2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic Building Blocks.
Funt, Liya D.; Krivolapova, Yulia V.; Khoroshilova, Olesya V.; Novikov, Mikhail Sergeevich; Khlebnikov, Alexander F.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03367

data_4038041
_publ_section_title
;
 2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic
 Building Blocks.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03367
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 F3 N2 O4 S'
_chemical_formula_sum            'C15 H11 F3 N2 O4 S'
_chemical_formula_weight         372.32
_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             2019-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                108.010(4)
_cell_angle_beta                 94.612(3)
_cell_angle_gamma                103.904(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4324(3)
_cell_length_b                   14.3291(5)
_cell_length_c                   15.9268(7)
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      69.8800
_cell_measurement_theta_min      2.9460
_cell_volume                     1543.68(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (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(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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    -80.00 -12.00   0.50    0.20    --  -38.70 141.00-170.00  136
  2  \w    -89.00 -43.00   0.50    0.20    --  -38.70 129.00  17.00   92
  3  \w     53.00  85.00   0.50    0.20    --   38.70-141.00 131.00   64
  4  \w     12.00  61.00   0.50    0.20    --   38.70-129.00 -56.00   98
  5  \w     81.00 106.00   0.50    0.67    --  100.00-141.00 131.00   50
  6  \w     66.00  92.00   0.50    0.67    --  100.00-129.00 -56.00   52
  7  \w     85.00 112.00   0.50    0.67    --  100.00 141.00-170.00   54
  8  \w    114.00 139.00   0.50    0.67    --  100.00 129.00  17.00   50
  9  \w    -41.00 -15.00   0.50    0.20    --  -38.70 -65.00-180.00   52
 10  \w    -52.00 -26.00   0.50    0.20    --  -38.70  43.00 -90.00   52
 11  \w    -56.00  15.00   0.50    0.20    --  -38.70  65.00 120.00  142
 12  \w     -1.00  24.00   0.50    0.20    --  -38.70  65.00-150.00   50
 13  \w    -84.00 -28.00   0.50    0.20    --  -38.70 -65.00 -60.00  112
 14  \w    -19.00   6.00   0.50    0.20    --  -38.70  43.00 -90.00   50
 15  \w    -63.00  15.00   0.50    0.20    --  -38.70 104.00 120.00  156
 16  \w    -39.00 -13.00   0.50    0.20    --  -38.70  21.00 150.00   52
 17  \w     -8.00  21.00   0.50    0.20    --  -38.70  21.00 150.00   58
 18  \w    -58.00  -7.00   0.50    0.20    --  -38.70  65.00-150.00  102
 19  \w   -104.00 -51.00   0.50    0.20    --  -38.70 -65.00-180.00  106
 20  \w     23.00  99.00   0.50    0.20    --   38.70  21.00-180.00  152
 21  \w     14.00  61.00   0.50    0.20    --   38.70 -65.00 -90.00   94
 22  \w     19.00  58.00   0.50    0.20    --   38.70  21.00  90.00   78
 23  \w    -24.00  58.00   0.50    0.20    --   38.70 -54.00 -60.00  164
 24  \w     62.00 107.00   0.50    0.20    --   38.70  21.00  90.00   90
 25  \w     22.00  83.00   0.50    0.20    --   38.70  43.00  60.00  122
 26  \w     82.00 110.00   0.50    0.67    --  100.00  93.00-120.00   56
 27  \w     78.00 120.00   0.50    0.67    --  100.00  69.00 -60.00   84
 28  \w     92.00 127.00   0.50    0.67    --  100.00 111.00   0.00   70
 29  \w     58.00  84.00   0.50    0.67    --  100.00 -93.00 150.00   52
 30  \w     41.00  67.00   0.50    0.67    --  100.00-133.00-180.00   52
 31  \w     86.00 142.00   0.50    0.67    --  100.00  61.00  60.00  112
 32  \w    121.00 148.00   0.50    0.67    --  100.00  37.00-180.00   54
 33  \w     98.00 123.00   0.50    0.67    --  100.00-133.00-180.00   50
 34  \w    103.00 135.00   0.50    0.67    --  100.00  30.00 120.00   64
 35  \w     42.00  77.00   0.50    0.67    --  100.00 -45.00   0.00   70
 36  \w     37.00  79.00   0.50    0.67    --  100.00 -61.00-180.00   84
 37  \w     46.00  72.00   0.50    0.67    --  100.00-133.00  60.00   52
 38  \w     83.00 123.00   0.50    0.67    --  100.00-133.00  60.00   80
 39  \w    105.00 131.00   0.50    0.67    --  100.00 111.00  60.00   52
 40  \w     44.00 108.00   0.50    0.67    --  100.00 -53.00  60.00  128
 41  \w    121.00 150.00   0.50    0.67    --  100.00  77.00  30.00   58
 42  \w     77.00 103.00   0.50    0.67    --  100.00  77.00  30.00   52
 43  \w     87.00 119.00   0.50    0.67    --  100.00  37.00-180.00   64
 44  \w     51.00 119.00   0.50    0.67    --  100.00 -69.00 -60.00  136
 45  \w     75.00 107.00   0.50    0.67    --  100.00-111.00  60.00   64
 46  \w     81.00 113.00   0.50    0.67    --  100.00-133.00-120.00   64
