# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 21 02:59:57 2022
#   Inital geometry file: a 142 line input string
#   Ligand name: 4-[5-[2-(2-hydroxyethyloxy)ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrazolo[1,5-a]pyrimidin-3-yl]-2-oxidanyl-benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(C)OC(=O)N(CCOCCO)c1ccn2ncc(c3ccc(C(O)=O)c(O)c3)c2n1
#
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
 PQ8  PQ8  '4-[5-[2-(2-hydroxyethyloxy)ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrazolo[1,5-a]pyrimidin-3-yl]-2-oxidanyl-benzoic acid'  ligand  58  33  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_PQ8
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
 PQ8  C1   C  CT     0   0.185  43.7916   3.3484   3.2504
 PQ8  C2   C  CH3    0  -0.666  43.2265   4.3174   4.2800
 PQ8  O5   O  O      0  -0.596  45.5887   2.9250  -9.1178
 PQ8  C7   C  CH2    0  -0.175  46.1238   1.2790  -1.8048
 PQ8  C8   C  CH2    0  -0.185  47.5420   1.0116  -2.2399
 PQ8  C9   C  CR6    0   0.532  42.5011   5.3969  -0.9359
 PQ8  C10  C  CR56   0   0.601  41.9683   5.6871  -3.1319
 PQ8  C11  C  CR5    0  -0.212  41.9695   5.5969  -4.5222
 PQ8  C12  C  CR6    0   0.140  42.8734   4.8289  -5.3695
 PQ8  C13  C  CR16   0  -0.365  42.6499   4.6975  -6.7420
 PQ8  C14  C  CR16   0  -0.264  43.5386   3.9751  -7.5181
 PQ8  C15  C  CR6    0  -0.196  44.6567   3.3242  -6.9959
 PQ8  C16  C  C      0   0.381  45.5425   2.5159  -7.9402
 PQ8  N    N  NT     0  -0.599  43.3901   4.8254  -0.0250
 PQ8  C    C  C      0   0.773  42.9560   4.4521   1.2380
 PQ8  O    O  O      0  -0.477  41.8068   4.5355   1.5991
 PQ8  N3   N  N      0  -0.374  40.9350   6.5329  -2.8018
 PQ8  O4   O  OC    -1  -0.586  46.1146   1.5148  -7.4739
 PQ8  C17  C  CR6    0   0.382  44.8728   3.4583  -5.6173
 PQ8  C18  C  CR16   0  -0.544  44.0001   4.2083  -4.8327
 PQ8  C19  C  CR15   0  -0.078  40.8959   6.4266  -4.8950
 PQ8  N2   N  N      0  -0.297  40.2771   6.9890  -3.8707
 PQ8  N1   N  N      0  -0.490  42.7283   5.1255  -2.1893
 PQ8  C20  C  CR16   0   0.072  40.6923   6.8483  -1.5104
 PQ8  C21  C  CR16   0  -0.404  41.4624   6.2953  -0.5408
 PQ8  O1   O  O2     0  -0.488  43.9642   4.0021   1.9555
 PQ8  C4   C  CH3    0  -0.676  42.9377   2.0970   3.0998
 PQ8  C3   C  CH3    0  -0.657  45.2161   2.9636   3.6257
 PQ8  C5   C  CH2    0  -0.363  44.6960   4.3926  -0.5299
 PQ8  C6   C  CH2    0  -0.133  44.6906   2.9364  -0.9728
 PQ8  O2   O  O2     0  -0.493  45.9528   2.6492  -1.5221
 PQ8  O3   O  OH1    0  -0.666  48.4128   1.2592  -1.1615
 PQ8  H1   H  HCH3   0   0.238  43.2905   3.8582   5.2670
 PQ8  H2   H  HCH3   0   0.238  43.8090   5.2393   4.3074
 PQ8  H3   H  HCH3   0   0.247  42.1842   4.5652   4.0955
 PQ8  H4   H  HCH2   0   0.209  45.4448   0.9536  -2.6048
 PQ8  H5   H  HCH2   0   0.216  45.8889   0.6707  -0.9201
 PQ8  H6   H  HCH2   0   0.203  47.5854  -0.0327  -2.5748
