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_4126234
_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 4S,5R,6R
_chemical_formula_sum            'C17 H16 I N O2'
_chemical_formula_weight         393.20
_chemical_name_common
;
(4S,5R,6R)-4-(2-iodophenyl)-5-methyl-6-phenyl-1,3-oxazinan-2-one
;
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 100.247(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.657(3)
_cell_length_b                   7.8904(13)
_cell_length_c                   20.662(3)
_cell_measurement_reflns_used    6179
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      3.026
_cell_volume                     3153.6(8)
_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 0.978
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13313
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         3.006
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       prism
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         2.359
_refine_diff_density_min         -1.131
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
;
 Flack x determined using 2503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6441
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+44.0305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.840
_reflns_Friedel_fraction_max     0.784
_reflns_number_gt                6275
_reflns_number_total             6441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04795_si_003.cif
_cod_data_source_block           CrystalClear
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C34 H32 I2 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     786.41
_cod_database_code               4126234
_shelx_estimated_absorpt_t_min   0.580
_shelx_estimated_absorpt_t_max   0.822
_shelxl_version_number           2014/6
_shelx_res_checksum              93151
_shelx_hkl_checksum              37880