 47  \w     70.00 122.00   0.50    0.67    --  100.00 133.00 -30.00  104
 48  \w     40.00  66.00   0.50    0.67    --  100.00-111.00  60.00   52
 49  \w     73.00 156.00   0.50    0.67    --  100.00  77.00 -30.00  166
 50  \w     35.00  60.00   0.50    0.67    --  100.00 -86.00-180.00   50
 51  \w     98.00 129.00   0.50    0.67    --  100.00 -86.00-180.00   62
 52  \w     96.00 157.00   0.50    0.67    --  100.00  45.00-120.00  122
 53  \w     37.00 117.00   0.50    0.67    --  100.00 -61.00  60.00  160
 54  \w    131.00 156.00   0.50    0.67    --  100.00 133.00-180.00   50
 55  \w     69.00 108.00   0.50    0.67    --  100.00 133.00-180.00   78
 56  \w     71.00 153.00   0.50    0.67    --  100.00 133.00 -90.00  164
 57  \w     35.00 106.00   0.50    0.67    --  100.00 -93.00  90.00  142
 58  \w     80.00 121.00   0.50    0.67    --  100.00  15.00 -30.00   82
 59  \w    124.00 156.00   0.50    0.67    --  100.00  93.00-120.00   64
 60  \w     75.00 101.00   0.50    0.67    --  100.00 -81.00 -42.26   52
 61  \w     85.00 154.00   0.50    0.67    --  100.00  37.00 120.00  138
 62  \w     92.00 117.00   0.50    0.67    --  100.00  93.00 150.00   50
 63  \w     30.00  98.00   0.50    0.67    --  100.00 -93.00 -60.00  136
 64  \w     40.00 113.00   0.50    0.67    --  100.00 -53.00 -90.00  146
 65  \w     36.00 101.00   0.50    0.67    --  100.00 -53.00-180.00  130
 66  \w     87.00 134.00   0.50    0.67    --  100.00  53.00   0.00   94
 67  \w     86.00 111.00   0.50    0.67    --  100.00-111.00-120.00   50
 68  \w     36.00  75.00   0.50    0.67    --  100.00-111.00 -30.00   78
 69  \w     67.00  92.00   0.50    0.67    --  100.00-111.00 120.00   50
 70  \w     34.00 108.00   0.50    0.67    --  100.00 -93.00-150.00  148
 71  \w    125.00 152.00   0.50    0.67    --  100.00  30.00 150.00   54
 72  \w     89.00 115.00   0.50    0.67    --  100.00  30.00 150.00   52
 73  \w     18.00  44.00   0.50    0.20    --   38.70  77.00 -90.00   52
 74  \w    -51.00 -25.00   0.50    0.20    --    0.00 130.00-157.41   52
 75  \w    -33.00  -8.00   0.50    0.20    --   16.00 122.00  -3.35   50
 76  \w     -9.00  16.00   0.50    0.20    --   28.00 102.00 -56.17   50
 77  \w     -9.00  16.00   0.50    0.20    --   28.00 102.00 -87.97   50
 78  \w     -9.00  16.00   0.50    0.20    --   28.00 102.00  89.00   50
 79  \w     -1.00  24.00   0.50    0.20    --   32.00  94.00  17.20   50
 80  \w     -1.00  24.00   0.50    0.20    --   32.00  93.00 134.72   50
 81  \w      5.00  30.00   0.50    0.20    --   36.00  89.00  57.89   50
 82  \w      4.00  29.00   0.50    0.20    --   36.00  90.00-152.84   50
 83  \w      4.00  29.00   0.50    0.20    --   36.00  90.00-173.10   50
 84  \w      9.00  34.00   0.50    0.20    --   38.70  85.00 -73.27   50
 85  \w     11.00  36.00   0.50    0.20    --   40.00  84.00 -17.70   50
 86  \w     11.00  32.00   0.50    0.20    --   40.00  83.00-166.60   42
;
_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      -0.0036784000
_diffrn_orient_matrix_UB_12      0.0021090000
_diffrn_orient_matrix_UB_13      0.0971352000
_diffrn_orient_matrix_UB_21      -0.1411336000
_diffrn_orient_matrix_UB_22      -0.1072163000
_diffrn_orient_matrix_UB_23      -0.0344578000
_diffrn_orient_matrix_UB_31      0.1642631000
_diffrn_orient_matrix_UB_32      -0.0486396000
_diffrn_orient_matrix_UB_33      -0.0046319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16833
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.501
_diffrn_reflns_theta_min         2.959
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
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    1.602
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0852P)^2^+0.6020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4969
_reflns_number_total             5838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03367_si_005.cif
_cod_data_source_block           10681-13821_lia680
_cod_original_cell_volume        1543.68(11)
_cod_database_code               4038041
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C15 F3 N2 O4 S'
_shelx_estimated_absorpt_t_max   0.683
_shelx_estimated_absorpt_t_min   0.617
_reflns_odcompleteness_completeness 95.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 N1(H1), N1A(H1A), C9(H9), C12(H12), C12A(H12A), C10A(H10A), C9A(H9A),
 C10(H10), C11A(H11A), C11(H11)
2.b Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5(H5A,H5B,H5C), C1(H1B,H1C,H1D), C1A(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              43503
_shelx_hkl_checksum              96423
_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 2.531
_oxdiff_exptl_absorpt_empirical_full_min 0.580