The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst.
Cheng, Ping; Guo, Wengang; Chen, Ping; Liu, Yan; Du, Xin; Li, Can; Chemical communications (Cambridge, England) 52 (2016) 3418–3421; doi:10.1039/c5cc10292h

data_7118693
_publ_section_title
;
 The enantioselective construction of chiral spirooxindole-based
 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a
 bifunctional catalyst.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3418
_journal_page_last               3421
_journal_paper_doi               10.1039/c5cc10292h
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H23 Br N2 O4 S'
_chemical_formula_weight         491.39
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-01-26 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.504(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3517(8)
_cell_length_b                   17.5995(15)
_cell_length_c                   13.2555(11)
_cell_measurement_reflns_used    1146
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.240
_cell_measurement_theta_min      4.662
_cell_volume                     2348.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.1466
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13809
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         1.958
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.037(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         8545
_refine_ls_number_restraints     82
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4040
_reflns_number_total             8545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10292h2.cif
_cod_data_source_block           cd15013
_cod_depositor_comments
'Adding full bibliography for 7118693--7118694.cif.'
_cod_database_code               7118693
_shelx_estimated_absorpt_t_min   0.730
_shelx_estimated_absorpt_t_max   0.821
_shelxl_version_number           2013-4
_shelx_res_checksum              14547