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_7131765
_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         'C15 H14 F2 N2 O6 S2'
_chemical_formula_sum            'C15 H14 F2 N2 O6 S2'
_chemical_formula_weight         420.40
_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_block_doi                 10.5517/ccdc.csd.cc2f02q8
_audit_creation_date             2021-03-18
_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                 117.306(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6054(6)
_cell_length_b                   8.9495(3)
_cell_length_c                   14.5067(6)
_cell_measurement_reflns_used    16291
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      30.3490
_cell_measurement_theta_min      2.7480
_cell_volume                     1684.89(14)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -15.00  28.00   0.50    3.61    --   20.00  54.00 -90.00   86
  2  \w     34.00  80.00   0.50    3.61    --   20.00  54.00 -90.00   92
  3  \w    -74.00  28.00   0.50    3.61    --   20.00  54.00  30.00  204
  4  \w     32.00  99.00   0.50    3.61    --   20.00  54.00  30.00  134
  5  \w     11.00  43.00   0.50    3.61    --   20.00  54.00 150.00   64
  6  \w     65.00  90.00   0.50    3.61    --   20.00  54.00 150.00   50
  7  \w    -74.00 108.00   0.50    3.61    --   20.00  54.00-150.00  364
  8  \w    -73.00 -48.00   0.50    3.61    --   20.00  54.00  90.00   50
  9  \w     75.00 100.00   0.50    3.61    --   20.00  54.00  90.00   50
 10  \w    -73.00  46.00   0.50    3.61    --   20.00  54.00 -60.00  238
 11  \w     53.00  78.00   0.50    3.61    --   20.00  54.00 -60.00   50
 12  \w    -67.00  69.00   0.50    3.61    --   20.00  54.00 120.00  272
 13  \w    -70.00 -43.00   0.50    3.61    --   20.00  54.00   0.00   54
 14  \w     79.00 104.00   0.50    3.61    --   20.00  54.00   0.00   50
 15  \w    -67.00 -40.00   0.50    3.61    --   20.00  54.00 -30.00   54
 16  \w    -12.00  13.00   0.50    3.61    --   20.00  54.00 -30.00   50
 17  \w     69.00  94.00   0.50    3.61    --   20.00  54.00 -30.00   50
 18  \w    -69.00  34.00   0.50    3.61    --   20.00  54.00-180.00  206
 19  \w     84.00 109.00   0.50    3.61    --   20.00  54.00-180.00   50
 20  \w    -69.00 -44.00   0.50    3.61    --   20.00  54.00-120.00   50
 21  \w     46.00  71.00   0.50    3.61    --   20.00  54.00-120.00   50
 22  \w    -20.00   5.00   0.50    3.61    --   20.00  54.00  60.00   50
 23  \w     16.00  41.00   0.50    3.61    --   20.00  54.00  60.00   50
 24  \w    -72.00 -47.00   0.50    3.61    --   20.00  54.00 -90.00   50
;
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28297
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.765
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97793
_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    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.237
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0408P)^2^+0.7290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3042
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02292g2.cif
_cod_data_source_block           20-01-122-2_auto
_cod_original_cell_volume        1684.89(13)
_cod_database_code               7131765
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00O(H00O),
 C00Q(H00Q), C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00P(H00C,H00D,H00G)
;
_shelx_res_checksum              66963
_shelx_hkl_checksum              32203
_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
;