Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives.
Huang, Jian Qiang; Nairoukh, Zackaria; Marek, Ilan; Organic & biomolecular chemistry 16 (2018) 1079–1082; doi:10.1039/c8ob00067k

data_7156067
_publ_section_title
;
 Electrophilic fluorination of stereodefined disubstituted silyl ketene
 hemiaminals en route to tertiary \a-fluorinated carbonyl derivatives.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1079
_journal_page_last               1082
_journal_paper_doi               10.1039/c8ob00067k
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H13 Br F N O4'
_chemical_formula_sum            'C16 H13 Br F N O4'
_chemical_formula_weight         382.18
_chemical_name_common            'Marek135 (Jian Qiang Huang)'
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-09-14 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.8490(2)
_cell_length_b                   7.0020(2)
_cell_length_c                   7.6880(8)
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      0.68
_cell_volume                     1606.81(17)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Mercury 3.7'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1551
_diffrn_reflns_theta_full        24.38
_diffrn_reflns_theta_max         24.38
_diffrn_reflns_theta_min         1.36
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_T_max  0.6531
_exptl_absorpt_correction_T_min  0.4623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'   
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0485
_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^)+(0.1011P)^2^+0.7687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                1417
_reflns_number_total             1551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob00067k2.cif
_cod_data_source_block           Marek135
_cod_depositor_comments          'Adding full bibliography for 7156067.cif.'
_cod_database_code               7156067