2-Azidoazirines suitable for click chemistry: synthesis of 1-(2H-azirin-2-yl)-1H-1,2,3-triazoles
Golubev, Artem A.; Simdianov, Ivan V.; Smetanin, Ilia A.; Agafonova, Anastasiya V.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; New Journal of Chemistry 48 (2024) 19957–19962; doi:10.1039/D4NJ03517H

data_7063528
_publ_section_title
;
 2-Azidoazirines suitable for click chemistry: synthesis of
 1-(2H-azirin-2-yl)-1H-1,2,3-triazoles
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19957
_journal_page_last               19962
_journal_paper_doi               10.1039/D4NJ03517H
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C10 H7 Br N4 O2'
_chemical_formula_sum            'C10 H7 Br N4 O2'
_chemical_formula_weight         295.11
_chemical_name_systematic
'methyl 2-azido-3-(2-bromophenyl)-2H-azirine-2-carboxylate'
_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             2023-01-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-06 deposited with the CCDC.	2024-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.223(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1274(4)
_cell_length_b                   19.4244(7)
_cell_length_c                   7.4857(3)
_cell_measurement_reflns_used    3530
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      68.0200
_cell_measurement_theta_min      4.5480
_cell_volume                     1108.92(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -23.00   9.00   0.50    0.50    --   39.58 -89.00  33.00   64
  2  \w     16.00  70.00   0.50    0.50    --   39.58 -89.00  33.00  108
  3  \w     29.00 101.00   0.50    2.60    --   94.79 -89.00  33.00  144
  4  \w     82.00 146.00   0.50    2.60    --   94.79  89.00 148.00  128
  5  \w   -103.00 -28.00   0.50    0.50    --  -39.58 -43.00 -60.00  150
  6  \w    -15.00  16.00   0.50    0.50    --  -39.58  89.00 148.00   62
  7  \w   -106.00 -76.00   0.50    0.50    --  -39.58 -21.00-180.00   60
  8  \w    -51.00 -26.00   0.50    0.50    --  -39.58 -21.00-180.00   50
  9  \w     23.00 100.00   0.50    0.50    --   39.58  54.00  90.00  154
 10  \w     29.00  54.00   0.50    0.50    --   39.58  32.00-150.00   50
 11  \w     15.00  44.00   0.50    0.50    --   39.58-138.00   0.00   58
 12  \w      1.00  58.00   0.50    0.50    --   39.58 -54.00  90.00  114
 13  \w     61.00  86.00   0.50    0.50    --   39.58-138.00   0.00   50
 14  \w     85.00 147.00   0.50    2.60    --   94.79  25.00 -60.00  124
 15  \w     35.00 116.00   0.50    2.60    --   94.79 -68.00 150.00  162
 16  \w     53.00 126.00   0.50    2.60    --   94.79-145.00-150.00  146
 17  \w     35.00 109.00   0.50    2.60    --   94.79 -42.00  30.00  148
 18  \w     23.00  49.00   0.50    2.60    --   94.79 -96.00   0.00   52
 19  \w     50.00 102.00   0.50    2.60    --   94.79 -33.00 -30.00  104
 20  \w     45.00 105.00   0.50    2.60    --   94.79 -33.00-150.00  120
 21  \w     83.00 143.00   0.50    2.60    --   94.79  77.00 -60.00  120
 22  \w     44.00 102.00   0.50    2.60    --   94.79 -96.00-120.00  116
 23  \w     99.00 150.00   0.50    2.60    --   94.79  77.00-180.00  102
 24  \w     39.00  77.00   0.50    2.60    --   94.79 -59.00  30.00   76
 25  \w     86.00 111.00   0.50    2.60    --   94.79 -59.00  30.00   50
 26  \w     61.00 129.00   0.50    2.60    --   94.79   8.00 120.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1051857000
_diffrn_orient_matrix_UB_12      -0.0012558000
_diffrn_orient_matrix_UB_13      -0.1360591000
_diffrn_orient_matrix_UB_21      0.0739299000
_diffrn_orient_matrix_UB_22      0.0719804000
_diffrn_orient_matrix_UB_23      0.0704437000
_diffrn_orient_matrix_UB_31      0.1557078000
_diffrn_orient_matrix_UB_32      -0.0334185000
_diffrn_orient_matrix_UB_33      0.1568641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5008
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        64.984
_diffrn_reflns_theta_max         64.984
_diffrn_reflns_theta_min         4.553
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0446P)^2^+1.1677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1652
_reflns_number_total             1882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03517h2.cif
_cod_data_source_block           18442_lol2
_cod_depositor_comments
'Adding full bibliography for 7063527--7063529.cif.'
_cod_database_code               7063528
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C10 H7 Br1 N4 O2'
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.719
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              13870
_shelx_hkl_checksum              95687
_olex2_submission_original_sample_id 18442_LOL2
_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 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.709