Synthesis of Diaryliodonium Salts Having Pentafluorosulfanylarenes and Their Application to Electrophilic Pentafluorosulfanylarylation of C-, O-, N-, and S-Nucleophiles.
Matsuzaki, Kohei; Okuyama, Kenta; Tokunaga, Etsuko; Saito, Norimichi; Shiro, Motoo; Shibata, Norio; Organic letters 17 (2015) 3038–3041; doi:10.1021/acs.orglett.5b01323

data_1520117
_publ_section_title
;
 Synthesis of Diaryliodonium Salts Having Pentafluorosulfanylarenes and
 Their Application to Electrophilic Pentafluorosulfanylarylation of C-,
 O-, N-, and S-Nucleophiles.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3038
_journal_page_last               3041
_journal_paper_doi               10.1021/acs.orglett.5b01323
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H15 F5 I S, C1 F3 O3 S, 0.5(C3 H6 O)'
_chemical_formula_sum            'C17.5 H18 F8 I O3.5 S2'
_chemical_formula_weight         627.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                63.1630(10)
_cell_angle_beta                 87.5260(10)
_cell_angle_gamma                77.6000(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9435(2)
_cell_length_b                   12.1892(3)
_cell_length_c                   12.2642(3)
_cell_measurement_reflns_used    11064
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.23
_cell_volume                     1162.92(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5276
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.226
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.640
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.11
_refine_diff_density_min         -0.70
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5276
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.5814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                5017
_reflns_number_total             5276
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol5b01323_si_002.cif
_cod_data_source_block           20141118
_cod_depositor_comments          'Adding full bibliography for 1520117.cif.'
_cod_database_code               1520117
_shelxl_res_file
;
TITL 20141118
CELL  0.71075 8.94350 12.18920 12.26420 63.163 87.526 77.600
ZERR  2 0.00020 0.00030 0.00030 0.001 0.001 0.001
LATT 1
SFAC C H F I O S
UNIT 35 36 16 2 7 4
L.S. 10
FMAP 2
PLAN -20
WPDB -2
HTAB
LIST 4
TEMP -100.0
ACTA
SIZE 0.200 0.200 0.200
DELU 0.01 0.01 S2 > F8
SIMU 0.01 0.01 S2 > F8
SIMU 0.01 0.01 O4 > C19A
WGHT    0.059200    0.581400
FVAR       1.00131
I1    4    0.794873    0.377103    0.446086    11.00000    0.03577    0.02345 =
         0.03285   -0.00880   -0.00688   -0.00865
S1    6    0.432415    0.708785   -0.006820    11.00000    0.05094    0.03007 =
         0.03130   -0.00856   -0.00772   -0.00312
F1    3    0.330258    0.638995   -0.045325    11.00000    0.08281    0.05265 =
         0.04036   -0.01537   -0.02002   -0.01805
F2    3    0.581327    0.629485   -0.032830    11.00000    0.06686    0.05407 =
         0.03579   -0.01091    0.00516    0.00632
F3    3    0.533123    0.785092    0.021330    11.00000    0.08168    0.04235 =
         0.04788   -0.00734   -0.00843   -0.02954
F4    3    0.282156    0.794986    0.008032    11.00000    0.06472    0.03525 =
         0.05218   -0.00726   -0.00477    0.01009
F5    3    0.423390    0.808123   -0.146476    11.00000    0.07817    0.04549 =
         0.03292   -0.00030   -0.00867   -0.00679
C1    1    0.768837    0.189652    0.512777    11.00000    0.02952    0.02068 =
         0.03087   -0.00896   -0.00462   -0.00495
C2    1    0.708568    0.133665    0.627697    11.00000    0.03402    0.02866 =
         0.03288   -0.01368    0.00007   -0.00603
C3    1    0.679263    0.014710    0.663166    11.00000    0.04156    0.02821 =
         0.04001   -0.01127    0.00586   -0.00917
AFIX  43
H3    2    0.637675   -0.026360    0.740106    11.00000   -1.20000
AFIX   0
C4    1    0.709268   -0.045509    0.588942    11.00000    0.03888    0.02664 =
         0.05083   -0.01676    0.00155   -0.00794
C5    1    0.774449    0.012384    0.478588    11.00000    0.04158    0.03043 =
         0.04374   -0.02067   -0.00135   -0.00485
AFIX  43
H5    2    0.798422   -0.030434    0.429638    11.00000   -1.20000
AFIX   0
C6    1    0.806052    0.131515    0.436961    11.00000    0.03056    0.03012 =
         0.03141   -0.01434   -0.00403   -0.00272
C7    1    0.675586    0.193636    0.712540    11.00000    0.05642    0.03912 =
         0.03788   -0.02138    0.00883   -0.01395
AFIX 137
