Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines
Krivolapova, Yulia V.; Tomashenko, Olesya A.; Funt, Liya D.; Spiridonova, Dar’ya V.; Novikov, Mikhail Sergeevich; Khlebnikov, Alexander F.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00908K

data_7158735
_publ_section_title
;
 Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-,
 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and
 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00908K
_journal_year                    2022
_chemical_formula_moiety         'C22 H20 N4 O3 S'
_chemical_formula_sum            'C22 H20 N4 O3 S'
_chemical_formula_weight         420.48
_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             2022-04-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-04-21 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                111.2290(10)
_cell_angle_beta                 91.7750(10)
_cell_angle_gamma                99.4960(10)
_cell_formula_units_Z            4
_cell_length_a                   6.89270(10)
_cell_length_b                   17.0842(2)
_cell_length_c                   19.2068(2)
_cell_measurement_reflns_used    15778
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.5530
_cell_measurement_theta_min      2.4610
_cell_volume                     2069.21(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -28.00  16.00   0.50    0.25    --   39.58 -87.00 127.00   88
  2  \w     22.00  57.00   0.50    0.25    --   39.58 -87.00 127.00   70
  3  \w     34.00  76.00   0.50    1.80    --  100.00 -87.00 127.00   84
  4  \w     90.00 118.00   0.50    1.80    --  100.00 -87.00 127.00   56
  5  \w    -84.00 -21.00   0.50    0.25    --  -39.58 -54.00 120.00  126
  6  \w    -12.00  28.00   0.50    0.25    --  -39.58  32.00  60.00   80
  7  \w     -8.00  18.00   0.50    0.25    --  -39.58  87.00-115.00   52
  8  \w    -48.00 -15.00   0.50    0.25    --  -39.58  32.00  60.00   66
  9  \w    -56.00 -18.00   0.50    0.25    --  -39.58 138.00 -90.00   76
 10  \w    -54.00  22.00   0.50    0.25    --  -39.58  43.00 -60.00  152
 11  \w    -68.00 -25.00   0.50    0.25    --  -39.58 -43.00 150.00   86
 12  \w   -104.00 -76.00   0.50    0.25    --  -39.58 -43.00 150.00   56
 13  \w     -4.00  21.00   0.50    0.25    --  -39.58  77.00 150.00   50
 14  \w    -44.00 -19.00   0.50    0.25    --  -39.58  77.00 150.00   50
 15  \w    -57.00 -16.00   0.50    0.25    --  -39.58  87.00-115.00   82
 16  \w    -89.00 -59.00   0.50    0.25    --  -39.58 138.00 -90.00   60
 17  \w     32.00  91.00   0.50    0.25    --   39.58  65.00  90.00  118
 18  \w     29.00  55.00   0.50    0.25    --   39.58 -54.00 -60.00   52
 19  \w     44.00  70.00   0.50    0.25    --   39.58-104.00  90.00   52
 20  \w    -24.00   3.00   0.50    0.25    --   39.58 -54.00 -60.00   54
 21  \w     17.00  96.00   0.50    0.25    --   39.58-138.00 120.00  158
 22  \w    -23.00  51.00   0.50    0.25    --   39.58 -32.00-150.00  148
 23  \w    -29.00   7.00   0.50    0.25    --   39.58 -89.00 -30.00   72
 24  \w     45.00  70.00   0.50    0.25    --   39.58 -89.00 -30.00   50
 25  \w     48.00 108.00   0.50    0.25    --   39.58  21.00  30.00  120
 26  \w    -10.00  17.00   0.50    0.25    --   39.58-104.00  90.00   54
 27  \w     72.00  98.00   0.50    0.25    --   39.58  43.00-120.00   52
 28  \w     57.00  82.00   0.50    0.25    --   39.58  32.00  60.00   50
 29  \w     43.00  69.00   0.50    0.25    --   39.58  43.00-120.00   52
 30  \w     36.00  81.00   0.50    1.80    --  100.00 -53.00  30.00   90
 31  \w     94.00 147.00   0.50    1.80    --  100.00 111.00 150.00  106
 32  \w     56.00 119.00   0.50    1.80    --  100.00 -69.00-150.00  126
 33  \w    102.00 129.00   0.50    1.80    --  100.00  22.00 -60.00   54
 34  \w     36.00 118.00   0.50    1.80    --  100.00-133.00  90.00  164
 35  \w     60.00 117.00   0.50    1.80    --  100.00 -61.00  30.00  114
 36  \w     79.00 108.00   0.50    1.80    --  100.00-111.00 -30.00   58
 37  \w     95.00 121.00   0.50    1.80    --  100.00 -86.00  60.00   52
 38  \w     33.00  78.00   0.50    1.80    --  100.00 -86.00  60.00   90
 39  \w     75.00 112.00   0.50    1.80    --  100.00 -37.00  30.00   74
