Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines
Wang, Chao; Chen, Xiao-Hua; Zhou, Shi-Ming; Gong, Liu-Zhu; Chemical Communications (Cambridge, United Kingdom) 46 (2010) 1275–1277; doi:10.1039/b917246g

data_7111563
_publ_section_title
;
 Asymmetric organocatalytic formal double-arylation of azomethines for the
 synthesis of highly enantiomerically enriched isoindolines
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   8
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1275
_journal_page_last               1277
_journal_paper_doi               10.1039/b917246g
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H21 Cl2 N O6'
_chemical_formula_weight         490.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 94.055(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.314(5)
_cell_length_b                   22.630(5)
_cell_length_c                   12.582(5)
_cell_measurement_reflns_used    23144
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.6295
_cell_measurement_theta_min      1.9465
_cell_volume                     2361.3(18)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29413
_diffrn_reflns_theta_full        62.78
_diffrn_reflns_theta_max         62.78
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_T_max  0.5509
_exptl_absorpt_correction_T_min  0.4137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         7332
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+1.9006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                6900
_reflns_number_total             7332
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7105251
_cod_data_source_file            b917246gsup1.cif
_cod_data_source_block           080927-cu
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7111563