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_7160455
_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         'C15 H11 F N2 O2'
_chemical_formula_sum            'C15 H11 F N2 O2'
_chemical_formula_weight         270.265
_chemical_name_common
3-(4-fluorophenyl)-4-phenyl-4H-1,2,4-oxadiazin-5(6H)-one
_chemical_name_systematic        UBJ-1072
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-11-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-07 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.568(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1769(3)
_cell_length_b                   7.4272(2)
_cell_length_c                   18.6039(6)
_cell_measurement_reflns_used    3296
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2340
_cell_measurement_theta_min      4.8260
_cell_volume                     1242.26(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.9658
_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   -114.00 -18.00   1.00    1.25    --  -41.56 -57.00  30.00   96
  2  \w    -86.00 -51.00   1.00    1.25    --  -41.56 178.00-150.00   35
  3  \w    -18.00  32.00   1.00    1.25    --   41.56 -77.00-120.00   50
  4  \w     66.00 125.00   1.00    1.25    --   41.56 178.00 120.00   59
  5  \w    135.00 169.00   1.00    5.00    --  112.00  30.00 150.00   34
  6  \w     47.00 135.00   1.00    5.00    --  112.00 -45.00  30.00   88
  7  \w    143.00 174.00   1.00    5.00    --  112.00  15.00 120.00   31
  8  \w    112.00 172.00   1.00    5.00    --  112.00 125.00 -30.00   60
  9  \w     64.00  93.00   1.00    5.00    --  112.00 -61.00-120.00   29
 10  \w     92.00 118.00   1.00    5.00    --  112.00  30.00 150.00   26
 11  \w     56.00 126.00   1.00    5.00    --  112.00 -30.00-150.00   70
 12  \w    111.00 136.00   1.00    5.00    --  112.00  77.00   0.00   25
 13  \w     39.00  83.00   1.00    5.00    --  112.00-125.00 -60.00   44
 14  \w     64.00 140.00   1.00    5.00    --  112.00  15.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024240000
_diffrn_orient_matrix_UB_12      0.0021027000
_diffrn_orient_matrix_UB_13      -0.0831035000
_diffrn_orient_matrix_UB_21      0.1146868000
_diffrn_orient_matrix_UB_22      -0.1540616000
_diffrn_orient_matrix_UB_23      0.0098221000
_diffrn_orient_matrix_UB_31      -0.1271319000
_diffrn_orient_matrix_UB_32      -0.1388283000
_diffrn_orient_matrix_UB_33      -0.0122788000
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.9884
_diffrn_reflns_Laue_measured_fraction_max 0.9658
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5035
_diffrn_reflns_point_group_measured_fraction_full 0.9884
_diffrn_reflns_point_group_measured_fraction_max 0.9658
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.38
_diffrn_reflns_theta_min         4.85
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (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    1.445
_exptl_crystal_description       prism
_exptl_crystal_F_000             562.135
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method -
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.2852
_refine_diff_density_min         -0.3115
_refine_diff_density_rms         0.0669
_refine_ls_d_res_high            0.7932
_refine_ls_d_res_low             9.1130
_refine_ls_goodness_of_fit_ref   1.0548
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0548
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0602P)^2^+0.6355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -8
_reflns_number_gt                2208
_reflns_number_total             2514
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00204d2.cif
_cod_data_source_block           UBJ-1072
_cod_depositor_comments
'Adding full bibliography for 7160455--7160458.cif.'
_cod_original_cell_volume        1242.25(7)
_cod_database_code               7160455
_chemical_oxdiff_formula         'C15 H11 F 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 2.616
_oxdiff_exptl_absorpt_empirical_full_min 0.598