Catalytic Asymmetric Synthesis of Axially Chiralo-Iodoanilides by Phase-Transfer Catalyzed Alkylations
Seiji Shirakawa; Kun Liu; Keiji Maruoka; Journal of the American Chemical Society 134 (2012) 916–919; doi:10.1021/ja211069f

data_4117321
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Axially Chiralo-Iodoanilides by
 Phase-Transfer Catalyzed Alkylations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              916
_journal_page_last               919
_journal_paper_doi               10.1021/ja211069f
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C61 H51 F12 I N2 O'
_chemical_formula_sum            'C61 H51 F12 I N2 O'
_chemical_formula_weight         1182.97
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.435(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   16.2335(3)
_cell_length_b                   20.7081(4)
_cell_length_c                   18.2329(4)
_cell_measurement_reflns_used    28588
_cell_measurement_temperature    153
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.48
_cell_volume                     6063.0(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35417
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.805
_exptl_absorpt_correction_T_max  0.618
_exptl_absorpt_correction_T_min  0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             2400.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_platon_squeeze_details
;
;
_refine_diff_density_max         3.750
_refine_diff_density_min         -0.690
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  5106 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.050(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     771
_refine_ls_number_reflns         10748
_refine_ls_number_restraints     921
_refine_ls_R_factor_gt           0.1197
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1763P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3059
_reflns_number_gt                5725
_reflns_number_total             10748
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja211069f_si_002.cif
_cod_data_source_block           KYOUDAI_SHIRAKAWA_vai2_proc
_cod_original_cell_volume        6063.0(3)
_cod_database_code               4117321