# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 03:48:59 2020
#   Inital geometry file: a 131 line input string
#   Ligand name: (4R,8E)-18-chloro-4-[(R)-ethoxy-hydroxy-methyl]-15,17-dihydroxy-12-azabicyclo[12.4.0]octadeca-1(18),8,14,16-tetraene-3,13-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCO[C@@H](O)[C@H]1CCC/C=C/CCNC(=O)c2c(O)cc(O)c(Cl)c2CC1=O
#
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
 13I  13I  (4R,8E)-18-chloro-4-[(R)-ethoxy-hydroxy-methyl]-15,17-dihydroxy-12-azabicyclo[12.4.0]octadeca-1(18),8,14,16-tetraene-3,13-dione  ligand  54  28  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_13I
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
 13I  C01   C   CR6   0   0.409   0.5921  -3.6105   0.7182
 13I  C02   C   CR16  0  -0.498  -0.6096  -4.2914   0.6036
 13I  C03   C   CR6   0   0.457  -1.7241  -3.6520   0.0752
 13I  C04   C   CR6   0  -0.293  -1.6091  -2.3241  -0.3364
 13I  C05   C   CR6   0   0.299  -0.4038  -1.6366  -0.2432
 13I  C06   C   CR6   0  -0.256   0.7047  -2.2864   0.2875
 13I  C07   C   C     0   0.478   2.0054  -1.5684   0.5277
 13I  O08   O   O     0  -0.469   2.1569  -0.8508   1.5048
 13I  N09   N   NH1   0  -0.594   2.9550  -1.8082  -0.3849
 13I  C10   C   CH2   0  -0.301   4.3481  -1.4394  -0.2335
 13I  C11   C   CH2   0  -0.484   4.7747  -0.1699  -0.9697
 13I  C12   C   C1    0  -0.185   4.2877   1.1012  -0.3495
 13I  C13   C   C1    0  -0.225   3.7313   2.1143  -1.0074
 13I  C14   C   CH2   0  -0.488   3.2697   3.3981  -0.3884
 13I  C15   C   CH2   0  -0.436   1.7467   3.5496  -0.4741
 13I  C16   C   CH2   0  -0.448   1.0345   2.5036   0.3775
 13I  C17   C   CH1   0  -0.437  -0.4143   2.2274  -0.0554
 13I  C18   C   C     0   0.446  -0.7361   0.8008   0.3241
 13I  C19   C   CH2   0  -0.720  -0.2985  -0.2197  -0.7054
 13I  O20   O   O     0  -0.391  -1.2551   0.4864   1.3700
 13I  C21   C   CH1   0   0.313  -1.4209   3.2384   0.4915
 13I  O22   O   OH1   0  -0.667  -1.4255   3.3299   1.8820
 13I  O23   O   O2    0  -0.497  -2.6623   2.8668  -0.0288
 13I  C24   C   CH2   0  -0.154  -3.6860   3.8355   0.1091
 13I  C25   C   CH3   0  -0.687  -4.9371   3.3164  -0.5630
 13I  CL    CL  CL    0  -0.117  -3.0254  -1.5429  -0.9719
 13I  O27   O   OH1   0  -0.611  -2.8590  -4.3539  -0.0109
 13I  O28   O   OH1   0  -0.618   1.6896  -4.1781   1.2445
 13I  H02   H   HCR6  0   0.291  -0.6974  -5.3227   0.9259
 13I  H28   H   HOH1  0   0.483   1.4988  -5.0726   1.5499
 13I  H27   H   HOH1  0   0.471  -3.5637  -3.8336  -0.4184
 13I  H191  H   HCH2  0   0.303   0.7203   0.0203  -1.0222
 13I  H192  H   HCH2  0   0.318  -0.9066  -0.0461  -1.5983
 13I  H09   H   HNH1  0   0.407   2.7232  -2.4198  -1.1512
 13I  H101  H   HCH2  0   0.245   4.5696  -1.3416   0.8299
 13I  H102  H   HCH2  0   0.259   4.9388  -2.2770  -0.6050
 13I  H111  H   HCH2  0   0.241   5.8704  -0.1678  -0.9587
 13I  H112  H   HCH2  0   0.239   4.4782  -0.2282  -2.0201
 13I  H12   H   H     0   0.227   4.4480   1.1974   0.7227
 13I  H13   H   H     0   0.226   3.5621   2.0182  -2.0788
 13I  H141  H   HCH2  0   0.229   3.5907   3.4517   0.6563
 13I  H142  H   HCH2  0   0.240   3.7369   4.2427  -0.9032
