A novel one-pot multi-component synthesis of 3, 3’disubstituted oxindoles and spirooxindoles scaffold via Sn-catalyzed C(sp3)-H functionalization of azaarenes by sequential Knoevenagel-Michael-Cyclization reaction
Mulla, Shafeek Abdul Rashid; Chavan, Santosh S.; Pathan, Mohsinkhan Y.; Thorat, Sridhar Hanamant; Gonnade, Rajesh G.; RSC Adv.  (2015) –; doi:10.1039/C5RA16334J

data_7222052
_publ_section_title
;
 A novel one-pot multi-component synthesis of 3, 3&#x2019;disubstituted
 oxindoles and spirooxindoles scaffold via Sn-catalyzed C(sp3)-H
 functionalization of azaarenes by sequential
 Knoevenagel-Michael-Cyclization reaction
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA16334J
_journal_year                    2015
_chemical_formula_moiety         'C22 H19 N5 O'
_chemical_formula_sum            'C22 H19 N5 O'
_chemical_formula_weight         369.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.570(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3799(12)
_cell_length_b                   13.0555(12)
_cell_length_c                   11.5532(11)
_cell_measurement_reflns_used    7218
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      3.04
_cell_volume                     1846.4(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19861
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.046
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0810P)^2^+0.5940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                3086
_reflns_number_total             4016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra16334j2.cif
_cod_data_source_block           expt_363
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7222052