# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 22 17:29:37 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: (5E)-14-chloro-15,17-dihydroxy-4,7,8,9,10,11-hexahydro-2-benzoxacyclopentadecine-1,12(3H,13H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(O)c2C(=O)OCC/C=C/CCCCCC(=O)Cc2c1Cl
#
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
 M1S  M1S  (5E)-14-chloro-15,17-dihydroxy-4,7,8,9,10,11-hexahydro-2-benzoxacyclopentadecine-1,12(3H,13H)-dione  ligand  45  24  .  2021-08-14  2021-08-14  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_M1S
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
 M1S  C1    C   C     0   0.610  -0.2842   1.4851  -0.8056
 M1S  C2    C   CR6   0  -0.305   1.0252   1.0375  -0.2688
 M1S  C3    C   CR6   0   0.380   1.8881   1.9562   0.3728
 M1S  C4    C   CR16  0  -0.496   3.1864   1.5906   0.7117
 M1S  C5    C   CR6   0   0.463   3.6466   0.3147   0.4585
 M1S  C6    C   CR6   0  -0.228   2.7798  -0.6161  -0.1268
 M1S  C7    C   CR6   0   0.272   1.4908  -0.2797  -0.4969
 M1S  C8    C   CH2   0  -0.739   0.6111  -1.3800  -1.0081
 M1S  C9    C   C     0   0.411   0.1088  -2.2784   0.1012
 M1S  C10   C   CH2   0  -0.548  -0.8270  -3.3862  -0.3229
 M1S  C11   C   CH2   0  -0.429  -2.1846  -3.2450   0.3675
 M1S  C12   C   CH2   0  -0.418  -2.9102  -1.9615  -0.0177
 M1S  C13   C   CH2   0  -0.424  -4.2171  -1.7687   0.7346
 M1S  C14   C   CH2   0  -0.487  -4.9634  -0.5024   0.3105
 M1S  C15   C   C1    0  -0.210  -4.2307   0.7597   0.6430
 M1S  C16   C   C1    0  -0.200  -3.8121   1.6550  -0.2460
 M1S  C17   C   CH2   0  -0.510  -3.1789   2.9671   0.0934
 M1S  C18   C   CH2   0  -0.194  -1.8952   3.2818  -0.6491
 M1S  O2    O   O     0  -0.428  -0.8486   1.0176  -1.7615
 M1S  O3    O   OH1   0  -0.623   1.5617   3.2153   0.6706
 M1S  O4    O   OH1   0  -0.598   4.8784  -0.0871   0.7654
 M1S  CL1   CL  CL    0  -0.102   3.3856  -2.2243  -0.3421
 M1S  O5    O   O     0  -0.388   0.3994  -2.1060   1.2610
 M1S  O1    O   O2    0  -0.517  -0.7747   2.5340  -0.1312
 M1S  H4    H   HCR6  0   0.293   3.8304   2.3226   1.1858
 M1S  H8C1  H   HCH2  0   0.307   1.1343  -2.0096  -1.7335
 M1S  H8C2  H   HCH2  0   0.330  -0.2599  -1.0115  -1.5449
 M1S  H101  H   HCH2  0   0.277  -0.3665  -4.3390  -0.0459
 M1S  H102  H   HCH2  0   0.248  -0.9501  -3.3930  -1.4078
 M1S  H111  H   HCH2  0   0.224  -2.0398  -3.2824   1.4503
 M1S  H112  H   HCH2  0   0.237  -2.8020  -4.1086   0.1080
 M1S  H121  H   HCH2  0   0.212  -3.1080  -1.9669  -1.0953
 M1S  H122  H   HCH2  0   0.223  -2.2691  -1.0919   0.1616
 M1S  H131  H   HCH2  0   0.215  -4.0194  -1.7346   1.8111
 M1S  H132  H   HCH2  0   0.224  -4.8667  -2.6337   0.5720