 13I  H151  H   HCH2  0   0.237   1.4571   4.5588  -0.1719
 13I  H152  H   HCH2  0   0.223   1.4424   3.4424  -1.5204
 13I  H161  H   HCH2  0   0.265   1.6097   1.5767   0.3187
 13I  H162  H   HCH2  0   0.243   1.0556   2.7890   1.4313
 13I  H17   H   HCH1  0   0.274  -0.4522   2.2922  -1.1482
 13I  H21   H   HCH1  0   0.217  -1.1481   4.2424   0.1353
 13I  H22   H   HOH1  0   0.447  -1.5282   2.4375   2.2392
 13I  H241  H   HCH2  0   0.206  -3.8900   4.0430   1.1647
 13I  H242  H   HCH2  0   0.200  -3.3719   4.7821  -0.3505
 13I  H251  H   HCH3  0   0.230  -5.7358   4.0525  -0.4731
 13I  H252  H   HCH3  0   0.227  -4.7726   3.1271  -1.6241
 13I  H253  H   HCH3  0   0.228  -5.2810   2.3925  -0.0973

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
 13I  C01  C02   aromatic  1.386  0.020  1.386
 13I  C01  C06   single    1.397  0.020  1.397
 13I  C01  O28   single    1.343  0.020  1.343
 13I  C02  C03   aromatic  1.389  0.020  1.389
 13I  C03  C04   aromatic  1.395  0.020  1.395
 13I  C03  O27   single    1.337  0.020  1.337
 13I  C04  C05   single    1.391  0.020  1.391
 13I  C04  CL    single    1.738  0.020  1.738
 13I  C05  C06   aromatic  1.390  0.020  1.390
 13I  C05  C19   single    1.494  0.020  1.494
 13I  C06  C07   single    1.505  0.020  1.505
 13I  C07  O08   double    1.222  0.020  1.222
 13I  C07  N09   single    1.339  0.020  1.339
 13I  N09  C10   single    1.449  0.020  1.449
 13I  C10  C11   single    1.528  0.020  1.528
 13I  C11  C12   single    1.496  0.020  1.496
 13I  C12  C13   double    1.330  0.020  1.330
 13I  C13  C14   single    1.498  0.020  1.498
 13I  C14  C15   single    1.533  0.020  1.533
 13I  C15  C16   single    1.525  0.020  1.525
 13I  C16  C17   single    1.537  0.020  1.537
 13I  C17  C18   single    1.511  0.020  1.511
 13I  C17  C21   single    1.528  0.020  1.528
 13I  C18  C19   single    1.514  0.020  1.514
 13I  C18  O20   double    1.209  0.020  1.209
 13I  C21  O22   single    1.394  0.020  1.394
 13I  C21  O23   single    1.396  0.020  1.396
 13I  O23  C24   single    1.416  0.020  1.416
 13I  C24  C25   single    1.512  0.020  1.512
 13I  C02  H02   single    0.930  0.020  1.080
 13I  O28  H28   single    0.850  0.020  0.980
 13I  O27  H27   single    0.850  0.020  0.980
 13I  C19  H191  single    0.970  0.020  1.090
 13I  C19  H192  single    0.970  0.020  1.090
 13I  N09  H09   single    0.860  0.020  1.020
 13I  C10  H101  single    0.970  0.020  1.090
 13I  C10  H102  single    0.970  0.020  1.090
 13I  C11  H111  single    0.970  0.020  1.090
 13I  C11  H112  single    0.970  0.020  1.090
 13I  C12  H12   single    0.930  0.020  1.080
 13I  C13  H13   single    0.930  0.020  1.080
 13I  C14  H141  single    0.970  0.020  1.090
 13I  C14  H142  single    0.970  0.020  1.090
 13I  C15  H151  single    0.970  0.020  1.090
 13I  C15  H152  single    0.970  0.020  1.090
 13I  C16  H161  single    0.970  0.020  1.090
 13I  C16  H162  single    0.970  0.020  1.090
 13I  C17  H17   single    0.970  0.020  1.090
 13I  C21  H21   single    0.970  0.020  1.090
 13I  O22  H22   single    0.850  0.020  0.980
 13I  C24  H241  single    0.970  0.020  1.090
 13I  C24  H242  single    0.970  0.020  1.090
