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_4038040
_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         'C24 H16 N2 O2, H2 O, 0.5(C2 H6 O S)'
_chemical_formula_sum            'C25 H21 N2 O3.5 S0.5'
_chemical_formula_weight         421.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 93.043(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3641(3)
_cell_length_b                   20.0600(7)
_cell_length_c                   24.7230(7)
_cell_measurement_reflns_used    6889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5820
_cell_measurement_theta_min      4.2000
_cell_volume                     4142.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -63.00  24.00   1.00    3.81    --  -40.38  38.00 120.00   87
  2  \w      2.00  58.00   1.00    3.81    --   40.38 -99.00-150.00   56
  3  \w     38.00 121.00   1.00   15.23    --  113.00 -45.00-150.00   83
  4  \w    120.00 175.00   1.00   15.23    --  113.00  61.00-150.00   55
  5  \w    121.00 167.00   1.00   15.23    --  113.00 112.00 -60.00   46
  6  \w    102.00 133.00   1.00   15.23    --  113.00 112.00-150.00   31
  7  \w     94.00 170.00   1.00   15.23    --  113.00  77.00   0.00   76
  8  \w     95.00 167.00   1.00   15.23    --  113.00  45.00 120.00   72
  9  \w     42.00 111.00   1.00   15.23    --  113.00 -61.00  60.00   69
 10  \w     30.00  87.00   1.00   15.23    --  113.00 -95.00  60.00   57
 11  \w     29.00  92.00   1.00   15.23    --  113.00 -95.00   0.00   63
 12  \w   -119.00  -8.00   1.00    3.81    --  -40.38 -19.00 -60.00  111
 13  \w   -112.00 -31.00   1.00    3.81    --  -40.38 -38.00-180.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1588028000
_diffrn_orient_matrix_UB_12      -0.0388944000
_diffrn_orient_matrix_UB_13      0.0003892000
_diffrn_orient_matrix_UB_21      -0.0741059000
_diffrn_orient_matrix_UB_22      -0.0483074000
_diffrn_orient_matrix_UB_23      -0.0428344000
_diffrn_orient_matrix_UB_31      0.0573839000
_diffrn_orient_matrix_UB_32      0.0452642000
_diffrn_orient_matrix_UB_33      -0.0454249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20122
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.482
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         8500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1172P)^2^+1.0478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6786
_reflns_number_total             8500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03367_si_004.cif
_cod_data_source_block           10681-13821_lia685
_cod_original_cell_volume        4142.3(3)
_cod_original_formula_sum        'C25 H21 N2 O3.50 S0.50'
_cod_database_code               4038040
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C15 F3 N2 O4 S'
_shelx_estimated_absorpt_t_max   0.842
_shelx_estimated_absorpt_t_min   0.797
_reflns_odcompleteness_completeness 99.88
_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, All O(H,H) groups
2.a Free rotating group:
 O2S(H2SD,H2SE), O1S(H1SD,H1SE)
2.b Aromatic/amide H refined with riding coordinates:
 N2A(H2A), N2(H2), N1(H1), N1A(H1A), C20A(H20A), C23(H23), C20(H20),
 C22A(H22A), C3A(H3A), C23A(H23A), C5A(H5A), C21(H21), C15(H15), C3(H3),
 C22(H22), C11A(H11A), C11(H11), C2A(H2AA), C15A(H15A), C21A(H21A), C12(H12),
 C6A(H6A), C1A(H1AA), C14(H14), C2(H2B), C5(H5), C14A(H14A), C13A(H13A),
 C13(H13), C12A(H12A), C1(H1B), C6(H6)
2.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              14601
_shelx_hkl_checksum              47595
_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 1.715
_oxdiff_exptl_absorpt_empirical_full_min 0.559