# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 10:41:30 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: (5E)-14-chloro-15,17-dihydroxy-2-methyl-2,3,4,7,8,9,10,11-octahydro-1H-2-benzazacyclopentadecine-1,12(13H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN1CC/C=C/CCCCCC(=O)Cc2c(Cl)c(O)cc(O)c2C1=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
 BO5  BO5  (5E)-14-chloro-15,17-dihydroxy-2-methyl-2,3,4,7,8,9,10,11-octahydro-1H-2-benzazacyclopentadecine-1,12(13H)-dione  ligand  49  25  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_BO5
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
 BO5  O3    O   O     0  -0.483   0.3463   1.7414   1.9931
 BO5  C18   C   C     0   0.505   0.1029   1.6704   0.7948
 BO5  N     N   NT    0  -0.420   0.9300   2.1365  -0.1614
 BO5  C     C   CH3   0  -0.529   0.6865   1.9563  -1.5755
 BO5  C17   C   CR6   0  -0.285  -1.2175   1.1052   0.3479
 BO5  C16   C   CR6   0   0.426  -2.2014   2.0218  -0.0428
 BO5  O2    O   OH1   0  -0.619  -1.8414   3.3149  -0.0953
 BO5  C15   C   CR16  0  -0.496  -3.4854   1.6032  -0.3468
 BO5  C14   C   CR6   0   0.454  -3.8135   0.2555  -0.2655
 BO5  O1    O   OH1   0  -0.610  -5.0658  -0.0977  -0.5733
 BO5  C13   C   CR6   0  -0.273  -2.8322  -0.6515   0.1287
 BO5  CL    CL  CL    0  -0.116  -3.2617  -2.3355   0.1991
 BO5  C12   C   CR6   0   0.276  -1.5421  -0.2419   0.4568
 BO5  C11   C   CH2   0  -0.720  -0.5360  -1.2713   0.8613
 BO5  C10   C   C     0   0.407  -0.0293  -2.1021  -0.2990
 BO5  O     O   O     0  -0.387  -0.2334  -1.7886  -1.4481
 BO5  C9    C   CH2   0  -0.552   0.7850  -3.3202   0.0646
 BO5  C8    C   CH2   0  -0.422   2.2131  -3.2294  -0.4740
 BO5  C7    C   CH2   0  -0.427   2.9527  -2.0107   0.0600
 BO5  C6    C   CH2   0  -0.423   4.4123  -1.9552  -0.3630
 BO5  C5    C   CH2   0  -0.489   5.1208  -0.7012   0.1549
 BO5  C4    C   C1    0  -0.213   4.5376   0.5554  -0.4093
 BO5  C3    C   C1    0  -0.184   3.9191   1.4992   0.2935
 BO5  C2    C   CH2   0  -0.514   3.3709   2.7640  -0.2841
 BO5  C1    C   CH2   0  -0.301   1.9589   3.1062   0.1818
 BO5  HC1   H   HCH3  0   0.266  -0.0288   1.1582  -1.7493
 BO5  HC2   H   HCH3  0   0.237   0.3157   2.8732  -2.0391
 BO5  HC3   H   HCH3  0   0.252   1.6130   1.6731  -2.0743
 BO5  H11C  H   HCH2  0   0.249   1.6709   4.0668  -0.2587
 BO5  H12C  H   HCH2  0   0.257   1.9572   3.2354   1.2614
 BO5  H2    H   HOH1  0   0.482  -2.5771   3.8637  -0.3907
 BO5  H15   H   HCR6  0   0.290  -4.2485   2.3158  -0.6393
 BO5  H1    H   HOH1  0   0.471  -5.1912  -1.0519  -0.4902
 BO5  H111  H   HCH2  0   0.312   0.3422  -0.8235   1.3356
 BO5  H112  H   HCH2  0   0.306  -0.9433  -1.9409   1.6228
 BO5  H91C  H   HCH2  0   0.250   0.8051  -3.4540   1.1481
 BO5  H92C  H   HCH2  0   0.279   0.2804  -4.1955  -0.3549
 BO5  H81C  H   HCH2  0   0.236   2.7430  -4.1420  -0.1901
 BO5  H82C  H   HCH2  0   0.226   2.1957  -3.2059  -1.5665
