Water Enables Diastereodivergency in Bispidine-Based Chiral Amine-Catalyzed Asymmetric Mannich Reaction of Cyclic N-Sulfonyl Ketimines with Ketones
Li, Gonglin; Zhang, Yan; Zeng, Hongkun; Feng, Xiaoming; Su, Zhishan; Lin, Lili; Chemical Science  (2022) –; doi:10.1039/D2SC00446A

data_1566685
_publ_section_title
;
 Water Enables Diastereodivergency in Bispidine-Based Chiral
 Amine-Catalyzed Asymmetric Mannich Reaction of Cyclic N-Sulfonyl
 Ketimines with Ketones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00446A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 N2 O6 S'
_chemical_formula_sum            'C16 H20 N2 O6 S'
_chemical_formula_weight         368.40
_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-2018/3
_audit_update_record
;
2021-06-17 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1051(4)
_cell_length_b                   14.1921(6)
_cell_length_c                   15.2659(7)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      4.25
_cell_volume                     1756.01(14)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0699
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24936
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.361
_diffrn_reflns_theta_min         4.253
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.5546
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
; 
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.072(10)
_refine_ls_extinction_coef       0.0063(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0581P)^2^+0.6637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3065
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00446a2.cif
_cod_data_source_block           lgl013
_cod_database_code               1566685
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.414
_shelx_estimated_absorpt_t_max   0.870
_shelx_res_checksum              10390
_shelx_hkl_checksum              31388