Organocatalytic stereocontrolled synthesis of 3,3'-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones
Liang-Liang Wang; Jian-Fei Bai; Lin Peng; Liang-Wen Qi; Li-Na Jia; Yun-Long Guo; Xi-Ya Luo; Xiaoying Xu; Li-xin Wang; Chem.Commun. 48 (2012) 5175–; doi:10.1039/c2cc30746d

data_7107701
_publ_section_title
;
 Organocatalytic stereocontrolled synthesis of 3,3'-pyrrolidinyl
 spirooxindoles by [3+2] annulation of isocyanoesters with
 methyleneindolinones
;
_journal_name_full               Chem.Commun.
_journal_page_first              5175
_journal_paper_doi               10.1039/c2cc30746d
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H27 Br N2 O7'
_chemical_formula_sum            'C27 H27 Br N2 O7'
_chemical_formula_weight         571.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9894(7)
_cell_length_b                   13.0968(8)
_cell_length_c                   17.2527(10)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      2.30
_cell_volume                     2709.1(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28898
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    1.564
_exptl_absorpt_correction_T_max  0.6958
_exptl_absorpt_correction_T_min  0.6105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(4)
_refine_ls_extinction_coef       0.0004(2)
_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   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         7693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0141P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0529
_reflns_number_gt                6997
_reflns_number_total             7693
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30746d.txt
_cod_data_source_block           mo_1847_7_sad
_cod_database_code               7107701