Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes
Gianna Reginato; Bernardo Pezzati; Andrea Ienco; Gabriele Manca; Andrea Rossin; Alessandro Mordini; Journal of Organic Chemistry 76 (2011) 7415–7422; doi:10.1021/jo2010878

data_4026570
_publ_contact_author_address     'ICCOM-CNR, Firenze (Italy)'
_publ_contact_author_email       a.ienco@iccom.cnr.it
_publ_contact_author_fax         39(055)5225203
_publ_contact_author_name        'Ienco, Andrea'
_publ_contact_author_phone       39(055)5225284
_publ_section_title
;
 Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from
 Acyclic Chiral Amino Allylsilanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7415
_journal_page_last               7422
_journal_paper_doi               10.1021/jo2010878
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H17 N1 O2 S1'
_chemical_formula_sum            'C19 H17 N O2 S'
_chemical_formula_weight         323.4
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-02-19T16:03:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.472(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1880(15)
_cell_length_b                   8.0710(7)
_cell_length_c                   16.170(2)
_cell_measurement_reflns_used    2762
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.4065
_cell_measurement_theta_min      3.7976
_cell_measurement_wavelength     0.71073
_cell_volume                     1713.3(3)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.4547
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.843
_diffrn_orient_matrix_UB_11      -0.015727701
_diffrn_orient_matrix_UB_12      -0.0429424385
_diffrn_orient_matrix_UB_13      -0.0374536398
_diffrn_orient_matrix_UB_21      -0.0498132279
_diffrn_orient_matrix_UB_22      -0.0076479532
_diffrn_orient_matrix_UB_23      0.012848815
_diffrn_orient_matrix_UB_31      -0.0137780246
_diffrn_orient_matrix_UB_32      0.0764039302
_diffrn_orient_matrix_UB_33      -0.0196685562
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9972
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.8
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.86607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1134P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                1397
_reflns_number_total             2636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2010878_si_001_1.cif
_cod_data_source_block           c8
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026570