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_7063527
_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         'C18 H14 N4 O2, C18 H15 N4 O2'
_chemical_formula_sum            'C36 H29 N8 O4'
_chemical_formula_weight         637.67
_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             2024-04-02
_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                97.1059(8)
_cell_angle_beta                 91.7213(10)
_cell_angle_gamma                94.7055(10)
_cell_formula_units_Z            2
_cell_length_a                   7.88082(11)
_cell_length_b                   12.52489(13)
_cell_length_c                   16.01630(14)
_cell_measurement_reflns_used    20384
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      77.1760
_cell_measurement_theta_min      2.7580
_cell_volume                     1562.19(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    -25.00  28.00   0.50    0.50    --  -47.20  19.00  60.00  106
  2  \w    -26.00  26.00   0.50    0.50    --   47.20 -19.00-120.00  104
  3  \w    -27.00  25.00   0.50    0.50    --   47.20 -19.00-180.00  104
  4  \w     33.00  70.00   0.50    0.50    --   47.20  57.00 -60.00   74
  5  \w     74.00 115.00   0.50    0.50    --   47.20  57.00 -60.00   82
  6  \w     80.00 108.00   0.50    0.50    --   47.20 125.00  60.00   56
  7  \w     90.00 139.00   0.50    2.10    --  107.75 117.00  94.00   98
  8  \w    142.00 171.00   0.50    2.10    --  107.75 125.00  60.00   58
  9  \w    106.00 178.00   0.50    2.10    --  107.75  15.00 -30.00  144
 10  \w    126.00 176.00   0.50    2.10    --  107.75  45.00-120.00  100
 11  \w     95.00 178.00   0.50    2.10    --  107.75  45.00-180.00  166
 12  \w     90.00 116.00   0.50    0.50    --   47.20 162.00-114.00   52
 13  \w     53.00  87.00   0.50    0.50    --   47.20 162.00-114.00   68
 14  \w     91.00 117.00   0.50    2.10    --  107.75 162.00-114.00   52
 15  \w    126.00 155.00   0.50    2.10    --  107.75 162.00-114.00   58
 16  \w     85.00 111.00   0.50    2.10    --  107.75 125.00  60.00   52
 17  \w     39.00  71.00   0.50    2.10    --  107.75 -61.00-120.00   64
 18  \w     59.00  99.00   0.50    2.10    --  107.75 -94.00-150.00   80
 19  \w     62.00  88.00   0.50    2.10    --  107.75 -94.00-180.00   52
 20  \w     62.00  87.00   0.50    2.10    --  107.75-162.00-142.00   50
 21  \w     76.00 112.00   0.50    2.10    --  107.75-125.00 -60.00   72
 22  \w     82.00 109.00   0.50    2.10    --  107.75-117.00   7.00   54
 23  \w     78.00 104.00   0.50    2.10    --  107.75 -94.00  30.00   52
 24  \w     63.00 111.00   0.50    2.10    --  107.75-125.00 120.00   96
 25  \w     45.00  71.00   0.50    2.10    --  107.75 -61.00  30.00   52
 26  \w     35.00  71.00   0.50    2.10    --  107.75 -61.00  60.00   72
 27  \w     36.00 104.00   0.50    2.10    --  107.75 -94.00   0.00  136
 28  \w     35.00 112.00   0.50    2.10    --  107.75-125.00 -90.00  154
 29  \w     83.00 108.00   0.50    0.50    --   47.20-162.00-142.00   50
 30  \w     43.00 112.00   0.50    2.10    --  107.75-125.00-150.00  138
 31  \w     35.00 110.00   0.50    2.10    --  107.75-125.00-180.00  150
 32  \w     38.00  68.00   0.50    2.10    --  107.75 -61.00 -90.00   60
 33  \w     37.00  70.00   0.50    2.10    --  107.75 -61.00-180.00   66
 34  \w     22.00  48.00   0.50    0.50    --   47.20-117.00   7.00   52
 35  \w     36.00  70.00   0.50    2.10    --  107.75 -94.00  30.00   68
 36  \w    -90.00 -11.00   0.50    0.50    --  -47.20 117.00  94.00  158
 37  \w    -68.00 -38.00   0.50    2.10    -- -106.00  61.00  60.00   60
 38  \w    -72.00 -34.00   0.50    2.10    -- -106.00 125.00   0.00   76
 39  \w    -58.00 -33.00   0.50    2.10    -- -106.00 108.00 -81.47   50
 40  \w    -65.00 -39.00   0.50    2.10    -- -106.00  61.00 -90.00   52
 41  \w    -62.00 -33.00   0.50    2.10    -- -106.00  61.00 -60.00   58
 42  \w    -99.00 -74.00   0.50    0.50    --  -47.20 162.00-114.00   50
 43  \w   -100.00 -75.00   0.50    0.50    --  -47.20-125.00  60.00   50
 44  \w   -139.00-113.00   0.50    2.10    -- -106.00-117.00   7.00   52
 45  \w   -140.00 -99.00   0.50    2.10    -- -106.00 -61.00 -60.00   82
 46  \w   -135.00 -86.00   0.50    2.10    -- -106.00 -94.00-120.00   98
 47  \w   -127.00-102.00   0.50    2.10    -- -106.00-162.00-142.00   50
 48  \w    -96.00 -50.00   0.50    0.50    --  -47.20-162.00-142.00   92
 49  \w   -125.00 -92.00   0.50    2.10    -- -106.00 -15.00  60.00   66
 50  \w    -98.00 -34.00   0.50    2.10    -- -106.00  77.00 120.00  128
 51  \w   -108.00 -68.00   0.50    2.10    -- -106.00 117.00  94.00   80
 52  \w   -112.00 -56.00   0.50    2.10    -- -106.00 125.00 150.00  112
