# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 09:35:01 2022
#   Inital geometry file: a 141 line input string
#   Ligand name: (4S,4aS,6S,8aS)-6-[(1S)-7-chloro-4-hydroxy-1-methyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl]-4-(dimethylamino)-3,8a-dihydroxy-1,8-dioxo-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(C)[C@H]1[C@@H]2C[C@@H](CC(=O)[C@]2(O)C(=O)C(=C1O)C(N)=O)[C@]3(C)OC(=O)c4c(O)ccc(Cl)c34
#
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
 ITC  ITC  (4S,4aS,6S,8aS)-6-[(1S)-7-chloro-4-hydroxy-1-methyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl]-4-(dimethylamino)-3,8a-dihydroxy-1,8-dioxo-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxamide  ligand  56  33  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_ITC
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
 ITC  C1    C   C     0   0.396  -2.2173   0.8341  -1.1448
 ITC  O1    O   O     0  -0.402  -1.8206   1.6605  -1.9451
 ITC  C2    C   C     0  -0.351  -3.1868   1.1482  -0.1119
 ITC  C2'   C   C     0   0.482  -3.8793   2.4692  -0.2018
 ITC  O2'   O   O     0  -0.439  -4.4039   2.8566  -1.2264
 ITC  N2'   N   NH2   0  -0.823  -3.9547   3.1459   0.9751
 ITC  C3    C   C     0   0.447  -3.5001   0.2473   0.8622
 ITC  O3    O   OH1   0  -0.569  -4.3601   0.4715   1.8372
 ITC  C4    C   CH1   0  -0.140  -2.9431  -1.1492   0.9209
 ITC  N4    N   NT    0  -0.404  -3.9449  -2.1706   0.6310
 ITC  C4'   C   CH3   0  -0.528  -4.3495  -2.9317   1.7945
 ITC  C4D   C   CH3   0  -0.545  -5.0879  -1.8075  -0.1828
 ITC  C4A   C   CH1   0  -0.304  -1.6396  -1.2815   0.1153
 ITC  C5    C   CH2   0  -0.452  -0.4734  -0.7123   0.9317
 ITC  C5A   C   CH1   0  -0.241   0.8635  -0.8381   0.2054
 ITC  C6    C   CR5   0   0.163   2.0516  -0.3617   1.0622
 ITC  O6    O   O     0  -0.462   1.8243   1.0216   1.4209
 ITC  C6'   C   CH3   0  -0.649   2.2189  -1.1549   2.3507
 ITC  C6A   C   CR56  0   0.279   3.3453  -0.2968   0.2842
 ITC  C7    C   CR6   0  -0.227   4.1007  -1.2600  -0.3460
 ITC  CL7   CL  CL    0  -0.117   3.6296  -2.9246  -0.3728
 ITC  C8    C   CR16  0  -0.189   5.2736  -0.8682  -0.9908
 ITC  C9    C   CR16  0  -0.365   5.6897   0.4523  -1.0080
 ITC  C10   C   CR6   0   0.371   4.9338   1.4376  -0.3723
 ITC  O10   O   OH1   0  -0.600   5.3472   2.7029  -0.3984
 ITC  C6B   C   CR56  0  -0.249   3.7675   1.0212   0.2620
 ITC  C5B   C   CH2   0  -0.579   0.8017  -0.1080  -1.1404
 ITC  C12   C   C     0   0.421  -0.3641  -0.5954  -1.9448
 ITC  O12   O   O     0  -0.375  -0.2718  -0.9723  -3.0883
 ITC  C4B   C   CT    0   0.040  -1.7298  -0.6191  -1.2569
 ITC  O4B   O   OH1   0  -0.647  -2.6550  -1.2914  -2.0601
