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_7063529
_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 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-04-11 deposited with the CCDC.	2024-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                101.346(4)
_cell_angle_beta                 99.374(4)
_cell_angle_gamma                99.632(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9685(3)
_cell_length_b                   9.2906(4)
_cell_length_c                   9.6913(4)
_cell_measurement_reflns_used    4294
_cell_measurement_temperature    99.8(7)
_cell_measurement_theta_max      68.8740
_cell_measurement_theta_min      4.7520
_cell_volume                     508.69(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     68.00  93.00   0.50    0.53    --   35.61  33.00-154.00   50
  2  \w     25.00  61.00   0.50    0.53    --   35.61  33.00-154.00   72
  3  \w    -35.00  22.00   0.50    0.53    --   35.61 -33.00  47.00  114
  4  \w     82.00 108.00   0.50    2.14    --  100.00 -33.00  47.00   52
  5  \w    132.00 157.00   0.50    2.14    --  100.00  33.00-154.00   50
  6  \w     31.00  57.00   0.50    2.14    --  100.00 -33.00  47.00   52
  7  \w    -56.00  -9.00   0.50    0.53    --  -35.61  77.00-120.00   94
  8  \w    -63.00 -38.00   0.50    0.53    --  -35.61  21.00  30.00   50
  9  \w     -6.00  35.00   0.50    0.53    --  -35.61  77.00-120.00   82
 10  \w    -22.00   4.00   0.50    0.53    --  -35.61  33.00-154.00   52
 11  \w    -49.00 -15.00   0.50    0.53    --  -35.61 -54.00 -90.00   68
 12  \w    -80.00 -54.00   0.50    0.53    --  -35.61 -54.00 -90.00   52
 13  \w    -82.00 -56.00   0.50    0.53    --  -35.61 138.00 -60.00   52
 14  \w   -100.00 -54.00   0.50    0.53    --  -35.61 -33.00  47.00   92
 15  \w    -99.00 -16.00   0.50    0.53    --  -35.61 -65.00 120.00  166
 16  \w    -45.00 -14.00   0.50    0.53    --  -35.61 138.00 -60.00   62
 17  \w    -27.00  36.00   0.50    0.53    --  -35.61  21.00  30.00  126
 18  \w     15.00  87.00   0.50    0.53    --   35.61-138.00 -30.00  144
 19  \w      8.00  44.00   0.50    0.53    --   35.61 -32.00 -90.00   72
 20  \w     23.00  59.00   0.50    0.53    --   35.61-138.00  90.00   72
 21  \w     60.00 102.00   0.50    0.53    --   35.61  43.00-150.00   84
 22  \w     49.00  74.00   0.50    0.53    --   35.61-138.00-180.00   50
 23  \w     67.00  96.00   0.50    0.53    --   35.61-138.00  90.00   58
 24  \w     11.00  69.00   0.50    0.53    --   35.61-104.00  90.00  116
 25  \w     87.00 140.00   0.50    2.14    --  100.00  30.00 150.00  106
 26  \w     91.00 155.00   0.50    2.14    --  100.00  77.00   0.00  128
 27  \w    101.00 142.00   0.50    2.14    --  100.00  15.00 -60.00   82
 28  \w     62.00 115.00   0.50    2.14    --  100.00  15.00   0.00  106
 29  \w     92.00 129.00   0.50    2.14    --  100.00-149.00  30.00   74
 30  \w     62.00  88.00   0.50    2.14    --  100.00-149.00  30.00   52
 31  \w     34.00 125.00   0.50    2.14    --  100.00 -61.00-150.00  182
 32  \w    121.00 151.00   0.50    2.14    --  100.00  15.00   0.00   60
 33  \w     33.00 107.00   0.50    2.14    --  100.00 -45.00  30.00  148
 34  \w     64.00  89.00   0.50    2.14    --  100.00  15.00 -60.00   50
 35  \w     37.00  92.00   0.50    2.14    --  100.00 -91.00-150.00  110
 36  \w     35.00  60.00   0.50    2.14    --  100.00-125.00  90.00   50
 37  \w    107.00 157.00   0.50    2.14    --  100.00  15.00-120.00  100
 38  \w     35.00  87.00   0.50    2.14    --  100.00-107.00-180.00  104
 39  \w     80.00 115.00   0.50    2.14    --  100.00 -30.00 -60.00   70
 40  \w     80.00 105.00   0.50    2.14    --  100.00 -91.00-120.00   50
 41  \w    119.00 157.00   0.50    2.14    --  100.00  53.00-180.00   76
 42  \w     28.00  56.00   0.50    2.14    --  100.00 -30.00 -60.00   56
 43  \w     23.00  67.00   0.50    2.14    --  100.00 -91.00  30.00   88
 44  \w     80.00 111.00   0.50    2.14    --  100.00  53.00-180.00   62
 45  \w     45.00 127.00   0.50    2.14    --  100.00-149.00 -90.00  164
