Aminonitrones as Highly Reactive Bifunctional Synthons. Expedient One-pot Route to 5-Amino-1,2,4-triazoles and 5-Amino-1,2,4-oxadiazoles – Potential Antimicrobials Targeting Multi-drug Resistant Bacteria
Il’in, Mikhail; Sysoeva, Alexandra A.; Bolotin, Dmitrii S.; Novikov, Alexander S.; Suslonov, Vitalii V.; Rogacheva, Elizaveta V.; Kraeva, Liudmila A.; Kukushkin, Vadim Yu.; New Journal of Chemistry 43 (2019) 17358–17366; doi:10.1039/C9NJ04529E

data_7058898
_publ_section_title
;
 Aminonitrones as Highly Reactive Bifunctional Synthons. Expedient One-pot
 Route to 5-Amino-1,2,4-triazoles and 5-Amino-1,2,4-oxadiazoles --
 Potential Antimicrobials Targeting Multi-drug Resistant Bacteria
;
_journal_issue                   44
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17358
_journal_page_last               17366
_journal_paper_doi               10.1039/C9NJ04529E
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C21 H24 N4'
_chemical_formula_sum            'C21 H24 N4'
_chemical_formula_weight         332.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-07 deposited with the CCDC.    2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.8112(2)
_cell_length_b                   16.1728(2)
_cell_length_c                   9.07050(10)
_cell_measurement_reflns_used    18901
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.7120
_cell_measurement_theta_min      1.7520
_cell_volume                     3637.42(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -44.00  -6.00   0.50    1.08    --  -38.95 129.00-171.00   76
  2  \w    -89.00 -48.00   0.50    1.08    --  -38.95 129.00-171.00   82
  3  \w     42.00  69.00   0.50    1.08    --   38.95-129.00 115.00   54
  4  \w     65.00  90.00   0.50    1.08    --   38.95-140.00 -57.00   50
  5  \w    111.00 157.00   0.50    4.31    --  107.00 129.00-171.00   92
  6  \w     55.00 104.00   0.50    4.31    --  107.00-140.00 -57.00   98
  7  \w     87.00 112.00   0.50    4.31    --  107.00 140.00   1.00   50
  8  \w     97.00 122.00   0.50    4.31    --  107.00-129.00 115.00   50
  9  \w    -69.00 -15.00   0.50    1.08    --  -38.95 -77.00 120.00  108
 10  \w   -102.00 -73.00   0.50    1.08    --  -38.95 -77.00 120.00   58
 11  \w   -103.00 -22.00   0.50    1.08    --  -38.95 -54.00-120.00  162
 12  \w    -96.00 -21.00   0.50    1.08    --  -38.95 138.00 -90.00  150
 13  \w    -49.00 -23.00   0.50    1.08    --  -38.95 -54.00 -60.00   52
 14  \w   -103.00 -38.00   0.50    1.08    --  -38.95 -54.00   0.00  130
 15  \w   -101.00 -55.00   0.50    1.08    --  -38.95 -54.00 -60.00   92
 16  \w    -51.00 -15.00   0.50    1.08    --  -38.95 140.00   1.00   72
 17  \w     74.00 104.00   0.50    1.08    --   38.95  54.00 150.00   60
 18  \w     25.00  68.00   0.50    1.08    --   38.95  65.00-120.00   86
 19  \w     20.00 104.00   0.50    1.08    --   38.95  65.00-150.00  168
 20  \w     79.00 104.00   0.50    1.08    --   38.95  65.00-120.00   50
 21  \w     11.00  37.00   0.50    1.08    --   38.95 -32.00   0.00   52
 22  \w     27.00  61.00   0.50    1.08    --   38.95  54.00 150.00   68
 23  \w     57.00  82.00   0.50    1.08    --   38.95  32.00-150.00   50
 24  \w     39.00  78.00   0.50    4.31    --  107.00-111.00 120.00   78
 25  \w    131.00 157.00   0.50    4.31    --  107.00  37.00 150.00   52
 26  \w     86.00 157.00   0.50    4.31    --  107.00  61.00-150.00  142
 27  \w     93.00 119.00   0.50    4.31    --  107.00  37.00 150.00   52
 28  \w     99.00 125.00   0.50    4.31    --  107.00-133.00-120.00   52
 29  \w     88.00 121.00   0.50    4.31    --  107.00 -30.00-120.00   66
