Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles
Kohsuke Ohmatsu; Mari Kiyokawa; Takashi Ooi; Journal of the American Chemical Society 133 (2011) 1307–1309; doi:10.1021/ja1102844

data_4105609
_publ_section_title
;
 Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with
 Anion-Recognition Ability: Application to Asymmetric Alkylation of
 Oxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1307
_journal_page_last               1309
_journal_paper_doi               10.1021/ja1102844
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration S
_chemical_formula_moiety         'C43 H37 N4 O, 3(C H Cl3), Cl'
_chemical_formula_sum            'C46 H40 Cl10 N4 O'
_chemical_formula_weight         1019.32
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.076(4)
_cell_angle_beta                 92.249(3)
_cell_angle_gamma                90.223(3)
_cell_formula_units_Z            2
_cell_length_a                   12.291(2)
_cell_length_b                   13.669(3)
_cell_length_c                   14.416(3)
_cell_measurement_reflns_used    6019
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.22
_cell_volume                     2420.1(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      153
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18010
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.9410
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1107
_refine_ls_number_reflns         14326
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0510P)^2^+1.0737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                13602
_reflns_number_total             14326
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1102844_si_002.cif
_cod_data_source_block           1aCl
_cod_original_cell_volume        2420.0(8)
_cod_database_code               4105609