H7A   2    0.765807    0.222592    0.722510    11.00000   -1.20000
H7B   2    0.651478    0.131717    0.792452    11.00000   -1.20000
H7C   2    0.588027    0.265591    0.677823    11.00000   -1.20000
AFIX   0
C8    1    0.670926   -0.172176    0.626816    11.00000    0.06646    0.03699 =
         0.07328   -0.02798    0.01417   -0.02294
AFIX 137
H8A   2    0.691221   -0.223528    0.715457    11.00000   -1.20000
H8B   2    0.734361   -0.215055    0.584284    11.00000   -1.20000
H8C   2    0.562329   -0.160095    0.605271    11.00000   -1.20000
AFIX   0
C9    1    0.877230    0.190023    0.316021    11.00000    0.05219    0.04272 =
         0.03301   -0.01615    0.00354   -0.00889
AFIX 137
H9A   2    0.972326    0.211713    0.328422    11.00000   -1.20000
H9B   2    0.805538    0.266459    0.259223    11.00000   -1.20000
H9C   2    0.900102    0.129936    0.281790    11.00000   -1.20000
AFIX   0
C10   1    0.583898    0.455623    0.340463    11.00000    0.03539    0.02202 =
         0.03286   -0.01093   -0.00732   -0.00442
C11   1    0.583030    0.542644    0.218677    11.00000    0.03707    0.02590 =
         0.03237   -0.01141   -0.00232   -0.00710
AFIX  43
H11   2    0.674360    0.566115    0.182187    11.00000   -1.20000
AFIX   0
C12   1    0.441846    0.593843    0.152619    11.00000    0.04217    0.02196 =
         0.03000   -0.01041   -0.00518   -0.00284
C13   1    0.308516    0.561187    0.204718    11.00000    0.03591    0.02761 =
         0.04043   -0.01499   -0.00744    0.00005
AFIX  43
H13   2    0.213621    0.598055    0.157376    11.00000   -1.20000
AFIX   0
C14   1    0.314038    0.473943    0.326990    11.00000    0.03586    0.02872 =
         0.04206   -0.01384   -0.00030   -0.00540
AFIX  43
H14   2    0.222420    0.451291    0.363572    11.00000   -1.20000
AFIX   0
C15   1    0.453078    0.419464    0.396299    11.00000    0.03914    0.02421 =
         0.03379   -0.01021   -0.00057   -0.00637
AFIX  43
H15   2    0.457982    0.358998    0.479807    11.00000   -1.20000
AFIX   0
S2    6    1.131901    0.290377    0.665874    11.00000    0.02979    0.02730 =
         0.04355   -0.01241   -0.00104   -0.00592
O1    5    1.084525    0.261936    0.572546    11.00000    0.05585    0.05444 =
         0.06644   -0.03128   -0.01882   -0.00287
O2    5    1.265608    0.341656    0.644001    11.00000    0.05071    0.05017 =
         0.06192   -0.01161   -0.00228   -0.02479
O3    5    1.008114    0.354936    0.706710    11.00000    0.06027    0.10764 =
         0.11167   -0.06952    0.00418    0.01712
C16   1    1.190527    0.136709    0.794579    11.00000    0.09467    0.05837 =
         0.07722    0.00421   -0.02608   -0.04078
F6    3    1.315170    0.070834    0.763545    11.00000    0.11267    0.05157 =
         0.17326   -0.02989   -0.05607    0.02766
F7    3    1.235184    0.141855    0.890101    11.00000    0.15063    0.13261 =
         0.05413    0.00700   -0.03091   -0.05995
F8    3    1.086045    0.072573    0.819785    11.00000    0.15436    0.11348 =
         0.13321    0.04177   -0.03638   -0.10231
AFIX   6
PART -1
O4    5    0.926108    0.484726    0.128800    10.25000    0.06887
C17   1    0.959074    0.550569    0.024333    10.25000    0.04942
C18   1    0.933943    0.691399   -0.026949    10.25000    0.05927
AFIX  33
H18A  2    0.967075    0.726793   -0.110846    10.25000   -1.20000
H18B  2    0.824763    0.727311   -0.027240    10.25000   -1.20000
H18C  2    0.993623    0.711806    0.023841    10.25000   -1.20000
AFIX   5
C19   1    1.026509    0.494248   -0.058442    10.25000    0.05923
AFIX  33
H19A  2    1.044721    0.561420   -0.137262    10.25000   -1.20000
H19B  2    1.123792    0.434572   -0.020446    10.25000   -1.20000
H19C  2    0.954934    0.450072   -0.071527    10.25000   -1.20000
AFIX   6
PART -2
O4A   5    1.005046    0.448384    0.140142    10.25000    0.08725
C17A  1    1.018917    0.439496    0.044041    10.25000    0.06935
C18A  1    0.977951    0.553103   -0.078656    10.25000    0.08172
AFIX  33
H18D  2    0.996790    0.526956   -0.143665    10.25000   -1.20000
H18E  2    0.869329    0.593189   -0.083680    10.25000   -1.20000
H18F  2    1.041055    0.613151   -0.088529    10.25000   -1.20000
AFIX   5
C19A  1    1.077686    0.314498    0.043405    10.25000    0.07232
AFIX  33
H19D  2    1.080448    0.326811   -0.041278    10.25000   -1.20000
H19E  2    1.181303    0.277623    0.083112    10.25000   -1.20000
H19F  2    1.009581    0.257652    0.087966    10.25000   -1.20000
PART 0
AFIX   0
HKLF 4
 
