# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 19 21:09:21 2020
#   Inital geometry file: a 125 line input string
#   Ligand name: [(3~{S})-3-carboxy-7-(naphthalen-1-ylmethyl)-5-oxidanylidene-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridin-8-yl]-dimethyl-azanium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[NH+](C)C1=C2SC[C@@H](N2C(=O)C=C1Cc3cccc4ccccc34)C(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
 C8N  C8N  '[(3~{S})-3-carboxy-7-(naphthalen-1-ylmethyl)-5-oxidanylidene-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridin-8-yl]-dimethyl-azanium'  ligand  47  27  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C8N
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
 C8N  O01   O  OC    -1  -0.593  -5.1232   2.0622  -1.0577
 C8N  C02   C  C      0   0.450  -3.9655   1.6140  -1.0319
 C8N  O03   O  O      0  -0.569  -3.1698   1.4482  -1.9644
 C8N  C04   C  CR15   0  -0.257  -3.4793   1.2138   0.3952
 C8N  C05   C  CH2    0  -0.564  -4.3645   0.1551   1.0290
 C8N  S06   S  S2     0   0.095  -3.7499  -1.4036   0.3102
 C8N  C07   C  CR56   0   0.234  -2.1424  -0.7260   0.2131
 C8N  C08   C  CR6    0   0.092  -0.9852  -1.4275   0.0281
 C8N  N09   N  NT1    1  -0.635  -1.1149  -2.8851  -0.0378
 C8N  C10   C  CH3    0  -0.551  -1.1585  -3.4091  -1.4367
 C8N  C11   C  CH3    0  -0.571  -0.1790  -3.6776   0.8198
 C8N  C12   C  CR6    0   0.329   0.2381  -0.7081  -0.1279
 C8N  C13   C  CH2    0  -0.649   1.5536  -1.4112  -0.3803
 C8N  C14   C  CR6    0   0.114   2.7120  -0.5177  -0.7297
 C8N  C15   C  CR16   0  -0.317   3.0521  -0.3400  -2.0460
 C8N  C16   C  CR16   0  -0.245   4.1466   0.4626  -2.4223
 C8N  C17   C  CR16   0  -0.328   4.9026   1.0808  -1.4671
 C8N  C18   C  CR66   0   0.108   4.5894   0.9276  -0.0966
 C8N  C19   C  CR16   0  -0.308   5.3633   1.5609   0.9044
 C8N  C20   C  CR16   0  -0.261   5.0516   1.4177   2.2280
 C8N  C21   C  CR16   0  -0.248   3.9446   0.6330   2.6087
 C8N  C22   C  CR16   0  -0.332   3.1803   0.0051   1.6629
 C8N  C23   C  CR66   0   0.097   3.4800   0.1249   0.2839
 C8N  C24   C  CR16   0  -0.558   0.1875   0.6494  -0.0425
 C8N  C25   C  CR6    0   0.598  -1.0167   1.3955   0.1973
 C8N  O26   O  O      0  -0.495  -1.0848   2.6127   0.2893
 C8N  N27   N  N      0  -0.538  -2.1524   0.6135   0.3414
 C8N  H041  H  HCR5   0   0.310  -3.4494   2.0969   1.0340
 C8N  H052  H  HCH2   0   0.319  -4.2637   0.1084   2.1122
 C8N  H051  H  HCH2   0   0.318  -5.4090   0.2822   0.7603
 C8N  H101  H  HCH3   0   0.297  -0.2017  -3.2327  -1.9152
 C8N  H103  H  HCH3   0   0.303  -1.3662  -4.4745  -1.3992
 C8N  H102  H  HCH3   0   0.298  -1.9452  -2.8952  -1.9811
 C8N  H112  H  HCH3   0   0.305  -0.0351  -3.1591   1.7618
 C8N  H113  H  HCH3   0   0.318  -0.6461  -4.6409   0.9993
 C8N  H111  H  HCH3   0   0.301   0.7633  -3.8305   0.3089
 C8N  H132  H  HCH2   0   0.296   1.8103  -2.0073   0.4975
 C8N  H131  H  HCH2   0   0.296   1.4280  -2.1279  -1.1944
 C8N  H151  H  HCR6   0   0.257   2.4726  -0.8327  -2.8177
 C8N  H161  H  HCR6   0   0.261   4.3873   0.5779  -3.4708
