Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.
Mennie, Katrina M.; Banik, Steven M.; Reichert, Elaine C.; Jacobsen, Eric N.; Journal of the American Chemical Society 140 (2018) 4797–4802; doi:10.1021/jacs.8b02143

data_4132181
_publ_section_title
;
 Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4797
_journal_page_last               4802
_journal_paper_doi               10.1021/jacs.8b02143
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 F2 N2 O4 S'
_chemical_formula_weight         370.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.176(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7281(5)
_cell_length_b                   7.7633(3)
_cell_length_c                   15.1716(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.7
_cell_measurement_theta_min      2.85
_cell_volume                     1607.53(10)
_computing_cell_refinement       'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27659
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.643
_diffrn_reflns_theta_min         2.930
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  0.8637
_exptl_absorpt_correction_T_min  0.8148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1083P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.827
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                4476
_reflns_number_total             5129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02143_si_003.cif
_cod_data_source_block           ER-1-16
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132181
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.616
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              13695
_shelx_hkl_checksum              14576