Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Brønsted Acid Catalyst.
Hatano, Manabu; Nishikawa, Keisuke; Ishihara, Kazuaki; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b04795

data_4126233
_publ_section_title
;
 Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a
 Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral
 Br\/onsted Acid Catalyst.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b04795
_journal_year                    2017
_chemical_absolute_configuration (R)
_chemical_formula_sum            'C120 H108 K3.5 Mg1.5 O21.5 S6'
_chemical_formula_weight         2259.73
_chemical_name_common
;
(R)-BINSA-trimer potasium magnesium salt
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 104.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.261(2)
_cell_length_b                   25.280(3)
_cell_length_c                   32.387(4)
_cell_measurement_reflns_used    15349
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      3.013
_cell_volume                     15300(3)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            60588
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         3.013
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    0.981
_exptl_crystal_description       prism
_exptl_crystal_F_000             4722
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 5668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.099(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.637
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1394
_refine_ls_number_reflns         28622
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.637
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.1095
_refine_ls_shift/su_max          0.198
_refine_ls_shift/su_mean         0.060
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2703
_refine_ls_wR_factor_ref         0.2849
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.709
_reflns_Friedel_fraction_max     0.636
_reflns_number_gt                15869
_reflns_number_total             28622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04795_si_004.cif
_cod_data_source_block           CrystalClear
_cod_original_formula_sum        'C120 H108 K3.50 Mg1.50 O21.50 S6'
_cod_database_code               4126233
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2014/6
_shelx_res_checksum              62605
_shelx_hkl_checksum              47033