 40  \w     34.00  70.00   0.50    1.80    --  100.00 -37.00  30.00   72
 41  \w     97.00 149.00   0.50    1.80    --  100.00  93.00 150.00  104
 42  \w    131.00 157.00   0.50    1.80    --  100.00  77.00-180.00   52
 43  \w     49.00  91.00   0.50    1.80    --  100.00-111.00   0.00   84
 44  \w     88.00 136.00   0.50    1.80    --  100.00 111.00-180.00   96
 45  \w     36.00 115.00   0.50    1.80    --  100.00 -45.00-150.00  158
 46  \w     47.00 107.00   0.50    1.80    --  100.00 -61.00 120.00  120
 47  \w     83.00 156.00   0.50    1.80    --  100.00  15.00 -90.00  146
 48  \w     78.00 104.00   0.50    1.80    --  100.00 -93.00-120.00   52
 49  \w     77.00 151.00   0.50    1.80    --  100.00  15.00-120.00  148
 50  \w     97.00 155.00   0.50    1.80    --  100.00  45.00 -30.00  116
 51  \w     61.00 106.00   0.50    1.80    --  100.00 -93.00  30.00   90
 52  \w    124.00 150.00   0.50    1.80    --  100.00 111.00 120.00   52
 53  \w     84.00 118.00   0.50    1.80    --  100.00-133.00 -60.00   68
 54  \w     39.00  65.00   0.50    1.80    --  100.00-133.00 -60.00   52
 55  \w     36.00 116.00   0.50    1.80    --  100.00 -45.00 120.00  160
 56  \w     91.00 116.00   0.50    1.80    --  100.00-133.00-150.00   50
 57  \w     30.00  56.00   0.50    1.80    --  100.00 -15.00   0.00   52
 58  \w     81.00 121.00   0.50    1.80    --  100.00 -15.00   0.00   80
 59  \w     97.00 122.00   0.50    1.80    --  100.00  30.00 150.00   50
 60  \w     45.00  70.00   0.50    1.80    --  100.00-133.00-150.00   50
 61  \w    123.00 148.00   0.50    1.80    --  100.00  30.00 120.00   50
 62  \w     69.00 118.00   0.50    1.80    --  100.00 -53.00 -90.00   98
 63  \w    111.00 155.00   0.50    1.80    --  100.00  93.00 -30.00   88
 64  \w     84.00 127.00   0.50    1.80    --  100.00  77.00 -30.00   86
 65  \w     75.00 108.00   0.50    1.80    --  100.00-111.00-180.00   66
 66  \w     39.00  66.00   0.50    1.80    --  100.00-111.00 -90.00   54
 67  \w     92.00 117.00   0.50    1.80    --  100.00  30.00 120.00   50
 68  \w     47.00  90.00   0.50    1.80    --  100.00 -93.00   0.00   86
 69  \w     96.00 121.00   0.50    1.80    --  100.00  30.00  90.00   50
 70  \w     84.00 157.00   0.50    1.80    --  100.00  53.00 -60.00  146
 71  \w     86.00 112.00   0.50    1.80    --  100.00 111.00 120.00   52
 72  \w    132.00 157.00   0.50    1.80    --  100.00  93.00-120.00   50
 73  \w     45.00  70.00   0.50    1.80    --  100.00 -93.00 150.00   50
 74  \w     88.00 117.00   0.50    1.80    --  100.00-133.00 150.00   58
 75  \w     85.00 111.00   0.50    1.80    --  100.00  87.00-115.00   52
;
_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      0.0238028000
_diffrn_orient_matrix_UB_12      0.0737796000
_diffrn_orient_matrix_UB_13      0.0770940000
_diffrn_orient_matrix_UB_21      -0.2213255000
_diffrn_orient_matrix_UB_22      -0.0243742000
_diffrn_orient_matrix_UB_23      0.0078377000
_diffrn_orient_matrix_UB_31      0.0480192000
_diffrn_orient_matrix_UB_32      -0.0605646000
_diffrn_orient_matrix_UB_33      0.0383690000
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22886
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_min         2.480
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0405P)^2^+1.1166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7023
_reflns_number_total             7834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00908k2.cif
_cod_data_source_block           19485_lia036
_cod_database_code               7158735
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H20 N4 O3 S'
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.801
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1), C4(H4A), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19),
  C20(H20), C21(H21), N4'(H4'), C1'(H1'), C4'(H4'A), C5'(H5'), C7'(H7'),
 C8'(H8'), C17'(H17'), C18'(H18'), C19'(H19'), C20'(H20'), C21'(H21')
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C9'(H9'A,H9'B,
 H9'C), C15'(H15D,H15E,H15F), C22'(H22D,H22E,H22F)
;
_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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.749