Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines.
Rong, Zi-Qiang; Zhang, Yao; Chua, Raymond Hong Bing; Pan, Hui-Jie; Zhao, Yu; Journal of the American Chemical Society 137 (2015) 4944–4947; doi:10.1021/jacs.5b02212

data_4129410
_publ_section_title
;
 Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four
 Isomers to Diastereo- and Enantiopure \a-Branched Amines.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4944
_journal_page_last               4947
_journal_paper_doi               10.1021/jacs.5b02212
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C22 H24 N'
_chemical_formula_sum            'C22 H24 N'
_chemical_formula_weight         302.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7245(2)
_cell_length_b                   8.5410(3)
_cell_length_c                   29.6456(11)
_cell_measurement_reflns_used    7363
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.2
_cell_measurement_theta_min      4.474
_cell_volume                     1702.66(10)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX v2014.9.0'
_computing_data_reduction        'Saint, APEX v2014.9.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2014.9.0.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Sir 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            6775
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.299
_diffrn_reflns_theta_min         5.970
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.002(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0523
_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^)+(0.1065P)^2^+0.1779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                3193
_reflns_number_total             3224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b02212_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4129410
_shelx_estimated_absorpt_t_min   0.843
_shelx_estimated_absorpt_t_max   0.950
_shelxl_version_number           2014/6
_shelx_res_checksum              54660
_shelx_hkl_checksum              31940