Divergent functionalization of alkenes enabled by photoredox activation of CDFA and α-halo carboxylic acids.
Giri, Rahul; Zhilin, Egor; Katayev, Dmitry; Chemical science 15 (2024) 10659–10667; doi:10.1039/d4sc01084a

data_1571787
_publ_section_title
;
 Divergent functionalization of alkenes enabled by photoredox activation
 of CDFA and &#x3b1;-halo carboxylic acids.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10659
_journal_page_last               10667
_journal_paper_doi               10.1039/d4sc01084a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H12 F2 O2'
_chemical_formula_weight         298.28
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-02T14:24:07-00:00
_audit_update_record
;
2023-10-02 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5648(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.05628(17)
_cell_length_b                   5.83820(12)
_cell_length_c                   23.8712(4)
_cell_measurement_reflns_used    17569
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      80.116
_cell_measurement_theta_min      3.771
_cell_volume                     1377.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.988
_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    -25.00  23.00   0.50    1.50    --  -49.99  17.00  88.00   96
  2  \w   -121.00 -45.00   0.50    1.50    --  -49.99 -17.00 -80.00  152
  3  \w    -21.00  25.00   0.50    1.50    --   49.99 -17.00 -80.00   92
  4  \w     46.00 122.00   0.50    1.50    --   49.99  17.00  88.00  152
  5  \w   -161.00 -85.00   0.50    5.00    --  -90.00 -17.00 -80.00  152
  6  \w   -121.00 -38.00   0.50    1.50    --  -49.99 -57.00 150.00  166
  7  \w   -121.00 -38.00   0.50    1.50    --  -49.99 -57.00-180.00  166
  8  \w    -26.00  22.00   0.50    1.50    --  -49.99  19.00-120.00   96
  9  \w   -121.00 -30.00   0.50    1.50    --  -49.99 -77.00-150.00  182
 10  \w     34.00  66.00   0.50    1.50    --   49.99  77.00 150.00   64
 11  \w     46.00  84.00   0.50    1.50    --   49.99  38.00-180.00   76
 12  \w     49.00  77.00   0.50    1.50    --   49.99  38.00 150.00   56
 13  \w     36.00  90.00   0.50    1.50    --   49.99-125.00-150.00  108
 14  \w     55.00  81.00   0.50    1.50    --   49.99  19.00-180.00   52
 15  \w     38.00  81.00   0.50    1.50    --   49.99  57.00-120.00   86
 16  \w   -105.00 -74.00   0.50    5.00    --  -90.00 -77.00 -90.00   62
 17  \w   -105.00 -79.00   0.50    5.00    --  -90.00 -65.00-173.16   52
 18  \w   -140.00-114.00   0.50    5.00    --  -90.00 -77.00-150.00   52
 19  \w   -114.00 -78.00   0.50    5.00    --  -90.00 -61.00-120.00   72
 20  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -72.00-120.41   52
 21  \w   -100.00 -74.00   0.50    5.00    --  -90.00 -67.00 175.07   52
 22  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -77.00-150.00   52
 23  \w    -98.00 -73.00   0.50    5.00    --  -90.00 -71.00 139.01   50
 24  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -77.00 150.00   52
 25  \w   -101.00 -75.00   0.50    5.00    --  -90.00 -66.00 179.51   52
 26  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00-120.00   52
 27  \w   -113.00 -79.00   0.50    5.00    --  -90.00 -61.00 150.00   68
 28  \w   -103.00 -77.00   0.50    5.00    --  -90.00 -61.00-161.40   52
 29  \w    -99.00 -74.00   0.50    5.00    --  -90.00 -67.00-155.10   50
 30  \w    -95.00 -70.00   0.50    5.00    --  -90.00 -77.00-180.00   50
 31  \w    -97.00 -70.00   0.50    5.00    --  -90.00 -77.00 136.45   54
 32  \w   -161.00-128.00   0.50    5.00    --  -90.00 -77.00 150.00   66
 33  \w   -101.00 -74.00   0.50    5.00    --  -90.00 -70.00 146.58   54
 34  \w   -106.00 -77.00   0.50    5.00    --  -90.00 -61.00 120.00   58
 35  \w   -110.00 -76.00   0.50    5.00    --  -90.00 -64.00-146.48   68
 36  \w   -108.00 -78.00   0.50    5.00    --  -90.00 -64.00-150.33   60
 37  \w   -106.00 -73.00   0.50    5.00    --  -90.00 -74.00-110.62   66
 38  \w   -101.00 -74.00   0.50    5.00    --  -90.00 -69.00 150.48   54
 39  \w   -100.00 -73.00   0.50    5.00    --  -90.00 -73.00 126.28   54
 40  \w   -101.00 -74.00   0.50    5.00    --  -90.00 -69.00 153.75   54
