Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines.
Song, Yong-Xing; Du, Da-Ming; The Journal of organic chemistry 83 (2018) 9278–9290; doi:10.1021/acs.joc.8b01245

data_4035361
_publ_section_title
;
 Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via
 Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of
 Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9278
_journal_page_last               9290
_journal_paper_doi               10.1021/acs.joc.8b01245
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H23 Br F3 N3 O4 S2'
_chemical_formula_weight         690.54
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9251(4)
_cell_length_b                   11.4490(4)
_cell_length_c                   24.8360(10)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.65
_cell_measurement_theta_min      2.42
_cell_volume                     3106.5(2)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.034
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         1.640
_exptl_absorpt_coefficient_mu    1.515
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.805
_exptl_transmission_factor_min   0.751
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0593P)^2^+1.0655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4735
_reflns_number_total             5468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01245_si_002.cif
_cod_data_source_block           syx342
_cod_database_code               4035361
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              38112
_shelx_hkl_checksum              19390