The Crystallographic Structure of a Lewis Acid-Assisted Chiral Brønsted Acid as an Enantioselective Protonation Reagent for Silyl Enol Ethers
Kazuaki Ishihara; Daisuke Nakashima; Yukihiro Hiraiwa; Hisashi Yamamoto; Journal of the American Chemical Society 125 (2003) 24–25; doi:10.1021/ja021000x

data_4113373
_publ_contact_author_address
;
Graduate School of Engineering, Nagoya University, Furo-cho,
Chikusa, Nagoya 464-8603, Japan
;
_publ_section_title
;
 The Crystallographic Structure of a Lewis Acid-Assisted Chiral Br\/onsted
 Acid as an Enantioselective Protonation Reagent for Silyl Enol Ethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              24
_journal_page_last               25
_journal_paper_doi               10.1021/ja021000x
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C15 H16 Cl4 O2 Sn'
_chemical_formula_weight         488.77
_chemical_name_systematic
; 

? 

;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9736(5)
_cell_length_b                   14.2108(8)
_cell_length_c                   14.8927(8)
_cell_measurement_reflns_used    9556
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.27
_cell_volume                     1899.15(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10718
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        -0.02
_diffrn_standards_interval_time  198
_diffrn_standards_number         321
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.3936
_exptl_absorpt_correction_T_min  0.3482
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;

SADABS; Sheldric, 1996

;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.66
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+0.2539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0441
_reflns_number_gt                3905
_reflns_number_total             3970
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021000x_s1.cif
_cod_data_source_block           lbadiph
_cod_database_code               4113373