Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids.
Lu, Yanhui; Nakatsuji, Hidefumi; Okumura, Yukimasa; Yao, Lu; Ishihara, Kazuaki; Journal of the American Chemical Society 140 (2018) 6039–6043; doi:10.1021/jacs.8b02607

data_4132250
_publ_section_title
;
 Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral
 Amidophosphate Catalysts and Halo-Lewis Acids.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6039
_journal_page_last               6043
_journal_paper_doi               10.1021/jacs.8b02607
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C64 H50 I2 N O3 P Si2'
_chemical_formula_sum            'C64 H50 I2 N O3 P Si2'
_chemical_formula_weight         1222.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.5142(17)
_cell_length_b                   13.629(2)
_cell_length_c                   33.558(5)
_cell_measurement_reflns_used    6744
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.40
_cell_volume                     5266.2(13)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1848
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            34992
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         3.004
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.320
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2456.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.20
_refine_diff_density_min         -1.23
_refine_ls_abs_structure_details
;
 Flack x determined using 2833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     658
_refine_ls_number_reflns         11214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0598P)^2^+20.5137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1899
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                8776
_reflns_number_total             11214
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8b02607_si_004.cif
_cod_data_source_block           20180126-1
_cod_database_code               4132250
_shelx_res_checksum              22952
_shelx_hkl_checksum              13125