Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons.
Chen, Tian; Wang, Hao-Yang; Xu, Ronghua; Xu, Guangqing; Yang, He; Sun, Jiangtao; Chung, Lung Wa; Tang, Wenjun; Chemical science 16 (2025) 13298–13305; doi:10.1039/d5sc03633j

data_1574886
_publ_section_title
;
 Asymmetric intramolecular reductive coupling of bisimines templated by
 chiral diborons.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              13298
_journal_page_last               13305
_journal_paper_doi               10.1039/d5sc03633j
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br N2 O'
_chemical_formula_sum            'C17 H15 Br N2 O'
_chemical_formula_weight         343.22
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-03-03 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1594(4)
_cell_length_b                   15.0950(11)
_cell_length_c                   18.2386(13)
_cell_measurement_reflns_used    5603
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4490
_cell_measurement_theta_min      3.7710
_cell_volume                     1420.44(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8693
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.125
_diffrn_reflns_theta_min         3.801
_exptl_absorpt_coefficient_mu    3.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.179
_refine_diff_density_min         -1.465
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.035(17)
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0523P)^2^+3.8115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.589
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                2384
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03633j2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 1574884--1574886.cif.'
_cod_database_code               1574886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.478
_shelx_estimated_absorpt_t_max   0.537
_shelx_res_checksum              96448