 C8N  H171  H  HCR6   0   0.258   5.7526   1.6915  -1.7466
 C8N  H191  H  HCR6   0   0.257   6.2123   2.1631   0.6037
 C8N  H201  H  HCR6   0   0.260   5.6507   1.9063   2.9852
 C8N  H211  H  HCR6   0   0.261   3.6963   0.5284   3.6567
 C8N  H221  H  HCR6   0   0.245   2.3298  -0.5828   1.9833
 C8N  H241  H  HCR6   0   0.278   1.0834   1.2390  -0.1702
 C8N  H091  H  HNT1   0   0.466  -2.0319  -3.0993   0.3651

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
 C8N  O03  C02   deloc     1.237  0.020  1.237
 C8N  O01  C02   deloc     1.242  0.020  1.242
 C8N  C02  C04   single    1.560  0.020  1.560
 C8N  O26  C25   double    1.222  0.020  1.222
 C8N  C04  C05   single    1.519  0.020  1.519
 C8N  C04  N27   single    1.457  0.020  1.457
 C8N  C05  S06   single    1.823  0.020  1.823
 C8N  C25  N27   single    1.386  0.020  1.386
 C8N  C25  C24   single    1.437  0.020  1.437
 C8N  N27  C07   single    1.346  0.020  1.346
 C8N  C24  C12   double    1.361  0.020  1.361
 C8N  S06  C07   single    1.747  0.020  1.747
 C8N  C07  C08   double    1.366  0.020  1.366
 C8N  C12  C08   single    1.428  0.020  1.428
 C8N  C12  C13   single    1.513  0.020  1.513
 C8N  C08  N09   single    1.465  0.020  1.465
 C8N  C13  C14   single    1.504  0.020  1.504
 C8N  C11  N09   single    1.497  0.020  1.497
 C8N  N09  C10   single    1.494  0.020  1.494
 C8N  C15  C14   aromatic  1.371  0.020  1.371
 C8N  C15  C16   aromatic  1.408  0.020  1.408
 C8N  C14  C23   aromatic  1.425  0.020  1.425
 C8N  C16  C17   aromatic  1.366  0.020  1.366
 C8N  C23  C22   aromatic  1.416  0.020  1.416
 C8N  C23  C18   aromatic  1.421  0.020  1.421
 C8N  C17  C18   aromatic  1.414  0.020  1.414
 C8N  C22  C21   aromatic  1.369  0.020  1.369
 C8N  C18  C19   aromatic  1.415  0.020  1.415
 C8N  C21  C20   aromatic  1.409  0.020  1.409
 C8N  C19  C20   aromatic  1.367  0.020  1.367
 C8N  C04  H041  single    0.970  0.020  1.090
 C8N  C05  H052  single    0.970  0.020  1.090
 C8N  C05  H051  single    0.970  0.020  1.090
 C8N  C10  H101  single    0.970  0.020  1.090
 C8N  C10  H103  single    0.970  0.020  1.090
 C8N  C10  H102  single    0.970  0.020  1.090
 C8N  C11  H112  single    0.970  0.020  1.090
 C8N  C11  H113  single    0.970  0.020  1.090
 C8N  C11  H111  single    0.970  0.020  1.090
 C8N  C13  H132  single    0.970  0.020  1.090
 C8N  C13  H131  single    0.970  0.020  1.090
 C8N  C15  H151  single    0.930  0.020  1.080
 C8N  C16  H161  single    0.930  0.020  1.080
 C8N  C17  H171  single    0.930  0.020  1.080
 C8N  C19  H191  single    0.930  0.020  1.080
 C8N  C20  H201  single    0.930  0.020  1.080
 C8N  C21  H211  single    0.930  0.020  1.080
 C8N  C22  H221  single    0.930  0.020  1.080
 C8N  C24  H241  single    0.930  0.020  1.080
 C8N  N09  H091  single    0.890  0.020  1.040

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
 C8N  C04   C02  O03   117.05  3.000
 C8N  C04   C02  O01   113.72  3.000
 C8N  O03   C02  O01   129.23  3.000
 C8N  H041  C04  N27   109.29  3.000
 C8N  H041  C04  C05   109.64  3.000
 C8N  N27   C04  C05   105.01  3.000
