Fluoroalkyl sulfides as photoredox-active coupling reagents for alkene difunctionalization.
Kosobokov, Mikhail D.; Zubkov, Mikhail O.; Levin, Vitalij V.; Kokorekin, Vladimir A.; Dilman, Alexander D.; Chemical communications (Cambridge, England) 56 (2020) 9453–9456; doi:10.1039/d0cc04617e

data_7126853
_publ_section_title
;
 Fluoroalkyl sulfides as photoredox-active coupling reagents for alkene
 difunctionalization.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9453
_journal_page_last               9456
_journal_paper_doi               10.1039/d0cc04617e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H12 F6 N2 O S'
_chemical_formula_sum            'C17 H12 F6 N2 O S'
_chemical_formula_weight         406.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-07 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1213(2)
_cell_length_b                   9.6599(3)
_cell_length_c                   24.5371(8)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.79
_cell_measurement_theta_min      2.68
_cell_volume                     1687.93(9)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
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_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
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_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            59793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.208
_diffrn_reflns_theta_min         2.684
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.6843
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Crystalized from the racemic mixture.
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         6462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.3413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5749
_reflns_number_total             6462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04617e2.cif
_cod_data_source_block           KM11201
_cod_depositor_comments          'Adding full bibliography for 7126853.cif.'
_cod_database_code               7126853
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              35970