The synthesis of sterically hindered amines by a direct reductive amination of ketones.
Yagafarov, Niyaz Z.; Kolesnikov, Pavel N.; Usanov, Dmitry L.; Novikov, Valentin V.; Nelyubina, Yulia V.; Chusov, Denis; Chemical communications (Cambridge, England) 52 (2016) 1397–1400; doi:10.1039/c5cc08577b

data_7118463
_publ_section_title
;
 The synthesis of sterically hindered amines by a direct reductive
 amination of ketones.
;
_journal_issue                   7
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1397
_journal_page_last               1400
_journal_paper_doi               10.1039/c5cc08577b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C12 H20 N O, C2 F3 O2'
_chemical_formula_sum            'C14 H20 F3 N O3'
_chemical_formula_weight         307.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-07-10 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7764(12)
_cell_length_b                   15.755(2)
_cell_length_c                   25.521(4)
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     3126.8(8)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0858
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_diffrn_reflns_laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_l_min       -32
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_min         2.586
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
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_exptl_crystal_description       needle
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_exptl_crystal_size_max          0.350
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_refine_ls_extinction_coef       0.0062(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.376
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0734
_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^)+(0.0500P)^2^+2.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc08577b2.cif
_cod_data_source_block           1e
_cod_original_cell_volume        3126.7(8)
_cod_database_code               7118463
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014/6
_shelx_res_checksum              94448