Photocatalytic redox-neutral selective single C(sp<sup>3</sup>)-F bond activation of perfluoroalkyl iminosulfides with alkenes and water.
Wang, Tao; Zong, Yuan-Yuan; Huang, Tao; Jin, Xiao-Ling; Wu, Li-Zhu; Liu, Qiang; Chemical science 14 (2023) 11566–11572; doi:10.1039/d3sc03771a

data_1570069
_publ_section_title
;
 Photocatalytic redox-neutral selective single C(sp<sup>3</sup>)-F bond
 activation of perfluoroalkyl iminosulfides with alkenes and water.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              11566
_journal_page_last               11572
_journal_paper_doi               10.1039/d3sc03771a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C16 H12 F4 N2 O'
_chemical_formula_sum            'C16 H12 F4 N2 O'
_chemical_formula_weight         324.28
_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             2021-06-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.812(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5988(5)
_cell_length_b                   8.2297(4)
_cell_length_c                   12.1249(6)
_cell_measurement_reflns_used    2307
_cell_measurement_temperature    295(7)
_cell_measurement_theta_max      71.7130
_cell_measurement_theta_min      5.7760
_cell_volume                     1523.56(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.942
_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    -85.00 -55.00   0.50    4.00    --  -46.57-161.00 -49.00   60
  2  \w    -73.00 -48.00   0.50    4.00    --  -46.57 117.00-170.00   50
  3  \w     65.00 110.00   0.50    4.00    --   46.57 161.00 -20.00   90
  4  \w     16.00  89.00   0.50    4.00    --   46.57-117.00 101.00  146
  5  \w   -109.00 -30.00   0.50    9.00    -- -102.00 117.00-170.00  158
  6  \w   -119.00 -85.00   0.50    9.00    -- -102.00-117.00 101.00   68
  7  \w   -128.00-103.00   0.50    9.00    -- -102.00-161.00 -49.00   50
  8  \w     70.00 102.00   0.50    9.00    --  104.25-117.00 101.00   64
  9  \w    128.00 154.00   0.50    9.00    --  104.25 161.00 -20.00   52
 10  \w   -119.00 -77.00   0.50    4.00    --  -46.57-125.00 -30.00   84
 11  \w   -119.00 -79.00   0.50    4.00    --  -46.57-125.00 150.00   80
 12  \w    -28.00  28.00   0.50    4.00    --   46.57 -19.00 -30.00  112
 13  \w    -24.00  29.00   0.50    4.00    --   46.57 -19.00-120.00  106
 14  \w    -67.00 -30.00   0.50    9.00    -- -102.00  61.00 150.00   74
 15  \w   -112.00 -72.00   0.50    9.00    -- -102.00 125.00 -60.00   80
 16  \w    -66.00 -29.00   0.50    9.00    -- -102.00  61.00   0.00   74
 17  \w    -69.00 -29.00   0.50    9.00    -- -102.00  61.00-150.00   80
 18  \w    -63.00 -29.00   0.50    9.00    -- -102.00  61.00  90.00   68
 19  \w    -69.00 -30.00   0.50    9.00    -- -102.00  61.00  60.00   78
 20  \w     33.00  59.00   0.50    9.00    --  104.25 -61.00 150.00   52
 21  \w     48.00  73.00   0.50    9.00    --  104.25 -61.00-120.00   50
 22  \w     33.00 112.00   0.50    9.00    --  104.25-125.00 150.00  158
 23  \w     93.00 170.00   0.50    9.00    --  104.25  30.00   0.00  154
 24  \w    128.00 153.00   0.50    9.00    --  104.25  45.00 -60.00   50
 25  \w     96.00 154.00   0.50    9.00    --  104.25  45.00 -90.00  116
 26  \w     44.00  73.00   0.50    9.00    --  104.25 -61.00 -90.00   58
;
_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      -0.0116452000
_diffrn_orient_matrix_UB_12      -0.1479188000
_diffrn_orient_matrix_UB_13      -0.0795728000
_diffrn_orient_matrix_UB_21      0.0036688000
_diffrn_orient_matrix_UB_22      0.1128452000
_diffrn_orient_matrix_UB_23      -0.1003607000
_diffrn_orient_matrix_UB_31      0.1001082000
_diffrn_orient_matrix_UB_32      -0.0212534000
_diffrn_orient_matrix_UB_33      0.0211064000
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11261
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.552
_diffrn_reflns_theta_min         2.894
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.307
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0722
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2044
_refine_ls_wR_factor_ref         0.2354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1541
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03771a2.cif
_cod_data_source_block           wangtao_0625-3_auto
_cod_depositor_comments          'Adding full bibliography for 1570069.cif.'
_cod_database_code               1570069
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 98.98
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C6(H6), C16(H16), C15(H15), C2(H2), C5(H5), C4(H4), C3(H3)
;
_shelx_res_checksum              40293
_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 1.838
_oxdiff_exptl_absorpt_empirical_full_min 0.752