 PQ8  H7   H  HCH2   0   0.200  47.7868   1.6311  -3.1129
 PQ8  H8   H  HCR6   0   0.234  41.7870   5.1552  -7.2089
 PQ8  H9   H  HCR6   0   0.239  43.3571   3.8986  -8.5822
 PQ8  H10  H  HOH1   0   0.463  45.9846   3.1401  -4.1083
 PQ8  H12  H  HCR6   0   0.286  44.2074   4.3058  -3.7737
 PQ8  H13  H  HCR5   0   0.273  40.5512   6.6420  -5.8958
 PQ8  H14  H  HCR6   0   0.326  39.8932   7.5495  -1.3175
 PQ8  H15  H  HCR6   0   0.301  41.2886   6.5709   0.4846
 PQ8  H16  H  HCH3   0   0.242  42.9588   1.5400   4.0370
 PQ8  H17  H  HCH3   0   0.247  41.8978   2.3213   2.8718
 PQ8  H18  H  HCH3   0   0.241  43.3372   1.4460   2.3205
 PQ8  H19  H  HCH3   0   0.234  45.2129   2.4481   4.5854
 PQ8  H20  H  HCH3   0   0.240  45.6548   2.2932   2.8852
 PQ8  H21  H  HCH3   0   0.240  45.8539   3.8437   3.7185
 PQ8  H22  H  HCH2   0   0.277  45.4480   4.5565   0.2387
 PQ8  H23  H  HCH2   0   0.270  44.9534   5.0310  -1.3724
 PQ8  H24  H  HCH2   0   0.213  43.8940   2.7695  -1.7085
 PQ8  H25  H  HCH2   0   0.213  44.4863   2.2815  -0.1149
 PQ8  H26  H  HOH1   0   0.453  49.3119   1.0900  -1.4564
 PQ8  O6   O  OH1    0  -0.626  45.9577   2.8961  -5.0417

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
 PQ8  O5   C16  deloc     1.247  0.020  1.247
 PQ8  C16  O4   deloc     1.244  0.020  1.244
 PQ8  C16  C15  single    1.526  0.020  1.526
 PQ8  C14  C15  aromatic  1.395  0.020  1.395
 PQ8  C14  C13  aromatic  1.383  0.020  1.383
 PQ8  C15  C17  aromatic  1.402  0.020  1.402
 PQ8  C13  C12  aromatic  1.397  0.020  1.397
 PQ8  C17  O6   single    1.351  0.020  1.351
 PQ8  C17  C18  aromatic  1.393  0.020  1.393
 PQ8  C12  C18  aromatic  1.394  0.020  1.394
 PQ8  C12  C11  single    1.458  0.020  1.458
 PQ8  C19  C11  aromatic  1.407  0.020  1.407
 PQ8  C19  N2   aromatic  1.322  0.020  1.322
 PQ8  C11  C10  aromatic  1.393  0.020  1.393
 PQ8  N2   N3   aromatic  1.335  0.020  1.335
 PQ8  C10  N3   aromatic  1.375  0.020  1.375
 PQ8  C10  N1   aromatic  1.335  0.020  1.335
 PQ8  N3   C20  aromatic  1.351  0.020  1.351
 PQ8  N1   C9   aromatic  1.302  0.020  1.302
 PQ8  C7   C8   single    1.507  0.020  1.507
 PQ8  C7   O2   single    1.409  0.020  1.409
 PQ8  C20  C21  aromatic  1.356  0.020  1.356
 PQ8  C8   O3   single    1.408  0.020  1.408
 PQ8  C9   C21  aromatic  1.429  0.020  1.429
 PQ8  C9   N    single    1.395  0.020  1.395
 PQ8  C6   O2   single    1.406  0.020  1.406
 PQ8  C6   C5   single    1.522  0.020  1.522
 PQ8  C5   N    single    1.465  0.020  1.465
 PQ8  N    C    single    1.387  0.020  1.387
 PQ8  C    O    double    1.208  0.020  1.208
 PQ8  C    O1   single    1.317  0.020  1.317
 PQ8  O1   C1   single    1.461  0.020  1.461
 PQ8  C3   C1   single    1.523  0.020  1.523
 PQ8  C4   C1   single    1.522  0.020  1.522
 PQ8  C1   C2   single    1.523  0.020  1.523
 PQ8  C2   H1   single    0.970  0.020  1.090
 PQ8  C2   H2   single    0.970  0.020  1.090
