2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic Building Blocks.
Funt, Liya D.; Krivolapova, Yulia V.; Khoroshilova, Olesya V.; Novikov, Mikhail Sergeevich; Khlebnikov, Alexander F.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03367

data_4038039
_publ_section_title
;
 2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic
 Building Blocks.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03367
_journal_year                    2020
_chemical_formula_moiety         'C9 H5 Br N4 O'
_chemical_formula_sum            'C9 H5 Br N4 O'
_chemical_formula_weight         265.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.064(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7524(5)
_cell_length_b                   5.31180(10)
_cell_length_c                   12.5363(3)
_cell_measurement_reflns_used    4681
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.1730
_cell_measurement_theta_min      3.5840
_cell_volume                     964.11(5)
_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(2)
_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 0.992
_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     22.00  63.00   1.00    1.00    --   40.13  38.00 120.00   41
  2  \w    127.00 154.00   1.00    1.00    --  113.00 112.00  90.00   27
  3  \w     89.00 176.00   1.00    1.00    --  113.00  45.00 120.00   87
  4  \w    102.00 132.00   1.00    1.00    --  113.00 -61.00 -30.00   30
  5  \w     66.00 100.00   1.00    1.00    --  113.00-112.00-150.00   34
  6  \w     38.00  90.00   1.00    1.00    --  113.00 -95.00   0.00   52
  7  \w     39.00 112.00   1.00    1.00    --  113.00-112.00  60.00   73
  8  \w     57.00  84.00   1.00    1.00    --   40.13-128.00 122.00   27
  9  \w     83.00 178.00   1.00    1.00    --  113.00  61.00  60.00   95
 10  \w     65.00 150.00   1.00    1.00    --  113.00 178.00-120.00   85
 11  \w    114.00 140.00   1.00    1.00    --  113.00 112.00-180.00   26
 12  \w    -67.00  35.00   1.00    1.00    --  -40.13  38.00-120.00  102
 13  \w   -100.00 -37.00   1.00    1.00    --  -40.13 178.00 -90.00   63
 14  \w    -65.00  36.00   1.00    1.00    --  -40.13  38.00 150.00  101
 15  \w   -114.00 -88.00   1.00    1.00    --  -40.13-143.00 -47.00   26
 16  \w     64.00 101.00   1.00    1.00    --   40.13-178.00  60.00   37
 17  \w     38.00 106.00   1.00    1.00    --   40.13  38.00-120.00   68
 18  \w     71.00  98.00   1.00    1.00    --   40.13-128.00 122.00   27
 19  \w     85.00 126.00   1.00    1.00    --  113.00 178.00-150.00   41
 20  \w    114.00 139.00   1.00    1.00    --  113.00 -45.00 -30.00   25
 21  \w     58.00 108.00   1.00    1.00    --  113.00 -95.00-120.00   50
 22  \w     44.00  90.00   1.00    1.00    --  113.00-112.00 -30.00   46
 23  \w     72.00  99.00   1.00    1.00    --  113.00 -45.00 -30.00   27
 24  \w    129.00 161.00   1.00    1.00    --  113.00 112.00 -60.00   32
 25  \w    143.00 178.00   1.00    1.00    --  113.00  45.00 150.00   35
 26  \w     89.00 115.00   1.00    1.00    --  113.00-112.00   0.00   26
 27  \w    113.00 144.00   1.00    1.00    --  113.00 112.00   0.00   31
 28  \w     75.00 115.00   1.00    1.00    --  113.00-112.00 150.00   40
 29  \w     24.00 147.00   1.00    1.00    --  113.00   0.00 -30.00  123
;
_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      -0.0993391000
_diffrn_orient_matrix_UB_12      -0.1040641000
_diffrn_orient_matrix_UB_13      -0.0205316000
_diffrn_orient_matrix_UB_21      0.0378000000
_diffrn_orient_matrix_UB_22      -0.2649537000
_diffrn_orient_matrix_UB_23      0.0329128000
_diffrn_orient_matrix_UB_31      -0.0060458000
_diffrn_orient_matrix_UB_32      0.0552170000
_diffrn_orient_matrix_UB_33      0.1190285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.153
_diffrn_reflns_theta_min         3.052
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41457
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         2.222
_refine_diff_density_min         -1.459
_refine_diff_density_rms         0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0576
_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^)+(0.1262P)^2^+0.3669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1921
_reflns_number_total             2000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03367_si_002.cif
_cod_data_source_block           10681-12999_lia584
_cod_original_cell_volume        964.11(4)
_cod_database_code               4038039
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C9 N4 Br O'
_shelx_estimated_absorpt_t_max   0.384
_shelx_estimated_absorpt_t_min   0.274
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C5(H5)
;
_shelx_res_checksum              67642
_shelx_hkl_checksum              1737
_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 4.171
_oxdiff_exptl_absorpt_empirical_full_min 0.324