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_4120951
_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_formula_moiety         'C11 H15 Br N2 O'
_chemical_formula_sum            'C11 H15 Br N2 O'
_chemical_formula_weight         271.16
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.43119(19)
_cell_length_b                   11.1622(4)
_cell_length_c                   16.6648(6)
_cell_measurement_reflns_used    10510
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.96
_cell_volume                     1196.30(7)
_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    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13848
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.500
_exptl_absorpt_correction_T_max  0.487
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       block
_exptl_crystal_F_000             552.00
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.230
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  899 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.0249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0535
_reflns_number_gt                2147
_reflns_number_total             2194
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja408296h_si_005.cif
_cod_data_source_block           GP-502
_cod_database_code               4120951