 BO5  H71C  H   HCH2  0   0.228   2.4552  -1.0958  -0.2790
 BO5  H72C  H   HCH2  0   0.212   2.8927  -1.9983   1.1545
 BO5  H61C  H   HCH2  0   0.225   4.9372  -2.8417   0.0049
 BO5  H62C  H   HCH2  0   0.214   4.4814  -1.9887  -1.4556
 BO5  H51C  H   HCH2  0   0.226   5.0706  -0.6794   1.2475
 BO5  H52C  H   HCH2  0   0.237   6.1815  -0.7610  -0.1082
 BO5  H4    H   H     0   0.225   4.6247   0.6781  -1.4882
 BO5  H3    H   H     0   0.225   3.8216   1.3782   1.3709
 BO5  H21C  H   HCH2  0   0.251   3.9940   3.6080   0.0317
 BO5  H22C  H   HCH2  0   0.239   3.4370   2.7412  -1.3748

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
 BO5  O3   C18   double    1.225  0.020  1.225
 BO5  C18  N     single    1.347  0.020  1.347
 BO5  C18  C17   single    1.504  0.020  1.504
 BO5  N    C     single    1.446  0.020  1.446
 BO5  N    C1    single    1.455  0.020  1.455
 BO5  C17  C16   single    1.400  0.020  1.400
 BO5  C17  C12   aromatic  1.390  0.020  1.390
 BO5  C16  O2    single    1.343  0.020  1.343
 BO5  C16  C15   aromatic  1.384  0.020  1.384
 BO5  C15  C14   aromatic  1.389  0.020  1.389
 BO5  C14  O1    single    1.337  0.020  1.337
 BO5  C14  C13   aromatic  1.393  0.020  1.393
 BO5  C13  CL    single    1.739  0.020  1.739
 BO5  C13  C12   single    1.393  0.020  1.393
 BO5  C12  C11   single    1.495  0.020  1.495
 BO5  C11  C10   single    1.514  0.020  1.514
 BO5  C10  O     double    1.209  0.020  1.209
 BO5  C10  C9    single    1.510  0.020  1.510
 BO5  C9   C8    single    1.529  0.020  1.529
 BO5  C8   C7    single    1.522  0.020  1.522
 BO5  C7   C6    single    1.521  0.020  1.521
 BO5  C6   C5    single    1.531  0.020  1.531
 BO5  C5   C4    single    1.496  0.020  1.496
 BO5  C4   C3    double    1.329  0.020  1.329
 BO5  C3   C2    single    1.495  0.020  1.495
 BO5  C2   C1    single    1.526  0.020  1.526
 BO5  C    HC1   single    0.970  0.020  1.090
 BO5  C    HC2   single    0.970  0.020  1.090
 BO5  C    HC3   single    0.970  0.020  1.090
 BO5  C1   H11C  single    0.970  0.020  1.090
 BO5  C1   H12C  single    0.970  0.020  1.090
 BO5  O2   H2    single    0.850  0.020  0.980
 BO5  C15  H15   single    0.930  0.020  1.080
 BO5  O1   H1    single    0.850  0.020  0.980
 BO5  C11  H111  single    0.970  0.020  1.090
 BO5  C11  H112  single    0.970  0.020  1.090
 BO5  C9   H91C  single    0.970  0.020  1.090
 BO5  C9   H92C  single    0.970  0.020  1.090
 BO5  C8   H81C  single    0.970  0.020  1.090
 BO5  C8   H82C  single    0.970  0.020  1.090
 BO5  C7   H71C  single    0.970  0.020  1.090
 BO5  C7   H72C  single    0.970  0.020  1.090
 BO5  C6   H61C  single    0.970  0.020  1.090
 BO5  C6   H62C  single    0.970  0.020  1.090
 BO5  C5   H51C  single    0.970  0.020  1.090
 BO5  C5   H52C  single    0.970  0.020  1.090
 BO5  C4   H4    single    0.930  0.020  1.080
 BO5  C3   H3    single    0.930  0.020  1.080
 BO5  C2   H21C  single    0.970  0.020  1.090
