Simple generation of various α-monofluoroalkyl radicals by organic photoredox catalysis: modular synthesis of β-monofluoroketones.
Taniguchi, Ryo; Noto, Naoki; Tanaka, Seiya; Takahashi, Keigo; Sarkar, Sujan K.; Oyama, Ryoko; Abe, Manabu; Koike, Takashi; Akita, Munetaka; Chemical communications (Cambridge, England) 57 (2021) 2609–2612; doi:10.1039/d0cc08060h

data_7127954
_publ_section_title
;
 Simple generation of various \a-monofluoroalkyl radicals by organic
 photoredox catalysis: modular synthesis of \b-monofluoroketones.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2609
_journal_page_last               2612
_journal_paper_doi               10.1039/d0cc08060h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C42 H42 N2'
_chemical_formula_sum            'C42 H42 N2'
_chemical_formula_weight         574.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-29
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-30 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.606(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.060(2)
_cell_length_b                   10.1206(8)
_cell_length_c                   19.139(2)
_cell_measurement_reflns_used    2503
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.3220
_cell_measurement_theta_min      4.6590
_cell_volume                     3267.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.72a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.72a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.72a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     35.00 119.00   0.50    6.00    --   46.20  30.00 -17.00  168
  2  \w    152.00 178.00   0.50   13.00    --  104.61  30.00 -17.00   52
  3  \w     92.00 120.00   0.50   13.00    --  104.61  30.00 -17.00   56
  4  \w     38.00  65.00   0.50   13.00    --  104.61 -61.00 120.00   54
  5  \w     41.00 108.00   0.50   13.00    --  104.61-125.00 150.00  134
  6  \w     34.00  73.00   0.50   13.00    --  104.61 -61.00 -90.00   78
  7  \w     32.00  98.00   0.50   13.00    --  104.61 -94.00-150.00  132
  8  \w     32.00  72.00   0.50   13.00    --  104.61 -61.00-120.00   80
  9  \w     32.00  58.00   0.50   13.00    --  104.61 -61.00-150.00   52
 10  \w    -20.00   5.00   0.50    6.00    --   46.20 -30.00-178.00   50
 11  \w    -29.00   9.00   0.50    6.00    --  -46.20  30.00 -17.00   76
 12  \w    -13.00  27.00   0.50    6.00    --  -46.20  37.00  60.00   80
 13  \w    -39.00  23.00   0.50    6.00    --  -46.20  37.00 120.00  124
 14  \w    -59.00 -31.00   0.50   13.00    -- -102.00  61.00  30.00   56
 15  \w    -60.00 -33.00   0.50   13.00    -- -102.00  61.00   0.00   54
 16  \w    -65.00 -40.00   0.50   13.00    -- -102.00  61.00 -30.00   50
 17  \w    -62.00 -35.00   0.50   13.00    -- -102.00  61.00 -90.00   54
 18  \w    -48.00  10.00   0.50    6.00    --  -46.20  57.00 -90.00  116
 19  \w    -64.00 -29.00   0.50   13.00    -- -102.00  61.00-180.00   70
 20  \w    -98.00 -72.00   0.50    6.00    --  -46.20 -30.00-178.00   52
 21  \w    -61.00 -29.00   0.50   13.00    -- -102.00  61.00 150.00   64
 22  \w    -67.00 -38.00   0.50   13.00    -- -102.00  61.00 120.00   58
 23  \w    -69.00 -34.00   0.50   13.00    -- -102.00  61.00  90.00   70
 24  \w    -66.00 -29.00   0.50   13.00    -- -102.00  61.00  60.00   74
 25  \w   -175.00 -89.00   0.50   13.00    -- -102.00 -30.00-178.00  172
 26  \w   -171.00 -91.00   0.50   13.00    -- -102.00 -45.00  90.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0906450000
_diffrn_orient_matrix_UB_12      0.0077439000
_diffrn_orient_matrix_UB_13      0.0208139000
_diffrn_orient_matrix_UB_21      0.0073897000
_diffrn_orient_matrix_UB_22      0.0579232000
_diffrn_orient_matrix_UB_23      -0.0731691000
_diffrn_orient_matrix_UB_31      -0.0080904000
_diffrn_orient_matrix_UB_32      0.1405381000
_diffrn_orient_matrix_UB_33      0.0290787000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22964
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.360
_diffrn_reflns_theta_min         3.238
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.72a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/MeOH'
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.0958
_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^)+(0.1568P)^2^+1.6104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2462
_refine_ls_wR_factor_ref         0.2998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3390
_reflns_number_total             6521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08060h2.cif
_cod_data_source_block           rt064
_cod_depositor_comments
'Adding full bibliography for 7127952--7127955.cif.'
_cod_original_cell_volume        3267.2(6)
_cod_database_code               7127954
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.838
_diffrn_oxdiff_digest_frames
;
013933dbeda400d61c54df1cc2f8554e7e000257f8c
;
_diffrn_oxdiff_digest_hkl
;
01d0fde241e3affc8fcaa56e01ce7809c58651
;
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C35(H35), C19(H19), C22(H22), C12(H12), C16(H16), C18(H18),
 C37(H37), C9(H9), C6(H6), C34(H34), C31(H31), C2(H2), C38(H38), C15(H15),
 C13(H13), C32(H32), C28(H28), C8(H8), C7(H7), C30(H30), C14(H14), C29(H29),
 C3(H3)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C41(H41A,H41B,H41C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C42(H42A,H42B,H42C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              48406
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.552