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_7127955
_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         'C15 H16 F N O3 S2'
_chemical_formula_sum            'C15 H16 F N O3 S2'
_chemical_formula_weight         341.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-18
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5254(2)
_cell_length_b                   5.72610(10)
_cell_length_c                   34.5954(5)
_cell_measurement_reflns_used    55654
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.4350
_cell_measurement_theta_min      5.0670
_cell_volume                     3075.53(8)
_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      93.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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     32.00 121.00   0.50    0.22    --   46.70  12.00  54.00  178
  2  \w    108.00 156.00   0.50    0.88    --  104.75  45.00 -30.00   96
  3  \w     93.00 161.00   0.50    0.88    --  104.75  12.00  54.00  136
  4  \w     52.00 108.00   0.50    0.88    --  104.75-133.00  28.00  112
  5  \w     43.00  73.00   0.50    0.88    --  104.75 -61.00  90.00   60
  6  \w     47.00  96.00   0.50    0.22    --   46.70-136.00-149.00   98
  7  \w     36.00  72.00   0.50    0.88    --  104.75 -61.00-180.00   72
  8  \w    -24.00  20.00   0.50    0.22    --  -46.70  19.00-150.00   88
  9  \w    -63.00 -37.00   0.50    0.88    -- -102.00 115.00-162.00   52
 10  \w   -106.00 -67.00   0.50    0.88    -- -102.00 115.00-162.00   78
 11  \w    -67.00 -33.00   0.50    0.88    -- -102.00  61.00 150.00   68
 12  \w    -53.00 -27.00   0.50    0.22    --  -46.70 -70.00 127.04   52
 13  \w    -96.00 -34.00   0.50    0.22    --  -46.70 -37.00-180.00  124
 14  \w    -24.00  13.00   0.50    0.22    --  -46.70  19.00-180.00   74
 15  \w    -61.00 -34.00   0.50    0.22    --  -46.70 -41.00 -44.04   54
 16  \w    -86.00 -35.00   0.50    0.22    --  -46.70 -40.00 109.98  102
 17  \w    -94.00 -35.00   0.50    0.22    --  -46.70 -37.00-120.00  118
 18  \w   -108.00 -69.00   0.50    0.22    --  -46.70 -41.00 -44.04   78
 19  \w     24.00  58.00   0.50    0.22    --   46.70  77.00  30.00   68
 20  \w     24.00  62.00   0.50    0.22    --   46.70  77.00-120.00   76
 21  \w     24.00  79.00   0.50    0.22    --   46.70  77.00 -30.00  110
 22  \w     31.00  94.00   0.50    0.22    --   46.70-125.00  60.00  126
 23  \w     24.00  63.00   0.50    0.22    --   46.70  77.00  60.00   78
 24  \w     93.00 119.00   0.50    0.22    --   46.70  77.00 120.00   52
 25  \w     24.00  71.00   0.50    0.22    --   46.70  77.00-180.00   94
 26  \w     24.00  88.00   0.50    0.22    --   46.70  77.00  90.00  128
 27  \w     24.00  88.00   0.50    0.22    --   46.70  77.00 120.00  128
 28  \w     24.00  55.00   0.50    0.22    --   46.70  77.00 -90.00   62
 29  \w     20.00  72.00   0.50    0.22    --   46.70-125.00   0.00  104
 30  \w     24.00  67.00   0.50    0.22    --   46.70  77.00 -60.00   86
 31  \w   -106.00 -79.00   0.50    0.88    -- -102.00 -76.00-167.35   54
 32  \w   -152.00-126.00   0.50    0.88    -- -102.00 -72.00  42.34   52
 33  \w   -137.00 -85.00   0.50    0.88    -- -102.00 -61.00 -90.00  104
 34  \w   -107.00 -78.00   0.50    0.88    -- -102.00 -79.00 144.94   58
 35  \w   -175.00-125.00   0.50    0.88    -- -102.00 -78.00 -62.03  100
 36  \w   -175.00-112.00   0.50    0.88    -- -102.00 -79.00 144.94  126
 37  \w   -171.00 -79.00   0.50    0.88    -- -102.00 -78.00-137.76  184
 38  \w   -162.00 -79.00   0.50    0.88    -- -102.00 -78.00  -8.85  166
 39  \w   -104.00 -79.00   0.50    0.88    -- -102.00 -78.00 -62.03   50
 40  \w   -117.00 -82.00   0.50    0.88    -- -102.00 -70.00 -29.20   70
 41  \w   -167.00 -79.00   0.50    0.88    -- -102.00 -77.00-121.04  176
 42  \w   -106.00 -81.00   0.50    0.88    -- -102.00 -73.00  -2.81   50
 43  \w   -137.00 -79.00   0.50    0.88    -- -102.00 -76.00-173.79  116
 44  \w   -111.00 -85.00   0.50    0.88    -- -102.00 -61.00  50.05   52
 45  \w   -137.00 -79.00   0.50    0.88    -- -102.00 -77.00  90.00  116
 46  \w   -173.00 -86.00   0.50    0.88    -- -102.00 -60.00 -67.22  174
 47  \w   -105.00 -79.00   0.50    0.88    -- -102.00 -77.00  30.00   52
 48  \w   -175.00-141.00   0.50    0.88    -- -102.00 -61.00  50.05   68
 49  \w   -105.00 -80.00   0.50    0.88    -- -102.00 -82.00 172.22   50
 50  \w   -103.00 -72.00   0.50    0.88    -- -102.00  77.00   0.00   62
 51  \w   -106.00 -81.00   0.50    0.88    -- -102.00 -73.00 -85.69   50
