# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 30 07:10:18 2020
#   Inital geometry file: a 112 line input string
#   Ligand name: ~{N}-[(~{E})-(6-bromanylimidazo[1,2-a]pyridin-3-yl)methylideneamino]-~{N},2-dimethyl-5-nitro-benzenesulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(/N=C/c1cnc2ccc(Br)cn12)[S](=O)(=O)c3cc(ccc3C)[N+]([O-])=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
 F4N  F4N  ~{N}-[(~{E})-(6-bromanylimidazo[1,2-a]pyridin-3-yl)methylideneamino]-~{N},2-dimethyl-5-nitro-benzenesulfonamide  ligand  41  27  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_F4N
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
 F4N  O11  O   OS     0  -0.622  -2.8754   1.1461   2.4435
 F4N  C7   C   CH3    0  -0.747  -3.2825   2.6571  -1.8618
 F4N  C1   C   CR6    0   0.184  -3.7240   1.3104  -1.3809
 F4N  C2   C   CR16   0  -0.297  -4.3378   0.4380  -2.2785
 F4N  C3   C   CR16   0  -0.230  -4.7546  -0.8274  -1.9108
 F4N  C4   C   CR6    0   0.258  -4.5491  -1.2441  -0.6063
 F4N  C5   C   CR16   0  -0.249  -3.9486  -0.4180   0.3261
 F4N  C6   C   CR6    0  -0.237  -3.5509   0.8467  -0.0691
 F4N  O22  O   O     -1  -0.372  -4.7329  -2.9257   0.9302
 F4N  O21  O   O      0  -0.370  -5.5236  -3.2660  -1.0231
 F4N  S9   S   S      0   1.403  -2.8299   1.8748   1.1891
 F4N  O10  O   OS     0  -0.636  -3.3963   3.2097   1.1421
 F4N  N12  N   N      0  -0.437  -1.2523   2.0087   0.6308
 F4N  C13  C   CH3    0  -0.568  -0.4883   3.2256   0.8446
 F4N  N14  N   N      0  -0.192  -0.6875   0.7864   0.5758
 F4N  C15  C   C1     0  -0.125   0.5761   0.6580   0.4829
 F4N  C17  C   CR5    0   0.298   1.1282  -0.6684   0.3702
 F4N  C16  C   CR15   0  -0.194   0.5265  -1.9089   0.2957
 F4N  N20  N   N      0  -0.458   1.4270  -2.9010   0.1958
 F4N  C19  C   CR56   0   0.535   2.6106  -2.3098   0.2040
 F4N  N18  N   N      0  -0.589   2.4779  -0.9354   0.3094
 F4N  C23  C   CR16   0   0.057   3.5522  -0.0976   0.3395
 F4N  C24  C   CR6    0  -0.249   4.7960  -0.6360   0.2585
 F4N  BR2  BR  BR     0  -0.004   6.2890   0.5025   0.2965
 F4N  C25  C   CR16   0  -0.122   4.9886  -2.0357   0.1483
 F4N  C26  C   CR16   0  -0.387   3.9025  -2.8586   0.1229
 F4N  H1   H   HCH3   0   0.268  -2.2205   2.8182  -1.6778
 F4N  H2   H   HCH3   0   0.267  -3.4539   2.7468  -2.9315
 F4N  H3   H   HCH3   0   0.276  -3.8250   3.4583  -1.3632
 F4N  H4   H   HCR6   0   0.287  -4.4897   0.7609  -3.2996
 F4N  H5   H   HCR6   0   0.311  -5.2260  -1.4695  -2.6406
 F4N  H6   H   HCR6   0   0.320  -3.7930  -0.7520   1.3414
 F4N  H7   H   HCH3   0   0.266   0.0872   3.1841   1.7720
 F4N  H8   H   HCH3   0   0.274   0.1896   3.3729   0.0047
 F4N  H9   H   HCH3   0   0.292  -1.1614   4.0756   0.8782
 F4N  H10  H   H      0   0.273   1.2641   1.5006   0.4729
 F4N  H11  H   HCR5   0   0.267  -0.5360  -2.1002   0.3092
