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_1560204
_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 ad
_chemical_formula_moiety         'C19 H18 N2 O2 S2'
_chemical_formula_sum            'C19 H18 N2 O2 S2'
_chemical_formula_weight         370.47
_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-2017/1
_audit_update_record
;
2020-02-11 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.2220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6009(2)
_cell_length_b                   10.3983(2)
_cell_length_c                   9.9867(2)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      74.75
_cell_measurement_theta_min      4.89
_cell_volume                     901.95(3)
_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-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16275
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.738
_diffrn_reflns_theta_min         4.895
_exptl_absorpt_coefficient_mu    2.797
_exptl_absorpt_correction_T_max  0.8321
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1633 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.036(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0284P)^2^+0.1612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3574
_reflns_number_total             3635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc07052a2.cif
_cod_data_source_block           zhx002
_cod_depositor_comments
'Adding full bibliography for 1560204--1560206.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1560204
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.619
_shelx_estimated_absorpt_t_max   0.769
_shelx_res_checksum              89117