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_7160456
_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         'C9 H7 F N2 O2'
_chemical_formula_sum            'C9 H7 F N2 O2'
_chemical_formula_weight         194.167
_chemical_name_systematic        3-(4-fluorophenyl)-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             2024-11-15
_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                88.303(4)
_cell_angle_beta                 68.988(4)
_cell_angle_gamma                76.975(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9399(3)
_cell_length_b                   7.2091(4)
_cell_length_c                   9.0838(4)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    99.98(19)
_cell_measurement_theta_max      68.9570
_cell_measurement_theta_min      5.2160
_cell_volume                     412.68(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_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
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9779
_diffrn_measured_fraction_theta_max 0.9746
_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   -102.00 -56.00   0.50    0.25    --  -35.49 -60.00 -24.00   92
  2  \w      0.00  26.00   0.50    0.25    --  -35.49  60.00 114.00   52
  3  \w    -26.00  40.00   0.50    0.25    --   35.49 -60.00 -24.00  132
  4  \w     57.00  82.00   0.50    0.25    --   35.49  60.00 114.00   50
  5  \w     33.00 113.00   0.50    1.00    --  100.00 -60.00 -24.00  160
  6  \w     94.00 157.00   0.50    1.00    --  100.00  60.00 114.00  126
  7  \w   -103.00 -35.00   0.50    0.25    --  -35.49 -65.00-120.00  136
  8  \w   -101.00 -59.00   0.50    0.25    --  -35.49 -65.00 120.00   84
  9  \w    -35.00 -10.00   0.50    0.25    --  -35.49 -21.00 -60.00   50
 10  \w    -68.00 -43.00   0.50    0.25    --  -35.49 -21.00 -60.00   50
 11  \w    -54.00  -9.00   0.50    0.25    --  -35.49 -65.00 120.00   90
 12  \w     46.00  95.00   0.50    0.25    --   35.49-138.00   0.00   98
 13  \w    -31.00  51.00   0.50    0.25    --   35.49 -65.00-180.00  164
 14  \w    -24.00   4.00   0.50    0.25    --   35.49 -89.00  90.00   56
 15  \w    -12.00  53.00   0.50    0.25    --   35.49-104.00  60.00  130
 16  \w     11.00  52.00   0.50    0.25    --   35.49 -89.00  90.00   82
 17  \w     49.00  74.00   0.50    0.25    --   35.49  43.00-150.00   50
 18  \w     51.00  78.00   0.50    0.25    --   35.49-138.00-120.00   54
 19  \w    -32.00  58.00   0.50    0.25    --   35.49 -54.00 -90.00  180
 20  \w     68.00  99.00   0.50    1.00    --  100.00-149.00-120.00   62
 21  \w    129.00 155.00   0.50    1.00    --  100.00  77.00  60.00   52
 22  \w     33.00  63.00   0.50    1.00    --  100.00-149.00-120.00   60
 23  \w     92.00 123.00   0.50    1.00    --  100.00 -53.00-180.00   62
 24  \w     83.00 125.00   0.50    1.00    --  100.00  77.00  60.00   84
 25  \w     83.00 156.00   0.50    1.00    --  100.00  77.00  30.00  146
 26  \w     60.00  87.00   0.50    1.00    --  100.00 -91.00   0.00   54
 27  \w     25.00  54.00   0.50    1.00    --  100.00 -91.00   0.00   58
 28  \w     33.00  88.00   0.50    1.00    --  100.00 -53.00-180.00  110
 29  \w     74.00 124.00   0.50    1.00    --  100.00  69.00   0.00  100
 30  \w     66.00 118.00   0.50    1.00    --  100.00 -37.00  60.00  104
 31  \w     34.00  67.00   0.50    1.00    --  100.00-107.00 -60.00   66
 32  \w     74.00 103.00   0.50    1.00    --  100.00-107.00 -60.00   58
 33  \w    108.00 142.00   0.50    1.00    --  100.00  91.00   0.00   68
 34  \w     43.00 103.00   0.50    1.00    --  100.00-107.00 120.00  120