 F4N  H12  H   HCR6   0   0.328   3.3633   0.9616   0.4281
 F4N  H13  H   HCR6   0   0.296   5.9863  -2.4466   0.0851
 F4N  H14  H   HCR6   0   0.296   4.0098  -3.9307   0.0416
 F4N  N8   N   N      1   0.330  -4.9665  -2.5778  -0.2025

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
 F4N  C16  N20  aromatic  1.343  0.020  1.343
 F4N  C16  C17  aromatic  1.381  0.020  1.381
 F4N  N20  C19  aromatic  1.323  0.020  1.323
 F4N  C17  C15  single    1.441  0.020  1.441
 F4N  C17  N18  aromatic  1.377  0.020  1.377
 F4N  C13  N12  single    1.453  0.020  1.453
 F4N  C15  N14  double    1.274  0.020  1.274
 F4N  C19  C26  aromatic  1.406  0.020  1.406
 F4N  C19  N18  aromatic  1.385  0.020  1.385
 F4N  C26  C25  aromatic  1.363  0.020  1.363
 F4N  N18  C23  aromatic  1.363  0.020  1.363
 F4N  N14  N12  single    1.348  0.020  1.348
 F4N  N12  S9   single    1.679  0.020  1.679
 F4N  C7   C1   single    1.497  0.020  1.497
 F4N  C25  C24  aromatic  1.417  0.020  1.417
 F4N  C23  C24  aromatic  1.358  0.020  1.358
 F4N  S9   O11  double    1.451  0.020  1.451
 F4N  S9   C6   single    1.778  0.020  1.778
 F4N  S9   O10  double    1.451  0.020  1.451
 F4N  C24  BR2  single    1.878  0.020  1.878
 F4N  C1   C6   aromatic  1.402  0.020  1.402
 F4N  C1   C2   aromatic  1.394  0.020  1.394
 F4N  C6   C5   aromatic  1.383  0.020  1.383
 F4N  C2   C3   aromatic  1.382  0.020  1.382
 F4N  C5   C4   aromatic  1.383  0.020  1.383
 F4N  C3   C4   aromatic  1.385  0.020  1.385
 F4N  C4   N8   single    1.455  0.020  1.455
 F4N  N8   O21  double    1.207  0.020  1.207
 F4N  N8   O22  single    1.208  0.020  1.208
 F4N  C7   H1   single    0.970  0.020  1.090
 F4N  C7   H2   single    0.970  0.020  1.090
 F4N  C7   H3   single    0.970  0.020  1.090
 F4N  C2   H4   single    0.930  0.020  1.080
 F4N  C3   H5   single    0.930  0.020  1.080
 F4N  C5   H6   single    0.930  0.020  1.080
 F4N  C13  H7   single    0.970  0.020  1.090
 F4N  C13  H8   single    0.970  0.020  1.090
 F4N  C13  H9   single    0.970  0.020  1.090
 F4N  C15  H10  single    0.930  0.020  1.080
 F4N  C16  H11  single    0.930  0.020  1.080
 F4N  C23  H12  single    0.930  0.020  1.080
 F4N  C25  H13  single    0.930  0.020  1.080
 F4N  C26  H14  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
 F4N  H3   C7   H2   108.15  3.000
 F4N  H3   C7   H1   107.43  3.000
 F4N  H2   C7   H1   107.91  3.000
 F4N  H3   C7   C1   111.60  3.000
 F4N  H2   C7   C1   110.12  3.000
 F4N  H1   C7   C1   111.48  3.000
 F4N  C6   C1   C2   116.73  3.000
 F4N  C2   C1   C7   119.08  3.000
 F4N  C6   C1   C7   124.18  3.000
 F4N  H4   C2   C3   118.82  3.000
 F4N  H4   C2   C1   118.87  3.000
 F4N  C3   C2   C1   122.31  3.000
 F4N  H5   C3   C4   121.49  3.000
 F4N  H5   C3   C2   119.74  3.000
 F4N  C4   C3   C2   118.77  3.000