 41  \w     98.00 178.00   0.50    5.00    --  111.50  77.00-150.00  160
 42  \w     92.00 147.00   0.50    5.00    --  111.50  77.00 150.00  110
 43  \w    120.00 172.00   0.50    5.00    --  111.50  30.00-180.00  104
 44  \w    152.00 177.00   0.50    5.00    --  111.50  45.00  60.00   50
 45  \w     81.00 114.00   0.50    5.00    --  111.50-131.00  56.96   66
 46  \w     44.00  76.00   0.50    5.00    --  111.50-131.00  56.96   64
 47  \w    150.00 177.00   0.50    5.00    --  111.50  45.00  90.00   54
 48  \w     45.00  71.00   0.50    5.00    --  111.50 -61.00   0.00   52
 49  \w    103.00 146.00   0.50    5.00    --  111.50  61.00-120.00   86
 50  \w     41.00  66.00   0.50    5.00    --  111.50 -61.00-120.00   50
 51  \w     45.00  71.00   0.50    5.00    --  111.50 -61.00 -30.00   52
 52  \w     42.00  71.00   0.50    5.00    --  111.50 -61.00  90.00   58
 53  \w    147.00 178.00   0.50    5.00    --  111.50  61.00-180.00   62
 54  \w     98.00 125.00   0.50    5.00    --  111.50  61.00-180.00   54
 55  \w    103.00 148.00   0.50    5.00    --  111.50  61.00 120.00   90
 56  \w     93.00 174.00   0.50    5.00    --  111.50  77.00 120.00  162
 57  \w     79.00 105.00   0.50    5.00    --  111.50 -77.00  60.00   52
 58  \w     43.00  69.00   0.50    5.00    --  111.50 -61.00 -90.00   52
 59  \w     78.00 104.00   0.50    5.00    --  111.50 -77.00   0.00   52
 60  \w     70.00 117.00   0.50    5.00    --  111.50-132.00-178.80   94
 61  \w     41.00  67.00   0.50    5.00    --  111.50 -77.00  60.00   52
 62  \w     75.00 111.00   0.50    5.00    --  111.50-125.00-150.00   72
 63  \w     43.00  70.00   0.50    5.00    --  111.50 -61.00 120.00   54
 64  \w    108.00 136.00   0.50    5.00    --  111.50  61.00-150.00   56
 65  \w    123.00 175.00   0.50    5.00    --  111.50  45.00 -60.00  104
 66  \w    141.00 177.00   0.50    5.00    --  111.50  77.00-180.00   72
 67  \w     81.00 106.00   0.50    5.00    --  111.50 -94.00-180.00   50
 68  \w     51.00  77.00   0.50    5.00    --  111.50 -94.00-180.00   52
 69  \w     92.00 133.00   0.50    5.00    --  111.50  77.00-180.00   82
 70  \w     47.00  73.00   0.50    5.00    --  111.50-125.00-150.00   52
 71  \w    130.00 156.00   0.50    5.00    --  111.50  77.00-120.00   52
 72  \w     97.00 123.00   0.50    5.00    --  111.50  77.00  90.00   52
 73  \w     92.00 123.00   0.50    5.00    --  111.50  77.00-120.00   62
 74  \w     43.00  71.00   0.50    5.00    --  111.50 -61.00-180.00   56
 75  \w     41.00  71.00   0.50    5.00    --  111.50 -61.00 -60.00   60
 76  \w     70.00 108.00   0.50    5.00    --  111.50-125.00 120.00   76
 77  \w    147.00 173.00   0.50    5.00    --  111.50  17.00  88.00   52
 78  \w    113.00 139.00   0.50    5.00    --  111.50  17.00  88.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.126752
_diffrn_orient_matrix_UB_12      -0.0592391
_diffrn_orient_matrix_UB_13      -0.0248744
_diffrn_orient_matrix_UB_21      -0.0864794
_diffrn_orient_matrix_UB_22      -0.0053985
_diffrn_orient_matrix_UB_23      -0.060367
_diffrn_orient_matrix_UB_31      0.0272812
_diffrn_orient_matrix_UB_32      0.2570798
_diffrn_orient_matrix_UB_33      -0.0068588
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28713
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.686
_diffrn_reflns_theta_min         3.767
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_coef       0.0043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     497
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.2780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                5224
_reflns_number_total             5747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01084a2.cif
_cod_data_source_block           23DK001_RG-41
_cod_depositor_comments          'Adding full bibliography for 1571787.cif.'
_cod_original_cell_volume        1377.74(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1571787
_shelx_estimated_absorpt_t_min   0.897
_shelx_estimated_absorpt_t_max   0.949
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
        - B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.826
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              7451