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_7057421
_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_formula_moiety         'Br, C15 H20 N3 O, H2 O'
_chemical_formula_sum            'C15 H22 Br N3 O2'
_chemical_formula_weight         356.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-28
_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            4
_cell_length_a                   5.56160(10)
_cell_length_b                   14.0149(4)
_cell_length_c                   20.3191(5)
_cell_measurement_reflns_used    6912
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1000
_cell_measurement_theta_min      3.8010
_cell_volume                     1583.78(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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     29.00  64.00   1.00    1.00    --   40.38 -38.00 120.00   35
  2  \w     81.00 106.00   1.00    1.03    --  113.00 -95.00 120.00   25
  3  \w     62.00  96.00   1.00    1.03    --  113.00 -77.00 150.00   34
  4  \w     48.00  74.00   1.00    1.03    --  113.00 -95.00 120.00   26
  5  \w     46.00 115.00   1.00    1.03    --  113.00-112.00 120.00   69
  6  \w     43.00 144.00   1.00    1.03    --  113.00 -30.00 -30.00  101
  7  \w     95.00 120.00   1.00    1.03    --  113.00  45.00-180.00   25
  8  \w    138.00 163.00   1.00    1.03    --  113.00  45.00-180.00   25
  9  \w     69.00 117.00   1.00    1.03    --  113.00 178.00 -90.00   48
 10  \w    115.00 177.00   1.00    1.03    --  113.00 112.00  60.00   62
 11  \w    105.00 130.00   1.00    1.03    --  113.00 114.00 168.00   25
 12  \w     55.00  80.00   1.00    1.03    --  113.00 -95.00 -30.00   25
 13  \w      8.00  34.00   1.00    1.00    --   40.38 -99.00 -60.00   26
 14  \w    -70.00  34.00   1.00    1.00    --  -40.38  57.00  30.00  104
 15  \w      7.00  33.00   1.00    1.00    --   40.38 -99.00 120.00   26
 16  \w     41.00  72.00   1.00    1.00    --   40.38 -99.00 120.00   31
 17  \w     34.00  73.00   1.00    1.00    --   40.38 -99.00 -60.00   39
 18  \w     36.00  64.00   1.00    1.03    --  113.00 -95.00-180.00   28
 19  \w     95.00 121.00   1.00    1.03    --  113.00 -77.00 -60.00   26
 20  \w     90.00 116.00   1.00    1.03    --  113.00 178.00-150.00   26
 21  \w     52.00  91.00   1.00    1.03    --  113.00 -30.00 120.00   39
 22  \w     38.00  80.00   1.00    1.03    --  113.00 -95.00 150.00   42
 23  \w     57.00  86.00   1.00    1.03    --  113.00 178.00  90.00   29
 24  \w    121.00 147.00   1.00    1.03    --  113.00 178.00  90.00   26
 25  \w     46.00  90.00   1.00    1.03    --  113.00 -45.00 -90.00   44
 26  \w    102.00 135.00   1.00    1.03    --  113.00 112.00 -30.00   33
 27  \w    -73.00 -34.00   1.00    1.00    --  -40.38 178.00-180.00   39
 28  \w    105.00 130.00   1.00    1.00    --   40.38 178.00-120.00   25
 29  \w     63.00 101.00   1.00    1.03    --  113.00 -95.00  30.00   38
 30  \w     42.00  68.00   1.00    1.03    --  113.00 -45.00-180.00   26
 31  \w    140.00 168.00   1.00    1.03    --  113.00   0.00-180.00   28
 32  \w     45.00  86.00   1.00    1.03    --  113.00   0.00-180.00   41
 33  \w     84.00 109.00   1.00    1.03    --  113.00 178.00   0.00   25
 34  \w     60.00  85.00   1.00    1.03    --  113.00 -95.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1469845000
_diffrn_orient_matrix_UB_12      0.0594622000
_diffrn_orient_matrix_UB_13      -0.0494307000
_diffrn_orient_matrix_UB_21      0.0484794000
_diffrn_orient_matrix_UB_22      -0.0904707000
_diffrn_orient_matrix_UB_23      -0.0409611000
_diffrn_orient_matrix_UB_31      -0.2297679000
_diffrn_orient_matrix_UB_32      0.0189784000
_diffrn_orient_matrix_UB_33      -0.0403302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11976
_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         76.260
_diffrn_reflns_theta_min         3.832
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.494
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.092(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0234
_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^)+(0.0307P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3164
_reflns_number_total             3290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01682h2.cif
_cod_data_source_block           4_H2O
_cod_database_code               7057421
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'N3 O Br C15'
_shelx_estimated_absorpt_t_max   0.714
_shelx_estimated_absorpt_t_min   0.563
_reflns_odcompleteness_completeness 95.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.908(19)
 0.092(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Riding coordinates:
 C12(H1SA,H1SB)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B)
3.d Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C4(H4), C5(H5), C8(H8), C7(H7)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              83612
_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 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.856