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_7131760
_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         'C13 H9 F N2 O5 S'
_chemical_formula_sum            'C13 H9 F N2 O5 S'
_chemical_formula_weight         324.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f02k3
_audit_creation_date             2022-05-06
_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                89.555(4)
_cell_angle_beta                 88.085(4)
_cell_angle_gamma                88.797(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0221(3)
_cell_length_b                   7.3175(4)
_cell_length_c                   13.1378(7)
_cell_measurement_reflns_used    5281
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      30.5510
_cell_measurement_theta_min      2.7670
_cell_volume                     674.53(6)
_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 0.993
_diffrn_measured_fraction_theta_max 0.990
_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     24.00  81.00   0.50    3.15    --   20.00  54.00-150.00  114
  2  \w    -73.00 109.00   0.50    3.15    --   20.00  54.00   0.00  364
  3  \w    -72.00  87.00   0.50    3.15    --   20.00  54.00 -60.00  318
  4  \w    -70.00 -15.00   0.50    3.15    --   20.00  54.00  60.00  110
  5  \w     23.00  51.00   0.50    3.15    --   20.00  54.00  60.00   56
  6  \w    -50.00 -25.00   0.50    3.15    --   20.00  54.00 -90.00   50
  7  \w     -6.00  19.00   0.50    3.15    --   20.00  54.00 -90.00   50
  8  \w    -68.00 -20.00   0.50    3.15    --   20.00  54.00 150.00   96
  9  \w    -74.00 -39.00   0.50    3.15    --   20.00  54.00-120.00   70
 10  \w    -20.00   5.00   0.50    3.15    --   20.00  54.00-180.00   50
 11  \w     42.00  67.00   0.50    3.15    --   20.00  54.00-180.00   50
 12  \w    -68.00   6.00   0.50    3.15    --   20.00  54.00 120.00  148
 13  \w     53.00  78.00   0.50    3.15    --   20.00  54.00 120.00   50
 14  \w    -23.00   2.00   0.50    3.15    --   20.00  54.00-150.00   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  0.0213
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7601
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.784
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90842
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       cube
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.269
_refine_diff_density_max         1.347
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0726P)^2^+0.4467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2416
_reflns_number_total             2732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02292g2.cif
_cod_data_source_block           nsbznf_auto
_cod_database_code               7131760
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
;
_shelx_res_checksum              35203
_shelx_hkl_checksum              3116
_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
;