The diacetyliminoxyl radical in oxidative functionalization of alkenes.
Budnikov, Alexander S.; Krylov, Igor B.; Lastovko, Andrey V.; Dolotov, Roman A.; Shevchenko, Mikhail I.; Terent'ev, Alexander O.; Organic & biomolecular chemistry 21 (2023) 7758–7766; doi:10.1039/d3ob00925d

data_7159553
_publ_section_title
;
 The diacetyliminoxyl radical in oxidative functionalization of alkenes.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7758
_journal_page_last               7766
_journal_paper_doi               10.1039/d3ob00925d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C24 H22 N2 O5'
_chemical_formula_sum            'C24 H22 N2 O5'
_chemical_formula_weight         418.43
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.950(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6766(3)
_cell_length_b                   15.1780(4)
_cell_length_c                   12.1389(3)
_cell_measurement_reflns_used    15408
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      77.4360
_cell_measurement_theta_min      3.7450
_cell_volume                     2078.53(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_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    -81.00   0.00   0.50    4.11    --  -48.70 103.00 121.00  162
  2  \w     31.00  57.00   0.50    4.11    --   48.70-103.00  18.00   52
  3  \w    -73.00 -48.00   0.50   17.87    --  -86.25 103.00 121.00   50
  4  \w   -120.00 -91.00   0.50   17.87    --  -86.25-103.00  18.00   58
  5  \w     64.00  90.00   0.50   17.87    --  107.75-103.00  18.00   52
  6  \w    135.00 161.00   0.50   17.87    --  107.75 103.00 121.00   52
  7  \w   -116.00 -74.00   0.50    4.11    --  -48.70-125.00 -60.00   84
  8  \w   -115.00 -74.00   0.50    4.11    --  -48.70-125.00-180.00   82
  9  \w    -26.00  25.00   0.50    4.11    --  -48.70  19.00  30.00  102
 10  \w   -107.00 -74.00   0.50    4.11    --  -48.70-125.00 150.00   66
 11  \w   -115.00 -74.00   0.50    4.11    --  -48.70-125.00 120.00   82
 12  \w     77.00 103.00   0.50   17.87    --  107.75 -95.00  30.00   52
 13  \w     76.00 101.00   0.50   17.87    --  107.75-107.00 132.60   50
 14  \w     36.00  61.00   0.50   17.87    --  107.75 -54.00  -3.08   50
 15  \w    116.00 158.00   0.50   17.87    --  107.75  77.00-180.00   84
 16  \w     38.00  65.00   0.50   17.87    --  107.75 -61.00 120.00   54
 17  \w     44.00 105.00   0.50   17.87    --  107.75 -77.00  90.00  122
 18  \w     36.00  70.00   0.50   17.87    --  107.75 -95.00  30.00   68
 19  \w     54.00  79.00   0.50   17.87    --  107.75-144.00  13.18   50
 20  \w     99.00 165.00   0.50   17.87    --  107.75  15.00-180.00  132
 21  \w     37.00  70.00   0.50   17.87    --  107.75 -61.00 -90.00   66
 22  \w    105.00 177.00   0.50   17.87    --  107.75  45.00   0.00  144
 23  \w     38.00  90.00   0.50   17.87    --  107.75 -77.00  30.00  104
 24  \w     39.00  71.00   0.50   17.87    --  107.75 -61.00 -60.00   64
 25  \w     49.00  78.00   0.50   17.87    --  107.75-125.00 120.00   58
 26  \w     86.00 111.00   0.50   17.87    --  107.75-125.00 120.00   50
 27  \w    135.00 163.00   0.50   17.87    --  107.75   0.00-180.00   56
 28  \w     93.00 139.00   0.50   17.87    --  107.75  61.00-150.00   92
 29  \w     38.00  63.00   0.50   17.87    --  107.75 -77.00   0.00   50
 30  \w     67.00  94.00   0.50   17.87    --  107.75 -77.00   0.00   54
 31  \w     58.00 108.00   0.50   17.87    --  107.75-107.00-138.08  100
 32  \w     63.00  97.00   0.50   17.87    --  107.75 -77.00  54.21   68
 33  \w     36.00  80.00   0.50   17.87    --  107.75   0.00-180.00   88
