# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 02:56:48 2020
#   Inital geometry file: a 107 line input string
#   Ligand name: (5E)-13-chloro-14,16-dihydroxy-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,11(12H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(O)c2C(=O)OCC/C=C/CCCCC(=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
 P2N  P2N  (5E)-13-chloro-14,16-dihydroxy-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,11(12H)-dione  ligand  42  23  .  2021-08-19  2021-08-19  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_P2N
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
 P2N  C1    C   C     0   0.554  -0.4247   1.3802  -0.6090
 P2N  C2    C   CR6   0  -0.260   0.9058   0.9584  -0.1080
 P2N  C3    C   CR6   0   0.392   1.9594   1.8788  -0.0026
 P2N  C4    C   CR16  0  -0.499   3.2451   1.4334   0.2831
 P2N  C5    C   CR6   0   0.462   3.4904   0.0889   0.4964
 P2N  C6    C   CR6   0  -0.266   2.4258  -0.8196   0.4453
 P2N  C7    C   CR6   0   0.309   1.1395  -0.4020   0.1568
 P2N  C8    C   CH2   0  -0.725  -0.0003  -1.3748   0.2101
 P2N  C9    C   C     0   0.430  -0.2361  -2.1330  -1.0774
 P2N  C10   C   CH2   0  -0.558  -1.4995  -2.9554  -1.1456
 P2N  C11   C   CH2   0  -0.480  -2.7807  -2.1500  -0.8638
 P2N  C12   C   CH2   0  -0.445  -3.2852  -2.2207   0.5756
 P2N  C13   C   CH2   0  -0.490  -4.3304  -1.1384   0.8705
 P2N  C14   C   C1    0  -0.218  -3.7249   0.2143   1.1038
 P2N  C15   C   C1    0  -0.199  -3.7370   1.2250   0.2391
 P2N  C16   C   CH2   0  -0.512  -3.2111   2.6006   0.5117
 P2N  C17   C   CH2   0  -0.201  -2.1052   3.0855  -0.4136
 P2N  O1    O   O2    0  -0.484  -0.8292   2.5206  -0.0528
 P2N  O2    O   O     0  -0.417  -1.0524   0.7797  -1.4417
 P2N  O3    O   OH1   0  -0.621   1.8256   3.1955  -0.2066
 P2N  O4    O   OH1   0  -0.602   4.7047  -0.3900   0.7705
 P2N  CL1   CL  CL    0  -0.104   2.7761  -2.4838   0.7645
 P2N  O5    O   O     0  -0.392   0.5677  -2.1055  -1.9794
 P2N  H4    H   HCR6  0   0.294   4.0545   2.1521   0.3375
 P2N  H8C1  H   HCH2  0   0.303  -0.9205  -0.8789   0.5172
 P2N  H8C2  H   HCH2  0   0.307   0.1782  -2.1237   0.9883
 P2N  H101  H   HCH2  0   0.264  -1.4111  -3.7732  -0.4208
 P2N  H102  H   HCH2  0   0.263  -1.5414  -3.4165  -2.1331
 P2N  H111  H   HCH2  0   0.249  -3.5718  -2.5285  -1.5146
 P2N  H112  H   HCH2  0   0.260  -2.6364  -1.1086  -1.1575
 P2N  H121  H   HCH2  0   0.227  -2.4654  -2.1298   1.2943
 P2N  H122  H   HCH2  0   0.237  -3.7183  -3.2096   0.7487
 P2N  H131  H   HCH2  0   0.239  -4.8974  -1.4239   1.7606
 P2N  H132  H   HCH2  0   0.230  -5.0484  -1.0938   0.0463
 P2N  H14   H   H     0   0.231  -3.2467   0.3582   2.0712
 P2N  H15   H   H     0   0.230  -4.2053   1.0837  -0.7328
 P2N  H161  H   HCH2  0   0.252  -2.8809   2.6936   1.5493
 P2N  H162  H   HCH2  0   0.254  -4.0319   3.3150   0.3883
 P2N  H171  H   HCH2  0   0.265  -1.9688   4.1585  -0.2933
 P2N  H172  H   HCH2  0   0.249  -2.3319   2.8844  -1.4610
 P2N  H3    H   HOH1  0   0.482   0.8928   3.4502  -0.2254
 P2N  HA    H   HOH1  0   0.487   5.3551   0.3227   0.7834

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
 P2N  C1   C2    single    1.483  0.020  1.483
 P2N  C1   O1    single    1.332  0.020  1.332
 P2N  C1   O2    double    1.203  0.020  1.203
 P2N  C2   C3    single    1.403  0.020  1.403
 P2N  C2   C7    aromatic  1.405  0.020  1.405