 ITC  C11   C   CR5   0   0.576   2.7959   1.8272   0.9872
 ITC  H2'1  H   HNH2  0   0.419  -3.2152   3.0345   1.6528
 ITC  H2'2  H   HNH2  0   0.410  -4.3821   4.0611   0.9640
 ITC  H3    H   HOH1  0   0.482  -4.7207   1.3757   1.8017
 ITC  H4    H   HCH1  0   0.289  -2.6503  -1.2889   1.9676
 ITC  H4A   H   HCH1  0   0.281  -1.4644  -2.3510  -0.0347
 ITC  H4'1  H   HCH3  0   0.203  -4.9684  -2.3658   2.5052
 ITC  H4'2  H   HCH3  0   0.234  -4.9291  -3.7994   1.4750
 ITC  H4'3  H   HCH3  0   0.238  -3.4751  -3.3041   2.3293
 ITC  H4D1  H   HCH3  0   0.253  -4.7847  -1.2442  -1.0603
 ITC  H4D2  H   HCH3  0   0.239  -5.5664  -2.7214  -0.5396
 ITC  H4D3  H   HCH3  0   0.199  -5.8521  -1.2308   0.3560
 ITC  H51C  H   HCH2  0   0.251  -0.6606   0.3334   1.1942
 ITC  H52C  H   HCH2  0   0.275  -0.4384  -1.2654   1.8709
 ITC  H5A   H   HCH1  0   0.270   1.0418  -1.9002   0.0098
 ITC  H5B1  H   HCH2  0   0.288   0.6700   0.9682  -0.9825
 ITC  H5B2  H   HCH2  0   0.289   1.7074  -0.2430  -1.7317
 ITC  H6'1  H   HCH3  0   0.245   2.3518  -2.2127   2.1308
 ITC  H6'2  H   HCH3  0   0.260   3.0958  -0.8103   2.8978
 ITC  H6'3  H   HCH3  0   0.264   1.3503  -1.0477   2.9974
 ITC  H8    H   HCR6  0   0.297   5.8773  -1.6111  -1.4948
 ITC  H9    H   HCR6  0   0.292   6.6059   0.7189  -1.5180
 ITC  H10   H   HOH1  0   0.480   4.7284   3.2781   0.0748
 ITC  H4B   H   HOH1  0   0.455  -2.3412  -1.2450  -2.9749
 ITC  O11   O   O     0  -0.432   2.8046   3.0149   1.1960

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
 ITC  C1   O1    double    1.217  0.020  1.217
 ITC  C1   C2    single    1.451  0.020  1.451
 ITC  C1   C4B   single    1.537  0.020  1.537
 ITC  C2   C2'   single    1.494  0.020  1.494
 ITC  C2   C3    double    1.363  0.020  1.363
 ITC  C2'  O2'   double    1.214  0.020  1.214
 ITC  C2'  N2'   single    1.360  0.020  1.360
 ITC  C3   O3    single    1.319  0.020  1.319
 ITC  C3   C4    single    1.505  0.020  1.505
 ITC  C4   N4    single    1.460  0.020  1.460
 ITC  C4   C4A   single    1.538  0.020  1.538
 ITC  N4   C4'   single    1.448  0.020  1.448
 ITC  N4   C4D   single    1.449  0.020  1.449
 ITC  C4A  C5    single    1.533  0.020  1.533
 ITC  C4A  C4B   single    1.526  0.020  1.526
 ITC  C5   C5A   single    1.527  0.020  1.527
 ITC  C5A  C6    single    1.540  0.020  1.540
 ITC  C5A  C5B   single    1.532  0.020  1.532
 ITC  C6   O6    single    1.447  0.020  1.447
 ITC  C6   C6'   single    1.522  0.020  1.522
 ITC  C6   C6A   single    1.511  0.020  1.511
 ITC  O6   C11   single    1.335  0.020  1.335
 ITC  C6A  C7    aromatic  1.377  0.020  1.377
 ITC  C6A  C6B   aromatic  1.384  0.020  1.384
