Visible-light-driven asymmetric aldol reaction of ketones and glycinates <i>via</i> synergistic Lewis acid/photoredox catalysis.
Tan, Jiuqi; Yang, Longqing; Su, Hanyu; Yang, Yuntian; Zhong, Ziwei; Feng, Xiaoming; Liu, Xiaohua; Chemical science 15 (2024) 16050–16058; doi:10.1039/d4sc04900d

data_1573010
_publ_section_title
;
 Visible-light-driven asymmetric aldol reaction of ketones and glycinates
 <i>via</i> synergistic Lewis acid/photoredox catalysis.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16050
_journal_page_last               16058
_journal_paper_doi               10.1039/d4sc04900d
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H34 N2 O3'
_chemical_formula_sum            'C28 H34 N2 O3'
_chemical_formula_weight         446.57
_chemical_melting_point          'DCM, PE'
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-12-20 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.99400(10)
_cell_length_b                   16.4455(4)
_cell_length_c                   24.7082(6)
_cell_measurement_reflns_used    8960
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      79.31
_cell_measurement_theta_min      3.23
_cell_volume                     2435.59(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15096
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.484
_diffrn_reflns_theta_min         3.228
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8638
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.171
_refine_ls_abs_structure_details
; 
 Flack x determined using 1844 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0713
_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^)+(0.1100P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                4718
_reflns_number_total             5087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04900d2.cif
_cod_data_source_block           shb026
_cod_database_code               1573010
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.956
_shelx_res_checksum              43836
_shelx_hkl_checksum              93380