Photoredox-catalyzed C(sp<sup>2</sup>)-H trifluoromethylation of 3-methylene-isoindolin-1-ones under metal-free conditions.
Zhou, Yuan-Xia; Liu, Feng-Qian; Wang, Guo-Qin; Yang, Dan; Han, Pan; Jing, Lin-Hai; Organic & biomolecular chemistry 22 (2024) 6928–6932; doi:10.1039/d4ob01046a

data_7160093
_publ_section_title
;
 Photoredox-catalyzed C(sp<sup>2</sup>)-H trifluoromethylation of
 3-methylene-isoindolin-1-ones under metal-free conditions.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6928
_journal_page_last               6932
_journal_paper_doi               10.1039/d4ob01046a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H9 F4 N O'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-15 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.929(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1519(17)
_cell_length_b                   9.9600(11)
_cell_length_c                   8.6943(9)
_cell_measurement_reflns_used    1299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4740
_cell_measurement_theta_min      3.1240
_cell_volume                     1381.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.855
_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    -16.00  78.00   1.00    5.00    --   16.96  19.00 150.00   94
  2  \w    -39.00  -9.00   1.00    5.00    --  -17.28 -77.00 -90.00   30
  3  \w    -73.00 -44.00   1.00    5.00    --  -17.28 137.00  53.00   29
  4  \w    -12.00  18.00   1.00    5.00    --  -17.28  77.00-150.00   30
  5  \w    -31.00  11.00   1.00    5.00    --  -17.28 -77.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0159032000
_diffrn_orient_matrix_UB_12      0.0657424000
_diffrn_orient_matrix_UB_13      0.0069824000
_diffrn_orient_matrix_UB_21      0.0392226000
_diffrn_orient_matrix_UB_22      0.0273371000
_diffrn_orient_matrix_UB_23      -0.0108005000
_diffrn_orient_matrix_UB_31      -0.0135549000
_diffrn_orient_matrix_UB_32      0.0020357000
_diffrn_orient_matrix_UB_33      -0.0815874000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         2.411
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0365P)^2^+0.2360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1702
_reflns_number_total             3175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01046a2.cif
_cod_data_source_block           exp_13717_auto
_cod_depositor_comments          'Adding full bibliography for 7160093.cif.'
_cod_database_code               7160093
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00J(H00J), C00L(H00L), C00M(H00M)
;
_shelx_res_checksum              33460
_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 1.090
_oxdiff_exptl_absorpt_empirical_full_min 0.839