Ligand-free Ullmann-type arylation of oxazolidinones by diaryliodonium salts.
Podrezova, Ekaterina V.; Okhina, Alina A.; Rogachev, Artem D.; Baykov, Sergey V.; Kirschning, Andreas; Yusubov, Mekhman S.; Soldatova, Natalia S.; Postnikov, Pavel S.; Organic & biomolecular chemistry 21 (2023) 1952–1957; doi:10.1039/d2ob02122f

data_7159173
_publ_section_title
;
 Ligand-free Ullmann-type arylation of oxazolidinones by diaryliodonium
 salts.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1952
_journal_page_last               1957
_journal_paper_doi               10.1039/d2ob02122f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H10 Cl N O2'
_chemical_formula_sum            'C10 H10 Cl N O2'
_chemical_formula_weight         211.64
_chemical_name_systematic        (S)-3-(4-chlorophenyl)-4-methyloxazolidin-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqqb
_audit_creation_date             2022-11-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-10 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.371(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.53040(10)
_cell_length_b                   8.5314(2)
_cell_length_c                   10.1412(2)
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7840
_cell_measurement_theta_min      4.3660
_cell_volume                     477.655(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -57.00 -32.00   0.50    3.20    --  -35.49  73.00  -9.00   50
  2  \w      5.00  31.00   0.50    3.20    --  -35.49  73.00  -9.00   52
  3  \w    120.00 153.00   0.50    9.43    --  100.00  73.00  -9.00   66
  4  \w     40.00 123.00   0.50    9.43    --  100.00 -73.00-138.00  166
  5  \w    -95.00 -49.00   0.50    3.20    --  -35.49 138.00 -30.00   92
  6  \w    -45.00 -16.00   0.50    3.20    --  -35.49 138.00 -30.00   58
  7  \w    -32.00   2.00   0.50    3.20    --   35.49 -65.00 120.00   68
  8  \w     24.00  53.00   0.50    3.20    --   35.49 -43.00 -60.00   58
  9  \w    -21.00  21.00   0.50    3.20    --   35.49 -43.00 -60.00   84
 10  \w     26.00  59.00   0.50    3.20    --   35.49 -89.00-150.00   66
 11  \w    -28.00  -1.00   0.50    3.20    --   35.49 -73.00-138.00   54
 12  \w    -25.00  17.00   0.50    3.20    --   35.49 -89.00-150.00   84
 13  \w      6.00  55.00   0.50    3.20    --   35.49 -65.00 120.00   98
 14  \w      3.00  28.00   0.50    3.20    --   35.49-104.00 150.00   50
 15  \w     39.00  64.00   0.50    3.20    --   35.49 -73.00-138.00   50
 16  \w     39.00  89.00   0.50    3.20    --   35.49-138.00 -90.00  100
 17  \w    118.00 144.00   0.50    9.43    --  100.00  37.00 120.00   52
 18  \w     81.00 115.00   0.50    9.43    --  100.00  37.00 120.00   68
 19  \w     36.00  80.00   0.50    9.43    --  100.00 -45.00  60.00   88
 20  \w     96.00 123.00   0.50    9.43    --  100.00  77.00 120.00   54
 21  \w     43.00  69.00   0.50    9.43    --  100.00-125.00-120.00   52
 22  \w     81.00 125.00   0.50    9.43    --  100.00-149.00  90.00   88
 23  \w    110.00 135.00   0.50    9.43    --  100.00  61.00 -90.00   50
 24  \w    124.00 157.00   0.50    9.43    --  100.00 149.00-180.00   66
 25  \w     33.00 117.00   0.50    9.43    --  100.00 -45.00-150.00  168
 26  \w     87.00 120.00   0.50    9.43    --  100.00 149.00-180.00   66
 27  \w     78.00 156.00   0.50    9.43    --  100.00  53.00-120.00  156
 28  \w     75.00 112.00   0.50    9.43    --  100.00-125.00-120.00   74
 29  \w     83.00 147.00   0.50    9.43    --  100.00  77.00 -30.00  128
 30  \w     74.00 116.00   0.50    9.43    --  100.00  69.00   0.00   84
 31  \w    131.00 156.00   0.50    9.43    --  100.00  69.00   0.00   50
 32  \w     88.00 126.00   0.50    9.43    --  100.00 107.00-120.00   76
 33  \w     88.00 118.00   0.50    9.43    --  100.00 -45.00  60.00   60
 34  \w     87.00 147.00   0.50    9.43    --  100.00  91.00 -60.00  120
 35  \w    -27.00  -1.00   0.50    3.20    --  -35.49  73.00  -9.00   52
 36  \w     -7.00  31.00   0.50    3.20    --  -35.49  54.00 -90.00   76
 37  \w     41.00 103.00   0.50    3.20    --   35.49  43.00  60.00  124
 38  \w    -35.00  -9.00   0.50    3.20    --   35.49 -21.00-150.00   52
 39  \w     69.00 101.00   0.50    3.20    --   35.49  32.00 150.00   64