 M1S  H141  H   HCH2  0   0.237  -5.9373  -0.4877   0.8102
 M1S  H142  H   HCH2  0   0.226  -5.1661  -0.5409  -0.7640
 M1S  H15   H   H     0   0.228  -4.0512   0.9450   1.7011
 M1S  H16   H   H     0   0.229  -3.9838   1.4674  -1.3038
 M1S  H171  H   HCH2  0   0.251  -3.0186   3.0577   1.1708
 M1S  H172  H   HCH2  0   0.252  -3.8727   3.7709  -0.1777
 M1S  H181  H   HCH2  0   0.265  -1.6258   4.3256  -0.4935
 M1S  H182  H   HCH2  0   0.252  -1.9998   3.1114  -1.7201
 M1S  H3    H   HOH1  0   0.488   0.6089   3.3419   0.5275
 M1S  HA    H   HOH1  0   0.489   5.3831   0.6360   1.1574

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
 M1S  C1   C2    single    1.484  0.020  1.484
 M1S  C1   O2    double    1.205  0.020  1.205
 M1S  C1   O1    single    1.340  0.020  1.340
 M1S  C2   C3    single    1.414  0.020  1.414
 M1S  C2   C7    aromatic  1.416  0.020  1.416
 M1S  C3   C4    aromatic  1.391  0.020  1.391
 M1S  C3   O3    single    1.334  0.020  1.334
 M1S  C4   C5    aromatic  1.380  0.020  1.380
 M1S  C4   H4    single    0.930  0.020  1.080
 M1S  C5   C6    aromatic  1.400  0.020  1.400
 M1S  C5   O4    single    1.332  0.020  1.332
 M1S  C6   C7    single    1.383  0.020  1.383
 M1S  C6   CL1   single    1.732  0.020  1.732
 M1S  C7   C8    single    1.499  0.020  1.499
 M1S  C8   C9    single    1.513  0.020  1.513
 M1S  C8   H8C1  single    0.970  0.020  1.090
 M1S  C8   H8C2  single    0.970  0.020  1.090
 M1S  C9   C10   single    1.511  0.020  1.511
 M1S  C9   O5    double    1.208  0.020  1.208
 M1S  C10  C11   single    1.530  0.020  1.530
 M1S  C10  H101  single    0.970  0.020  1.090
 M1S  C10  H102  single    0.970  0.020  1.090
 M1S  C11  C12   single    1.524  0.020  1.524
 M1S  C11  H111  single    0.970  0.020  1.090
 M1S  C11  H112  single    0.970  0.020  1.090
 M1S  C12  C13   single    1.520  0.020  1.520
 M1S  C12  H121  single    0.970  0.020  1.090
 M1S  C12  H122  single    0.970  0.020  1.090
 M1S  C13  C14   single    1.530  0.020  1.530
 M1S  C13  H131  single    0.970  0.020  1.090
 M1S  C13  H132  single    0.970  0.020  1.090
 M1S  C14  C15   single    1.497  0.020  1.497
 M1S  C14  H141  single    0.970  0.020  1.090
 M1S  C14  H142  single    0.970  0.020  1.090
 M1S  C15  C16   double    1.329  0.020  1.329
 M1S  C15  H15   single    0.930  0.020  1.080
 M1S  C16  C17   single    1.496  0.020  1.496
 M1S  C16  H16   single    0.930  0.020  1.080
 M1S  C17  C18   single    1.516  0.020  1.516
 M1S  C17  H171  single    0.970  0.020  1.090
 M1S  C17  H172  single    0.970  0.020  1.090
 M1S  C18  O1    single    1.443  0.020  1.443
 M1S  C18  H181  single    0.970  0.020  1.090
 M1S  C18  H182  single    0.970  0.020  1.090
