Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines.
Cui, Jian; Jia, Qun; Feng, Ruo-Zhu; Liu, Shan-Shan; He, Tian; Zhang, Chi; Organic letters 16 (2014) 1442–1445; doi:10.1021/ol500238k

data_1513814
_publ_section_title
;
 Boron trifluoride etherate functioning as a fluorine source in an
 iodosobenzene-mediated intramolecular aminofluorination of homoallylic
 amines.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1442
_journal_page_last               1445
_journal_paper_doi               10.1021/ol500238k
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 F N O2 S'
_chemical_formula_sum            'C17 H18 F N O2 S'
_chemical_formula_weight         319.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.605(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1325(10)
_cell_length_b                   7.0271(12)
_cell_length_c                   34.947(4)
_cell_measurement_reflns_used    6204
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      31.30
_cell_measurement_theta_min      2.30
_cell_volume                     1505.9(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       40
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            14011
_diffrn_reflns_point_group_measured_fraction_full 0.816
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_min         2.331
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5705
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0514P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.583
_reflns_Friedel_fraction_full    0.632
_reflns_Friedel_fraction_max     0.584
_reflns_number_gt                4986
_reflns_number_total             5705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500238k_si_004.cif
_cod_data_source_block           shelxl
_cod_database_code               1513814
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.951
_shelxl_version_number           2013-3
_shelx_res_checksum              17571
_shelx_hkl_checksum              5718