Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
Meyer, Andreas U.; Slanina, Tomáš; Yao, Chang-Jiang; König, Burkhard; ACS Catalysis 6 (2016) 369–; doi:10.1021/acscatal.5b02410

data_4513753
_publ_section_title
;
 Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              369
_journal_paper_doi               10.1021/acscatal.5b02410
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C13 H4 F5 N S'
_chemical_formula_sum            'C13 H4 F5 N S'
_chemical_formula_weight         301.23
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-17
_audit_creation_method
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Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.808(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4070(11)
_cell_length_b                   7.3079(5)
_cell_length_c                   11.1275(9)
_cell_measurement_reflns_used    4295
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.2550
_cell_measurement_theta_min      4.2780
_cell_volume                     1102.24(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega -117.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064  -37.0000   90.0000 93

  2 omega -117.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega -110.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064  -57.0000 -180.0000 98

  4 omega  -94.00  -69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064  125.0000  -30.0000 25

  5 omega   39.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000  -30.0000 31

  6 omega   30.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  -90.0000 37

  7 omega   29.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   90.0000 25

  8 omega   44.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -125.0000  -30.0000 77

  9 omega   32.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   60.0000 33

 10 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000 -150.0000 26

 11 omega   35.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  -60.0000 25

 12 omega   43.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000 -180.0000 25

 13 omega   41.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  120.0000 25

 14 omega   58.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -125.0000  -60.0000 33

 15 omega   32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   30.0000 31

 16 omega   40.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000    0.0000 36

 17 omega   58.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -94.0000    0.0000 43

 18 omega  -70.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064   57.0000   60.0000 103

 19 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064  -57.0000  -60.0000 104

 20 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064  -57.0000   30.0000 104

 21 omega  -70.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7064   57.0000  -60.0000 103

 22 omega    2.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7064 -125.0000 -150.0000 96

 23 omega   46.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   15.0000 -120.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1047933000
_diffrn_orient_matrix_UB_12      0.0513867000
_diffrn_orient_matrix_UB_13      -0.0043409000
_diffrn_orient_matrix_UB_21      -0.0262857000
_diffrn_orient_matrix_UB_22      0.0577982000
_diffrn_orient_matrix_UB_23      -0.1408719000
_diffrn_orient_matrix_UB_31      -0.0352028000
_diffrn_orient_matrix_UB_32      -0.1959941000
_diffrn_orient_matrix_UB_33      -0.0425299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7171
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_min         6.532
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.195
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.2807
_exptl_crystal_size_min          0.0974
_refine_diff_density_max         0.245
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_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0446P)^2^+0.4707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1949
_reflns_number_total             2157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b02410_si_003.cif
_cod_data_source_block           o012
_cod_depositor_comments
'Adding full bibliography for 4513753--4513756.cif.'
_cod_database_code               4513753
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C13 H4 F5 N1 S1'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H8(0.022) H9(0.023) H10(0.023) H13(0.025)
 Fixed X: H8(0.4003) H9(0.3638) H10(0.2148) H13(-0.0099)
 Fixed Y: H8(0.4168) H9(0.421) H10(0.5376) H13(0.813)
 Fixed Z: H8(0.9756) H9(1.1623) H10(1.1663) H13(0.7386)
;
_shelx_res_checksum              12862
_shelx_hkl_checksum              29421
_olex2_date_sample_data_collection 2015-02-16
_olex2_submission_special_instructions 'No special instructions were received'