Metal-free and atom-efficient protocol for diarylation of selenocyanate by diaryliodonium salts.
Radzhabov, Amirbek D.; Soldatova, Natalia S.; Ivanov, Daniil M.; Yusubov, Mekhman S.; Kukushkin, Vadim Yu; Postnikov, Pavel S.; Organic & biomolecular chemistry 21 (2023) 6743–6749; doi:10.1039/d3ob00833a

data_7159502
_publ_section_title
;
 Metal-free and atom-efficient protocol for diarylation of selenocyanate
 by diaryliodonium salts.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6743
_journal_page_last               6749
_journal_paper_doi               10.1039/d3ob00833a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H15 N O3 Se'
_chemical_formula_sum            'C16 H15 N O3 Se'
_chemical_formula_weight         348.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2023-03-20 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.016(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6406(9)
_cell_length_b                   4.3593(3)
_cell_length_c                   23.6861(19)
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.2630
_cell_measurement_theta_min      3.0980
_cell_volume                     1466.71(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -26.00   2.00   0.50    0.05    --  -47.35  18.00  19.00   56
  2  \w   -112.00 -41.00   0.50    0.05    --  -47.35 -18.00-148.00  142
  3  \w    -26.00  26.00   0.50    0.05    --   47.35 -18.00-148.00  104
  4  \w     36.00 122.00   0.50    0.05    --   47.35  18.00  19.00  172
  5  \w   -170.00-116.00   0.50    0.05    -- -106.00 -18.00-148.00  108
  6  \w    102.00 127.00   0.50    0.05    --  113.25  18.00  19.00   50
  7  \w    -20.00  41.00   0.50    0.05    --   47.35 -37.00  60.00  122
  8  \w    -93.00 -67.00   0.50    0.05    -- -106.00 125.00  90.00   52
  9  \w    -64.00 -33.00   0.50    0.05    -- -106.00  61.00 120.00   62
 10  \w   -112.00 -86.00   0.50    0.05    -- -106.00 125.00  60.00   52
 11  \w    -66.00 -34.00   0.50    0.05    -- -106.00  61.00 -60.00   64
 12  \w    -60.00 -35.00   0.50    0.05    -- -106.00 125.00  90.00   50
 13  \w    -60.00 -34.00   0.50    0.05    -- -106.00  61.00-180.00   52
 14  \w    -70.00 -45.00   0.50    0.05    -- -106.00  61.00 -30.00   50
 15  \w    -64.00 -34.00   0.50    0.05    -- -106.00  61.00  90.00   60
 16  \w    -72.00 -40.00   0.50    0.05    -- -106.00 125.00  60.00   64
 17  \w    126.00 177.00   0.50    0.05    --  113.25  45.00 -60.00  102
 18  \w     73.00 106.00   0.50    0.05    --  113.25 -94.00 120.00   66
 19  \w    106.00 168.00   0.50    0.05    --  113.25  30.00  60.00  124
 20  \w    126.00 176.00   0.50    0.05    --  113.25  45.00 -30.00  100
 21  \w     42.00  67.00   0.50    0.05    --  113.25 -61.00   0.00   50
 22  \w     60.00  86.00   0.50    0.05    --  113.25-125.00  90.00   52
 23  \w     42.00  67.00   0.50    0.05    --  113.25 -61.00 120.00   50
 24  \w     44.00 104.00   0.50    0.05    --  113.25 -77.00 120.00  120
 25  \w    100.00 170.00   0.50    0.05    --  113.25  15.00 -60.00  140
 26  \w     42.00  67.00   0.50    0.05    --  113.25 -61.00 150.00   50
 27  \w    -82.00 -31.00   0.50    0.05    --  -47.35 108.00-177.00  102
 28  \w    -15.00  21.00   0.50    0.05    --   18.00  99.00-135.08   72
 29  \w    -14.00  11.00   0.50    0.05    --   18.00  96.00 142.74   50
 30  \w    -11.00  14.00   0.50    0.05    --   22.00  99.00  40.69   50
