Azides as an unconventional source of iminyl radicals: electrochemically induced synthesis of <i>O</i>-imido oximes from benzyl azides and <i>N</i>-hydroxyimides <i>via</i> N-O coupling.
Paveliev, Stanislav A.; Dvoretskiy, Andrey; Segida, Oleg O.; Krylov, Igor B.; Terent'ev, Alexander O.; Chemical communications (Cambridge, England) 61 (2025) 14426–14429; doi:10.1039/d5cc03556b

data_1575451
_publ_section_title
;
 Azides as an unconventional source of iminyl radicals: electrochemically
 induced synthesis of <i>O</i>-imido oximes from benzyl azides and
 <i>N</i>-hydroxyimides <i>via</i> N-O coupling.
;
_journal_issue                   75
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14426
_journal_page_last               14429
_journal_paper_doi               10.1039/d5cc03556b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dual
_audit_creation_date             2022-11-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.30880(10)
_cell_length_b                   14.40790(10)
_cell_length_c                   14.70280(10)
_cell_measurement_reflns_used    15185
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6030
_cell_measurement_theta_min      3.5730
_cell_volume                     2607.45(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.997
_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   -116.00 -80.00   0.50    0.18    --  -48.70-125.00-120.00   72
  2  \w   -102.00 -73.00   0.50    0.18    --  -48.70-125.00-180.00   58
  3  \w   -140.00-115.00   0.50    0.75    --  -86.25 -51.00 -66.00   50
  4  \w   -145.00-120.00   0.50    0.75    --  -86.25-100.00  68.00   50
  5  \w    -20.00   5.00   0.50    0.18    --  -48.70  19.00  90.00   50
  6  \w    -68.00  -4.00   0.50    0.18    --  -48.70  78.00 -74.00  128
  7  \w     36.00  88.00   0.50    0.75    --  107.75 -95.00-150.00  104
  8  \w     48.00  81.00   0.50    0.75    --  107.75 -95.00 -60.00   66
  9  \w     55.00  81.00   0.50    0.75    --  107.75-125.00  90.00   52
 10  \w     40.00  95.00   0.50    0.75    --  107.75-101.00 120.53  110
 11  \w     40.00  91.00   0.50    0.75    --  107.75 -97.00  94.69  102
 12  \w     60.00  85.00   0.50    0.75    --  107.75 -78.00 160.00   50
 13  \w     36.00  65.00   0.50    0.75    --  107.75 -61.00 120.00   58
 14  \w    -15.00  11.00   0.50    0.18    --   48.70 -19.00 150.00   52
 15  \w     75.00 100.00   0.50    0.75    --  107.75 -77.00  60.00   50
 16  \w     36.00  61.00   0.50    0.75    --  107.75 -70.00  -7.53   50
 17  \w     37.00  69.00   0.50    0.75    --  107.75 -61.00-120.00   64
 18  \w    117.00 143.00   0.50    0.75    --  107.75  15.00-150.00   52
 19  \w    115.00 141.00   0.50    0.75    --  107.75  78.00 -74.00   52
 20  \w    141.00 178.00   0.50    0.75    --  107.75  77.00  60.00   74
 21  \w     96.00 169.00   0.50    0.75    --  107.75  51.00  79.00  146
 22  \w     94.00 120.00   0.50    0.75    --  107.75  77.00  60.00   52
 23  \w    105.00 148.00   0.50    0.75    --  107.75  45.00  30.00   86
 24  \w    117.00 159.00   0.50    0.75    --  107.75  30.00   0.00   84
 25  \w     97.00 137.00   0.50    0.75    --  107.75  45.00-150.00   80
 26  \w     95.00 164.00   0.50    0.75    --  107.75 125.00-120.00  138
 27  \w    119.00 169.00   0.50    0.75    --  107.75 125.00 -90.00  100
 28  \w    126.00 153.00   0.50    0.75    --  107.75 100.00 173.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0768680000
_diffrn_orient_matrix_UB_12      -0.0657542000
_diffrn_orient_matrix_UB_13      0.0517797000
_diffrn_orient_matrix_UB_21      0.0724775000
_diffrn_orient_matrix_UB_22      -0.0079053000
_diffrn_orient_matrix_UB_23      -0.0850584000
_diffrn_orient_matrix_UB_31      0.0670472000
_diffrn_orient_matrix_UB_32      0.0839743000
_diffrn_orient_matrix_UB_33      0.0326152000
_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  0.0195
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.791
_diffrn_reflns_theta_min         5.604
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00142(13)
_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   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0386P)^2^+1.0744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2749
_reflns_number_total             2777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03556b2.cif
_cod_data_source_block           ad230
_cod_depositor_comments          'Adding full bibliography for 1575451.cif.'
_cod_database_code               1575451
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H12N2O3
_chemical_oxdiff_usercomment     AD230
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.879
_olex2_refinement_description
;
;
_shelx_res_checksum              73578
_shelx_hkl_checksum              78719
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.756