Diastereo- and Enantioselective Construction of 3,3'-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions.
Dai, Wei; Jiang, Xiao-Li; Wu, Qiong; Shi, Feng; Tu, Shu-Jiang; The Journal of organic chemistry 80 (2015) 5737–5744; doi:10.1021/acs.joc.5b00708

data_4030975
_publ_section_title
;
 Diastereo- and Enantioselective Construction of
 3,3'-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric
 1,3-Dipolar Cycloadditions.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5737
_journal_page_last               5744
_journal_paper_doi               10.1021/acs.joc.5b00708
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C35 H35 N3 O8'
_chemical_formula_weight         625.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.01
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8930(3)
_cell_length_b                   25.5926(8)
_cell_length_c                   14.1377(4)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      132.466
_cell_measurement_theta_min      6.252
_cell_volume                     3217.67(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28387
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.493
_diffrn_reflns_theta_min         1.726
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
; 
 Flack x determined using 3998 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     839
_refine_ls_number_reflns         10177
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0799
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1461P)^2^+0.4905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1989
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                9466
_reflns_number_total             10177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00708_si_002.cif
_cod_data_source_block           dm15006
_cod_depositor_comments          'Adding full bibliography for 4030975.cif.'
_cod_database_code               4030975
_shelx_estimated_absorpt_t_min   0.833
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2013-4
_shelx_res_checksum              12844
_shelx_hkl_checksum              90255