A copper(i)-catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines: enantioselective synthesis of 3-substituted 3-aminooxindoles
Zhu, Jing-Yan; Yang, Wu-Lin; Liu, Yang-Zi; Shang, Shao-Jing; Deng, Wei-Ping; Organic Chemistry Frontiers 5 (2018) 70–; doi:10.1039/C7QO00691H

data_1553872
_publ_section_title
;
 A copper(i)-catalyzed asymmetric Mannich reaction of glycine Schiff bases
 with isatin-derived ketimines: enantioselective synthesis of
 3-substituted 3-aminooxindoles
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              70
_journal_paper_doi               10.1039/C7QO00691H
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H30 I N3 O5'
_chemical_formula_weight         639.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-07-27 deposited with the CCDC.
2017-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1518(14)
_cell_length_b                   12.3848(15)
_cell_length_c                   19.412(2)
_cell_measurement_reflns_used    6244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.672
_cell_measurement_theta_min      4.696
_cell_volume                     2921.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.950
_exptl_absorpt_coefficient_mu    1.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 1953 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.019(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0443P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4858
_reflns_number_total             5433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00691h2.cif
_cod_data_source_block           cd17236
_cod_database_code               1553872
_shelx_estimated_absorpt_t_min   0.804
_shelx_estimated_absorpt_t_max   0.866
_shelxl_version_number           2013-4
_shelx_res_checksum              69644
_shelx_hkl_checksum              77378