13  single    0.930  0.020  1.080
 AE6  C2   H14  single    0.930  0.020  1.080
 AE6  C9   H15  single    0.970  0.020  1.090
 AE6  C9   H16  single    0.970  0.020  1.090
 AE6  C9   H17  single    0.970  0.020  1.090
 AE6  C6   H18  single    0.930  0.020  1.080
 AE6  C1   H19  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
 AE6  C22  C21  N3   114.65  3.000
 AE6  N3   C21  O3   120.93  3.000
 AE6  C22  C21  O3   124.43  3.000
 AE6  H1   N3   C18  116.98  3.000
 AE6  H1   N3   C21  117.47  3.000
 AE6  C18  N3   C21  125.55  3.000
 AE6  C19  C18  N2   123.57  3.000
 AE6  N2   C18  N3   117.29  3.000
 AE6  C19  C18  N3   119.14  3.000
 AE6  C17  N2   C18  117.86  3.000
 AE6  H2   C17  C16  120.19  3.000
 AE6  H2   C17  N2   115.42  3.000
 AE6  C16  C17  N2   124.40  3.000
 AE6  H3   C22  C23  121.31  3.000
 AE6  H3   C22  C21  116.96  3.000
 AE6  C23  C22  C21  121.73  3.000
 AE6  H4   C23  C19  118.74  3.000
 AE6  H4   C23  C22  120.37  3.000
 AE6  C19  C23  C22  120.88  3.000
 AE6  C20  C19  C23  124.73  3.000
 AE6  C20  C19  C18  117.21  3.000
 AE6  C23  C19  C18  118.05  3.000
 AE6  H5   C20  C16  120.32  3.000
 AE6  H5   C20  C19  119.44  3.000
 AE6  C16  C20  C19  120.23  3.000
 AE6  C15  C16  C20  119.90  3.000
 AE6  C15  C16  C17  123.37  3.000
 AE6  C20  C16  C17  116.73  3.000
 AE6  H6   C15  C14  118.03  3.000
 AE6  H6   C15  C16  115.09  3.000
 AE6  C14  C15  C16  126.87  3.000
 AE6  H7   C14  C13  118.06  3.000
 AE6  H7   C14  C15  121.40  3.000
 AE6  C13  C14  C15  120.54  3.000
 AE6  N1   C13  O2   121.43  3.000
 AE6  O2   C13  C14  123.55  3.000
 AE6  N1   C13  C14  115.02  3.000
 AE6  C12  N1   C11   95.64  3.000
 AE6  C11  N1   C13  129.29  3.000
 AE6  C12  N1   C13  134.93  3.000
 AE6  H9   C11  H8   108.99  3.000
 AE6  H9   C11  C10  114.62  3.000
 AE6  H8   C11  C10  115.60  3.000
 AE6  H9   C11  N1   114.34  3.000
 AE6  H8   C11  N1   113.84  3.000
 AE6  C10  C11  N1    88.41  3.000
 AE6  H11  C12  H10  109.12  3.000
 AE6  H11  C12  C10  115.40  3.000
 AE6  H10  C12  C10  114.34  3.000
 AE6  H11  C12  N1   114.12  3.000
 AE6  H10  C12  N1   114.55  3.000
 AE6  C10  C12  N1    88.22  3.000
 AE6  H12  C10  C7   109.13  3.000
 AE6  H12  C10  C12  111.92  3.000
 AE6  C7   C10  C12  117.30  3.000
 AE6  H12  C10  C11  111.90  3.000
 AE6  C12  C10  C11   87.66  3.000
 AE6  C7   C10  C11  117.60  3.000
 AE6  C8   C7   O1   111.72  3.000
 AE6  O1   C7   C10  116.18  3.000
 AE6  C8   C7   C10  132.10  3.000
 AE6  C4   O1   C7   107.00  3.000
 AE6  C5   C4   C3   123.55  3.000
 AE6  C3   C4   O1   126.55  3.000
 AE6  C5   C4   O1   109.90  3.000
 AE6  H13  C3   C2   121.70  3.000
 AE6  H13  C3   C4   121.98  3.000
 AE6  C2   C3   C4   116.32  3.000
 AE6  H14  C2   C1   119.34  3.000
 AE6  H14  C2   C3   119.22  3.000
 AE6  C1   C2   C3   121.44  3.000
 AE6  C5   C8   C9   125.79  3.000
 AE6  C5   C8   C7   105.45  3.000
 AE6  C9   C8   C7   128.76  3.000
 AE6  H17  C9   H16  107.68  3.000
 AE6  H17  C9   H15  107.61  3.000
 AE6  H16  C9   H15  107.18  3.000
 AE6  H17  C9   C8   112.05  3.000
 AE6  H16  C9   C8   111.04  3.000
 AE6  H15  C9   C8   111.05  3.000
 AE6  C6   C5   C8   134.80  3.000
 AE6  C8   C5   C4   105.92  3.000
 AE6  C6   C5   C4   119.28  3.000
 AE6  H18  C6   C1   120.77  3.000
 AE6  H18  C6   C5   121.02  3.000
 AE6  C1   C6   C5   118.21  3.000
 AE6  H19  C1   C6   119.66  3.000
 AE6  H19  C1   C2   119.13  3.000
 AE6  C6   C1   C2   121.20  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
 AE6  CONST_01  C16  C20  C19  C18    0.00   0.0  0
 AE6  CONST_02  C16  C17  N2   C18    0.00   0.0  0
 AE6  CONST_03  C20  C19  C18  N2     0.00   0.0  0
