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_7160457
_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 Br N2 O2'
_chemical_formula_sum            'C15 H11 Br N2 O2'
_chemical_formula_weight         331.170
_chemical_name_common
3-(4-bromophenyl)-4-phenyl-4H-1,2,4-oxadiazin-5(6H)-one
_chemical_name_systematic        UBJ-1124
_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
_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                105.632(3)
_cell_angle_beta                 92.203(3)
_cell_angle_gamma                100.013(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7761(3)
_cell_length_b                   9.1850(4)
_cell_length_c                   12.8929(4)
_cell_measurement_reflns_used    5469
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4650
_cell_measurement_theta_min      3.6340
_cell_volume                     646.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9772
_diffrn_measured_fraction_theta_max 0.9742
_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    -71.00 -43.00   0.50    0.20    -- -106.00  61.00-148.00   56
  2  \w    -39.00  24.00   0.50    0.05    --  -47.14  61.00-148.00  126
  3  \w    -68.00 -41.00   0.50    0.20    -- -106.00  61.00 -30.00   54
  4  \w    -67.00 -42.00   0.50    0.20    -- -106.00  61.00   0.00   50
  5  \w    -71.00 -35.00   0.50    0.20    -- -106.00  61.00  60.00   72
  6  \w    -16.00  14.00   0.50    0.05    --  -47.14  19.00   0.00   60
  7  \w    -17.00  24.00   0.50    0.05    --   47.14 -19.00  60.00   82
  8  \w     -9.00  19.00   0.50    0.05    --   47.14 -19.00 120.00   56
  9  \w    -13.00  14.00   0.50    0.05    --   47.14 -61.00  72.00   54
 10  \w     20.00  64.00   0.50    0.05    --   47.14 -61.00  72.00   88
 11  \w     68.00 110.00   0.50    0.20    --  113.25-125.00 150.00   84
 12  \w     77.00 104.00   0.50    0.20    --  113.25 -94.00 120.00   54
 13  \w     84.00 109.00   0.50    0.20    --  113.25-125.00  60.00   50
 14  \w     52.00  95.00   0.50    0.20    --  113.25 -94.00  60.00   86
 15  \w     62.00 103.00   0.50    0.20    --  113.25 -94.00 -30.00   82
 16  \w     45.00  86.00   0.50    0.20    --  113.25-125.00-120.00   82
 17  \w     74.00 110.00   0.50    0.20    --  113.25-125.00-150.00   72
 18  \w     50.00 102.00   0.50    0.20    --  113.25 -94.00-120.00  104
 19  \w     81.00 106.00   0.50    0.20    --  113.25 -77.00-120.00   50
 20  \w     42.00  67.00   0.50    0.20    --  113.25 -61.00-120.00   50
 21  \w     43.00  68.00   0.50    0.20    --  113.25 -61.00   0.00   50
 22  \w     42.00  67.00   0.50    0.20    --  113.25 -61.00  60.00   50
 23  \w     42.00  67.00   0.50    0.20    --  113.25 -61.00  72.00   50
 24  \w     44.00  69.00   0.50    0.20    --  113.25 -61.00  90.00   50
 25  \w     43.00  69.00   0.50    0.20    --  113.25 -61.00 120.00   52
 26  \w    140.00 178.00   0.50    0.20    --  113.25  15.00   0.00   76
 27  \w    122.00 169.00   0.50    0.20    --  113.25  45.00 150.00   94
 28  \w    100.00 178.00   0.50    0.20    --  113.25  15.00 120.00  156
 29  \w    102.00 169.00   0.50    0.20    --  113.25  61.00-148.00  134
 30  \w     70.00 117.00   0.50    0.05    --   47.14  61.00-148.00   94
 31  \w     33.00  67.00   0.50    0.05    --   47.14  61.00-148.00   68
 32  \w    -89.00 -16.00   0.50    0.05    --  -47.14 125.00 -30.00  146
 33  \w    -73.00 -37.00   0.50    0.20    -- -106.00 113.00-135.10   72
 34  \w    -71.00 -38.00   0.50    0.20    -- -106.00 125.00 -30.00   66
 35  \w   -112.00 -73.00   0.50    0.20    -- -106.00 125.00 -30.00   78
 36  \w   -108.00 -82.00   0.50    0.20    -- -106.00 113.00-135.10   52
 37  \w   -107.00 -78.00   0.50    0.20    -- -106.00 108.00 -39.80   58
 38  \w    -63.00 -36.00   0.50    0.20    -- -106.00 108.00 -39.80   54
 39  \w   -112.00 -86.00   0.50    0.20    -- -106.00 125.00  60.00   52
 40  \w    -62.00 -36.00   0.50    0.20    -- -106.00 125.00 150.00   52
 41  \w   -150.00 -96.00   0.50    0.20    -- -106.00 -30.00 -90.00  108
 42  \w   -133.00-107.00   0.50    0.20    -- -106.00 -61.00-180.00   52
 43  \w   -175.00-136.00   0.50    0.20    -- -106.00 -61.00-180.00   78
 44  \w   -106.00 -37.00   0.50    0.05    --  -47.14 -61.00  72.00  138
 45  \w   -147.00 -89.00   0.50    0.20    -- -106.00 -61.00  72.00  116
 46  \w   -176.00 -89.00   0.50    0.20    -- -106.00 -61.00 150.00  174
;
_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      -0.2082638000
_diffrn_orient_matrix_UB_12      -0.1182241000
_diffrn_orient_matrix_UB_13      -0.0698923000
_diffrn_orient_matrix_UB_21      -0.1733868000
_diffrn_orient_matrix_UB_22      0.1000480000
_diffrn_orient_matrix_UB_23      0.0549640000
_diffrn_orient_matrix_UB_31      0.0226755000
_diffrn_orient_matrix_UB_32      0.0866146000
_diffrn_orient_matrix_UB_33      -0.0872643000
_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  0.0427
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.9772
_diffrn_reflns_Laue_measured_fraction_max 0.9742
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6851
_diffrn_reflns_point_group_measured_fraction_full 0.9772
_diffrn_reflns_point_group_measured_fraction_max 0.9742
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
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    1.702
_exptl_crystal_description       prism
_exptl_crystal_F_000             331.620
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.0018
_refine_diff_density_min         -0.4183
_refine_diff_density_rms         0.1087
_refine_ls_d_res_high            0.8204
_refine_ls_d_res_low             12.3657
_refine_ls_goodness_of_fit_ref   1.0424
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0424
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.1267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2311
_reflns_number_total             2382
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob00204d2.cif
_cod_data_source_block           UBJ-1124
_cod_depositor_comments
'Adding full bibliography for 7160455--7160458.cif.'
_cod_database_code               7160457
_chemical_oxdiff_formula         'C15 H11 Br 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:
 C2(H2), C6(H6), C3(H3), C14(H14), C15(H15), C5(H5), C11(H11), C13(H13),
 C12(H12)
;
_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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.751