Asymmetric Synthesis of α-Fluoro-β-Amino-oxindoles with Tetrasubstituted C-F Stereogenic Centers via Cooperative Cation-Binding Catalysis.
Paladhi, Sushovan; Park, Sang Yeon; Yang, Jung Woon; Song, Choong Eui; Organic letters 19 (2017) 5336–5339; doi:10.1021/acs.orglett.7b02628

data_1547394
_publ_section_title
;
 Asymmetric Synthesis of \a-Fluoro-\b-Amino-oxindoles with
 Tetrasubstituted C-F Stereogenic Centers via Cooperative Cation-Binding
 Catalysis.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5336
_journal_page_last               5339
_journal_paper_doi               10.1021/acs.orglett.7b02628
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H27 F N2 O3'
_chemical_formula_sum            'C23 H27 F N2 O3'
_chemical_formula_weight         398.46
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1934(9)
_cell_length_b                   11.1437(10)
_cell_length_c                   19.3947(18)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      2.26
_cell_volume                     2203.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
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_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1441
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68177
_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         26.086
_diffrn_reflns_theta_min         2.100
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       Block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.5568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2895
_reflns_number_total             4382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02628_si_002.cif
_cod_data_source_block           195K-chiral
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547394.cif.
;
_cod_database_code               1547394
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              44958
_shelx_hkl_checksum              39741