 F4N  N8   C4   C5   119.02  3.000
 F4N  N8   C4   C3   119.66  3.000
 F4N  C5   C4   C3   121.32  3.000
 F4N  H6   C5   C6   120.66  3.000
 F4N  H6   C5   C4   120.77  3.000
 F4N  C6   C5   C4   118.57  3.000
 F4N  S9   C6   C5   116.30  3.000
 F4N  C5   C6   C1   122.29  3.000
 F4N  S9   C6   C1   121.40  3.000
 F4N  N12  S9   O10  106.42  3.000
 F4N  O10  S9   C6   110.54  3.000
 F4N  N12  S9   C6   101.06  3.000
 F4N  O10  S9   O11  118.54  3.000
 F4N  C6   S9   O11  107.98  3.000
 F4N  N12  S9   O11  110.91  3.000
 F4N  N14  N12  C13  123.05  3.000
 F4N  N14  N12  S9   109.58  3.000
 F4N  C13  N12  S9   120.80  3.000
 F4N  H9   C13  H8   107.70  3.000
 F4N  H9   C13  H7   109.30  3.000
 F4N  H8   C13  H7   109.39  3.000
 F4N  H9   C13  N12  109.54  3.000
 F4N  H8   C13  N12  109.09  3.000
 F4N  H7   C13  N12  111.73  3.000
 F4N  C15  N14  N12  120.68  3.000
 F4N  H10  C15  C17  118.02  3.000
 F4N  H10  C15  N14  123.38  3.000
 F4N  C17  C15  N14  118.59  3.000
 F4N  N18  C17  C16  104.50  3.000
 F4N  N18  C17  C15  123.88  3.000
 F4N  C16  C17  C15  131.62  3.000
 F4N  H11  C16  N20  121.98  3.000
 F4N  H11  C16  C17  125.96  3.000
 F4N  N20  C16  C17  112.05  3.000
 F4N  C19  N20  C16  105.61  3.000
 F4N  C26  C19  N18  118.68  3.000
 F4N  N18  C19  N20  110.99  3.000
 F4N  C26  C19  N20  130.34  3.000
 F4N  C23  N18  C19  122.43  3.000
 F4N  C23  N18  C17  130.72  3.000
 F4N  C19  N18  C17  106.84  3.000
 F4N  H12  C23  C24  123.66  3.000
 F4N  H12  C23  N18  117.85  3.000
 F4N  C24  C23  N18  118.49  3.000
 F4N  C25  C24  BR2  119.49  3.000
 F4N  BR2  C24  C23  119.12  3.000
 F4N  C25  C24  C23  121.39  3.000
 F4N  H13  C25  C26  120.33  3.000
 F4N  H13  C25  C24  120.36  3.000
 F4N  C26  C25  C24  119.30  3.000
 F4N  H14  C26  C25  121.42  3.000
 F4N  H14  C26  C19  118.87  3.000
 F4N  C25  C26  C19  119.71  3.000
 F4N  O21  N8   O22  124.24  3.000
 F4N  O22  N8   C4   117.96  3.000
 F4N  O21  N8   C4   117.80  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
 F4N  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 F4N  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 F4N  CONST_03  C5   C6   C1   C2      0.00   0.0  0
 F4N  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 F4N  CONST_05  C6   C1   C2   C3      0.00   0.0  0
 F4N  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 F4N  CONST_07  C19  N20  C16  C17     0.00   0.0  0
 F4N  CONST_08  N20  C19  N18  C17     0.00   0.0  0
 F4N  CONST_09  C26  C19  N18  C17   180.00   0.0  0
 F4N  CONST_10  C24  C23  N18  C17   180.00   0.0  0
 F4N  CONST_11  C26  C19  N20  C16   180.00   0.0  0
 F4N  CONST_12  N18  C19  N20  C16     0.00   0.0  0
 F4N  CONST_13  C19  N18  C17  C16     0.00   0.0  0
 F4N  CONST_14  C23  N18  C17  C16   180.00   0.0  0
 F4N  CONST_15  N18  C17  C16  N20     0.00   0.0  0
