Transition-Metal-Free Carbofluorination of TBS-Protected Nitrogen-Containing Cyclic Enynols: Synthesis of Fluorinated Azabicycles
Ming-Chang P. Yeh; Chia-Jung Liang; Tzu-Lin Huang; Hsiao-Ju Hsu; Yu-Shuo Tsau; Journal of Organic Chemistry 78 (2013) 5521–5529; doi:10.1021/jo400634c

data_4028313
_publ_section_title
;
 Transition-Metal-Free Carbofluorination of TBS-Protected
 Nitrogen-Containing Cyclic Enynols: Synthesis of Fluorinated Azabicycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5521
_journal_page_last               5529
_journal_paper_doi               10.1021/jo400634c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C27 H27 N O3 S'
_chemical_formula_sum            'C27 H27 N O3 S'
_chemical_formula_weight         445.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.101(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.3782(16)
_cell_length_b                   28.013(4)
_cell_length_c                   17.254(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     4507.2(13)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.2143
_diffrn_reflns_av_sigmaI/netI    0.4762
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21434
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.8796
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         8037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.3432
_refine_ls_R_factor_gt           0.0901
_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^)+(0.0536P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.2249
_reflns_number_gt                2270
_reflns_number_total             8037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400634c_si_010.cif
_cod_data_source_block           a14167
_cod_original_cell_volume        4507.3(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028313