Asymmetric synthesis of (3S,1'S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one derivatives by addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones.
Qian, Ping; Xie, Chen; Wu, Lingmin; Mei, Haibo; Soloshonok, Vadim A.; Han, Jianlin; Pan, Yi; Organic & biomolecular chemistry 12 (2014) 7909–7913; doi:10.1039/c4ob01453g

data_7154029
_publ_section_title
;
 Asymmetric synthesis of
 (3S,1'S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one
 derivatives by addition of
 (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to
 1-(alkyl)-indolin-2-ones.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7909
_journal_page_last               7913
_journal_paper_doi               10.1039/c4ob01453g
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H19 F3 N2 O2 S'
_chemical_formula_sum            'C15 H19 F3 N2 O2 S'
_chemical_formula_weight         348.38
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7933(6)
_cell_length_b                   15.9715(17)
_cell_length_c                   18.559(2)
_cell_measurement_reflns_used    2098
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.10
_cell_measurement_theta_min      2.19
_cell_volume                     1717.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11787
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9581
_exptl_absorpt_correction_T_min  0.9288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     833
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0644P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                2505
_reflns_number_total             3969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01453g2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7154029.cif.
;
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7154029