# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 18:32:07 2021
#   Inital geometry file: a 111 line input string
#   Ligand name: [(~{E})-4-(7-bromanyl-6-chloranyl-4-oxidanylidene-quinazolin-3-yl)but-2-enyl] (2~{S},3~{R})-2-azanyl-3-oxidanyl-butanoate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H](O)[C@H](N)C(=O)OC/C=C/CN1C=Nc2cc(Br)c(Cl)cc2C1=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
 FQR  FQR  '[(~{E})-4-(7-bromanyl-6-chloranyl-4-oxidanylidene-quinazolin-3-yl)but-2-enyl] (2~{S},3~{R})-2-azanyl-3-oxidanyl-butanoate'  ligand  42  25  .  2022-03-18  2022-07-25
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FQR
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
 FQR  O1   O   O2    0  -0.455   3.2160   -5.9965  -2.4593
 FQR  C2   C   C     0   0.562   2.6086   -5.8994  -3.6398
 FQR  C3   C   CH1   0  -0.221   3.4317   -6.4931  -4.7752
 FQR  O4   O   O     0  -0.432   1.5078   -5.4339  -3.7905
 FQR  C5   C   CH1   0   0.069   3.8184   -5.3868  -5.7618
 FQR  C6   C   CH3   0  -0.708   4.5461   -4.2398  -5.0726
 FQR  N7   N   NH2   0  -0.779   2.7052   -7.5547  -5.4442
 FQR  O8   O   OH1   0  -0.664   4.6278   -5.9917  -6.7444
 FQR  C9   C   CH2   0  -0.234   2.4527   -5.6841  -1.2962
 FQR  C10  C   C1    0  -0.252   1.5073   -6.7844  -0.9331
 FQR  C11  C   C1    0  -0.200   1.5209   -8.0013  -1.4610
 FQR  C12  C   CH2   0  -0.388   0.5248   -9.0604  -1.1107
 FQR  N13  N   NR6   0  -0.512  -0.4613   -9.2389  -2.1866
 FQR  C14  C   CR6   0   0.609  -0.0575   -9.8406  -3.3635
 FQR  C15  C   CR66  0  -0.101  -1.1055   -9.9227  -4.3740
 FQR  C16  C   CR66  0   0.267  -2.3745   -9.4060  -4.0914
 FQR  N17  N   N     0  -0.462  -2.6698   -8.8209  -2.8868
 FQR  C18  C   CR16  0   0.158  -1.7263   -8.7639  -2.0216
 FQR  C19  C   CR16  0  -0.225  -0.8387  -10.5057  -5.6121
 FQR  C20  C   CR6   0  -0.029  -1.8283  -10.5791  -6.5649
 FQR  C21  C   CR6   0  -0.055  -3.1061  -10.0644  -6.2865
 FQR  C22  C   CR16  0  -0.293  -3.3757   -9.4855  -5.0671
 FQR  CL2  CL  CL    0  -0.086  -1.4788  -11.3031  -8.0853
 FQR  BR2  BR  BR    0   0.022  -4.4657  -10.1550  -7.5710
 FQR  O25  O   O     0  -0.454   1.0798  -10.2496  -3.5108
 FQR  H1   H   HCH1  0   0.265   4.3520   -6.9159  -4.3636
 FQR  H2   H   HCH1  0   0.203   2.8937   -4.9942  -6.2108
 FQR  H3   H   HCH3  0   0.233   3.9033   -3.7092  -4.3693
 FQR  H4   H   HCH3  0   0.233   5.4265   -4.5953  -4.5336
 FQR  H5   H   HCH3  0   0.244   4.8734   -3.5043  -5.8095
 FQR  H6   H   HNH2  0   0.353   2.5907   -8.3538  -4.8342
 FQR  H7   H   HNH2  0   0.346   1.7781   -7.2405  -5.7044
 FQR  H9   H   HOH1  0   0.451   4.8667   -5.3156  -7.3858
 FQR  H10  H   HCH2  0   0.276   3.1825   -5.5320  -0.4993
 FQR  H11  H   HCH2  0   0.257   1.9094   -4.7448  -1.4195
 FQR  H12  H   H     0   0.269   0.7759   -6.5246  -0.1732
 FQR  H13  H   H     0   0.257   2.2613   -8.2723  -2.2041
 FQR  H14  H   HCH2  0   0.287  -0.0234   -8.7998  -0.2070
 FQR  H15  H   HCH2  0   0.291   1.0099  -10.0196  -0.9327
 FQR  H16  H   HCR6  0   0.300  -1.9225   -8.3070  -1.0591
 FQR  H17  H   HCR6  0   0.297   0.1462  -10.8995  -5.8236
 FQR  H18  H   HCR6  0   0.299  -4.3547   -9.0852  -4.8404

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
 FQR  CL2  C20  single    1.720  0.020  1.720
 FQR  BR2  C21  single    1.873  0.020  1.873
