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_4132387
_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         'C15 H11 N O3'
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 93.510(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.6526(15)
_cell_length_b                   7.9132(5)
_cell_length_c                   6.8187(4)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    123
_cell_measurement_theta_max      72.0890
_cell_measurement_theta_min      5.8910
_cell_volume                     1219.99(13)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9971
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.390
_diffrn_reflns_theta_min         3.910
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1506P)^2^+0.2693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2038
_refine_ls_wR_factor_ref         0.2272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1835
_reflns_number_total             2431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03626_si_002.cif
_cod_data_source_block           3av
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4132387
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              27901
_shelx_hkl_checksum              5941