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_7127953
_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         'C12 H13 F O3'
_chemical_formula_sum            'C12 H13 F O3'
_chemical_formula_weight         224.22
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-28
_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                 95.629(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.0397(16)
_cell_length_b                   5.8337(3)
_cell_length_c                   7.1864(5)
_cell_measurement_reflns_used    5576
_cell_measurement_temperature    93
_cell_measurement_theta_max      74.5700
_cell_measurement_theta_min      3.4420
_cell_volume                     1086.41(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.984
_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    -50.00   8.00   0.50    2.00    --  -46.57  77.00  -3.00  116
  2  \w    -68.00 -30.00   0.50    4.00    -- -102.00  61.00-150.00   76
  3  \w    -65.00 -37.00   0.50    4.00    -- -102.00  61.00-180.00   56
  4  \w    -64.00 -38.00   0.50    4.00    -- -102.00  61.00 -30.00   52
  5  \w    -68.00 -31.00   0.50    4.00    -- -102.00  61.00  60.00   74
  6  \w    -64.00 -39.00   0.50    4.00    -- -102.00  61.00 150.00   50
  7  \w    -96.00 -30.00   0.50    4.00    -- -102.00  77.00  -3.00  132
  8  \w   -119.00 -52.00   0.50    2.00    --  -46.57 -77.00-129.00  134
  9  \w    -16.00  58.00   0.50    2.00    --   46.57 -77.00-129.00  148
 10  \w     40.00  91.00   0.50    2.00    --   46.57-125.00-180.00  102
 11  \w     47.00  93.00   0.50    4.00    --  104.75 -77.00-129.00   92
 12  \w     93.00 152.00   0.50    4.00    --  104.75  30.00 -90.00  118
 13  \w     99.00 171.00   0.50    4.00    --  104.75  30.00 -60.00  144
 14  \w     83.00 173.00   0.50    4.00    --  104.75  77.00  -3.00  180
 15  \w     33.00 100.00   0.50    4.00    --  104.75-125.00  90.00  134
 16  \w   -119.00 -80.00   0.50    2.00    --  -46.57-125.00  30.00   78
 17  \w   -151.00-126.00   0.50    4.00    -- -102.00 -77.00-129.00   50
 18  \w    -75.00 -34.00   0.50    2.00    --  -46.57 -37.00 -90.00   82
 19  \w    -63.00 -32.00   0.50    2.00    --  -46.57 -57.00-150.00   62
 20  \w    -22.00  11.00   0.50    2.00    --  -46.57  19.00 150.00   66
 21  \w     33.00 101.00   0.50    2.00    --   46.57  57.00   0.00  136
 22  \w     26.00  85.00   0.50    2.00    --   46.57  77.00  60.00  118
 23  \w     41.00  66.00   0.50    2.00    --   46.57  37.00  90.00   50
 24  \w     24.00  61.00   0.50    2.00    --   46.57  77.00-120.00   74
 25  \w     44.00  90.00   0.50    2.00    --   46.57  37.00 -30.00   92
 26  \w     41.00  71.00   0.50    2.00    --   46.57  19.00-180.00   60
 27  \w     90.00 119.00   0.50    2.00    --   46.57  77.00-120.00   58
 28  \w     26.00  76.00   0.50    2.00    --   46.57  77.00   0.00  100
 29  \w     24.00  58.00   0.50    2.00    --   46.57  77.00 -60.00   68
 30  \w     24.00  61.00   0.50    2.00    --   46.57  77.00-180.00   74
 31  \w     25.00  63.00   0.50    2.00    --   46.57  77.00 150.00   76
 32  \w     24.00  71.00   0.50    2.00    --   46.57  77.00  90.00   94
 33  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -77.00 150.00   52
 34  \w   -110.00 -79.00   0.50    4.00    -- -102.00 -77.00-150.00   62
 35  \w   -165.00-140.00   0.50    4.00    -- -102.00 -74.00 124.10   50
 36  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -76.00  92.46   52
 37  \w   -112.00 -79.00   0.50    4.00    -- -102.00 -77.00-120.00   66
 38  \w   -173.00 -88.00   0.50    4.00    -- -102.00 -51.00 152.76  170
 39  \w   -146.00-119.00   0.50    4.00    -- -102.00 -77.00 150.00   54
 40  \w   -110.00 -85.00   0.50    4.00    -- -102.00 -61.00  30.00   50
 41  \w   -132.00 -83.00   0.50    4.00    -- -102.00 -70.00 -15.83   98
 42  \w   -160.00-135.00   0.50    4.00    -- -102.00 -77.00  60.00   50
 43  \w   -107.00 -81.00   0.50    4.00    -- -102.00 -77.00  60.00   52
 44  \w   -165.00-138.00   0.50    4.00    -- -102.00 -84.00-117.86   54
 45  \w   -105.00 -80.00   0.50    4.00    -- -102.00 -84.00-117.86   50
 46  \w   -111.00 -85.00   0.50    4.00    -- -102.00 -62.00   4.16   52
 47  \w   -163.00-137.00   0.50    4.00    -- -102.00 -61.00  30.00   52
 48  \w   -134.00 -85.00   0.50    4.00    -- -102.00 -64.00  87.33   98
