Asymmetric Mannich Reaction: Highly Enantioselective Synthesis of 3-Amino-oxindoles via Chiral Squaramide Based H-bond Donor Catalysis
Trivedi, Rajiv; Kadiyala, Srinivasa Rao; Pambala, Ramesh; Chowhan, Raju; RSC Adv.  (2016) –; doi:10.1039/C6RA16877A

data_7226442
_publ_section_title
;
 Asymmetric Mannich Reaction: Highly Enantioselective Synthesis of
 3-Amino-oxindoles via Chiral Squaramide Based H-bond Donor Catalysis
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA16877A
_journal_year                    2016
_chemical_formula_moiety         'C19 H23 Br N2 O5'
_chemical_formula_sum            'C19 H23 Br N2 O5'
_chemical_formula_weight         439.31
_chemical_melting_point          442.0(10)
_chemical_name_common            7-Br
_chemical_name_systematic
'tert-butyl (7-bromo-3-(2,4-dioxopentan-3-yl)-1-methyl-2-oxoindolin-3-yl)carbamate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-02-04 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.596(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.9423(8)
_cell_length_b                   10.7137(10)
_cell_length_c                   10.4490(9)
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      3.46
_cell_volume                     997.85(16)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10269
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_T_max  0.511
_exptl_absorpt_correction_T_min  0.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             452.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.540
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2140 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.036(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                3733
_reflns_number_total             4547
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6ra16877a2.cif
_cod_data_source_block           7-Br-Ist_in_P21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '441-443' was changed to '442.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7226442