Copper-catalyzed <i>N</i>-arylation of 1,2,4-oxadiazin-5(6<i>H</i>)-ones by diaryliodonium salts.
Presnukhina, Sofia I.; Baykova, Svetlana O.; Chukanova, Elizaveta A.; Metalnikova, Nadezhda M.; Baykov, Sergey V.; Soldatova, Natalia S.; Postnikov, Pavel S.; Boyarskiy, Vadim P.; Organic & biomolecular chemistry 23 (2025) 4217–4225; doi:10.1039/d5ob00204d

data_7160458
_publ_section_title
;
 Copper-catalyzed <i>N</i>-arylation of 1,2,4-oxadiazin-5(6<i>H</i>)-ones
 by diaryliodonium salts.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4217
_journal_page_last               4225
_journal_paper_doi               10.1039/d5ob00204d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C10 H7 F3 N2 O2'
_chemical_formula_sum            'C10 H7 F3 N2 O2'
_chemical_formula_weight         244.174
_chemical_name_systematic
3-(4-(trifluoromethyl)phenyl)-4H-1,2,4-oxadiazin-5(6H)-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-11-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-20 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                116.505(3)
_cell_angle_beta                 94.639(3)
_cell_angle_gamma                100.632(3)
_cell_formula_units_Z            4
_cell_length_a                   8.2385(3)
_cell_length_b                   11.3733(3)
_cell_length_c                   12.0528(4)
_cell_measurement_reflns_used    7188
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.2680
_cell_measurement_theta_min      4.4810
_cell_volume                     976.03(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9387
_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     26.00  72.00   0.50    0.15    --   47.38  77.00 -60.00   92
  2  \w     77.00 120.00   0.50    0.15    --   47.38  77.00 -60.00   86
  3  \w     99.00 130.00   0.50    0.60    --  113.25  61.00-150.00   62
  4  \w    139.00 177.00   0.50    0.60    --  113.25  61.00-150.00   76
  5  \w    121.00 172.00   0.50    0.60    --  113.25  30.00-120.00  102
  6  \w     92.00 178.00   0.50    0.60    --  113.25  77.00 120.00  172
  7  \w     56.00  81.00   0.50    0.60    --  113.25 -94.00-120.00   50
  8  \w     79.00 120.00   0.50    0.60    --  113.25-140.00-105.00   82
  9  \w     59.00 103.00   0.50    0.15    --   47.38-140.00-105.00   88
 10  \w     42.00  80.00   0.50    0.60    --  113.25-125.00 -30.00   76
 11  \w     83.00 109.00   0.50    0.60    --  113.25-125.00 -30.00   52
 12  \w     45.00  96.00   0.50    0.60    --  113.25-125.00   0.00  102
 13  \w     41.00  89.00   0.50    0.15    --   47.38-129.00  68.00   96
 14  \w     43.00 106.00   0.50    0.60    --  113.25-125.00 150.00  126
 15  \w     42.00 101.00   0.50    0.60    --  113.25-125.00 120.00  118
 16  \w     73.00  99.00   0.50    0.60    --  113.25-129.00  68.00   52
 17  \w     42.00  84.00   0.50    0.60    --  113.25 -77.00  30.00   84
 18  \w     45.00  71.00   0.50    0.60    --  113.25 -61.00  60.00   52
 19  \w     79.00 106.00   0.50    0.60    --  113.25 -77.00  90.00   54
 20  \w     45.00  70.00   0.50    0.60    --  113.25 -61.00 -60.00   50
 21  \w     42.00  67.00   0.50    0.60    --  113.25 -61.00 -90.00   50
 22  \w     43.00  70.00   0.50    0.60    --  113.25 -61.00-120.00   54
 23  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00-150.00   52
 24  \w     95.00 129.00   0.50    0.60    --  113.25 140.00 -45.00   68
 25  \w     71.00  96.00   0.50    0.15    --   47.38 129.00 140.00   50
 26  \w     73.00  98.00   0.50    0.60    --  113.25 129.00 140.00   50
 27  \w    101.00 139.00   0.50    0.60    --  113.25 129.00 140.00   76
