Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.
Hu, Qiupeng; Kondoh, Azusa; Terada, Masahiro; Chemical science 9 (2018) 4348–4351; doi:10.1039/c8sc00808f

data_1549269
_publ_section_title
;
 Enantioselective direct Mannich-type reactions of 2-benzylpyridine
 N-oxides catalyzed by chiral bis(guanidino)iminophosphorane
 organosuperbase.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              4348
_journal_page_last               4351
_journal_paper_doi               10.1039/c8sc00808f
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C28 H33 Br N2 O3'
_chemical_formula_sum            'C28 H33 Br N2 O3'
_chemical_formula_weight         525.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_update_record
;
2017-12-15 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.627(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.4738(9)
_cell_length_b                   16.810(3)
_cell_length_c                   14.183(2)
_cell_measurement_reflns_used    9459
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1298.8(4)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r15'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2013/4 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11065
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.131
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             548.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.65
_refine_ls_abs_structure_details
;
 Flack x determined using 1502 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.075(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5645
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.1471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1407
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                4109
_reflns_number_total             5645
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8sc00808f2.cif
_cod_data_source_block           01
_cod_depositor_comments          'Adding full bibliography for 1549269.cif.'
_cod_database_code               1549269
_shelxl_version_number           2013-4
_shelx_res_checksum              42384
_shelx_hkl_checksum              2243