Fluoride-Catalyzed Addition of PhSCF2SiMe3 to N-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of gem-Difluoromethylenated 1-Azabicyclic Compounds
Teerawut Bootwicha; Duanghathai Panichakul; Chutima Kuhakarn; Samran Prabpai; Palangpon Kongsaeree; Patoomratana Tuchinda; Vichai Reutrakul; Manat Pohmakotr; Journal of Organic Chemistry 74 (2009) 3798–3805; doi:10.1021/jo802794u

data_4024522
_publ_section_title
;
Fluoride-Catalyzed Addition of PhSCF2SiMe3 to N-Substituted Cyclic Imides
Followed by Radical Cyclization: General Synthetic Strategy
of gem-Difluoromethylenated 1-Azabicyclic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3798
_journal_page_last               3805
_journal_paper_doi               10.1021/jo802794u
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C13 H13 F2 N O2 '
_chemical_formula_sum            'C13 H13 F2 N O2'
_chemical_formula_weight         253.248
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 112.362(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0530(5)
_cell_length_b                   10.2639(3)
_cell_length_c                   10.4166(3)
_cell_measurement_reflns_used    3372
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1191.74(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.06440
_diffrn_orient_matrix_UB_12      0.07712
_diffrn_orient_matrix_UB_13      -0.02610
_diffrn_orient_matrix_UB_21      -0.05624
_diffrn_orient_matrix_UB_22      -0.02099
_diffrn_orient_matrix_UB_23      0.07674
_diffrn_orient_matrix_UB_31      0.02288
_diffrn_orient_matrix_UB_32      0.07794
_diffrn_orient_matrix_UB_33      0.03809
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14866
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.12
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.366
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.366
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1886
_reflns_number_gt                2598
_reflns_number_total             3339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802794u_si_003.cif
_cod_data_source_block           trans6a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C13 H13 F2 N O2 '
_cod_database_code               4024522