Selective Synthesis of Functionalized Spiro[indoline-3,2'-pyridines] and Spiro[indoline-3,4'-pyridines] by Lewis Acid Catalyzed Reactions of Acetylenedicarboxylate, Arylamines, and Isatins.
Gao, Hong; Sun, Jing; Yan, Chao-Guo; The Journal of organic chemistry 79 (2014) 4131–4136; doi:10.1021/jo500144z

data_4029300
_publ_section_title
;
 Selective Synthesis of Functionalized Spiro[indoline-3,2'-pyridines] and
 Spiro[indoline-3,4'-pyridines] by Lewis Acid Catalyzed Reactions of
 Acetylenedicarboxylate, Arylamines, and Isatins.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4131
_journal_page_last               4136
_journal_paper_doi               10.1021/jo500144z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C38 H38 N2 O9'
_chemical_formula_sum            'C38 H38 N2 O9'
_chemical_formula_weight         666.70
_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
_cell_angle_alpha                105.457(3)
_cell_angle_beta                 108.034(3)
_cell_angle_gamma                98.027(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2438(11)
_cell_length_b                   13.8664(15)
_cell_length_c                   14.1071(15)
_cell_measurement_reflns_used    6524
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.90
_cell_measurement_theta_min      2.34
_cell_volume                     1781.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28605
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_platon_squeeze_details          ' '
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         8180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0654
_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^)+(0.0782P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                4176
_reflns_number_total             8296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500144z_si_001.cif
_cod_data_source_block           1k
_cod_depositor_comments
'Adding full bibliography for 4029299--4029301.cif.'
_cod_database_code               4029300