Facile Selective Synthesis of 2-Methyl-5-amino-1,2,4-oxadiazolium Bromides as Further Targets for Nucleophilic Additions
Il’in, Mikhail; Bolotin, Dmitrii S.; Suslonov, Vitalii V.; Kukushkin, Vadim Yu.; New Journal of Chemistry 42 (2018) 9373–9376; doi:10.1039/C8NJ01682H

data_7057425
_publ_section_title
;
 Facile Selective Synthesis of 2-Methyl-5-amino-1,2,4-oxadiazolium
 Bromides as Further Targets for Nucleophilic Additions
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9373
_journal_page_last               9376
_journal_paper_doi               10.1039/C8NJ01682H
_journal_volume                  42
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         '0.5(H4 O2), 2(C14 H18 N4)'
_chemical_formula_sum            'C28 H38 N8 O'
_chemical_formula_weight         502.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-02 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.3835(2)
_cell_length_b                   18.9731(2)
_cell_length_c                   14.30664(17)
_cell_measurement_reflns_used    14147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.3830
_cell_measurement_theta_min      4.4640
_cell_volume                     5261.48(10)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(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    -50.00   6.00   0.50    0.83    --  -41.35 112.00  90.00  112
  2  \w    -83.00 -43.00   0.50    0.83    --  -41.35 -21.00  94.00   80
  3  \w     -3.00  22.00   0.50    0.83    --   41.35-112.00  -2.00   50
  4  \w    -23.00  13.00   0.50    0.83    --   41.35 -21.00  94.00   72
  5  \w     29.00  55.00   0.50    0.83    --   41.35-112.00  -2.00   52
  6  \w     24.00 104.00   0.50    3.32    --   93.71 -21.00  94.00  160
  7  \w     81.00 127.00   0.50    3.32    --   93.71 112.00  -1.00   92
  8  \w     67.00  93.00   0.50    3.32    --   93.71-112.00  -2.00   52
  9  \w    113.00 147.00   0.50    3.32    --   93.71 112.00  90.00   68
 10  \w    -60.00 -34.00   0.50    0.83    --  -41.35 112.00  -1.00   52
 11  \w    -10.00  15.00   0.50    0.83    --   41.35 -32.00  30.00   50
 12  \w     69.00  94.00   0.50    0.83    --   41.35  32.00-180.00   50
 13  \w     18.00  48.00   0.50    0.83    --   41.35 -32.00  30.00   60
 14  \w     85.00 155.00   0.50    3.32    --   93.71 117.00 120.00  140
 15  \w     65.00 108.00   0.50    3.32    --   93.71 -96.00-150.00   86
 16  \w     25.00  90.00   0.50    3.32    --   93.71 -96.00 -90.00  130
 17  \w     27.00  52.00   0.50    3.32    --   93.71 -96.00-150.00   50
 18  \w     77.00 102.00   0.50    3.32    --   93.71 -33.00 -90.00   50
 19  \w     69.00 107.00   0.50    3.32    --   93.71 -42.00   0.00   76
 20  \w     39.00  64.00   0.50    0.83    --   41.35  65.00 -90.00   50
 21  \w    -83.00 -57.00   0.50    0.83    --  -41.35 -77.00   0.00   52
 22  \w    -42.00 -16.00   0.50    0.83    --  -41.35 -77.00 -30.00   52
 23  \w    -41.00 -16.00   0.50    0.83    --  -41.35 -77.00   0.00   50
 24  \w     29.00  55.00   0.50    0.83    --   41.35  43.00 -60.00   52
 25  \w     22.00  49.00   0.50    0.83    --   41.35  77.00  30.00   54
 26  \w     17.00  48.00   0.50    0.83    --   41.35  77.00  60.00   62
 27  \w     28.00  70.00   0.50    0.83    --   41.35  43.00   0.00   84
 28  \w     22.00  47.00   0.50    0.83    --   41.35  65.00 -30.00   50