 FQR  O8   C5   single    1.409  0.020  1.409
 FQR  N7   C3   single    1.450  0.020  1.450
 FQR  C20  C21  aromatic  1.405  0.020  1.405
 FQR  C20  C19  aromatic  1.376  0.020  1.376
 FQR  C21  C22  aromatic  1.376  0.020  1.376
 FQR  C5   C3   single    1.532  0.020  1.532
 FQR  C5   C6   single    1.523  0.020  1.523
 FQR  C19  C15  aromatic  1.394  0.020  1.394
 FQR  C3   C2   single    1.523  0.020  1.523
 FQR  C22  C16  aromatic  1.400  0.020  1.400
 FQR  O4   C2   double    1.205  0.020  1.205
 FQR  C15  C16  aromatic  1.399  0.020  1.399
 FQR  C15  C14  single    1.458  0.020  1.458
 FQR  C2   O1   single    1.331  0.020  1.331
 FQR  C16  N17  single    1.371  0.020  1.371
 FQR  O25  C14  double    1.218  0.020  1.218
 FQR  C14  N13  single    1.382  0.020  1.382
 FQR  O1   C9   single    1.426  0.020  1.426
 FQR  N17  C18  double    1.281  0.020  1.281
 FQR  N13  C18  single    1.361  0.020  1.361
 FQR  N13  C12  single    1.470  0.020  1.470
 FQR  C11  C10  double    1.327  0.020  1.327
 FQR  C11  C12  single    1.495  0.020  1.495
 FQR  C9   C10  single    1.495  0.020  1.495
 FQR  C3   H1   single    0.970  0.020  1.090
 FQR  C5   H2   single    0.970  0.020  1.090
 FQR  C6   H3   single    0.970  0.020  1.090
 FQR  C6   H4   single    0.970  0.020  1.090
 FQR  C6   H5   single    0.970  0.020  1.090
 FQR  N7   H6   single    0.890  0.020  1.040
 FQR  N7   H7   single    0.890  0.020  1.040
 FQR  O8   H9   single    0.850  0.020  0.980
 FQR  C9   H10  single    0.970  0.020  1.090
 FQR  C9   H11  single    0.970  0.020  1.090
 FQR  C10  H12  single    0.930  0.020  1.080
 FQR  C11  H13  single    0.930  0.020  1.080
 FQR  C12  H14  single    0.970  0.020  1.090
 FQR  C12  H15  single    0.970  0.020  1.090
 FQR  C18  H16  single    0.930  0.020  1.080
 FQR  C19  H17  single    0.930  0.020  1.080
 FQR  C22  H18  single    0.930  0.020  1.080

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
 FQR  C9   O1   C2   117.59  3.000
 FQR  O4   C2   C3   123.46  3.000
 FQR  O4   C2   O1   123.79  3.000
 FQR  C3   C2   O1   112.71  3.000
 FQR  H1   C3   N7   108.20  3.000
 FQR  H1   C3   C5   108.01  3.000
 FQR  N7   C3   C5   110.98  3.000
 FQR  H1   C3   C2   108.98  3.000
 FQR  C5   C3   C2   109.58  3.000
 FQR  N7   C3   C2   111.02  3.000
 FQR  H2   C5   O8   110.57  3.000
 FQR  H2   C5   C6   108.51  3.000
 FQR  O8   C5   C6   111.36  3.000
 FQR  H2   C5   C3   107.96  3.000
 FQR  C6   C5   C3   111.90  3.000
 FQR  O8   C5   C3   106.50  3.000
 FQR  H5   C6   H4   108.11  3.000
 FQR  H5   C6   H3   106.52  3.000
 FQR  H4   C6   H3   108.38  3.000
 FQR  H5   C6   C5   110.19  3.000
 FQR  H4   C6   C5   111.31  3.000
 FQR  H3   C6   C5   112.13  3.000
 FQR  H7   N7   H6   107.23  3.000
 FQR  H7   N7   C3   110.49  3.000
 FQR  H6   N7   C3   110.90  3.000
 FQR  H9   O8   C5   107.81  3.000
 FQR  H11  C9   H10  107.17  3.000
 FQR  H11  C9   C10  110.23  3.000
 FQR  H10  C9   C10  110.37  3.000
 FQR  H11  C9   O1   111.26  3.000
 FQR  H10  C9   O1   105.56  3.000
 FQR  C10  C9   O1   112.04  3.000
 FQR  H12  C10  C11  120.31  3.000
 FQR  H12  C10  C9   114.81  3.000
 FQR  C11  C10  C9   124.88  3.000
 FQR  H13  C11  C12  116.03  3.000
 FQR  H13  C11  C10  120.62  3.000
 FQR  C12  C11  C10  123.34  3.000
 FQR  H15  C12  H14  107.42  3.000
 FQR  H15  C12  N13  108.13  3.000
