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_7158734
_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         'C17 H14 N4 O2 S'
_chemical_formula_sum            'C17 H14 N4 O2 S'
_chemical_formula_weight         338.38
_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     direct
_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                90
_cell_angle_beta                 110.866(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6565(4)
_cell_length_b                   44.4687(14)
_cell_length_c                   9.8470(4)
_cell_measurement_reflns_used    13904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.9440
_cell_measurement_theta_min      2.8630
_cell_volume                     3132.8(3)
_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 1.5 (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, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2096
_diffrn_detector_type            Eos
_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    -44.00   5.50   0.75   22.66    --  -25.43  57.00   0.00   66
  2  \w    -94.00 -67.00   0.75   22.66    --  -25.43 -57.00  30.00   36
  3  \w     11.50  43.00   0.75   22.66    --  -25.43  57.00   0.00   42
  4  \w      1.75  43.00   0.75   22.66    --  -25.43  57.00-180.00   55
  5  \w    -42.00  56.25   0.75   22.66    --   26.52 -77.00 120.00  131
  6  \w     -2.00  91.00   0.75   22.66    --   26.52  77.00-120.00  124
  7  \w     36.00 101.25   0.75   22.66    --   26.52 178.00 -60.00   87
  8  \w    -12.00  67.50   0.75   22.66    --   26.52 -99.00  60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0004799000
_diffrn_orient_matrix_UB_12      0.0155864000
_diffrn_orient_matrix_UB_13      0.0154817000
_diffrn_orient_matrix_UB_21      0.0774353000
_diffrn_orient_matrix_UB_22      -0.0020985000
_diffrn_orient_matrix_UB_23      0.0653821000
_diffrn_orient_matrix_UB_31      0.0616153000
_diffrn_orient_matrix_UB_32      0.0027566000
_diffrn_orient_matrix_UB_33      -0.0379668000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34619
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.605
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78129
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         9126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.299
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.1175
_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^)+21.1826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8458
_reflns_number_total             9126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00908k2.cif
_cod_data_source_block           12570-lia603
_cod_original_cell_volume        3132.8(2)
_cod_database_code               7158734
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H14 N4 O2 S'
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.916
_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 Ternary CH refined with riding coordinates:
 C3(H3), C3'(H3')
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C1'(H1'), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'),
 C10'(H10'), C12'(H12'), C13'(H13'), C15'(H15'), C16'(H16')
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F)
;
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.806