Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism
Philip C. Bulman Page; Christopher J. Bartlett; Yohan Chan; David Day; Phillip Parker; Benjamin R. Buckley; Geracimos A. Rassias; Alexandra M. Z. Slawin; Steven M. Allin; Jérôme Lacour; André Pinto; Journal of Organic Chemistry 77 (2012) 6128–6138; doi:10.1021/jo300915u

data_4027324
_publ_section_title
;
 Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring
 Dynamically Controlled Atropoisomerism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6128
_journal_page_last               6138
_journal_paper_doi               10.1021/jo300915u
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H32 N O2,C24 H20 B,3(C H2 Cl2)'
_chemical_formula_sum            'C62 H58 B Cl6 N O2'
_chemical_formula_weight         1072.60
_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                   11.458(2)
_cell_length_b                   17.247(3)
_cell_length_c                   27.663(6)
_cell_measurement_reflns_used    5125
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.2075
_cell_measurement_theta_min      1.8872
_cell_volume                     5466.7(18)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_method       '\w and \f 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  0.3112
_diffrn_reflns_av_sigmaI/netI    0.4355
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34687
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.83251
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.2400
_exptl_crystal_size_mid          0.0500
_exptl_crystal_size_min          0.0500
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     644
_refine_ls_number_reflns         9884
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.3058
_refine_ls_R_factor_gt           0.1056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2036
_refine_ls_wR_factor_ref         0.2796
_reflns_number_gt                3000
_reflns_number_total             9884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300915u_si_001_3.cif
_cod_data_source_block           30
_cod_original_cell_volume        5466.5(19)
_cod_database_code               4027324