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_4513755
_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 H5 F7'
_chemical_formula_sum            'C13 H5 F7'
_chemical_formula_weight         294.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2015-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.92801(16)
_cell_length_b                   7.5738(2)
_cell_length_c                   23.6364(5)
_cell_measurement_reflns_used    3393
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.6550
_cell_measurement_theta_min      3.7250
_cell_volume                     1061.22(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_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    'ShelXD (Sheldrick, 2008)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -70.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939   57.0000  150.0000 28

  2 omega   16.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939   37.0000  -60.0000 96

  3 omega   29.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939   37.0000 -150.0000 76

  4 omega   29.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  120.0000 40

  5 omega   18.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800    0.0000  -30.0000 140

  6 omega   37.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000   90.0000 39

  7 omega   35.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000    0.0000 41

  8 omega   40.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  -60.0000 29

  9 omega   35.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -61.0000 -180.0000 102

 10 omega  -20.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939  -99.0000 -180.0000 103

 11 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939   57.0000   90.0000 104
;
_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      -0.1049072000
_diffrn_orient_matrix_UB_12      0.0666669000
_diffrn_orient_matrix_UB_13      0.0556735000
_diffrn_orient_matrix_UB_21      -0.1820747000
_diffrn_orient_matrix_UB_22      0.0994680000
_diffrn_orient_matrix_UB_23      -0.0338217000
_diffrn_orient_matrix_UB_31      -0.1528888000
_diffrn_orient_matrix_UB_32      -0.1644414000
_diffrn_orient_matrix_UB_33      0.0021126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4549
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         72.910
_diffrn_reflns_theta_min         3.740
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
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 colourless'
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2602
_exptl_crystal_size_mid          0.2045
_exptl_crystal_size_min          0.1736
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0485P)^2^+0.1295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                1992
_reflns_number_total             2044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b02410_si_005.cif
_cod_data_source_block           o038
_cod_depositor_comments
'Adding full bibliography for 4513753--4513756.cif.'
_cod_database_code               4513755
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C13 H5 F7'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H010(0.028) H011(0.027) H016(0.023) H017(0.029) H019(0.023)
 Fixed X: H010(1.3471) H011(0.7229) H016(1.3263) H017(1.0465) H019(0.6991)
 Fixed Y: H010(0.1338) H011(-0.0696) H016(0.1346) H017(0.0302) H019(-0.066)
 Fixed Z: H010(0.3727) H011(0.381) H016(0.2744) H017(0.4257) H019(0.2829)
;
_shelx_res_checksum              32379
_shelx_hkl_checksum              19092
_olex2_date_sample_data_collection 2015-05-04
_olex2_submission_special_instructions 'No special instructions were received'