Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron.
Zhou, Mingkang; Li, Kaidi; Chen, Dongping; Xu, Ronghua; Xu, Guangqing; Tang, Wenjun; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c04558

data_4135037
_publ_section_title
;
 Enantioselective Reductive Coupling of Imines Templated by Chiral
 Diboron.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c04558
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H28 N2 O2'
_chemical_formula_weight         376.48
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                85.704(2)
_cell_angle_beta                 77.910(2)
_cell_angle_gamma                89.183(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0937(3)
_cell_length_b                   10.1710(6)
_cell_length_c                   10.7742(6)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.226
_cell_measurement_theta_min      11.673
_cell_volume                     544.28(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14368
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.493
_diffrn_reflns_theta_min         5.836
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             202
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
; 
 Flack x determined using 1710 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.10(9)
_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   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.0459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                3634
_reflns_number_total             3748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c04558_si_002.cif
_cod_data_source_block           cu_d8v19398_0m
_cod_database_code               4135037
_shelx_estimated_absorpt_t_min   0.899
_shelx_estimated_absorpt_t_max   0.955
_shelxl_version_number           2013-4
_shelx_res_checksum              39275
_shelx_hkl_checksum              98724