 P2N  C3   C4    aromatic  1.390  0.020  1.390
 P2N  C3   O3    single    1.339  0.020  1.339
 P2N  C4   C5    aromatic  1.383  0.020  1.383
 P2N  C4   H4    single    0.930  0.020  1.080
 P2N  C5   C6    aromatic  1.401  0.020  1.401
 P2N  C5   O4    single    1.334  0.020  1.334
 P2N  C6   C7    single    1.383  0.020  1.383
 P2N  C6   CL1   single    1.730  0.020  1.730
 P2N  C7   C8    single    1.499  0.020  1.499
 P2N  C8   C9    single    1.513  0.020  1.513
 P2N  C8   H8C1  single    0.970  0.020  1.090
 P2N  C8   H8C2  single    0.970  0.020  1.090
 P2N  C9   C10   single    1.509  0.020  1.509
 P2N  C9   O5    double    1.208  0.020  1.208
 P2N  C10  C11   single    1.539  0.020  1.539
 P2N  C10  H101  single    0.970  0.020  1.090
 P2N  C10  H102  single    0.970  0.020  1.090
 P2N  C11  C12   single    1.527  0.020  1.527
 P2N  C11  H111  single    0.970  0.020  1.090
 P2N  C11  H112  single    0.970  0.020  1.090
 P2N  C12  C13   single    1.533  0.020  1.533
 P2N  C12  H121  single    0.970  0.020  1.090
 P2N  C12  H122  single    0.970  0.020  1.090
 P2N  C13  C14   single    1.500  0.020  1.500
 P2N  C13  H131  single    0.970  0.020  1.090
 P2N  C13  H132  single    0.970  0.020  1.090
 P2N  C14  C15   double    1.330  0.020  1.330
 P2N  C14  H14   single    0.930  0.020  1.080
 P2N  C15  C16   single    1.498  0.020  1.498
 P2N  C15  H15   single    0.930  0.020  1.080
 P2N  C16  C17   single    1.521  0.020  1.521
 P2N  C16  H161  single    0.970  0.020  1.090
 P2N  C16  H162  single    0.970  0.020  1.090
 P2N  C17  O1    single    1.441  0.020  1.441
 P2N  C17  H171  single    0.970  0.020  1.090
 P2N  C17  H172  single    0.970  0.020  1.090
 P2N  O3   H3    single    0.850  0.020  0.980
 P2N  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
 P2N  O2    C1   O1    123.91  3.000
 P2N  O2    C1   C2    124.05  3.000
 P2N  O1    C1   C2    112.02  3.000
 P2N  C7    C2   C3    119.74  3.000
 P2N  C7    C2   C1    119.22  3.000
 P2N  C3    C2   C1    120.83  3.000
 P2N  O3    C3   C4    116.03  3.000
 P2N  O3    C3   C2    123.95  3.000
 P2N  C4    C3   C2    119.98  3.000
 P2N  H4    C4   C5    120.29  3.000
 P2N  H4    C4   C3    119.24  3.000
 P2N  C5    C4   C3    120.47  3.000
 P2N  O4    C5   C6    117.82  3.000
 P2N  O4    C5   C4    122.83  3.000
 P2N  C6    C5   C4    119.35  3.000
 P2N  CL1   C6   C7    121.15  3.000
 P2N  CL1   C6   C5    117.60  3.000
 P2N  C7    C6   C5    121.25  3.000
 P2N  C8    C7   C6    120.24  3.000
 P2N  C8    C7   C2    120.55  3.000
 P2N  C6    C7   C2    119.10  3.000
 P2N  H8C2  C8   H8C1  104.40  3.000
 P2N  H8C2  C8   C9    106.72  3.000
 P2N  H8C1  C8   C9    109.66  3.000
 P2N  H8C2  C8   C7    110.19  3.000
 P2N  H8C1  C8   C7    110.90  3.000
 P2N  C9    C8   C7    114.43  3.000
 P2N  O5    C9   C10   122.38  3.000
 P2N  O5    C9   C8    121.34  3.000
 P2N  C10   C9   C8    116.25  3.000
 P2N  H102  C10  H101  106.64  3.000
 P2N  H102  C10  C11   110.79  3.000
 P2N  H101  C10  C11   109.65  3.000
 P2N  H102  C10  C9    107.67  3.000
 P2N  H101  C10  C9    108.01  3.000
 P2N  C11   C10  C9    113.79  3.000
 P2N  H112  C11  H111  105.43  3.000
 P2N  H112  C11  C12   109.97  3.000
 P2N  H111  C11  C12   107.84  3.000
 P2N  H112  C11  C10   109.87  3.000
 P2N  H111  C11  C10   108.21  3.000
 P2N  C12   C11  C10   115.05  3.000
 P2N  H122  C12  H121  105.54  3.000