 PQ8  C2   H3   single    0.970  0.020  1.090
 PQ8  C7   H4   single    0.970  0.020  1.090
 PQ8  C7   H5   single    0.970  0.020  1.090
 PQ8  C8   H6   single    0.970  0.020  1.090
 PQ8  C8   H7   single    0.970  0.020  1.090
 PQ8  C13  H8   single    0.930  0.020  1.080
 PQ8  C14  H9   single    0.930  0.020  1.080
 PQ8  O6   H10  single    0.850  0.020  0.980
 PQ8  C18  H12  single    0.930  0.020  1.080
 PQ8  C19  H13  single    0.930  0.020  1.080
 PQ8  C20  H14  single    0.930  0.020  1.080
 PQ8  C21  H15  single    0.930  0.020  1.080
 PQ8  C4   H16  single    0.970  0.020  1.090
 PQ8  C4   H17  single    0.970  0.020  1.090
 PQ8  C4   H18  single    0.970  0.020  1.090
 PQ8  C3   H19  single    0.970  0.020  1.090
 PQ8  C3   H20  single    0.970  0.020  1.090
 PQ8  C3   H21  single    0.970  0.020  1.090
 PQ8  C5   H22  single    0.970  0.020  1.090
 PQ8  C5   H23  single    0.970  0.020  1.090
 PQ8  C6   H24  single    0.970  0.020  1.090
 PQ8  C6   H25  single    0.970  0.020  1.090
 PQ8  O3   H26  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
 PQ8  C3   C1   C4   109.96  3.000
 PQ8  C4   C1   O1   110.27  3.000
 PQ8  C3   C1   O1   102.77  3.000
 PQ8  C4   C1   C2   112.45  3.000
 PQ8  C3   C1   C2   109.96  3.000
 PQ8  O1   C1   C2   111.01  3.000
 PQ8  H3   C2   H2   108.88  3.000
 PQ8  H3   C2   H1   107.81  3.000
 PQ8  H2   C2   H1   107.56  3.000
 PQ8  H3   C2   C1   112.71  3.000
 PQ8  H2   C2   C1   110.89  3.000
 PQ8  H1   C2   C1   108.80  3.000
 PQ8  H5   C7   H4   106.86  3.000
 PQ8  H5   C7   O2   110.53  3.000
 PQ8  H4   C7   O2   111.04  3.000
 PQ8  H5   C7   C8   109.59  3.000
 PQ8  H4   C7   C8   108.59  3.000
 PQ8  O2   C7   C8   110.15  3.000
 PQ8  H7   C8   H6   106.58  3.000
 PQ8  H7   C8   O3   111.83  3.000
 PQ8  H6   C8   O3   112.12  3.000
 PQ8  H7   C8   C7   109.82  3.000
 PQ8  H6   C8   C7   107.10  3.000
 PQ8  O3   C8   C7   109.24  3.000
 PQ8  C21  C9   N1   121.59  3.000
 PQ8  C21  C9   N    122.69  3.000
 PQ8  N1   C9   N    115.59  3.000
 PQ8  N1   C10  N3   121.13  3.000
 PQ8  N1   C10  C11  132.61  3.000
 PQ8  N3   C10  C11  106.26  3.000
 PQ8  C19  C11  C12  129.03  3.000
 PQ8  C19  C11  C10  103.04  3.000
 PQ8  C12  C11  C10  127.93  3.000
 PQ8  C18  C12  C13  117.77  3.000
 PQ8  C18  C12  C11  120.79  3.000
 PQ8  C13  C12  C11  121.44  3.000
 PQ8  H8   C13  C14  119.40  3.000
 PQ8  H8   C13  C12  120.76  3.000
 PQ8  C14  C13  C12  119.84  3.000
 PQ8  H9   C14  C15  118.00  3.000
 PQ8  H9   C14  C13  118.74  3.000
 PQ8  C15  C14  C13  123.26  3.000
 PQ8  C17  C15  C16  124.72  3.000
 PQ8  C17  C15  C14  116.55  3.000
 PQ8  C16  C15  C14  118.73  3.000
 PQ8  O4   C16  C15  117.47  3.000
 PQ8  C15  C16  O5   115.58  3.000
 PQ8  O4   C16  O5   126.93  3.000
 PQ8  C5   N    C    120.88  3.000
 PQ8  C    N    C9   120.37  3.000
 PQ8  C5   N    C9   117.63  3.000
 PQ8  O1   C    O    126.11  3.000
