Organocatalytic Asymmetric Domino oxa-Michael-Mannich-[1,3]-Amino Rearrangement Reaction of N-Tosylsalicylimines to α,β-Unsaturated Aldehydes by Diarylprolinol Silyl Ethers.
Hu, Sha; Wang, Jiaqi; Huang, Guanxin; Zhu, Kejie; Chen, Fener; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02939

data_4037753
_publ_section_title
;
 Organocatalytic Asymmetric Domino oxa-Michael-Mannich-[1,3]-Amino
 Rearrangement Reaction of N-Tosylsalicylimines to \a,\b-Unsaturated
 Aldehydes by Diarylprolinol Silyl Ethers.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02939
_journal_year                    2019
_chemical_formula_sum            'C23 H18 Br N O3 S'
_chemical_formula_weight         468.35
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9348(6)
_cell_length_b                   20.2930(6)
_cell_length_c                   5.3935(2)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      58.07
_cell_measurement_theta_min      3.79
_cell_volume                     2072.42(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            40366
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.066
_diffrn_reflns_theta_min         4.301
_exptl_absorpt_coefficient_mu    2.538
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       rod
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.001(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0194
_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^)+(0.0280P)^2^+0.3312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0523
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4318
_reflns_number_total             4389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02939_si_001.cif
_cod_data_source_block           ga_90827aa_a
_cod_database_code               4037753
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.750
_shelx_estimated_absorpt_t_max   0.905
_shelx_res_checksum              38645
_shelx_hkl_checksum              90843