 P2N  H122  C12  C13   109.75  3.000
 P2N  H121  C12  C13   109.02  3.000
 P2N  H122  C12  C11   108.79  3.000
 P2N  H121  C12  C11   111.58  3.000
 P2N  C13   C12  C11   111.95  3.000
 P2N  H132  C13  H131  106.48  3.000
 P2N  H132  C13  C14   110.19  3.000
 P2N  H131  C13  C14   108.55  3.000
 P2N  H132  C13  C12   109.34  3.000
 P2N  H131  C13  C12   109.01  3.000
 P2N  C14   C13  C12   113.03  3.000
 P2N  H14   C14  C15   118.76  3.000
 P2N  H14   C14  C13   115.76  3.000
 P2N  C15   C14  C13   125.48  3.000
 P2N  H15   C15  C16   115.65  3.000
 P2N  H15   C15  C14   119.07  3.000
 P2N  C16   C15  C14   125.20  3.000
 P2N  H162  C16  H161  106.13  3.000
 P2N  H162  C16  C17   105.57  3.000
 P2N  H161  C16  C17   109.31  3.000
 P2N  H162  C16  C15   108.39  3.000
 P2N  H161  C16  C15   110.92  3.000
 P2N  C17   C16  C15   115.93  3.000
 P2N  H172  C17  H171  108.31  3.000
 P2N  H172  C17  O1    110.63  3.000
 P2N  H171  C17  O1    104.35  3.000
 P2N  H172  C17  C16   111.98  3.000
 P2N  H171  C17  C16   109.77  3.000
 P2N  O1    C17  C16   111.49  3.000
 P2N  C17   O1   C1    120.00  3.000
 P2N  H3    O3   C3    111.00  3.000
 P2N  HA    O4   C5    110.56  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
 P2N  CONST_01  C5   C4   C3   C2      0.00   0.0  0
 P2N  CONST_02  C5   C6   C7   C2      0.00   0.0  0
 P2N  CONST_03  C6   C7   C2   C3      0.00   0.0  0
 P2N  CONST_04  C6   C5   C4   C3      0.00   0.0  0
 P2N  CONST_05  C7   C2   C3   C4      0.00   0.0  0
 P2N  CONST_06  C7   C6   C5   C4      0.00   0.0  0
 P2N  CONST_07  O3   C3   C2   C1      0.00   0.0  0
 P2N  CONST_08  CL1  C6   C7   C2    180.00   0.0  0
 P2N  CONST_09  O4   C5   C4   C3    180.00   0.0  0
 P2N  CONST_10  CL1  C6   C5   C4    180.00   0.0  0
 P2N  CONST_11  O3   C3   C4   C5    180.00   0.0  0
 P2N  CONST_12  O3   C3   C2   C7    180.00   0.0  0
 P2N  CONST_13  O4   C5   C6   C7    180.00   0.0  0
 P2N  CONST_14  CL1  C6   C7   C8      0.00   0.0  0
 P2N  CONST_15  H4   C4   C3   C2    180.00   0.0  0
 P2N  Var_01    C16  C15  C14  C13   175.72   0.0  0
 P2N  Var_02    C16  C17  O1   C1     91.33  30.0  1
 P2N  Var_03    C9   C8   C7   C2     96.49  30.0  1
 P2N  Var_04    O1   C1   C2   C3    -45.57  30.0  1
 P2N  Var_05    C10  C9   C8   C7   -170.54  30.0  1
 P2N  Var_06    C11  C10  C9   C8     55.35  30.0  1
 P2N  Var_07    C12  C11  C10  C9    -96.13  30.0  1
 P2N  Var_08    C13  C12  C11  C10   165.54  30.0  1
 P2N  Var_09    C14  C13  C12  C11   -78.18  30.0  1
 P2N  Var_10    C15  C14  C13  C12   104.72  30.0  1
 P2N  Var_11    C17  C16  C15  C14   121.04  30.0  1
 P2N  Var_12    O1   C17  C16  C15   -78.71  30.0  1
 P2N  Var_13    H14  C14  C15  C16    -3.89   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
 P2N  plan-1  C1   0.020
 P2N  plan-1  C2   0.020
 P2N  plan-1  C3   0.020
 P2N  plan-1  C4   0.020
 P2N  plan-1  C5   0.020
 P2N  plan-1  C6   0.020
 P2N  plan-1  C7   0.020
 P2N  plan-1  C8   0.020
 P2N  plan-1  O3   0.020
 P2N  plan-1  O4   0.020
 P2N  plan-1  CL1  0.020
 P2N  plan-1  H4   0.020
 P2N  plan-2  C8   0.020
 P2N  plan-2  C9   0.020
 P2N  plan-2  C10  0.020
 P2N  plan-2  O5   0.020
 P2N  plan-3  C1   0.020
 P2N  plan-3  C2   0.020
 P2N  plan-3  O1   0.020
 P2N  plan-3  O2   0.020
 P2N  plan-4  C13  0.020
 P2N  plan-4  C14  0.020
 P2N  plan-4  C15  0.020
 P2N  plan-4  C16  0.020
 P2N  plan-4  H14  0.020
 P2N  plan-4  H15  0.020