 M1S  O3   H3    single    0.850  0.020  0.980
 M1S  O4   HA    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
 M1S  O1    C1   O2    122.12  3.000
 M1S  O1    C1   C2    112.15  3.000
 M1S  O2    C1   C2    125.68  3.000
 M1S  C7    C2   C3    118.48  3.000
 M1S  C7    C2   C1    120.83  3.000
 M1S  C3    C2   C1    120.42  3.000
 M1S  O3    C3   C4    114.96  3.000
 M1S  O3    C3   C2    124.40  3.000
 M1S  C4    C3   C2    120.62  3.000
 M1S  H4    C4   C5    120.43  3.000
 M1S  H4    C4   C3    118.92  3.000
 M1S  C5    C4   C3    120.65  3.000
 M1S  O4    C5   C6    117.93  3.000
 M1S  O4    C5   C4    123.05  3.000
 M1S  C6    C5   C4    119.02  3.000
 M1S  CL1   C6   C7    121.24  3.000
 M1S  CL1   C6   C5    116.92  3.000
 M1S  C7    C6   C5    121.82  3.000
 M1S  C8    C7   C6    117.38  3.000
 M1S  C8    C7   C2    123.03  3.000
 M1S  C6    C7   C2    119.33  3.000
 M1S  H8C2  C8   H8C1  104.52  3.000
 M1S  H8C2  C8   C9    107.29  3.000
 M1S  H8C1  C8   C9    107.65  3.000
 M1S  H8C2  C8   C7    112.94  3.000
 M1S  H8C1  C8   C7    111.60  3.000
 M1S  C9    C8   C7    112.38  3.000
 M1S  O5    C9   C10   121.54  3.000
 M1S  O5    C9   C8    122.62  3.000
 M1S  C10   C9   C8    115.80  3.000
 M1S  H102  C10  H101  107.08  3.000
 M1S  H102  C10  C11   110.42  3.000
 M1S  H101  C10  C11   109.86  3.000
 M1S  H102  C10  C9    110.69  3.000
 M1S  H101  C10  C9    107.87  3.000
 M1S  C11   C10  C9    110.81  3.000
 M1S  H112  C11  H111  106.44  3.000
 M1S  H112  C11  C12   109.67  3.000
 M1S  H111  C11  C12   110.02  3.000
 M1S  H112  C11  C10   108.74  3.000
 M1S  H111  C11  C10   109.05  3.000
 M1S  C12   C11  C10   112.72  3.000
 M1S  H122  C12  H121  105.70  3.000
 M1S  H122  C12  C13   108.76  3.000
 M1S  H121  C12  C13   109.40  3.000
 M1S  H122  C12  C11   110.41  3.000
 M1S  H121  C12  C11   109.29  3.000
 M1S  C13   C12  C11   113.02  3.000
 M1S  H132  C13  H131  106.13  3.000
 M1S  H132  C13  C14   108.88  3.000
 M1S  H131  C13  C14   109.56  3.000
 M1S  H132  C13  C12   109.68  3.000
 M1S  H131  C13  C12   109.59  3.000
 M1S  C14   C13  C12   112.78  3.000
 M1S  H142  C14  H141  106.50  3.000
 M1S  H142  C14  C15   109.79  3.000
 M1S  H141  C14  C15   108.83  3.000
 M1S  H142  C14  C13   109.48  3.000
 M1S  H141  C14  C13   108.57  3.000
 M1S  C15   C14  C13   113.43  3.000
 M1S  H15   C15  C16   118.90  3.000
 M1S  H15   C15  C14   116.10  3.000
 M1S  C16   C15  C14   124.99  3.000
 M1S  H16   C16  C17   116.02  3.000
 M1S  H16   C16  C15   118.98  3.000
 M1S  C17   C16  C15   124.91  3.000
 M1S  H172  C17  H171  106.02  3.000
 M1S  H172  C17  C18   105.22  3.000
 M1S  H171  C17  C18   109.96  3.000
 M1S  H172  C17  C16   108.62  3.000