 BO5  C2   H22C  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
 BO5  C17   C18  N     117.26  3.000
 BO5  C17   C18  O3    119.14  3.000
 BO5  N     C18  O3    123.52  3.000
 BO5  C1    N    C     115.64  3.000
 BO5  C1    N    C18   119.82  3.000
 BO5  C     N    C18   123.19  3.000
 BO5  HC3   C    HC2   108.21  3.000
 BO5  HC3   C    HC1   107.21  3.000
 BO5  HC2   C    HC1   108.99  3.000
 BO5  HC3   C    N     109.68  3.000
 BO5  HC2   C    N     111.57  3.000
 BO5  HC1   C    N     111.04  3.000
 BO5  C12   C17  C16   119.48  3.000
 BO5  C12   C17  C18   123.09  3.000
 BO5  C16   C17  C18   116.98  3.000
 BO5  C15   C16  O2    122.07  3.000
 BO5  C15   C16  C17   121.00  3.000
 BO5  O2    C16  C17   116.92  3.000
 BO5  H2    O2   C16   110.82  3.000
 BO5  H15   C15  C14   119.15  3.000
 BO5  H15   C15  C16   120.89  3.000
 BO5  C14   C15  C16   119.96  3.000
 BO5  C13   C14  O1    123.56  3.000
 BO5  C13   C14  C15   118.80  3.000
 BO5  O1    C14  C15   117.64  3.000
 BO5  H1    O1   C14   111.27  3.000
 BO5  C12   C13  CL    120.26  3.000
 BO5  C12   C13  C14   121.84  3.000
 BO5  CL    C13  C14   117.89  3.000
 BO5  C11   C12  C13   118.98  3.000
 BO5  C11   C12  C17   122.09  3.000
 BO5  C13   C12  C17   118.88  3.000
 BO5  H112  C11  H111  104.35  3.000
 BO5  H112  C11  C10   108.81  3.000
 BO5  H111  C11  C10   106.75  3.000
 BO5  H112  C11  C12   111.08  3.000
 BO5  H111  C11  C12   112.07  3.000
 BO5  C10   C11  C12   113.30  3.000
 BO5  C9    C10  O     121.96  3.000
 BO5  C9    C10  C11   116.02  3.000
 BO5  O     C10  C11   121.99  3.000
 BO5  H92C  C9   H91C  106.92  3.000
 BO5  H92C  C9   C8    110.08  3.000
 BO5  H91C  C9   C8    109.85  3.000
 BO5  H92C  C9   C10   107.73  3.000
 BO5  H91C  C9   C10   110.35  3.000
 BO5  C8    C9   C10   111.78  3.000
 BO5  H82C  C8   H81C  106.58  3.000
 BO5  H82C  C8   C7    109.95  3.000
 BO5  H81C  C8   C7    109.99  3.000
 BO5  H82C  C8   C9    109.79  3.000
 BO5  H81C  C8   C9    108.17  3.000
 BO5  C7    C8   C9    112.19  3.000
 BO5  H72C  C7   H71C  105.94  3.000
 BO5  H72C  C7   C6    109.26  3.000
 BO5  H71C  C7   C6    108.63  3.000
 BO5  H72C  C7   C8    109.43  3.000
 BO5  H71C  C7   C8    109.85  3.000
 BO5  C6    C7   C8    113.45  3.000
 BO5  H62C  C6   H61C  106.28  3.000
 BO5  H62C  C6   C5    109.47  3.000
 BO5  H61C  C6   C5    109.15  3.000
 BO5  H62C  C6   C7    109.69  3.000
 BO5  H61C  C6   C7    109.72  3.000
 BO5  C5    C6   C7    112.34  3.000
 BO5  H52C  C5   H51C  106.60  3.000
 BO5  H52C  C5   C4    109.46  3.000
 BO5  H51C  C5   C4    110.00  3.000
 BO5  H52C  C5   C6    108.82  3.000
 BO5  H51C  C5   C6    109.45  3.000
 BO5  C4    C5   C6    112.34  3.000
 BO5  H4    C4   C3    118.74  3.000
 BO5  H4    C4   C5    115.91  3.000
 BO5  C3    C4   C5    125.34  3.000
 BO5  H3    C3   C2    116.34  3.000
 BO5  H3    C3   C4    119.08  3.000
 BO5  C2    C3   C4    124.55  3.000