 FQR  H14  C12  N13  107.38  3.000
 FQR  H15  C12  C11  111.42  3.000
 FQR  H14  C12  C11  111.12  3.000
 FQR  N13  C12  C11  111.18  3.000
 FQR  C18  N13  C14  121.78  3.000
 FQR  C18  N13  C12  119.48  3.000
 FQR  C14  N13  C12  118.69  3.000
 FQR  O25  C14  C15  124.65  3.000
 FQR  O25  C14  N13  121.48  3.000
 FQR  C15  C14  N13  113.87  3.000
 FQR  C19  C15  C16  120.49  3.000
 FQR  C16  C15  C14  119.41  3.000
 FQR  C19  C15  C14  120.10  3.000
 FQR  C22  C16  N17  118.84  3.000
 FQR  N17  C16  C15  122.03  3.000
 FQR  C22  C16  C15  119.13  3.000
 FQR  C18  N17  C16  116.97  3.000
 FQR  H16  C18  N17  119.03  3.000
 FQR  H16  C18  N13  115.04  3.000
 FQR  N17  C18  N13  125.93  3.000
 FQR  H17  C19  C20  120.01  3.000
 FQR  H17  C19  C15  120.01  3.000
 FQR  C20  C19  C15  119.98  3.000
 FQR  CL2  C20  C21  120.93  3.000
 FQR  C21  C20  C19  119.82  3.000
 FQR  CL2  C20  C19  119.24  3.000
 FQR  BR2  C21  C22  119.07  3.000
 FQR  C22  C21  C20  120.50  3.000
 FQR  BR2  C21  C20  120.43  3.000
 FQR  H18  C22  C21  121.23  3.000
 FQR  H18  C22  C16  118.69  3.000
 FQR  C21  C22  C16  120.08  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
 FQR  CONST_01  C21  C20  C19  C15     0.00   0.0  0
 FQR  CONST_02  C21  C22  C16  C15     0.00   0.0  0
 FQR  CONST_03  C20  C21  C22  C16     0.00   0.0  0
 FQR  CONST_04  C20  C19  C15  C16     0.00   0.0  0
 FQR  CONST_05  C22  C21  C20  C19     0.00   0.0  0
 FQR  CONST_06  C22  C16  C15  C19     0.00   0.0  0
 FQR  CONST_07  C16  N17  C18  N13     0.00   0.0  0
 FQR  CONST_08  N17  C18  N13  C14     0.00   0.0  0
 FQR  CONST_09  C18  N13  C14  C15     0.00   0.0  0
 FQR  CONST_10  CL2  C20  C19  C15   180.00   0.0  0
 FQR  CONST_11  BR2  C21  C22  C16   180.00   0.0  0
 FQR  CONST_12  BR2  C21  C20  C19   180.00   0.0  0
 FQR  CONST_13  CL2  C20  C21  C22   180.00   0.0  0
 FQR  CONST_14  C15  C14  N13  C12   180.00   0.0  0
 FQR  CONST_15  N17  C18  N13  C12   180.00   0.0  0
 FQR  CONST_16  O25  C14  N13  C18   180.00   0.0  0
 FQR  CONST_17  H17  C19  C15  C14     0.00   0.0  0
 FQR  CONST_18  H18  C22  C16  C15   180.00   0.0  0
 FQR  CONST_19  H16  C18  N13  C14   180.00   0.0  0
 FQR  CONST_20  O25  C14  N13  C12     0.00   0.0  0
 FQR  Var_01    C14  N13  C12  C11    71.52  30.0  3
 FQR  Var_02    N13  C12  C11  C10   104.66  30.0  3
 FQR  Var_03    C12  C11  C10  C9   -177.55   0.0  2
 FQR  Var_04    C11  C10  C9   O1     11.27  30.0  3
 FQR  Var_05    C10  C9   O1   C2     76.39  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
 FQR  chir_01  C3  N7  C5  C2  negativ
 FQR  chir_02  C5  O8  C3  C6  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
 FQR  plan-1  C12  0.020
 FQR  plan-1  N13  0.020
 FQR  plan-1  C14  0.020
 FQR  plan-1  C15  0.020
 FQR  plan-1  C16  0.020
 FQR  plan-1  N17  0.020
 FQR  plan-1  C18  0.020
 FQR  plan-1  C19  0.020
 FQR  plan-1  C20  0.020
 FQR  plan-1  C21  0.020
 FQR  plan-1  C22  0.020
 FQR  plan-1  CL2  0.020
 FQR  plan-1  BR2  0.020
 FQR  plan-1  O25  0.020
 FQR  plan-1  H16  0.020
 FQR  plan-1  H17  0.020
 FQR  plan-1  H18  0.020
 FQR  plan-2  O1   0.020
 FQR  plan-2  C2   0.020
 FQR  plan-2  C3   0.020
 FQR  plan-2  O4   0.020
 FQR  plan-3  C9   0.020
 FQR  plan-3  C10  0.020
 FQR  plan-3  C11  0.020
 FQR  plan-3  C12  0.020
 FQR  plan-3  H12  0.020
 FQR  plan-3  H13  0.020