 49  \w   -110.00 -84.00   0.50    4.00    -- -102.00 -65.00   2.43   52
 50  \w   -115.00 -90.00   0.50    4.00    -- -102.00 -51.00 114.33   50
 51  \w   -110.00 -85.00   0.50    4.00    -- -102.00 -61.00 -90.00   50
 52  \w   -124.00 -81.00   0.50    4.00    -- -102.00 -74.00 112.87   86
 53  \w   -144.00-118.00   0.50    4.00    -- -102.00 -65.00   2.43   52
 54  \w   -131.00 -93.00   0.50    4.00    -- -102.00 -47.00  55.13   76
 55  \w   -111.00 -85.00   0.50    4.00    -- -102.00 -61.00-120.00   52
 56  \w   -115.00 -85.00   0.50    4.00    -- -102.00 -64.00-171.13   60
 57  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -78.00-158.91   52
 58  \w   -111.00 -85.00   0.50    4.00    -- -102.00 -61.00  13.57   52
 59  \w   -110.00 -84.00   0.50    4.00    -- -102.00 -65.00  28.55   52
 60  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -77.00 -30.00   52
 61  \w   -141.00-116.00   0.50    4.00    -- -102.00 -61.00-120.00   50
 62  \w   -112.00 -85.00   0.50    4.00    -- -102.00 -62.00 -63.04   54
 63  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -77.00 -60.00   52
 64  \w   -173.00-146.00   0.50    4.00    -- -102.00 -78.00-158.91   54
 65  \w   -166.00-140.00   0.50    4.00    -- -102.00 -61.00 -90.00   52
 66  \w   -115.00 -80.00   0.50    4.00    -- -102.00 -77.00   0.00   70
 67  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -76.00 -17.61   52
 68  \w   -105.00 -79.00   0.50    4.00    -- -102.00 -77.00 -90.00   52
 69  \w   -114.00 -83.00   0.50    4.00    -- -102.00 -68.00 -94.46   62
 70  \w   -105.00 -80.00   0.50    4.00    -- -102.00 -74.00 124.10   50
 71  \w   -115.00 -89.00   0.50    4.00    -- -102.00 -49.00 -70.20   52
 72  \w   -144.00 -90.00   0.50    4.00    -- -102.00 -52.00-134.72  108
 73  \w   -161.00-135.00   0.50    4.00    -- -102.00 -51.00 114.33   52
 74  \w    125.00 150.00   0.50    4.00    --  104.75  77.00 120.00   50
 75  \w     82.00 121.00   0.50    4.00    --  104.75  77.00 120.00   78
 76  \w    127.00 163.00   0.50    4.00    --  104.75  61.00 150.00   72
 77  \w     88.00 122.00   0.50    4.00    --  104.75  61.00 150.00   68
 78  \w     56.00 111.00   0.50    4.00    --  104.75-125.00-120.00  110
 79  \w     71.00 106.00   0.50    4.00    --  104.75 -94.00 120.00   70
 80  \w     59.00  86.00   0.50    4.00    --  104.75 -94.00-150.00   54
 81  \w     38.00  64.00   0.50    4.00    --  104.75 -94.00 120.00   52
 82  \w     80.00 106.00   0.50    4.00    --  104.75 -94.00 -30.00   52
 83  \w     76.00 106.00   0.50    4.00    --  104.75 -96.00   2.54   60
 84  \w    124.00 176.00   0.50    4.00    --  104.75  68.00  53.62  104
 85  \w     87.00 121.00   0.50    4.00    --  104.75  68.00  53.62   68
 86  \w     81.00 106.00   0.50    4.00    --  104.75 -94.00-120.00   50
 87  \w     35.00  60.00   0.50    4.00    --  104.75 -94.00-120.00   50
 88  \w     33.00 109.00   0.50    4.00    --  104.75-125.00 120.00  152
;
_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      -0.0044530000
_diffrn_orient_matrix_UB_12      -0.0872787000
_diffrn_orient_matrix_UB_13      0.2002768000
_diffrn_orient_matrix_UB_21      0.0328911000
_diffrn_orient_matrix_UB_22      0.2035473000
_diffrn_orient_matrix_UB_23      0.0790843000
_diffrn_orient_matrix_UB_31      -0.0492881000
_diffrn_orient_matrix_UB_32      0.1437628000
_diffrn_orient_matrix_UB_33      0.0093350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.462
_diffrn_reflns_theta_min         3.411
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.077
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0885
_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^)+(0.0720P)^2^+2.4269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             2243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08060h2.cif
_cod_data_source_block           rt217
_cod_depositor_comments
'Adding full bibliography for 7127952--7127955.cif.'
_cod_database_code               7127953
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H13FO3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.933
_diffrn_oxdiff_digest_frames
;
016a66f8ce3ab09370dabd71fb9152553000027c301
;
_diffrn_oxdiff_digest_hkl
;
01aaa6c5030e41244503224697c8846e1693a6
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              80481
_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.748