 46  \w     28.00  53.00   0.50    2.14    --  100.00 -91.00-120.00   50
 47  \w     34.00  96.00   0.50    2.14    --  100.00-107.00  90.00  124
 48  \w     46.00 127.00   0.50    2.14    --  100.00 -69.00  60.00  162
 49  \w     26.00  79.00   0.50    2.14    --  100.00 -91.00   0.00  106
 50  \w     61.00  92.00   0.50    2.14    --  100.00  15.00-120.00   62
 51  \w     66.00 109.00   0.50    2.14    --  100.00-125.00  90.00   86
 52  \w     84.00 129.00   0.50    2.14    --  100.00-149.00-150.00   90
 53  \w     83.00 147.00   0.50    2.14    --  100.00  77.00-120.00  128
 54  \w     97.00 122.00   0.50    2.14    --  100.00  77.00  60.00   50
 55  \w     81.00 106.00   0.50    2.14    --  100.00-107.00-150.00   50
 56  \w     72.00 107.00   0.50    2.14    --  100.00-125.00  30.00   70
 57  \w     33.00 118.00   0.50    2.14    --  100.00 -37.00-150.00  170
 58  \w     94.00 119.00   0.50    2.14    --  100.00 -33.00  47.00   50
 59  \w    -42.00 -17.00   0.50    0.53    --   12.00 129.00 -63.86   50
 60  \w    -22.00   3.00   0.50    0.53    --   20.00 110.00  28.70   50
 61  \w      3.00  28.00   0.50    0.53    --   35.61  88.00  -6.32   50
 62  \w     18.00  58.00   0.50    0.53    --   35.61-138.00  30.00   80
 63  \w     30.00  56.00   0.50    0.53    --   35.61 -65.00 120.00   52
 64  \w      3.00  28.00   0.50    0.53    --   35.61  86.00  21.84   50
 65  \w      3.00  28.00   0.50    0.53    --   35.61  88.00-172.29   50
 66  \w      3.00  28.00   0.50    0.53    --   35.61  87.00 122.73   50
 67  \w    -10.00  16.00   0.50    0.53    --   35.61 -65.00 120.00   52
 68  \w      3.00  28.00   0.50    0.53    --   36.00  86.00  75.46   50
 69  \w      2.00  27.00   0.50    0.53    --   36.00  90.00-102.15   50
 70  \w      2.00  27.00   0.50    0.53    --   36.00  90.00-160.38   50
 71  \w     11.00  37.00   0.50    0.53    --   40.00  80.00 -49.27   52
 72  \w     14.00  39.00   0.50    0.53    --   44.00  81.00  75.75   50
 73  \w     14.00  39.00   0.50    0.53    --   44.00  80.00   0.53   50
 74  \w     13.00  38.00   0.50    0.53    --   44.00  82.00-101.21   50
 75  \w     16.00  42.00   0.50    0.53    --   44.00  82.00 146.83   52
 76  \w     13.00  38.00   0.50    0.53    --   44.00  82.00 111.66   50
 77  \w     26.00  52.00   0.50    0.53    --   48.00  68.00-149.07   52
 78  \w     90.00 116.00   0.50    0.53    --   56.00  70.00 -32.63   52
 79  \w     30.00  58.00   0.50    0.53    --   56.00  70.00 -32.63   56
 80  \w     36.00  71.00   0.50    0.53    --   56.00  71.00 143.24   70
 81  \w     95.00 121.00   0.50    0.53    --   60.00  70.00 109.26   52
 82  \w     85.00 111.00   0.50    0.53    --   60.00  71.00 -77.51   52
 83  \w     37.00  77.00   0.50    0.53    --   60.00  71.00 -77.51   80
 84  \w     45.00  75.00   0.50    0.53    --   60.00  70.00 109.26   60
 85  \w     37.00  68.00   0.50    0.53    --   60.00  53.00-130.15   62
 86  \w     36.00  78.00   0.50    0.53    --   60.00  66.00  17.39   84
 87  \w     84.00 110.00   0.50    0.53    --   60.00  66.00  17.39   52
 88  \w    107.00 132.00   0.50    0.53    --   64.00  59.00  58.92   50
 89  \w     40.00  66.00   0.50    0.53    --   64.00  59.00  58.92   52
 90  \w     98.00 124.00   0.50    2.14    --   68.00  51.00-167.04   52
 91  \w     45.00  70.00   0.50    2.14    --   68.00  51.00-167.04   50
 92  \w     43.00  69.00   0.50    2.14    --   68.00  60.00-104.27   52
 93  \w     41.00  73.00   0.50    2.14    --   68.00  68.00  81.66   64
 94  \w     47.00  85.00   0.50    2.14    --   72.00  60.00 -31.93   76
 95  \w     54.00  80.00   0.50    2.14    --   80.00  70.00 -92.66   52
 96  \w     91.00 143.00   0.50    2.14    --   80.00  70.00 -92.66  104
 97  \w    101.00 142.00   0.50    2.14    --   88.00  68.00 -28.75   82
 98  \w     61.00  92.00   0.50    2.14    --   88.00  68.00 -28.75   62
 99  \w     64.00  90.00   0.50    2.14    --   88.00  70.00-124.87   52
100  \w     73.00 113.00   0.50    2.14    --  100.00  69.00   0.00   80
