Catalytic dynamic kinetic reductive addition of simple aldehydes and aldimines with heterobiaryl triflates: harnessing both central and axial chirality.
Ni, Hui; Liu, Anyao; Fu, Xiaoying; Zhang, Xinyi; Xue, Xiaowen; Lyu, Xiang; Lin, Aijun; He, Yuli; Organic & biomolecular chemistry 23 (2025) 5666–5671; doi:10.1039/d5ob00521c

data_7160560
_publ_section_title
;
 Catalytic dynamic kinetic reductive addition of simple aldehydes and
 aldimines with heterobiaryl triflates: harnessing both central and axial
 chirality.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5666
_journal_page_last               5671
_journal_paper_doi               10.1039/d5ob00521c
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H21 N O2'
_chemical_formula_sum            'C27 H21 N O2'
_chemical_formula_weight         391.45
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-27
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-28 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                73.8100(10)
_cell_angle_beta                 73.5040(10)
_cell_angle_gamma                85.1640(10)
_cell_formula_units_Z            1
_cell_length_a                   6.3648(2)
_cell_length_b                   9.0644(3)
_cell_length_c                   9.3365(3)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    173
_cell_measurement_theta_max      74.437
_cell_measurement_theta_min      6.184
_cell_volume                     495.99(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16750
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.428
_diffrn_reflns_theta_min         6.184
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1481 before and 0.0927 after correction.
The Ratio of minimum to maximum transmission is 0.7487.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0815P)^2^+0.0541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                3716
_reflns_number_total             3796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00521c2.cif
_cod_data_source_block           cu_20241641_0m
_cod_depositor_comments          'Adding full bibliography for 7160560.cif.'
_cod_database_code               7160560
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C6(H6), C14(H14), C18(H18), C13(H13), C26(H26), C17(H17), C2(H2),
 C15(H15), C22(H22), C5(H5), C25(H25), C4(H4), C3(H3), C16(H16), C23(H23)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'