Synthesis of di(hetero)aryl sulfides by defluorinative sulfenylation of polyfluoroalkyl ketones with sodium sulfinates or arylsulfonyl chlorides.
Chu, Xue-Qiang; Xie, Ting; Wang, Ya-Wen; Li, Xiang-Rui; Rao, Weidong; Xu, Haiyan; Shen, Zhi-Liang; Chemical communications (Cambridge, England) 56 (2020) 8699–8702; doi:10.1039/d0cc03303k

data_7126749
_publ_section_title
;
 Synthesis of di(hetero)aryl sulfides by defluorinative sulfenylation of
 polyfluoroalkyl ketones with sodium sulfinates or arylsulfonyl chlorides.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8699
_journal_page_last               8702
_journal_paper_doi               10.1039/d0cc03303k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C20 H10 Br F5 O S'
_chemical_formula_sum            'C20 H10 Br F5 O S'
_chemical_formula_weight         473.25
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-05 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   31.0847(14)
_cell_length_b                   31.0847(14)
_cell_length_c                   7.6891(5)
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    292.59(10)
_cell_measurement_theta_max      76.6200
_cell_measurement_theta_min      4.0220
_cell_volume                     7429.7(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      292.59(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -109.00  -13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -57.0000  120.0000 96

  2 omega   57.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.9843 -151.0000  135.0000 26

  3 omega   36.00   76.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   90.0000 40

  4 omega   39.00   96.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  -60.0000 57

  5 omega   37.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -180.0000 46

  6 omega  101.00  137.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000  -30.0000 36

  7 omega   38.00   64.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -34.0000  155.0000 26

  8 omega  148.00  173.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000  -30.0000 25

  9 omega   61.00   96.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000    0.0000 35

 10 omega   57.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000  -90.0000 52

 11 omega  118.00  149.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000  -90.0000 31

 12 omega  152.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000  150.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0453172000
_diffrn_orient_matrix_UB_12      0.0152492000
_diffrn_orient_matrix_UB_13      -0.0525771000
_diffrn_orient_matrix_UB_21      0.0192623000
_diffrn_orient_matrix_UB_22      0.0420165000
_diffrn_orient_matrix_UB_23      -0.0723777000
_diffrn_orient_matrix_UB_31      0.0055532000
_diffrn_orient_matrix_UB_32      -0.0214205000
_diffrn_orient_matrix_UB_33      -0.1793695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8417
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.572
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         4.022
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_description       block
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0973
_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^)+(0.1900P)^2^+13.0575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2749
_refine_ls_wR_factor_ref         0.3106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2447
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03303k2.cif
_cod_data_source_block           g200605b
_cod_depositor_comments          'Adding full bibliography for 7126749.cif.'
_cod_original_cell_volume        7429.7(8)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7126749
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N F'
_reflns_odcompleteness_completeness 94.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C19-C20
 1.43 with sigma of 0.01
 F4-C20 \\sim F5-C20 \\sim F3-C20
 with sigma of 0.01
 F2-C19 \\sim F1-C19
 with sigma of 0.01
 F3-F5 \\sim F5-F4
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20: within 1.5A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 1.5A
C18 \\sim C19: within 1.5A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 1.5A
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3)
\\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq: with
sigma of 0.02 and sigma for terminal atoms of 0.04
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C15(H15), C13(H13), C3(H3), C12(H12), C2(H2), C4(H4), C14(H14),
 C10(H10), C5(H5)
;
_shelx_res_checksum              81079
_olex2_submission_special_instructions 'No special instructions were received'