Efficient metal-free aminoiodination of alkenes with N-fluorobenzenesulfonimide under mild conditions.
Lei, Bowen; Miao, Qi; Ma, Lifang; Fu, Ruoqi; Hu, Fangrong; Ni, Ni; Li, Ziyuan; Organic & biomolecular chemistry 17 (2019) 2126–2133; doi:10.1039/c8ob03019g

data_7156658
_publ_section_title
;
 Efficient metal-free aminoiodination of alkenes with
 N-fluorobenzenesulfonimide under mild conditions.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2126
_journal_page_last               2133
_journal_paper_doi               10.1039/c8ob03019g
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C18 H20 I N O4 S2'
_chemical_formula_sum            'C18 H20 I N O4 S2'
_chemical_formula_weight         505.37
_chemical_name_systematic
N-(trans-2-Iodocyclohexyl)-N-(phenylsulfonyl)benzenesulfonamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc20bcd4
_audit_creation_date             2018-05-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2018-07-20 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                112.022(14)
_cell_angle_beta                 102.093(11)
_cell_angle_gamma                104.464(7)
_cell_formula_units_Z            4
_cell_length_a                   10.9656(8)
_cell_length_b                   14.1670(12)
_cell_length_c                   14.562(3)
_cell_measurement_reflns_used    6408
_cell_measurement_temperature    108.0(10)
_cell_measurement_theta_max      29.2220
_cell_measurement_theta_min      3.7710
_cell_volume                     1911.4(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.8317
_diffrn_measurement_details
;
  1 omega   -5.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000   30.0000 25

  2 omega  -25.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -37.0000 -120.0000 61

  3 omega   10.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   57.0000    0.0000 72

  4 omega    9.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   57.0000  -90.0000 50

  5 omega    2.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   57.0000 -150.0000 83

  6 omega    2.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   57.0000   90.0000 80

  7 omega  -80.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -77.0000  150.0000 71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0182888000
_diffrn_orient_matrix_UB_12      0.0168767000
_diffrn_orient_matrix_UB_13      0.0549339000
_diffrn_orient_matrix_UB_21      -0.0596668000
_diffrn_orient_matrix_UB_22      0.0110259000
_diffrn_orient_matrix_UB_23      0.0000239000
_diffrn_orient_matrix_UB_31      -0.0338622000
_diffrn_orient_matrix_UB_32      -0.0543031000
_diffrn_orient_matrix_UB_33      -0.0098409000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16808
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.432
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         7508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+2.0916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                6548
_reflns_number_total             7508
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob03019g2.cif
_cod_data_source_block           exp_5467
_cod_depositor_comments          'Adding full bibliography for 7156658.cif.'
_cod_original_cell_volume        1911.3(5)
_cod_database_code               7156658
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32