101  \w    132.00 157.00   0.50    2.14    --  100.00  53.00   0.00   50
102  \w     80.00 108.00   0.50    2.14    --  100.00  53.00   0.00   56
103  \w     81.00 114.00   0.50    2.14    --  100.00  53.00-150.00   66
104  \w     34.00  59.00   0.50    2.14    --  100.00 -37.00 120.00   50
105  \w     74.00 151.00   0.50    2.14    --  100.00  69.00  30.00  154
106  \w     80.00 121.00   0.50    2.14    --  100.00 125.00 -90.00   82
107  \w    132.00 157.00   0.50    2.14    --  100.00  69.00 -30.00   50
108  \w    122.00 155.00   0.50    2.14    --  100.00  69.00  90.00   66
109  \w    132.00 157.00   0.50    2.14    --  100.00  69.00-120.00   50
110  \w     77.00 103.00   0.50    2.14    --  100.00  69.00-120.00   52
111  \w    123.00 152.00   0.50    2.14    --  100.00  61.00  60.00   58
112  \w     87.00 113.00   0.50    2.14    --  100.00 -37.00 120.00   52
113  \w     76.00 119.00   0.50    2.14    --  100.00  61.00  60.00   86
114  \w     73.00 115.00   0.50    2.14    --  100.00  69.00 -30.00   84
115  \w    132.00 157.00   0.50    2.14    --  100.00  69.00 -90.00   50
116  \w     73.00 105.00   0.50    2.14    --  100.00  69.00 -90.00   64
117  \w    122.00 148.00   0.50    2.14    --  100.00  61.00 150.00   52
118  \w     73.00  99.00   0.50    2.14    --  100.00  69.00  90.00   52
119  \w     75.00 101.00   0.50    2.14    --  100.00  65.00 162.93   52
120  \w    131.00 157.00   0.50    2.14    --  100.00  65.00 162.93   52
121  \w    127.00 153.00   0.50    2.14    --  100.00  69.00 -60.00   52
122  \w     83.00 110.00   0.50    2.14    --  100.00  69.00 -60.00   54
123  \w     73.00  98.00   0.50    2.14    --  100.00  69.00-180.00   50
124  \w    111.00 152.00   0.50    2.14    --  100.00  65.00  81.02   82
125  \w    117.00 146.00   0.50    2.14    --  100.00  69.00 120.00   58
126  \w     75.00 113.00   0.50    2.14    --  100.00  61.00 150.00   76
127  \w     75.00 101.00   0.50    2.14    --  100.00  65.00  81.02   52
128  \w     73.00 100.00   0.50    2.14    --  100.00  69.00 120.00   54
129  \w     80.00 112.00   0.50    2.14    --  100.00  45.00 120.00   64
130  \w     80.00 124.00   0.50    2.14    --  100.00  53.00  30.00   88
131  \w     76.00 102.00   0.50    2.14    --  100.00  61.00 -60.00   52
132  \w    107.00 132.00   0.50    2.14    --  100.00  61.00 -60.00   50
133  \w     73.00 108.00   0.50    2.14    --  100.00  69.00-150.00   70
;
_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      -0.0222868000
_diffrn_orient_matrix_UB_12      -0.1523960000
_diffrn_orient_matrix_UB_13      0.0422864000
_diffrn_orient_matrix_UB_21      0.2202612000
_diffrn_orient_matrix_UB_22      -0.0249930000
_diffrn_orient_matrix_UB_23      -0.0568409000
_diffrn_orient_matrix_UB_31      0.1498770000
_diffrn_orient_matrix_UB_32      0.0776048000
_diffrn_orient_matrix_UB_33      0.1496410000
_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  0.0517
_diffrn_reflns_av_unetI/netI     0.0404
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7082
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.490
_diffrn_reflns_theta_max         67.490
_diffrn_reflns_theta_min         4.752
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
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    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0596P)^2^+0.0488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1584
_reflns_number_total             1838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03517h2.cif
_cod_data_source_block           077-028_auto
_cod_depositor_comments
'Adding full bibliography for 7063527--7063529.cif.'
_cod_database_code               7063529
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C10 H8 N4 O2 '
_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:
 C4(H4), C8(H8), C6(H6), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              76874
_shelx_hkl_checksum              28631
_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 4.225
_oxdiff_exptl_absorpt_empirical_full_min 0.515