Catalytic asymmetric addition of thiols to silyl glyoxylates for synthesis of multi-hetero-atom substituted carbon stereocenters.
Guan, Mingming; Wang, Shiyu; Luo, Yao; Cao, Weidi; Liu, Xiaohua; Feng, Xiaoming; Chemical science 12 (2021) 7498–7503; doi:10.1039/d1sc01096d

data_1562058
_publ_section_title
;
 Catalytic asymmetric addition of thiols to silyl glyoxylates for
 synthesis of multi-hetero-atom substituted carbon stereocenters.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              7498
_journal_page_last               7503
_journal_paper_doi               10.1039/d1sc01096d
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety
'C39 H56 N4 O4 Y, 3(C F3 O3 S), C4 H10 O, 3(C H4 O)'
_chemical_formula_sum            'C49 H78 F9 N4 O17 S3 Y'
_chemical_formula_weight         1351.24
_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
;
2021-02-24 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.2310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9751(5)
_cell_length_b                   20.8149(9)
_cell_length_c                   12.9319(6)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      80.63
_cell_measurement_theta_min      3.56
_cell_volume                     3094.9(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 0.998
_diffrn_measured_fraction_theta_max 0.993
_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  0.0393
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            127367
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.719
_diffrn_reflns_theta_min         3.560
_exptl_absorpt_coefficient_mu    3.102
_exptl_absorpt_correction_T_max  0.8979
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.062(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         13286
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+1.3804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                13233
_reflns_number_total             13286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01096d2.cif
_cod_data_source_block           loy015
_cod_depositor_comments
'Adding full bibliography for 1562057--1562058.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1562058
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.378
_shelx_estimated_absorpt_t_max   0.632
_shelx_res_checksum              35407
_shelx_hkl_checksum              89473