 13I  C25  H251  single    0.970  0.020  1.090
 13I  C25  H252  single    0.970  0.020  1.090
 13I  C25  H253  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
 13I  O28   C01  C06   117.10  3.000
 13I  O28   C01  C02   122.23  3.000
 13I  C06   C01  C02   120.67  3.000
 13I  H02   C02  C03   119.08  3.000
 13I  H02   C02  C01   120.86  3.000
 13I  C03   C02  C01   120.06  3.000
 13I  O27   C03  C04   123.41  3.000
 13I  O27   C03  C02   117.63  3.000
 13I  C04   C03  C02   118.96  3.000
 13I  CL    C04  C05   120.57  3.000
 13I  CL    C04  C03   117.94  3.000
 13I  C05   C04  C03   121.48  3.000
 13I  C19   C05  C06   120.34  3.000
 13I  C19   C05  C04   120.61  3.000
 13I  C06   C05  C04   119.05  3.000
 13I  C07   C06  C05   121.81  3.000
 13I  C07   C06  C01   118.21  3.000
 13I  C05   C06  C01   119.76  3.000
 13I  N09   C07  O08   124.23  3.000
 13I  N09   C07  C06   114.76  3.000
 13I  O08   C07  C06   121.00  3.000
 13I  H09   N09  C10   117.08  3.000
 13I  H09   N09  C07   117.65  3.000
 13I  C10   N09  C07   124.41  3.000
 13I  H102  C10  H101  106.92  3.000
 13I  H102  C10  C11   108.83  3.000
 13I  H101  C10  C11   109.79  3.000
 13I  H102  C10  N09   106.84  3.000
 13I  H101  C10  N09   108.66  3.000
 13I  C11   C10  N09   115.43  3.000
 13I  H112  C11  H111  106.32  3.000
 13I  H112  C11  C12   110.82  3.000
 13I  H111  C11  C12   108.65  3.000
 13I  H112  C11  C10   110.05  3.000
 13I  H111  C11  C10   106.01  3.000
 13I  C12   C11  C10   114.54  3.000
 13I  H12   C12  C13   118.78  3.000
 13I  H12   C12  C11   115.83  3.000
 13I  C13   C12  C11   125.34  3.000
 13I  H13   C13  C14   115.74  3.000
 13I  H13   C13  C12   118.97  3.000
 13I  C14   C13  C12   125.26  3.000
 13I  H142  C14  H141  106.62  3.000
 13I  H142  C14  C15   108.77  3.000
 13I  H141  C14  C15   109.88  3.000
 13I  H142  C14  C13   109.61  3.000
 13I  H141  C14  C13   110.25  3.000
 13I  C15   C14  C13   111.58  3.000
 13I  H152  C15  H151  106.32  3.000
 13I  H152  C15  C16   109.67  3.000
 13I  H151  C15  C16   110.81  3.000
 13I  H152  C15  C14   108.66  3.000
 13I  H151  C15  C14   109.83  3.000
 13I  C16   C15  C14   111.40  3.000
 13I  H162  C16  H161  105.28  3.000
 13I  H162  C16  C17   109.69  3.000
 13I  H161  C16  C17   109.19  3.000
 13I  H162  C16  C15   110.52  3.000
 13I  H161  C16  C15   107.82  3.000
 13I  C17   C16  C15   113.96  3.000
 13I  H17   C17  C21   107.17  3.000
 13I  H17   C17  C18   107.40  3.000
 13I  C21   C17  C18   113.24  3.000
 13I  H17   C17  C16   107.63  3.000
 13I  C21   C17  C16   113.66  3.000
 13I  C18   C17  C16   107.44  3.000
 13I  O20   C18  C19   122.47  3.000
 13I  O20   C18  C17   123.66  3.000
 13I  C19   C18  C17   113.83  3.000
 13I  H192  C19  H191  104.26  3.000
 13I  H192  C19  C18   106.70  3.000
 13I  H191  C19  C18   108.56  3.000
 13I  H192  C19  C05   111.33  3.000
 13I  H191  C19  C05   111.31  3.000
 13I  C18   C19  C05   114.11  3.000
 13I  H21   C21  O23   110.05  3.000
 13I  H21   C21  O22   105.32  3.000
 13I  O23   C21  O22   112.73  3.000
 13I  H21   C21  C17   108.95  3.000
 13I  O23   C21  C17   106.04  3.000
 13I  O22   C21  C17   113.75  3.000