 ITC  C7   CL7   single    1.730  0.020  1.730
 ITC  C7   C8    aromatic  1.395  0.020  1.395
 ITC  C8   C9    aromatic  1.385  0.020  1.385
 ITC  C9   C10   aromatic  1.395  0.020  1.395
 ITC  C10  O10   single    1.331  0.020  1.331
 ITC  C10  C6B   aromatic  1.391  0.020  1.391
 ITC  C6B  C11   single    1.456  0.020  1.456
 ITC  O11  C11   double    1.206  0.020  1.206
 ITC  C5B  C12   single    1.498  0.020  1.498
 ITC  C12  O12   double    1.208  0.020  1.208
 ITC  C12  C4B   single    1.529  0.020  1.529
 ITC  C4B  O4B   single    1.398  0.020  1.398
 ITC  N2'  H2'1  single    0.890  0.020  1.040
 ITC  N2'  H2'2  single    0.890  0.020  1.040
 ITC  O3   H3    single    0.850  0.020  0.980
 ITC  C4   H4    single    0.970  0.020  1.090
 ITC  C4A  H4A   single    0.970  0.020  1.090
 ITC  C4'  H4'1  single    0.970  0.020  1.090
 ITC  C4'  H4'2  single    0.970  0.020  1.090
 ITC  C4'  H4'3  single    0.970  0.020  1.090
 ITC  C4D  H4D1  single    0.970  0.020  1.090
 ITC  C4D  H4D2  single    0.970  0.020  1.090
 ITC  C4D  H4D3  single    0.970  0.020  1.090
 ITC  C5   H51C  single    0.970  0.020  1.090
 ITC  C5   H52C  single    0.970  0.020  1.090
 ITC  C5A  H5A   single    0.970  0.020  1.090
 ITC  C5B  H5B1  single    0.970  0.020  1.090
 ITC  C5B  H5B2  single    0.970  0.020  1.090
 ITC  C6'  H6'1  single    0.970  0.020  1.090
 ITC  C6'  H6'2  single    0.970  0.020  1.090
 ITC  C6'  H6'3  single    0.970  0.020  1.090
 ITC  C8   H8    single    0.930  0.020  1.080
 ITC  C9   H9    single    0.930  0.020  1.080
 ITC  O10  H10   single    0.850  0.020  0.980
 ITC  O4B  H4B   single    0.850  0.020  0.980

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
 ITC  C4B   C1   C2    117.94  3.000
 ITC  C4B   C1   O1    119.39  3.000
 ITC  C2    C1   O1    122.61  3.000
 ITC  C3    C2   C2'   121.38  3.000
 ITC  C3    C2   C1    121.27  3.000
 ITC  C2'   C2   C1    117.27  3.000
 ITC  N2'   C2'  O2'   123.19  3.000
 ITC  N2'   C2'  C2    114.43  3.000
 ITC  O2'   C2'  C2    122.21  3.000
 ITC  H2'2  N2'  H2'1  114.66  3.000
 ITC  H2'2  N2'  C2'   117.70  3.000
 ITC  H2'1  N2'  C2'   119.06  3.000
 ITC  C4    C3   O3    111.73  3.000
 ITC  C4    C3   C2    123.79  3.000
 ITC  O3    C3   C2    124.44  3.000
 ITC  H3    O3   C3    111.85  3.000
 ITC  H4    C4   C4A   105.24  3.000
 ITC  H4    C4   N4    106.49  3.000
 ITC  C4A   C4   N4    114.67  3.000
 ITC  H4    C4   C3    104.75  3.000
 ITC  C4A   C4   C3    111.91  3.000
 ITC  N4    C4   C3    112.81  3.000
 ITC  C4D   N4   C4'   111.26  3.000
 ITC  C4D   N4   C4    118.52  3.000
 ITC  C4'   N4   C4    113.57  3.000
 ITC  H4'3  C4'  H4'2  107.33  3.000
