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_7057422
_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         'C21 H22 N4'
_chemical_formula_sum            'C21 H22 N4'
_chemical_formula_weight         330.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-02
_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                86.090(6)
_cell_angle_beta                 89.456(6)
_cell_angle_gamma                67.095(7)
_cell_formula_units_Z            4
_cell_length_a                   11.2501(8)
_cell_length_b                   12.7520(10)
_cell_length_c                   13.2943(10)
_cell_measurement_reflns_used    2641
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2650
_cell_measurement_theta_min      3.4860
_cell_volume                     1752.4(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega    9.00   47.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   57.0000  -60.0000 38

  2 omega  -82.00  -50.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000  150.0000 32

  3 omega  -38.00   48.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   77.0000    0.0000 86

  4 omega  -89.00  -36.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000  -30.0000 53

  5 omega  -19.00   20.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   60.0000 39

  6 omega   25.00   60.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -60.0000 35

  7 omega    5.00   92.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -90.0000 87

  8 omega  -35.00   40.00   1.0000   78.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000  150.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0156964000
_diffrn_orient_matrix_UB_12      0.0384475000
_diffrn_orient_matrix_UB_13      -0.0435850000
_diffrn_orient_matrix_UB_21      0.0318422000
_diffrn_orient_matrix_UB_22      0.0316030000
_diffrn_orient_matrix_UB_23      0.0215755000
_diffrn_orient_matrix_UB_31      0.0585325000
_diffrn_orient_matrix_UB_32      -0.0344558000
_diffrn_orient_matrix_UB_33      -0.0222653000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15832
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.514
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91551
_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    1.252
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0431P)^2^+0.2403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5434
_reflns_number_total             7989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01682h2.cif
_cod_data_source_block           19
_cod_database_code               7057422
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30
_reflns_odcompleteness_completeness 99.15
_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:
 C16A(H16A), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17A(H17A,H17B), C21A(H21A,H21B), C20A(H20A,H20B), C18A(H18A,H18B), C19A(H19A,
 H19B), C17(H17C,H17D), C18(H18C,H18D), C21(H21C,H21D), C19(H19C,H19D),
 C20(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C12A(H12A), C6A(H6A), C15A(H15A), C13A(H13A), C9A(H9A), N4A(H4A),
 C7A(H7A), C5A(H5A), C8A(H8A), C14A(H14A), N4(H4), C9(H9), C11(H11), C7(H7),
 C14(H14), C5(H5), C13(H13), C12(H12), C15(H15), C6(H6), C8(H8)
;
_shelx_res_checksum              9635
_olex2_submission_special_instructions 'No special instructions were received'