 13I  H22   O22  C21   107.97  3.000
 13I  C24   O23  C21   115.11  3.000
 13I  H242  C24  H241  107.07  3.000
 13I  H242  C24  C25   110.28  3.000
 13I  H241  C24  C25   109.84  3.000
 13I  H242  C24  O23   110.00  3.000
 13I  H241  C24  O23   110.99  3.000
 13I  C25   C24  O23   108.66  3.000
 13I  H253  C25  H252  108.43  3.000
 13I  H253  C25  H251  107.82  3.000
 13I  H252  C25  H251  107.94  3.000
 13I  H253  C25  C24   111.22  3.000
 13I  H252  C25  C24   111.55  3.000
 13I  H251  C25  C24   109.74  3.000
 13I  H27   O27  C03   111.32  3.000
 13I  H28   O28  C01   110.76  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
 13I  CONST_01  C04   C03  C02  C01     0.00   0.0  0
 13I  CONST_02  C04   C05  C06  C01     0.00   0.0  0
 13I  CONST_03  C05   C06  C01  C02     0.00   0.0  0
 13I  CONST_04  C05   C04  C03  C02     0.00   0.0  0
 13I  CONST_05  C06   C01  C02  C03     0.00   0.0  0
 13I  CONST_06  C06   C05  C04  C03     0.00   0.0  0
 13I  CONST_07  C10   N09  C07  C06   180.00   0.0  0
 13I  CONST_08  O27   C03  C02  C01   180.00   0.0  0
 13I  CONST_09  CL    C04  C03  C02   180.00   0.0  0
 13I  CONST_10  O28   C01  C02  C03   180.00   0.0  0
 13I  CONST_11  O27   C03  C04  C05   180.00   0.0  0
 13I  CONST_12  O28   C01  C06  C05   180.00   0.0  0
 13I  CONST_13  CL    C04  C05  C06   180.00   0.0  0
 13I  CONST_14  O28   C01  C06  C07     0.00   0.0  0
 13I  CONST_15  CL    C04  C05  C19     0.00   0.0  0
 13I  CONST_16  C10   N09  C07  O08     0.00   0.0  0
 13I  CONST_17  H02   C02  C03  C04   180.00   0.0  0
 13I  CONST_18  H09   N09  C07  C06     0.00   0.0  0
 13I  Var_01    C14   C13  C12  C11  -178.68   0.0  0
 13I  Var_02    N09   C07  C06  C01    82.79  30.0  1
 13I  Var_03    C18   C19  C05  C04    84.17  30.0  1
 13I  Var_04    C17   C18  C19  C05   170.34  30.0  1
 13I  Var_05    C11   C10  N09  C07  -100.43  30.0  1
 13I  Var_06    C12   C11  C10  N09    73.62  30.0  1
 13I  Var_07    C13   C12  C11  C10  -133.85  30.0  1
 13I  Var_08    C15   C14  C13  C12  -113.79  30.0  1
 13I  Var_09    C16   C15  C14  C13    66.35  30.0  1
 13I  Var_10    C17   C16  C15  C14  -157.53  30.0  1
 13I  Var_11    H12   C12  C13  C14    -1.24   0.0  0
 13I  Var_12    C25   C24  O23  C21   177.05  30.0  3
 13I  Var_13    H251  C25  C24  O23  -179.61  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
 13I  chir_01  C17  C16  C18  C21  negativ
 13I  chir_02  C21  O23  O22  C17  negativ

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
 13I  plan-1  C01  0.020
 13I  plan-1  C02  0.020
 13I  plan-1  C03  0.020
 13I  plan-1  C04  0.020
 13I  plan-1  C05  0.020
 13I  plan-1  C06  0.020
 13I  plan-1  C07  0.020
 13I  plan-1  C19  0.020
 13I  plan-1  CL   0.020
 13I  plan-1  O27  0.020
 13I  plan-1  O28  0.020
 13I  plan-1  H02  0.020
 13I  plan-2  C06  0.020
 13I  plan-2  C07  0.020
 13I  plan-2  O08  0.020
 13I  plan-2  N09  0.020
 13I  plan-2  C10  0.020
 13I  plan-2  H09  0.020
 13I  plan-3  C17  0.020
 13I  plan-3  C18  0.020
 13I  plan-3  C19  0.020
 13I  plan-3  O20  0.020
 13I  plan-4  C11  0.020
 13I  plan-4  C12  0.020
 13I  plan-4  C13  0.020
 13I  plan-4  C14  0.020
 13I  plan-4  H12  0.020
 13I  plan-4  H13  0.020