 C8N  H041  C04  C02   109.67  3.000
 C8N  N27   C04  C02   110.83  3.000
 C8N  C05   C04  C02   112.27  3.000
 C8N  H051  C05  H052  109.89  3.000
 C8N  H051  C05  S06   109.07  3.000
 C8N  H052  C05  S06   108.93  3.000
 C8N  H051  C05  C04   112.07  3.000
 C8N  H052  C05  C04   113.02  3.000
 C8N  S06   C05  C04   103.59  3.000
 C8N  C07   S06  C05    90.03  3.000
 C8N  N27   C07  C08   122.04  3.000
 C8N  C08   C07  S06   126.01  3.000
 C8N  N27   C07  S06   111.96  3.000
 C8N  C12   C08  N09   124.91  3.000
 C8N  N09   C08  C07   116.24  3.000
 C8N  C12   C08  C07   118.82  3.000
 C8N  H091  N09  C11   102.93  3.000
 C8N  H091  N09  C10   105.59  3.000
 C8N  C11   N09  C10   111.65  3.000
 C8N  H091  N09  C08   105.65  3.000
 C8N  C10   N09  C08   113.18  3.000
 C8N  C11   N09  C08   116.48  3.000
 C8N  H102  C10  H103  110.05  3.000
 C8N  H102  C10  H101  109.95  3.000
 C8N  H103  C10  H101  110.10  3.000
 C8N  H102  C10  N09   108.93  3.000
 C8N  H103  C10  N09   108.49  3.000
 C8N  H101  C10  N09   109.29  3.000
 C8N  H111  C11  H113  109.10  3.000
 C8N  H111  C11  H112  111.21  3.000
 C8N  H113  C11  H112  109.73  3.000
 C8N  H111  C11  N09   110.40  3.000
 C8N  H113  C11  N09   107.20  3.000
 C8N  H112  C11  N09   109.11  3.000
 C8N  C24   C12  C13   120.42  3.000
 C8N  C13   C12  C08   121.95  3.000
 C8N  C24   C12  C08   117.64  3.000
 C8N  H131  C13  H132  105.56  3.000
 C8N  H131  C13  C14   107.78  3.000
 C8N  H132  C13  C14   109.27  3.000
 C8N  H131  C13  C12   109.23  3.000
 C8N  H132  C13  C12   108.91  3.000
 C8N  C14   C13  C12   115.62  3.000
 C8N  C23   C14  C15   119.39  3.000
 C8N  C23   C14  C13   121.19  3.000
 C8N  C15   C14  C13   119.41  3.000
 C8N  H151  C15  C16   118.98  3.000
 C8N  H151  C15  C14   119.48  3.000
 C8N  C16   C15  C14   121.54  3.000
 C8N  H161  C16  C17   120.42  3.000
 C8N  H161  C16  C15   119.50  3.000
 C8N  C17   C16  C15   120.07  3.000
 C8N  H171  C17  C18   119.00  3.000
 C8N  H171  C17  C16   120.59  3.000
 C8N  C18   C17  C16   120.41  3.000
 C8N  C23   C18  C19   119.36  3.000
 C8N  C19   C18  C17   121.07  3.000
 C8N  C23   C18  C17   119.57  3.000
 C8N  H191  C19  C20   120.36  3.000
 C8N  H191  C19  C18   118.75  3.000
 C8N  C20   C19  C18   120.89  3.000
 C8N  H201  C20  C21   119.81  3.000
 C8N  H201  C20  C19   120.26  3.000
 C8N  C21   C20  C19   119.93  3.000
 C8N  H211  C21  C22   119.78  3.000
 C8N  H211  C21  C20   119.72  3.000
 C8N  C22   C21  C20   120.50  3.000
 C8N  H221  C22  C23   120.03  3.000
 C8N  H221  C22  C21   118.92  3.000
 C8N  C23   C22  C21   121.06  3.000
 C8N  C22   C23  C18   118.27  3.000
 C8N  C18   C23  C14   119.02  3.000
 C8N  C22   C23  C14   122.71  3.000
 C8N  H241  C24  C25   115.56  3.000
 C8N  H241  C24  C12   120.41  3.000
 C8N  C25   C24  C12   124.02  3.000
 C8N  N27   C25  O26   120.54  3.000
 C8N  N27   C25  C24   114.27  3.000
 C8N  O26   C25  C24   125.19  3.000
 C8N  C25   N27  C07   123.06  3.000
 C8N  C07   N27  C04   114.85  3.000
 C8N  C25   N27  C04   121.15  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
 C8N  CONST_01  C17   C16  C15  C14     0.00   0.0  0