 28  \w     73.00 106.00   0.50    0.15    --   47.38 140.00 -45.00   66
 29  \w     75.00 119.00   0.50    0.15    --   47.38 125.00-180.00   88
 30  \w    -26.00  28.00   0.50    0.15    --  -47.38  19.00 -90.00  108
 31  \w    -25.00  20.00   0.50    0.15    --  -47.38  19.00 -30.00   90
 32  \w    -23.00  28.00   0.50    0.15    --  -47.38  19.00-180.00  102
 33  \w    -71.00 -42.00   0.50    0.60    -- -106.00  61.00-150.00   58
 34  \w    -71.00 -46.00   0.50    0.60    -- -106.00  61.00 -30.00   50
 35  \w   -108.00 -66.00   0.50    0.60    -- -106.00 110.00  36.79   84
 36  \w   -122.00 -93.00   0.50    0.60    -- -106.00 140.00 -45.00   58
 37  \w    -84.00 -34.00   0.50    0.60    -- -106.00 125.00-180.00  100
 38  \w    -73.00 -46.00   0.50    0.60    -- -106.00 125.00-120.00   54
 39  \w   -111.00 -82.00   0.50    0.60    -- -106.00 125.00-120.00   58
 40  \w    -86.00 -61.00   0.50    0.15    --  -47.38 140.00 -45.00   50
 41  \w   -115.00 -33.00   0.50    0.60    -- -106.00 129.00 140.00  164
 42  \w    -78.00 -52.00   0.50    0.15    --  -47.38 129.00 140.00   52
 43  \w   -118.00 -93.00   0.50    0.60    -- -106.00 -15.00 120.00   50
 44  \w   -176.00-129.00   0.50    0.60    -- -106.00 -15.00 120.00   94
 45  \w   -127.00-102.00   0.50    0.60    -- -106.00 -30.00 -30.00   50
 46  \w   -174.00-106.00   0.50    0.60    -- -106.00 -61.00 -90.00  136
 47  \w   -172.00-147.00   0.50    0.60    -- -106.00 -30.00 -30.00   50
 48  \w   -143.00 -92.00   0.50    0.60    -- -106.00-125.00  30.00  102
 49  \w   -111.00 -73.00   0.50    0.15    --  -47.38-129.00  68.00   76
 50  \w   -116.00 -90.00   0.50    0.15    --  -47.38-140.00-105.00   52
 51  \w   -149.00 -64.00   0.50    0.60    -- -106.00-140.00-105.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0168523000
_diffrn_orient_matrix_UB_12      0.1501609000
_diffrn_orient_matrix_UB_13      0.0350677000
_diffrn_orient_matrix_UB_21      -0.0402849000
_diffrn_orient_matrix_UB_22      -0.0391878000
_diffrn_orient_matrix_UB_23      -0.1409519000
_diffrn_orient_matrix_UB_31      -0.1886366000
_diffrn_orient_matrix_UB_32      -0.0178720000
_diffrn_orient_matrix_UB_33      0.0055473000
_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  0.0486
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.9949
_diffrn_reflns_Laue_measured_fraction_max 0.9387
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12441
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9387
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         80.01
_diffrn_reflns_theta_min         4.17
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_description       prism
_exptl_crystal_F_000             498.355
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.5013
_refine_diff_density_min         -0.5385
_refine_diff_density_rms         0.1128
_refine_ls_d_res_high            0.7828
_refine_ls_d_res_low             10.5987
_refine_ls_goodness_of_fit_ref   1.0471
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0471
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0816P)^2^+0.5690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3459
_reflns_number_total             4010
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00204d2.cif
_cod_data_source_block           UBJ-988
_cod_depositor_comments
'Adding full bibliography for 7160455--7160458.cif.'
_cod_database_code               7160458
_chemical_oxdiff_formula         'C10 H7 F3 N2 O2'
_olex2_refinement_description
;
;
_olex2_exptl_crystal_mounting_method -
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.332