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_7159172
_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         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_chemical_name_systematic        (S)-4-(tert-butyl)-3-phenyloxazolidin-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqp9
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2495(2)
_cell_length_b                   12.5730(3)
_cell_length_c                   15.1106(5)
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.9380
_cell_measurement_theta_min      4.5540
_cell_volume                     1187.31(6)
_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 1.000
_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   -106.00 -56.00   0.50    0.84    --  -35.49-163.00  -8.00  100
  2  \w    -58.00   9.00   0.50    0.84    --  -35.49  52.00  -1.00  134
  3  \w    -72.00 -47.00   0.50    0.84    --  -35.49 116.00-130.00   50
  4  \w     32.00  57.00   0.50    0.84    --   35.49-163.00  -8.00   50
  5  \w     60.00  94.00   0.50    0.84    --   35.49  52.00  -1.00   68
  6  \w     81.00 106.00   0.50    0.84    --   35.49-163.00  -8.00   50
  7  \w     23.00  54.00   0.50    0.84    --   35.49  52.00  -1.00   62
  8  \w      8.00  45.00   0.50    0.84    --   35.49  69.00 154.00   74
  9  \w     89.00 115.00   0.50    3.36    --  100.00 163.00  18.00   52
 10  \w     73.00 140.00   0.50    3.36    --  100.00  69.00 154.00  134
 11  \w     77.00 128.00   0.50    3.36    --  100.00  52.00  -1.00  102
 12  \w     60.00  86.00   0.50    3.36    --  100.00 -69.00  22.00   52
 13  \w     77.00 112.00   0.50    3.36    --  100.00 -52.00-146.00   70
 14  \w     65.00  91.00   0.50    3.36    --  100.00-116.00 141.00   52
 15  \w    -73.00  -6.00   0.50    0.84    --  -35.49 104.00   0.00  134
 16  \w    -38.00  -8.00   0.50    0.84    --  -35.49 116.00-130.00   60
 17  \w    -79.00 -54.00   0.50    0.84    --  -35.49 -69.00  22.00   50
 18  \w     23.00  48.00   0.50    0.84    --   35.49-138.00-120.00   50
 19  \w      4.00  42.00   0.50    0.84    --   35.49-116.00 141.00   76
 20  \w     83.00 121.00   0.50    3.36    --  100.00  77.00 120.00   76
 21  \w    110.00 156.00   0.50    3.36    --  100.00 107.00-180.00   92
 22  \w     90.00 149.00   0.50    3.36    --  100.00  91.00  90.00  118
 23  \w     55.00 107.00   0.50    3.36    --  100.00 -45.00-180.00  104
 24  \w     88.00 156.00   0.50    3.36    --  100.00 107.00-120.00  136
 25  \w     85.00 143.00   0.50    3.36    --  100.00  91.00 -90.00  116
 26  \w    127.00 154.00   0.50    3.36    --  100.00  77.00 120.00   54
 27  \w     86.00 157.00   0.50    3.36    --  100.00  37.00  60.00  142
 28  \w    -33.00  -7.00   0.50    0.84    --   35.49 -69.00  22.00   52
 29  \w      0.00  26.00   0.50    0.84    --  -35.49  32.00-150.00   52
 30  \w   -107.00 -81.00   0.50    0.84    --  -35.49 -32.00 120.00   52
 31  \w    -43.00 -17.00   0.50    0.84    --  -35.49 -32.00 120.00   52
 32  \w    -49.00  -9.00   0.50    0.84    --  -35.49  32.00-150.00   80
 33  \w     61.00 105.00   0.50    0.84    --   35.49  43.00 150.00   88
 34  \w     53.00 103.00   0.50    0.84    --   35.49  65.00 -90.00  100
 35  \w     -9.00  27.00   0.50    0.84    --   35.49 -32.00   0.00   72
 36  \w     17.00  49.00   0.50    0.84    --   35.49  43.00 150.00   64
 37  \w     18.00  44.00   0.50    0.84    --   35.49  43.00 -90.00   52
 38  \w     75.00 105.00   0.50    0.84    --   35.49  43.00 -90.00   60
 39  \w    -40.00  10.00   0.50    0.84    --   35.49 -21.00  30.00  100
 40  \w     24.00  50.00   0.50    0.84    --   35.49 -69.00  22.00   52
 41  \w     12.00  37.00   0.50    0.84    --   35.49  65.00 -90.00   50
 42  \w     37.00  63.00   0.50    0.84    --   35.49 -21.00  30.00   52
 43  \w     13.00  43.00   0.50    0.84    --   35.49  54.00 -60.00   60
 44  \w     40.00  78.00   0.50    3.36    --  100.00 -30.00-120.00   76
 45  \w     31.00  57.00   0.50    3.36    --  100.00-107.00  90.00   52
 46  \w     77.00 103.00   0.50    3.36    --  100.00 -91.00-150.00   52
 47  \w    132.00 157.00   0.50    3.36    --  100.00  69.00 -90.00   50
 48  \w     26.00  83.00   0.50    3.36    --  100.00-107.00  60.00  114
 49  \w     75.00 101.00   0.50    3.36    --  100.00  61.00 -90.00   52
 50  \w     25.00  99.00   0.50    3.36    --  100.00 -22.00 150.00  148
 51  \w    125.00 151.00   0.50    3.36    --  100.00 107.00-150.00   52
 52  \w     90.00 116.00   0.50    3.36    --  100.00 107.00 -60.00   52
 53  \w     74.00 100.00   0.50    3.36    --  100.00  69.00 -90.00   52
 54  \w     56.00  82.00   0.50    3.36    --  100.00 -53.00  30.00   52
 55  \w    122.00 149.00   0.50    3.36    --  100.00  30.00 150.00   54
 56  \w     86.00 112.00   0.50    3.36    --  100.00-125.00-180.00   52
 57  \w     75.00 107.00   0.50    3.36    --  100.00-107.00  90.00   64
 58  \w     77.00 102.00   0.50    3.36    --  100.00  53.00 -90.00   50
 59  \w     79.00 104.00   0.50    3.36    --  100.00  45.00  90.00   50
;
_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      -0.0430028000
_diffrn_orient_matrix_UB_12      -0.0035783000
_diffrn_orient_matrix_UB_13      0.1004175000
_diffrn_orient_matrix_UB_21      0.1506175000
_diffrn_orient_matrix_UB_22      -0.0963471000
_diffrn_orient_matrix_UB_23      0.0086642000
_diffrn_orient_matrix_UB_31      0.1903278000
_diffrn_orient_matrix_UB_32      0.0755195000
_diffrn_orient_matrix_UB_33      0.0157136000
_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  0.0553
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6810
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        64.985
_diffrn_reflns_theta_max         64.985
_diffrn_reflns_theta_min         4.575
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52057
_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    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0499P)^2^+0.0574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                1792
_reflns_number_total             1980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02122f2.cif
_cod_data_source_block           evk-548_auto
_cod_depositor_comments
'Adding full bibliography for 7159171--7159173.cif.'
_cod_database_code               7159172
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C13 H17 N O2 '
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.931
_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:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              28693
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.257