 34  \w     94.00 125.00   0.50   17.87    --  107.75-144.00  13.18   62
 35  \w    104.00 130.00   0.50   17.87    --  107.75  77.00  30.00   52
 36  \w     83.00 114.00   0.50   17.87    --  107.75 -82.00 132.39   62
 37  \w     56.00 107.00   0.50   17.87    --  107.75-125.00  90.00  102
 38  \w     36.00  72.00   0.50   17.87    --  107.75 -77.00-120.00   72
 39  \w     56.00  91.00   0.50   17.87    --  107.75 -95.00  60.00   70
 40  \w     38.00  70.00   0.50   17.87    --  107.75 -61.00  30.00   64
 41  \w     43.00  70.00   0.50   17.87    --  107.75 -77.00-150.00   54
 42  \w     37.00  92.00   0.50   17.87    --  107.75 -77.00 150.00  110
 43  \w     38.00  89.00   0.50   17.87    --  107.75 -95.00 -90.00  102
 44  \w     55.00  81.00   0.50   17.87    --  107.75-125.00-150.00   52
 45  \w    124.00 178.00   0.50   17.87    --  107.75  45.00 -60.00  108
 46  \w    100.00 164.00   0.50   17.87    --  107.75  45.00  90.00  128
 47  \w     40.00  82.00   0.50   17.87    --  107.75 -87.00 -86.11   84
 48  \w     85.00 111.00   0.50   17.87    --  107.75 -87.00 -86.11   52
 49  \w     36.00  69.00   0.50   17.87    --  107.75 -61.00-180.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25662
_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         77.826
_diffrn_reflns_theta_min         4.686
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0741P)^2^+2.2397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3958
_reflns_number_total             4433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00925d3.cif
_cod_data_source_block           la-293
_cod_depositor_comments
'Adding full bibliography for 7159551--7159553.cif.'
_cod_database_code               7159553
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.913
_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. Restrained distances
 C1-C8A \\sim C1-C8B
 with sigma of 0.003
 C8A-C9A \\sim C8B-C9B
 with sigma of 0.003
 C8A-C13A \\sim C8B-C13B
 with sigma of 0.003
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.003
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.003
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.003
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.003
 C1-C19A \\sim C1-C19B
 with sigma of 0.003
 O4A-C19A \\sim O4B-C19B
 with sigma of 0.003
 O4A-C20A \\sim O4B-C20B
 with sigma of 0.003
 C20A-C21A \\sim C20B-C21B
 with sigma of 0.003
 C21A-N2A \\sim C21B-N2B
 with sigma of 0.003
 C19A-N2A \\sim N2B-C19B
 with sigma of 0.003
 C20A-C22A \\sim C20B-C22B
 with sigma of 0.003
 O5A-C23A \\sim O5B-C23B
 with sigma of 0.003
 C21A-C23A \\sim C21B-C23B
 with sigma of 0.003
 C23A-C24A \\sim C23B-C24B
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C19A) = Uanis(C19B)
Uanis(N2A) = Uanis(O4B)
Uanis(O4A) = Uanis(N2B)
Uanis(C20A) = Uanis(C20B)
Uanis(C21A) = Uanis(C21B)
Uanis(C24A) = Uanis(C22B)
Uanis(C24B) = Uanis(C22A)
Uanis(C23A) = Uanis(C23B)
Uanis(O5A) = Uanis(O5B)
4. Others
 Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
 Sof(O4B)=Sof(O5B)=Sof(N2B)=Sof(C19B)=Sof(C20B)=Sof(C21B)=Sof(C22B)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=Sof(C23B)=Sof(C24B)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(O4A)=Sof(O5A)=Sof(N2A)=Sof(C19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9A(H9A), C9B(H9B), C10A(H10A),
 C10B(H10B), C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B), C13A(H13A),
 C13B(H13B)
5.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C22A(H22A,H22B,H22C), C22B(H22D,
 H22E,H22F), C24A(H24A,H24B,H24C), C24B(H24D,H24E,H24F)
;
_shelx_res_checksum              19739
_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
;