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_4132255
_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         'C21 H25 I O2'
_chemical_formula_sum            'C21 H25 I O2'
_chemical_formula_weight         436.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.591(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.059(3)
_cell_length_b                   9.733(3)
_cell_length_c                   10.770(3)
_cell_measurement_reflns_used    3780
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.10
_cell_volume                     926.8(5)
_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    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.978
_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  0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7891
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.385
_diffrn_reflns_theta_min         3.113
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details
;
 Flack x determined using 1601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0155
_refine_ls_R_factor_gt           0.0152
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0223P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0407
_refine_ls_wR_factor_ref         0.0408
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                3784
_reflns_number_total             3837
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8b02607_si_002.cif
_cod_data_source_block           20171219-1
_cod_database_code               4132255
_shelx_res_checksum              7797
_shelx_hkl_checksum              28873