Cobalt-catalyzed diastereo- and enantioselective reductive coupling of cyclobutenes and aldehydes through umpolung reactivity.
Lin, Chuiyi; Zhang, Jiwu; Zhang, Zhihan; Chong, Qinglei; Meng, Fanke; Chemical science 16 (2025) 16250–16258; doi:10.1039/d5sc03755g

data_1575312
_publ_section_title
;
 Cobalt-catalyzed diastereo- and enantioselective reductive coupling of
 cyclobutenes and aldehydes through umpolung reactivity.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              16250
_journal_page_last               16258
_journal_paper_doi               10.1039/d5sc03755g
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 F3 N O3'
_chemical_formula_sum            'C21 H18 F3 N O3'
_chemical_formula_weight         389.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-07-26 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.317(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.1984(5)
_cell_length_b                   6.0121(5)
_cell_length_c                   29.4619(10)
_cell_measurement_reflns_used    14155
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4320
_cell_measurement_theta_min      2.9790
_cell_volume                     3574.8(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.989
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            29298
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.937
_diffrn_reflns_theta_min         3.002
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87673
_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    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         6698
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0161P)^2^+9.8367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.779
_reflns_number_gt                6264
_reflns_number_total             6698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03755g2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 1575312--1575313.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1575312
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.825
_shelx_estimated_absorpt_t_max   0.864
_shelx_res_checksum              60611