REM  20141118
REM R1 =  0.0275 for    5017 Fo > 4sig(Fo)  and  0.0292 for all    5276 data
REM    294 parameters refined using     75 restraints
 
END  
     
WGHT      0.0592      0.5814 

REM Instructions for potential hydrogen bonds
HTAB C11 O4
EQIV $1 x-1, y, z
HTAB C15 O2_$1
EQIV $2 -x+2, -y+1, -z
HTAB C19 F2_$2
HTAB C18A F2
HTAB C19A F2_$2

REM Highest difference peak  1.110,  deepest hole -0.701,  1-sigma level  0.195
Q1    1   1.0063  0.1611  0.8494  11.00000  0.05    1.11
Q2    1   1.3053  0.2668  0.6447  11.00000  0.05    0.96
Q3    1   1.1657  0.2263  0.8884  11.00000  0.05    0.92
Q4    1   0.9487  0.6191 -0.0188  11.00000  0.05    0.74
Q5    1   1.1209  0.0547  0.7911  11.00000  0.05    0.71
Q6    1   1.1941  0.0474  0.8027  11.00000  0.05    0.65
Q7    1   0.4510  0.6160  0.1256  11.00000  0.05    0.61
Q8    1   1.1486  0.1881  0.8328  11.00000  0.05    0.55
Q9    1   0.7619  0.1647  0.7690  11.00000  0.05    0.53
Q10   1   0.5626  0.5920 -0.0053  11.00000  0.05    0.53
Q11   1   0.6428  0.8593 -0.0939  11.00000  0.05    0.51
Q12   1   0.7591 -0.2217  0.6756  11.00000  0.05    0.50
Q13   1   1.1569  0.2137  0.7363  11.00000  0.05    0.50
Q14   1   0.9350  0.4988  0.5879  11.00000  0.05    0.49
Q15   1   0.9552  0.4670  0.5676  11.00000  0.05    0.49
Q16   1   0.6959  0.2868  0.2487  11.00000  0.05    0.47
Q17   1   0.5415  0.5331 -0.0647  11.00000  0.05    0.47
Q18   1   1.0000  0.0000  1.0000  10.50000  0.05    0.47
Q19   1   0.6489  0.2365  0.2687  11.00000  0.05    0.46
Q20   1   0.5732  0.0195  0.3996  11.00000  0.05    0.46
;