 29  \w     75.00 124.00   0.50    3.32    --   93.71  59.00   0.00   98
 30  \w     80.00 105.00   0.50    3.32    --   93.71  50.00-180.00   50
 31  \w     69.00 141.00   0.50    3.32    --   93.71  77.00 -30.00  144
 32  \w    132.00 157.00   0.50    3.32    --   93.71  50.00-180.00   50
 33  \w     72.00 133.00   0.50    3.32    --   93.71  68.00   0.00  122
 34  \w     72.00 112.00   0.50    3.32    --   93.71  68.00 -30.00   80
 35  \w     68.00  94.00   0.50    3.32    --   93.71  77.00  30.00   52
 36  \w    125.00 157.00   0.50    3.32    --   93.71  77.00   0.00   64
 37  \w     78.00 104.00   0.50    3.32    --   93.71  59.00  30.00   52
 38  \w    120.00 146.00   0.50    3.32    --   93.71  68.00  30.00   52
 39  \w     74.00 105.00   0.50    3.32    --   93.71 -96.00 -60.00   62
 40  \w     72.00 100.00   0.50    3.32    --   93.71  68.00  30.00   56
 41  \w     68.00  93.00   0.50    3.32    --   93.71  77.00   0.00   50
 42  \w    101.00 126.00   0.50    3.32    --   93.71  77.00 -60.00   50
 43  \w     69.00  98.00   0.50    3.32    --   93.71  77.00 -60.00   58
 44  \w     88.00 114.00   0.50    3.32    --   93.71 112.00  90.00   52
 45  \w    -73.00 -34.00   0.50    0.83    --  -41.35 -32.00-180.00   78
 46  \w      4.00  35.00   0.50    0.83    --   41.35 -43.00 150.00   62
 47  \w     93.00 119.00   0.50    3.32    --   93.71-145.00 120.00   52
 48  \w     73.00  99.00   0.50    3.32    --   93.71 -42.00  30.00   52
 49  \w     94.00 131.00   0.50    3.32    --   93.71-145.00-150.00   74
 50  \w     30.00  55.00   0.50    3.32    --   93.71-145.00-150.00   50
 51  \w     38.00  63.00   0.50    3.32    --   93.71 -42.00  30.00   50
 52  \w     38.00  68.00   0.50    3.32    --   93.71-145.00 120.00   60
 53  \w     49.00  97.00   0.50    3.32    --   93.71 -68.00 -60.00   96
 54  \w     25.00 108.00   0.50    3.32    --   93.71 -96.00 120.00  166
 55  \w     52.00  78.00   0.50    0.83    --   41.35-112.00  -2.00   52
 56  \w    -56.00 -16.00   0.50    0.83    --  -41.35 -77.00-120.00   80
 57  \w    -58.00 -33.00   0.50    0.83    --  -41.35 -32.00  30.00   50
 58  \w   -107.00 -78.00   0.50    0.83    --  -41.35 -32.00  30.00   58
 59  \w     39.00  65.00   0.50    0.83    --   41.35  32.00  90.00   52
 60  \w     22.00  48.00   0.50    0.83    --   41.35 -32.00 -60.00   52
 61  \w     75.00 107.00   0.50    0.83    --   41.35  32.00  90.00   64
 62  \w     42.00  68.00   0.50    0.83    --   41.35 -89.00-150.00   52
 63  \w    -23.00   4.00   0.50    0.83    --   41.35 -89.00-150.00   54
 64  \w    127.00 153.00   0.50    3.32    --   93.71  17.00-180.00   52
 65  \w     31.00 103.00   0.50    3.32    --   93.71 -59.00 120.00  144
 66  \w     77.00 117.00   0.50    3.32    --   93.71-117.00-150.00   80
 67  \w     68.00 114.00   0.50    3.32    --   93.71 145.00 150.00   92
 68  \w     47.00  73.00   0.50    3.32    --   93.71-117.00-150.00   52
 69  \w     65.00 100.00   0.50    3.32    --   93.71-117.00 -30.00   70
 70  \w     95.00 121.00   0.50    3.32    --   93.71  17.00-180.00   52
 71  \w     84.00 113.00   0.50    3.32    --   93.71 -68.00  60.00   58
 72  \w     34.00  60.00   0.50    3.32    --   93.71 -68.00  60.00   52
 73  \w     52.00  93.00   0.50    3.32    --   93.71 -42.00 -30.00   82
 74  \w     71.00  97.00   0.50    3.32    --   93.71 -17.00-120.00   52
