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_7057423
_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 H19 Br N3 O'
_chemical_formula_sum            'C15 H19 Br2 N3 O'
_chemical_formula_weight         417.15
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                120
_cell_formula_units_Z            18
_cell_length_a                   36.6338(19)
_cell_length_b                   36.6338(19)
_cell_length_c                   6.4707(4)
_cell_measurement_reflns_used    4543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.3530
_cell_measurement_theta_min      4.1470
_cell_volume                     7520.5(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -36.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000 -120.0000 27

  2 omega -112.00  -19.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -38.0000 -180.0000 93

  3 omega    5.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  -99.0000   60.0000 75

  4 omega   70.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000  -90.0000 48

  5 omega   57.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000 -150.0000 26

  6 omega   82.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000   60.0000 45

  7 omega   56.00  100.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 44

  8 omega   45.00   91.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 46

  9 omega   36.00   84.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 48

 10 omega   39.00   77.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 38

 11 omega   35.00   69.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 34

 12 omega  101.00  165.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 64

 13 omega   53.00   80.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 27

 14 omega   40.00   95.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 55

 15 omega   30.00   91.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 61

 16 omega   33.00  139.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000   60.0000 106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0396898000
_diffrn_orient_matrix_UB_12      0.0006015000
_diffrn_orient_matrix_UB_13      0.0834712000
_diffrn_orient_matrix_UB_21      -0.0274121000
_diffrn_orient_matrix_UB_22      -0.0356997000
_diffrn_orient_matrix_UB_23      0.1518173000
_diffrn_orient_matrix_UB_31      -0.0052449000
_diffrn_orient_matrix_UB_32      -0.0328685000
_diffrn_orient_matrix_UB_33      -0.1635120000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10753
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.196
_diffrn_reflns_theta_min         4.180
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.658
_exptl_crystal_description       needle
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+45.5199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3239
_reflns_number_total             3449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01682h2.cif
_cod_data_source_block           6
_cod_original_cell_volume        7520.5(9)
_cod_database_code               7057423
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Br2 C18'
_shelx_estimated_absorpt_t_max   0.577
_shelx_estimated_absorpt_t_min   0.458
_reflns_odcompleteness_completeness 99.80
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              81045
_shelx_fab_checksum              87835
_olex2_submission_special_instructions 'No special instructions were received'