Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles
Zhu, Wen-Run; Chen, Qing; Lin, Ning; Chen, Kai-Bin; Zhang, Zhen-Wei; Fang, Gang; Weng, Jiang; Lu, Gui; Organic Chemistry Frontiers 5 (2018) 1375–; doi:10.1039/C8QO00044A

data_1554253
_publ_section_title
;
 Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato
 oxindoles with 3-trifluoroethylidene oxindoles: an approach for the
 synthesis of 3&#x2032;-trifluoromethyl substituted
 3,2&#x2032;-pyrrolidinyl-bispirooxindoles
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1375
_journal_paper_doi               10.1039/C8QO00044A
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H21 Br F3 N3 O4 S'
_chemical_formula_weight         596.42
_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
_audit_update_record
;
2018-01-08 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.81190(10)
_cell_length_b                   10.41340(10)
_cell_length_c                   27.1396(3)
_cell_measurement_reflns_used    13428
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.1800
_cell_measurement_theta_min      3.2370
_cell_volume                     2490.38(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            24246
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.363
_diffrn_reflns_theta_min         3.257
_exptl_absorpt_coefficient_mu    3.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.8828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4705
_reflns_number_total             4911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00044a2.cif
_cod_data_source_block           B
_cod_database_code               1554253
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.413
_shelx_estimated_absorpt_t_max   0.716
_shelx_res_checksum              39022