Organocatalytic Asymmetric Mannich Reaction of 3-Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated N-Boc-Protected Aldimines for the Synthesis of Vicinal Oxindole-Diamines/Amino Alcohols.
Shan, Jing; Cui, Baodong; Wang, Yu; Yang, Chengli; Zhou, Xiaojian; Han, Wenyong; Chen, Yongzheng; The Journal of organic chemistry 81 (2016) 5270–5277; doi:10.1021/acs.joc.6b00278

data_4036677
_publ_section_title
;
 Organocatalytic Asymmetric Mannich Reaction of
 3-Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated
 N-Boc-Protected Aldimines for the Synthesis of Vicinal
 Oxindole-Diamines/Amino Alcohols.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5270
_journal_page_last               5277
_journal_paper_doi               10.1021/acs.joc.6b00278
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H27 N3 O5 S'
_chemical_formula_weight         445.53
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.402(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9327(6)
_cell_length_b                   12.6785(7)
_cell_length_c                   17.6556(9)
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.42
_cell_volume                     2519.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16442
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
;
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.17(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     658
_refine_ls_number_reflns         8907
_refine_ls_number_restraints     361
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.067
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                5864
_reflns_number_total             8907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00278_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4036677