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_7159552
_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 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-12-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.9970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2566(2)
_cell_length_b                   5.41860(10)
_cell_length_c                   18.4668(3)
_cell_measurement_reflns_used    8909
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7980
_cell_measurement_theta_min      3.9040
_cell_volume                     1124.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.995
_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    104.00 130.00   0.50    0.23    --  111.50  30.00  60.00   52
  2  \w    107.00 138.00   0.50    0.23    --  111.50  45.00 -30.00   62
  3  \w     96.00 178.00   0.50    0.23    --  111.50  61.00 -60.00  164
  4  \w    102.00 128.00   0.50    0.23    --  111.50  45.00-150.00   52
  5  \w    124.00 164.00   0.50    0.23    --  111.50  15.00-120.00   80
  6  \w    101.00 178.00   0.50    0.23    --  111.50  30.00 -90.00  154
  7  \w     68.00 178.00   0.50    0.23    --  111.50   4.00  42.00  220
  8  \w    145.00 178.00   0.50    0.23    --  111.50  30.00  60.00   66
  9  \w    110.00 136.00   0.50    0.23    --  111.50  30.00 120.00   52
 10  \w      5.00 120.00   0.50    0.06    --   48.51   4.00  42.00  230
 11  \w    -44.00  23.00   0.50    0.06    --  -48.51   4.00  42.00  134
 12  \w    -44.00 -18.00   0.50    0.23    --  -90.00   4.00  42.00   52
 13  \w    -51.00 -18.00   0.50    0.23    --  -90.00  45.00 -30.00   66
 14  \w    -26.00  26.00   0.50    0.06    --  -48.51  19.00-120.00  104
 15  \w   -120.00 -31.00   0.50    0.06    --  -48.51  -4.00-135.00  178
 16  \w   -162.00 -72.00   0.50    0.23    --  -90.00  -4.00-135.00  180
 17  \w    131.00 165.00   0.50    0.23    --  111.50 125.00 -60.00   68
 18  \w     40.00  66.00   0.50    0.23    --  111.50 -61.00  30.00   52
 19  \w     41.00  66.00   0.50    0.23    --  111.50 -61.00 -30.00   50
 20  \w    -23.00  63.00   0.50    0.06    --   48.51 -57.00-180.00  172
 21  \w     43.00  69.00   0.50    0.23    --  111.50 -61.00-150.00   52
 22  \w     60.00  86.00   0.50    0.23    --  111.50 -77.00-120.00   52
 23  \w     41.00  97.00   0.50    0.23    --  111.50 -77.00 -90.00  112
 24  \w     40.00 114.00   0.50    0.23    --  111.50-129.00 -10.28  148
 25  \w     78.00 104.00   0.50    0.23    --  111.50 -95.00  90.00   52
 26  \w     40.00 105.00   0.50    0.23    --  111.50 -95.00 120.00  130
 27  \w     55.00  81.00   0.50    0.23    --  111.50 -86.00 -48.96   52
 28  \w     64.00 109.00   0.50    0.23    --  111.50-125.00 -60.00   90
 29  \w     40.00 111.00   0.50    0.23    --  111.50-125.00-120.00  142
 30  \w     40.00 105.00   0.50    0.23    --  111.50 -95.00-180.00  130
 31  \w     47.00  73.00   0.50    0.23    --  111.50 -95.00-150.00   52
 32  \w     85.00 111.00   0.50    0.23    --  111.50 -86.00 -48.96   52
 33  \w     55.00  81.00   0.50    0.23    --  111.50 -81.00 142.57   52
 34  \w     40.00 136.00   0.50    0.23    --  111.50 -82.00 147.63  192
 35  \w    108.00 135.00   0.50    0.23    --  111.50 -81.00 142.57   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      -0.1078615000
_diffrn_orient_matrix_UB_12      0.0092898000
_diffrn_orient_matrix_UB_13      0.0479577000
_diffrn_orient_matrix_UB_21      -0.0846250000
_diffrn_orient_matrix_UB_22      -0.0097497000
_diffrn_orient_matrix_UB_23      -0.0682257000
_diffrn_orient_matrix_UB_31      -0.0006361000
_diffrn_orient_matrix_UB_32      -0.2840576000
_diffrn_orient_matrix_UB_33      0.0039242000
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12674
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.466
_diffrn_reflns_theta_min         3.932
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0045(8)
_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   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0585P)^2^+0.4312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2227
_reflns_number_total             2420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00925d3.cif
_cod_data_source_block           b699-1
_cod_depositor_comments
'Adding full bibliography for 7159551--7159553.cif.'
_cod_database_code               7159552
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     B.699-1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.886
_reflns_odcompleteness_completeness 95.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_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:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              1348
_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 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.582