Photocatalytic 1,3-difluoroalkylcarboxylation of alkenes by triple kinetic-controlled radical self-ordering.
Fu, Hong; Wang, Zuo-Shuai; Li, Si-Jia; Zhu, Lin-Yuan; Wang, Xiao-Jian; Wang, Hong-Chen; Han, Bing; Chemical science 16 (2025) 5849–5856; doi:10.1039/d4sc08607d

data_1573927
_publ_section_title
;
 Photocatalytic 1,3-difluoroalkylcarboxylation of alkenes by triple
 kinetic-controlled radical self-ordering.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              5849
_journal_page_last               5856
_journal_paper_doi               10.1039/d4sc08607d
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C20 H21 F2 N O3'
_chemical_formula_sum            'C20 H21 F2 N O3'
_chemical_formula_weight         361.38
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-31
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-09-02 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.8088(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.45569(15)
_cell_length_b                   18.57018(19)
_cell_length_c                   10.44754(14)
_cell_measurement_reflns_used    18609
_cell_measurement_temperature    280(1)
_cell_measurement_theta_max      76.3460
_cell_measurement_theta_min      2.3250
_cell_volume                     1826.19(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      280(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_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  65.00   0.50    0.05    --  104.75 -61.00-180.00   66
  2  \w     46.00  71.00   0.50    0.05    --  104.75 -61.00 -60.00   50
  3  \w     41.00 106.00   0.50    0.05    --  104.75-108.00  35.00  130
  4  \w     77.00 102.00   0.50    0.05    --  104.75-100.00 126.00   50
  5  \w    -23.00  25.00   0.50    0.05    --   46.68 -19.00 120.00   96
  6  \w   -118.00 -36.00   0.50    0.05    --  -46.68 -29.00-120.00  164
  7  \w    -67.00 -42.00   0.50    0.05    -- -102.00  61.00  30.00   50
  8  \w    -71.00 -45.00   0.50    0.05    -- -102.00 125.00  90.00   52
  9  \w    -24.00   4.00   0.50    0.05    --  -46.68  19.00-150.00   56
 10  \w    -69.00 -30.00   0.50    0.05    -- -102.00  61.00-120.00   78
 11  \w   -106.00 -40.00   0.50    0.05    -- -102.00 100.00-128.00  132
 12  \w   -170.00 -92.00   0.50    0.05    -- -102.00 -29.00-120.00  156
 13  \w     36.00  61.00   0.50    0.05    --  104.75-108.00  35.00   50
 14  \w   -119.00 -34.00   0.50    0.05    --  -46.68 -37.00 -30.00  170
 15  \w     45.00  79.00   0.50    0.05    --   46.68-108.00  35.00   68
 16  \w     -8.00  43.00   0.50    0.05    --   46.68 -37.00 150.00  102
 17  \w    -27.00  28.00   0.50    0.05    --   46.68 -19.00-180.00  110
 18  \w     15.00  53.00   0.50    0.05    --   46.68 -57.00  90.00   76
 19  \w    -26.00  28.00   0.50    0.05    --   46.68 -37.00  60.00  108
 20  \w    -25.00  13.00   0.50    0.05    --   46.68 -57.00  90.00   76
 21  \w   -125.00 -80.00   0.50    0.05    -- -102.00 143.00-164.64   90
 22  \w   -132.00-106.00   0.50    0.05    -- -102.00 -30.00  30.00   52
 23  \w    -94.00 -32.00   0.50    0.05    -- -102.00 125.00 150.00  124
 24  \w    -68.00 -42.00   0.50    0.05    -- -102.00  61.00  90.00   52
 25  \w    -81.00 -40.00   0.50    0.05    -- -102.00  77.00-180.00   82
 26  \w    -64.00 -39.00   0.50    0.05    -- -102.00  61.00 120.00   50
 27  \w   -106.00 -80.00   0.50    0.05    -- -102.00 108.00 132.00   52
 28  \w    -54.00 -29.00   0.50    0.05    -- -102.00 143.00-164.64   50
 29  \w   -175.00-111.00   0.50    0.05    -- -102.00 -30.00 -60.00  128
 30  \w     34.00  60.00   0.50    0.05    --  104.75 -94.00-180.00   52
 31  \w     93.00 177.00   0.50    0.05    --  104.75  30.00   0.00  168
 32  \w     39.00  72.00   0.50    0.05    --  104.75 -61.00 -90.00   66
 33  \w     92.00 175.00   0.50    0.05    --  104.75  45.00  60.00  166
 34  \w    102.00 178.00   0.50    0.05    --  104.75  30.00 150.00  152
 35  \w     65.00 111.00   0.50    0.05    --  104.75-125.00   0.00   92
 36  \w     40.00  75.00   0.50    0.05    --  104.75 -94.00  90.00   70
 37  \w     33.00  65.00   0.50    0.05    --  104.75 -77.00 -90.00   64
 38  \w    143.00 169.00   0.50    0.05    --  104.75  61.00 -30.00   52
 39  \w    107.00 133.00   0.50    0.05    --  104.75  61.00 -30.00   52
 40  \w     69.00 111.00   0.50    0.05    --  104.75-125.00 -30.00   84
 41  \w     38.00  71.00   0.50    0.05    --  104.75 -94.00-120.00   66
 42  \w     38.00 106.00   0.50    0.05    --  104.75 -94.00  30.00  136
 43  \w     38.00 111.00   0.50    0.05    --  104.75-125.00 150.00  146
 44  \w     39.00  64.00   0.50    0.05    --  104.75 -61.00  30.00   50
 45  \w    115.00 159.00   0.50    0.05    --  104.75  45.00 120.00   88
 46  \w     82.00 107.00   0.50    0.05    --  104.75-108.00  35.00   50
;
_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      -0.1570851000
_diffrn_orient_matrix_UB_12      0.0089022000
_diffrn_orient_matrix_UB_13      -0.1065971000
_diffrn_orient_matrix_UB_21      0.0263213000
_diffrn_orient_matrix_UB_22      0.0802673000
_diffrn_orient_matrix_UB_23      -0.0171677000
_diffrn_orient_matrix_UB_31      0.0375773000
_diffrn_orient_matrix_UB_32      -0.0189431000
_diffrn_orient_matrix_UB_33      -0.1231873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25143
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.319
_diffrn_reflns_theta_min         4.698
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0478P)^2^+0.2871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3473
_reflns_number_total             3741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08607d2.cif
_cod_data_source_block           fuhong-hb_0831_auto
_cod_depositor_comments
'Adding full bibliography for 1573927--1573928.cif.'
_cod_database_code               1573927
_shelx_shelxl_version_number     2018/3
_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:
 C6(H6), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C17(H17), C20(H20)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              24262
_shelx_hkl_checksum              3421
_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 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.743