 AE6  CONST_04  C20  C16  C17  N2     0.00   0.0  0
 AE6  CONST_05  C19  C20  C16  C17    0.00   0.0  0
 AE6  CONST_06  C19  C18  N2   C17    0.00   0.0  0
 AE6  CONST_07  C6   C5   C8   C7   180.00   0.0  0
 AE6  CONST_08  C4   C5   C8   C7     0.00   0.0  0
 AE6  CONST_09  C5   C4   O1   C7     0.00   0.0  0
 AE6  CONST_10  C3   C4   O1   C7   180.00   0.0  0
 AE6  CONST_11  C6   C5   C4   O1   180.00   0.0  0
 AE6  CONST_12  C8   C5   C4   O1     0.00   0.0  0
 AE6  CONST_13  C2   C3   C4   O1   180.00   0.0  0
 AE6  CONST_14  C5   C8   C7   O1     0.00   0.0  0
 AE6  CONST_15  C1   C6   C5   C4     0.00   0.0  0
 AE6  CONST_16  C1   C2   C3   C4     0.00   0.0  0
 AE6  CONST_17  C8   C7   O1   C4     0.00   0.0  0
 AE6  CONST_18  C6   C1   C2   C3     0.00   0.0  0
 AE6  CONST_19  C6   C5   C4   C3     0.00   0.0  0
 AE6  CONST_20  C8   C5   C4   C3   180.00   0.0  0
 AE6  CONST_21  C5   C6   C1   C2     0.00   0.0  0
 AE6  CONST_22  C5   C4   C3   C2     0.00   0.0  0
 AE6  CONST_23  C1   C6   C5   C8   180.00   0.0  0
 AE6  CONST_24  C5   C8   C7   C10  180.00   0.0  0
 AE6  CONST_25  C4   O1   C7   C10  180.00   0.0  0
 AE6  CONST_26  C22  C21  N3   C18    0.00   0.0  0
 AE6  CONST_27  C15  C16  C17  N2   180.00   0.0  0
 AE6  CONST_28  C15  C16  C20  C19  180.00   0.0  0
 AE6  CONST_29  C9   C8   C7   C10    0.00   0.0  0
 AE6  CONST_30  C9   C8   C7   O1   180.00   0.0  0
 AE6  CONST_31  C9   C8   C5   C4   180.00   0.0  0
 AE6  CONST_32  C6   C5   C8   C9     0.00   0.0  0
 AE6  CONST_33  C18  N3   C21  O3   180.00   0.0  0
 AE6  CONST_34  H5   C20  C19  C18  180.00   0.0  0
 AE6  CONST_35  H2   C17  N2   C18  180.00   0.0  0
 AE6  CONST_36  H13  C3   C4   O1     0.00   0.0  0
 AE6  CONST_37  H18  C6   C5   C4   180.00   0.0  0
 AE6  CONST_38  H14  C2   C3   C4   180.00   0.0  0
 AE6  CONST_39  H19  C1   C2   C3   180.00   0.0  0
 AE6  CONST_40  H1   N3   C21  C22  180.00   0.0  0
 AE6  CONST_41  C12  N1   C13  C14    0.00   0.0  0
 AE6  CONST_42  C11  N1   C13  C14  180.00   0.0  0
 AE6  CONST_43  C12  N1   C13  O2   180.00   0.0  0
 AE6  CONST_44  C11  N1   C13  O2     0.00   0.0  0
 AE6  Var_01    C10  C12  N1   C11    2.16  30.0  1
 AE6  Var_02    C14  C15  C16  C17   -5.79  30.0  2
 AE6  Var_03    H15  C9   C8   C7   123.35  30.0  2
 AE6  Var_04    C13  C14  C15  C16  179.82   0.0  2
 AE6  Var_05    N1   C13  C14  C15  175.77  30.0  2

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
 AE6  chir_01  C10  C7  C12  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
 AE6  plan-1  C10  0.020
 AE6  plan-1  C7   0.020
 AE6  plan-1  O1   0.020
 AE6  plan-1  C4   0.020
 AE6  plan-1  C3   0.020
 AE6  plan-1  C2   0.020
 AE6  plan-1  C8   0.020
 AE6  plan-1  C9   0.020
 AE6  plan-1  C5   0.020
 AE6  plan-1  C6   0.020
 AE6  plan-1  C1   0.020
 AE6  plan-1  H13  0.020
 AE6  plan-1  H14  0.020
 AE6  plan-1  H18  0.020
 AE6  plan-1  H19  0.020
 AE6  plan-2  O3   0.020
 AE6  plan-2  C21  0.020
 AE6  plan-2  N3   0.020
 AE6  plan-2  C18  0.020
 AE6  plan-2  N2   0.020
 AE6  plan-2  C17  0.020
 AE6  plan-2  C22  0.020
 AE6  plan-2  C23  0.020
 AE6  plan-2  C19  0.020
 AE6  plan-2  C20  0.020
 AE6  plan-2  C16  0.020
 AE6  plan-2  C15  0.020
 AE6  plan-2  H1   0.020
 AE6  plan-2  H2   0.020
 AE6  plan-2  H3   0.020
 AE6  plan-2  H4   0.020
 AE6  plan-2  H5   0.020
 AE6  plan-3  C14  0.020
 AE6  plan-3  C13  0.020
 AE6  plan-3  O2   0.020
 AE6  plan-3  N1   0.020
 AE6  plan-3  C11  0.020
 AE6  plan-3  C12  0.020
 AE6  plan-4  C16  0.020
 AE6  plan-4  C15  0.020
 AE6  plan-4  C14  0.020
 AE6  plan-4  C13  0.020
 AE6  plan-4  H6   0.020
 AE6  plan-4  H7   0.020

