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_1560206
_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
'C39 H56 N4 O4 Yb, 3(C F3 O3 S), C4 H10 O, 3(C H4 O)'
_chemical_formula_sum            'C49 H78 F9 N4 O17 S3 Yb'
_chemical_formula_weight         1435.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 106.2930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9789(5)
_cell_length_b                   20.7474(9)
_cell_length_c                   12.9099(5)
_cell_measurement_reflns_used    9597
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      79.77
_cell_measurement_theta_min      4.16
_cell_volume                     3079.7(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            235169
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.757
_diffrn_reflns_theta_min         4.155
_exptl_absorpt_coefficient_mu    4.592
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7666
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1470
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH, Et2O'
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.192
_refine_diff_density_max         0.619
_refine_diff_density_min         -1.010
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.062(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         13247
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0217
_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^)+(0.0329P)^2^+1.9498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0560
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                13218
_reflns_number_total             13247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc07052a2.cif
_cod_data_source_block           zhx008
_cod_depositor_comments
'Adding full bibliography for 1560204--1560206.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1560206
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.400
_shelx_estimated_absorpt_t_max   0.473
_shelx_res_checksum              18169