 75  \w     26.00  52.00   0.50    3.32    --   93.71 -17.00-120.00   52
 76  \w     38.00 107.00   0.50    3.32    --   93.71 -17.00   0.00  138
 77  \w     24.00  56.00   0.50    3.32    --   93.71 -96.00  30.00   64
 78  \w     64.00 103.00   0.50    3.32    --   93.71 -96.00  30.00   78
 79  \w    108.00 134.00   0.50    3.32    --   93.71  33.00  60.00   52
 80  \w     47.00 100.00   0.50    3.32    --   93.71 -77.00  30.00  106
 81  \w     85.00 111.00   0.50    3.32    --   93.71  33.00-120.00   52
 82  \w     90.00 157.00   0.50    3.32    --   93.71  33.00-150.00  134
 83  \w   -100.00 -74.00   0.50    0.83    --  -41.35 -21.00  95.00   52
 84  \w     54.00  80.00   0.50    0.83    --   41.35  32.00-120.00   52
 85  \w     36.00  74.00   0.50    0.83    --   41.35-138.00-150.00   76
 86  \w     31.00  71.00   0.50    3.32    --   93.71 -68.00-150.00   80
 87  \w     97.00 123.00   0.50    3.32    --   93.71  33.00  30.00   52
 88  \w     85.00 131.00   0.50    3.32    --   93.71  33.00 -90.00   92
 89  \w     72.00  97.00   0.50    3.32    --   93.71  77.00 -90.00   50
 90  \w     68.00  98.00   0.50    3.32    --   93.71 -68.00  90.00   60
 91  \w    104.00 130.00   0.50    3.32    --   93.71  77.00 -90.00   52
 92  \w     86.00 112.00   0.50    3.32    --   93.71 -68.00-150.00   52
 93  \w    105.00 135.00   0.50    3.32    --   93.71 117.00  30.00   60
 94  \w    107.00 156.00   0.50    3.32    --   93.71  96.00  60.00   98
;
_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      -0.0038637000
_diffrn_orient_matrix_UB_12      -0.0780521000
_diffrn_orient_matrix_UB_13      -0.0292901000
_diffrn_orient_matrix_UB_21      -0.0793771500
_diffrn_orient_matrix_UB_22      0.0039861500
_diffrn_orient_matrix_UB_23      0.0007556000
_diffrn_orient_matrix_UB_31      0.0005218000
_diffrn_orient_matrix_UB_32      0.0220927000
_diffrn_orient_matrix_UB_33      -0.1036016000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17184
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        66.993
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_min         4.493
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76077
_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    1.269
_exptl_crystal_description       plate
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0355P)^2^+3.0408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0630
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2201
_reflns_number_total             2222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01682h2.cif
_cod_data_source_block           18_H2O
_cod_original_cell_volume        5261.49(10)
_cod_database_code               7057425
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'N4 C14'
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.915
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Riding coordinates:
 C6(H3)
3.b Free rotating group:
 O1(H1A,H1B)
3.c Ternary CH refined with riding coordinates:
 C9(H9)
3.d Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
3.e Aromatic/amide H refined with riding coordinates:
 N4(H4), C4(H4A), C5(H5), C8(H8), C7(H7), C6(H6)
;
_shelx_res_checksum              45716
_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 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.798