Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines.
Penger, Alexander; von Hahmann, Cortney N.; Filatov, Alexander S.; Welch, John T.; Beilstein journal of organic chemistry 9 (2013) 2675–2680; doi:10.3762/bjoc.9.303

data_4029711
_publ_section_title
;
 Diastereoselectivity in the Staudinger reaction of
 pentafluorosulfanylaldimines and ketimines.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              2675
_journal_page_last               2680
_journal_paper_doi               10.3762/bjoc.9.303
_journal_volume                  9
_journal_year                    2013
_chemical_formula_moiety         'C20 H22 F5 N O3 S'
_chemical_formula_sum            'C20 H22 F5 N O3 S'
_chemical_formula_weight         451.45
_chemical_name_systematic
; 
 (3SR,4RS)-3-(benzyloxy)-4-((1SR)-pentafluorosulfanyl-propyl)-
 -1-(4-methoxyphenyl)azetidin-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.168(13)
_cell_angle_beta                 95.116(14)
_cell_angle_gamma                97.126(13)
_cell_formula_units_Z            2
_cell_length_a                   6.809(7)
_cell_length_b                   10.145(10)
_cell_length_c                   14.616(15)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.39
_cell_volume                     995.6(17)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
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_diffrn_reflns_av_R_equivalents  0.0721
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6182
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.159
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     414
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.2002
_refine_ls_R_factor_gt           0.1262
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+17.3100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2922
_refine_ls_wR_factor_ref         0.3241
_reflns_number_gt                1667
_reflns_number_total             3390
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            1860-5397-9-303-S2.cif
_cod_data_source_block           7c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/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 
;
_cod_original_cell_volume        995.6(18)
_cod_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1        '
_cod_database_code               4029711