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_7131767
_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 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f02r9
_audit_creation_date             2022-01-04
_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                 91.882(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0255(3)
_cell_length_b                   10.1690(4)
_cell_length_c                   21.2063(9)
_cell_measurement_reflns_used    19818
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      30.7180
_cell_measurement_theta_min      2.0290
_cell_volume                     2160.80(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -73.00  65.00   0.50    6.20    --   20.00  54.00-172.56  276
  2  \w    -73.00  35.00   0.50    6.20    --   20.00  54.00 -60.00  216
  3  \w     77.00 108.00   0.50    6.20    --   20.00  54.00 -60.00   62
  4  \w    -70.00  75.00   0.50    6.20    --   20.00  54.00 120.00  290
  5  \w    -69.00  49.00   0.50    6.20    --   20.00  54.00-120.00  236
  6  \w     76.00 101.00   0.50    6.20    --   20.00  54.00-120.00   50
  7  \w    -64.00  -5.00   0.50    6.20    --   20.00  54.00 -30.00  118
  8  \w     78.00 103.00   0.50    6.20    --   20.00  54.00 -30.00   50
  9  \w    -62.00  86.00   0.50    6.20    --   20.00  54.00-150.00  296
 10  \w    -64.00  13.00   0.50    6.20    --   20.00  54.00   0.00  154
 11  \w     50.00  75.00   0.50    6.20    --   20.00  54.00   0.00   50
 12  \w    -42.00 -17.00   0.50    6.20    --   20.00  54.00 -90.00   50
 13  \w      8.00  33.00   0.50    6.20    --   20.00  54.00 -90.00   50
 14  \w     43.00  69.00   0.50    6.20    --   20.00  54.00 -90.00   52
 15  \w    -74.00 -46.00   0.50    6.20    --   20.00  54.00  90.00   56
 16  \w     39.00  64.00   0.50    6.20    --   20.00  54.00  90.00   50
 17  \w    -67.00 -40.00   0.50    6.20    --   20.00  54.00  30.00   54
 18  \w     40.00  65.00   0.50    6.20    --   20.00  54.00  30.00   50
 19  \w    -64.00  37.00   0.50    6.20    --   20.00  54.00 150.00  202
 20  \w     72.00  97.00   0.50    6.20    --   20.00  54.00  39.28   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  0.0302
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36386
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.922
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0389
_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^)+(0.0501P)^2^+1.4407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3888
_reflns_number_total             4416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02292g2.cif
_cod_data_source_block           3fa_auto
_cod_database_code               7131767
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.822
_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:
 C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00T(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
;
_shelx_res_checksum              69543
_shelx_hkl_checksum              48027
_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
;