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_7226100
_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'
_chemical_formula_sum            'C19 H12 Br N3 O2'
_chemical_formula_weight         394.23
_chemical_melting_point          388
_chemical_name_common            ketone
_chemical_name_systematic
2-(5-bromo-2-oxo-3-(2-oxo-2-phenylethyl)indolin-3-yl)malononitrile
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_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                72.6120(10)
_cell_angle_beta                 68.3510(10)
_cell_angle_gamma                78.5860(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9365(8)
_cell_length_b                   10.0229(9)
_cell_length_c                   10.5846(10)
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.46
_cell_volume                     836.80(13)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7437
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  0.7726
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0268P)^2^+0.3259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                2521
_reflns_number_total             2952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra16975a2.cif
_cod_data_source_block           a18075
_cod_database_code               7226100