Molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction: an efficient and mild condition for the synthesis of 3,3-disubstituted oxindoles with all carbon quaternary center
Guo, Yi-Lin; Li, Yu-Hsun; Chang, Hsuan-Hao; Kuo, Ting-Shen; Han, Jeng-Liang; RSC Adv.  (2016) –; doi:10.1039/C6RA16975A

data_7226099
_publ_section_title
;
 Molecular sieve mediated sequential Knoevenagel
 condensation/decarboxylative Michael addition reaction: an efficient and
 mild condition for the synthesis of 3,3-disubstituted oxindoles with all
 carbon quaternary center
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA16975A
_journal_year                    2016
_chemical_compound_source        Synthesized
_chemical_formula_moiety         'C19 H12 Br N3 O2 S'
_chemical_formula_sum            'C19 H12 Br N3 O2 S'
_chemical_formula_weight         426.29
_chemical_melting_point          446
_chemical_name_common            thioester
_chemical_name_systematic
'S-phenyl 2-(5-bromo-3-(dicyanomethyl)-2-oxoindolin-3-yl)ethanethioate'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-05-23 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1742(7)
_cell_length_b                   9.5722(6)
_cell_length_c                   34.645(2)
_cell_measurement_reflns_used    7667
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.86
_cell_volume                     3705.7(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            18717
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_T_max  0.7821
_exptl_absorpt_correction_T_min  0.3747
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+1.0254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                2733
_reflns_number_total             3277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra16975a2.cif
_cod_data_source_block           18074
_cod_database_code               7226099