Synthesis of (E)-3-(Isobenzofuran-3(1H)-ylidene)indolin-2-ones by the Palladium-Catalyzed Intramolecular C-H Functionalization Process
Peng Peng; Bo-Xiao Tang; Shao-Feng Pi; Yun Liang; Jin-Heng Li; Journal of Organic Chemistry 74 (2009) 3569–3572; doi:10.1021/jo900437p

data_4024517
_publ_section_title
;
Synthesis of (E)-3-(Isobenzofuran-3(1H)-ylidene)indolin-2-ones by the
Palladium-Catalyzed Intramolecular C-H Functionalization Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3569
_journal_page_last               3572
_journal_paper_doi               10.1021/jo900437p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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                 105.711(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5969(17)
_cell_length_b                   7.8980(10)
_cell_length_c                   14.3767(19)
_cell_measurement_reflns_used    2294
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.515
_cell_volume                     1376.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7011
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0644P)^2^+0.3939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2061
_reflns_number_total             2429
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo900437p_si_002.cif
_cod_data_source_block           6191m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024517