 52  \w   -174.00-137.00   0.50    0.88    -- -102.00 -77.00  30.00   74
 53  \w   -104.00 -79.00   0.50    0.88    -- -102.00 -76.00  37.58   50
 54  \w   -172.00 -78.00   0.50    0.88    -- -102.00 -79.00 169.93  188
 55  \w   -174.00 -79.00   0.50    0.88    -- -102.00 -77.00 177.34  190
 56  \w   -144.00 -89.00   0.50    0.88    -- -102.00 -51.00 -85.62  110
 57  \w   -103.00 -78.00   0.50    0.88    -- -102.00 -79.00 129.41   50
 58  \w   -105.00 -78.00   0.50    0.88    -- -102.00 -80.00-152.69   54
 59  \w   -105.00 -79.00   0.50    0.88    -- -102.00 -76.00  22.04   52
 60  \w   -105.00 -79.00   0.50    0.88    -- -102.00 -79.00 -93.17   52
 61  \w   -107.00 -82.00   0.50    0.88    -- -102.00 -69.00   3.74   50
 62  \w   -150.00-124.00   0.50    0.88    -- -102.00 -73.00 -85.69   52
 63  \w   -106.00 -80.00   0.50    0.88    -- -102.00 -77.00 -30.00   52
 64  \w   -155.00 -83.00   0.50    0.88    -- -102.00 -68.00-115.87  144
 65  \w   -103.00 -78.00   0.50    0.88    -- -102.00 -80.00-108.99   50
 66  \w   -104.00 -78.00   0.50    0.88    -- -102.00 -79.00 139.25   52
 67  \w   -136.00 -85.00   0.50    0.88    -- -102.00 -61.00 -60.00  102
 68  \w   -107.00 -81.00   0.50    0.88    -- -102.00 -73.00  98.57   52
 69  \w   -175.00-127.00   0.50    0.88    -- -102.00 -70.00 -29.20   96
 70  \w   -110.00 -79.00   0.50    0.88    -- -102.00 -77.00 150.00   62
 71  \w   -111.00 -85.00   0.50    0.88    -- -102.00 -61.00-149.16   52
 72  \w   -105.00 -79.00   0.50    0.88    -- -102.00 -77.00 -90.00   52
 73  \w   -106.00 -80.00   0.50    0.88    -- -102.00 -77.00 120.00   52
 74  \w   -165.00-123.00   0.50    0.88    -- -102.00 -79.00 139.25   84
 75  \w   -106.00 -81.00   0.50    0.88    -- -102.00 -72.00  42.34   50
 76  \w   -104.00 -79.00   0.50    0.88    -- -102.00 -77.00  60.00   50
 77  \w   -168.00 -85.00   0.50    0.88    -- -102.00 -61.00  90.00  166
 78  \w   -111.00 -85.00   0.50    0.88    -- -102.00 -61.00  60.00   52
 79  \w     32.00  78.00   0.50    0.88    --  104.75 -94.00-180.00   92
 80  \w     60.00 103.00   0.50    0.88    --  104.75-125.00  30.00   86
 81  \w     43.00  95.00   0.50    0.88    --  104.75 -94.00  30.00  104
 82  \w     37.00 100.00   0.50    0.88    --  104.75-125.00 -60.00  126
 83  \w     73.00 105.00   0.50    0.88    --  104.75 -94.00 120.00   64
 84  \w     32.00  64.00   0.50    0.88    --  104.75 -94.00 120.00   64
 85  \w     38.00 105.00   0.50    0.88    --  104.75 -94.00  60.00  134
;
_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      -0.0456671000
_diffrn_orient_matrix_UB_12      0.0367919000
_diffrn_orient_matrix_UB_13      0.0390823000
_diffrn_orient_matrix_UB_21      -0.0881373000
_diffrn_orient_matrix_UB_22      -0.0223201000
_diffrn_orient_matrix_UB_23      -0.0201499000
_diffrn_orient_matrix_UB_31      0.0010629000
_diffrn_orient_matrix_UB_32      -0.2653883000
_diffrn_orient_matrix_UB_33      0.0071217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            75912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.241
_diffrn_reflns_theta_min         5.114
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79720
_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    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane/Et2O'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.158(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6261
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0373P)^2^+3.6371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                6165
_reflns_number_total             6261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08060h2.cif
_cod_data_source_block           rt052
_cod_depositor_comments
;
Adding full bibliography for 7127952--7127955.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C15 H16 F N O3 S2)'
_cod_original_formula_sum        'C30 H32 F2 N2 O6 S4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     682.81
_cod_database_code               7127955
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H16FNO3S2
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.646
_diffrn_oxdiff_digest_frames
;
01d6e149a3cc72c36f1735642dc4a530bb00055bf68
;
_diffrn_oxdiff_digest_hkl
;
0159b68c3cd317400965a103abbecabc08aec4
;
_reflns_odcompleteness_completeness 99.91
_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 Ternary CH refined with riding coordinates:
 C1(H1), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              49544
_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 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.872