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_7131759
_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         'C12 H8 F N3 O8 S2'
_chemical_formula_sum            'C12 H8 F N3 O8 S2'
_chemical_formula_weight         405.33
_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.cc2f02n6
_audit_creation_date             2021-11-28
_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                 94.123(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6151(3)
_cell_length_b                   12.0228(4)
_cell_length_c                   17.3608(7)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      30.3360
_cell_measurement_theta_min      2.1040
_cell_volume                     1585.35(10)
_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 0.952
_diffrn_measured_fraction_theta_max 0.939
_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    -13.00 109.00   0.50  120.00    --   20.00  54.00 -60.00  244
  2  \w    -72.00 -37.00   0.50  120.00    --   20.00  54.00   0.00   70
  3  \w     -1.00  25.00   0.50  120.00    --   20.00  54.00   0.00   52
  4  \w     78.00 109.00   0.50  120.00    --   20.00  54.00   0.00   62
  5  \w      4.00  72.00   0.50  120.00    --   20.00  54.00-150.00  136
  6  \w    -35.00 -10.00   0.50  120.00    --   20.00  54.00-180.00   50
  7  \w     69.00  94.00   0.50  120.00    --   20.00  54.00-180.00   50
  8  \w    -57.00 -32.00   0.50  120.00    --   20.00  54.00 -60.00   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  0.0154
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7826
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.062
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.851
_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    1.698
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0021(7)
_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   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0361P)^2^+0.6669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2660
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02292g2.cif
_cod_data_source_block           4-nsnsnf_auto
_cod_database_code               7131759
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.832
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_shelx_res_checksum              64751
_shelx_hkl_checksum              61221
_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
;