 30  \w     43.00  80.00   0.50    4.31    --  107.00-133.00-120.00   74
 31  \w     81.00 156.00   0.50    4.31    --  107.00  77.00  30.00  150
 32  \w     46.00 116.00   0.50    4.31    --  107.00 -45.00  60.00  140
 33  \w     81.00 152.00   0.50    4.31    --  107.00  93.00  60.00  142
 34  \w     38.00 109.00   0.50    4.31    --  107.00-111.00 -60.00  142
 35  \w     98.00 157.00   0.50    4.31    --  107.00  30.00   0.00  118
 36  \w    100.00 154.00   0.50    4.31    --  107.00  37.00 120.00  108
 37  \w     75.00 140.00   0.50    4.31    --  107.00 -93.00 -30.00  130
 38  \w     79.00 109.00   0.50    4.31    --  107.00-111.00-150.00   60
 39  \w     64.00 134.00   0.50    4.31    --  107.00 -77.00 -90.00  140
 40  \w     46.00  81.00   0.50    4.31    --  107.00 -30.00-120.00   70
 41  \w     73.00  99.00   0.50    4.31    --  107.00-129.00 115.00   52
 42  \w    -12.00  26.00   0.50    1.08    --  -38.95  21.00  30.00   76
 43  \w   -100.00 -75.00   0.50    1.08    --  -38.95 -77.00   0.00   50
 44  \w    -49.00 -23.00   0.50    1.08    --  -38.95 -77.00   0.00   52
 45  \w     15.00  44.00   0.50    1.08    --   38.95-138.00-150.00   58
 46  \w     34.00  59.00   0.50    1.08    --   38.95 -21.00  60.00   50
 47  \w     73.00  98.00   0.50    1.08    --   38.95  54.00 120.00   50
 48  \w     50.00  84.00   0.50    1.08    --   38.95-138.00-150.00   68
 49  \w     13.00  58.00   0.50    1.08    --   38.95 -65.00 150.00   90
 50  \w    -17.00   9.00   0.50    1.08    --   38.95 -21.00  60.00   52
 51  \w    -30.00  -4.00   0.50    1.08    --   38.95 -89.00 120.00   52
 52  \w     45.00  71.00   0.50    1.08    --   38.95  54.00 120.00   52
 53  \w     31.00  69.00   0.50    1.08    --   38.95 -89.00 120.00   76
 54  \w     91.00 117.00   0.50    4.31    --  107.00  53.00 -30.00   52
 55  \w     99.00 133.00   0.50    4.31    --  107.00  22.00  90.00   68
 56  \w    120.00 156.00   0.50    4.31    --  107.00  30.00 -90.00   72
 57  \w     73.00 106.00   0.50    4.31    --  107.00 -45.00 -60.00   66
 58  \w    110.00 136.00   0.50    4.31    --  107.00  30.00 150.00   52
 59  \w     53.00 127.00   0.50    4.31    --  107.00 -53.00-120.00  148
 60  \w     99.00 125.00   0.50    4.31    --  107.00-133.00 -60.00   52
 61  \w     48.00  78.00   0.50    4.31    --  107.00-133.00 -60.00   60
 62  \w    100.00 125.00   0.50    4.31    --  107.00-133.00  30.00   50
 63  \w     54.00  96.00   0.50    4.31    --  107.00-133.00 -90.00   84
 64  \w    112.00 153.00   0.50    4.31    --  107.00  93.00-120.00   82
 65  \w     51.00  77.00   0.50    4.31    --  107.00-133.00  30.00   52
 66  \w    115.00 155.00   0.50    4.31    --  107.00 111.00 -30.00   80
 67  \w     90.00 150.00   0.50    4.31    --  107.00  45.00-180.00  120
 68  \w     35.00  82.00   0.50    4.31    --  107.00 -22.00  60.00   94
 69  \w     60.00  86.00   0.50    4.31    --  107.00-133.00-150.00   52
 70  \w     96.00 122.00   0.50    4.31    --  107.00 111.00-150.00   52
 71  \w    123.00 157.00   0.50    4.31    --  107.00  53.00 -30.00   68
 72  \w     87.00 113.00   0.50    4.31    --  107.00 -86.00  30.00   52
 73  \w     84.00 110.00   0.50    4.31    --  107.00  93.00-120.00   52
 74  \w    123.00 154.00   0.50    4.31    --  107.00 111.00-150.00   62
 75  \w     74.00 114.00   0.50    4.31    --  107.00-111.00  90.00   80
 76  \w     53.00 134.00   0.50    4.31    --  107.00 -77.00  90.00  162
 77  \w     75.00 125.00   0.50    4.31    --  107.00-133.00  90.00  100
 78  \w    118.00 157.00   0.50    4.31    --  107.00  77.00   0.00   78
