Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions.
Basavaiah, Deevi; Reddy, Kanumuri Ramesh; Organic letters 9 (2007) 57–60; doi:10.1021/ol062561m

data_1505237
_publ_section_title
;
 Simple and one-pot protocol for synthesis of indene-spiro-oxindoles
 involving tandem Prins and Friedel-Crafts reactions.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              57
_journal_page_last               60
_journal_paper_doi               10.1021/ol062561m
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_chemical_melting_point          122(2)
_chemical_name_systematic
; 
 (3-Phenyl-1H-indene)-1-spiro-3'-(1'-ethylindolin-2'-one) 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.892(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.038(2)
_cell_length_b                   12.112(2)
_cell_length_c                   14.089(2)
_cell_measurement_temperature    298
_cell_volume                     1863.4(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega 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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10110
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABAS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                2342
_reflns_number_total             3673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062561msi20061017_041629.cif
_cod_data_source_block           14
_cod_original_cell_volume        1863.5(5)
_cod_original_sg_symbol_H-M      'p 21/n'
_cod_database_code               1505237