# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  8 10:17:00 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: (1S)-1-carboxy-2-(5-{2-[(3-chlorophenyl)methyl]-2H-tetrazol-5-yl}-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)ethan-1-aminium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: [NH3+][C@@H](CC1=C(ONC1=O)c2nnn(Cc3cccc(Cl)c3)n2)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
 5XN  5XN  (1S)-1-carboxy-2-(5-{2-[(3-chlorophenyl)methyl]-2H-tetrazol-5-yl}-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)ethan-1-aminium  ligand  38  25  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_5XN
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
 5XN  C1    C   CR5    0  -0.238  -2.6682  -0.9709   0.4924
 5XN  C2    C   CR5    0   0.477  -1.6601  -1.4984  -0.2238
 5XN  O3    O   O      0  -0.338  -1.7333  -2.8330  -0.3356
 5XN  N4    N   NR15   0  -0.374  -2.8198  -3.1989   0.4096
 5XN  C5    C   CR5    0   0.565  -3.5091  -2.1053   0.8618
 5XN  C6    C   CR5    0   0.360  -0.5358  -0.8675  -0.8794
 5XN  N7    N   N      0  -0.381  -0.5688   0.3994  -1.3176
 5XN  N8    N   N      0  -0.007   0.5877   0.6304  -1.8416
 5XN  N9    N   NR5    0  -0.097   1.2697  -0.4699  -1.7216
 5XN  N10   N   N      0  -0.228   0.6242  -1.4366  -1.1285
 5XN  C11   C   CH2    0  -0.413   2.6600  -0.5896  -2.1430
 5XN  C12   C   C1     0  -0.214   5.2157  -0.4661   1.2993
 5XN  C13   C   C      0  -0.024   4.7978   0.7030   0.6815
 5XN  C14   C   C1     0  -0.239   3.9827   0.6756  -0.4380
 5XN  C15   C   C      0   0.111   3.5769  -0.5507  -0.9527
 5XN  C16   C   C1     0  -0.272   3.9899  -1.7297  -0.3448
 5XN  C17   C   C1     0  -0.247   4.8060  -1.6836   0.7762
 5XN  O23   O   O      0  -0.467  -4.5656  -2.1332   1.4664
 5XN  C24   C   CH2    0  -0.577  -2.9473   0.4326   0.9007
 5XN  C25   C   CH1    0  -0.234  -3.9399   1.1527  -0.0046
 5XN  C26   C   C      0   0.470  -4.2886   2.5849   0.4950
 5XN  O27   O   O      0  -0.587  -4.2905   3.4673  -0.3865
 5XN  O28   O   OC    -1  -0.567  -4.5495   2.6891   1.6967
 5XN  N29   N   NT3    1  -0.832  -3.4281   1.2804  -1.3960
 5XN  H1    H   HNR5   0   0.443  -3.2082  -4.0893   0.1276
 5XN  H111  H   HCH2   0   0.323   2.7496  -1.5243  -2.6930
 5XN  H112  H   HCH2   0   0.321   2.8448   0.2325  -2.8306
 5XN  H14   H   H      0   0.286   3.6705   1.5995  -0.9087
 5XN  H16   H   H      0   0.270   3.6792  -2.6851  -0.7480
 5XN  H17   H   H      0   0.276   5.1273  -2.6015   1.2493
 5XN  H241  H   HCH2   0   0.296  -3.3779   0.4220   1.9015
 5XN  H242  H   HCH2   0   0.283  -2.0197   1.0046   0.9658
 5XN  H25   H   HCH1   0   0.311  -4.8677   0.5802  -0.0623
 5XN  H293  H   HNT3   0   0.471  -2.4025   1.2037  -1.4606
 5XN  H291  H   HNT3   0   0.459  -3.8331   0.6090  -2.0437
 5XN  H292  H   HNT3   0   0.450  -3.6948   2.2367  -1.6851
 5XN  CL1   CL  CL     0  -0.121   5.3068   2.2310   1.3189
 5XN  H12   H   H      0   0.286   5.8541  -0.4289   2.1713

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
 5XN  O27  C26   deloc     1.247  0.020  1.247
 5XN  O28  C26   deloc     1.234  0.020  1.234
 5XN  C26  C25   single    1.556  0.020  1.556
 5XN  C25  N29   single    1.488  0.020  1.488
 5XN  C25  C24   single    1.524  0.020  1.524
 5XN  C24  C1    single    1.488  0.020  1.488
