Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
Noto, Naoki; Koike, Takashi; Akita, Munetaka; Chem. Sci.  (2017) –; doi:10.1039/C7SC01703K

data_1546516
_publ_section_title
;
 Metal-free di- and tri-fluoromethylation of alkenes realized by
 visible-light-induced perylene photoredox catalysis
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01703K
_journal_year                    2017
_chemical_formula_sum            'C11 H12 F3 N O'
_chemical_formula_weight         231.22
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-02-17 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                80.3440(10)
_cell_angle_beta                 83.0720(10)
_cell_angle_gamma                88.4000(10)
_cell_formula_units_Z            2
_cell_length_a                   5.0215(5)
_cell_length_b                   8.6681(9)
_cell_length_c                   12.6928(13)
_cell_measurement_reflns_used    2998
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.769
_cell_measurement_theta_min      2.384
_cell_volume                     540.66(10)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0070
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2564
_diffrn_reflns_point_group_measured_fraction_full 0.553
_diffrn_reflns_point_group_measured_fraction_max 0.565
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.011
_diffrn_reflns_theta_min         1.639
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       tip
_exptl_crystal_F_000             240
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.17(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0210
_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^)+(0.0271P)^2^+0.1434P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0545
_reflns_Friedel_coverage         0.163
_reflns_Friedel_fraction_full    0.155
_reflns_Friedel_fraction_max     0.159
_reflns_number_gt                2141
_reflns_number_total             2146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01703k2.cif
_cod_data_source_block           NN1091R_0m
_cod_database_code               1546516
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-2
_shelx_res_checksum              26636