 35  \w     28.00 128.00   0.50    1.00    --  100.00 -22.00   0.00  200
 36  \w     61.00 103.00   0.50    1.00    --  100.00 -91.00 -30.00   84
 37  \w    123.00 149.00   0.50    1.00    --  100.00 149.00 -90.00   52
 38  \w     91.00 125.00   0.50    1.00    --  100.00 -61.00-150.00   68
 39  \w    129.00 154.00   0.50    1.00    --  100.00  15.00 -30.00   50
 40  \w     65.00 113.00   0.50    1.00    --  100.00  15.00 -30.00   96
 41  \w     60.00 108.00   0.50    1.00    --  100.00 -30.00 -60.00   96
 42  \w     22.00  54.00   0.50    1.00    --  100.00 -91.00 -30.00   64
 43  \w    113.00 153.00   0.50    1.00    --  100.00 125.00-120.00   80
 44  \w     70.00 112.00   0.50    1.00    --  100.00-125.00-120.00   84
 45  \w     33.00  60.00   0.50    1.00    --  100.00-125.00-120.00   54
 46  \w     81.00 107.00   0.50    1.00    --  100.00 125.00-120.00   52
 47  \w     94.00 128.00   0.50    1.00    --  100.00-149.00 150.00   68
 48  \w     89.00 126.00   0.50    1.00    --  100.00  91.00-150.00   74
 49  \w     81.00 150.00   0.50    1.00    --  100.00  53.00   0.00  138
 50  \w     67.00 110.00   0.50    1.00    --  100.00 -77.00-150.00   86
 51  \w     37.00  62.00   0.50    1.00    --  100.00-125.00-180.00   50
 52  \w     71.00  96.00   0.50    1.00    --  100.00-125.00-180.00   50
 53  \w     67.00  99.00   0.50    1.00    --  100.00 149.00 -90.00   64
 54  \w     96.00 122.00   0.50    1.00    --  100.00 107.00-120.00   52
 55  \w     65.00  94.00   0.50    1.00    --  100.00 -91.00-150.00   58
 56  \w     34.00  61.00   0.50    1.00    --  100.00 -91.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0044968000
_diffrn_orient_matrix_UB_12      0.1825171000
_diffrn_orient_matrix_UB_13      -0.0925149000
_diffrn_orient_matrix_UB_21      -0.1194239000
_diffrn_orient_matrix_UB_22      -0.0753192000
_diffrn_orient_matrix_UB_23      -0.0903977000
_diffrn_orient_matrix_UB_31      -0.2131437000
_diffrn_orient_matrix_UB_32      0.0963215000
_diffrn_orient_matrix_UB_33      0.1279834000
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.9779
_diffrn_reflns_Laue_measured_fraction_max 0.9746
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2997
_diffrn_reflns_point_group_measured_fraction_full 0.9779
_diffrn_reflns_point_group_measured_fraction_max 0.9746
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.12
_diffrn_reflns_theta_min         5.22
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
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    1.563
_exptl_crystal_description       prism
_exptl_crystal_F_000             200.837
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2165
_refine_diff_density_min         -0.2854
_refine_diff_density_rms         0.0632
_refine_ls_d_res_high            0.8251
_refine_ls_d_res_low             8.4664
_refine_ls_goodness_of_fit_ref   1.0873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0873
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.0391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1317
_reflns_number_total             1499
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00204d2.cif
_cod_data_source_block           UBJ-760
_cod_depositor_comments
'Adding full bibliography for 7160455--7160458.cif.'
_cod_original_cell_volume        412.67(4)
_cod_database_code               7160456
_chemical_oxdiff_formula         'C9 H7 F N2 O2'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2a), C5(H5), C6(H6)
;
_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 2.583
_oxdiff_exptl_absorpt_empirical_full_min 0.690