 31  \w     -9.00  17.00   0.50    0.05    --   22.00  97.00 -33.08   52
 32  \w     17.00  42.00   0.50    0.05    --   46.00  90.00  99.25   50
 33  \w     17.00  42.00   0.50    0.05    --   46.00  90.00 157.95   50
 34  \w     26.00  52.00   0.50    0.05    --   47.35  77.00 -60.00   52
 35  \w     43.00  89.00   0.50    0.05    --   47.35  19.00  90.00   92
 36  \w     25.00  51.00   0.50    0.05    --   47.35  77.00   0.00   52
 37  \w     56.00  95.00   0.50    0.05    --   47.35-125.00  90.00   78
 38  \w     25.00  52.00   0.50    0.05    --   47.35-125.00  90.00   54
 39  \w     28.00  54.00   0.50    0.05    --   50.00  76.00 139.87   52
 40  \w     30.00  67.00   0.50    0.05    --   50.00  75.00-136.35   74
 41  \w     55.00  81.00   0.50    0.05    --   50.00  76.00 139.87   52
 42  \w     32.00  64.00   0.50    0.05    --   54.00  77.00  75.71   64
 43  \w     99.00 125.00   0.50    0.05    --   54.00  77.00  75.71   52
 44  \w    -72.00 -36.00   0.50    0.05    --  -58.00 -74.00 165.36   72
 45  \w    -63.00 -38.00   0.50    0.05    --  -58.00 -74.00  35.11   50
 46  \w     35.00  61.00   0.50    0.05    --   58.00  77.00  35.63   52
 47  \w     35.00  65.00   0.50    0.05    --   58.00  77.00-119.58   60
 48  \w   -135.00 -99.00   0.50    0.05    --  -62.00 -74.00-168.16   72
 49  \w    -65.00 -40.00   0.50    0.05    --  -62.00 -74.00-168.16   50
 50  \w     41.00  66.00   0.50    0.05    --   62.00  74.00 -93.91   50
 51  \w    -72.00 -46.00   0.50    0.05    --  -66.00 -69.00  -9.73   52
 52  \w    -80.00 -54.00   0.50    0.05    --  -66.00 -60.00 132.24   52
 53  \w    -70.00 -44.00   0.50    0.05    --  -66.00 -74.00 -48.58   52
 54  \w    -74.00 -48.00   0.50    0.05    --  -66.00 -65.00  -4.05   52
 55  \w    -75.00 -49.00   0.50    0.05    --  -66.00 -65.00  13.81   52
 56  \w    -77.00 -51.00   0.50    0.05    --  -70.00 -67.00-172.57   52
 57  \w     47.00  73.00   0.50    0.05    --   70.00  77.00 -32.54   52
 58  \w     50.00  76.00   0.50    0.05    --   70.00  74.00  14.57   52
 59  \w     49.00  75.00   0.50    0.05    --   70.00  76.00 -90.33   52
 60  \w    -85.00 -59.00   0.50    0.05    --  -74.00 -63.00  -1.72   52
 61  \w    -83.00 -57.00   0.50    0.05    --  -74.00 -63.00 114.20   52
 62  \w    -84.00 -58.00   0.50    0.05    --  -74.00 -59.00  41.10   52
 63  \w    -88.00 -62.00   0.50    0.05    --  -78.00 -60.00  11.10   52
 64  \w    -87.00 -61.00   0.50    0.05    --  -78.00 -63.00-176.70   52
 65  \w    -86.00 -61.00   0.50    0.05    --  -78.00 -61.00 169.41   50
 66  \w    -91.00 -64.00   0.50    0.05    --  -78.00 -52.00  79.61   54
 67  \w    -83.00 -57.00   0.50    0.05    --  -78.00 -75.00 -84.16   52
 68  \w    -81.00 -56.00   0.50    0.05    --  -78.00 -74.00 -19.02   50
 69  \w    -93.00 -67.00   0.50    0.05    --  -82.00 -56.00 153.60   52
 70  \w    -94.00 -68.00   0.50    0.05    --  -82.00 -57.00  35.70   52
 71  \w    -85.00 -60.00   0.50    0.05    --  -82.00 -74.00-131.31   50
 72  \w    -89.00 -64.00   0.50    0.05    --  -82.00 -64.00   1.03   50
 73  \w    -91.00 -66.00   0.50    0.05    --  -82.00 -59.00  22.32   50
 74  \w    -88.00 -62.00   0.50    0.05    --  -82.00 -71.00  -3.00   52
 75  \w    -89.00 -63.00   0.50    0.05    --  -82.00 -69.00 -59.82   52