 PQ8  O1   C    N    110.41  3.000
 PQ8  O    C    N    123.48  3.000
 PQ8  C20  N3   N2   126.64  3.000
 PQ8  C20  N3   C10  120.51  3.000
 PQ8  N2   N3   C10  112.83  3.000
 PQ8  C18  C17  O6   119.17  3.000
 PQ8  C18  C17  C15  120.59  3.000
 PQ8  O6   C17  C15  120.20  3.000
 PQ8  H12  C18  C17  118.63  3.000
 PQ8  H12  C18  C12  119.41  3.000
 PQ8  C17  C18  C12  121.96  3.000
 PQ8  H13  C19  N2   118.92  3.000
 PQ8  H13  C19  C11  127.34  3.000
 PQ8  N2   C19  C11  113.74  3.000
 PQ8  C19  N2   N3   104.13  3.000
 PQ8  C10  N1   C9   119.51  3.000
 PQ8  H14  C20  C21  123.85  3.000
 PQ8  H14  C20  N3   117.05  3.000
 PQ8  C21  C20  N3   119.09  3.000
 PQ8  H15  C21  C20  119.02  3.000
 PQ8  H15  C21  C9   122.82  3.000
 PQ8  C20  C21  C9   118.13  3.000
 PQ8  C    O1   C1   123.06  3.000
 PQ8  H18  C4   H17  108.86  3.000
 PQ8  H18  C4   H16  107.57  3.000
 PQ8  H17  C4   H16  107.69  3.000
 PQ8  H18  C4   C1   110.84  3.000
 PQ8  H17  C4   C1   112.79  3.000
 PQ8  H16  C4   C1   108.91  3.000
 PQ8  H21  C3   H20  108.56  3.000
 PQ8  H21  C3   H19  107.97  3.000
 PQ8  H20  C3   H19  107.96  3.000
 PQ8  H21  C3   C1   111.35  3.000
 PQ8  H20  C3   C1   111.36  3.000
 PQ8  H19  C3   C1   109.52  3.000
 PQ8  H23  C5   H22  107.18  3.000
 PQ8  H23  C5   C6   109.68  3.000
 PQ8  H22  C5   C6   110.62  3.000
 PQ8  H23  C5   N    107.72  3.000
 PQ8  H22  C5   N    109.16  3.000
 PQ8  C6   C5   N    112.31  3.000
 PQ8  H25  C6   H24  107.34  3.000
 PQ8  H25  C6   O2   110.51  3.000
 PQ8  H24  C6   O2   111.02  3.000
 PQ8  H25  C6   C5   110.10  3.000
 PQ8  H24  C6   C5   110.08  3.000
 PQ8  O2   C6   C5   107.81  3.000
 PQ8  C6   O2   C7   112.69  3.000
 PQ8  H26  O3   C8   108.22  3.000
 PQ8  H10  O6   C17  109.22  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
 PQ8  CONST_01  C11  C10  N1   C9    180.00   0.0  0
 PQ8  CONST_02  N3   C10  N1   C9      0.00   0.0  0
 PQ8  CONST_03  N3   C20  C21  C9      0.00   0.0  0
 PQ8  CONST_04  C13  C12  C11  C10   180.00   0.0  0
 PQ8  CONST_05  C18  C12  C11  C10     0.00   0.0  0
 PQ8  CONST_06  N2   C19  C11  C10     0.00   0.0  0
 PQ8  CONST_07  C19  N2   N3   C10     0.00   0.0  0
 PQ8  CONST_08  C21  C20  N3   C10     0.00   0.0  0
 PQ8  CONST_09  C21  C9   N1   C10     0.00   0.0  0
 PQ8  CONST_10  C14  C13  C12  C11   180.00   0.0  0
 PQ8  CONST_11  C17  C18  C12  C11   180.00   0.0  0
 PQ8  CONST_12  N3   N2   C19  C11     0.00   0.0  0
 PQ8  CONST_13  N2   N3   C10  C11     0.00   0.0  0
 PQ8  CONST_14  C20  N3   C10  C11   180.00   0.0  0
 PQ8  CONST_15  C15  C14  C13  C12     0.00   0.0  0
 PQ8  CONST_16  C15  C17  C18  C12     0.00   0.0  0
 PQ8  CONST_17  N2   C19  C11  C12   180.00   0.0  0
 PQ8  CONST_18  N3   C10  C11  C12   180.00   0.0  0
 PQ8  CONST_19  N1   C10  C11  C12     0.00   0.0  0
 PQ8  CONST_20  C17  C15  C14  C13     0.00   0.0  0
 PQ8  CONST_21  C17  C18  C12  C13     0.00   0.0  0
