Organocatalytic cascade Michael/Michael reaction for the asymmetric synthesis of spirooxindoles containing five contiguous stereocenters
Bo-Liang Zhao; Da-Ming Du; Chem.Commun. 52 (2016) 6162–; doi:

data_7119058
_publ_section_title
;
 Organocatalytic cascade Michael/Michael reaction for the asymmetric
 synthesis of spirooxindoles containing five contiguous stereocenters
;
_journal_name_full               Chem.Commun.
_journal_page_first              6162
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         C35H39BrN2O9
_chemical_formula_sum            'C35 H39 Br N2 O9'
_chemical_formula_weight         711.59
_chemical_melting_point          141.5(5)
_chemical_name_systematic
'(3aS,3'R,4S,6R,6aS)-Tri-tert-butyl 4-(2-bromophenyl)-1,2',3-trioxo-3a,4,6,6a-tetrahydro -1H-spiro[cyclopenta[c]pyrrole-5,3'-indoline]-1',2,6(3H)-tricarboxylate'
_chemical_properties_physical    Light-sensitive
_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
_audit_update_record
;
2016-01-08 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.919(2)
_cell_length_b                   15.875(3)
_cell_length_c                   17.332(3)
_cell_measurement_reflns_used    14245
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.507
_cell_measurement_theta_min      2.032
_cell_volume                     3554.6(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35914
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.211
_exptl_absorpt_correction_T_max  0.8115
_exptl_absorpt_correction_T_min  0.7128
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         11767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0095P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0559
_reflns_number_gt                9833
_reflns_number_total             11767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00705h2.cif
_cod_data_source_block           bo4267
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '141-142' was changed to '141.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 
;
_cod_original_cell_volume        3554.7(11)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7119058