Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2'-pyrrolidines].
Akaev, Andrey A.; Bezzubov, Stanislav I.; Desyatkin, Victor G.; Vorobyeva, Nataliya S.; Majouga, Alexander G.; Melnikov, Mikhail Ya; Budynina, Ekaterina M.; The Journal of organic chemistry 84 (2019) 3340–3356; doi:10.1021/acs.joc.8b03208

data_4033924
_publ_contact_author             'Ekaterina Budynina'
_publ_section_title
;
 Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to
 Iminooxindoles: Access to Spiro[oxindole-3,2'-pyrrolidines].
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3340
_journal_page_last               3356
_journal_paper_doi               10.1021/acs.joc.8b03208
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C31 H25 N3 O2, 2(C2 H6 S O)'
_chemical_formula_sum            'C35 H37 N3 O4 S2'
_chemical_formula_weight         627.79
_chemical_melting_point_gt       433
_chemical_melting_point_lt       434
_chemical_name_systematic
;
(3RS,3&#x0092;RS,5&#x0092;RS)-1&#x0092;&#x0092;-Methyl-1&#x0092;,5&#x0092;-diphenyldispiro[indoline-3,2&#x0092;-pyrrolidine-3&#x0092;,3&#x0092;&#x0092;-indoline]-2,2&#x0092;&#x0092;-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 113.2280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9951(8)
_cell_length_b                   33.343(3)
_cell_length_c                   10.4541(8)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.522
_cell_measurement_theta_min      2.206
_cell_volume                     3201.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37696
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.206
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_transmission_factor_max   0.930
_exptl_transmission_factor_min   0.893
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         9311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+1.6016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8375
_reflns_number_total             9311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03208_si_002.cif
_cod_data_source_block           3ao
_cod_original_cell_volume        3201.6(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4033924
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.893
_shelx_estimated_absorpt_t_max   0.930
_shelx_res_checksum              19365
_shelx_hkl_checksum              56707