A Highly Regio- and Stereoselective Synthesis of α-Fluorinated Imides via Fluorination of Chiral Enamides.
Xu, Yan-Shuang; Tang, Yu; Feng, He-Jing; Liu, Ji-Tian; Hsung, Richard P.; Organic letters 17 (2015) 572–575; doi:10.1021/ol503591d

data_1518581
_publ_section_title
;
 A Highly Regio- and Stereoselective Synthesis of \a-Fluorinated Imides
 via Fluorination of Chiral Enamides.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              572
_journal_page_last               575
_journal_paper_doi               10.1021/ol503591d
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration empirical
_chemical_formula_sum            'C14 H16 F N O3'
_chemical_formula_weight         265.28
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.01(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.680(2)
_cell_length_b                   10.806(2)
_cell_length_c                   12.352(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1363.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0868
_diffrn_reflns_av_sigmaI/netI    0.1427
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13403
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9755
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(13)
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6112
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1916
_reflns_number_gt                3236
_reflns_number_total             6112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503591d_si_003.cif
_cod_data_source_block           b
_cod_depositor_comments
'Adding full bibliography for 1518581--1518582.cif.'
_cod_original_cell_volume        1363.0(5)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1518581