 79  \w    -73.00 -48.00   0.50    1.08    --  -38.95 129.00-171.00   50
 80  \w     56.00  82.00   0.50    4.31    --  107.00-124.00  21.00   52
 81  \w      3.00  28.00   0.50    1.08    --  -38.95  77.00 -60.00   50
 82  \w    -62.00 -36.00   0.50    1.08    --  -38.95  77.00 -60.00   52
 83  \w    -46.00 -20.00   0.50    1.08    --  -38.95  21.00  60.00   52
 84  \w     -3.00  23.00   0.50    1.08    --  -38.95  21.00  60.00   52
 85  \w     83.00 108.00   0.50    1.08    --   38.95  32.00-120.00   50
 86  \w     73.00 127.00   0.50    4.31    --  107.00 -53.00 150.00  108
 87  \w    128.00 154.00   0.50    4.31    --  107.00  37.00  60.00   52
 88  \w     73.00  99.00   0.50    4.31    --  107.00 133.00-180.00   52
 89  \w     97.00 122.00   0.50    4.31    --  107.00  37.00  60.00   50
 90  \w    123.00 156.00   0.50    4.31    --  107.00  61.00 -60.00   66
 91  \w    122.00 148.00   0.50    4.31    --  107.00 133.00-180.00   52
 92  \w     97.00 138.00   0.50    4.31    --  107.00 178.00 -90.00   82
 93  \w     93.00 119.00   0.50    4.31    --  107.00  30.00 -90.00   52
 94  \w     93.00 137.00   0.50    4.31    --  107.00  45.00  30.00   88
 95  \w    121.00 156.00   0.50    4.31    --  107.00  61.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0291672000
_diffrn_orient_matrix_UB_12      -0.0841123000
_diffrn_orient_matrix_UB_13      -0.0032419000
_diffrn_orient_matrix_UB_21      -0.0545991000
_diffrn_orient_matrix_UB_22      0.0445191000
_diffrn_orient_matrix_UB_23      -0.0213004000
_diffrn_orient_matrix_UB_31      0.0052404000
_diffrn_orient_matrix_UB_32      -0.0039997000
_diffrn_orient_matrix_UB_33      -0.1686072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            42786
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.997
_diffrn_reflns_theta_min         1.782
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         6891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.9067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5999
_reflns_number_total             6891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj04529e2.cif
_cod_data_source_block           14
_cod_database_code               7058898
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C18 N3'
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.894
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(H9AA)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(H11A)=Sof(H11B)=
 Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(C14A)=
 Sof(H14A)=Sof(H14B)=1-FVAR(1)
 Sof(H9A)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C11B)=Sof(H11C)=Sof(H11D)=
 Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(H13C)=Sof(H13D)=Sof(C14B)=
 Sof(H14C)=Sof(H14D)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A), C9A(H9AA)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10E,H10F), C11(H11E,H11F), C12(H12E,H12F), C13(H13E,H13F), C14(H14E,
 H14F), C15(H15C,H15D), C10A(H10A,H10B), C11A(H11A,H11B), C12A(H12A,H12B),
 C13A(H13A,H13B), C14A(H14A,H14B), C15A(H15A,H15B), C10B(H10C,H10D), C11B(H11C,
 H11D), C12B(H12C,H12D), C13B(H13C,H13D), C14B(H14C,H14D)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C4(H4B), C5(H5), C6(H6), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19),
  C20(H20), C21(H21), N4A(H4A), C4A(H4AA), C5A(H5A), C6A(H6A), C7A(H7A),
 C8A(H8A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A)
;
_shelx_res_checksum              16509
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.853
_oxdiff_exptl_absorpt_empirical_full_min 0.542