 5XN  O23  C5    double    1.218  0.020  1.218
 5XN  C1   C5    single    1.460  0.020  1.460
 5XN  C1   C2    double    1.344  0.020  1.344
 5XN  C5   N4    single    1.370  0.020  1.370
 5XN  N10  C6    aromatic  1.316  0.020  1.316
 5XN  N10  N9    aromatic  1.305  0.020  1.305
 5XN  C2   C6    single    1.446  0.020  1.446
 5XN  C2   O3    single    1.341  0.020  1.341
 5XN  N4   O3    single    1.367  0.020  1.367
 5XN  C11  N9    single    1.458  0.020  1.458
 5XN  C11  C15   single    1.503  0.020  1.503
 5XN  C6   N7    aromatic  1.341  0.020  1.341
 5XN  N9   N8    aromatic  1.300  0.020  1.300
 5XN  C15  C16   aromatic  1.389  0.020  1.389
 5XN  C15  C14   aromatic  1.390  0.020  1.390
 5XN  N7   N8    aromatic  1.291  0.020  1.291
 5XN  C16  C17   aromatic  1.387  0.020  1.387
 5XN  C14  C13   aromatic  1.385  0.020  1.385
 5XN  C17  C12   aromatic  1.387  0.020  1.387
 5XN  C13  C12   aromatic  1.387  0.020  1.387
 5XN  C13  CL1   single    1.732  0.020  1.732
 5XN  N4   H1    single    0.890  0.020  1.040
 5XN  C11  H111  single    0.970  0.020  1.090
 5XN  C11  H112  single    0.970  0.020  1.090
 5XN  C12  H12   single    0.930  0.020  1.080
 5XN  C14  H14   single    0.930  0.020  1.080
 5XN  C16  H16   single    0.930  0.020  1.080
 5XN  C17  H17   single    0.930  0.020  1.080
 5XN  C24  H241  single    0.970  0.020  1.090
 5XN  C24  H242  single    0.970  0.020  1.090
 5XN  C25  H25   single    0.970  0.020  1.090
 5XN  N29  H293  single    0.890  0.020  1.040
 5XN  N29  H291  single    0.890  0.020  1.040
 5XN  N29  H292  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
 5XN  C24   C1   C5    123.75  3.000
 5XN  C5    C1   C2    105.18  3.000
 5XN  C24   C1   C2    131.06  3.000
 5XN  C6    C2   O3    116.02  3.000
 5XN  O3    C2   C1    113.20  3.000
 5XN  C6    C2   C1    130.78  3.000
 5XN  N4    O3   C2    105.32  3.000
 5XN  H1    N4   C5    126.99  3.000
 5XN  H1    N4   O3    112.88  3.000
 5XN  C5    N4   O3    111.48  3.000
 5XN  O23   C5   N4    125.62  3.000
 5XN  N4    C5   C1    104.31  3.000
 5XN  O23   C5   C1    130.04  3.000
 5XN  N10   C6   N7    111.62  3.000
 5XN  N7    C6   C2    122.76  3.000
 5XN  N10   C6   C2    125.62  3.000
 5XN  N8    N7   C6    106.25  3.000
 5XN  N9    N8   N7    106.32  3.000
 5XN  C11   N9   N10   122.84  3.000
 5XN  C11   N9   N8    122.90  3.000
 5XN  N10   N9   N8    114.17  3.000
 5XN  N9    N10  C6    101.64  3.000
 5XN  H112  C11  H111  108.41  3.000
 5XN  H112  C11  C15   112.18  3.000
 5XN  H111  C11  C15   111.86  3.000
 5XN  H112  C11  N9    106.42  3.000
 5XN  H111  C11  N9    107.16  3.000
 5XN  C15   C11  N9    110.53  3.000
 5XN  H12   C12  C17   120.58  3.000
 5XN  H12   C12  C13   120.54  3.000
 5XN  C17   C12  C13   118.88  3.000
 5XN  CL1   C13  C14   119.20  3.000
 5XN  CL1   C13  C12   119.42  3.000
 5XN  C14   C13  C12   121.38  3.000
 5XN  H14   C14  C15   120.50  3.000
 5XN  H14   C14  C13   120.27  3.000
 5XN  C15   C14  C13   119.23  3.000
 5XN  C16   C15  C14   119.99  3.000
 5XN  C14   C15  C11   119.60  3.000
 5XN  C16   C15  C11   120.39  3.000
 5XN  H16   C16  C17   119.95  3.000
 5XN  H16   C16  C15   120.04  3.000
 5XN  C17   C16  C15   120.01  3.000
 5XN  H17   C17  C16   120.00  3.000
 5XN  H17   C17  C12   119.49  3.000
