Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed Ring-Opening Formal [3 + 2]-Cycloaddition of Spirovinylcyclopropyl Oxindole and 3-Oxindole Derivatives.
Xiao, Jun-An; Li, Yu-Chun; Luo, Zhi-Jin; Cheng, Xiu-Liang; Deng, Zhi-Xiong; Chen, Wen-Qiang; Su, Wei; Yang, Hua; The Journal of organic chemistry 84 (2019) 2297–2306; doi:10.1021/acs.joc.8b02889

data_4033740
_publ_section_title
;
 Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed
 Ring-Opening Formal [3 + 2]-Cycloaddition of Spirovinylcyclopropyl
 Oxindole and 3-Oxindole Derivatives.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2297
_journal_page_last               2306
_journal_paper_doi               10.1021/acs.joc.8b02889
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C28 H24 N2 O3'
_chemical_formula_weight         436.48
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           Triclini
_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                92.194(5)
_cell_angle_beta                 93.218(5)
_cell_angle_gamma                96.830(5)
_cell_formula_units_Z            2
_cell_length_a                   9.3074(13)
_cell_length_b                   9.6932(14)
_cell_length_c                   12.3596(18)
_cell_measurement_reflns_used    4191
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.87
_cell_volume                     1104.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21025
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       CUBE
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0602P)^2^+0.2267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                3226
_reflns_number_total             4191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02889_si_003.cif
_cod_data_source_block           ja
_cod_depositor_comments
;

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C2.55 H2.18 N0.18 O0.27'
_cod_original_formula_units_Z    22
_cod_original_formula_weight     39.68
_cod_database_code               4033740