 76  \w    -85.00 -59.00   0.50    0.05    --  -82.00 -77.00-130.92   52
 77  \w    -93.00 -68.00   0.50    0.05    --  -82.00 -54.00  56.98   50
 78  \w    -86.00 -60.00   0.50    0.05    --  -82.00 -77.00 103.16   52
 79  \w    -96.00 -70.00   0.50    0.05    --  -86.00 -62.00  15.17   52
 80  \w    -97.00 -71.00   0.50    0.05    --  -86.00 -60.00 179.93   52
 81  \w    -94.00 -69.00   0.50    0.05    --  -90.00 -73.00-132.61   50
 82  \w   -100.00 -74.00   0.50    0.05    --  -90.00 -59.00  33.93   52
 83  \w   -102.00 -76.00   0.50    0.05    --  -90.00 -55.00 -83.25   52
 84  \w   -101.00 -76.00   0.50    0.05    --  -90.00 -53.00-113.35   50
 85  \w    -94.00 -68.00   0.50    0.05    --  -90.00 -74.00-140.39   52
 86  \w   -107.00 -82.00   0.50    0.05    --  -98.00 -64.00 164.41   50
 87  \w   -165.00-136.00   0.50    0.05    --  -98.00 -64.00 164.41   58
 88  \w   -101.00 -75.00   0.50    0.05    --  -98.00 -77.00-138.52   52
 89  \w   -109.00 -84.00   0.50    0.05    --  -98.00 -51.00  74.52   50
 90  \w   -149.00-123.00   0.50    0.05    --  -98.00 -51.00  74.52   52
 91  \w   -108.00 -82.00   0.50    0.05    --  -98.00 -60.00 -82.02   52
 92  \w   -106.00 -80.00   0.50    0.05    -- -102.00 -75.00-155.10   52
 93  \w   -170.00-130.00   0.50    0.05    -- -102.00 -75.00-155.10   80
 94  \w   -130.00 -89.00   0.50    0.05    -- -102.00 -54.00 146.95   82
 95  \w   -162.00-137.00   0.50    0.05    -- -102.00 -54.00 146.95   50
 96  \w   -176.00-139.00   0.50    0.05    -- -106.00 -54.00 138.32   74
 97  \w   -176.00-150.00   0.50    0.05    -- -106.00 -61.00 174.35   52
 98  \w   -140.00-115.00   0.50    0.05    -- -106.00 -82.00  22.14   50
;
_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      0.0603256000
_diffrn_orient_matrix_UB_12      0.0363162000
_diffrn_orient_matrix_UB_13      -0.0445705000
_diffrn_orient_matrix_UB_21      0.0891403000
_diffrn_orient_matrix_UB_22      -0.0768545000
_diffrn_orient_matrix_UB_23      0.0476622000
_diffrn_orient_matrix_UB_31      -0.0135377000
_diffrn_orient_matrix_UB_32      -0.3429021000
_diffrn_orient_matrix_UB_33      -0.0154411000
_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  0.1605
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25265
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.490
_diffrn_reflns_theta_max         67.490
_diffrn_reflns_theta_min         3.111
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.554
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
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    1.577
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.124
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0892P)^2^+5.6094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1981
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00833a2.cif
_cod_data_source_block           2i
_cod_depositor_comments
'Adding full bibliography for 7159500--7159502.cif.'
_cod_database_code               7159502
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C16 H15 N O3 Se '
_shelx_estimated_absorpt_t_max   0.618
_shelx_estimated_absorpt_t_min   0.522
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C6(H6), C3(H3), C9(H9), C5(H5)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              7132
_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 2.504
_oxdiff_exptl_absorpt_empirical_full_min 0.416