 53  \w   -109.00 -83.00   0.50    2.10    -- -106.00 115.00  63.26   52
 54  \w   -120.00 -94.00   0.50    2.10    -- -106.00 137.00 -38.04   52
 55  \w   -107.00 -70.00   0.50    2.10    -- -106.00 108.00 -81.47   74
 56  \w   -136.00 -98.00   0.50    2.10    -- -106.00 162.00-114.00   76
 57  \w   -149.00 -92.00   0.50    2.10    -- -106.00 -15.00 -30.00  114
 58  \w   -172.00-147.00   0.50    2.10    -- -106.00 -61.00 -60.00   50
 59  \w   -176.00-151.00   0.50    2.10    -- -106.00 -94.00-120.00   50
 60  \w   -176.00-121.00   0.50    2.10    -- -106.00 -45.00 -90.00  110
 61  \w     82.00 117.00   0.50    0.50    --   47.20 125.00 150.00   70
 62  \w    -56.00 -31.00   0.50    0.50    --   10.00 156.00 170.94   50
 63  \w    -20.00   9.00   0.50    0.50    --   14.00 101.00  22.26   58
 64  \w     -8.00  17.00   0.50    0.50    --   26.00 100.00 150.86   50
 65  \w     -3.00  22.00   0.50    0.50    --   30.00  98.00-117.21   50
 66  \w     12.00  37.00   0.50    0.50    --   38.00  85.00 -29.26   50
 67  \w     15.00  40.00   0.50    0.50    --   42.00  87.00 137.21   50
 68  \w     17.00  42.00   0.50    0.50    --   46.00  90.00-137.66   50
 69  \w    -67.00 -40.00   0.50    0.50    --  -47.20 -19.00-150.00   54
 70  \w     25.00  54.00   0.50    0.50    --   47.20  77.00   0.00   58
 71  \w     30.00  56.00   0.50    0.50    --   54.00  79.00 164.31   52
 72  \w     33.00  59.00   0.50    0.50    --   54.00  78.00 -65.50   52
 73  \w     30.00  83.00   0.50    0.50    --   54.00  79.00   3.32  106
 74  \w     35.00  61.00   0.50    0.50    --   54.00  79.00  19.25   52
 75  \w     35.00  69.00   0.50    0.50    --   58.00  78.00  63.28   68
 76  \w     35.00  60.00   0.50    0.50    --   58.00  77.00 119.16   50
 77  \w     35.00  61.00   0.50    0.50    --   58.00  77.00-167.89   52
 78  \w     38.00  63.00   0.50    0.50    --   62.00  80.00-108.83   50
 79  \w     41.00  67.00   0.50    0.50    --   62.00  75.00-146.05   52
 80  \w    -72.00 -43.00   0.50    0.50    --  -66.00 -78.00 -48.27   58
 81  \w     44.00  70.00   0.50    0.50    --   66.00  76.00  22.00   52
 82  \w     44.00  81.00   0.50    0.50    --   66.00  76.00 141.21   74
 83  \w     42.00  68.00   0.50    0.50    --   66.00  79.00 -68.39   52
 84  \w    -77.00 -51.00   0.50    0.50    --  -70.00 -68.00  82.37   52
 85  \w     48.00  73.00   0.50    0.50    --   70.00  76.00  81.39   50
 86  \w     47.00  73.00   0.50    0.50    --   70.00  77.00  40.54   52
 87  \w    -79.00 -53.00   0.50    0.50    --  -74.00 -75.00-173.38   52
 88  \w    -76.00 -51.00   0.50    0.50    --  -74.00 -76.00-114.15   50
 89  \w     52.00  78.00   0.50    0.50    --   74.00  76.00 167.33   52
 90  \w    -93.00 -58.00   0.50    2.10    --  -78.00 -70.00-127.69   70
 91  \w    -85.00 -59.00   0.50    2.10    --  -78.00 -73.00 -73.95   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0932076000
_diffrn_orient_matrix_UB_12      -0.0931255000
_diffrn_orient_matrix_UB_13      -0.0603959000
_diffrn_orient_matrix_UB_21      0.0929561000
_diffrn_orient_matrix_UB_22      0.0412669000
_diffrn_orient_matrix_UB_23      -0.0745677000
_diffrn_orient_matrix_UB_31      0.1456277000
_diffrn_orient_matrix_UB_32      -0.0714460000
_diffrn_orient_matrix_UB_33      0.0142558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34701
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.438
_diffrn_reflns_theta_min         2.783
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
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    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0485P)^2^+0.4770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5757
_reflns_number_total             6491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03517h2.cif
_cod_data_source_block           15347_agf16
_cod_depositor_comments
'Adding full bibliography for 7063527--7063529.cif.'
_cod_database_code               7063527
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H14 O2 N4'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.929
_diffrn_oxdiff_digest_frames
;
0182137e6bc5cecce76d73b736b07ba89d00031650b
;
_diffrn_oxdiff_digest_hkl
;
01975d05f5cb222f5ac498d91845406c1b1784
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N37(H37), C35(H35), C14(H14), C30(H30), C26(H26), C6(H6), C20(H20), C44(H44),
 C16(H16), C29(H29), C27(H27), C28(H28), C19(H19), C43(H43), C40(H40), C2(H2),
 C5(H5), C18(H18), C17(H17), C3(H3), C42(H42), C4(H4), C41(H41)
1.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C47(H47A,H47B,H47C)
;
_shelx_res_checksum              21400
_shelx_hkl_checksum              95047
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.727