 ITC  H4'3  C4'  H4'1  108.07  3.000
 ITC  H4'2  C4'  H4'1  107.43  3.000
 ITC  H4'3  C4'  N4    110.46  3.000
 ITC  H4'2  C4'  N4    109.33  3.000
 ITC  H4'1  C4'  N4    113.97  3.000
 ITC  H4D3  C4D  H4D2  107.15  3.000
 ITC  H4D3  C4D  H4D1  108.55  3.000
 ITC  H4D2  C4D  H4D1  107.02  3.000
 ITC  H4D3  C4D  N4    113.87  3.000
 ITC  H4D2  C4D  N4    108.64  3.000
 ITC  H4D1  C4D  N4    111.32  3.000
 ITC  H4A   C4A  C4B   108.08  3.000
 ITC  H4A   C4A  C5    108.31  3.000
 ITC  C4B   C4A  C5    111.25  3.000
 ITC  H4A   C4A  C4    106.96  3.000
 ITC  C4B   C4A  C4    112.55  3.000
 ITC  C5    C4A  C4    109.50  3.000
 ITC  H52C  C5   H51C  106.47  3.000
 ITC  H52C  C5   C5A   109.87  3.000
 ITC  H51C  C5   C5A   110.04  3.000
 ITC  H52C  C5   C4A   107.14  3.000
 ITC  H51C  C5   C4A   110.63  3.000
 ITC  C5A   C5   C4A   112.47  3.000
 ITC  H5A   C5A  C5B   108.18  3.000
 ITC  H5A   C5A  C6    105.89  3.000
 ITC  C5B   C5A  C6    111.86  3.000
 ITC  H5A   C5A  C5    107.92  3.000
 ITC  C5B   C5A  C5    110.08  3.000
 ITC  C6    C5A  C5    112.66  3.000
 ITC  C6A   C6   C6'   111.35  3.000
 ITC  C6A   C6   O6    102.77  3.000
 ITC  C6'   C6   O6    107.79  3.000
 ITC  C6A   C6   C5A   112.79  3.000
 ITC  C6'   C6   C5A   113.23  3.000
 ITC  O6    C6   C5A   108.20  3.000
 ITC  C11   O6   C6    112.47  3.000
 ITC  H6'3  C6'  H6'2  108.23  3.000
 ITC  H6'3  C6'  H6'1  108.26  3.000
 ITC  H6'2  C6'  H6'1  108.09  3.000
 ITC  H6'3  C6'  C6    111.34  3.000
 ITC  H6'2  C6'  C6    110.41  3.000
 ITC  H6'1  C6'  C6    110.41  3.000
 ITC  C6B   C6A  C7    119.43  3.000
 ITC  C6B   C6A  C6    108.08  3.000
 ITC  C7    C6A  C6    132.49  3.000
 ITC  C8    C7   CL7   119.48  3.000
 ITC  C8    C7   C6A   118.46  3.000
 ITC  CL7   C7   C6A   122.06  3.000
 ITC  H8    C8   C9    118.78  3.000
 ITC  H8    C8   C7    119.46  3.000
 ITC  C9    C8   C7    121.76  3.000
 ITC  H9    C9   C10   119.97  3.000
 ITC  H9    C9   C8    119.69  3.000
 ITC  C10   C9   C8    120.34  3.000
 ITC  C6B   C10  O10   123.61  3.000
 ITC  C6B   C10  C9    116.78  3.000
 ITC  O10   C10  C9    119.61  3.000
 ITC  H10   O10  C10   110.89  3.000
 ITC  C11   C6B  C10   128.38  3.000
 ITC  C11   C6B  C6A   108.39  3.000
 ITC  C10   C6B  C6A   123.23  3.000
 ITC  H5B2  C5B  H5B1  107.43  3.000
 ITC  H5B2  C5B  C12   108.37  3.000
 ITC  H5B1  C5B  C12   107.66  3.000
 ITC  H5B2  C5B  C5A   112.58  3.000
 ITC  H5B1  C5B  C5A   110.26  3.000
 ITC  C12   C5B  C5A   110.37  3.000
 ITC  C4B   C12  O12   119.30  3.000
 ITC  C4B   C12  C5B   117.29  3.000
 ITC  O12   C12  C5B   123.41  3.000
 ITC  O4B   C4B  C12   109.88  3.000
 ITC  O4B   C4B  C4A   110.30  3.000