 F4N  CONST_16  C25  C26  C19  N20   180.00   0.0  0
 F4N  CONST_17  C23  N18  C19  N20   180.00   0.0  0
 F4N  CONST_18  C24  C25  C26  C19     0.00   0.0  0
 F4N  CONST_19  C24  C23  N18  C19     0.00   0.0  0
 F4N  CONST_20  C25  C26  C19  N18     0.00   0.0  0
 F4N  CONST_21  C25  C24  C23  N18     0.00   0.0  0
 F4N  CONST_22  C26  C19  N18  C23     0.00   0.0  0
 F4N  CONST_23  C26  C25  C24  C23     0.00   0.0  0
 F4N  CONST_24  C5   C6   C1   C7    180.00   0.0  0
 F4N  CONST_25  C3   C2   C1   C7    180.00   0.0  0
 F4N  CONST_26  S9   C6   C1   C2    180.00   0.0  0
 F4N  CONST_27  N8   C4   C3   C2    180.00   0.0  0
 F4N  CONST_28  S9   C6   C5   C4    180.00   0.0  0
 F4N  CONST_29  N8   C4   C5   C6    180.00   0.0  0
 F4N  CONST_30  N20  C16  C17  C15   180.00   0.0  0
 F4N  CONST_31  C19  N18  C17  C15   180.00   0.0  0
 F4N  CONST_32  C23  N18  C17  C15     0.00   0.0  0
 F4N  CONST_33  BR2  C24  C23  N18   180.00   0.0  0
 F4N  CONST_34  C26  C25  C24  BR2   180.00   0.0  0
 F4N  CONST_35  H6   C5   C6   C1    180.00   0.0  0
 F4N  CONST_36  H5   C3   C2   C1    180.00   0.0  0
 F4N  CONST_37  H4   C2   C3   C4    180.00   0.0  0
 F4N  CONST_38  H12  C23  N18  C17     0.00   0.0  0
 F4N  CONST_39  H14  C26  C19  N20     0.00   0.0  0
 F4N  CONST_40  H11  C16  N20  C19   180.00   0.0  0
 F4N  CONST_41  H13  C25  C26  C19   180.00   0.0  0
 F4N  CONST_42  O21  N8   C4   C3      0.00   0.0  0
 F4N  CONST_43  O22  N8   C4   C3    180.00   0.0  0
 F4N  CONST_44  O21  N8   C4   C5    180.00   0.0  0
 F4N  CONST_45  O22  N8   C4   C5      0.00   0.0  0
 F4N  Var_01    C1   C6   S9   O11   176.09  30.0  2
 F4N  Var_02    C16  C17  C15  N14     2.48  30.0  2
 F4N  Var_03    H1   C7   C1   C2   -123.78  30.0  2
 F4N  Var_04    C17  C15  N14  N12  -177.41   0.0  2
 F4N  Var_05    C13  N12  S9   C6    146.60  30.0  2
 F4N  Var_06    H7   C13  N12  S9     91.44  30.0  3

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
 F4N  plan-1  C7   0.020
 F4N  plan-1  C1   0.020
 F4N  plan-1  C2   0.020
 F4N  plan-1  C3   0.020
 F4N  plan-1  C4   0.020
 F4N  plan-1  C5   0.020
 F4N  plan-1  C6   0.020
 F4N  plan-1  S9   0.020
 F4N  plan-1  H4   0.020
 F4N  plan-1  H5   0.020
 F4N  plan-1  H6   0.020
 F4N  plan-1  N8   0.020
 F4N  plan-2  C15  0.020
 F4N  plan-2  C17  0.020
 F4N  plan-2  C16  0.020
 F4N  plan-2  N20  0.020
 F4N  plan-2  C19  0.020
 F4N  plan-2  N18  0.020
 F4N  plan-2  C23  0.020
 F4N  plan-2  C24  0.020
 F4N  plan-2  BR2  0.020
 F4N  plan-2  C25  0.020
 F4N  plan-2  C26  0.020
 F4N  plan-2  H11  0.020
 F4N  plan-2  H12  0.020
 F4N  plan-2  H13  0.020
 F4N  plan-2  H14  0.020
 F4N  plan-3  C4   0.020
 F4N  plan-3  O22  0.020
 F4N  plan-3  O21  0.020
 F4N  plan-3  N8   0.020
 F4N  plan-4  N12  0.020
 F4N  plan-4  N14  0.020
 F4N  plan-4  C15  0.020
 F4N  plan-4  C17  0.020
 F4N  plan-4  H10  0.020

