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_7058897
_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         'C20 H22 N4'
_chemical_formula_sum            'C20 H22 N4'
_chemical_formula_weight         318.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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                 91.807(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8183(4)
_cell_length_b                   9.0129(4)
_cell_length_c                   32.7415(11)
_cell_measurement_reflns_used    7703
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7180
_cell_measurement_theta_min      2.9330
_cell_volume                     3485.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -17.00   18.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -      -25.5873   57.0000 -150.0000 35

  2 omega  -86.00  -32.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -      -25.5873  178.0000  150.0000 54

  3 omega    8.00   92.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -       26.6811   57.0000    0.0000 84

  4 omega  -38.00   67.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -19.0000    0.0000 105

  5 omega  -33.00   21.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -      -25.5873   77.0000  150.0000 54

  6 omega  -29.00   21.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -      -25.5873   19.0000  -90.0000 50

  7 omega   54.00   91.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -       26.6811  178.0000   60.0000 37

  8 omega   76.00  103.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -       26.6811  178.0000    0.0000 27

  9 omega   19.00   44.00   1.0000   89.5500
omega____ theta____ kappa____ phi______ frames
    -       26.6811   57.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0014206000
_diffrn_orient_matrix_UB_12      -0.0150055000
_diffrn_orient_matrix_UB_13      -0.0212753000
_diffrn_orient_matrix_UB_21      0.0457474000
_diffrn_orient_matrix_UB_22      -0.0502968000
_diffrn_orient_matrix_UB_23      0.0027867000
_diffrn_orient_matrix_UB_31      -0.0388617000
_diffrn_orient_matrix_UB_32      -0.0586653000
_diffrn_orient_matrix_UB_33      0.0030313000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            31128
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.843
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.213
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         8009
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+1.5820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6289
_reflns_number_total             8009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj04529e2.cif
_cod_data_source_block           13
_cod_database_code               7058897
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 N4'
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 H4AA-N4A
 0.885 with sigma of 0.002
3.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C10A(H10C,H10D), C11A(H11C,H11D), C12A(H12C,H12D), C13A(H13C,H13D),
 C14A(H14C,H14D)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C4A(H4AB), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A),
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
;
_shelx_res_checksum              92723
_olex2_submission_special_instructions 'No special instructions were received'