Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H<sub>2</sub>.
Hoshimoto, Yoichi; Kinoshita, Takuya; Hazra, Sunit; Ohashi, Masato; Ogoshi, Sensuke; Journal of the American Chemical Society 140 (2018) 7292–7300; doi:10.1021/jacs.8b03626

data_4132388
_publ_section_title
;
 Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines
 with Aldehydes Using H<sub>2</sub>.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7292
_journal_page_last               7300
_journal_paper_doi               10.1021/jacs.8b03626
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C16 H11 N O5'
_chemical_formula_sum            'C16 H11 N O5'
_chemical_formula_weight         297.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.7992(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   13.67230(17)
_cell_length_b                   7.88868(8)
_cell_length_c                   24.8410(3)
_cell_measurement_reflns_used    6607
_cell_measurement_temperature    213
_cell_measurement_theta_max      74.07
_cell_measurement_theta_min      6.46
_cell_volume                     2679.00(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      213
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13138
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         74.428
_diffrn_reflns_theta_min         3.559
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0522P)^2^+1.0302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2408
_reflns_number_total             2681
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8b03626_si_002.cif
_cod_data_source_block           3ou
_cod_database_code               4132388
_shelx_res_checksum              54267
_shelx_hkl_checksum              57390