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_4513754
_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         'C12 H6 F4'
_chemical_formula_sum            'C12 H6 F4'
_chemical_formula_weight         226.17
_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             2015-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.223(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8062(4)
_cell_length_b                   5.84755(16)
_cell_length_c                   12.6869(4)
_cell_measurement_reflns_used    2286
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.1680
_cell_measurement_theta_min      7.1260
_cell_volume                     916.72(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    'ShelXS (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 0.983
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
  1 omega  -53.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939   37.0000   60.0000 83

  2 omega   57.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939  155.0000   29.0000 49

  3 omega   13.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000 -180.0000 76

  4 omega   73.00  158.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   77.0000  -30.0000 85

  5 omega   29.00   66.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000 -120.0000 37

  6 omega   79.00  157.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   30.0000   90.0000 78

  7 omega   35.00   65.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   90.0000 30

  8 omega   35.00   66.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   60.0000 31

  9 omega   28.00  125.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000 -150.0000 97

 10 omega   47.00   73.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000   30.0000 26

 11 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939  -57.0000   60.0000 104

 12 omega -115.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939  -57.0000  150.0000 25

 13 omega -115.00  -11.00   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      -0.1217042000
_diffrn_orient_matrix_UB_12      0.0554413000
_diffrn_orient_matrix_UB_13      -0.0273293000
_diffrn_orient_matrix_UB_21      -0.0223202000
_diffrn_orient_matrix_UB_22      -0.1820558000
_diffrn_orient_matrix_UB_23      -0.0909355000
_diffrn_orient_matrix_UB_31      -0.0148762000
_diffrn_orient_matrix_UB_32      -0.1822420000
_diffrn_orient_matrix_UB_33      0.0825427000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3786
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.498
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70733
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2223
_exptl_crystal_size_mid          0.1009
_exptl_crystal_size_min          0.0534
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0593P)^2^+0.0533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1512
_reflns_number_total             1733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b02410_si_004.cif
_cod_data_source_block           o037
_cod_depositor_comments
'Adding full bibliography for 4513753--4513756.cif.'
_cod_database_code               4513754
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C12H6F4
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4(0.029) H10(0.032) H8(0.027) H11(0.03) H12(0.026) H9(0.032)
 Fixed X: H4(0.0403) H10(0.4741) H8(0.3645) H11(0.3606) H12(0.2511) H9(0.4771)
 Fixed Y: H4(0.7918) H10(0.7517) H8(0.4527) H11(1.061) H12(1.0694) H9(0.4492)
 Fixed Z: H4(0.4829) H10(0.032) H8(0.2673) H11(0.0315) H12(0.1505) H9(0.151)
;
_shelx_res_checksum              99719
_shelx_hkl_checksum              70251
_olex2_date_sample_data_collection 2015-05-04
_olex2_submission_original_sample_id Yao-3-81-5
_olex2_submission_special_instructions 'No special instructions were received'