Catalytic Enantioselective Desymmetrization ofmeso-Diamines: A Dual Small-Molecule Catalysis Approach
Chandra Kanta De; Daniel Seidel; Journal of the American Chemical Society 133 (2011) 14538–14541; doi:10.1021/ja2060462

data_4106779
_publ_section_title
;
 Catalytic Enantioselective Desymmetrization ofmeso-Diamines: A Dual
 Small-Molecule Catalysis Approach
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14538
_journal_page_last               14541
_journal_paper_doi               10.1021/ja2060462
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H37 Cl2 N5 O4'
_chemical_formula_weight         650.59
_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                90.00
_cell_angle_beta                 97.186(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5424(14)
_cell_length_b                   14.242(3)
_cell_length_c                   17.525(3)
_cell_measurement_reflns_used    1127
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.34
_cell_volume                     1620.1(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX CCD diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0752
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11739
_diffrn_reflns_theta_full        23.56
_diffrn_reflns_theta_max         23.56
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  .925
_exptl_absorpt_correction_T_min  .795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       needle
_exptl_crystal_F_000             684
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .01
_exptl_crystal_size_min          .005
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     640
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0380P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                3598
_reflns_number_total             4806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2060462_si_002.cif
_cod_data_source_block           chandra_180
_cod_database_code               4106779