Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged Organosuperbase for the Enantioselective Amination of Ketones
Tadahiro Takeda; Masahiro Terada; Journal of the American Chemical Society 135 (2013) 15306–15309; doi:10.1021/ja408296h

data_4120948
_publ_section_title
;
 Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged
 Organosuperbase for the Enantioselective Amination of Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15306
_journal_page_last               15309
_journal_paper_doi               10.1021/ja408296h
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C49.50 H53 Cl N8 O P'
_chemical_formula_sum            'C49.5 H53 Cl N8 O P'
_chemical_formula_weight         842.44
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.4604(11)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   18.3361(4)
_cell_length_b                   10.44041(19)
_cell_length_c                   23.7115(5)
_cell_measurement_reflns_used    40385
_cell_measurement_temperature    103
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.20
_cell_volume                     4518.65(16)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      103
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            50955
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       prism
_exptl_crystal_F_000             1784.00
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.530
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  7391 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     1127
_refine_ls_number_reflns         16007
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0749
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1337P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2232
_reflns_number_gt                10642
_reflns_number_total             16013
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja408296h_si_002.cif
_cod_data_source_block           130614
_cod_original_cell_volume        4518.66(15)
_cod_original_formula_sum        'C49.50 H53 Cl N8 O P'
_cod_database_code               4120948