 5XN  C16   C17  C12   120.51  3.000
 5XN  H242  C24  H241  106.63  3.000
 5XN  H242  C24  C25   109.95  3.000
 5XN  H241  C24  C25   107.02  3.000
 5XN  H242  C24  C1    110.56  3.000
 5XN  H241  C24  C1    108.48  3.000
 5XN  C25   C24  C1    113.87  3.000
 5XN  H25   C25  N29   106.74  3.000
 5XN  H25   C25  C26   108.01  3.000
 5XN  N29   C25  C26   107.35  3.000
 5XN  H25   C25  C24   109.69  3.000
 5XN  N29   C25  C24   111.83  3.000
 5XN  C26   C25  C24   112.95  3.000
 5XN  O28   C26  O27   128.92  3.000
 5XN  O28   C26  C25   115.95  3.000
 5XN  O27   C26  C25   115.11  3.000
 5XN  H292  N29  H291  109.25  3.000
 5XN  H292  N29  H293  107.94  3.000
 5XN  H291  N29  H293  107.89  3.000
 5XN  H292  N29  C25   104.60  3.000
 5XN  H291  N29  C25   113.70  3.000
 5XN  H293  N29  C25   113.24  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
 5XN  CONST_01  N8   N9   N10  C6     0.00   0.0  0
 5XN  CONST_02  N9   N8   N7   C6     0.00   0.0  0
 5XN  CONST_03  N9   N10  C6   N7     0.00   0.0  0
 5XN  CONST_04  N10  N9   N8   N7     0.00   0.0  0
 5XN  CONST_05  N10  C6   N7   N8     0.00   0.0  0
 5XN  CONST_06  C15  C16  C17  C12    0.00   0.0  0
 5XN  CONST_07  C15  C14  C13  C12    0.00   0.0  0
 5XN  CONST_08  C16  C15  C14  C13    0.00   0.0  0
 5XN  CONST_09  C16  C17  C12  C13    0.00   0.0  0
 5XN  CONST_10  C17  C16  C15  C14    0.00   0.0  0
 5XN  CONST_11  C17  C12  C13  C14    0.00   0.0  0
 5XN  CONST_12  N9   N10  C6   C2   180.00   0.0  0
 5XN  CONST_13  N8   N7   C6   C2   180.00   0.0  0
 5XN  CONST_14  O3   N4   C5   C1     0.00   0.0  0
 5XN  CONST_15  C11  N9   N10  C6   180.00   0.0  0
 5XN  CONST_16  C11  N9   N8   N7   180.00   0.0  0
 5XN  CONST_17  C17  C16  C15  C11  180.00   0.0  0
 5XN  CONST_18  C13  C14  C15  C11  180.00   0.0  0
 5XN  CONST_19  CL1  C13  C14  C15  180.00   0.0  0
 5XN  CONST_20  CL1  C13  C12  C17  180.00   0.0  0
 5XN  CONST_21  O23  C5   N4   O3   180.00   0.0  0
 5XN  CONST_22  H16  C16  C17  C12  180.00   0.0  0
 5XN  CONST_23  H14  C14  C13  C12  180.00   0.0  0
 5XN  CONST_24  H17  C17  C12  C13  180.00   0.0  0
 5XN  CONST_25  H12  C12  C13  C14  180.00   0.0  0
 5XN  Var_01    N10  C6   C2   C1   153.56  30.0  2
 5XN  Var_02    C15  C11  N9   N8   103.29  30.0  1
 5XN  Var_03    C16  C15  C11  N9    93.49  30.0  2
 5XN  Var_04    C25  C24  C1   C2    97.62  30.0  1

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
 5XN  chir_01  C25  C26  N29  C24  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
 5XN  plan-1  C1   0.020
 5XN  plan-1  C2   0.020
 5XN  plan-1  O3   0.020
 5XN  plan-1  N4   0.020
 5XN  plan-1  C5   0.020
 5XN  plan-1  C6   0.020
 5XN  plan-1  O23  0.020
 5XN  plan-1  C24  0.020
 5XN  plan-1  H1   0.020
 5XN  plan-2  C2   0.020
 5XN  plan-2  C6   0.020
 5XN  plan-2  N7   0.020
 5XN  plan-2  N8   0.020
 5XN  plan-2  N9   0.020
 5XN  plan-2  N10  0.020
 5XN  plan-2  C11  0.020
 5XN  plan-3  C11  0.020
 5XN  plan-3  C12  0.020
 5XN  plan-3  C13  0.020
 5XN  plan-3  C14  0.020
 5XN  plan-3  C15  0.020
 5XN  plan-3  C16  0.020
 5XN  plan-3  C17  0.020
 5XN  plan-3  H14  0.020
 5XN  plan-3  H16  0.020
 5XN  plan-3  H17  0.020
 5XN  plan-3  CL1  0.020
 5XN  plan-3  H12  0.020
 5XN  plan-4  C25  0.020
 5XN  plan-4  C26  0.020
 5XN  plan-4  O27  0.020
 5XN  plan-4  O28  0.020

