Chiral Lewis acid-bonded picolinaldehyde enables enantiodivergent carbonyl catalysis in the Mannich/condensation reaction of glycine ester
Zhong, Xia; Zhong, Ziwei; Wu, Zhikun; Ye, Zhen; Feng, Yuxiang; Dong, Shunxi; Liu, Xiaohua; Peng, Qian; Feng, Xiaoming; Chemical Science 12 (2021) 4353–4360; doi:10.1039/D0SC07052A

data_1560205
_publ_section_title
;
 Chiral Lewis acid-bonded picolinaldehyde enables enantiodivergent
 carbonyl catalysis in the Mannich/condensation reaction of glycine ester
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4353
_journal_page_last               4360
_journal_paper_doi               10.1039/D0SC07052A
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety
'C31 H44 N4 O4 Yb, C4 H8 O, 3(C F3 O3 S), 2(H2 O)'
_chemical_formula_sum            'C38 H56 F9 N4 O16 S3 Yb'
_chemical_formula_weight         1265.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-20 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.0690(11)
_cell_length_b                   24.5839(12)
_cell_length_c                   9.5501(4)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.42
_cell_volume                     5416.1(4)
_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'
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_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            320140
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.288
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.6163
_exptl_absorpt_correction_T_min  0.3526
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       block
_exptl_crystal_F_000             2556
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF, EA, Hexane'
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.963
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.019(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         12456
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0215
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0251P)^2^+5.4420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0572
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                12275
_reflns_number_total             12456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc07052a2.cif
_cod_data_source_block           zhx009
_cod_depositor_comments
'Adding full bibliography for 1560204--1560206.cif.'
_cod_database_code               1560205
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.488
_shelx_estimated_absorpt_t_max   0.737
_shelx_res_checksum              88672
_shelx_fab_checksum              94732