 PQ8  CONST_22  C19  C11  C12  C13     0.00   0.0  0
 PQ8  CONST_23  C18  C17  C15  C14     0.00   0.0  0
 PQ8  CONST_24  C18  C12  C13  C14     0.00   0.0  0
 PQ8  CONST_25  C19  C11  C10  N3      0.00   0.0  0
 PQ8  CONST_26  C19  C11  C12  C18   180.00   0.0  0
 PQ8  CONST_27  N1   C10  C11  C19   180.00   0.0  0
 PQ8  CONST_28  C20  N3   N2   C19   180.00   0.0  0
 PQ8  CONST_29  N1   C10  N3   N2    180.00   0.0  0
 PQ8  CONST_30  C21  C20  N3   N2    180.00   0.0  0
 PQ8  CONST_31  C20  N3   C10  N1      0.00   0.0  0
 PQ8  CONST_32  C20  C21  C9   N1      0.00   0.0  0
 PQ8  CONST_33  N    C9   N1   C10   180.00   0.0  0
 PQ8  CONST_34  O6   C17  C18  C12   180.00   0.0  0
 PQ8  CONST_35  C16  C15  C14  C13   180.00   0.0  0
 PQ8  CONST_36  O6   C17  C15  C14   180.00   0.0  0
 PQ8  CONST_37  C18  C17  C15  C16   180.00   0.0  0
 PQ8  CONST_38  C20  C21  C9   N     180.00   0.0  0
 PQ8  CONST_39  H14  C20  C21  C9    180.00   0.0  0
 PQ8  CONST_40  H13  C19  C11  C10   180.00   0.0  0
 PQ8  CONST_41  H8   C13  C12  C11     0.00   0.0  0
 PQ8  CONST_42  H12  C18  C12  C11     0.00   0.0  0
 PQ8  CONST_43  H9   C14  C13  C12   180.00   0.0  0
 PQ8  CONST_44  H15  C21  C20  N3    180.00   0.0  0
 PQ8  CONST_49  O    C    N    C9      0.00   0.0  0
 PQ8  CONST_50  O1   C    N    C9    180.00   0.0  0
 PQ8  Var_01    C14  C15  C16  O5     30.12  30.0  2
 PQ8  Var_02    C6   C5   N    C9    -91.65  30.0  2
 PQ8  Var_03    N    C    O1   C1   -170.45  30.0  2
 PQ8  Var_04    C5   C6   O2   C7    172.08  30.0  2
 PQ8  Var_05    O2   C6   C5   N     175.99  30.0  2
 PQ8  Var_06    C3   C1   O1   C     177.33  30.0  3
 PQ8  Var_07    O3   C8   C7   O2     65.82  30.0  3
 PQ8  Var_08    H19  C3   C1   C2     62.46  30.0  3
 PQ8  Var_09    H16  C4   C1   C2    -64.77  30.0  3
 PQ8  Var_10    H1   C2   C1   O1   -169.28  30.0  3
 PQ8  Var_11    H4   C7   O2   C6     66.13  30.0  1

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
 PQ8  plan-1  C11  0.020
 PQ8  plan-1  C12  0.020
 PQ8  plan-1  C13  0.020
 PQ8  plan-1  C14  0.020
 PQ8  plan-1  C15  0.020
 PQ8  plan-1  C16  0.020
 PQ8  plan-1  C17  0.020
 PQ8  plan-1  C18  0.020
 PQ8  plan-1  H8   0.020
 PQ8  plan-1  H9   0.020
 PQ8  plan-1  H12  0.020
 PQ8  plan-1  O6   0.020
 PQ8  plan-2  C9   0.020
 PQ8  plan-2  C10  0.020
 PQ8  plan-2  C11  0.020
 PQ8  plan-2  C12  0.020
 PQ8  plan-2  N    0.020
 PQ8  plan-2  N3   0.020
 PQ8  plan-2  C19  0.020
 PQ8  plan-2  N2   0.020
 PQ8  plan-2  N1   0.020
 PQ8  plan-2  C20  0.020
 PQ8  plan-2  C21  0.020
 PQ8  plan-2  H13  0.020
 PQ8  plan-2  H14  0.020
 PQ8  plan-2  H15  0.020
 PQ8  plan-3  C9   0.020
 PQ8  plan-3  N    0.020
 PQ8  plan-3  C    0.020
 PQ8  plan-3  C5   0.020
 PQ8  plan-4  O5   0.020
 PQ8  plan-4  C15  0.020
 PQ8  plan-4  C16  0.020
 PQ8  plan-4  O4   0.020
 PQ8  plan-5  N    0.020
 PQ8  plan-5  C    0.020
 PQ8  plan-5  O    0.020
 PQ8  plan-5  O1   0.020