 C8N  CONST_02  C21   C22  C23  C14   180.00   0.0  0
 C8N  CONST_03  C17   C18  C23  C14     0.00   0.0  0
 C8N  CONST_04  C19   C18  C23  C14   180.00   0.0  0
 C8N  CONST_05  C22   C23  C14  C15   180.00   0.0  0
 C8N  CONST_06  C18   C23  C14  C15     0.00   0.0  0
 C8N  CONST_07  C18   C17  C16  C15     0.00   0.0  0
 C8N  CONST_08  C23   C14  C15  C16     0.00   0.0  0
 C8N  CONST_09  C23   C18  C17  C16     0.00   0.0  0
 C8N  CONST_10  C19   C18  C17  C16   180.00   0.0  0
 C8N  CONST_11  C22   C23  C18  C17   180.00   0.0  0
 C8N  CONST_12  C20   C19  C18  C17   180.00   0.0  0
 C8N  CONST_13  C21   C22  C23  C18     0.00   0.0  0
 C8N  CONST_14  C21   C20  C19  C18     0.00   0.0  0
 C8N  CONST_15  C22   C23  C18  C19     0.00   0.0  0
 C8N  CONST_16  C22   C21  C20  C19     0.00   0.0  0
 C8N  CONST_17  C23   C22  C21  C20     0.00   0.0  0
 C8N  CONST_18  C23   C18  C19  C20     0.00   0.0  0
 C8N  CONST_19  C24   C25  N27  C04   180.00   0.0  0
 C8N  CONST_20  C24   C25  N27  C07     0.00   0.0  0
 C8N  CONST_21  C16   C15  C14  C13   180.00   0.0  0
 C8N  CONST_22  C22   C23  C14  C13     0.00   0.0  0
 C8N  CONST_23  C18   C23  C14  C13   180.00   0.0  0
 C8N  CONST_24  O26   C25  N27  C04     0.00   0.0  0
 C8N  CONST_25  O26   C25  N27  C07   180.00   0.0  0
 C8N  CONST_26  H161  C16  C15  C14   180.00   0.0  0
 C8N  CONST_27  H221  C22  C23  C14     0.00   0.0  0
 C8N  CONST_28  H171  C17  C16  C15   180.00   0.0  0
 C8N  CONST_29  H151  C15  C16  C17   180.00   0.0  0
 C8N  CONST_30  H191  C19  C18  C17     0.00   0.0  0
 C8N  CONST_31  H201  C20  C19  C18   180.00   0.0  0
 C8N  CONST_32  H211  C21  C20  C19   180.00   0.0  0
 C8N  Var_01    N27   C07  S06  C05   -16.06  30.0  1
 C8N  Var_02    C14   C13  C12  C08   171.06  30.0  3
 C8N  Var_03    C15   C14  C13  C12   -97.56  30.0  2
 C8N  Var_04    H052  C05  S06  C07   -89.19  30.0  1
 C8N  Var_05    C11   N09  C08  C07  -131.04  30.0  3
 C8N  Var_06    H112  C11  N09  C08    37.35  30.0  3
 C8N  Var_07    H101  C10  N09  C08    66.20  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
 C8N  chir_01  C04  C02  C05  N27  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
 C8N  plan-1  C13   0.020
 C8N  plan-1  C14   0.020
 C8N  plan-1  C15   0.020
 C8N  plan-1  C16   0.020
 C8N  plan-1  C17   0.020
 C8N  plan-1  C18   0.020
 C8N  plan-1  C19   0.020
 C8N  plan-1  C20   0.020
 C8N  plan-1  C21   0.020
 C8N  plan-1  C22   0.020
 C8N  plan-1  C23   0.020
 C8N  plan-1  H151  0.020
 C8N  plan-1  H161  0.020
 C8N  plan-1  H171  0.020
 C8N  plan-1  H191  0.020
 C8N  plan-1  H201  0.020
 C8N  plan-1  H211  0.020
 C8N  plan-1  H221  0.020
 C8N  plan-2  C04   0.020
 C8N  plan-2  S06   0.020
 C8N  plan-2  C07   0.020
 C8N  plan-2  C08   0.020
 C8N  plan-2  N09   0.020
 C8N  plan-2  C12   0.020
 C8N  plan-2  C13   0.020
 C8N  plan-2  C24   0.020
 C8N  plan-2  C25   0.020
 C8N  plan-2  O26   0.020
 C8N  plan-2  N27   0.020
 C8N  plan-2  H241  0.020
 C8N  plan-3  O01   0.020
 C8N  plan-3  C02   0.020
 C8N  plan-3  O03   0.020
 C8N  plan-3  C04   0.020

