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_7057424
_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         'C14 H17 N3 O'
_chemical_formula_sum            'C14 H17 N3 O'
_chemical_formula_weight         243.30
_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   geom
_atom_sites_solution_primary     iterative
_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                 91.401(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8808(4)
_cell_length_b                   12.3009(8)
_cell_length_c                   17.6105(11)
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9550
_cell_measurement_theta_min      3.3160
_cell_volume                     1273.55(14)
_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  -85.00  -54.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  134.0000  175.0000 31

  2 omega   66.00   99.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000   30.0000 33

  3 omega   -5.00   93.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -150.0000 98

  4 omega  -48.00   28.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616    0.0000   60.0000 76

  5 omega   -7.00   37.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  150.0000 44

  6 omega   57.00   93.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  150.0000 36

  7 omega  -24.00   26.00   1.0000   62.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   30.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0059737000
_diffrn_orient_matrix_UB_12      0.0356990000
_diffrn_orient_matrix_UB_13      -0.0314986000
_diffrn_orient_matrix_UB_21      -0.0018248000
_diffrn_orient_matrix_UB_22      0.0452952000
_diffrn_orient_matrix_UB_23      0.0250339000
_diffrn_orient_matrix_UB_31      0.1205114000
_diffrn_orient_matrix_UB_32      0.0024671000
_diffrn_orient_matrix_UB_33      -0.0002775000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8991
_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         27.498
_diffrn_reflns_theta_min         2.845
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74001
_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    1.269
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0391P)^2^+0.4339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2352
_reflns_number_total             2922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01682h2.cif
_cod_data_source_block           17
_cod_original_cell_volume        1273.55(15)
_cod_database_code               7057424
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'N3 O Br C13'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B), C14(H14A,H14B), C13(H13A,H13B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C8(H8), C7(H7), C5(H5), C6(H6)
;
_shelx_res_checksum              83533
_olex2_submission_special_instructions 'No special instructions were received'