Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF3 to Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active Tetrasubstituted 3-Aminooxindoles.
Chen, Diao; Xu, Ming-Hua; The Journal of organic chemistry 79 (2014) 7746–7751; doi:10.1021/jo501360g

data_4029835
_publ_section_title
;
 Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF3 to
 Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active
 Tetrasubstituted 3-Aminooxindoles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7746
_journal_page_last               7751
_journal_paper_doi               10.1021/jo501360g
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_sum            'C13 H15 N3 O3 S'
_chemical_formula_weight         293.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.089(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2469(6)
_cell_length_b                   9.3854(5)
_cell_length_c                   14.4662(7)
_cell_measurement_temperature    296(2)
_cell_volume                     1619.57(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13771
_diffrn_reflns_theta_full        27.70
_diffrn_reflns_theta_max         27.70
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_correction_T_min  0.9082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.2
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.212
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5870
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0761
_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^)+(0.2000P)^2^+0.6544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2232
_reflns_number_gt                5179
_reflns_number_total             5870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501360g_si_002.cif
_cod_data_source_block           mo_2014194_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029835--4029836.cif.

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C26 H30 N6 O6 S2'
_cod_original_formula_weight         586.86
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4029835