N-Fluorobenzenesulfonimide (NFSI) analogs with deprotectable substituents: Synthesis of b-fluoroamines via catalytic aminofluorination of styrenes
Ito, Yuki; Adachi, Akiya; Aikawa, Kohsuke; Nozaki, Kyoko; Okazoe, Takashi; Chemical Communications  (2023) –; doi:10.1039/D3CC02292G

data_7131766
_publ_section_title
;
 N-Fluorobenzenesulfonimide (NFSI) analogs with deprotectable
 substituents: Synthesis of b-fluoroamines via catalytic aminofluorination
 of styrenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02292G
_journal_year                    2023
_chemical_formula_moiety         'C20 H15 F2 N3 O8 S2'
_chemical_formula_sum            'C20 H15 F2 N3 O8 S2'
_chemical_formula_weight         527.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f02p7
_audit_creation_date             2021-04-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.130(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5286(5)
_cell_length_b                   8.3039(2)
_cell_length_c                   16.6083(5)
_cell_measurement_reflns_used    13763
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      30.6300
_cell_measurement_theta_min      2.1280
_cell_volume                     2166.35(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -71.00  -3.00   0.50   18.50    --   20.00  54.00  86.78  136
  2  \w      2.00 104.00   0.50   18.50    --   20.00  54.00  86.78  204
  3  \w    -74.00  98.00   0.50   18.50    --   20.00  54.00-120.00  344
  4  \w    -73.00 -35.00   0.50   18.50    --   20.00  54.00  -2.78   76
  5  \w    -26.00   1.00   0.50   18.50    --   20.00  54.00  -2.78   54
  6  \w     26.00  51.00   0.50   18.50    --   20.00  54.00  -2.78   50
  7  \w     68.00 107.00   0.50   18.50    --   20.00  54.00  -2.78   78
  8  \w    -74.00  64.00   0.50   18.50    --   20.00  54.00-150.00  276
  9  \w     81.00 106.00   0.50   18.50    --   20.00  54.00-150.00   50
 10  \w    -70.00 -44.00   0.50   18.50    --   20.00  54.00 -60.00   52
 11  \w    -31.00  -5.00   0.50   18.50    --   20.00  54.00 -60.00   52
 12  \w     20.00  51.00   0.50   18.50    --   20.00  54.00 -60.00   62
 13  \w     60.00  85.00   0.50   18.50    --   20.00  54.00 -60.00   50
 14  \w    -67.00 -16.00   0.50   18.50    --   20.00  54.00  60.00  102
 15  \w     56.00  81.00   0.50   18.50    --   20.00  54.00  60.00   50
 16  \w    -67.00 -18.00   0.50   18.50    --   20.00  54.00  30.00   98
 17  \w    -70.00 -43.00   0.50   18.50    --   20.00  54.00-180.00   54
 18  \w    -13.00  12.00   0.50   18.50    --   20.00  54.00-180.00   50
 19  \w     15.00  49.00   0.50   18.50    --   20.00  54.00-180.00   68
 20  \w    -29.00  -4.00   0.50   18.50    --   20.00  54.00 -90.00   50
 21  \w     19.00  44.00   0.50   18.50    --   20.00  54.00 -90.00   50
 22  \w    -70.00  45.00   0.50   18.50    --   20.00  54.00 146.72  230
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.607
_diffrn_reflns_theta_min         2.581
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.056
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0540P)^2^+1.0522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5066
_reflns_number_total             6519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02292g2.cif
_cod_data_source_block           3aa_auto
_cod_database_code               7131766
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.891
_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:
 C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N), C00P(H00P), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X), C00Z(H00Z)
;
_shelx_res_checksum              33463
_shelx_hkl_checksum              71976
_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
;