 BO5  H22C  C2   H21C  105.63  3.000
 BO5  H22C  C2   C1    111.43  3.000
 BO5  H21C  C2   C1    105.40  3.000
 BO5  H22C  C2   C3    110.23  3.000
 BO5  H21C  C2   C3    109.38  3.000
 BO5  C1    C2   C3    114.28  3.000
 BO5  H12C  C1   H11C  107.14  3.000
 BO5  H12C  C1   C2    109.35  3.000
 BO5  H11C  C1   C2    108.50  3.000
 BO5  H12C  C1   N     108.20  3.000
 BO5  H11C  C1   N     107.68  3.000
 BO5  C2    C1   N     115.65  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
 BO5  CONST_01  C14  C15  C16  C17     0.00   0.0  0
 BO5  CONST_02  C14  C13  C12  C17     0.00   0.0  0
 BO5  CONST_03  C13  C12  C17  C16     0.00   0.0  0
 BO5  CONST_04  C13  C14  C15  C16     0.00   0.0  0
 BO5  CONST_05  C12  C17  C16  C15     0.00   0.0  0
 BO5  CONST_06  C12  C13  C14  C15     0.00   0.0  0
 BO5  CONST_08  O2   C16  C17  C18     0.00   0.0  0
 BO5  CONST_09  CL   C13  C12  C17   180.00   0.0  0
 BO5  CONST_10  O1   C14  C15  C16   180.00   0.0  0
 BO5  CONST_11  C12  C17  C16  O2    180.00   0.0  0
 BO5  CONST_12  C14  C15  C16  O2    180.00   0.0  0
 BO5  CONST_13  CL   C13  C14  C15   180.00   0.0  0
 BO5  CONST_14  C12  C13  C14  O1    180.00   0.0  0
 BO5  CONST_15  C11  C12  C13  CL      0.00   0.0  0
 BO5  CONST_17  C17  C18  N    C       0.00   0.0  0
 BO5  CONST_18  H15  C15  C16  C17   180.00   0.0  0
 BO5  CONST_19  C    N    C18  O3    180.00   0.0  0
 BO5  Var_01    C2   C3   C4   C5    178.49   0.0  0
 BO5  Var_02    C2   C1   N    C18   128.97  30.0  1
 BO5  Var_03    C16  C17  C18  N     -75.31  30.0  1
 BO5  Var_04    C3   C2   C1   N     -61.54  30.0  1
 BO5  Var_05    C10  C11  C12  C17  -103.63  30.0  1
 BO5  Var_06    C9   C10  C11  C12  -168.97  30.0  1
 BO5  Var_07    C8   C9   C10  C11  -117.63  30.0  1
 BO5  Var_08    C7   C8   C9   C10    59.25  30.0  1
 BO5  Var_09    C6   C7   C8   C9    175.11  30.0  1
 BO5  Var_10    C5   C6   C7   C8    178.41  30.0  1
 BO5  Var_11    C4   C5   C6   C7    -63.39  30.0  1
 BO5  Var_12    C3   C4   C5   C6    115.54  30.0  1
 BO5  Var_13    C1   C2   C3   C4    133.63  30.0  1
 BO5  Var_14    H4   C4   C3   C2     -2.56   0.0  0
 BO5  Var_15    HC1  C    N    C18   -18.28  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
 BO5  plan-1  C18  0.020
 BO5  plan-1  C17  0.020
 BO5  plan-1  C16  0.020
 BO5  plan-1  O2   0.020
 BO5  plan-1  C15  0.020
 BO5  plan-1  C14  0.020
 BO5  plan-1  O1   0.020
 BO5  plan-1  C13  0.020
 BO5  plan-1  CL   0.020
 BO5  plan-1  C12  0.020
 BO5  plan-1  C11  0.020
 BO5  plan-1  H15  0.020
 BO5  plan-2  O3   0.020
 BO5  plan-2  C18  0.020
 BO5  plan-2  N    0.020
 BO5  plan-2  C    0.020
 BO5  plan-2  C17  0.020
 BO5  plan-2  C1   0.020
 BO5  plan-3  C11  0.020
 BO5  plan-3  C10  0.020
 BO5  plan-3  O    0.020
 BO5  plan-3  C9   0.020
 BO5  plan-4  C5   0.020
 BO5  plan-4  C4   0.020
 BO5  plan-4  C3   0.020
 BO5  plan-4  C2   0.020
 BO5  plan-4  H4   0.020
 BO5  plan-4  H3   0.020

