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_7159500
_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 F3 O3 Se'
_chemical_formula_sum            'C16 H15 F3 O3 Se'
_chemical_formula_weight         391.24
_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                 119.088(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4142(2)
_cell_length_b                   25.3815(4)
_cell_length_c                   8.4387(2)
_cell_measurement_reflns_used    13532
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.6040
_cell_measurement_theta_min      3.4880
_cell_volume                     1574.91(7)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    -76.00   3.00   0.50    0.09    --  -47.35 101.00 -67.00  158
  2  \w    -10.00  27.00   0.50    0.09    --   47.35-101.00-172.00   74
  3  \w   -125.00 -86.00   0.50    0.37    -- -106.00-101.00-172.00   78
  4  \w   -169.00-129.00   0.50    0.37    -- -106.00-101.00-172.00   80
  5  \w     93.00 124.00   0.50    0.37    --  113.25 101.00 -67.00   62
  6  \w     78.00 106.00   0.50    0.37    --  113.25-101.00-172.00   56
  7  \w     -7.00  23.00   0.50    0.09    --  -47.35  19.00-120.00   60
  8  \w    -26.00  28.00   0.50    0.09    --  -47.35  19.00-150.00  108
  9  \w   -119.00 -93.00   0.50    0.09    --  -47.35-125.00 -30.00   52
 10  \w    -38.00  26.00   0.50    0.09    --  -47.35  37.00 -60.00  128
 11  \w    -25.00  12.00   0.50    0.09    --  -47.35  19.00  90.00   74
 12  \w    -42.00  -4.00   0.50    0.09    --  -47.35  37.00-180.00   76
 13  \w     63.00  88.00   0.50    0.09    --   47.35-125.00-180.00   50
 14  \w   -107.00 -33.00   0.50    0.37    -- -106.00 114.00  96.49  148
 15  \w   -106.00 -54.00   0.50    0.37    -- -106.00 125.00 -30.00  104
 16  \w   -177.00 -95.00   0.50    0.37    -- -106.00 -45.00 -90.00  164
 17  \w   -177.00 -95.00   0.50    0.37    -- -106.00 -94.00-120.00  164
 18  \w    -82.00 -36.00   0.50    0.37    -- -106.00  77.00 120.00   92
 19  \w    -61.00 -33.00   0.50    0.37    -- -106.00 111.00 -72.73   56
 20  \w   -127.00-101.00   0.50    0.37    -- -106.00 146.00-172.13   52
 21  \w   -176.00-100.00   0.50    0.37    -- -106.00 -45.00 -60.00  152
 22  \w   -110.00 -34.00   0.50    0.37    -- -106.00 125.00   0.00  152
 23  \w    -73.00 -36.00   0.50    0.37    -- -106.00 125.00-180.00   74
 24  \w    -66.00 -35.00   0.50    0.37    -- -106.00 125.00  30.00   62
 25  \w   -108.00 -74.00   0.50    0.37    -- -106.00 125.00  30.00   68
 26  \w   -176.00 -92.00   0.50    0.37    -- -106.00 -15.00-180.00  168
 27  \w   -105.00 -73.00   0.50    0.37    -- -106.00 108.00  35.35   64
 28  \w   -124.00 -73.00   0.50    0.37    -- -106.00 142.00  24.26  102
 29  \w    -78.00 -51.00   0.50    0.37    -- -106.00 146.00-172.13   54
 30  \w   -121.00 -77.00   0.50    0.37    -- -106.00 138.00 159.41   88
 31  \w   -103.00 -77.00   0.50    0.37    -- -106.00 141.00  36.11   52
 32  \w   -108.00 -73.00   0.50    0.37    -- -106.00 111.00 -72.73   70
 33  \w   -102.00 -72.00   0.50    0.37    -- -106.00 101.00 -67.00   60
 34  \w    -64.00 -34.00   0.50    0.37    -- -106.00  61.00 -60.00   60
 35  \w     42.00  71.00   0.50    0.37    --  113.25 -61.00  90.00   58
 36  \w    103.00 171.00   0.50    0.37    --  113.25  15.00  30.00  136
 37  \w     58.00  95.00   0.50    0.37    --  113.25 -94.00 150.00   74
 38  \w     42.00  98.00   0.50    0.37    --  113.25 -77.00-180.00  112
 39  \w     52.00  91.00   0.50    0.37    --  113.25-125.00 -60.00   78
 40  \w     43.00  70.00   0.50    0.37    --  113.25 -61.00  30.00   54
 41  \w    103.00 171.00   0.50    0.37    --  113.25  45.00  90.00  136
 42  \w    146.00 174.00   0.50    0.37    --  113.25 125.00  90.00   56
 43  \w     72.00 102.00   0.50    0.37    --  113.25 -94.00 120.00   60
 44  \w    100.00 126.00   0.50    0.37    --  113.25 125.00  90.00   52
;
_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      0.0844815000
_diffrn_orient_matrix_UB_12      -0.0289291000
_diffrn_orient_matrix_UB_13      0.1835334000
_diffrn_orient_matrix_UB_21      -0.1069511000
_diffrn_orient_matrix_UB_22      -0.0501310000
_diffrn_orient_matrix_UB_23      -0.0956734000
_diffrn_orient_matrix_UB_31      0.1590102000
_diffrn_orient_matrix_UB_32      -0.0183207000
_diffrn_orient_matrix_UB_33      -0.0282337000
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18825
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.495
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_min         3.483
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81649
_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    1.650
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.422
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0767
_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^)+22.3191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.1807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2747
_reflns_number_total             2812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00833a2.cif
_cod_data_source_block           2g
_cod_depositor_comments
'Adding full bibliography for 7159500--7159502.cif.'
_cod_original_cell_volume        1574.90(7)
_cod_database_code               7159500
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C16 H14 F3 O3 Se '
_shelx_estimated_absorpt_t_max   0.611
_shelx_estimated_absorpt_t_min   0.529
_reflns_odcompleteness_completeness 99.91
_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:
 C2(H2), C11(H11), C9(H9), C6(H6), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              84005
_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 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.830