 40  \w     29.00  55.00   0.50    3.20    --   35.49-138.00  60.00   52
 41  \w     23.00  50.00   0.50    3.20    --   35.49 -21.00-150.00   54
 42  \w     47.00 102.00   0.50    3.20    --   35.49  65.00  90.00  110
 43  \w     28.00  61.00   0.50    3.20    --   35.49  32.00 150.00   66
 44  \w     79.00 157.00   0.50    9.43    --  100.00  53.00  30.00  156
 45  \w     74.00 102.00   0.50    9.43    --  100.00  69.00  60.00   56
 46  \w    119.00 145.00   0.50    9.43    --  100.00  69.00 120.00   52
 47  \w    117.00 143.00   0.50    9.43    --  100.00  69.00  60.00   52
 48  \w     39.00  65.00   0.50    9.43    --  100.00-125.00   0.00   52
 49  \w     82.00 108.00   0.50    9.43    --  100.00-125.00   0.00   52
 50  \w    111.00 147.00   0.50    9.43    --  100.00  45.00  90.00   72
 51  \w     30.00  55.00   0.50    9.43    --  100.00 -30.00-180.00   50
 52  \w     79.00 105.00   0.50    9.43    --  100.00  69.00 120.00   52
 53  \w    116.00 141.00   0.50    9.43    --  100.00 107.00 120.00   50
 54  \w    130.00 155.00   0.50    9.43    --  100.00  -7.00 150.00   50
 55  \w     69.00 120.00   0.50    9.43    --  100.00 -30.00-180.00  102
 56  \w     75.00 107.00   0.50    9.43    --  100.00-107.00-120.00   64
 57  \w     81.00 111.00   0.50    9.43    --  100.00 -77.00  30.00   60
 58  \w     87.00 113.00   0.50    9.43    --  100.00  45.00 150.00   52
 59  \w    116.00 144.00   0.50    9.43    --  100.00  45.00 150.00   56
 60  \w    113.00 152.00   0.50    9.43    --  100.00  53.00  60.00   78
 61  \w     73.00  99.00   0.50    9.43    --  100.00  69.00  90.00   52
 62  \w     29.00  67.00   0.50    9.43    --  100.00 -91.00  30.00   76
 63  \w     81.00 106.00   0.50    9.43    --  100.00 -91.00  30.00   50
 64  \w     27.00  73.00   0.50    9.43    --  100.00-107.00   0.00   92
 65  \w     35.00  61.00   0.50    9.43    --  100.00-125.00 -60.00   52
 66  \w     67.00  93.00   0.50    9.43    --  100.00-125.00 -60.00   52
 67  \w     49.00  75.00   0.50    9.43    --  100.00 -77.00  30.00   52
 68  \w     66.00 116.00   0.50    9.43    --  100.00 -61.00  30.00  100
 69  \w     20.00  46.00   0.50    9.43    --  100.00  -7.00 150.00   52
 70  \w     26.00  68.00   0.50    9.43    --  100.00-107.00-120.00   84
 71  \w     81.00 107.00   0.50    9.43    --  100.00  53.00 120.00   52
 72  \w     80.00 105.00   0.50    9.43    --  100.00  45.00  90.00   50
 73  \w     98.00 145.00   0.50    9.43    --  100.00  37.00  60.00   94
;
_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      0.0749331000
_diffrn_orient_matrix_UB_12      -0.0395502000
_diffrn_orient_matrix_UB_13      -0.1400594000
_diffrn_orient_matrix_UB_21      -0.1462552000
_diffrn_orient_matrix_UB_22      0.1415174000
_diffrn_orient_matrix_UB_23      -0.0552728000
_diffrn_orient_matrix_UB_31      0.2256245000
_diffrn_orient_matrix_UB_32      0.1049519000
_diffrn_orient_matrix_UB_33      0.0217378000
_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  0.0112
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3560
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        64.867
_diffrn_reflns_theta_max         64.867
_diffrn_reflns_theta_min         4.367
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       prism
_exptl_crystal_F_000             220
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1613
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0197
_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^)+(0.0312P)^2^+0.0971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0523
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1591
_reflns_number_total             1613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02122f2.cif
_cod_data_source_block           evk-557_auto
_cod_depositor_comments
'Adding full bibliography for 7159171--7159173.cif.'
_cod_database_code               7159173
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C10 H10 Cl N O2 '
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.619
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C3(H3)
1.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              12669
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.789