 ITC  C12   C4B  C4A   111.00  3.000
 ITC  O4B   C4B  C1    106.66  3.000
 ITC  C12   C4B  C1    107.54  3.000
 ITC  C4A   C4B  C1    111.31  3.000
 ITC  H4B   O4B  C4B   107.78  3.000
 ITC  O11   C11  C6B   128.80  3.000
 ITC  O11   C11  O6    122.92  3.000
 ITC  C6B   C11  O6    108.28  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
 ITC  CONST_01  C9    C8   C7   C6A    0.00   0.0  0
 ITC  CONST_02  C9    C10  C6B  C6A    0.00   0.0  0
 ITC  CONST_03  C10   C6B  C6A  C7     0.00   0.0  0
 ITC  CONST_04  C10   C9   C8   C7     0.00   0.0  0
 ITC  CONST_05  C6B   C6A  C7   C8     0.00   0.0  0
 ITC  CONST_06  C6B   C10  C9   C8     0.00   0.0  0
 ITC  CONST_07  CL7   C7   C6A  C6     0.00   0.0  0
 ITC  CONST_08  O10   C10  C6B  C6A  180.00   0.0  0
 ITC  CONST_09  C6B   C6A  C7   CL7  180.00   0.0  0
 ITC  CONST_10  C9    C8   C7   CL7  180.00   0.0  0
 ITC  CONST_11  O10   C10  C9   C8   180.00   0.0  0
 ITC  CONST_12  C11   C6B  C10  O10    0.00   0.0  0
 ITC  CONST_13  H8    C8   C7   C6A  180.00   0.0  0
 ITC  CONST_14  H9    C9   C8   C7   180.00   0.0  0
 ITC  CONST_16  H2'2  N2'  C2'  C2   180.00   0.0  0
 ITC  Var_01    C4    C3   C2   C1    -3.29  30.0  1
 ITC  Var_02    C4B   C1   C2   C3    10.25  30.0  1
 ITC  Var_03    C4B   C12  C5B  C5A   50.85  30.0  1
 ITC  Var_04    C6B   C11  O6   C6     0.98  30.0  1
 ITC  Var_05    C6A   C6B  C11  O6    -0.32  30.0  1
 ITC  Var_06    O2'   C2'  C2   C1    49.64  30.0  2
 ITC  Var_07    H4'1  C4'  N4   C4    71.58  30.0  3
 ITC  Var_08    H4D1  C4D  N4   C4    46.09  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
 ITC  chir_01  C4   C3   N4   C4A  negativ
 ITC  chir_02  C4A  C4   C5   C4B  positiv
 ITC  chir_03  C5A  C5   C6   C5B  positiv
 ITC  chir_04  C6   C6A  O6   C5A  negativ
 ITC  chir_05  C4B  C12  C4A  C1   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
 ITC  plan-1  C2    0.020
 ITC  plan-1  C2'   0.020
 ITC  plan-1  O2'   0.020
 ITC  plan-1  N2'   0.020
 ITC  plan-1  H2'1  0.020
 ITC  plan-1  H2'2  0.020
 ITC  plan-2  C6    0.020
 ITC  plan-2  C6A   0.020
 ITC  plan-2  C7    0.020
 ITC  plan-2  CL7   0.020
 ITC  plan-2  C8    0.020
 ITC  plan-2  C9    0.020
 ITC  plan-2  C10   0.020
 ITC  plan-2  O10   0.020
 ITC  plan-2  C6B   0.020
 ITC  plan-2  C11   0.020
 ITC  plan-2  H8    0.020
 ITC  plan-2  H9    0.020
 ITC  plan-3  C1    0.020
 ITC  plan-3  O1    0.020
 ITC  plan-3  C2    0.020
 ITC  plan-3  C4B   0.020
 ITC  plan-4  C5B   0.020
 ITC  plan-4  C12   0.020
 ITC  plan-4  O12   0.020
 ITC  plan-4  C4B   0.020
 ITC  plan-5  O6    0.020
 ITC  plan-5  C6B   0.020
 ITC  plan-5  C11   0.020
 ITC  plan-5  O11   0.020

