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_7118694
_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 H21 Br N2 O5 S'
_chemical_formula_weight         444.47
_chemical_name_systematic
; 
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0059(11)
_cell_length_b                   12.9439(15)
_cell_length_c                   18.305(2)
_cell_measurement_reflns_used    3617
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.719
_cell_measurement_theta_min      4.450
_cell_volume                     2133.8(4)
_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'
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_computing_structure_solution    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_max 1.000
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_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
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_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12095
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        25.242
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_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colorless
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_exptl_crystal_description       prismatic
_exptl_crystal_F_000             928
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_refine_ls_abs_structure_details
; 
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0491
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_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^)+(0.0669P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.752
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     0.999
_reflns_number_gt                3685
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10292h2.cif
_cod_data_source_block           cd16057
_cod_depositor_comments
'Adding full bibliography for 7118693--7118694.cif.'
_cod_original_cell_volume        2133.9(4)
_cod_database_code               7118694
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              32049