 M1S  H171  C17  C16   111.01  3.000
 M1S  C18   C17  C16   115.43  3.000
 M1S  H182  C18  H181  108.30  3.000
 M1S  H182  C18  O1    110.25  3.000
 M1S  H181  C18  O1    104.67  3.000
 M1S  H182  C18  C17   111.58  3.000
 M1S  H181  C18  C17   109.79  3.000
 M1S  O1    C18  C17   111.97  3.000
 M1S  H3    O3   C3    109.26  3.000
 M1S  HA    O4   C5    110.57  3.000
 M1S  C18   O1   C1    120.61  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
 M1S  CONST_01  C5   C4   C3   C2      0.00   0.0  0
 M1S  CONST_02  C5   C6   C7   C2      0.00   0.0  0
 M1S  CONST_03  C6   C7   C2   C3      0.00   0.0  0
 M1S  CONST_04  C6   C5   C4   C3      0.00   0.0  0
 M1S  CONST_05  C7   C2   C3   C4      0.00   0.0  0
 M1S  CONST_06  C7   C6   C5   C4      0.00   0.0  0
 M1S  CONST_07  O3   C3   C2   C1      0.00   0.0  0
 M1S  CONST_08  CL1  C6   C7   C2    180.00   0.0  0
 M1S  CONST_09  O4   C5   C4   C3    180.00   0.0  0
 M1S  CONST_10  CL1  C6   C5   C4    180.00   0.0  0
 M1S  CONST_11  O3   C3   C4   C5    180.00   0.0  0
 M1S  CONST_12  O3   C3   C2   C7    180.00   0.0  0
 M1S  CONST_13  O4   C5   C6   C7    180.00   0.0  0
 M1S  CONST_14  CL1  C6   C7   C8      0.00   0.0  0
 M1S  CONST_15  H4   C4   C3   C2    180.00   0.0  0
 M1S  Var_01    C17  C16  C15  C14   174.79   0.0  0
 M1S  Var_02    C17  C18  O1   C1    104.77  30.0  1
 M1S  Var_03    C9   C8   C7   C2    -98.73  30.0  1
 M1S  Var_04    O1   C1   C2   C3    -28.13  30.0  1
 M1S  Var_05    C10  C9   C8   C7    177.88  30.0  1
 M1S  Var_06    C11  C10  C9   C8   -119.63  30.0  1
 M1S  Var_07    C12  C11  C10  C9     63.18  30.0  1
 M1S  Var_08    C13  C12  C11  C10  -176.15  30.0  1
 M1S  Var_09    C14  C13  C12  C11  -178.10  30.0  1
 M1S  Var_10    C15  C14  C13  C12   -64.97  30.0  1
 M1S  Var_11    C16  C15  C14  C13   118.72  30.0  1
 M1S  Var_12    C18  C17  C16  C15   131.25  30.0  1
 M1S  Var_13    O1   C18  C17  C16   -75.83  30.0  1
 M1S  Var_14    H15  C15  C16  C17    -4.23   0.0  0

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
 M1S  plan-1  C1   0.020
 M1S  plan-1  C2   0.020
 M1S  plan-1  C3   0.020
 M1S  plan-1  C4   0.020
 M1S  plan-1  C5   0.020
 M1S  plan-1  C6   0.020
 M1S  plan-1  C7   0.020
 M1S  plan-1  C8   0.020
 M1S  plan-1  O3   0.020
 M1S  plan-1  O4   0.020
 M1S  plan-1  CL1  0.020
 M1S  plan-1  H4   0.020
 M1S  plan-2  C8   0.020
 M1S  plan-2  C9   0.020
 M1S  plan-2  C10  0.020
 M1S  plan-2  O5   0.020
 M1S  plan-3  C1   0.020
 M1S  plan-3  C2   0.020
 M1S  plan-3  O2   0.020
 M1S  plan-3  O1   0.020
 M1S  plan-4  C14  0.020
 M1S  plan-4  C15  0.020
 M1S  plan-4  C16  0.020
 M1S  plan-4  C17  0.020
 M1S  plan-4  H15  0.020
 M1S  plan-4  H16  0.020

